#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238981.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2238981
loop_
_publ_author_name
'Sreenivasa, S.'
'Nanjundaswamy, M. S.'
'Sudha, A. G.'
'Pampa, K. J.'
'Lokanath, N. K.'
'Suchetan, P. A.'
_publ_section_title
;
 N-(4-Methylphenylsulfonyl)-3-nitrobenzamide
;
_journal_coeditor_code           HB7184
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o191
_journal_paper_doi               10.1107/S1600536814001317
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H12 N2 O5 S'
_chemical_formula_moiety         'C14 H12 N2 O5 S'
_chemical_formula_sum            'C14 H12 N2 O5 S'
_chemical_formula_weight         320.32
_chemical_melting_point          459
_chemical_name_systematic
;
N-(4-Methylphenylsulfonyl)-3-nitrobenzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.820(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9736(5)
_cell_length_b                   23.245(2)
_cell_length_c                   12.7197(11)
_cell_measurement_reflns_used    1127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.5
_cell_measurement_theta_min      3.8
_cell_volume                     1444.4(2)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12115
_diffrn_reflns_theta_full        64.50
_diffrn_reflns_theta_max         64.50
_diffrn_reflns_theta_min         3.80
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  1
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.244
_exptl_absorpt_correction_T_max  0.638
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0393
_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)+(0.0621P)²+0.3691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2053
_reflns_number_total             2378
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7184sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238981
_cod_database_fobs_code          2238981
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
S S1 1.10155(10) 0.50190(2) 0.32699(4) 0.0546(2) Uani d . 1 1
C C8 0.6073(4) 0.63811(8) 0.33442(15) 0.0481(5) Uani d . 1 1
C C9 0.4226(4) 0.66836(8) 0.25927(16) 0.0481(5) Uani d . 1 1
H H9 0.4108 0.6615 0.1865 0.058 Uiso calc R 1 1
O O2 1.1994(3) 0.47252(7) 0.42557(13) 0.0667(4) Uani d . 1 1
N N2 0.0629(4) 0.74082(8) 0.21424(15) 0.0570(4) Uani d . 1 1
O O1 1.2908(3) 0.52526(7) 0.26821(15) 0.0720(5) Uani d . 1 1
N N1 0.9164(4) 0.55519(7) 0.36288(16) 0.0534(4) Uani d . 1 1
C C10 0.2572(4) 0.70859(8) 0.29425(15) 0.0471(5) Uani d . 1 1
O O3 0.8066(3) 0.59550(7) 0.19878(13) 0.0695(5) Uani d . 1 1
O O4 -0.1159(4) 0.76822(9) 0.24399(15) 0.0891(6) Uani d . 1 1
O O5 0.0900(4) 0.73809(9) 0.12131(13) 0.0853(6) Uani d . 1 1
C C4 0.4935(5) 0.38740(9) 0.11605(18) 0.0593(5) Uani d . 1 1
C C3 0.5450(5) 0.38158(10) 0.22531(18) 0.0646(6) Uani d . 1 1
H H3 0.4508 0.3537 0.2563 0.077 Uiso calc R 1 1
C C7 0.7819(4) 0.59512(9) 0.29113(17) 0.0518(5) Uani d . 1 1
C C5 0.6344(5) 0.42936(10) 0.07092(18) 0.0680(6) Uani d . 1 1
H H5 0.6014 0.4341 -0.0030 0.082 Uiso calc R 1 1
C C11 0.2669(5) 0.71991(9) 0.40117(17) 0.0583(5) Uani d . 1 1
H H11 0.1494 0.7467 0.4229 0.070 Uiso calc R 1 1
C C1 0.8710(4) 0.45716(8) 0.24416(16) 0.0490(5) Uani d . 1 1
C C6 0.8239(5) 0.46431(10) 0.13467(19) 0.0630(6) Uani d . 1 1
H H6 0.9182 0.4923 0.1039 0.076 Uiso calc R 1 1
C C13 0.6243(5) 0.64965(9) 0.44227(17) 0.0602(6) Uani d . 1 1
H H13 0.7500 0.6298 0.4928 0.072 Uiso calc R 1 1
