#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/61/2016122.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_2016122
loop_
_publ_author_name
'Zhang, Jing'
'Zhu, Long-Guan'
_publ_section_title
;
 Different supramolecular assemblies in two 1:1 proton-transfer
 compounds of sulfobenzoic acids with aromatic amines
;
_journal_coeditor_code           SQ3086
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o484
_journal_page_last               o486
_journal_paper_doi               10.1107/S0108270107033008
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H11 N2 +, C7 H5 O5 S -'
_chemical_formula_moiety         'C12 H11 N2 +, C7 H5 O5 S -'
_chemical_formula_sum            'C19 H16 N2 O5 S'
_chemical_formula_weight         384.40
_chemical_name_systematic
;
4-[2-(4-pyridyl)ethenyl]pyridinium 2-carboxybenzenesulfonate
;
_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                95.3770(10)
_cell_angle_beta                 104.9540(10)
_cell_angle_gamma                104.047(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7451(11)
_cell_length_b                   10.0346(13)
_cell_length_c                   10.7877(14)
_cell_measurement_reflns_used    2034
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.5
_cell_volume                     874.82(19)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4632
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.51
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_correction_T_min  0.9349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.350
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0654P)²+0.5901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2534
_reflns_number_total             3095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3086.cif
_cod_data_source_block           I
_cod_database_code               2016122
_cod_database_fobs_code          2016122
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
S S1 0.42777(7) 0.78017(5) 0.80645(5) 0.03731(17) Uani d . 1
O O1 0.0436(2) 0.45903(17) 0.68689(17) 0.0557(5) Uani d D 1
O O2 0.2524(2) 0.45248(16) 0.85457(16) 0.0515(4) Uani d . 1
O O3 0.54928(18) 0.73581(16) 0.90142(14) 0.0443(4) Uani d . 1
O O4 0.4846(2) 0.92381(17) 0.79259(18) 0.0593(5) Uani d . 1
O O5 0.3627(2) 0.68389(17) 0.68485(14) 0.0501(4) Uani d . 1
C C1 0.1534(3) 0.5088(2) 0.7994(2) 0.0385(5) Uani d . 1
C C2 0.1417(3) 0.6458(2) 0.86118(19) 0.0357(5) Uani d . 1
C C3 0.2594(3) 0.7712(2) 0.87205(18) 0.0346(5) Uani d . 1
C C4 0.2484(3) 0.8932(2) 0.9374(2) 0.0452(5) Uani d . 1
H H4 0.3260 0.9773 0.9437 0.054 Uiso calc R 1
C C5 0.1222(3) 0.8891(3) 0.9928(2) 0.0563(7) Uani d . 1
H H5 0.1175 0.9703 1.0390 0.068 Uiso calc R 1
C C6 0.0037(3) 0.7669(3) 0.9807(2) 0.0575(7) Uani d . 1
