#------------------------------------------------------------------------------
#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102703.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102703
loop_
_publ_author_name
'Geng-Xu Yang'
'Shi-Zhen Zhang'
'Zi-Liang Wang'
_publ_contact_author
;
  Ziliang Wang     
;
_publ_section_title
;
 Crystal structure of bis(2-aminopyridinium) 2,2'-dithiobis(benzoate)
 dihydrate, [C5H7N2]2[C14H8O4S2] · 2H2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              367
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C14 H8 O4 S2, 2(C5 H7 N2), 2(H2 O)'
_chemical_formula_sum            'C24 H26 N4 O6 S2'
_chemical_formula_weight         530.61
_chemical_name_systematic
; 
2(C₅H₇N₂⁺).(C₁₄H₈O₄S₂²⁻).2(H₂O)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.808(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4290(13)
_cell_length_b                   9.7934(9)
_cell_length_c                   20.331(2)
_cell_measurement_reflns_used    1710
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.96
_cell_volume                     2572.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick,1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick,1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART Apex CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6999
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.9511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0370P)²+1.1019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                1851
_reflns_number_total             2520
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2976.cff
_cod_data_source_block
;
;
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2572.8(4)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8102703
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.04241(4) 0.12501(5) 0.30001(3) 0.05356(18) Uani 1 1 d . . .
O1 O 0.33145(11) 0.10483(16) 0.44974(8) 0.0710(5) Uani 1 1 d . . .
O2 O 0.16068(11) 0.09688(16) 0.42730(8) 0.0702(5) Uani 1 1 d . . .
O1W O 0.49470(14) 0.2359(2) 0.54357(11) 0.0795(5) Uani 1 1 d D . .
H1WA H 0.4511(18) 0.203(3) 0.5096(11) 0.096(10) Uiso 1 1 d D . .
H1WB H 0.458(2) 0.290(3) 0.5579(14) 0.114(13) Uiso 1 1 d D . .
N1 N 0.66096(14) 0.06815(18) 0.44288(9) 0.0560(4) Uani 1 1 d D . .
H1A H 0.6680(15) 0.0113(19) 0.4773(9) 0.059(6) Uiso 1 1 d D . .
N2 N 0.83487(16) 0.1142(2) 0.47828(10) 0.0637(5) Uani 1 1 d D . .
H2A H 0.8900(14) 0.156(2) 0.4743(11) 0.065(7) Uiso 1 1 d D . .
H2B H 0.8415(16) 0.0512(19) 0.5093(9) 0.061(7) Uiso 1 1 d D . .
C1 C 0.74370(16) 0.1380(2) 0.43563(10) 0.0522(5) Uani 1 1 d . . .
C2 C 0.72691(19) 0.2352(2) 0.38259(11) 0.0649(6) Uani 1 1 d . . .
H2 H 0.7818 0.2865 0.3761 0.078 Uiso 1 1 calc R . .
C3 C 0.6301(2) 0.2531(3) 0.34111(12) 0.0762(7) Uani 1 1 d . . .
H3 H 0.6190 0.3172 0.3061 0.091 Uiso 1 1 calc R . .
C4 C 0.5471(2) 0.1773(3) 0.34987(13) 0.0781(7) Uani 1 1 d . . .
H4 H 0.4810 0.1893 0.3208 0.094 Uiso 1 1 calc R . .
C5 C 0.56443(17) 0.0865(3) 0.40112(12) 0.0695(6) Uani 1 1 d . . .
H5 H 0.5097 0.0357 0.4081 0.083 Uiso 1 1 calc R . .
C6 C 0.14275(14) 0.24854(18) 0.30453(9) 0.0446(4) Uani 1 1 d . . .
C7 C 0.23119(14) 0.24370(18) 0.36015(10) 0.0455(4) Uani 1 1 d . . .
C8 C 0.30938(15) 0.3382(2) 0.36324(11) 0.0578(5) Uani 1 1 d . . .
H8 H 0.3688 0.3350 0.3997 0.069 Uiso 1 1 calc R . .
C9 C 0.30104(17) 0.4362(2) 0.31379(12) 0.0659(6) Uani 1 1 d . . .
H9 H 0.3538 0.4996 0.3172 0.079 Uiso 1 1 calc R . .
C10 C 0.21404(18) 0.4400(2) 0.25919(12) 0.0646(6) Uani 1 1 d . . .
H10 H 0.2080 0.5062 0.2255 0.078 Uiso 1 1 calc R . .
C11 C 0.13551(16) 0.3460(2) 0.25418(11) 0.0555(5) Uani 1 1 d . . .
H11 H 0.0775 0.3482 0.2167 0.067 Uiso 1 1 calc R . .
C12 C 0.24240(15) 0.1409(2) 0.41680(10) 0.0514(5) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 S1 104.97(7) . 2 ?
H1WA O1W H1WB 101(3) . . ?
C1 N1 C5 122.8(2) . . ?
C1 N1 H1A 119.8(13) . . ?
C5 N1 H1A 117.4(13) . . ?
C1 N2 H2A 121.2(14) . . ?
C1 N2 H2B 119.8(14) . . ?
H2A N2 H2B 119(2) . . ?
N2 C1 N1 119.1(2) . . ?
N2 C1 C2 123.4(2) . . ?
N1 C1 C2 117.5(2) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 N1 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
N1 C5 H5 119.7 . . ?
C11 C6 C7 119.62(17) . . ?
C11 C6 S1 121.78(14) . . ?
C7 C6 S1 118.59(14) . . ?
C8 C7 C6 118.61(18) . . ?
C8 C7 C12 119.62(17) . . ?
C6 C7 C12 121.76(16) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.42(19) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
O2 C12 O1 124.50(19) . . ?
O2 C12 C7 116.84(17) . . ?
O1 C12 C7 118.66(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7946(19) . ?
S1 S1 2.0424(10) 2 ?
O1 C12 1.252(2) . ?
O2 C12 1.250(2) . ?
O1W H1WA 0.837(17) . ?
O1W H1WB 0.827(17) . ?
N1 C1 1.347(3) . ?
N1 C5 1.354(3) . ?
N1 H1A 0.879(15) . ?
N2 C1 1.314(3) . ?
N2 H2A 0.870(15) . ?
N2 H2B 0.870(15) . ?
C1 C2 1.410(3) . ?
C2 C3 1.354(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C11 1.383(3) . ?
C6 C7 1.400(2) . ?
C7 C8 1.388(3) . ?
C7 C12 1.506(3) . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O2 0.870(15) 1.945(16) 2.810(3) 173(2) 5_656
N2 H2A O1W 0.870(15) 1.988(16) 2.854(3) 173(2) 7_656
N1 H1A O1 0.879(15) 1.867(16) 2.743(2) 174.0(19) 5_656
O1W H1WB O2 0.827(17) 2.032(19) 2.839(3) 165(3) 7_556
O1W H1WA O1 0.837(17) 1.982(18) 2.796(2) 164(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139207267
