#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/20/2212079.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_2212079
loop_
_publ_author_name
'Xiao-Wei Yan'
'Mao-Lin Hu'
'Jing Xiong'
_publ_section_title
;
 2-(5-Bromothiophene-2-sulfonamido)benzoic acid
;
_journal_coeditor_code           BX2058
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o678
_journal_page_last               o679
_journal_paper_doi               10.1107/S1600536807000852
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H8 Br N O4 S2'
_chemical_formula_moiety         'C11 H8 Br N O4 S2'
_chemical_formula_sum            'C11 H8 Br N O4 S2'
_chemical_formula_weight         362.21
_chemical_name_systematic
;
2-(2-bromothiophene-5-sulfonamido)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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.064(2)
_cell_length_b                   8.7216(7)
_cell_length_c                   10.7416(9)
_cell_measurement_reflns_used    2353
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.45
_cell_volume                     2581.4(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6547
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.516
_exptl_absorpt_correction_T_max  0.5761
_exptl_absorpt_correction_T_min  0.4013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0311
_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)+(0.037P)²+2.6357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                1878
_reflns_number_total             2287
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2058.cif
_cod_data_source_block           I
_cod_original_cell_volume        2581.5(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212079
_cod_database_fobs_code          2212079
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Br Br1 0.311413(12) 0.05488(4) 1.03021(3) 0.06301(16) Uani d . 1
S S1 0.12881(2) 0.04637(8) 0.65041(7) 0.03489(18) Uani d . 1
S S2 0.20606(3) 0.00995(9) 0.88666(7) 0.0454(2) Uani d . 1
O O1 0.00898(8) 0.2119(3) 1.0106(2) 0.0549(6) Uani d D 1
O O2 0.03287(7) 0.0292(2) 0.89142(19) 0.0438(5) Uani d . 1
O O3 0.12311(7) -0.1165(2) 0.6486(2) 0.0477(5) Uani d . 1
O O4 0.12511(7) 0.1294(2) 0.53483(17) 0.0439(5) Uani d . 1
N N1 0.08883(8) 0.1074(3) 0.7295(2) 0.0383(6) Uani d D 1
C C1 0.03179(9) 0.1646(4) 0.9213(3) 0.0403(7) Uani d . 1
C C2 0.05446(9) 0.2890(3) 0.8596(3) 0.0362(6) Uani d . 1
C C3 0.08139(9) 0.2597(3) 0.7645(2) 0.0331(6) Uani d . 1
C C4 0.09972(10) 0.3830(3) 0.7050(3) 0.0408(7) Uani d . 1
H H4 0.1171 0.3646 0.6410 0.049 Uiso calc R 1
C C5 0.09219(12) 0.5315(3) 0.7403(3) 0.0475(8) Uani d . 1
H H5 0.1043 0.6127 0.6995 0.057 Uiso calc R 1
C C6 0.06692(12) 0.5604(4) 0.8356(3) 0.0526(8) Uani d . 1
H H6 0.0626 0.6607 0.8606 0.063 Uiso calc R 1
C C7 0.04805(11) 0.4401(3) 0.8939(3) 0.0480(8) Uani d . 1
H H7 0.0307 0.4606 0.9576 0.058 Uiso calc R 1
C C8 0.18553(10) 0.0903(3) 0.7397(3) 0.0345(6) Uani d . 1
C C9 0.22004(10) 0.1771(3) 0.7015(3) 0.0451(7) Uani d . 1
H H9 0.2151 0.2304 0.6251 0.054 Uiso calc R 1
C C10 0.26424(11) 0.1784(4) 0.7894(3) 0.0498(8) Uani d . 1
H H10 0.2918 0.2315 0.7778 0.060 Uiso calc R 1
C C11 0.26155(10) 0.0932(3) 0.8924(3) 0.0427(7) Uani d . 1
H H1 0.0768(12) 0.039(3) 0.766(3) 0.051 Uiso d D 1
H H1A -0.0006(12) 0.135(3) 1.036(3) 0.051 Uiso d D 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O4 S1 O3 120.29(12) ?
O4 S1 N1 110.30(12) ?
O3 S1 N1 104.26(12) ?
O4 S1 C8 106.07(13) ?
O3 S1 C8 108.36(12) ?
N1 S1 C8 106.91(13) ?
C11 S2 C8 90.24(14) yes
C1 O1 H1A 103(3) ?
C3 N1 S1 127.06(19) ?
C3 N1 H1 118(2) ?
S1 N1 H1 114(2) ?
