debian/0000755000000000000000000000000012146413116007165 5ustar debian/watch0000644000000000000000000000012711760660652010230 0ustar version=3 http://code.google.com/p/cinfony/downloads/list .*/cinfony-([\d.]+)\.tar\.gz debian/upstream0000644000000000000000000000071411760252453010760 0ustar Name: Cinfony Homepage: http://code.google.com/p/cinfony/ Reference: - Author: N. M. O'Boyle and G. R. Hutchison Title: "Cinfony - combining Open Source cheminformatics toolkits behind a common interface" Journal: Chem. Cent. J. Year: 2008 Volume: 2 Number: 1 Pages: 24444 URL: http://journal.chemistrycentral.com/content/2/1/24 eprint: http://journal.chemistrycentral.com/content/pdf/1752-153X-2-24.pdf DOI: 10.1186/1752-153X-2-24 debian/rules0000755000000000000000000000030711760660652010257 0ustar #!/usr/bin/make -f # -*- makefile -*- %: dh $@ --with python2 --parallel override_dh_clean: dh_clean test/*.png override_dh_auto_test: (cd test && PYTHONPATH=.. python testall.py) || /bin/true debian/copyright0000644000000000000000000000753412146410502011125 0ustar Format: http://www.debian.org/doc/packaging-manuals/copyright-format/1.0/ Upstream-Name: Cinfony Upstream-Contact: Noel O'Boyle Source: http://code.google.com/p/cinfony/downloads/list Disclaimer: Please cite N.M. O'Boyle, G.R. Hutchison, Chem. Cent. J., 2008, 2, 24 to support continued development of Cinfony. Files: * Copyright: 2008-2011, Noel O'Boyle 2012, Adrià Cereto-Massagué License: BSD Files: cinfony/pybel.py Copyright: 2008-2012, Noel O'Boyle 2012, Adrià Cereto-Massagué License: GPL-2+ This program is free software; you can redistribute it and/or modify it under the terms of the GNU General Public License as published by the Free Software Foundation; either version 2 of the License, or (at your option) any later version. . This program is distributed in the hope that it will be useful, but WITHOUT ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the GNU General Public License for more details. . You should have received a copy of the GNU General Public License along with this program; if not, write to the Free Software Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA 02110-1301 USA. Comment: On Debian systems the full text is also available as the file `/usr/share/common-licenses/GPL-2'. Files: cinfony/indy.py Copyright: 2011, Noel O'Boyle 2012, Adrià Cereto-Massagué License: GPL-3+ This program is free software: you can redistribute it and/or modify it under the terms of the GNU General Public License as published by the Free Software Foundation, either version 3 of the License, or (at your option) any later version. . This program is distributed in the hope that it will be useful, but WITHOUT ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE. See the GNU General Public License for more details. . You should have received a copy of the GNU General Public License along with this program. If not, see . Comment: On Debian systems the full text is also available as the file `/usr/share/common-licenses/GPL-3'. Files: debian/* Comment: This work was packaged for Debian by Michael Banck on Sat, 29 Oct 2011 21:12:19 +0200. Copyright: 2011 Michael Banck 2012,2013 Debichem Team License: BSD License: BSD Redistribution and use in source and binary forms, with or without modification, are permitted provided that the following conditions are met: 1. Redistributions of source code must retain the above copyright notice, this list of conditions and the following disclaimer. 2. Redistributions in binary form must reproduce the above copyright notice, this list of conditions and the following disclaimer in the documentation and/or other materials provided with the distribution. 3. Neither the name of the University nor the names of its contributors may be used to endorse or promote products derived from this software without specific prior written permission. . THIS SOFTWARE IS PROVIDED BY THE REGENTS AND CONTRIBUTORS ``AS IS'' AND ANY EXPRESS OR IMPLIED WARRANTIES, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE REGENTS OR CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL, SPECIAL, EXEMPLARY, OR CONSEQUENTIAL DAMAGES (INCLUDING, BUT NOT LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES; LOSS OF USE, DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER IN CONTRACT, STRICT LIABILITY, OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT OF THE USE OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE. debian/source/0000755000000000000000000000000012146413116010465 5ustar debian/source/format0000644000000000000000000000001411653073144011700 0ustar 3.0 (quilt) debian/compat0000644000000000000000000000000211653073144010370 0ustar 7 debian/control0000644000000000000000000000306012146413033010565 0ustar Source: cinfony Section: science Priority: optional Maintainer: Debichem Team Uploaders: Michael Banck Build-Depends: debhelper (>> 7.0.50~), libcdk-java, libopsin-java, python (>> 2.6.6-3~), python-jpype, python-openbabel, python-rdkit Standards-Version: 3.9.4 Homepage: http://code.google.com/p/cinfony/ Vcs-Browser: http://svn.debian.org/wsvn/debichem/unstable/cinfony/ Vcs-Svn: svn://svn.debian.org/svn/debichem/unstable/cinfony/ Package: python-cinfony Section: python Architecture: all XB-Python-Version: ${python:Versions} Depends: ${misc:Depends}, ${python:Depends}, ${shlibs:Depends} Recommends: libcdk-java, libopsin-java, python-imaging-tk, python-indigo, python-jpype, python-openbabel, python-rdkit Suggests: ironpython, jython Provides: ${python:Provides} Description: Python abstraction layer to cheminformatics toolkits Cinfoy provides a common Python interface to various cheminformatics toolkits. This makes it possible to use the complementary features of cheminformatics toolktis using a common interface. If functionality is provided by more than one toolkit, the Cinfony user can choose the implementation they prefer. . Cinfony supports the following toolkits: * OpenBabel * RDKit * CDK * Indigo . Cinfony also includes the Opsin module for translating IUPAC names to chemical data and the Webel web services module. debian/patches/0000755000000000000000000000000012146413116010614 5ustar debian/patches/series0000644000000000000000000000004211653073144012032 0ustar testsuite_missing_datafiles.patch debian/patches/testsuite_missing_datafiles.patch0000644000000000000000000104611412146407674017456 0ustar Author: Michael Banck Description: Add missing testfiles. Forwarded: should-be --- /dev/null 2011-09-24 09:52:54.343281093 +0200 +++ ./test/head.sdf 2008-04-13 17:17:37.000000000 +0200 @@ -0,0 +1,107 @@ +NSC 1 + ccorina 04030319103D 1 1.00000 0.00000 +CORINA 2.61 0041 25.10.2001 + 15 15 0 0 0 0 0 0 0 0 1 V2000 + 0.0021 -0.0041 0.0020 O 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0691 5.2414 0.0323 O 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0144 1.2102 0.0087 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.3034 1.9312 0.0310 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2546 1.9661 0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 + -1.3215 3.2712 0.0389 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.2365 3.3061 0.0085 C 0 0 0 0 0 0 0 0 0 0 0 0 + -0.0526 4.0271 0.0252 C 0 0 0 0 0 0 0 0 0 0 0 0 + -2.5980 1.1600 0.0445 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1971 1.4389 -0.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.2641 3.7984 0.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 + 2.1643 3.8588 -0.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 + -2.3843 0.0912 0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 + -3.1608 1.4105 0.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 + -3.1853 1.4206 -0.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 3 2 0 0 0 0 + 2 8 2 0 0 0 0 + 3 5 1 0 0 0 0 + 3 4 1 0 0 0 0 + 4 6 2 0 0 0 0 + 4 9 1 0 0 0 0 + 5 7 2 0 0 0 0 + 5 10 1 0 0 0 0 + 6 8 1 0 0 0 0 + 6 11 1 0 0 0 0 + 7 8 1 0 0 0 0 + 7 12 1 0 0 0 0 + 9 13 1 0 0 0 0 + 9 14 1 0 0 0 0 + 9 15 1 0 0 0 0 +M END +> +1 + +$$$$ +NSC 2 + ccorina 04030319103D 1 1.00000 0.00000 +CORINA 2.61 0041 25.10.2001 + 28 31 0 0 0 0 0 0 0 0 1 V2000 + -0.0165 1.3666 0.0096 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.2041 6.9305 2.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 + 0.0021 -0.0041 0.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1892 2.1056 0.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.5286 4.0208 -0.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 + 4.7319 5.7338 2.3165 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.0224 6.1538 2.5156 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.4205 6.3592 2.7733 C 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1946 -0.7124 -0.0132 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3840 1.3506 -0.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 + 7.1801 4.7823 2.8185 C 0 0 0 0 0 0 0 0 0 0 0 0 + 9.5376 5.0085 3.0668 C 0 0 0 0 0 0 0 0 0 0 0 0 + 2.3930 -0.0213 -0.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 + 8.4019 4.2188 3.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 + 5.7567 6.5587 2.2741 N 0 0 0 0 0 0 0 0 0 0 0 0 + 5.5106 4.1804 2.7344 S 0 0 0 0 0 0 0 0 0 0 0 0 + 3.0264 6.0746 2.0342 S 0 0 0 0 0 0 0 0 0 0 0 0 + 2.9255 5.7375 0.0045 S 0 0 0 0 0 0 0 0 0 0 0 0 + 3.6321 2.6151 -0.0192 S 0 0 0 0 0 0 0 0 0 0 0 0 + 1.3439 3.4473 0.0074 N 0 0 0 0 0 0 0 0 0 0 0 0 + -0.9624 1.8878 0.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 + 8.1482 7.9844 2.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 + -0.9329 -0.5446 0.0084 H 0 0 0 0 0 0 0 0 0 0 0 0 + 10.3079 6.9745 2.7570 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1.1876 -1.7924 -0.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 + 10.5055 4.5777 3.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 + 3.3299 -0.5584 -0.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 + 8.4764 3.1655 3.3136 H 0 0 0 0 0 0 0 0 0 0 0 0 + 1 3 2 0 0 0 0 + 1 4 1 0 0 0 0 + 1 21 1 0 0 0 0 + 2 8 2 0 0 0 0 + 2 7 1 0 0 0 0 + 2 22 1 0 0 0 0 + 3 9 1 0 0 0 0 + 3 23 1 0 0 0 0 + 4 10 2 0 0 0 0 + 4 20 1 0 0 0 0 + 5 18 1 0 0 0 0 + 5 20 2 0 0 0 0 + 5 19 1 0 0 0 0 + 6 17 1 0 0 0 0 + 6 15 2 0 0 0 0 + 6 16 1 0 0 0 0 + 7 15 1 0 0 0 0 + 7 11 2 0 0 0 0 + 8 12 1 0 0 0 0 + 8 24 1 0 0 0 0 + 9 13 2 0 0 0 0 + 9 25 1 0 0 0 0 + 10 19 1 0 0 0 0 + 10 13 1 0 0 0 0 + 11 16 1 0 0 0 0 + 11 14 1 0 0 0 0 + 12 14 2 0 0 0 0 + 12 26 1 0 0 0 0 + 13 27 1 0 0 0 0 + 14 28 1 0 0 0 0 + 17 18 1 0 0 0 0 +M END +> +2 + +$$$$ --- /dev/null 2011-09-24 09:52:54.343281093 +0200 +++ ./test/hashizume.cif 2008-04-13 17:17:37.000000000 +0200 @@ -0,0 +1,7205 @@ +############################################################################## +# # +# This CIF contains the data in a paper accepted for publication in Acta # +# Crystallographica Section B. It has been peer reviewed under the auspices # +# of the IUCr Commission on Journals. # +# # +# Full details of the Crystallographic Information File format # +# are given in the paper "The Crystallographic Information File (CIF): # +# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # +# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # +# # +# The current version of the core CIF dictionary may be obtained from # +# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # +# # +# Software is freely available for graphical display of the structure(s) in # +# this CIF. For information consult the CIF home page http://www.iucr.org/ # +# cif/home.html # +# # +# Copyright International Union of Crystallography # +# # +############################################################################## + +data_global +_audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' +_journal_date_recd_electronic 2002-11-14 +_journal_date_accepted 2003-03-12 +_journal_name_full 'Acta Crystallographica, Section B' +_journal_year 2003 +_journal_volume 59 +_journal_issue 3 +_journal_page_first 404 +_journal_page_last 415 +_journal_paper_category FA +_publ_contact_author_name 'Dr. Daisuke Hashizume' +_publ_contact_author_address +; + Molecular Characterization Division + RIKEN (The Institute of Physical and Chemical Research + 2-1, Hirosawa, Wako, Saitama 351-0198, Japan +; +_publ_contact_author_email 'hashi@postman.riken.go.jp' +_publ_contact_author_fax '81(48462)4628' +_publ_contact_author_phone '81(48467)9363' +_publ_section_title +; +Mechanism of First Order Phase Transition of Acylurea Derivative Crystal: +Observation of Intermediate Stages of Transformation +with a Detailed Temperature Resolved Single Crystal Diffraction Method +; +loop_ + _publ_author_name + _publ_author_address + 'Hashizume, Daisuke' +; + Department of Applied Physics and Chemistry + The University of Electro-Communications + Chofugaoka, Chofu, Tokyo 182-8585 + Japan +; + 'Miki, Naoko' +; + Department of Applied Physics and Chemistry + The University of Electro-Communications + Chofugaoka, Chofu, Tokyo 182-8585 + Japan +; + 'Yamazaki, Toshiyuki' +; + Department of Applied Physics and Chemistry + The University of Electro-Communications + Chofugaoka, Chofu, Tokyo 182-8585 + Japan +; + 'Aoyagi, Yosuke' +; + Department of Applied Physics and Chemistry + The University of Electro-Communications + Chofugaoka, Chofu, Tokyo 182-8585 + Japan +; + 'Tomokuni, Arisato' +; + Department of Chemistry + Aoyama Gakuin University + Chitosedai, Setagaya, Tokyo 157-8572 + Japan +; + 'Hiroki, Uchiyama' +; + Department of Chemistry + Aoyama Gakuin University + Chitosedai, Setagaya, Tokyo 157-8572 + Japan +; + 'Tadashi, Endo' +; + Department of Chemistry + Aoyama Gakuin University + Chitosedai, Setagaya, Tokyo 157-8572 + Japan +; + 'Yasui, Masanori' +; + Department of Applied Physics and Chemistry + The University of Electro-Communications + Chofugaoka, Chofu, Tokyo 182-8585 + Japan +; + 'Iwasaki, Fujiko' +; + Department of Applied Physics and Chemistry + The University of Electro-Communications + Chofugaoka, Chofu, Tokyo 182-8585 + Japan +; +_publ_section_synopsis +; ? +; +data_ethyl98K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7038(14) +_cell_length_b 12.204(3) +_cell_length_c 4.9747(10) +_cell_angle_alpha 93.021(11) +_cell_angle_beta 90.616(7) +_cell_angle_gamma 90.319(10) +_cell_volume 527.64(19) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 4199 +_cell_measurement_theta_min 2.34 +_cell_measurement_theta_max 27.485 +_cell_measurement_temperature 98 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.172 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.083 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal is being low temperature phase. +; +_diffrn_ambient_temperature 98 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6068 +_diffrn_reflns_av_R_equivalents 0.035 +_diffrn_reflns_av_sigmaI/netI 0.0133 +_diffrn_reflns_theta_min 2.34 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.857 +_diffrn_measured_fraction_theta_full 0.857 +_diffrn_reflns_limit_h_min -10 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -15 +_diffrn_reflns_limit_k_max 15 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2076 +_reflns_number_gt 1992 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.0468 +_refine_ls_R_factor_gt 0.0453 +_refine_ls_wR_factor_gt 0.1263 +_refine_ls_wR_factor_ref 0.1282 +_refine_ls_goodness_of_fit_ref 1.101 +_refine_ls_restrained_S_all 1.101 +_refine_ls_number_reflns 2076 +_refine_ls_number_parameters 190 +_refine_ls_number_restraints 0 +_refine_ls_hydrogen_treatment refall +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens difmap +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.272 +_refine_diff_density_min -0.236 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution 'SIR-97 (Sheldrick, 1990)' +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.44032(10) 0.57459(7) 0.24164(18) 0.0197(2) Uani d . 1 . . O + O2 0.02166(10) 0.40706(7) 0.22035(18) 0.0195(2) Uani d . 1 . . O + N1 0.19696(12) 0.53547(8) 0.3825(2) 0.0165(3) Uani d . 1 . . N + H11 0.128(2) 0.5538(14) 0.506(4) 0.021(4) Uiso d . 1 . . H + N2 0.25049(12) 0.41607(8) 0.0069(2) 0.0167(2) Uani d . 1 . . N + H21 0.338(2) 0.4465(14) 0.003(4) 0.023(4) Uiso d . 1 . . H + C1 0.33545(14) 0.59050(9) 0.4018(2) 0.0158(3) Uani d . 1 . . C + C2 0.15101(14) 0.44889(9) 0.1958(2) 0.0162(3) Uani d . 1 . . C + C11 0.35090(15) 0.67433(10) 0.6398(2) 0.0178(3) Uani d . 1 . . C + H111 0.439(2) 0.6487(13) 0.745(3) 0.021(4) Uiso d . 1 . . H + H112 0.2602(19) 0.6735(13) 0.748(3) 0.018(4) Uiso d . 1 . . H + C12 0.38521(15) 0.79070(10) 0.5489(3) 0.0198(3) Uani d . 1 . . C + H121 0.405(2) 0.8406(15) 0.712(4) 0.027(4) Uiso d . 1 . . H + H122 0.4770(19) 0.7875(13) 0.445(3) 0.018(4) Uiso d . 1 . . H + C13 0.25484(18) 0.84117(10) 0.3886(3) 0.0260(3) Uani d . 1 . . C + H131 0.232(2) 0.7902(16) 0.225(4) 0.033(5) Uiso d . 1 . . H + C14 0.3084(3) 0.95237(12) 0.2891(3) 0.0387(4) Uani d . 1 . . C + H141 0.332(2) 1.0040(17) 0.440(4) 0.040(5) Uiso d . 1 . . H + H142 0.397(3) 0.9434(18) 0.175(5) 0.047(6) Uiso d . 1 . . H + H143 0.224(3) 0.9838(19) 0.185(5) 0.053(6) Uiso d . 1 . . H + C15 0.10882(18) 0.85613(13) 0.5535(4) 0.0354(4) Uani d . 1 . . C + H151 0.131(2) 0.9070(17) 0.722(4) 0.041(5) Uiso d . 1 . . H + H152 0.065(3) 0.7830(19) 0.622(5) 0.050(6) Uiso d . 1 . . H + H153 0.026(3) 0.8914(19) 0.445(5) 0.052(6) Uiso d . 1 . . H + C21 0.21377(14) 0.32246(10) -0.1823(2) 0.0181(3) Uani d . 1 . . C + H211 0.2767(18) 0.3308(13) -0.340(3) 0.017(4) Uiso d . 1 . . H + H212 0.107(2) 0.3260(13) -0.231(3) 0.019(4) Uiso d . 1 . . H + C22 0.24513(17) 0.21233(11) -0.0605(3) 0.0252(3) Uani d . 1 . . C + H221 0.355(2) 0.2097(16) -0.005(4) 0.039(5) Uiso d . 1 . . H + H222 0.179(2) 0.2045(15) 0.100(4) 0.033(5) Uiso d . 1 . . H + H223 0.221(2) 0.1502(16) -0.196(4) 0.037(5) Uiso d . 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0159(4) 0.0238(5) 0.0191(4) -0.0018(3) 0.0033(4) -0.0007(3) + O2 0.0150(4) 0.0237(5) 0.0195(4) -0.0031(3) 0.0032(3) -0.0011(3) + N1 0.0139(5) 0.0198(5) 0.0155(5) -0.0004(4) 0.0037(4) -0.0015(4) + N2 0.0136(5) 0.0197(5) 0.0164(5) -0.0017(4) 0.0012(4) -0.0018(4) + C1 0.0158(6) 0.0165(5) 0.0154(6) 0.0006(4) -0.0010(5) 0.0030(4) + C2 0.0165(6) 0.0171(5) 0.0151(5) 0.0006(4) -0.0008(4) 0.0024(4) + C11 0.0169(6) 0.0210(6) 0.0153(6) -0.0003(4) 0.0001(5) -0.0010(4) + C12 0.0192(6) 0.0196(6) 0.0204(6) -0.0026(4) 0.0016(5) -0.0018(4) + C13 0.0374(8) 0.0186(6) 0.0215(6) 0.0000(5) -0.0086(6) -0.0014(5) + C14 0.0656(12) 0.0217(7) 0.0289(8) -0.0009(7) -0.0022(8) 0.0029(6) + C15 0.0244(7) 0.0270(7) 0.0544(10) 0.0034(5) -0.0106(7) -0.0002(7) + C21 0.0170(6) 0.0214(6) 0.0156(6) -0.0004(4) -0.0001(5) -0.0030(4) + C22 0.0274(7) 0.0213(6) 0.0267(7) 0.0014(5) 0.0014(6) -0.0010(5) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.2275(15) ? + O2 C2 . 1.2435(15) ? + N1 C1 . 1.3766(15) ? + N1 C2 . 1.4224(15) ? + N1 H11 . 0.880(19) ? + N2 C2 . 1.3321(16) ? + N2 C21 . 1.4730(15) ? + N2 H21 . 0.846(18) ? + C1 C11 . 1.5280(16) ? + C11 C12 . 1.5417(17) ? + C11 H111 . 0.984(18) ? + C11 H112 . 0.961(17) ? + C12 C13 . 1.5304(19) ? + C12 H121 . 1.003(18) ? + C12 H122 . 0.955(17) ? + C13 C15 . 1.527(2) ? + C13 C14 . 1.540(2) ? + C13 H131 . 1.01(2) ? + C14 H141 . 0.98(2) ? + C14 H142 . 0.97(2) ? + C14 H143 . 0.99(2) ? + C15 H151 . 1.03(2) ? + C15 H152 . 1.04(2) ? + C15 H153 . 1.01(3) ? + C21 C22 . 1.5280(18) ? + C21 H211 . 0.971(16) ? + C21 H212 . 0.959(17) ? + C22 H221 . 0.99(2) ? + C22 H222 . 0.997(19) ? + C22 H223 . 1.01(2) ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 128.59(10) ? + C1 N1 H11 . . 116.4(11) ? + C2 N1 H11 . . 114.9(11) ? + C2 N2 C21 . . 120.62(11) ? + C2 N2 H21 . . 119.6(12) ? + C21 N2 H21 . . 119.6(12) ? + O1 C1 N1 . . 123.40(11) ? + O1 C1 C11 . . 121.49(11) ? + N1 C1 C11 . . 115.11(10) ? + O2 C2 N2 . . 123.75(11) ? + O2 C2 N1 . . 118.33(11) ? + N2 C2 N1 . . 117.90(11) ? + C1 C11 C12 . . 112.12(10) ? + C1 C11 H111 . . 104.6(10) ? + C12 C11 H111 . . 109.3(9) ? + C1 C11 H112 . . 110.2(10) ? + C12 C11 H112 . . 111.1(10) ? + H111 C11 H112 . . 109.3(14) ? + C13 C12 C11 . . 114.44(11) ? + C13 C12 H121 . . 107.3(10) ? + C11 C12 H121 . . 108.8(10) ? + C13 C12 H122 . . 110.3(10) ? + C11 C12 H122 . . 107.9(9) ? + H121 C12 H122 . . 107.8(14) ? + C15 C13 C12 . . 112.30(12) ? + C15 C13 C14 . . 110.07(13) ? + C12 C13 C14 . . 109.30(13) ? + C15 C13 H131 . . 109.2(11) ? + C12 C13 H131 . . 107.8(11) ? + C14 C13 H131 . . 108.1(11) ? + C13 C14 H141 . . 110.9(12) ? + C13 C14 H142 . . 110.9(13) ? + H141 C14 H142 . . 109.8(18) ? + C13 C14 H143 . . 108.6(13) ? + H141 C14 H143 . . 107.5(18) ? + H142 C14 H143 . . 109.1(19) ? + C13 C15 H151 . . 109.7(11) ? + C13 C15 H152 . . 113.7(13) ? + H151 C15 H152 . . 106.7(17) ? + C13 C15 H153 . . 110.8(13) ? + H151 C15 H153 . . 107.7(18) ? + H152 C15 H153 . . 108.0(18) ? + N2 C21 C22 . . 112.23(10) ? + N2 C21 H211 . . 106.7(9) ? + C22 C21 H211 . . 110.5(9) ? + N2 C21 H212 . . 108.5(10) ? + C22 C21 H212 . . 109.0(10) ? + H211 C21 H212 . . 109.9(14) ? + C21 C22 H221 . . 108.9(12) ? + C21 C22 H222 . . 109.5(11) ? + H221 C22 H222 . . 109.7(17) ? + C21 C22 H223 . . 110.3(12) ? + H221 C22 H223 . . 109.7(17) ? + H222 C22 H223 . . 