#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:13:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178426 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024798.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024798
loop_
_publ_author_name
'Guillaume Lessene'
'Brian J. Smith'
'Robert W. Gable'
'Jonathan B. Baell'
_publ_section_title
;
Characterization of the Two Fundamental Conformations of Benzoylureas and
Elucidation of the Factors That Facilitate Their Conformational Interchange
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6511
_journal_page_last               6525
_journal_paper_doi               10.1021/jo900871a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C19 H22 N2 O2'
_chemical_formula_sum            'C19 H22 N2 O2'
_chemical_formula_weight         310.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.426(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4300(8)
_cell_length_b                   19.336(2)
_cell_length_c                   8.9636(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      19.2
_cell_volume                     1715.1(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'PROCESS_DATA (Gable et al. 1993)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4MachS diffractometer'
_diffrn_measurement_method       ω:2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4487
_diffrn_reflns_theta_full        74.95
_diffrn_reflns_theta_max         74.95
_diffrn_reflns_theta_min         4.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0616P)²+0.1078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                1988
_reflns_number_total             3530
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo900871a_si_003.cif
_cod_data_source_block           jb_23
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21 /c'
_cod_database_code               4024798
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1232(2) 0.30636(11) 0.3977(3) 0.0434(5) Uani 1 1 d . . .
C2 C 0.1144(2) 0.37089(12) 0.3272(3) 0.0540(6) Uani 1 1 d . . .
H2 H 0.1680 0.3810 0.2645 0.052(6) Uiso 1 1 calc R . .
C3 C 0.0263(3) 0.41999(14) 0.3499(3) 0.0668(7) Uani 1 1 d . . .
H3 H 0.0205 0.4630 0.3018 0.086(9) Uiso 1 1 calc R . .
C4 C -0.0519(3) 0.40606(15) 0.4420(4) 0.0749(8) Uani 1 1 d . . .
H4 H -0.1108 0.4394 0.4573 0.080(8) Uiso 1 1 calc R . .
C5 C -0.0434(3) 0.34267(14) 0.5120(4) 0.0755(8) Uani 1 1 d . . .
H5 H -0.0969 0.3332 0.5752 0.083(9) Uiso 1 1 calc R . .
C6 C 0.0438(2) 0.29236(13) 0.4903(3) 0.0610(7) Uani 1 1 d . . .
H6 H 0.0484 0.2494 0.5382 0.064(8) Uiso 1 1 calc R . .
N1 N 0.21894(18) 0.25995(9) 0.3710(2) 0.0457(5) Uani 1 1 d . . .
H1N H 0.274(2) 0.2762(13) 0.313(3) 0.063(7) Uiso 1 1 d . . .
C7 C 0.2450(2) 0.19508(11) 0.4278(3) 0.0459(5) Uani 1 1 d . . .
O1 O 0.18334(16) 0.16528(8) 0.5018(2) 0.0667(5) Uani 1 1 d . . .
N2 N 0.35632(16) 0.16121(8) 0.3966(2) 0.0421(4) Uani 1 1 d . . .
C8 C 0.3787(2) 0.08721(10) 0.4505(3) 0.0517(6) Uani 1 1 d . . .
H8 H 0.4529 0.0702 0.4155 0.036(5) Uiso 1 1 calc R . .
C9 C 0.2572(3) 0.04197(14) 0.3690(4) 0.0850(10) Uani 1 1 d . . .
H9A H 0.1854 0.0515 0.4116 0.114(7) Uiso 1 1 calc R . .
H9B H 0.2824 -0.0059 0.3856 0.114(7) Uiso 1 1 calc R . .
H9C H 0.2272 0.0517 0.2583 0.114(7) Uiso 1 1 calc R . .
C10 C 0.4262(3) 0.08004(14) 0.6278(3) 0.0726(8) Uani 1 1 d . . .
H10A H 0.5073 0.1066 0.6715 0.130(8) Uiso 1 1 calc R . .
