#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224376.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_2224376
loop_
_publ_author_name
'Nirmala, P. G.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 4-Methyl-N-(2-methylphenyl)benzenesulfonamide
;
_journal_coeditor_code           NG2688
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3184
_journal_paper_doi               10.1107/S1600536809049411
_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-(2-methylphenyl)benzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.650(3)
_cell_length_b                   12.0190(10)
_cell_length_c                   15.634(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      18.67
_cell_measurement_theta_min      5.67
_cell_volume                     2752.8(8)
_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 scans'
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3596
_diffrn_reflns_theta_full        66.83
_diffrn_reflns_theta_max         66.83
_diffrn_reflns_theta_min         5.54
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  0.5354
_exptl_absorpt_correction_T_min  0.4000
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.233
_refine_ls_extinction_coef       0.0052(4)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0436
_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)+(0.0660P)²+0.6125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1899
_reflns_number_total             2450
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2688.cif
_cod_data_source_block           I
_cod_database_code               2224376
_cod_database_fobs_code          2224376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 -0.03969(15) 0.17693(18) 0.64937(14) 0.0620(6) Uani d . 1 . .
C C2 -0.12664(19) 0.1429(2) 0.6286(2) 0.0857(8) Uani d . 1 . .
H H2 -0.1359 0.0754 0.6008 0.103 Uiso calc R 1 . .
C C3 -0.19886(19) 0.2088(3) 0.6489(2) 0.0898(8) Uani d . 1 . .
H H3 -0.2574 0.1845 0.6356 0.108 Uiso calc R 1 . .
C C4 -0.18818(18) 0.3102(2) 0.68837(15) 0.0733(6) Uani d . 1 . .
C C5 -0.10123(19) 0.3429(2) 0.70810(17) 0.0817(7) Uani d . 1 . .
H H5 -0.0923 0.4112 0.7348 0.098 Uiso calc R 1 . .
C C6 -0.02714(18) 0.2779(2) 0.68964(16) 0.0744(7) Uani d . 1 . .
H H6 0.0313 0.3017 0.7041 0.089 Uiso calc R 1 . .
C C7 0.12097(16) 0.2537(2) 0.52015(16) 0.0689(6) Uani d . 1 . .
C C8 0.07178(18) 0.3294(2) 0.47154(17) 0.0722(7) Uani d . 1 . .
C C9 0.1070(2) 0.4370(2) 0.4659(2) 0.0922(9) Uani d . 1 . .
H H9 0.0766 0.4895 0.4328 0.111 Uiso calc R 1 . .
C C10 0.1853(3) 0.4672(3) 0.5079(3) 0.1076(11) Uani d . 1 . .
H H10 0.2063 0.5400 0.5040 0.129 Uiso calc R 1 . .
C C11 0.2329(2) 0.3912(3) 0.5557(2) 0.1046(11) Uani d . 1 . .
H H11 0.2862 0.4118 0.5839 0.125 Uiso calc R 1 . .
C C12 0.20070(18) 0.2843(2) 0.5612(2) 0.0871(8) Uani d . 1 . .
H H12 0.2329 0.2318 0.5928 0.105 Uiso calc R 1 . .
C C13 -0.2691(2) 0.3820(3) 0.7071(2) 0.1058(10) Uani d . 1 . .
H H13A -0.3106 0.3425 0.7437 0.127 Uiso calc R 1 . .
H H13B -0.2993 0.4008 0.6546 0.127 Uiso calc R 1 . .
H H13C -0.2493 0.4489 0.7352 0.127 Uiso calc R 1 . .
C C14 -0.0145(2) 0.2995(2) 0.4273(2) 0.0950(9) Uani d . 1 . .
H H14A -0.0583 0.2740 0.4686 0.114 Uiso calc R 1 . .
H H14B -0.0028 0.2415 0.3865 0.114 Uiso calc R 1 . .
H H14C -0.0381 0.3637 0.3983 0.114 Uiso calc R 1 . .
N N1 0.09033(14) 0.14056(16) 0.52843(14) 0.0700(5) Uani d D 1 . .
H H1N 0.0544(16) 0.118(2) 0.4904(15) 0.084 Uiso d D 1 . .
O O1 0.02213(13) -0.01564(13) 0.60343(13) 0.0853(6) Uani d . 1 . .
O O2 0.12395(13) 0.11202(15) 0.68176(13) 0.0885(6) Uani d . 1 . .