108.7(15) ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 4.1(2) ? + C2 N1 C1 C11 . . . . -175.84(11) ? + C21 N2 C2 O2 . . . . -2.54(18) ? + C21 N2 C2 N1 . . . . 176.29(10) ? + C1 N1 C2 O2 . . . . 177.05(11) ? + C1 N1 C2 N2 . . . . -1.85(19) ? + O1 C1 C11 C12 . . . . 58.34(15) ? + N1 C1 C11 C12 . . . . -121.68(12) ? + C1 C11 C12 C13 . . . . 65.93(14) ? + C11 C12 C13 C15 . . . . 62.45(15) ? + C11 C12 C13 C14 . . . . -175.11(12) ? + C2 N2 C21 C22 . . . . -81.62(14) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.846(18) 2.300(18) 2.9778(15) 137.4(16) + N1 H11 O2 2_566 0.880(19) 1.942(19) 2.8222(14) 179.3(17) +data_ethyl298K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.8173(5) +_cell_length_b 12.4339(12) +_cell_length_c 5.09630(10) +_cell_angle_alpha 92.912(12) +_cell_angle_beta 89.876(3) +_cell_angle_gamma 90.152(10) +_cell_volume 558.00(6) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 3690 +_cell_measurement_theta_min 2.31 +_cell_measurement_theta_max 27.485 +_cell_measurement_temperature 298 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.109 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.078 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 298 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6494 +_diffrn_reflns_av_R_equivalents 0.026 +_diffrn_reflns_av_sigmaI/netI 0.0128 +_diffrn_reflns_theta_min 2.31 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.890 +_diffrn_measured_fraction_theta_full 0.890 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2292 +_reflns_number_gt 2041 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.0623 +_refine_ls_R_factor_gt 0.0572 +_refine_ls_wR_factor_gt 0.1642 +_refine_ls_wR_factor_ref 0.1709 +_refine_ls_goodness_of_fit_ref 1.090 +_refine_ls_restrained_S_all 1.090 +_refine_ls_number_reflns 2292 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 0 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.1104P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens difmap +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.161 +_refine_diff_density_min -0.205 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 98K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.43498(13) 0.57527(10) 0.2374(2) 0.0566(3) Uani d . 1 . . O + O2 0.02574(12) 0.40870(10) 0.2301(2) 0.0559(3) Uani d . 1 . . O + N1 0.19711(14) 0.53487(11) 0.3806(3) 0.0458(3) Uani d . 1 . . N + H11 0.1303 0.5546 0.4964 0.055 Uiso calc R 1 . . H + N2 0.25183(14) 0.41611(11) 0.0194(3) 0.0467(3) Uani d . 1 . . N + H21 0.3377 0.4486 0.0081 0.056 Uiso calc R 1 . . H + C1 0.33136(17) 0.59074(12) 0.3945(3) 0.0434(3) Uani d . 1 . . C + C2 0.15267(17) 0.44949(12) 0.2036(3) 0.0435(3) Uani d . 1 . . C + C11 0.34433(19) 0.67384(13) 0.6232(3) 0.0506(4) Uani d . 1 . . C + H111 0.4235 0.6518 0.7407 0.061 Uiso calc R 1 . . H + H112 0.2497 0.6756 0.7206 0.061 Uiso calc R 1 . . H + C12 0.3802(2) 0.78742(14) 0.5365(4) 0.0593(5) Uani d . 1 . . C + H122 0.4721 0.7845 0.4314 0.071 Uiso calc R 1 . . H + H121 0.4003 0.8337 0.6917 0.071 Uiso calc R 1 . . H + C13 0.2540(3) 0.83858(16) 0.3773(4) 0.0796(7) Uani d . 1 . . C + H131 0.2317 0.7905 0.2237 0.096 Uiso calc R 1 . . H + C14 0.3089(5) 0.9478(2) 0.2795(6) 0.1270(14) Uani d . 1 . . C + H142 0.4010 0.9374 0.1807 0.152 Uiso calc R 1 . . H + H141 0.3273 0.9970 0.4276 0.152 Uiso calc R 1 . . H + H143 0.2326 0.9770 0.1696 0.152 Uiso calc R 1 . . H + C15 0.1085(3) 0.8545(2) 0.5371(8) 0.1137(11) Uani d . 1 . . C + H152 0.0752 0.7865 0.5975 0.136 Uiso calc R 1 . . H + H153 0.0313 0.8837 0.4289 0.136 Uiso calc R 1 . . H + H151 0.1275 0.9034 0.6853 0.136 Uiso calc R 1 . . H + C21 0.21680(19) 0.32495(14) -0.1641(3) 0.0521(4) Uani d . 1 . . C + H211 0.2769 0.3309 -0.3224 0.062 Uiso calc R 1 . . H + H212 0.1107 0.3281 -0.2130 0.062 Uiso calc R 1 . . H + C22 0.2482(3) 0.21723(17) -0.0493(5) 0.0752(6) Uani d . 1 . . C + H223 0.2233 0.1603 -0.1764 0.090 Uiso calc R 1 . . H + H222 0.1875 0.2102 0.1056 0.090 Uiso calc R 1 . . H + H221 0.3536 0.2129 -0.0045 0.090 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0431(6) 0.0655(7) 0.0603(7) -0.0078(5) 0.0161(5) -0.0055(5) + O2 0.0417(6) 0.0639(7) 0.0611(7) -0.0104(5) 0.0151(5) -0.0057(5) + N1 0.0388(6) 0.0504(7) 0.0478(7) -0.0021(5) 0.0119(5) -0.0017(5) + N2 0.0373(6) 0.0524(7) 0.0500(7) -0.0035(5) 0.0094(5) -0.0028(5) + C1 0.0393(7) 0.0459(7) 0.0454(7) 0.0009(6) 0.0040(6) 0.0075(6) + C2 0.0375(7) 0.0473(8) 0.0459(8) 0.0003(5) 0.0075(6) 0.0044(6) + C11 0.0484(8) 0.0565(9) 0.0464(8) -0.0022(7) 0.0016(7) -0.0007(7) + C12 0.0574(10) 0.0546(9) 0.0648(10) -0.0081(7) 0.0072(8) -0.0070(8) + C13 0.1154(19) 0.0504(10) 0.0725(13) 0.0025(11) -0.0222(13) -0.0023(9) + C14 0.222(4) 0.0612(14) 0.099(2) 0.0031(19) 0.000(2) 0.0182(14) + C15 0.0764(17) 0.0853(18) 0.179(3) 0.0166(13) -0.027(2) 0.0036(19) + C21 0.0456(8) 0.0586(9) 0.0512(9) 0.0001(7) 0.0038(7) -0.0056(7) + C22 0.0866(15) 0.0569(11) 0.0815(14) 0.0030(10) 0.0070(12) -0.0040(9) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.2227(19) ? + O2 C2 . 1.2375(18) ? + N1 C1 . 1.3710(19) ? + N1 C2 . 1.413(2) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.3328(19) ? + N2 C21 . 1.465(2) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.522(2) ? + C11 C12 . 1.533(2) ? + C11 H111 . 0.9700 ? + C11 H112 . 0.9700 ? + C12 C13 . 1.537(3) ? + C12 H122 . 0.9700 ? + C12 H121 . 0.9700 ? + C13 C15 . 1.526(4) ? + C13 C14 . 1.547(3) ? + C13 H131 . 0.9800 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C14 H143 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C21 C22 . 1.515(3) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.32(13) ? + C1 N1 H11 . . 115.3 ? + C2 N1 H11 . . 115.3 ? + C2 N2 C21 . . 121.00(13) ? + C2 N2 H21 . . 119.5 ? + C21 N2 H21 . . 119.5 ? + O1 C1 N1 . . 123.17(15) ? + O1 C1 C11 . . 121.57(14) ? + N1 C1 C11 . . 115.25(13) ? + O2 C2 N2 . . 123.65(15) ? + O2 C2 N1 . . 118.60(13) ? + N2 C2 N1 . . 117.74(13) ? + C1 C11 C12 . . 113.22(13) ? + C1 C11 H111 . . 108.9 ? + C12 C11 H111 . . 108.9 ? + C1 C11 H112 . . 108.9 ? + C12 C11 H112 . . 108.9 ? + H111 C11 H112 . . 107.7 ? + C11 C12 C13 . . 114.62(16) ? + C11 C12 H122 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + C11 C12 H121 . . 108.6 ? + C13 C12 H121 . . 108.6 ? + H122 C12 H121 . . 107.6 ? + C15 C13 C12 . . 112.0(2) ? + C15 C13 C14 . . 109.9(2) ? + C12 C13 C14 . . 109.8(2) ? + C15 C13 H131 . . 108.4 ? + C12 C13 H131 . . 108.4 ? + C14 C13 H131 . . 108.4 ? + C13 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C14 H143 . . 109.5 ? + H142 C14 H143 . . 109.5 ? + H141 C14 H143 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H152 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + N2 C21 C22 . . 112.64(15) ? + N2 C21 H211 . . 109.1 ? + C22 C21 H211 . . 109.1 ? + N2 C21 H212 . . 109.1 ? + C22 C21 H212 . . 109.1 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 3.1(3) ? + C2 N1 C1 C11 . . . . -176.24(14) ? + C21 N2 C2 O2 . . . . -1.4(2) ? + C21 N2 C2 N1 . . . . 177.30(13) ? + C1 N1 C2 O2 . . . . 178.47(14) ? + C1 N1 C2 N2 . . . . -0.3(2) ? + O1 C1 C11 C12 . . . . 56.7(2) ? + N1 C1 C11 C12 . . . . -123.93(15) ? + C1 C11 C12 C13 . . . . 66.0(2) ? + C11 C12 C13 C15 . . . . 62.9(2) ? + C11 C12 C13 C14 . . . . -174.74(19) ? + C2 N2 C21 C22 . . . . -82.8(2) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.37 3.0573(17) 136.9 + N1 H11 O2 2_566 0.86 1.99 2.8525(17) 176.6 +data_ethyl328K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7817(18) +_cell_length_b 12.381(2) +_cell_length_c 5.1113(11) +_cell_angle_alpha 92.491(8) +_cell_angle_beta 90.164(9) +_cell_angle_gamma 89.589(9) +_cell_volume 555.17(19) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 3475 +_cell_measurement_theta_min 2.31 +_cell_measurement_theta_max 27.47 +_cell_measurement_temperature 328 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.114 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.079 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 328 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 7578 +_diffrn_reflns_av_R_equivalents 0.026 +_diffrn_reflns_av_sigmaI/netI 0.0148 +_diffrn_reflns_theta_min 2.32 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.849 +_diffrn_measured_fraction_theta_full 0.849 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -15 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2169 +_reflns_number_gt 1728 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.0738 +_refine_ls_R_factor_gt 0.0599 +_refine_ls_wR_factor_gt 0.1475 +_refine_ls_wR_factor_ref 0.1621 +_refine_ls_goodness_of_fit_ref 1.077 +_refine_ls_restrained_S_all 1.077 +_refine_ls_number_reflns 2169 +_refine_ls_number_parameters 166 +_refine_ls_number_restraints 0 +_refine_ls_hydrogen_treatment mixed +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.1725P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.174 +_refine_diff_density_min -0.177 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 298K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.43409(16) 0.57524(13) 0.2348(3) 0.0691(5) Uani d . 1 . . O + O2 0.02639(15) 0.40900(13) 0.2335(3) 0.0688(5) Uani d . 1 . . O + N1 0.19755(18) 0.53428(14) 0.3789(4) 0.0565(4) Uani d . 1 . . N + H11 0.134(3) 0.5526(18) 0.491(5) 0.063(6) Uiso d . 1 . . H + N2 0.25155(19) 0.41618(14) 0.0232(3) 0.0589(5) Uani d . 1 . . N + H21 0.331(3) 0.4469(19) 0.017(5) 0.070(7) Uiso d . 1 . . H + C1 0.3307(2) 0.59059(15) 0.3924(4) 0.0537(5) Uani d . 1 . . C + C2 0.1534(2) 0.44946(16) 0.2065(4) 0.0543(5) Uani d . 1 . . C + C11 0.3432(3) 0.67318(18) 0.6154(5) 0.0641(5) Uani d . 1 . . C + H112 0.252(3) 0.676(2) 0.715(5) 0.081(7) Uiso d . 1 . . H + H111 0.427(3) 0.650(2) 0.729(6) 0.097(9) Uiso d . 1 . . H + C12 0.3788(3) 0.7864(2) 0.5310(6) 0.0760(7) Uani d . 1 . . C + H121 0.400(3) 0.842(2) 0.704(6) 0.101(9) Uiso d . 1 . . H + H122 0.480(4) 0.782(2) 0.415(6) 0.103(9) Uiso d . 1 . . H + C13 0.2550(4) 0.8377(2) 0.3726(7) 0.0996(10) Uani d . 1 . . C + H131 0.234(4) 0.790(3) 0.224(8) 0.131(12) Uiso d . 1 . . H + C14 0.3084(7) 0.9468(3) 0.2766(9) 0.1566(19) Uani d . 1 . . C + H143 0.2285 0.9790 0.1770 0.188 Uiso calc R 1 . . H + H142 0.3968 0.9359 0.1683 0.188 Uiso calc R 1 . . H + H141 0.3333 0.9939 0.4245 0.188 Uiso calc R 1 . . H + C15 0.1083(4) 0.8540(3) 0.5295(11) 0.1496(18) Uani d . 1 . . C + H153 0.0324 0.8869 0.4228 0.179 Uiso calc R 1 . . H + H151 0.1279 0.9000 0.6817 0.179 Uiso calc R 1 . . H + H152 0.0725 0.7852 0.5827 0.179 Uiso calc R 1 . . H + C21 0.2176(3) 0.32596(19) -0.1566(5) 0.0652(6) Uani d . 1 . . C + H212 0.111(3) 0.3305(18) -0.210(5) 0.069(6) Uiso d . 1 . . H + H211 0.279(3) 0.3354(19) -0.316(5) 0.078(7) Uiso d . 1 . . H + C22 0.2497(5) 0.2186(2) -0.0422(8) 0.0929(9) Uani d . 1 . . C + H223 0.229(4) 0.161(3) -0.165(7) 0.110(10) Uiso d . 1 . . H + H222 0.188(4) 0.209(2) 0.100(7) 0.104(10) Uiso d . 1 . . H + H221 0.363(4) 0.214(3) 0.001(6) 0.114(11) Uiso d . 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0488(7) 0.0798(10) 0.0782(10) -0.0104(6) 0.0217(7) -0.0042(8) + O2 0.0478(8) 0.0781(10) 0.0802(10) -0.0124(7) 0.0188(7) -0.0034(8) + N1 0.0449(8) 0.0618(10) 0.0630(10) -0.0027(7) 0.0163(7) 0.0010(8) + N2 0.0429(8) 0.0654(10) 0.0683(11) -0.0045(7) 0.0120(7) 0.0013(8) + C1 0.0434(9) 0.0560(10) 0.0625(11) 0.0012(7) 0.0067(8) 0.0122(9) + C2 0.0422(9) 0.0583(11) 0.0631(11) 0.0002(7) 0.0106(8) 0.0099(9) + C11 0.0565(12) 0.0684(13) 0.0673(13) -0.0027(10) 0.0054(10) 0.0014(10) + C12 0.0675(14) 0.0705(14) 0.0896(17) -0.0082(11) 0.0109(12) -0.0023(13) + C13 0.133(3) 0.0673(16) 0.098(2) 0.0028(16) -0.0226(19) 0.0039(15) + C14 0.258(6) 0.080(2) 0.135(3) 0.004(3) 0.005(4) 0.030(2) + C15 0.089(2) 0.113(3) 0.247(6) 0.024(2) -0.025(3) 0.011(3) + C21 0.0526(11) 0.0728(14) 0.0698(14) -0.0016(9) 0.0059(10) -0.0026(11) + C22 0.102(2) 0.0703(17) 0.106(2) 0.0013(15) 0.0101(19) -0.0013(16) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.224(2) ? + O2 C2 . 1.236(2) ? + N1 C1 . 1.366(2) ? + N1 C2 . 1.398(3) ? + N1 H11 . 0.82(3) ? + N2 C2 . 1.325(2) ? + N2 C21 . 1.448(3) ? + N2 H21 . 0.80(2) ? + C1 C11 . 1.502(3) ? + C11 C12 . 1.519(3) ? + C11 H112 . 0.95(3) ? + C11 H111 . 0.98(3) ? + C12 C13 . 1.507(4) ? + C12 H121 . 1.12(3) ? + C12 H122 . 1.07(3) ? + C13 C15 . 1.527(5) ? + C13 C14 . 1.534(5) ? + C13 H131 . 0.96(4) ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C21 C22 . 1.500(4) ? + C21 H212 . 0.98(2) ? + C21 H211 . 0.99(3) ? + C22 H223 . 0.95(3) ? + C22 H222 . 0.92(3) ? + C22 H221 . 1.02(4) ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.89(17) ? + C1 N1 H11 . . 115.1(16) ? + C2 N1 H11 . . 115.0(16) ? + C2 N2 C21 . . 121.34(18) ? + C2 N2 H21 . . 117.7(18) ? + C21 N2 H21 . . 120.9(18) ? + O1 C1 N1 . . 122.75(19) ? + O1 C1 C11 . . 121.63(18) ? + N1 C1 C11 . . 115.62(17) ? + O2 C2 N2 . . 123.54(19) ? + O2 C2 N1 . . 118.75(17) ? + N2 C2 N1 . . 117.71(17) ? + C1 C11 C12 . . 114.0(2) ? + C1 C11 H112 . . 110.6(15) ? + C12 C11 H112 . . 108.5(16) ? + C1 C11 H111 . . 107.6(17) ? + C12 C11 H111 . . 107.6(16) ? + H112 C11 H111 . . 108(2) ? + C13 C12 C11 . . 114.6(2) ? + C13 C12 H121 . . 106.5(15) ? + C11 C12 H121 . . 111.0(15) ? + C13 C12 H122 . . 108.0(16) ? + C11 C12 H122 . . 108.2(16) ? + H121 C12 H122 . . 108(2) ? + C12 C13 C15 . . 111.8(3) ? + C12 C13 C14 . . 110.2(3) ? + C15 C13 C14 . . 109.5(3) ? + C12 C13 H131 . . 108(2) ? + C15 C13 H131 . . 108(2) ? + C14 C13 H131 . . 109(2) ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H153 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + N2 C21 C22 . . 112.8(2) ? + N2 C21 H212 . . 109.0(13) ? + C22 C21 H212 . . 110.1(13) ? + N2 C21 H211 . . 107.1(14) ? + C22 C21 H211 . . 111.2(14) ? + H212 C21 H211 . . 106(2) ? + C21 C22 H223 . . 111(2) ? + C21 C22 H222 . . 110(2) ? + H223 C22 H222 . . 107(3) ? + C21 C22 H221 . . 108.9(18) ? + H223 C22 H221 . . 106(3) ? + H222 C22 H221 . . 113(3) ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 3.4(3) ? + C2 N1 C1 C11 . . . . -176.41(19) ? + C21 N2 C2 O2 . . . . -2.0(3) ? + C21 N2 C2 N1 . . . . 177.44(18) ? + C1 N1 C2 O2 . . . . 178.90(19) ? + C1 N1 C2 N2 . . . . -0.5(3) ? + O1 C1 C11 C12 . . . . 55.6(3) ? + N1 C1 C11 C12 . . . . -124.7(2) ? + C1 C11 C12 C13 . . . . 65.7(3) ? + C11 C12 C13 C15 . . . . 63.1(4) ? + C11 C12 C13 C14 . . . . -174.8(3) ? + C2 N2 C21 C22 . . . . -82.2(3) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.80(2) 2.44(3) 3.067(2) 136(2) + N1 H11 O2 2_566 0.82(3) 2.04(3) 2.858(2) 177(2) +data_ethyl348K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.740(2) +_cell_length_b 12.357(2) +_cell_length_c 5.1473(12) +_cell_angle_alpha 91.509(8) +_cell_angle_beta 90.236(11) +_cell_angle_gamma 89.525(13) +_cell_volume 555.7(2) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2704 +_cell_measurement_theta_min 1.65 +_cell_measurement_theta_max 26.93 +_cell_measurement_temperature 348 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.113 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.079 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 348 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6205 +_diffrn_reflns_av_R_equivalents 0.036 +_diffrn_reflns_av_sigmaI/netI 0.0177 +_diffrn_reflns_theta_min 2.33 +_diffrn_reflns_theta_max 27.46 +_diffrn_reflns_theta_full 27.46 +_diffrn_measured_fraction_theta_max 0.760 +_diffrn_measured_fraction_theta_full 0.760 +_diffrn_reflns_limit_h_min -10 +_diffrn_reflns_limit_h_max 10 +_diffrn_reflns_limit_k_min -15 +_diffrn_reflns_limit_k_max 15 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 1939 +_reflns_number_gt 1418 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1003 +_refine_ls_R_factor_gt 0.0816 +_refine_ls_wR_factor_gt 0.2314 +_refine_ls_wR_factor_ref 0.2549 +_refine_ls_goodness_of_fit_ref 1.059 +_refine_ls_restrained_S_all 1.065 +_refine_ls_number_reflns 1939 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1229P)^2^+0.2315P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.269 +_refine_diff_density_min -0.211 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 328K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4329(2) 0.5747(2) 0.2314(5) 0.0846(7) Uani d . 1 . . O + O2 0.0266(2) 0.4099(2) 0.2382(5) 0.0837(7) Uani d . 1 . . O + N1 0.1972(3) 0.5337(2) 0.3770(5) 0.0701(7) Uani d . 1 . . N + H11 0.1302 0.5530 0.4913 0.084 Uiso calc R 1 . . H + N2 0.2522(3) 0.4162(2) 0.0286(5) 0.0732(7) Uani d . 1 . . N + H21 0.3388 0.4483 0.0170 0.088 Uiso calc R 1 . . H + C1 0.3299(3) 0.5903(2) 0.3881(6) 0.0684(8) Uani d . 1 . . C + C2 0.1534(3) 0.4499(3) 0.2098(6) 0.0689(8) Uani d . 1 . . C + C11 0.3418(4) 0.6722(3) 0.6063(7) 0.0805(9) Uani d D 1 . . C + H112 0.4210 0.6488 0.7254 0.097 Uiso calc R 1 . . H + H111 0.2459 0.6740 0.7005 0.097 Uiso calc R 1 . . H + C12 0.3776(5) 0.7849(3) 0.5237(9) 0.1003(12) Uani d D 1 . . C + H122 0.4711 0.7827 0.4229 0.120 Uiso calc R 1 . . H + H121 0.3961 0.8299 0.6777 0.120 Uiso calc R 1 . . H + C13 0.2532(6) 0.8367(4) 0.3649(10) 0.1236(17) Uani d D 1 . . C + H131 0.2302 0.7897 0.2137 0.148 Uiso calc R 1 . . H + C14 0.3071(11) 0.9462(5) 0.2717(15) 0.196(4) Uani d D 1 . . C + H143 0.2280 0.9787 0.1692 0.235 Uiso calc R 1 . . H + H142 0.3975 0.9361 0.1682 0.235 Uiso calc R 1 . . H + H141 0.3298 0.9926 0.4192 0.235 Uiso calc R 1 . . H + C15 0.1075(6) 0.8540(5) 0.5253(17) 0.185(3) Uani d D 1 . . C + H152 0.0729 0.7856 0.5861 0.222 Uiso calc R 1 . . H + H153 0.0294 0.8857 0.4191 0.222 Uiso calc R 1 . . H + H151 0.1287 0.9015 0.6714 0.222 Uiso calc R 1 . . H + C21 0.2180(4) 0.3277(3) -0.1486(7) 0.0808(9) Uani d D 1 . . C + H211 0.2786 0.3345 -0.3046 0.097 Uiso calc R 1 . . H + H212 0.1109 0.3317 -0.1981 0.097 Uiso calc R 1 . . H + C22 0.2497(6) 0.2198(3) -0.0343(10) 0.1109(14) Uani d D 1 . . C + H223 0.2247 0.1635 -0.1591 0.133 Uiso calc R 1 . . H + H222 0.1887 0.2120 0.1187 0.133 Uiso calc R 1 . . H + H221 0.3561 0.2145 0.0110 0.133 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0539(12) 0.0981(16) 0.1021(16) -0.0133(10) 0.0244(11) -0.0008(13) + O2 0.0553(13) 0.0932(15) 0.1029(17) -0.0144(10) 0.0238(11) -0.0022(13) + N1 0.0513(13) 0.0771(15) 0.0822(16) -0.0061(11) 0.0199(11) 0.0039(13) + N2 0.0508(13) 0.0810(16) 0.0878(17) -0.0061(11) 0.0168(12) 0.0008(14) + C1 0.0514(15) 0.0752(17) 0.0796(19) -0.0018(12) 0.0091(13) 0.0186(15) + C2 0.0480(15) 0.0787(18) 0.0809(19) -0.0023(12) 0.0141(13) 0.0139(15) + C11 0.0653(19) 0.084(2) 0.092(2) -0.0069(15) 0.0076(16) 0.0038(18) + C12 0.085(3) 0.095(3) 0.121(3) -0.013(2) 0.016(2) -0.004(2) + C13 0.157(5) 0.094(3) 0.120(4) 0.001(3) -0.020(3) 0.011(3) + C14 0.299(11) 0.105(4) 0.186(7) -0.006(5) 0.006(7) 0.048(4) + C15 0.102(4) 0.143(5) 0.312(10) 0.027(3) -0.020(5) 0.028(6) + C21 0.0619(19) 0.092(2) 0.089(2) -0.0042(15) 0.0082(16) 0.0021(18) + C22 0.115(3) 0.086(3) 0.131(4) 0.001(2) 0.007(3) 0.004(2) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.222(4) ? + O2 C2 . 1.228(3) ? + N1 C1 . 1.359(4) ? + N1 C2 . 1.385(4) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.330(4) ? + N2 C21 . 1.439(4) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.496(5) ? + C11 C12 . 1.503(5) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.506(7) ? + C12 H122 . 0.9700 ? + C12 H121 . 0.9700 ? + C13 C14 . 1.526(8) ? + C13 C15 . 1.531(9) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C21 C22 . 1.495(5) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.9(3) ? + C1 N1 H11 . . 115.1 ? + C2 N1 H11 . . 115.1 ? + C2 N2 C21 . . 121.7(3) ? + C2 N2 H21 . . 119.2 ? + C21 N2 H21 . . 119.2 ? + O1 C1 N1 . . 122.3(3) ? + O1 C1 C11 . . 122.2(3) ? + N1 C1 C11 . . 115.5(3) ? + O2 C2 N2 . . 123.6(3) ? + O2 C2 N1 . . 118.4(3) ? + N2 C2 N1 . . 118.0(3) ? + C1 C11 C12 . . 114.6(3) ? + C1 C11 H112 . . 108.6 ? + C12 C11 H112 . . 108.6 ? + C1 C11 H111 . . 108.6 ? + C12 C11 H111 . . 108.6 ? + H112 C11 H111 . . 107.6 ? + C11 C12 C13 . . 114.1(3) ? + C11 C12 H122 . . 108.7 ? + C13 C12 H122 . . 108.7 ? + C11 C12 H121 . . 108.7 ? + C13 C12 H121 . . 108.7 ? + H122 C12 H121 . . 107.6 ? + C12 C13 C14 . . 109.6(5) ? + C12 C13 C15 . . 111.0(4) ? + C14 C13 C15 . . 108.8(5) ? + C12 C13 H131 . . 109.1 ? + C14 C13 H131 . . 109.1 ? + C15 C13 H131 . . 109.1 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H152 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + N2 C21 C22 . . 112.6(3) ? + N2 C21 H211 . . 109.1 ? + C22 C21 H211 . . 109.1 ? + N2 C21 H212 . . 109.1 ? + C22 C21 H212 . . 109.1 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 3.0(5) ? + C2 N1 C1 C11 . . . . -176.5(3) ? + C21 N2 C2 O2 . . . . -1.0(5) ? + C21 N2 C2 N1 . . . . 178.3(3) ? + C1 N1 C2 O2 . . . . 179.3(3) ? + C1 N1 C2 N2 . . . . 0.1(5) ? + O1 C1 C11 C12 . . . . 55.3(4) ? + N1 C1 C11 C12 . . . . -125.3(3) ? + C1 C11 C12 C13 . . . . 65.7(5) ? + C11 C12 C13 C14 . . . . -175.0(4) ? + C11 C12 C13 C15 . . . . 