#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/78/2207886.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_2207886
loop_
_publ_author_name
'S. Athimoolam'
'R. K. Rajaram'
_publ_section_title
;
 Thiaminium chloride perchlorate
;
_journal_coeditor_code           SJ6170
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o202
_journal_page_last               o204
_journal_paper_doi               10.1107/S1600536805039358
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H18 N4 O S 2+ , Cl - , Cl O4 -'
_chemical_formula_moiety         'C12 H18 N4 O S 2+ , Cl - , Cl O4 -'
_chemical_formula_sum            'C12 H18 Cl2 N4 O5 S'
_chemical_formula_weight         401.26
_chemical_name_common            'Thiaminium chloride perchlorate'
_chemical_name_systematic
;
Thiaminium chloride perchlorate
;
_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           SHELXL97
_cell_angle_alpha                107.61(3)
_cell_angle_beta                 97.39(3)
_cell_angle_gamma                111.30(3)
_cell_formula_units_Z            2
_cell_length_a                   8.076(3)
_cell_length_b                   10.896(4)
_cell_length_c                   11.594(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.14
_cell_measurement_theta_min      10.20
_cell_volume                     872.7(7)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius MACH3 sealed-tube'
_diffrn_measurement_method       ω/2θ
_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  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3775
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      1.514
_exptl_crystal_density_method
'flotation, using a mixture of xylene and carbon tetrachloride'
_exptl_crystal_description       Block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0416P)²+0.338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                2474
_reflns_number_total             3065
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6170.cif
_cod_data_source_block           I
_cod_database_code               2207886
_cod_database_fobs_code          2207886
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 -0.2519(2) 0.29966(19) 0.58224(16) 0.0407(4) Uani d . 1 N
H1 -0.3676 0.2684 0.5479 0.049 Uiso calc R 1 H
C2 -0.1398(3) 0.4370(2) 0.61258(18) 0.0394(5) Uani d . 1 C
C21 -0.2287(3) 0.5311(3) 0.5953(2) 0.0544(6) Uani d . 1 C
H21A -0.2926 0.5471 0.6587 0.082 Uiso calc R 1 H
H21B -0.3149 0.4862 0.5137 0.082 Uiso calc R 1 H
H21C -0.1359 0.6204 0.6025 0.082 Uiso calc R 1 H
N3 0.0388(2) 0.48969(18) 0.65775(16) 0.0393(4) Uani d . 1 N
C4 0.1130(3) 0.4014(2) 0.67884(18) 0.0354(4) Uani d . 1 C
N41 0.2928(2) 0.45598(19) 0.72131(17) 0.0458(4) Uani d . 1 N
H41A 0.3585 0.5437 0.7346 0.055 Uiso calc R 1 H
