#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/99/2219951.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_2219951
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 N-(3,5-Dichlorophenyl)benzenesulfonamide
;
_journal_coeditor_code           NG2501
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2190
_journal_paper_doi               10.1107/S1600536808034351
_journal_volume                  64
_journal_year                    2008
_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-(3,5-Dichlorophenyl)benzenesulfonamide
;
_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                90.00
_cell_angle_beta                 99.490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.299(2)
_cell_length_b                   7.2150(10)
_cell_length_c                   21.954(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      19.36
_cell_measurement_theta_min      5.40
_cell_volume                     1296.6(4)
_computing_cell_refinement       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2518
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         4.08
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.959
_exptl_absorpt_correction_T_max  0.2292
_exptl_absorpt_correction_T_min  0.1288
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.384
_refine_ls_extinction_coef       0.0105(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0571
_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)+(0.0987P)²+0.7373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1564
_reflns_number_gt                2153
_reflns_number_total             2311
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2501.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2219951
_cod_database_fobs_code          2219951
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
C C1 0.3043(3) 0.1779(4) 0.79280(13) 0.0445(6) Uani d . 1
C C2 0.4358(4) 0.1697(5) 0.84058(17) 0.0604(8) Uani d . 1
H H2 0.4201 0.1476 0.8809 0.072 Uiso calc R 1
C C3 0.5911(4) 0.1953(6) 0.8269(2) 0.0783(12) Uani d . 1
H H3 0.6811 0.1914 0.8584 0.094 Uiso calc R 1
C C4 0.6130(4) 0.2267(6) 0.7670(2) 0.0773(11) Uani d . 1
H H4 0.7180 0.2427 0.7582 0.093 Uiso calc R 1
C C5 0.4818(5) 0.2344(5) 0.7202(2) 0.0746(10) Uani d . 1
H H5 0.4980 0.2547 0.6798 0.090 Uiso calc R 1
C C6 0.3257(4) 0.2121(4) 0.73293(15) 0.0562(7) Uani d . 1
H H6 0.2360 0.2200 0.7015 0.067 Uiso calc R 1
C C7 0.1252(3) 0.3838(4) 0.90059(11) 0.0400(6) Uani d . 1
C C8 0.2051(4) 0.5522(4) 0.90920(13) 0.0484(6) Uani d . 1
H H8 0.2132 0.6288 0.8758 0.058 Uiso calc R 1
C C9 0.2725(4) 0.6041(4) 0.96827(15) 0.0558(7) Uani d . 1
C C10 0.2645(4) 0.4935(4) 1.01861(14) 0.0590(8) Uani d . 1
H H10 0.3122 0.5293 1.0582 0.071 Uiso calc R 1
C C11 0.1830(4) 0.3278(4) 1.00819(13) 0.0534(7) Uani d . 1
C C12 0.1118(3) 0.2699(4) 0.95062(12) 0.0480(6) Uani d . 1
H H12 0.0561 0.1577 0.9451 0.058 Uiso calc R 1
N N1 0.0494(3) 0.3297(3) 0.84009(10) 0.0441(5) Uani d D 1
H H1N 0.038(4) 0.418(3) 0.8138(12) 0.053 Uiso d D 1
O O1 -0.0021(3) 0.1298(3) 0.74998(9) 0.0527(5) Uani d . 1
O O2 0.1112(3) -0.0066(3) 0.85135(10) 0.0574(6) Uani d . 1
Cl Cl1 0.37237(16) 0.81541(13) 0.97944(5) 0.0927(4) Uani d . 1
Cl Cl2 0.16462(15) 0.18752(15) 1.07089(4) 0.0834(4) Uani d . 1
S S1 0.10584(7) 0.14095(9) 0.80800(3) 0.0412(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C6 C1 C2 121.4(3)
C6 C1 S1 118.8(2)
C2 C1 S1 119.8(2)
C3 C2 C1 118.5(4)
C3 C2 H2 120.8
C1 C2 H2 120.8
C4 C3 C2 120.3(4)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 120.6(3)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.0(4)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 119.2(3)
C1 C6 H6 120.4
C5 C6 H6 120.4
C8 C7 C12 120.7(2)
C8 C7 N1 119.7(2)
C12 C7 N1 119.5(2)
C9 C8 C7 118.6(3)
C9 C8 H8 120.7
C7 C8 H8 120.7
C10 C9 C8 122.3(3)
C10 C9 Cl1 118.9(2)
C8 C9 Cl1 118.9(2)
C11 C10 C9 117.3(3)
C11 C10 H10 121.3
C9 C10 H10 121.3
C12 C11 C10 123.0(3)
C12 C11 Cl2 118.2(2)
C10 C11 Cl2 118.7(2)
C11 C12 C7 118.0(3)
C11 C12 H12 121.0
C7 C12 H12 121.0
C7 N1 S1 120.98(18)
C7 N1 H1N 114(2)
S1 N1 H1N 110(2)
O2 S1 O1 119.87(14)
O2 S1 N1 108.29(12)
O1 S1 N1 104.34(12)
O2 S1 C1 108.30(14)
O1 S1 C1 107.97(13)
N1 S1 C1 107.45(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.377(4)
C1 C2 1.385(4)
C1 S1 1.754(3)
C2 C3 1.383(5)
C2 H2 0.9300
C3 C4 1.376(6)
C3 H3 0.9300
C4 C5 1.370(6)
C4 H4 0.9300
C5 C6 1.379(5)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.382(4)
C7 C12 1.391(4)
C7 N1 1.427(3)
C8 C9 1.377(4)
C8 H8 0.9300
C9 C10 1.374(5)
C9 Cl1 1.734(3)
C10 C11 1.374(5)
C10 H10 0.9300
C11 C12 1.369(4)
C11 Cl2 1.736(3)
C12 H12 0.9300
N1 S1 1.637(2)
N1 H1N 0.856(10)
O1 S1 1.433(2)
O2 S1 1.424(2)
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_556 0.856(10) 2.059(11) 2.915(3) 178(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
C6 C1 C2 C3 -0.5(5)
S1 C1 C2 C3 178.6(3)
C1 C2 C3 C4 -0.5(5)
C2 C3 C4 C5 0.5(6)
C3 C4 C5 C6 0.5(6)
C2 C1 C6 C5 1.5(5)
S1 C1 C6 C5 -177.6(3)
C4 C5 C6 C1 -1.5(5)
C12 C7 C8 C9 0.6(4)
N1 C7 C8 C9 177.8(3)
C7 C8 C9 C10 0.7(5)
C7 C8 C9 Cl1 -179.8(2)
C8 C9 C10 C11 -1.2(5)
Cl1 C9 C10 C11 179.4(3)
C9 C10 C11 C12 0.3(5)
C9 C10 C11 Cl2 -178.0(3)
C10 C11 C12 C7 1.0(5)
Cl2 C11 C12 C7 179.2(2)
C8 C7 C12 C11 -1.4(4)
N1 C7 C12 C11 -178.6(3)
C8 C7 N1 S1 119.8(2)
C12 C7 N1 S1 -62.9(3)
C7 N1 S1 O2 48.5(2)
C7 N1 S1 O1 177.3(2)
C7 N1 S1 C1 -68.3(2)
C6 C1 S1 O2 138.8(2)
C2 C1 S1 O2 -40.3(3)
C6 C1 S1 O1 7.6(3)
C2 C1 S1 O1 -171.5(2)
C6 C1 S1 N1 -104.5(2)
C2 C1 S1 N1 76.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4166260
