#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224564.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_2224564
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(3,5-Dimethylphenyl)-4-methylbenzenesulfonamide
;
_journal_coeditor_code           BT5135
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o144
_journal_paper_doi               10.1107/S1600536809053057
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H17 N O2 S'
_chemical_formula_moiety         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.36
_chemical_name_systematic
;
N-(3,5-Dimethylphenyl)-4-methylbenzenesulfonamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.860(10)
_cell_angle_beta                 97.620(10)
_cell_angle_gamma                108.140(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3110(10)
_cell_length_b                   8.5210(10)
_cell_length_c                   11.4120(10)
_cell_measurement_reflns_used    2279
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.62
_cell_volume                     741.60(15)
_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      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi 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  0.0121
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4897
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.63
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.9187
_exptl_absorpt_correction_T_min  0.9092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.308
_refine_ls_extinction_coef       0.087(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   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0643P)²+0.1701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                2525
_reflns_number_total             3025
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bt5135.cif
_cod_data_source_block           I
_cod_original_cell_volume        741.60(14)
_cod_database_code               2224564
_cod_database_fobs_code          2224564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.81313(5) 1.06718(5) 0.37422(4) 0.04434(17) Uani d . 1 . .
O O1 0.91624(16) 1.14988(15) 0.49312(11) 0.0528(3) Uani d . 1 . .
O O2 0.76542(18) 1.16623(17) 0.29675(13) 0.0587(4) Uani d . 1 . .
N N1 0.92841(19) 0.9671(2) 0.30816(13) 0.0485(4) Uani d D 1 . .
H H1N 0.977(3) 0.928(3) 0.3581(17) 0.058 Uiso d D 1 . .
C C1 0.6248(2) 0.9101(2) 0.38708(15) 0.0413(4) Uani d . 1 . .
C C2 0.4799(2) 0.8575(3) 0.29635(18) 0.0550(5) Uani d . 1 . .
H H2 0.4794 0.9097 0.2312 0.066 Uiso calc R 1 . .
C C3 0.3358(2) 0.7272(3) 0.3029(2) 0.0612(5) Uani d . 1 . .
H H3 0.2378 0.6926 0.2418 0.073 Uiso calc R 1 . .
C C4 0.3338(2) 0.6468(2) 0.3982(2) 0.0565(5) Uani d . 1 . .
C C5 0.4797(3) 0.7038(3) 0.4893(2) 0.0617(5) Uani d . 1 . .
H H5 0.4794 0.6531 0.5552 0.074 Uiso calc R 1 . .
C C6 0.6256(2) 0.8341(2) 0.48470(17) 0.0541(5) Uani d . 1 . .
H H6 0.7230 0.8701 0.5464 0.065 Uiso calc R 1 . .
C C7 0.8582(2) 0.8517(2) 0.19231(15) 0.0457(4) Uani d . 1 . .
C C8 0.8165(3) 0.9108(3) 0.09055(17) 0.0566(5) Uani d . 1 . .
H H8 0.8323 1.0252 0.0976 0.068 Uiso calc R 1 . .
C C9 0.7514(3) 0.7991(3) -0.02150(18) 0.0640(5) Uani d . 1 . .
C C10 0.7315(3) 0.6301(3) -0.03010(19) 0.0695(6) Uani d . 1 . .
H H10 0.6872 0.5549 -0.1054 0.083 Uiso calc R 1 . .
C C11 0.7759(3) 0.5689(3) 0.07052(19) 0.0629(5) Uani d . 1 . .
C C12 0.8382(2) 0.6827(3) 0.18233(17) 0.0530(4) Uani d . 1 . .
H H12 0.8668 0.6447 0.2512 0.064 Uiso calc R 1 . .
C C13 0.1768(3) 0.5018(3) 0.4026(3) 0.0824(8) Uani d . 1 . .
H H13A 0.0804 0.5406 0.4061 0.099 Uiso calc R 1 . .
H H13B 0.1993 0.4592 0.4734 0.099 Uiso calc R 1 . .
H H13C 0.1505 0.4131 0.3313 0.099 Uiso calc R 1 . .
C C14 0.7039(4) 0.8623(4) -0.1327(2) 0.0946(9) Uani d . 1 . .
H H14A 0.5812 0.8369 -0.1510 0.113 Uiso calc R 1 . .
H H14B 0.7392 0.8075 -0.2003 0.113 Uiso calc R 1 . .
H H14C 0.7613 0.9827 -0.1174 0.113 Uiso calc R 1 . .
C C15 0.7573(4) 0.3850(3) 0.0585(3) 0.0952(9) Uani d . 1 . .
H H15A 0.6505 0.3153 0.0046 0.114 Uiso calc R 1 . .
