#------------------------------------------------------------------------------
#$Date: 2024-06-01 05:13:04 +0300 (Sat, 01 Jun 2024) $
#$Revision: 292154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/31/2023142.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_2023142
loop_
_publ_author_name
'Sow, Salif'
'Thiam, Mariama'
'Odame, Felix'
'Thiam, Elhadj Ibrahima'
'Diouf, Ousmane'
'Ellena, Javier'
'Gaye, Mohamed'
'Tshentu, Zenixole'
_publ_section_title
;
 Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea
;
_journal_coeditor_code           PK2706
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              663
_journal_page_last               666
_journal_paper_doi               10.1107/S2056989024004742
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C15 H10 Br N3 O S2'
_chemical_formula_moiety         'C15 H10 Br N3 O S2'
_chemical_formula_sum            'C15 H10 Br N3 O S2'
_chemical_formula_weight         392.29
_chemical_name_systematic
;
1-(1,3-Benzothiazol-2-yl)-3-(4-bromobenzoyl)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 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.606(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5009(5)
_cell_length_b                   6.4130(2)
_cell_length_c                   17.9147(7)
_cell_measurement_reflns_used    9123
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      33.9080
_cell_measurement_theta_min      3.0900
_cell_volume                     1507.55(10)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18792
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.105
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0240
_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)+(0.0191P)²+1.3729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0570
_reflns_number_gt                2581
_reflns_number_total             3074
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2706.cif
_cod_data_source_block           I
_cod_original_cell_volume        1507.54(10)
_cod_database_code               2023142
_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   0.749
_shelx_estimated_absorpt_t_max   0.847
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 0.07298(2) -0.50717(3) 0.27034(2) 0.01865(7) Uani d 1 . .
S S1 0.24869(4) 0.98772(8) 0.63447(3) 0.01659(12) Uani d 1 . .
S S2 0.10718(4) 0.61809(8) 0.59446(3) 0.02191(13) Uani d 1 . .
O O1 0.29683(11) 0.3918(2) 0.43225(8) 0.0182(3) Uani d 1 . .
N N3 0.16341(14) 0.3897(3) 0.48987(10) 0.0172(4) Uani d 1 . .
H H3 0.106967 0.322341 0.490909 0.021 Uiso calc 1 . .
N N1 0.38000(13) 0.9461(3) 0.54899(10) 0.0155(4) Uani d 1 . .
N N2 0.26397(13) 0.6774(3) 0.52923(10) 0.0148(4) Uani d 1 . .
H H2 0.298111 0.627829 0.496902 0.018 Uiso calc 1 . .
C C10 0.18323(16) 0.1035(3) 0.40497(12) 0.0145(4) Uani d 1 . .
C C11 0.24401(17) 0.0071(3) 0.36228(12) 0.0183(4) Uani d 1 . .
H H11 0.307296 0.068130 0.359855 0.022 Uiso calc 1 . .
C C8 0.18301(16) 0.5657(3) 0.53592(12) 0.0167(4) Uani d 1 . .
C C9 0.22053(16) 0.3057(3) 0.44251(12) 0.0152(4) Uani d 1 . .
C C13 0.12063(17) -0.2631(3) 0.32704(12) 0.0162(4) Uani d 1 . .
C C6 0.40504(15) 1.1298(3) 0.59049(11) 0.0139(4) Uani d 1 . .
C C4 0.49993(17) 1.4411(3) 0.62991(13) 0.0208(5) Uani d 1 . .
H H4 0.553913 1.533414 0.626970 0.025 Uiso calc 1 . .
C C12 0.21305(17) -0.1773(3) 0.32321(13) 0.0199(5) Uani d 1 . .
H H12 0.254784 -0.243387 0.294303 0.024 Uiso calc 1 . .
C C14 0.05956(16) -0.1731(3) 0.37025(13) 0.0178(4) Uani d 1 . .
H H14 -0.003263 -0.235813 0.372947 0.021 Uiso calc 1 . .
C C3 0.43652(17) 1.4872(3) 0.67971(13) 0.0200(5) Uani d 1 . .
