#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/53/2205391.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_2205391
loop_
_publ_author_name
'Liu, Bing-Xin'
'Xu, Duan-Jun'
_publ_section_title
;
 2,2'-Diamino-4,4'-bi-1,3-thiazolium (2R,3R)-tartrate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o753
_journal_page_last               o755
_journal_paper_doi               10.1107/S1600536805005313
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H8 N4 S2 2+ , C4 H4 O6 2-'
_chemical_formula_moiety         'C6 H8 N4 S2 2+ , C4 H4 O6 2-'
_chemical_formula_sum            'C10 H12 N4 O6 S2'
_chemical_formula_weight         348.36
_chemical_name_systematic
;
2,2'-Diamino-4,4'-bi-1,3-thiazolium (2R,3R)-tartrate
;
_space_group_IT_number           154
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   11.0122(7)
_cell_length_b                   11.0122(7)
_cell_length_c                   18.8285(14)
_cell_measurement_reflns_used    3278
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.5
_cell_volume                     1977.4(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18080
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details 'Flack (1983), with 1280 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_gt           0.030
_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)+(0.0407P)²+0.5513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.075
_refine_ls_wR_factor_ref         0.076
_reflns_number_gt                2895
_reflns_number_total             3030
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6361.cif
_cod_data_source_block           I
_cod_database_code               2205391
_cod_database_fobs_code          2205391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'
loop_
_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_type_symbol
S1 0.19828(6) -0.07871(5) 0.39358(3) 0.03867(12) Uani d . 1 S
S2 0.09436(6) 0.45087(5) 0.43278(3) 0.04235(13) Uani d . 1 S
N1 0.31206(17) 0.18704(18) 0.39482(8) 0.0321(3) Uani d . 1 N
H1 0.3775 0.2771 0.3944 0.050 Uiso d R 1 H
N2 0.4722(2) 0.1122(2) 0.37104(10) 0.0463(4) Uani d . 1 N
H2A 0.5046 0.0591 0.3737 0.050 Uiso d R 1 H
H2B 0.5417 0.2014 0.3622 0.050 Uiso d R 1 H
N3 -0.02272(17) 0.18381(16) 0.42103(8) 0.0304(3) Uani d . 1 N
H3 -0.0855 0.0956 0.4239 0.050 Uiso d R 1 H
N4 -0.1839(2) 0.2604(2) 0.43696(10) 0.0447(4) Uani d . 1 N
H4A -0.2475 0.1756 0.4413 0.050 Uiso d R 1 H
H4B -0.2084 0.3155 0.4542 0.050 Uiso d R 1 H
C1 0.3440(2) 0.0869(2) 0.38547(10) 0.0340(4) Uani d . 1 C
C2 0.0946(2) -0.0043(2) 0.40895(10) 0.0338(4) Uani d . 1 C
H2 -0.0014 -0.0553 0.4175 0.041 Uiso calc R 1 H
C3 0.17032(19) 0.1364(2) 0.40704(9) 0.0293(4) Uani d . 1 C
C4 -0.0545(2) 0.2844(2) 0.43048(10) 0.0328(4) Uani d . 1 C
C5 0.1990(2) 0.3756(2) 0.42163(11) 0.0394(4) Uani d . 1 C
H5 0.2964 0.4259 0.4197 0.047 Uiso calc R 1 H
C6 0.1211(2) 0.2354(2) 0.41610(9) 0.0301(4) Uani d . 1 C
O1 0.97093(16) 0.61372(17) 0.58530(9) 0.0443(4) Uani d . 1 O
O2 0.92489(16) 0.78120(15) 0.55299(8) 0.0430(3) Uani d . 1 O
O3 0.52424(16) 0.44140(17) 0.42107(9) 0.0464(4) Uani d . 1 O
O4 0.66525(16) 0.40504(17) 0.35003(8) 0.0474(4) Uani d . 1 O
O5 0.72860(16) 0.40769(14) 0.53231(7) 0.0389(3) Uani d . 1 O
H5A 0.7624 0.4069 0.5803 0.050 Uiso d R 1 H
O6 0.89572(15) 0.58660(18) 0.41414(8) 0.0449(4) Uani d . 1 O
H6A 0.8747 0.5461 0.3714 0.050 Uiso d R 1 H
C7 0.8974(2) 0.6547(2) 0.55649(10) 0.0332(4) Uani d . 1 C
C8 0.75943(19) 0.54780(19) 0.52094(10) 0.0306(4) Uani d . 1 C
H8 0.6829 0.5588 0.5404 0.037 Uiso calc R 1 H
C9 0.7704(2) 0.5772(2) 0.44086(10) 0.0330(4) Uani d . 1 C
H9 0.7757 0.6677 0.4334 0.040 Uiso calc R 1 H
C10 0.6418(2) 0.4645(2) 0.40095(10) 0.0348(4) Uani d . 1 C
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
C1 S1 C2 90.00(10) y
C4 S2 C5 89.70(10) y
C1 N1 C3 113.56(17) ?
C1 N1 H1 121.6 ?
C3 N1 H1 124.8 ?
C1 N2 H2A 129.3 ?
C1 N2 H2B 119.9 ?
H2A N2 H2B 110.4 ?
C4 N3 C6 112.81(16) ?
C4 N3 H3 122.0 ?
C6 N3 H3 124.6 ?
C4 N4 H4A 116.4 ?
C4 N4 H4B 126.5 ?
H4A N4 H4B 111.8 ?
