#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/78/2017881.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_2017881
loop_
_publ_author_name
'Li, Shu-Qiang'
'Hu, Ning-Hai'
_publ_section_title
;
 Interaction of thiamine with anions in the triclinic form of thiamine
 iodide:
 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
 iodide 1.25-hydrate
;
_journal_coeditor_code           FA3240
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o581
_journal_page_last               o584
_journal_paper_doi               10.1107/S0108270110043325
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H17 N4 O S + , I - , 1.25H2 O'
_chemical_formula_moiety         'C12 H17 N4 O S +, I -, 1.25(H2 O)'
_chemical_formula_sum            'C12 H19.5 I N4 O2.25 S'
_chemical_formula_weight         414.78
_chemical_name_common            'thiamiine iodide'
_chemical_name_systematic
;
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-
1,3-thiazol-3-ium iodide 1.25-hydrate
;
_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                104.9000(10)
_cell_angle_beta                 100.968(2)
_cell_angle_gamma                115.1290(10)
_cell_formula_units_Z            4
_cell_length_a                   11.9437(10)
_cell_length_b                   12.5913(12)
_cell_length_c                   13.8768(13)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.52
_cell_volume                     1715.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9403
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    1.997
_exptl_absorpt_correction_T_max  0.9068
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             826
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.623
_refine_diff_density_min         -0.977
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6271
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0816P)²+2.7224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                5141
_reflns_number_total             6271
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3240.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C12 H19.50 I N4 O2.25 S'
_cod_database_code               2017881
_cod_database_fobs_code          2017881
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
I I1 0.71720(4) 0.46470(4) 0.43520(3) 0.06377(17) Uani d . 1 . .
I I2 0.49286(6) 0.77149(5) 0.11844(3) 0.0793(2) Uani d . 1 . .
S S1 0.3254(2) 0.41301(17) 0.29637(17) 0.0825(6) Uani d . 1 . .
O O11 0.1852(14) 0.1485(13) 0.1563(11) 0.120(5) Uani d PD 0.50 A 1
H H1A 0.2101 0.1360 0.2120 0.144 Uiso d P 0.50 B 1
O O12 0.1357(11) 0.2533(16) 0.0662(11) 0.127(5) Uani d PD 0.50 C 2
H H12 0.0821 0.1789 0.0442 0.153 Uiso d P 0.50 D 2
N N1 0.5361(5) 0.6006(4) 0.3243(4) 0.0502(11) Uani d . 1 . .
N N2 0.7423(6) 0.8898(5) 0.6678(4) 0.0634(13) Uani d . 1 . .
N N3 0.6008(5) 0.9473(4) 0.5783(4) 0.0544(11) Uani d . 1 . .
N N4 0.5181(5) 0.8742(5) 0.3979(4) 0.0629(13) Uani d . 1 . .
H H4A 0.4781 0.9171 0.4050 0.075 Uiso calc R 1 . .
H H4B 0.5098 0.8301 0.3356 0.075 Uiso calc R 1 . .
C C1 0.4464(6) 0.5616(6) 0.3687(5) 0.0588(15) Uani d . 1 . .
H H1 0.4500 0.6112 0.4331 0.071 Uiso calc R 1 . .
C C2 0.5116(6) 0.5101(6) 0.2288(5) 0.0562(14) Uani d . 1 . .
C C3 0.3989(7) 0.4036(7) 0.2004(6) 0.078(2) Uani d . 1 . .
C C4 0.6101(8) 0.5371(7) 0.1731(6) 0.0717(18) Uani d . 1 . .
H H4C 0.5774 0.4657 0.1083 0.086 Uiso calc R 1 . .
H H4D 0.6916 0.5523 0.2179 0.086 Uiso calc R 1 . .
H H4E 0.6246 0.6108 0.1572 0.086 Uiso calc R 1 . .
C C5 0.3410(10) 0.2843(8) 0.1036(8) 0.122(4) Uani d D 1 . .
