#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:53:19 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022289.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_2022289
loop_
_publ_author_name
'Rosiak, Damian'
'Okuniewski, Andrzej'
'Chojnacki, Jarosław'
_publ_section_title
;
 The influence of the type of halogen substituent and its position on the
 molecular conformation, intermolecular interactions and crystal packing
 for a series of 1-benzoyl-3-(halogenophenyl)thioureas
;
_journal_coeditor_code           WP3011
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              11
_journal_page_last               19
_journal_paper_doi               10.1107/S2053229620015594
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C14 H11 Br N2 O S'
_chemical_formula_moiety         'C14 H11 Br N2 O S'
_chemical_formula_sum            'C14 H11 Br N2 O S'
_chemical_formula_weight         335.23
_chemical_name_common            1-Benzoyl-3-o-bromophenylthiourea
_chemical_name_systematic
;
1-Benzoyl-3-(2-bromophenyl)thiourea
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.183(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9592(4)
_cell_length_b                   15.142(2)
_cell_length_c                   22.250(2)
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.66
_cell_measurement_theta_min      2.69
_cell_volume                     1328.4(3)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.690
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.243
_exptl_absorpt_correction_T_max  0.8920
_exptl_absorpt_correction_T_min  0.3786
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration,
analogous to Coppens (1970)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.034
_refine_diff_density_max         1.061
_refine_diff_density_min         -1.475
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0967P)²+0.6126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                2917
_reflns_number_total             3566
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            wp3011sup1.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 2022286--2022290.cif.'
_cod_database_code               2022289
_cod_database_fobs_code          2022289
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.192
_shelx_estimated_absorpt_t_max   0.898
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.83362(8) 0.34433(2) 0.77092(2) 0.01943(14) Uani d 1 . .
S S1 0.6259(2) 0.54961(5) 0.58644(4) 0.01665(18) Uani d 1 . .
O O1 0.2706(9) 0.27419(16) 0.62856(12) 0.0297(6) Uani d 1 . .
N N1 0.3562(7) 0.39130(16) 0.56653(12) 0.0161(5) Uani d 1 . .
H H1 0.353938 0.406926 0.528399 0.019 Uiso calc 1 . .
N N2 0.4080(8) 0.43571(16) 0.66660(13) 0.0173(5) Uani d 1 . .
H H2 0.329777 0.382603 0.673484 0.021 Uiso calc 1 . .
C C26 0.6616(8) 0.46142(19) 0.76882(15) 0.0162(6) Uani d 1 . .
C C21 0.4747(8) 0.49224(19) 0.71708(14) 0.0154(6) Uani d 1 . .
C C23 0.3934(9) 0.6301(2) 0.76853(16) 0.0189(6) Uani d 1 . .
H H23 0.297239 0.687607 0.768823 0.023 Uiso calc 1 . .
C C25 0.7230(8) 0.5146(2) 0.81993(15) 0.0190(6) Uani d 1 . .
H H25 0.853494 0.492943 0.854762 0.023 Uiso calc 1 . .
C C22 0.3352(8) 0.5774(2) 0.71732(15) 0.0175(6) Uani d 1 . .
H H22 0.201802 0.598914 0.682784 0.021 Uiso calc 1 . .
C C1 0.4536(8) 0.45618(19) 0.60940(14) 0.0140(5) Uani d 1 . .
C C11 0.1546(8) 0.25167(18) 0.52290(14) 0.0160(6) Uani d 1 . .
C C14 -0.0510(9) 0.1466(2) 0.42403(17) 0.0221(7) Uani d 1 . .
H H14 -0.119601 0.110393 0.390232 0.026 Uiso calc 1 . .
C C24 0.5898(9) 0.5998(2) 0.81905(16) 0.0201(6) Uani d 1 . .
H H24 0.633754 0.637177 0.853146 0.024 Uiso calc 1 . .
C C16 -0.0313(8) 0.2886(2) 0.47280(15) 0.0171(6) Uani d 1 . .
H H16 -0.084947 0.349728 0.472294 0.021 Uiso calc 1 . .
C C12 0.2344(9) 0.16178(19) 0.52423(16) 0.0192(6) Uani d 1 . .
H H12 0.353727 0.136073 0.558862 0.023 Uiso calc 1 . .
