#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013144.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_2013144
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o57
_journal_page_last  o59
_publ_section_title
;
Two new heterocyclic [3.3.3.0^1,5^] propellanoid compounds:
2,8-dioxatricyclo[3.3.3.0^1,5^]undecane-3,7-dione and a related dimer
;
loop_
_publ_author_name
  'Tsao, Jonglin F.'
  'Faruqi, Sana R.'
  'Thompson, Hugh W.'
  'Lalancette, Roger A.'
_chemical_formula_moiety  'C9 H10 O4'
_chemical_formula_sum  'C9 H10 O4'
_chemical_formula_weight  182.17
_chemical_melting_point  379
_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  12.697(3)
_cell_length_b  12.240(5)
_cell_length_c  11.509(4)
_cell_angle_alpha  90
_cell_angle_beta  106.79(2)
_cell_angle_gamma  90
_cell_volume  1712.4(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.413
_diffrn_ambient_temperature  296(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
  C1 0.8734(2) 0.6685(2) 0.0381(2) 0.0586(7) Uani d . 1 B . C
  O2 0.97789(16) 0.62141(15) 0.05275(18) 0.0649(6) Uani d . 1 . . O
  O3 1.12482(19) 0.57662(19) 0.2010(2) 0.0901(7) Uani d . 1 . . O
  C3 1.0336(3) 0.6111(2) 0.1718(3) 0.0631(7) Uani d . 1 . . C
  C4 0.9644(2) 0.6465(3) 0.2485(3) 0.0680(8) Uani d . 1 . . C
  H4A 1.0037 0.6989 0.3088 0.082 Uiso calc R 1 . . H
  H4B 0.9446 0.5844 0.2902 0.082 Uiso calc R 1 . . H
  C5 0.8629(2) 0.6980(2) 0.1649(2) 0.0506(6) Uani d . 1 B . C
  C6 0.8635(2) 0.8211(2) 0.1637(3) 0.0645(8) Uani d . 1 . . C
  H6A 0.7974 0.8495 0.1791 0.077 Uiso calc R 1 . . H
  H6B 0.9270 0.8490 0.2255 0.077 Uiso calc R 1 . . H
  O7 0.8671(2) 0.9431(2) 0.0000(3) 0.1242(11) Uani d . 1 . . O
  C7 0.8679(3) 0.8538(3) 0.0411(3) 0.0777(10) Uani d . 1 . . C
  O8 0.87170(18) 0.7662(2) -0.02718(18) 0.0807(7) Uani d . 1 . . O
  C9 0.7788(3) 0.5961(3) -0.0246(4) 0.0985(12) Uani d . 1 . . C
  H9A 0.8000 0.5198 -0.0166 0.118 Uiso calc R 1 A 1 H
  H9B 0.7507 0.6143 -0.1101 0.118 Uiso calc R 1 A 1 H
  C10 0.6944(7) 0.6206(11) 0.0419(6) 0.085(3) Uani d P 0.59(2) B 1 C
  H10A 0.6484 0.6815 0.0039 0.102 Uiso calc PR 0.59(2) B 1 H
  H10B 0.6477 0.5575 0.0397 0.102 Uiso calc PR 0.59(2) B 1 H
  C10A 0.7274(7) 0.5698(11) 0.0618(6) 0.090(4) Uani d PR 0.41(2) B 2 C
  H10E 0.7498 0.4970 0.0923 0.107 Uiso d PR 0.41(2) B 2 H
  H10F 0.6485 0.5688 0.0243 0.107 Uiso d PR 0.41(2) B 2 H
