#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/52/2215201.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_2215201
loop_
_publ_author_name
'Yu, Hai-Jun'
'Chen, Jin-Zhe'
'Simpson, Jim'
'Li, Jiang-Sheng'
'Bai, Guo-Yi'
_publ_section_title
;
 A zwitterionic form of N-(4-pyridyl)benzenesulfonamide
;
_journal_coeditor_code           LH2469
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3720
_journal_page_last               o3720
_journal_paper_doi               10.1107/S1600536807037713
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C11 H10 N2 O2 S'
_chemical_formula_sum            'C11 H10 N2 O2 S'
_chemical_formula_weight         234.27
_chemical_name_common
;
N-(4-pyridyl)benzenesulfonamide
;
_chemical_name_systematic
;
N-(4-pyridinio)benzenesulfonamidate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.231(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.238(6)
_cell_length_b                   7.459(4)
_cell_length_c                   12.124(6)
_cell_measurement_reflns_used    2352
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      3.26
_cell_volume                     1038.4(9)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL  (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5733
_diffrn_reflns_theta_full        26.53
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.6075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                1685
_reflns_number_total             2139
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2469.cif
_cod_data_source_block           I
_cod_original_cell_volume        1038.5(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215201
_cod_database_fobs_code          2215201
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_disorder_assembly
_atom_site_disorder_group
S S1 0.31544(6) 0.16315(8) 0.92018(5) 0.0360(2) Uani d D 1 . .
O O1 0.37860(16) 0.2910(2) 1.00505(15) 0.0434(5) Uani d . 1 A .
O O2 0.31798(19) 0.1853(2) 0.80497(15) 0.0525(5) Uani d . 1 A .
N N1 0.37226(18) -0.2772(3) 1.26144(18) 0.0359(5) Uani d . 1 A .
N N2 0.35106(17) -0.0376(3) 0.95349(16) 0.0335(5) Uani d . 1 A .
C C6 0.1697(5) 0.1746(11) 0.9082(8) 0.030(3) Uani d PGDU 0.59(4) A 1
C C7 0.0798(9) 0.0865(11) 0.8225(7) 0.053(2) Uani d PGU 0.59(4) A 1
H H7 0.0953 0.0206 0.7644 0.063 Uiso calc PR 0.59(4) A 1
C C8 -0.0333(7) 0.0967(12) 0.8235(11) 0.061(3) Uani d PGU 0.59(4) A 1
H H8 -0.0934 0.0377 0.7662 0.074 Uiso calc PR 0.59(4) A 1
C C9 -0.0565(4) 0.1951(14) 0.9103(13) 0.058(2) Uani d PGU 0.59(4) A 1
H H9 -0.1321 0.2020 0.9110 0.069 Uiso calc PR 0.59(4) A 1
C C10 0.0334(9) 0.2833(14) 0.9960(9) 0.064(2) Uani d PGU 0.59(4) A 1
H H10 0.0179 0.3492 1.0541 0.077 Uiso calc PR 0.59(4) A 1
C C11 0.1465(6) 0.2731(11) 0.9950(7) 0.060(3) Uani d PGU 0.59(4) A 1
H H11 0.2066 0.3321 1.0523 0.072 Uiso calc PR 0.59(4) A 1
C C1 0.3656(2) -0.1014(3) 1.2553(2) 0.0374(6) Uani d . 1 . .
H H1 0.3650 -0.0370 1.3207 0.045 Uiso calc R 1 . .
C C2 0.3596(2) -0.0120(3) 1.15722(19) 0.0342(5) Uani d . 1 A .
H H2 0.3545 0.1125 1.1553 0.041 Uiso calc R 1 . .
C C3 0.36113(19) -0.1056(3) 1.05825(19) 0.0289(5) Uani d . 1 . .
C C4 0.3726(2) -0.2902(3) 1.0710(2) 0.0353(5) Uani d . 1 A .
