#------------------------------------------------------------------------------
#$Date: 2016-04-20 04:24:51 +0300 (Wed, 20 Apr 2016) $
#$Revision: 182209 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/31/1543144.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_1543144
loop_
_publ_author_name
'Rodrigues, Vinola Z.'
'Naveen, S.'
'Lokanath, N. K.'
'Suchetan, P. A.'
_publ_section_title
;
 4-Bromo-N-(4-bromophenyl)benzenesulfonamide
;
_journal_coeditor_code           ZQ4006
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x160631
_journal_paper_doi               10.1107/S2414314616006313
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C12 H9 Br2 N O2 S'
_chemical_formula_moiety         'C12 H9 Br2 N O2 S'
_chemical_formula_sum            'C12 H9 Br2 N O2 S'
_chemical_formula_weight         391.08
_chemical_melting_point          413
_chemical_name_systematic
;
4-Bromo-N-(4-bromophenyl)benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 91.076(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0643(3)
_cell_length_b                   12.8006(7)
_cell_length_c                   20.5540(11)
_cell_measurement_reflns_used    167
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.5
_cell_measurement_theta_min      4.1
_cell_volume                     1332.20(13)
_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_detector_area_resol_mean 1
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ 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  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9589
_diffrn_reflns_theta_full        64.46
_diffrn_reflns_theta_max         64.46
_diffrn_reflns_theta_min         4.07
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  1
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    9.138
_exptl_absorpt_correction_T_max  0.2384
_exptl_absorpt_correction_T_min  0.1840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.154
_refine_diff_density_min         -1.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0613
_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)+(0.1331P)²+1.7178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1797
_refine_ls_wR_factor_ref         0.1811
_reflns_number_gt                2092
_reflns_number_total             2142
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            zq4006sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1543144
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.5612(9) 0.6558(3) 0.1853(2) 0.0144(9) Uani d . 1 1
C C2 0.6912(9) 0.5603(4) 0.1886(2) 0.0212(10) Uani d . 1 1
H H2 0.8316 0.5506 0.2178 0.025 Uiso calc R 1 1
C C3 0.6100(11) 0.4798(4) 0.1481(3) 0.0246(11) Uani d . 1 1
H H3 0.6959 0.4157 0.1497 0.030 Uiso calc R 1 1
C C4 0.3999(10) 0.4956(3) 0.1053(2) 0.0195(10) Uani d . 1 1
C C5 0.2722(10) 0.5905(4) 0.1016(2) 0.0225(10) Uani d . 1 1
H H5 0.1330 0.5999 0.0720 0.027 Uiso calc R 1 1
C C6 0.3507(10) 0.6715(4) 0.1418(2) 0.0174(10) Uani d . 1 1
H H6 0.2646 0.7356 0.1398 0.021 Uiso calc R 1 1
C C7 0.5220(8) 0.6491(3) 0.3422(2) 0.0122(9) Uani d . 1 1
C C8 0.3527(9) 0.5641(4) 0.3350(3) 0.0227(10) Uani d . 1 1