64.8(6) ? + C2 N2 C21 C22 . . . . -82.8(4) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.39 3.069(3) 136.8 + N1 H11 O2 2_566 0.86 2.00 2.859(3) 177.2 +data_ethyl350K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7514(15) +_cell_length_b 12.460(2) +_cell_length_c 5.1254(9) +_cell_angle_alpha 91.510(5) +_cell_angle_beta 90.273(9) +_cell_angle_gamma 89.642(8) +_cell_volume 558.69(16) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 4431 +_cell_measurement_theta_min 2.855 +_cell_measurement_theta_max 27.425 +_cell_measurement_temperature 350 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.107 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.078 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 350 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6495 +_diffrn_reflns_av_R_equivalents 0.021 +_diffrn_reflns_av_sigmaI/netI 0.0130 +_diffrn_reflns_theta_min 2.33 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.826 +_diffrn_measured_fraction_theta_full 0.826 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2118 +_reflns_number_gt 1790 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1347 +_refine_ls_R_factor_gt 0.1195 +_refine_ls_wR_factor_gt 0.2409 +_refine_ls_wR_factor_ref 0.2498 +_refine_ls_goodness_of_fit_ref 1.344 +_refine_ls_restrained_S_all 1.348 +_refine_ls_number_reflns 2118 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 6 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.4679P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.201 +_refine_diff_density_min -0.217 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 348K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4331(3) 0.5744(2) 0.2313(6) 0.0800(9) Uani d . 1 . . O + O2 0.0270(3) 0.4095(2) 0.2386(6) 0.0797(9) Uani d . 1 . . O + N1 0.1970(3) 0.5338(3) 0.3786(7) 0.0657(9) Uani d . 1 . . N + H11 0.1304 0.5529 0.4939 0.079 Uiso calc R 1 . . H + N2 0.2526(4) 0.4162(3) 0.0302(7) 0.0683(9) Uani d D 1 . . N + H12 0.3392 0.4478 0.0190 0.082 Uiso calc R 1 . . H + C1 0.3300(4) 0.5901(3) 0.3871(8) 0.0623(10) Uani d . 1 . . C + C2 0.1535(4) 0.4499(3) 0.2105(8) 0.0633(10) Uani d D 1 . . C + C11 0.3413(5) 0.6722(3) 0.6048(9) 0.0775(12) Uani d D 1 . . C + H112 0.4203 0.6496 0.7252 0.093 Uiso calc R 1 . . H + H111 0.2453 0.6739 0.6988 0.093 Uiso calc R 1 . . H + C12 0.3767(6) 0.7844(4) 0.5202(11) 0.1012(17) Uani d D 1 . . C + H122 0.3968 0.8289 0.6746 0.121 Uiso calc R 1 . . H + H121 0.4694 0.7820 0.4172 0.121 Uiso calc R 1 . . H + C13 0.2530(8) 0.8371(5) 0.3637(13) 0.123(2) Uani d D 1 . . C + H131 0.2292 0.7913 0.2107 0.148 Uiso calc R 1 . . H + C14 0.3071(13) 0.9459(5) 0.2724(18) 0.201(5) Uani d D 1 . . C + H143 0.2277 0.9788 0.1718 0.242 Uiso calc R 1 . . H + H142 0.3966 0.9362 0.1666 0.242 Uiso calc R 1 . . H + H141 0.3310 0.9911 0.4214 0.242 Uiso calc R 1 . . H + C15 0.1083(8) 0.8548(7) 0.523(2) 0.192(4) Uani d D 1 . . C + H152 0.0741 0.7873 0.5872 0.230 Uiso calc R 1 . . H + H153 0.0301 0.8852 0.4154 0.230 Uiso calc R 1 . . H + H151 0.1294 0.9030 0.6681 0.230 Uiso calc R 1 . . H + C21 0.2183(5) 0.3279(4) -0.1466(9) 0.0788(12) Uani d D 1 . . C + H211 0.2785 0.3348 -0.3037 0.095 Uiso calc R 1 . . H + H212 0.1113 0.3317 -0.1959 0.095 Uiso calc R 1 . . H + C22 0.2505(7) 0.2204(4) -0.0324(12) 0.1091(18) Uani d D 1 . . C + H223 0.2262 0.1647 -0.1586 0.131 Uiso calc R 1 . . H + H222 0.1891 0.2121 0.1205 0.131 Uiso calc R 1 . . H + H221 0.3567 0.2155 0.0141 0.131 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0511(15) 0.095(2) 0.094(2) -0.0123(14) 0.0241(15) -0.0030(17) + O2 0.0525(16) 0.092(2) 0.095(2) -0.0142(14) 0.0228(14) -0.0050(17) + N1 0.0484(17) 0.073(2) 0.076(2) -0.0032(14) 0.0209(15) -0.0020(17) + N2 0.0504(17) 0.074(2) 0.080(2) -0.0057(15) 0.0134(16) -0.0016(18) + C1 0.049(2) 0.067(2) 0.072(2) 0.0016(17) 0.0082(18) 0.0141(19) + C2 0.0451(19) 0.071(2) 0.075(3) 0.0033(17) 0.0150(18) 0.010(2) + C11 0.064(3) 0.082(3) 0.087(3) -0.006(2) 0.010(2) 0.004(2) + C12 0.087(4) 0.097(4) 0.120(4) -0.012(3) 0.026(3) -0.005(3) + C13 0.145(6) 0.105(4) 0.120(5) 0.005(4) -0.020(4) 0.015(4) + C14 0.316(14) 0.098(5) 0.192(9) -0.006(7) 0.019(9) 0.047(6) + C15 0.109(6) 0.147(7) 0.321(14) 0.029(5) -0.021(7) 0.029(8) + C21 0.060(2) 0.092(3) 0.084(3) -0.003(2) 0.010(2) -0.001(3) + C22 0.114(4) 0.086(4) 0.127(5) 0.002(3) 0.010(4) -0.001(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.219(4) ? + O2 C2 . 1.230(4) ? + N1 C1 . 1.362(5) ? + N1 C2 . 1.391(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.329(5) ? + N2 C21 . 1.438(5) ? + N2 H12 . 0.8600 ? + C1 C11 . 1.496(6) ? + C11 C12 . 1.510(7) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.502(9) ? + C12 H122 . 0.9700 ? + C12 H121 . 0.9700 ? + C13 C15 . 1.523(11) ? + C13 C14 . 1.524(10) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C21 C22 . 1.501(7) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.3(3) ? + C1 N1 H11 . . 115.3 ? + C2 N1 H11 . . 115.3 ? + C2 N2 C21 . . 121.6(3) ? + C2 N2 H12 . . 119.2 ? + C21 N2 H12 . . 119.2 ? + O1 C1 N1 . . 122.8(4) ? + O1 C1 C11 . . 122.3(4) ? + N1 C1 C11 . . 115.0(3) ? + O2 C2 N2 . . 123.3(4) ? + O2 C2 N1 . . 118.7(3) ? + N2 C2 N1 . . 118.0(3) ? + C1 C11 C12 . . 114.8(4) ? + C1 C11 H112 . . 108.6 ? + C12 C11 H112 . . 108.6 ? + C1 C11 H111 . . 108.6 ? + C12 C11 H111 . . 108.6 ? + H112 C11 H111 . . 107.5 ? + C13 C12 C11 . . 115.0(4) ? + C13 C12 H122 . . 108.5 ? + C11 C12 H122 . . 108.5 ? + C13 C12 H121 . . 108.5 ? + C11 C12 H121 . . 108.5 ? + H122 C12 H121 . . 107.5 ? + C12 C13 C15 . . 111.6(6) ? + C12 C13 C14 . . 110.0(6) ? + C15 C13 C14 . . 108.2(7) ? + C12 C13 H131 . . 109.0 ? + C15 C13 H131 . . 109.0 ? + C14 C13 H131 . . 109.0 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H152 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + N2 C21 C22 . . 113.1(4) ? + N2 C21 H211 . . 109.0 ? + C22 C21 H211 . . 109.0 ? + N2 C21 H212 . . 109.0 ? + C22 C21 H212 . . 109.0 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 2.3(7) ? + C2 N1 C1 C11 . . . . -176.9(4) ? + C21 N2 C2 O2 . . . . -0.4(6) ? + C21 N2 C2 N1 . . . . 178.3(4) ? + C1 N1 C2 O2 . . . . 179.4(4) ? + C1 N1 C2 N2 . . . . 0.7(6) ? + O1 C1 C11 C12 . . . . 55.4(6) ? + N1 C1 C11 C12 . . . . -125.3(4) ? + C1 C11 C12 C13 . . . . 66.8(6) ? + C11 C12 C13 C15 . . . . 64.3(7) ? + C11 C12 C13 C14 . . . . -175.6(5) ? + C2 N2 C21 C22 . . . . -83.5(5) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H12 O1 2_665 0.86 2.39 3.070(4) 136.9 + N1 H11 O2 2_566 0.86 1.99 2.853(4) 177.5 +data_ethyl352K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7503(15) +_cell_length_b 12.4205(13) +_cell_length_c 5.0998(3) +_cell_angle_alpha 90.921(8) +_cell_angle_beta 89.723(12) +_cell_angle_gamma 89.714(10) +_cell_volume 554.18(12) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2561 +_cell_measurement_theta_min 1.64 +_cell_measurement_theta_max 27.165 +_cell_measurement_temperature 352 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.116 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.079 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 352 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6495 +_diffrn_reflns_av_R_equivalents 0.043 +_diffrn_reflns_av_sigmaI/netI 0.0258 +_diffrn_reflns_theta_min 2.84 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.773 +_diffrn_measured_fraction_theta_full 0.773 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 1968 +_reflns_number_gt 1242 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1531 +_refine_ls_R_factor_gt 0.1090 +_refine_ls_wR_factor_gt 0.3116 +_refine_ls_wR_factor_ref 0.3573 +_refine_ls_goodness_of_fit_ref 2.279 +_refine_ls_restrained_S_all 2.288 +_refine_ls_number_reflns 1968 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.245 +_refine_diff_density_min -0.272 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 350K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4334(3) 0.5747(3) 0.2302(6) 0.0916(10) Uani d . 1 . . O + O2 0.0271(3) 0.4095(2) 0.2407(6) 0.0884(10) Uani d . 1 . . O + N1 0.1975(4) 0.5334(3) 0.3774(6) 0.0736(10) Uani d . 1 . . N + H11 0.1306 0.5514 0.4943 0.088 Uiso calc R 1 . . H + N2 0.2528(4) 0.4164(3) 0.0297(6) 0.0762(10) Uani d . 1 . . N + H21 0.3397 0.4480 0.0171 0.091 Uiso calc R 1 . . H + C1 0.3279(4) 0.5905(3) 0.3858(8) 0.0713(10) Uani d . 1 . . C + C2 0.1544(5) 0.4503(3) 0.2098(8) 0.0745(10) Uani d . 1 . . C + C11 0.3418(5) 0.6719(3) 0.6031(9) 0.0841(12) Uani d D 1 . . C + H112 0.4200 0.6475 0.7228 0.101 Uiso calc R 1 . . H + H111 0.2460 0.6746 0.6992 0.101 Uiso calc R 1 . . H + C12 0.3806(6) 0.7842(4) 0.5206(11) 0.1075(17) Uani d D 1 . . C + H122 0.4733 0.7820 0.4156 0.129 Uiso calc R 1 . . H + H121 0.4004 0.8281 0.6756 0.129 Uiso calc R 1 . . H + C13 0.2535(8) 0.8365(5) 0.3631(12) 0.131(2) Uani d D 1 . . C + H131 0.2308 0.7903 0.2109 0.157 Uiso calc R 1 . . H + C14 0.3088(15) 0.9449(6) 0.2663(19) 0.220(6) Uani d D 1 . . C + H142 0.4007 0.9348 0.1651 0.264 Uiso calc R 1 . . H + H141 0.3291 0.9916 0.4139 0.264 Uiso calc R 1 . . H + H143 0.2315 0.9768 0.1589 0.264 Uiso calc R 1 . . H + C15 0.1084(8) 0.8520(7) 0.524(2) 0.188(4) Uani d D 1 . . C + H152 0.0739 0.7835 0.5849 0.225 Uiso calc R 1 . . H + H153 0.0308 0.8839 0.4178 0.225 Uiso calc R 1 . . H + H151 0.1289 0.8984 0.6722 0.225 Uiso calc R 1 . . H + C21 0.2191(5) 0.3275(4) -0.1474(9) 0.0883(13) Uani d D 1 . . C + H211 0.2798 0.3347 -0.3057 0.106 Uiso calc R 1 . . H + H212 0.1122 0.3313 -0.1964 0.106 Uiso calc R 1 . . H + C22 0.2506(8) 0.2200(4) -0.0318(13) 0.1205(19) Uani d D 1 . . C + H223 0.2263 0.1644 -0.1575 0.145 Uiso calc R 1 . . H + H222 0.1890 0.2115 0.1227 0.145 Uiso calc R 1 . . H + H221 0.3567 0.2150 0.0136 0.145 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0625(17) 0.104(2) 0.108(2) -0.0180(14) 0.0261(15) -0.0071(17) + O2 0.0576(17) 0.101(2) 0.106(2) -0.0170(13) 0.0298(14) -0.0096(16) + N1 0.0580(18) 0.081(2) 0.0813(19) -0.0088(14) 0.0220(14) -0.0016(16) + N2 0.0542(18) 0.085(2) 0.089(2) -0.0068(14) 0.0168(15) -0.0017(17) + C1 0.0460(18) 0.081(2) 0.087(2) 0.0021(15) 0.0141(15) 0.017(2) + C2 0.055(2) 0.082(2) 0.086(2) -0.0021(16) 0.0158(17) 0.010(2) + C11 0.071(3) 0.082(2) 0.098(3) -0.0082(19) 0.010(2) 0.004(2) + C12 0.084(3) 0.103(4) 0.135(4) -0.012(3) 0.024(3) -0.009(3) + C13 0.162(7) 0.108(4) 0.123(5) 0.003(4) -0.011(4) 0.011(3) + C14 0.34(2) 0.125(6) 0.193(9) 0.002(7) 0.005(10) 0.047(6) + C15 0.105(6) 0.165(7) 0.294(12) 0.022(5) -0.012(7) 0.029(7) + C21 0.067(3) 0.096(3) 0.101(3) -0.008(2) 0.018(2) -0.005(2) + C22 0.133(5) 0.098(4) 0.130(5) 0.008(3) 0.007(4) -0.003(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.228(4) ? + O2 C2 . 1.237(5) ? + N1 C1 . 1.346(5) ? + N1 C2 . 1.384(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.319(5) ? + N2 C21 . 1.448(5) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.494(6) ? + C11 C12 . 1.503(6) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.524(8) ? + C12 H122 . 0.9700 ? + C12 H121 . 0.9700 ? + C13 C15 . 1.519(11) ? + C13 C14 . 1.522(10) ? + C13 H131 . 0.9800 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C14 H143 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C21 C22 . 1.493(7) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 130.1(3) ? + C1 N1 H11 . . 114.9 ? + C2 N1 H11 . . 114.9 ? + C2 N2 C21 . . 122.0(4) ? + C2 N2 H21 . . 119.0 ? + C21 N2 H21 . . 119.0 ? + O1 C1 N1 . . 122.4(4) ? + O1 C1 C11 . . 120.8(4) ? + N1 C1 C11 . . 116.7(3) ? + O2 C2 N2 . . 123.1(4) ? + O2 C2 N1 . . 118.5(3) ? + N2 C2 N1 . . 118.4(4) ? + C1 C11 C12 . . 115.6(4) ? + C1 C11 H112 . . 108.4 ? + C12 C11 H112 . . 108.4 ? + C1 C11 H111 . . 108.4 ? + C12 C11 H111 . . 108.4 ? + H112 C11 H111 . . 107.4 ? + C11 C12 C13 . . 112.7(4) ? + C11 C12 H122 . . 109.1 ? + C13 C12 H122 . . 109.1 ? + C11 C12 H121 . . 109.1 ? + C13 C12 H121 . . 109.1 ? + H122 C12 H121 . . 107.8 ? + C15 C13 C14 . . 109.7(8) ? + C15 C13 C12 . . 112.0(5) ? + C14 C13 C12 . . 108.9(6) ? + C15 C13 H131 . . 108.7 ? + C14 C13 H131 . . 108.7 ? + C12 C13 H131 . . 108.7 ? + C13 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C14 H143 . . 109.5 ? + H142 C14 H143 . . 109.5 ? + H141 C14 H143 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H152 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + N2 C21 C22 . . 113.2(4) ? + N2 C21 H211 . . 108.9 ? + C22 C21 H211 . . 108.9 ? + N2 C21 H212 . . 108.9 ? + C22 C21 H212 . . 108.9 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 0.6(6) ? + C2 N1 C1 C11 . . . . -176.8(3) ? + C21 N2 C2 O2 . . . . -0.2(6) ? + C21 N2 C2 N1 . . . . 177.8(3) ? + C1 N1 C2 O2 . . . . 179.9(4) ? + C1 N1 C2 N2 . . . . 1.8(6) ? + O1 C1 C11 C12 . . . . 55.9(5) ? + N1 C1 C11 C12 . . . . -126.7(4) ? + C1 C11 C12 C13 . . . . 66.3(6) ? + C11 C12 C13 C15 . . . . 63.9(8) ? + C11 C12 C13 C14 . . . . -174.6(6) ? + C2 N2 C21 C22 . . . . -83.5(5) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.36 3.047(4) 137.0 + N1 H11 O2 2_566 0.86 1.98 2.840(4) 178.6 +data_ethyl354K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7270(4) +_cell_length_b 12.6010(13) +_cell_length_c 5.1459(3) +_cell_angle_alpha 91.317(9) +_cell_angle_beta 90.331(11) +_cell_angle_gamma 89.001(9) +_cell_volume 565.65(7) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 4364 +_cell_measurement_theta_min 2.865 +_cell_measurement_theta_max 27.455 +_cell_measurement_temperature 354 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.40 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.094 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.077 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 354 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6513 +_diffrn_reflns_av_R_equivalents 0.026 +_diffrn_reflns_av_sigmaI/netI 0.0175 +_diffrn_reflns_theta_min 2.33 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.815 +_diffrn_measured_fraction_theta_full 0.815 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2122 +_reflns_number_gt 1551 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1465 +_refine_ls_R_factor_gt 0.1175 +_refine_ls_wR_factor_gt 0.2594 +_refine_ls_wR_factor_ref 0.2768 +_refine_ls_goodness_of_fit_ref 1.305 +_refine_ls_restrained_S_all 1.309 +_refine_ls_number_reflns 2122 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.4317P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.221 +_refine_diff_density_min -0.222 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 352K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4326(3) 0.5747(3) 0.2307(7) 0.0861(10) Uani d . 1 . . O + O2 0.0267(3) 0.4098(3) 0.2401(7) 0.0852(10) Uani d . 1 . . O + N1 0.1973(4) 0.5339(3) 0.3778(7) 0.0709(10) Uani d . 1 . . N + H11 0.1303 0.5531 0.4923 0.085 Uiso calc R 1 . . H + N2 0.2522(4) 0.4164(3) 0.0306(7) 0.0712(10) Uani d . 1 . . N + H21 0.3383 0.4480 0.0169 0.085 Uiso calc R 1 . . H + C1 0.3297(4) 0.5903(3) 0.3861(9) 0.0666(11) Uani d . 1 . . C + C2 0.1532(4) 0.4496(3) 0.2123(9) 0.0661(11) Uani d . 1 . . C + C11 0.3404(5) 0.6721(4) 0.6014(10) 0.0811(13) Uani d D 1 . . C + H112 0.4189 0.6492 0.7229 0.097 Uiso calc R 1 . . H + H111 0.2437 0.6747 0.6937 0.097 Uiso calc R 1 . . H + C12 0.3767(7) 0.7834(4) 0.5180(13) 0.112(2) Uani d D 1 . . C + H121 0.3964 0.8268 0.6723 0.134 Uiso calc R 1 . . H + H122 0.4702 0.7803 0.4168 0.134 Uiso calc R 1 . . H + C13 0.2538(8) 0.8369(5) 0.3608(14) 0.131(2) Uani d D 1 . . C + H131 0.2307 0.7922 0.2078 0.157 Uiso calc R 1 . . H + C14 0.3074(14) 0.9447(6) 0.271(2) 0.219(5) Uani d D 1 . . C + H143 0.2279 0.9777 0.1698 0.262 Uiso calc R 1 . . H + H142 0.3976 0.9350 0.1663 0.262 Uiso calc R 1 . . H + H141 0.3305 0.9890 0.4195 0.262 Uiso calc R 1 . . H + C15 0.1081(9) 0.8545(7) 0.518(2) 0.209(5) Uani d D 1 . . C + H152 0.0748 0.7879 0.5821 0.250 Uiso calc R 1 . . H + H153 0.0296 0.8843 0.4088 0.250 Uiso calc R 1 . . H + H151 0.1280 0.9024 0.6613 0.250 Uiso calc R 1 . . H + C21 0.2180(5) 0.3283(4) -0.1443(10) 0.0819(13) Uani d D 1 . . C + H211 0.2783 0.3345 -0.3009 0.098 Uiso calc R 1 . . H + H212 0.1107 0.3328 -0.1938 0.098 Uiso calc R 1 . . H + C22 0.2503(8) 0.2210(4) -0.0295(13) 0.116(2) Uani d D 1 . . C + H223 0.2251 0.1663 -0.1547 0.140 Uiso calc R 1 . . H + H222 0.1893 0.2134 0.1234 0.140 Uiso calc R 1 . . H + H221 0.3569 0.2150 0.0157 0.140 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0583(17) 0.102(2) 0.098(2) -0.0109(15) 0.0267(16) -0.0047(19) + O2 0.0544(16) 0.100(2) 0.102(2) -0.0142(15) 0.0237(15) -0.0063(18) + N1 0.0523(18) 0.079(2) 0.082(2) -0.0025(16) 0.0237(17) 0.001(2) + N2 0.0510(18) 0.082(2) 0.081(2) -0.0032(16) 0.0158(16) -0.0026(19) + C1 0.053(2) 0.071(3) 0.077(3) 0.0035(18) 0.0116(19) 0.016(2) + C2 0.049(2) 0.074(3) 0.076(3) 0.0056(18) 0.0106(19) 0.014(2) + C11 0.068(3) 0.083(3) 0.092(3) -0.003(2) 0.014(2) 0.005(3) + C12 0.098(4) 0.106(4) 0.132(5) -0.011(3) 0.028(4) -0.010(4) + C13 0.151(7) 0.113(5) 0.129(6) 0.014(5) -0.017(5) 0.025(4) + C14 0.342(16) 0.108(6) 0.208(10) -0.001(8) 0.033(10) 0.045(6) + C15 0.120(7) 0.166(8) 0.340(16) 0.035(6) -0.023(9) 0.032(9) + C21 0.062(2) 0.098(3) 0.086(3) -0.002(2) 0.012(2) 0.000(3) + C22 0.121(5) 0.092(4) 0.136(5) 0.003(3) 0.012(4) -0.001(4) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.217(5) ? + O2 C2 . 1.232(5) ? + N1 C1 . 1.367(5) ? + N1 C2 . 1.403(6) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.332(5) ? + N2 C21 . 1.447(6) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.499(6) ? + C11 C12 . 1.516(7) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.500(9) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.520(11) ? + C13 C14 . 1.527(11) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C21 C22 . 1.510(8) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 130.3(3) ? + C1 N1 H11 . . 114.9 ? + C2 N1 H11 . . 114.9 ? + C2 N2 C21 . . 121.4(4) ? + C2 N2 H21 . . 119.3 ? + C21 N2 H21 . . 119.3 ? + O1 C1 N1 . . 122.4(4) ? + O1 C1 C11 . . 122.1(4) ? + N1 C1 C11 . . 115.5(4) ? + O2 C2 N2 . . 123.0(4) ? + O2 C2 N1 . . 119.4(4) ? + N2 C2 N1 . . 117.6(3) ? + C1 C11 C12 . . 115.6(4) ? + C1 C11 H112 . . 108.4 ? + C12 C11 H112 . . 108.4 ? + C1 C11 H111 . . 108.4 ? + C12 C11 H111 . . 108.4 ? + H112 C11 H111 . . 107.4 ? + C13 C12 C11 . . 115.0(5) ? + C13 C12 H121 . . 108.5 ? + C11 C12 H121 . . 108.5 ? + C13 C12 H122 . . 108.5 ? + C11 C12 H122 . . 108.5 ? + H121 C12 H122 . . 107.5 ? + C12 C13 C15 . . 111.4(6) ? + C12 C13 C14 . . 110.5(7) ? + C15 C13 C14 . . 108.2(8) ? + C12 C13 H131 . . 108.9 ? + C15 C13 H131 . . 108.9 ? + C14 C13 H131 . . 108.9 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H152 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + N2 C21 C22 . . 113.7(4) ? + N2 C21 H211 . . 108.8 ? + C22 C21 H211 . . 108.8 ? + N2 C21 H212 . . 108.8 ? + C22 C21 H212 . . 108.8 ? + H211 C21 H212 . . 107.7 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 2.7(7) ? + C2 N1 C1 C11 . . . . -176.8(4) ? + C21 N2 C2 O2 . . . . -1.5(7) ? + C21 N2 C2 N1 . . . . 178.4(4) ? + C1 N1 C2 O2 . . . . 179.8(4) ? + C1 N1 C2 N2 . . . . -0.1(6) ? + O1 C1 C11 C12 . . . . 54.2(6) ? + N1 C1 C11 C12 . . . . -126.4(4) ? + C1 C11 C12 C13 . . . . 66.9(6) ? + C11 C12 C13 C15 . . . . 64.0(8) ? + C11 C12 C13 C14 . . . . -175.8(6) ? + C2 N2 C21 C22 . . . . -82.3(5) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.39 3.073(4) 137.1 + N1 H11 O2 2_566 0.86 1.99 2.850(5) 177.3 +data_ethyl356K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.726(3) +_cell_length_b 12.460(3) +_cell_length_c 5.1382(12) +_cell_angle_alpha 91.423(6) +_cell_angle_beta 90.143(10) +_cell_angle_gamma 89.297(11) +_cell_volume 558.5(2) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2070 +_cell_measurement_theta_min 2.335 +_cell_measurement_theta_max 27.48 +_cell_measurement_temperature 356 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.80 +_exptl_crystal_size_mid 0.80 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.108 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.078 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 356 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6409 +_diffrn_reflns_av_R_equivalents 0.035 +_diffrn_reflns_av_sigmaI/netI 0.0210 +_diffrn_reflns_theta_min 2.33 +_diffrn_reflns_theta_max 27.47 +_diffrn_reflns_theta_full 27.47 +_diffrn_measured_fraction_theta_max 0.668 +_diffrn_measured_fraction_theta_full 0.668 +_diffrn_reflns_limit_h_min -10 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -15 +_diffrn_reflns_limit_k_max 15 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 1713 +_reflns_number_gt 1306 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.0991 +_refine_ls_R_factor_gt 0.0792 +_refine_ls_wR_factor_gt 0.2200 +_refine_ls_wR_factor_ref 0.2495 +_refine_ls_goodness_of_fit_ref 1.081 +_refine_ls_restrained_S_all 1.087 +_refine_ls_number_reflns 1713 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1254P)^2^+0.2162P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.228 +_refine_diff_density_min -0.243 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 354K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4321(3) 0.5743(2) 0.2297(5) 0.0906(8) Uani d . 1 . . O + O2 0.0271(3) 0.4103(2) 0.2409(5) 0.0873(8) Uani d . 1 . . O + N1 0.1970(3) 0.5337(2) 0.3769(5) 0.0726(8) Uani d . 1 . . N + H11 0.1302 0.5527 0.4923 0.087 Uiso calc R 1 . . H + N2 0.2523(3) 0.4164(2) 0.0323(5) 0.0759(8) Uani d . 1 . . N + H21 0.3390 0.4479 0.0207 0.091 Uiso calc R 1 . . H + C1 0.3290(4) 0.5900(3) 0.3840(6) 0.0721(9) Uani d . 1 . . C + C2 0.1537(4) 0.4496(3) 0.2106(6) 0.0708(8) Uani d . 