H H15B 0.7577 0.3579 0.1368 0.114 Uiso calc R 1 . .
H H15C 0.8520 0.3645 0.0266 0.114 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
O2 S1 O1 . . 119.35(8) ?
O2 S1 N1 . . 108.43(8) ?
O1 S1 N1 . . 104.34(8) ?
O2 S1 C1 . . 108.50(8) ?
O1 S1 C1 . . 109.14(8) ?
N1 S1 C1 . . 106.34(8) ?
C7 N1 S1 . . 120.83(12) ?
C7 N1 H1N . . 112.8(15) ?
S1 N1 H1N . . 109.6(15) ?
C2 C1 C6 . . 120.44(16) ?
C2 C1 S1 . . 119.58(13) ?
C6 C1 S1 . . 119.90(13) ?
C3 C2 C1 . . 119.53(18) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 121.32(18) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C5 C4 C3 . . 118.06(17) ?
C5 C4 C13 . . 121.2(2) ?
C3 C4 C13 . . 120.7(2) ?
C4 C5 C6 . . 121.66(19) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 118.96(18) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
C12 C7 C8 . . 120.51(18) ?
C12 C7 N1 . . 119.34(16) ?
C8 C7 N1 . . 120.11(17) ?
C9 C8 C7 . . 119.83(19) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C10 C9 C8 . . 119.03(19) ?
C10 C9 C14 . . 120.8(2) ?
C8 C9 C14 . . 120.1(2) ?
C9 C10 C11 . . 122.0(2) ?
C9 C10 H10 . . 119.0 ?
C11 C10 H10 . . 119.0 ?
C12 C11 C10 . . 117.9(2) ?
C12 C11 C15 . . 121.0(2) ?
C10 C11 C15 . . 121.1(2) ?
C7 C12 C11 . . 120.66(17) ?
C7 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
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 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 O2 . 1.4220(13) ?
S1 O1 . 1.4353(13) ?
S1 N1 . 1.6414(16) ?
S1 C1 . 1.7570(17) ?
N1 C7 . 1.431(2) ?
N1 H1N . 0.830(15) ?
C1 C2 . 1.378(2) ?
C1 C6 . 1.381(2) ?
C2 C3 . 1.378(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(3) ?
C4 C13 . 1.506(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.380(3) ?
C7 C8 . 1.387(2) ?
C8 C9 . 1.383(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.382(3) ?
C9 C14 . 1.513(3) ?
C10 C11 . 1.393(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.388(3) ?
C11 C15 . 1.506(3) ?
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 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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 O1 2_776 0.830(15) 2.111(16) 2.933(2) 170(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
O2 S1 N1 C7 . . . . -59.70(15) ?
O1 S1 N1 C7 . . . . 172.11(13) ?
C1 S1 N1 C7 . . . . 56.80(15) ?
O2 S1 C1 C2 . . . . 24.58(17) ?
O1 S1 C1 C2 . . . . 156.11(15) ?
N1 S1 C1 C2 . . . . -91.87(16) ?
O2 S1 C1 C6 . . . . -158.72(15) ?
O1 S1 C1 C6 . . . . -27.19(17) ?
N1 S1 C1 C6 . . . . 84.83(16) ?
C6 C1 C2 C3 . . . . -0.6(3) ?
S1 C1 C2 C3 . . . . 176.04(15) ?
C1 C2 C3 C4 . . . . -0.5(3) ?
C2 C3 C4 C5 . . . . 1.6(3) ?
C2 C3 C4 C13 . . . . -178.55(19) ?
C3 C4 C5 C6 . . . . -1.7(3) ?
C13 C4 C5 C6 . . . . 178.5(2) ?
C4 C5 C6 C1 . . . . 0.6(3) ?
C2 C1 C6 C5 . . . . 0.6(3) ?
S1 C1 C6 C5 . . . . -176.08(15) ?
S1 N1 C7 C12 . . . . -116.91(17) ?
S1 N1 C7 C8 . . . . 65.4(2) ?
C12 C7 C8 C9 . . . . 1.2(3) ?
N1 C7 C8 C9 . . . . 178.92(17) ?
C7 C8 C9 C10 . . . . -1.0(3) ?
C7 C8 C9 C14 . . . . 179.4(2) ?
C8 C9 C10 C11 . . . . -0.3(4) ?
C14 C9 C10 C11 . . . . 179.3(2) ?
C9 C10 C11 C12 . . . . 1.4(4) ?
C9 C10 C11 C15 . . . . -178.5(3) ?
C8 C7 C12 C11 . . . . -0.1(3) ?
N1 C7 C12 C11 . . . . -177.81(17) ?
C10 C11 C12 C7 . . . . -1.2(3) ?
C15 C11 C12 C7 . . . . 178.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 676082
