#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/38/1543875.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_1543875
loop_
_publ_author_name
'Rodrigues, Vinola Z.'
'Suchetan, P. A.'
'Saritha, L.'
'Lokanath, N. K.'
'Naveen, S.'
_publ_section_title
;
 4-Bromo-N-(4-fluorophenyl)benzenesulfonamide
;
_journal_coeditor_code           LH4010
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x161256
_journal_paper_doi               10.1107/S2414314616012566
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C12 H9 Br F N O2 S'
_chemical_formula_moiety         'C12 H9 Br F N O2 S'
_chemical_formula_sum            'C12 H9 Br F N O2 S'
_chemical_formula_weight         330.17
_chemical_name_systematic
;
4-Bromo-N-(4-fluorophenyl)benzenesulfonamide
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.7608(6)
_cell_length_b                   12.4156(4)
_cell_length_c                   5.0776(2)
_cell_measurement_reflns_used    137
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.1
_cell_measurement_theta_min      5.7
_cell_volume                     1245.75(7)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5649
_diffrn_reflns_theta_full        64.09
_diffrn_reflns_theta_max         64.09
_diffrn_reflns_theta_min         5.72
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  1
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    6.144
_exptl_absorpt_correction_T_max  0.311
_exptl_absorpt_correction_T_min  0.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.360
_refine_ls_abs_structure_details 'Flack (1983), 547 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1688
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                1621
_reflns_number_total             1688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh4010sup1.cif
_cod_data_source_block           I
_cod_database_code               1543875
_cod_database_fobs_code          1543875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.39127(18) 0.1909(3) 0.1353(8) 0.0265(8) Uani d . 1 1
C C2 0.34960(19) 0.1649(3) 0.3425(9) 0.0296(9) Uani d . 1 1
H H2 0.3549 0.0997 0.4302 0.036 Uiso calc R 1 1
C C3 0.2997(2) 0.2365(3) 0.4200(8) 0.0289(9) Uani d . 1 1
H H3 0.2707 0.2196 0.5580 0.035 Uiso calc R 1 1
C C4 0.29376(18) 0.3337(3) 0.2885(7) 0.0217(8) Uani d . 1 1
C C5 0.3370(2) 0.3607(4) 0.0829(8) 0.0300(10) Uani d . 1 1
H H5 0.3328 0.4267 -0.0022 0.036 Uiso calc R 1 1
C C6 0.38626(18) 0.2882(3) 0.0067(10) 0.0326(9) Uani d . 1 1
H H6 0.4157 0.3049 -0.1301 0.039 Uiso calc R 1 1
C C7 0.13069(18) 0.2839(3) 0.2275(7) 0.0227(8) Uani d . 1 1
C C8 0.08360(19) 0.2754(3) 0.4302(7) 0.0266(9) Uani d . 1 1
H H8 0.0739 0.3348 0.5351 0.032 Uiso calc R 1 1
C C9 0.05147(18) 0.1789(3) 0.4750(9) 0.0296(10) Uani d . 1 1
H H9 0.0208 0.1717 0.6129 0.035 Uiso calc R 1 1
C C10 0.0654(2) 0.0936(3) 0.3131(9) 0.0272(10) Uani d . 1 1
