data_2008406
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
1\a,4\a,4a\b,9\b,9a\b,10\b-Hexahydro-9,10-epithioanthracene-1,4-diol
;
loop_
_publ_author_name
  'Bats, Jan W.'
  'Kr\"amer, Norbert H.'
  'Linde, Hermann F.G.'
_chemical_formula_sum  'C14 H14 O2 S'
_chemical_formula_weight  246.31
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y+1/2, z+1/2'
  '-x, -y, -z'
  '-x, y-1/2, -z-1/2'
_cell_length_a  7.3176(6)
_cell_length_b  8.9755(6)
_cell_length_c  17.9090(10)
_cell_angle_alpha  90.00
_cell_angle_beta  93.636(5)
_cell_angle_gamma  90.00
_cell_volume  1173.88(14)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.394
_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
  S 0.28530(5) 0.25110(4) 0.206905(18) 0.0438(2) Uani d . 1 . . S
  O1 -0.10012(15) 0.44931(15) 0.37100(7) 0.0548(4) Uani d . 1 . . O
  O2 0.62467(16) 0.29136(17) 0.43276(8) 0.0604(4) Uani d . 1 . . O
  C1 0.10759(17) 0.28773(16) 0.27281(7) 0.0346(3) Uani d . 1 . . C
  C2 0.19611(17) 0.42131(14) 0.31740(7) 0.0330(3) Uani d . 1 . . C
  C3 0.09300(19) 0.46077(15) 0.38740(8) 0.0402(4) Uani d . 1 . . C
  C4 0.1463(2) 0.36367(16) 0.45304(8) 0.0420(4) Uani d . 1 . . C
  C5 0.3190(2) 0.32463(17) 0.46701(7) 0.0423(4) Uani d . 1 . . C
  C6 0.46409(19) 0.37787(16) 0.41787(8) 0.0426(4) Uani d . 1 . . C
  C7 0.40122(17) 0.37594(14) 0.33384(7) 0.0353(3) Uani d . 1 . . C
  C8 0.42005(19) 0.22126(17) 0.29595(8) 0.0389(4) Uani d . 1 . . C
  C9 0.30301(19) 0.11084(14) 0.33487(7) 0.0369(3) Uani d . 1 . . C
  C10 0.11978(18) 0.15052(14) 0.32191(7) 0.0327(3) Uani d . 1 . . C
  C11 -0.0160(2) 0.07793(15) 0.35804(7) 0.0392(4) Uani d . 1 . . C
  C12 0.0356(2) -0.03949(16) 0.40609(8) 0.0488(4) Uani d . 1 . . C
  C13 0.2174(3) -0.07945(17) 0.41849(9) 0.0545(4) Uani d . 1 . . C
  C14 0.3538(2) -0.00296(17) 0.38365(9) 0.0489(4) Uani d . 1 . . C
  H1 -0.020(3) 0.317(2) 0.2455(10) 0.048(4) Uiso d . 1 . . H
  H2 0.193(2) 0.5069(17) 0.2848(8) 0.031(4) Uiso d . 1 . . H
  H3 0.112(2) 0.566(2) 0.4018(10) 0.045(4) Uiso d . 1 . . H
  H4 0.044(3) 0.337(3) 0.4884(13) 0.073(6) Uiso d . 1 . . H
  H5 0.364(4) 0.261(2) 0.5052(14) 0.063(7) Uiso d . 1 . . H
  H6 0.497(2) 0.4849(19) 0.4311(9) 0.037(4) Uiso d . 1 . . H
  H7 0.488(2) 0.449(2) 0.3064(9) 0.047(5) Uiso d . 1 . . H
  H8 0.542(3) 0.195(2) 0.2882(11) 0.052(5) Uiso d . 1 . . H
