#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/78/2237879.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_2237879
loop_
_publ_author_name
'Munir, Ayesha'
'Mubashar-ur-Rehman, Hafiz'
'Asiri, Abdullah M.'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
_publ_section_title
;
 2-Chloro-6-(2,3-dichlorobenzenesulfonamido)benzoic acid
;
_journal_coeditor_code           HG5312
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o832
_journal_paper_doi               10.1107/S1600536813011574
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H8 Cl3 N O4 S'
_chemical_formula_moiety         'C13 H8 Cl3 N O4 S'
_chemical_formula_sum            'C13 H8 Cl3 N O4 S'
_chemical_formula_weight         380.61
_chemical_name_systematic
;
2-Chloro-6-(2,3-dichlorobenzenesulfonamido)benzoic 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                90.00
_cell_angle_beta                 111.653(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0164(3)
_cell_length_b                   18.6017(5)
_cell_length_c                   9.8574(3)
_cell_measurement_reflns_used    5339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.9694
_cell_measurement_theta_min      4.7506
_cell_volume                     1536.62(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001)
;
_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
;
Agilent SuperNova (Dual, Cu at zero, Atlas, CCD)
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11742
_diffrn_reflns_theta_full        73.13
_diffrn_reflns_theta_max         73.13
_diffrn_reflns_theta_min         5.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.597
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0382
_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)+(0.0471P)²+1.0131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                2597
_reflns_number_total             3018
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5312.cif
_cod_data_source_block           I
_cod_original_cell_volume        1536.62(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2237879
_cod_database_fobs_code          2237879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl Cl1 0.21203(15) 0.41272(5) 0.58195(14) 0.1161(5) Uani d . 1 1
Cl Cl2 0.17428(9) 0.55156(5) 0.74492(8) 0.0718(3) Uani d . 1 1
Cl Cl3 0.94473(9) 0.58369(5) 1.01517(11) 0.0797(3) Uani d . 1 1
S S1 0.24536(6) 0.70690(3) 0.62789(6) 0.03763(17) Uani d . 1 1
O O1 0.1045(2) 0.71147(11) 0.6596(2) 0.0562(5) Uani d . 1 1
O O2 0.2792(2) 0.76184(9) 0.54279(18) 0.0482(4) Uani d . 1 1
O O3 0.5137(2) 0.59728(8) 1.02304(19) 0.0460(4) Uani d . 1 1
H H3 0.4816 0.5600 1.0473 0.055 Uiso calc R 1 1
O O4 0.6012(2) 0.52066(9) 0.8971(2) 0.0572(5) Uani d . 1 1
N N1 0.3928(2) 0.70318(10) 0.78616(19) 0.0357(4) Uani d . 1 1
H H1 0.3706 0.7032 0.8638 0.043 Uiso calc R 1 1
C C1 0.2524(3) 0.62421(13) 0.5405(2) 0.0417(5) Uani d . 1 1
C C2 0.2255(3) 0.55805(14) 0.5932(3) 0.0510(6) Uani d . 1 1
C C3 0.2403(4) 0.49629(16) 0.5195(4) 0.0693(9) Uani d . 1 1
C C4 0.2779(4) 0.5009(2) 0.3962(4) 0.0843(11) Uani d . 1 1
H H4 0.2867 0.4592 0.3476 0.101 Uiso calc R 1 1
C C5 0.3022(5) 0.5663(2) 0.3450(4) 0.0804(10) Uani d . 1 1
H H5 0.3269 0.5691 0.2615 0.096 Uiso calc R 1 1
C C6 0.2903(4) 0.62797(17) 0.4168(3) 0.0583(7) Uani d . 1 1
H H6 0.3078 0.6724 0.3823 0.070 Uiso calc R 1 1
C C7 0.5563(2) 0.69989(11) 0.8019(2) 0.0327(4) Uani d . 1 1