H H5A 0.2728 0.2845 0.0530 0.146 Uiso calc PR 0.50 E 1
H H5B 0.4096 0.2933 0.0732 0.146 Uiso calc PR 0.50 E 1
H H5C 0.4100 0.2844 0.0763 0.146 Uiso calc PR 0.50 E 2
H H5D 0.3064 0.2116 0.1237 0.146 Uiso calc PR 0.50 E 2
C C61 0.283(2) 0.1551(16) 0.1068(18) 0.138(9) Uani d PD 0.50 A 1
H H6A 0.2425 0.0903 0.0358 0.165 Uiso calc PR 0.50 A 1
H H6B 0.3495 0.1444 0.1484 0.165 Uiso calc PR 0.50 A 1
C C62 0.2346(13) 0.2716(16) 0.0190(10) 0.088(5) Uani d PD 0.50 C 2
H H6C 0.2621 0.3477 0.0032 0.105 Uiso calc PR 0.50 C 2
H H6D 0.2048 0.1993 -0.0455 0.105 Uiso calc PR 0.50 C 2
C C7 0.6571(6) 0.7268(5) 0.3755(5) 0.0528(13) Uani d . 1 . .
H H7A 0.6632 0.7707 0.3269 0.063 Uiso calc R 1 . .
H H7B 0.7331 0.7154 0.3891 0.063 Uiso calc R 1 . .
C C8 0.6753(6) 0.9517(5) 0.6658(5) 0.0549(14) Uani d . 1 . .
C C9 0.5919(6) 0.8759(5) 0.4825(4) 0.0488(12) Uani d . 1 . .
C C10 0.6609(6) 0.8075(5) 0.4774(4) 0.0499(13) Uani d . 1 . .
C C11 0.7328(6) 0.8178(5) 0.5713(5) 0.0575(14) Uani d . 1 . .
H H11 0.7782 0.7732 0.5697 0.069 Uiso calc R 1 . .
C C12 0.6836(8) 1.0319(7) 0.7700(5) 0.0750(19) Uani d . 1 . .
H H12A 0.7393 1.0271 0.8267 0.090 Uiso d . 1 . .
H H12B 0.5968 1.0009 0.7751 0.090 Uiso d . 1 . .
H H12C 0.7187 1.1180 0.7758 0.090 Uiso d . 1 . .
S S2 1.01658(16) 0.41512(19) 0.30887(15) 0.0726(5) Uani d . 1 . .
O O21 1.0241(13) 0.3624(12) 0.0769(10) 0.096(3) Uani d PD 0.50 F 1
H H21 1.0643 0.4401 0.1022 0.115 Uiso calc PR 0.50 F 1
O O22 1.0497(12) 0.5528(12) 0.1665(9) 0.099(4) Uani d PD 0.50 G 2
H H22 1.0839 0.6280 0.2029 0.119 Uiso d P 0.50 H 2
N N5 0.8249(5) 0.2441(4) 0.3255(4) 0.0524(11) Uani d . 1 . .
N N6 0.8830(6) 0.2498(5) 0.6642(5) 0.0723(15) Uani d . 1 . .
N N7 0.9590(5) 0.1186(5) 0.5783(5) 0.0657(14) Uani d . 1 . .
N N8 0.9046(6) 0.0376(6) 0.3984(5) 0.0749(16) Uani d . 1 . .
H H8A 0.9520 0.0029 0.4074 0.090 Uiso calc R 1 . .
H H8B 0.8647 0.0275 0.3354 0.090 Uiso calc R 1 . .
C C13 0.9506(6) 0.3282(6) 0.3766(5) 0.0549(14) Uani d . 1 . .
H H13 0.9974 0.3379 0.4431 0.066 Uiso calc R 1 . .
C C14 0.7743(6) 0.2479(6) 0.2291(5) 0.0665(17) Uani d . 1 . .
C C15 0.8669(7) 0.3354(8) 0.2065(6) 0.079(2) Uani d . 1 . .
C C16 0.6316(7) 0.1645(8) 0.1653(6) 0.090(3) Uani d . 1 . .
H H16A 0.6111 0.1876 0.1063 0.108 Uiso calc R 1 . .
