#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224366.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_2224366
loop_
_publ_author_name
'Nirmala, P. G.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 4-Methyl-N-(3-methylphenyl)benzenesulfonamide
;
_journal_coeditor_code           LX2127
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3208
_journal_paper_doi               10.1107/S1600536809049332
_journal_volume                  65
_journal_year                    2009
_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
;
4-Methyl-N-(3-methylphenyl)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                90.00
_cell_angle_beta                 98.10(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.076(3)
_cell_length_b                   14.519(3)
_cell_length_c                   13.482(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      5.23
_cell_volume                     2727.8(9)
_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  0.1478
_diffrn_reflns_av_sigmaI/netI    0.1192
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5405
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         4.40
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_T_max  0.5327
_exptl_absorpt_correction_T_min  0.4259
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.423
_refine_ls_extinction_coef       0.0092(7)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0612
_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)+(0.0638P)²+2.2735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1630
_reflns_number_gt                2285
_reflns_number_total             2436
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lx2127.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2224366
_cod_database_fobs_code          2224366
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
C C1 0.03543(17) 0.26890(18) 0.04684(16) 0.0478(6) Uani d . 1 . .
C C2 -0.0487(2) 0.2802(3) 0.0874(3) 0.0769(9) Uani d . 1 . .
H H2 -0.0754 0.3384 0.0915 0.092 Uiso calc R 1 . .
C C3 -0.0921(2) 0.2041(4) 0.1217(3) 0.0927(13) Uani d U 1 . .
H H3 -0.1487 0.2117 0.1490 0.111 Uiso calc R 1 . .
C C4 -0.0551(3) 0.1180(3) 0.1169(2) 0.0767(10) Uani d U 1 . .
C C5 0.0301(2) 0.1079(3) 0.0788(2) 0.0706(8) Uani d . 1 . .
H H5 0.0576 0.0499 0.0768 0.085 Uiso calc R 1 . .
C C6 0.0746(2) 0.1826(2) 0.0439(2) 0.0576(7) Uani d . 1 . .
H H6 0.1319 0.1748 0.0180 0.069 Uiso calc R 1 . .
C C7 0.17516(16) 0.41609(16) 0.18078(17) 0.0450(5) Uani d . 1 . .
C C8 0.24019(18) 0.34436(19) 0.19055(18) 0.0509(6) Uani d . 1 . .
H H8 0.2450 0.3058 0.1364 0.061 Uiso calc R 1 . .
C C9 0.2985(2) 0.3297(2) 0.2811(2) 0.0584(7) Uani d . 1 . .
C C10 0.2903(2) 0.3882(3) 0.3600(2) 0.0690(8) Uani d . 1 . .
H H10 0.3293 0.3793 0.4208 0.083 Uiso calc R 1 . .
C C11 0.2259(2) 0.4588(2) 0.3501(2) 0.0695(8) Uani d . 1 . .
H H11 0.2217 0.4975 0.4043 0.083 Uiso calc R 1 . .
C C12 0.1671(2) 0.47364(19) 0.2610(2) 0.0561(6) Uani d . 1 . .
H H12 0.1227 0.5215 0.2548 0.067 Uiso calc R 1 . .
C C13 -0.1073(4) 0.0352(4) 0.1498(3) 0.1229(19) Uani d . 1 . .
H H13A -0.1598 0.0199 0.0990 0.148 Uiso calc R 1 . .
H H13B -0.1314 0.0491 0.2112 0.148 Uiso calc R 1 . .
H H13C -0.0639 -0.0160 0.1601 0.148 Uiso calc R 1 . .
C C14 0.3672(3) 0.2506(3) 0.2921(3) 0.0958(13) Uani d . 1 . .
H H14A 0.3922 0.2412 0.2302 0.115 Uiso calc R 1 . .
H H14B 0.3346 0.1959 0.3088 0.115 Uiso calc R 1 . .
H H14C 0.4191 0.2638 0.3444 0.115 Uiso calc R 1 . .
N N1 0.11662(17) 0.43561(15) 0.08911(16) 0.0578(6) Uani d D 1 . .
H H1N 0.0746(19) 0.475(2) 0.096(3) 0.069 Uiso d D 1 . .
O O1 0.17370(14) 0.33270(13) -0.03761(13) 0.0573(5) Uani d . 1 . .
O O2 0.01925(16) 0.41182(14) -0.07129(14) 0.0680(6) Uani d . 1 . .
