#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012321.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_2012321
_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  Monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  27.666(9)
_cell_length_b  5.066(2)
_cell_length_c  22.793(7)
_cell_angle_alpha  90
_cell_angle_beta  105.149(5)
_cell_angle_gamma  90
_cell_volume  3084(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.328
_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  .13422(6)  .0558(3)  .23845(8)  .0219(4) Uani d . 1 . . C
  C2  .16556(6)  -.1087(3)  .22076(8)  .0227(4) Uani d . 1 . . C
  C3  .20772(6)  -.2482(4)  .26506(9)  .0247(4) Uani d . 1 . . C
  H3A  .1983  -.4352  .2683  .030 Uiso calc R 1 . . H
  H3B  .2379  -.2445  .2493  .030 Uiso calc R 1 . . H
  C4  .22005(7)  -.1257(4)  .32688(9)  .0269(4) Uani d . 1 . . C
  H4A  .2512  -.1680  .3545  .032 Uiso calc R 1 . . H
  C4a  .18963(6)  .0393(4)  .34516(8)  .0246(4) Uani d . 1 . . C
  C5  .20257(7)  .1559(4)  .40837(9)  .0327(5) Uani d . 1 . . C
  H5A  .1855  .3283  .4073  .039 Uiso calc R 1 . . H
  H5B  .2391  .1873  .4219  .039 Uiso calc R 1 . . H
  C6  .18702(7)  -.0257(5)  .45417(9)  .0374(5) Uani d . 1 . . C
  H6A  .2119  -.1700  .4652  .045 Uiso calc R 1 . . H
  H6B  .1885  .0769  .4916  .045 Uiso calc R 1 . . H
  O7  .12693(6)  -.3669(3)  .44837(7)  .0400(4) Uani d . 1 . . O
  C7  .13553(7)  -.1467(4)  .43262(8)  .0276(4) Uani d . 1 . . C
  C8  .09399(6)  .0128(4)  .38959(8)  .0230(4) Uani d . 1 . . C
  H8A  .0982  .2048  .3998  .028 Uiso calc R 1 . . H
  C9a  .13862(6)  .1112(4)  .30472(8)  .0217(4) Uani d . 1 . . C
  H9  .1338  .3052  .3090  .026 Uiso calc R 1 . . H
  C9  .09571(6)  -.0321(4)  .32386(8)  .0220(4) Uani d . 1 . . C
  H9A  .0634  .0261  .2966  .026 Uiso calc R 1 . . H
  H9B  .0989  -.2240  .3175  .026 Uiso calc R 1 . . H
  C10  .16304(6)  -.1652(4)  .15539(9)  .0243(4) Uani d . 1 . . C
  O10  .18388(5)  -.0343(3)  .12509(7)  .0341(3) Uani d . 1 . . O
  O11  .13893(5)  -.3903(3)  .13737(6)  .0292(3) Uani d . 1 . . O
  C12  .13454(8)  -.4625(4)  .07486(9)  .0331(4) Uani d . 1 . . C
  H12A  .1163  -.6297  .0658  .050 Uiso calc R 1 . . H
  H12B  .1680  -.4827  .0685  .050 Uiso calc R 1 . . H
  H12C  .1163  -.3242  .0479  .050 Uiso calc R 1 . . H
  O13  .07926(5)  .1123(3)  .13907(6)  .0288(3) Uani d . 1 . . O
  C13  .09221(6)  .1790(4)  .19162(9)  .0237(4) Uani d . 1 . . C
  O14  .06994(5)  .3708(3)  .21563(6)  .0294(3) Uani d . 1 . . O
  C15  .02879(7)  .5047(4)  .17351(10)  .0342(5) Uani d . 1 . . C
  H15A  .0151  .6406  .1953  .051 Uiso calc R 1 . . H
  H15B  .0025  .3766  .1557  .051 Uiso calc R 1 . . H
  H15C  .0409  .5873  .1412  .051 Uiso calc R 1 . . H