H H16B 0.5805 0.1743 0.2090 0.108 Uiso calc R 1 . .
H H16C 0.6113 0.0777 0.1395 0.108 Uiso calc R 1 . .
C C17 0.8522(10) 0.3704(11) 0.1122(9) 0.139(5) Uani d D 1 . .
H H17A 0.7607 0.3467 0.0830 0.167 Uiso calc PR 0.50 I 1
H H17B 0.9036 0.4621 0.1372 0.167 Uiso calc PR 0.50 I 1
H H17C 0.8812 0.3252 0.0647 0.167 Uiso calc PR 0.50 I 2
H H17D 0.7583 0.3328 0.0775 0.167 Uiso calc PR 0.50 I 2
C C181 0.8894(14) 0.3177(16) 0.0248(11) 0.100(6) Uani d PD 0.50 F 1
H H18A 0.8390 0.2257 -0.0053 0.120 Uiso calc PR 0.50 F 1
H H18B 0.8779 0.3496 -0.0308 0.120 Uiso calc PR 0.50 F 1
C C182 0.9126(14) 0.5010(14) 0.1131(18) 0.129(8) Uani d PD 0.50 G 2
H H18C 0.8961 0.4996 0.0415 0.154 Uiso calc PR 0.50 G 2
H H18D 0.8787 0.5495 0.1512 0.154 Uiso calc PR 0.50 G 2
C C19 0.7412(6) 0.1590(6) 0.3703(5) 0.0570(14) Uani d . 1 . .
H H19A 0.6973 0.0721 0.3200 0.068 Uiso calc R 1 . .
H H19B 0.6741 0.1802 0.3806 0.068 Uiso calc R 1 . .
C C20 0.9517(7) 0.1888(7) 0.6632(6) 0.0695(18) Uani d . 1 . .
C C21 0.8931(6) 0.1073(6) 0.4820(5) 0.0586(15) Uani d . 1 . .
C C22 0.8195(6) 0.1692(6) 0.4747(5) 0.0574(15) Uani d . 1 . .
C C23 0.8182(7) 0.2380(6) 0.5677(5) 0.0626(16) Uani d . 1 . .
H H23 0.7697 0.2793 0.5643 0.075 Uiso calc R 1 . .
C C24 1.0256(8) 0.2015(8) 0.7703(6) 0.085(2) Uani d . 1 . .
H H24A 1.0117 0.2548 0.8244 0.102 Uiso d . 1 . .
H H24B 1.1174 0.2388 0.7802 0.102 Uiso d . 1 . .
H H24C 0.9932 0.1193 0.7738 0.102 Uiso d . 1 . .
O O3 0.8210(8) 0.0114(8) 0.1872(6) 0.138(3) Uani d . 1 . .
H H3A 0.7482 -0.0544 0.1586 0.165 Uiso d R 1 . .
H H3B 0.8671 0.0074 0.1509 0.165 Uiso d R 1 . .
O O41 1.1893(15) 0.6083(13) 0.1754(11) 0.141(6) Uani d P 0.50 J 1
H H41A 1.2025 0.6667 0.2274 0.170 Uiso d PR 0.50 J 1
H H41B 1.2349 0.5771 0.1905 0.170 Uiso d PR 0.50 J 1
O O51 -0.0605(19) 0.0937(18) 0.0465(18) 0.172(8) Uani d P 0.50 K 1
H H51A 0.0023 0.0954 0.0811 0.207 Uiso d P 0.50 L 1
H H51B -0.0417 0.1681 0.0592 0.207 Uiso d P 0.50 M 1
O O52 0.0411(17) 0.0647(16) 0.1534(15) 0.176(9) Uani d P 0.50 N 2
H H52A 0.1009 0.0779 0.2037 0.211 Uiso d PR 0.50 N 2
H H52B 0.0345 0.0106 0.1013 0.211 Uiso d PR 0.50 N 2
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'
I I -0.4742 1.8119 '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
C1 S1 C3 . . 90.9(3) ?
C61 O11 H1A . . 104.4 ?
C62 O12 H12 . . 109.9 ?
