data_2009129
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1899
_journal_page_last  1902
_publ_section_title
;
(+)-trans-Pinononic acid: hydrogen-bonding patterns in a nonracemic \d-
keto acid
;
loop_
_publ_author_name
  'Barcon, Alan'
  'Brunskill, Andrew P. J.'
  'Thompson, Hugh W.'
  'Lalancette, Roger A.'
_chemical_name_common  '(+)-trans-Pinononic acid'
_chemical_formula_moiety  'C9 H14 O3'
_chemical_formula_sum  'C9 H14 O3'
_chemical_formula_weight  170.20
_chemical_melting_point  348
_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  7.3872(9)
_cell_length_b  9.6082(13)
_cell_length_c  7.4972(14)
_cell_angle_alpha  90.00
_cell_angle_beta  115.444(10)
_cell_angle_gamma  90.00
_cell_volume  480.52(13)
_cell_formula_units_Z  2
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.176
_diffrn_ambient_temperature  298(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  .1888(3)  .8924(2)  .7080(3)  .0726(6) Uani d . 1 . . O
  O2  .3516(3)  .4922(3)  .2570(3)  .0803(6) Uani d . 1 . . O
  O3  .6495(3)  .5433(3)  .4932(3)  .0807(7) Uani d . 1 . . O
  H3  .688(5)  .491(5)  .418(5)  .100(12) Uiso d . 1 . . H
  C1  .3744(4)  .6471(3)  .5166(4)  .0512(6) Uani d . 1 . . C
  C2  .3645(3)  .5845(3)  .7053(4)  .0517(6) Uani d . 1 . . C
  C3  .1473(4)  .6514(3)  .6298(4)  .0554(6) Uani d . 1 . . C
  C4  .1500(4)  .6761(3)  .4281(4)  .0622(7) Uani d . 1 . . C
  C5  .3494(5)  .4263(3)  .7012(5)  .0740(9) Uani d . 1 . . C
  C6  .5270(4)  .6363(4)  .8992(4)  .0714(8) Uani d . 1 . . C
  C7  .1400(4)  .7782(3)  .7422(4)  .0560(7) Uani d . 1 . . C
  C8  .0718(5)  .7592(4)  .9012(5)  .0830(10) Uani d . 1 . . C
  C9  .4519(4)  .5548(3)  .4060(4)  .0555(6) Uani d . 1 . . C
  H1  .4493  .7349  .5495  .064(5) Uiso calc R 1 . . H
  H3A  .0463  .5825  .6218  .064(5) Uiso calc R 1 . . H
  H4A  .0706  .6093  .3280  .081(6) Uiso calc R 1 . . H
  H4B  .1151  .7705  .3796  .081(6) Uiso calc R 1 . . H
  H5A  .2508  .3967  .5743  .083(6) Uiso calc R 1 . . H
  H5B  .3108  .3957  .8018  .083(6) Uiso calc R 1 . . H
  H5C  .4771  .3868  .7250  .083(6) Uiso calc R 1 . . H
  H6A  .5315  .7361  .8977  .097(7) Uiso calc R 1 . . H
  H6B  .6542  .5994  .9164  .097(7) Uiso calc R 1 . . H
  H6C  .4980  .6061 1.0063  .097(7) Uiso calc R 1 . . H
  H8A  .0859  .8454  .9708  .129(9) Uiso calc R 1 . . H
  H8B  .1518  .6888  .9916  .129(9) Uiso calc R 1 . . H
  H8C  -.0664  .7311  .8436  .129(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  .0783(13)  .0623(12)  .0922(14)  -.0019(10)  .0510(12)  .0006(11)
  O2  .0772(13)  .0907(15)  .0717(12)  -.0004(12)  .0308(11)  -.0225(12)
  O3  .0591(12)  .0915(16)  .0947(16)  -.0002(10)  .0362(11)  -.0290(13)
  C1  .0566(14)  .0457(13)  .0557(13)  -.0034(11)  .0284(11)  .0007(11)
  C2  .0525(13)  .0521(14)  .0523(13)  .0019(11)  .0243(11)  .0061(11)
  C3  .0448(12)  .0587(15)  .0621(14)  -.0052(12)  .0223(11)  .0016(12)
  C4  .0630(16)  .0665(17)  .0526(14)  .0112(13)  .0205(12)  .0033(13)
  C5  .087(2)  .0562(17)  .085(2)  .0049(15)  .0430(17)  .0198(15)
  C6  .0599(15)  .090(2)  .0586(15)  .0089(15)  .0205(12)  .0028(15)
  C7  .0444(13)  .0658(17)  .0599(15)  .0044(13)  .0245(11)  .0055(13)
  C8  .091(2)  .097(2)  .082(2)  .013(2)  .0567(18)  .0114(19)
  C9  .0617(15)  .0505(14)  .0600(14)  -.0015(12)  .0317(12)  .0037(12)
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 . 1.216(3) y
  O2 C9 . 1.203(3) y
  O3 C9 . 1.323(3) y
  C1 C9 . 1.487(4) ?
  C1 C4 . 1.524(3) ?
  C1 C2 . 1.568(3) ?
  C2 C6 . 1.517(4) ?
  C2 C5 . 1.523(4) ?
  C2 C3 . 1.590(3) ?
  C3 C7 . 1.496(4) ?
  C3 C4 . 1.540(4) ?
  C7 C8 . 1.492(4) ?