#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008815.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_2008815
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1357
_journal_page_last  1360
_publ_section_title
;
 2,11-Dithia[3.3.1]paracyclophane, (I), and 2,11-dithia[3.3.2]paracyclophane,
  (II)
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  'Itoh*, Kuniaki'
  'Nishikawa, Kazuyoshi'
  'Hashimoto, Masao'
  'Yamada, Hiroaki'
_chemical_name_common  2,11-dithia[3.3.1]paracyclophane
_chemical_formula_moiety  'C23 H22 S2'
_chemical_formula_sum  'C23 H22 S2'
_chemical_formula_weight  362.55
_chemical_melting_point  492.3-493.2
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '1/2-x,1/2+y,1/2-z'
  '  -x,  -y,  -z'
  '1/2+x,1/2-y,1/2+z'
_cell_length_a  12.565(2)
_cell_length_b  10.7840(10)
_cell_length_c  14.5120(10)
_cell_angle_alpha  90
_cell_angle_beta  105.716(8)
_cell_angle_gamma  90
_cell_volume  1892.8(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  296.2
_exptl_crystal_density_diffrn  1.272
_exptl_crystal_density_meas  1.23
_diffrn_ambient_temperature  296.2
_refine_ls_R_factor_obs  0.0613
_refine_ls_wR_factor_obs  0.0535
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  S1 0.23288(8) 0.35550(7) 0.10647(6) 0.0776(3) Uani d . . 1.00
  S2 0.38706(7) -0.34955(7) 0.01606(7) 0.0739(3) Uani d . . 1.00
  C1 0.1740(2) 0.2036(3) 0.1112(2) 0.0679(10) Uani d . . 1.00
  C2 0.2240(2) 0.1000(2) 0.0676(2) 0.0479(7) Uani d . . 1.00
  C3 0.3358(2) 0.0718(2) 0.1003(2) 0.0484(7) Uani d . . 1.00
  C4 0.3804(2) -0.0255(2) 0.0627(2) 0.0490(7) Uani d . . 1.00
  C5 0.3156(2) -0.0999(2) -0.0083(2) 0.0488(8) Uani d . . 1.00
  C6 0.2046(2) -0.0716(3) -0.0416(2) 0.0613(9) Uani d . . 1.00
  C7 0.1603(2) 0.0277(3) -0.0039(2) 0.0619(9) Uani d . . 1.00
  C8 0.3649(2) -0.2052(3) -0.0518(2) 0.0662(9) Uani d . . 1.00
  C9 0.5336(3) -0.3448(3) 0.0762(2) 0.0750(10)
  Uani d . . 1.00
  C10 0.5682(2) -0.2517(2) 0.1560(2) 0.0555(8) Uani d . . 1.00
  C11 0.5184(2) -0.2490(3) 0.2306(2) 0.0654(10) Uani d . . 1.00
  C12 0.5448(2) -0.1595(3) 0.3001(2) 0.0637(9) Uani d . . 1.00
  C13 0.6231(2) -0.0688(3) 0.2998(2) 0.0521(8) Uani d . . 1.00
  C14 0.6749(2) -0.0742(3) 0.2273(2) 0.0556(8) Uani d . . 1.00
  C15 0.6475(2) -0.1643(3) 0.1562(2) 0.0546(8) Uani d . . 1.00