H H4 0.3777 -0.3587 1.0089 0.042 Uiso calc R 1 . .
C C5 0.3765(2) -0.3719(3) 1.1703(2) 0.0347(5) Uani d . 1 . .
H H5 0.3823 -0.4961 1.1756 0.042 Uiso calc R 1 A .
C C6' 0.1758(6) 0.180(2) 0.9147(12) 0.057(7) Uani d PGDU 0.41(4) A 2
C C7' 0.1019(13) 0.090(2) 0.8167(11) 0.066(4) Uani d PGU 0.41(4) A 2
H H7' 0.1320 0.0348 0.7646 0.079 Uiso calc PR 0.41(4) A 2
C C8' -0.0169(11) 0.0831(17) 0.7966(13) 0.071(4) Uani d PGU 0.41(4) A 2
H H8' -0.0664 0.0232 0.7310 0.086 Uiso calc PR 0.41(4) A 2
C C9' -0.0619(5) 0.1657(18) 0.8744(17) 0.051(3) Uani d PGU 0.41(4) A 2
H H9' -0.1414 0.1610 0.8610 0.062 Uiso calc PR 0.41(4) A 2
C C10' 0.0120(11) 0.2552(18) 0.9724(13) 0.043(3) Uani d PGU 0.41(4) A 2
H H10' -0.0181 0.3105 1.0245 0.051 Uiso calc PR 0.41(4) A 2
C C11' 0.1309(9) 0.2622(16) 0.9925(9) 0.034(3) Uani d PGU 0.41(4) A 2
H H11' 0.1803 0.3221 1.0581 0.041 Uiso calc PR 0.41(4) A 2
H H1A 0.375(3) -0.329(4) 1.322(3) 0.057(9) Uiso d . 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
O2 S1 O1 116.35(12)
O2 S1 N2 105.41(11)
O1 S1 N2 114.85(11)
O2 S1 C6' 108.6(5)
O1 S1 C6' 105.6(4)
N2 S1 C6' 105.4(5)
O2 S1 C6 106.4(3)
O1 S1 C6 108.2(3)
N2 S1 C6 104.7(3)
C1 N1 C5 120.2(2)
C1 N1 H1A 120(2)
C5 N1 H1A 119(2)
C3 N2 S1 122.23(16)
C7 C6 C11 120.0
C7 C6 S1 124.2(6)
C11 C6 S1 115.7(6)
C6 C7 C8 120.0
C6 C7 H7 120.0
C8 C7 H7 120.0
C7 C8 C9 120.0
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C10 120.0
C8 C9 H9 120.0
C10 C9 H9 120.0
C11 C10 C9 120.0
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C6 120.0
C10 C11 H11 120.0
C6 C11 H11 120.0
N1 C1 C2 122.0(2)
N1 C1 H1 119.0
C2 C1 H1 119.0
C1 C2 C3 120.0(2)
C1 C2 H2 120.0
C3 C2 H2 120.0
N2 C3 C4 117.2(2)
N2 C3 C2 127.2(2)
C4 C3 C2 115.6(2)
C5 C4 C3 121.6(2)
C5 C4 H4 119.2
C3 C4 H4 119.2
N1 C5 C4 120.5(2)
N1 C5 H5 119.7
C4 C5 H5 119.7
C7' C6' C11' 120.0
C7' C6' S1 110.4(9)
C11' C6' S1 129.6(9)
C8' C7' C6' 120.0
C8' C7' H7' 120.0
C6' C7' H7' 120.0
C7' C8' C9' 120.0
C7' C8' H8' 120.0
C9' C8' H8' 120.0
C10' C9' C8' 120.0
C10' C9' H9' 120.0
C8' C9' H9' 120.0
C9' C10' C11' 120.0
C9' C10' H10' 120.0
C11' C10' H10' 120.0