C C11 0.1114(2) 0.0990(3) 0.1087(9) 0.0290(10) Uani d . 1 1
H H11 0.1195 0.0398 0.0009 0.035 Uiso calc R 1 1
C C12 0.14518(19) 0.1957(3) 0.0700(8) 0.0276(9) Uani d . 1 1
H H12 0.1776 0.2014 -0.0620 0.033 Uiso calc R 1 1
N N1 0.16334(17) 0.3861(3) 0.1795(6) 0.0221(7) Uani d D 1 1
O O1 0.24522(13) 0.5284(2) 0.2820(5) 0.0270(6) Uani d . 1 1
O O2 0.20711(16) 0.4034(2) 0.6338(6) 0.0283(7) Uani d . 1 1
F F1 0.03373(12) -0.0025(2) 0.3541(6) 0.0388(6) Uani d . 1 1
S S1 0.22670(5) 0.42265(7) 0.3659(2) 0.0217(2) Uani d . 1 1
Br Br1 0.457510(19) 0.09041(3) 0.01845(10) 0.03674(18) Uani d . 1 1
H H1 0.170(2) 0.393(3) 0.005(3) 0.030(12) Uiso d D 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C2 C1 C6 121.7(4)
C2 C1 Br1 119.8(3)
C6 C1 Br1 118.5(3)
C1 C2 C3 119.6(4)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 118.9(4)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C5 121.4(4)
C3 C4 S1 120.0(3)
C5 C4 S1 118.4(3)
C6 C5 C4 119.1(4)
C6 C5 H5 120.5
C4 C5 H5 120.5
C1 C6 C5 119.3(4)
C1 C6 H6 120.3
C5 C6 H6 120.3
C12 C7 C8 120.3(4)
C12 C7 N1 120.3(3)
C8 C7 N1 119.4(4)
C9 C8 C7 119.8(4)
C9 C8 H8 120.1
C7 C8 H8 120.1
C10 C9 C8 118.8(4)
C10 C9 H9 120.6
C8 C9 H9 120.6
F1 C10 C9 119.6(4)
F1 C10 C11 117.3(4)
C9 C10 C11 123.1(4)
C10 C11 C12 117.7(4)
C10 C11 H11 121.1
C12 C11 H11 121.1
C7 C12 C11 120.2(4)
C7 C12 H12 119.9
C11 C12 H12 119.9
C7 N1 S1 119.2(2)
C7 N1 H1 108(3)
S1 N1 H1 116(3)
O1 S1 O2 120.34(16)
O1 S1 N1 106.20(17)
O2 S1 N1 107.23(17)
O1 S1 C4 108.41(17)
O2 S1 C4 107.98(18)
N1 S1 C4 105.81(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.374(6)
C1 C6 1.377(6)
C1 Br1 1.903(4)
C2 C3 1.385(6)
C2 H2 0.9300
C3 C4 1.384(6)
C3 H3 0.9300
C4 C5 1.390(5)
C4 S1 1.769(4)
C5 C6 1.382(6)
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.386(5)
C7 C8 1.392(5)
C7 N1 1.445(5)
C8 C9 1.375(6)
C8 H8 0.9300
C9 C10 1.369(6)
C9 H9 0.9300
C10 F1 1.363(5)
C10 C11 1.382(7)
C11 C12 1.388(6)
C11 H11 0.9300
C12 H12 0.9300
N1 S1 1.634(3)
N1 H1 0.900(10)
O1 S1 1.428(3)
O2 S1 1.434(3)
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
N1 H1 O2 1_554 0.900(17) 2.03(2) 2.911(4) 167(4)
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
C6 C1 C2 C3 2.1(6)
Br1 C1 C2 C3 -177.4(3)
C1 C2 C3 C4 -1.0(6)
C2 C3 C4 C5 -0.4(6)
C2 C3 C4 S1 175.3(3)
C3 C4 C5 C6 0.8(6)
S1 C4 C5 C6 -174.9(3)
C2 C1 C6 C5 -1.7(6)
Br1 C1 C6 C5 177.8(3)
C4 C5 C6 C1 0.2(6)
C12 C7 C8 C9 0.2(6)
N1 C7 C8 C9 179.0(4)
C7 C8 C9 C10 -1.8(6)
C8 C9 C10 F1 -179.7(4)
C8 C9 C10 C11 1.4(7)
F1 C10 C11 C12 -178.3(4)
C9 C10 C11 C12 0.6(7)
C8 C7 C12 C11 1.8(6)
N1 C7 C12 C11 -177.0(4)
C10 C11 C12 C7 -2.1(6)
C12 C7 N1 S1 -101.4(4)
C8 C7 N1 S1 79.8(4)
C7 N1 S1 O1 -176.5(3)
C7 N1 S1 O2 -46.7(3)
C7 N1 S1 C4 68.4(3)
C3 C4 S1 O1 158.8(3)
C5 C4 S1 O1 -25.4(4)
C3 C4 S1 O2 26.9(4)
C5 C4 S1 O2 -157.3(3)
C3 C4 S1 N1 -87.7(3)
C5 C4 S1 N1 88.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3447682
