#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224375.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_2224375
loop_
_publ_author_name
'Suchetan, P. A.'
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 N-(4-Chlorobenzoyl)benzenesulfonamide
;
_journal_coeditor_code           NG2687
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3156
_journal_paper_doi               10.1107/S1600536809048399
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 Cl N O3 S'
_chemical_formula_moiety         'C13 H10 Cl N O3 S'
_chemical_formula_sum            'C13 H10 Cl N O3 S'
_chemical_formula_weight         295.73
_chemical_name_systematic
;
N-(4-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                86.666(9)
_cell_angle_beta                 83.903(9)
_cell_angle_gamma                81.823(8)
_cell_formula_units_Z            2
_cell_length_a                   5.4176(4)
_cell_length_b                   10.7170(10)
_cell_length_c                   10.9800(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.02
_cell_measurement_theta_min      5.89
_cell_volume                     626.85(10)
_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, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2490
_diffrn_reflns_theta_full        66.91
_diffrn_reflns_theta_max         66.91
_diffrn_reflns_theta_min         4.05
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.298
_exptl_absorpt_correction_T_max  0.4381
_exptl_absorpt_correction_T_min  0.2321
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.520
_refine_ls_extinction_coef       0.063(5)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0509
_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)+(0.1034P)²+0.2756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                2058
_reflns_number_total             2233
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2687.cif
_cod_data_source_block           I
_cod_original_cell_volume        626.85(9)
_cod_database_code               2224375
_cod_database_fobs_code          2224375
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 0.5435(4) 0.1733(2) 0.8771(2) 0.0411(6) Uani d . 1 . .
C C2 0.7400(5) 0.0803(3) 0.8980(3) 0.0532(7) Uani d . 1 . .
H H2 0.8601 0.0939 0.9485 0.064 Uiso calc R 1 . .
C C3 0.7552(6) -0.0338(3) 0.8426(3) 0.0630(8) Uani d . 1 . .
H H3 0.8860 -0.0976 0.8562 0.076 Uiso calc R 1 . .
C C4 0.5779(6) -0.0531(3) 0.7674(3) 0.0583(7) Uani d . 1 . .
H H4 0.5904 -0.1295 0.7296 0.070 Uiso calc R 1 . .
C C5 0.3821(6) 0.0403(3) 0.7480(3) 0.0555(7) Uani d . 1 . .
H H5 0.2622 0.0263 0.6976 0.067 Uiso calc R 1 . .
C C6 0.3620(5) 0.1542(3) 0.8027(2) 0.0469(6) Uani d . 1 . .
H H6 0.2292 0.2171 0.7900 0.056 Uiso calc R 1 . .
C C7 0.6462(5) 0.4535(2) 0.7460(2) 0.0408(6) Uani d . 1 . .
C C8 0.7940(4) 0.5520(2) 0.6881(2) 0.0387(5) Uani d . 1 . .
C C9 0.7425(5) 0.5974(3) 0.5720(2) 0.0519(7) Uani d . 1 . .
H H9 0.6201 0.5657 0.5343 0.062 Uiso calc R 1 . .
C C10 0.8682(6) 0.6884(3) 0.5111(2) 0.0534(7) Uani d . 1 . .
H H10 0.8306 0.7190 0.4332 0.064 Uiso calc R 1 . .
C C11 1.0517(5) 0.7341(2) 0.5673(2) 0.0441(6) Uani d . 1 . .
C C12 1.1054(5) 0.6914(3) 0.6829(3) 0.0472(6) Uani d . 1 . .
H H12 1.2279 0.7236 0.7201 0.057 Uiso calc R 1 . .
C C13 0.9770(5) 0.6006(2) 0.7438(2) 0.0426(6) Uani d . 1 . .
H H13 1.0125 0.5716 0.8224 0.051 Uiso calc R 1 . .
N N1 0.7013(4) 0.4043(2) 0.8612(2) 0.0465(5) Uani d . 1 . .
H H1N 0.8365 0.4200 0.8882 0.056 Uiso calc R 1 . .
O O1 0.2646(4) 0.37670(19) 0.95259(19) 0.0590(6) Uani d . 1 . .
O O2 0.6378(5) 0.2966(2) 1.05960(18) 0.0655(6) Uani d . 1 . .
O O3 0.4823(4) 0.41570(18) 0.69711(17) 0.0524(5) Uani d . 1 . .
Cl Cl1 1.21303(15) 0.84797(7) 0.48922(7) 0.0649(3) Uani d . 1 . .
