#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222598.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_2222598
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Nirmala, P. G.'
'Fuess, Hartmut'
_publ_section_title
;
 2,4-Dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide
;
_journal_coeditor_code           BT5008
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1940
_journal_paper_doi               10.1107/S1600536809027883
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H7 Cl4 N O2 S'
_chemical_formula_moiety         'C12 H7 Cl4 N O2 S'
_chemical_formula_sum            'C12 H7 Cl4 N O2 S'
_chemical_formula_weight         371.05
_chemical_name_systematic
;
2,4-Dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide
;
_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                81.857(9)
_cell_angle_beta                 72.728(9)
_cell_angle_gamma                78.213(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1498(9)
_cell_length_b                   8.2633(9)
_cell_length_c                   11.8870(10)
_cell_measurement_reflns_used    3818
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.52
_cell_volume                     745.49(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      100(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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7103
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.7805
_exptl_absorpt_correction_T_min  0.6635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.484
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.265
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                2388
_reflns_number_total             2722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5008.cif
_cod_data_source_block           I
_cod_original_cell_volume        745.49(13)
_cod_database_code               2222598
_cod_database_fobs_code          2222598
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
C C1 0.3911(3) 0.5584(3) 0.7834(2) 0.0400(6) Uani d . 1 . .
C C2 0.3221(3) 0.4144(4) 0.8289(2) 0.0464(6) Uani d . 1 . .
H H2 0.3248 0.3369 0.7785 0.056 Uiso calc R 1 . .
C C3 0.2503(3) 0.3869(4) 0.9484(3) 0.0551(7) Uani d . 1 . .
C C4 0.2429(4) 0.5027(4) 1.0245(2) 0.0559(7) Uani d . 1 . .
C C5 0.3100(4) 0.6460(4) 0.9785(3) 0.0590(7) Uani d . 1 . .
H H5 0.3034 0.7251 1.0288 0.071 Uiso calc R 1 . .
C C6 0.3868(4) 0.6734(4) 0.8589(2) 0.0509(7) Uani d . 1 . .
H H6 0.4355 0.7685 0.8291 0.061 Uiso calc R 1 . .
C C7 0.2467(3) 0.8593(3) 0.61967(19) 0.0337(5) Uani d . 1 . .
C C8 0.1074(3) 0.7982(3) 0.6056(2) 0.0352(5) Uani d . 1 . .
C C9 -0.0613(3) 0.8837(3) 0.6440(2) 0.0428(6) Uani d . 1 . .
H H9 -0.1543 0.8439 0.6338 0.051 Uiso calc R 1 . .
C C10 -0.0895(3) 1.0267(3) 0.6968(2) 0.0447(6) Uani d . 1 . .
C C11 0.0473(3) 1.0924(4) 0.7108(3) 0.0513(7) Uani d . 1 . .
H H11 0.0262 1.1911 0.7458 0.062 Uiso calc R 1 . .
C C12 0.2136(3) 1.0071(3) 0.6715(2) 0.0448(6) Uani d . 1 . .
H H12 0.3063 1.0493 0.6798 0.054 Uiso calc R 1 . .
N N1 0.4667(3) 0.5772(3) 0.65959(18) 0.0410(5) Uani d D 1 . .
H H1N 0.478(4) 0.500(3) 0.618(2) 0.049 Uiso d D 1 . .
O O1 0.5157(2) 0.7111(2) 0.46042(14) 0.0419(4) Uani d . 1 . .
O O2 0.5641(2) 0.8522(2) 0.61286(16) 0.0485(5) Uani d . 1 . .
Cl Cl1 0.16795(16) 0.20525(13) 1.00219(9) 0.0922(4) Uani d . 1 . .
Cl Cl2 0.15005(13) 0.47338(13) 1.17468(7) 0.0813(3) Uani d . 1 . .
Cl Cl3 0.13671(8) 0.61471(9) 0.54309(6) 0.0544(3) Uani d . 1 . .
Cl Cl4 -0.30088(9) 1.12858(12) 0.75011(8) 0.0705(3) Uani d . 1 . .
S S1 0.46469(7) 0.75391(7) 0.57981(5) 0.0351(2) 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
C6 C1 C2 . . 119.9(2) ?
C6 C1 N1 . . 123.2(2) ?
C2 C1 N1 . . 116.9(2) ?
C3 C2 C1 . . 119.9(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 120.7(3) ?
C2 C3 Cl1 . . 118.6(2) ?
C4 C3 Cl1 . . 120.7(2) ?
C5 C4 C3 . . 119.2(3) ?
C5 C4 Cl2 . . 119.1(2) ?
C3 C4 Cl2 . . 121.8(2) ?
