#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/39/2233947.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_2233947
loop_
_publ_author_name
'Suchetan, P. A.'
'Foro, Sabine'
'Gowda, B. Thimme'
'Prakash, M. Shet'
_publ_section_title
;
 N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide
;
_journal_coeditor_code           NC2268
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o786
_journal_paper_doi               10.1107/S160053681200640X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H9 Cl N2 O5 S'
_chemical_formula_moiety         'C13 H9 Cl N2 O5 S'
_chemical_formula_sum            'C13 H9 Cl N2 O5 S'
_chemical_formula_weight         340.73
_chemical_name_systematic
;
N-(3-Chlorobenzoyl)-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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.2046(8)
_cell_length_b                   12.6121(9)
_cell_length_c                   18.4330(10)
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.55
_cell_volume                     2837.3(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Xcalibur diffractometer with Sapphire CCD detector'
_diffrn_measurement_method
'Rotation method data acquisition using ω and φ scans'
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11298
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_correction_T_min  0.8863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0362P)²+4.7309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1473
_reflns_number_gt                1911
_reflns_number_total             2889
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2268.cif
_cod_data_source_block           I
_cod_database_code               2233947
_cod_database_fobs_code          2233947
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 -0.0112(3) 0.7252(3) 0.0676(2) 0.0347(9) Uani d . 1 1
C C2 -0.0862(3) 0.7030(3) 0.0131(2) 0.0402(10) Uani d . 1 1
C C3 -0.1369(4) 0.6063(4) 0.0079(3) 0.0503(12) Uani d . 1 1
H H3 -0.1854 0.5924 -0.0298 0.060 Uiso calc R 1 1
C C4 -0.1152(4) 0.5307(4) 0.0590(3) 0.0552(13) Uani d . 1 1
H H4 -0.1498 0.4652 0.0563 0.066 Uiso calc R 1 1
C C5 -0.0427(4) 0.5506(4) 0.1143(3) 0.0537(13) Uani d . 1 1
H H5 -0.0286 0.4986 0.1488 0.064 Uiso calc R 1 1
C C6 0.0092(4) 0.6469(3) 0.1188(2) 0.0450(11) Uani d . 1 1
H H6 0.0582 0.6598 0.1564 0.054 Uiso calc R 1 1
C C7 -0.0490(3) 0.9234(3) 0.1845(2) 0.0389(10) Uani d . 1 1
C C8 -0.1239(3) 1.0094(3) 0.2089(2) 0.0354(9) Uani d . 1 1
C C9 -0.1284(3) 1.1061(3) 0.1738(2) 0.0390(10) Uani d . 1 1
H H9 -0.0812 1.1205 0.1354 0.047 Uiso calc R 1 1
C C10 -0.2036(4) 1.1812(3) 0.1960(2) 0.0400(10) Uani d . 1 1
C C11 -0.2730(4) 1.1613(4) 0.2528(2) 0.0456(11) Uani d . 1 1
H H11 -0.3240 1.2119 0.2672 0.055 Uiso calc R 1 1
C C12 -0.2663(4) 1.0654(4) 0.2884(2) 0.0499(12) Uani d . 1 1
H H12 -0.3127 1.0518 0.3273 0.060 Uiso calc R 1 1
C C13 -0.1921(4) 0.9897(3) 0.2670(2) 0.0452(11) Uani d . 1 1
H H13 -0.1879 0.9254 0.2915 0.054 Uiso calc R 1 1
N N1 -0.0153(3) 0.9315(3) 0.11212(18) 0.0400(9) Uani d D 1 1
H H1N -0.050(3) 0.966(3) 0.0794(18) 0.048 Uiso d D 1 1