O2 C1 O1 122.2(3) ?
O2 C1 C2 123.8(3) ?
O1 C1 C2 114.0(3) ?
C7 C2 C3 118.7(3) ?
C7 C2 C1 119.3(3) ?
C3 C2 C1 122.0(3) ?
C4 C3 C2 119.3(3) ?
C4 C3 N1 121.2(2) ?
C2 C3 N1 119.6(2) ?
C5 C4 C3 120.5(3) ?
C5 C4 H4 119.7 ?
C3 C4 H4 119.7 ?
C6 C5 C4 120.4(3) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C5 C6 C7 119.7(3) ?
C5 C6 H6 120.1 ?
C7 C6 H6 120.1 ?
C6 C7 C2 121.4(3) ?
C6 C7 H7 119.3 ?
C2 C7 H7 119.3 ?
C9 C8 S2 111.8(2) yes
C9 C8 S1 126.1(2) ?
S2 C8 S1 121.86(16) ?
C8 C9 C10 113.0(3) ?
C8 C9 H9 123.5 ?
C10 C9 H9 123.5 ?
C11 C10 C9 111.5(3) ?
C11 C10 H10 124.2 ?
C9 C10 H10 124.2 ?
C10 C11 S2 113.4(2) yes
C10 C11 Br1 126.9(2) ?
S2 C11 Br1 119.61(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C11 1.864(3) yes
S1 O4 1.424(2) yes
S1 O3 1.430(2) ?
S1 N1 1.620(2) yes
S1 C8 1.738(3) yes
S2 C11 1.709(3) yes
S2 C8 1.723(3) yes
O1 C1 1.317(3) yes
O1 H1A 0.792(18) no
O2 C1 1.225(3) ?
N1 C3 1.407(3) ?
N1 H1 0.823(18) no
C1 C2 1.476(4) ?
C2 C7 1.390(4) ?
C2 C3 1.405(4) ?
C3 C4 1.398(4) ?
C4 C5 1.377(4) ?
C4 H4 0.9300 ?
C5 C6 1.375(5) ?
C5 H5 0.9300 ?
C6 C7 1.378(5) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.353(4) ?
C9 C10 1.410(4) ?
C9 H9 0.9300 ?
C10 C11 1.346(4) ?
C10 H10 0.9300 ?
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
C5 H5 O3 1_565 0.93 2.50 3.387(4) 158.8 yes
C7 H7 O1 . 0.93 2.35 2.694(4) 101.4 yes
C4 H4 O4 . 0.93 2.38 3.039(4) 127.9 yes
N1 H1 O2 . 0.823(18) 1.99(3) 2.644(3) 136(3) yes
O1 H1A O2 5_557 0.792(18) 1.934(19) 2.716(3) 169(4) 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
O4 S1 N1 C3 -53.4(3)
O3 S1 N1 C3 176.1(2)
C8 S1 N1 C3 61.5(3)
O2 C1 C2 C7 175.2(3)
O1 C1 C2 C7 -3.4(4)
O2 C1 C2 C3 -3.1(4)
O1 C1 C2 C3 178.3(2)
C7 C2 C3 C4 -1.8(4)
C1 C2 C3 C4 176.5(2)
C7 C2 C3 N1 179.2(3)
C1 C2 C3 N1 -2.5(4)
S1 N1 C3 C4 17.5(4)
S1 N1 C3 C2 -163.4(2)
C2 C3 C4 C5 1.0(4)
N1 C3 C4 C5 -179.9(3)
C3 C4 C5 C6 0.6(5)
C4 C5 C6 C7 -1.5(5)
C5 C6 C7 C2 0.8(5)
C3 C2 C7 C6 0.9(4)
C1 C2 C7 C6 -177.5(3)
C11 S2 C8 C9 -0.9(2)
C11 S2 C8 S1 173.71(18)
O4 S1 C8 C9 -4.4(3)
O3 S1 C8 C9 126.0(3)
N1 S1 C8 C9 -122.1(3)
O4 S1 C8 S2 -178.25(16)
O3 S1 C8 S2 -47.8(2)
N1 S1 C8 S2 64.0(2)
S2 C8 C9 C10 1.0(3)
S1 C8 C9 C10 -173.3(2)
C8 C9 C10 C11 -0.6(4)
C9 C10 C11 S2 -0.2(4)
C9 C10 C11 Br1 177.5(2)
C8 S2 C11 C10 0.6(3)
C8 S2 C11 Br1 -177.20(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3693604
