#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225231.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_2225231
loop_
_publ_author_name
'Temel, Ersin'
'Tokgöz, Beratiye'
'Yazıcılar, Turan Kaya'
'Büyükgüngör, Orhan'
_publ_section_title
;
 2,2'-Bipyridin-1-ium 3-nitrobenzenesulfonate
;
_journal_coeditor_code           FJ2270
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o563
_journal_paper_doi               10.1107/S1600536810003909
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H9 N2 +, C6 H4 N O5 S -'
_chemical_formula_moiety         'C10 H9 N2 +, C6 H4 N O5 S -'
_chemical_formula_sum            'C16 H13 N3 O5 S'
_chemical_formula_weight         359.36
_chemical_name_systematic
;
2,2'-Bipyridin-1-ium 3-nitrobenzenesulfonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                79.085(3)
_cell_angle_beta                 89.121(4)
_cell_angle_gamma                87.939(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9527(3)
_cell_length_b                   7.4674(3)
_cell_length_c                   17.8800(7)
_cell_measurement_reflns_used    3236
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.32
_cell_volume                     779.87(6)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17821
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_correction_T_min  0.8593
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32, Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.507
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_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)+(0.0399P)²+0.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2997
_reflns_number_total             3069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2270.cif
_cod_data_source_block           I
_cod_database_code               2225231
_cod_database_fobs_code          2225231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.9249(3) 0.6631(2) 0.55700(9) 0.0472(3) Uani d . 1 . .
H H1 0.7963 0.6145 0.5410 0.057 Uiso calc R 1 . .
C C2 1.0720(3) 0.7523(2) 0.50459(9) 0.0518(4) Uani d . 1 . .
H H2 1.0453 0.7652 0.4527 0.062 Uiso calc R 1 . .
C C3 1.2602(3) 0.8224(2) 0.53019(10) 0.0551(4) Uani d . 1 . .
H H3 1.3633 0.8815 0.4953 0.066 Uiso calc R 1 . .
C C4 1.2977(3) 0.8059(2) 0.60717(9) 0.0495(4) Uani d . 1 . .
H H4 1.4235 0.8563 0.6241 0.059 Uiso calc R 1 . .
C C5 1.1473(2) 0.71416(19) 0.65879(8) 0.0393(3) Uani d . 1 . .
C C6 1.1649(2) 0.68668(19) 0.74248(8) 0.0399(3) Uani d . 1 . .
C C7 1.3558(3) 0.7287(2) 0.77801(9) 0.0475(4) Uani d . 1 . .
H H7 1.4820 0.7711 0.7497 0.057 Uiso calc R 1 . .
C C8 1.3540(3) 0.7062(2) 0.85644(10) 0.0534(4) Uani d . 1 . .
H H8 1.4785 0.7354 0.8820 0.064 Uiso calc R 1 . .
C C9 1.1657(3) 0.6399(2) 0.89627(9) 0.0554(4) Uani d . 1 . .
H H9 1.1601 0.6244 0.9491 0.066 Uiso calc R 1 . .
C C10 0.9862(3) 0.5970(2) 0.85640(9) 0.0532(4) Uani d . 1 . .
H H10 0.8611 0.5490 0.8838 0.064 Uiso calc R 1 . .
C C11 0.2858(2) 0.1898(2) 0.87745(8) 0.0416(3) Uani d . 1 . .
C C12 0.4108(2) 0.24262(19) 0.81181(8) 0.0383(3) Uani d . 1 . .
H H12 0.5512 0.2924 0.8135 0.046 Uiso calc R 1 . .
C C13 0.3213(2) 0.21927(18) 0.74351(8) 0.0362(3) Uani d . 1 . .
C C14 0.1093(2) 0.1485(2) 0.74167(9) 0.0416(3) Uani d . 1 . .
H H14 0.0484 0.1353 0.6955 0.050 Uiso calc R 1 . .
