#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/33/2233367.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_2233367
loop_
_publ_author_name
'Suchetan, P. A.'
'Foro, Sabine'
'Gowda, B. Thimme'
'Nirmala, B.'
_publ_section_title
;
 N-Benzoyl-2-nitrobenzenesulfonamide
;
_journal_coeditor_code           BQ2330
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o339
_journal_paper_doi               10.1107/S1600536811055917
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H10 N2 O5 S'
_chemical_formula_moiety         'C13 H10 N2 O5 S'
_chemical_formula_sum            'C13 H10 N2 O5 S'
_chemical_formula_weight         306.29
_chemical_name_systematic
;
N-Benzoyl-2-nitrobenzenesulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.1127(8)
_cell_length_b                   11.7625(8)
_cell_length_c                   18.7300(10)
_cell_measurement_reflns_used    2597
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.64
_cell_volume                     2668.6(3)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega
;
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6396
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.9008
_exptl_absorpt_correction_T_min  0.8827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0434
_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)+(0.0388P)²+2.8009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                2010
_reflns_number_total             2711
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2330.cif
_cod_data_source_block           I
_cod_database_code               2233367
_cod_database_fobs_code          2233367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_symmetry_multiplicity
C C1 1.01092(19) 0.2867(2) 0.42850(12) 0.0320(5) Uani d . 1 1
C C2 1.08964(19) 0.3142(2) 0.47986(13) 0.0352(5) Uani d . 1 1
C C3 1.1400(2) 0.4186(2) 0.48146(15) 0.0458(6) Uani d . 1 1
H H3 1.1912 0.4360 0.5168 0.055 Uiso calc R 1 1
C C4 1.1134(2) 0.4975(2) 0.42959(15) 0.0503(7) Uani d . 1 1
H H4 1.1473 0.5684 0.4298 0.060 Uiso calc R 1 1
C C5 1.0369(2) 0.4717(2) 0.37750(15) 0.0496(7) Uani d . 1 1
H H5 1.0201 0.5249 0.3424 0.060 Uiso calc R 1 1
C C6 0.9851(2) 0.3670(2) 0.37733(14) 0.0413(6) Uani d . 1 1
H H6 0.9326 0.3505 0.3426 0.050 Uiso calc R 1 1
C C7 1.0522(2) 0.0708(2) 0.31993(13) 0.0344(5) Uani d . 1 1
C C8 1.13311(19) -0.01632(19) 0.29607(12) 0.0332(5) Uani d . 1 1
C C9 1.2011(2) 0.0112(2) 0.23910(13) 0.0400(6) Uani d . 1 1
H H9 1.1942 0.0816 0.2170 0.048 Uiso calc R 1 1
C C10 1.2786(2) -0.0652(2) 0.21516(14) 0.0436(6) Uani d . 1 1
H H10 1.3247 -0.0458 0.1773 0.052 Uiso calc R 1 1
C C11 1.2882(2) -0.1697(2) 0.24688(14) 0.0482(7) Uani d . 1 1
H H11 1.3412 -0.2209 0.2309 0.058 Uiso calc R 1 1
C C12 1.2194(3) -0.1986(2) 0.30227(16) 0.0589(8) Uani d . 1 1
H H12 1.2252 -0.2701 0.3231 0.071 Uiso calc R 1 1
C C13 1.1419(2) -0.1227(2) 0.32734(14) 0.0482(7) Uani d . 1 1
H H13 1.0959 -0.1428 0.3650 0.058 Uiso calc R 1 1
N N1 1.01881(17) 0.06273(17) 0.39120(11) 0.0355(5) Uani d D 1 1
H H1N 1.051(2) 0.021(2) 0.4206(12) 0.043 Uiso d D 1 1
N N2 1.12183(18) 0.2319(2) 0.53570(13) 0.0467(6) Uani d . 1 1