C10' C11' C6' 120.0
C10' C11' H11' 120.0
C6' C11' H11' 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4174(19)
S1 O1 1.4195(18)
S1 N2 1.573(2)
S1 C6' 1.692(5)
S1 C6 1.742(4)
N1 C1 1.315(3)
N1 C5 1.328(3)
N1 H1A 0.82(3)
N2 C3 1.333(3)
C6 C7 1.3900
C6 C11 1.3900
C7 C8 1.3900
C7 H7 0.9300
C8 C9 1.3900
C8 H8 0.9300
C9 C10 1.3900
C9 H9 0.9300
C10 C11 1.3900
C10 H10 0.9300
C11 H11 0.9300
C1 C2 1.343(3)
C1 H1 0.9300
C2 C3 1.394(3)
C2 H2 0.9300
C3 C4 1.387(3)
C4 C5 1.335(3)
C4 H4 0.9300
C5 H5 0.9300
C6' C7' 1.3900
C6' C11' 1.3900
C7' C8' 1.3900
C7' H7' 0.9300
C8' C9' 1.3900
C8' H8' 0.9300
C9' C10' 1.3900
C9' H9' 0.9300
C10' C11' 1.3900
C10' H10' 0.9300
C11' H11' 0.9300
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 H1A N2 4_556 0.82(3) 1.99(3) 2.795(3) 170(3)
C2 H2 O2 4_566 0.93 2.52 3.168(3) 127.5
C5 H5 O1 1_545 0.93 2.60 3.221(3) 125.0
C4 H4 O1 1_545 0.93 2.61 3.232(3) 124.5
C5 H5 O2 4_556 0.93 2.43 3.075(3) 126.1
C9 H9 Cg 3_557 0.93 2.71 3.603(8) 161.1
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
O2 S1 N2 C3 178.12(19)
O1 S1 N2 C3 48.7(2)
C6' S1 N2 C3 -67.1(5)
C6 S1 N2 C3 -69.8(3)
O2 S1 C6 C7 45.2(5)
O1 S1 C6 C7 170.9(4)
N2 S1 C6 C7 -66.2(5)
C6' S1 C6 C7 -173(18)
O2 S1 C6 C11 -137.9(4)
O1 S1 C6 C11 -12.1(5)
N2 S1 C6 C11 110.8(4)
C6' S1 C6 C11 4(17)
C11 C6 C7 C8 0.0
S1 C6 C7 C8 176.9(6)
C6 C7 C8 C9 0.0
C7 C8 C9 C10 0.0
C8 C9 C10 C11 0.0
C9 C10 C11 C6 0.0
C7 C6 C11 C10 0.0
S1 C6 C11 C10 -177.1(6)
C5 N1 C1 C2 1.9(4)
N1 C1 C2 C3 -0.4(4)
S1 N2 C3 C4 168.89(18)
S1 N2 C3 C2 -10.0(3)
C1 C2 C3 N2 177.0(2)
C1 C2 C3 C4 -1.9(3)
N2 C3 C4 C5 -176.1(2)
C2 C3 C4 C5 2.9(4)
C1 N1 C5 C4 -0.9(4)
C3 C4 C5 N1 -1.6(4)
O2 S1 C6' C7' 41.3(6)
O1 S1 C6' C7' 166.7(5)
N2 S1 C6' C7' -71.3(6)
C6 S1 C6' C7' 3(17)
O2 S1 C6' C11' -140.4(9)
O1 S1 C6' C11' -14.9(11)
N2 S1 C6' C11' 107.0(9)
C6 S1 C6' C11' -179(18)
C11' C6' C7' C8' 0.0
S1 C6' C7' C8' 178.5(10)
C6' C7' C8' C9' 0.0
C7' C8' C9' C10' 0.0
C8' C9' C10' C11' 0.0
C9' C10' C11' C6' 0.0
C7' C6' C11' C10' 0.0
S1 C6' C11' C10' -178.2(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 669138
