#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222383.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_2222383
loop_
_publ_author_name
'Arshad, Muhammad Nadeem'
'Khan, Islam Ullah'
'Akkurt, Mehmet'
'Shafiq, Muhammad'
'Mustafa, Ghulam'
_publ_section_title
;
 2-(4-Bromobenzenesulfonamido)benzoic acid
;
_journal_coeditor_code           IS2431
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1610
_journal_page_last               o1611
_journal_paper_doi               10.1107/S1600536809022545
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 Br N O4 S'
_chemical_formula_moiety         'C13 H10 Br N O4 S'
_chemical_formula_sum            'C13 H10 Br N O4 S'
_chemical_formula_weight         356.19
_chemical_name_systematic
;
2-(4-Bromobenzenesulfonamido)benzoic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.196(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.8316(11)
_cell_length_b                   8.5684(4)
_cell_length_c                   11.6632(5)
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.04
_cell_measurement_theta_min      2.49
_cell_volume                     2752.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa-APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14822
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    3.149
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
'[Cubic fit to sin(θ)/λ - 24 parameters; Parkin et al., 1995]'
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.033P)²+1.5317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                1764
_reflns_number_total             3416
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2431.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222383
_cod_database_fobs_code          2222383
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.819170(10) 0.43825(6) 0.51473(4) 0.1153(2) Uani . . 1.000
S S1 0.62425(3) 0.44674(8) 0.15544(6) 0.0547(2) Uani . . 1.000
O O1 0.53281(7) 0.4722(2) 0.39261(16) 0.0628(7) Uani . . 1.000
O O2 0.50891(7) 0.2889(2) 0.50674(17) 0.0721(8) Uani . . 1.000
O O3 0.61345(8) 0.6071(2) 0.13563(17) 0.0713(8) Uani . . 1.000
O O4 0.63014(7) 0.3473(2) 0.06120(15) 0.0665(7) Uani . . 1.000
N N1 0.58022(7) 0.3824(2) 0.22029(18) 0.0555(8) Uani . . 1.000
C C1 0.67716(9) 0.4336(3) 0.2571(2) 0.0514(9) Uani . . 1.000
C C2 0.71403(11) 0.3319(3) 0.2413(3) 0.0659(11) Uani . . 1.000
C C3 0.75605(11) 0.3324(4) 0.3185(3) 0.0788(14) Uani . . 1.000
C C4 0.76082(11) 0.4310(4) 0.4111(3) 0.0705(11) Uani . . 1.000
C C5 0.72375(12) 0.5304(4) 0.4281(3) 0.0782(14) Uani . . 1.000
C C6 0.68182(12) 0.5303(4) 0.3517(3) 0.0714(12) Uani . . 1.000
C C7 0.57612(8) 0.2291(3) 0.2636(2) 0.0488(9) Uani . . 1.000
C C8 0.55269(8) 0.2054(3) 0.3611(2) 0.0505(9) Uani . . 1.000
C C9 0.54903(10) 0.0538(4) 0.4003(3) 0.0685(11) Uani . . 1.000