C C15 -0.0112(2) 0.0977(2) 0.80866(10) 0.0475(4) Uani d . 1 . .
H H15 -0.1527 0.0497 0.8072 0.057 Uiso calc R 1 . .
C C16 0.0758(3) 0.1174(2) 0.87731(9) 0.0476(4) Uani d . 1 . .
H H16 -0.0047 0.0828 0.9224 0.057 Uiso calc R 1 . .
N N1 0.9666(2) 0.64630(17) 0.63119(7) 0.0415(3) Uani d . 1 . .
N N2 0.9811(2) 0.62032(18) 0.78077(7) 0.0467(3) Uani d . 1 . .
N N3 0.3810(3) 0.2146(2) 0.94976(7) 0.0536(3) Uani d . 1 . .
O O1 0.5688(2) 0.2735(2) 0.94961(8) 0.0795(5) Uani d . 1 . .
O O2 0.2667(3) 0.1770(3) 1.00732(8) 0.0897(5) Uani d . 1 . .
O O3 0.6150(2) 0.42572(17) 0.66965(7) 0.0617(3) Uani d . 1 . .
O O4 0.3309(2) 0.3147(2) 0.59711(7) 0.0657(4) Uani d . 1 . .
O O5 0.62591(19) 0.11015(17) 0.65774(7) 0.0547(3) Uani d . 1 . .
S S1 0.48694(6) 0.27252(5) 0.659004(19) 0.04088(12) Uani d . 1 . .
H H1A 0.875(3) 0.581(3) 0.6636(12) 0.062(5) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 119.67(14) ?
N1 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C1 C2 C3 . . 118.59(15) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C2 C3 C4 . . 120.66(15) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.53(14) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
N1 C5 C4 . . 117.78(14) ?
N1 C5 C6 . . 116.68(13) ?
C4 C5 C6 . . 125.53(13) ?
N2 C6 C7 . . 123.11(14) ?
N2 C6 C5 . . 114.67(13) ?
C7 C6 C5 . . 122.21(14) ?
C8 C7 C6 . . 118.32(15) ?
C8 C7 H7 . . 120.8 ?
C6 C7 H7 . . 120.8 ?
C9 C8 C7 . . 119.08(15) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
C10 C9 C8 . . 118.62(15) ?
C10 C9 H9 . . 120.7 ?
C8 C9 H9 . . 120.7 ?
N2 C10 C9 . . 123.73(16) ?
N2 C10 H10 . . 118.1 ?
C9 C10 H10 . . 118.1 ?
C16 C11 C12 . . 122.74(14) ?
C16 C11 N3 . . 119.28(13) ?
C12 C11 N3 . . 117.98(13) ?
C11 C12 C13 . . 118.09(13) ?
C11 C12 H12 . . 121.0 ?
C13 C12 H12 . . 121.0 ?
C12 C13 C14 . . 120.33(13) ?
C12 C13 S1 . . 118.88(10) ?
C14 C13 S1 . . 120.75(11) ?
C15 C14 C13 . . 119.86(14) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C16 C15 C14 . . 120.79(14) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C11 . . 118.18(14) ?
C15 C16 H16 . . 120.9 ?
C11 C16 H16 . . 120.9 ?
C1 N1 C5 . . 123.75(13) ?
C1 N1 H1A . . 117.7(13) ?
C5 N1 H1A . . 118.4(13) ?
C10 N2 C6 . . 117.10(14) ?
O1 N3 O2 . . 122.94(16) ?
O1 N3 C11 . . 118.79(13) ?
O2 N3 C11 . . 118.26(15) ?
O4 S1 O3 . . 113.69(8) ?
O4 S1 O5 . . 113.72(8) ?
O3 S1 O5 . . 112.77(8) ?
O4 S1 C13 . . 106.14(7) ?
O3 S1 C13 . . 104.51(7) ?
O5 S1 C13 . . 104.90(7) ?
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
C1 N1 . 1.335(2) ?
