Received 29 July 2008
The title compound, C16H20O2, was synthesized to study the hydrogen-bonding interaction of the two enantiomers in the solid state. The racemate is made up of carboxylic acid RS dimers. Intermolecular O-HO hydrogen bonds produce centrosymmetric R22(8) rings which dimerize the two chiral enantiomers through their carboxyl groups. The chirality of this compound is generated by the presence of the double bond in the cyclohexene ring and a chiral axis due to the meta-methyl substituent on the aromatic ring.
In similar compounds previously reported (Xie et al., 2002, 2007a, 2008), the racemates also consist of carboxylic acid RS dimers. For related literature, see: Xie et al. (2007b, 2004); Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2254 ).
SX and HS are grateful to the departmental fund and the Grant-in-aid for Faculty Research from Indiana University Kokomo, as well as a Senior Research Grant from Indiana Academy of Science.
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