Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
Wang, Ning; Guo, Ya-Fei; Ma, Jun-Ying; Liu, Ming-Ming; Qu, Yu-Long; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 1211–1213; doi:10.1515/ncrs-2023-0409

data_8107705
_publ_section_title
;
 Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1211
_journal_page_last               1213
_journal_paper_doi               10.1515/ncrs-2023-0409
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H10 Br N S'
_chemical_formula_sum            'C14 H10 Br N S'
_chemical_formula_weight         304.20
_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   mixed
_atom_sites_solution_primary     heavy
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6392(2)
_cell_length_b                   7.7930(3)
_cell_length_c                   28.2476(8)
_cell_measurement_reflns_used    2284
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4410
_cell_measurement_theta_min      5.8790
_cell_volume                     1241.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -56.00 -15.00   1.00    1.00    --  -33.50  37.00-150.00   41
  2  \w      1.00  35.00   1.00    1.00    --  -33.50  37.00-150.00   34
  3  \w    -88.00 -62.00   1.00    1.00    --  -33.50 -57.00 -30.00   26
  4  \w    -72.00 -39.00   1.00    1.00    --  -33.50 178.00  90.00   33
  5  \w    -44.00 -18.00   1.00    1.00    --  -33.50 -57.00 -30.00   26
  6  \w   -107.00 -80.00   1.00    1.00    --  -33.50 178.00-180.00   27
  7  \w     73.00  99.00   1.00    1.00    --   36.47 178.00  90.00   26
  8  \w    104.00 139.00   1.00    1.00    --  108.00 111.00   0.00   35
  9  \w     52.00  99.00   1.00    1.00    --  108.00 -94.00  30.00   47
 10  \w     44.00  97.00   1.00    1.00    --  108.00 -61.00  90.00   53
 11  \w     41.00  82.00   1.00    1.00    --  108.00-111.00 120.00   41
 12  \w     59.00  99.00   1.00    1.00    --  108.00 -94.00-180.00   40
 13  \w     88.00 170.00   1.00    1.00    --  108.00  45.00 -90.00   82
 14  \w   -102.00 -71.00   1.00    1.00    --  -33.50 -57.00   0.00   31
 15  \w    -46.00 -20.00   1.00    1.00    --  -33.50 -57.00   0.00   26
 16  \w     70.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   40
 17  \w     57.00  83.00   1.00    1.00    --  108.00 -45.00 -60.00   26
 18  \w    143.00 175.00   1.00    1.00    --  108.00  77.00 -60.00   32
 19  \w     42.00  68.00   1.00    1.00    --  108.00-111.00 -90.00   26
 20  \w    101.00 127.00   1.00    1.00    --  108.00  77.00 -60.00   26
 21  \w     97.00 128.00   1.00    1.00    --  108.00 -45.00 -60.00   31
 22  \w    109.00 140.00   1.00    1.00    --  108.00 111.00-150.00   31
 23  \w   -104.00 -51.00   1.00    1.00    --  -33.50 -37.00 150.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1903804000
_diffrn_orient_matrix_UB_12      0.0603638000
_diffrn_orient_matrix_UB_13      -0.0354064000
_diffrn_orient_matrix_UB_21      -0.1747599000
_diffrn_orient_matrix_UB_22      0.0284362000
_diffrn_orient_matrix_UB_23      0.0411875000
_diffrn_orient_matrix_UB_31      0.0884593000
_diffrn_orient_matrix_UB_32      0.1860304000
_diffrn_orient_matrix_UB_33      0.0051715000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4577
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.272
_diffrn_reflns_theta_min         5.890
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       0.0061(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.1847P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2077
_reflns_number_total             2320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0409_suppl_001.cif
_cod_data_source_block           2
_cod_original_cell_volume        1241.37(8)
_cod_database_code               8107705
_shelx_estimated_absorpt_t_max   0.591
_shelx_estimated_absorpt_t_min   0.473
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.800