#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226343.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_2226343
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Suchetan, P. A.'
'Fuess, Hartmut'
_publ_section_title
;
 4-Chloro-N-(2-chlorobenzoyl)benzenesulfonamide
;
_journal_coeditor_code           XU2765
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1467
_journal_paper_doi               10.1107/S1600536810019057
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 Cl2 N O3 S'
_chemical_formula_moiety         'C13 H9 Cl2 N O3 S'
_chemical_formula_sum            'C13 H9 Cl2 N O3 S'
_chemical_formula_weight         330.17
_chemical_name_systematic
;
4-Chloro-N-(2-chlorobenzoyl)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                79.010(10)
_cell_angle_beta                 74.470(10)
_cell_angle_gamma                84.760(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3882(9)
_cell_length_b                   10.3110(10)
_cell_length_c                   11.1710(10)
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.52
_cell_volume                     695.32(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      299(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4417
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.9181
_exptl_absorpt_correction_T_min  0.8652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.516
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.1863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                2378
_reflns_number_total             2825
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2765.cif
_cod_data_source_block           I
_cod_original_cell_volume        695.32(13)
_cod_database_code               2226343
_cod_database_fobs_code          2226343
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 0.3004(3) 0.27841(17) 0.07988(17) 0.0364(4) Uani d . 1 . .
C C2 0.1714(3) 0.39202(19) 0.0968(2) 0.0464(5) Uani d . 1 . .
H H2 0.0437 0.4059 0.0703 0.056 Uiso calc R 1 . .
C C3 0.2338(4) 0.4844(2) 0.1532(2) 0.0561(6) Uani d . 1 . .
H H3 0.1510 0.5624 0.1634 0.067 Uiso calc R 1 . .
C C4 0.4198(4) 0.4596(2) 0.1942(2) 0.0520(5) Uani d . 1 . .
C C5 0.5482(4) 0.3465(2) 0.1791(2) 0.0543(5) Uani d . 1 . .
H H5 0.6730 0.3317 0.2085 0.065 Uiso calc R 1 . .
C C6 0.4895(3) 0.2553(2) 0.1198(2) 0.0478(5) Uani d . 1 . .
H H6 0.5760 0.1791 0.1068 0.057 Uiso calc R 1 . .
C C7 0.0089(3) 0.02215(18) 0.22952(18) 0.0384(4) Uani d . 1 . .
C C8 0.0163(3) -0.09961(18) 0.32606(17) 0.0396(4) Uani d . 1 . .
C C9 0.1632(3) -0.1155(2) 0.39978(18) 0.0451(4) Uani d . 1 . .
C C10 0.1579(5) -0.2246(3) 0.4941(2) 0.0641(7) Uani d . 1 . .
H H10 0.2565 -0.2347 0.5436 0.077 Uiso calc R 1 . .
C C11 0.0073(6) -0.3171(3) 0.5141(2) 0.0757(8) Uani d . 1 . .
H H11 0.0043 -0.3908 0.5771 0.091 Uiso calc R 1 . .
C C12 -0.1402(5) -0.3025(3) 0.4422(3) 0.0730(7) Uani d . 1 . .
H H12 -0.2424 -0.3663 0.4568 0.088 Uiso calc R 1 . .
C C13 -0.1370(4) -0.1940(2) 0.3487(2) 0.0554(5) Uani d . 1 . .
H H13 -0.2378 -0.1840 0.3007 0.066 Uiso calc R 1 . .
Cl Cl1 0.34983(10) 0.00381(7) 0.37663(6) 0.0664(2) Uani d . 1 . .
Cl Cl2 0.49683(16) 0.57327(7) 0.26873(8) 0.0938(3) Uani d . 1 . .
N N1 0.1748(3) 0.02815(15) 0.12059(15) 0.0398(4) Uani d D 1 . .
H H1N 0.276(3) -0.0255(19) 0.114(2) 0.048 Uiso d D 1 . .
O O1 0.0294(3) 0.20637(15) -0.02823(14) 0.0550(4) Uani d . 1 . .
O O2 0.4074(3) 0.11865(14) -0.08329(13) 0.0537(4) Uani d . 1 . .
O O3 -0.1307(2) 0.10807(16) 0.24443(16) 0.0602(4) Uani d . 1 . .
S S1 0.22277(8) 0.15972(4) 0.00846(4) 0.04047(15) 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'
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
C6 C1 C2 . . 121.20(18) ?
