#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012320.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_2012320
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1326
_journal_page_last  1329
_publ_section_title
;
Diels-Alder adducts of medium-ring carbocyclic dienes prepared by
rearrangement of catalytically generated cyclic oxonium ylides
;
loop_
_publ_author_name
  'Wilson, Claire'
  'Clark, J. Stephen'
  'Bate, Andrea L.'
  'Blake, Alexander J.'
  'Grinter, Trevor'
  'Teat, Simon J.'
_chemical_formula_moiety  'C16 H20 O6'
_chemical_formula_sum  'C16 H20 O6'
_chemical_formula_iupac  'C16 H20 O6'
_chemical_formula_weight  308.32
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.4878(9)
_cell_length_b  10.1793(12)
_cell_length_c  11.0220(13)
_cell_angle_alpha  69.955(2)
_cell_angle_beta  83.957(2)
_cell_angle_gamma  79.806(2)
_cell_volume  775.85(16)
_cell_formula_units_Z  2
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.320
_diffrn_ambient_temperature  150(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  .65089(14)  -.13152(10)  .83490(9)  .0201(2) Uani d . 1 . . C
  C2  .80308(14)  -.14744(11)  .89538(10)  .0215(2) Uani d . 1 . . C
  C3  .94629(15)  -.05316(12)  .84004(11)  .0294(2) Uani d . 1 . . C
  H3A  .9429  .0107  .8910  .035 Uiso calc R 1 . . H
  H3B 1.0674  -.1123  .8482  .035 Uiso calc R 1 . . H
  C4a  .77001(14)  .05129(10)  .63967(10)  .0207(2) Uani d . 1 . . C
  C4  .92117(14)  .03402(11)  .70076(11)  .0251(2) Uani d . 1 . . C
  H4 1.0191  .0798  .6531  .030 Uiso calc R 1 . . H
  C5  .75280(14)  .13882(11)  .49805(10)  .0236(2) Uani d . 1 . . C
  H5A  .6749  .0967  .4588  .028 Uiso calc R 1 . . H
  H5B  .8745  .1345  .4535  .028 Uiso calc R 1 . . H
  C6  .67159(14)  .29555(11)  .47509(10)  .0255(2) Uani d . 1 . . C
  H6A  .7713  .3500  .4689  .031 Uiso calc R 1 . . H
  H6B  .6118  .3342  .3915  .031 Uiso calc R 1 . . H
  O7  .54631(12)  .39702(8)  .63726(8)  .0324(2) Uani d . 1 . . O
  C7  .53540(14)  .31555(11)  .58072(10)  .0229(2) Uani d . 1 . . C
  C8  .38436(14)  .22350(11)  .62452(10)  .0222(2) Uani d . 1 . . C
  H8  .2759  .2789  .6549  .027 Uiso calc R 1 . . H
  C9  .44706(14)  .09198(11)  .73858(10)  .0224(2) Uani d . 1 . . C
  H9A  .3417  .0419  .7752  .027 Uiso calc R 1 . . H
  H9B  .4853  .1232  .8063  .027 Uiso calc R 1 . . H
  C9a  .60482(13)  -.01491(10)  .70789(9)  .0194(2) Uani d . 1 . . C
  H9  .5589  -.0578  .6503  .023 Uiso calc R 1 . . H
  O10  .89137(11)  -.22613(9) 1.11288(7)  .02906(19) Uani d . 1 . . O
  C10  .84307(13)  -.25517(11) 1.02548(10)  .0215(2) Uani d . 1 . . C
  O11  .82751(11)  -.38646(8) 1.03209(7)  .02792(19) Uani d . 1 . . O
  C12  .85284(18)  -.49222(12) 1.15919(11)  .0332(3) Uani d . 1 . . C
  H12A  .9768  -.4998 1.1846  .050 Uiso calc R 1 . . H
  H12B  .8331  -.5839 1.1567  .050 Uiso calc R 1 . . H
  H12C  .7657  -.4644 1.2221  .050 Uiso calc R 1 . . H
  C13  .50841(14)  -.22576(11)  .88904(10)  .0219(2) Uani d . 1 . . C
  O13  .43812(13)  -.27538(10)  .82533(8)  .0391(2) Uani d . 1 . . O
  O14  .46497(11)  -.24372(9) 1.01364(7)  .02925(19) Uani d . 1 . . O
