data_2013375
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o254
_journal_page_last  o256
_publ_section_title
;
The sesquiterpenoid nootkatone and the absolute configuration of a
dibromo derivative
;
loop_
_publ_author_name
  'Sauer, Anne M.'
  'Fronczek, Frank R.'
  'Zhu, Betty C. R.'
  'Crowe, William E.'
  'Henderson, Gregg'
  'Laine, Roger A.'
_chemical_name_common  nootkatone
_chemical_formula_moiety  'C15 H22 O'
_chemical_formula_sum  'C15 H22 O'
_chemical_formula_iupac  'C15 H22 O'
_chemical_formula_weight  218.33
_chemical_melting_point  '309-311K'
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  5.903(2)
_cell_length_b  9.495(4)
_cell_length_c  11.630(6)
_cell_angle_alpha  90
_cell_angle_beta  96.09(2)
_cell_angle_gamma  90
_cell_volume  648.2(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  150
_exptl_crystal_density_diffrn  1.119
_diffrn_ambient_temperature  150
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 0.9245(3) 0.4298(2) 0.40302(15) 0.0544(5) Uani d . 1 . . O
  C1 0.8374(4) 0.3090(3) 0.56883(19) 0.0324(5) Uani d . 1 . . C
  H1 0.9146 0.2268 0.5475 0.039 Uiso calc R 1 . . H
  C2 0.8218(4) 0.4282(3) 0.4894(2) 0.0379(6) Uani d . 1 . . C
  C3 0.6720(4) 0.5467(3) 0.5196(2) 0.0393(6) Uani d . 1 . . C
  H3A 0.5118 0.5248 0.4912 0.047 Uiso calc R 1 . . H
  H3B 0.7157 0.6337 0.4806 0.047 Uiso calc R 1 . . H
  C4 0.6917(4) 0.5713(2) 0.65075(19) 0.0317(6) Uani d . 1 . . C
  H4 0.8555 0.5923 0.6758 0.038 Uiso calc R 1 . . H
  C5 0.6313(3) 0.4369(3) 0.71613(18) 0.0274(5) Uani d . 1 . . C
  C6 0.7166(4) 0.4560(2) 0.84551(18) 0.0287(5) Uani d . 1 . . C
  H6A 0.8755 0.4908 0.8514 0.034 Uiso calc R 1 . . H
  H6B 0.6231 0.5299 0.8777 0.034 Uiso calc R 1 . . H
  C7 0.7101(4) 0.3238(2) 0.92099(19) 0.0280(5) Uani d . 1 . . C
  H7 0.5486 0.2903 0.9148 0.034 Uiso calc R 1 . . H
  C8 0.8507(4) 0.2093(3) 0.8705(2) 0.0343(6) Uani d . 1 . . C
  H8A 0.8446 0.1222 0.9169 0.041 Uiso calc R 1 . . H
  H8B 1.0117 0.2398 0.8744 0.041 Uiso calc R 1 . . H
  C9 0.7605(4) 0.1786(3) 0.7443(2) 0.0352(6) Uani d . 1 . . C
  H9A 0.8611 0.1087 0.7122 0.042 Uiso calc R 1 . . H
  H9B 0.6065 0.1367 0.7419 0.042 Uiso calc R 1 . . H
  C10 0.7490(3) 0.3088(2) 0.67038(18) 0.0283(5) Uani d . 1 . . C
  C11 0.7807(4) 0.3577(2) 1.04696(19) 0.0328(6) Uani d . 1 . . C
  C12 0.6291(4) 0.4579(3) 1.1030(2) 0.0431(7) Uani d . 1 . . C
  H12A 0.6755 0.4612 1.1864 0.065 Uiso calc R 1 . . H
  H12B 0.4709 0.4257 1.0892 0.065 Uiso calc R 1 . . H
  H12C 0.6421 0.5522 1.0700 0.065 Uiso calc R 1 . . H
  C13 0.9638(4) 0.3046(3) 1.1070(2) 0.0452(7) Uani d . 1 . . C
