#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228233
loop_
_publ_author_name
'Nirmala, P. G.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,3-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide
;
_journal_coeditor_code           BT5400
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3060
_journal_paper_doi               10.1107/S1600536810044338
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H13 Cl2 N O2 S'
_chemical_formula_moiety         'C14 H13 Cl2 N O2 S'
_chemical_formula_sum            'C14 H13 Cl2 N O2 S'
_chemical_formula_weight         330.21
_chemical_name_systematic
;
N-(2,3-dichlorophenyl)-2,4-dimethylbenzenesulfonamide
;
_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                 99.1000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1980(10)
_cell_length_b                   9.9330(10)
_cell_length_c                   16.099(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      22.47
_cell_measurement_theta_min      4.86
_cell_volume                     1452.4(3)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3394
_diffrn_reflns_theta_full        66.90
_diffrn_reflns_theta_max         66.90
_diffrn_reflns_theta_min         4.87
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.370
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.656
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0415
_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)+(0.0691P)²+0.3328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2367
_reflns_number_total             2581
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5400.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228233
_cod_database_fobs_code          2228233
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
Cl Cl1 0.25244(6) -0.10202(6) 0.09534(4) 0.05416(19) Uani d . 1 . .
Cl Cl2 -0.08838(6) -0.14100(6) 0.06647(4) 0.0576(2) Uani d . 1 . .
S S1 0.45032(5) 0.26140(5) 0.21630(3) 0.04180(18) Uani d . 1 . .
O O1 0.60015(16) 0.22571(19) 0.21346(11) 0.0561(4) Uani d . 1 . .
O O2 0.41640(18) 0.33596(18) 0.28705(10) 0.0545(4) Uani d . 1 . .
N N1 0.36407(18) 0.11597(18) 0.21294(12) 0.0432(4) Uani d D 1 . .
H H1N 0.409(3) 0.052(2) 0.1949(16) 0.052 Uiso d D 1 . .
C C1 0.3736(2) 0.3504(2) 0.12509(13) 0.0385(4) Uani d . 1 . .
C C2 0.3976(2) 0.3127(2) 0.04461(13) 0.0418(5) Uani d . 1 . .
C C3 0.3316(3) 0.3909(2) -0.02241(14) 0.0492(5) Uani d . 1 . .
H H3 0.3482 0.3688 -0.0763 0.059 Uiso calc R 1 . .
C C4 0.2427(3) 0.4999(2) -0.01297(16) 0.0535(6) Uani d . 1 . .
C C5 0.2205(3) 0.5337(2) 0.06777(17) 0.0592(6) Uani d . 1 . .
H H5 0.1606 0.6065 0.0757 0.071 Uiso calc R 1 . .
C C6 0.2859(3) 0.4606(2) 0.13590(15) 0.0509(5) Uani d . 1 . .
H H6 0.2713 0.4852 0.1897 0.061 Uiso calc R 1 . .
C C7 0.2086(2) 0.10239(19) 0.19856(12) 0.0366(4) Uani d . 1 . .
C C8 0.1436(2) 0.00162(19) 0.14533(12) 0.0370(4) Uani d . 1 . .
C C9 -0.0078(2) -0.0153(2) 0.13289(13) 0.0409(5) Uani d . 1 . .
C C10 -0.0959(2) 0.0673(2) 0.17213(14) 0.0482(5) Uani d . 1 . .
H H10 -0.1975 0.0555 0.1634 0.058 Uiso calc R 1 . .
C C11 -0.0319(2) 0.1676(3) 0.22442(15) 0.0513(5) Uani d . 1 . .
H H11 -0.0910 0.2245 0.2506 0.062 Uiso calc R 1 . .
C C12 0.1197(2) 0.1853(2) 0.23870(14) 0.0467(5) Uani d . 1 . .
H H12 0.1617 0.2524 0.2751 0.056 Uiso calc R 1 . .
C C13 0.4877(3) 0.1928(3) 0.02611(16) 0.0583(6) Uani d . 1 . .
H H13A 0.5892 0.2075 0.0494 0.070 Uiso calc R 1 . .
H H13B 0.4789 0.1809 -0.0337 0.070 Uiso calc R 1 . .
H H13C 0.4526 0.1136 0.0508 0.070 Uiso calc R 1 . .
C C14 0.1715(4) 0.5790(3) -0.0878(2) 0.0778(9) Uani d . 1 . .
H H14A 0.2434 0.5993 -0.1232 0.093 Uiso calc R 1 . .
H H14B 0.1324 0.6613 -0.0692 0.093 Uiso calc R 1 . .
H H14C 0.0933 0.5270 -0.1189 0.093 Uiso calc R 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'
Cl Cl 0.3639 0.7018 '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'
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
O1 S1 O2 . . 119.02(10) ?
O1 S1 N1 . . 104.09(10) ?
O2 S1 N1 . . 108.37(10) ?
O1 S1 C1 . . 111.01(10) ?
O2 S1 C1 . . 107.10(10) ?
