#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/39/2223972.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_2223972
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,5-Dimethylphenyl)benzenesulfonamide
;
_journal_coeditor_code           PK2200
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2763
_journal_paper_doi               10.1107/S1600536809041841
_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
;
N-(2,5-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                 101.860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5230(10)
_cell_length_b                   8.5631(7)
_cell_length_c                   15.135(2)
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.62
_cell_volume                     1334.7(2)
_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_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer
with 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  0.0098
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5236
_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    0.236
_exptl_absorpt_correction_T_max  0.9241
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.255
_refine_ls_extinction_coef       0.0149(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0366
_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)+(0.0568P)²+0.2974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2221
_reflns_number_total             2727
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            pk2200.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2223972
_cod_database_fobs_code          2223972
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_disorder_assembly
_atom_site_disorder_group
S S1 0.78193(4) 0.44572(5) -0.00630(3) 0.03753(16) Uani d . 1 . .
O O1 0.88777(11) 0.35489(14) -0.02510(9) 0.0504(3) Uani d . 1 . .
O O2 0.68808(12) 0.37259(15) 0.03523(9) 0.0476(3) Uani d . 1 . .
N N1 0.84891(13) 0.58790(18) 0.05948(10) 0.0417(4) Uani d . 1 . .
H H1N 0.9148(19) 0.619(2) 0.0428(13) 0.050 Uiso d . 1 . .
C C1 0.70021(15) 0.53338(19) -0.10743(11) 0.0381(4) Uani d . 1 . .
C C2 0.57570(16) 0.5897(2) -0.11257(13) 0.0474(4) Uani d . 1 . .
H H2 0.5335 0.5753 -0.0649 0.057 Uiso calc R 1 . .
C C3 0.5152(2) 0.6672(3) -0.18942(16) 0.0647(6) Uani d . 1 . .
H H3 0.4315 0.7057 -0.1937 0.078 Uiso calc R 1 . .
C C4 0.5778(2) 0.6880(3) -0.25983(16) 0.0722(7) Uani d . 1 . .
H H4 0.5361 0.7404 -0.3115 0.087 Uiso calc R 1 . .
C C5 0.7015(2) 0.6322(3) -0.25444(14) 0.0672(6) Uani d . 1 . .
H H5 0.7429 0.6467 -0.3025 0.081 Uiso calc R 1 . .
C C6 0.76449(19) 0.5545(2) -0.17803(13) 0.0513(5) Uani d . 1 . .
H H6 0.8484 0.5170 -0.1739 0.062 Uiso calc R 1 . .
C C7 0.76772(16) 0.7043(2) 0.08868(12) 0.0437(4) Uani d . 1 . .
C C8 0.7529(2) 0.8517(2) 0.04985(15) 0.0607(5) Uani d . 1 . .
C C9 0.6695(3) 0.9543(3) 0.0839(2) 0.0831(8) Uani d . 1 . .
H H9 0.6550 1.0538 0.0593 0.100 Uiso calc R 1 . .
C C10 0.6091(3) 0.9108(3) 0.1524(2) 0.0825(8) Uani d . 1 . .
H H10 0.5540 0.9815 0.1722 0.099 Uiso calc R 1 . .
C C11 0.62731(19) 0.7668(3) 0.19244(15) 0.0622(6) Uani d . 1 . .
C C12 0.70773(16) 0.6642(2) 0.15926(13) 0.0486(4) Uani d . 1 . .
H H12 0.7221 0.5655 0.1849 0.058 Uiso calc R 1 . .
C C13 0.8207(3) 0.9011(3) -0.0238(2) 0.0899(8) Uani d . 1 . .
H H13A 0.9091 0.8655 -0.0099 0.108 Uiso calc R 1 . .
H H13B 0.8193 1.0129 -0.0285 0.108 Uiso calc R 1 . .
H H13C 0.7771 0.8565 -0.0801 0.108 Uiso calc R 1 . .
C C14 0.5648(2) 0.7236(4) 0.27002(18) 0.0873(9) Uani d . 1 . .
H H14A 0.5622 0.8136 0.3074 0.105 Uiso calc R 1 . .
H H14B 0.6143 0.6425 0.3050 0.105 Uiso calc R 1 . .