S S1 0.51961(12) 0.31704(6) 0.94915(5) 0.0456(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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.3(2) ?
C2 C1 S1 . . 119.1(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 . . 120.3(3) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.6(3) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.8(3) ?
C5 C6 H6 . . 120.6 ?
C1 C6 H6 . . 120.6 ?
O3 C7 N1 . . 119.6(2) ?
O3 C7 C8 . . 122.9(2) ?
N1 C7 C8 . . 117.5(2) ?
C9 C8 C13 . . 118.9(2) ?
C9 C8 C7 . . 116.9(2) ?
C13 C8 C7 . . 124.2(2) ?
C10 C9 C8 . . 121.3(2) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C9 C10 C11 . . 118.9(2) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C12 C11 C10 . . 121.0(2) ?
C12 C11 Cl1 . . 120.2(2) ?
C10 C11 Cl1 . . 118.8(2) ?
C11 C12 C13 . . 119.7(2) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C12 C13 C8 . . 120.2(2) ?
C12 C13 H13 . . 119.9 ?
C8 C13 H13 . . 119.9 ?
C7 N1 S1 . . 123.18(18) ?
C7 N1 H1N . . 118.4 ?
S1 N1 H1N . . 118.4 ?
O2 S1 O1 . . 119.60(14) ?
O2 S1 N1 . . 103.57(12) ?
O1 S1 N1 . . 109.22(12) ?
O2 S1 C1 . . 109.18(12) ?
O1 S1 C1 . . 108.42(12) ?
N1 S1 C1 . . 106.02(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 C2 . 1.379(4) ?
C1 C6 . 1.387(4) ?
C1 S1 . 1.755(2) ?
C2 C3 . 1.385(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.376(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.212(3) ?
C7 N1 . 1.387(3) ?
C7 C8 . 1.488(3) ?
C8 C9 . 1.381(3) ?
C8 C13 . 1.393(4) ?
C9 C10 . 1.371(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.383(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.371(4) ?
C11 Cl1 . 1.735(3) ?
C12 C13 . 1.377(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
N1 S1 . 1.653(2) ?
N1 H1N . 0.8600 ?
O1 S1 . 1.435(2) ?
O2 S1 . 1.422(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 1_655 0.86 2.47 3.281(3) 157.7
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(4) ?
S1 C1 C2 C3 . . . . 178.9(2) ?
C1 C2 C3 C4 . . . . 0.4(5) ?
C2 C3 C4 C5 . . . . -0.8(5) ?
C3 C4 C5 C6 . . . . 0.5(5) ?
C4 C5 C6 C1 . . . . 0.3(4) ?
C2 C1 C6 C5 . . . . -0.8(4) ?
S1 C1 C6 C5 . . . . -179.2(2) ?
O3 C7 C8 C9 . . . . -1.9(4) ?
N1 C7 C8 C9 . . . . 178.1(2) ?
O3 C7 C8 C13 . . . . 177.6(3) ?
N1 C7 C8 C13 . . . . -2.4(4) ?
C13 C8 C9 C10 . . . . 0.3(4) ?
C7 C8 C9 C10 . . . . 179.8(3) ?
C8 C9 C10 C11 . . . . 0.7(4) ?
C9 C10 C11 C12 . . . . -1.2(4) ?
C9 C10 C11 Cl1 . . . . 179.3(2) ?
C10 C11 C12 C13 . . . . 0.7(4) ?
Cl1 C11 C12 C13 . . . . -179.7(2) ?
C11 C12 C13 C8 . . . . 0.2(4) ?
C9 C8 C13 C12 . . . . -0.8(4) ?
C7 C8 C13 C12 . . . . 179.8(2) ?
O3 C7 N1 S1 . . . . -12.7(3) ?
C8 C7 N1 S1 . . . . 167.24(17) ?
C7 N1 S1 O2 . . . . -175.7(2) ?
C7 N1 S1 O1 . . . . -47.2(2) ?
C7 N1 S1 C1 . . . . 69.4(2) ?
C2 C1 S1 O2 . . . . -26.5(3) ?
C6 C1 S1 O2 . . . . 151.9(2) ?
C2 C1 S1 O1 . . . . -158.4(2) ?
C6 C1 S1 O1 . . . . 20.1(2) ?
C2 C1 S1 N1 . . . . 84.5(2) ?
C6 C1 S1 N1 . . . . -97.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1759281
