#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010341.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_2010341
loop_
_publ_author_name
'Kopf, J\"urgen'
'Maelger, Harald'
'Thiemann, Carolin'
'Margaretha, Paul'
_publ_section_title
;
(6a\a,6b\b,12b\b,12c\a)-6a,6b,12b,12c-Tetrahydrocyclobuta[1,2-c:4,3-c']-
di[1]benzothiopyran-6,7-dione
;
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1922
_journal_page_last               1924
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C18 H12 O2 S2'
_chemical_formula_weight         324.40
_chemical_melting_point          512.5(5)
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'P 65'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            12
_cell_length_a                   9.9360(10)
_cell_length_b                   9.9360(10)
_cell_length_c                   52.270(10)
_cell_measurement_temperature    293.0(10)
_cell_volume                     4469.0(10)
_diffrn_ambient_temperature      293.0(10)
_exptl_crystal_density_diffrn    1.446
_refine_ls_R_factor_obs          0.0663
_refine_ls_wR_factor_obs         0.1817
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '512-513 K' was changed to '512.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2010341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
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 0.1121(12) 0.0745(8) 0.1088(12) 0.0683(9) -0.0236(9) -0.0104(8)
S2 0.0614(6) 0.0802(8) 0.0801(8) 0.0460(6) 0.0046(5) -0.0040(6)
O1 0.130(4) 0.064(2) 0.078(3) 0.045(2) 0.020(3) 0.019(2)
O2 0.070(2) 0.088(3) 0.113(4) 0.032(2) 0.033(2) 0.003(2)
C1 0.076(3) 0.060(2) 0.069(3) 0.041(2) 0.012(2) 0.001(2)
C2 0.120(5) 0.076(3) 0.054(3) 0.064(3) 0.011(3) 0.007(2)
C3 0.088(3) 0.078(3) 0.061(3) 0.064(3) -0.003(2) -0.003(2)
C4 0.102(4) 0.129(5) 0.073(4) 0.093(5) 0.001(3) 0.003(3)
C5 0.067(3) 0.118(5) 0.074(4) 0.055(3) 0.008(2) 0.010(3)
C6 0.062(3) 0.096(4) 0.084(4) 0.040(3) 0.011(3) 0.020(3)
C7 0.060(3) 0.075(3) 0.097(4) 0.042(2) 0.005(3) 0.015(3)
C8 0.069(3) 0.070(3) 0.055(2) 0.048(2) 0.001(2) 0.003(2)
C9 0.062(2) 0.055(2) 0.065(3) 0.038(2) 0.010(2) 0.003(2)
C11 0.059(2) 0.049(2) 0.072(3) 0.025(2) 0.010(2) -0.002(2)
C12 0.051(2) 0.057(2) 0.091(4) 0.021(2) 0.011(2) -0.002(2)
C13 0.050(2) 0.057(2) 0.058(2) 0.028(2) -0.010(2) -0.009(2)
C14 0.064(3) 0.064(3) 0.071(3) 0.032(2) -0.014(2) -0.005(2)
C15 0.078(3) 0.073(3) 0.076(4) 0.031(3) -0.011(3) 0.016(3)
C16 0.076(3) 0.086(4) 0.068(4) 0.034(3) 0.010(3) 0.004(3)