C C10 0.56676(11) -0.0710(4) 0.3463(3) 0.0788(14) Uani . . 1.000
C C11 0.58873(11) -0.0459(3) 0.2499(3) 0.0726(11) Uani . . 1.000
C C12 0.59331(10) 0.1022(3) 0.2086(3) 0.0606(10) Uani . . 1.000
C C13 0.53137(9) 0.3347(4) 0.4206(2) 0.0562(10) Uani . . 1.000
H H1 0.55740 0.44700 0.22910 0.0670 Uiso calc R 1.000
H H2 0.71040 0.26350 0.17880 0.0790 Uiso calc R 1.000
H H2A 0.49850 0.36530 0.53760 0.1080 Uiso calc R 1.000
H H3 0.78130 0.26550 0.30760 0.0940 Uiso calc R 1.000
H H5 0.72720 0.59740 0.49150 0.0940 Uiso calc R 1.000
H H6 0.65640 0.59580 0.36380 0.0860 Uiso calc R 1.000
H H9 0.53410 0.03640 0.46550 0.0820 Uiso calc R 1.000
H H10 0.56390 -0.17150 0.37460 0.0940 Uiso calc R 1.000
H H11 0.60060 -0.13020 0.21220 0.0870 Uiso calc R 1.000
H H12 0.60810 0.11760 0.14300 0.0730 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O4 . . . 120.06(12) no
O3 S1 N1 . . . 104.36(12) no
O3 S1 C1 . . . 108.04(13) no
O4 S1 N1 . . . 109.57(11) no
O4 S1 C1 . . . 107.82(12) no
N1 S1 C1 . . . 106.21(11) no
C13 O2 H2A . . . 109.00 no
S1 N1 C7 . . . 125.76(16) no
C7 N1 H1 . . . 117.00 no
S1 N1 H1 . . . 117.00 no
S1 C1 C2 . . . 121.2(2) no
S1 C1 C6 . . . 118.6(2) no
C2 C1 C6 . . . 120.2(3) no
C1 C2 C3 . . . 119.5(3) no
C2 C3 C4 . . . 120.0(3) no
Br1 C4 C3 . . . 120.5(2) no
Br1 C4 C5 . . . 118.9(3) no
C3 C4 C5 . . . 120.6(3) no
C4 C5 C6 . . . 119.7(3) no
C1 C6 C5 . . . 120.0(3) no
C8 C7 C12 . . . 119.6(2) no
N1 C7 C12 . . . 120.9(2) no
N1 C7 C8 . . . 119.5(2) no
C7 C8 C9 . . . 117.9(2) no
C7 C8 C13 . . . 122.5(2) no
C9 C8 C13 . . . 119.7(2) no
C8 C9 C10 . . . 122.2(3) no
C9 C10 C11 . . . 119.2(3) no
C10 C11 C12 . . . 120.6(3) no
C7 C12 C11 . . . 120.7(3) no
O1 C13 O2 . . . 121.8(3) no
O1 C13 C8 . . . 124.5(2) no
O2 C13 C8 . . . 113.7(3) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
C8 C9 H9 . . . 119.00 no
C10 C9 H9 . . . 119.00 no
C9 C10 H10 . . . 120.00 no
C11 C10 H10 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C7 C12 H12 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 . . 1.882(3) no
S1 O3 . . 1.4184(19) no
S1 O4 . . 1.4186(19) no
S1 N1 . . 1.625(2) no
S1 C1 . . 1.758(3) no
O1 C13 . . 1.225(4) no
O2 C13 . . 1.317(3) no
O2 H2A . . 0.8200 no
N1 C7 . . 1.418(3) no
N1 H1 . . 0.8600 no
C1 C6 . . 1.371(4) no
C1 C2 . . 1.379(4) no
C2 C3 . . 1.371(5) no
C3 C4 . . 1.363(5) no
C4 C5 . . 1.374(5) no
C5 C6 . . 1.364(5) no
C7 C12 . . 1.382(4) no
C7 C8 . . 1.404(3) no
C8 C13 . . 1.476(4) no
C8 C9 . . 1.386(4) no
C9 C10 . . 1.368(5) no
C10 C11 . . 1.371(5) no
C11 C12 . . 1.370(4) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 C9 3.662(3) . 7_656 no
Br1 C10 3.540(3) . 7_656 no
Br1 C11 3.599(3) . 7_656 no
S1 H12 2.8600 . . no
O1 N1 2.670(3) . . no
O1 O2 2.703(3) . 3_666 no
O2 O3 3.205(3) . 4_565 no
O2 O1 2.703(3) . 3_666 no
O3 C11 3.369(3) . 1_565 no
O3 C13 3.182(3) . 4_564 no
O3 O2 3.205(3) . 4_564 no
