#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/54/2225475.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_2225475
loop_
_publ_author_name
'Nirmala, P. G.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 2,4-Dichloro-N-(4-chlorophenyl)benzenesulfonamide
;
_journal_coeditor_code           CI5064
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o918
_journal_paper_doi               10.1107/S1600536810010494
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H8 Cl3 N O2 S'
_chemical_formula_moiety         'C12 H8 Cl3 N O2 S'
_chemical_formula_sum            'C12 H8 Cl3 N O2 S'
_chemical_formula_weight         336.60
_chemical_name_systematic
;
2,4-Dichloro-N-(4-chlorophenyl)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                69.510(10)
_cell_angle_beta                 77.960(10)
_cell_angle_gamma                77.300(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3925(9)
_cell_length_b                   10.524(2)
_cell_length_c                   11.684(2)
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      3.24
_cell_volume                     710.8(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_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur single-crystal X-ray diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using ω and φ 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  0.0077
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4462
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  0.7984
_exptl_absorpt_correction_T_min  0.7439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.468
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0348
_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)+(0.0386P)²+0.4934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2514
_reflns_number_total             2873
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5064.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2225475
_cod_database_fobs_code          2225475
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 0.2300(3) -0.1157(2) 0.30386(18) 0.0362(4) Uani d . 1 . .
C C2 0.1233(3) -0.1828(2) 0.25451(18) 0.0370(4) Uani d . 1 . .
C C3 -0.0339(4) -0.2602(2) 0.3281(2) 0.0449(5) Uani d . 1 . .
H H3 -0.1049 -0.3044 0.2949 0.054 Uiso calc R 1 . .
C C4 -0.0835(4) -0.2707(2) 0.4523(2) 0.0504(5) Uani d . 1 . .
C C5 0.0190(4) -0.2058(3) 0.5036(2) 0.0553(6) Uani d . 1 . .
H H5 -0.0168 -0.2136 0.5869 0.066 Uiso calc R 1 . .
C C6 0.1766(4) -0.1286(2) 0.4290(2) 0.0477(5) Uani d . 1 . .
H H6 0.2472 -0.0850 0.4629 0.057 Uiso calc R 1 . .
C C7 0.1442(3) 0.2193(2) 0.13604(18) 0.0357(4) Uani d . 1 . .
C C8 0.1996(3) 0.3448(2) 0.1231(2) 0.0430(5) Uani d . 1 . .
H H8 0.3429 0.3588 0.0971 0.052 Uiso calc R 1 . .
C C9 0.0426(4) 0.4488(2) 0.1487(2) 0.0473(5) Uani d . 1 . .
H H9 0.0792 0.5329 0.1397 0.057 Uiso calc R 1 . .
C C10 -0.1696(3) 0.4259(2) 0.1880(2) 0.0421(5) Uani d . 1 . .
C C11 -0.2275(3) 0.3009(2) 0.2035(2) 0.0420(5) Uani d . 1 . .
H H11 -0.3703 0.2865 0.2317 0.050 Uiso calc R 1 . .
C C12 -0.0694(3) 0.1975(2) 0.17658(19) 0.0397(4) Uani d . 1 . .
H H12 -0.1065 0.1135 0.1857 0.048 Uiso calc R 1 . .
N N1 0.3104(3) 0.11422(18) 0.10621(17) 0.0432(4) Uani d D 1 . .
H H1N 0.312(4) 0.100(3) 0.0395(18) 0.052 Uiso d D 1 . .
O O1 0.4832(3) 0.04803(18) 0.29394(16) 0.0551(4) Uani d . 1 . .
O O2 0.5937(2) -0.08756(17) 0.14887(15) 0.0529(4) Uani d . 1 . .
Cl Cl1 0.17630(10) -0.16945(7) 0.09860(5) 0.05343(17) Uani d . 1 . .
Cl Cl2 -0.28179(14) -0.36791(9) 0.54410(7) 0.0830(3) Uani d . 1 . .
Cl Cl3 -0.36952(11) 0.55863(7) 0.21560(8) 0.0699(2) Uani d . 1 . .
S S1 0.42695(8) -0.00974(5) 0.21258(5) 0.03973(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
C6 C1 C2 . . 118.88(19) ?
C6 C1 S1 . . 118.25(16) ?
C2 C1 S1 . . 122.84(15) ?