H H14C 0.4780 0.6873 0.2471 0.105 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 . . 119.19(8) ?
O2 S1 N1 . . 108.07(8) ?
O1 S1 N1 . . 105.61(8) ?
O2 S1 C1 . . 108.22(8) ?
O1 S1 C1 . . 108.61(8) ?
N1 S1 C1 . . 106.47(8) ?
C7 N1 S1 . . 119.53(11) ?
C7 N1 H1N . . 117.4(15) ?
S1 N1 H1N . . 109.5(14) ?
C2 C1 C6 . . 121.13(16) ?
C2 C1 S1 . . 119.01(13) ?
C6 C1 S1 . . 119.72(13) ?
C3 C2 C1 . . 118.92(18) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C4 C3 C2 . . 120.4(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C5 C4 C3 . . 120.5(2) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.3(2) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 118.76(19) ?
C5 C6 H6 . . 120.6 ?
C1 C6 H6 . . 120.6 ?
C8 C7 C12 . . 121.37(18) ?
C8 C7 N1 . . 121.47(18) ?
C12 C7 N1 . . 117.14(16) ?
C7 C8 C9 . . 115.8(2) ?
C7 C8 C13 . . 122.8(2) ?
C9 C8 C13 . . 121.4(2) ?
C10 C9 C8 . . 121.7(2) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C11 C10 C9 . . 122.3(2) ?
C11 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C10 C11 C12 . . 116.8(2) ?
C10 C11 C14 . . 121.5(2) ?
C12 C11 C14 . . 121.7(2) ?
C11 C12 C7 . . 122.0(2) ?
C11 C12 H12 . . 119.0 ?
C7 C12 H12 . . 119.0 ?
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 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 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 O2 . 1.4205(12) ?
S1 O1 . 1.4340(12) ?
S1 N1 . 1.6377(15) ?
S1 C1 . 1.7620(17) ?
N1 C7 . 1.440(2) ?
N1 H1N . 0.828(19) ?
C1 C2 . 1.383(2) ?
C1 C6 . 1.389(2) ?
C2 C3 . 1.376(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.387(3) ?
C7 C12 . 1.391(3) ?
C8 C9 . 1.412(3) ?
C8 C13 . 1.503(4) ?
C9 C10 . 1.374(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.384(3) ?
C11 C14 . 1.505(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 ?
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 3_765 0.828(19) 2.16(2) 2.9634(19) 163.3(19)
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 . . . . -53.36(15) ?
O1 S1 N1 C7 . . . . 178.05(13) ?
C1 S1 N1 C7 . . . . 62.70(15) ?
O2 S1 C1 C2 . . . . 31.30(16) ?
O1 S1 C1 C2 . . . . 162.03(14) ?
N1 S1 C1 C2 . . . . -84.66(15) ?
O2 S1 C1 C6 . . . . -153.10(14) ?
O1 S1 C1 C6 . . . . -22.37(16) ?
N1 S1 C1 C6 . . . . 90.94(15) ?
C6 C1 C2 C3 . . . . 0.2(3) ?
S1 C1 C2 C3 . . . . 175.78(15) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . -0.1(4) ?
C4 C5 C6 C1 . . . . 0.4(3) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
S1 C1 C6 C5 . . . . -175.98(16) ?
S1 N1 C7 C8 . . . . -102.82(18) ?
S1 N1 C7 C12 . . . . 78.98(18) ?
C12 C7 C8 C9 . . . . -2.6(3) ?
N1 C7 C8 C9 . . . . 179.28(17) ?
C12 C7 C8 C13 . . . . 177.4(2) ?
N1 C7 C8 C13 . . . . -0.8(3) ?
C7 C8 C9 C10 . . . . 1.2(3) ?
C13 C8 C9 C10 . . . . -178.8(2) ?
C8 C9 C10 C11 . . . . 0.8(4) ?
C9 C10 C11 C12 . . . . -1.5(3) ?
C9 C10 C11 C14 . . . . 177.4(2) ?
C10 C11 C12 C7 . . . . 0.0(3) ?
C14 C11 C12 C7 . . . . -178.80(18) ?
C8 C7 C12 C11 . . . . 2.1(3) ?
N1 C7 C12 C11 . . . . -179.74(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 502332
