#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226704.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_2226704
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 4-Chloro-N-(3-chlorophenyl)-2-methylbenzenesulfonamide
;
_journal_coeditor_code           VM2031
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1702
_journal_paper_doi               10.1107/S1600536810022968
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H11 Cl2 N O2 S'
_chemical_formula_moiety         'C13 H11 Cl2 N O2 S'
_chemical_formula_sum            'C13 H11 Cl2 N O2 S'
_chemical_formula_weight         316.19
_chemical_name_systematic
;
4-Chloro-N-(3-chlorophenyl)-2-methylbenzenesulfonamide
;
_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                 91.490(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9757(7)
_cell_length_b                   11.3472(8)
_cell_length_c                   15.5690(10)
_cell_measurement_reflns_used    2107
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.55
_cell_volume                     1408.55(18)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi scans
;
_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  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5849
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.8117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.518
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2866
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0554
_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)+(0.0763P)²+0.8836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                1853
_reflns_number_total             2866
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            vm2031.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226704
_cod_database_fobs_code          2226704
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_disorder_assembly
_atom_site_disorder_group
C C1 0.3431(4) 0.2031(3) 0.66150(19) 0.0451(7) Uani d . 1 . .
C C2 0.3719(5) 0.2761(3) 0.7319(2) 0.0571(9) Uani d . 1 . .
H H2 0.4793 0.2818 0.7563 0.069 Uiso calc R 1 . .
C C3 0.2436(6) 0.3398(3) 0.7657(2) 0.0642(10) Uani d . 1 . .
H H3 0.2638 0.3897 0.8122 0.077 Uiso calc R 1 . .
C C4 0.0858(5) 0.3293(3) 0.7305(2) 0.0617(10) Uani d . 1 . .
C C5 0.0557(5) 0.2571(3) 0.6608(3) 0.0630(10) Uani d . 1 . .
H H5 -0.0530 0.2507 0.6383 0.076 Uiso calc R 1 . .
C C6 0.1829(4) 0.1936(3) 0.6234(2) 0.0508(8) Uani d . 1 . .
C C7 0.6346(4) 0.2765(3) 0.5046(2) 0.0486(8) Uani d . 1 . .
C C8 0.6426(4) 0.3741(3) 0.5575(2) 0.0543(8) Uani d . 1 . .
H H8 0.5940 0.3729 0.6111 0.065 Uiso calc R 1 . .
C C9 0.7240(5) 0.4732(3) 0.5292(2) 0.0585(9) Uani d . 1 . .
C C10 0.7951(6) 0.4781(4) 0.4506(3) 0.0809(13) Uani d . 1 . .
H H10 0.8492 0.5459 0.4325 0.097 Uiso calc R 1 . .
C C11 0.7847(6) 0.3796(4) 0.3983(3) 0.0887(15) Uani d . 1 . .
H H11 0.8319 0.3815 0.3444 0.106 Uiso calc R 1 . .
C C12 0.7061(5) 0.2795(4) 0.4249(2) 0.0641(10) Uani d . 1 . .
H H12 0.7007 0.2137 0.3893 0.077 Uiso calc R 1 . .
C C13 0.1457(5) 0.1168(3) 0.5412(2) 0.0595(10) Uani d . 1 . .
H H13A 0.1807 0.0371 0.5519 0.071 Uiso calc R 1 . .
H H13B 0.2060 0.1481 0.4937 0.071 Uiso calc R 1 . .
H H13C 0.0276 0.1182 0.5276 0.071 Uiso calc R 1 . .
N N1 0.5495(4) 0.1719(3) 0.5270(2) 0.0640(9) Uani d D 1 . .
H H1N 0.539(5) 0.120(3) 0.488(2) 0.077 Uiso d D 1 . .
O O1 0.6571(3) 0.1510(2) 0.67778(17) 0.0697(7) Uani d . 1 . .
O O2 0.4690(3) 0.0031(2) 0.61100(16) 0.0660(7) Uani d . 1 . .
Cl Cl1 -0.0771(2) 0.41129(13) 0.77137(10) 0.1162(6) Uani d . 1 . .
Cl Cl2 0.73479(16) 0.59549(9) 0.59594(8) 0.0858(4) Uani d . 1 . .
S S1 0.51639(11) 0.12421(7) 0.62307(6) 0.0533(3) Uani 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'
Cl Cl 0.1484 0.1585 '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'
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_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.7(3) ?
C2 C1 S1 . . 117.1(3) ?
C6 C1 S1 . . 122.1(2) ?
C3 C2 C1 . . 120.6(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.3(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.6(4) ?
C3 C4 Cl1 . . 119.9(3) ?