H H3A 0.448160 1.611081 0.709576 0.024 Uiso calc 1 . .
C C2 0.35797(17) 1.3570(3) 0.68620(12) 0.0196(5) Uani d 1 . .
H H2A 0.315825 1.387679 0.720416 0.023 Uiso calc 1 . .
C C1 0.34260(16) 1.1782(3) 0.64059(12) 0.0158(4) Uani d 1 . .
C C7 0.30166(16) 0.8612(3) 0.56641(12) 0.0144(4) Uani d 1 . .
C C15 0.09165(17) 0.0100(3) 0.40956(13) 0.0185(4) Uani d 1 . .
H H15 0.050806 0.072576 0.439944 0.022 Uiso calc 1 . .
C C5 0.48474(16) 1.2633(3) 0.58523(12) 0.0179(4) Uani d 1 . .
H H5 0.527660 1.232504 0.551582 0.021 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0518
0 1 0 0.0505
1 0 -1 0.0256
-2 -1 2 0.0440
2 -1 -2 0.0513
0 0 1 0.0265
0 0 -1 0.0307
-1 0 -1 0.0328
-2 0 1 0.0289
-1 -2 0 0.0456
-1 -1 1 0.0438
2 0 1 0.0265
8 -2 19 0.0268
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 S1 C7 . . 87.61(9) ?
C8 N3 H3 . . 115.6 ?
C9 N3 H3 . . 115.6 ?
C9 N3 C8 . . 128.78(18) ?
C7 N1 C6 . . 109.74(17) ?
C8 N2 H2 . . 115.6 ?
C8 N2 C7 . . 128.81(17) ?
C7 N2 H2 . . 115.6 ?
C11 C10 C9 . . 116.96(18) ?
C11 C10 C15 . . 119.18(19) ?
C15 C10 C9 . . 123.85(18) ?
C10 C11 H11 . . 119.7 ?
C12 C11 C10 . . 120.6(2) ?
C12 C11 H11 . . 119.7 ?
N3 C8 S2 . . 118.68(15) ?
N2 C8 S2 . . 125.92(16) ?
N2 C8 N3 . . 115.40(17) ?
O1 C9 N3 . . 121.88(19) ?
O1 C9 C10 . . 122.19(18) ?
N3 C9 C10 . . 115.92(18) ?
C12 C13 Br1 . . 119.98(16) ?
C12 C13 C14 . . 121.79(19) ?
C14 C13 Br1 . . 118.22(16) ?
N1 C6 C1 . . 114.95(18) ?
N1 C6 C5 . . 125.29(18) ?
C5 C6 C1 . . 119.76(18) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C5 C4 C3 . . 120.8(2) ?
C11 C12 H12 . . 120.6 ?
C13 C12 C11 . . 118.89(19) ?
C13 C12 H12 . . 120.6 ?
C13 C14 H14 . . 120.6 ?
C13 C14 C15 . . 118.80(19) ?
C15 C14 H14 . . 120.6 ?
C4 C3 H3A . . 119.3 ?
C2 C3 C4 . . 121.5(2) ?
C2 C3 H3A . . 119.3 ?
C3 C2 H2A . . 121.3 ?
C3 C2 C1 . . 117.4(2) ?
C1 C2 H2A . . 121.3 ?
C6 C1 S1 . . 110.00(15) ?
C2 C1 S1 . . 128.16(16) ?
C2 C1 C6 . . 121.83(19) ?
N1 C7 S1 . . 117.69(15) ?
N1 C7 N2 . . 118.04(18) ?
N2 C7 S1 . . 124.26(15) ?
C10 C15 H15 . . 119.7 ?
C14 C15 C10 . . 120.69(19) ?
C14 C15 H15 . . 119.7 ?
C6 C5 H5 . . 120.7 ?
C4 C5 C6 . . 118.65(19) ?
C4 C5 H5 . . 120.7 ?
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 C13 . 1.894(2) ?
S1 C1 . 1.745(2) ?
S1 C7 . 1.751(2) ?
S2 C8 . 1.663(2) ?
O1 C9 . 1.220(2) ?
N3 H3 . 0.8800 ?