  H11 -0.157(3) 0.107(2) 0.3509(11) 0.055(5) Uiso d . 1 . . H
  H12 -0.062(3) -0.092(2) 0.4328(12) 0.062(6) Uiso d . 1 . . H
  H13 0.242(4) -0.149(3) 0.4534(15) 0.081(7) Uiso d . 1 . . H
  H14 0.481(4) -0.026(3) 0.3956(13) 0.074(6) Uiso d . 1 . . H
  H01 -0.143(4) 0.530(4) 0.3531(16) 0.097(9) Uiso d . 1 . . H
  H02 0.718(4) 0.346(3) 0.4161(13) 0.087(7) 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
  S 0.0462(3) 0.0530(3) 0.0328(3) -0.00381(13) 0.0080(2) 0.00008(11)
  O1 0.0356(6) 0.0568(7) 0.0735(8) 0.0127(5) 0.0157(5) 0.0159(5)
  O2 0.0321(6) 0.0779(8) 0.0694(9) -0.0063(6) -0.0104(5) 0.0259(7)
  C1 0.0285(7) 0.0410(7) 0.0340(7) -0.0012(5) 0.0002(5) 0.0047(5)
  C2 0.0295(6) 0.0320(6) 0.0376(7) -0.0009(4) 0.0032(5) 0.0056(5)
  C3 0.0373(7) 0.0348(7) 0.0493(8) 0.0007(5) 0.0098(6) -0.0015(5)
  C4 0.0461(8) 0.0442(7) 0.0365(7) -0.0042(5) 0.0092(5) -0.0071(5)
  C5 0.0455(8) 0.0481(8) 0.0328(7) -0.0085(6) -0.0021(6) -0.0009(5)
  C6 0.0339(7) 0.0481(8) 0.0446(8) -0.0085(5) -0.0071(6) 0.0037(5)
  C7 0.0260(6) 0.0397(7) 0.0404(7) -0.0053(5) 0.0031(5) 0.0043(5)
  C8 0.0292(7) 0.0478(7) 0.0401(8) 0.0051(5) 0.0053(6) 0.0020(5)
  C9 0.0380(8) 0.0345(6) 0.0382(7) 0.0029(5) 0.0027(5) -0.0033(5)
  C10 0.0341(7) 0.0322(6) 0.0316(6) -0.0032(5) 0.0011(5) -0.0026(4)
  C11 0.0406(7) 0.0411(7) 0.0359(7) -0.0103(5) 0.0018(5) -0.0028(5)
  C12 0.0642(10) 0.0433(8) 0.0389(7) -0.0169(7) 0.0043(6) 0.0013(6)
  C13 0.0772(12) 0.0362(7) 0.0492(9) -0.0009(7) -0.0024(8) 0.0090(6)
  C14 0.0518(9) 0.0413(7) 0.0531(8) 0.0121(6) -0.0014(7) 0.0028(6)
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
  S C1 . 1.8403(13) ?
  S C8 . 1.8405(15) ?
  O1 C3 . 1.4287(18) ?
  O1 H01 . 0.84(3) ?
  O2 C6 . 1.4195(19) ?
  O2 H02 . 0.91(3) ?
  C1 C10 . 1.5125(17) ?
  C1 C2 . 1.5586(18) ?
  C1 H1 . 1.058(19) ?
  C2 C3 . 1.5448(18) ?
  C2 C7 . 1.5650(17) ?
  C2 H2 . 0.964(15) ?
  C3 C4 . 1.495(2) ?
  C3 H3 . 0.988(18) ?
  C4 C5 . 1.320(2) ?
  C4 H4 . 1.04(2) ?
  C5 C6 . 1.499(2) ?
  C5 H5 . 0.93(2) ?
  C6 C7 . 1.5455(19) ?
  C6 H6 . 1.015(18) ?
  C7 C8 . 1.5553(19) ?
  C7 H7 . 1.055(18) ?
  C8 C9 . 1.5091(19) ?
  C8 H8 . 0.94(2) ?
  C9 C14 . 1.380(2) ?
  C9 C10 . 1.3925(19) ?
  C10 C11 . 1.3828(18) ?
  C11 C12 . 1.397(2) ?
  C11 H11 . 1.06(2) ?
  C12 C13 . 1.383(3) ?
  C12 H12 . 1.00(2) ?
  C13 C14 . 1.391(3) ?
  C13 H13 . 0.89(3) ?
  C14 H14 . 0.96(3) ?