S S1 0.05391(4) 0.09508(5) 0.62032(4) 0.0692(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
C2 C1 C6 . . 119.5(2) ?
C2 C1 S1 . . 119.82(18) ?
C6 C1 S1 . . 120.62(18) ?
C3 C2 C1 . . 119.5(2) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 122.2(3) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C5 C4 C3 . . 117.5(3) ?
C5 C4 C13 . . 121.9(3) ?
C3 C4 C13 . . 120.6(3) ?
C6 C5 C4 . . 121.8(2) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C1 . . 119.5(2) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
C12 C7 C8 . . 121.2(2) ?
C12 C7 N1 . . 118.3(3) ?
C8 C7 N1 . . 120.5(2) ?
C7 C8 C9 . . 116.8(3) ?
C7 C8 C14 . . 122.6(2) ?
C9 C8 C14 . . 120.6(3) ?
C10 C9 C8 . . 121.6(3) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C11 C10 C9 . . 120.7(3) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 118.9(3) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C11 C12 C7 . . 120.7(3) ?
C11 C12 H12 . . 119.6 ?
C7 C12 H12 . . 119.6 ?
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 ?
C8 C14 H14A . . 109.5 ?
C8 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C8 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C7 N1 S1 . . 119.98(16) ?
C7 N1 H1N . . 115.9(19) ?
S1 N1 H1N . . 108(2) ?
O2 S1 O1 . . 119.47(11) ?
O2 S1 N1 . . 108.19(12) ?
O1 S1 N1 . . 104.81(11) ?
O2 S1 C1 . . 108.08(11) ?
O1 S1 C1 . . 108.39(11) ?
N1 S1 C1 . . 107.32(10) ?
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 . 1.377(3) ?
C1 C6 . 1.380(3) ?
C1 S1 . 1.748(2) ?
C2 C3 . 1.359(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.368(4) ?
C4 C13 . 1.495(4) ?
C5 C6 . 1.368(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.382(4) ?
C7 C8 . 1.387(4) ?
C7 N1 . 1.437(3) ?
C8 C9 . 1.395(4) ?
C8 C14 . 1.484(4) ?
C9 C10 . 1.371(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.371(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 . 1.627(2) ?
N1 H1N . 0.838(17) ?
O1 S1 . 1.4344(17) ?
O2 S1 . 1.4203(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 O1 5_556 0.838(17) 2.219(18) 3.036(3) 165(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
C6 C1 C2 C3 . . . . -0.7(4) ?
S1 C1 C2 C3 . . . . -177.8(2) ?
C1 C2 C3 C4 . . . . 1.3(5) ?
C2 C3 C4 C5 . . . . -0.9(5) ?
C2 C3 C4 C13 . . . . 178.0(3) ?
C3 C4 C5 C6 . . . . -0.1(4) ?
C13 C4 C5 C6 . . . . -178.9(3) ?
C4 C5 C6 C1 . . . . 0.6(4) ?
C2 C1 C6 C5 . . . . -0.2(4) ?
S1 C1 C6 C5 . . . . 176.9(2) ?
C12 C7 C8 C9 . . . . 0.3(4) ?
N1 C7 C8 C9 . . . . -179.1(2) ?
C12 C7 C8 C14 . . . . -179.5(2) ?
N1 C7 C8 C14 . . . . 1.1(4) ?
C7 C8 C9 C10 . . . . -1.4(4) ?
C14 C8 C9 C10 . . . . 178.4(3) ?
C8 C9 C10 C11 . . . . 1.5(5) ?
C9 C10 C11 C12 . . . . -0.3(5) ?
C10 C11 C12 C7 . . . . -0.8(5) ?
C8 C7 C12 C11 . . . . 0.8(4) ?
N1 C7 C12 C11 . . . . -179.8(3) ?
C12 C7 N1 S1 . . . . 68.5(3) ?
C8 C7 N1 S1 . . . . -112.0(2) ?
C7 N1 S1 O2 . . . . -56.3(2) ?
C7 N1 S1 O1 . . . . 175.17(18) ?
C7 N1 S1 C1 . . . . 60.1(2) ?
C2 C1 S1 O2 . . . . -150.3(2) ?
C6 C1 S1 O2 . . . . 32.6(2) ?
C2 C1 S1 O1 . . . . -19.5(3) ?
C6 C1 S1 O1 . . . . 163.5(2) ?
C2 C1 S1 N1 . . . . 93.2(2) ?
C6 C1 S1 N1 . . . . -83.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 59829
