#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/63/2236398.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_2236398
loop_
_publ_author_name
'Sivakumar, P. K.'
'Krishnakumar, M.'
'Kanagadurai, R.'
'Chakkaravarthi, G.'
'Mohankumar, R.'
_publ_section_title
;
 4-Nitroanilinium p-toluenesulfonate
;
_journal_coeditor_code           IS5199
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3059
_journal_paper_doi               10.1107/S1600536812040664
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H7 N2 O2 +, C7 H7 O3 S -'
_chemical_formula_moiety         'C6 H7 N2 O2 +, C7 H7 O3 S -'
_chemical_formula_sum            'C13 H14 N2 O5 S'
_chemical_formula_weight         310.32
_chemical_name_systematic
;
4-Nitroanilinium p-toluenesulfonate
;
_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           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 97.048(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   6.216(5)
_cell_length_b                   30.674(4)
_cell_length_c                   7.405(5)
_cell_measurement_reflns_used    4052
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      1.83
_cell_volume                     1401.2(15)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13942
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.33
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9508
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.537
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0528
_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)+(0.0471P)²+0.9840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                3232
_reflns_number_total             3509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            is5199.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2236398
_cod_database_fobs_code          2236398
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 0.4464(3) 0.15687(6) 1.0932(3) 0.0291(4) Uani d . 1 1
C C2 0.3478(4) 0.11695(7) 1.0557(3) 0.0413(5) Uani d . 1 1
H H2 0.2032 0.1156 1.0056 0.050 Uiso calc R 1 1
C C3 0.4649(5) 0.07893(8) 1.0928(4) 0.0526(6) Uani d . 1 1
H H3 0.3974 0.0522 1.0676 0.063 Uiso calc R 1 1
C C4 0.6802(5) 0.07991(9) 1.1666(4) 0.0513(6) Uani d . 1 1
C C5 0.7754(4) 0.11997(9) 1.2045(4) 0.0508(6) Uani d . 1 1
H H5 0.9198 0.1212 1.2550 0.061 Uiso calc R 1 1
C C6 0.6614(3) 0.15854(8) 1.1694(3) 0.0410(5) Uani d . 1 1
H H6 0.7286 0.1852 1.1966 0.049 Uiso calc R 1 1
C C7 0.8092(6) 0.03827(11) 1.2035(5) 0.0829(11) Uani d . 1 1
H H7A 0.8506 0.0272 1.0914 0.124 Uiso calc R 1 1
H H7B 0.7220 0.0170 1.2558 0.124 Uiso calc R 1 1
H H7C 0.9369 0.0442 1.2866 0.124 Uiso calc R 1 1
C C8 0.4640(3) 0.17612(6) 0.6035(2) 0.0287(4) Uani d . 1 1
C C9 0.3447(4) 0.13903(8) 0.5530(3) 0.0415(5) Uani d . 1 1
H H9 0.2015 0.1413 0.5002 0.050 Uiso calc R 1 1
C C10 0.4402(4) 0.09860(8) 0.5817(4) 0.0480(6) Uani d . 1 1
H H10 0.3627 0.0732 0.5504 0.058 Uiso calc R 1 1
C C11 0.6539(4) 0.09694(7) 0.6584(3) 0.0411(5) Uani d . 1 1
C C12 0.7739(4) 0.13364(7) 0.7077(3) 0.0400(5) Uani d . 1 1
H H12 0.9177 0.1313 0.7590 0.048 Uiso calc R 1 1
C C13 0.6768(3) 0.17402(7) 0.6797(3) 0.0345(4) Uani d . 1 1
H H13 0.7543 0.1994 0.7118 0.041 Uiso calc R 1 1
