#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222908.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_2222908
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide
;
_journal_coeditor_code           TK2510
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1976
_journal_paper_doi               10.1107/S1600536809028840
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H13 Cl2 N O2 S'
_chemical_formula_moiety         'C14 H13 Cl2 N O2 S'
_chemical_formula_sum            'C14 H13 Cl2 N O2 S'
_chemical_formula_weight         330.21
_chemical_name_systematic
;
N-(3,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 99.644(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8046(7)
_cell_length_b                   9.2688(8)
_cell_length_c                   18.9470(10)
_cell_measurement_reflns_used    4751
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1524.4(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      303(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.013
_diffrn_reflns_av_sigmaI/netI    0.012
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10274
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0506P)²+0.7353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                2618
_reflns_number_total             3064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2510.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222908
_cod_database_fobs_code          2222908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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 0.7751(2) 0.1105(2) 0.26937(9) 0.0342(4) Uani d . 1 . .
C C2 0.7595(2) 0.0272(2) 0.32852(10) 0.0405(4) Uani d . 1 . .
H H2 0.8407 -0.0308 0.3497 0.049 Uiso calc R 1 . .
C C3 0.6243(2) 0.0301(2) 0.35611(10) 0.0425(5) Uani d . 1 . .
C C4 0.5020(2) 0.1148(2) 0.32506(10) 0.0425(5) Uani d . 1 . .
C C5 0.5178(2) 0.1972(3) 0.26616(10) 0.0472(5) Uani d . 1 . .
H H5 0.4360 0.2544 0.2449 0.057 Uiso calc R 1 . .
C C6 0.6528(2) 0.1963(2) 0.23813(10) 0.0441(5) Uani d . 1 . .
H H6 0.6618 0.2529 0.1985 0.053 Uiso calc R 1 . .
C C7 0.8600(2) 0.1276(2) 0.09846(9) 0.0334(4) Uani d . 1 . .
C C8 0.8733(2) -0.0147(2) 0.07500(10) 0.0363(4) Uani d . 1 . .
C C9 0.7833(2) -0.0518(2) 0.01025(10) 0.0410(4) Uani d . 1 . .
H H9 0.7907 -0.1453 -0.0067 0.049 Uiso calc R 1 . .
C C10 0.6828(2) 0.0432(2) -0.03070(10) 0.0403(4) Uani d . 1 . .
C C11 0.6726(2) 0.1824(2) -0.00542(10) 0.0434(5) Uani d . 1 . .
H H11 0.6057 0.2479 -0.0317 0.052 Uiso calc R 1 . .
C C12 0.7608(2) 0.2250(2) 0.05836(10) 0.0406(4) Uani d . 1 . .
H H12 0.7537 0.3191 0.0746 0.049 Uiso calc R 1 . .
C C13 0.9776(3) -0.1262(2) 0.11551(13) 0.0515(5) Uani d . 1 . .
H H13A 0.9396 -0.1519 0.1584 0.062 Uiso calc R 1 . .
H H13B 1.0797 -0.0874 0.1277 0.062 Uiso calc R 1 . .
H H13C 0.9800 -0.2103 0.0862 0.062 Uiso calc R 1 . .
C C14 0.5881(3) -0.0036(3) -0.10031(11) 0.0529(5) Uani d . 1 . .
H H14A 0.5855 -0.1071 -0.1026 0.064 Uiso calc R 1 . .
H H14B 0.6331 0.0336 -0.1394 0.064 Uiso calc R 1 . .
H H14C 0.4851 0.0328 -0.1035 0.064 Uiso calc R 1 . .
N N1 0.91696(19) 0.1015(2) 0.24438(8) 0.0407(4) Uani d D 1 . .
H H1N 0.976(2) 0.035(2) 0.2605(12) 0.049 Uiso d D 1 . .
O O1 0.92732(17) 0.33947(15) 0.18616(7) 0.0471(4) Uani d . 1 . .
O O2 1.12802(16) 0.15602(19) 0.18124(8) 0.0530(4) Uani d . 1 . .
Cl Cl1 0.61158(9) -0.07351(7) 0.43079(4) 0.0753(2) Uani d . 1 . .
Cl Cl2 0.33330(7) 0.12189(9) 0.36022(3) 0.0680(2) Uani d . 1 . .
S S1 0.96962(5) 0.19135(5) 0.17881(2) 0.03717(14) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 119.25(18) ?
C2 C1 N1 . . 116.83(17) ?
C6 C1 N1 . . 123.92(17) ?