C C2 0.7316(5) 0.41580(10) 0.29029(17) 0.0588(5) Uani d . 1 1
H H2 0.7635 0.4111 0.3642 0.071 Uiso calc R 1 1
C C12 0.4558(5) 0.69042(10) 0.47530(18) 0.0669(6) Uani d . 1 1
H H12 0.4696 0.6981 0.5479 0.080 Uiso calc R 1 1
C C14 0.2854(6) 0.34997(12) 0.0463(2) 0.0845(8) Uani d . 1 1
H H14A 0.1814 0.3292 0.0903 0.127 Uiso calc R 1 1
H H14B 0.3776 0.3232 0.0078 0.127 Uiso calc R 1 1
H H14C 0.1647 0.3736 -0.0035 0.127 Uiso calc R 1 1
H HN1 0.860(5) 0.5495(10) 0.417(2) 0.062(8) Uiso 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 0.0181 0.0091 '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'
H H 0.0000 0.0000 '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
O1 S1 O2 119.71(11)
O1 S1 N1 108.51(10)
O2 S1 N1 103.33(10)
O1 S1 C1 109.63(10)
O2 S1 C1 108.74(10)
N1 S1 C1 105.96(9)
C13 C8 C9 119.62(18)
C13 C8 C7 124.23(18)
C9 C8 C7 116.14(18)
C10 C9 C8 118.78(18)
C10 C9 H9 120.6
C8 C9 H9 120.6
O4 N2 O5 123.57(19)
O4 N2 C10 118.53(19)
O5 N2 C10 117.89(18)
C7 N1 S1 123.00(17)
C7 N1 HN1 118.4(18)
S1 N1 HN1 114.5(17)
C9 C10 C11 122.56(18)
C9 C10 N2 118.58(17)
C11 C10 N2 118.86(18)
C3 C4 C5 118.4(2)
C3 C4 C14 121.1(2)
C5 C4 C14 120.5(2)
C4 C3 C2 121.9(2)
C4 C3 H3 119.0
C2 C3 H3 119.0
O3 C7 N1 121.6(2)
O3 C7 C8 121.82(19)
N1 C7 C8 116.62(19)
C6 C5 C4 120.8(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
C10 C11 C12 118.2(2)
C10 C11 H11 120.9
C12 C11 H11 120.9
C6 C1 C2 120.7(2)
C6 C1 S1 120.36(16)
C2 C1 S1 118.94(16)
C1 C6 C5 119.3(2)
C1 C6 H6 120.4
C5 C6 H6 120.4
C12 C13 C8 120.42(19)
C12 C13 H13 119.8
C8 C13 H13 119.8
C3 C2 C1 119.0(2)
C3 C2 H2 120.5
C1 C2 H2 120.5
C11 C12 C13 120.4(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
C4 C14 H14A 109.5
C4 C14 H14B 109.5
H14A C14 H14B 109.5
C4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4156(17)
S1 O2 1.4305(16)
S1 N1 1.6580(18)
S1 C1 1.747(2)
C8 C13 1.385(3)
C8 C9 1.386(3)
C8 C7 1.495(3)
C9 C10 1.373(3)
C9 H9 0.9300
N2 O4 1.211(2)
N2 O5 1.216(2)
N2 C10 1.470(3)
N1 C7 1.383(3)
N1 HN1 0.80(2)
C10 C11 1.377(3)
O3 C7 1.204(3)
C4 C3 1.372(3)
C4 C5 1.387(3)
C4 C14 1.507(3)
C3 C2 1.375(3)
C3 H3 0.9300
C5 C6 1.385(3)
C5 H5 0.9300
C11 C12 1.382(3)
C11 H11 0.9300
C1 C6 1.378(3)
C1 C2 1.379(3)
C6 H6 0.9300
C13 C12 1.382(3)
C13 H13 0.9300
C2 H2 0.9300
C12 H12 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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 HN1 O2 3_766 0.80(3) 2.14(3) 2.927(3) 167
C13 H13 O2 3_766 0.93 2.59 3.333(3) 137
C3 H3 O4 2_545 0.93 2.58 3.459(3) 155
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
C13 C8 C9 C10 -1.0(3)
C7 C8 C9 C10 -179.78(17)
O1 S1 N1 C7 51.79(19)
O2 S1 N1 C7 179.85(17)
C1 S1 N1 C7 -65.87(19)
C8 C9 C10 C11 -0.3(3)
C8 C9 C10 N2 179.61(17)
O4 N2 C10 C9 166.6(2)
O5 N2 C10 C9 -12.9(3)
O4 N2 C10 C11 -13.5(3)
O5 N2 C10 C11 167.0(2)
C5 C4 C3 C2 -0.3(4)
C14 C4 C3 C2 -179.2(2)
S1 N1 C7 O3 -4.9(3)
S1 N1 C7 C8 175.83(14)
C13 C8 C7 O3 -162.5(2)
C9 C8 C7 O3 16.1(3)
C13 C8 C7 N1 16.8(3)
C9 C8 C7 N1 -164.58(18)
C3 C4 C5 C6 0.4(4)
C14 C4 C5 C6 179.3(2)
C9 C10 C11 C12 1.7(3)
N2 C10 C11 C12 -178.2(2)
O1 S1 C1 C6 -23.4(2)
O2 S1 C1 C6 -155.95(17)
N1 S1 C1 C6 93.55(19)
O1 S1 C1 C2 158.45(17)
O2 S1 C1 C2 25.9(2)
N1 S1 C1 C2 -84.63(19)
C2 C1 C6 C5 -0.1(3)
S1 C1 C6 C5 -178.20(18)
C4 C5 C6 C1 -0.2(4)
C9 C8 C13 C12 1.0(3)
C7 C8 C13 C12 179.6(2)
C4 C3 C2 C1 0.0(4)
C6 C1 C2 C3 0.2(3)
S1 C1 C2 C3 178.32(18)
C10 C11 C12 C13 -1.7(4)
C8 C13 C12 C11 0.4(4)