N1 S1 C1 . . 106.58(9) ?
C7 N1 S1 . . 123.88(14) ?
C7 N1 H1N . . 114.4(18) ?
S1 N1 H1N . . 114.7(18) ?
C6 C1 C2 . . 120.5(2) ?
C6 C1 S1 . . 117.09(16) ?
C2 C1 S1 . . 122.40(16) ?
C3 C2 C1 . . 117.1(2) ?
C3 C2 C13 . . 118.4(2) ?
C1 C2 C13 . . 124.5(2) ?
C4 C3 C2 . . 123.2(2) ?
C4 C3 H3 . . 118.4 ?
C2 C3 H3 . . 118.4 ?
C3 C4 C5 . . 118.1(2) ?
C3 C4 C14 . . 120.9(3) ?
C5 C4 C14 . . 121.0(3) ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 120.5(2) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
C12 C7 C8 . . 119.07(18) ?
C12 C7 N1 . . 121.33(19) ?
C8 C7 N1 . . 119.57(17) ?
C9 C8 C7 . . 120.06(18) ?
C9 C8 Cl1 . . 120.38(16) ?
C7 C8 Cl1 . . 119.56(15) ?
C10 C9 C8 . . 120.9(2) ?
C10 C9 Cl2 . . 119.20(16) ?
C8 C9 Cl2 . . 119.90(17) ?
C9 C10 C11 . . 119.14(19) ?
C9 C10 H10 . . 120.4 ?
C11 C10 H10 . . 120.4 ?
C10 C11 C12 . . 121.0(2) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C11 C12 C7 . . 119.9(2) ?
C11 C12 H12 . . 120.1 ?
C7 C12 H12 . . 120.1 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C4 C14 H14A . . 109.5 ?
C4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
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
Cl1 C8 . 1.7221(19) ?
Cl2 C9 . 1.733(2) ?
S1 O1 . 1.4307(16) ?
S1 O2 . 1.4338(16) ?
S1 N1 . 1.6448(18) ?
S1 C1 . 1.763(2) ?
N1 C7 . 1.419(2) ?
N1 H1N . 0.839(17) ?
C1 C6 . 1.387(3) ?
C1 C2 . 1.399(3) ?
C2 C3 . 1.389(3) ?
C2 C13 . 1.507(3) ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.388(4) ?
C4 C14 . 1.499(4) ?
C5 C6 . 1.372(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.389(3) ?
C7 C8 . 1.390(3) ?
C8 C9 . 1.385(3) ?
C9 C10 . 1.375(3) ?
C10 C11 . 1.375(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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 Cl1 . 0.839(17) 2.50(2) 2.9517(19) 115(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C7 . . . . -167.74(17) ?
O2 S1 N1 C7 . . . . 64.64(19) ?
C1 S1 N1 C7 . . . . -50.33(19) ?
O1 S1 C1 C6 . . . . -138.08(17) ?
O2 S1 C1 C6 . . . . -6.64(19) ?
N1 S1 C1 C6 . . . . 109.19(17) ?
O1 S1 C1 C2 . . . . 42.39(19) ?
O2 S1 C1 C2 . . . . 173.83(16) ?
N1 S1 C1 C2 . . . . -70.35(18) ?
C6 C1 C2 C3 . . . . 0.7(3) ?
S1 C1 C2 C3 . . . . -179.79(15) ?
C6 C1 C2 C13 . . . . -178.4(2) ?
S1 C1 C2 C13 . . . . 1.1(3) ?
C1 C2 C3 C4 . . . . -1.5(3) ?
C13 C2 C3 C4 . . . . 177.6(2) ?
C2 C3 C4 C5 . . . . 1.0(3) ?
C2 C3 C4 C14 . . . . -178.6(2) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
C14 C4 C5 C6 . . . . 179.9(3) ?
C4 C5 C6 C1 . . . . -1.0(4) ?
C2 C1 C6 C5 . . . . 0.5(3) ?
S1 C1 C6 C5 . . . . -179.00(19) ?
S1 N1 C7 C12 . . . . -44.1(3) ?
S1 N1 C7 C8 . . . . 137.91(17) ?
C12 C7 C8 C9 . . . . 0.0(3) ?
N1 C7 C8 C9 . . . . 177.98(17) ?
C12 C7 C8 Cl1 . . . . -179.87(16) ?
N1 C7 C8 Cl1 . . . . -1.9(2) ?
C7 C8 C9 C10 . . . . 0.5(3) ?
Cl1 C8 C9 C10 . . . . -179.67(16) ?
C7 C8 C9 Cl2 . . . . 179.99(14) ?
Cl1 C8 C9 Cl2 . . . . -0.2(2) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
Cl2 C9 C10 C11 . . . . -179.59(17) ?
C9 C10 C11 C12 . . . . -0.8(3) ?
C10 C11 C12 C7 . . . . 1.2(3) ?
C8 C7 C12 C11 . . . . -0.8(3) ?
N1 C7 C12 C11 . . . . -178.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6798392
2 PubChem 8500826