O O1 0.84056(14) 0.17061(15) 0.38774(10) 0.0455(5) Uani d . 1 1
O O2 0.92831(15) 0.11935(15) 0.50171(9) 0.0418(4) Uani d . 1 1
O O3 1.01759(16) 0.14595(15) 0.28213(9) 0.0468(5) Uani d . 1 1
O O4 1.09678(19) 0.2545(2) 0.59685(11) 0.0660(6) Uani d . 1 1
O O5 1.1726(2) 0.14835(19) 0.51681(13) 0.0695(6) Uani d . 1 1
S S1 0.93749(5) 0.15669(5) 0.42926(3) 0.03293(17) Uani d . 1 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'
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
C6 C1 C2 118.4(2)
C6 C1 S1 118.86(19)
C2 C1 S1 122.61(18)
C3 C2 C1 121.8(2)
C3 C2 N2 117.0(2)
C1 C2 N2 121.2(2)
C2 C3 C4 118.8(3)
C2 C3 H3 120.6
C4 C3 H3 120.6
C5 C4 C3 120.4(3)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.2(3)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 120.3(2)
C1 C6 H6 119.8
C5 C6 H6 119.8
O3 C7 N1 120.7(2)
O3 C7 C8 123.8(2)
N1 C7 C8 115.5(2)
C9 C8 C13 119.4(2)
C9 C8 C7 117.5(2)
C13 C8 C7 123.1(2)
C10 C9 C8 120.3(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 120.2(2)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 119.9(2)
C10 C11 H11 120.1
C12 C11 H11 120.1
C11 C12 C13 120.7(3)
C11 C12 H12 119.7
C13 C12 H12 119.7
C12 C13 C8 119.6(2)
C12 C13 H13 120.2
C8 C13 H13 120.2
C7 N1 S1 122.79(17)
C7 N1 H1N 122.4(18)
S1 N1 H1N 112.9(18)
O5 N2 O4 125.5(2)
O5 N2 C2 117.3(2)
O4 N2 C2 117.3(2)
O1 S1 O2 119.43(11)
O1 S1 N1 109.64(11)
O2 S1 N1 104.57(10)
O1 S1 C1 108.18(11)
O2 S1 C1 108.18(11)
N1 S1 C1 106.06(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.381(3)
C1 C2 1.392(3)
C1 S1 1.769(2)
C2 C3 1.372(4)
C2 N2 1.477(3)
C3 C4 1.382(4)
C3 H3 0.9300
C4 C5 1.379(4)
C4 H4 0.9300
C5 C6 1.382(4)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.207(3)
C7 N1 1.398(3)
C7 C8 1.487(3)
C8 C9 1.386(3)
C8 C13 1.386(3)
C9 C10 1.375(3)
C9 H9 0.9300
C10 C11 1.370(4)
C10 H10 0.9300
C11 C12 1.374(4)
C11 H11 0.9300
C12 C13 1.377(4)
C12 H12 0.9300
C13 H13 0.9300
N1 S1 1.643(2)
N1 H1N 0.835(17)
N2 O5 1.211(3)
N2 O4 1.214(3)
O1 S1 1.4177(18)
O2 S1 1.4308(17)
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 5_756 0.835(17) 2.214(19) 3.003(3) 158(2)
C11 H11 O3 7_855 0.93 2.51 3.267(3) 138.8
C13 H13 O2 5_756 0.93 2.53 3.313(3) 142.3
C6 H6 Cg1 4_755 0.93 2.82 3.678(13) 153.3
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 1.2(4)
S1 C1 C2 C3 -175.2(2)
C6 C1 C2 N2 -179.4(2)
S1 C1 C2 N2 4.2(3)
C1 C2 C3 C4 -1.5(4)
N2 C2 C3 C4 179.1(2)
C2 C3 C4 C5 0.4(4)
C3 C4 C5 C6 0.8(4)
C2 C1 C6 C5 0.1(4)
S1 C1 C6 C5 176.7(2)
C4 C5 C6 C1 -1.1(4)
O3 C7 C8 C9 23.9(4)
N1 C7 C8 C9 -154.7(2)
O3 C7 C8 C13 -155.1(3)
N1 C7 C8 C13 26.2(3)
C13 C8 C9 C10 -1.8(4)
C7 C8 C9 C10 179.1(2)
C8 C9 C10 C11 0.9(4)
C9 C10 C11 C12 0.7(4)
C10 C11 C12 C13 -1.2(5)
C11 C12 C13 C8 0.3(5)
C9 C8 C13 C12 1.2(4)
C7 C8 C13 C12 -179.8(3)
O3 C7 N1 S1 -3.5(3)
C8 C7 N1 S1 175.16(16)
C3 C2 N2 O5 -112.1(3)
C1 C2 N2 O5 68.4(3)
C3 C2 N2 O4 66.7(3)
C1 C2 N2 O4 -112.7(3)
C7 N1 S1 O1 53.2(2)
C7 N1 S1 O2 -177.62(19)
C7 N1 S1 C1 -63.4(2)
C6 C1 S1 O1 -16.5(2)
C2 C1 S1 O1 159.83(19)
C6 C1 S1 O2 -147.3(2)
C2 C1 S1 O2 29.1(2)
C6 C1 S1 N1 101.0(2)
C2 C1 S1 N1 -82.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 845139