H H6 -0.0821 0.7654 1.0171 0.069 Uiso calc R 1
C C7 0.0126(3) 0.6453(3) 0.9138(2) 0.0480(6) Uani d . 1
H H7 -0.0689 0.5627 0.9040 0.058 Uiso calc R 1
N N1 0.8844(2) -0.2544(2) 0.4335(2) 0.0487(5) Uani d . 1
N N2 0.5713(2) 0.4792(2) 0.79293(17) 0.0412(4) Uani d D 1
C C8 0.8208(3) -0.1638(2) 0.3702(2) 0.0487(6) Uani d . 1
H H8 0.8111 -0.1695 0.2818 0.058 Uiso calc R 1
C C9 0.7684(3) -0.0619(2) 0.4281(2) 0.0437(5) Uani d . 1
H H9 0.7257 -0.0004 0.3798 0.052 Uiso calc R 1
C C10 0.7803(3) -0.0525(2) 0.5594(2) 0.0400(5) Uani d . 1
C C11 0.8444(3) -0.1490(2) 0.6244(2) 0.0539(6) Uani d . 1
H H11 0.8528 -0.1480 0.7122 0.065 Uiso calc R 1
C C12 0.8954(3) -0.2457(3) 0.5592(3) 0.0560(6) Uani d . 1
H H12 0.9397 -0.3081 0.6052 0.067 Uiso calc R 1
C C13 0.7306(3) 0.0539(2) 0.6308(2) 0.0426(5) Uani d . 1
H H13 0.7207 0.0406 0.7129 0.051 Uiso calc R 1
C C14 0.6987(3) 0.1666(2) 0.5887(2) 0.0429(5) Uani d . 1
H H14 0.7065 0.1794 0.5060 0.051 Uiso calc R 1
C C15 0.6522(2) 0.2728(2) 0.66169(19) 0.0362(5) Uani d . 1
C C16 0.6112(3) 0.2570(2) 0.7770(2) 0.0394(5) Uani d . 1
H H16 0.6110 0.1750 0.8106 0.047 Uiso calc R 1
C C17 0.5712(3) 0.3618(2) 0.8410(2) 0.0411(5) Uani d . 1
H H17 0.5439 0.3509 0.9179 0.049 Uiso calc R 1
C C18 0.6486(3) 0.3971(2) 0.6148(2) 0.0425(5) Uani d . 1
H H18 0.6740 0.4109 0.5376 0.051 Uiso calc R 1
C C19 0.6080(3) 0.4984(2) 0.6820(2) 0.0463(5) Uani d . 1
H H19 0.6057 0.5813 0.6505 0.056 Uiso calc R 1
H H1A 0.062(4) 0.389(2) 0.647(3) 0.080 Uiso d D 1
H H2A 0.548(4) 0.543(2) 0.833(3) 0.080 Uiso d 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
_geom_angle_publ_flag
O4 S1 O5 114.20(10) ?
O4 S1 O3 112.94(11) ?
O5 S1 O3 111.78(9) ?
O4 S1 C3 105.51(10) ?
O5 S1 C3 105.87(10) ?
O3 S1 C3 105.69(9) ?
C1 O1 H1A 112(2) ?
O2 C1 O1 125.7(2) ?
O2 C1 C2 121.3(2) ?
O1 C1 C2 113.00(18) ?
C7 C2 C3 119.1(2) ?
C7 C2 C1 118.6(2) ?
C3 C2 C1 122.31(18) ?
C4 C3 C2 119.9(2) ?
C4 C3 S1 118.40(18) ?
C2 C3 S1 121.66(15) ?
C5 C4 C3 119.9(2) ?
C5 C4 H4 120.1 ?
C3 C4 H4 120.1 ?
C6 C5 C4 120.8(2) ?
C6 C5 H5 119.6 ?
C4 C5 H5 119.6 ?
C5 C6 C7 119.6(2) ?
C5 C6 H6 120.2 ?
C7 C6 H6 120.2 ?
C6 C7 C2 120.7(2) ?
C6 C7 H7 119.6 ?
C2 C7 H7 119.6 ?
C12 N1 C8 117.2(2) yes
C17 N2 C19 121.94(18) yes
C17 N2 H2A 119(2) ?
C19 N2 H2A 119(2) ?
N1 C8 C9 123.7(2) ?
N1 C8 H8 118.1 ?
C9 C8 H8 118.1 ?
C8 C9 C10 119.1(2) ?
C8 C9 H9 120.5 ?
C10 C9 H9 120.5 ?
C9 C10 C11 116.8(2) ?
C9 C10 C13 123.3(2) ?
C11 C10 C13 119.8(2) ?
C12 C11 C10 120.1(2) ?
C12 C11 H11 120.0 ?
C10 C11 H11 120.0 ?
N1 C12 C11 123.0(2) ?
N1 C12 H12 118.5 ?
C11 C12 H12 118.5 ?
C14 C13 C10 125.8(2) ?
C14 C13 H13 117.1 ?
C10 C13 H13 117.1 ?
C13 C14 C15 125.2(2) ?
C13 C14 H14 117.4 ?
C15 C14 H14 117.4 ?
C16 C15 C18 117.54(18) ?
C16 C15 C14 123.51(19) ?
C18 C15 C14 118.95(18) ?
