#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/34/2233402.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_2233402
loop_
_publ_author_name
'Suchetan, P. A.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N-(2-Chlorobenzoyl)-3-nitrobenzenesulfonamide
;
_journal_coeditor_code           BT5798
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o543
_journal_paper_doi               10.1107/S1600536812003236
_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-(2-Chlorobenzoyl)-3-nitrobenzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 93.336(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.606(2)
_cell_length_b                   5.1159(4)
_cell_length_c                   18.742(2)
_cell_measurement_reflns_used    1612
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      2.64
_cell_volume                     1398.1(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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Oxford Xcalibur diffractometer with Sapphire CCD detector'
_diffrn_measurement_method       'Rotation method data acquisition using ω'
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5313
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.44
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.8553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0576
_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)+(0.0156P)²+1.9016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                2005
_reflns_number_total             2844
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5798.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2233402
_cod_database_fobs_code          2233402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.1617(2) 0.3605(6) 0.91163(16) 0.0303(7) Uani d . 1 1
C C2 0.2244(2) 0.5563(6) 0.92952(17) 0.0327(8) Uani d . 1 1
H H2 0.2658 0.6146 0.8971 0.039 Uiso calc R 1 1
C C3 0.2233(2) 0.6616(7) 0.99714(17) 0.0340(8) Uani d . 1 1
C C4 0.1637(2) 0.5785(7) 1.04683(18) 0.0405(9) Uani d . 1 1
H H4 0.1647 0.6535 1.0921 0.049 Uiso calc R 1 1
C C5 0.1028(3) 0.3823(8) 1.02791(18) 0.0454(10) Uani d . 1 1
H H5 0.0627 0.3218 1.0610 0.055 Uiso calc R 1 1
C C6 0.1003(2) 0.2736(7) 0.96009(18) 0.0395(9) Uani d . 1 1
H H6 0.0580 0.1437 0.9472 0.047 Uiso calc R 1 1
C C7 0.0183(2) 0.4942(6) 0.77389(16) 0.0301(7) Uani d . 1 1
C C8 -0.0148(2) 0.6786(6) 0.71599(16) 0.0292(7) Uani d . 1 1
C C9 -0.0867(2) 0.8548(7) 0.72383(17) 0.0343(8) Uani d . 1 1
C C10 -0.1108(3) 1.0338(7) 0.67100(19) 0.0443(9) Uani d . 1 1
H H10 -0.1579 1.1521 0.6774 0.053 Uiso calc R 1 1
C C11 -0.0651(3) 1.0377(8) 0.60867(19) 0.0498(10) Uani d . 1 1
H H11 -0.0807 1.1605 0.5735 0.060 Uiso calc R 1 1
C C12 0.0037(3) 0.8594(8) 0.59861(18) 0.0491(10) Uani d . 1 1
H H12 0.0333 0.8586 0.5560 0.059 Uiso calc R 1 1
C C13 0.0285(2) 0.6831(7) 0.65139(16) 0.0381(8) Uani d . 1 1
H H13 0.0751 0.5639 0.6440 0.046 Uiso calc R 1 1
N N1 0.10998(18) 0.4193(5) 0.76979(13) 0.0299(6) Uani d D 1 1
H H1N 0.1464(19) 0.515(6) 0.7492(16) 0.036 Uiso d D 1 1