C C10 0.2633(9) 0.30534(19) 0.57767(15) 0.0185(6) Uani d 1 . .
C C13 0.1350(9) 0.1106(2) 0.47352(17) 0.0227(7) Uani d 1 . .
H H13 0.196328 0.049976 0.473065 0.027 Uiso calc 1 . .
C C15 -0.1383(9) 0.2354(2) 0.42343(15) 0.0201(6) Uani d 1 . .
H H15 -0.269855 0.259882 0.389659 0.024 Uiso calc 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'
Br Br -0.2901 2.4595 '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'
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 H1 . . 116.5 ?
C10 N1 H1 . . 116.5 ?
C10 N1 C1 . . 126.9(3) ?
C21 N2 H2 . . 117.2 ?
C1 N2 H2 . . 117.2 ?
C1 N2 C21 . . 125.6(3) ?
C21 C26 Br1 . . 119.8(2) ?
C21 C26 C25 . . 121.4(3) ?
C25 C26 Br1 . . 118.9(2) ?
C26 C21 N2 . . 120.0(3) ?
C26 C21 C22 . . 119.0(3) ?
C22 C21 N2 . . 120.8(3) ?
C22 C23 H23 . . 119.6 ?
C24 C23 H23 . . 119.6 ?
C24 C23 C22 . . 120.8(3) ?
C26 C25 H25 . . 120.5 ?
C24 C25 C26 . . 119.0(3) ?
C24 C25 H25 . . 120.5 ?
C21 C22 H22 . . 120.2 ?
C23 C22 C21 . . 119.6(3) ?
C23 C22 H22 . . 120.2 ?
N1 C1 S1 . . 118.8(2) ?
N2 C1 S1 . . 125.5(2) ?
N2 C1 N1 . . 115.7(3) ?
C16 C11 C12 . . 120.6(3) ?
C16 C11 C10 . . 121.7(3) ?
C12 C11 C10 . . 117.7(3) ?
C13 C14 H14 . . 119.9 ?
C13 C14 C15 . . 120.3(3) ?
C15 C14 H14 . . 119.9 ?
C23 C24 C25 . . 120.2(3) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C11 C16 H16 . . 120.1 ?
C11 C16 C15 . . 119.9(3) ?
C15 C16 H16 . . 120.1 ?
C11 C12 H12 . . 120.8 ?
C13 C12 C11 . . 118.5(3) ?
C13 C12 H12 . . 120.8 ?
O1 C10 N1 . . 123.0(3) ?
O1 C10 C11 . . 121.7(3) ?
N1 C10 C11 . . 115.3(3) ?
C14 C13 C12 . . 121.1(3) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C14 C15 C16 . . 119.6(3) ?
C14 C15 H15 . . 120.2 ?
C16 C15 H15 . . 120.2 ?
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
Br1 C26 . 1.898(3) ?
S1 C1 . 1.671(3) ?
O1 C10 . 1.225(4) ?
N1 H1 . 0.8800 ?
N1 C1 . 1.399(4) ?
N1 C10 . 1.381(4) ?
N2 H2 . 0.8800 ?
N2 C21 . 1.418(4) ?
N2 C1 . 1.338(4) ?
C26 C21 . 1.392(5) ?
C26 C25 . 1.396(4) ?
C21 C22 . 1.402(4) ?
C23 H23 . 0.9500 ?
C23 C22 . 1.394(5) ?
C23 C24 . 1.386(5) ?
C25 H25 . 0.9500 ?
C25 C24 . 1.394(5) ?
C22 H22 . 0.9500 ?
C11 C16 . 1.396(5) ?
C11 C12 . 1.397(4) ?
C11 C10 . 1.495(4) ?
C14 H14 . 0.9500 ?
C14 C13 . 1.380(6) ?
C14 C15 . 1.389(5) ?
C24 H24 . 0.9500 ?
C16 H16 . 0.9500 ?
C16 C15 . 1.396(5) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.396(5) ?
C13 H13 . 0.9500 ?
C15 H15 . 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
_geom_hbond_publ_flag
N1 H1 S1 3_666 0.88 2.65 3.526(3) 177.4 yes
N2 H2 O1 . 0.88 1.93 2.629(4) 135.8 yes
