#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/14/2201407.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_2201407
loop_
_publ_author_name
'Chan, Kannie Wai Yan'
'Yang, Chi'
'Szeto, Lap'
_publ_section_title
;cyclo-Bis[2-methylsulfanyl-6-([1,3,4]thiadiazol-2-ylsulfanylmethyl)pyridinium]
 diperchlorate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1277
_journal_page_last               o1279
_journal_paper_doi               10.1107/S1600536802019050
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C18 H16 N6 S6 2+, 2Cl O4 2-'
_chemical_formula_moiety         'C18 H16 N6 S6 2+, 2Cl O4 2-'
_chemical_formula_sum            'C18 H16 Cl2 N6 O8 S6'
_chemical_formula_weight         707.69
_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'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 98.79(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.311(3)
_cell_length_b                   14.700(2)
_cell_length_c                   15.205(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    301.2
_cell_measurement_theta_max      14
_cell_measurement_theta_min      2.5
_cell_volume                     2719.4(9)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1992)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      301.2
_diffrn_measured_fraction_theta_full 25
_diffrn_measured_fraction_theta_max 25
_diffrn_measurement_device       'Rigaku AFC-7R'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2629
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0.05
_diffrn_standards_interval_count 250
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       5.8529
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_ref   1.398
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'calc w = 1/[(σ)²(Fo)+(p/2)²(Fo)²] p = 0.016'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0505
_reflns_number_gt                2399
_reflns_number_total             2399
_reflns_threshold_expression     I>0
_cod_data_source_file            ci6171.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 29 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2719.2(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2201407
_cod_database_fobs_code          2201407
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,  +y,1/2-z'
'  -x,  -y,  -z'
'  +x,  -y,1/2+z'
'1/2+x,1/2+y,  +z'
'1/2 -x,1/2+y,1/2-z'
'1/2 -x,1/2-y,  -z'
1/2+x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
Cl1 0.19844(8) -0.38394(7) 0.33487(6) 0.0526(3) Uani ? ?
S1 0.0000 -0.10926(9) 0.2500 0.0590(5) Uani ? ?
S2 0.13640(10) -0.05186(7) 0.42083(7) 0.0577(3) Uani ? ?
S3 -0.05192(8) 0.38241(7) 0.42764(6) 0.0511(3) Uani ? ?
S4 0.0000 0.43897(9) 0.2500 0.0643(5) Uani ? ?
O1 0.1958(3) -0.2868(2) 0.3430(2) 0.0830(10) Uani ? ?
O2 0.1213(3) -0.4248(2) 0.3847(2) 0.0770(10) Uani ? ?
O3 0.3052(3) -0.4153(2) 0.3726(2) 0.0940(10) Uani ? ?
O4 0.1762(3) -0.4092(2) 0.2446(2) 0.0970(10) Uani ? ?
N1 0.0323(2) 0.0578(2) 0.2915(2) 0.0462(9) Uani ? ?
N2 0.0825(2) 0.1636(2) 0.4615(2) 0.0353(8) Uani ? ?
N3 -0.0119(3) 0.2733(2) 0.2932(2) 0.0540(10) Uani ? ?
C1 0.0556(3) -0.0239(2) 0.3201(2) 0.0430(10) Uani ? ?
C2 0.2206(3) 0.0499(2) 0.4376(2) 0.0450(10) Uani ? ?
C3 0.1767(3) 0.1200(2) 0.4936(2) 0.0384(9) Uani ? ?
C4 0.2292(3) 0.1428(2) 0.5771(2) 0.0470(10) Uani ? ?
C5 0.1865(3) 0.2098(3) 0.6251(2) 0.0520(10) Uani ? ?
C6 0.0899(3) 0.2515(2) 0.5908(2) 0.0460(10) Uani ? ?
C7 0.0360(3) 0.2278(2) 0.5080(2) 0.0352(9) Uani ? ?
C8 -0.0704(3) 0.2691(2) 0.4688(2) 0.0450(10) Uani ? ?
C9 -0.0214(3) 0.3548(2) 0.3227(2) 0.0387(10) Uani ? ?
H2A 0.2920 0.0329 0.4657 0.0543 Uani ? ?
H2B 0.2253 0.0759 0.3811 0.0543 Uani ? ?
H2N 0.0511 0.1469 0.4087 0.0787 Uani ? ?
H4 0.2950 0.1124 0.6016 0.0558 Uani ? ?
H5 0.2240 0.2269 0.6819 0.0621 Uani ? ?
H6 0.0599 0.2971 0.6243 0.0552 Uani ? ?
H8A -0.1170 0.2720 0.5131 0.0536 Uani ? ?
