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###                                                                        ###
###        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 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2007-11-07
_journal_date_accepted     2007-12-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o254
_journal_page_last     o254
_journal_paper_category     QO
_journal_coeditor_code     HB2642
_publ_contact_author_name     'Bin Zhou'
_publ_contact_author_address
; School of Pharmacy,
 Jiangxi Science and Technology Normal University,
 Nanchang 330013,
 P. R. China
;
_publ_contact_author_email     tju_zhoubin@yahoo.com.cn
_publ_contact_author_fax     '+86 791-3805385'
_publ_contact_author_phone     '+86 791-3805385'
_publ_section_title
;
4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhou, Bin'
;
School of Pharmacy,
Jiangxi Science and Technology Normal University,
Nangchang 330013,
People's Republic of China
;
    'Zheng, Peng-Wu'
;
School of Pharmacy,
Jiangxi Science and Technology Normal University,
Nangchang 330013,
People's Republic of China
;
    'Liu, Ke-Yue'
;
Medical College,
Jiujiang University,
Jiujiang 332000,
People's Republic of China
;
    'Dan Cheng'
;
School of Pharmacy,
Jiangxi Science and Technology Normal University,
Nangchang 330013,
People's Republic of China
;
data_I
_chemical_name_systematic
;
4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 N3 O4 S +, C2 Cl3 O2 -'
_chemical_formula_sum     'C13 H10 Cl3 N3 O6 S'
_chemical_formula_iupac     'C11 H10 N3 O4 S +, C2 Cl3 O2 -'
_chemical_formula_weight     442.65
_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     5.9929(11)
_cell_length_b     17.790(3)
_cell_length_c     16.325(3)
_cell_angle_alpha     90.00
_cell_angle_beta     98.377(3)
_cell_angle_gamma     90.00
_cell_volume     1721.9(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2690
_cell_measurement_theta_min     2.52
_cell_measurement_theta_max     25.71
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.707
_exptl_crystal_density_meas     .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     896
_exptl_absorpt_coefficient_mu     0.691
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.852
_exptl_absorpt_correction_T_max     0.886
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1K CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9742
_diffrn_reflns_av_R_equivalents     0.0379
_diffrn_reflns_av_sigmaI/netI     0.0476
_diffrn_reflns_theta_min     1.70
_diffrn_reflns_theta_max     26.43
_diffrn_reflns_theta_full     26.43
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
_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 > 2sigma(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     3528
_reflns_number_gt     2427
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0716
_refine_ls_R_factor_gt     0.0392
_refine_ls_wR_factor_gt     0.0806
_refine_ls_wR_factor_ref     0.0940
_refine_ls_goodness_of_fit_ref     1.014
_refine_ls_restrained_S_all     1.014
_refine_ls_number_reflns     3528
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0353P)²+0.9782P] 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     0.366
_refine_diff_density_min     -0.383
_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'
    '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'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL (Bruker, 1997)'
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 0.20681(12) 0.30768(4) 0.84918(4) 0.03291(18) Uani d . 1 . .
    O O1 0.2730(4) 0.26231(11) 0.92092(11) 0.0449(5) Uani d . 1 . .
    O O2 -0.0263(3) 0.32167(11) 0.82059(13) 0.0448(5) Uani d . 1 . .
    O O3 0.8738(4) 0.60031(12) 0.95523(13) 0.0495(5) Uani d . 1 . .
    O O4 0.5848(4) 0.65976(12) 0.89304(15) 0.0575(6) Uani d . 1 . .
    N N1 0.2323(4) 0.30604(14) 0.52313(15) 0.0413(6) Uani d . 1 . .
    H H1 0.215(5) 0.3155(17) 0.470(2) 0.050 Uiso d . 1 . .
    N N2 0.3239(4) 0.26681(13) 0.77572(13) 0.0321(5) Uani d . 1 . .
    H H2A 0.422(5) 0.2386(17) 0.7939(18) 0.039 Uiso d . 1 . .
    N N3 0.6823(4) 0.60178(14) 0.91655(14) 0.0372(6) Uani d . 1 . .
    C C1 0.2886(4) 0.28291(14) 0.69149(15) 0.0270(6) Uani d . 1 . .
    C C2 0.4432(5) 0.25395(16) 0.64290(16) 0.0358(7) Uani d . 1 . .
    H H2 0.5671 0.2263 0.6673 0.043 Uiso calc R 1 . .
    C C3 0.4103(5) 0.26665(16) 0.55900(17) 0.0416(7) Uani d . 1 . .
    H H3 0.5130 0.2476 0.5267 0.050 Uiso calc R 1 . .
    C C4 0.0846(5) 0.33458(17) 0.56820(18) 0.0430(7) Uani d . 1 . .
    H H4 -0.0383 0.3615 0.5418 0.052 Uiso calc R 1 . .