C17 C16 C15 120.3(2) ?
C17 C16 H16 119.9 ?
C15 C16 H16 119.9 ?
N2 C17 C16 119.92(19) ?
N2 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C19 C18 C15 120.04(19) ?
C19 C18 H18 120.0 ?
C15 C18 H18 120.0 ?
N2 C19 C18 120.3(2) ?
N2 C19 H19 119.9 ?
C18 C19 H19 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O4 1.4414(17) ?
S1 O5 1.4451(16) ?
S1 O3 1.4596(15) ?
S1 C3 1.778(2) ?
O1 C1 1.303(3) ?
O1 H1A 0.86(3) ?
O2 C1 1.207(2) ?
C1 C2 1.509(3) ?
C2 C7 1.388(3) ?
C2 C3 1.393(3) ?
C3 C4 1.391(3) ?
C4 C5 1.378(4) ?
C4 H4 0.9300 ?
C5 C6 1.371(4) ?
C5 H5 0.9300 ?
C6 C7 1.387(3) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
N1 C12 1.328(3) yes
N1 C8 1.329(3) yes
N2 C17 1.331(3) yes
N2 C19 1.335(3) yes
N2 H2A 0.83(3) ?
C8 C9 1.379(3) ?
C8 H8 0.9300 ?
C9 C10 1.385(3) ?
C9 H9 0.9300 ?
C10 C11 1.390(3) ?
C10 C13 1.471(3) ?
C11 C12 1.370(3) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C13 C14 1.322(3) ?
C13 H13 0.9300 ?
C14 C15 1.463(3) ?
C14 H14 0.9300 ?
C15 C16 1.393(3) ?
C15 C18 1.394(3) ?
C16 C17 1.368(3) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 C19 1.362(3) ?
C18 H18 0.9300 ?
C19 H19 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
_geom_hbond_publ_flag
N2 H2A O3 . 0.83(3) 2.004(14) 2.798(2) 160(3) yes
O1 H1A N1 2_656 0.86(3) 1.76(3) 2.617(2) 175(3) yes
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 C1 C2 C7 -103.8(3)
O1 C1 C2 C7 73.7(3)
O2 C1 C2 C3 73.5(3)
O1 C1 C2 C3 -109.1(2)
C7 C2 C3 C4 1.4(3)
C1 C2 C3 C4 -175.81(18)
C7 C2 C3 S1 -179.68(16)
C1 C2 C3 S1 3.1(3)
O4 S1 C3 C4 -21.65(19)
O5 S1 C3 C4 -143.06(16)
O3 S1 C3 C4 98.22(17)
O4 S1 C3 C2 159.40(17)
O5 S1 C3 C2 38.00(19)
O3 S1 C3 C2 -80.73(18)
C2 C3 C4 C5 0.9(3)
S1 C3 C4 C5 -178.04(17)
C3 C4 C5 C6 -2.2(4)
C4 C5 C6 C7 1.1(4)
C5 C6 C7 C2 1.2(4)
C3 C2 C7 C6 -2.5(3)
C1 C2 C7 C6 174.8(2)
C12 N1 C8 C9 0.8(4)
N1 C8 C9 C10 -0.6(4)
C8 C9 C10 C11 -0.4(3)
C8 C9 C10 C13 178.9(2)
C9 C10 C11 C12 1.3(4)
C13 C10 C11 C12 -178.1(2)
C8 N1 C12 C11 0.1(4)
C10 C11 C12 N1 -1.1(4)
C9 C10 C13 C14 -13.3(4)
C11 C10 C13 C14 166.0(2)
C10 C13 C14 C15 -178.8(2)
C13 C14 C15 C16 -10.3(4)
C13 C14 C15 C18 169.5(2)
C18 C15 C16 C17 -0.8(3)
C14 C15 C16 C17 179.1(2)
C19 N2 C17 C16 0.7(3)
C15 C16 C17 N2 0.0(3)
C16 C15 C18 C19 0.8(3)
C14 C15 C18 C19 -179.1(2)
C17 N2 C19 C18 -0.7(4)
C15 C18 C19 N2 0.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654069
