#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225023.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225023
loop_
_publ_author_name
'Okuniewski, Andrzej'
'Chojnacki, Jaroslaw'
'Becker, Barbara'
_publ_section_title
;
 N-Benzoyl-N'-phenylurea
;
_journal_coeditor_code           IM2175
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o414
_journal_paper_doi               10.1107/S1600536810001807
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 N2 O2'
_chemical_formula_moiety         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_chemical_melting_point          482(2)
_chemical_name_systematic
;
N-Benzoyl-N'-phenylurea
;
_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_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 128.716(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5641(8)
_cell_length_b                   4.6564(3)
_cell_length_c                   21.1029(15)
_cell_measurement_reflns_used    2481
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3943
_cell_measurement_theta_min      2.47
_cell_volume                     1193.31(15)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.1883
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a
Sapphire2 (large Be window) detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Mo K\a radiation'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4425
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis Pro (Oxford Diffraction, 2009); analytical numeric absorption
correction using a multi-faceted crystal model based on expressions derived
by Clark & Reid (1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.5366
_exptl_crystal_size_mid          0.1027
_exptl_crystal_size_min          0.0901
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                1575
_reflns_number_total             2221
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2175.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225023
_cod_database_fobs_code          2225023
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_type_symbol
_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
O O1 0.58625(7) 0.6582(2) -0.00745(6) 0.0384(3) Uani d . 1 . .
O O2 0.82393(7) 0.2951(2) 0.21526(6) 0.0396(3) Uani d . 1 . .
N N1 0.77093(9) 0.6517(3) 0.09887(7) 0.0295(3) Uani d . 1 . .
N N2 0.64890(9) 0.3566(3) 0.09771(7) 0.0284(3) Uani d . 1 . .
C C1 0.66640(10) 0.5660(3) 0.05886(8) 0.0274(3) Uani d . 1 . .
C C2 0.72519(10) 0.2381(3) 0.17319(8) 0.0282(3) Uani d . 1 . .
C C11 0.81196(11) 0.8530(3) 0.07373(9) 0.0297(4) Uani d . 1 . .
C C12 0.74750(12) 0.9966(3) -0.00011(9) 0.0330(4) Uani d . 1 . .
C C13 0.79673(13) 1.1897(4) -0.01876(10) 0.0393(4) Uani d . 1 . .
C C14 0.90876(14) 1.2390(4) 0.03479(11) 0.0469(5) Uani d . 1 . .
C C15 0.97228(13) 1.0949(4) 0.10784(12) 0.0516(5) Uani d . 1 . .
C C16 0.92476(12) 0.9038(4) 0.12780(11) 0.0411(4) Uani d . 1 . .
C C21 0.68355(10) 0.0351(3) 0.20329(8) 0.0275(3) Uani d . 1 . .
C C22 0.75435(12) -0.0253(3) 0.28626(9) 0.0336(4) Uani d . 1 . .
C C23 0.72257(13) -0.2128(4) 0.31894(10) 0.0389(4) Uani d . 1 . .
C C24 0.61969(13) -0.3423(4) 0.26921(10) 0.0390(4) Uani d . 1 . .
C C25 0.54898(12) -0.2851(3) 0.18661(10) 0.0368(4) Uani d . 1 . .
C C26 0.58046(11) -0.0960(3) 0.15362(9) 0.0316(4) Uani d . 1 . .
H H1 0.8205(12) 0.559(3) 0.1480(10) 0.039(4) Uiso d . 1 . .
H H13 0.7502(12) 1.291(4) -0.0711(10) 0.041(4) Uiso d . 1 . .
H H12 0.6663(12) 0.961(3) -0.0395(8) 0.032(4) Uiso d . 1 . .
H H2 0.5745(13) 0.328(3) 0.0717(9) 0.041(4) Uiso d . 1 . .
H H23 0.7751(12) -0.257(3) 0.3782(10) 0.040(4) Uiso d . 1 . .
H H26 0.5289(12) -0.059(3) 0.0951(9) 0.032(4) Uiso d . 1 . .
H H22 0.8256(13) 0.077(4) 0.3210(9) 0.044(4) Uiso d . 1 . .
H H25 0.4762(13) -0.375(3) 0.1504(9) 0.043(4) Uiso d . 1 . .
H H24 0.5963(12) -0.477(4) 0.2916(9) 0.043(4) Uiso d . 1 . .
H H14 0.9397(13) 1.385(4) 0.0187(10) 0.056(5) Uiso d . 1 . .