    C C5 0.1084(5) 0.32541(16) 0.65210(17) 0.0386(7) Uani d . 1 . .
    H H5 0.0059 0.3472 0.6826 0.046 Uiso calc R 1 . .
    C C6 0.3464(4) 0.39542(14) 0.86639(15) 0.0284(6) Uani d . 1 . .
    C C7 0.2334(4) 0.46213(15) 0.84301(16) 0.0320(6) Uani d . 1 . .
    H H7 0.0850 0.4610 0.8166 0.038 Uiso calc R 1 . .
    C C8 0.3429(4) 0.53001(15) 0.85921(16) 0.0337(6) Uani d . 1 . .
    H H8 0.2698 0.5751 0.8443 0.040 Uiso calc R 1 . .
    C C9 0.5640(4) 0.52928(15) 0.89817(15) 0.0299(6) Uani d . 1 . .
    C C10 0.6797(5) 0.46378(16) 0.92142(17) 0.0347(7) Uani d . 1 . .
    H H10 0.8285 0.4653 0.9474 0.042 Uiso calc R 1 . .
    C C11 0.5696(4) 0.39591(15) 0.90528(16) 0.0334(6) Uani d . 1 . .
    H H11 0.6438 0.3510 0.9202 0.040 Uiso calc R 1 . .
    O O5 0.1076(4) 0.40196(11) 0.23515(11) 0.0457(5) Uani d . 1 . .
    O O6 0.1360(3) 0.33610(11) 0.35309(11) 0.0412(5) Uani d . 1 . .
    Cl Cl1 0.23049(13) 0.47867(4) 0.44855(4) 0.0447(2) Uani d . 1 . .
    Cl Cl2 0.60598(13) 0.41336(5) 0.37668(6) 0.0579(3) Uani d . 1 . .
    Cl Cl3 0.34546(14) 0.53626(4) 0.29679(5) 0.0486(2) Uani d . 1 . .
    C C12 0.1730(4) 0.39111(15) 0.30852(16) 0.0293(6) Uani d . 1 . .
    C C13 0.3314(4) 0.45299(15) 0.35494(16) 0.0305(6) Uani d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 O2 . 1.429(2) ?
    S1 O1 . 1.430(2) ?
    S1 N2 . 1.645(2) ?
    S1 C6 . 1.774(3) ?
    O3 N3 . 1.227(3) ?
    O4 N3 . 1.220(3) ?
    N1 C4 . 1.331(4) ?
    N1 C3 . 1.338(4) ?
    N1 H1 . 0.87(3) ?
    N2 C1 . 1.390(3) ?
    N2 H2A . 0.79(3) ?
    N3 C9 . 1.481(3) ?
    C1 C5 . 1.396(4) ?
    C1 C2 . 1.402(3) ?
    C2 C3 . 1.374(4) ?
    C2 H2 . 0.9300 ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.366(4) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.392(3) ?
    C6 C11 . 1.395(4) ?
    C7 C8 . 1.381(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.384(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.381(4) ?
    C10 C11 . 1.383(4) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    O5 C12 . 1.220(3) ?
    O6 C12 . 1.258(3) ?
    Cl1 C13 . 1.783(3) ?
    Cl2 C13 . 1.778(3) ?
    Cl3 C13 . 1.768(3) ?
    C12 C13 . 1.574(4) ?
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
    O2 S1 O1 . . 120.47(13) ?
    O2 S1 N2 . . 109.85(12) ?
    O1 S1 N2 . . 104.53(12) ?
    O2 S1 C6 . . 108.34(12) ?
    O1 S1 C6 . . 107.38(12) ?
    N2 S1 C6 . . 105.25(12) ?
    C4 N1 C3 . . 120.6(2) ?
    C4 N1 H1 . . 119(2) ?
    C3 N1 H1 . . 120(2) ?
    C1 N2 S1 . . 127.63(19) ?
    C1 N2 H2A . . 120(2) ?
    S1 N2 H2A . . 112(2) ?
    O4 N3 O3 . . 123.3(3) ?
    O4 N3 C9 . . 118.6(2) ?
    O3 N3 C9 . . 118.0(2) ?
    N2 C1 C5 . . 124.3(2) ?
    N2 C1 C2 . . 117.8(2) ?
    C5 C1 C2 . . 118.0(2) ?
    C3 C2 C1 . . 119.5(3) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    N1 C3 C2 . . 120.8(3) ?
    N1 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    N1 C4 C5 . . 121.8(3) ?
    N1 C4 H4 . . 119.1 ?
    C5 C4 H4 . . 119.1 ?
    C4 C5 C1 . . 119.2(3) ?
    C4 C5 H5 . . 120.4 ?
    C1 C5 H5 . . 120.4 ?
    C7 C6 C11 . . 121.0(2) ?