  C15  .34015(17)  -.34413(15) 1.07634(12)  .0359(3) Uani d . 1 . . C
  H15A  .2379  -.3259 1.0212  .054 Uiso calc R 1 . . H
  H15B  .2947  -.3335 1.1597  .054 Uiso calc R 1 . . H
  H15C  .4037  -.4406 1.0904  .054 Uiso calc R 1 . . H
  O16  .33115(10)  .18194(8)  .52459(7)  .02434(17) Uani d . 1 . . O
  C17  .22164(16)  .29506(12)  .43400(11)  .0300(2) Uani d . 1 . . C
  H17A  .1121  .3275  .4792  .045 Uiso calc R 1 . . H
  H17B  .1868  .2617  .3676  .045 Uiso calc R 1 . . H
  H17C  .2909  .3735  .3931  .045 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  .0219(5)  .0182(5)  .0205(5)  -.0042(4)  .0006(4)  -.0065(4)
  C2  .0225(5)  .0196(5)  .0215(5)  -.0038(4)  -.0006(4)  -.0053(4)
  C3  .0246(5)  .0301(6)  .0298(6)  -.0106(4)  -.0068(4)  -.0006(4)
  C4a  .0220(5)  .0175(4)  .0214(5)  -.0031(4)  .0020(4)  -.0057(4)
  C4  .0227(5)  .0234(5)  .0267(5)  -.0074(4)  .0006(4)  -.0036(4)
  C5  .0240(5)  .0249(5)  .0204(5)  -.0056(4)  .0018(4)  -.0057(4)
  C6  .0250(5)  .0230(5)  .0252(5)  -.0073(4)  -.0004(4)  -.0024(4)
  O7  .0501(5)  .0218(4)  .0270(4)  -.0074(3)  -.0083(4)  -.0073(3)
  C7  .0279(5)  .0166(5)  .0213(5)  -.0021(4)  -.0060(4)  -.0019(4)
  C8  .0222(5)  .0216(5)  .0218(5)  -.0013(4)  .0000(4)  -.0075(4)
  C9  .0213(5)  .0221(5)  .0213(5)  -.0031(4)  .0017(4)  -.0049(4)
  C9a  .0199(5)  .0189(5)  .0192(4)  -.0045(4)  -.0007(4)  -.0053(4)
  O10  .0325(4)  .0313(4)  .0243(4)  -.0079(3)  -.0035(3)  -.0082(3)
  C10  .0169(4)  .0231(5)  .0226(5)  -.0028(4)  .0004(4)  -.0057(4)
  O11  .0372(4)  .0216(4)  .0229(4)  -.0053(3)  -.0029(3)  -.0037(3)
  C12  .0443(7)  .0243(5)  .0246(5)  -.0063(5)  -.0020(5)  .0005(4)
  C13  .0217(5)  .0205(5)  .0217(5)  -.0040(4)  -.0019(4)  -.0039(4)
  O13  .0505(5)  .0475(5)  .0262(4)  -.0316(4)  .0005(4)  -.0095(4)
  O14  .0284(4)  .0378(5)  .0230(4)  -.0147(3)  .0040(3)  -.0086(3)
  C15  .0308(6)  .0475(7)  .0260(6)  -.0194(5)  .0027(4)  -.0025(5)
  O16  .0248(4)  .0225(4)  .0256(4)  -.0024(3)  -.0052(3)  -.0073(3)
  C17  .0275(5)  .0294(6)  .0301(6)  -.0022(4)  -.0082(4)  -.0051(5)
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 C2 . 1.3379(15) ?
  C1 C13 . 1.5001(13) ?
  C1 C9a . 1.5184(13) ?
  C2 C10 . 1.4982(14) ?
  C2 C3 . 1.5060(14) ?
  C3 C4 . 1.4992(15) ?
  C3 H3A .  .990 ?
  C3 H3B .  .990 ?
  C4a C4 . 1.3320(15) ?
  C4a C5 . 1.5150(14) ?
  C4a C9a . 1.5170(13) ?
  C4 H4 .  .950 ?
  C5 C6 . 1.5464(15) ?
  C5 H5A .  .990 ?
  C5 H5B .  .990 ?
  C6 C7 . 1.5085(15) ?
  C6 H6A .  .990 ?
  C6 H6B .  .990 ?
  O7 C7 . 1.2132(13) ?
  C7 C8 . 1.5297(14) ?
  C8 O16 . 1.4221(12) ?
  C8 C9 . 1.5301(14) ?
  C8 H8 . 1.000 ?
  C9 C9a . 1.5514(14) ?
  C9 H9A .  .990 ?
  C9 H9B .  .990 ?
  C9a H9 . 1.000 ?
  O10 C10 . 1.2052(13) ?
  C10 O11 . 1.3385(13) ?
  O11 C12 . 1.4516(13) ?
  C12 H12A .  .980 ?
  C12 H12B .  .980 ?
  C12 H12C .  .980 ?
  C13 O13 . 1.2002(13) ?
  C13 O14 . 1.3342(13) ?
  O14 C15 . 1.4538(13) ?
  C15 H15A .  .980 ?
  C15 H15B .  .980 ?
  C15 H15C .  .980 ?
  O16 C17 . 1.4301(13) ?
  C17 H17A .  .980 ?
  C17 H17B .  .980 ?
  C17 H17C .  .980 ?