#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220975.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_2220975
loop_
_publ_author_name
'Liu, Bing-Xin'
'Yu, Yan-Ping'
'Lin, Yuan-Yuan'
'Du, Mei'
_publ_section_title
;
 2,2'-Diamino-4,4'-bi-1,3-thiazolium bis(3-nitrobenzoate)
;
_journal_coeditor_code           BH2208
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o590
_journal_paper_doi               10.1107/S1600536809005856
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H8 N4 S2 2+, 2C7 H4 N O4 -'
_chemical_formula_moiety         'C6 H8 N4 S2 2+, 2(C7 H4 N O4 -)'
_chemical_formula_sum            'C20 H16 N6 O8 S2'
_chemical_formula_weight         532.51
_chemical_name_systematic
;
2,2'-Diamino-4,4'-bi-1,3-thiazolium bis(3-nitrobenzoate)
;
_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                74.747(2)
_cell_angle_beta                 89.721(2)
_cell_angle_gamma                70.483(2)
_cell_formula_units_Z            1
_cell_length_a                   6.5670(13)
_cell_length_b                   7.4538(15)
_cell_length_c                   12.301(2)
_cell_measurement_reflns_used    1780
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     545.25(18)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2771
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.353
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0505
_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)+(0.0733P)²+0.0511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                1325
_reflns_number_total             1880
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2208.cif
_cod_data_source_block           I
_cod_original_cell_volume        545.26(19)
_cod_database_code               2220975
_cod_database_fobs_code          2220975
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
N N11 0.8309(4) 0.3447(4) 0.4956(2) 0.0409(7) Uani d . 1 . .
H H11A 0.7922 0.3044 0.5705 0.049 Uiso d R 1 . .
N N12 0.6759(5) 0.1415(4) 0.4388(2) 0.0573(8) Uani d . 1 . .
H H12A 0.6577 0.0819 0.3869 0.069 Uiso d R 1 . .
H H12B 0.5903 0.1378 0.4984 0.069 Uiso d R 1 . .
S S11 0.97982(15) 0.25520(13) 0.31830(7) 0.0483(3) Uani d . 1 . .
C C12 1.0789(5) 0.4030(5) 0.3738(2) 0.0398(8) Uani d . 1 . .
H H12 1.1856 0.4523 0.3432 0.048 Uiso calc R 1 . .
C C11 0.9837(5) 0.4382(4) 0.4663(2) 0.0358(7) Uani d . 1 . .
C C13 0.8101(5) 0.2415(5) 0.4254(3) 0.0422(8) Uani d . 1 . .
O O21 0.4454(4) 0.1470(3) 0.62785(19) 0.0555(7) Uani d . 1 . .
O O22 0.6468(4) 0.2977(4) 0.6861(2) 0.0613(7) Uani d . 1 . .
O O23 0.3437(6) 0.3196(5) 1.1652(2) 0.0933(11) Uani d . 1 . .
O O24 0.6375(4) 0.2992(4) 1.0836(2) 0.0616(7) Uani d . 1 . .
N N21 0.4533(6) 0.2964(4) 1.0853(2) 0.0539(8) Uani d . 1 . .
C C21 0.3836(5) 0.2210(4) 0.8031(3) 0.0386(7) Uani d . 1 . .
C C22 0.4661(5) 0.2654(4) 0.8919(3) 0.0395(8) Uani d . 1 . .
H H22 0.5923 0.2963 0.8868 0.047 Uiso calc R 1 . .
C C23 0.3564(5) 0.2627(4) 0.9888(3) 0.0419(8) Uani d . 1 . .
C C24 0.1652(6) 0.2268(5) 0.9973(3) 0.0537(9) Uani d . 1 . .
H H24 0.0916 0.2314 1.0618 0.064 Uiso calc R 1 . .
C C25 0.0836(6) 0.1837(5) 0.9081(3) 0.0561(10) Uani d . 1 . .
H H25 -0.0461 0.1585 0.9124 0.067 Uiso calc R 1 . .
C C26 0.1939(5) 0.1776(5) 0.8120(3) 0.0474(8) Uani d . 1 . .
H H26 0.1403 0.1441 0.7532 0.057 Uiso calc R 1 . .
C C27 0.5007(5) 0.2205(5) 0.6972(3) 0.0429(8) Uani 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
C13 N11 C11 . . 113.5(2) ?
C13 N11 H11A . . 116.6 ?
C11 N11 H11A . . 124.5 ?
C13 N12 H12A . . 120.5 ?
C13 N12 H12B . . 121.6 ?
H12A N12 H12B . . 117.7 ?
C13 S11 C12 . . 90.11(14) ?
C11 C12 S11 . . 111.9(2) ?
C11 C12 H12 . . 124.0 ?
S11 C12 H12 . . 124.0 ?
C12 C11 N11 . . 112.7(3) ?
C12 C11 C11 . 2_766 128.3(3) ?
N11 C11 C11 . 2_766 119.0(3) ?
N12 C13 N11 . . 122.9(3) ?
N12 C13 S11 . . 125.3(2) ?
N11 C13 S11 . . 111.8(2) ?
O24 N21 O23 . . 122.9(3) ?
O24 N21 C23 . . 119.1(3) ?
O23 N21 C23 . . 118.0(3) ?
C22 C21 C26 . . 119.7(3) ?
C22 C21 C27 . . 119.8(3) ?
C26 C21 C27 . . 120.5(3) ?
C21 C22 C23 . . 118.6(3) ?
C21 C22 H22 . . 120.7 ?
C23 C22 H22 . . 120.7 ?
C24 C23 C22 . . 122.3(3) ?
C24 C23 N21 . . 119.6(3) ?
C22 C23 N21 . . 118.1(3) ?
C23 C24 C25 . . 118.6(3) ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
C24 C25 C26 . . 120.4(3) ?
C24 C25 H25 . . 119.8 ?
C26 C25 H25 . . 119.8 ?
C21 C26 C25 . . 120.3(3) ?
C21 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
O21 C27 O22 . . 125.3(3) ?
O21 C27 C21 . . 118.0(3) ?
O22 C27 C21 . . 116.7(3) ?
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
N11 C13 . 1.333(4) ?
N11 C11 . 1.398(4) ?
N11 H11A . 0.9526 ?
N12 C13 . 1.316(4) ?
N12 H12A . 0.8973 ?
N12 H12B . 0.9215 ?
S11 C13 . 1.726(3) ?
S11 C12 . 1.727(3) ?
C12 C11 . 1.339(4) ?
C12 H12 . 0.9300 ?
C11 C11 2_766 1.456(5) ?
O21 C27 . 1.242(4) ?
O22 C27 . 1.263(4) ?
O23 N21 . 1.230(4) ?
O24 N21 . 1.217(4) ?
N21 C23 . 1.466(4) ?
C21 C22 . 1.383(4) ?
C21 C26 . 1.384(4) ?
C21 C27 . 1.510(4) ?
C22 C23 . 1.388(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.367(5) ?
C24 C25 . 1.378(5) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.386(5) ?
C25 H25 . 0.9300 ?
C26 H26 . 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
N11 H11A O22 . 0.95 1.71 2.627(4) 161 yes
N12 H12B O21 . 0.92 1.86 2.770(4) 171 yes
N12 H12A O21 2_656 0.90 2.08 2.830(4) 140 yes