H10B H 0.4442 0.0323 0.6557 0.130(8) Uiso 1 1 calc R . .
H10C H 0.3573 0.0968 0.6687 0.130(8) Uiso 1 1 calc R . .
O2 O 0.42485(16) 0.24972(8) 0.2710(2) 0.0667(5) Uani 1 1 d . . .
C11 C 0.4442(2) 0.19187(10) 0.3307(3) 0.0436(5) Uani 1 1 d . . .
C12 C 0.5728(2) 0.15522(10) 0.3368(3) 0.0435(5) Uani 1 1 d . . .
C13 C 0.5783(2) 0.11385(11) 0.2115(3) 0.0509(6) Uani 1 1 d . . .
C14 C 0.7015(3) 0.08548(14) 0.2162(4) 0.0678(8) Uani 1 1 d . . .
H14 H 0.7066 0.0571 0.1346 0.076(9) Uiso 1 1 calc R . .
C15 C 0.8158(3) 0.09874(15) 0.3396(5) 0.0786(9) Uani 1 1 d . . .
H15 H 0.8980 0.0795 0.3411 0.083(8) Uiso 1 1 calc R . .
C16 C 0.8091(2) 0.14012(15) 0.4598(4) 0.0719(8) Uani 1 1 d . . .
H16 H 0.8875 0.1488 0.5428 0.092(10) Uiso 1 1 calc R . .
C17 C 0.6884(2) 0.16976(12) 0.4620(3) 0.0554(6) Uani 1 1 d . . .
C18 C 0.4532(3) 0.09996(16) 0.0739(3) 0.0800(9) Uani 1 1 d . . .
H18A H 0.4790 0.0823 -0.0126 0.079(8) Uiso 0.51(3) 1 calc PR . .
H18B H 0.4034 0.1422 0.0431 0.079(8) Uiso 0.51(3) 1 calc PR . .
H18C H 0.3977 0.0665 0.1038 0.079(8) Uiso 0.51(3) 1 calc PR . .
H18D H 0.3744 0.1117 0.1021 0.079(8) Uiso 0.49(3) 1 calc PR . .
H18E H 0.4500 0.0519 0.0464 0.079(8) Uiso 0.49(3) 1 calc PR . .
H18F H 0.4557 0.1275 -0.0143 0.079(8) Uiso 0.49(3) 1 calc PR . .
C19 C 0.6850(3) 0.21726(17) 0.5933(4) 0.0887(10) Uani 1 1 d . . .
H19A H 0.6069 0.2071 0.6242 0.080(8) Uiso 0.65(3) 1 calc PR . .
H19B H 0.6807 0.2644 0.5582 0.080(8) Uiso 0.65(3) 1 calc PR . .
H19C H 0.7651 0.2107 0.6814 0.080(8) Uiso 0.65(3) 1 calc PR . .
H19D H 0.7616 0.2477 0.6183 0.080(8) Uiso 0.35(3) 1 calc PR . .
H19E H 0.6878 0.1904 0.6843 0.080(8) Uiso 0.35(3) 1 calc PR . .
H19F H 0.6034 0.2441 0.5611 0.080(8) Uiso 0.35(3) 1 calc PR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.1(2) . . ?
C6 C1 N1 124.7(2) . . ?
C2 C1 N1 116.1(2) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C7 N1 C1 126.39(19) . . ?
C7 N1 H1N 115.6(15) . . ?
C1 N1 H1N 117.9(15) . . ?
O1 C7 N1 125.0(2) . . ?
O1 C7 N2 119.60(19) . . ?
N1 C7 N2 115.42(19) . . ?
C11 N2 C7 125.34(16) . . ?
C11 N2 C8 119.50(16) . . ?
C7 N2 C8 115.08(16) . . ?
N2 C8 C10 112.97(19) . . ?
N2 C8 C9 111.8(2) . . ?
C10 C8 C9 113.4(2) . . ?
N2 C8 H8 106.0 . . ?
C10 C8 H8 106.0 . . ?
