##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-04-16
_journal_date_accepted     2009-04-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      6
_journal_page_first     o1228
_journal_page_last     o1228
_journal_paper_category     QO
_journal_coeditor_code     HB2956
_publ_contact_author_name     'Jiang-Sheng Li'
_publ_contact_author_address
; School of Chemistry and Biological Engineering,
  Changsha University of Science & Technology
  Changsha 410004
  People's Republic of China
;
_publ_contact_author_email     'js_li@yahoo.com.cn'
_publ_contact_author_fax     '86 731 5258733'
_publ_contact_author_phone     '86 731 5258733'
_publ_section_title
;
2-(Benzenesulfonamido)pyridinium nitrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Li, Jiang-Sheng'
; School of Chemistry and Biological Engineering,
  Changsha University of Science & Technology
  Changsha 410004
  People's Republic of China
;
    'Li, Xun'
; School of Chemistry and Biological Engineering,
  Changsha University of Science & Technology
  Changsha 410004
  People's Republic of China
;
data_I
_chemical_name_systematic
;
2-(Benzenesulfonamido)pyridinium nitrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H11 N2 O2 S +, N O3 -'
_chemical_formula_sum     'C11 H11 N3 O5 S'
_chemical_formula_iupac     'C11 H11 N2 O2 S +, N O3 -'
_chemical_formula_weight     297.29
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     5.3309(11)
_cell_length_b     10.067(2)
_cell_length_c     23.837(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.44(3)
_cell_angle_gamma     90.00
_cell_volume     1279.2(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3934
_cell_measurement_theta_min     2.563
_cell_measurement_theta_max     27.849
_cell_measurement_temperature     113(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.544
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.277
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 2005)'
_exptl_absorpt_correction_T_min     0.947
_exptl_absorpt_correction_T_max     0.968
_exptl_special_details
;
;
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     confocal
_diffrn_measurement_device_type     'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     9882
_diffrn_reflns_av_R_equivalents     0.0266
_diffrn_reflns_av_sigmaI/netI     0.0303
_diffrn_reflns_theta_min     2.65
_diffrn_reflns_theta_max     27.86
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.976
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     31
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2959
_reflns_number_gt     2547
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0475
_refine_ls_R_factor_gt     0.0413
_refine_ls_wR_factor_gt     0.1014
_refine_ls_wR_factor_ref     0.1070
_refine_ls_goodness_of_fit_ref     1.079
_refine_ls_restrained_S_all     1.079
_refine_ls_number_reflns     2959
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0535P)²+0.6301P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.389
_refine_diff_density_min     -0.500
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'CrystalStructure (Rigaku, 2005)'
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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.91800(7) 0.56853(4) 0.160276(15) 0.01836(13) Uani d . 1 . .
    O O1 1.0236(2) 0.43908(12) 0.15364(5) 0.0236(3) Uani d . 1 . .
    O O2 1.0764(2) 0.68341(12) 0.16025(5) 0.0246(3) Uani d . 1 . .
    N N1 0.7169(3) 0.57948(14) 0.10753(5) 0.0202(3) Uani d . 1 . .
    N N2 0.3909(3) 0.66605(13) 0.05567(5) 0.0176(3) Uani d . 1 . .
    C C1 0.7348(3) 0.57165(15) 0.22140(6) 0.0172(3) Uani d . 1 . .
    C C2 0.8103(3) 0.65238(16) 0.26571(7) 0.0228(3) Uani d . 1 . .
    H H2 0.9534 0.7080 0.2624 0.027 Uiso calc R 1 . .
    C C3 0.6718(4) 0.65010(17) 0.31498(7) 0.0279(4) Uani d . 1 . .
    H H3 0.7205 0.7042 0.3459 0.033 Uiso calc R 1 . .
    C C4 0.4630(4) 0.56891(17) 0.31892(7) 0.0274(4) Uani d . 1 . .
    H H4 0.3674 0.5687 0.3524 0.033 Uiso calc R 1 . .
    C C5 0.3915(3) 0.48754(17) 0.27435(7) 0.0256(4) Uani d . 1 . .
    H H5 0.2491 0.4315 0.2777 0.031 Uiso calc R 1 . .
    C C6 0.5277(3) 0.48821(16) 0.22514(7) 0.0206(3) Uani d . 1 . .
    H H6 0.4806 0.4328 0.1945 0.025 Uiso calc R 1 . .
    C C7 0.5852(3) 0.69057(15) 0.09074(6) 0.0178(3) Uani d . 1 . .
    C C8 0.6390(3) 0.82204(16) 0.10529(7) 0.0212(3) Uani d . 1 . .