C6 C1 S1 . . 118.92(14) ?
C2 C1 S1 . . 119.87(15) ?
C3 C2 C1 . . 119.35(19) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 119.03(19) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 122.2(2) ?
C3 C4 Cl2 . . 119.51(17) ?
C5 C4 Cl2 . . 118.31(18) ?
C4 C5 C6 . . 119.0(2) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 119.17(18) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
O3 C7 N1 . . 122.05(18) ?
O3 C7 C8 . . 123.12(18) ?
N1 C7 C8 . . 114.82(15) ?
C13 C8 C9 . . 119.07(19) ?
C13 C8 C7 . . 119.35(17) ?
C9 C8 C7 . . 121.40(17) ?
C10 C9 C8 . . 120.5(2) ?
C10 C9 Cl1 . . 119.64(18) ?
C8 C9 Cl1 . . 119.82(16) ?
C11 C10 C9 . . 119.6(2) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 120.7(2) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.2(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C8 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
C7 N1 S1 . . 124.25(13) ?
C7 N1 H1N . . 121.9(16) ?
S1 N1 H1N . . 112.1(16) ?
O1 S1 O2 . . 119.26(9) ?
O1 S1 N1 . . 110.18(9) ?
O2 S1 N1 . . 103.74(8) ?
O1 S1 C1 . . 108.96(9) ?
O2 S1 C1 . . 109.21(9) ?
N1 S1 C1 . . 104.43(8) ?
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 . 1.382(3) ?
C1 C2 . 1.383(3) ?
C1 S1 . 1.7537(19) ?
C2 C3 . 1.377(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.370(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(3) ?
C4 Cl2 . 1.733(2) ?
C5 C6 . 1.379(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.200(2) ?
C7 N1 . 1.379(3) ?
C7 C8 . 1.497(3) ?
C8 C13 . 1.385(3) ?
C8 C9 . 1.386(3) ?
C9 C10 . 1.382(3) ?
C9 Cl1 . 1.727(2) ?
C10 C11 . 1.363(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.375(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
N1 S1 . 1.6510(16) ?
N1 H1N . 0.810(15) ?
O1 S1 . 1.4185(15) ?
O2 S1 . 1.4311(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 2_655 0.810(15) 2.127(16) 2.914(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 . . . . 0.7(3) ?
S1 C1 C2 C3 . . . . 179.87(16) ?
C1 C2 C3 C4 . . . . -1.7(3) ?
C2 C3 C4 C5 . . . . 1.0(3) ?
C2 C3 C4 Cl2 . . . . -178.50(16) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
Cl2 C4 C5 C6 . . . . -179.85(17) ?
C4 C5 C6 C1 . . . . -1.6(3) ?
C2 C1 C6 C5 . . . . 0.9(3) ?
S1 C1 C6 C5 . . . . -178.23(16) ?
O3 C7 C8 C13 . . . . 70.4(3) ?
N1 C7 C8 C13 . . . . -109.1(2) ?
O3 C7 C8 C9 . . . . -104.8(2) ?
N1 C7 C8 C9 . . . . 75.7(2) ?
C13 C8 C9 C10 . . . . 0.4(3) ?
C7 C8 C9 C10 . . . . 175.66(18) ?
C13 C8 C9 Cl1 . . . . -177.81(16) ?
C7 C8 C9 Cl1 . . . . -2.6(3) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
Cl1 C9 C10 C11 . . . . 178.50(19) ?
C9 C10 C11 C12 . . . . -0.5(4) ?
C10 C11 C12 C13 . . . . 0.1(4) ?
C11 C12 C13 C8 . . . . 0.6(4) ?
C9 C8 C13 C12 . . . . -0.9(3) ?
C7 C8 C13 C12 . . . . -176.2(2) ?
O3 C7 N1 S1 . . . . 9.1(3) ?
C8 C7 N1 S1 . . . . -171.37(13) ?
C7 N1 S1 O1 . . . . -51.19(18) ?
C7 N1 S1 O2 . . . . -179.94(15) ?
C7 N1 S1 C1 . . . . 65.68(17) ?
C6 C1 S1 O1 . . . . -178.06(15) ?
C2 C1 S1 O1 . . . . 2.78(18) ?
C6 C1 S1 O2 . . . . -46.22(18) ?
C2 C1 S1 O2 . . . . 134.61(15) ?
C6 C1 S1 N1 . . . . 64.23(17) ?
C2 C1 S1 N1 . . . . -114.93(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 845690