1 . . C + C11 0.3411(4) 0.6720(3) 0.5999(7) 0.0851(10) Uani d D 1 . . C + H112 0.4200 0.6487 0.7200 0.102 Uiso calc R 1 . . H + H111 0.2448 0.6746 0.6940 0.102 Uiso calc R 1 . . H + C12 0.3775(5) 0.7834(3) 0.5164(10) 0.1125(14) Uani d D 1 . . C + H122 0.4708 0.7803 0.4140 0.135 Uiso calc R 1 . . H + H121 0.3975 0.8276 0.6705 0.135 Uiso calc R 1 . . H + C13 0.2533(7) 0.8369(4) 0.3592(11) 0.138(2) Uani d D 1 . . C + H131 0.2304 0.7911 0.2066 0.165 Uiso calc R 1 . . H + C14 0.3084(12) 0.9448(5) 0.2669(17) 0.217(4) Uani d D 1 . . C + H143 0.2299 0.9777 0.1636 0.260 Uiso calc R 1 . . H + H142 0.3993 0.9343 0.1639 0.260 Uiso calc R 1 . . H + H141 0.3309 0.9905 0.4149 0.260 Uiso calc R 1 . . H + C15 0.1063(8) 0.8539(6) 0.5178(19) 0.205(4) Uani d D 1 . . C + H152 0.0722 0.7861 0.5793 0.246 Uiso calc R 1 . . H + H153 0.0283 0.8849 0.4100 0.246 Uiso calc R 1 . . H + H151 0.1262 0.9014 0.6637 0.246 Uiso calc R 1 . . H + C21 0.2181(4) 0.3286(3) -0.1433(7) 0.0846(10) Uani d D 1 . . C + H211 0.2787 0.3350 -0.3000 0.102 Uiso calc R 1 . . H + H212 0.1109 0.3328 -0.1926 0.102 Uiso calc R 1 . . H + C22 0.2501(7) 0.2215(3) -0.0277(10) 0.1194(15) Uani d D 1 . . C + H223 0.2260 0.1656 -0.1528 0.143 Uiso calc R 1 . . H + H222 0.1882 0.2137 0.1248 0.143 Uiso calc R 1 . . H + H221 0.3564 0.2163 0.0189 0.143 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0631(14) 0.1048(18) 0.1040(17) -0.0101(12) 0.0276(13) -0.0024(14) + O2 0.0605(15) 0.0961(16) 0.1052(18) -0.0090(11) 0.0257(12) -0.0039(13) + N1 0.0594(15) 0.0782(17) 0.0803(16) -0.0007(12) 0.0216(12) 0.0030(13) + N2 0.0572(15) 0.0836(18) 0.0868(18) -0.0003(12) 0.0171(12) 0.0004(14) + C1 0.0579(18) 0.0747(19) 0.085(2) 0.0035(14) 0.0125(15) 0.0196(16) + C2 0.0550(17) 0.0787(19) 0.079(2) 0.0058(14) 0.0136(14) 0.0123(16) + C11 0.078(2) 0.082(2) 0.095(2) -0.0011(17) 0.0099(18) 0.0000(18) + C12 0.100(3) 0.103(3) 0.135(4) -0.010(2) 0.025(3) -0.006(3) + C13 0.165(6) 0.107(3) 0.142(4) 0.012(3) -0.021(4) 0.016(3) + C14 0.333(14) 0.110(4) 0.210(8) -0.003(6) 0.015(8) 0.047(5) + C15 0.122(6) 0.162(6) 0.331(12) 0.038(4) -0.011(7) 0.022(7) + C21 0.065(2) 0.097(2) 0.091(2) 0.0017(17) 0.0127(16) -0.0025(19) + C22 0.134(4) 0.092(3) 0.132(4) 0.007(3) 0.007(3) 0.003(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.211(4) ? + O2 C2 . 1.225(4) ? + N1 C1 . 1.357(4) ? + N1 C2 . 1.390(4) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.314(4) ? + N2 C21 . 1.435(4) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.494(5) ? + C11 C12 . 1.501(6) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.509(8) ? + C12 H122 . 0.9700 ? + C12 H121 . 0.9700 ? + C13 C14 . 1.520(9) ? + C13 C15 . 1.532(10) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C21 C22 . 1.497(6) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.6(3) ? + C1 N1 H11 . . 115.2 ? + C2 N1 H11 . . 115.2 ? + C2 N2 C21 . . 121.3(3) ? + C2 N2 H21 . . 119.3 ? + C21 N2 H21 . . 119.3 ? + O1 C1 N1 . . 122.9(3) ? + O1 C1 C11 . . 121.7(3) ? + N1 C1 C11 . . 115.5(3) ? + O2 C2 N2 . . 124.1(3) ? + O2 C2 N1 . . 118.2(3) ? + N2 C2 N1 . . 117.7(3) ? + C1 C11 C12 . . 115.1(3) ? + C1 C11 H112 . . 108.5 ? + C12 C11 H112 . . 108.5 ? + C1 C11 H111 . . 108.5 ? + C12 C11 H111 . . 108.5 ? + H112 C11 H111 . . 107.5 ? + C11 C12 C13 . . 114.7(4) ? + C11 C12 H122 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + C11 C12 H121 . . 108.6 ? + C13 C12 H121 . . 108.6 ? + H122 C12 H121 . . 107.6 ? + C12 C13 C14 . . 109.9(6) ? + C12 C13 C15 . . 111.6(5) ? + C14 C13 C15 . . 109.2(6) ? + C12 C13 H131 . . 108.7 ? + C14 C13 H131 . . 108.7 ? + C15 C13 H131 . . 108.7 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H152 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + N2 C21 C22 . . 112.7(3) ? + N2 C21 H211 . . 109.0 ? + C22 C21 H211 . . 109.0 ? + N2 C21 H212 . . 109.0 ? + C22 C21 H212 . . 109.0 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 2.0(5) ? + C2 N1 C1 C11 . . . . -176.7(3) ? + C21 N2 C2 O2 . . . . -0.5(5) ? + C21 N2 C2 N1 . . . . 178.6(3) ? + C1 N1 C2 O2 . . . . 180.0(3) ? + C1 N1 C2 N2 . . . . 0.8(5) ? + O1 C1 C11 C12 . . . . 55.1(5) ? + N1 C1 C11 C12 . . . . -126.2(3) ? + C1 C11 C12 C13 . . . . 66.6(5) ? + C11 C12 C13 C14 . . . . -175.2(5) ? + C11 C12 C13 C15 . . . . 63.5(6) ? + C2 N2 C21 C22 . . . . -83.1(4) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.39 3.073(4) 137.0 + N1 H11 O2 2_566 0.86 1.98 2.844(4) 177.3 +data_ethyl358K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7438(6) +_cell_length_b 12.5269(10) +_cell_length_c 5.1573(4) +_cell_angle_alpha 90.802(6) +_cell_angle_beta 90.388(7) +_cell_angle_gamma 89.224(3) +_cell_volume 564.77(7) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2719 +_cell_measurement_theta_min 3.95 +_cell_measurement_theta_max 27.385 +_cell_measurement_temperature 358 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.095 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.078 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 358 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6499 +_diffrn_reflns_av_R_equivalents 0.058 +_diffrn_reflns_av_sigmaI/netI 0.0351 +_diffrn_reflns_theta_min 2.33 +_diffrn_reflns_theta_max 27.41 +_diffrn_reflns_theta_full 27.41 +_diffrn_measured_fraction_theta_max 0.931 +_diffrn_measured_fraction_theta_full 0.931 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2397 +_reflns_number_gt 1516 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1360 +_refine_ls_R_factor_gt 0.1033 +_refine_ls_wR_factor_gt 0.2800 +_refine_ls_wR_factor_ref 0.2975 +_refine_ls_goodness_of_fit_ref 1.829 +_refine_ls_restrained_S_all 1.839 +_refine_ls_number_reflns 2397 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.360 +_refine_diff_density_min -0.278 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 356K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4322(2) 0.57411(19) 0.2289(5) 0.0866(7) Uani d . 1 . . O + O2 0.0270(2) 0.40995(18) 0.2426(5) 0.0839(7) Uani d . 1 . . O + N1 0.1973(2) 0.53358(18) 0.3763(5) 0.0685(7) Uani d . 1 . . N + H11 0.1306 0.5524 0.4905 0.082 Uiso calc R 1 . . H + N2 0.2522(3) 0.4163(2) 0.0331(5) 0.0731(7) Uani d . 1 . . N + H21 0.3389 0.4474 0.0215 0.088 Uiso calc R 1 . . H + C1 0.3293(3) 0.5898(2) 0.3831(6) 0.0685(8) Uani d . 1 . . C + C2 0.1542(3) 0.4499(2) 0.2113(6) 0.0677(7) Uani d . 1 . . C + C11 0.3410(4) 0.6723(2) 0.6002(7) 0.0828(9) Uani d D 1 . . C + H112 0.2446 0.6749 0.6923 0.099 Uiso calc R 1 . . H + H111 0.4194 0.6489 0.7215 0.099 Uiso calc R 1 . . H + C12 0.3775(5) 0.7827(3) 0.5155(9) 0.1082(13) Uani d D 1 . . C + H122 0.4706 0.7795 0.4142 0.130 Uiso calc R 1 . . H + H121 0.3976 0.8264 0.6683 0.130 Uiso calc R 1 . . H + C13 0.2537(6) 0.8362(4) 0.3571(10) 0.1355(18) Uani d D 1 . . C + H131 0.2316 0.7911 0.2050 0.163 Uiso calc R 1 . . H + C14 0.3083(11) 0.9447(5) 0.2640(17) 0.222(4) Uani d D 1 . . C + H143 0.2295 0.9776 0.1607 0.267 Uiso calc R 1 . . H + H142 0.3988 0.9349 0.1619 0.267 Uiso calc R 1 . . H + H141 0.3306 0.9897 0.4113 0.267 Uiso calc R 1 . . H + C15 0.1067(7) 0.8530(6) 0.5095(17) 0.204(4) Uani d D 1 . . C + H153 0.0307 0.8861 0.4009 0.244 Uiso calc R 1 . . H + H151 0.1263 0.8981 0.6577 0.244 Uiso calc R 1 . . H + H152 0.0704 0.7852 0.5662 0.244 Uiso calc R 1 . . H + C21 0.2184(4) 0.3287(3) -0.1431(7) 0.0823(9) Uani d D 1 . . C + H211 0.2797 0.3354 -0.2980 0.099 Uiso calc R 1 . . H + H212 0.1117 0.3333 -0.1946 0.099 Uiso calc R 1 . . H + C22 0.2493(5) 0.2215(3) -0.0267(10) 0.1145(14) Uani d D 1 . . C + H223 0.2248 0.1665 -0.1510 0.137 Uiso calc R 1 . . H + H222 0.1876 0.2138 0.1249 0.137 Uiso calc R 1 . . H + H221 0.3555 0.2157 0.0205 0.137 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0643(12) 0.0974(15) 0.0986(16) -0.0124(10) 0.0275(11) -0.0013(12) + O2 0.0601(12) 0.0913(14) 0.1009(16) -0.0127(9) 0.0233(10) -0.0026(12) + N1 0.0559(12) 0.0734(14) 0.0766(15) -0.0013(10) 0.0194(10) 0.0026(12) + N2 0.0567(13) 0.0770(15) 0.0859(17) -0.0015(10) 0.0183(11) -0.0011(12) + C1 0.0560(14) 0.0729(16) 0.0771(18) 0.0034(11) 0.0139(12) 0.0141(13) + C2 0.0534(13) 0.0737(16) 0.0764(18) 0.0043(11) 0.0155(12) 0.0136(14) + C11 0.0733(18) 0.0785(19) 0.097(2) 0.0010(14) 0.0112(16) 0.0006(17) + C12 0.104(3) 0.094(3) 0.127(3) -0.011(2) 0.027(2) -0.009(2) + C13 0.163(5) 0.101(3) 0.142(4) 0.008(3) -0.022(4) 0.014(3) + C14 0.351(13) 0.109(4) 0.208(8) -0.010(5) 0.035(8) 0.048(5) + C15 0.132(5) 0.145(5) 0.332(11) 0.029(4) -0.038(7) 0.009(6) + C21 0.0658(17) 0.091(2) 0.090(2) 0.0008(14) 0.0127(15) -0.0019(17) + C22 0.120(3) 0.089(3) 0.134(3) 0.006(2) 0.009(3) 0.004(2) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.217(3) ? + O2 C2 . 1.238(3) ? + N1 C1 . 1.361(4) ? + N1 C2 . 1.395(4) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.322(4) ? + N2 C21 . 1.447(4) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.516(5) ? + C11 C12 . 1.495(5) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.508(7) ? + C12 H122 . 0.9700 ? + C12 H121 . 0.9700 ? + C13 C15 . 1.522(9) ? + C13 C14 . 1.531(8) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C21 C22 . 1.498(5) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.5(2) ? + C1 N1 H11 . . 115.2 ? + C2 N1 H11 . . 115.2 ? + C2 N2 C21 . . 122.1(2) ? + C2 N2 H21 . . 118.9 ? + C21 N2 H21 . . 118.9 ? + O1 C1 N1 . . 122.6(3) ? + O1 C1 C11 . . 122.1(3) ? + N1 C1 C11 . . 115.3(2) ? + O2 C2 N2 . . 123.5(3) ? + O2 C2 N1 . . 118.2(3) ? + N2 C2 N1 . . 118.3(2) ? + C12 C11 C1 . . 115.1(3) ? + C12 C11 H112 . . 108.5 ? + C1 C11 H112 . . 108.5 ? + C12 C11 H111 . . 108.5 ? + C1 C11 H111 . . 108.5 ? + H112 C11 H111 . . 107.5 ? + C11 C12 C13 . . 114.6(3) ? + C11 C12 H122 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + C11 C12 H121 . . 108.6 ? + C13 C12 H121 . . 108.6 ? + H122 C12 H121 . . 107.6 ? + C12 C13 C15 . . 112.2(5) ? + C12 C13 C14 . . 110.0(5) ? + C15 C13 C14 . . 108.7(6) ? + C12 C13 H131 . . 108.6 ? + C15 C13 H131 . . 108.6 ? + C14 C13 H131 . . 108.6 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H153 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + N2 C21 C22 . . 112.9(3) ? + N2 C21 H211 . . 109.0 ? + C22 C21 H211 . . 109.0 ? + N2 C21 H212 . . 109.0 ? + C22 C21 H212 . . 109.0 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 2.1(5) ? + C2 N1 C1 C11 . . . . -176.8(3) ? + C21 N2 C2 O2 . . . . 0.1(4) ? + C21 N2 C2 N1 . . . . 178.8(2) ? + C1 N1 C2 O2 . . . . 179.5(3) ? + C1 N1 C2 N2 . . . . 0.8(4) ? + O1 C1 C11 C12 . . . . 54.6(4) ? + N1 C1 C11 C12 . . . . -126.5(3) ? + C1 C11 C12 C13 . . . . 66.9(5) ? + C11 C12 C13 C15 . . . . 63.1(6) ? + C11 C12 C13 C14 . . . . -175.7(5) ? + C2 N2 C21 C22 . . . . -82.7(4) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.40 3.085(3) 137.1 + N1 H11 O2 2_566 0.86 2.00 2.861(3) 177.7 +data_ethyl360K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7564(14) +_cell_length_b 12.5792(14) +_cell_length_c 5.1472(6) +_cell_angle_alpha 90.683(10) +_cell_angle_beta 90.707(6) +_cell_angle_gamma 89.216(6) +_cell_volume 566.82(13) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2770 +_cell_measurement_theta_min 2.815 +_cell_measurement_theta_max 27.3 +_cell_measurement_temperature 360 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.091 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.077 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 360 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6442 +_diffrn_reflns_av_R_equivalents 0.055 +_diffrn_reflns_av_sigmaI/netI 0.0305 +_diffrn_reflns_theta_min 2.33 +_diffrn_reflns_theta_max 27.43 +_diffrn_reflns_theta_full 27.43 +_diffrn_measured_fraction_theta_max 0.923 +_diffrn_measured_fraction_theta_full 0.923 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2389 +_reflns_number_gt 1518 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1332 +_refine_ls_R_factor_gt 0.0998 +_refine_ls_wR_factor_gt 0.2768 +_refine_ls_wR_factor_ref 0.3155 +_refine_ls_goodness_of_fit_ref 1.039 +_refine_ls_restrained_S_all 1.043 +_refine_ls_number_reflns 2389 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1605P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.305 +_refine_diff_density_min -0.286 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 358K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4323(3) 0.5741(2) 0.2286(6) 0.0901(8) Uani d . 1 . . O + O2 0.0268(3) 0.4099(2) 0.2428(5) 0.0870(8) Uani d . 1 . . O + N1 0.1970(3) 0.5334(2) 0.3761(6) 0.0710(8) Uani d . 1 . . N + H11 0.1304 0.5521 0.4898 0.085 Uiso calc R 1 . . H + N2 0.2524(3) 0.4167(2) 0.0336(6) 0.0747(8) Uani d . 1 . . N + H21 0.3385 0.4483 0.0205 0.090 Uiso calc R 1 . . H + C1 0.3288(4) 0.5898(3) 0.3835(7) 0.0698(9) Uani d . 1 . . C + C2 0.1541(4) 0.4501(3) 0.2124(7) 0.0712(9) Uani d . 1 . . C + C11 0.3405(5) 0.6718(3) 0.5965(8) 0.0845(10) Uani d D 1 . . C + H112 0.4188 0.6486 0.7190 0.101 Uiso calc R 1 . . H + H111 0.2443 0.6743 0.6881 0.101 Uiso calc R 1 . . H + C12 0.3769(6) 0.7824(4) 0.5126(11) 0.1170(16) Uani d D 1 . . C + H121 0.4692 0.7795 0.4104 0.140 Uiso calc R 1 . . H + H122 0.3979 0.8254 0.6662 0.140 Uiso calc R 1 . . H + C13 0.2526(7) 0.8365(4) 0.3553(13) 0.140(2) Uani d D 1 . . C + H131 0.2293 0.7922 0.2024 0.168 Uiso calc R 1 . . H + C14 0.3085(14) 0.9442(5) 0.264(2) 0.233(5) Uani d D 1 . . C + H143 0.2299 0.9782 0.1622 0.279 Uiso calc R 1 . . H + H142 0.3982 0.9340 0.1610 0.279 Uiso calc R 1 . . H + H141 0.3327 0.9881 0.4127 0.279 Uiso calc R 1 . . H + C15 0.1069(8) 0.8536(7) 0.509(2) 0.218(5) Uani d D 1 . . C + H153 0.0310 0.8877 0.4020 0.261 Uiso calc R 1 . . H + H151 0.1281 0.8977 0.6588 0.261 Uiso calc R 1 . . H + H152 0.0699 0.7862 0.5650 0.261 Uiso calc R 1 . . H + C21 0.2183(4) 0.3289(3) -0.1393(8) 0.0845(10) Uani d D 1 . . C + H211 0.2780 0.3356 -0.2956 0.101 Uiso calc R 1 . . H + H212 0.1113 0.3331 -0.1895 0.101 Uiso calc R 1 . . H + C22 0.2504(7) 0.2222(4) -0.0241(11) 0.1191(16) Uani d D 1 . . C + H223 0.2252 0.1676 -0.1486 0.143 Uiso calc R 1 . . H + H222 0.1899 0.2141 0.1285 0.143 Uiso calc R 1 . . H + H221 0.3567 0.2165 0.0220 0.143 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0673(14) 0.1010(18) 0.1031(18) -0.0140(12) 0.0296(13) -0.0023(14) + O2 0.0617(14) 0.0968(17) 0.1034(19) -0.0135(11) 0.0254(12) -0.0052(14) + N1 0.0581(14) 0.0739(16) 0.0816(17) -0.0041(11) 0.0225(12) 0.0009(13) + N2 0.0576(14) 0.0799(17) 0.0870(19) -0.0035(12) 0.0198(13) -0.0010(14) + C1 0.0573(16) 0.0748(19) 0.078(2) -0.0007(13) 0.0135(14) 0.0148(15) + C2 0.0556(16) 0.0758(19) 0.083(2) 0.0048(13) 0.0173(14) 0.0131(16) + C11 0.079(2) 0.080(2) 0.095(3) 0.0000(17) 0.0101(19) 0.0035(19) + C12 0.110(3) 0.106(3) 0.135(4) -0.014(3) 0.026(3) -0.008(3) + C13 0.162(6) 0.111(4) 0.148(5) 0.011(4) -0.020(4) 0.018(3) + C14 0.371(16) 0.107(5) 0.222(9) -0.005(6) 0.024(10) 0.049(5) + C15 0.125(6) 0.169(7) 0.357(14) 0.028(5) -0.041(8) 0.009(8) + C21 0.068(2) 0.093(2) 0.093(2) -0.0001(17) 0.0115(18) -0.004(2) + C22 0.129(4) 0.089(3) 0.139(4) 0.004(3) 0.012(3) -0.004(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.227(4) ? + O2 C2 . 1.243(4) ? + N1 C1 . 1.363(4) ? + N1 C2 . 1.390(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.328(4) ? + N2 C21 . 1.443(5) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.499(5) ? + C11 C12 . 1.502(6) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.508(8) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.522(11) ? + C13 C14 . 1.527(10) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C21 C22 . 1.495(6) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.7(3) ? + C1 N1 H11 . . 115.2 ? + C2 N1 H11 . . 115.2 ? + C2 N2 C21 . . 121.6(3) ? + C2 N2 H21 . . 119.2 ? + C21 N2 H21 . . 119.2 ? + O1 C1 N1 . . 122.5(3) ? + O1 C1 C11 . . 121.9(3) ? + N1 C1 C11 . . 115.6(3) ? + O2 C2 N2 . . 123.4(3) ? + O2 C2 N1 . . 118.4(3) ? + N2 C2 N1 . . 118.2(3) ? + C1 C11 C12 . . 115.9(3) ? + C1 C11 H112 . . 108.3 ? + C12 C11 H112 . . 108.3 ? + C1 C11 H111 . . 108.3 ? + C12 C11 H111 . . 108.3 ? + H112 C11 H111 . . 107.4 ? + C11 C12 C13 . . 114.7(4) ? + C11 C12 H121 . . 108.6 ? + C13 C12 H121 . . 108.6 ? + C11 C12 H122 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + H121 C12 H122 . . 107.6 ? + C12 C13 C15 . . 112.3(6) ? + C12 C13 C14 . . 109.5(6) ? + C15 C13 C14 . . 108.9(7) ? + C12 C13 H131 . . 108.7 ? + C15 C13 H131 . . 108.7 ? + C14 C13 H131 . . 108.7 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H153 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + N2 C21 C22 . . 113.8(4) ? + N2 C21 H211 . . 108.8 ? + C22 C21 H211 . . 108.8 ? + N2 C21 H212 . . 108.8 ? + C22 C21 H212 . . 108.8 ? + H211 C21 H212 . . 107.7 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 2.1(6) ? + C2 N1 C1 C11 . . . . -177.0(3) ? + C21 N2 C2 O2 . . . . -0.7(5) ? + C21 N2 C2 N1 . . . . 178.3(3) ? + C1 N1 C2 O2 . . . . 179.6(3) ? + C1 N1 C2 N2 . . . . 0.5(5) ? + O1 C1 C11 C12 . . . . 54.4(5) ? + N1 C1 C11 C12 . . . . -126.5(4) ? + C1 C11 C12 C13 . . . . 67.5(6) ? + C11 C12 C13 C15 . . . . 63.5(7) ? + C11 C12 C13 C14 . . . . -175.5(6) ? + C2 N2 C21 C22 . . . . -82.8(4) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.41 3.092(4) 137.0 + N1 H11 O2 2_566 0.86 2.01 2.867(3) 177.9 +data_ethyl362K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.6700(10) +_cell_length_b 12.5515(9) +_cell_length_c 5.1490(5) +_cell_angle_alpha 90.036(7) +_cell_angle_beta 91.078(4) +_cell_angle_gamma 88.834(4) +_cell_volume 560.11(9) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2412 +_cell_measurement_theta_min 2.83 +_cell_measurement_theta_max 27.425 +_cell_measurement_temperature 362 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.104 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.078 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 362 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6484 +_diffrn_reflns_av_R_equivalents 0.032 +_diffrn_reflns_av_sigmaI/netI 0.0197 +_diffrn_reflns_theta_min 2.35 +_diffrn_reflns_theta_max 27.47 +_diffrn_reflns_theta_full 27.47 +_diffrn_measured_fraction_theta_max 0.920 +_diffrn_measured_fraction_theta_full 0.920 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2361 +_reflns_number_gt 1478 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1277 +_refine_ls_R_factor_gt 0.0938 +_refine_ls_wR_factor_gt 0.2883 +_refine_ls_wR_factor_ref 0.3316 +_refine_ls_goodness_of_fit_ref 1.056 +_refine_ls_restrained_S_all 1.064 +_refine_ls_number_reflns 2361 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1819P)^2^+0.1580P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.367 +_refine_diff_density_min -0.341 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 360K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4317(3) 0.5740(2) 0.2258(5) 0.0949(9) Uani d . 1 . . O + O2 0.0275(3) 0.4100(2) 0.2453(5) 0.0914(9) Uani d . 1 . . O + N1 0.1969(3) 0.5334(2) 0.3743(6) 0.0748(8) Uani d . 1 . . N + H11 0.1295 0.5524 0.4868 0.090 Uiso calc R 1 . . H + N2 0.2531(3) 0.4165(2) 0.0370(6) 0.0797(9) Uani d . 1 . . N + H21 0.3405 0.4471 0.0254 0.096 Uiso calc R 1 . . H + C1 0.3285(3) 0.5898(3) 0.3805(7) 0.0746(9) Uani d . 1 . . C + C2 0.1545(4) 0.4502(3) 0.2152(7) 0.0743(9) Uani d . 1 . . C + C11 0.3404(5) 0.6710(3) 0.5935(8) 0.0920(11) Uani d D 1 . . C + H112 0.4198 0.6471 0.7166 0.110 Uiso calc R 1 . . H + H111 0.2434 0.6736 0.6845 0.110 Uiso calc R 1 . . H + C12 0.3768(6) 0.7819(4) 0.5084(11) 0.1242(17) Uani d D 1 . . C + H121 0.3985 0.8246 0.6615 0.149 Uiso calc R 1 . . H + H122 0.4697 0.7789 0.4064 0.149 Uiso calc R 1 . . H + C13 0.2523(8) 0.8363(4) 0.3527(13) 0.152(2) Uani d D 1 . . C + H131 0.2281 0.7923 0.2006 0.183 Uiso calc R 1 . . H + C14 0.3107(14) 0.9435(6) 0.260(2) 0.251(6) Uani d D 1 . . C + H143 0.2318 0.9787 0.1563 0.301 Uiso calc R 1 . . H + H142 0.4010 0.9322 0.1577 0.301 Uiso calc R 1 . . H + H141 0.3358 0.9870 0.4075 0.301 Uiso calc R 1 . . H + C15 0.1059(8) 0.8539(7) 0.507(2) 0.227(5) Uani d D 1 . . C + H153 0.0287 0.8887 0.3991 0.273 Uiso calc R 1 . . H + H151 0.1280 0.8976 0.6555 0.273 Uiso calc R 1 . . H + H152 0.0686 0.7864 0.5635 0.273 Uiso calc R 1 . . H + C21 0.2176(4) 0.3298(3) -0.1379(8) 0.0913(11) Uani d D 1 . . C + H211 0.2779 0.3365 -0.2936 0.110 Uiso calc R 1 . . H + H212 0.1094 0.3346 -0.1887 0.110 Uiso calc R 1 . . H + C22 0.2508(6) 0.2234(4) -0.0178(11) 0.1232(16) Uani d D 1 . . C + H223 0.2254 0.1684 -0.1399 0.148 Uiso calc R 1 . . H + H222 0.1900 0.2159 0.1348 0.148 Uiso calc R 1 . . H + H221 0.3583 0.2176 0.0291 0.148 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0658(13) 0.1088(19) 0.1116(19) -0.0130(12) 0.0314(13) -0.0022(14) + O2 0.0629(13) 0.0996(17) 0.1131(19) -0.0112(11) 0.0291(12) -0.0031(14) + N1 0.0582(14) 0.0805(17) 0.0866(17) -0.0030(11) 0.0229(12) 0.0022(13) + N2 0.0590(14) 0.0865(18) 0.0943(19) 0.0009(12) 0.0211(13) 0.0013(15) + C1 0.0584(15) 0.0772(19) 0.089(2) 0.0043(13) 0.0159(14) 0.0167(16) + C2 0.0570(15) 0.0818(19) 0.085(2) 0.0020(13) 0.0165(14) 0.0119(16) + C11 0.080(2) 0.089(2) 0.107(3) -0.0002(18) 0.0159(19) 0.000(2) + C12 0.117(4) 0.109(3) 0.148(4) -0.010(3) 0.034(3) -0.007(3) + C13 0.177(6) 0.112(4) 0.166(6) 0.012(4) -0.020(5) 0.023(4) + C14 0.389(17) 0.115(5) 0.250(11) -0.002(7) 0.047(11) 0.062(6) + C15 0.129(6) 0.163(7) 0.387(15) 0.039(5) -0.026(8) 0.019(8) + C21 0.072(2) 0.100(3) 0.102(3) 0.0020(18) 0.0164(18) -0.004(2) + C22 0.129(4) 0.096(3) 0.144(4) 0.005(3) 0.010(3) 0.003(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.222(4) ? + O2 C2 . 