C3 C2 C1 . . 120.29(18) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.68(18) ?
C2 C3 Cl1 . . 118.55(16) ?
C4 C3 Cl1 . . 120.77(15) ?
C5 C4 C3 . . 118.87(18) ?
C5 C4 Cl2 . . 120.05(16) ?
C3 C4 Cl2 . . 121.06(16) ?
C4 C5 C6 . . 121.20(19) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C5 C6 C1 . . 119.71(18) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
C12 C7 C8 . . 121.01(17) ?
C12 C7 S1 . . 117.22(14) ?
C8 C7 S1 . . 121.76(14) ?
C9 C8 C7 . . 116.59(17) ?
C9 C8 C13 . . 119.36(18) ?
C7 C8 C13 . . 124.05(18) ?
C8 C9 C10 . . 123.55(18) ?
C8 C9 H9 . . 118.2 ?
C10 C9 H9 . . 118.2 ?
C11 C10 C9 . . 118.01(18) ?
C11 C10 C14 . . 120.96(19) ?
C9 C10 C14 . . 121.03(19) ?
C12 C11 C10 . . 120.66(18) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C7 . . 120.17(18) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
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 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C1 N1 S1 . . 127.44(14) ?
C1 N1 H1N . . 117.1(16) ?
S1 N1 H1N . . 114.8(16) ?
O2 S1 O1 . . 119.00(9) ?
O2 S1 N1 . . 105.08(9) ?
O1 S1 N1 . . 107.69(9) ?
O2 S1 C7 . . 109.99(9) ?
O1 S1 C7 . . 106.92(9) ?
N1 S1 C7 . . 107.66(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 C2 . 1.387(3) ?
C1 C6 . 1.389(3) ?
C1 N1 . 1.410(2) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.382(3) ?
C3 Cl1 . 1.729(2) ?
C4 C5 . 1.378(3) ?
C4 Cl2 . 1.7283(19) ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.391(3) ?
C7 C8 . 1.403(3) ?
C7 S1 . 1.7623(18) ?
C8 C9 . 1.387(3) ?
C8 C13 . 1.505(3) ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.385(3) ?
C10 C14 . 1.501(3) ?
C11 C12 . 1.380(3) ?
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 . 1.6264(17) ?
N1 H1N . 0.833(16) ?
O1 S1 . 1.4353(15) ?
O2 S1 . 1.4258(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 O1 2_745 0.833(16) 2.176(17) 2.984(2) 164(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 . . . . -0.2(3) ?
N1 C1 C2 C3 . . . . -179.96(17) ?
C1 C2 C3 C4 . . . . 0.5(3) ?
C1 C2 C3 Cl1 . . . . -179.00(14) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
Cl1 C3 C4 C5 . . . . 179.16(16) ?
C2 C3 C4 Cl2 . . . . -178.74(15) ?
Cl1 C3 C4 Cl2 . . . . 0.7(2) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
Cl2 C4 C5 C6 . . . . 178.33(16) ?
C4 C5 C6 C1 . . . . 0.4(3) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
N1 C1 C6 C5 . . . . 179.52(18) ?
C12 C7 C8 C9 . . . . 0.3(3) ?
S1 C7 C8 C9 . . . . -178.82(13) ?
C12 C7 C8 C13 . . . . -179.77(19) ?
S1 C7 C8 C13 . . . . 1.1(3) ?
C7 C8 C9 C10 . . . . -0.6(3) ?
C13 C8 C9 C10 . . . . 179.49(19) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C8 C9 C10 C14 . . . . -179.83(18) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C14 C10 C11 C12 . . . . -179.54(19) ?
C10 C11 C12 C7 . . . . -0.7(3) ?
C8 C7 C12 C11 . . . . 0.3(3) ?
S1 C7 C12 C11 . . . . 179.45(15) ?
C2 C1 N1 S1 . . . . -177.17(15) ?
C6 C1 N1 S1 . . . . 3.1(3) ?
C1 N1 S1 O2 . . . . 173.04(16) ?
C1 N1 S1 O1 . . . . 45.23(19) ?
C1 N1 S1 C7 . . . . -69.74(18) ?
C12 C7 S1 O2 . . . . -129.57(15) ?
C8 C7 S1 O2 . . . . 49.56(17) ?
C12 C7 S1 O1 . . . . 0.97(17) ?
C8 C7 S1 O1 . . . . -179.90(14) ?
C12 C7 S1 N1 . . . . 116.45(15) ?
C8 C7 S1 N1 . . . . -64.42(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12777331
