data_2011481
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1284
_journal_page_last  1286
_publ_section_title
;
Oxythiamine hexafluorophosphate monohydrate, a thiamine antagonist
with the same conformation as thiamine
;
loop_
_publ_author_name
  'Hu, Ning-Hai'
  'Kiyota, Yasuhiro'
  'Aoki, Katsuyuki'
_chemical_name_common  'oxythiamine hexafluorophosphate monohydrate'
_chemical_formula_moiety  'C12 H16 N3 O2 S + , P F6 - , H2 O'
_chemical_formula_sum  'C12 H18 F6 N3 O3 P S'
_chemical_formula_weight  429.32
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.2881(12)
_cell_length_b  11.9318(13)
_cell_length_c  8.8201(7)
_cell_angle_alpha  91.607(8)
_cell_angle_beta  92.081(9)
_cell_angle_gamma  112.925(9)
_cell_volume  898.73(17)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.586
_diffrn_ambient_temperature  293(2)
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  S1  .40635(8)  .86132(6)  .15537(8)  .0537(2) Uani d . 1 . . S
  C2  .4008(3)  .9916(2)  .2232(3)  .0474(5) Uani d . 1 . . C
  N3  .2572(2)  .98628(16)  .2318(2)  .0400(4) Uani d . 1 . . N
  C4  .1420(3)  .8743(2)  .1806(3)  .0425(5) Uani d . 1 . . C
  C5  .2047(3)  .7949(2)  .1374(3)  .0456(5) Uani d . 1 . . C
  C41  -.0269(3)  .8550(3)  .1793(4)  .0615(7) Uani d . 1 . . C
  C51  .1207(4)  .6631(2)  .0881(3)  .0543(6) Uani d . 1 . . C
  C52  .1507(4)  .5807(2)  .2025(3)  .0554(6) Uani d . 1 . . C
  O53  .3078(3)  .59020(19)  .1953(2)  .0616(5) Uani d D 1 . . O
  C35'  .2172(3) 1.0846(2)  .3007(3)  .0463(5) Uani d . 1 . . C
  N1'  .5453(2) 1.34237(19)  .5172(2)  .0487(5) Uani d . 1 . . N
  C2'  .6023(3) 1.4149(2)  .4062(3)  .0434(5) Uani d . 1 . . C
  N3'  .5424(2) 1.38797(16)  .2621(2)  .0425(4) Uani d . 1 . . N
  C4'  .4204(3) 1.27990(19)  .2150(3)  .0417(5) Uani d . 1 . . C
  C5'  .3573(3) 1.20005(19)  .3367(3)  .0410(5) Uani d . 1 . . C
  C6'  .4216(3) 1.2356(2)  .4789(3)  .0473(5) Uani d . 1 . . C
  C2'1  .7412(4) 1.5313(3)  .4354(4)  .0583(7) Uani d D 1 . . C
  O4'1  .3731(2) 1.25819(16)  .0813(2)  .0576(5) Uani d . 1 . . O
  P1  .84895(8) 1.18195(6)  .34821(7)  .04941(19) Uani d . 1 . . P
  F1  .9845(3) 1.2331(3)  .2361(3)  .1013(8) Uani d . 1 . . F
  F2  .9592(3) 1.1428(4)  .4530(3)  .1376(13) Uani d . 1 . . F
  F3  .7109(3) 1.1293(3)  .4597(3)  .1057(9) Uani d . 1 . . F
  F4  .7331(2) 1.2172(2)  .2428(3)  .0892(7) Uani d . 1 . . F
  F5  .7868(4) 1.0553(3)  .2631(5)  .1556(14) Uani d . 1 . . F
  F6  .9051(4) 1.3075(3)  .4328(5)  .1571(15) Uani d . 1 . . F
  OW  .3090(2)  .44654(16)  -.0501(2)  .0521(4) Uani d . 1 . . O
  H2  .491(3) 1.057(3)  .260(3)  .051(7) Uiso d . 1 . . H
  H41A  -.091(5)  .783(4)  .130(5)  .095(13) Uiso d . 1 . . H
  H41B  -.042(5)  .914(4)  .124(5)  .107(15) Uiso d . 1 . . H
  H41C  -.064(6)  .858(4)  .286(6)  .125(17) Uiso d . 1 . . H
  H51A  .008(4)  .649(3)  .068(4)  .072(10) Uiso d . 1 . . H
  H51B  .154(4)  .649(3)  .002(4)  .062(9) Uiso d . 1 . . H
  H52A  .082(4)  .497(3)  .179(3)  .060(8) Uiso d . 1 . . H
  H52B  .130(3)  .597(3)  .309(4)  .055(8) Uiso d . 1 . . H
  H53  .359(5)  .608(4)  .279(3)  .113(16) Uiso d D 1 . . H
  H351  .145(3) 1.102(3)  .225(3)  .053(7) Uiso d . 1 . . H
  H352  .162(4) 1.052(3)  .395(4)  .067(9) Uiso d . 1 . . H
  H3'  .585(3) 1.441(3)  .194(3)  .048(7) Uiso d . 1 . . H
