#------------------------------------------------------------------------------
#$Date: 2023-01-06 10:37:04 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280151 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106422.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106422
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Smith, Keith'
'Hegazy, Amany S.'
'Hayal Alotaibi, Mohammad'
'Kariuki, Benson M.'
_publ_section_title
;
 Crystal structure of 3-(2-bromophenyl)-1,1-dimethylthiourea, C9H11BrN2S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              31
_journal_page_last               32
_journal_paper_doi               10.1515/ncrs-2016-0116
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C9 H11 Br N2 S'
_chemical_formula_sum            'C9 H11 Br N2 S'
_chemical_formula_weight         259.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5187(3)
_cell_length_b                   8.0634(3)
_cell_length_c                   17.5320(6)
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      73.4900
_cell_measurement_theta_min      5.0380
_cell_volume                     1062.90(7)
_computing_cell_refinement       'CrysAlis PRO [12]'
_computing_data_collection       'CrysAlis PRO [12]'
_computing_data_reduction        'CrysAlis PRO [12]'
_computing_molecular_graphics    'ORTEP-3 for Windows [14]'
_computing_publication_material  'WinGX [14] and CHEMDRAW Ultra [15]'
_computing_structure_refinement  'SHELXS2013 [13]'
_computing_structure_solution    'SHELXS2013 [13]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3493
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.728
_diffrn_reflns_theta_min         5.045
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.748
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.005(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0216
_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)+(0.0255P)²+0.1941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0536
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                1969
_reflns_number_total             2052
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0116_suppl.cif
_cod_data_source_block           ks1407
_cod_database_code               8106422
_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   0.173
_shelx_estimated_absorpt_t_max   0.798
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1300(4) 0.7897(4) 0.18698(16) 0.0385(6) Uani 1 1 d . . . . .
C2 C -0.0864(4) 0.8683(4) 0.11919(15) 0.0397(6) Uani 1 1 d . . . . .
C3 C -0.2084(6) 0.8842(5) 0.06025(18) 0.0516(9) Uani 1 1 d . . . . .
H3 H -0.1772 0.9373 0.0151 0.062 Uiso 1 1 calc R U . . .
C4 C -0.3767(6) 0.8197(5) 0.0699(2) 0.0580(10) Uani 1 1 d . . . . .
H4 H -0.4603 0.8305 0.0312 0.070 Uiso 1 1 calc R U . . .
C5 C -0.4225(5) 0.7389(6) 0.1369(3) 0.0606(10) Uani 1 1 d . . . . .
H5 H -0.5360 0.6949 0.1427 0.073 Uiso 1 1 calc R U . . .
C6 C -0.2998(5) 0.7239(5) 0.1949(2) 0.0513(8) Uani 1 1 d . . . . .
H6 H -0.3310 0.6693 0.2397 0.062 Uiso 1 1 calc R U . . .
C7 C -0.0060(4) 0.8368(4) 0.31579(16) 0.0383(6) Uani 1 1 d . . . . .
C8 C 0.3063(5) 0.7520(6) 0.3259(2) 0.0573(9) Uani 1 1 d . . . . .
H8A H 0.2932 0.6364 0.3140 0.086 Uiso 1 1 calc R U . . .
H8B H 0.4003 0.7659 0.3623 0.086 Uiso 1 1 calc R U . . .
H8C H 0.3345 0.8123 0.2802 0.086 Uiso 1 1 calc R U . . .
C9 C 0.1465(7) 0.8677(6) 0.43742(19) 0.0663(11) Uani 1 1 d . . . . .
H9A H 0.1900 0.9795 0.4402 0.100 Uiso 1 1 calc R U . . .
H9B H 0.2242 0.7958 0.4656 0.100 Uiso 1 1 calc R U . . .
H9C H 0.0291 0.8627 0.4588 0.100 Uiso 1 1 calc R U . . .
N1 N 0.0001(4) 0.7701(4) 0.24471(16) 0.0427(6) Uani 1 1 d . . . . .
H1 H 0.0914 0.7105 0.2337 0.051 Uiso 1 1 calc R U . . .
N2 N 0.1406(4) 0.8148(4) 0.35780(15) 0.0471(6) Uani 1 1 d . . . . .
S1 S -0.18713(11) 0.94115(11) 0.34745(4) 0.0500(2) Uani 1 1 d . . . . .
Br1 Br 0.14459(5) 0.95693(5) 0.10617(2) 0.05486(12) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 118.5(3) . .
C2 C1 N1 120.0(3) . .
C6 C1 N1 121.4(3) . .
C1 C2 C3 121.6(3) . .
C1 C2 Br1 119.5(2) . .
C3 C2 Br1 118.8(3) . .
C4 C3 C2 118.7(3) . .
C4 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
C3 C4 C5 120.6(3) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 120.0(4) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C1 120.5(4) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
N2 C7 N1 115.2(3) . .
N2 C7 S1 123.2(2) . .
N1 C7 S1 121.6(2) . .
N2 C8 H8A 109.5 . .
N2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 N1 C1 126.1(3) . .
C7 N1 H1 117.0 . .
C1 N1 H1 117.0 . .
C7 N2 C8 122.6(3) . .
C7 N2 C9 120.8(4) . .
C8 N2 C9 116.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.386(4) .
C1 C6 1.390(5) .
C1 N1 1.416(4) .
C2 C3 1.387(5) .
C2 Br1 1.892(3) .
C3 C4 1.379(6) .
C3 H3 0.9300 .
C4 C5 1.386(6) .
C4 H4 0.9300 .
C5 C6 1.379(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N2 1.337(5) .
C7 N1 1.358(4) .
C7 S1 1.694(3) .
C8 N2 1.457(5) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 N2 1.460(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
N1 H1 0.8600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.86 2.69 3.410(3) 141.5 3_545