  C16 0.6443(2) 0.0332(3) 0.3736(2) 0.0683(9) Uani d . . 1.00
  C17 0.5584(2) 0.1346(3) 0.3470(2) 0.0545(8) Uani d . . 1.00
  C18 0.4621(2) 0.1309(3) 0.3757(2) 0.0592(9) Uani d . . 1.00
  C19 0.3783(2) 0.2168(3) 0.3422(2) 0.0626(9) Uani d . . 1.00
  C20 0.3885(3) 0.3090(3) 0.2793(2) 0.0626(9) Uani d . . 1.00
  C21 0.4872(3) 0.3177(3) 0.2543(2) 0.0690(10)
  Uani d . . 1.00
  C22 0.5702(2) 0.2325(3) 0.2874(2) 0.0643(10) Uani d . . 1.00
  C23 0.2935(3) 0.3924(3) 0.2326(2) 0.0870(10)
  Uani d . . 1.00
  H1 0.1787 0.1896 0.1725 0.0714 Uiso calc . . 1.00
  H2 0.0948 0.2094 0.0731 0.0811 Uiso calc . . 1.00
  H3 0.3815 0.1190 0.1493 0.0538 Uiso calc . . 1.00
  H4 0.4572 -0.0464 0.0873 0.0511 Uiso calc . . 1.00
  H5 0.1568 -0.1194 -0.0925 0.0885 Uiso calc . . 1.00
  H6 0.0897 0.0437 -0.0279 0.0680 Uiso calc . . 1.00
  H7 0.3149 -0.2271 -0.1138 0.0919 Uiso calc . . 1.00
  H8 0.4367 -0.1823 -0.0599 0.0808 Uiso calc . . 1.00
  H9 0.5480 -0.4277 0.1011 0.0963 Uiso calc . . 1.00
  H10 0.5720 -0.3313 0.0295 0.0777 Uiso calc . . 1.00
  H11 0.4627 -0.3081 0.2294 0.0969 Uiso calc . . 1.00
  H12 0.5081 -0.1563 0.3466 0.0708 Uiso calc . . 1.00
  H13 0.7310 -0.0118 0.2269 0.0609 Uiso calc . . 1.00
  H14 0.6833 -0.1646 0.1056 0.0613 Uiso calc . . 1.00
  H15 0.7150 0.0702 0.3780 0.0698 Uiso calc . . 1.00
  H16 0.6457 -0.0029 0.4351 0.0821 Uiso calc . . 1.00
  H17 0.4524 0.0655 0.4124 0.0702 Uiso calc . . 1.00
  H18 0.3108 0.2130 0.3614 0.0793 Uiso calc . . 1.00
  H19 0.4949 0.3831 0.2086 0.0987 Uiso calc . . 1.00
  H20 0.6365 0.2394 0.2698 0.0764 Uiso calc . . 1.00
  H21 0.2375 0.3932 0.2611 0.0862 Uiso calc . . 1.00
  H22 0.3185 0.4822 0.2296 0.1464 Uiso calc . . 1.00
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 0.1128(7) 0.0524(4) 0.0736(6) 0.0354(5) 0.0356(5) 0.0152(4)
  S2 0.0827(6) 0.0396(4) 0.1049(7) -0.0092(4) .0348(5) -0.0218(4)
  C1 0.070(2) 0.072(2) 0.068(2) 0.026(2) 0.030(2) 0.004(2)
  C2 0.051(2) 0.0510(10)
  0.0460(10)
  0.0080(10)
  0.0210(10)
  0.0050(10)
  C3 0.051(2) 0.0450(10)
  0.0450(10)
  0.0060(10)
  0.0070(10)
  -0.0060(10)
  C4 0.0440(10)
  0.0460(10)
  0.053(2) 0.0080(10)
  0.0080(10)
  -0.0030(10)
  C5 0.057(2) 0.0450(10)
  0.047(2) -0.0050(10)
  .0190(10)
  -0.0050(10)
  C6 0.054(2) 0.067(2) 0.059(2) -0.0140(10)
  .0100(10)
  -0.0120(10)
  C7 0.0380(10)
  0.079(2) 0.066(2) 0.0030(10)