H8B -0.1037 0.2321 0.4209 0.0536 Uani ? ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl 0.148 0.159 'International Tables'
O 0.011 0.006 'International Tables'
N 0.006 0.003 'International Tables'
C 0.003 0.002 'International Tables'
H 0.000 0.000 'International Tables'
S 0.125 0.123 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -6 0
-3 -3 2
4 0 -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
O1 Cl1 O2 ? ? 110.2(2) n
O1 Cl1 O3 ? ? 108.5(2) n
O1 Cl1 O4 ? ? 110.1(2) n
O2 Cl1 O3 ? ? 107.2(2) n
O2 Cl1 O4 ? ? 111.0(2) n
O3 Cl1 O4 ? ? 109.7(2) n
C1 S1 C1 ? 2 86.3(2) yes
C1 S2 C2 ? ? 99.6(2) yes
C8 S3 C9 ? ? 99.1(2) yes
C9 S4 C9 2 ? 87.1(2) yes
N1 N1 C1 2 ? 111.9(2) yes
C3 N2 C7 ? ? 123.3(3) yes
C3 N2 H2N ? ? 115.8 n
C7 N2 H2N ? ? 120.8 n
N3 N3 C9 2 ? 111.9(2) yes
S1 C1 S2 ? ? 119.5(2) yes
S1 C1 N1 ? ? 115.0(3) yes
S2 C1 N1 ? ? 125.5(3) yes
S2 C2 C3 ? ? 113.6(2) yes
S2 C2 H2A ? ? 108.4 n
S2 C2 H2B ? ? 108.4 n
C3 C2 H2A ? ? 108.4 n
C3 C2 H2B ? ? 108.4 n
H2A C2 H2B ? ? 109.5 n
N2 C3 C2 ? ? 119.2(3) yes
N2 C3 C4 ? ? 118.4(3) yes
C2 C3 C4 ? ? 122.4(3) yes
C3 C4 C5 ? ? 120.0(3) yes
C3 C4 H4 ? ? 120.0 n
C5 C4 H4 ? ? 120.0 n
C4 C5 C6 ? ? 119.9(3) yes
C4 C5 H5 ? ? 120.0 n
C6 C5 H5 ? ? 120.0 n
C5 C6 C7 ? ? 120.3(3) yes
C5 C6 H6 ? ? 119.8 n
C7 C6 H6 ? ? 119.8 n
N2 C7 C6 ? ? 118.0(3) yes
N2 C7 C8 ? ? 119.4(3) yes
C6 C7 C8 ? ? 122.5(3) yes
S3 C8 C7 ? ? 111.5(2) yes
S3 C8 H8A ? ? 109.0 n
S3 C8 H8B ? ? 109.0 n
C7 C8 H8A ? ? 109.0 n
C7 C8 H8B ? ? 109.0 n
H8A C8 H8B ? ? 109.5 n
S3 C9 S4 ? ? 120.1(2) yes
S3 C9 N3 ? ? 125.3(3) yes
S4 C9 N3 ? ? 114.6(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 O1 ? ? 1.434(3) n
Cl1 O2 ? ? 1.434(3) n
Cl1 O3 ? ? 1.428(3) n
Cl1 O4 ? ? 1.408(3) n
S1 C1 ? ? 1.719(4) yes
S1 C1 ? 2 1.719(4) yes
S2 C1 ? ? 1.743(4) yes
S2 C2 ? ? 1.816(4) yes
S3 C8 ? ? 1.806(4) yes
S3 C9 ? ? 1.742(4) yes
S4 C9 ? ? 1.706(4) yes
S4 C9 ? 2 1.706(4) yes
N1 N1 ? 2 1.384(6) yes
N1 C1 ? ? 1.295(4) yes
N2 C3 ? ? 1.349(4) yes
N2 C7 ? ? 1.357(4) yes
N2 H2N ? ? 0.87 n
N3 N3 ? 2 1.388(6) yes
N3 C9 ? ? 1.292(4) yes
C2 C3 ? ? 1.490(4) yes
C2 H2A ? ? 0.95 n
C2 H2B ? ? 0.95 n
C3 C4 ? ? 1.374(5) yes
C4 C5 ? ? 1.377(5) yes
C4 H4 ? ? 0.95 n
C5 C6 ? ? 1.369(5) yes
C5 H5 ? ? 0.95 n
C6 C7 ? ? 1.375(4) yes
C6 H6 ? ? 0.95 n
C7 C8 ? ? 1.484(5) yes
C8 H8A ? ? 0.95 n
C8 H8B ? ? 0.95 n
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
N2 H2N N1 . 0.87 2.20 2.999(4) 153
N2 H2N N3 . 0.87 2.59 3.097(4) 118
C2 H2B N1 . 0.95 2.57 2.958(4) 105
C8 H8B N3 . 0.95 2.47 2.870(4) 105
C2 H2B O4 6_555 0.95 2.42 3.275(5) 149
C8 H8A O1 3_556 0.95 2.53 3.463(5) 165
C8 H8B O1 5_455 0.95 2.58 3.307(5) 133
C8 H8B O3 5_455 0.95 2.50 3.339(4) 148