C1 N1 C2 . . 114.0(5) ?
C1 N1 C7 . . 122.7(5) ?
C2 N1 C7 . . 123.1(5) ?
C8 N2 C11 . . 115.9(5) ?
C8 N3 C9 . . 118.7(5) ?
C9 N4 H4A . . 120.0 ?
C9 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
N1 C1 S1 . . 112.3(4) ?
N1 C1 H1 . . 123.9 ?
S1 C1 H1 . . 123.9 ?
C3 C2 N1 . . 112.1(5) ?
C3 C2 C4 . . 127.6(6) ?
N1 C2 C4 . . 120.2(6) ?
C2 C3 C5 . . 127.4(7) ?
C2 C3 S1 . . 110.6(5) ?
C5 C3 S1 . . 121.8(6) ?
C2 C4 H4C . . 109.5 ?
C2 C4 H4D . . 109.5 ?
H4C C4 H4D . . 109.5 ?
C2 C4 H4E . . 109.5 ?
H4C C4 H4E . . 109.5 ?
H4D C4 H4E . . 109.5 ?
C62 C5 C3 . . 112.6(10) ?
C61 C5 C3 . . 123.2(12) ?
C61 C5 H5A . . 106.5 ?
C3 C5 H5A . . 106.5 ?
C61 C5 H5B . . 106.5 ?
C3 C5 H5B . . 106.5 ?
H5A C5 H5B . . 106.5 ?
C62 C5 H5C . . 109.1 ?
C3 C5 H5C . . 109.1 ?
C62 C5 H5D . . 109.1 ?
C3 C5 H5D . . 109.1 ?
H5C C5 H5D . . 107.8 ?
O11 C61 C5 . . 104.3(12) ?
O11 C61 H6A . . 110.9 ?
C5 C61 H6A . . 110.9 ?
O11 C61 H6B . . 110.9 ?
C5 C61 H6B . . 110.9 ?
H6A C61 H6B . . 108.9 ?
O12 C62 C5 . . 101.4(10) ?
O12 C62 H6C . . 111.5 ?
C5 C62 H6C . . 111.5 ?
O12 C62 H6D . . 111.5 ?
C5 C62 H6D . . 111.5 ?
H6C C62 H6D . . 109.3 ?
N1 C7 C10 . . 113.2(5) ?
N1 C7 H7A . . 108.9 ?
C10 C7 H7A . . 108.9 ?
N1 C7 H7B . . 108.9 ?
C10 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.7 ?
N3 C8 N2 . . 125.3(5) ?
N3 C8 C12 . . 117.3(6) ?
N2 C8 C12 . . 117.4(6) ?
N4 C9 N3 . . 117.0(5) ?
N4 C9 C10 . . 123.3(5) ?
N3 C9 C10 . . 119.6(5) ?
C11 C10 C9 . . 116.8(5) ?
C11 C10 C7 . . 119.9(5) ?
C9 C10 C7 . . 123.3(5) ?
C10 C11 N2 . . 123.7(6) ?
C10 C11 H11 . . 118.2 ?
N2 C11 H11 . . 118.2 ?
C8 C12 H12A . . 109.6 ?
C8 C12 H12B . . 109.3 ?
H12A C12 H12B . . 109.0 ?
C8 C12 H12C . . 109.9 ?
H12A C12 H12C . . 109.7 ?
H12B C12 H12C . . 109.4 ?
C13 S2 C15 . . 90.9(3) ?
C182 O22 H22 . . 110.5 ?
C13 N5 C14 . . 114.2(5) ?
C13 N5 C19 . . 123.5(5) ?
C14 N5 C19 . . 122.2(5) ?
C20 N6 C23 . . 114.9(6) ?
C20 N7 C21 . . 118.0(6) ?
C21 N8 H8A . . 120.0 ?
C21 N8 H8B . . 120.0 ?
H8A N8 H8B . . 120.0 ?
N5 C13 S2 . . 112.5(4) ?
N5 C13 H13 . . 123.7 ?
S2 C13 H13 . . 123.7 ?
C15 C14 N5 . . 111.9(6) ?
