#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012315.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_2012315
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1316
_journal_page_last  1318
_publ_section_title
;
Key tricyclic synthetic intermediates for the preparation of the sesquiterpenes
\a- and \b-cedrene
;
loop_
_publ_author_name
  'Kennedy, Alan R.'
  'Kerr, William J.'
  'McLaughlin, Mark'
  'Pauson, Peter L.'
_chemical_formula_moiety  'C16 H24 O3'
_chemical_formula_sum  'C16 H24 O3'
_chemical_formula_weight  264.35
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  8.3280(3)
_cell_length_b  8.3930(3)
_cell_length_c  10.2120(4)
_cell_angle_alpha  90
_cell_angle_beta  106.696(2)
_cell_angle_gamma  90
_cell_volume  683.70(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.284
_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
  O1  .48780(17)  -.38785(19)  .53438(12)  .0344(3) Uani d . 1 . . O
  O2  -.39000(14)  -.31606(19)  .09467(12)  .0284(3) Uani d . 1 . . O
  O3  -.23261(14)  -.38265(16)  -.04680(11)  .0213(3) Uani d . 1 . . O
  C1  .3698(2)  -.3367(2)  .44531(16)  .0228(4) Uani d . 1 . . C
  C2  .2414(2)  -.2175(2)  .46290(17)  .0251(4) Uani d . 1 . . C
  H2A  .2696  -.1084  .4399  .030 Uiso calc R 1 . . H
  H2B  .2334  -.2184  .5578  .030 Uiso calc R 1 . . H
  C3  .07774(19)  -.2755(2)  .36180(15)  .0178(3) Uani d . 1 . . C
  H3  .0257  -.3548  .4104  .021 Uiso calc R 1 . . H
  C4  .12928(19)  -.3659(2)  .24538(15)  .0162(3) Uani d . 1 . . C
  C5  .32299(19)  -.3867(2)  .29559(16)  .0196(3) Uani d . 1 . . C
  H5  .3718  -.3053  .2466  .024 Uiso calc R 1 . . H
  C6  .3965(2)  -.5464(3)  .27365(18)  .0280(4) Uani d . 1 . . C
  H6A  .3591  -.6284  .3267  .042 Uiso calc R 1 . . H
  H6B  .5191  -.5400  .3037  .042 Uiso calc R 1 . . H
  H6C  .3587  -.5741  .1764  .042 Uiso calc R 1 . . H
  C7  -.0616(2)  -.1534(2)  .28849(16)  .0203(3) Uani d . 1 . . C
  C8  -.1065(2)  -.2061(2)  .13533(16)  .0182(3) Uani d . 1 . . C
  H8  -.1520  -.1138  .0740  .022 Uiso calc R 1 . . H
  C9  .06617(19)  -.2550(2)  .12185(15)  .0173(3) Uani d . 1 . . C
  H9A  .0559  -.3118  .0349  .021 Uiso calc R 1 . . H
  H9B  .1406  -.1616  .1282  .021 Uiso calc R 1 . . H
  C10  .0321(2)  -.5234(2)  .21179(16)  .0194(3) Uani d . 1 . . C
  H10A  .0553  -.5729  .1311  .023 Uiso calc R 1 . . H
  H10B  .0713  -.5976  .2899  .023 Uiso calc R 1 . . H
  C11  -.1575(2)  -.4974(2)  .18208(17)  .0219(4) Uani d . 1 . . C
  H11A  -.2170  -.5930  .1355  .026 Uiso calc R 1 . . H
  H11B  -.1845  -.4855  .2699  .026 Uiso calc R 1 . . H
  C12  -.22193(19)  -.3511(2)  .09335(15)  .0189(3) Uani d . 1 . . C
  C13  .0031(3)  .0192(2)  .2963(2)  .0288(4) Uani d . 1 . . C
  H13A  .0422  .0527  .3922  .043 Uiso calc R 1 . . H
  H13B  -.0878  .0895  .2463  .043 Uiso calc R 1 . . H
  H13C  .0960  .0251  .2555  .043 Uiso calc R 1 . . H