C C8 0.6539(2) 0.64427(11) 0.8821(2) 0.0329(4) Uani d . 1 1
C C9 0.8156(3) 0.64584(13) 0.9024(3) 0.0418(5) Uani d . 1 1
C C10 0.8775(3) 0.69735(14) 0.8382(3) 0.0485(6) Uani d . 1 1
H H10 0.9852 0.6970 0.8518 0.058 Uiso calc R 1 1
C C11 0.7777(3) 0.74919(15) 0.7535(3) 0.0536(7) Uani d . 1 1
H H11 0.8175 0.7829 0.7061 0.064 Uiso calc R 1 1
C C12 0.6188(3) 0.75223(13) 0.7376(3) 0.0467(6) Uani d . 1 1
H H12 0.5540 0.7892 0.6840 0.056 Uiso calc R 1 1
C C13 0.5870(3) 0.58240(11) 0.9374(2) 0.0348(4) Uani 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'
Cl Cl 0.3639 0.7018 '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
O1 S1 O2 119.37(11)
O1 S1 N1 105.73(10)
O2 S1 N1 108.47(10)
O1 S1 C1 110.74(12)
O2 S1 C1 106.38(11)
N1 S1 C1 105.32(10)
C13 O3 H3 109.5
C7 N1 S1 123.33(14)
C7 N1 H1 118.3
S1 N1 H1 118.3
C6 C1 C2 120.5(2)
C6 C1 S1 116.6(2)
C2 C1 S1 122.88(19)
C1 C2 C3 118.2(3)
C1 C2 Cl2 121.7(2)
C3 C2 Cl2 120.2(2)
C4 C3 C2 120.7(3)
C4 C3 Cl1 119.1(3)
C2 C3 Cl1 120.2(3)
C5 C4 C3 120.4(3)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.0(3)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 120.3(3)
C5 C6 H6 119.9
C1 C6 H6 119.9
C12 C7 C8 120.0(2)
C12 C7 N1 119.82(19)
C8 C7 N1 120.19(18)
C9 C8 C7 118.12(19)
C9 C8 C13 120.35(19)
C7 C8 C13 121.44(18)
C10 C9 C8 121.9(2)
C10 C9 Cl3 118.17(18)
C8 C9 Cl3 119.94(18)
C11 C10 C9 118.9(2)
C11 C10 H10 120.5
C9 C10 H10 120.5
C10 C11 C12 121.2(2)
C10 C11 H11 119.4
C12 C11 H11 119.4
C11 C12 C7 119.8(2)
C11 C12 H12 120.1
C7 C12 H12 120.1
O4 C13 O3 123.6(2)
O4 C13 C8 119.58(19)
O3 C13 C8 116.82(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.725(3)
Cl2 C2 1.725(3)
Cl3 C9 1.724(2)
S1 O1 1.4179(17)
S1 O2 1.4247(17)
S1 N1 1.6357(18)
S1 C1 1.776(2)
O3 C13 1.279(3)
O3 H3 0.8200
O4 C13 1.238(3)
N1 C7 1.426(3)
N1 H1 0.8600
C1 C6 1.384(3)
C1 C2 1.391(3)
C2 C3 1.391(4)
C3 C4 1.380(5)
C4 C5 1.366(5)
C4 H4 0.9300
C5 C6 1.373(4)
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.389(3)
C7 C8 1.399(3)
C8 C9 1.397(3)
C8 C13 1.493(3)
C9 C10 1.375(3)
C10 C11 1.372(4)
C10 H10 0.9300
C11 C12 1.383(3)
C11 H11 0.9300
C12 H12 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
N1 H1 O3 . 0.86 2.55 2.940(2) 108.4
C12 H12 O3 4_575 0.93 2.59 3.425(3) 150.3
O3 H3 O4 3_667 0.82 1.85 2.666(2) 176.4
N1 H1 O2 4_576 0.86 2.30 3.128(2) 161.9
C5 H5 O4 3_666 0.93 2.53 3.256(4) 135.2
C10 H10 O1 1_655 0.93 2.51 3.165(3) 127.2
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
O1 S1 N1 C7 -178.47(17)
O2 S1 N1 C7 -49.3(2)
C1 S1 N1 C7 64.24(19)
O1 S1 C1 C6 132.5(2)
O2 S1 C1 C6 1.4(2)
N1 S1 C1 C6 -113.6(2)
O1 S1 C1 C2 -49.0(2)
O2 S1 C1 C2 179.83(19)
N1 S1 C1 C2 64.8(2)
C6 C1 C2 C3 1.0(4)
S1 C1 C2 C3 -177.45(19)
C6 C1 C2 Cl2 -178.7(2)
S1 C1 C2 Cl2 2.9(3)
C1 C2 C3 C4 -1.1(4)
Cl2 C2 C3 C4 178.6(2)
C1 C2 C3 Cl1 178.77(19)
Cl2 C2 C3 Cl1 -1.5(3)
C2 C3 C4 C5 0.4(5)
Cl1 C3 C4 C5 -179.4(3)
C3 C4 C5 C6 0.4(6)
C4 C5 C6 C1 -0.5(5)
C2 C1 C6 C5 -0.2(4)
S1 C1 C6 C5 178.3(3)
S1 N1 C7 C12 55.1(3)
S1 N1 C7 C8 -125.01(19)
C12 C7 C8 C9 3.9(3)
N1 C7 C8 C9 -175.94(19)
C12 C7 C8 C13 -172.5(2)
N1 C7 C8 C13 7.6(3)
C7 C8 C9 C10 -4.4(3)
C13 C8 C9 C10 172.1(2)
C7 C8 C9 Cl3 173.60(17)
C13 C8 C9 Cl3 -9.9(3)
C8 C9 C10 C11 1.0(4)
Cl3 C9 C10 C11 -177.0(2)
C9 C10 C11 C12 3.0(4)
C10 C11 C12 C7 -3.4(4)
C8 C7 C12 C11 -0.2(4)
N1 C7 C12 C11 179.7(2)
C9 C8 C13 O4 -56.9(3)
C7 C8 C13 O4 119.5(2)
C9 C8 C13 O3 124.7(2)
C7 C8 C13 O3 -58.9(3)