  0.0100(10)
  0.005(2)
  C8 0.080(2) 0.058(2) 0.065(2) -0.004(2) .029(2) -0.0190(10)
  C9 0.085(2) 0.051(2) 0.098(2) 0.015(2) 0.040(2) -0.011(2)
  C10 0.057(2) 0.0450(10)
  0.068(2) 0.0170(10)
  0.0230(10)
  0.0050(10)
  C11 0.072(2) 0.053(2) 0.081(2) 0.0000(10)
  0.037(2) 0.006(2)
  C12 0.068(2) 0.073(2) 0.059(2) 0.003(2) 0.032(2) 0.007(2)
  C13 0.0390(10)
  0.066(2) 0.047(2) 0.0070(10)
  0.0050(10)
  0.0060(10)
  C14 0.0370(10)
  0.070(2) 0.059(2) 0.0040(10)
  0.0110(10)
  0.0070(10)
  C15 0.047(2) 0.063(2) 0.058(2) 0.0170(10)
  0.0220(10)
  0.0120(10)
  C16 0.047(2) 0.098(2) 0.053(2) -0.002(2) .0020(10)
  -0.010(2)
  C17 0.049(2) 0.069(2) 0.0420(10)
  -0.0120(10)
  .0080(10)
  -0.0170(10)
  C18 0.066(2) 0.069(2) 0.043(2) -0.006(2) 0.0150(10)
  0.0020(10)
  C19 0.067(2) 0.075(2) 0.052(2) -0.001(2) .027(2) -0.011(2)
  C20 0.085(2) 0.047(2) 0.061(2) 0.000(2) 0.029(2) -0.0170(10)
  C21 0.094(2) 0.046(2) 0.068(2) -0.016(2) .028(2) -0.0090(10)
  C22 0.064(2) 0.074(2) 0.060(2) -0.028(2) .026(2) -0.020(2)
  C23 0.122(3) 0.057(2) 0.092(2) 0.027(2) 0.044(2) -0.013(2)
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 C1 . . 1.806(3) yes
  S1 C23 . . 1.826(3) yes
  S2 C8 . . 1.825(3) yes
  S2 C9 . . 1.812(3) yes
  C1 C2 . . 1.504(3) yes
  C2 C3 . . 1.389(3) no
  C2 C7 . . 1.369(4) no
  C3 C4 . . 1.371(3) no
  C4 C5 . . 1.383(3) no
  C5 C6 . . 1.381(4) no
  C5 C8 . . 1.511(3) yes
  C6 C7 . . 1.386(4) no
  C9 C10 . . 1.505(4) yes
  C10 C11 . . 1.390(4) no
  C10 C15 . . 1.371(4) no
  C11 C12 . . 1.370(4) no
  C12 C13 . . 1.388(4) no
  C13 C14 . . 1.379(3) no
  C13 C16 . . 1.509(4) yes
  C14 C15 . . 1.391(4) no
  C16 C17 . . 1.511(4) yes
  C17 C18 . . 1.383(4) no
  C17 C22 . . 1.395(4) no
  C18 C19 . . 1.388(4) no
  C19 C20 . . 1.378(4) no
  C20 C21 . . 1.387(4) no
  C20 C23 . . 1.502(4) yes
  C21 C22 . . 1.375(4) no
  C1 H1 . . 0.888 no
  C1 H2 . . 1.000 no
  C3 H3 . . 0.934 no
  C4 H4 . . 0.961 no
  C6 H5 . . 0.965 no
  C7 H6 . . 0.878 no
  C8 H7 . . 0.977 no
  C8 H8 . . 0.972 no
  C9 H9 . . 0.963 no
  C9 H10 . . 0.944 no
  C11 H11 . . 0.944 no
  C12 H12 . . 0.916 no
  C14 H13 . . 0.976 no
  C15 H14 . . 0.960 no
  C16 H15 . . 0.960 no
  C16 H16 . . 0.970 no
  C18 H17 . . 0.912 no
  C19 H18 . . 0.962 no
  C21 H19 . . 0.990 no
  C22 H20 . . 0.938 no
  C23 H21 . . 0.908 no
  C23 H22 . . 1.023 no