#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/40/2234058.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_2234058
loop_
_publ_author_name
'Suchetan, P. A.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N-(4-Methylbenzoyl)-4-nitrobenzenesulfonamide
;
_journal_coeditor_code           YK2044
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o888
_journal_paper_doi               10.1107/S1600536812007854
_journal_volume                  68
_journal_year                    2012
_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_name_systematic
;
N-(4-Methylbenzoyl)-4-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                   13.9690(10)
_cell_length_b                   9.6591(6)
_cell_length_c                   21.026(2)
_cell_measurement_reflns_used    818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.56
_cell_volume                     2837.0(4)
_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 Diffraction Xcalibur diffractometer with a Sapphire CCD detector
;
_diffrn_measurement_method       'ω and φ'
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7163
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9556
_exptl_absorpt_correction_T_min  0.9051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0409P)²+3.5546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                1836
_reflns_number_total             2864
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2044.cif
_cod_data_source_block           I
_cod_database_code               2234058
_cod_database_fobs_code          2234058
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 0.5261(3) 0.2260(4) 0.55537(17) 0.0407(9) Uani d . 1 1
C C2 0.4949(3) 0.1161(4) 0.5903(2) 0.0490(10) Uani d . 1 1
H H2 0.5302 0.0345 0.5911 0.059 Uiso calc R 1 1
C C3 0.4113(3) 0.1260(4) 0.6240(2) 0.0533(11) Uani d . 1 1
H H3 0.3899 0.0521 0.6486 0.064 Uiso calc R 1 1
C C4 0.3601(3) 0.2459(4) 0.62105(19) 0.0450(9) Uani d . 1 1
C C5 0.3893(3) 0.3565(5) 0.5862(2) 0.0669(13) Uani d . 1 1
H H5 0.3531 0.4372 0.5847 0.080 Uiso calc R 1 1
C C6 0.4737(4) 0.3461(5) 0.5534(2) 0.0708(14) Uani d . 1 1
H H6 0.4956 0.4209 0.5296 0.085 Uiso calc R 1 1
C C7 0.7385(3) 0.3573(4) 0.59457(17) 0.0405(9) Uani d . 1 1
C C8 0.8213(3) 0.3558(4) 0.63877(17) 0.0385(8) Uani d . 1 1
C C9 0.9003(3) 0.2694(4) 0.63104(19) 0.0449(9) Uani d . 1 1
H H9 0.9018 0.2066 0.5975 0.054 Uiso calc R 1 1
C C10 0.9763(3) 0.2765(4) 0.67281(19) 0.0490(10) Uani d . 1 1
H H10 1.0293 0.2199 0.6664 0.059 Uiso calc R 1 1
C C11 0.9750(3) 0.3668(4) 0.72441(19) 0.0463(10) Uani d . 1 1
C C12 0.8959(3) 0.4520(4) 0.73124(19) 0.0497(10) Uani d . 1 1
H H12 0.8938 0.5135 0.7652 0.060 Uiso calc R 1 1
C C13 0.8207(3) 0.4481(4) 0.68931(18) 0.0458(10) Uani d . 1 1
H H13 0.7691 0.5076 0.6948 0.055 Uiso calc R 1 1
C C14 1.0575(3) 0.3736(5) 0.7701(2) 0.0638(12) Uani d . 1 1
H H14A 1.1160 0.3865 0.7469 0.077 Uiso calc R 1 1
H H14B 1.0609 0.2889 0.7939 0.077 Uiso calc R 1 1
H H14C 1.0484 0.4499 0.7988 0.077 Uiso calc R 1 1
N N1 0.7201(2) 0.2339(3) 0.56360(15) 0.0421(8) Uani d D 1 1