C6 C5 C4 . . 120.8(3) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 119.6(3) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
C12 C7 C8 . . 119.0(2) ?
C12 C7 S1 . . 117.67(17) ?
C8 C7 S1 . . 123.32(18) ?
C9 C8 C7 . . 120.2(2) ?
C9 C8 Cl3 . . 117.83(17) ?
C7 C8 Cl3 . . 121.98(19) ?
C10 C9 C8 . . 119.3(2) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C9 C10 C11 . . 121.9(2) ?
C9 C10 Cl4 . . 119.22(19) ?
C11 C10 Cl4 . . 118.8(2) ?
C12 C11 C10 . . 118.0(3) ?
C12 C11 H11 . . 121.0 ?
C10 C11 H11 . . 121.0 ?
C11 C12 C7 . . 121.5(2) ?
C11 C12 H12 . . 119.2 ?
C7 C12 H12 . . 119.2 ?
C1 N1 S1 . . 124.52(17) ?
C1 N1 H1N . . 121(2) ?
S1 N1 H1N . . 110(2) ?
O2 S1 O1 . . 118.63(10) ?
O2 S1 N1 . . 109.79(11) ?
O1 S1 N1 . . 104.74(10) ?
O2 S1 C7 . . 105.89(11) ?
O1 S1 C7 . . 111.08(10) ?
N1 S1 C7 . . 106.12(11) ?
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 . 1.386(4) ?
C1 C2 . 1.391(4) ?
C1 N1 . 1.416(3) ?
C2 C3 . 1.372(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.388(4) ?
C3 Cl1 . 1.731(3) ?
C4 C5 . 1.380(4) ?
C4 Cl2 . 1.723(3) ?
C5 C6 . 1.380(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.387(3) ?
C7 C8 . 1.394(3) ?
C7 S1 . 1.768(2) ?
C8 C9 . 1.385(3) ?
C8 Cl3 . 1.724(2) ?
C9 C10 . 1.363(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.396(4) ?
C10 Cl4 . 1.729(3) ?
C11 C12 . 1.371(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
N1 S1 . 1.625(2) ?
N1 H1N . 0.833(17) ?
O1 S1 . 1.4297(17) ?
O2 S1 . 1.4208(16) ?
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_666 0.833(17) 2.079(18) 2.903(3) 170(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
C6 C1 C2 C3 . . . . 0.0(4) ?
N1 C1 C2 C3 . . . . 178.6(2) ?
C1 C2 C3 C4 . . . . 1.1(4) ?
C1 C2 C3 Cl1 . . . . -179.28(19) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
Cl1 C3 C4 C5 . . . . 179.9(2) ?
C2 C3 C4 Cl2 . . . . 178.9(2) ?
Cl1 C3 C4 Cl2 . . . . -0.8(4) ?
C3 C4 C5 C6 . . . . -1.3(5) ?
Cl2 C4 C5 C6 . . . . 179.4(2) ?
C4 C5 C6 C1 . . . . 2.3(5) ?
C2 C1 C6 C5 . . . . -1.7(4) ?
N1 C1 C6 C5 . . . . 179.8(2) ?
C12 C7 C8 C9 . . . . -0.5(4) ?
S1 C7 C8 C9 . . . . 176.96(18) ?
C12 C7 C8 Cl3 . . . . -179.53(19) ?
S1 C7 C8 Cl3 . . . . -2.0(3) ?
C7 C8 C9 C10 . . . . -0.8(4) ?
Cl3 C8 C9 C10 . . . . 178.2(2) ?
C8 C9 C10 C11 . . . . 1.7(4) ?
C8 C9 C10 Cl4 . . . . -177.29(18) ?
C9 C10 C11 C12 . . . . -1.1(4) ?
Cl4 C10 C11 C12 . . . . 177.9(2) ?
C10 C11 C12 C7 . . . . -0.3(4) ?
C8 C7 C12 C11 . . . . 1.1(4) ?
S1 C7 C12 C11 . . . . -176.5(2) ?
C6 C1 N1 S1 . . . . -34.0(3) ?
C2 C1 N1 S1 . . . . 147.43(19) ?
C1 N1 S1 O2 . . . . 65.2(2) ?
C1 N1 S1 O1 . . . . -166.37(17) ?
C1 N1 S1 C7 . . . . -48.8(2) ?
C12 C7 S1 O2 . . . . 0.2(2) ?
C8 C7 S1 O2 . . . . -177.34(19) ?
C12 C7 S1 O1 . . . . -129.9(2) ?
C8 C7 S1 O1 . . . . 52.6(2) ?
C12 C7 S1 N1 . . . . 116.8(2) ?
C8 C7 S1 N1 . . . . -60.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742885