  O16  .04589(5)  -.0722(3)  .39226(6)  .0315(3) Uani d . 1 . . O
  C17  .03486(8)  -.0094(5)  .44818(9)  .0402(5) Uani d . 1 . . C
  H17A  .0013  -.0736  .4474  .060 Uiso calc R 1 . . H
  H17B  .0362  .1824  .4540  .060 Uiso calc R 1 . . H
  H17C  .0595  -.0936  .4817  .060 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  .0220(8)  .0152(8)  .0297(9)  -.0028(6)  .0087(7)  .0002(7)
  C2  .0231(8)  .0157(8)  .0308(9)  -.0043(7)  .0100(7)  -.0006(7)
  C3  .0229(8)  .0186(8)  .0347(10)  .0018(7)  .0114(7)  -.0009(8)
  C4  .0201(8)  .0263(9)  .0329(10)  .0012(7)  .0044(7)  -.0005(8)
  C4a  .0197(8)  .0220(9)  .0308(9)  -.0034(7)  .0042(7)  -.0039(7)
  C5  .0204(8)  .0376(11)  .0367(11)  -.0002(8)  .0014(8)  -.0144(9)
  C6  .0277(10)  .0518(14)  .0282(10)  .0071(9)  -.0006(8)  -.0074(10)
  O7  .0576(10)  .0290(8)  .0345(8)  .0094(7)  .0143(7)  .0038(6)
  C7  .0337(10)  .0274(10)  .0217(9)  .0066(8)  .0075(7)  -.0048(7)
  C8  .0208(8)  .0216(9)  .0265(9)  -.0007(7)  .0058(7)  -.0037(7)
  C9a  .0201(8)  .0152(8)  .0300(9)  .0017(6)  .0068(7)  -.0023(7)
  C9  .0203(8)  .0214(9)  .0239(8)  -.0016(7)  .0051(7)  -.0012(7)
  C10  .0239(8)  .0176(8)  .0331(10)  .0005(7)  .0106(7)  -.0005(7)
  O10  .0361(7)  .0318(8)  .0394(8)  -.0100(6)  .0188(6)  .0000(6)
  O11  .0420(8)  .0204(7)  .0282(7)  -.0082(6)  .0145(6)  -.0037(5)
  C12  .0470(12)  .0273(10)  .0257(9)  -.0047(9)  .0108(8)  -.0018(8)
  O13  .0279(6)  .0263(7)  .0306(7)  -.0028(6)  .0046(5)  -.0004(6)
  C13  .0219(8)  .0190(9)  .0315(9)  -.0024(7)  .0094(7)  .0027(7)
  O14  .0293(7)  .0266(7)  .0323(7)  .0094(6)  .0080(5)  .0037(6)
  C15  .0294(9)  .0324(11)  .0399(11)  .0089(8)  .0077(8)  .0083(9)
  O16  .0253(6)  .0459(9)  .0250(7)  -.0082(6)  .0098(5)  -.0067(6)
  C17  .0311(10)  .0643(16)  .0278(10)  -.0006(10)  .0122(8)  -.0070(10)
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 . 1.338(2) ?
  C1 C13 . 1.494(3) ?
  C1 C9a . 1.510(2) ?
  C2 C10 . 1.501(3) ?
  C2 C3 . 1.504(3) ?
  C3 C4 . 1.495(3) ?
  C3 H3A .  .990 ?
  C3 H3B .  .990 ?
  C4 C4a . 1.328(3) ?
  C4 H4A .  .950 ?
  C4a C5 . 1.511(3) ?
  C4a C9a . 1.515(2) ?
  C5 C6 . 1.535(3) ?
  C5 H5A .  .990 ?
  C5 H5B .  .990 ?
  C6 C7 . 1.510(3) ?
  C6 H6A .  .990 ?
  C6 H6B .  .990 ?
  O7 C7 . 1.214(3) ?
  C7 C8 . 1.532(3) ?
  C8 O16 . 1.415(2) ?
  C8 C9 . 1.528(2) ?
  C8 H8A . 1.000 ?
  C9a C9 . 1.548(2) ?
  C9a H9 . 1.000 ?
  C9 H9A .  .990 ?
  C9 H9B .  .990 ?
  C10 O10 . 1.207(2) ?
  C10 O11 . 1.331(2) ?
  O11 C12 . 1.445(2) ?
  C12 H12A .  .980 ?
  C12 H12B .  .980 ?
  C12 H12C .  .980 ?
  O13 C13 . 1.205(2) ?
  C13 O14 . 1.342(2) ?
  O14 C15 . 1.451(2) ?
  C15 H15A .  .980 ?
  C15 H15B .  .980 ?
  C15 H15C .  .980 ?
  O16 C17 . 1.422(2) ?
  C17 H17A .  .980 ?
  C17 H17B .  .980 ?
  C17 H17C .  .980 ?