1.232(4) ? + N1 C1 . 1.355(4) ? + N1 C2 . 1.378(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.329(4) ? + N2 C21 . 1.447(5) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.500(5) ? + C11 C12 . 1.501(6) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.487(8) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.522(11) ? + C13 C14 . 1.527(11) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C21 C22 . 1.492(6) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.8(3) ? + C1 N1 H11 . . 115.1 ? + C2 N1 H11 . . 115.1 ? + C2 N2 C21 . . 121.9(3) ? + C2 N2 H21 . . 119.0 ? + C21 N2 H21 . . 119.0 ? + O1 C1 N1 . . 122.1(4) ? + O1 C1 C11 . . 122.4(3) ? + N1 C1 C11 . . 115.5(3) ? + O2 C2 N2 . . 122.9(4) ? + O2 C2 N1 . . 118.7(3) ? + N2 C2 N1 . . 118.4(3) ? + C1 C11 C12 . . 115.6(4) ? + C1 C11 H112 . . 108.4 ? + C12 C11 H112 . . 108.4 ? + C1 C11 H111 . . 108.4 ? + C12 C11 H111 . . 108.4 ? + H112 C11 H111 . . 107.4 ? + C13 C12 C11 . . 114.7(4) ? + C13 C12 H121 . . 108.6 ? + C11 C12 H121 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + C11 C12 H122 . . 108.6 ? + H121 C12 H122 . . 107.6 ? + C12 C13 C15 . . 112.3(6) ? + C12 C13 C14 . . 108.8(7) ? + C15 C13 C14 . . 109.5(7) ? + C12 C13 H131 . . 108.7 ? + C15 C13 H131 . . 108.7 ? + C14 C13 H131 . . 108.7 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H153 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + N2 C21 C22 . . 112.2(4) ? + N2 C21 H211 . . 109.2 ? + C22 C21 H211 . . 109.2 ? + N2 C21 H212 . . 109.2 ? + C22 C21 H212 . . 109.2 ? + H211 C21 H212 . . 107.9 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 2.6(5) ? + C2 N1 C1 C11 . . . . -175.9(3) ? + C21 N2 C2 O2 . . . . 0.6(5) ? + C21 N2 C2 N1 . . . . -179.9(3) ? + C1 N1 C2 O2 . . . . 179.7(3) ? + C1 N1 C2 N2 . . . . 0.2(5) ? + O1 C1 C11 C12 . . . . 54.3(5) ? + N1 C1 C11 C12 . . . . -127.2(4) ? + C1 C11 C12 C13 . . . . 67.6(6) ? + C11 C12 C13 C15 . . . . 63.7(8) ? + C11 C12 C13 C14 . . . . -175.0(6) ? + C2 N2 C21 C22 . . . . -83.2(4) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.39 3.077(4) 137.0 + N1 H11 O2 2_566 0.86 2.01 2.866(3) 177.5 +data_ethyl364K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7109(12) +_cell_length_b 12.6454(10) +_cell_length_c 5.1787(6) +_cell_angle_alpha 90.134(7) +_cell_angle_beta 90.557(4) +_cell_angle_gamma 88.953(4) +_cell_volume 570.32(11) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2832 +_cell_measurement_theta_min 2.815 +_cell_measurement_theta_max 27.465 +_cell_measurement_temperature 364 +_exptl_crystal_description 'triclinic' +_exptl_crystal_colour 'P -1' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.085 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.077 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 364 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 7726 +_diffrn_reflns_av_R_equivalents 0.028 +_diffrn_reflns_av_sigmaI/netI 0.0248 +_diffrn_reflns_theta_min 2.34 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.956 +_diffrn_measured_fraction_theta_full 0.956 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2503 +_reflns_number_gt 1474 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1327 +_refine_ls_R_factor_gt 0.0914 +_refine_ls_wR_factor_gt 0.2586 +_refine_ls_wR_factor_ref 0.3005 +_refine_ls_goodness_of_fit_ref 1.054 +_refine_ls_restrained_S_all 1.061 +_refine_ls_number_reflns 2503 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1424P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.327 +_refine_diff_density_min -0.335 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 362K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4319(3) 0.5736(2) 0.2249(5) 0.0986(9) Uani d . 1 . . O + O2 0.0272(2) 0.4103(2) 0.2467(5) 0.0946(8) Uani d . 1 . . O + N1 0.1969(3) 0.5332(2) 0.3748(5) 0.0782(8) Uani d . 1 . . N + H11 0.1299 0.5519 0.4879 0.094 Uiso calc R 1 . . H + N2 0.2527(3) 0.4164(2) 0.0378(5) 0.0816(8) Uani d . 1 . . N + H21 0.3394 0.4473 0.0241 0.098 Uiso calc R 1 . . H + C1 0.3282(3) 0.5898(3) 0.3795(7) 0.0773(9) Uani d . 1 . . C + C2 0.1543(3) 0.4501(3) 0.2157(7) 0.0770(9) Uani d . 1 . . C + C11 0.3393(4) 0.6712(3) 0.5878(8) 0.0947(11) Uani d D 1 . . C + H112 0.4174 0.6478 0.7108 0.114 Uiso calc R 1 . . H + H111 0.2423 0.6741 0.6781 0.114 Uiso calc R 1 . . H + C12 0.3765(6) 0.7815(4) 0.5040(12) 0.1366(19) Uani d D 1 . . C + H121 0.3983 0.8236 0.6563 0.164 Uiso calc R 1 . . H + H122 0.4690 0.7784 0.4012 0.164 Uiso calc R 1 . . H + C13 0.2526(8) 0.8360(5) 0.3510(13) 0.164(2) Uani d D 1 . . C + H131 0.2278 0.7921 0.2005 0.197 Uiso calc R 1 . . H + C14 0.3093(14) 0.9432(6) 0.256(2) 0.268(6) Uani d D 1 . . C + H143 0.2300 0.9774 0.1545 0.321 Uiso calc R 1 . . H + H142 0.3988 0.9324 0.1516 0.321 Uiso calc R 1 . . H + H141 0.3345 0.9869 0.4013 0.321 Uiso calc R 1 . . H + C15 0.1066(9) 0.8549(7) 0.506(2) 0.254(5) Uani d D 1 . . C + H153 0.0311 0.8906 0.3998 0.305 Uiso calc R 1 . . H + H151 0.1294 0.8977 0.6542 0.305 Uiso calc R 1 . . H + H152 0.0674 0.7882 0.5612 0.305 Uiso calc R 1 . . H + C21 0.2184(4) 0.3296(3) -0.1327(8) 0.0941(11) Uani d D 1 . . C + H211 0.2785 0.3363 -0.2883 0.113 Uiso calc R 1 . . H + H212 0.1108 0.3342 -0.1821 0.113 Uiso calc R 1 . . H + C22 0.2509(6) 0.2236(4) -0.0161(11) 0.1308(17) Uani d D 1 . . C + H223 0.2256 0.1694 -0.1385 0.157 Uiso calc R 1 . . H + H222 0.1902 0.2157 0.1362 0.157 Uiso calc R 1 . . H + H221 0.3579 0.2177 0.0291 0.157 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0688(13) 0.1134(18) 0.1148(19) -0.0135(12) 0.0318(13) -0.0016(14) + O2 0.0659(13) 0.1035(17) 0.1153(19) -0.0122(11) 0.0291(12) -0.0042(14) + N1 0.0613(14) 0.0823(16) 0.0916(18) -0.0019(11) 0.0244(12) 0.0028(14) + N2 0.0597(14) 0.0895(18) 0.0961(19) -0.0029(12) 0.0200(13) 0.0002(15) + C1 0.0602(16) 0.0814(19) 0.090(2) 0.0025(13) 0.0160(14) 0.0168(16) + C2 0.0569(15) 0.086(2) 0.088(2) 0.0057(14) 0.0179(14) 0.0129(17) + C11 0.083(2) 0.087(2) 0.115(3) -0.0018(17) 0.0169(19) 0.002(2) + C12 0.124(4) 0.118(4) 0.169(5) -0.011(3) 0.040(3) -0.007(3) + C13 0.175(6) 0.133(4) 0.183(6) 0.019(4) -0.013(5) 0.039(4) + C14 0.416(18) 0.120(5) 0.268(11) -0.021(7) 0.024(11) 0.065(6) + C15 0.138(6) 0.191(8) 0.432(16) 0.044(5) -0.026(8) 0.027(9) + C21 0.073(2) 0.103(3) 0.106(3) 0.0018(17) 0.0162(18) -0.001(2) + C22 0.135(4) 0.100(3) 0.157(4) 0.007(3) 0.013(3) 0.001(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.226(4) ? + O2 C2 . 1.236(4) ? + N1 C1 . 1.360(4) ? + N1 C2 . 1.388(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.329(4) ? + N2 C21 . 1.440(5) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.494(5) ? + C11 C12 . 1.503(6) ? + C11 H112 . 0.9700 ? + C11 H111 . 0.9700 ? + C12 C13 . 1.492(8) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.525(11) ? + C13 C14 . 1.536(10) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C21 C22 . 1.493(6) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.9(3) ? + C1 N1 H11 . . 115.0 ? + C2 N1 H11 . . 115.0 ? + C2 N2 C21 . . 121.9(3) ? + C2 N2 H21 . . 119.1 ? + C21 N2 H21 . . 119.1 ? + O1 C1 N1 . . 122.0(3) ? + O1 C1 C11 . . 122.3(3) ? + N1 C1 C11 . . 115.7(3) ? + O2 C2 N2 . . 123.0(3) ? + O2 C2 N1 . . 118.7(3) ? + N2 C2 N1 . . 118.3(3) ? + C1 C11 C12 . . 116.5(4) ? + C1 C11 H112 . . 108.2 ? + C12 C11 H112 . . 108.2 ? + C1 C11 H111 . . 108.2 ? + C12 C11 H111 . . 108.2 ? + H112 C11 H111 . . 107.3 ? + C13 C12 C11 . . 114.6(4) ? + C13 C12 H121 . . 108.6 ? + C11 C12 H121 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + C11 C12 H122 . . 108.6 ? + H121 C12 H122 . . 107.6 ? + C12 C13 C15 . . 112.7(6) ? + C12 C13 C14 . . 109.7(6) ? + C15 C13 C14 . . 108.4(7) ? + C12 C13 H131 . . 108.6 ? + C15 C13 H131 . . 108.6 ? + C14 C13 H131 . . 108.6 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H153 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + N2 C21 C22 . . 113.5(4) ? + N2 C21 H211 . . 108.9 ? + C22 C21 H211 . . 108.9 ? + N2 C21 H212 . . 108.9 ? + C22 C21 H212 . . 108.9 ? + H211 C21 H212 . . 107.7 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 1.9(5) ? + C2 N1 C1 C11 . . . . -176.9(3) ? + C21 N2 C2 O2 . . . . -0.4(5) ? + C21 N2 C2 N1 . . . . 179.1(3) ? + C1 N1 C2 O2 . . . . -179.9(3) ? + C1 N1 C2 N2 . . . . 0.6(5) ? + O1 C1 C11 C12 . . . . 53.8(5) ? + N1 C1 C11 C12 . . . . -127.3(4) ? + C1 C11 C12 C13 . . . . 68.3(6) ? + C11 C12 C13 C15 . . . . 64.2(8) ? + C11 C12 C13 C14 . . . . -174.8(6) ? + C2 N2 C21 C22 . . . . -83.0(4) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.39 3.083(3) 137.4 + N1 H11 O2 2_566 0.86 2.00 2.860(3) 177.9 +data_ethyl366K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.7157(12) +_cell_length_b 12.6307(7) +_cell_length_c 5.1642(7) +_cell_angle_alpha 89.780(10) +_cell_angle_beta 90.522(6) +_cell_angle_gamma 88.757(5) +_cell_volume 568.34(11) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2373 +_cell_measurement_theta_min 2.81 +_cell_measurement_theta_max 27.39 +_cell_measurement_temperature 366 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.088 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.077 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being low temperature phase. +; +_diffrn_ambient_temperature 366 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6593 +_diffrn_reflns_av_R_equivalents 0.033 +_diffrn_reflns_av_sigmaI/netI 0.0237 +_diffrn_reflns_theta_min 2.34 +_diffrn_reflns_theta_max 27.47 +_diffrn_reflns_theta_full 27.47 +_diffrn_measured_fraction_theta_max 0.912 +_diffrn_measured_fraction_theta_full 0.912 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2383 +_reflns_number_gt 1377 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1455 +_refine_ls_R_factor_gt 0.1004 +_refine_ls_wR_factor_gt 0.2914 +_refine_ls_wR_factor_ref 0.3424 +_refine_ls_goodness_of_fit_ref 1.051 +_refine_ls_restrained_S_all 1.058 +_refine_ls_number_reflns 2383 +_refine_ls_number_parameters 118 +_refine_ls_number_restraints 5 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1637P)^2^+0.2294P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.319 +_refine_diff_density_min -0.351 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 364K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4312(3) 0.5736(2) 0.2226(6) 0.1031(10) Uani d . 1 . . O + O2 0.0275(3) 0.4105(2) 0.2482(6) 0.0982(10) Uani d . 1 . . O + N1 0.1970(3) 0.5329(2) 0.3746(6) 0.0805(9) Uani d . 1 . . N + H11 0.1307 0.5513 0.4892 0.097 Uiso calc R 1 . . H + N2 0.2532(3) 0.4167(2) 0.0410(7) 0.0849(10) Uani d . 1 . . N + H21 0.3401 0.4471 0.0282 0.102 Uiso calc R 1 . . H + C1 0.3274(4) 0.5894(3) 0.3763(8) 0.0797(10) Uani d . 1 . . C + C2 0.1540(4) 0.4501(3) 0.2168(8) 0.0822(11) Uani d . 1 . . C + C11 0.3390(5) 0.6702(3) 0.5821(10) 0.1012(13) Uani d D 1 . . C + H111 0.4173 0.6465 0.7051 0.121 Uiso calc R 1 . . H + H112 0.2423 0.6733 0.6734 0.121 Uiso calc R 1 . . H + C12 0.3760(7) 0.7804(4) 0.4976(15) 0.154(3) Uani d D 1 . . C + H121 0.3992 0.8220 0.6500 0.185 Uiso calc R 1 . . H + H122 0.4675 0.7773 0.3922 0.185 Uiso calc R 1 . . H + C13 0.2512(9) 0.8357(6) 0.3477(17) 0.176(3) Uani d D 1 . . C + H131 0.2261 0.7926 0.1964 0.212 Uiso calc R 1 . . H + C14 0.3096(17) 0.9424(7) 0.252(3) 0.299(8) Uani d D 1 . . C + H143 0.2313 0.9775 0.1498 0.358 Uiso calc R 1 . . H + H142 0.3994 0.9309 0.1489 0.358 Uiso calc R 1 . . H + H141 0.3349 0.9857 0.3983 0.358 Uiso calc R 1 . . H + C15 0.1057(10) 0.8541(9) 0.503(3) 0.271(6) Uani d D 1 . . C + H153 0.0293 0.8889 0.3954 0.325 Uiso calc R 1 . . H + H151 0.1278 0.8977 0.6496 0.325 Uiso calc R 1 . . H + H152 0.0680 0.7874 0.5609 0.325 Uiso calc R 1 . . H + C21 0.2180(5) 0.3301(4) -0.1300(9) 0.1003(13) Uani d D 1 . . C + H211 0.2777 0.3365 -0.2867 0.120 Uiso calc R 1 . . H + H212 0.1102 0.3348 -0.1785 0.120 Uiso calc R 1 . . H + C22 0.2515(7) 0.2241(4) -0.0079(13) 0.135(2) Uani d D 1 . . C + H223 0.2260 0.1692 -0.1277 0.162 Uiso calc R 1 . . H + H222 0.1915 0.2169 0.1459 0.162 Uiso calc R 1 . . H + H221 0.3586 0.2183 0.0363 0.162 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0734(16) 0.117(2) 0.120(2) -0.0134(14) 0.0366(15) -0.0011(17) + O2 0.0680(15) 0.107(2) 0.121(2) -0.0110(13) 0.0309(14) -0.0051(16) + N1 0.0627(16) 0.0837(19) 0.096(2) -0.0030(13) 0.0232(14) -0.0002(16) + N2 0.0622(16) 0.092(2) 0.101(2) -0.0023(14) 0.0219(15) -0.0020(17) + C1 0.0637(18) 0.082(2) 0.093(2) 0.0011(15) 0.0165(17) 0.0163(18) + C2 0.0587(17) 0.091(2) 0.097(3) 0.0060(16) 0.0196(17) 0.016(2) + C11 0.089(3) 0.089(3) 0.126(4) -0.001(2) 0.020(2) 0.004(2) + C12 0.145(5) 0.119(4) 0.201(7) -0.007(4) 0.053(5) -0.008(4) + C13 0.181(7) 0.140(5) 0.207(8) 0.017(5) -0.013(6) 0.043(5) + C14 0.47(2) 0.117(6) 0.308(15) -0.035(9) 0.053(15) 0.050(7) + C15 0.140(8) 0.223(10) 0.45(2) 0.056(7) -0.018(10) 0.008(11) + C21 0.077(2) 0.113(3) 0.112(3) 0.000(2) 0.018(2) -0.004(3) + C22 0.138(5) 0.102(3) 0.166(5) 0.004(3) 0.013(4) 0.004(3) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.222(4) ? + O2 C2 . 1.233(4) ? + N1 C1 . 1.355(5) ? + N1 C2 . 1.385(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.323(5) ? + N2 C21 . 1.445(5) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.481(6) ? + C11 C12 . 1.499(7) ? + C11 H111 . 0.9700 ? + C11 H112 . 0.9700 ? + C12 C13 . 1.490(10) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.520(13) ? + C13 C14 . 1.532(13) ? + C13 H131 . 0.9800 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H141 . 0.9600 ? + C15 H153 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C21 C22 . 1.500(7) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.9(3) ? + C1 N1 H11 . . 115.0 ? + C2 N1 H11 . . 115.0 ? + C2 N2 C21 . . 121.2(3) ? + C2 N2 H21 . . 119.4 ? + C21 N2 H21 . . 119.4 ? + O1 C1 N1 . . 122.6(4) ? + O1 C1 C11 . . 121.6(4) ? + N1 C1 C11 . . 115.7(3) ? + O2 C2 N2 . . 123.4(4) ? + O2 C2 N1 . . 118.9(3) ? + N2 C2 N1 . . 117.6(3) ? + C1 C11 C12 . . 116.8(5) ? + C1 C11 H111 . . 108.1 ? + C12 C11 H111 . . 108.1 ? + C1 C11 H112 . . 108.1 ? + C12 C11 H112 . . 108.1 ? + H111 C11 H112 . . 107.3 ? + C13 C12 C11 . . 114.5(5) ? + C13 C12 H121 . . 108.6 ? + C11 C12 H121 . . 108.6 ? + C13 C12 H122 . . 108.6 ? + C11 C12 H122 . . 108.6 ? + H121 C12 H122 . . 107.6 ? + C12 C13 C15 . . 113.4(7) ? + C12 C13 C14 . . 108.9(8) ? + C15 C13 C14 . . 109.2(9) ? + C12 C13 H131 . . 108.4 ? + C15 C13 H131 . . 108.4 ? + C14 C13 H131 . . 108.4 ? + C13 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C14 H141 . . 109.5 ? + H143 C14 H141 . . 109.5 ? + H142 C14 H141 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + H153 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H153 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + N2 C21 C22 . . 112.4(4) ? + N2 C21 H211 . . 109.1 ? + C22 C21 H211 . . 109.1 ? + N2 C21 H212 . . 109.1 ? + C22 C21 H212 . . 109.1 ? + H211 C21 H212 . . 107.9 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 1.1(6) ? + C2 N1 C1 C11 . . . . -177.2(4) ? + C21 N2 C2 O2 . . . . 0.4(6) ? + C21 N2 C2 N1 . . . . 179.5(3) ? + C1 N1 C2 O2 . . . . -179.3(3) ? + C1 N1 C2 N2 . . . . 1.6(6) ? + O1 C1 C11 C12 . . . . 53.9(6) ? + N1 C1 C11 C12 . . . . -127.7(4) ? + C1 C11 C12 C13 . . . . 69.0(7) ? + C11 C12 C13 C15 . . . . 63.5(10) ? + C11 C12 C13 C14 . . . . -174.6(7) ? + C2 N2 C21 C22 . . . . -83.6(5) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.40 3.085(4) 137.3 + N1 H11 O2 2_566 0.86 2.00 2.855(4) 177.9 +data_ethyl368K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.6912(5) +_cell_length_b 12.7757(6) +_cell_length_c 5.15870(10) +_cell_angle_alpha 88.386(2) +_cell_angle_beta 91.168(6) +_cell_angle_gamma 88.4630(19) +_cell_volume 572.24(4) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2775 +_cell_measurement_theta_min 2.8 +_cell_measurement_theta_max 27.465 +_cell_measurement_temperature 368 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.081 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.077 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being high temperature phase. +; +_diffrn_ambient_temperature 368 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 7417 +_diffrn_reflns_av_R_equivalents 0.021 +_diffrn_reflns_av_sigmaI/netI 0.0210 +_diffrn_reflns_theta_min 2.34 +_diffrn_reflns_theta_max 27.47 +_diffrn_reflns_theta_full 27.47 +_diffrn_measured_fraction_theta_max 0.868 +_diffrn_measured_fraction_theta_full 0.868 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2283 +_reflns_number_gt 1212 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1569 +_refine_ls_R_factor_gt 0.0989 +_refine_ls_wR_factor_gt 0.2561 +_refine_ls_wR_factor_ref 0.3081 +_refine_ls_goodness_of_fit_ref 1.067 +_refine_ls_restrained_S_all 1.069 +_refine_ls_number_reflns 2283 +_refine_ls_number_parameters 131 +_refine_ls_number_restraints 17 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1263P)^2^+0.2311P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.241 +_refine_diff_density_min -0.276 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 366K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4310(3) 0.5728(2) 0.2201(6) 0.1095(11) Uani d . 1 A . O + O2 0.0279(3) 0.4107(2) 0.2539(6) 0.1050(10) Uani d . 1 A . O + N1 0.1966(3) 0.5326(2) 0.3729(6) 0.0858(10) Uani d . 1 A . N + H11 0.1302 0.5513 0.4852 0.103 Uiso calc R 1 . . H + N2 0.2532(3) 0.4167(3) 0.0458(7) 0.0928(10) Uani d D 1 A . N + H21 0.3403 0.4466 0.0329 0.111 Uiso calc R 1 . . H + C1 0.3272(4) 0.5884(3) 0.3710(7) 0.0866(11) Uani d D 1 . . C + C2 0.1542(4) 0.4496(3) 0.2198(8) 0.0861(11) Uani d . 1 . . C + C11A 0.3370(5) 0.6696(3) 0.5749(9) 0.1098(14) Uani d PD 0.874(6) A 1 C + H111 0.4138 0.6454 0.7035 0.132 Uiso calc PR 0.874(6) A 1 H + H112 0.2388 0.6729 0.6609 0.132 Uiso calc PR 0.874(6) A 1 H + C12A 0.3760(7) 0.7806(4) 0.4893(15) 0.158(3) Uani d PD 0.874(6) A 1 C + H121 0.4671 0.7782 0.3839 0.190 Uiso calc PR 0.874(6) A 1 H + H122 0.3993 0.8208 0.6412 0.190 Uiso calc PR 0.874(6) A 1 H + C13A 0.2445(9) 0.8353(6) 0.3344(16) 0.179(4) Uani d PD 0.874(6) A 1 C + H131 0.2167 0.7941 0.1839 0.214 Uiso calc PR 0.874(6) A 1 H + C14A 0.3006(18) 0.9430(6) 0.245(3) 0.288(8) Uani d PD 0.874(6) A 1 C + H142 0.3886 0.9340 0.1373 0.433 Uiso calc PR 0.874(6) A 1 H + H141 0.3286 0.9824 0.3935 0.433 Uiso calc PR 0.874(6) A 1 H + H143 0.2198 0.9799 0.1477 0.433 Uiso calc PR 0.874(6) A 1 H + C15A 0.1029(11) 0.8553(9) 0.500(3) 0.265(6) Uani d PD 0.874(6) A 1 C + H153 0.0226 0.8887 0.3940 0.397 Uiso calc PR 0.874(6) A 1 H + H151 0.1296 0.8998 0.6394 0.397 Uiso calc PR 0.874(6) A 1 H + H152 0.0678 0.7898 0.5688 0.397 Uiso calc PR 0.874(6) A 1 H + C11B 0.3370(5) 0.6696(3) 0.5749(9) 0.1098(14) Uani d PD 0.126(6) A 2 C + H113 0.4414 0.6943 0.5864 0.132 Uiso calc PR 0.126(6) A 2 H + H114 0.3120 0.6385 0.7419 0.132 Uiso calc PR 0.126(6) A 2 H + C12B 0.226(2) 0.7623(11) 0.511(5) 0.158(3) Uani d PD 0.126(6) A 2 C + H123 0.1857 0.7549 0.3363 0.190 Uiso calc PR 0.126(6) A 2 H + H124 0.1400 0.7581 0.6276 0.190 Uiso calc PR 0.126(6) A 2 H + C13B 0.293(4) 0.8711(8) 0.531(7) 0.179(4) Uani d PD 0.126(6) A 2 C + H132 0.2095 0.9233 0.5035 0.214 Uiso calc PR 0.126(6) A 2 H + C14B 0.411(8) 0.888(4) 0.317(11) 0.288(8) Uani d PD 0.126(6) A 2 C + H144 0.4524 0.9566 0.3303 0.433 Uiso calc PR 0.126(6) A 2 H + H145 0.3611 0.8819 0.1507 0.433 Uiso calc PR 0.126(6) A 2 H + H146 0.4925 0.8361 0.3371 0.433 Uiso calc PR 0.126(6) A 2 H + C15B 0.368(6) 0.888(3) 0.797(10) 0.265(6) Uani d PD 0.126(6) A 2 C + H154 0.3793 0.9611 0.8222 0.397 Uiso calc PR 0.126(6) A 2 H + H155 0.4667 0.8526 0.8076 0.397 Uiso calc PR 0.126(6) A 2 H + H156 0.3031 0.8593 0.9295 0.397 Uiso calc PR 0.126(6) A 2 H + C21 0.2181(5) 0.3309(3) -0.1245(9) 0.1067(14) Uani d D 1 . . C + H211 0.2772 0.3384 -0.2811 0.128 Uiso calc R 1 A . H + H212 0.1099 0.3358 -0.1742 0.128 Uiso calc R 1 . . H + C22 0.2527(7) 0.2252(4) -0.0027(12) 0.145(2) Uani d D 1 A . C + H223 0.2259 0.1722 -0.1225 0.174 Uiso calc R 1 . . H + H222 0.1940 0.2169 0.1517 0.174 Uiso calc R 1 . . H + H221 0.3605 0.2187 0.0409 0.174 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0768(16) 0.125(2) 0.129(2) -0.0137(14) 0.0384(16) -0.0026(18) + O2 0.0712(16) 0.116(2) 0.129(2) -0.0131(14) 0.0339(15) -0.0055(17) + N1 0.0638(16) 0.091(2) 0.103(2) -0.0010(14) 0.0245(15) 0.0014(18) + N2 0.0661(17) 0.104(2) 0.109(2) -0.0023(15) 0.0234(16) -0.0014(19) + C1 0.068(2) 0.085(2) 0.106(3) 0.0029(17) 0.0175(19) 0.017(2) + C2 0.0628(19) 0.092(2) 0.102(3) 0.0040(17) 0.0193(19) 0.016(2) + C11A 0.092(3) 0.099(3) 0.139(4) 0.001(2) 0.022(3) 0.004(3) + C12A 0.151(6) 0.120(5) 0.209(8) -0.018(4) 0.075(6) -0.013(5) + C13A 0.201(9) 0.152(7) 0.178(8) 0.009(6) -0.019(7) 0.049(6) + C14A 0.48(2) 0.098(6) 0.287(14) -0.008(8) 0.042(14) 0.056(7) + C15A 0.151(8) 0.209(10) 0.432(19) 0.052(7) 0.029(10) -0.005(11) + C11B 0.092(3) 0.099(3) 0.139(4) 0.001(2) 0.022(3) 0.004(3) + C12B 0.151(6) 0.120(5) 0.209(8) -0.018(4) 0.075(6) -0.013(5) + C13B 0.201(9) 0.152(7) 0.178(8) 0.009(6) -0.019(7) 0.049(6) + C14B 0.48(2) 0.098(6) 0.287(14) -0.008(8) 0.042(14) 0.056(7) + C15B 0.151(8) 0.209(10) 0.432(19) 0.052(7) 0.029(10) -0.005(11) + C21 0.085(3) 0.113(3) 0.123(3) 0.002(2) 0.021(2) 0.000(3) + C22 0.150(5) 0.115(4) 0.169(5) 0.005(3) 0.017(4) 0.000(4) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.219(4) ? + O2 C2 . 1.231(4) ? + N1 C1 . 