#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226894.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_2226894
loop_
_publ_author_name
'John, Peter'
'Sharif, Shahzad'
'Khan, Islam Ullah'
'Khizar, Saima'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N-(3,4-Dimethylphenyl)benzenesulfonamide
;
_journal_coeditor_code           HB5533
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1983
_journal_paper_doi               10.1107/S1600536810026656
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H15 N O2 S'
_chemical_formula_moiety         'C14 H15 N O2 S'
_chemical_formula_sum            'C14 H15 N O2 S'
_chemical_formula_weight         261.33
_chemical_name_systematic
;
N-(3,4-Dimethylphenyl)benzenesulfonamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 132.014(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2129(12)
_cell_length_b                   9.2616(5)
_cell_length_c                   16.5584(16)
_cell_measurement_reflns_used    2975
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.5
_cell_volume                     2758.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11486
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.65
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.21
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1221P)²+0.6451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.164
_refine_ls_wR_factor_ref         0.196
_reflns_number_gt                2112
_reflns_number_total             2864
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5533.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226894
_cod_database_fobs_code          2226894
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
S S1 0.21969(4) 0.08206(8) 0.26474(6) 0.0437(3) Uani d . 1 . .
O O1 0.16507(13) 0.0323(3) 0.15598(16) 0.0610(6) Uani d . 1 . .
O O2 0.22892(12) 0.2337(2) 0.28664(18) 0.0567(6) Uani d . 1 . .
N N1 0.29812(14) 0.0196(3) 0.3083(2) 0.0492(6) Uani d D 1 . .
H H1n 0.291(2) -0.063(2) 0.280(3) 0.059 Uiso d D 1 . .
C C1 0.20212(16) 0.0052(3) 0.3427(2) 0.0448(7) Uani d U 1 . .
C C2 0.2297(2) 0.0696(4) 0.4375(3) 0.0690(10) Uani d U 1 . .
H H2 0.2586 0.1526 0.4613 0.083 Uiso calc R 1 . .
C C3 0.2149(3) 0.0117(5) 0.4979(3) 0.0875(13) Uani d U 1 . .
H H3 0.2337 0.0557 0.5625 0.105 Uiso calc R 1 . .
C C4 0.1730(3) -0.1089(5) 0.4635(4) 0.0935(14) Uani d U 1 . .
H H4 0.1643 -0.1497 0.5054 0.112 Uiso calc R 1 . .
C C5 0.1437(4) -0.1704(6) 0.3671(5) 0.1114(18) Uani d U 1 . .
H H5 0.1129 -0.2507 0.3418 0.134 Uiso calc R 1 . .
C C6 0.1591(3) -0.1147(5) 0.3065(4) 0.0851(13) Uani d U 1 . .
H H6 0.1403 -0.1588 0.2420 0.102 Uiso calc R 1 . .
C C7 0.36691(17) 0.0393(3) 0.4183(2) 0.0470(7) Uani d . 1 . .
C C8 0.39442(19) 0.1756(3) 0.4603(3) 0.0537(8) Uani d . 1 . .
H H8 0.3673 0.2562 0.4178 0.064 Uiso calc R 1 . .
C C9 0.46209(19) 0.1938(4) 0.5652(3) 0.0607(9) Uani d . 1 . .
C C10 0.50388(19) 0.0737(4) 0.6287(3) 0.0638(10) Uani d . 1 . .
C C11 0.4750(2) -0.0623(4) 0.5834(3) 0.0683(10) Uani d . 1 . .
H H11 0.5022 -0.1436 0.6246 0.082 Uiso calc R 1 . .
C C12 0.4080(2) -0.0805(4) 0.4804(3) 0.0581(8) Uani d . 1 . .
H H12 0.3902 -0.1728 0.4523 0.070 Uiso calc R 1 . .
C C13 0.4905(3) 0.3462(5) 0.6065(4) 0.1030(16) Uani d . 1 . .
H H13A 0.5075 0.3559 0.6778 0.154 Uiso calc R 1 . .
H H13B 0.4511 0.4139 0.5581 0.154 Uiso calc R 1 . .
H H13C 0.5309 0.3653 0.6096 0.154 Uiso calc R 1 . .
C C14 0.5778(2) 0.0900(6) 0.7430(3) 0.0921(15) Uani d . 1 . .
H H14A 0.6053 0.1672 0.7454 0.138 Uiso calc R 1 . .
H H14B 0.6054 0.0017 0.7654 0.138 Uiso calc R 1 . .