N N2 -0.1148(3) 0.7825(3) -0.0428(2) 0.0528(10) Uani d . 1 1
O O1 0.0765(2) 0.8844(2) -0.00038(15) 0.0478(8) Uani d . 1 1
O O2 0.1576(2) 0.8265(2) 0.11536(16) 0.0514(8) Uani d . 1 1
O O3 -0.0201(3) 0.8509(2) 0.22210(16) 0.0538(8) Uani d . 1 1
O O4 -0.1559(3) 0.8640(3) -0.0218(2) 0.0730(11) Uani d . 1 1
O O5 -0.0955(3) 0.7592(3) -0.10577(18) 0.0747(11) Uani d . 1 1
Cl Cl1 -0.20968(12) 1.29932(10) 0.14917(7) 0.0697(4) Uani d . 1 1
S S1 0.06425(8) 0.84464(8) 0.07160(6) 0.0381(3) 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'
Cl Cl 0.1484 0.1585 '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 117.8(4)
C6 C1 S1 119.0(3)
C2 C1 S1 123.1(3)
C3 C2 C1 121.9(4)
C3 C2 N2 116.7(4)
C1 C2 N2 121.5(4)
C4 C3 C2 119.0(4)
C4 C3 H3 120.5
C2 C3 H3 120.5
C3 C4 C5 120.7(4)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 120.2(4)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 120.4(4)
C5 C6 H6 119.8
C1 C6 H6 119.8
O3 C7 N1 121.3(4)
O3 C7 C8 124.1(4)
N1 C7 C8 114.5(4)
C13 C8 C9 119.9(4)
C13 C8 C7 118.3(4)
C9 C8 C7 121.7(4)
C10 C9 C8 119.5(4)
C10 C9 H9 120.2
C8 C9 H9 120.2
C11 C10 C9 120.8(4)
C11 C10 Cl1 121.0(3)
C9 C10 Cl1 118.2(3)
C10 C11 C12 119.2(4)
C10 C11 H11 120.4
C12 C11 H11 120.4
C13 C12 C11 120.8(4)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C8 119.7(4)
C12 C13 H13 120.2
C8 C13 H13 120.2
C7 N1 S1 123.9(3)
C7 N1 H1N 124(3)
S1 N1 H1N 108(3)
O4 N2 O5 126.1(4)
O4 N2 C2 116.9(4)
O5 N2 C2 117.0(4)
O2 S1 O1 120.19(19)
O2 S1 N1 108.94(18)
O1 S1 N1 104.51(18)
O2 S1 C1 107.76(19)
O1 S1 C1 108.41(19)
N1 S1 C1 106.23(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.388(5)
C1 C2 1.389(6)
C1 S1 1.767(4)
C2 C3 1.371(6)
C2 N2 1.479(5)
C3 C4 1.366(6)
C3 H3 0.9300
C4 C5 1.373(6)
C4 H4 0.9300
C5 C6 1.372(6)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.201(5)
C7 N1 1.399(5)
C7 C8 1.489(6)
C8 C13 1.379(5)
C8 C9 1.382(5)
C9 C10 1.381(6)
C9 H9 0.9300
C10 C11 1.369(6)
C10 Cl1 1.723(4)
C11 C12 1.378(6)
C11 H11 0.9300
C12 C13 1.374(6)
C12 H12 0.9300
C13 H13 0.9300
N1 S1 1.643(4)
N1 H1N 0.857(19)
N2 O4 1.207(5)
N2 O5 1.221(5)
O1 S1 1.426(3)
O2 S1 1.414(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 5_575 0.857(19) 2.41(3) 3.193(4) 153(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
C6 C1 C2 C3 -1.8(6)
S1 C1 C2 C3 174.5(3)
C6 C1 C2 N2 178.6(4)
S1 C1 C2 N2 -5.0(6)
C1 C2 C3 C4 1.8(7)
N2 C2 C3 C4 -178.7(4)
C2 C3 C4 C5 -0.7(7)
C3 C4 C5 C6 -0.2(7)
C4 C5 C6 C1 0.1(7)
C2 C1 C6 C5 0.9(6)
S1 C1 C6 C5 -175.6(3)
O3 C7 C8 C13 -22.3(6)
N1 C7 C8 C13 156.3(4)
O3 C7 C8 C9 159.5(4)
N1 C7 C8 C9 -21.9(6)
C13 C8 C9 C10 -1.7(6)
C7 C8 C9 C10 176.4(4)
C8 C9 C10 C11 0.5(6)
C8 C9 C10 Cl1 -178.1(3)
C9 C10 C11 C12 0.7(7)
Cl1 C10 C11 C12 179.3(3)
C10 C11 C12 C13 -0.7(7)
C11 C12 C13 C8 -0.4(7)
C9 C8 C13 C12 1.7(6)
C7 C8 C13 C12 -176.5(4)
O3 C7 N1 S1 0.6(6)
C8 C7 N1 S1 -178.1(3)
C3 C2 N2 O4 119.2(5)
C1 C2 N2 O4 -61.2(6)
C3 C2 N2 O5 -60.2(6)
C1 C2 N2 O5 119.4(5)
C7 N1 S1 O2 -50.4(4)
C7 N1 S1 O1 179.9(3)
C7 N1 S1 C1 65.4(4)
C6 C1 S1 O2 17.3(4)
C2 C1 S1 O2 -159.0(3)
C6 C1 S1 O1 148.9(3)
C2 C1 S1 O1 -27.4(4)
C6 C1 S1 N1 -99.3(3)
C2 C1 S1 N1 84.4(4)
