#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011268.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_2011268
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e361
_journal_page_last  e362
_publ_section_title
;
(1R,8R,11R)-3,3,11-Trimethyl-6,6-ethylenedioxybicyclo[6.3.0]undecan-2-one and
(1R,2R,8R,11R)-3,3,11-trimethyl-6,6-ethylenedioxybicyclo[6.3.0]undecan-2-ol
;
loop_
_publ_author_name
  'Yoshinobu Inouye'
_chemical_formula_moiety  'C16 H26 O3'
_chemical_formula_sum  'C16 H26 O3'
_chemical_formula_weight  266.37
_chemical_melting_point  '361-362'
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  15.594(3)
_cell_length_b  16.837(2)
_cell_length_c  5.6919(8)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1494.4(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.184
_diffrn_ambient_temperature  293(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
  C1  .0939(3)  .1546(2)  .0449(8)  .0401(9) Uani d . 1 . C
  H1  .079(3)  .174(2)  -.093(9)  .033(11) Uiso d . 1 . H
  C2  .0153(3)  .1583(3)  .2012(7)  .0434(9) Uani d . 1 . C
  C3  -.0642(3)  .2008(3)  .1090(8)  .0497(11) Uani d . 1 . C
  C4  -.0418(4)  .2782(3)  -.0232(10)  .0616(13) Uani d . 1 . C
  H4A  -.003(4)  .269(3)  -.183(12)  .076(17) Uiso d . 1 . H
  H4B  -.106(5)  .298(4)  -.062(15)  .11(2)  Uiso d . 1 . H
  C5  .0053(5)  .3437(4)  .1119(12)  .076(2) Uani d . 1 . C
  H5A  -.018(4)  .350(3)  .290(13)  .073(16) Uiso d . 1 . H
  H5B  -.013(4)  .390(5)  .060(15)  .11(2)  Uiso d . 1 . H
  C6  .1029(4)  .3440(3)  .1102(9)  .0613(14) Uani d . 1 . C
  C7  .1445(4)  .2828(3)  .2711(10)  .0585(13) Uani d . 1 . C
  H7A  .194(4)  .307(3)  .289(12)  .074(17) Uiso d . 1 . H
  H7B  .108(3)  .275(3)  .426(10)  .053(13) Uiso d . 1 . H
  C8  .1673(3)  .2030(3)  .1597(9)  .0502(11) Uani d . 1 . C
  H8  .200(3)  .207(3)  .039(10)  .048(13) Uiso d . 1 . H
  C9  .2080(4)  .1444(4)  .3337(12)  .071(2) Uani d . 1 . C
  H9A  .182(4)  .151(3)  .499(14)  .079(18) Uiso d . 1 . H
  H9B  .266(4)  .151(3)  .354(11)  .074(17) Uiso d . 1 . H
  C10  .1874(4)  .0618(4)  .2433(13)  .071(2) Uani d . 1 . C
  H10A  .235(5)  .031(4)  .240(15)  .10(2)  Uiso d . 1 . H
  H10B  .157(4)  .038(3)  .353(11)  .061(17) Uiso d . 1 . H
  C11  .1350(3)  .0721(3)  .0209(9)  .0509(11) Uani d . 1 . C
  H11  .176(2)  .078(2)  -.107(8)  .025(9) Uiso d . 1 . H
  O12  .0156(2)  .1274(2)  .3950(6)  .0616(10) Uani d . 1 . O
  C13  -.1064(4)  .1418(4)  -.0611(10)  .0699(15) Uani d . 1 . C
  H13A  -.1597  .1634  -.1164  .105 Uiso calc R 1 . H
  H13B  -.1170  .0926  .0189  .105 Uiso calc R 1 . H
  H13C  -.0689  .1326  -.1920  .105 Uiso calc R 1 . H
  C14  -.1266(3)  .2166(4)  .3179(10)  .072(2) Uani d . 1 . C
  H14A  -.1777  .2417  .2603  .108 Uiso calc R 1 . H
  H14B  -.0993  .2507  .4304  .108 Uiso calc R 1 . H
  H14C  -.1413  .1671  .3915  .108 Uiso calc R 1 . H
  O15  .1365(3)  .3371(2)  -.1187(6)  .0677(11) Uani d . 1 . O