S S1 0.08931(4) 0.36406(4) -0.00253(4) 0.0483(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 0.0181 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'
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 . . 119.4(3) ?
C6 C1 S1 . . 120.79(19) ?
C2 C1 S1 . . 119.8(2) ?
C3 C2 C1 . . 119.0(3) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C4 C3 C2 . . 122.1(3) ?
C4 C3 H3 . . 118.9 ?
C2 C3 H3 . . 118.9 ?
C3 C4 C5 . . 118.4(4) ?
C3 C4 C13 . . 120.9(4) ?
C5 C4 C13 . . 120.7(4) ?
C6 C5 C4 . . 120.6(4) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 120.5(3) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
C8 C7 C12 . . 120.5(2) ?
C8 C7 N1 . . 122.1(2) ?
C12 C7 N1 . . 117.4(2) ?
C7 C8 C9 . . 120.1(2) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C10 C9 C8 . . 118.7(3) ?
C10 C9 C14 . . 121.4(3) ?
C8 C9 C14 . . 119.9(3) ?
C11 C10 C9 . . 121.1(3) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.8(3) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C11 C12 C7 . . 118.8(3) ?
C11 C12 H12 . . 120.6 ?
C7 C12 H12 . . 120.6 ?
C4 C13 H13A . . 109.5 ?
C4 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C4 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 . . 125.80(17) ?
C7 N1 H1N . . 112(2) ?
S1 N1 H1N . . 115(2) ?
O1 S1 O2 . . 118.24(12) ?
O1 S1 N1 . . 109.97(12) ?
O2 S1 N1 . . 104.53(12) ?
O1 S1 C1 . . 107.58(11) ?
O2 S1 C1 . . 109.39(13) ?
N1 S1 C1 . . 106.57(12) ?
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 . 1.372(4) ?
C1 C2 . 1.382(4) ?
C1 S1 . 1.752(3) ?
C2 C3 . 1.375(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.358(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(5) ?
C4 C13 . 1.508(5) ?
C5 C6 . 1.369(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.380(4) ?
C7 C12 . 1.384(4) ?
C7 N1 . 1.414(3) ?
C8 C9 . 1.388(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.378(4) ?
C9 C14 . 1.496(5) ?
C10 C11 . 1.362(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.377(4) ?
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 . 1.619(2) ?
N1 H1N . 0.839(18) ?
O1 S1 . 1.414(2) ?
O2 S1 . 1.4335(18) ?
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 5_565 0.839(18) 2.10(2) 2.914(3) 163(3)
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 . . . . -1.5(4) ?
S1 C1 C2 C3 . . . . 177.1(2) ?
C1 C2 C3 C4 . . . . 0.0(5) ?
C2 C3 C4 C5 . . . . 1.8(5) ?
C2 C3 C4 C13 . . . . -176.6(4) ?
C3 C4 C5 C6 . . . . -1.9(5) ?
C13 C4 C5 C6 . . . . 176.4(3) ?
C4 C5 C6 C1 . . . . 0.4(5) ?
C2 C1 C6 C5 . . . . 1.4(4) ?
S1 C1 C6 C5 . . . . -177.3(2) ?
C12 C7 C8 C9 . . . . -0.3(4) ?
N1 C7 C8 C9 . . . . 177.8(3) ?
C7 C8 C9 C10 . . . . -0.4(4) ?
C7 C8 C9 C14 . . . . 178.6(3) ?
C8 C9 C10 C11 . . . . 0.5(5) ?
C14 C9 C10 C11 . . . . -178.4(4) ?
C9 C10 C11 C12 . . . . 0.1(5) ?
C10 C11 C12 C7 . . . . -0.8(5) ?
C8 C7 C12 C11 . . . . 0.9(4) ?
N1 C7 C12 C11 . . . . -177.3(3) ?
C8 C7 N1 S1 . . . . 21.5(4) ?
C12 C7 N1 S1 . . . . -160.3(2) ?
C7 N1 S1 O1 . . . . -59.6(3) ?
C7 N1 S1 O2 . . . . 172.5(2) ?
C7 N1 S1 C1 . . . . 56.7(3) ?
C6 C1 S1 O1 . . . . -1.9(2) ?
C2 C1 S1 O1 . . . . 179.5(2) ?
C6 C1 S1 O2 . . . . 127.7(2) ?
C2 C1 S1 O2 . . . . -50.9(3) ?
C6 C1 S1 N1 . . . . -119.8(2) ?
C2 C1 S1 N1 . . . . 61.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 174558
