#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:04:16 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179824 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/20/7012013.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_7012013
loop_
_publ_author_name
'Hu, Ning-Hai'
'Norifusa, Toshio'
'Aoki, Katsuyuki'
_publ_section_title
;
 Anion coordination and molecular assembly in C2-substituted
 thiamine--anion systems: effects of the anion and molecular
 conformation
;
_journal_issue                   3
_journal_name_full               'Dalton Transactions'
_journal_page_first              335
_journal_paper_doi               10.1039/b206765j
_journal_year                    2003
_chemical_compound_source
;
Crystallization from a solution of 2-(α-hydroxypropyl)thiamine
hydrochloride and HgBr2 in methanol and water.
;
_chemical_formula_sum            'C15 H24 Br6 Hg2 N4 O2 S'
_chemical_formula_weight         1205.08
_chemical_name_common            (2-(α-hydroxypropyl)thiamine)(Hg2Br6)
_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                95.61(2)
_cell_angle_beta                 98.67(3)
_cell_angle_gamma                94.53(3)
_cell_formula_units_Z            2
_cell_length_a                   11.049(5)
_cell_length_b                   15.229(4)
_cell_length_c                   8.243(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      14.8
_cell_volume                     1358.4(8)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Rigaku AFC7R diffractometer'
_diffrn_measurement_method       'ω-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '18kW rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6914
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    20.210
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.317
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.946
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.182
_refine_diff_density_min         -2.129
_refine_diff_density_rms         0.262
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         6224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0880P)²+18.3467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1780
_reflns_number_gt                4040
_reflns_number_total             6224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b206765j.txt
_cod_data_source_block           (hpt)(Hg2Br6)(3)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7012013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Hg1 Hg -0.13627(6) 0.90556(4) 0.48162(8) 0.0566(2) Uani 1 1 d . . .
Hg2 Hg 0.64205(6) 0.58590(4) 0.09445(9) 0.0598(2) Uani 1 1 d . . .
Br1 Br 0.05285(13) 0.98453(10) 0.73366(18) 0.0503(3) Uani 1 1 d . . .
Br2 Br -0.05903(15) 0.76038(11) 0.4236(3) 0.0665(5) Uani 1 1 d . . .
Br3 Br -0.33675(13) 0.95688(9) 0.5310(2) 0.0549(4) Uani 1 1 d . . .
Br4 Br 0.53071(16) 0.43406(13) 0.1793(2) 0.0694(5) Uani 1 1 d . . .
Br5 Br 0.58501(18) 0.71862(16) 0.2628(3) 0.0862(6) Uani 1 1 d . . .
Br6 Br 0.86069(13) 0.56654(10) 0.0777(2) 0.0527(4) Uani 1 1 d . . .
S1 S 0.2212(3) 0.62297(18) 0.2075(4) 0.0346(6) Uani 1 1 d . . .
C2 C 0.2525(10) 0.7259(7) 0.3018(14) 0.030(2) Uani 1 1 d . . .
N3 N 0.2396(7) 0.7305(5) 0.4618(10) 0.0231(17) Uani 1 1 d . . .
C4 C 0.1997(9) 0.6482(7) 0.5120(13) 0.025(2) Uani 1 1 d . . .
C5 C 0.1867(9) 0.5823(6) 0.3860(14) 0.026(2) Uani 1 1 d . . .
C21 C 0.2880(10) 0.8033(7) 0.2139(14) 0.030(2) Uani 1 1 d . . .
H2A H 0.3546 0.8418 0.2843 0.036 Uiso 1 1 calc R . .
O21 O 0.3304(10) 0.7677(7) 0.0659(13) 0.059(3) Uani 1 1 d . . .
H2B H 0.3927 0.7429 0.0911 0.071 Uiso 1 1 calc R . .
C22 C 0.1805(11) 0.8569(8) 0.1630(15) 0.036(3) Uani 1 1 d . . .
H22A H 0.1466 0.8765 0.2609 0.044 Uiso 1 1 calc R . .
H22B H 0.2116 0.9095 0.1189 0.044 Uiso 1 1 calc R . .
C23 C 0.0780(13) 0.8081(11) 0.0364(19) 0.056(4) Uani 1 1 d . . .
H23A H 0.1121 0.7796 -0.0531 0.067 Uiso 1 1 calc R . .
H23B H 0.0229 0.8493 -0.0051 0.067 Uiso 1 1 calc R . .
H23C H 0.0337 0.7643 0.0869 0.067 Uiso 1 1 calc R . .
C41 C 0.1749(13) 0.6422(8) 0.6850(16) 0.041(3) Uani 1 1 d . . .
H41A H 0.1261 0.6888 0.7153 0.050 Uiso 1 1 calc R . .
