#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230248.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_2230248
loop_
_publ_author_name
'Shakuntala, K.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 4-Chloro-N-(2,3-dimethylphenyl)benzenesulfonamide
;
_journal_coeditor_code           BT5537
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1328
_journal_paper_doi               10.1107/S1600536811016321
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H14 Cl N O2 S'
_chemical_formula_moiety         'C14 H14 Cl N O2 S'
_chemical_formula_sum            'C14 H14 Cl N O2 S'
_chemical_formula_weight         295.77
_chemical_name_systematic
;
4-Chloro-N-(2,3-dimethylphenyl)benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9926(6)
_cell_length_b                   22.296(3)
_cell_length_c                   12.793(2)
_cell_measurement_reflns_used    1658
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      3.16
_cell_volume                     1424.1(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5341
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.9600
_exptl_absorpt_correction_T_min  0.8528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0545
_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)+(0.0284P)²+1.6874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                1882
_reflns_number_total             2669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5537.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230248
_cod_database_fobs_code          2230248
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.0055(6) 0.22651(14) 0.3463(2) 0.0406(7) Uani d . 1 1 . .
C C2 0.1101(6) 0.21646(17) 0.2488(3) 0.0536(9) Uani d . 1 1 . .
H H2 0.2466 0.2413 0.2249 0.064 Uiso calc R 1 1 . .
C C3 0.0209(7) 0.16946(18) 0.1881(3) 0.0573(9) Uani d . 1 1 . .
H H3 0.0973 0.1623 0.1230 0.069 Uiso calc R 1 1 . .
C C4 -0.1806(7) 0.13352(15) 0.2240(3) 0.0516(9) Uani d . 1 1 . .
C C5 -0.2940(7) 0.14244(16) 0.3206(3) 0.0544(9) Uani d . 1 1 . .
H H5 -0.4285 0.1170 0.3443 0.065 Uiso calc R 1 1 . .
C C6 -0.2071(6) 0.18932(15) 0.3820(3) 0.0490(8) Uani d . 1 1 . .
H H6 -0.2837 0.1959 0.4472 0.059 Uiso calc R 1 1 . .
C C7 -0.0479(6) 0.37146(15) 0.2783(2) 0.0426(8) Uani d . 1 1 . .
C C8 0.1300(6) 0.41952(15) 0.2693(2) 0.0425(7) Uani d . 1 1 . .
C C9 0.1703(6) 0.44421(16) 0.1699(3) 0.0487(8) Uani d . 1 1 . .
C C10 0.0308(8) 0.42138(18) 0.0854(3) 0.0612(10) Uani d . 1 1 . .
H H10 0.0579 0.4379 0.0195 0.073 Uiso calc R 1 1 . .
C C11 -0.1469(8) 0.37484(19) 0.0965(3) 0.0656(11) Uani d . 1 1 . .
H H11 -0.2390 0.3603 0.0386 0.079 Uiso calc R 1 1 . .
C C12 -0.1889(7) 0.34977(17) 0.1933(3) 0.0565(9) Uani d . 1 1 . .
H H12 -0.3108 0.3186 0.2014 0.068 Uiso calc R 1 1 . .
C C13 0.2732(7) 0.44507(16) 0.3628(3) 0.0551(9) Uani d . 1 1 . .
H H13A 0.2268 0.4866 0.3706 0.066 Uiso calc R 1 1 . .
H H13B 0.4631 0.4414 0.3531 0.066 Uiso calc R 1 1 . .
H H13C 0.2211 0.4234 0.4244 0.066 Uiso calc R 1 1 . .
C C14 0.3601(8) 0.49621(18) 0.1552(3) 0.0665(11) Uani d . 1 1 . .
H H14A 0.5360 0.4849 0.1783 0.080 Uiso calc R 1 1 . .
H H14B 0.2988 0.5299 0.1953 0.080 Uiso calc R 1 1 . .
H H14C 0.3663 0.5069 0.0825 0.080 Uiso calc R 1 1 . .
N N1 -0.0959(5) 0.34539(12) 0.3801(2) 0.0448(7) Uani d . 1 1 . .
H H1N -0.2211 0.3596 0.4190 0.054 Uiso calc R 1 1 . .
O O1 0.0057(5) 0.27818(11) 0.52703(17) 0.0567(6) Uani d . 1 1 . .
O O2 0.3577(4) 0.30355(11) 0.3984(2) 0.0584(7) Uani d . 1 1 . .
Cl Cl1 -0.2989(3) 0.07532(5) 0.14708(8) 0.0827(4) Uani d . 1 1 . .
S S1 0.08490(15) 0.28949(4) 0.42182(7) 0.0439(2) 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 0.0033 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
C6 C1 C2 . . 120.1(3) ?
