#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223575.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_2223575
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Suchetan, P. A.'
'Fuess, Hartmut'
_publ_section_title
;
 N-Benzoylbenzenesulfonamide
;
_journal_coeditor_code           TK2540
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2516
_journal_paper_doi               10.1107/S1600536809037222
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H11 N O3 S'
_chemical_formula_moiety         'C13 H11 N O3 S'
_chemical_formula_sum            'C13 H11 N O3 S'
_chemical_formula_weight         261.29
_chemical_name_systematic
;
N-Benzoylbenzenesulfonamide
;
_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           SHELXL97
_cell_angle_alpha                90.187(8)
_cell_angle_beta                 99.074(9)
_cell_angle_gamma                99.617(9)
_cell_formula_units_Z            2
_cell_length_a                   5.8396(7)
_cell_length_b                   10.1780(10)
_cell_length_c                   10.4050(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      22.9
_cell_measurement_theta_min      4.3
_cell_volume                     601.83(11)
_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      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  0.011
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2354
_diffrn_reflns_theta_full        66.9
_diffrn_reflns_theta_max         66.9
_diffrn_reflns_theta_min         4.3
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_T_max  0.8893
_exptl_absorpt_correction_T_min  0.3796
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al.,  1968'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'long plate'
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.36
_refine_ls_extinction_coef       0.024(3)
_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   1.18
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.19
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0862P)²+0.5464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.169
_refine_ls_wR_factor_ref         0.171
_reflns_number_gt                1962
_reflns_number_total             2125
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2540.cif
_cod_data_source_block           I
_cod_database_code               2223575
_cod_database_fobs_code          2223575
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 0.3607(5) 0.8198(3) 0.8908(3) 0.0337(6) Uani d . 1 . .
C C2 0.2344(5) 0.9229(3) 0.8901(3) 0.0407(7) Uani d . 1 . .
H H2 0.1021 0.9143 0.9307 0.049 Uiso calc R 1 . .
C C3 0.3058(7) 1.0380(3) 0.8289(4) 0.0539(9) Uani d . 1 . .
H H3 0.2219 1.1081 0.8283 0.065 Uiso calc R 1 . .
C C4 0.5004(7) 1.0503(4) 0.7686(4) 0.0589(10) Uani d . 1 . .
H H4 0.5482 1.1288 0.7274 0.071 Uiso calc R 1 . .
C C5 0.6248(6) 0.9472(4) 0.7688(4) 0.0583(10) Uani d U 1 . .
H H5 0.7553 0.9559 0.7266 0.070 Uiso calc R 1 . .
C C6 0.5584(5) 0.8304(4) 0.8311(3) 0.0470(8) Uani d . 1 . .
H H6 0.6442 0.7611 0.8329 0.056 Uiso calc R 1 . .
C C7 0.0114(5) 0.5480(3) 0.7670(3) 0.0400(7) Uani d . 1 . .
C C8 -0.0390(5) 0.4316(3) 0.6753(3) 0.0368(7) Uani d . 1 . .
C C9 -0.2525(6) 0.4135(4) 0.5908(3) 0.0500(8) Uani d . 1 . .
H H9 -0.3577 0.4717 0.5965 0.060 Uiso calc R 1 . .
C C10 -0.3098(6) 0.3115(4) 0.4997(4) 0.0602(10) Uani d . 1 . .
H H10 -0.4533 0.3009 0.4441 0.072 Uiso calc R 1 . .
C C11 -0.1570(7) 0.2248(4) 0.4897(4) 0.0564(9) Uani d . 1 . .
H H11 -0.1958 0.1557 0.4273 0.068 Uiso calc R 1 . .
C C12 0.0539(7) 0.2408(4) 0.5727(4) 0.0589(10) Uani d . 1 . .
H H12 0.1576 0.1818 0.5664 0.071 Uiso calc R 1 . .
C C13 0.1137(6) 0.3429(4) 0.6649(3) 0.0492(8) Uani d . 1 . .
H H13 0.2571 0.3526 0.7205 0.059 Uiso calc R 1 . .
N N1 0.2045(5) 0.5551(3) 0.8642(3) 0.0436(7) Uani d D 1 . .
H H1N 0.262(7) 0.491(3) 0.882(4) 0.052 Uiso d D 1 . .
O O1 0.4799(5) 0.6424(2) 1.0568(3) 0.0629(8) Uani d . 1 . .
