#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/69/2206932.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_2206932
loop_
_publ_author_name
'Su, Bi-Quan'
_publ_section_title
;
 N-(4-Chlorophenyl)-N'-(4-nitrobenzoyl)urea
;
_journal_coeditor_code           CV6577
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3492
_journal_page_last               o3494
_journal_paper_doi               10.1107/S160053680503076X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H10 Cl N3 O4'
_chemical_formula_moiety         'C14 H10 Cl N3 O4'
_chemical_formula_sum            'C14 H10 Cl N3 O4'
_chemical_formula_weight         319.70
_chemical_name_systematic
;
N-(4-Chlorophenyl)-N'-(4-nitrobenzoyl)urea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.418(2)
_cell_angle_beta                 106.157(2)
_cell_angle_gamma                99.400(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1737(10)
_cell_length_b                   8.2486(12)
_cell_length_c                   12.1873(17)
_cell_measurement_reflns_used    1727
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.51
_cell_volume                     681.50(17)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3693
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0326
_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)+(0.0423P)²+0.161P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                1941
_reflns_number_total             2368
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6577.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206932
_cod_database_fobs_code          2206932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
Cl1 1.28679(9) -0.00089(7) 0.27008(5) 0.0716(2) Uani d . 1 Cl
N1 0.9143(2) 0.32409(17) 0.56999(12) 0.0412(3) Uani d D 1 N
H1 0.984(2) 0.337(2) 0.6415(9) 0.050(5) Uiso d D 1 H
N2 0.70475(19) 0.46082(17) 0.63786(11) 0.0395(3) Uani d D 1 N
H2 0.5996(18) 0.5037(19) 0.6185(14) 0.044(5) Uiso d D 1 H
N3 0.5108(2) 0.8111(2) 1.06294(14) 0.0567(4) Uani d . 1 N
O1 0.64018(16) 0.39301(16) 0.44858(9) 0.0496(3) Uani d . 1 O
O2 0.97614(18) 0.44473(16) 0.78491(10) 0.0534(3) Uani d . 1 O
O3 0.3401(2) 0.8288(2) 1.03227(15) 0.0918(6) Uani d . 1 O
O4 0.6206(3) 0.8557(2) 1.15750(13) 0.0884(5) Uani d . 1 O
C1 0.7506(2) 0.39051(19) 0.54468(14) 0.0367(4) Uani d . 1 C
C2 0.8153(2) 0.4858(2) 0.74984(14) 0.0399(4) Uani d . 1 C
C3 0.9940(2) 0.24722(19) 0.49319(14) 0.0377(4) Uani d . 1 C
C4 1.1752(2) 0.2006(2) 0.54013(15) 0.0436(4) Uani d . 1 C
H4 1.2364 0.2206 0.6184 0.052 Uiso calc R 1 H
C5 1.2654(3) 0.1254(2) 0.47245(17) 0.0494(4) Uani d . 1 C
H5 1.3874 0.0954 0.5045 0.059 Uiso calc R 1 H
C6 1.1737(3) 0.0946(2) 0.35684(16) 0.0488(4) Uani d . 1 C
C7 0.9928(3) 0.1375(2) 0.30907(16) 0.0490(4) Uani d . 1 C
H7 0.9313 0.1149 0.2310 0.059 Uiso calc R 1 H
C8 0.9018(3) 0.2141(2) 0.37664(15) 0.0452(4) Uani d . 1 C
H8 0.7795 0.2432 0.3442 0.054 Uiso calc R 1 H
C9 0.7284(2) 0.5695(2) 0.82916(13) 0.0385(4) Uani d . 1 C
C10 0.8574(2) 0.6555(2) 0.92800(14) 0.0466(4) Uani d . 1 C
H10 0.9923 0.6585 0.9426 0.056 Uiso calc R 1 H
C11 0.7882(3) 0.7360(2) 1.00432(15) 0.0481(4) Uani d . 1 C
H11 0.8744 0.7947 1.0700 0.058 Uiso calc R 1 H
C12 0.5877(3) 0.7274(2) 0.98081(14) 0.0423(4) Uani d . 1 C
C13 0.4555(2) 0.6416(2) 0.88505(14) 0.0456(4) Uani d . 1 C
H13 0.3206 0.6373 0.8718 0.055 Uiso calc R 1 H
C14 0.5269(2) 0.5619(2) 0.80906(14) 0.0433(4) Uani d . 1 C
H14 0.4396 0.5028 0.7439 0.052 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C1 N1 C3 127.58(14) y
C1 N1 H1 115.7(12) ?
C3 N1 H1 116.5(12) ?
C2 N2 C1 128.49(13) y
C2 N2 H2 117.3(12) ?
C1 N2 H2 113.7(12) ?
O4 N3 O3 123.72(17) ?
O4 N3 C12 118.26(17) ?
O3 N3 C12 118.01(16) ?
O1 C1 N1 125.27(15) ?
O1 C1 N2 118.64(14) ?