  H6'  .376(3) 1.178(3)  .569(3)  .055(8) Uiso d . 1 . . H
  H2'1  .735(5) 1.592(4)  .372(5)  .084(11) Uiso d . 1 . . H
  H2'2  .741(5) 1.557(4)  .534(6)  .115(16) Uiso d . 1 . . H
  H2'3  .819(3) 1.526(4)  .407(5)  .097(15) Uiso d D 1 . . H
  HW1  .3056  .4959  .0472  .060 Uiso d . 1 . . H
  HW2  .3400  .3893  -.0254  .060 Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  S1  .0477(3)  .0420(3)  .0677(4)  .0144(3)  .0025(3)  -.0062(3)
  C2  .0390(11)  .0346(10)  .0611(14)  .0070(9)  -.0016(10)  -.0008(10)
  N3  .0389(9)  .0315(8)  .0444(10)  .0084(7)  -.0035(7)  .0030(7)
  C4  .0411(11)  .0370(10)  .0403(11)  .0062(9)  -.0077(8)  .0028(8)
  C5  .0495(12)  .0387(11)  .0401(11)  .0092(9)  -.0081(9)  -.0020(9)
  C41  .0410(13)  .0512(15)  .082(2)  .0091(11)  -.0146(13)  -.0047(14)
  C51  .0619(16)  .0415(12)  .0495(14)  .0118(11)  -.0150(12)  -.0116(10)
  C52  .0651(16)  .0377(12)  .0509(14)  .0073(11)  -.0026(12)  -.0055(10)
  O53  .0734(13)  .0608(11)  .0493(10)  .0266(10)  -.0097(9)  -.0098(9)
  C35'  .0409(11)  .0353(10)  .0600(14)  .0123(9)  .0006(10)  .0009(10)
  N1'  .0517(11)  .0451(10)  .0426(10)  .0127(9)  -.0052(8)  -.0010(8)
  C2'  .0443(11)  .0357(10)  .0488(12)  .0149(9)  -.0035(9)  -.0028(9)
  N3'  .0479(10)  .0311(9)  .0439(10)  .0106(8)  -.0005(8)  .0033(8)
  C4'  .0466(12)  .0314(10)  .0448(11)  .0135(9)  -.0038(9)  -.0007(8)
  C5'  .0407(11)  .0315(10)  .0490(12)  .0123(8)  -.0009(9)  .0026(8)
  C6'  .0491(13)  .0427(11)  .0465(12)  .0137(10)  .0016(10)  .0051(9)
  C2'1  .0519(15)  .0437(13)  .0664(18)  .0058(12)  -.0071(13)  -.0032(12)
  O4'1  .0749(12)  .0423(9)  .0457(9)  .0137(8)  -.0106(8)  -.0007(7)
  P1  .0449(3)  .0563(4)  .0490(4)  .0214(3)  .0033(3)  .0073(3)
  F1  .0755(13)  .142(2)  .1048(17)  .0558(14)  .0417(12)  .0579(15)
  F2  .1020(18)  .255(4)  .1028(18)  .113(2)  .0262(14)  .088(2)
  F3  .0731(13)  .173(3)  .0805(14)  .0529(15)  .0292(11)  .0524(15)
  F4  .0659(11)  .1194(17)  .0904(14)  .0425(12)  .0035(10)  .0423(13)
  F5  .168(3)  .0786(17)  .210(4)  .0412(19)  .015(3)  -.048(2)
  F6  .0992(19)  .128(2)  .211(4)  .0171(17)  -.011(2)  -.097(2)
  OW  .0600(10)  .0457(9)  .0459(9)  .0158(8)  -.0018(8)  .0044(7)
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 C2 . 1.670(2) yes
  S1 C5 . 1.725(2) yes
  C2 N3 . 1.316(3) yes
  C2 H2 .  .94(3) ?
  N3 C4 . 1.397(3) yes
  N3 C35' . 1.482(3) yes
  C4 C5 . 1.345(4) yes
  C4 C41 . 1.493(4) yes
  C5 C51 . 1.500(3) yes
  C41 H41A .  .91(4) ?
  C41 H41B .  .92(5) ?
  C41 H41C . 1.02(5) ?
  C51 C52 . 1.520(4) yes
  C51 H51A . 1.00(4) ?
  C51 H51B .  .87(3) ?
  C52 O53 . 1.423(4) yes
  C52 H52A .  .96(3) ?
  C52 H52B .  .99(3) ?
  O53 H53 .  .840(19) ?
  C35' C5' . 1.497(3) yes
  C35' H351 . 1.01(3) ?
  C35' H352 . 1.00(3) ?
  N1' C2' . 1.310(3) yes
  N1' C6' . 1.366(3) yes
  C2' N3' . 1.347(3) yes
  C2' C2'1 . 1.490(3) yes
  N3' C4' . 1.384(3) yes
  N3' H3' .  .88(3) ?
  C4' O4'1 . 1.228(3) yes
  C4' C5' . 1.439(3) yes
  C5' C6' . 1.352(3) yes
  C6' H6' . 1.05(3) ?
  C2'1 H2'1 .  .94(4) ?
  C2'1 H2'2 .  .92(5) ?
  C2'1 H2'3 .  .798(19) ?
  P1 F6 . 1.541(3) ?
  P1 F5 . 1.551(3) ?
  P1 F2 . 1.565(2) ?
  P1 F1 . 1.569(2) ?
  P1 F4 . 1.5819(19) ?
  P1 F3 . 1.583(2) ?
  OW HW1 . 1.0359 ?
  OW HW2 .  .8683 ?