1.356(5) ? + N1 C2 . 1.393(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.326(5) ? + N2 C21 . 1.459(6) ? + N2 H21 . 0.8600 ? + C1 C11A . 1.501(6) ? + C11A C12A . 1.522(6) ? + C11A H111 . 0.9700 ? + C11A H112 . 0.9700 ? + C11A C12B . 1.530(18) ? + C12A C13A . 1.524(10) ? + C12A H121 . 0.9700 ? + C12A H122 . 0.9700 ? + C13A C15A . 1.531(14) ? + C13A C14A . 1.533(12) ? + C13A H131 . 0.9800 ? + C14A H142 . 0.9600 ? + C14A H141 . 0.9600 ? + C14A H143 . 0.9600 ? + C15A H153 . 0.9600 ? + C15A H151 . 0.9600 ? + C15A H152 . 0.9600 ? + C12B C13B . 1.53(2) ? + C12B H123 . 0.9700 ? + C12B H124 . 0.9700 ? + C13B C15B . 1.53(6) ? + C13B C14B . 1.53(7) ? + C13B H132 . 0.9800 ? + C14B H144 . 0.9600 ? + C14B H145 . 0.9600 ? + C14B H146 . 0.9600 ? + C15B H154 . 0.9600 ? + C15B H155 . 0.9600 ? + C15B H156 . 0.9600 ? + C21 C22 . 1.493(7) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.5(3) ? + C1 N1 H11 . . 115.2 ? + C2 N1 H11 . . 115.2 ? + C2 N2 C21 . . 121.6(3) ? + C2 N2 H21 . . 119.2 ? + C21 N2 H21 . . 119.2 ? + O1 C1 N1 . . 123.1(4) ? + O1 C1 C11A . . 122.0(4) ? + N1 C1 C11A . . 114.8(3) ? + O2 C2 N2 . . 123.7(4) ? + O2 C2 N1 . . 118.5(3) ? + N2 C2 N1 . . 117.8(3) ? + C1 C11A C12A . . 118.0(4) ? + C1 C11A H111 . . 107.8 ? + C12A C11A H111 . . 107.8 ? + C1 C11A H112 . . 107.8 ? + C12A C11A H112 . . 107.8 ? + H111 C11A H112 . . 107.2 ? + C11A C12A C13A . . 112.2(5) ? + C11A C12A H121 . . 109.2 ? + C13A C12A H121 . . 109.2 ? + C11A C12A H122 . . 109.2 ? + C13A C12A H122 . . 109.2 ? + H121 C12A H122 . . 107.9 ? + C12A C13A C15A . . 112.2(7) ? + C12A C13A C14A . . 107.4(7) ? + C15A C13A C14A . . 106.7(10) ? + C12A C13A H131 . . 110.1 ? + C15A C13A H131 . . 110.1 ? + C14A C13A H131 . . 110.1 ? + C13A C14A H142 . . 109.5 ? + C13A C14A H141 . . 109.5 ? + H142 C14A H141 . . 109.5 ? + C13A C14A H143 . . 109.5 ? + H142 C14A H143 . . 109.5 ? + H141 C14A H143 . . 109.5 ? + C13A C15A H153 . . 109.5 ? + C13A C15A H151 . . 109.5 ? + H153 C15A H151 . . 109.5 ? + C13A C15A H152 . . 109.5 ? + H153 C15A H152 . . 109.5 ? + H151 C15A H152 . . 109.5 ? + C13B C12B H123 . . 108.3 ? + C13B C12B H124 . . 108.3 ? + H123 C12B H124 . . 107.4 ? + C12B C13B C15B . . 111.8(7) ? + C12B C13B C14B . . 109.9(7) ? + C15B C13B C14B . . 110.4(7) ? + C12B C13B H132 . . 108.2 ? + C15B C13B H132 . . 108.2 ? + C14B C13B H132 . . 108.2 ? + C13B C14B H144 . . 109.5 ? + C13B C14B H145 . . 109.5 ? + H144 C14B H145 . . 109.5 ? + C13B C14B H146 . . 109.5 ? + H144 C14B H146 . . 109.5 ? + H145 C14B H146 . . 109.5 ? + C13B C15B H154 . . 109.5 ? + C13B C15B H155 . . 109.5 ? + H154 C15B H155 . . 109.5 ? + C13B C15B H156 . . 109.5 ? + H154 C15B H156 . . 109.5 ? + H155 C15B H156 . . 109.5 ? + N2 C21 C22 . . 113.3(4) ? + N2 C21 H211 . . 108.9 ? + C22 C21 H211 . . 108.9 ? + N2 C21 H212 . . 108.9 ? + C22 C21 H212 . . 108.9 ? + H211 C21 H212 . . 107.7 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 1.4(6) ? + C2 N1 C1 C11A . . . . -177.0(4) ? + C21 N2 C2 O2 . . . . 0.9(6) ? + C21 N2 C2 N1 . . . . -179.4(3) ? + C1 N1 C2 O2 . . . . -179.4(4) ? + C1 N1 C2 N2 . . . . 0.9(6) ? + O1 C1 C11A C12A . . . . 52.5(6) ? + N1 C1 C11A C12A . . . . -129.1(5) ? + C1 C11A C12A C13A . . . . 70.6(7) ? + C11A C12A C13A C15A . . . . 66.5(9) ? + C11A C12A C13A C14A . . . . -176.5(7) ? + C2 N2 C21 C22 . . . . -84.0(5) ? + C2 N1 C1 C11B . . . . -177.0(4) ? + O1 C1 C11B C12B . . . . 109.5(13) ? + N1 C1 C11B C12B . . . . -72.0(13) ? + C1 C11B C12B C13B . . . . -132.0(18) ? + C11B C12B C13B C15B . . . . -55(3) ? + C11B C12B C13B C14B . . . . 68(3) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.41 3.098(4) 137.1 + N1 H11 O2 2_566 0.86 2.00 2.863(4) 177.8 +data_ethyl370K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.605(2) +_cell_length_b 12.855(2) +_cell_length_c 5.1699(10) +_cell_angle_alpha 87.263(16) +_cell_angle_beta 92.266(9) +_cell_angle_gamma 88.060(8) +_cell_volume 570.39(19) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2605 +_cell_measurement_theta_min 2.895 +_cell_measurement_theta_max 27.445 +_cell_measurement_temperature 370 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 1.00 +_exptl_crystal_size_min 0.20 +_exptl_crystal_density_diffrn 1.084 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.077 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being high temperature phase. +; +_diffrn_ambient_temperature 370 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 9055 +_diffrn_reflns_av_R_equivalents 0.031 +_diffrn_reflns_av_sigmaI/netI 0.0325 +_diffrn_reflns_theta_min 2.37 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.863 +_diffrn_measured_fraction_theta_full 0.863 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2263 +_reflns_number_gt 1016 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1977 +_refine_ls_R_factor_gt 0.1160 +_refine_ls_wR_factor_gt 0.3094 +_refine_ls_wR_factor_ref 0.3859 +_refine_ls_goodness_of_fit_ref 1.065 +_refine_ls_restrained_S_all 1.065 +_refine_ls_number_reflns 2263 +_refine_ls_number_parameters 131 +_refine_ls_number_restraints 17 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1627P)^2^+0.2588P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.278 +_refine_diff_density_min -0.271 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 368K was used as an initial model. + The minor part of the disordered 3-methylbutyl group was + deleted to avoid some viases for disorder analysis. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4305(4) 0.5716(3) 0.2153(8) 0.1207(14) Uani d . 1 A . O + O2 0.0278(4) 0.4110(3) 0.2582(8) 0.1167(14) Uani d . 1 A . O + N1 0.1965(4) 0.5326(3) 0.3720(8) 0.0955(13) Uani d . 1 A . N + H11 0.1305 0.5508 0.4836 0.115 Uiso calc R 1 . . H + N2 0.2530(4) 0.4165(3) 0.0519(8) 0.1012(14) Uani d D 1 A . N + H21 0.3406 0.4461 0.0375 0.121 Uiso calc R 1 . . H + C1 0.3268(5) 0.5873(4) 0.3646(10) 0.0971(15) Uani d D 1 . . C + C2 0.1552(5) 0.4504(4) 0.2223(11) 0.0985(15) Uani d . 1 . . C + C11A 0.3352(7) 0.6690(4) 0.5612(11) 0.124(2) Uani d PD 0.813(8) A 1 C + H111 0.4121 0.6450 0.6949 0.148 Uiso calc PR 0.813(8) A 1 H + H112 0.2355 0.6728 0.6420 0.148 Uiso calc PR 0.813(8) A 1 H + C12A 0.3745(11) 0.7794(5) 0.472(2) 0.177(4) Uani d PD 0.813(8) A 1 C + H121 0.4654 0.7767 0.3666 0.212 Uiso calc PR 0.813(8) A 1 H + H122 0.3997 0.8191 0.6216 0.212 Uiso calc PR 0.813(8) A 1 H + C13A 0.2393(13) 0.8341(8) 0.314(2) 0.190(5) Uani d PD 0.813(8) A 1 C + H131 0.2089 0.7940 0.1649 0.228 Uiso calc PR 0.813(8) A 1 H + C14A 0.292(3) 0.9422(9) 0.226(4) 0.333(12) Uani d PD 0.813(8) A 1 C + H142 0.3805 0.9348 0.1191 0.499 Uiso calc PR 0.813(8) A 1 H + H141 0.3210 0.9802 0.3748 0.499 Uiso calc PR 0.813(8) A 1 H + H143 0.2090 0.9793 0.1283 0.499 Uiso calc PR 0.813(8) A 1 H + C15A 0.0990(16) 0.8579(13) 0.477(4) 0.307(10) Uani d PD 0.813(8) A 1 C + H153 0.0174 0.8920 0.3691 0.461 Uiso calc PR 0.813(8) A 1 H + H151 0.1291 0.9026 0.6126 0.461 Uiso calc PR 0.813(8) A 1 H + H152 0.0623 0.7940 0.5525 0.461 Uiso calc PR 0.813(8) A 1 H + C11B 0.3352(7) 0.6690(4) 0.5612(11) 0.124(2) Uani d PD 0.187(8) A 2 C + H113 0.4408 0.6926 0.5774 0.148 Uiso calc PR 0.187(8) A 2 H + H114 0.3077 0.6393 0.7286 0.148 Uiso calc PR 0.187(8) A 2 H + C12B 0.224(2) 0.7617(10) 0.482(5) 0.177(4) Uani d PD 0.187(8) A 2 C + H123 0.1895 0.7551 0.3029 0.212 Uiso calc PR 0.187(8) A 2 H + H124 0.1336 0.7572 0.5866 0.212 Uiso calc PR 0.187(8) A 2 H + C13B 0.290(4) 0.8698(8) 0.507(7) 0.190(5) Uani d PD 0.187(8) A 2 C + H132 0.2034 0.9212 0.4914 0.228 Uiso calc PR 0.187(8) A 2 H + C14B 0.399(8) 0.893(4) 0.286(10) 0.333(12) Uani d PD 0.187(8) A 2 C + H144 0.4386 0.9616 0.3013 0.499 Uiso calc PR 0.187(8) A 2 H + H145 0.3428 0.8897 0.1230 0.499 Uiso calc PR 0.187(8) A 2 H + H146 0.4843 0.8427 0.2957 0.499 Uiso calc PR 0.187(8) A 2 H + C15B 0.376(5) 0.881(3) 0.769(9) 0.307(10) Uani d PD 0.187(8) A 2 C + H154 0.3904 0.9533 0.7959 0.461 Uiso calc PR 0.187(8) A 2 H + H155 0.4749 0.8445 0.7707 0.461 Uiso calc PR 0.187(8) A 2 H + H156 0.3148 0.8518 0.9044 0.461 Uiso calc PR 0.187(8) A 2 H + C21 0.2180(6) 0.3318(4) -0.1106(12) 0.1171(19) Uani d D 1 . . C + H211 0.2776 0.3384 -0.2656 0.140 Uiso calc R 1 A . H + H212 0.1085 0.3371 -0.1638 0.140 Uiso calc R 1 . . H + C22 0.2534(9) 0.2264(5) 0.0197(17) 0.167(3) Uani d D 1 A . C + H223 0.2272 0.1734 -0.0975 0.200 Uiso calc R 1 . . H + H222 0.1934 0.2187 0.1717 0.200 Uiso calc R 1 . . H + H221 0.3622 0.2198 0.0684 0.200 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.080(2) 0.146(3) 0.139(3) -0.0148(19) 0.037(2) -0.006(2) + O2 0.077(2) 0.129(3) 0.147(3) -0.0122(18) 0.034(2) -0.011(2) + N1 0.070(2) 0.100(3) 0.117(3) -0.0018(19) 0.025(2) -0.001(2) + N2 0.071(2) 0.114(3) 0.120(3) -0.003(2) 0.023(2) -0.004(3) + C1 0.070(3) 0.098(3) 0.123(4) 0.000(2) 0.017(3) 0.008(3) + C2 0.062(2) 0.114(4) 0.119(4) 0.005(2) 0.027(2) 0.016(3) + C11A 0.095(4) 0.110(4) 0.166(6) -0.002(3) 0.021(3) 0.002(4) + C12A 0.168(9) 0.138(7) 0.231(11) -0.024(6) 0.088(9) 0.000(7) + C13A 0.191(11) 0.173(9) 0.197(12) -0.007(8) -0.029(9) 0.054(9) + C14A 0.54(4) 0.117(9) 0.34(2) 0.007(13) 0.04(2) 0.053(11) + C15A 0.143(11) 0.246(16) 0.53(3) 0.046(10) 0.048(14) -0.045(17) + C11B 0.095(4) 0.110(4) 0.166(6) -0.002(3) 0.021(3) 0.002(4) + C12B 0.168(9) 0.138(7) 0.231(11) -0.024(6) 0.088(9) 0.000(7) + C13B 0.191(11) 0.173(9) 0.197(12) -0.007(8) -0.029(9) 0.054(9) + C14B 0.54(4) 0.117(9) 0.34(2) 0.007(13) 0.04(2) 0.053(11) + C15B 0.143(11) 0.246(16) 0.53(3) 0.046(10) 0.048(14) -0.045(17) + C21 0.088(3) 0.125(4) 0.138(5) 0.006(3) 0.016(3) -0.004(4) + C22 0.153(7) 0.126(5) 0.222(9) 0.008(5) 0.020(6) -0.018(6) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.221(6) ? + O2 C2 . 1.241(6) ? + N1 C1 . 1.345(6) ? + N1 C2 . 1.386(7) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.321(6) ? + N2 C21 . 1.440(7) ? + N2 H21 . 0.8600 ? + C1 C11A . 1.497(7) ? + C11A C12A . 1.525(9) ? + C11A H111 . 0.9700 ? + C11A H112 . 0.9700 ? + C11A C12B . 1.530(17) ? + C12A C13A . 1.526(14) ? + C12A H121 . 0.9700 ? + C12A H122 . 0.9700 ? + C13A C15A . 1.53(2) ? + C13A C14A . 1.532(18) ? + C13A H131 . 0.9800 ? + C14A H142 . 0.9600 ? + C14A H141 . 0.9600 ? + C14A H143 . 0.9600 ? + C15A H153 . 0.9600 ? + C15A H151 . 0.9600 ? + C15A H152 . 0.9600 ? + C12B C13B . 1.53(2) ? + C12B H123 . 0.9700 ? + C12B H124 . 0.9700 ? + C13B C15B . 1.53(6) ? + C13B C14B . 1.53(7) ? + C13B H132 . 0.9800 ? + C14B H144 . 0.9600 ? + C14B H145 . 0.9600 ? + C14B H146 . 0.9600 ? + C15B H154 . 0.9600 ? + C15B H155 . 0.9600 ? + C15B H156 . 0.9600 ? + C21 C22 . 1.500(9) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 128.1(4) ? + C1 N1 H11 . . 115.9 ? + C2 N1 H11 . . 115.9 ? + C2 N2 C21 . . 122.3(4) ? + C2 N2 H21 . . 118.9 ? + C21 N2 H21 . . 118.9 ? + O1 C1 N1 . . 123.7(5) ? + O1 C1 C11A . . 122.6(5) ? + N1 C1 C11A . . 113.7(4) ? + O2 C2 N2 . . 122.9(6) ? + O2 C2 N1 . . 117.9(4) ? + N2 C2 N1 . . 119.2(4) ? + C1 C11A C12A . . 118.6(6) ? + C1 C11A H111 . . 107.7 ? + C12A C11A H111 . . 107.7 ? + C1 C11A H112 . . 107.7 ? + C12A C11A H112 . . 107.7 ? + H111 C11A H112 . . 107.1 ? + C11A C12A C13A . . 111.5(7) ? + C11A C12A H121 . . 109.3 ? + C13A C12A H121 . . 109.3 ? + C11A C12A H122 . . 109.3 ? + C13A C12A H122 . . 109.3 ? + H121 C12A H122 . . 108.0 ? + C12A C13A C15A . . 112.9(10) ? + C12A C13A C14A . . 107.4(11) ? + C15A C13A C14A . . 103.6(14) ? + C12A C13A H131 . . 110.9 ? + C15A C13A H131 . . 110.9 ? + C14A C13A H131 . . 110.9 ? + C13A C14A H142 . . 109.5 ? + C13A C14A H141 . . 109.5 ? + H142 C14A H141 . . 109.5 ? + C13A C14A H143 . . 109.5 ? + H142 C14A H143 . . 109.5 ? + H141 C14A H143 . . 109.5 ? + C13A C15A H153 . . 109.5 ? + C13A C15A H151 . . 109.5 ? + H153 C15A H151 . . 109.5 ? + C13A C15A H152 . . 109.5 ? + H153 C15A H152 . . 109.5 ? + H151 C15A H152 . . 109.5 ? + C13B C12B H123 . . 108.2 ? + C13B C12B H124 . . 108.2 ? + H123 C12B H124 . . 107.4 ? + C12B C13B C15B . . 112.2(7) ? + C12B C13B C14B . . 109.9(7) ? + C15B C13B C14B . . 110.3(7) ? + C12B C13B H132 . . 108.1 ? + C15B C13B H132 . . 108.1 ? + C14B C13B H132 . . 108.1 ? + C13B C14B H144 . . 109.5 ? + C13B C14B H145 . . 109.5 ? + H144 C14B H145 . . 109.5 ? + C13B C14B H146 . . 109.5 ? + H144 C14B H146 . . 109.5 ? + H145 C14B H146 . . 109.5 ? + C13B C15B H154 . . 109.5 ? + C13B C15B H155 . . 109.5 ? + H154 C15B H155 . . 109.5 ? + C13B C15B H156 . . 109.5 ? + H154 C15B H156 . . 109.5 ? + H155 C15B H156 . . 109.5 ? + N2 C21 C22 . . 113.4(5) ? + N2 C21 H211 . . 108.9 ? + C22 C21 H211 . . 108.9 ? + N2 C21 H212 . . 108.9 ? + C22 C21 H212 . . 108.9 ? + H211 C21 H212 . . 107.7 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 0.7(8) ? + C2 N1 C1 C11A . . . . -178.1(5) ? + C21 N2 C2 O2 . . . . 1.3(8) ? + C21 N2 C2 N1 . . . . -179.8(5) ? + C1 N1 C2 O2 . . . . -179.2(4) ? + C1 N1 C2 N2 . . . . 1.8(8) ? + O1 C1 C11A C12A . . . . 50.8(8) ? + N1 C1 C11A C12A . . . . -130.3(6) ? + C1 C11A C12A C13A . . . . 72.2(10) ? + C11A C12A C13A C15A . . . . 68.4(13) ? + C11A C12A C13A C14A . . . . -178.0(11) ? + C2 N2 C21 C22 . . . . -83.3(6) ? + C2 N1 C1 C11B . . . . -178.1(5) ? + O1 C1 C11B C12B . . . . 107.1(13) ? + N1 C1 C11B C12B . . . . -74.1(12) ? + C1 C11B C12B C13B . . . . -134.6(18) ? + C11B C12B C13B C15B . . . . -47(3) ? + C11B C12B C13B C14B . . . . 76(3) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.42 3.107(5) 137.7 + N1 H11 O2 2_566 0.86 2.01 2.870(5) 178.0 +data_ethyl372K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.6137(18) +_cell_length_b 12.994(3) +_cell_length_c 5.1906(11) +_cell_angle_alpha 86.197(10) +_cell_angle_beta 91.616(12) +_cell_angle_gamma 88.099(6) +_cell_volume 579.1(2) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 2962 +_cell_measurement_theta_min 2.79 +_cell_measurement_theta_max 27.48 +_cell_measurement_temperature 372 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 0.60 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.068 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.076 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being high temperature phase. +; +_diffrn_ambient_temperature 372 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 8178 +_diffrn_reflns_av_R_equivalents 0.040 +_diffrn_reflns_av_sigmaI/netI 0.0291 +_diffrn_reflns_theta_min 2.80 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.868 +_diffrn_measured_fraction_theta_full 0.868 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2312 +_reflns_number_gt 1114 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1865 +_refine_ls_R_factor_gt 0.1244 +_refine_ls_wR_factor_gt 0.3045 +_refine_ls_wR_factor_ref 0.3336 +_refine_ls_goodness_of_fit_ref 1.753 +_refine_ls_restrained_S_all 1.772 +_refine_ls_number_reflns 2312 +_refine_ls_number_parameters 131 +_refine_ls_number_restraints 17 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.387 +_refine_diff_density_min -0.293 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 370K was used as an initial model. + The minor part of the disordered 3-methylbutyl group was + deleted to avoid some viases for disorder analysis. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4299(3) 0.5710(2) 0.2076(6) 0.1290(10) Uani d . 1 A . O + O2 0.0275(2) 0.41152(19) 0.2663(5) 0.1204(9) Uani d . 1 A . O + N1 0.1962(3) 0.5315(2) 0.3685(6) 0.1017(9) Uani d . 1 A . N + H11 0.1302 0.5501 0.4793 0.122 Uiso calc R 1 . . H + N2 0.2536(3) 0.4159(2) 0.0604(6) 0.1066(10) Uani d D 1 A . N + H21 0.3419 0.4445 0.0464 0.128 Uiso calc R 1 . . H + C1 0.3266(4) 0.5868(2) 0.3546(7) 0.1013(11) Uani d D 1 . . C + C2 0.1551(4) 0.4493(3) 0.2288(7) 0.1005(10) Uani d . 1 . . C + C11A 0.3342(5) 0.6684(2) 0.5442(8) 0.1283(14) Uani d PD 0.774(6) A 1 C + H111 0.4095 0.6449 0.6797 0.154 Uiso calc PR 0.774(6) A 1 H + H112 0.2338 0.6734 0.6235 0.154 Uiso calc PR 0.774(6) A 1 H + C12A 0.3760(7) 0.7768(3) 0.4458(17) 0.203(4) Uani d PD 0.774(6) A 1 C + H121 0.4117 0.8143 0.5903 0.243 Uiso calc PR 0.774(6) A 1 H + H122 0.4606 0.7720 0.3273 0.243 Uiso calc PR 0.774(6) A 1 H + C13A 0.2389(8) 0.8363(6) 0.3087(18) 0.219(5) Uani d PD 0.774(6) A 1 C + H131 0.2028 0.7964 0.1663 0.263 Uiso calc PR 0.774(6) A 1 H + C14A 0.284(2) 0.9425(7) 0.195(3) 0.382(11) Uani d PD 0.774(6) A 1 C + H142 0.3715 0.9348 0.0870 0.574 Uiso calc PR 0.774(6) A 1 H + H141 0.3097 0.9854 0.3320 0.574 Uiso calc PR 0.774(6) A 1 H + H143 0.1976 0.9739 0.0932 0.574 Uiso calc PR 0.774(6) A 1 H + C15A 0.0997(13) 0.8609(12) 0.471(3) 0.343(8) Uani d PD 0.774(6) A 1 C + H153 0.0187 0.8947 0.3623 0.515 Uiso calc PR 0.774(6) A 1 H + H151 0.1302 0.9055 0.6023 0.515 Uiso calc PR 0.774(6) A 1 H + H152 0.0623 0.7981 0.5506 0.515 Uiso calc PR 0.774(6) A 1 H + C11B 0.3342(5) 0.6684(2) 0.5442(8) 0.1283(14) Uani d PD 0.226(6) A 2 C + H113 0.4411 0.6872 0.5726 0.154 Uiso calc PR 0.226(6) A 2 H + H114 0.2940 0.6429 0.7082 0.154 Uiso calc PR 0.226(6) A 2 H + C12B 0.2364(14) 0.7629(5) 0.434(3) 0.203(4) Uani d PD 0.226(6) A 2 C + H123 0.2284 0.7604 0.2479 0.243 Uiso calc PR 0.226(6) A 2 H + H124 0.1322 0.7575 0.4991 0.243 Uiso calc PR 0.226(6) A 2 H + C13B 0.2968(16) 0.8678(6) 0.495(2) 0.219(5) Uani d PD 0.226(6) A 2 C + H132 0.2084 0.9173 0.4930 0.263 Uiso calc PR 0.226(6) A 2 H + C14B 0.408(3) 0.904(2) 0.287(4) 0.382(11) Uani d PD 0.226(6) A 2 C + H144 0.4415 0.9723 0.3196 0.574 Uiso calc PR 0.226(6) A 2 H + H145 0.3566 0.9061 0.1206 0.574 Uiso calc PR 0.226(6) A 2 H + H146 0.4974 0.8577 0.2904 0.574 Uiso calc PR 0.226(6) A 2 H + C15B 0.378(3) 0.8645(19) 0.761(3) 0.343(8) Uani d PD 0.226(6) A 2 C + H154 0.3968 0.9336 0.8066 0.515 Uiso calc PR 0.226(6) A 2 H + H155 0.4755 0.8264 0.7572 0.515 Uiso calc PR 0.226(6) A 2 H + H156 0.3137 0.8314 0.8874 0.515 Uiso calc PR 0.226(6) A 2 H + C21 0.2183(4) 0.3335(3) -0.1002(8) 0.1250(14) Uani d D 1 . . C + H211 0.2782 0.3406 -0.2555 0.150 Uiso calc R 1 A . H + H212 0.1091 0.3391 -0.1519 0.150 Uiso calc R 1 . . H + C22 0.2530(7) 0.2286(4) 0.0324(12) 0.171(2) Uani d D 1 A . C + H223 0.2273 0.1765 -0.0827 0.205 Uiso calc R 1 . . H + H222 0.1925 0.2205 0.1845 0.205 Uiso calc R 1 . . H + H221 0.3615 0.2219 0.0803 0.205 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0883(14) 0.142(2) 0.160(2) -0.0232(14) 0.0507(15) -0.0064(17) + O2 0.0841(14) 0.1289(19) 0.153(2) -0.0235(13) 0.0434(14) -0.0172(16) + N1 0.0761(14) 0.110(2) 0.121(2) -0.0094(14) 0.0330(14) -0.0047(17) + N2 0.0749(15) 0.114(2) 0.134(2) -0.0090(14) 0.0292(16) -0.0123(18) + C1 0.0783(18) 0.100(2) 0.124(3) -0.0042(16) 0.0224(18) 0.017(2) + C2 0.0698(17) 0.112(2) 0.118(3) -0.0006(17) 0.0233(18) 0.007(2) + C11A 0.104(3) 0.111(3) 0.171(4) -0.009(2) 0.025(3) -0.006(3) + C12A 0.182(7) 0.128(5) 0.304(10) -0.031(5) 0.103(8) -0.009(5) + C13A 0.230(9) 0.173(7) 0.241(11) -0.039(6) -0.060(8) 0.074(7) + C14A 0.63(3) 0.120(7) 0.385(19) -0.002(10) 0.07(2) 0.054(8) + C15A 0.177(9) 0.357(17) 0.51(2) 0.045(10) 0.075(12) -0.105(15) + C11B 0.104(3) 0.111(3) 0.171(4) -0.009(2) 0.025(3) -0.006(3) + C12B 0.182(7) 0.128(5) 0.304(10) -0.031(5) 0.103(8) -0.009(5) + C13B 0.230(9) 0.173(7) 0.241(11) -0.039(6) -0.060(8) 0.074(7) + C14B 0.63(3) 0.120(7) 0.385(19) -0.002(10) 0.07(2) 0.054(8) + C15B 0.177(9) 0.357(17) 0.51(2) 0.045(10) 0.075(12) -0.105(15) + C21 0.101(2) 0.131(3) 0.144(4) -0.004(2) 0.031(2) -0.008(3) + C22 0.178(5) 0.141(4) 0.193(5) 0.007(3) 0.006(4) -0.014(4) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.210(4) ? + O2 C2 . 1.233(4) ? + N1 C1 . 1.354(4) ? + N1 C2 . 1.381(5) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.319(4) ? + N2 C21 . 1.436(5) ? + N2 H21 . 0.8600 ? + C1 C11A . 1.496(5) ? + C11A C12A . 1.523(6) ? + C11A H111 . 0.9700 ? + C11A H112 . 0.9700 ? + C11A C12B . 1.534(10) ? + C12A C13A . 1.522(9) ? + C12A H121 . 0.9700 ? + C12A H122 . 0.9700 ? + C13A C15A . 1.522(16) ? + C13A C14A . 1.530(14) ? + C13A H131 . 0.9800 ? + C14A H142 . 0.9600 ? + C14A H141 . 0.9600 ? + C14A H143 . 0.9600 ? + C15A H153 . 0.9600 ? + C15A H151 . 0.9600 ? + C15A H152 . 0.9600 ? + C12B C13B . 1.525(12) ? + C12B H123 . 0.9700 ? + C12B H124 . 0.9700 ? + C13B C15B . 1.53(2) ? + C13B C14B . 1.53(3) ? + C13B H132 . 0.9800 ? + C14B H144 . 0.9600 ? + C14B H145 . 0.9600 ? + C14B H146 . 0.9600 ? + C15B H154 . 0.9600 ? + C15B H155 . 0.9600 ? + C15B H156 . 0.9600 ? + C21 C22 . 1.502(6) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 128.7(3) ? + C1 N1 H11 . . 115.7 ? + C2 N1 H11 . . 115.7 ? + C2 N2 C21 . . 122.2(3) ? + C2 N2 H21 . . 118.9 ? + C21 N2 H21 . . 118.9 ? + O1 C1 N1 . . 123.8(3) ? + O1 C1 C11A . . 122.4(3) ? + N1 C1 C11A . . 113.8(3) ? + O2 C2 N2 . . 123.4(4) ? + O2 C2 N1 . . 118.3(3) ? + N2 C2 N1 . . 118.3(3) ? + C1 C11A C12A . . 118.2(4) ? + C1 C11A H111 . . 107.8 ? + C12A C11A H111 . . 107.8 ? + C1 C11A H112 . . 107.8 ? + C12A C11A H112 . . 107.8 ? + H111 C11A H112 . . 107.1 ? + C13A C12A C11A . . 112.3(5) ? + C13A C12A H121 . . 109.1 ? + C11A C12A H121 . . 109.1 ? + C13A C12A H122 . . 109.1 ? + C11A C12A H122 . . 109.1 ? + H121 C12A H122 . . 107.9 ? + C12A C13A C15A . . 117.0(8) ? + C12A C13A C14A . . 112.3(9) ? + C15A C13A C14A . . 103.3(11) ? + C12A C13A H131 . . 108.0 ? + C15A C13A H131 . . 108.0 ? + C14A C13A H131 . . 108.0 ? + C13A C14A H142 . . 109.5 ? + C13A C14A H141 . . 109.5 ? + H142 C14A H141 . . 109.5 ? + C13A C14A H143 . . 