#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221367.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_2221367
loop_
_publ_author_name
'Arshad, Muhammad Nadeem'
'Tahir, M. Nawaz'
'Khan, Islam Ullah'
'Shafiq, Muhammad'
'Sharif, Hafiz Muhammad Adeel'
_publ_section_title
;
 5-Benzenesulfonamido-2-chlorobenzoic acid
;
_journal_coeditor_code           HB2925
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o831
_journal_paper_doi               10.1107/S1600536809009787
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 Cl N O4 S'
_chemical_formula_moiety         'C13 H10 Cl N O4 S'
_chemical_formula_sum            'C13 H10 Cl N O4 S'
_chemical_formula_weight         311.73
_chemical_name_systematic
;
5-Benzenesulfonamido-2-chlorobenzoic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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
_cell_angle_beta                 91.483(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7139(4)
_cell_length_b                   5.3957(2)
_cell_length_c                   20.7565(8)
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.10
_cell_volume                     1311.47(8)
_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) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14693
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0387
_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)+(0.048P)²+0.7097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                2513
_reflns_number_total             3269
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2925.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221367
_cod_database_fobs_code          2221367
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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
Cl Cl1 0.34738(5) 1.16021(13) -0.01036(3) 0.0671(2) Uani . . 1.000
S S1 0.18337(4) 0.37106(8) 0.24025(2) 0.03170(10) Uani . . 1.000
O O1 -0.00951(12) 1.2492(3) 0.05816(8) 0.0530(5) Uani . . 1.000
O O2 0.12244(13) 1.3665(3) -0.00925(8) 0.0557(5) Uani . . 1.000
O O3 0.08966(12) 0.2790(3) 0.27620(7) 0.0460(5) Uani . . 1.000
O O4 0.25750(12) 0.2023(3) 0.20902(7) 0.0420(4) Uani . . 1.000
N N1 0.12278(13) 0.5510(3) 0.18667(8) 0.0370(5) Uani . . 1.000
C C1 0.16292(15) 1.0292(3) 0.06222(9) 0.0320(5) Uani . . 1.000
C C2 0.11598(15) 0.8798(3) 0.10932(9) 0.0311(5) Uani . . 1.000
C C3 0.17784(15) 0.6911(3) 0.13923(9) 0.0313(5) Uani . . 1.000
C C4 0.28911(17) 0.6482(4) 0.12081(10) 0.0420(6) Uani . . 1.000
C C5 0.33651(18) 0.7953(4) 0.07447(11) 0.0465(7) Uani . . 1.000
C C6 0.27543(17) 0.9845(4) 0.04525(10) 0.0385(6) Uani . . 1.000
C C7 0.09147(16) 1.2312(4) 0.03343(9) 0.0344(6) Uani . . 1.000
C C8 0.26803(15) 0.5589(3) 0.29150(9) 0.0322(5) Uani . . 1.000
C C9 0.21566(19) 0.7353(4) 0.32856(11) 0.0484(7) Uani . . 1.000
C C10 0.2813(2) 0.8817(5) 0.36915(13) 0.0645(9) Uani . . 1.000
C C11 0.3978(2) 0.8482(5) 0.37292(13) 0.0655(10) Uani . . 1.000
C C12 0.4499(2) 0.6723(5) 0.33606(12) 0.0558(8) Uani . . 1.000
C C13 0.38461(17) 0.5253(4) 0.29468(10) 0.0432(7) Uani . . 1.000
H H1N 0.04957 0.56188 0.18730 0.0444 Uiso . . 1.000
H H1O -0.04283 1.36994 0.04279 0.0636 Uiso . . 1.000
H H2 0.04096 0.90730 0.12110 0.0374 Uiso . . 1.000
H H4 0.33146 0.52045 0.13970 0.0503 Uiso . . 1.000
H H5 0.41138 0.76657 0.06261 0.0558 Uiso . . 1.000
H H9 0.13680 0.75516 0.32615 0.0580 Uiso . . 1.000
H H10 0.24711 1.00298 0.39397 0.0773 Uiso . . 1.000
H H11 0.44182 0.94605 0.40084 0.0786 Uiso . . 1.000
H H12 0.52867 0.65190 0.33884 0.0670 Uiso . . 1.000
H H13 0.41898 0.40565 0.26941 0.0519 Uiso . . 1.000
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'