H41B 0.3452 0.4041 0.7359 0.055 Uiso calc R 1 H
C5 -0.0021(3) 0.2568(2) 0.65576(17) 0.0337(4) Uani d . 1 C
C6 -0.1851(3) 0.2102(2) 0.60504(18) 0.0370(4) Uani d . 1 C
H6 -0.2649 0.1159 0.5859 0.044 Uiso calc R 1 H
C7 0.0708(3) 0.1562(2) 0.67989(18) 0.0363(4) Uani d . 1 C
H7A -0.0201 0.0594 0.6310 0.044 Uiso calc R 1 H
H7B 0.1814 0.1695 0.6513 0.044 Uiso calc R 1 H
N8 0.1148(2) 0.17545(16) 0.81449(15) 0.0315(3) Uani d . 1 N
C9 0.1692(3) 0.0820(2) 0.85155(19) 0.0365(4) Uani d . 1 C
C91 0.1703(3) -0.0435(2) 0.7539(2) 0.0543(6) Uani d . 1 C
H91A 0.2660 -0.0117 0.7143 0.082 Uiso calc R 1 H
H91B 0.0531 -0.0951 0.6920 0.082 Uiso calc R 1 H
H91C 0.1925 -0.1045 0.7926 0.082 Uiso calc R 1 H
C10 0.2123(3) 0.1217(2) 0.9777(2) 0.0392(5) Uani d . 1 C
S11 0.18620(8) 0.27557(6) 1.04821(5) 0.04205(15) Uani d . 1 S
C12 0.1154(3) 0.2801(2) 0.90818(18) 0.0356(4) Uani d . 1 C
H12 0.0803 0.3493 0.8977 0.043 Uiso calc R 1 H
C13 0.2753(3) 0.0508(2) 1.0559(2) 0.0493(5) Uani d . 1 C
H13A 0.1819 0.0166 1.0975 0.059 Uiso calc R 1 H
H13B 0.2863 -0.0311 1.0006 0.059 Uiso calc R 1 H
C14 0.4567(3) 0.1467(3) 1.1534(2) 0.0521(6) Uani d . 1 C
H14A 0.4910 0.0933 1.1978 0.063 Uiso calc R 1 H
H14B 0.5516 0.1798 1.1124 0.063 Uiso calc R 1 H
O15 0.4466(2) 0.26551(17) 1.24080(17) 0.0539(4) Uani d . 1 O
H15 0.412(4) 0.244(3) 1.298(3) 0.079(10) Uiso d . 1 H
Cl1 0.65996(7) 0.32484(5) 0.88251(5) 0.04121(14) Uani d . 1 Cl
O11 0.8239(2) 0.42779(16) 0.87423(15) 0.0507(4) Uani d . 1 O
O12 0.5156(8) 0.2984(9) 0.7803(5) 0.0760(17) Uani d P 0.63 O
O12' 0.5013(17) 0.3274(16) 0.8330(14) 0.139(7) Uani d P 0.37 O
O13 0.6123(9) 0.3805(7) 0.9943(6) 0.0859(19) Uani d P 0.63 O
O13' 0.6878(18) 0.3501(17) 1.0096(11) 0.142(6) Uani d P 0.37 O
O14 0.6728(14) 0.1959(11) 0.8660(11) 0.096(3) Uani d P 0.63 O
O14' 0.654(3) 0.1938(18) 0.830(2) 0.133(7) Uani d P 0.37 O
Cl2 -0.66976(7) 0.16989(6) 0.45121(5) 0.04722(16) Uani d . 1 Cl
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C6 120.67(18) y
C2 N1 H1 119.7 ?
C6 N1 H1 119.7 ?
N3 C2 N1 122.93(19) ?
N3 C2 C21 120.2(2) ?
N1 C2 C21 116.84(19) ?
C2 C21 H21A 109.5 ?
C2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C2 N3 C4 118.18(18) ?
N41 C4 N3 116.95(18) ?
N41 C4 C5 122.22(19) ?
N3 C4 C5 120.83(18) ?
C4 N41 H41A 120.0 ?
C4 N41 H41B 120.0 ?
H41A N41 H41B 120.0 ?
C6 C5 C4 116.83(18) ?
C6 C5 C7 119.90(18) ?
C4 C5 C7 123.22(17) ?
N1 C6 C5 120.37(19) ?
N1 C6 H6 119.8 ?
C5 C6 H6 119.8 ?
N8 C7 C5 113.38(16) ?
N8 C7 H7A 108.9 ?
C5 C7 H7A 108.9 ?
N8 C7 H7B 108.9 ?
C5 C7 H7B 108.9 ?
H7A C7 H7B 107.7 ?
C12 N8 C9 114.03(16) ?
C12 N8 C7 125.33(16) ?
C9 N8 C7 120.58(16) ?
C10 C9 N8 111.52(17) ?
C10 C9 C91 129.09(19) ?
N8 C9 C91 119.38(19) ?
C9 C91 H91A 109.5 ?
C9 C91 H91B 109.5 ?
H91A C91 H91B 109.5 ?
