data_2202133
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o745
_journal_page_last  o746
_publ_section_title
;
4,5,9,10-Tetrahydro-4,9-methanodithieno[3,2-b:3',2'-f][1,5]diazocine
;
loop_
_publ_author_name
  'Tomoshige Kobayashi'
  'Takashi Moriwaki'
  'Motoo Shiro'
_chemical_formula_moiety  'C11 H10 N2 S2'
_chemical_formula_sum  'C11 H10 N2 S2'
_chemical_formula_iupac  'C11 H10 N2 S2'
_chemical_formula_weight  234.33
_chemical_melting_point  444
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  -x,1/2+y,1/2-z
  -x,-y,-z
  x,1/2-y,1/2+z
_cell_length_a  7.700(2)
_cell_length_b  19.601(5)
_cell_length_c  7.332(2)
_cell_angle_alpha  90
_cell_angle_beta  112.58(2)
_cell_angle_gamma  90
_cell_volume  1021.8(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  93.2
_exptl_crystal_density_diffrn  1.523
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 0.77185(7) 0.69813(3) 0.84722(8) 0.01800(10)
  Uani d . 1.00 . . S
  S6 0.26015(7) 0.46034(2) 0.45873(7) 0.01420(10)
  Uani d . 1.00 . . S
  N4 0.2836(2) 0.62489(8) 0.8129(2) 0.0131(3) Uani d . 1.00 . . N
  N9 0.2245(2) 0.66101(8) 0.4729(2) 0.0128(4) Uani d . 1.00 . . N
  C2 0.7892(3) 0.65890(10)
  1.0647(3) 0.0180(4) Uani d . 1.00 . . C
  C3 0.6215(3) 0.63271(10) 1.0528(3) 0.0157(4) Uani d . 1.00 . . C
  C5 0.2550(3) 0.55097(9) 0.7655(3) 0.0131(4) Uani d . 1.00 . . C
  C7 0.2474(3) 0.49660(10)
  0.2395(3) 0.0157(4) Uani d . 1.00 . . C
  C8 0.2354(3) 0.56620(10)
  0.2430(3) 0.0145(4) Uani d . 1.00 . . C
  C10 0.4067(3) 0.69710(10)
  0.5264(3) 0.0149(4) Uani d . 1.00 . . C
  C11 0.5355(3) 0.67843(10) 0.7346(3) 0.0139(4) Uani d . 1.00 . . C
  C12 0.4761(3) 0.64410(10) 0.8628(3) 0.0131(4) Uani d . 1.00 . . C
  C13 0.2490(3) 0.53886(9) 0.5597(3) 0.0115(4) Uani d . 1.00 . . C
  C14 0.2376(2) 0.59025(10) 0.4287(3) 0.0117(4) Uani d . 1.00 . . C
  C15 0.1636(3) 0.66537(10) 0.6405(3) 0.0142(4) Uani d . 1.00 . . C
  H2 0.9023 0.6560 1.1789 0.0216 Uiso calc . 1.00 . . H
  H3 0.6032 0.6096 1.1579 0.0189 Uiso calc . 1.00 . . H
  H5a 0.3558 0.5257 0.8580 0.0158 Uiso calc . 1.00 . . H
  H5b 0.1397 0.5366 0.7721 0.0158 Uiso calc . 1.00 . . H
  H7 0.2487 0.4713 0.1295 0.0188 Uiso calc . 1.00 . . H
  H8 0.2266 0.5951 0.1357 0.0174 Uiso calc . 1.00 . . H
  H10a 0.4639 0.6842 0.4375 0.0179 Uiso calc . 1.00 . . H
  H10b 0.3856 0.7450 0.5184 0.0179 Uiso calc . 1.00 . . H
  H15a 0.0381 0.6490 0.5986 0.0170 Uiso calc . 1.00 . . H
  H15b 0.1678 0.7118 0.6793 0.0170 Uiso calc . 1.00 . . 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 0.0145(2) 0.0187(2) 0.0187(2) -0.0030(2) 0.0042(2) -0.0010(2)
  S6 0.0157(2) 0.0125(2) 0.0138(2) -0.0002(2) 0.0051(2) -0.0006(2)
  N4 0.0144(7) 0.0132(7) 0.0112(7) 0.0011(6) 0.0044(6) -0.0001(6)
  N9 0.0153(7) 0.0111(7) 0.0120(7) 0.0002(6) 0.0053(6) 0.0010(6)
  C2 0.0170(9) 0.0171(9) 0.0160(9) 0.0033(7) 0.0021(7) -0.0007(7)
  C3 0.0194(9) 0.0145(8) 0.0110(8) 0.0033(7) 0.0033(7) -0.0006(6)
  C5 0.0158(8) 0.0129(8) 0.0114(8) 0.0001(6) 0.0060(7) 0.0025(6)
  C7 0.0161(9) 0.0206(9) 0.0118(8) -0.0003(7) 0.0069(7) -0.0022(7)
  C8 0.0139(8) 0.0191(9) 0.0103(8) 0.0002(7) 0.0047(7) 0.0000(7)
  C10 0.0172(9) 0.0144(8) 0.0127(8) -0.0016(7) 0.0053(7) 0.0014(7)
  C11 0.0138(8) 0.0131(8) 0.0138(8) -0.0006(6) 0.0040(7) -0.0006(7)
  C12 0.0142(8) 0.0119(8) 0.0124(8) 0.0010(6) 0.0043(7) -0.0013(6)
  C13 0.0123(8) 0.0114(7) 0.0105(7) 0.0002(6) 0.0039(6) -0.0002(6)
  C14 0.0113(8) 0.0132(8) 0.0096(7) 0.0013(6) 0.0030(6) 0.0007(6)
  C15 0.0139(8) 0.0149(8) 0.0127(8) 0.0024(7) 0.0039(7) 0.0002(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 C2 . . 1.728(2) yes
  S1 C11 . . 1.729(2) yes
  S6 C7 . . 1.726(2) yes
  S6 C13 . . 1.724(2) yes
  N4 C5 . . 1.486(2) yes
  N4 C12 . . 1.433(2) yes
  N4 C15 . . 1.478(2) yes
  N9 C10 . . 1.483(3) yes
  N9 C14 . . 1.437(2) yes
  N9 C15 . . 1.477(2) yes
  C2 C3 . . 1.362(3) yes
  C2 H2 . . 0.950 no
  C3 C12 . . 1.430(3) yes
  C3 H3 . . 0.950 no
  C5 C13 . . 1.511(3) yes
  C5 H5a . . 0.950 no
  C5 H5b . . 0.950 no
  C7 C8 . . 1.368(3) yes
  C7 H7 . . 0.950 no
  C8 C14 . . 1.434(3) yes
  C8 H8 . . 0.950 no
  C10 C11 . . 1.512(3) yes
  C10 H10a . . 0.950 no
  C10 H10b . . 0.950 no
  C11 C12 . . 1.370(3) yes
  C13 C14 . . 1.371(3) yes
  C15 H15a . . 0.950 no
  C15 H15b . . 0.950 no