H41B H 0.2514 0.6483 0.7596 0.050 Uiso 1 1 calc R . .
H41C H 0.1312 0.5858 0.6908 0.050 Uiso 1 1 calc R . .
C51 C 0.1524(11) 0.4847(7) 0.3871(16) 0.034(3) Uani 1 1 d . . .
H51A H 0.0977 0.4618 0.2858 0.041 Uiso 1 1 calc R . .
H51B H 0.1092 0.4755 0.4791 0.041 Uiso 1 1 calc R . .
C52 C 0.2664(11) 0.4354(8) 0.4024(18) 0.041(3) Uani 1 1 d . . .
H52A H 0.3214 0.4583 0.3320 0.049 Uiso 1 1 calc R . .
H52B H 0.3088 0.4456 0.5155 0.049 Uiso 1 1 calc R . .
O53 O 0.2369(9) 0.3417(5) 0.3565(13) 0.047(2) Uani 1 1 d . . .
H53 H 0.2157 0.3187 0.4349 0.056 Uiso 1 1 calc R . .
C35' C 0.2657(10) 0.8115(7) 0.5784(14) 0.030(2) Uani 1 1 d . . .
H35A H 0.2058 0.8122 0.6531 0.036 Uiso 1 1 calc R . .
H35B H 0.2580 0.8628 0.5179 0.036 Uiso 1 1 calc R . .
N1' N 0.5902(8) 0.7688(6) 0.7372(13) 0.034(2) Uani 1 1 d . . .
H1' H 0.6417 0.7312 0.7175 0.041 Uiso 1 1 calc R . .
C2' C 0.6225(10) 0.8353(8) 0.8570(15) 0.034(2) Uani 1 1 d . . .
N3' N 0.5469(8) 0.8929(6) 0.8985(12) 0.031(2) Uani 1 1 d . . .
C4' C 0.4328(9) 0.8876(6) 0.8102(12) 0.024(2) Uani 1 1 d . . .
C5' C 0.3924(9) 0.8172(6) 0.6762(13) 0.023(2) Uani 1 1 d . . .
C6' C 0.4771(10) 0.7602(7) 0.6466(14) 0.027(2) Uani 1 1 d . . .
H6' H 0.4564 0.7142 0.5616 0.033 Uiso 1 1 calc R . .
C2'1 C 0.7499(11) 0.8416(10) 0.9529(19) 0.051(4) Uani 1 1 d . . .
H2'1 H 0.7901 0.8996 0.9509 0.061 Uiso 1 1 calc R . .
H2'2 H 0.7956 0.7979 0.9042 0.061 Uiso 1 1 calc R . .
H2'3 H 0.7455 0.8314 1.0651 0.061 Uiso 1 1 calc R . .
N4'1 N 0.3594(9) 0.9477(6) 0.8462(12) 0.034(2) Uani 1 1 d . . .
H4'1 H 0.3842 0.9896 0.9248 0.041 Uiso 1 1 calc R . .
H4'2 H 0.2864 0.9453 0.7911 0.041 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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
Br2 Hg1 Br3 135.24(6) . . ?
Br2 Hg1 Br1 107.34(6) . 2_576 ?
Br3 Hg1 Br1 105.21(5) . 2_576 ?
Br2 Hg1 Br1 99.94(6) . . ?
Br3 Hg1 Br1 110.10(6) . . ?
Br1 Hg1 Br1 89.80(5) 2_576 . ?
Br6 Hg2 Br5 120.47(7) . . ?
Br6 Hg2 Br4 121.33(7) . 2_665 ?
Br5 Hg2 Br4 103.45(7) . 2_665 ?
Br6 Hg2 Br4 109.52(6) . . ?
Br5 Hg2 Br4 109.96(8) . . ?
Br4 Hg2 Br4 86.99(6) 2_665 . ?
Hg1 Br1 Hg1 90.20(5) 2_576 . ?
Hg2 Br4 Hg2 93.01(6) 2_665 . ?
C2 S1 C5 92.1(5) . . ?
N3 C2 C21 125.1(10) . . ?
N3 C2 S1 112.1(8) . . ?
C21 C2 S1 122.8(8) . . ?
C2 N3 C4 113.7(8) . . ?
C2 N3 C35' 124.6(9) . . ?
C4 N3 C35' 121.6(9) . . ?
C5 C4 N3 111.2(9) . . ?
C5 C4 C41 128.1(10) . . ?
N3 C4 C41 120.6(9) . . ?
C4 C5 C51 128.9(11) . . ?
C4 C5 S1 110.9(8) . . ?
C51 C5 S1 120.2(8) . . ?
O21 C21 C2 106.9(9) . . ?
O21 C21 C22 108.1(10) . . ?
C2 C21 C22 112.9(9) . . ?
O21 C21 H2A 109.6 . . ?