O O2 0.0786(5) 0.6940(3) 1.0349(3) 0.0597(7) Uani d . 1 . .
O O3 -0.1033(4) 0.6374(3) 0.7564(3) 0.0562(7) Uani d . 1 . .
S S1 0.27661(14) 0.67612(7) 0.97654(7) 0.0416(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'
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(3) ?
C2 C1 S1 . . 119.0(2) ?
C6 C1 S1 . . 119.6(2) ?
C3 C2 C1 . . 119.4(3) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 120.3(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 118.1(3) ?
C1 C6 H6 . . 121.0 ?
C5 C6 H6 . . 121.0 ?
O3 C7 N1 . . 120.1(3) ?
O3 C7 C8 . . 122.6(3) ?
N1 C7 C8 . . 117.2(3) ?
C13 C8 C9 . . 118.2(3) ?
C13 C8 C7 . . 124.8(3) ?
C9 C8 C7 . . 117.0(3) ?
C10 C9 C8 . . 121.0(3) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C9 C10 C11 . . 120.4(3) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 119.4(3) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C11 C12 C13 . . 120.8(3) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C13 C8 . . 120.2(3) ?
C12 C13 H13 . . 119.9 ?
C8 C13 H13 . . 119.9 ?
C7 N1 S1 . . 122.6(2) ?
C7 N1 H1N . . 120(3) ?
S1 N1 H1N . . 114(3) ?
O2 S1 O1 . . 119.09(18) ?
O2 S1 N1 . . 110.97(15) ?
O1 S1 N1 . . 103.63(14) ?
O2 S1 C1 . . 108.38(15) ?
O1 S1 C1 . . 109.23(15) ?
N1 S1 C1 . . 104.55(14) ?
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 . 1.384(4) ?
C1 S1 . 1.756(3) ?
C2 C3 . 1.370(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.370(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.383(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.212(4) ?
C7 N1 . 1.383(4) ?
C7 C8 . 1.479(4) ?
C8 C13 . 1.385(5) ?
C8 C9 . 1.392(4) ?
C9 C10 . 1.366(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.373(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
N1 S1 . 1.650(3) ?
N1 H1N . 0.79(3) ?
O1 S1 . 1.432(2) ?
O2 S1 . 1.425(3) ?
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_667 0.79(3) 2.22(3) 2.981(4) 163(4)
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 . . . . 0.1(5) ?
S1 C1 C2 C3 . . . . 176.8(2) ?
C1 C2 C3 C4 . . . . 0.2(5) ?
C2 C3 C4 C5 . . . . 0.1(5) ?
C3 C4 C5 C6 . . . . -0.9(5) ?
C2 C1 C6 C5 . . . . -0.9(5) ?
S1 C1 C6 C5 . . . . -177.5(2) ?
C4 C5 C6 C1 . . . . 1.3(5) ?
O3 C7 C8 C13 . . . . 164.9(3) ?
N1 C7 C8 C13 . . . . -12.2(5) ?
O3 C7 C8 C9 . . . . -12.7(5) ?
N1 C7 C8 C9 . . . . 170.2(3) ?
C13 C8 C9 C10 . . . . -0.3(5) ?
C7 C8 C9 C10 . . . . 177.5(3) ?
C8 C9 C10 C11 . . . . -0.1(6) ?
C9 C10 C11 C12 . . . . 0.3(6) ?
C10 C11 C12 C13 . . . . -0.3(6) ?
C11 C12 C13 C8 . . . . 0.0(6) ?
C9 C8 C13 C12 . . . . 0.3(5) ?
C7 C8 C13 C12 . . . . -177.3(3) ?
O3 C7 N1 S1 . . . . 5.1(4) ?
C8 C7 N1 S1 . . . . -177.7(2) ?
C7 N1 S1 O2 . . . . 49.8(3) ?
C7 N1 S1 O1 . . . . 178.7(3) ?
C7 N1 S1 C1 . . . . -66.9(3) ?
C2 C1 S1 O2 . . . . -0.3(3) ?
C6 C1 S1 O2 . . . . 176.3(2) ?
C2 C1 S1 O1 . . . . -131.5(2) ?
C6 C1 S1 O1 . . . . 45.2(3) ?
C2 C1 S1 N1 . . . . 118.1(2) ?
C6 C1 S1 N1 . . . . -65.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 199907