  C14  -.2077(2)  -.1542(3)  .35251(18)  .0290(4) Uani d . 1 . . C
  H14A  -.2968  -.0835  .3002  .044 Uiso calc R 1 . . H
  H14B  -.1678  -.1167  .4473  .044 Uiso calc R 1 . . H
  H14C  -.2515  -.2627  .3509  .044 Uiso calc R 1 . . H
  C15  -.5019(2)  -.3494(3)  -.03634(17)  .0279(4) Uani d . 1 . . C
  H15A  -.5447  -.2496  -.0857  .034 Uiso calc R 1 . . H
  H15B  -.5981  -.4139  -.0282  .034 Uiso calc R 1 . . H
  C16  -.3975(2)  -.4416(2)  -.10943(17)  .0241(4) Uani d . 1 . . C
  H16A  -.4043  -.5577  -.0946  .029 Uiso calc R 1 . . H
  H16B  -.4335  -.4193  -.2088  .029 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
  O1  .0298(7)  .0395(8)  .0240(6)  .0062(6)  -.0083(5)  -.0033(6)
  O2  .0147(5)  .0452(9)  .0235(6)  .0015(6)  .0028(4)  -.0075(6)
  O3  .0173(5)  .0290(7)  .0153(5)  .0005(5)  .0008(4)  -.0031(5)
  C1  .0195(8)  .0238(9)  .0216(8)  -.0059(7)  .0002(6)  -.0012(7)
  C2  .0230(8)  .0283(9)  .0199(8)  -.0015(7)  -.0003(6)  -.0072(7)
  C3  .0181(7)  .0203(8)  .0145(7)  -.0012(6)  .0040(6)  -.0012(6)
  C4  .0160(7)  .0172(8)  .0143(6)  .0001(6)  .0025(5)  -.0003(6)
  C5  .0159(7)  .0230(8)  .0181(7)  -.0009(7)  .0020(6)  .0008(6)
  C6  .0212(8)  .0338(11)  .0251(8)  .0082(8)  .0006(7)  -.0033(8)
  C7  .0195(8)  .0232(9)  .0172(8)  .0013(7)  .0039(6)  -.0029(7)
  C8  .0196(7)  .0190(8)  .0153(7)  .0027(6)  .0038(6)  .0004(6)
  C9  .0176(7)  .0180(8)  .0154(7)  -.0010(6)  .0035(5)  .0012(6)
  C10  .0214(8)  .0166(8)  .0181(7)  -.0026(7)  .0023(6)  -.0001(6)
  C11  .0190(8)  .0234(9)  .0214(8)  -.0053(7)  .0030(6)  .0011(7)
  C12  .0143(7)  .0260(9)  .0156(7)  -.0002(7)  .0032(5)  -.0023(7)
  C13  .0337(10)  .0208(9)  .0294(9)  .0028(8)  .0052(7)  -.0049(7)
  C14  .0244(9)  .0423(12)  .0212(8)  .0052(8)  .0077(7)  -.0069(8)
  C15  .0170(7)  .0385(11)  .0241(8)  .0002(8)  -.0009(6)  -.0013(8)
  C16  .0197(8)  .0268(9)  .0211(8)  -.0026(7)  -.0016(6)  -.0030(7)
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
  O1 C1 . 1.210(2) y
  O2 C15 . 1.421(2) ?
  O2 C12 . 1.4341(19) ?
  O3 C16 . 1.427(2) ?
  O3 C12 . 1.4329(17) ?
  C1 C2 . 1.513(3) y
  C1 C5 . 1.524(2) y
  C2 C3 . 1.533(2) ?
  C2 H2A .  .990 ?
  C2 H2B .  .990 ?
  C3 C7 . 1.568(2) y
  C3 C4 . 1.571(2) y
  C3 H3 . 1.000 ?
  C4 C9 . 1.534(2) ?
  C4 C10 . 1.536(2) ?
  C4 C5 . 1.556(2) y
  C5 C6 . 1.517(3) ?
  C5 H5 . 1.000 ?
  C6 H6A .  .980 ?
  C6 H6B .  .980 ?
  C6 H6C .  .980 ?
  C7 C14 . 1.538(2) ?
  C7 C13 . 1.539(3) ?
  C7 C8 . 1.564(2) ?
  C8 C12 . 1.533(2) ?
  C8 C9 . 1.539(2) ?
  C8 H8 . 1.000 ?
  C9 H9A .  .990 ?
  C9 H9B .  .990 ?
  C10 C11 . 1.536(2) ?
  C10 H10A .  .990 ?
  C10 H10B .  .990 ?
  C11 C12 . 1.529(2) ?
  C11 H11A .  .990 ?
  C11 H11B .  .990 ?
  C13 H13A .  .980 ?
  C13 H13B .  .980 ?
  C13 H13C .  .980 ?
  C14 H14A .  .980 ?
  C14 H14B .  .980 ?
  C14 H14C .  .980 ?
  C15 C16 . 1.511(3) ?
  C15 H15A .  .990 ?
  C15 H15B .  .990 ?
  C16 H16A .  .990 ?
  C16 H16B .  .990 ?