O4 C6 3.185(4) . 4_564 no
O4 C5 3.384(4) . 4_564 no
O4 C12 2.987(3) . . no
O1 H1 2.1300 . . no
O1 H2A 1.8900 . 3_666 no
O1 H1 2.7100 . 2_655 no
O2 H9 2.3500 . . no
O2 H10 2.8000 . 3_656 no
O3 H11 2.4700 . 1_565 no
O3 H6 2.7600 . . no
O4 H12 2.3100 . . no
O4 H2 2.5500 . . no
O4 H6 2.5600 . 4_564 no
N1 O1 2.670(3) . . no
N1 C13 3.325(3) . 2_655 no
C5 O4 3.384(4) . 4_565 no
C6 O4 3.185(4) . 4_565 no
C7 C13 3.543(3) . 2_655 no
C9 Br1 3.661(3) . 7_656 no
C10 Br1 3.540(3) . 7_656 no
C11 Br1 3.599(3) . 7_656 no
C11 O3 3.369(3) . 1_545 no
C12 O4 2.987(3) . . no
C13 N1 3.325(3) . 2_655 no
C13 O3 3.182(3) . 4_565 no
C13 C7 3.543(3) . 2_655 no
C2 H5 3.0500 . 4_564 no
C5 H2 3.0900 . 6_655 no
C6 H3 3.0200 . 6_655 no
C9 H9 3.0700 . 3_656 no
C13 H1 2.6300 . . no
C13 H1 2.9700 . 2_655 no
C13 H2A 2.7700 . 3_666 no
H1 O1 2.1300 . . no
H1 C13 2.6300 . . no
H1 O1 2.7100 . 2_655 no
H1 C13 2.9700 . 2_655 no
H2 O4 2.5500 . . no
H2 H5 2.5900 . 4_564 no
H2 C5 3.0900 . 6_645 no
H2A O1 1.8900 . 3_666 no
H2A C13 2.7700 . 3_666 no
H2A H2A 2.4700 . 3_666 no
H3 C6 3.0200 . 6_645 no
H5 C2 3.0500 . 4_565 no
H5 H2 2.5900 . 4_565 no
H6 O3 2.7600 . . no
H6 O4 2.5600 . 4_565 no
H9 O2 2.3500 . . no
H9 C9 3.0700 . 3_656 no
H9 H9 2.2500 . 3_656 no
H10 O2 2.8000 . 3_656 no
H11 O3 2.4700 . 1_545 no
H12 S1 2.8600 . . no
H12 O4 2.3100 . . no
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
N1 H1 O1 . 0.86 2.13 2.670(3) 121 yes
O2 H2A O1 3_666 0.82 1.89 2.703(3) 173 yes
C6 H6 O4 4_565 0.93 2.56 3.185(4) 125 yes
C11 H11 O3 1_545 0.93 2.47 3.369(3) 164 yes
C12 H12 O4 . 0.93 2.31 2.987(3) 130 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
O3 S1 N1 C7 . . . . -176.5(2) no
O4 S1 N1 C7 . . . . 53.8(2) no
C1 S1 N1 C7 . . . . -62.4(2) no
O3 S1 C1 C2 . . . . -135.0(2) no
O4 S1 C1 C2 . . . . -3.8(3) no
N1 S1 C1 C2 . . . . 113.6(2) no
O3 S1 C1 C6 . . . . 43.2(3) no
O4 S1 C1 C6 . . . . 174.3(2) no
N1 S1 C1 C6 . . . . -68.3(3) no
S1 N1 C7 C8 . . . . 149.12(19) no
S1 N1 C7 C12 . . . . -33.3(3) no
S1 C1 C6 C5 . . . . -175.6(3) no
S1 C1 C2 C3 . . . . 175.7(2) no
C6 C1 C2 C3 . . . . -2.4(4) no
C2 C1 C6 C5 . . . . 2.5(5) no
C1 C2 C3 C4 . . . . 1.1(5) no
C2 C3 C4 C5 . . . . 0.1(5) no
C2 C3 C4 Br1 . . . . -177.7(2) no
Br1 C4 C5 C6 . . . . 177.9(3) no
C3 C4 C5 C6 . . . . 0.0(5) no
C4 C5 C6 C1 . . . . -1.3(5) no
N1 C7 C8 C9 . . . . 179.5(2) no
N1 C7 C8 C13 . . . . 0.7(3) no
C12 C7 C8 C9 . . . . 1.8(4) no
C12 C7 C8 C13 . . . . -177.0(2) no
N1 C7 C12 C11 . . . . -179.2(3) no
C8 C7 C12 C11 . . . . -1.6(4) no
C7 C8 C9 C10 . . . . -0.9(4) no
C13 C8 C9 C10 . . . . 177.9(3) no
C7 C8 C13 O1 . . . . -1.4(4) no
C7 C8 C13 O2 . . . . 176.9(2) no
C9 C8 C13 O1 . . . . 179.9(3) no
C9 C8 C13 O2 . . . . -1.9(3) no
C8 C9 C10 C11 . . . . -0.3(5) no
C9 C10 C11 C12 . . . . 0.6(5) no
C10 C11 C12 C7 . . . . 0.3(5) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 36442
