#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222756.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_2222756
loop_
_publ_author_name
'Saeed, Sohail'
'Rashid, Naghmana'
'Tahir, Arifa'
'Jones, Peter G.'
_publ_section_title
;
 1-(4-Bromophenyl)-1-(4-nitrobenzoyl)thiourea
;
_journal_coeditor_code           IM2125
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1870
_journal_page_last               o1871
_journal_paper_doi               10.1107/S1600536809025884
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 Br N3 O3 S'
_chemical_formula_moiety         'C14 H10 Br N3 O3 S'
_chemical_formula_sum            'C14 H10 Br N3 O3 S'
_chemical_formula_weight         380.22
_chemical_melting_point          454
_chemical_name_systematic
;
1-(4-Bromophenyl)-1-(4-nitrobenzoyl)thiourea
;
_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                87.386(5)
_cell_angle_beta                 75.044(4)
_cell_angle_gamma                87.511(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0112(3)
_cell_length_b                   8.9697(5)
_cell_length_c                   11.9693(6)
_cell_measurement_reflns_used    13461
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6702
_cell_measurement_theta_min      2.2680
_cell_volume                     726.08(6)
_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    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24890
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    2.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.795
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0305P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0513
_reflns_number_gt                3438
_reflns_number_total             4234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2125.cif
_cod_data_source_block           I
_cod_database_code               2222756
_cod_database_fobs_code          2222756
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S S 0.23307(5) 0.59552(4) 0.59750(3) 0.01794(7) Uani d . 1 . .
Br Br -0.60756(2) 1.070560(16) 0.782568(13) 0.02754(5) Uani d . 1 . .
O O1 0.14426(13) 0.61950(11) 0.23224(8) 0.0212(2) Uani d . 1 . .
O O2 1.06603(14) 0.23725(12) -0.03589(9) 0.0267(2) Uani d . 1 . .
O O3 0.84622(15) 0.09309(11) -0.06698(9) 0.0266(2) Uani d . 1 . .
N N1 0.03832(16) 0.71824(12) 0.44897(10) 0.0159(2) Uani d D 1 . .
H H01 0.015(2) 0.7119(19) 0.3861(13) 0.030(5) Uiso d D 1 . .
N N2 0.31103(16) 0.56699(12) 0.37204(9) 0.0152(2) Uani d D 1 . .
H H02 0.4011(19) 0.5244(16) 0.3860(13) 0.015(4) Uiso d D 1 . .
N N3 0.89393(17) 0.20238(13) -0.02463(9) 0.0190(2) Uani d . 1 . .
C C1 -0.10821(18) 0.79834(14) 0.53147(11) 0.0151(3) Uani d . 1 . .
C C2 -0.3000(2) 0.79948(15) 0.52021(13) 0.0220(3) Uani d . 1 . .
H H2 -0.3305 0.7441 0.4616 0.026 Uiso calc R 1 . .
C C3 -0.4475(2) 0.88188(16) 0.59493(14) 0.0259(3) Uani d . 1 . .
H H3 -0.5792 0.8833 0.5874 0.031 Uiso calc R 1 . .
C C4 -0.4023(2) 0.96140(15) 0.67991(12) 0.0205(3) Uani d . 1 . .
C C5 -0.2115(2) 0.96202(15) 0.69167(12) 0.0217(3) Uani d . 1 . .
H H5 -0.1817 1.0176 0.7503 0.026 Uiso calc R 1 . .
C C6 -0.0636(2) 0.88033(15) 0.61667(12) 0.0199(3) Uani d . 1 . .
H H6 0.0683 0.8805 0.6237 0.024 Uiso calc R 1 . .
C C7 0.18736(18) 0.63277(14) 0.46887(11) 0.0143(2) Uani d . 1 . .
C C8 0.28512(19) 0.56083(14) 0.26223(11) 0.0159(3) Uani d . 1 . .
C C9 0.44489(18) 0.47137(14) 0.18279(10) 0.0146(2) Uani d . 1 . .
C C10 0.39423(19) 0.35787(15) 0.12081(11) 0.0180(3) Uani d . 1 . .
H H10 0.2593 0.3415 0.1258 0.022 Uiso calc R 1 . .
C C11 0.5409(2) 0.26914(15) 0.05200(11) 0.0181(3) Uani d . 1 . .
H H11 0.5087 0.1905 0.0103 0.022 Uiso calc R 1 . .
C C12 0.73630(19) 0.29840(14) 0.04574(11) 0.0160(3) Uani d . 1 . .
C C13 0.79035(19) 0.41304(14) 0.10333(11) 0.0157(3) Uani d . 1 . .
H H13 0.9256 0.4315 0.0956 0.019 Uiso calc R 1 . .
C C14 0.64264(19) 0.50033(14) 0.17260(11) 0.0154(3) Uani d . 1 . .
H H14 0.6760 0.5798 0.2131 0.018 Uiso calc R 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 0.0000 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 127.15(11) ?
C8 N2 C7 . . 128.71(11) ?
O3 N3 O2 . . 124.19(11) ?
O3 N3 C12 . . 118.26(11) ?
O2 N3 C12 . . 117.54(11) ?
C2 C1 C6 . . 119.98(12) ?
C2 C1 N1 . . 117.26(12) ?
C6 C1 N1 . . 122.66(12) ?
C1 C2 C3 . . 119.77(13) ?