    H H8 0.7726 0.8421 0.1305 0.025 Uiso calc R 1 . .
    C C9 0.4944(3) 0.92219(16) 0.08236(7) 0.0241(4) Uani d . 1 . .
    H H9 0.5298 1.0120 0.0917 0.029 Uiso calc R 1 . .
    C C10 0.2968(3) 0.89326(17) 0.04570(7) 0.0236(3) Uani d . 1 . .
    H H10 0.1983 0.9625 0.0298 0.028 Uiso calc R 1 . .
    C C11 0.2475(3) 0.76278(17) 0.03302(6) 0.0209(3) Uani d . 1 . .
    H H11 0.1128 0.7407 0.0084 0.025 Uiso calc R 1 . .
    H H1 0.666(4) 0.502(2) 0.0974(9) 0.035(6) Uiso d . 1 . .
    H H2A 0.347(4) 0.580(2) 0.0487(9) 0.030(6) Uiso d . 1 . .
    N N3 0.3198(3) 0.31725(13) 0.05623(5) 0.0188(3) Uani d . 1 . .
    O O3 0.2271(2) 0.41507(11) 0.02985(5) 0.0213(3) Uani d . 1 . .
    O O4 0.2173(3) 0.20711(11) 0.05331(5) 0.0280(3) Uani d . 1 . .
    O O5 0.5183(2) 0.33211(12) 0.08439(5) 0.0261(3) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0160(2) 0.0236(2) 0.01549(19) 0.00131(14) -0.00045(14) -0.00020(13)
    O1 0.0220(7) 0.0279(6) 0.0210(6) 0.0079(5) -0.0009(5) -0.0034(4)
    O2 0.0190(6) 0.0307(6) 0.0243(6) -0.0058(5) 0.0000(5) 0.0028(5)
    N1 0.0244(8) 0.0196(7) 0.0166(6) 0.0031(5) -0.0039(5) -0.0009(5)
    N2 0.0177(7) 0.0199(7) 0.0153(6) 0.0003(5) 0.0005(5) -0.0015(5)
    C1 0.0167(8) 0.0188(7) 0.0161(7) 0.0027(5) -0.0007(5) 0.0010(5)
    C2 0.0269(9) 0.0196(7) 0.0219(8) -0.0014(6) -0.0019(6) -0.0011(6)
    C3 0.0393(11) 0.0256(8) 0.0187(7) 0.0052(7) -0.0012(7) -0.0029(6)
    C4 0.0302(10) 0.0311(9) 0.0211(8) 0.0080(7) 0.0062(7) 0.0048(6)
    C5 0.0200(9) 0.0279(9) 0.0290(8) 0.0016(6) 0.0027(7) 0.0066(7)
    C6 0.0178(8) 0.0215(8) 0.0224(7) 0.0019(6) -0.0030(6) -0.0009(6)
    C7 0.0173(8) 0.0231(8) 0.0131(6) 0.0006(6) 0.0022(5) 0.0003(5)
    C8 0.0188(9) 0.0240(8) 0.0207(7) -0.0012(6) -0.0003(6) -0.0023(6)
    C9 0.0246(9) 0.0210(8) 0.0267(8) 0.0005(6) 0.0030(7) -0.0012(6)
    C10 0.0229(9) 0.0237(8) 0.0242(8) 0.0037(6) -0.0009(6) 0.0010(6)
    C11 0.0163(8) 0.0272(8) 0.0191(7) 0.0033(6) 0.0001(6) 0.0014(6)
    N3 0.0201(7) 0.0198(6) 0.0166(6) 0.0035(5) -0.0004(5) -0.0015(5)
    O3 0.0238(7) 0.0204(6) 0.0197(5) 0.0027(4) -0.0040(4) 0.0022(4)
    O4 0.0322(8) 0.0184(6) 0.0334(7) -0.0018(5) -0.0079(5) 0.0002(5)
    O5 0.0240(7) 0.0254(6) 0.0288(6) 0.0038(5) -0.0106(5) -0.0029(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.4288(12) ?
    S1 O2 . 1.4322(12) ?
    S1 N1 . 1.6498(15) ?
    S1 C1 . 1.7607(16) ?
    N1 C7 . 1.378(2) ?
    N1 H1 . 0.86(2) ?
    N2 C11 . 1.348(2) ?
    N2 C7 . 1.349(2) ?
    N2 H2A . 0.91(2) ?
    C1 C2 . 1.390(2) ?
    C1 C6 . 1.391(2) ?
    C2 C3 . 1.392(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.385(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.392(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.384(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.397(2) ?
    C8 C9 . 1.380(2) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.394(3) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.373(2) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
    N3 O4 . 1.2378(18) ?