C15 C14 C16 . . 127.6(6) ?
N5 C14 C16 . . 120.5(6) ?
C14 C15 C17 . . 128.6(7) ?
C14 C15 S2 . . 110.5(5) ?
C17 C15 S2 . . 120.8(6) ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C181 C17 C15 . . 119.3(11) ?
C182 C17 C15 . . 126.1(12) ?
C181 C17 H17A . . 107.5 ?
C15 C17 H17A . . 107.5 ?
C181 C17 H17B . . 107.5 ?
C15 C17 H17B . . 107.5 ?
H17A C17 H17B . . 107.0 ?
C182 C17 H17C . . 105.8 ?
C15 C17 H17C . . 105.8 ?
C182 C17 H17D . . 105.8 ?
C15 C17 H17D . . 105.8 ?
H17C C17 H17D . . 106.2 ?
O21 C181 C17 . . 101.7(11) ?
O21 C181 H18A . . 111.4 ?
C17 C181 H18A . . 111.4 ?
O21 C181 H18B . . 111.4 ?
C17 C181 H18B . . 111.4 ?
H18A C181 H18B . . 109.3 ?
O22 C182 C17 . . 103.6(11) ?
O22 C182 H18C . . 111.1 ?
C17 C182 H18C . . 111.1 ?
O22 C182 H18D . . 111.0 ?
C17 C182 H18D . . 111.0 ?
H18C C182 H18D . . 109.0 ?
N5 C19 C22 . . 112.4(5) ?
N5 C19 H19A . . 109.1 ?
C22 C19 H19A . . 109.1 ?
N5 C19 H19B . . 109.1 ?
C22 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.9 ?
N7 C20 N6 . . 126.4(6) ?
N7 C20 C24 . . 117.8(7) ?
N6 C20 C24 . . 115.7(7) ?
N8 C21 N7 . . 116.3(6) ?
N8 C21 C22 . . 123.8(6) ?
N7 C21 C22 . . 119.9(6) ?
C23 C22 C21 . . 116.9(6) ?
C23 C22 C19 . . 120.1(6) ?
C21 C22 C19 . . 123.0(6) ?
N6 C23 C22 . . 123.9(6) ?
N6 C23 H23 . . 118.1 ?
C22 C23 H23 . . 118.1 ?
C20 C24 H24A . . 108.9 ?
C20 C24 H24B . . 109.4 ?
H24A C24 H24B . . 109.6 ?
C20 C24 H24C . . 109.3 ?
H24A C24 H24C . . 109.6 ?
H24B C24 H24C . . 110.0 ?
H3A O3 H3B . . 108.4 ?
H41A O41 H41B . . 111.1 ?
H51A O51 H51B . . 106.7 ?
H52A O52 H52B . . 107.2 ?
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
S1 C1 . 1.668(6) ?
S1 C3 . 1.736(7) ?
O11 C61 . 1.446(10) ?
O11 H1A . 0.8522 ?
O11 H52A . 1.4254 ?
O12 C62 . 1.421(9) ?
O12 H12 . 0.8061 ?
N1 C1 . 1.315(7) ?
N1 C2 . 1.390(7) ?
N1 C7 . 1.482(7) ?
N2 C8 . 1.335(8) ?
N2 C11 . 1.362(8) ?
N3 C8 . 1.335(8) ?
N3 C9 . 1.356(7) ?
N4 C9 . 1.316(8) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
C1 H1 . 0.9300 ?
C2 C3 . 1.326(9) ?
C2 C4 . 1.497(8) ?
C3 C5 . 1.504(9) ?
C4 H4C . 0.9600 ?
C4 H4D . 0.9600 ?
C4 H4E . 0.9600 ?
C5 C62 . 1.478(9) ?
C5 C61 . 1.491(10) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C5 H5C . 0.9700 ?
C5 H5D . 0.9700 ?
C61 H6A . 0.9700 ?
C61 H6B . 0.9700 ?
C62 H6C . 0.9700 ?
C62 H6D . 0.9700 ?