C5 C4 Cl1 . . 119.5(3) ?
C4 C5 C6 . . 121.8(4) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 116.9(3) ?
C5 C6 C13 . . 120.4(3) ?
C1 C6 C13 . . 122.7(3) ?
C12 C7 C8 . . 120.2(3) ?
C12 C7 N1 . . 117.0(3) ?
C8 C7 N1 . . 122.8(3) ?
C9 C8 C7 . . 118.7(3) ?
C9 C8 H8 . . 120.7 ?
C7 C8 H8 . . 120.7 ?
C10 C9 C8 . . 122.1(4) ?
C10 C9 Cl2 . . 119.4(3) ?
C8 C9 Cl2 . . 118.5(3) ?
C9 C10 C11 . . 118.4(4) ?
C9 C10 H10 . . 120.8 ?
C11 C10 H10 . . 120.8 ?
C12 C11 C10 . . 121.0(4) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C11 C12 C7 . . 119.7(4) ?
C11 C12 H12 . . 120.1 ?
C7 C12 H12 . . 120.1 ?
C6 C13 H13A . . 109.5 ?
C6 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C6 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C7 N1 S1 . . 126.7(3) ?
C7 N1 H1N . . 116(3) ?
S1 N1 H1N . . 115(3) ?
O1 S1 O2 . . 118.89(17) ?
O1 S1 N1 . . 109.67(17) ?
O2 S1 N1 . . 104.33(16) ?
O1 S1 C1 . . 107.51(16) ?
O2 S1 C1 . . 108.91(15) ?
N1 S1 C1 . . 106.97(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.388(4) ?
C1 C6 . 1.399(5) ?
C1 S1 . 1.764(3) ?
C2 C3 . 1.369(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.365(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(5) ?
C4 Cl1 . 1.733(4) ?
C5 C6 . 1.386(5) ?
C5 H5 . 0.9300 ?
C6 C13 . 1.571(5) ?
C7 C12 . 1.380(5) ?
C7 C8 . 1.380(5) ?
C7 N1 . 1.416(4) ?
C8 C9 . 1.377(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.362(6) ?
C9 Cl2 . 1.734(4) ?
C10 C11 . 1.384(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.366(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 S1 . 1.619(3) ?
N1 H1N . 0.850(18) ?
O1 S1 . 1.424(3) ?
O2 S1 . 1.436(2) ?
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 H1N O2 3_656 0.850(18) 2.08(2) 2.926(4) 175(4)
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
C6 C1 C2 C3 . . . . 0.4(5) ?
S1 C1 C2 C3 . . . . -179.7(3) ?
C1 C2 C3 C4 . . . . 1.2(5) ?
C2 C3 C4 C5 . . . . -1.0(5) ?
C2 C3 C4 Cl1 . . . . -178.9(3) ?
C3 C4 C5 C6 . . . . -0.7(6) ?
Cl1 C4 C5 C6 . . . . 177.2(3) ?
C4 C5 C6 C1 . . . . 2.1(5) ?
C4 C5 C6 C13 . . . . -177.0(3) ?
C2 C1 C6 C5 . . . . -2.0(5) ?
S1 C1 C6 C5 . . . . 178.1(2) ?
C2 C1 C6 C13 . . . . 177.2(3) ?
S1 C1 C6 C13 . . . . -2.8(4) ?
C12 C7 C8 C9 . . . . -0.5(5) ?
N1 C7 C8 C9 . . . . -178.1(3) ?
C7 C8 C9 C10 . . . . 0.6(6) ?
C7 C8 C9 Cl2 . . . . -179.7(3) ?
C8 C9 C10 C11 . . . . -0.2(7) ?
Cl2 C9 C10 C11 . . . . -179.9(4) ?
C9 C10 C11 C12 . . . . -0.4(7) ?
C10 C11 C12 C7 . . . . 0.5(7) ?
C8 C7 C12 C11 . . . . -0.1(6) ?
N1 C7 C12 C11 . . . . 177.6(4) ?
C12 C7 N1 S1 . . . . 155.4(3) ?
C8 C7 N1 S1 . . . . -27.0(5) ?
C7 N1 S1 O1 . . . . -36.2(4) ?
C7 N1 S1 O2 . . . . -164.6(3) ?
C7 N1 S1 C1 . . . . 80.1(3) ?
C2 C1 S1 O1 . . . . 2.0(3) ?
C6 C1 S1 O1 . . . . -178.1(3) ?
C2 C1 S1 O2 . . . . 132.0(3) ?
C6 C1 S1 O2 . . . . -48.0(3) ?
C2 C1 S1 N1 . . . . -115.7(3) ?
C6 C1 S1 N1 . . . . 64.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745330