N1 C1 N2 116.09(14) y
O2 C2 N2 123.12(15) ?
O2 C2 C9 120.95(15) ?
N2 C2 C9 115.93(14) y
C4 C3 C8 119.24(15) ?
C4 C3 N1 116.38(15) ?
C8 C3 N1 124.37(15) ?
C5 C4 C3 120.81(17) ?
C5 C4 H4 119.6 ?
C3 C4 H4 119.6 ?
C4 C5 C6 119.46(16) ?
C4 C5 H5 120.3 ?
C6 C5 H5 120.3 ?
C7 C6 C5 120.58(16) ?
C7 C6 Cl1 119.56(15) ?
C5 C6 Cl1 119.86(14) ?
C6 C7 C8 120.21(17) ?
C6 C7 H7 119.9 ?
C8 C7 H7 119.9 ?
C7 C8 C3 119.68(16) ?
C7 C8 H8 120.2 ?
C3 C8 H8 120.2 ?
C14 C9 C10 119.38(15) ?
C14 C9 C2 122.93(15) ?
C10 C9 C2 117.68(15) ?
C11 C10 C9 120.85(16) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C10 C11 C12 118.09(16) ?
C10 C11 H11 121.0 ?
C12 C11 H11 121.0 ?
C13 C12 C11 122.74(15) ?
C13 C12 N3 118.50(15) ?
C11 C12 N3 118.74(15) ?
C12 C13 C14 118.57(15) ?
C12 C13 H13 120.7 ?
C14 C13 H13 120.7 ?
C13 C14 C9 120.35(15) ?
C13 C14 H14 119.8 ?
C9 C14 H14 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 1.7442(17) ?
N1 C1 1.338(2) y
N1 C3 1.412(2) y
N1 H1 0.871(9) ?
N2 C2 1.365(2) y
N2 C1 1.404(2) y
N2 H2 0.861(9) ?
N3 O4 1.210(2) ?
N3 O3 1.212(2) ?
N3 C12 1.477(2) ?
O1 C1 1.2207(19) y
O2 C2 1.2204(19) y
C2 C9 1.498(2) y
C3 C4 1.387(2) ?
C3 C8 1.389(2) ?
C4 C5 1.374(2) ?
C4 H4 0.9300 ?
C5 C6 1.376(3) ?
C5 H5 0.9300 ?
C6 C7 1.374(3) ?
C7 C8 1.382(2) ?
C7 H7 0.9300 ?
C8 H8 0.9300 ?
C9 C14 1.388(2) ?
C9 C10 1.391(2) ?
C10 C11 1.374(2) ?
C10 H10 0.9300 ?
C11 C12 1.375(2) ?
C11 H11 0.9300 ?
C12 C13 1.374(2) ?
C13 C14 1.376(2) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
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 . 0.871(9) 1.959(14) 2.6699(18) 137.9(16)
C8 H8 O1 . 0.93 2.275 2.868(2) 121
N2 H2 O1 2_666 0.861(9) 2.021(10) 2.8763(17) 172.0(17)
C10 H10 O3 1_655 0.93 2.579 3.390(2) 146
C14 H14 O1 2_666 0.93 2.466 3.089(2) 124
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
C3 N1 C1 O1 1.1(3)
C3 N1 C1 N2 -179.51(15)
C2 N2 C1 O1 -173.13(16)
C2 N2 C1 N1 7.4(3)
C1 N2 C2 O2 -1.4(3)
C1 N2 C2 C9 178.00(15)
C1 N1 C3 C4 174.64(16)
C1 N1 C3 C8 -6.5(3)
C8 C3 C4 C5 1.3(3)
N1 C3 C4 C5 -179.81(15)
C3 C4 C5 C6 -0.6(3)
C4 C5 C6 C7 -0.4(3)
C4 C5 C6 Cl1 180.00(13)
C5 C6 C7 C8 0.8(3)
Cl1 C6 C7 C8 -179.65(14)
C6 C7 C8 C3 -0.1(3)
C4 C3 C8 C7 -0.9(3)
N1 C3 C8 C7 -179.74(16)
O2 C2 C9 C14 -154.16(17)
N2 C2 C9 C14 26.5(2)
O2 C2 C9 C10 24.6(3)
N2 C2 C9 C10 -154.76(15)
C14 C9 C10 C11 -1.5(3)
C2 C9 C10 C11 179.64(16)
C9 C10 C11 C12 0.8(3)
C10 C11 C12 C13 0.3(3)
C10 C11 C12 N3 179.05(16)
O4 N3 C12 C13 164.33(18)
O3 N3 C12 C13 -14.5(3)
O4 N3 C12 C11 -14.5(3)
O3 N3 C12 C11 166.71(19)
C11 C12 C13 C14 -0.5(3)
N3 C12 C13 C14 -179.30(16)
C12 C13 C14 C9 -0.3(3)
C10 C9 C14 C13 1.3(3)
C2 C9 C14 C13 -179.96(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128820
2 PubChem 71412019