C7 C10 . 1.493(7) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C12 . 1.493(8) ?
C9 C10 . 1.421(8) ?
C10 C11 . 1.359(9) ?
C11 H11 . 0.9300 ?
C12 H12A . 0.9608 ?
C12 H12B . 0.9647 ?
C12 H12C . 0.9564 ?
S2 C13 . 1.668(6) ?
S2 C15 . 1.731(7) ?
O21 C181 . 1.416(9) ?
O21 H21 . 0.8200 ?
O22 C182 . 1.428(10) ?
O22 H22 . 0.8164 ?
N5 C13 . 1.318(7) ?
N5 C14 . 1.381(8) ?
N5 C19 . 1.484(7) ?
N6 C20 . 1.340(10) ?
N6 C23 . 1.349(9) ?
N7 C20 . 1.322(9) ?
N7 C21 . 1.353(8) ?
N8 C21 . 1.332(9) ?
N8 H8A . 0.8600 ?
N8 H8B . 0.8600 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.345(9) ?
C14 C16 . 1.490(9) ?
C15 C17 . 1.487(10) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C181 . 1.467(9) ?
C17 C182 . 1.484(10) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 H17C . 0.9700 ?
C17 H17D . 0.9700 ?
C181 H18A . 0.9700 ?
C181 H18B . 0.9700 ?
C182 H18C . 0.9700 ?
C182 H18D . 0.9700 ?
C19 C22 . 1.509(8) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C24 . 1.507(10) ?
C21 C22 . 1.406(9) ?
C22 C23 . 1.363(9) ?
C23 H23 . 0.9300 ?
C24 H24A . 0.9616 ?
C24 H24B . 0.9563 ?
C24 H24C . 0.9570 ?
O3 H3A . 0.8296 ?
O3 H3B . 0.8237 ?
O41 H22 . 1.4804 ?
O41 H41A . 0.8194 ?
O41 H41B . 0.8221 ?
O51 H51A . 0.7978 ?
O51 H51B . 0.8249 ?
O52 H51A . 1.2440 ?
O52 H52A . 0.8216 ?
O52 H52B . 0.8206 ?
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
C1 H1 I1 2_666 0.93 2.98 3.643(6) 129 y
C13 H13 I1 2_766 0.93 3.02 3.623(6) 124 y
N4 H4A N3 2_676 0.86 2.26 3.112(7) 172 y
N4 H4B I2 . 0.86 2.86 3.667(5) 158 y
N8 H8A N7 2_756 0.86 2.23 3.079(8) 170 y
N8 H8B O3 . 0.86 1.96 2.793(9) 164 y
O11 H1A N2 2_666 0.85 1.81 2.665(15) 178 y
O12 H12 O52 . 0.81 2.33 2.85(2) 123 y
O21 H21 O41 . 0.82 1.84 2.637(18) 165 y
O22 H22 N6 2_766 0.82 1.92 2.632(14) 146 y
O3 H3A I2 1_545 0.83 2.73 3.526(9) 161 y
O3 H3B O51 1_655 0.82 2.12 2.78(2) 137 y
O3 H3B O52 1_655 0.82 1.88 2.59(2) 144 y
O41 H41A N6 2_766 0.82 2.26 2.982(16) 148 y
O51 H51A O11 . 0.80 1.96 2.73(3) 162 y
O51 H51B O21 1_455 0.82 2.16 2.97(2) 172 y
O52 H52A N2 2_666 0.82 2.14 2.957(16) 179 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 S1 . . . . -0.8(7) ?
C7 N1 C1 S1 . . . . -176.8(4) ?
C3 S1 C1 N1 . . . . -0.6(6) ?
C1 N1 C2 C3 . . . . 2.3(9) ?
C7 N1 C2 C3 . . . . 178.2(6) ?
C1 N1 C2 C4 . . . . -175.3(6) ?
C7 N1 C2 C4 . . . . 0.7(9) ?
N1 C2 C3 C5 . . . . -178.8(9) ?
C4 C2 C3 C5 . . . . -1.5(15) ?
N1 C2 C3 S1 . . . . -2.6(8) ?