C3 C2 C1 . . 120.79(18) ?
C3 C2 Cl1 . . 117.32(16) ?
C1 C2 Cl1 . . 121.87(15) ?
C2 C3 C4 . . 118.9(2) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 121.7(2) ?
C5 C4 Cl2 . . 119.76(18) ?
C3 C4 Cl2 . . 118.58(19) ?
C4 C5 C6 . . 119.0(2) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 120.8(2) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
C12 C7 C8 . . 119.89(18) ?
C12 C7 N1 . . 121.13(18) ?
C8 C7 N1 . . 118.99(18) ?
C9 C8 C7 . . 120.31(19) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C10 C9 C8 . . 119.11(19) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C9 C10 C11 . . 121.48(19) ?
C9 C10 Cl3 . . 119.21(17) ?
C11 C10 Cl3 . . 119.30(16) ?
C10 C11 C12 . . 119.08(19) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C11 C12 C7 . . 120.12(18) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
C7 N1 S1 . . 121.38(14) ?
C7 N1 H1N . . 117.2(18) ?
S1 N1 H1N . . 117.4(18) ?
O1 S1 O2 . . 119.68(10) ?
O1 S1 N1 . . 108.21(10) ?
O2 S1 N1 . . 105.97(10) ?
O1 S1 C1 . . 105.62(10) ?
O2 S1 C1 . . 109.05(10) ?
N1 S1 C1 . . 107.86(10) ?
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 . 1.395(3) ?
C1 C2 . 1.398(3) ?
C1 S1 . 1.787(2) ?
C2 C3 . 1.387(3) ?
C2 Cl1 . 1.743(2) ?
C3 C4 . 1.389(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(4) ?
C4 Cl2 . 1.743(2) ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 C12 . 1.391(3) ?
C7 C8 . 1.391(3) ?
C7 N1 . 1.440(3) ?
C8 C9 . 1.384(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.384(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.384(3) ?
C10 Cl3 . 1.746(2) ?
C11 C12 . 1.389(3) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
N1 S1 . 1.6203(19) ?
N1 H1N . 0.839(16) ?
O1 S1 . 1.4305(17) ?
O2 S1 . 1.4398(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 O2 2_655 0.84(2) 2.20(2) 3.014(3) 163(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 . . . . 0.4(3) ?
S1 C1 C2 C3 . . . . -177.75(16) ?
C6 C1 C2 Cl1 . . . . 178.71(16) ?
S1 C1 C2 Cl1 . . . . 0.6(2) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
Cl1 C2 C3 C4 . . . . -178.66(17) ?
C2 C3 C4 C5 . . . . 0.2(4) ?
C2 C3 C4 Cl2 . . . . 179.86(17) ?
C3 C4 C5 C6 . . . . -0.3(4) ?
Cl2 C4 C5 C6 . . . . -179.93(19) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
C2 C1 C6 C5 . . . . -0.5(3) ?
S1 C1 C6 C5 . . . . 177.76(19) ?
C12 C7 C8 C9 . . . . -0.9(3) ?
N1 C7 C8 C9 . . . . 178.7(2) ?
C7 C8 C9 C10 . . . . 0.3(3) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
C8 C9 C10 Cl3 . . . . -177.94(18) ?
C9 C10 C11 C12 . . . . -1.4(3) ?
Cl3 C10 C11 C12 . . . . 177.38(17) ?
C10 C11 C12 C7 . . . . 0.8(3) ?
C8 C7 C12 C11 . . . . 0.3(3) ?
N1 C7 C12 C11 . . . . -179.30(19) ?
C12 C7 N1 S1 . . . . -81.8(2) ?
C8 C7 N1 S1 . . . . 98.6(2) ?
C7 N1 S1 O1 . . . . -46.02(19) ?
C7 N1 S1 O2 . . . . -175.53(16) ?
C7 N1 S1 C1 . . . . 67.79(18) ?
C6 C1 S1 O1 . . . . -2.80(19) ?
C2 C1 S1 O1 . . . . 175.37(16) ?
C6 C1 S1 O2 . . . . 127.02(17) ?
C2 C1 S1 O2 . . . . -54.81(19) ?
C6 C1 S1 N1 . . . . -118.33(17) ?
C2 C1 S1 N1 . . . . 59.84(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744735