H H14C 0.5697 0.1115 0.7912 0.138 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 0.0033 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'
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 . . 119.67(15) ?
O1 S1 N1 . . 105.54(14) ?
O2 S1 N1 . . 107.46(13) ?
O1 S1 C1 . . 108.80(14) ?
O2 S1 C1 . . 106.57(13) ?
N1 S1 C1 . . 108.39(14) ?
C7 N1 S1 . . 122.54(19) ?
C7 N1 H1N . . 117(2) ?
S1 N1 H1N . . 109(2) ?
C6 C1 C2 . . 120.5(3) ?
C6 C1 S1 . . 119.9(2) ?
C2 C1 S1 . . 119.6(2) ?
C1 C2 C3 . . 120.0(4) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 120.1(4) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.7(4) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.7(4) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 119.0(4) ?
C1 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C8 C7 C12 . . 119.7(3) ?
C8 C7 N1 . . 121.0(3) ?
C12 C7 N1 . . 119.2(3) ?
C7 C8 C9 . . 120.7(3) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C8 C9 C10 . . 120.1(3) ?
C8 C9 C13 . . 118.5(4) ?
C10 C9 C13 . . 121.4(4) ?
C11 C10 C9 . . 117.8(3) ?
C11 C10 C14 . . 120.9(4) ?
C9 C10 C14 . . 121.3(4) ?
C12 C11 C10 . . 122.2(3) ?
C12 C11 H11 . . 118.9 ?
C10 C11 H11 . . 118.9 ?
C11 C12 C7 . . 119.5(3) ?
C11 C12 H12 . . 120.2 ?
C7 C12 H12 . . 120.2 ?
C9 C13 H13A . . 109.5 ?
C9 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C9 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 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
S1 O1 . 1.420(2) ?
S1 O2 . 1.430(2) ?
S1 N1 . 1.621(3) ?
S1 C1 . 1.758(3) ?
N1 C7 . 1.436(4) ?
N1 H1n . 0.85(3) ?
C1 C6 . 1.356(5) ?
C1 C2 . 1.364(4) ?
C2 C3 . 1.379(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.351(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.363(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(6) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.379(4) ?
C7 C12 . 1.381(4) ?
C8 C9 . 1.386(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.394(5) ?
C9 C13 . 1.518(6) ?
C10 C11 . 1.392(5) ?
C10 C14 . 1.508(5) ?
C11 C12 . 1.365(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 ?
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 4_545 0.85(3) 2.07(2) 2.921(3) 177(5)
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 . . . . -176.1(2) ?
O2 S1 N1 C7 . . . . 55.1(3) ?
C1 S1 N1 C7 . . . . -59.7(3) ?
O1 S1 C1 C6 . . . . 19.3(4) ?
O2 S1 C1 C6 . . . . 149.6(3) ?
N1 S1 C1 C6 . . . . -95.0(4) ?
O1 S1 C1 C2 . . . . -158.3(3) ?
O2 S1 C1 C2 . . . . -28.0(3) ?
N1 S1 C1 C2 . . . . 87.4(3) ?
C6 C1 C2 C3 . . . . 0.9(6) ?
S1 C1 C2 C3 . . . . 178.6(3) ?
C1 C2 C3 C4 . . . . 0.1(7) ?
C2 C3 C4 C5 . . . . -2.1(9) ?
C3 C4 C5 C6 . . . . 3.1(10) ?
C2 C1 C6 C5 . . . . 0.1(7) ?
S1 C1 C6 C5 . . . . -177.6(4) ?
C4 C5 C6 C1 . . . . -2.1(9) ?
S1 N1 C7 C8 . . . . -60.8(4) ?
S1 N1 C7 C12 . . . . 123.0(3) ?
C12 C7 C8 C9 . . . . -1.6(4) ?
N1 C7 C8 C9 . . . . -177.7(3) ?
C7 C8 C9 C10 . . . . 1.4(5) ?
C7 C8 C9 C13 . . . . 178.7(3) ?
C8 C9 C10 C11 . . . . -0.5(5) ?
C13 C9 C10 C11 . . . . -177.8(4) ?
C8 C9 C10 C14 . . . . 179.9(3) ?
C13 C9 C10 C14 . . . . 2.6(5) ?
C9 C10 C11 C12 . . . . -0.2(5) ?
C14 C10 C11 C12 . . . . 179.4(3) ?
C10 C11 C12 C7 . . . . -0.1(5) ?
C8 C7 C12 C11 . . . . 0.9(5) ?
N1 C7 C12 C11 . . . . 177.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 502334