H H1N 0.750(3) 0.161(3) 0.5748(17) 0.051 Uiso d D 1 1
N N2 0.2706(3) 0.2572(4) 0.65756(17) 0.0569(9) Uani d . 1 1
O O1 0.6446(2) 0.0697(3) 0.49280(14) 0.0605(8) Uani d . 1 1
O O2 0.6361(2) 0.3183(3) 0.46528(13) 0.0647(9) Uani d . 1 1
O O3 0.68781(18) 0.4583(3) 0.58609(13) 0.0519(7) Uani d . 1 1
O O4 0.2492(3) 0.1639(4) 0.6926(2) 0.1066(14) Uani d U 1 1
O O5 0.2239(2) 0.3613(4) 0.65262(17) 0.0805(10) Uani d . 1 1
S S1 0.63333(7) 0.21032(11) 0.51121(5) 0.0474(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'
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
C2 C1 C6 120.3(4)
C2 C1 S1 119.1(3)
C6 C1 S1 120.5(3)
C1 C2 C3 119.9(4)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 118.9(4)
C4 C3 H3 120.6
C2 C3 H3 120.6
C5 C4 C3 122.4(4)
C5 C4 N2 118.6(4)
C3 C4 N2 119.0(4)
C4 C5 C6 118.2(4)
C4 C5 H5 120.9
C6 C5 H5 120.9
C5 C6 C1 120.4(4)
C5 C6 H6 119.8
C1 C6 H6 119.8
O3 C7 N1 120.9(3)
O3 C7 C8 123.5(3)
N1 C7 C8 115.6(3)
C13 C8 C9 118.6(4)
C13 C8 C7 118.0(3)
C9 C8 C7 123.4(3)
C10 C9 C8 120.4(4)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 121.2(4)
C9 C10 H10 119.4
C11 C10 H10 119.4
C12 C11 C10 117.6(4)
C12 C11 C14 121.3(4)
C10 C11 C14 121.1(4)
C13 C12 C11 121.9(4)
C13 C12 H12 119.1
C11 C12 H12 119.1
C12 C13 C8 120.4(4)
C12 C13 H13 119.8
C8 C13 H13 119.8
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 S1 124.7(3)
C7 N1 H1N 119(3)
S1 N1 H1N 116(3)
O4 N2 O5 123.0(4)
O4 N2 C4 118.4(4)
O5 N2 C4 118.6(4)
O1 S1 O2 120.89(19)
O1 S1 N1 103.42(17)
O2 S1 N1 109.36(17)
O1 S1 C1 108.56(18)
O2 S1 C1 108.45(18)
N1 S1 C1 105.02(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.362(5)
C1 C6 1.373(5)
C1 S1 1.769(4)
C2 C3 1.369(5)
C2 H2 0.9300
C3 C4 1.363(5)
C3 H3 0.9300
C4 C5 1.359(6)
C4 N2 1.471(5)
C5 C6 1.369(6)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.218(4)
C7 N1 1.383(4)
C7 C8 1.484(5)
C8 C13 1.387(5)
C8 C9 1.393(5)
C9 C10 1.380(5)
C9 H9 0.9300
C10 C11 1.392(5)
C10 H10 0.9300
C11 C12 1.385(5)
C11 C14 1.502(5)
C12 C13 1.372(5)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 S1 1.654(3)
N1 H1N 0.852(19)
N2 O4 1.202(5)
N2 O5 1.203(4)
O1 S1 1.421(3)
O2 S1 1.422(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 O3 7_755 0.852(19) 2.16(2) 2.994(4) 168(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 -0.7(6)
S1 C1 C2 C3 -179.1(3)
C1 C2 C3 C4 1.1(6)
C2 C3 C4 C5 -0.6(7)
C2 C3 C4 N2 -179.6(4)
C3 C4 C5 C6 -0.3(7)
N2 C4 C5 C6 178.7(4)
C4 C5 C6 C1 0.7(8)
C2 C1 C6 C5 -0.2(7)
S1 C1 C6 C5 178.2(4)
O3 C7 C8 C13 25.4(5)
N1 C7 C8 C13 -153.2(3)
O3 C7 C8 C9 -152.8(4)
N1 C7 C8 C9 28.5(5)
C13 C8 C9 C10 -0.3(6)
C7 C8 C9 C10 177.9(3)
C8 C9 C10 C11 1.8(6)
C9 C10 C11 C12 -1.8(6)
C9 C10 C11 C14 179.6(4)
C10 C11 C12 C13 0.4(6)
C14 C11 C12 C13 179.1(4)
C11 C12 C13 C8 1.0(6)
C9 C8 C13 C12 -1.0(5)
C7 C8 C13 C12 -179.4(3)
O3 C7 N1 S1 2.5(5)
C8 C7 N1 S1 -178.8(3)
C5 C4 N2 O4 -173.7(5)
C3 C4 N2 O4 5.4(6)
C5 C4 N2 O5 3.9(6)
C3 C4 N2 O5 -177.0(4)
C7 N1 S1 O1 179.3(3)
C7 N1 S1 O2 49.2(4)
C7 N1 S1 C1 -67.0(3)
C2 C1 S1 O1 29.9(4)
C6 C1 S1 O1 -148.6(4)
C2 C1 S1 O2 162.9(3)
C6 C1 S1 O2 -15.5(4)
C2 C1 S1 N1 -80.2(3)
C6 C1 S1 N1 101.3(4)