N2 C1 N1 123.4(2) ?
N2 C1 S1 124.67(17) ?
N1 C1 S1 111.90(15) ?
C3 C2 S1 111.43(15) ?
C3 C2 H2 124.3 ?
S1 C2 H2 124.3 ?
C2 C3 N1 113.12(17) ?
C2 C3 C6 127.88(18) ?
N1 C3 C6 119.00(17) ?
N4 C4 N3 123.6(2) ?
N4 C4 S2 124.15(17) ?
N3 C4 S2 112.24(14) ?
C6 C5 S2 111.27(15) ?
C6 C5 H5 124.4 ?
S2 C5 H5 124.4 ?
C5 C6 N3 113.98(16) ?
C5 C6 C3 127.51(18) ?
N3 C6 C3 118.50(17) ?
C8 O5 H5A 105.3 ?
C9 O6 H6A 106.4 ?
O1 C7 O2 125.74(19) ?
O1 C7 C8 119.36(17) ?
O2 C7 C8 114.90(16) ?
O5 C8 C7 112.04(15) ?
O5 C8 C9 109.13(15) ?
C7 C8 C9 108.87(15) ?
O5 C8 H8 108.9 ?
C7 C8 H8 108.9 ?
C9 C8 H8 108.9 ?
O6 C9 C10 110.84(16) ?
O6 C9 C8 109.55(15) ?
C10 C9 C8 111.55(16) ?
O6 C9 H9 108.3 ?
C10 C9 H9 108.3 ?
C8 C9 H9 108.3 ?
O3 C10 O4 126.0(2) ?
O3 C10 C9 117.46(18) ?
O4 C10 C9 116.55(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.731(2) y
S1 C2 1.730(2) y
S2 C4 1.745(2) y
S2 C5 1.735(2) y
N1 C1 1.326(3) ?
N1 C3 1.389(2) ?
N1 H1 0.8880 ?
N2 C1 1.324(3) ?
N2 H2A 0.8246 ?
N2 H2B 0.9094 ?
N3 C4 1.330(3) ?
N3 C6 1.392(2) ?
N3 H3 0.8673 ?
N4 C4 1.319(3) ?
N4 H4A 0.8464 ?
N4 H4B 0.8423 ?
C2 C3 1.343(3) ?
C2 H2 0.9300 ?
C3 C6 1.451(3) ?
C5 C6 1.344(3) ?
C5 H5 0.9300 ?
O1 C7 1.233(2) ?
O2 C7 1.270(2) ?
O3 C10 1.247(3) ?
O4 C10 1.259(2) ?
O5 C8 1.421(2) ?
O5 H5A 0.9798 ?
O6 C9 1.423(2) ?
O6 H6A 0.8935 ?
C7 C8 1.534(3) ?
C8 C9 1.534(2) ?
C8 H8 0.9800 ?
C9 C10 1.534(3) ?
C9 H9 0.9800 ?
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
N1 H1 O3 . 0.89 1.79 2.647(2) 161 y
N2 H2A O1 6_546 0.82 2.04 2.819(3) 158 y
N2 H2B O4 . 0.91 1.97 2.867(3) 169 y
N3 H3 O2 6_446 0.87 1.77 2.622(2) 169 y
N4 H4A O1 6_446 0.85 2.05 2.864(2) 160 y
N4 H4B O5 1_455 0.84 2.09 2.889(3) 157 y
O5 H5A O4 3_665 0.98 2.06 2.975(2) 154 y
O6 H6A O4 . 0.89 2.08 2.612(2) 118 y
C2 H2 O2 6_446 0.93 2.36 3.216(3) 153 y
C5 H5 O3 . 0.93 2.43 3.280(3) 152 y
C8 H8 O3 6_556 0.98 2.59 3.552(3) 165 y
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
C3 N1 C1 N2 177.93(18)
C3 N1 C1 S1 -1.5(2)
C2 S1 C1 N2 -178.76(18)
C2 S1 C1 N1 0.65(15)
C1 S1 C2 C3 0.36(15)
S1 C2 C3 N1 -1.3(2)
S1 C2 C3 C6 178.81(14)
C1 N1 C3 C2 1.8(2)
C1 N1 C3 C6 -178.26(15)
C6 N3 C4 N4 -179.65(18)
C6 N3 C4 S2 0.7(2)
C5 S2 C4 N4 179.55(19)
C5 S2 C4 N3 -0.79(16)
C4 S2 C5 C6 0.68(16)
S2 C5 C6 N3 -0.4(2)
S2 C5 C6 C3 -179.37(14)
C4 N3 C6 C5 -0.2(2)
C4 N3 C6 C3 178.86(15)
C2 C3 C6 C5 172.3(2)
N1 C3 C6 C5 -7.6(3)
C2 C3 C6 N3 -6.6(3)
N1 C3 C6 N3 173.50(16)
O1 C7 C8 O5 5.4(2)
O2 C7 C8 O5 -174.63(17)
O1 C7 C8 C9 -115.40(19)
O2 C7 C8 C9 64.6(2)
O5 C8 C9 O6 -71.6(2)
C7 C8 C9 O6 50.9(2)
O5 C8 C9 C10 51.5(2)
C7 C8 C9 C10 174.05(15)
O6 C9 C10 O3 177.16(18)
C8 C9 C10 O3 54.8(2)
O6 C9 C10 O4 -3.7(2)
C8 C9 C10 O4 -126.08(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173541