C17 0.063(3) 0.082(3) 0.062(3) 0.039(2) 0.010(2) 0.002(2)
C18 0.049(2) 0.062(2) 0.050(2) 0.029(2) -0.003(2) -0.009(2)
C19 0.056(2) 0.059(2) 0.056(2) 0.035(2) 0.007(2) 0.000(2)
S51 0.0788(8) 0.0764(8) 0.0706(8) 0.0383(7) 0.0077(6) -0.0073(6)
S52 0.1089(11) 0.0588(6) 0.0692(8) 0.0403(7) 0.0259(7) 0.0083(5)
O51 0.089(3) 0.072(2) 0.116(4) 0.028(2) 0.007(2) -0.043(2)
O52 0.087(3) 0.049(2) 0.096(3) 0.027(2) 0.011(2) 0.010(2)
C51 0.060(2) 0.044(2) 0.073(3) 0.029(2) 0.000(2) -0.002(2)
C52 0.062(3) 0.054(2) 0.100(4) 0.031(2) -0.001(3) -0.015(2)
C53 0.056(2) 0.051(2) 0.079(3) 0.031(2) 0.002(2) 0.007(2)
C54 0.058(3) 0.070(3) 0.096(4) 0.036(2) 0.012(3) 0.026(3)
C55 0.053(3) 0.081(3) 0.114(5) 0.034(3) 0.009(3) 0.040(3)
C56 0.054(2) 0.050(2) 0.119(5) 0.015(2) -0.012(3) 0.011(3)
C57 0.054(2) 0.048(2) 0.095(4) 0.026(2) -0.005(2) 0.000(2)
C58 0.046(2) 0.048(2) 0.068(3) 0.025(2) -0.002(2) 0.005(2)
C59 0.049(2) 0.041(2) 0.067(3) 0.024(2) 0.001(2) 0.001(2)
C61 0.051(2) 0.047(2) 0.064(3) 0.022(2) -0.001(2) -0.007(2)
C62 0.054(2) 0.047(2) 0.066(3) 0.019(2) 0.007(2) 0.004(2)
C63 0.052(2) 0.054(2) 0.060(2) 0.024(2) 0.001(2) -0.009(2)
C64 0.057(2) 0.069(3) 0.072(3) 0.030(2) 0.003(2) -0.018(2)
C65 0.065(3) 0.065(3) 0.079(3) 0.041(2) -0.013(2) -0.019(2)
C66 0.084(3) 0.057(2) 0.087(4) 0.046(2) -0.010(3) -0.005(2)
C67 0.066(3) 0.056(2) 0.071(3) 0.036(2) 0.001(2) 0.008(2)
C68 0.046(2) 0.046(2) 0.063(2) 0.024(2) -0.002(2) -0.004(2)
C69 0.055(2) 0.048(2) 0.056(2) 0.030(2) -0.001(2) 0.001(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S1 1.1579(2) -0.1056(2) 0.70268(4) 0.0888(5) Uani d . 1 . S
S2 0.73510(10) 0.1658(2) 0.66093(3) 0.0692(3) Uani d . 1 . S
O1 0.8662(6) -0.2775(5) 0.70780(10) 0.0920(10) Uani d . 1 . O
O2 0.5992(5) -0.0665(5) 0.69150(10) 0.0940(10) Uani d . 1 . O
C1 0.9244(6) -0.0205(6) 0.69880(10) 0.0660(10) Uani d . 1 . C
H1 0.8788(6) 0.0017(6) 0.71370(11) 0.14(3) Uiso calc R 1 . H
C2 0.9654(9) -0.1443(7) 0.70400(10) 0.077(2) Uani d . 1 . C
C3 1.2764(7) 0.0961(6) 0.69750(10) 0.0660(10) Uani d . 1 . C
C4 1.4353(8) 0.1562(9) 0.70230(10) 0.085(2) Uani d . 1 . C
H4 1.4731(8) 0.0912(9) 0.70714(12) 0.061(14) Uiso calc R 1 . H
C5 1.5351(7) 0.3153(9) 0.69960(10) 0.082(2) Uani d . 1 . C
H5 1.6401(7) 0.3567(9) 0.70323(13) 0.081(19) Uiso calc R 1 . H
C6 1.4827(7) 0.4126(8) 0.69160(10) 0.080(2) Uani d . 1 . C
H6 1.5516(7) 0.5181(8) 0.68929(13) 0.12(3) Uiso calc R 1 . H
C7 1.3254(6) 0.3505(7) 0.68720(10) 0.0740(10) Uani d . 1 . C