  C11 0.7537(3) 0.6472(3) 0.1657(3) 0.0786(9) Uani d . 1 . . C
  H11A 0.7664 0.5818 0.2153 0.094 Uiso calc R 1 B 1 H
  H11B 0.7117 0.6984 0.1990 0.094 Uiso calc R 1 B 1 H
  C1' 0.6211(2) 0.3713(3) 0.3302(2) 0.0626(8) Uani d . 1 . . C
  O2' 0.69620(18) 0.3770(2) 0.26048(19) 0.0854(7) Uani d . 1 . . O
  O3' 0.8705(2) 0.3466(2) 0.2786(3) 0.1194(10) Uani d . 1 . . O
  C3' 0.7978(3) 0.3440(3) 0.3246(3) 0.0762(9) Uani d . 1 . . C
  C4' 0.7971(2) 0.3069(3) 0.4451(3) 0.0752(9) Uani d . 1 . . C
  H4'A 0.8484 0.3495 0.5074 0.090 Uiso calc R 1 . . H
  H4'B 0.8184 0.2306 0.4563 0.090 Uiso calc R 1 . . H
  C5' 0.6815(2) 0.3217(2) 0.4533(2) 0.0556(7) Uani d . 1 . . C
  C6' 0.6683(3) 0.4093(3) 0.5407(3) 0.0714(9) Uani d . 1 . . C
  H6'A 0.6202 0.3841 0.5870 0.086 Uiso calc R 1 . . H
  H6'B 0.7391 0.4279 0.5967 0.086 Uiso calc R 1 . . H
  O7' 0.6025(2) 0.5935(2) 0.5001(3) 0.1211(11) Uani d . 1 . . O
  C7' 0.6204(2) 0.5042(3) 0.4671(4) 0.0758(9) Uani d . 1 . . C
  O8' 0.59176(17) 0.47929(19) 0.3478(2) 0.0827(7) Uani d . 1 . . O
  C9' 0.5256(3) 0.2979(4) 0.2718(3) 0.0935(12) Uani d . 1 . . C
  H9'A 0.4585 0.3240 0.2865 0.112 Uiso calc R 1 . . H
  H9'B 0.5144 0.2925 0.1850 0.112 Uiso calc R 1 . . H
  C10' 0.5600(4) 0.1920(4) 0.3323(5) 0.1297(17) Uani d . 1 . . C
  H10C 0.4963 0.1467 0.3278 0.156 Uiso calc R 1 . . H
  H10D 0.6077 0.1535 0.2938 0.156 Uiso calc R 1 . . H
  C11' 0.6177(4) 0.2165(3) 0.4566(4) 0.0990(12) Uani d . 1 . . C
  H11C 0.6676 0.1576 0.4925 0.119 Uiso calc R 1 . . H
  H11D 0.5663 0.2268 0.5037 0.119 Uiso calc R 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
  C1 0.0563(16) 0.0664(18) 0.0557(16) 0.0044(13) 0.0206(13) -0.0052(14)
  O2 0.0651(12) 0.0674(12) 0.0685(13) 0.0086(10) 0.0293(10) -0.0074(10)
  O3 0.0681(14) 0.0922(17) 0.1095(18) 0.0319(12) 0.0250(12) 0.0122(14)
  C3 0.0633(18) 0.0527(16) 0.074(2) 0.0088(14) 0.0218(15) 0.0080(14)
  C4 0.0679(18) 0.077(2) 0.0612(17) 0.0139(15) 0.0229(14) 0.0159(15)
  C5 0.0506(14) 0.0559(15) 0.0489(14) -0.0004(12) 0.0199(11) 0.0001(12)
  C6 0.0676(18) 0.0611(18) 0.0721(19) 0.0087(14) 0.0315(15) -0.0008(15)
  O7 0.145(3) 0.0855(18) 0.176(3) 0.0422(16) 0.100(2) 0.0645(19)
  C7 0.074(2) 0.071(2) 0.103(3) 0.0252(16) 0.0497(19) 0.030(2)
  O8 0.0946(16) 0.0955(17) 0.0612(13) 0.0282(13) 0.0373(12) 0.0212(12)
  C9 0.076(2) 0.117(3) 0.098(3) -0.015(2) 0.017(2) -0.046(2)