Cl Cl 0.1484 0.1585 '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 . . . 119.97(9) no
O3 S1 N1 . . . 103.69(9) no
O3 S1 C8 . . . 108.23(9) no
O4 S1 N1 . . . 109.31(9) no
O4 S1 C8 . . . 107.63(9) no
N1 S1 C8 . . . 107.41(8) no
C7 O1 H1O . . . 109.00 no
S1 N1 C3 . . . 126.74(13) no
C3 N1 H1N . . . 117.00 no
S1 N1 H1N . . . 117.00 no
C2 C1 C6 . . . 118.08(16) no
C2 C1 C7 . . . 118.53(16) no
C6 C1 C7 . . . 123.38(17) no
C1 C2 C3 . . . 121.90(16) no
N1 C3 C2 . . . 117.57(16) no
N1 C3 C4 . . . 123.56(16) no
C2 C3 C4 . . . 118.87(17) no
C3 C4 C5 . . . 119.72(19) no
C4 C5 C6 . . . 121.4(2) no
C1 C6 C5 . . . 120.03(19) no
Cl1 C6 C5 . . . 116.31(16) no
Cl1 C6 C1 . . . 123.64(16) no
O1 C7 O2 . . . 122.32(19) no
O1 C7 C1 . . . 113.71(17) no
O2 C7 C1 . . . 123.97(17) no
S1 C8 C9 . . . 118.95(15) no
S1 C8 C13 . . . 119.76(14) no
C9 C8 C13 . . . 121.29(18) no
C8 C9 C10 . . . 119.3(2) no
C9 C10 C11 . . . 119.8(2) no
C10 C11 C12 . . . 120.9(2) no
C11 C12 C13 . . . 119.7(2) no
C8 C13 C12 . . . 119.03(19) no
C1 C2 H2 . . . 119.00 no
C3 C2 H2 . . . 119.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 119.00 no
C6 C5 H5 . . . 119.00 no
C8 C9 H9 . . . 120.00 no
C10 C9 H9 . . . 120.00 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
C11 C12 H12 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C8 C13 H13 . . . 120.00 no
C12 C13 H13 . . . 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
Cl1 C6 . . 1.730(2) no
S1 O3 . . 1.4321(15) no
S1 O4 . . 1.4257(16) no
S1 N1 . . 1.6255(17) no
S1 C8 . . 1.7572(18) no
O1 C7 . . 1.305(2) no
O2 C7 . . 1.211(3) no
O1 H1O . . 0.8200 no
N1 C3 . . 1.411(2) no
N1 H1N . . 0.8600 no
C1 C6 . . 1.394(3) no
C1 C7 . . 1.490(3) no
C1 C2 . . 1.391(3) no
C2 C3 . . 1.387(2) no
C3 C4 . . 1.387(3) no
C4 C5 . . 1.375(3) no
C5 C6 . . 1.378(3) no
C8 C13 . . 1.378(3) no
C8 C9 . . 1.378(3) no
C9 C10 . . 1.375(3) no
C10 C11 . . 1.377(3) no
C11 C12 . . 1.372(4) no
C12 C13 . . 1.385(3) no
C2 H2 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 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
O1 H1O O2 3_585 0.82 1.83 2.648(2) 178 yes
N1 H1N O3 2_555 0.86 2.16 2.898(2) 144 yes
C4 H4 O4 . 0.93 2.41 3.052(3) 126 yes
C6 Cl1 CgB 4_564 1.730(2) 3.8131(12) 4.605(2) 106.16(8) yes
S1 O4 CgA 1_545 1.4257(16) 3.1405(17) 4.2532(9) 133.77(8) 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 C3 . . . . 179.16(16) no
O4 S1 N1 C3 . . . . -51.79(18) no
C8 S1 N1 C3 . . . . 64.71(17) no
O3 S1 C8 C9 . . . . -47.55(18) no
O3 S1 C8 C13 . . . . 131.51(16) no
O4 S1 C8 C9 . . . . -178.57(16) no
O4 S1 C8 C13 . . . . 0.48(18) no
N1 S1 C8 C9 . . . . 63.83(18) no
N1 S1 C8 C13 . . . . -117.12(16) no
S1 N1 C3 C2 . . . . -163.64(14) no
S1 N1 C3 C4 . . . . 17.0(3) no
C6 C1 C2 C3 . . . . 0.1(3) no
C7 C1 C2 C3 . . . . -178.76(17) no
C2 C1 C6 Cl1 . . . . -177.75(15) no
C2 C1 C6 C5 . . . . 0.6(3) no
C7 C1 C6 Cl1 . . . . 1.1(3) no
C7 C1 C6 C5 . . . . 179.40(19) no
C2 C1 C7 O1 . . . . 2.0(3) no
C2 C1 C7 O2 . . . . -177.51(19) no
C6 C1 C7 O1 . . . . -176.84(18) no
C6 C1 C7 O2 . . . . 3.7(3) no
C1 C2 C3 N1 . . . . 179.62(16) no
C1 C2 C3 C4 . . . . -1.0(3) no
N1 C3 C4 C5 . . . . -179.45(19) no
C2 C3 C4 C5 . . . . 1.2(3) no
C3 C4 C5 C6 . . . . -0.6(3) no
C4 C5 C6 Cl1 . . . . 178.09(17) no
C4 C5 C6 C1 . . . . -0.4(3) no
S1 C8 C9 C10 . . . . 179.51(18) no
C13 C8 C9 C10 . . . . 0.5(3) no
S1 C8 C13 C12 . . . . -179.00(17) no
C9 C8 C13 C12 . . . . 0.0(3) no
C8 C9 C10 C11 . . . . -0.9(4) no
C9 C10 C11 C12 . . . . 0.8(4) no
C10 C11 C12 C13 . . . . -0.3(4) no
C11 C12 C13 C8 . . . . -0.1(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741986
