#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/82/2228217.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228217
loop_
_publ_author_name
'Nirmala, P. G.'
'Foro, Sabine'
'Gowda, B. Thimme'
'Fuess, Hartmut'
_publ_section_title
;
 N-(2,6-Dichlorophenyl)benzenesulfonamide
;
_journal_coeditor_code           BQ2247
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3061
_journal_paper_doi               10.1107/S160053681004420X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H9 Cl2 N O2 S'
_chemical_formula_moiety         'C12 H9 Cl2 N O2 S'
_chemical_formula_sum            'C12 H9 Cl2 N O2 S'
_chemical_formula_weight         302.16
_chemical_name_systematic
;
N-(2,6-Dichlorophenyl)benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.43(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0590(10)
_cell_length_b                   17.143(4)
_cell_length_c                   15.351(3)
_cell_measurement_reflns_used    1612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.92
_cell_volume                     1331.3(5)
_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 omega and phi
;
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4603
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_correction_T_min  0.8834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0399
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                1389
_reflns_number_total             2423
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2247.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228217
_cod_database_fobs_code          2228217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 -0.0324(5) 0.27365(16) 0.83013(17) 0.0403(7) Uani d . 1 . .
C C2 -0.2352(5) 0.22113(18) 0.8401(2) 0.0619(9) Uani d . 1 . .
H H2 -0.3479 0.2095 0.7937 0.074 Uiso calc R 1 . .
C C3 -0.2686(8) 0.1860(2) 0.9200(3) 0.0893(13) Uani d . 1 . .
H H3 -0.4066 0.1509 0.9277 0.107 Uiso calc R 1 . .
C C4 -0.1019(9) 0.2020(3) 0.9883(3) 0.0926(14) Uani d . 1 . .
H H4 -0.1254 0.1775 1.0417 0.111 Uiso calc R 1 . .
C C5 0.0986(8) 0.2541(3) 0.9776(2) 0.0850(12) Uani d . 1 . .
H H5 0.2113 0.2654 1.0241 0.102 Uiso calc R 1 . .
C C6 0.1354(6) 0.2900(2) 0.89885(19) 0.0610(9) Uani d . 1 . .
H H6 0.2732 0.3253 0.8918 0.073 Uiso calc R 1 . .
C C7 -0.0445(5) 0.46992(17) 0.76239(19) 0.0444(7) Uani d . 1 . .
C C8 -0.1209(5) 0.49608(17) 0.8443(2) 0.0507(8) Uani d . 1 . .
C C9 -0.0221(7) 0.5630(2) 0.8804(3) 0.0782(11) Uani d . 1 . .
H H9 -0.0799 0.5794 0.9348 0.094 Uiso calc R 1 . .
C C10 0.1620(9) 0.6057(2) 0.8364(4) 0.0954(14) Uani d . 1 . .
H H10 0.2337 0.6503 0.8616 0.115 Uiso calc R 1 . .
C C11 0.2409(8) 0.5827(2) 0.7553(4) 0.0965(14) Uani d . 1 . .
H H11 0.3652 0.6121 0.7254 0.116 Uiso calc R 1 . .
C C12 0.1356(6) 0.5151(2) 0.7169(2) 0.0657(9) Uani d . 1 . .
N N1 -0.1455(4) 0.40045(13) 0.72490(14) 0.0410(6) Uani d D 1 . .
H H1N -0.306(3) 0.3913(15) 0.7287(17) 0.049 Uiso d D 1 . .
O O1 0.2938(3) 0.33879(11) 0.72465(12) 0.0504(5) Uani d . 1 . .
O O2 -0.0928(4) 0.26891(12) 0.66336(12) 0.0588(6) Uani d . 1 . .
Cl Cl1 -0.35415(17) 0.44425(5) 0.90206(6) 0.0749(3) Uani d . 1 . .
Cl Cl2 0.2244(2) 0.49191(6) 0.61194(7) 0.1076(4) Uani d . 1 . .
S S1 0.02094(12) 0.31832(4) 0.72850(4) 0.0389(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
C2 C1 C6 . . 120.3(3) ?
C2 C1 S1 . . 120.2(2) ?