C4 C3 C2 . . 119.81(13) ?
C3 C4 C5 . . 121.04(12) ?
C3 C4 Br . . 118.99(10) ?
C5 C4 Br . . 119.97(11) ?
C4 C5 C6 . . 119.22(13) ?
C5 C6 C1 . . 120.18(13) ?
N1 C7 N2 . . 115.54(11) ?
N1 C7 S . . 126.05(10) ?
N2 C7 S . . 118.38(9) ?
O1 C8 N2 . . 123.94(12) ?
O1 C8 C9 . . 122.94(12) ?
N2 C8 C9 . . 113.11(11) ?
C14 C9 C10 . . 120.52(11) ?
C14 C9 C8 . . 119.93(12) ?
C10 C9 C8 . . 119.54(12) ?
C11 C10 C9 . . 119.96(12) ?
C10 C11 C12 . . 118.15(12) ?
C13 C12 C11 . . 122.97(11) ?
C13 C12 N3 . . 118.24(11) ?
C11 C12 N3 . . 118.78(12) ?
C12 C13 C14 . . 118.42(12) ?
C13 C14 C9 . . 119.91(12) ?
C7 N1 H01 . . 116.8(12) ?
C1 N1 H01 . . 114.9(12) ?
C8 N2 H02 . . 118.6(11) ?
C7 N2 H02 . . 112.5(11) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 H11 . . 120.9 ?
C12 C11 H11 . . 120.9 ?
C12 C13 H13 . . 120.8 ?
C14 C13 H13 . . 120.8 ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
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
S C7 . 1.6683(13) ?
Br C4 . 1.9011(13) ?
O1 C8 . 1.2254(15) ?
O2 N3 . 1.2316(15) ?
O3 N3 . 1.2212(15) ?
N1 C7 . 1.3337(16) ?
N1 C1 . 1.4226(15) ?
N2 C8 . 1.3763(17) ?
N2 C7 . 1.3938(15) ?
N3 C12 . 1.4751(15) ?
C1 C2 . 1.3848(19) ?
C1 C6 . 1.3898(19) ?
C2 C3 . 1.3903(18) ?
C3 C4 . 1.377(2) ?
C4 C5 . 1.381(2) ?
C5 C6 . 1.3898(18) ?
C8 C9 . 1.4982(16) ?
C9 C14 . 1.3948(18) ?
C9 C10 . 1.3963(19) ?
C10 C11 . 1.3860(17) ?
C11 C12 . 1.3882(19) ?
C12 C13 . 1.3818(19) ?
C13 C14 . 1.3852(16) ?
N1 H01 . 0.815(14) ?
N2 H02 . 0.774(12) ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
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 H01 O1 . 0.820(10) 2.03(2) 2.688(2) 138(2)
N2 H02 S 2_666 0.770(10) 2.790(10) 3.5530(10) 169.0(10)
C5 H5 O3 1_466 0.95 2.38 3.293(2) 162.2
C3 H3 S 1_455 0.95 2.93 3.474(2) 117.5
C14 H14 S 2_666 0.95 2.89 3.1670(10) 98.1
C14 H14 Br 2_576 0.95 3.15 3.8990(10) 136.7
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
C7 N1 C1 C2 . . . . -140.03(14) ?
C7 N1 C1 C6 . . . . 43.7(2) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
N1 C1 C2 C3 . . . . -176.90(13) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
C2 C3 C4 C5 . . . . 0.6(2) ?
C2 C3 C4 Br . . . . -178.99(11) ?
C3 C4 C5 C6 . . . . -0.3(2) ?
Br C4 C5 C6 . . . . 179.32(10) ?
C4 C5 C6 C1 . . . . -0.4(2) ?
C2 C1 C6 C5 . . . . 0.8(2) ?
N1 C1 C6 C5 . . . . 177.03(12) ?
C1 N1 C7 N2 . . . . -179.75(12) ?
C1 N1 C7 S . . . . 2.0(2) ?
C8 N2 C7 N1 . . . . -10.14(19) ?
C8 N2 C7 S . . . . 168.29(11) ?
C7 N2 C8 O1 . . . . 2.3(2) ?
C7 N2 C8 C9 . . . . -176.27(12) ?
O1 C8 C9 C14 . . . . 130.59(14) ?
N2 C8 C9 C14 . . . . -50.80(16) ?
O1 C8 C9 C10 . . . . -50.40(18) ?
N2 C8 C9 C10 . . . . 128.21(13) ?
C14 C9 C10 C11 . . . . 2.54(19) ?
C8 C9 C10 C11 . . . . -176.47(11) ?
C9 C10 C11 C12 . . . . -0.99(19) ?
C10 C11 C12 C13 . . . . -1.09(19) ?
C10 C11 C12 N3 . . . . 178.37(11) ?
O3 N3 C12 C13 . . . . 173.49(11) ?
O2 N3 C12 C13 . . . . -5.83(17) ?
O3 N3 C12 C11 . . . . -6.00(17) ?
O2 N3 C12 C11 . . . . 174.68(12) ?
C11 C12 C13 C14 . . . . 1.60(19) ?
N3 C12 C13 C14 . . . . -177.87(11) ?
C12 C13 C14 C9 . . . . -0.02(18) ?
C10 C9 C14 C13 . . . . -2.02(19) ?
C8 C9 C14 C13 . . . . 176.98(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2347279