  H13A 0.9998 0.3298 1.1859 0.054 Uiso calc R 1 . . H
  H13B 1.0593 0.2412 1.0712 0.054 Uiso calc R 1 . . H
  C14 0.3711(4) 0.4100(3) 0.7018(2) 0.0397(6) Uani d . 1 . . C
  H14A 0.3148 0.4110 0.6194 0.060 Uiso calc R 1 . . H
  H14B 0.2944 0.4839 0.7420 0.060 Uiso calc R 1 . . H
  H14C 0.3394 0.3181 0.7349 0.060 Uiso calc R 1 . . H
  C15 0.5564(5) 0.7019(3) 0.6779(2) 0.0473(7) Uani d . 1 . . C
  H15A 0.6193 0.7846 0.6422 0.071 Uiso calc R 1 . . H
  H15B 0.5665 0.7152 0.7619 0.071 Uiso calc R 1 . . H
  H15C 0.3965 0.6897 0.6471 0.071 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 0.0656(12) 0.0614(13) 0.0393(10) -0.0189(11) 0.0202(9) -0.0027(10)
  C1 0.0315(11) 0.0327(12) 0.0330(12) -0.0024(10) 0.0037(10) -0.0046(11)
  C2 0.0368(12) 0.0485(16) 0.0287(11) -0.0164(12) 0.0044(10) -0.0046(12)
  C3 0.0409(13) 0.0428(15) 0.0327(13) -0.0061(12) -0.0042(11) 0.0093(11)
  C4 0.0324(11) 0.0326(14) 0.0290(12) -0.0024(10) -0.0018(10) 0.0046(10)
  C5 0.0242(10) 0.0287(11) 0.0289(11) -0.0007(9) 0.0020(9) 0.0016(10)
  C6 0.0312(11) 0.0260(12) 0.0287(11) 0.0003(9) 0.0025(9) 0.0006(10)
  C7 0.0284(11) 0.0259(12) 0.0298(11) -0.0007(9) 0.0031(9) 0.0002(10)
  C8 0.0432(13) 0.0256(12) 0.0347(13) 0.0026(10) 0.0064(11) 0.0022(10)
  C9 0.0459(14) 0.0257(13) 0.0349(13) 0.0003(11) 0.0086(11) -0.0030(10)
  C10 0.0233(10) 0.0300(12) 0.0312(12) -0.0035(9) 0.0004(9) -0.0002(10)
  C11 0.0402(14) 0.0270(12) 0.0319(12) -0.0009(10) 0.0076(11) 0.0019(10)
  C12 0.0556(16) 0.0426(16) 0.0324(13) 0.0069(13) 0.0110(11) -0.0009(12)
  C13 0.0531(15) 0.0436(15) 0.0371(13) 0.0117(13) -0.0038(12) 0.0007(13)
  C14 0.0264(11) 0.0484(17) 0.0443(14) -0.0025(11) 0.0031(10) -0.0025(12)
  C15 0.0597(17) 0.0369(14) 0.0429(15) 0.0118(13) -0.0052(13) 0.0048(13)
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 C2 . 1.228(3) y
  C1 C10 . 1.341(3) y
  C1 C2 . 1.457(4) y
  C1 H1 . 0.9500 ?
  C2 C3 . 1.496(4) ?
  C3 C4 . 1.536(3) ?
  C3 H3A . 0.9900 ?
  C3 H3B . 0.9900 ?
  C4 C15 . 1.526(4) ?
  C4 C5 . 1.546(3) ?
  C4 H4 . 1.0000 ?
  C5 C10 . 1.524(3) ?
  C5 C6 . 1.546(3) ?
  C5 C14 . 1.549(3) ?
  C6 C7 . 1.535(3) ?
  C6 H6A . 0.9900 ?
  C6 H6B . 0.9900 ?
  C7 C11 . 1.515(3) ?
  C7 C8 . 1.523(3) ?
  C7 H7 . 1.0000 ?
  C8 C9 . 1.534(3) ?
  C8 H8A . 0.9900 ?
  C8 H8B . 0.9900 ?
  C9 C10 . 1.504(3) ?
  C9 H9A . 0.9900 ?
  C9 H9B . 0.9900 ?
  C11 C13 . 1.323(3) y
  C11 C12 . 1.501(3) y
  C12 H12A . 0.9800 ?
  C12 H12B . 0.9800 ?
  C12 H12C . 0.9800 ?
  C13 H13A . 0.9500 ?
  C13 H13B . 0.9500 ?
  C14 H14A . 0.9800 ?
  C14 H14B . 0.9800 ?
  C14 H14C . 0.9800 ?
  C15 H15A . 0.9800 ?
  C15 H15B . 0.9800 ?
  C15 H15C . 0.9800 ?