    N3 O5 . 1.2580(18) ?
    N3 O3 . 1.2665(17) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . 120.24(8) ?
    O1 S1 N1 . . 103.35(7) ?
    O2 S1 N1 . . 109.00(7) ?
    O1 S1 C1 . . 109.24(7) ?
    O2 S1 C1 . . 108.47(7) ?
    N1 S1 C1 . . 105.54(8) ?
    C7 N1 S1 . . 127.02(12) ?
    C7 N1 H1 . . 119.6(16) ?
    S1 N1 H1 . . 110.9(15) ?
    C11 N2 C7 . . 123.13(14) ?
    C11 N2 H2A . . 117.8(14) ?
    C7 N2 H2A . . 118.9(14) ?
    C2 C1 C6 . . 122.01(15) ?
    C2 C1 S1 . . 118.68(13) ?
    C6 C1 S1 . . 119.21(12) ?
    C1 C2 C3 . . 118.62(16) ?
    C1 C2 H2 . . 120.7 ?
    C3 C2 H2 . . 120.7 ?
    C4 C3 C2 . . 119.91(16) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 120.73(16) ?
    C3 C4 H4 . . 119.6 ?
    C5 C4 H4 . . 119.6 ?
    C6 C5 C4 . . 120.12(17) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C1 . . 118.60(15) ?
    C5 C6 H6 . . 120.7 ?
    C1 C6 H6 . . 120.7 ?
    N2 C7 N1 . . 114.73(14) ?
    N2 C7 C8 . . 118.83(15) ?
    N1 C7 C8 . . 126.41(15) ?
    C9 C8 C7 . . 118.75(16) ?
    C9 C8 H8 . . 120.6 ?
    C7 C8 H8 . . 120.6 ?
    C8 C9 C10 . . 120.85(16) ?
    C8 C9 H9 . . 119.6 ?
    C10 C9 H9 . . 119.6 ?
    C11 C10 C9 . . 118.72(16) ?
    C11 C10 H10 . . 120.6 ?
    C9 C10 H10 . . 120.6 ?
    N2 C11 C10 . . 119.71(16) ?
    N2 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    O4 N3 O5 . . 120.37(13) ?
    O4 N3 O3 . . 119.89(13) ?
    O5 N3 O3 . . 119.72(13) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 S1 N1 C7 . . . . -171.95(14) ?
    O2 S1 N1 C7 . . . . -42.97(16) ?
    C1 S1 N1 C7 . . . . 73.37(15) ?
    O1 S1 C1 C2 . . . . 114.78(13) ?
    O2 S1 C1 C2 . . . . -17.97(15) ?
    N1 S1 C1 C2 . . . . -134.67(13) ?
    O1 S1 C1 C6 . . . . -61.68(14) ?
    O2 S1 C1 C6 . . . . 165.56(12) ?
    N1 S1 C1 C6 . . . . 48.86(14) ?
    C6 C1 C2 C3 . . . . -0.7(2) ?
    S1 C1 C2 C3 . . . . -177.06(13) ?
    C1 C2 C3 C4 . . . . -0.3(3) ?
    C2 C3 C4 C5 . . . . 1.0(3) ?
    C3 C4 C5 C6 . . . . -0.8(3) ?
    C4 C5 C6 C1 . . . . -0.2(2) ?
    C2 C1 C6 C5 . . . . 0.9(2) ?
    S1 C1 C6 C5 . . . . 177.27(12) ?
    C11 N2 C7 N1 . . . . -177.09(13) ?
    C11 N2 C7 C8 . . . . 1.2(2) ?
    S1 N1 C7 N2 . . . . -164.75(11) ?
    S1 N1 C7 C8 . . . . 17.1(2) ?
    N2 C7 C8 C9 . . . . -1.3(2) ?
    N1 C7 C8 C9 . . . . 176.77(15) ?
    C7 C8 C9 C10 . . . . 0.5(3) ?
    C8 C9 C10 C11 . . . . 0.4(3) ?
    C7 N2 C11 C10 . . . . -0.2(2) ?
    C9 C10 C11 N2 . . . . -0.5(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 H1 O5 . 0.86(2) 1.91(2) 2.760(2) 171(2)
    N2 H2A O3 . 0.91(2) 1.84(2) 2.7417(18) 173(2)
    C8 H8 O2 . 0.95 2.38 3.009(2) 123
    C3 H3 O5 2_655 0.95 2.52 3.432(2) 162
    C10 H10 O4 1_565 0.95 2.53 3.193(2) 127
    C11 H11 O3 3_565 0.95 2.56 3.434(2) 153
    C11 H11 O4 3_565 0.95 2.34 3.223(2) 154