C6 C1 S1 . . 119.5(2) ?
C1 C2 C3 . . 118.8(3) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 121.0(4) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 119.7(4) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.4(4) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.8(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
C12 C7 C8 . . 117.5(3) ?
C12 C7 N1 . . 120.1(3) ?
C8 C7 N1 . . 122.4(3) ?
C9 C8 C7 . . 122.2(3) ?
C9 C8 Cl1 . . 118.2(3) ?
C7 C8 Cl1 . . 119.6(2) ?
C10 C9 C8 . . 119.8(4) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.0(4) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.5(4) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C7 C12 C11 . . 119.9(3) ?
C7 C12 Cl2 . . 121.2(3) ?
C11 C12 Cl2 . . 118.8(3) ?
C7 N1 S1 . . 121.60(17) ?
C7 N1 H1N . . 118.7(19) ?
S1 N1 H1N . . 109.7(19) ?
O1 S1 O2 . . 120.14(11) ?
O1 S1 N1 . . 106.50(12) ?
O2 S1 N1 . . 106.33(12) ?
O1 S1 C1 . . 107.38(12) ?
O2 S1 C1 . . 107.38(13) ?
N1 S1 C1 . . 108.71(12) ?
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 . 1.374(4) ?
C1 C6 . 1.378(4) ?
C1 S1 . 1.761(3) ?
C2 C3 . 1.378(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.367(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.363(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.370(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.388(4) ?
C7 C8 . 1.392(4) ?
C7 N1 . 1.417(3) ?
C8 C9 . 1.368(4) ?
C8 Cl1 . 1.728(3) ?
C9 C10 . 1.367(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.368(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.402(5) ?
C11 H11 . 0.9300 ?
C12 Cl2 . 1.723(4) ?
N1 S1 . 1.641(2) ?
N1 H1N . 0.832(16) ?
O1 S1 . 1.4259(17) ?
O2 S1 . 1.4284(19) ?
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 1_455 0.832(16) 2.214(18) 3.027(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
C6 C1 C2 C3 . . . . 0.7(4) ?
S1 C1 C2 C3 . . . . 178.8(3) ?
C1 C2 C3 C4 . . . . -0.8(5) ?
C2 C3 C4 C5 . . . . 0.8(6) ?
C3 C4 C5 C6 . . . . -0.6(6) ?
C4 C5 C6 C1 . . . . 0.4(6) ?
C2 C1 C6 C5 . . . . -0.5(5) ?
S1 C1 C6 C5 . . . . -178.5(3) ?
C12 C7 C8 C9 . . . . -0.9(4) ?
N1 C7 C8 C9 . . . . 179.7(3) ?
C12 C7 C8 Cl1 . . . . 177.5(2) ?
N1 C7 C8 Cl1 . . . . -1.9(4) ?
C7 C8 C9 C10 . . . . -1.3(5) ?
Cl1 C8 C9 C10 . . . . -179.8(3) ?
C8 C9 C10 C11 . . . . 2.0(6) ?
C9 C10 C11 C12 . . . . -0.5(6) ?
C8 C7 C12 C11 . . . . 2.5(4) ?
N1 C7 C12 C11 . . . . -178.2(3) ?
C8 C7 C12 Cl2 . . . . -175.1(2) ?
N1 C7 C12 Cl2 . . . . 4.2(4) ?
C10 C11 C12 C7 . . . . -1.8(5) ?
C10 C11 C12 Cl2 . . . . 175.8(3) ?
C12 C7 N1 S1 . . . . 81.8(3) ?
C8 C7 N1 S1 . . . . -98.9(3) ?
C7 N1 S1 O1 . . . . -32.9(2) ?
C7 N1 S1 O2 . . . . -162.2(2) ?
C7 N1 S1 C1 . . . . 82.5(2) ?
C2 C1 S1 O1 . . . . -153.7(2) ?
C6 C1 S1 O1 . . . . 24.4(3) ?
C2 C1 S1 O2 . . . . -23.2(3) ?
C6 C1 S1 O2 . . . . 154.9(2) ?
C2 C1 S1 N1 . . . . 91.5(2) ?
C6 C1 S1 N1 . . . . -90.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15152055