N3 C8 . 1.386(3) ?
N3 C9 . 1.383(3) ?
N1 C6 . 1.392(3) ?
N1 C7 . 1.291(3) ?
N2 H2 . 0.8800 ?
N2 C8 . 1.335(3) ?
N2 C7 . 1.390(3) ?
C10 C11 . 1.391(3) ?
C10 C9 . 1.492(3) ?
C10 C15 . 1.394(3) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.388(3) ?
C13 C12 . 1.380(3) ?
C13 C14 . 1.383(3) ?
C6 C1 . 1.403(3) ?
C6 C5 . 1.396(3) ?
C4 H4 . 0.9500 ?
C4 C3 . 1.406(3) ?
C4 C5 . 1.380(3) ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C14 C15 . 1.386(3) ?
C3 H3A . 0.9500 ?
C3 C2 . 1.376(3) ?
C2 H2A . 0.9500 ?
C2 C1 . 1.395(3) ?
C15 H15 . 0.9500 ?
C5 H5 . 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
N3 H3 S2 3_566 0.88 2.96 3.6102(19) 132.1 yes
N2 H2 O1 . 0.88 1.90 2.633(2) 139.1 yes
C14 H14 S2 3_556 0.95 2.95 3.779(2) 146.4 yes
C2 H2A S1 2_556 0.95 3.00 3.908(2) 160.7 yes
C5 H5 N1 3_676 0.95 2.68 3.604(3) 165.0 yes
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
Br1 C13 C12 C11 . . . . 176.90(16) ?
Br1 C13 C14 C15 . . . . -177.46(16) ?
N1 C6 C1 S1 . . . . -0.6(2) ?
N1 C6 C1 C2 . . . . 179.95(19) ?
N1 C6 C5 C4 . . . . 179.7(2) ?
C10 C11 C12 C13 . . . . 0.4(3) ?
C11 C10 C9 O1 . . . . 5.2(3) ?
C11 C10 C9 N3 . . . . -174.74(18) ?
C11 C10 C15 C14 . . . . -2.0(3) ?
C8 N3 C9 O1 . . . . -4.8(3) ?
C8 N3 C9 C10 . . . . 175.1(2) ?
C8 N2 C7 S1 . . . . 1.2(3) ?
C8 N2 C7 N1 . . . . -177.8(2) ?
C9 N3 C8 S2 . . . . -173.64(17) ?
C9 N3 C8 N2 . . . . 5.5(3) ?
C9 C10 C11 C12 . . . . -177.60(19) ?
C9 C10 C15 C14 . . . . 177.0(2) ?
C13 C14 C15 C10 . . . . 0.7(3) ?
C6 N1 C7 S1 . . . . -0.4(2) ?
C6 N1 C7 N2 . . . . 178.69(17) ?
C4 C3 C2 C1 . . . . -0.8(3) ?
C12 C13 C14 C15 . . . . 1.1(3) ?
C14 C13 C12 C11 . . . . -1.7(3) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C3 C2 C1 S1 . . . . -178.55(17) ?
C3 C2 C1 C6 . . . . 0.8(3) ?
C1 S1 C7 N1 . . . . 0.05(18) ?
C1 S1 C7 N2 . . . . -178.98(19) ?
C1 C6 C5 C4 . . . . 0.0(3) ?
C7 S1 C1 C6 . . . . 0.32(16) ?
C7 S1 C1 C2 . . . . 179.7(2) ?
C7 N1 C6 C1 . . . . 0.7(3) ?
C7 N1 C6 C5 . . . . -179.1(2) ?
C7 N2 C8 S2 . . . . -2.1(3) ?
C7 N2 C8 N3 . . . . 178.90(19) ?
C15 C10 C11 C12 . . . . 1.5(3) ?
C15 C10 C9 O1 . . . . -173.8(2) ?
C15 C10 C9 N3 . . . . 6.2(3) ?
C5 C6 C1 S1 . . . . 179.10(16) ?
C5 C6 C1 C2 . . . . -0.3(3) ?
C5 C4 C3 C2 . . . . 0.5(3) ?