H7 1.2886(6) 0.4154(7) 0.68180(14) 0.11(2) Uiso calc R 1 . H
C8 1.2216(6) 0.1938(6) 0.69070(10) 0.0590(10) Uani d . 1 . C
C9 1.0511(5) 0.1290(5) 0.68540(10) 0.0570(10) Uani d . 1 . C
H9 1.0267(5) 0.2119(5) 0.68842(10) 0.052(12) Uiso calc R 1 . H
C11 0.8241(6) -0.0559(5) 0.67450(10) 0.0610(10) Uani d . 1 . C
H11 0.7759(6) -0.1653(5) 0.66939(10) 0.13(3) Uiso calc R 1 . H
C12 0.7077(6) -0.0032(6) 0.67720(10) 0.0690(10) Uani d . 1 . C
C13 0.8745(5) 0.2037(5) 0.63710(10) 0.0540(10) Uani d . 1 . C
C14 0.8797(6) 0.2983(6) 0.61640(10) 0.0660(10) Uani d . 1 . C
H14 0.8115(6) 0.3368(6) 0.61590(11) 0.054(13) Uiso calc R 1 . H
C15 0.9835(7) 0.3324(7) 0.59740(10) 0.079(2) Uani d . 1 . C
H15 0.9859(7) 0.3939(7) 0.58384(13) 0.068(15) Uiso calc R 1 . H
C16 1.0866(7) 0.2773(8) 0.59790(10) 0.079(2) Uani d . 1 . C
H16 1.1614(7) 0.3057(8) 0.58516(12) 0.13(3) Uiso calc R 1 . H
C17 1.0774(6) 0.1809(7) 0.61710(10) 0.0680(10) Uani d . 1 . C
H17 1.1413(6) 0.1375(7) 0.61651(11) 0.070(16) Uiso calc R 1 . H
C18 0.9766(5) 0.1450(5) 0.63760(10) 0.0530(10) Uani d . 1 . C
C19 0.9756(5) 0.0486(5) 0.65950(10) 0.0540(10) Uani d . 1 . C
H19 1.0211(5) -0.0142(5) 0.65399(9) 0.052(12) Uiso calc R 1 . H
S51 1.0390(2) -0.5520(2) 0.72434(3) 0.0755(4) Uani d . 1 . S
S52 0.6399(2) -0.5912(2) 0.82387(3) 0.0796(4) Uani d . 1 . S
O51 0.8047(6) -0.8159(5) 0.73470(10) 0.098(2) Uani d . 1 . O
O52 0.6427(5) -0.8351(4) 0.81020(10) 0.0800(10) Uani d . 1 . O
C51 0.8778(5) -0.6551(5) 0.77160(10) 0.0570(10) Uani d . 1 . C
H51 0.8963(5) -0.7174(5) 0.78414(10) 0.048(12) Uiso calc R 1 . H
C52 0.8925(6) -0.6930(6) 0.74460(10) 0.0710(10) Uani d . 1 . C
C53 1.1611(5) -0.3943(5) 0.74460(10) 0.0600(10) Uani d . 1 . C
C54 1.3087(6) -0.2939(6) 0.73540(10) 0.0730(10) Uani d . 1 . C
H54 1.3388(6) -0.3141(6) 0.71970(13) 0.081(19) Uiso calc R 1 . H
C55 1.4112(6) -0.1659(7) 0.7490(2) 0.082(2) Uani d . 1 . C
H55 1.5093(6) -0.0977(7) 0.74245(15) 0.17(4) Uiso calc R 1 . H
C56 1.3662(6) -0.1393(6) 0.77280(10) 0.079(2) Uani d . 1 . C
H56 1.4353(6) -0.0532(6) 0.78235(14) 0.058(14) Uiso calc R 1 . H
C57 1.2185(5) -0.2405(5) 0.78250(10) 0.0660(10) Uani d . 1 . C
H57 1.1899(5) -0.2232(5) 0.79857(12) 0.063(15) Uiso calc R 1 . H
C58 1.1136(5) -0.3682(5) 0.76790(10) 0.0530(10) Uani d . 1 . C
C59 0.9581(5) -0.4784(4) 0.77850(10) 0.0520(10) Uani d . 1 . C
H59 0.9653(5) -0.4696(4) 0.79720(10) 0.051(12) Uiso calc R 1 . H
C61 0.7208(5) -0.6593(5) 0.77530(10) 0.0550(10) Uani d . 1 . C