H H15 1.0520(15) 1.117(4) 0.1465(10) 0.060(5) Uiso d . 1 . .
H H16 0.9654(14) 0.800(4) 0.1778(11) 0.055(5) Uiso d . 1 . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -6 4 0.2387
-2 6 -4 0.2637
-11 0 -18 0.081
-18 0 15 0.0428
16 0 -18 0.0576
12 0 18 0.0076
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 C11 . . 128.07(12) ?
C1 N1 H1 . . 113.5(9) ?
C11 N1 H1 . . 118.4(9) ?
C2 N2 C1 . . 127.79(11) ?
C2 N2 H2 . . 118.7(9) ?
C1 N2 H2 . . 112.3(10) ?
O1 C1 N1 . . 125.41(14) ?
O1 C1 N2 . . 118.47(11) ?
N1 C1 N2 . . 116.12(12) ?
O2 C2 N2 . . 122.27(13) ?
O2 C2 C21 . . 120.53(12) ?
N2 C2 C21 . . 117.20(12) ?
C12 C11 C16 . . 119.63(14) ?
C12 C11 N1 . . 124.25(12) ?
C16 C11 N1 . . 116.12(13) ?
C11 C12 C13 . . 119.38(14) ?
C11 C12 H12 . . 120.2(8) ?
C13 C12 H12 . . 120.4(8) ?
C14 C13 C12 . . 120.96(16) ?
C14 C13 H13 . . 120.3(9) ?
C12 C13 H13 . . 118.7(9) ?
C15 C14 C13 . . 119.33(16) ?
C15 C14 H14 . . 123.1(10) ?
C13 C14 H14 . . 117.5(10) ?
C14 C15 C16 . . 120.59(15) ?
C14 C15 H15 . . 122.2(10) ?
C16 C15 H15 . . 117.2(11) ?
C15 C16 C11 . . 120.10(16) ?
C15 C16 H16 . . 123.5(10) ?
C11 C16 H16 . . 116.4(10) ?
C26 C21 C22 . . 119.31(14) ?
C26 C21 C2 . . 123.99(13) ?
C22 C21 C2 . . 116.69(13) ?
C23 C22 C21 . . 120.37(14) ?
C23 C22 H22 . . 121.3(9) ?
C21 C22 H22 . . 118.3(9) ?
C22 C23 C24 . . 120.06(15) ?
C22 C23 H23 . . 119.3(9) ?
C24 C23 H23 . . 120.7(9) ?
C25 C24 C23 . . 120.03(15) ?
C25 C24 H24 . . 119.1(9) ?
C23 C24 H24 . . 120.9(9) ?
C24 C25 C26 . . 120.07(15) ?
C24 C25 H25 . . 121.3(9) ?
C26 C25 H25 . . 118.6(9) ?
C25 C26 C21 . . 120.16(14) ?
C25 C26 H26 . . 118.5(9) ?
C21 C26 H26 . . 121.4(9) ?
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 . 1.2308(16) ?
O2 C2 . 1.2304(15) ?
N1 C1 . 1.3419(16) ?
N1 C11 . 1.4114(18) ?
N1 H1 . 0.926(16) ?
N2 C2 . 1.3731(18) ?
N2 C1 . 1.4058(18) ?
N2 H2 . 0.930(15) ?
C2 C21 . 1.494(2) ?
C11 C12 . 1.388(2) ?
C11 C16 . 1.3907(19) ?
C12 C13 . 1.388(2) ?
C12 H12 . 1.001(14) ?
C13 C14 . 1.380(2) ?
C13 H13 . 0.984(17) ?
C14 C15 . 1.378(3) ?
C14 H14 . 1.007(19) ?
C15 C16 . 1.381(2) ?
C15 H15 . 0.975(18) ?
C16 H16 . 0.956(19) ?
C21 C26 . 1.394(2) ?
C21 C22 . 1.3950(19) ?
C22 C23 . 1.382(2) ?
C22 H22 . 0.988(16) ?
C23 C24 . 1.388(2) ?
C23 H23 . 0.998(16) ?
C24 C25 . 1.386(2) ?
C24 H24 . 0.983(17) ?
C25 C26 . 1.388(2) ?
C25 H25 . 0.980(16) ?
C26 H26 . 0.979(15) ?
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 H1 O2 . 0.93(2) 1.85(2) 2.634(2) 140.0(10)
N2 H2 O1 3_665 0.93(2) 1.97(2) 2.8820(10) 169.0(10)
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
N1 C1 N2 C2 . . . . 3.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67144