H H8 0.2089 0.5684 0.3063 0.027 Uiso calc R 1 1
C C9 0.3960(10) 0.4734(4) 0.3701(3) 0.0218(10) Uani d . 1 1
H H9 0.2810 0.4172 0.3655 0.026 Uiso calc R 1 1
C C10 0.6108(9) 0.4672(3) 0.4119(2) 0.0187(10) Uani d . 1 1
C C11 0.7797(10) 0.5524(4) 0.4209(2) 0.0230(10) Uani d . 1 1
H H11 0.9224 0.5483 0.4500 0.028 Uiso calc R 1 1
C C12 0.7313(10) 0.6431(4) 0.3860(2) 0.0201(10) Uani d . 1 1
H H12 0.8412 0.7006 0.3921 0.024 Uiso calc R 1 1
N N1 0.4784(7) 0.7427(3) 0.30503(18) 0.0142(8) Uani d D 1 1
O O1 0.5684(6) 0.8555(2) 0.21164(16) 0.0192(7) Uani d . 1 1
O O2 0.9253(6) 0.7423(2) 0.25806(16) 0.0189(7) Uani d . 1 1
S S1 0.65243(19) 0.75847(8) 0.23895(5) 0.0125(4) Uani d . 1 1
Br Br1 0.28679(13) 0.38445(4) 0.05096(3) 0.0339(3) Uani d . 1 1
Br Br2 0.68273(11) 0.34108(4) 0.45686(2) 0.0271(3) Uani d . 1 1
H H1 0.312(4) 0.751(4) 0.290(2) 0.010(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'
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 121.0(4)
C2 C1 S1 120.3(4)
C6 C1 S1 118.7(3)
C3 C2 C1 119.4(4)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 119.4(4)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 121.3(4)
C5 C4 Br1 119.6(4)
C3 C4 Br1 119.2(4)
C4 C5 C6 120.0(5)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 118.9(4)
C5 C6 H6 120.5
C1 C6 H6 120.5
C12 C7 C8 119.3(4)
C12 C7 N1 120.2(4)
C8 C7 N1 120.5(4)
C9 C8 C7 120.7(4)
C9 C8 H8 119.7
C7 C8 H8 119.7
C10 C9 C8 119.4(4)
C10 C9 H9 120.3
C8 C9 H9 120.3
C9 C10 C11 120.9(4)
C9 C10 Br2 119.8(3)
C11 C10 Br2 119.3(4)
C12 C11 C10 118.9(5)
C12 C11 H11 120.5
C10 C11 H11 120.5
C7 C12 C11 120.8(4)
C7 C12 H12 119.6
C11 C12 H12 119.6
C7 N1 S1 117.5(3)
C7 N1 H1 114(3)
S1 N1 H1 103(3)
O1 S1 O2 120.63(19)
O1 S1 N1 105.77(19)
O2 S1 N1 106.41(19)
O1 S1 C1 109.2(2)
O2 S1 C1 107.4(2)
N1 S1 C1 106.58(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.389(7)
C1 C6 1.393(7)
C1 S1 1.772(4)
C2 C3 1.381(7)
C2 H2 0.9300
C3 C4 1.382(7)
C3 H3 0.9300
C4 C5 1.377(7)
C4 Br1 1.892(5)
C5 C6 1.380(7)
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.380(7)
C7 C8 1.391(6)
C7 N1 1.435(6)
C8 C9 1.382(7)
C8 H8 0.9300
C9 C10 1.375(7)
C9 H9 0.9300
C10 C11 1.396(7)
C10 Br2 1.892(5)
C11 C12 1.385(7)
C11 H11 0.9300
C12 H12 0.9300
N1 S1 1.646(4)
N1 H1 0.895(10)
O1 S1 1.425(3)
O2 S1 1.445(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_455 0.90(3) 2.06(2) 2.945(5) 170(5)
C9 H9 O1 2_545 0.93 2.48 3.238(6) 138
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 -0.1(7)
S1 C1 C2 C3 177.3(4)
C1 C2 C3 C4 -0.4(7)
C2 C3 C4 C5 0.9(8)
C2 C3 C4 Br1 -179.1(4)
C3 C4 C5 C6 -1.0(8)
Br1 C4 C5 C6 179.0(4)
C4 C5 C6 C1 0.5(7)
C2 C1 C6 C5 0.0(7)
S1 C1 C6 C5 -177.5(4)
C12 C7 C8 C9 -1.5(7)
N1 C7 C8 C9 179.2(4)
C7 C8 C9 C10 -0.8(8)
C8 C9 C10 C11 2.3(8)
C8 C9 C10 Br2 -176.8(4)
C9 C10 C11 C12 -1.4(7)
Br2 C10 C11 C12 177.6(4)
C8 C7 C12 C11 2.3(7)
N1 C7 C12 C11 -178.4(4)
C10 C11 C12 C7 -0.9(7)
C12 C7 N1 S1 82.2(5)
C8 C7 N1 S1 -98.5(4)
C7 N1 S1 O1 179.3(3)
C7 N1 S1 O2 -51.3(4)
C7 N1 S1 C1 63.2(4)
C2 C1 S1 O1 158.4(4)
C6 C1 S1 O1 -24.1(4)
C2 C1 S1 O2 25.9(4)
C6 C1 S1 O2 -156.6(4)
C2 C1 S1 N1 -87.8(4)
C6 C1 S1 N1 89.7(4)

_cod_database_fobs_code 1543144