C4 C2 C3 S1 . . . . 174.7(6) ?
C1 S1 C3 C2 . . . . 1.8(7) ?
C1 S1 C3 C5 . . . . 178.3(9) ?
C2 C3 C5 C62 . . . . -102.0(12) ?
S1 C3 C5 C62 . . . . 82.2(11) ?
C2 C3 C5 C61 . . . . 134.8(13) ?
S1 C3 C5 C61 . . . . -41.0(16) ?
C3 C5 C61 O11 . . . . 55(2) ?
C3 C5 C62 O12 . . . . -67.5(14) ?
C1 N1 C7 C10 . . . . -4.4(8) ?
C2 N1 C7 C10 . . . . 179.9(5) ?
C9 N3 C8 N2 . . . . -0.9(9) ?
C9 N3 C8 C12 . . . . 179.6(5) ?
C11 N2 C8 N3 . . . . 0.6(9) ?
C11 N2 C8 C12 . . . . -179.8(6) ?
C8 N3 C9 N4 . . . . -179.7(5) ?
C8 N3 C9 C10 . . . . 0.4(8) ?
N4 C9 C10 C11 . . . . -179.7(6) ?
N3 C9 C10 C11 . . . . 0.2(8) ?
N4 C9 C10 C7 . . . . 0.2(9) ?
N3 C9 C10 C7 . . . . -179.9(5) ?
N1 C7 C10 C11 . . . . 100.3(6) ?
N1 C7 C10 C9 . . . . -79.6(7) ?
C9 C10 C11 N2 . . . . -0.5(9) ?
C7 C10 C11 N2 . . . . 179.6(5) ?
C8 N2 C11 C10 . . . . 0.1(9) ?
C14 N5 C13 S2 . . . . -1.5(7) ?
C19 N5 C13 S2 . . . . -176.9(5) ?
C15 S2 C13 N5 . . . . 0.5(6) ?
C13 N5 C14 C15 . . . . 1.9(9) ?
C19 N5 C14 C15 . . . . 177.4(7) ?
C13 N5 C14 C16 . . . . -176.0(7) ?
C19 N5 C14 C16 . . . . -0.5(10) ?
N5 C14 C15 C17 . . . . -178.8(10) ?
C16 C14 C15 C17 . . . . -1.1(17) ?
N5 C14 C15 S2 . . . . -1.4(9) ?
C16 C14 C15 S2 . . . . 176.3(7) ?
C13 S2 C15 C14 . . . . 0.6(7) ?
C13 S2 C15 C17 . . . . 178.2(9) ?
C14 C15 C17 C181 . . . . -99.1(13) ?
S2 C15 C17 C181 . . . . 83.8(12) ?
C14 C15 C17 C182 . . . . 137.6(13) ?
S2 C15 C17 C182 . . . . -39.5(17) ?
C15 C17 C181 O21 . . . . -59.4(15) ?
C15 C17 C182 O22 . . . . 55(2) ?
C13 N5 C19 C22 . . . . -6.6(8) ?
C14 N5 C19 C22 . . . . 178.3(6) ?
C21 N7 C20 N6 . . . . 1.1(10) ?
C21 N7 C20 C24 . . . . -179.8(6) ?
C23 N6 C20 N7 . . . . -1.3(10) ?
C23 N6 C20 C24 . . . . 179.6(6) ?
C20 N7 C21 N8 . . . . 178.8(6) ?
C20 N7 C21 C22 . . . . -0.1(9) ?
N8 C21 C22 C23 . . . . -179.4(6) ?
N7 C21 C22 C23 . . . . -0.5(9) ?
N8 C21 C22 C19 . . . . 2.4(10) ?
N7 C21 C22 C19 . . . . -178.7(5) ?
N5 C19 C22 C23 . . . . 101.7(7) ?
N5 C19 C22 C21 . . . . -80.1(7) ?
C20 N6 C23 C22 . . . . 0.6(9) ?
C21 C22 C23 N6 . . . . 0.3(9) ?
C19 C22 C23 N6 . . . . 178.6(6) ?