109.5 ? + H142 C14A H143 . . 109.5 ? + H141 C14A H143 . . 109.5 ? + C13A C15A H153 . . 109.5 ? + C13A C15A H151 . . 109.5 ? + H153 C15A H151 . . 109.5 ? + C13A C15A H152 . . 109.5 ? + H153 C15A H152 . . 109.5 ? + H151 C15A H152 . . 109.5 ? + C13B C12B H123 . . 108.3 ? + C13B C12B H124 . . 108.3 ? + H123 C12B H124 . . 107.4 ? + C12B C13B C15B . . 112.0(7) ? + C12B C13B C14B . . 109.5(7) ? + C15B C13B C14B . . 109.9(7) ? + C12B C13B H132 . . 108.4 ? + C15B C13B H132 . . 108.4 ? + C14B C13B H132 . . 108.4 ? + C13B C14B H144 . . 109.5 ? + C13B C14B H145 . . 109.5 ? + H144 C14B H145 . . 109.5 ? + C13B C14B H146 . . 109.5 ? + H144 C14B H146 . . 109.5 ? + H145 C14B H146 . . 109.5 ? + C13B C15B H154 . . 109.5 ? + C13B C15B H155 . . 109.5 ? + H154 C15B H155 . . 109.5 ? + C13B C15B H156 . . 109.5 ? + H154 C15B H156 . . 109.5 ? + H155 C15B H156 . . 109.5 ? + N2 C21 C22 . . 112.8(4) ? + N2 C21 H211 . . 109.0 ? + C22 C21 H211 . . 109.0 ? + N2 C21 H212 . . 109.0 ? + C22 C21 H212 . . 109.0 ? + H211 C21 H212 . . 107.8 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 0.6(6) ? + C2 N1 C1 C11A . . . . -177.8(3) ? + C21 N2 C2 O2 . . . . 1.7(5) ? + C21 N2 C2 N1 . . . . -177.6(3) ? + C1 N1 C2 O2 . . . . -177.8(3) ? + C1 N1 C2 N2 . . . . 1.6(5) ? + O1 C1 C11A C12A . . . . 49.9(5) ? + N1 C1 C11A C12A . . . . -131.7(4) ? + C1 C11A C12A C13A . . . . 78.5(7) ? + C11A C12A C13A C15A . . . . 64.5(11) ? + C11A C12A C13A C14A . . . . -176.3(9) ? + C2 N2 C21 C22 . . . . -84.1(5) ? + C2 N1 C1 C11B . . . . -177.8(3) ? + O1 C1 C11B C12B . . . . 100.4(7) ? + N1 C1 C11B C12B . . . . -81.1(7) ? + C1 C11B C12B C13B . . . . -145.1(10) ? + C11B C12B C13B C15B . . . . -33.4(17) ? + C11B C12B C13B C14B . . . . 88.8(17) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.41 3.100(3) 137.9 + N1 H11 O2 2_566 0.86 2.00 2.855(4) 177.8 +data_ethyl374K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-ethyl-3-(4-methylpentanoyl)urea +; +_chemical_name_common ? +_chemical_formula_moiety 'C9 H18 N2 O2' +_chemical_formula_sum 'C9 H18 N2 O2' +_chemical_formula_weight 186.25 +_chemical_melting_point 375 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 8.6337(14) +_cell_length_b 13.1782(16) +_cell_length_c 5.2242(18) +_cell_angle_alpha 85.948(12) +_cell_angle_beta 91.71(2) +_cell_angle_gamma 88.030(13) +_cell_volume 592.2(2) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 1921 +_cell_measurement_theta_min 1.55 +_cell_measurement_theta_max 27.435 +_cell_measurement_temperature 374 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 1.00 +_exptl_crystal_size_mid 0.60 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.044 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 204 +_exptl_absorpt_coefficient_mu 0.074 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + The crystal was being high temperature phase. +; +_diffrn_ambient_temperature 374 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 8267 +_diffrn_reflns_av_R_equivalents 0.041 +_diffrn_reflns_av_sigmaI/netI 0.0369 +_diffrn_reflns_theta_min 2.36 +_diffrn_reflns_theta_max 27.47 +_diffrn_reflns_theta_full 27.47 +_diffrn_measured_fraction_theta_max 0.724 +_diffrn_measured_fraction_theta_full 0.724 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 11 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 1962 +_reflns_number_gt 826 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.2397 +_refine_ls_R_factor_gt 0.1519 +_refine_ls_wR_factor_gt 0.3442 +_refine_ls_wR_factor_ref 0.3786 +_refine_ls_goodness_of_fit_ref 1.846 +_refine_ls_restrained_S_all 1.846 +_refine_ls_number_reflns 1962 +_refine_ls_number_parameters 131 +_refine_ls_number_restraints 17 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.001 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.220 +_refine_diff_density_min -0.222 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 372K was used as an initial model. + The minor part of the disordered 3-methylbutyl group was + deleted to avoid some viases for disorder analysis. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.4309(4) 0.5705(3) 0.2056(8) 0.1487(15) Uani d . 1 A . O + O2 0.0265(4) 0.4115(2) 0.2684(8) 0.1411(15) Uani d . 1 A . O + N1 0.1966(4) 0.5311(3) 0.3691(9) 0.1209(14) Uani d . 1 A . N + H11 0.1319 0.5483 0.4816 0.145 Uiso calc R 1 . . H + N2 0.2533(4) 0.4162(3) 0.0625(9) 0.1289(16) Uani d D 1 A . N + H21 0.3412 0.4442 0.0446 0.155 Uiso calc R 1 . . H + C1 0.3248(5) 0.5871(3) 0.3521(10) 0.1222(18) Uani d D 1 . . C + C2 0.1557(5) 0.4510(4) 0.2330(11) 0.1156(17) Uani d . 1 . . C + C11A 0.3332(6) 0.6684(3) 0.5374(11) 0.148(2) Uani d PD 0.765(6) A 1 C + H111 0.4093 0.6458 0.6715 0.178 Uiso calc PR 0.765(6) A 1 H + H112 0.2335 0.6734 0.6174 0.178 Uiso calc PR 0.765(6) A 1 H + C12A 0.3736(9) 0.7748(5) 0.435(2) 0.227(5) Uani d PD 0.765(6) A 1 C + H122 0.4541 0.7692 0.3107 0.272 Uiso calc PR 0.765(6) A 1 H + H121 0.4154 0.8108 0.5758 0.272 Uiso calc PR 0.765(6) A 1 H + C13A 0.2368(10) 0.8371(7) 0.309(2) 0.248(7) Uani d PD 0.765(6) A 1 C + H131 0.2004 0.7995 0.1650 0.298 Uiso calc PR 0.765(6) A 1 H + C14A 0.277(2) 0.9430(8) 0.194(3) 0.366(14) Uani d PD 0.765(6) A 1 C + H142 0.3645 0.9369 0.0865 0.549 Uiso calc PR 0.765(6) A 1 H + H141 0.3021 0.9855 0.3304 0.549 Uiso calc PR 0.765(6) A 1 H + H143 0.1898 0.9728 0.0944 0.549 Uiso calc PR 0.765(6) A 1 H + C15A 0.0940(18) 0.8608(14) 0.463(5) 0.396(14) Uani d PD 0.765(6) A 1 C + H153 0.0151 0.8944 0.3507 0.594 Uiso calc PR 0.765(6) A 1 H + H151 0.1215 0.9043 0.5954 0.594 Uiso calc PR 0.765(6) A 1 H + H152 0.0556 0.7985 0.5390 0.594 Uiso calc PR 0.765(6) A 1 H + C11B 0.3332(6) 0.6684(3) 0.5374(11) 0.148(2) Uani d PD 0.235(6) A 2 C + H113 0.4389 0.6904 0.5526 0.178 Uiso calc PR 0.235(6) A 2 H + H114 0.3028 0.6415 0.7054 0.178 Uiso calc PR 0.235(6) A 2 H + C12B 0.2253(14) 0.7593(6) 0.444(3) 0.227(5) Uani d PD 0.235(6) A 2 C + H123 0.2134 0.7607 0.2588 0.272 Uiso calc PR 0.235(6) A 2 H + H124 0.1240 0.7490 0.5149 0.272 Uiso calc PR 0.235(6) A 2 H + C13B 0.2811(16) 0.8627(6) 0.517(2) 0.248(7) Uani d PD 0.235(6) A 2 C + H132 0.1928 0.9117 0.5045 0.298 Uiso calc PR 0.235(6) A 2 H + C14B 0.403(3) 0.900(2) 0.328(4) 0.366(14) Uani d PD 0.235(6) A 2 C + H144 0.4330 0.9665 0.3660 0.549 Uiso calc PR 0.235(6) A 2 H + H145 0.3604 0.9014 0.1562 0.549 Uiso calc PR 0.235(6) A 2 H + H146 0.4923 0.8537 0.3447 0.549 Uiso calc PR 0.235(6) A 2 H + C15B 0.350(4) 0.856(2) 0.791(3) 0.396(14) Uani d PD 0.235(6) A 2 C + H154 0.3691 0.9235 0.8409 0.594 Uiso calc PR 0.235(6) A 2 H + H155 0.4452 0.8164 0.7993 0.594 Uiso calc PR 0.235(6) A 2 H + H156 0.2777 0.8247 0.9059 0.594 Uiso calc PR 0.235(6) A 2 H + C21 0.2164(6) 0.3329(4) -0.0932(10) 0.143(2) Uani d D 1 . . C + H211 0.2718 0.3396 -0.2520 0.172 Uiso calc R 1 A . H + H212 0.1062 0.3359 -0.1364 0.172 Uiso calc R 1 . . H + C22 0.2604(9) 0.2311(4) 0.0485(16) 0.204(4) Uani d D 1 A . C + H223 0.2366 0.1772 -0.0590 0.245 Uiso calc R 1 . . H + H222 0.2031 0.2235 0.2029 0.245 Uiso calc R 1 . . H + H221 0.3695 0.2281 0.0914 0.245 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.102(2) 0.168(3) 0.182(3) -0.029(2) 0.051(2) -0.024(3) + O2 0.094(2) 0.140(3) 0.196(4) -0.0257(18) 0.052(2) -0.027(2) + N1 0.083(2) 0.124(3) 0.160(4) -0.021(2) 0.039(3) -0.018(3) + N2 0.087(2) 0.132(3) 0.173(4) -0.013(2) 0.039(3) -0.026(3) + C1 0.084(3) 0.116(3) 0.165(5) 0.003(3) 0.027(3) 0.007(3) + C2 0.064(2) 0.138(4) 0.142(5) 0.003(3) 0.015(3) 0.010(3) + C11A 0.115(4) 0.119(4) 0.213(6) -0.017(3) 0.030(4) -0.018(4) + C12A 0.187(9) 0.172(7) 0.325(14) -0.015(7) 0.108(11) 0.005(8) + C13A 0.204(11) 0.269(12) 0.248(14) -0.030(10) -0.074(11) 0.118(12) + C14A 0.62(4) 0.131(9) 0.34(2) -0.042(13) -0.03(2) 0.072(10) + C15A 0.181(13) 0.35(2) 0.68(4) 0.033(13) 0.10(2) -0.17(2) + C11B 0.115(4) 0.119(4) 0.213(6) -0.017(3) 0.030(4) -0.018(4) + C12B 0.187(9) 0.172(7) 0.325(14) -0.015(7) 0.108(11) 0.005(8) + C13B 0.204(11) 0.269(12) 0.248(14) -0.030(10) -0.074(11) 0.118(12) + C14B 0.62(4) 0.131(9) 0.34(2) -0.042(13) -0.03(2) 0.072(10) + C15B 0.181(13) 0.35(2) 0.68(4) 0.033(13) 0.10(2) -0.17(2) + C21 0.103(4) 0.149(4) 0.178(6) 0.000(3) 0.037(4) -0.007(4) + C22 0.192(7) 0.147(5) 0.278(10) -0.009(5) 0.043(8) -0.039(6) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.234(6) ? + O2 C2 . 1.261(6) ? + N1 C1 . 1.353(6) ? + N1 C2 . 1.364(7) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.338(6) ? + N2 C21 . 1.450(7) ? + N2 H21 . 0.8600 ? + C1 C11A . 1.496(7) ? + C11A C12A . 1.521(9) ? + C11A H111 . 0.9700 ? + C11A H112 . 0.9700 ? + C11A C12B . 1.53(11) ? + C12A C13A . 1.521(12) ? + C12A H122 . 0.9700 ? + C12A H121 . 0.9700 ? + C13A C15A . 1.53(2) ? + C13A C14A . 1.534(16) ? + C13A H131 . 0.9800 ? + C14A H142 . 0.9600 ? + C14A H141 . 0.9600 ? + C14A H143 . 0.9600 ? + C15A H153 . 0.9600 ? + C15A H151 . 0.9600 ? + C15A H152 . 0.9600 ? + C12B C13B . 1.530(13) ? + C12B H123 . 0.9700 ? + C12B H124 . 0.9700 ? + C13B C15B . 1.53(2) ? + C13B C14B . 1.53(3) ? + C13B H132 . 0.9800 ? + C14B H144 . 0.9600 ? + C14B H145 . 0.9600 ? + C14B H146 . 0.9600 ? + C15B H154 . 0.9600 ? + C15B H155 . 0.9600 ? + C15B H156 . 0.9600 ? + C21 C22 . 1.517(8) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 H223 . 0.9600 ? + C22 H222 . 0.9600 ? + C22 H221 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.1(4) ? + C1 N1 H11 . . 115.5 ? + C2 N1 H11 . . 115.5 ? + C2 N2 C21 . . 122.5(4) ? + C2 N2 H21 . . 118.8 ? + C21 N2 H21 . . 118.8 ? + O1 C1 N1 . . 123.6(4) ? + O1 C1 C11A . . 121.8(4) ? + N1 C1 C11A . . 114.5(4) ? + O2 C2 N2 . . 121.1(6) ? + O2 C2 N1 . . 119.6(4) ? + N2 C2 N1 . . 119.3(4) ? + C1 C11A C12A . . 118.1(6) ? + C1 C11A H111 . . 107.8 ? + C12A C11A H111 . . 107.8 ? + C1 C11A H112 . . 107.8 ? + C12A C11A H112 . . 107.8 ? + H111 C11A H112 . . 107.1 ? + C11A C12A C13A . . 113.9(6) ? + C11A C12A H122 . . 108.8 ? + C13A C12A H122 . . 108.8 ? + C11A C12A H121 . . 108.8 ? + C13A C12A H121 . . 108.8 ? + H122 C12A H121 . . 107.7 ? + C12A C13A C15A . . 120.4(12) ? + C12A C13A C14A . . 114.5(10) ? + C15A C13A C14A . . 102.2(13) ? + C12A C13A H131 . . 106.3 ? + C15A C13A H131 . . 106.3 ? + C14A C13A H131 . . 106.3 ? + C13A C14A H142 . . 109.5 ? + C13A C14A H141 . . 109.5 ? + H142 C14A H141 . . 109.5 ? + C13A C14A H143 . . 109.5 ? + H142 C14A H143 . . 109.5 ? + H141 C14A H143 . . 109.5 ? + C13A C15A H153 . . 109.5 ? + C13A C15A H151 . . 109.5 ? + H153 C15A H151 . . 109.5 ? + C13A C15A H152 . . 109.5 ? + H153 C15A H152 . . 109.5 ? + H151 C15A H152 . . 109.5 ? + C13B C12B H123 . . 108.6 ? + C13B C12B H124 . . 108.6 ? + H123 C12B H124 . . 107.6 ? + C12B C13B C15B . . 111.2(7) ? + C12B C13B C14B . . 109.3(7) ? + C15B C13B C14B . . 109.9(7) ? + C12B C13B H132 . . 108.8 ? + C15B C13B H132 . . 108.8 ? + C14B C13B H132 . . 108.8 ? + C13B C14B H144 . . 109.5 ? + C13B C14B H145 . . 109.5 ? + H144 C14B H145 . . 109.5 ? + C13B C14B H146 . . 109.5 ? + H144 C14B H146 . . 109.5 ? + H145 C14B H146 . . 109.5 ? + C13B C15B H154 . . 109.5 ? + C13B C15B H155 . . 109.5 ? + H154 C15B H155 . . 109.5 ? + C13B C15B H156 . . 109.5 ? + H154 C15B H156 . . 109.5 ? + H155 C15B H156 . . 109.5 ? + N2 C21 C22 . . 110.9(5) ? + N2 C21 H211 . . 109.5 ? + C22 C21 H211 . . 109.5 ? + N2 C21 H212 . . 109.5 ? + C22 C21 H212 . . 109.5 ? + H211 C21 H212 . . 108.0 ? + C21 C22 H223 . . 109.5 ? + C21 C22 H222 . . 109.5 ? + H223 C22 H222 . . 109.5 ? + C21 C22 H221 . . 109.5 ? + H223 C22 H221 . . 109.5 ? + H222 C22 H221 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . -2.0(9) ? + C2 N1 C1 C11A . . . . -178.7(5) ? + C21 N2 C2 O2 . . . . 1.0(7) ? + C21 N2 C2 N1 . . . . -178.6(5) ? + C1 N1 C2 O2 . . . . -176.5(5) ? + C1 N1 C2 N2 . . . . 3.1(8) ? + O1 C1 C11A C12A . . . . 51.0(7) ? + N1 C1 C11A C12A . . . . -132.3(6) ? + C1 C11A C12A C13A . . . . 81.4(10) ? + C11A C12A C13A C15A . . . . 60.1(16) ? + C11A C12A C13A C14A . . . . -177.4(11) ? + C2 N2 C21 C22 . . . . -86.2(6) ? + C2 N1 C1 C11B . . . . -178.7(5) ? + O1 C1 C11B C12B . . . . 106.2(9) ? + N1 C1 C11B C12B . . . . -77.1(8) ? + C1 C11B C12B C13B . . . . -148.3(10) ? + C11B C12B C13B C15B . . . . -40.8(18) ? + C11B C12B C13B C14B . . . . 80.6(18) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N2 H21 O1 2_665 0.86 2.40 3.107(5) 139.2 + N1 H11 O2 2_566 0.86 2.00 2.862(5) 177.5 +data_propyl98K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-(4-methylpentanoyl)-3-propylurea +; +_chemical_name_common ? +_chemical_formula_moiety 'C10 H20 N2 O2' +_chemical_formula_sum 'C10 H20 N2 O2' +_chemical_formula_weight 200.28 +_chemical_melting_point 381 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 9.5437(19) +_cell_length_b 13.205(4) +_cell_length_c 4.8457(13) +_cell_angle_alpha 92.029(14) +_cell_angle_beta 98.767(9) +_cell_angle_gamma 78.875(17) +_cell_volume 592.2(3) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 3224 +_cell_measurement_theta_min 2.45 +_cell_measurement_theta_max 27.48 +_cell_measurement_temperature 98 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.50 +_exptl_crystal_size_mid 0.30 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.123 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 220 +_exptl_absorpt_coefficient_mu 0.078 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + ? +; +_diffrn_ambient_temperature 98 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 6949 +_diffrn_reflns_av_R_equivalents 0.051 +_diffrn_reflns_av_sigmaI/netI 0.0282 +_diffrn_reflns_theta_min 2.20 +_diffrn_reflns_theta_max 27.47 +_diffrn_reflns_theta_full 27.47 +_diffrn_measured_fraction_theta_max 0.797 +_diffrn_measured_fraction_theta_full 0.797 +_diffrn_reflns_limit_h_min -11 +_diffrn_reflns_limit_h_max 12 +_diffrn_reflns_limit_k_min -16 +_diffrn_reflns_limit_k_max 17 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2162 +_reflns_number_gt 1775 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.0772 +_refine_ls_R_factor_gt 0.0619 +_refine_ls_wR_factor_gt 0.1534 +_refine_ls_wR_factor_ref 0.1677 +_refine_ls_goodness_of_fit_ref 1.059 +_refine_ls_restrained_S_all 1.059 +_refine_ls_number_reflns 2162 +_refine_ls_number_parameters 207 +_refine_ls_number_restraints 0 +_refine_ls_hydrogen_treatment refall +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.7784P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens difmap +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.308 +_refine_diff_density_min -0.251 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution 'SIR-97 (Sheldrick, 1990)' +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.11921(18) 0.55649(14) -0.0569(4) 0.0314(4) Uani d . 1 . . O + O2 0.40312(18) 0.41157(13) 0.6112(3) 0.0297(4) Uani d . 1 . . O + N1 0.3321(2) 0.52101(15) 0.2434(4) 0.0245(4) Uani d . 1 . . N + H11 0.422(4) 0.542(2) 0.292(6) 0.042(8) Uiso d . 1 . . H + N2 0.1782(2) 0.41817(16) 0.3633(4) 0.0271(5) Uani d . 1 . . N + H21 0.115(4) 0.445(2) 0.224(7) 0.041(8) Uiso d . 1 . . H + C1 0.2423(2) 0.57155(18) 0.0234(5) 0.0248(5) Uani d . 1 . . C + C2 0.3061(2) 0.44630(17) 0.4180(5) 0.0246(5) Uani d . 1 . . C + C11 0.3039(3) 0.65149(18) -0.1090(5) 0.0252(5) Uani d . 1 . . C + H111 0.414(3) 0.626(2) -0.111(6) 0.042(8) Uiso d . 1 . . H + H112 0.255(3) 0.662(2) -0.304(6) 0.029(7) Uiso d . 1 . . H + C12 0.2811(3) 0.75336(19) 0.0561(5) 0.0296(5) Uani d . 1 . . C + H121 0.336(3) 0.744(2) 0.247(6) 0.034(7) Uiso d . 1 . . H + H122 0.174(4) 0.773(2) 0.079(7) 0.049(9) Uiso d . 1 . . H + C13 0.3259(3) 0.84217(19) -0.0817(6) 0.0318(6) Uani d . 1 . . C + H131 0.268(3) 0.851(2) -0.267(6) 0.037(8) Uiso d . 1 . . H + C14 0.2853(4) 0.9422(2) 0.0804(8) 0.0484(8) Uani d . 1 . . C + H141 0.177(4) 0.960(3) 0.084(7) 0.059(10) Uiso d . 1 . . H + H142 0.308(4) 1.002(3) -0.020(8) 0.064(11) Uiso d . 1 . . H + H143 0.336(4) 0.935(3) 0.277(9) 0.070(11) Uiso d . 1 . . H + C15 0.4853(3) 0.8202(3) -0.1093(8) 0.0471(8) Uani d . 1 . . C + H151 0.512(5) 0.880(3) -0.185(8) 0.079(13) Uiso d . 1 . . H + H152 0.539(4) 0.809(3) 0.077(7) 0.051(10) Uiso d . 1 . . H + H153 0.510(4) 0.755(3) -0.239(7) 0.061(10) Uiso d . 1 . . H + C21 0.1370(3) 0.34246(19) 0.5315(5) 0.0270(5) Uani d . 1 . . C + H211 0.204(3) 0.333(2) 0.707(6) 0.032(7) Uiso d . 1 . . H + H212 0.037(3) 0.369(2) 0.581(6) 0.032(7) Uiso d . 1 . . H + C22 0.1387(3) 0.2395(2) 0.3795(6) 0.0338(6) Uani d . 1 . . C + H221 0.241(4) 0.210(2) 0.341(7) 0.045(8) Uiso d . 1 . . H + H222 0.080(4) 0.252(3) 0.189(7) 0.057(10) Uiso d . 1 . . H + C23 0.0812(4) 0.1644(2) 0.5410(7) 0.0403(7) Uani d . 1 . . C + H231 0.136(4) 0.153(3) 0.729(7) 0.049(9) Uiso d . 1 . . H + H232 0.084(4) 0.096(3) 0.456(7) 0.063(11) Uiso d . 1 . . H + H233 -0.019(4) 0.195(3) 0.572(7) 0.053(10) Uiso d . 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0236(9) 0.0398(10) 0.0299(9) -0.0107(7) -0.0062(7) 0.0047(7) + O2 0.0252(9) 0.0352(9) 0.0268(9) -0.0087(7) -0.0067(7) 0.0045(7) + N1 0.0221(10) 0.0286(10) 0.0233(10) -0.0094(8) -0.0014(8) 0.0010(7) + N2 0.0236(11) 0.0332(11) 0.0244(10) -0.0108(8) -0.0041(8) 0.0038(8) + C1 0.0228(12) 0.0285(12) 0.0220(11) -0.0052(9) 0.0005(9) -0.0030(9) + C2 0.0241(12) 0.0287(11) 0.0207(11) -0.0082(9) -0.0010(9) -0.0036(8) + C11 0.0259(12) 0.0287(11) 0.0209(11) -0.0068(9) 0.0002(9) 0.0006(8) + C12 0.0344(14) 0.0294(12) 0.0263(12) -0.0087(10) 0.0061(10) -0.0019(9) + C13 0.0337(14) 0.0298(13) 0.0320(13) -0.0092(10) 0.0008(11) 0.0021(10) + C14 0.062(2) 0.0305(15) 0.0533(19) -0.0095(14) 0.0100(17) -0.0029(13) + C15 0.0377(17) 0.0450(17) 0.064(2) -0.0187(13) 0.0093(15) 0.0040(15) + C21 0.0249(12) 0.0323(12) 0.0243(11) -0.0099(9) -0.0009(10) 0.0029(9) + C22 0.0367(15) 0.0318(13) 0.0360(14) -0.0095(11) 0.0122(12) -0.0016(10) + C23 0.0489(18) 0.0333(14) 0.0438(17) -0.0143(12) 0.0148(14) -0.0007(12) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.231(3) ? + O2 C2 . 1.244(3) ? + N1 C1 . 1.367(3) ? + N1 C2 . 1.403(3) ? + N1 H11 . 0.95(3) ? + N2 C2 . 1.329(3) ? + N2 C21 . 1.458(3) ? + N2 H21 . 0.87(3) ? + C1 C11 . 1.508(3) ? + C11 C12 . 1.537(3) ? + C11 H111 . 1.04(3) ? + C11 H112 . 0.99(3) ? + C12 C13 . 1.530(3) ? + C12 H121 . 0.99(3) ? + C12 H122 . 1.03(3) ? + C13 C15 . 1.518(4) ? + C13 C14 . 1.528(4) ? + C13 H131 . 0.98(3) ? + C14 H141 . 1.01(4) ? + C14 H142 . 1.02(4) ? + C14 H143 . 1.00(4) ? + C15 H151 . 0.97(4) ? + C15 H152 . 0.97(4) ? + C15 H153 . 1.06(4) ? + C21 C22 . 1.522(4) ? + C21 H211 . 0.98(3) ? + C21 H212 . 1.01(3) ? + C22 C23 . 1.515(4) ? + C22 H221 . 1.03(3) ? + C22 H222 . 1.00(4) ? + C23 H231 . 0.98(3) ? + C23 H232 . 0.98(4) ? + C23 H233 . 1.00(4) ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 128.9(2) ? + C1 N1 H11 . . 116.0(18) ? + C2 N1 H11 . . 115.0(18) ? + C2 N2 C21 . . 122.3(2) ? + C2 N2 H21 . . 120(2) ? + C21 N2 H21 . . 117(2) ? + O1 C1 N1 . . 123.6(2) ? + O1 C1 C11 . . 122.0(2) ? + N1 C1 C11 . . 114.4(2) ? + O2 C2 N2 . . 125.0(2) ? + O2 C2 N1 . . 118.1(2) ? + N2 C2 N1 . . 116.9(2) ? + C1 C11 C12 . . 110.1(2) ? + C1 C11 H111 . . 110.4(17) ? + C12 C11 H111 . . 108.8(17) ? + C1 C11 H112 . . 108.5(15) ? + C12 C11 H112 . . 110.3(16) ? + H111 C11 H112 . . 109(2) ? + C13 C12 C11 . . 113.5(2) ? + C13 C12 H121 . . 108.4(16) ? + C11 C12 H121 . . 110.0(16) ? + C13 C12 H122 . . 109.8(18) ? + C11 C12 H122 . . 108.3(18) ? + H121 C12 H122 . . 107(2) ? + C15 C13 C14 . . 111.3(3) ? + C15 C13 C12 . . 112.3(2) ? + C14 C13 C12 . . 109.7(2) ? + C15 C13 H131 . . 109.7(17) ? + C14 C13 H131 . . 107.0(17) ? + C12 C13 H131 . . 106.6(17) ? + C13 C14 H141 . . 111(2) ? + C13 C14 H142 . . 110(2) ? + H141 C14 H142 . . 105(3) ? + C13 C14 H143 . . 110(2) ? + H141 C14 H143 . . 109(3) ? + H142 C14 H143 . . 113(3) ? + C13 C15 H151 . . 110(3) ? + C13 C15 H152 . . 107(2) ? + H151 C15 H152 . . 108(3) ? + C13 C15 H153 . . 111(2) ? + H151 C15 H153 . . 110(3) ? + H152 C15 H153 . . 111(3) ? + N2 C21 C22 . . 111.7(2) ? + N2 C21 H211 . . 108.6(16) ? + C22 C21 H211 . . 110.1(16) ? + N2 C21 H212 . . 110.0(16) ? + C22 C21 H212 . . 109.3(16) ? + H211 C21 H212 . . 107(2) ? + C23 C22 C21 . . 111.7(2) ? + C23 C22 H221 . . 111.5(17) ? + C21 C22 H221 . . 109.3(17) ? + C23 C22 H222 . . 111(2) ? + C21 C22 H222 . . 109(2) ? + H221 C22 H222 . . 104(3) ? + C22 C23 H231 . . 111.7(19) ? + C22 C23 H232 . . 115(2) ? + H231 C23 H232 . . 106(3) ? + C22 C23 H233 . . 109.7(19) ? + H231 C23 H233 . . 104(3) ? + H232 C23 H233 . . 110(3) ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . -0.7(4) ? + C2 N1 C1 C11 . . . . 177.0(2) ? + C21 N2 C2 O2 . . . . 0.8(4) ? + C21 N2 C2 N1 . . . . -179.1(2) ? + C1 N1 C2 O2 . . . . -178.6(2) ? + C1 N1 C2 N2 . . . . 1.3(4) ? + O1 C1 C11 C12 . . . . 94.6(3) ? + N1 C1 C11 C12 . . . . -83.1(3) ? + C1 C11 C12 C13 . . . . -173.8(2) ? + C11 C12 C13 C15 . . . . -61.3(3) ? + C11 C12 C13 C14 . . . . 