H61 0.6425(5) -0.7211(5) 0.76240(9) 0.27(7) Uiso calc R 1 . H
C62 0.6666(5) -0.7109(5) 0.80300(10) 0.0590(10) Uani d . 1 . C
C63 0.6755(5) -0.4245(5) 0.80630(10) 0.0560(10) Uani d . 1 . C
C64 0.6219(6) -0.3335(6) 0.81800(10) 0.0660(10) Uani d . 1 . C
H64 0.5700(6) -0.3637(6) 0.83360(11) 0.068(16) Uiso calc R 1 . H
C65 0.6464(6) -0.1987(6) 0.80630(10) 0.0660(10) Uani d . 1 . C
H65 0.6121(6) -0.1371(6) 0.81407(11) 0.057(13) Uiso calc R 1 . H
C66 0.7232(7) -0.1546(6) 0.78270(10) 0.0720(10) Uani d . 1 . C
H66 0.7397(7) -0.0643(6) 0.77458(12) 0.062(15) Uiso calc R 1 . H
C67 0.7747(6) -0.2490(6) 0.77150(10) 0.0620(10) Uani d . 1 . C
H67 0.8257(6) -0.2207(6) 0.75582(11) 0.09(2) Uiso calc R 1 . H
C68 0.7511(4) -0.3832(5) 0.78330(10) 0.0510(10) Uani d . 1 . C
C69 0.8050(5) -0.4825(5) 0.77030(10) 0.0510(10) Uani d . 1 . C
H69 0.8083(5) -0.4649(5) 0.75178(9) 0.056(14) Uiso calc R 1 . H
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 . 1.754(7) yes
S1 C3 . 1.765(6) yes
S2 C13 . 1.758(5) yes
S2 C12 . 1.777(6) yes
O1 C2 . 1.207(8) yes
O2 C12 . 1.201(7) yes
C1 C2 . 1.501(7) yes
C1 C11 . 1.543(8) yes
C1 C9 . 1.552(7) yes
C1 H1 . 0.98 ?
C3 C8 . 1.377(6) yes
C3 C4 . 1.403(9) ?
C4 C5 . 1.391(10) ?
C4 H4 . 0.93 ?
C5 C6 . 1.371(9) ?
C5 H5 . 0.93 ?
C6 C7 . 1.384(8) ?
C6 H6 . 0.93 ?
C7 C8 . 1.384(8) ?
C7 H7 . 0.93 ?
C8 C9 . 1.506(7) yes
C9 C19 . 1.561(7) yes
C9 H9 . 0.98 ?
C11 C12 . 1.495(7) yes
C11 C19 . 1.547(6) yes
C11 H11 . 0.98 ?
C13 C18 . 1.400(6) yes
C13 C14 . 1.418(7) ?
C14 C15 . 1.345(9) ?
C14 H14 . 0.93 ?
C15 C16 . 1.382(9) ?
C15 H15 . 0.93 ?
C16 C17 . 1.360(9) ?
C16 H16 . 0.93 ?
C17 C18 . 1.386(7) ?
C17 H17 . 0.93 ?
C18 C19 . 1.489(7) ?
C19 H19 . 0.98 ?
S51 C53 . 1.774(6) yes
S51 C52 . 1.778(6) yes
S52 C62 . 1.730(5) yes
S52 C63 . 1.768(5) yes
O51 C52 . 1.206(7) yes
O52 C62 . 1.195(6) yes
C51 C52 . 1.488(8) yes
C51 C61 . 1.551(6) yes
C51 C59 . 1.565(6) yes
C51 H51 . 0.98 ?
C53 C54 . 1.384(7) ?
C53 C58 . 1.378(7) yes
C54 C55 . 1.365(10) ?
C54 H54 . 0.93 ?
C55 C56 . 1.392(11) ?
C55 H55 . 0.93 ?
C56 C57 . 1.395(8) ?
C56 H56 . 0.93 ?
C57 C58 . 1.397(7) ?
C57 H57 . 0.93 ?
C58 C59 . 1.484(6) yes
C59 C69 . 1.562(5) yes
C59 H59 . 0.98 ?
C61 C69 . 1.545(6) yes
C61 C62 . 1.539(7) yes
C61 H61 . 0.98 ?
C63 C68 . 1.366(7) yes
C63 C64 . 1.400(6) ?
C64 C65 . 1.379(8) ?
C64 H64 . 0.93 ?
C65 C66 . 1.401(9) ?
C65 H65 . 0.93 ?
C66 C67 . 1.402(7) ?
C66 H66 . 0.93 ?
C67 C68 . 1.379(6) ?
C67 H67 . 0.93 ?
C68 C69 . 1.501(5) yes
C69 H69 . 0.98 ?