C2 C21 H2A 109.6 . . ?
C22 C21 H2A 109.6 . . ?
C21 O21 H2B 109.5 . . ?
C23 C22 C21 115.0(10) . . ?
C23 C22 H22A 108.5 . . ?
C21 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C21 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C5 C51 C52 110.3(9) . . ?
C5 C51 H51A 109.6 . . ?
C52 C51 H51A 109.6 . . ?
C5 C51 H51B 109.6 . . ?
C52 C51 H51B 109.6 . . ?
H51A C51 H51B 108.1 . . ?
O53 C52 C51 111.7(10) . . ?
O53 C52 H52A 109.3 . . ?
C51 C52 H52A 109.3 . . ?
O53 C52 H52B 109.3 . . ?
C51 C52 H52B 109.3 . . ?
H52A C52 H52B 107.9 . . ?
C52 O53 H53 109.5 . . ?
N3 C35' C5' 111.4(8) . . ?
N3 C35' H35A 109.3 . . ?
C5' C35' H35A 109.3 . . ?
N3 C35' H35B 109.3 . . ?
C5' C35' H35B 109.3 . . ?
H35A C35' H35B 108.0 . . ?
C2' N1' C6' 120.2(9) . . ?
C2' N1' H1' 119.9 . . ?
C6' N1' H1' 119.9 . . ?
N3' C2' N1' 123.2(10) . . ?
N3' C2' C2'1 119.0(11) . . ?
N1' C2' C2'1 117.7(10) . . ?
C2' N3' C4' 118.8(9) . . ?
N4'1 C4' N3' 118.9(9) . . ?
N4'1 C4' C5' 120.5(9) . . ?
N3' C4' C5' 120.6(9) . . ?
C6' C5' C4' 115.5(9) . . ?
C6' C5' C35' 123.9(9) . . ?
C4' C5' C35' 120.5(9) . . ?
N1' C6' C5' 121.6(10) . . ?
N1' C6' H6' 119.2 . . ?
C5' C6' H6' 119.2 . . ?
C2' C2'1 H2'1 109.5 . . ?
C2' C2'1 H2'2 109.5 . . ?
H2'1 C2'1 H2'2 109.5 . . ?
C2' C2'1 H2'3 109.5 . . ?
H2'1 C2'1 H2'3 109.5 . . ?
H2'2 C2'1 H2'3 109.5 . . ?
C4' N4'1 H4'1 120.0 . . ?
C4' N4'1 H4'2 120.0 . . ?
H4'1 N4'1 H4'2 120.0 . . ?
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
Hg1 Br2 2.4617(18) . ?
Hg1 Br3 2.4831(18) . ?
Hg1 Br1 2.7622(18) 2_576 ?
Hg1 Br1 2.817(2) . ?
Hg2 Br6 2.4793(18) . ?
Hg2 Br5 2.515(2) . ?
Hg2 Br4 2.703(2) 2_665 ?
Hg2 Br4 2.734(2) . ?
Br1 Hg1 2.7622(18) 2_576 ?
Br4 Hg2 2.703(2) 2_665 ?
S1 C2 1.666(11) . ?
S1 C5 1.733(11) . ?
C2 N3 1.344(14) . ?
C2 C21 1.499(16) . ?
N3 C4 1.416(13) . ?
N3 C35' 1.469(12) . ?
C4 C5 1.354(15) . ?
C4 C41 1.503(16) . ?
C5 C51 1.506(14) . ?
C21 O21 1.444(14) . ?
C21 C22 1.524(16) . ?
C21 H2A 0.9800 . ?
O21 H2B 0.8200 . ?
C22 C23 1.512(19) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C51 C52 1.512(15) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 O53 1.438(14) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
O53 H53 0.8200 . ?
C35' C5' 1.498(14) . ?
C35' H35A 0.9700 . ?
C35' H35B 0.9700 . ?
N1' C2' 1.330(15) . ?
N1' C6' 1.346(14) . ?
N1' H1' 0.8600 . ?
C2' N3' 1.315(14) . ?
C2' C2'1 1.497(16) . ?
N3' C4' 1.349(13) . ?
C4' N4'1 1.312(13) . ?
C4' C5' 1.454(14) . ?
C5' C6' 1.358(14) . ?
C6' H6' 0.9300 . ?
C2'1 H2'1 0.9600 . ?
C2'1 H2'2 0.9600 . ?
C2'1 H2'3 0.9600 . ?
N4'1 H4'1 0.8600 . ?
N4'1 H4'2 0.8600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3 C35' C5' -96.2(12) . . . . ?
N3 C35' C5' C4' -173.8(9) . . . . ?
S1 C5 C51 C52 79.0(12) . . . . ?
C5 C51 C52 O53 -163.2(10) . . . . ?