N N2 0.2880(2) 0.8740(6) 1.01653(16) 0.0460(8) Uani d . 1 1
O O1 0.11150(18) -0.0212(4) 0.82834(12) 0.0460(7) Uani d . 1 1
O O2 0.25475(16) 0.2152(5) 0.80566(12) 0.0443(6) Uani d . 1 1
O O3 -0.02699(16) 0.4097(5) 0.82055(12) 0.0427(6) Uani d . 1 1
O O4 0.2823(2) 0.9787(6) 1.07436(15) 0.0686(9) Uani d . 1 1
O O5 0.3436(2) 0.9354(6) 0.97376(15) 0.0724(10) Uani d . 1 1
Cl Cl1 -0.14856(7) 0.8669(2) 0.80000(5) 0.0528(3) Uani d . 1 1
S S1 0.16187(6) 0.21592(16) 0.82617(4) 0.0321(2) 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 121.1(3)
C6 C1 S1 119.7(3)
C2 C1 S1 119.1(2)
C3 C2 C1 117.5(3)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 122.9(3)
C2 C3 N2 118.3(3)
C4 C3 N2 118.8(3)
C5 C4 C3 118.4(3)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 C6 120.8(3)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 119.3(3)
C1 C6 H6 120.3
C5 C6 H6 120.3
O3 C7 N1 120.6(3)
O3 C7 C8 125.7(3)
N1 C7 C8 113.8(3)
C13 C8 C9 117.4(3)
C13 C8 C7 119.7(3)
C9 C8 C7 122.9(3)
C10 C9 C8 121.0(3)
C10 C9 Cl1 116.3(3)
C8 C9 Cl1 122.7(3)
C11 C10 C9 120.1(3)
C11 C10 H10 119.9
C9 C10 H10 119.9
C12 C11 C10 119.9(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 120.1(3)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C8 121.4(3)
C12 C13 H13 119.3
C8 C13 H13 119.3
C7 N1 S1 123.2(2)
C7 N1 H1N 120(2)
S1 N1 H1N 113(2)
O5 N2 O4 123.8(3)
O5 N2 C3 118.2(3)
O4 N2 C3 118.0(3)
O1 S1 O2 120.39(16)
O1 S1 N1 109.88(15)
O2 S1 N1 103.81(14)
O1 S1 C1 107.69(15)
O2 S1 C1 107.25(15)
N1 S1 C1 107.12(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(4)
C1 C2 1.386(4)
C1 S1 1.764(3)
C2 C3 1.378(4)
C2 H2 0.9300
C3 C4 1.379(5)
C3 N2 1.471(4)
C4 C5 1.374(5)
C4 H4 0.9300
C5 C6 1.386(5)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.207(4)
C7 N1 1.399(4)
C7 C8 1.497(4)
C8 C13 1.398(4)
C8 C9 1.398(5)
C9 C10 1.379(5)
C9 Cl1 1.735(3)
C10 C11 1.379(5)
C10 H10 0.9300
C11 C12 1.377(5)
C11 H11 0.9300
C12 C13 1.372(5)
C12 H12 0.9300
C13 H13 0.9300
N1 S1 1.637(3)
N1 H1N 0.834(18)
N2 O5 1.216(4)
N2 O4 1.216(4)
O1 S1 1.421(2)
O2 S1 1.431(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 2_556 0.834(18) 2.088(19) 2.919(3) 173(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 -0.2(5)
S1 C1 C2 C3 -178.9(2)
C1 C2 C3 C4 0.6(5)
C1 C2 C3 N2 -178.6(3)
C2 C3 C4 C5 0.0(5)
N2 C3 C4 C5 179.2(3)
C3 C4 C5 C6 -1.0(6)
C2 C1 C6 C5 -0.9(5)
S1 C1 C6 C5 177.9(3)
C4 C5 C6 C1 1.5(5)
O3 C7 C8 C13 -154.9(3)
N1 C7 C8 C13 24.4(4)
O3 C7 C8 C9 26.8(5)
N1 C7 C8 C9 -153.9(3)
C13 C8 C9 C10 -2.9(5)
C7 C8 C9 C10 175.4(3)
C13 C8 C9 Cl1 178.4(3)
C7 C8 C9 Cl1 -3.2(5)
C8 C9 C10 C11 1.3(6)
Cl1 C9 C10 C11 -180.0(3)
C9 C10 C11 C12 1.2(6)
C10 C11 C12 C13 -1.9(6)
C11 C12 C13 C8 0.2(6)
C9 C8 C13 C12 2.2(5)
C7 C8 C13 C12 -176.2(3)
O3 C7 N1 S1 0.2(4)
C8 C7 N1 S1 -179.1(2)
C2 C3 N2 O5 -4.8(5)
C4 C3 N2 O5 175.9(3)
C2 C3 N2 O4 174.9(3)
C4 C3 N2 O4 -4.4(5)
C7 N1 S1 O1 54.9(3)
C7 N1 S1 O2 -175.1(3)
C7 N1 S1 C1 -61.8(3)
C6 C1 S1 O1 -15.0(3)
C2 C1 S1 O1 163.7(2)
C6 C1 S1 O2 -146.0(3)
C2 C1 S1 O2 32.8(3)
C6 C1 S1 N1 103.1(3)
C2 C1 S1 N1 -78.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9984657