C6 C1 S1 . . 118.9(2) ?
C2 C1 S1 . . 120.8(3) ?
C3 C2 C1 . . 119.5(3) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C4 C3 C2 . . 119.6(3) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 Cl1 . . 119.9(3) ?
C5 C4 Cl1 . . 118.6(3) ?
C4 C5 C6 . . 119.5(3) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 C1 . . 119.7(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
C12 C7 C8 . . 121.8(3) ?
C12 C7 N1 . . 118.9(3) ?
C8 C7 N1 . . 119.3(3) ?
C7 C8 C9 . . 118.0(3) ?
C7 C8 C13 . . 121.7(3) ?
C9 C8 C13 . . 120.3(3) ?
C10 C9 C8 . . 119.5(3) ?
C10 C9 C14 . . 120.1(3) ?
C8 C9 C14 . . 120.4(3) ?
C11 C10 C9 . . 121.5(4) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 120.1(4) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C7 . . 119.2(3) ?
C11 C12 H12 . . 120.4 ?
C7 C12 H12 . . 120.4 ?
C8 C13 H13A . . 109.5 ?
C8 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C8 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C9 C14 H14A . . 109.5 ?
C9 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C7 N1 S1 . . 120.7(2) ?
C7 N1 H1N . . 119.7 ?
S1 N1 H1N . . 119.7 ?
O1 S1 O2 . . 120.18(15) ?
O1 S1 N1 . . 106.86(14) ?
O2 S1 N1 . . 106.92(14) ?
O1 S1 C1 . . 107.77(15) ?
O2 S1 C1 . . 107.62(15) ?
N1 S1 C1 . . 106.81(14) ?
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 C6 . 1.382(4) ?
C1 C2 . 1.393(4) ?
C1 S1 . 1.763(3) ?
C2 C3 . 1.378(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.366(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(5) ?
C4 Cl1 . 1.732(3) ?
C5 C6 . 1.377(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.382(4) ?
C7 C8 . 1.397(4) ?
C7 N1 . 1.447(4) ?
C8 C9 . 1.401(4) ?
C8 C13 . 1.505(4) ?
C9 C10 . 1.382(5) ?
C9 C14 . 1.509(5) ?
C10 C11 . 1.373(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(5) ?
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 ?
N1 S1 . 1.628(3) ?
N1 H1N . 0.8600 ?
O1 S1 . 1.426(2) ?
O2 S1 . 1.430(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 1_455 0.86 2.46 2.893(3) 112
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 . . . . -175.1(3) ?
C1 C2 C3 C4 . . . . 0.3(5) ?
C2 C3 C4 C5 . . . . -1.2(5) ?
C2 C3 C4 Cl1 . . . . 178.7(3) ?
C3 C4 C5 C6 . . . . 1.3(5) ?
Cl1 C4 C5 C6 . . . . -178.5(3) ?
C4 C5 C6 C1 . . . . -0.6(5) ?
C2 C1 C6 C5 . . . . -0.3(5) ?
S1 C1 C6 C5 . . . . 175.3(3) ?
C12 C7 C8 C9 . . . . -2.3(5) ?
N1 C7 C8 C9 . . . . -179.4(3) ?
C12 C7 C8 C13 . . . . 176.9(3) ?
N1 C7 C8 C13 . . . . -0.1(4) ?
C7 C8 C9 C10 . . . . 1.3(5) ?
C13 C8 C9 C10 . . . . -178.0(3) ?
C7 C8 C9 C14 . . . . 180.0(3) ?
C13 C8 C9 C14 . . . . 0.7(5) ?
C8 C9 C10 C11 . . . . -0.1(5) ?
C14 C9 C10 C11 . . . . -178.8(3) ?
C9 C10 C11 C12 . . . . -0.2(6) ?
C10 C11 C12 C7 . . . . -0.8(6) ?
C8 C7 C12 C11 . . . . 2.1(5) ?
N1 C7 C12 C11 . . . . 179.2(3) ?
C12 C7 N1 S1 . . . . 91.9(3) ?
C8 C7 N1 S1 . . . . -91.0(3) ?
C7 N1 S1 O1 . . . . 174.6(2) ?
C7 N1 S1 O2 . . . . 44.7(3) ?
C7 N1 S1 C1 . . . . -70.3(3) ?
C6 C1 S1 O1 . . . . 22.9(3) ?
C2 C1 S1 O1 . . . . -161.6(3) ?
C6 C1 S1 O2 . . . . 153.8(3) ?
C2 C1 S1 O2 . . . . -30.6(3) ?
C6 C1 S1 N1 . . . . -91.7(3) ?
C2 C1 S1 N1 . . . . 83.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 260471
