#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005125.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_2005125
loop_
_publ_author_name
'Zhang, D.-C.'
'Zhang, Y.-Q.'
'Cao, Y.'
'Zhao, B.'
_publ_section_title
;
 1-Benzoyl-3-(4-nitrophenyl)thiourea
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1716
_journal_page_last               1718
_journal_paper_doi               10.1107/S0108270196001047
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C14 H11 N3 O3 S'
_chemical_formula_sum            'C14 H11 N3 O3 S'
_chemical_formula_weight         301.32
_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'
_cell_angle_alpha                90
_cell_angle_beta                 97.22(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.098(3)
_cell_length_b                   25.665(2)
_cell_length_c                   12.989(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      23.27
_cell_volume                     1355.3(11)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN PROCESS (Molecular Structure Corporation, 1985, 1992)'
_computing_publication_material  'TEXSAN FINISH'
_computing_structure_refinement  'TEXSAN LS'
_computing_structure_solution
;
SAPI91 (Fan, 1991) and expanded using Fourier techniques (Beurskens et al.,
1992)
;
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Rigaku AFC-7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2804
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        0.60
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.2530
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type
'empirical via \y scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    none
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.630
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.034
_refine_ls_shift/esd_max         0.029
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(F)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.044
_reflns_number_observed          1736
_reflns_number_total             2445
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ha1152.cif
_cod_data_source_block           ha1152
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F)]' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/[\s^2^(F)]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1355.5(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005125
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,1/2-z'
'   -x,   -y,   -z'
'   +x,1/2-y,1/2+z'
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
S 0.0499(4) 0.0309(3) 0.0318(3) 0.0038(3) -0.0022(2) -0.0024(3)
O(1) 0.115(2) 0.0350(10) 0.0340(10) 0.0240(10) -0.0080(10) -0.0024(8)
O(2) 0.087(2) 0.0590(10) 0.0560(10) -0.0150(10) -0.0080(10) 0.0290(10)
O(3) 0.090(2) 0.0600(10) 0.0490(10) -0.0070(10) -0.0310(10) 0.0130(10)
N(1) 0.0610(10) 0.0280(10) 0.0260(10) 0.0099(10) -0.0023(9) 0.0025(9)
N(2) 0.0660(10) 0.0300(10) 0.0230(10) 0.0095(10) -0.0041(10) -0.0002(9)
N(3) 0.0550(10) 0.0410(10) 0.0310(10) 0.0080(10) -0.0014(10) 0.0078(10)
C(1) 0.056(2) 0.0360(10) 0.0310(10) 0.0080(10) 0.0030(10) -0.0010(10)
C(2) 0.0420(10) 0.0340(10) 0.0250(10) 0.0069(10) 0.0025(10) 0.0000(10)
C(3) 0.058(2) 0.041(2) 0.0370(10) -0.0040(10) 0.0050(10) -0.0020(10)
C(4) 0.052(2) 0.063(2) 0.0350(10) -0.0050(10) -0.0070(10) -0.0090(10)
C(5) 0.053(2) 0.063(2) 0.0310(10) 0.0110(10) -0.0050(10) 0.0050(10)
C(6) 0.059(2) 0.045(2) 0.0380(10) 0.0060(10) 0.0050(10) 0.0100(10)
C(7) 0.0450(10) 0.0400(10) 0.0290(10) 0.0030(10) 0.0040(10) -0.0010(10)
C(8) 0.0400(10) 0.0330(10) 0.0260(10) 0.0040(10) 0.0026(10) 0.0026(10)
C(9) 0.0430(10) 0.0320(10) 0.0260(10) 0.0080(10) 0.0031(10) 0.0024(10)
C(10) 0.054(2) 0.0310(10) 0.0310(10) 0.0040(10) -0.0050(10) -0.0040(10)
C(11) 0.051(2) 0.0270(10) 0.0350(10) 0.0000(10) 0.0030(10) 0.0020(10)