C9 C91 H91C 109.5 ?
H91A C91 H91C 109.5 ?
H91B C91 H91C 109.5 ?
C9 C10 C13 128.73(19) ?
C9 C10 S11 110.62(15) ?
C13 C10 S11 120.64(17) ?
C12 S11 C10 91.10(10) ?
N8 C12 S11 112.71(14) ?
N8 C12 H12 123.6 ?
S11 C12 H12 123.6 ?
C14 C13 C10 113.82(19) ?
C14 C13 H13A 108.8 ?
C10 C13 H13A 108.8 ?
C14 C13 H13B 108.8 ?
C10 C13 H13B 108.8 ?
H13A C13 H13B 107.7 ?
O15 C14 C13 111.39(19) ?
O15 C14 H14A 109.3 ?
C13 C14 H14A 109.3 ?
O15 C14 H14B 109.3 ?
C13 C14 H14B 109.3 ?
H14A C14 H14B 108.0 ?
C14 O15 H15 109(2) ?
O12' Cl1 O14' 110.4(11) ?
O12' Cl1 O13' 112.2(8) ?
O14' Cl1 O13' 104.5(11) ?
O12' Cl1 O14 121.3(8) ?
O13' Cl1 O14 87.4(8) ?
O12' Cl1 O13 80.0(7) ?
O14' Cl1 O13 127.8(9) ?
O14 Cl1 O13 113.6(6) ?
O12' Cl1 O11 115.4(5) ?
O14' Cl1 O11 109.2(9) ?
O13' Cl1 O11 104.6(6) ?
O14 Cl1 O11 111.3(5) ?
O13 Cl1 O11 111.3(3) ?
O14' Cl1 O12 92.4(10) ?
O13' Cl1 O12 137.7(6) ?
O14 Cl1 O12 107.6(5) ?
O13 Cl1 O12 106.6(3) ?
O11 Cl1 O12 105.9(3) ?
Cl1 O12' O13 51.8(5) ?
Cl1 O13 O12' 48.2(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.341(3) y
N1 C6 1.346(3) y
N1 H1 0.8600 ?
C2 N3 1.306(3) ?
C2 C21 1.493(3) ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
N3 C4 1.367(3) ?
C4 N41 1.310(3) ?
C4 C5 1.426(3) ?
N41 H41A 0.8600 ?
N41 H41B 0.8600 ?
C5 C6 1.355(3) ?
C5 C7 1.496(3) ?
C6 H6 0.9300 ?
C7 N8 1.487(3) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
N8 C12 1.314(2) ?
N8 C9 1.398(2) ?
C9 C10 1.351(3) ?
C9 C91 1.492(3) ?
C91 H91A 0.9600 ?
C91 H91B 0.9600 ?
C91 H91C 0.9600 ?
C10 C13 1.506(3) ?
C10 S11 1.731(2) ?
S11 C12 1.672(2) ?
C12 H12 0.9300 ?
C13 C14 1.505(3) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 O15 1.419(3) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
O15 H15 0.82(3) ?
Cl1 O12' 1.348(12) ?
Cl1 O14' 1.352(15) ?
Cl1 O13' 1.387(11) ?
Cl1 O14 1.404(9) ?
Cl1 O13 1.420(6) ?
Cl1 O11 1.4281(17) ?
Cl1 O12 1.429(6) ?
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
N1 H1 Cl2 . 0.86 2.24 3.100(2) 176
N41 H41A O15 2_667 0.86 2.01 2.854(3) 168
N41 H41B O12 . 0.86 2.19 3.048(8) 172
N41 H41B O12' . 0.86 2.13 2.955(12) 161
O15 H15 Cl2 1_656 0.82(3) 2.24(3) 3.056(2) 174(3)
C12 H12 O11 2_667 0.93 2.78 3.229(3) 111
C12 H12 O13 2_667 0.93 2.84 3.273(7) 110
C6 H6 Cl2 2_456 0.93 2.85 3.687(3) 151
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
_geom_torsion_publ_flag
C6 N1 C2 N3 4.4(3) ?
