#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220725.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_2220725
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,3-Dimethylphenyl)benzenesulfonamide
;
_journal_coeditor_code           BT2853
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o366
_journal_paper_doi               10.1107/S1600536809002098
_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-(2,3-Dimethylphenyl)benzenesulfonamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.3969(5)
_cell_length_b                   8.8767(6)
_cell_length_c                   23.082(2)
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.29
_cell_volume                     1310.67(18)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2004)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2004)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ
;
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5869
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_correction_T_min  0.8893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_ls_abs_structure_details 'Flack (1983), 1060 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0340
_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)+(0.0525P)²+0.1566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                2200
_reflns_number_total             2611
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2853.cif
_cod_data_source_block           I
_cod_database_code               2220725
_cod_database_fobs_code          2220725
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'
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 0.2823(3) -0.0378(2) 0.43543(9) 0.0389(5) Uani d . 1 . .
C C2 0.4720(4) -0.0422(3) 0.46456(11) 0.0507(6) Uani d . 1 . .
H H2 0.5124 0.0374 0.4882 0.061 Uiso calc R 1 . .
C C3 0.5998(4) -0.1662(3) 0.45797(13) 0.0651(7) Uani d . 1 . .
H H3 0.7262 -0.1708 0.4778 0.078 Uiso calc R 1 . .
C C4 0.5424(5) -0.2816(3) 0.42263(14) 0.0701(9) Uani d . 1 . .
H H4 0.6285 -0.3655 0.4189 0.084 Uiso calc R 1 . .
C C5 0.3566(6) -0.2746(3) 0.39226(13) 0.0740(9) Uani d . 1 . .
H H5 0.3206 -0.3519 0.3670 0.089 Uiso calc R 1 . .
C C6 0.2245(5) -0.1532(3) 0.39934(11) 0.0564(6) Uani d . 1 . .
H H6 0.0974 -0.1496 0.3798 0.068 Uiso calc R 1 . .
C C7 0.2683(4) 0.2922(2) 0.36164(9) 0.0419(5) Uani d . 1 . .
C C8 0.1257(4) 0.3805(2) 0.33190(9) 0.0441(5) Uani d . 1 . .
C C9 0.1664(4) 0.4088(3) 0.27267(10) 0.0536(6) Uani d . 1 . .
C C10 0.3383(5) 0.3483(3) 0.24667(12) 0.0701(8) Uani d . 1 . .
H H10 0.3632 0.3679 0.2077 0.084 Uiso calc R 1 . .
C C11 0.4762(5) 0.2585(3) 0.27715(13) 0.0757(9) Uani d . 1 . .
H H11 0.5909 0.2167 0.2583 0.091 Uiso calc R 1 . .
C C12 0.4452(4) 0.2308(3) 0.33475(11) 0.0566(7) Uani d . 1 . .
H H12 0.5395 0.1724 0.3557 0.068 Uiso calc R 1 . .
C C13 -0.0598(4) 0.4452(3) 0.36156(12) 0.0601(7) Uani d . 1 . .
H H13A -0.0457 0.5528 0.3637 0.072 Uiso calc R 1 . .
H H13B -0.0697 0.4045 0.4000 0.072 Uiso calc R 1 . .
H H13C -0.1837 0.4203 0.3402 0.072 Uiso calc R 1 . .
C C14 0.0210(6) 0.5071(4) 0.23845(14) 0.0840(10) Uani d . 1 . .
H H14A 0.0214 0.6070 0.2544 0.101 Uiso calc R 1 . .
H H14B -0.1179 0.4664 0.2402 0.101 Uiso calc R 1 . .
H H14C 0.0665 0.5108 0.1988 0.101 Uiso calc R 1 . .
N N1 0.2351(3) 0.2670(2) 0.42314(7) 0.0413(5) Uani d . 1 . .
H H1N 0.337(4) 0.290(3) 0.4439(10) 0.050 Uiso d . 1 . .
O O1 -0.0648(3) 0.09633(19) 0.41129(7) 0.0567(5) Uani d . 1 . .
O O2 0.0967(3) 0.13781(18) 0.50761(6) 0.0577(5) Uani d . 1 . .
S S1 0.11619(8) 0.11797(6) 0.44610(2) 0.04071(16) 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 0.0033 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
C6 C1 C2 . . 120.6(2) ?