C(12) 0.0410(10) 0.0340(10) 0.0260(10) 0.0060(10) 0.0023(10) 0.0054(10)
C(13) 0.0430(10) 0.0370(10) 0.0330(10) -0.0020(10) -0.0070(10) 0.0010(10)
C(14) 0.0420(10) 0.0310(10) 0.0400(10) -0.0020(10) 0.0000(10) 0.0080(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
S .6926(2) .03651(2) .37744(5) .0381 Uani
O(1) .7966(6) .16027(7) .62900(10) .0627 Uani
O(2) .2445(5) .26697(8) .0273(2) .0691 Uani
O(3) -.0982(6) .20465(8) -.0046(2) .0697 Uani
N(1) .8241(5) .07875(8) .56190(10) .0392 Uani
N(2) .5964(6) .13534(8) .4345(2) .0405 Uani
N(3) .1235(5) .22620(8) .0511(2) .0430 Uani
C(1) .8694(6) .11427(10) .6421(2) .0410 Uani
C(2) 1.0177(6) .09400(9) .7445(2) .0339 Uani
C(3) 1.2056(7) .12810(10) .8109(2) .0451 Uani
C(4) 1.3456(7) .11150(10) .9075(2) .0512 Uani
C(5) 1.2976(7) .06150(10) .9385(2) .0499 Uani
C(6) 1.1077(7) .02750(10) .8739(2) .0471 Uani
C(7) .9686(6) .04345(10) .7767(2) .0378 Uani
C(8) .6970(6) .08651(9) .4585(2) .0331 Uani
C(9) .4766(6) .15577(9) .3360(2) .0337 Uani
C(10) .5718(7) .20637(9) .3143(2) .0394 Uani
C(11) .4606(6) .22932(10) .2206(2) .0381 Uani
C(12) .2494(6) .20184(9) .1499(2) .0339 Uani
C(13) .1473(6) .15191(10) .1706(2) .0388 Uani
C(14) .2624(6) .12906(10) .2640(2) .0383 Uani
H(1) 1.241(6) .1620(10) .789(2) .048(7) Ueq
H(2) 1.483(6) .1343(10) .947(2) .051(8) Ueq
H(3) 1.401(7) .0506(10) 1.006(2) .058(8) Ueq
H(4) 1.076(7) -.0070(10) .897(2) .064(9) Ueq
H(5) .822(6) .0201(9) .732(2) .046(7) Ueq
H(6) .898(7) .0490(10) .576(2) .060(9) Ueq
H(7) .646(7) .1570(10) .484(2) .061(9) Ueq
H(8) .720(6) .2220(10) .362(2) .053(8) Ueq
H(9) .529(6) .2630(10) .202(2) .049(7) Ueq
H(10) .001(7) .1350(10) .123(2) .057(8) Ueq
H(11) .189(6) .0960(10) .280(2) .045(7) Ueq
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002 'Cromer \& Waber (1974)'
H 0.000 0.000 'Cromer \& Waber (1974)'
N 0.006 0.003 'Cromer \& Waber (1974)'
O 0.011 0.006 'Cromer \& Waber (1974)'
S 0.125 0.123 'Cromer \& Waber (1974)'
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
C(1) N(1) C(8) 129.2(2) yes
C(8) N(2) C(9) 128.1(2) yes
O(2) N(3) O(3) 122.5(2) yes
O(2) N(3) C(12) 118.8(2) yes
O(3) N(3) C(12) 118.7(2) yes
O(1) C(1) N(1) 121.7(2) yes
O(1) C(1) C(2) 121.8(2) yes
N(1) C(1) C(2) 116.5(2) yes
C(1) C(2) C(3) 117.9(2) yes
C(1) C(2) C(7) 122.7(2) yes
C(3) C(2) C(7) 119.4(2) no
C(2) C(3) C(4) 120.3(3) no
C(3) C(4) C(5) 119.9(3) no
C(4) C(5) C(6) 120.4(3) no
C(5) C(6) C(7) 120.3(3) no
C(2) C(7) C(6) 119.7(2) no
S C(8) N(1) 118.3(2) yes
S C(8) N(2) 126.6(2) yes
N(1) C(8) N(2) 115.0(2) yes
N(2) C(9) C(10) 117.0(2) yes
N(2) C(9) C(14) 123.2(2) yes
C(10) C(9) C(14) 119.7(2) no
C(9) C(10) C(11) 120.4(2) no
C(10) C(11) C(12) 118.8(2) no
N(3) C(12) C(11) 119.3(2) yes
N(3) C(12) C(13) 118.9(2) yes
C(11) C(12) C(13) 121.7(2) no
C(12) C(13) C(14) 119.1(2) no
C(9) C(14) C(13) 120.2(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C(8) 1.658(2) yes
O(1) C(1) 1.224(3) yes
O(2) N(3) 1.214(3) yes
O(3) N(3) 1.220(3) yes
N(1) C(1) 1.379(3) yes
N(1) C(8) 1.393(3) yes
N(2) C(8) 1.344(3) yes
N(2) C(9) 1.413(3) yes
N(3) C(12) 1.463(3) yes
C(1) C(2) 1.485(3) yes
C(2) C(3) 1.391(3) no
C(2) C(7) 1.386(3) no
C(3) C(4) 1.381(4) no
C(4) C(5) 1.366(4) no
C(5) C(6) 1.381(4) no
C(6) C(7) 1.381(3) no
C(9) C(10) 1.395(3) no
C(9) C(14) 1.381(3) no
C(10) C(11) 1.377(3) no
C(11) C(12) 1.375(3) no
C(12) C(13) 1.385(3) no
C(13) C(14) 1.377(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N(2) O(1) 2.635(3) . yes
N(1) S 3.592(2) 3_756 yes
N(2) O(2) 3.202(3) 4_555 yes
C(7) S 3.294(3) 3_756 yes
C(7) S 3.768(3) 3_656 yes
C(4) O(3) 3.294(4) 1_656 yes
C(4) O(3) 3.400(4) 1_756 yes
C(11) O(1) 3.428(3) 4_554 yes
C(10) O(3) 3.432(3) 4_655 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 2765772