##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-Benzoyl-2-nitrobenzenesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 N2 O5 S'
_chemical_formula_sum     'C13 H10 N2 O5 S'
_chemical_formula_iupac     'C13 H10 N2 O5 S'
_chemical_formula_weight     306.29
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_HALL     '-P 2ac 2ab'
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'
_cell_length_a     12.1127(8)
_cell_length_b     11.7625(8)
_cell_length_c     18.7300(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2668.6(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2597
_cell_measurement_theta_min     2.64
_cell_measurement_theta_max     27.80
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.44
_exptl_crystal_size_min     0.40
_exptl_crystal_density_diffrn     1.525
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1264
_exptl_absorpt_coefficient_mu     0.267
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.8827
_exptl_absorpt_correction_T_max     0.9008
_exptl_special_details
;
CrysAlis RED (Oxford Diffraction, 2009)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega
;
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6396
_diffrn_reflns_av_R_equivalents     0.0202
_diffrn_reflns_av_sigmaI/netI     0.0253
_diffrn_reflns_theta_min     2.65
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2711
_reflns_number_gt     2010
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0678
_refine_ls_R_factor_gt     0.0434
_refine_ls_wR_factor_gt     0.0976
_refine_ls_wR_factor_ref     0.1102
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     2711
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0388P)²+2.8009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.306
_refine_diff_density_min     -0.359
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0320(11) 0.0317(12) 0.0323(12) 0.0037(10) 0.0015(10) 0.0001(10)
    C2 0.0327(12) 0.0375(13) 0.0355(12) 0.0042(10) -0.0013(10) 0.0035(10)
    C3 0.0393(14) 0.0489(16) 0.0492(15) -0.0016(13) -0.0060(12) -0.0019(13)
    C4 0.0541(16) 0.0358(14) 0.0612(17) -0.0060(13) 0.0042(15) 0.0024(13)
    C5 0.0635(18) 0.0386(15) 0.0468(15) 0.0050(14) -0.0012(14) 0.0098(12)
    C6 0.0469(14) 0.0410(14) 0.0360(13) 0.0046(12) -0.0051(12) 0.0010(11)
    C7 0.0372(13) 0.0313(12) 0.0347(12) -0.0031(11) 0.0015(11) -0.0029(10)
    C8 0.0365(12) 0.0312(12) 0.0317(12) -0.0033(11) 0.0017(10) -0.0058(10)
    C9 0.0483(14) 0.0309(12) 0.0408(14) -0.0057(11) 0.0069(12) -0.0018(11)
    C10 0.0445(15) 0.0418(14) 0.0444(14) -0.0036(12) 0.0145(12) -0.0040(12)
    C11 0.0536(16) 0.0444(15) 0.0465(15) 0.0130(13) 0.0086(13) -0.0081(13)
    C12 0.087(2) 0.0385(15) 0.0512(16) 0.0179(16) 0.0180(16) 0.0066(13)
    C13 0.0654(18) 0.0397(14) 0.0395(14) 0.0059(14) 0.0193(13) 0.0026(12)
    N1 0.0412(12) 0.0330(11) 0.0324(11) 0.0076(9) 0.0019(9) 0.0004(9)
    N2 0.0417(12) 0.0494(14) 0.0490(14) 0.0001(11) -0.0116(11) 0.0062(11)
    O1 0.0335(9) 0.0494(11) 0.0535(11) 0.0024(8) -0.0053(8) -0.0030(9)
    O2 0.0489(10) 0.0402(10) 0.0361(9) 0.0012(8) 0.0105(8) 0.0004(8)
    O3 0.0561(11) 0.0424(10) 0.0420(10) 0.0097(9) 0.0068(9) 0.0063(9)
    O4 0.0764(15) 0.0815(16) 0.0400(12) -0.0017(13) -0.0101(11) 0.0097(11)
    O5 0.0756(15) 0.0536(13) 0.0794(15) 0.0219(12) -0.0179(13) 0.0069(12)
    S1 0.0321(3) 0.0332(3) 0.0335(3) 0.0027(3) 0.0028(3) -0.0015(2)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 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_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
    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_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 . . . . 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_
    _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
data_global
_journal_date_recd_electronic     2011-12-19
_journal_date_accepted     2011-12-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      2
_journal_page_first     o339
_journal_page_last     o339
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536811055917
_journal_coeditor_code     BQ2330
_publ_contact_author_name     'Prof. B. Thimme Gowda'
_publ_contact_author_address
;
  Department of Chemistry
  Mangalore University
  Mangalagangotri-574 199
  Mangalore, INDIA
;
_publ_contact_author_email     gowdabt@yahoo.com
_publ_contact_author_fax     '91 824 2287367'
_publ_contact_author_phone     '91 824 2287262'
_publ_section_title
;
N-Benzoyl-2-nitrobenzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'P. A. Suchetan'
; Department of Chemistry
  Mangalore University
  Mangalagangotri 574 199
  Mangalore, India
;
    'Sabine Foro'
; Institute of Materials Science
  Darmstadt University of Technology
  Petersenstrasse 23
  D-64287 Darmstadt, Germany
;
    'B. Thimme Gowda'
; Department of Chemistry
  Mangalore University
  Mangalagangotri 574 199
  Mangalore, India
;
    'B. Nirmala'
; Department of Chemistry
  University College of Science
  Tumkur University,
  Tumkur 572 102, India
;