N N2 0.3582(3) 0.21852(6) 0.5788(2) 0.0328(4) Uani d . 1 1
H H14A 0.4535 0.2395 0.6133 0.049 Uiso calc R 1 1
H H14B 0.2490 0.2198 0.6459 0.049 Uiso calc R 1 1
H H14C 0.3074 0.2221 0.4620 0.049 Uiso calc R 1 1
N N1 0.7608(5) 0.05441(7) 0.6924(4) 0.0669(7) Uani d . 1 1
O O1 0.4582(3) 0.23868(5) 1.0129(3) 0.0461(4) Uani d . 1 1
O O2 0.1910(3) 0.21560(5) 1.20530(19) 0.0384(3) Uani d . 1 1
O O3 0.1435(2) 0.19798(5) 0.8876(2) 0.0379(3) Uani d . 1 1
O O4 0.9550(4) 0.05402(8) 0.7374(5) 0.1119(12) Uani d . 1 1
O O5 0.6501(5) 0.02194(7) 0.6748(5) 0.1009(10) Uani d . 1 1
S S1 0.30084(7) 0.205912(15) 1.04561(6) 0.02737(14) 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 119.73(19)
C2 C1 S1 120.68(16)
C6 C1 S1 119.59(16)
C1 C2 C3 119.8(2)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 121.3(2)
C4 C3 H3 119.3
C2 C3 H3 119.3
C5 C4 C3 118.1(2)
C5 C4 C7 120.7(3)
C3 C4 C7 121.2(3)
C4 C5 C6 121.7(2)
C4 C5 H5 119.1
C6 C5 H5 119.1
C1 C6 C5 119.3(2)
C1 C6 H6 120.3
C5 C6 H6 120.3
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C13 C8 C9 121.95(19)
C13 C8 N2 119.34(17)
C9 C8 N2 118.70(18)
C10 C9 C8 119.4(2)
C10 C9 H9 120.3
C8 C9 H9 120.3
C9 C10 C11 118.1(2)
C9 C10 H10 121.0
C11 C10 H10 121.0
C12 C11 C10 122.9(2)
C12 C11 N1 117.5(2)
C10 C11 N1 119.7(2)
C11 C12 C13 118.8(2)
C11 C12 H12 120.6
C13 C12 H12 120.6
C8 C13 C12 118.96(19)
C8 C13 H13 120.5
C12 C13 H13 120.5
C8 N2 H14A 109.5
C8 N2 H14B 109.5
H14A N2 H14B 109.5
C8 N2 H14C 109.5
H14A N2 H14C 109.5
H14B N2 H14C 109.5
O5 N1 O4 123.8(3)
O5 N1 C11 118.2(3)
O4 N1 C11 118.0(2)
O1 S1 O3 112.65(11)
O1 S1 O2 112.71(10)
O3 S1 O2 110.50(11)
O1 S1 C1 106.57(10)
O3 S1 C1 107.22(9)
O2 S1 C1 106.79(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.382(3)
C1 C6 1.387(3)
C1 S1 1.768(2)
C2 C3 1.384(3)
C2 H2 0.9300
C3 C4 1.383(4)
C3 H3 0.9300
C4 C5 1.377(4)
C4 C7 1.515(4)
C5 C6 1.387(3)
C5 H5 0.9300
C6 H6 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C13 1.374(3)
C8 C9 1.385(3)
C8 N2 1.459(2)
C9 C10 1.380(3)
C9 H9 0.9300
C10 C11 1.380(4)
C10 H10 0.9300
C11 C12 1.375(3)
C11 N1 1.472(3)
C12 C13 1.382(3)
C12 H12 0.9300
C13 H13 0.9300
N2 H14A 0.8900
N2 H14B 0.8900
N2 H14C 0.8900
N1 O5 1.209(3)
N1 O4 1.212(4)
O1 S1 1.4436(16)
O2 S1 1.4665(16)
O3 S1 1.4507(16)
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
N2 H14B O3 . 0.89 2.09 2.856(3) 144
N2 H14A O2 4_665 0.89 2.07 2.961(3) 175
N2 H14B O1 4_565 0.89 2.33 2.801(3) 113
N2 H14C O2 1_554 0.89 1.96 2.834(3) 167
C12 H12 O3 1_655 0.93 2.59 3.193(3) 123
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 -0.6(3)
S1 C1 C2 C3 179.55(19)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 0.8(4)
C2 C3 C4 C7 -178.8(3)
C3 C4 C5 C6 -0.5(4)
C7 C4 C5 C6 179.0(3)
C2 C1 C6 C5 0.8(3)
S1 C1 C6 C5 -179.28(18)
C4 C5 C6 C1 -0.3(4)
C13 C8 C9 C10 0.9(3)
N2 C8 C9 C10 -177.6(2)
C8 C9 C10 C11 -0.8(4)
C9 C10 C11 C12 0.4(4)
C9 C10 C11 N1 179.5(2)
C10 C11 C12 C13 0.0(4)
N1 C11 C12 C13 -179.1(2)
C9 C8 C13 C12 -0.5(3)
N2 C8 C13 C12 178.06(18)
C11 C12 C13 C8 0.0(3)
C12 C11 N1 O5 169.4(3)
C10 C11 N1 O5 -9.8(4)
C12 C11 N1 O4 -10.3(4)
C10 C11 N1 O4 170.6(3)
C2 C1 S1 O1 -152.38(18)
C6 C1 S1 O1 27.7(2)
C2 C1 S1 O3 -31.5(2)
C6 C1 S1 O3 148.59(17)
C2 C1 S1 O2 86.92(19)
C6 C1 S1 O2 -92.96(19)
