#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230228.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_2230228
loop_
_publ_author_name
'Shakuntala, K.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 4-Chloro-N-(2,6-dimethylphenyl)benzenesulfonamide
;
_journal_coeditor_code           BQ2299
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1401
_journal_paper_doi               10.1107/S160053681101717X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H14 Cl N O2 S'
_chemical_formula_moiety         'C14 H14 Cl N O2 S'
_chemical_formula_sum            'C14 H14 Cl N O2 S'
_chemical_formula_weight         295.77
_chemical_name_systematic
;
4-Chloro-N-(2,6-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                   7.3816(4)
_cell_length_b                   10.2916(7)
_cell_length_c                   18.3120(10)
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.75
_cell_volume                     1391.13(14)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5356
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.9057
_exptl_absorpt_correction_T_min  0.8496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.245
_refine_ls_abs_structure_details 'Flack (1983), 1113 Friedel pairs'
_refine_ls_abs_structure_Flack   0.43(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0359
_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)+(0.0326P)²+0.3144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                2255
_reflns_number_total             2767
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2299.cif
_cod_data_source_block           I
_cod_database_code               2230228
_cod_database_fobs_code          2230228
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.42735(14) 0.03948(8) -0.04544(5) 0.0851(3) Uani d . 1 1 . .
S S1 0.96404(8) 0.20494(6) 0.19969(4) 0.04077(16) Uani d . 1 1 . .
O O1 0.9231(3) 0.33512(15) 0.22176(9) 0.0502(5) Uani d . 1 1 . .
O O2 1.1425(2) 0.1712(2) 0.17729(11) 0.0606(6) Uani d . 1 1 . .
N N1 0.9167(3) 0.11125(19) 0.26858(12) 0.0389(5) Uani d D 1 1 . .
H H1N 0.950(3) 0.0356(17) 0.2645(14) 0.047 Uiso d D 1 1 . .
C C1 0.8156(3) 0.1660(2) 0.12743(13) 0.0375(6) Uani d . 1 1 . .
C C2 0.8780(4) 0.0962(2) 0.06798(14) 0.0479(7) Uani d . 1 1 . .
H H2 1.0000 0.0745 0.0642 0.057 Uiso calc R 1 1 . .
C C3 0.7573(4) 0.0591(3) 0.01437(15) 0.0568(8) Uani d . 1 1 . .
H H3 0.7974 0.0119 -0.0258 0.068 Uiso calc R 1 1 . .
C C4 0.5788(4) 0.0917(3) 0.02047(14) 0.0513(7) Uani d . 1 1 . .
C C5 0.5165(4) 0.1648(3) 0.07828(15) 0.0524(7) Uani d . 1 1 . .
H H5 0.3949 0.1880 0.0811 0.063 Uiso calc R 1 1 . .
C C6 0.6357(3) 0.2032(3) 0.13178(14) 0.0450(6) Uani d . 1 1 . .
H H6 0.5958 0.2539 0.1706 0.054 Uiso calc R 1 1 . .
C C7 0.7516(3) 0.1254(2) 0.30961(13) 0.0357(5) Uani d . 1 1 . .
C C8 0.6035(3) 0.0460(2) 0.29430(14) 0.0424(6) Uani d . 1 1 . .
C C9 0.4451(4) 0.0670(3) 0.33397(15) 0.0560(7) Uani d . 1 1 . .
H H9 0.3433 0.0166 0.3244 0.067 Uiso calc R 1 1 . .
C C10 0.4376(4) 0.1614(3) 0.38707(17) 0.0620(8) Uani d . 1 1 . .
H H10 0.3302 0.1752 0.4124 0.074 Uiso calc R 1 1 . .
C C11 0.5853(4) 0.2345(3) 0.40283(14) 0.0555(8) Uani d . 1 1 . .
H H11 0.5782 0.2965 0.4397 0.067 Uiso calc R 1 1 . .
C C12 0.7464(4) 0.2189(3) 0.36519(13) 0.0433(6) Uani d . 1 1 . .
C C13 0.6103(4) -0.0616(3) 0.23877(15) 0.0573(7) Uani d . 1 1 . .
H H13A 0.6806 -0.0340 0.1975 0.069 Uiso calc R 1 1 . .
H H13B 0.4896 -0.0823 0.2232 0.069 Uiso calc R 1 1 . .
H H13C 0.6652 -0.1371 0.2602 0.069 Uiso calc R 1 1 . .
C C14 0.9069(4) 0.2998(3) 0.38620(16) 0.0642(8) Uani d . 1 1 . .
H H14A 1.0162 0.2550 0.3730 0.077 Uiso calc R 1 1 . .
H H14B 0.9055 0.3145 0.4380 0.077 Uiso calc R 1 1 . .