C9 C8 H8 106.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N2 122.71(18) . . ?
O2 C11 C12 117.86(18) . . ?
N2 C11 C12 119.37(17) . . ?
C17 C12 C13 121.3(2) . . ?
C17 C12 C11 118.0(2) . . ?
C13 C12 C11 120.3(2) . . ?
C14 C13 C12 118.4(2) . . ?
C14 C13 C18 120.5(2) . . ?
C12 C13 C18 121.0(2) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C12 117.6(2) . . ?
C16 C17 C19 120.6(3) . . ?
C12 C17 C19 121.8(2) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C13 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C13 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C19 H19D 109.5 . . ?
H19A C19 H19D 141.1 . . ?
H19B C19 H19D 56.3 . . ?
H19C C19 H19D 56.3 . . ?
C17 C19 H19E 109.5 . . ?
H19A C19 H19E 56.3 . . ?
H19B C19 H19E 141.1 . . ?
H19C C19 H19E 56.3 . . ?
H19D C19 H19E 109.5 . . ?
C17 C19 H19F 109.5 . . ?
H19A C19 H19F 56.3 . . ?
H19B C19 H19F 56.3 . . ?
H19C C19 H19F 141.1 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.372(3) . ?
C1 C2 1.389(3) . ?
C1 N1 1.418(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C7 1.349(3) . ?
N1 H1N 0.94(2) . ?
C7 O1 1.206(2) . ?
C7 N2 1.436(2) . ?
N2 C11 1.372(2) . ?
N2 C8 1.505(2) . ?
C8 C10 1.514(4) . ?
C8 C9 1.523(3) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O2 C11 1.229(2) . ?
C11 C12 1.502(3) . ?
C12 C17 1.392(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.386(3) . ?
C13 C18 1.509(4) . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C19 1.502(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18D 0.9600 . ?
C18 H18E 0.9600 . ?
C18 H18F 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19D 0.9600 . ?
C19 H19E 0.9600 . ?
C19 H19F 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.94(2) 1.80(2) 2.583(2) 138(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(4) . . . . ?
N1 C1 C2 C3 -178.4(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
N1 C1 C6 C5 177.9(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C6 C1 N1 C7 1.7(4) . . . . ?
C2 C1 N1 C7 179.8(2) . . . . ?
C1 N1 C7 O1 5.3(4) . . . . ?
C1 N1 C7 N2 -173.95(19) . . . . ?
O1 C7 N2 C11 -171.8(2) . . . . ?
N1 C7 N2 C11 7.4(3) . . . . ?
O1 C7 N2 C8 4.8(3) . . . . ?
N1 C7 N2 C8 -175.97(19) . . . . ?
C11 N2 C8 C10 108.7(2) . . . . ?
C7 N2 C8 C10 -68.1(3) . . . . ?
C11 N2 C8 C9 -121.9(2) . . . . ?
C7 N2 C8 C9 61.3(3) . . . . ?
C7 N2 C11 O2 -10.6(3) . . . . ?
C8 N2 C11 O2 173.0(2) . . . . ?
C7 N2 C11 C12 166.8(2) . . . . ?
C8 N2 C11 C12 -9.7(3) . . . . ?
O2 C11 C12 C17 84.8(3) . . . . ?
N2 C11 C12 C17 -92.7(2) . . . . ?
O2 C11 C12 C13 -88.4(3) . . . . ?
N2 C11 C12 C13 94.1(3) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C11 C12 C13 C14 174.9(2) . . . . ?
C17 C12 C13 C18 -178.2(2) . . . . ?
C11 C12 C13 C18 -5.3(3) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C18 C13 C14 C15 179.0(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C12 0.6(4) . . . . ?
C15 C16 C17 C19 -177.7(3) . . . . ?
C13 C12 C17 C16 -1.6(3) . . . . ?
C11 C12 C17 C16 -174.7(2) . . . . ?
C13 C12 C17 C19 176.7(2) . . . . ?
C11 C12 C17 C19 3.6(3) . . . . ?