C6 N1 C2 C21 -174.23(19) ?
N1 C2 N3 C4 -2.3(3) ?
C21 C2 N3 C4 176.23(19) ?
C2 N3 C4 N41 178.41(18) ?
C2 N3 C4 C5 -1.9(3) ?
N41 C4 C5 C6 -176.31(18) ?
N3 C4 C5 C6 4.0(3) ?
N41 C4 C5 C7 1.2(3) ?
N3 C4 C5 C7 -178.53(17) ?
C2 N1 C6 C5 -2.0(3) ?
C4 C5 C6 N1 -2.0(3) ?
C7 C5 C6 N1 -179.59(18) ?
C6 C5 C7 N8 -103.4(2) ?
C4 C5 C7 N8 79.2(2) y
C5 C7 N8 C12 -8.6(3) y
C5 C7 N8 C9 174.45(16) ?
C12 N8 C9 C10 -0.5(2) ?
C7 N8 C9 C10 176.71(17) ?
C12 N8 C9 C91 178.61(19) ?
C7 N8 C9 C91 -4.2(3) ?
N8 C9 C10 C13 179.5(2) ?
C91 C9 C10 C13 0.5(4) ?
N8 C9 C10 S11 -0.5(2) ?
C91 C9 C10 S11 -179.48(19) ?
C9 C10 S11 C12 0.98(16) ?
C13 C10 S11 C12 -178.98(18) ?
C9 N8 C12 S11 1.3(2) ?
C7 N8 C12 S11 -175.79(14) ?
C10 S11 C12 N8 -1.30(16) ?
C9 C10 C13 C14 123.7(3) ?
S11 C10 C13 C14 -56.3(3) y
C10 C13 C14 O15 61.2(3) y
O14' Cl1 O12 O12' 134(2) ?
O13' Cl1 O12 O12' 19(2) ?
O14 Cl1 O12 O12' 125.6(19) ?
O13 Cl1 O12 O12' 3(2) ?
O11 Cl1 O12 O12' -115.2(18) ?
Cl1 O12 O12' O13 -4(2) ?
O14' Cl1 O12' O12 -50(2) ?
O13' Cl1 O12' O12 -166.0(17) ?
O14 Cl1 O12' O12 -65(2) ?
O13 Cl1 O12' O12 -176.7(19) ?
O11 Cl1 O12' O12 74(2) ?
O14' Cl1 O12' O13 126.7(10) ?
O13' Cl1 O12' O13 10.7(10) ?
O14 Cl1 O12' O13 111.7(8) ?
O11 Cl1 O12' O13 -108.9(4) ?
O12 Cl1 O12' O13 176.7(19) ?
O12' Cl1 O13 O13' 162.0(16) ?
O14' Cl1 O13 O13' 53.9(19) ?
O14 Cl1 O13 O13' 42.1(16) ?
O11 Cl1 O13 O13' -84.5(15) ?
O12 Cl1 O13 O13' 160.5(14) ?
O14' Cl1 O13 O12' -108.1(12) ?
O13' Cl1 O13 O12' -162.0(16) ?
O14 Cl1 O13 O12' -119.9(7) ?
O11 Cl1 O13 O12' 113.5(6) ?
O12 Cl1 O13 O12' -1.5(9) ?
O12 O12' O13 O13' -14(4) ?
Cl1 O12' O13 O13' -19.0(17) ?
O12 O12' O13 Cl1 5(3) ?
O12' O13 O13' Cl1 14.9(13) ?
O12' Cl1 O13' O13 -19.1(17) ?
O14' Cl1 O13' O13 -138.7(15) ?
O14 Cl1 O13' O13 -142.0(14) ?
O11 Cl1 O13' O13 106.6(13) ?
O12 Cl1 O13' O13 -28(2) ?