H H14C 0.9017 0.3816 0.3611 0.077 Uiso calc R 1 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'
Cl Cl 0.1484 0.1585 '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 . . 120.37(12) ?
O2 S1 N1 . . 106.12(12) ?
O1 S1 N1 . . 106.90(10) ?
O2 S1 C1 . . 107.66(12) ?
O1 S1 C1 . . 107.05(11) ?
N1 S1 C1 . . 108.29(11) ?
C7 N1 S1 . . 121.78(16) ?
C7 N1 H1N . . 113.2(19) ?
S1 N1 H1N . . 115.5(19) ?
C2 C1 C6 . . 120.6(2) ?
C2 C1 S1 . . 120.11(19) ?
C6 C1 S1 . . 119.31(19) ?
C3 C2 C1 . . 119.3(3) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 121.3(3) ?
C3 C4 Cl1 . . 119.4(2) ?
C5 C4 Cl1 . . 119.3(2) ?
C6 C5 C4 . . 119.4(3) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.6(2) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
C8 C7 C12 . . 121.8(2) ?
C8 C7 N1 . . 120.0(2) ?
C12 C7 N1 . . 118.2(2) ?
C7 C8 C9 . . 117.5(2) ?
C7 C8 C13 . . 122.8(2) ?
C9 C8 C13 . . 119.7(2) ?
C10 C9 C8 . . 120.8(3) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C11 C10 C9 . . 120.7(3) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 121.4(3) ?
C10 C11 H11 . . 119.3 ?
C12 C11 H11 . . 119.3 ?
C11 C12 C7 . . 117.7(2) ?
C11 C12 C14 . . 119.1(2) ?
C7 C12 C14 . . 123.1(2) ?
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 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 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
Cl1 C4 . 1.731(3) ?
S1 O2 . 1.4228(18) ?
S1 O1 . 1.4316(17) ?
S1 N1 . 1.626(2) ?
S1 C1 . 1.764(2) ?
N1 C7 . 1.440(3) ?
N1 H1N . 0.818(16) ?
C1 C2 . 1.383(3) ?
C1 C6 . 1.385(3) ?
C2 C3 . 1.380(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.364(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(4) ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.393(3) ?
C7 C12 . 1.401(3) ?
C8 C9 . 1.393(4) ?
C8 C13 . 1.504(3) ?
C9 C10 . 1.375(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.356(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.383(4) ?
C11 H11 . 0.9300 ?
C12 C14 . 1.498(4) ?
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 4_745 0.818(16) 2.282(17) 3.083(3) 166(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
O2 S1 N1 C7 . . . . 174.71(18) ?
O1 S1 N1 C7 . . . . 45.1(2) ?
C1 S1 N1 C7 . . . . -69.9(2) ?
O2 S1 C1 C2 . . . . 9.0(2) ?
O1 S1 C1 C2 . . . . 139.75(19) ?
N1 S1 C1 C2 . . . . -105.3(2) ?
O2 S1 C1 C6 . . . . -172.5(2) ?
O1 S1 C1 C6 . . . . -41.8(2) ?
N1 S1 C1 C6 . . . . 73.1(2) ?
C6 C1 C2 C3 . . . . -2.8(4) ?
S1 C1 C2 C3 . . . . 175.7(2) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C2 C3 C4 C5 . . . . 2.0(4) ?
C2 C3 C4 Cl1 . . . . -177.7(2) ?
C3 C4 C5 C6 . . . . -1.5(4) ?
Cl1 C4 C5 C6 . . . . 178.1(2) ?
C4 C5 C6 C1 . . . . -1.1(4) ?
C2 C1 C6 C5 . . . . 3.3(4) ?
S1 C1 C6 C5 . . . . -175.2(2) ?
S1 N1 C7 C8 . . . . 97.6(2) ?
S1 N1 C7 C12 . . . . -83.4(3) ?
C12 C7 C8 C9 . . . . 3.2(4) ?
N1 C7 C8 C9 . . . . -177.8(2) ?
C12 C7 C8 C13 . . . . -175.3(2) ?
N1 C7 C8 C13 . . . . 3.7(4) ?
C7 C8 C9 C10 . . . . -1.1(4) ?
C13 C8 C9 C10 . . . . 177.4(2) ?
C8 C9 C10 C11 . . . . -1.2(4) ?
C9 C10 C11 C12 . . . . 1.5(4) ?
C10 C11 C12 C7 . . . . 0.5(4) ?
C10 C11 C12 C14 . . . . -178.4(3) ?
C8 C7 C12 C11 . . . . -2.9(4) ?
N1 C7 C12 C11 . . . . 178.1(2) ?
C8 C7 C12 C14 . . . . 175.9(2) ?
N1 C7 C12 C14 . . . . -3.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 260472