C1 C2 . 1.367(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.373(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.379(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(2) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.3446(18) ?
C5 C6 . 1.476(2) ?
C6 N2 . 1.3413(19) ?
C6 C7 . 1.384(2) ?
C7 C8 . 1.380(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.375(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.374(2) ?
C9 H9 . 0.9300 ?
C10 N2 . 1.331(2) ?
C10 H10 . 0.9300 ?
C11 C16 . 1.380(2) ?
C11 C12 . 1.381(2) ?
C11 N3 . 1.466(2) ?
C12 C13 . 1.383(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.3891(19) ?
C13 S1 . 1.7798(14) ?
C14 C15 . 1.383(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.375(2) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
N1 H1A . 0.88(2) ?
N3 O1 . 1.2153(19) ?
N3 O2 . 1.2180(19) ?
O3 S1 . 1.4406(12) ?
O4 S1 . 1.4371(12) ?
O5 S1 . 1.4466(12) ?
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
C1 H1 O4 2_666 0.93 2.55 3.1426(19) 122
C2 H2 O4 2_666 0.93 2.55 3.142(2) 122
C4 H4 O5 1_665 0.93 2.45 3.3089(19) 153
N1 H1A O3 . 0.88(2) 1.95(2) 2.7096(16) 142.9(18)
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
N1 C1 C2 C3 . . . . 0.0(3) ?
C1 C2 C3 C4 . . . . -1.1(3) ?
C2 C3 C4 C5 . . . . 1.6(3) ?
C3 C4 C5 N1 . . . . -1.0(2) ?
C3 C4 C5 C6 . . . . -179.67(15) ?
N1 C5 C6 N2 . . . . -9.30(19) ?
C4 C5 C6 N2 . . . . 169.42(15) ?
N1 C5 C6 C7 . . . . 171.48(14) ?
C4 C5 C6 C7 . . . . -9.8(2) ?
N2 C6 C7 C8 . . . . -2.0(2) ?
C5 C6 C7 C8 . . . . 177.20(14) ?
C6 C7 C8 C9 . . . . 1.3(2) ?
C7 C8 C9 C10 . . . . 0.5(3) ?
C8 C9 C10 N2 . . . . -1.8(3) ?
C16 C11 C12 C13 . . . . -0.8(2) ?
N3 C11 C12 C13 . . . . 179.98(13) ?
C11 C12 C13 C14 . . . . 1.5(2) ?
C11 C12 C13 S1 . . . . -175.98(11) ?
C12 C13 C14 C15 . . . . -1.3(2) ?
S1 C13 C14 C15 . . . . 176.12(11) ?
C13 C14 C15 C16 . . . . 0.4(2) ?
C14 C15 C16 C11 . . . . 0.3(2) ?
C12 C11 C16 C15 . . . . -0.1(2) ?
N3 C11 C16 C15 . . . . 179.13(14) ?
C2 C1 N1 C5 . . . . 0.6(2) ?
C4 C5 N1 C1 . . . . -0.1(2) ?
C6 C5 N1 C1 . . . . 178.68(14) ?
C9 C10 N2 C6 . . . . 1.2(3) ?
C7 C6 N2 C10 . . . . 0.8(2) ?
C5 C6 N2 C10 . . . . -178.46(13) ?
C16 C11 N3 O1 . . . . 177.87(16) ?
C12 C11 N3 O1 . . . . -2.9(2) ?
C16 C11 N3 O2 . . . . -2.9(2) ?
C12 C11 N3 O2 . . . . 176.31(16) ?
C12 C13 S1 O4 . . . . -154.95(12) ?
C14 C13 S1 O4 . . . . 27.62(14) ?
C12 C13 S1 O3 . . . . -34.49(13) ?
C14 C13 S1 O3 . . . . 148.08(12) ?
C12 C13 S1 O5 . . . . 84.36(12) ?
C14 C13 S1 O5 . . . . -93.07(13) ?
