data_2009082
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1908
_journal_page_last  1911
_publ_section_title
;
(+)-cis-Pinonic Acid: catemeric hydrogen bonding in a non-racemic \e-keto
acid
;
loop_
_publ_author_name
  'Lalancette, Roger A.'
  'Thompson, Hugh W.'
  'Brunskill, Andrew P. J.'
_chemical_name_common  '(+)-cis-Pinonic Acid'
_chemical_formula_moiety  'C10 H16 O3'
_chemical_formula_sum  'C10 H16 O3'
_chemical_formula_weight  184.23
_chemical_melting_point  341K
_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  6.6250(10)
_cell_length_b  11.4760(10)
_cell_length_c  7.1270(10)
_cell_angle_alpha  90.00
_cell_angle_beta  105.030(10)
_cell_angle_gamma  90.00
_cell_volume  523.32(12)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.169
_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_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  .9258(3)  .30659(15)  .4528(3)  .0707(6) Uani d . 1 . . O
  O2  .4676(3)  .78521(17)  .0241(3)  .0664(6) Uani d . 1 . . O
  O3  .1817(3)  .68570(19)  -.1143(3)  .0642(6) Uani d . 1 . . O
  H3  .172(6)  .732(4)  -.191(5)  .083(12) Uiso d . 1 . . H
  C1  .6010(3)  .60859(19)  .3181(3)  .0404(5) Uani d . 1 . . C
  C2  .6333(3)  .5405(2)  .5117(3)  .0439(5) Uani d . 1 . . C
  C3  .8547(3)  .50761(18)  .4859(3)  .0401(5) Uani d . 1 . . C
  C4  .7731(4)  .5350(2)  .2693(3)  .0465(6) Uani d . 1 . . C
  C5  .6291(6)  .6136(3)  .6882(4)  .0818(11) Uani d . 1 . . C
  C6  .4907(5)  .4341(3)  .4921(6)  .0703(9) Uani d . 1 . . C
  C7  .9364(3)  .3897(2)  .5583(3)  .0447(5) Uani d . 1 . . C
  C8 1.0276(4)  .3782(3)  .7726(4)  .0581(7) Uani d . 1 . . C
  C9  .3832(4)  .6137(3)  .1827(4)  .0539(6) Uani d . 1 . . C
  C10  .3555(4)  .7041(2)  .0258(3)  .0431(5) Uani d . 1 . . C
  H1A  .6528  .6883  .3471  .041(6) Uiso calc R 1 . . H
  H3A  .9562  .5672  .5476  .048(7) Uiso calc R 1 . . H
  H4A  .7216  .4673  .1896  .058(8) Uiso calc R 1 . . H
  H4B  .8699  .5794  .2162  .054(8) Uiso calc R 1 . . H
  H5A  .7270  .6766  .7004  .095(7) Uiso calc R 1 . . H
  H5B  .6663  .5659  .8027  .095(7) Uiso calc R 1 . . H
  H5C  .4911  .6446  .6732  .095(7) Uiso calc R 1 . . H
  H6A  .5011  .3889  .3817  .090(7) Uiso calc R 1 . . H
  H6B  .3488  .4592  .4748  .090(7) Uiso calc R 1 . . H
  H6C  .5325  .3874  .6074  .090(7) Uiso calc R 1 . . H
  H8A 1.1658  .4107  .8072  .077(9) Uiso calc PR  .62(4) . . H
  H8B 1.0342  .2973  .8081  .077(9) Uiso calc PR  .62(4) . . H
  H8C  .9413  .4191  .8402  .077(9) Uiso calc PR  .62(4) . . H
  H8D  .9284  .3407  .8298  .077(9) Uiso calc PR  .38(4) . . H
  H8E 1.0600  .4541  .8289  .077(9) Uiso calc PR  .38(4) . . H
  H8F 1.1529  .3323  .7968  .077(9) Uiso calc PR  .38(4) . . H
  H9A  .3494  .5380  .1223  .072(9) Uiso calc R 1 . . H
  H9B  .2844  .6294  .2589  .071(9) 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  .0845(14)  .0505(11)  .0604(11)  .0203(10)  -.0112(9)  -.0164(9)
  O2  .0721(13)  .0565(11)  .0562(11)  -.0144(10)  -.0092(9)  .0139(9)
  O3  .0585(11)  .0655(12)  .0538(11)  -.0083(10)  -.0120(9)  .0149(10)
  C1  .0439(11)  .0345(10)  .0388(11)  -.0023(9)  .0036(9)  .0041(9)
  C2  .0438(12)  .0458(12)  .0417(12)  .0091(10)  .0105(9)  .0091(10)
  C3  .0387(11)  .0365(11)  .0415(11)  -.0014(9)  .0036(8)  -.0030(9)
  C4  .0508(13)  .0467(13)  .0429(12)  -.0011(11)  .0139(10)  .0016(10)
  C5  .104(3)  .097(2)  .0461(14)  .052(2)  .0224(15)  .0052(16)
  C6  .0492(14)  .077(2)  .082(2)  -.0007(13)  .0135(13)  .0400(17)
  C7  .0395(11)  .0406(11)  .0488(12)  .0027(10)  .0020(10)  -.0067(10)
  C8  .0616(16)  .0526(15)  .0523(14)  .0106(13)  .0007(13)  .0029(12)
  C9  .0455(13)  .0556(14)  .0532(14)  -.0043(12)  -.0004(11)  .0131(12)
  C10  .0452(12)  .0420(12)  .0385(11)  .0008(11)  .0040(9)  .0002(9)
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 C7 . 1.206(3) y
  O2 C10 . 1.192(3) y
  O3 C10 . 1.331(3) y
  C1 C9 . 1.515(3) ?
  C1 C4 . 1.530(3) ?
  C1 C2 . 1.552(3) ?
  C2 C5 . 1.518(4) ?
  C2 C6 . 1.528(4) ?
  C2 C3 . 1.571(3) ?
  C3 C7 . 1.498(3) ?
  C3 C4 . 1.530(3) ?
  C7 C8 . 1.496(3) ?
  C9 C10 . 1.501(3) ?