  C16  .1498(5)  .4130(4)  -.2090(12)  .069(2) Uani d . 1 . C
  H16A  .108(3)  .428(3)  -.311(11)  .059(15) Uiso d . 1 . H
  H16B  .203(5)  .406(4)  -.272(13)  .08(2)  Uiso d . 1 . H
  C17  .1468(6)  .4677(4)  -.0039(14)  .085(2) Uani d . 1 . C
  H17A  .212(6)  .480(5)  .027(18)  .14(3)  Uiso d . 1 . H
  H17B  .136(5)  .512(5)  .032(17)  .12(3)  Uiso d . 1 . H
  O18  .1318(4)  .4204(2)  .1927(7)  .090(2) Uani d . 1 . O
  C19  .0740(4)  .0043(3)  -.0378(13)  .074(2) Uani d . 1 . C
  H19A  .0462  .0150  -.1850  .112 Uiso calc R 1 . H
  H19B  .0316  -.0003  .0837  .112 Uiso calc R 1 . H
  H19C  .1057  -.0444  -.0491  .112 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  .042(2)  .042(2)  .036(2)  .005(2)  .003(2)  .008(2)
  C2  .048(2)  .049(2)  .034(2)  .004(2)  .001(2)  .003(2)
  C3  .047(2)  .072(3)  .030(2)  .011(2)  .000(2)  .000(2)
  C4  .067(3)  .071(3)  .047(3)  .028(3)  -.004(3)  .006(3)
  C5  .113(5)  .052(3)  .063(4)  .027(3)  .002(4)  -.003(3)
  C6  .101(4)  .044(2)  .039(2)  -.003(2)  .012(3)  -.008(2)
  C7  .068(3)  .060(3)  .047(3)  -.007(3)  .009(3)  -.003(2)
  C8  .048(2)  .057(3)  .046(3)  -.003(2)  .002(2)  .003(2)
  C9  .045(3)  .089(4)  .080(4)  .011(3)  -.009(3)  .009(4)
  C10  .071(4)  .069(4)  .072(4)  .021(3)  -.005(3)  .017(3)
  C11  .053(2)  .045(2)  .054(3)  .010(2)  .011(2)  .009(2)
  O12  .055(2)  .086(2)  .044(2)  .013(2)  .013(2)  .023(2)
  C13  .057(3)  .099(4)  .054(3)  .003(3)  -.011(2)  -.010(3)
  C14  .051(3)  .114(4)  .050(3)  .028(3)  .003(2)  -.005(3)
  O15  .110(3)  .052(2)  .042(2)  -.010(2)  .019(2)  -.003(2)
  C16  .094(5)  .061(3)  .054(3)  .000(3)  .004(4)  .012(3)
  C17  .132(6)  .049(3)  .075(4)  -.021(4)  .001(5)  .002(3)
  O18  .173(5)  .048(2)  .050(2)  -.020(3)  .000(3)  -.010(2)
  C19  .088(4)  .048(3)  .087(4)  .003(2)  .012(4)  -.003(3)
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 . 1.515(6) ?
  C1 C11 . 1.537(6) ?
  C1 C8 . 1.550(7) ?
  C1 H1 .  .88(5) ?
  C2 O12 . 1.220(5) ?
  C2 C3 . 1.524(6) ?
  C3 C13 . 1.535(7) ?
  C3 C4 . 1.545(7) ?
  C3 C14 . 1.559(7) ?
  C4 C5 . 1.531(9) ?
  C4 H4A . 1.11(6) ?
  C4 H4B . 1.08(7) ?
  C5 C6 . 1.521(9) ?
  C5 H5A . 1.08(7) ?
  C5 H5B .  .88(8) ?
  C6 O15 . 1.410(6) ?
  C6 O18 . 1.441(6) ?
  C6 C7 . 1.525(8) ?
  C7 C8 . 1.528(7) ?
  C7 H7A .  .88(6) ?
  C7 H7B . 1.06(5) ?
  C8 C9 . 1.535(8) ?
  C8 H8 .  .86(5) ?
  C9 C10 . 1.517(9) ?
  C9 H9A . 1.03(8) ?
  C9 H9B .  .91(6) ?
  C10 C11 . 1.516(8) ?
  C10 H10A .  .90(7) ?
  C10 H10B .  .88(6) ?
  C11 C19 . 1.522(8) ?
  C11 H11 .  .97(4) ?
  C13 H13A .  .96 ?
  C13 H13B .  .96 ?
  C13 H13C .  .96 ?
  C14 H14A .  .96 ?
  C14 H14B .  .96 ?
  C14 H14C .  .96 ?
  O15 C16 . 1.393(7) ?
  C16 C17 . 1.487(10) ?
  C16 H16A .  .91(6) ?
  C16 H16B .  .91(7) ?
  C17 O18 . 1.393(8) ?
  C17 H17A . 1.05(9) ?
  C17 H17B .  .79(8) ?
  C19 H19A .  .96 ?
  C19 H19B .  .96 ?
  C19 H19C .  .96 ?