  C10 0.064(4) 0.095(6) 0.093(5) -0.019(4) 0.018(3) -0.011(4)
  C10A 0.103(8) 0.076(7) 0.086(7) -0.043(6) 0.022(6) 0.003(5)
  C11 0.068(2) 0.081(2) 0.097(2) -0.0159(17) 0.0396(18) -0.0055(19)
  C1' 0.0528(16) 0.081(2) 0.0556(17) 0.0057(14) 0.0188(13) 0.0081(15)
  O2' 0.0794(15) 0.1149(19) 0.0723(14) 0.0173(13) 0.0386(12) 0.0302(13)
  O3' 0.1009(19) 0.111(2) 0.183(3) 0.0148(16) 0.098(2) 0.020(2)
  C3' 0.067(2) 0.0644(19) 0.111(3) 0.0059(15) 0.047(2) 0.0065(19)
  C4' 0.0689(19) 0.0682(19) 0.083(2) 0.0198(16) 0.0126(16) -0.0009(17)
  C5' 0.0574(16) 0.0545(16) 0.0519(15) -0.0035(12) 0.0112(12) 0.0049(13)
  C6' 0.0601(17) 0.093(2) 0.0606(18) -0.0106(16) 0.0172(14) -0.0136(17)
  O7' 0.0827(17) 0.0784(18) 0.213(3) -0.0035(13) 0.060(2) -0.0432(19)
  C7' 0.0465(16) 0.068(2) 0.118(3) -0.0040(15) 0.0303(18) -0.009(2)
  O8' 0.0721(14) 0.0809(16) 0.0960(18) 0.0226(11) 0.0255(12) 0.0270(13)
  C9' 0.064(2) 0.152(4) 0.060(2) -0.010(2) 0.0108(16) -0.023(2)
  C10' 0.130(4) 0.122(4) 0.136(4) -0.058(3) 0.037(3) -0.041(3)
  C11' 0.139(3) 0.071(2) 0.093(3) -0.032(2) 0.043(2) 0.0000(19)
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
  C1 O8 . 1.409(3) ?
  C1 O2 . 1.411(3) ?
  C1 C9 . 1.500(4) ?
  C1 C5 . 1.547(4) ?
  O2 C3 . 1.354(3) ?
  O3 C3 . 1.186(3) ?
  C3 C4 . 1.480(4) ?
  C4 C5 . 1.505(4) ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 C6 . 1.506(4) ?
  C5 C11 . 1.522(4) ?
  C6 C7 . 1.483(4) ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  O7 C7 . 1.190(4) ?
  C7 O8 . 1.338(4) ?
  C9 C10A . 1.376(6) ?
  C9 C10 . 1.515(8) ?
  C9 H9A . 0.9700 ?
  C9 H9B . 0.9700 ?
  C10 C11 . 1.444(6) ?
  C10 H10A . 0.9700 ?
  C10 H10B . 0.9700 ?
  C10A C11 . 1.486(7) ?
  C10A H10E . 0.9699 ?
  C10A H10F . 0.9700 ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C1' O8' . 1.404(4) ?
  C1' O2' . 1.414(3) ?
  C1' C9' . 1.502(4) ?
  C1' C5' . 1.528(4) ?
  O2' C3' . 1.350(4) ?
  O3' C3' . 1.190(4) ?
  C3' C4' . 1.462(4) ?
  C4' C5' . 1.509(4) ?
  C4' H4'A . 0.9700 ?
  C4' H4'B . 0.9700 ?
  C5' C6' . 1.512(4) ?
  C5' C11' . 1.528(4) ?
  C6' C7' . 1.463(5) ?
  C6' H6'A . 0.9700 ?
  C6' H6'B . 0.9700 ?
  O7' C7' . 1.200(4) ?
  C7' O8' . 1.350(4) ?
  C9' C10' . 1.476(6) ?
  C9' H9'A . 0.9700 ?
  C9' H9'B . 0.9700 ?
  C10' C11' . 1.438(5) ?
  C10' H10C . 0.9700 ?
  C10' H10D . 0.9700 ?
  C11' H11C . 0.9700 ?
  C11' H11D . 0.9700 ?