C6 C1 S1 . . 120.57(19) ?
C2 C1 S1 . . 118.80(16) ?
C3 C2 C1 . . 119.2(2) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C4 C3 C2 . . 120.4(3) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.1(3) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.4(3) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C8 C7 C12 . . 122.2(2) ?
C8 C7 N1 . . 118.4(2) ?
C12 C7 N1 . . 119.4(2) ?
C7 C8 C9 . . 117.3(2) ?
C7 C8 C13 . . 121.1(2) ?
C9 C8 C13 . . 121.6(2) ?
C10 C9 C8 . . 120.3(2) ?
C10 C9 C14 . . 119.8(2) ?
C8 C9 C14 . . 119.9(2) ?
C9 C10 C11 . . 121.2(3) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C11 C10 . . 120.4(3) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C7 . . 118.6(3) ?
C11 C12 H12 . . 120.7 ?
C7 C12 H12 . . 120.7 ?
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 ?
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 . . 121.07(14) ?
C7 N1 H1N . . 114.0(17) ?
S1 N1 H1N . . 112.4(17) ?
O1 S1 O2 . . 120.28(11) ?
O1 S1 N1 . . 107.97(10) ?
O2 S1 N1 . . 105.37(10) ?
O1 S1 C1 . . 107.82(10) ?
O2 S1 C1 . . 106.68(10) ?
N1 S1 C1 . . 108.24(9) ?
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 . 1.371(3) ?
C1 C2 . 1.388(3) ?
C1 S1 . 1.762(2) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.360(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.385(3) ?
C7 C12 . 1.401(3) ?
C7 N1 . 1.453(3) ?
C8 C9 . 1.414(3) ?
C8 C13 . 1.485(3) ?
C9 C10 . 1.363(4) ?
C9 C14 . 1.500(4) ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.367(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 . 1.615(2) ?
N1 H1N . 0.84(3) ?
O1 S1 . 1.4221(17) ?
O2 S1 . 1.4362(15) ?
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 3_556 0.84(3) 2.10(3) 2.936(2) 176(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 . . . . -1.7(3) ?
S1 C1 C2 C3 . . . . 177.83(19) ?
C1 C2 C3 C4 . . . . 1.1(4) ?
C2 C3 C4 C5 . . . . 1.0(4) ?
C3 C4 C5 C6 . . . . -2.5(4) ?
C2 C1 C6 C5 . . . . 0.2(4) ?
S1 C1 C6 C5 . . . . -179.3(2) ?
C4 C5 C6 C1 . . . . 1.9(4) ?
C12 C7 C8 C9 . . . . -0.8(3) ?
N1 C7 C8 C9 . . . . 177.31(19) ?
C12 C7 C8 C13 . . . . -179.5(2) ?
N1 C7 C8 C13 . . . . -1.4(3) ?
C7 C8 C9 C10 . . . . 1.1(3) ?
C13 C8 C9 C10 . . . . 179.7(2) ?
C7 C8 C9 C14 . . . . -178.3(2) ?
C13 C8 C9 C14 . . . . 0.3(3) ?
C8 C9 C10 C11 . . . . 0.0(4) ?
C14 C9 C10 C11 . . . . 179.4(3) ?
C9 C10 C11 C12 . . . . -1.4(5) ?
C10 C11 C12 C7 . . . . 1.6(4) ?
C8 C7 C12 C11 . . . . -0.5(4) ?
N1 C7 C12 C11 . . . . -178.6(2) ?
C8 C7 N1 S1 . . . . 95.3(2) ?
C12 C7 N1 S1 . . . . -86.4(2) ?
C7 N1 S1 O1 . . . . -45.5(2) ?
C7 N1 S1 O2 . . . . -175.20(17) ?
C7 N1 S1 C1 . . . . 70.97(19) ?
C6 C1 S1 O1 . . . . -1.1(2) ?
C2 C1 S1 O1 . . . . 179.35(17) ?
C6 C1 S1 O2 . . . . 129.3(2) ?
C2 C1 S1 O2 . . . . -50.2(2) ?
C6 C1 S1 N1 . . . . -117.7(2) ?
C2 C1 S1 N1 . . . . 62.79(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 260502