174.3(2) ? + C2 N2 C21 C22 . . . . -106.1(3) ? + N2 C21 C22 C23 . . . . -174.1(2) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N1 H11 O2 2_666 0.95(3) 1.88(3) 2.820(3) 178(3) + N2 H21 O1 2_565 0.87(3) 2.26(3) 2.959(3) 137(3) +data_propyl298K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-(4-methylpentanoyl)-3-propylurea +; +_chemical_name_common ? +_chemical_formula_moiety 'C10 H20 N2 O2' +_chemical_formula_sum 'C10 H20 N2 O2' +_chemical_formula_weight 200.28 +_chemical_melting_point 381 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 9.547(4) +_cell_length_b 13.688(6) +_cell_length_c 5.1166(16) +_cell_angle_alpha 90.902(14) +_cell_angle_beta 97.109(8) +_cell_angle_gamma 80.47(2) +_cell_volume 654.3(4) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 3480 +_cell_measurement_theta_min 1.51 +_cell_measurement_theta_max 27.23 +_cell_measurement_temperature 298 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.50 +_exptl_crystal_size_mid 0.30 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.017 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 220 +_exptl_absorpt_coefficient_mu 0.071 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + ? +; +_diffrn_ambient_temperature 298 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 10255 +_diffrn_reflns_av_R_equivalents 0.071 +_diffrn_reflns_av_sigmaI/netI 0.0579 +_diffrn_reflns_theta_min 2.18 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.827 +_diffrn_measured_fraction_theta_full 0.827 +_diffrn_reflns_limit_h_min -12 +_diffrn_reflns_limit_h_max 12 +_diffrn_reflns_limit_k_min -17 +_diffrn_reflns_limit_k_max 17 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 6 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 2485 +_reflns_number_gt 1178 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.1872 +_refine_ls_R_factor_gt 0.1166 +_refine_ls_wR_factor_gt 0.3131 +_refine_ls_wR_factor_ref 0.3767 +_refine_ls_goodness_of_fit_ref 1.972 +_refine_ls_restrained_S_all 1.975 +_refine_ls_number_reflns 2485 +_refine_ls_number_parameters 127 +_refine_ls_number_restraints 6 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens difmap +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.335 +_refine_diff_density_min -0.319 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 98K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.1236(3) 0.5584(3) -0.0332(6) 0.1050(12) Uani d . 1 . . O + O2 0.3975(3) 0.4154(2) 0.5961(6) 0.0975(11) Uani d . 1 . . O + N1 0.3307(3) 0.5232(2) 0.2512(6) 0.0836(11) Uani d . 1 . . N + H11 0.4137 0.5401 0.2863 0.100 Uiso calc R 1 . . H + N2 0.1742(3) 0.4212(3) 0.3621(7) 0.0911(12) Uani d . 1 . . N + H21 0.1154 0.4484 0.2325 0.109 Uiso calc R 1 . . H + C1 0.2437(4) 0.5731(3) 0.0441(8) 0.0811(11) Uani d . 1 . . C + C2 0.3029(4) 0.4485(3) 0.4130(8) 0.0808(11) Uani d . 1 . . C + C11 0.3108(4) 0.6517(3) -0.0726(8) 0.0900(13) Uani d D 1 . . C + H111 0.2751 0.6597 -0.2582 0.108 Uiso calc R 1 . . H + H112 0.4137 0.6310 -0.0575 0.108 Uiso calc R 1 . . H + C12 0.2772(5) 0.7513(3) 0.0675(10) 0.1093(16) Uani d D 1 . . C + H121 0.1747 0.7661 0.0737 0.131 Uiso calc R 1 . . H + H122 0.3230 0.7439 0.2478 0.131 Uiso calc R 1 . . H + C13 0.3234(6) 0.8397(3) -0.0551(13) 0.134(2) Uani d D 1 . . C + H131 0.2810 0.8447 -0.2399 0.160 Uiso calc R 1 . . H + C14 0.2702(10) 0.9370(4) 0.0806(19) 0.217(5) Uani d D 1 . . C + H141 0.1681 0.9456 0.0758 0.261 Uiso calc R 1 . . H + H143 0.2956 0.9914 -0.0094 0.261 Uiso calc R 1 . . H + H142 0.3137 0.9351 0.2604 0.261 Uiso calc R 1 . . H + C15 0.4856(6) 0.8229(6) -0.049(2) 0.209(4) Uani d D 1 . . C + H151 0.5138 0.8783 -0.1293 0.251 Uiso calc R 1 . . H + H152 0.5156 0.7636 -0.1440 0.251 Uiso calc R 1 . . H + H153 0.5297 0.8161 0.1304 0.251 Uiso calc R 1 . . H + C21 0.1313(4) 0.3472(3) 0.5193(8) 0.0930(14) Uani d D 1 . . C + H211 0.0317 0.3671 0.5449 0.112 Uiso calc R 1 . . H + H212 0.1878 0.3433 0.6910 0.112 Uiso calc R 1 . . H + C22 0.1503(6) 0.2446(3) 0.3913(11) 0.1219(18) Uani d D 1 . . C + H221 0.0991 0.2492 0.2148 0.146 Uiso calc R 1 . . H + H222 0.2510 0.2224 0.3769 0.146 Uiso calc R 1 . . H + C23 0.0952(7) 0.1689(4) 0.5501(15) 0.150(2) Uani d D 1 . . C + H232 0.1068 0.1061 0.4624 0.180 Uiso calc R 1 . . H + H231 -0.0043 0.1908 0.5653 0.180 Uiso calc R 1 . . H + H233 0.1485 0.1622 0.7225 0.180 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.0711(15) 0.133(3) 0.109(2) -0.0320(15) -0.0182(15) 0.031(2) + O2 0.0768(16) 0.109(2) 0.104(2) -0.0281(15) -0.0173(16) 0.0273(17) + N1 0.0662(16) 0.100(3) 0.085(2) -0.0257(16) -0.0085(15) 0.0091(18) + N2 0.0703(17) 0.112(3) 0.093(2) -0.0310(17) -0.0100(16) 0.0215(19) + C1 0.0654(17) 0.098(3) 0.080(2) -0.0186(18) -0.0014(17) 0.002(2) + C2 0.0667(19) 0.091(3) 0.085(2) -0.0214(18) -0.0011(19) 0.006(2) + C11 0.087(2) 0.099(3) 0.086(2) -0.019(2) 0.011(2) 0.009(2) + C12 0.111(3) 0.100(4) 0.124(4) -0.023(3) 0.036(3) 0.007(3) + C13 0.147(5) 0.102(4) 0.160(5) -0.031(3) 0.037(4) 0.018(4) + C14 0.271(12) 0.101(5) 0.298(11) -0.032(6) 0.105(10) 0.005(6) + C15 0.153(6) 0.157(6) 0.347(13) -0.075(5) 0.080(8) 0.006(8) + C21 0.080(2) 0.105(3) 0.096(3) -0.027(2) 0.003(2) 0.017(3) + C22 0.122(4) 0.106(4) 0.144(4) -0.024(3) 0.035(4) 0.006(3) + C23 0.165(6) 0.110(4) 0.183(6) -0.029(4) 0.045(5) 0.016(4) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.213(5) ? + O2 C2 . 1.252(4) ? + N1 C1 . 1.377(5) ? + N1 C2 . 1.404(6) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.337(5) ? + N2 C21 . 1.444(6) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.506(6) ? + C11 C12 . 1.534(6) ? + C11 H111 . 0.9700 ? + C11 H112 . 0.9700 ? + C12 C13 . 1.524(7) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.524(8) ? + C13 C14 . 1.532(9) ? + C13 H131 . 0.9800 ? + C14 H141 . 0.9600 ? + C14 H143 . 0.9600 ? + C14 H142 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C21 C22 . 1.533(6) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 C23 . 1.524(9) ? + C22 H221 . 0.9700 ? + C22 H222 . 0.9700 ? + C23 H232 . 0.9600 ? + C23 H231 . 0.9600 ? + C23 H233 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 129.2(3) ? + C1 N1 H11 . . 115.4 ? + C2 N1 H11 . . 115.4 ? + C2 N2 C21 . . 121.7(3) ? + C2 N2 H21 . . 119.2 ? + C21 N2 H21 . . 119.2 ? + O1 C1 N1 . . 124.3(4) ? + O1 C1 C11 . . 122.7(4) ? + N1 C1 C11 . . 112.9(3) ? + O2 C2 N2 . . 125.5(4) ? + O2 C2 N1 . . 118.1(3) ? + N2 C2 N1 . . 116.4(3) ? + C1 C11 C12 . . 111.3(3) ? + C1 C11 H111 . . 109.4 ? + C12 C11 H111 . . 109.4 ? + C1 C11 H112 . . 109.4 ? + C12 C11 H112 . . 109.4 ? + H111 C11 H112 . . 108.0 ? + C13 C12 C11 . . 116.1(4) ? + C13 C12 H121 . . 108.3 ? + C11 C12 H121 . . 108.3 ? + C13 C12 H122 . . 108.3 ? + C11 C12 H122 . . 108.3 ? + H121 C12 H122 . . 107.4 ? + C12 C13 C15 . . 109.9(4) ? + C12 C13 C14 . . 111.9(4) ? + C15 C13 C14 . . 111.1(6) ? + C12 C13 H131 . . 107.9 ? + C15 C13 H131 . . 107.9 ? + C14 C13 H131 . . 107.9 ? + C13 C14 H141 . . 109.5 ? + C13 C14 H143 . . 109.5 ? + H141 C14 H143 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H141 C14 H142 . . 109.5 ? + H143 C14 H142 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H151 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + N2 C21 C22 . . 112.4(3) ? + N2 C21 H211 . . 109.1 ? + C22 C21 H211 . . 109.1 ? + N2 C21 H212 . . 109.1 ? + C22 C21 H212 . . 109.1 ? + H211 C21 H212 . . 107.9 ? + C23 C22 C21 . . 111.7(4) ? + C23 C22 H221 . . 109.3 ? + C21 C22 H221 . . 109.3 ? + C23 C22 H222 . . 109.3 ? + C21 C22 H222 . . 109.3 ? + H221 C22 H222 . . 107.9 ? + C22 C23 H232 . . 109.5 ? + C22 C23 H231 . . 109.5 ? + H232 C23 H231 . . 109.5 ? + C22 C23 H233 . . 109.5 ? + H232 C23 H233 . . 109.5 ? + H231 C23 H233 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . -0.4(7) ? + C2 N1 C1 C11 . . . . 177.4(4) ? + C21 N2 C2 O2 . . . . -0.5(7) ? + C21 N2 C2 N1 . . . . -178.3(4) ? + C1 N1 C2 O2 . . . . -178.0(4) ? + C1 N1 C2 N2 . . . . -0.1(6) ? + O1 C1 C11 C12 . . . . 89.0(5) ? + N1 C1 C11 C12 . . . . -88.8(5) ? + C1 C11 C12 C13 . . . . -172.6(4) ? + C11 C12 C13 C15 . . . . -62.5(8) ? + C11 C12 C13 C14 . . . . 173.6(6) ? + C2 N2 C21 C22 . . . . -98.4(5) ? + N2 C21 C22 C23 . . . . -176.1(5) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N1 H11 O2 2_666 0.86 2.02 2.873(4) 174.2 + N2 H21 O1 2_565 0.86 2.40 3.092(4) 138.2 +data_propyl348K +_audit_creation_method SHELXL-97 +_chemical_name_systematic +; + 1-(4-methylpentanoyl)-3-propylurea +; +_chemical_name_common ? +_chemical_formula_moiety 'C10 H20 N2 O2' +_chemical_formula_sum 'C10 H20 N2 O2' +_chemical_formula_weight 200.28 +_chemical_melting_point 381 +_symmetry_cell_setting 'triclinic' +_symmetry_space_group_name_H-M 'P -1' +loop_ + _symmetry_equiv_pos_as_xyz + 'x, y, z' + '-x, -y, -z' +_cell_length_a 9.405(2) +_cell_length_b 13.3600(19) +_cell_length_c 5.1686(8) +_cell_angle_alpha 93.609(13) +_cell_angle_beta 98.144(12) +_cell_angle_gamma 79.387(10) +_cell_volume 631.46(19) +_cell_formula_units_Z 2 +_cell_measurement_reflns_used 1956 +_cell_measurement_theta_min 2.215 +_cell_measurement_theta_max 25.73 +_cell_measurement_temperature 348 +_exptl_crystal_description 'plate' +_exptl_crystal_colour 'colourless' +_exptl_crystal_size_max 0.50 +_exptl_crystal_size_mid 0.30 +_exptl_crystal_size_min 0.10 +_exptl_crystal_density_diffrn 1.053 +_exptl_crystal_density_meas ? +_exptl_crystal_density_method 'not measured' +_exptl_crystal_F_000 220 +_exptl_absorpt_coefficient_mu 0.073 +_exptl_absorpt_correction_type none +_exptl_absorpt_process_details ? +_exptl_absorpt_correction_T_min ? +_exptl_absorpt_correction_T_max ? +_exptl_special_details +; + ? +; +_diffrn_ambient_temperature 348 +_diffrn_radiation_type MoK\a +_diffrn_radiation_wavelength 0.71073 +_diffrn_radiation_source 'fine-focus sealed tube' +_diffrn_radiation_monochromator graphite +_diffrn_measurement_device 'RIGAKU RAXIS-RAPID' +_diffrn_measurement_method 'Oscillation method' +_diffrn_detector_area_resol_mean 10 +_diffrn_reflns_number 10152 +_diffrn_reflns_av_R_equivalents 0.078 +_diffrn_reflns_av_sigmaI/netI 0.0527 +_diffrn_reflns_theta_min 2.22 +_diffrn_reflns_theta_max 27.48 +_diffrn_reflns_theta_full 27.48 +_diffrn_measured_fraction_theta_max 0.543 +_diffrn_measured_fraction_theta_full 0.543 +_diffrn_reflns_limit_h_min -10 +_diffrn_reflns_limit_h_max 12 +_diffrn_reflns_limit_k_min -13 +_diffrn_reflns_limit_k_max 16 +_diffrn_reflns_limit_l_min -6 +_diffrn_reflns_limit_l_max 5 +_diffrn_standards_number 0 +_diffrn_standards_interval_count none +_diffrn_standards_interval_time ? +_diffrn_standards_decay_% 0 +_refine_special_details +; + Refinement of F^2^ against ALL reflections. The weighted R-factor wR and + goodness of fit S are based on F^2^, conventional R-factors R are based + on F, with F set to zero for negative F^2^. The threshold expression of + F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is + not relevant to the choice of reflections for refinement. R-factors based + on F^2^ are statistically about twice as large as those based on F, and R- + factors based on ALL data will be even larger. +; +_reflns_number_total 1576 +_reflns_number_gt 861 +_reflns_threshold_expression >2\s(I) +_refine_ls_structure_factor_coef Fsqd +_refine_ls_matrix_type full +_refine_ls_R_factor_all 0.2108 +_refine_ls_R_factor_gt 0.1401 +_refine_ls_wR_factor_gt 0.3401 +_refine_ls_wR_factor_ref 0.3910 +_refine_ls_goodness_of_fit_ref 2.045 +_refine_ls_restrained_S_all 2.046 +_refine_ls_number_reflns 1576 +_refine_ls_number_parameters 127 +_refine_ls_number_restraints 6 +_refine_ls_hydrogen_treatment constr +_refine_ls_weighting_scheme calc +_refine_ls_weighting_details + 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' +_atom_sites_solution_hydrogens geom +_atom_sites_solution_primary direct +_atom_sites_solution_secondary difmap +_refine_ls_shift/su_max 0.000 +_refine_ls_shift/su_mean 0.000 +_refine_diff_density_max 0.229 +_refine_diff_density_min -0.183 +_refine_ls_extinction_method none +_refine_ls_extinction_coef ? +loop_ + _atom_type_symbol + _atom_type_description + _atom_type_scat_dispersion_real + _atom_type_scat_dispersion_imag + _atom_type_scat_source + 'C' 'C' 0.0033 0.0016 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'H' 'H' 0.0000 0.0000 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'N' 'N' 0.0061 0.0033 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' + 'O' 'O' 0.0106 0.0060 + 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' +_computing_data_collection 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_cell_refinement 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_data_reduction 'PROCESS-AUTO (Rigaku Corporation, 1998)' +_computing_structure_solution +; + The final structure at 298K was used as an initial model. +; +_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' +_computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' +_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' +loop_ + _atom_site_label + _atom_site_fract_x + _atom_site_fract_y + _atom_site_fract_z + _atom_site_U_iso_or_equiv + _atom_site_adp_type + _atom_site_calc_flag + _atom_site_refinement_flags + _atom_site_occupancy + _atom_site_disorder_assembly + _atom_site_disorder_group + _atom_site_type_symbol + O1 0.1244(5) 0.5604(4) -0.0247(11) 0.123(2) Uani d . 1 . . O + O2 0.3953(5) 0.4151(4) 0.5898(11) 0.118(2) Uani d . 1 . . O + N1 0.3332(5) 0.5239(4) 0.2559(12) 0.0920(18) Uani d . 1 . . N + H11 0.4181 0.5404 0.2946 0.110 Uiso calc R 1 . . H + N2 0.1729(6) 0.4231(4) 0.3557(12) 0.105(2) Uani d . 1 . . N + H21 0.1135 0.4495 0.2256 0.126 Uiso calc R 1 . . H + C1 0.2465(7) 0.5732(5) 0.0567(14) 0.089(2) Uani d . 1 . . C + C2 0.3033(7) 0.4487(5) 0.4096(16) 0.095(2) Uani d . 1 . . C + C11 0.3133(8) 0.6498(5) -0.0617(16) 0.110(2) Uani d D 1 . . C + H111 0.2753 0.6552 -0.2458 0.132 Uiso calc R 1 . . H + H112 0.4183 0.6279 -0.0472 0.132 Uiso calc R 1 . . H + C12 0.2778(9) 0.7532(5) 0.0799(19) 0.138(3) Uani d D 1 . . C + H121 0.3301 0.7499 0.2558 0.166 Uiso calc R 1 . . H + H122 0.1741 0.7682 0.0937 0.166 Uiso calc R 1 . . H + C13 0.3184(12) 0.8392(6) -0.060(2) 0.170(4) Uani d D 1 . . C + H131 0.2765 0.8399 -0.2447 0.204 Uiso calc R 1 . . H + C14 0.267(2) 0.9396(8) 0.084(4) 0.308(11) Uani d D 1 . . C + H141 0.1620 0.9515 0.0729 0.370 Uiso calc R 1 . . H + H142 0.2964 0.9943 0.0063 0.370 Uiso calc R 1 . . H + H143 0.3085 0.9361 0.2648 0.370 Uiso calc R 1 . . H + C15 0.4845(12) 0.8228(9) -0.028(3) 0.266(9) Uani d D 1 . . C + H151 0.5149 0.8774 -0.1057 0.319 Uiso calc R 1 . . H + H152 0.5213 0.7592 -0.1127 0.319 Uiso calc R 1 . . H + H153 0.5220 0.8215 0.1548 0.319 Uiso calc R 1 . . H + C21 0.1277(8) 0.3497(5) 0.5162(16) 0.118(3) Uani d D 1 . . C + H211 0.0241 0.3686 0.5281 0.141 Uiso calc R 1 . . H + H212 0.1800 0.3513 0.6917 0.141 Uiso calc R 1 . . H + C22 0.1598(12) 0.2423(5) 0.393(2) 0.162(4) Uani d D 1 . . C + H221 0.2640 0.2210 0.3921 0.194 Uiso calc R 1 . . H + H222 0.1121 0.2410 0.2142 0.194 Uiso calc R 1 . . H + C23 0.1023(15) 0.1705(7) 0.556(2) 0.192(5) Uani d D 1 . . C + H231 0.1530 0.1702 0.7306 0.231 Uiso calc R 1 . . H + H232 0.1181 0.1028 0.4782 0.231 Uiso calc R 1 . . H + H233 -0.0003 0.1935 0.5604 0.231 Uiso calc R 1 . . H +loop_ + _atom_site_aniso_label + _atom_site_aniso_U_11 + _atom_site_aniso_U_22 + _atom_site_aniso_U_33 + _atom_site_aniso_U_12 + _atom_site_aniso_U_13 + _atom_site_aniso_U_23 + O1 0.079(3) 0.154(5) 0.132(4) -0.029(3) -0.020(3) 0.023(3) + O2 0.090(3) 0.129(4) 0.131(4) -0.038(3) -0.031(3) 0.030(3) + N1 0.068(3) 0.103(4) 0.106(4) -0.030(3) -0.005(3) 0.007(4) + N2 0.079(3) 0.118(4) 0.122(5) -0.039(3) -0.009(3) 0.022(4) + C1 0.068(4) 0.106(5) 0.088(5) -0.014(3) -0.007(4) 0.007(4) + C2 0.067(4) 0.101(5) 0.114(6) -0.024(4) -0.007(4) -0.006(4) + C11 0.102(5) 0.121(6) 0.110(6) -0.028(4) 0.013(5) 0.005(5) + C12 0.121(6) 0.128(7) 0.180(9) -0.039(5) 0.049(6) 0.001(7) + C13 0.173(10) 0.123(7) 0.227(13) -0.043(7) 0.048(9) 0.006(8) + C14 0.39(2) 0.117(9) 0.46(3) -0.067(11) 0.16(2) 0.018(13) + C15 0.194(14) 0.175(11) 0.46(3) -0.078(10) 0.069(16) 0.046(15) + C21 0.081(4) 0.150(7) 0.122(6) -0.037(4) -0.004(4) 0.001(6) + C22 0.195(10) 0.124(7) 0.181(11) -0.063(7) 0.036(9) -0.015(8) + C23 0.255(14) 0.126(7) 0.216(13) -0.063(8) 0.062(11) 0.011(8) +_geom_special_details +; + All esds (except the esd in the dihedral angle between two l.s. planes) + are estimated using the full covariance matrix. The cell esds are taken + into account individually in the estimation of esds in distances, angles + and torsion angles; correlations between esds in cell parameters are only + used when they are defined by crystal symmetry. An approximate (isotropic) + treatment of cell esds is used for estimating esds involving l.s. planes. +; +loop_ + _geom_bond_atom_site_label_1 + _geom_bond_atom_site_label_2 + _geom_bond_site_symmetry_2 + _geom_bond_distance + _geom_bond_publ_flag + O1 C1 . 1.206(8) ? + O2 C2 . 1.224(9) ? + N1 C1 . 1.345(8) ? + N1 C2 . 1.410(10) ? + N1 H11 . 0.8600 ? + N2 C2 . 1.320(9) ? + N2 C21 . 1.479(11) ? + N2 H21 . 0.8600 ? + C1 C11 . 1.496(11) ? + C11 C12 . 1.526(10) ? + C11 H111 . 0.9700 ? + C11 H112 . 0.9700 ? + C12 C13 . 1.528(14) ? + C12 H121 . 0.9700 ? + C12 H122 . 0.9700 ? + C13 C15 . 1.524(15) ? + C13 C14 . 1.526(16) ? + C13 H131 . 0.9800 ? + C14 H141 . 0.9600 ? + C14 H142 . 0.9600 ? + C14 H143 . 0.9600 ? + C15 H151 . 0.9600 ? + C15 H152 . 0.9600 ? + C15 H153 . 0.9600 ? + C21 C22 . 1.528(10) ? + C21 H211 . 0.9700 ? + C21 H212 . 0.9700 ? + C22 C23 . 1.529(17) ? + C22 H221 . 0.9700 ? + C22 H222 . 0.9700 ? + C23 H231 . 0.9600 ? + C23 H232 . 0.9600 ? + C23 H233 . 0.9600 ? +loop_ + _geom_angle_atom_site_label_1 + _geom_angle_atom_site_label_2 + _geom_angle_atom_site_label_3 + _geom_angle_site_symmetry_1 + _geom_angle_site_symmetry_3 + _geom_angle + _geom_angle_publ_flag + C1 N1 C2 . . 128.5(5) ? + C1 N1 H11 . . 115.7 ? + C2 N1 H11 . . 115.7 ? + C2 N2 C21 . . 120.9(7) ? + C2 N2 H21 . . 119.6 ? + C21 N2 H21 . . 119.6 ? + O1 C1 N1 . . 125.1(7) ? + O1 C1 C11 . . 120.6(7) ? + N1 C1 C11 . . 114.3(6) ? + O2 C2 N2 . . 124.4(8) ? + O2 C2 N1 . . 118.8(6) ? + N2 C2 N1 . . 116.8(7) ? + C1 C11 C12 . . 109.5(6) ? + C1 C11 H111 . . 109.8 ? + C12 C11 H111 . . 109.8 ? + C1 C11 H112 . . 109.8 ? + C12 C11 H112 . . 109.8 ? + H111 C11 H112 . . 108.2 ? + C11 C12 C13 . . 112.5(7) ? + C11 C12 H121 . . 109.1 ? + C13 C12 H121 . . 109.1 ? + C11 C12 H122 . . 109.1 ? + C13 C12 H122 . . 109.1 ? + H121 C12 H122 . . 107.8 ? + C15 C13 C14 . . 107.1(11) ? + C15 C13 C12 . . 106.7(7) ? + C14 C13 C12 . . 108.1(7) ? + C15 C13 H131 . . 111.6 ? + C14 C13 H131 . . 111.6 ? + C12 C13 H131 . . 111.6 ? + C13 C14 H141 . . 109.5 ? + C13 C14 H142 . . 109.5 ? + H141 C14 H142 . . 109.5 ? + C13 C14 H143 . . 109.5 ? + H141 C14 H143 . . 109.5 ? + H142 C14 H143 . . 109.5 ? + C13 C15 H151 . . 109.5 ? + C13 C15 H152 . . 109.5 ? + H151 C15 H152 . . 109.5 ? + C13 C15 H153 . . 109.5 ? + H151 C15 H153 . . 109.5 ? + H152 C15 H153 . . 109.5 ? + N2 C21 C22 . . 110.0(6) ? + N2 C21 H211 . . 109.7 ? + C22 C21 H211 . . 109.7 ? + N2 C21 H212 . . 109.7 ? + C22 C21 H212 . . 109.7 ? + H211 C21 H212 . . 108.2 ? + C21 C22 C23 . . 108.0(7) ? + C21 C22 H221 . . 110.1 ? + C23 C22 H221 . . 110.1 ? + C21 C22 H222 . . 110.1 ? + C23 C22 H222 . . 110.1 ? + H221 C22 H222 . . 108.4 ? + C22 C23 H231 . . 109.5 ? + C22 C23 H232 . . 109.5 ? + H231 C23 H232 . . 109.5 ? + C22 C23 H233 . . 109.5 ? + H231 C23 H233 . . 109.5 ? + H232 C23 H233 . . 109.5 ? +loop_ + _geom_torsion_atom_site_label_1 + _geom_torsion_atom_site_label_2 + _geom_torsion_atom_site_label_3 + _geom_torsion_atom_site_label_4 + _geom_torsion_site_symmetry_1 + _geom_torsion_site_symmetry_2 + _geom_torsion_site_symmetry_3 + _geom_torsion_site_symmetry_4 + _geom_torsion + _geom_torsion_publ_flag + C2 N1 C1 O1 . . . . 0.1(11) ? + C2 N1 C1 C11 . . . . 179.4(6) ? + C21 N2 C2 O2 . . . . 0.2(11) ? + C21 N2 C2 N1 . . . . -176.2(6) ? + C1 N1 C2 O2 . . . . -177.4(6) ? + C1 N1 C2 N2 . . . . -0.8(10) ? + O1 C1 C11 C12 . . . . 89.5(9) ? + N1 C1 C11 C12 . . . . -89.8(8) ? + C1 C11 C12 C13 . . . . -169.7(8) ? + C11 C12 C13 C15 . . . . -69.9(11) ? + C11 C12 C13 C14 . . . . 175.2(11) ? + C2 N2 C21 C22 . . . . -93.9(8) ? + N2 C21 C22 C23 . . . . -176.4(8) ? +loop_ + _geom_hbond_atom_site_label_D + _geom_hbond_atom_site_label_H + _geom_hbond_atom_site_label_A + _geom_hbond_site_symmetry_A + _geom_hbond_distance_DH + _geom_hbond_distance_HA + _geom_hbond_distance_DA + _geom_hbond_angle_DHA + N1 H11 O2 2_666 0.86 1.96 2.815(7) 174.8 + N2 H21 O1 2_565 0.86 2.35 3.043(8) 137.5 + debian/changelog0000644000000000000000000000244412146413112011037 0ustar cinfony (1.2-1) unstable; urgency=low * New upstream release. [ Daniel Leidert ] * debian/control: Added XB-Python-Version and Provides fields. (Standards-Version): Bumped to 3.9.4. (DM-Upload-Allowed): Dropped obsolete field. (Build-Depends): Replace python-support by python for dh_python2 transition. (Recommends): Added python-imaging-tk. (Suggests): Added jython and ironpython. * debian/copyright: Added and updated license and copyright information. * debian/rules: Use dh_python2 module. Clean files via dh_clean. * debian/watch: Added. * debian/patches/testsuite_missing_datafiles.patch: Added header. -- Debichem Team Mon, 20 May 2013 14:25:39 +0200 cinfony (1.1-1) unstable; urgency=low * New upstream release (Closes: #674626). * debian/control (Build-Depends): Added libopsin-java. * debian/control (Depends): Added libopsin-java and python-indigo. * debian/control (Description): Updated. * debian/control (Depends): Demote all toolkits to Recommends. * debian/upstream: New file. -- Michael Banck Sun, 27 May 2012 00:16:05 +0200 cinfony (1.0-1) unstable; urgency=low * Initial release (Closes: #647050). -- Michael Banck Sat, 29 Oct 2011 23:43:13 +0200