    C7 C6 S1 . . 120.5(2) ?
    C11 C6 S1 . . 118.5(2) ?
    C8 C7 C6 . . 119.6(3) ?
    C8 C7 H7 . . 120.2 ?
    C6 C7 H7 . . 120.2 ?
    C7 C8 C9 . . 118.4(2) ?
    C7 C8 H8 . . 120.8 ?
    C9 C8 H8 . . 120.8 ?
    C10 C9 C8 . . 122.9(3) ?
    C10 C9 N3 . . 118.2(2) ?
    C8 C9 N3 . . 118.9(2) ?
    C9 C10 C11 . . 118.5(3) ?
    C9 C10 H10 . . 120.7 ?
    C11 C10 H10 . . 120.7 ?
    C10 C11 C6 . . 119.5(2) ?
    C10 C11 H11 . . 120.3 ?
    C6 C11 H11 . . 120.3 ?
    O5 C12 O6 . . 129.2(2) ?
    O5 C12 C13 . . 116.5(2) ?
    O6 C12 C13 . . 114.2(2) ?
    C12 C13 Cl3 . . 113.58(18) ?
    C12 C13 Cl2 . . 107.13(17) ?
    Cl3 C13 Cl2 . . 108.93(14) ?
    C12 C13 Cl1 . . 109.61(18) ?
    Cl3 C13 Cl1 . . 107.11(14) ?
    Cl2 C13 Cl1 . . 110.50(14) ?
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
    O2 S1 N2 C1 . . . . 40.4(3) ?
    O1 S1 N2 C1 . . . . 171.0(2) ?
    C6 S1 N2 C1 . . . . -76.0(3) ?
    S1 N2 C1 C5 . . . . -15.4(4) ?
    S1 N2 C1 C2 . . . . 165.2(2) ?
    N2 C1 C2 C3 . . . . 178.0(3) ?
    C5 C1 C2 C3 . . . . -1.5(4) ?
    C4 N1 C3 C2 . . . . 0.8(5) ?
    C1 C2 C3 N1 . . . . -0.2(4) ?
    C3 N1 C4 C5 . . . . 0.4(5) ?
    N1 C4 C5 C1 . . . . -2.1(5) ?
    N2 C1 C5 C4 . . . . -176.8(3) ?
    C2 C1 C5 C4 . . . . 2.6(4) ?
    O2 S1 C6 C7 . . . . -7.4(2) ?
    O1 S1 C6 C7 . . . . -138.9(2) ?
    N2 S1 C6 C7 . . . . 110.1(2) ?
    O2 S1 C6 C11 . . . . 171.35(19) ?
    O1 S1 C6 C11 . . . . 39.8(2) ?
    N2 S1 C6 C11 . . . . -71.2(2) ?
    C11 C6 C7 C8 . . . . -0.6(4) ?
    S1 C6 C7 C8 . . . . 178.0(2) ?
    C6 C7 C8 C9 . . . . 0.3(4) ?
    C7 C8 C9 C10 . . . . 0.1(4) ?
    C7 C8 C9 N3 . . . . -179.4(2) ?
    O4 N3 C9 C10 . . . . 176.8(2) ?
    O3 N3 C9 C10 . . . . -3.5(3) ?
    O4 N3 C9 C8 . . . . -3.6(4) ?
    O3 N3 C9 C8 . . . . 176.0(2) ?
    C8 C9 C10 C11 . . . . -0.2(4) ?
    N3 C9 C10 C11 . . . . 179.3(2) ?
    C9 C10 C11 C6 . . . . -0.1(4) ?
    C7 C6 C11 C10 . . . . 0.5(4) ?
    S1 C6 C11 C10 . . . . -178.2(2) ?
    O5 C12 C13 Cl3 . . . . 11.0(3) ?
    O6 C12 C13 Cl3 . . . . -170.43(19) ?
    O5 C12 C13 Cl2 . . . . -109.3(2) ?
    O6 C12 C13 Cl2 . . . . 69.2(3) ?
    O5 C12 C13 Cl1 . . . . 130.8(2) ?
    O6 C12 C13 Cl1 . . . . -50.7(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 H1 O6 . 0.87(3) 1.93(3) 2.803(3) 172(3)
    N2 H2A O6 4_666 0.79(3) 2.00(3) 2.785(3) 171(3)
    C2 H2 O5 4_666 0.93 2.53 3.240(3) 133
    C3 H3 O1 4_665 0.93 2.50 3.391(4) 162
    C8 H8 O5 3_566 0.93 2.47 3.149(3) 130
    C10 H10 O3 3_767 0.93 2.50 3.308(4) 146
    C5 H5 O2 . 0.93 2.33 2.978(4) 126
    C7 H7 O2 . 0.93 2.57 2.938(3) 104
