Received 17 January 2011
Crystals of the title compound, C18H26O2, were grown from ethyl acetate. Due to the racemic precursor, the title compound is also obtained as a racemate. Disorder was observed during structure refinement, originating from two possible half-chair conformations of the non-aromatic ring. The disorder was refined by introducing split positions in the cyclo-hexane ring regarding the two possible R and S-enantiomers at the chiral CH group [ratio 0.744 (3):0.256 (3)]. The crystal structure features pairs of inversion-related molecules connected by pairs of non-classical C-HO hydrogen bonds.
For the occurrence of the title compound in human breast milk and the fatty tissue of fish, see: Valdersnes et al. (2006). The title compound is the product of an esterification of 3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (AHTN-COOH) with methanol. For the synthesis of the acid, see: Kuhlich et al. (2010); Valdersnes et al. (2006). For the crystal structures of AHTN and AHTN-COOH, see: De Ridder et al. (1990) and Kuhlich et al. (2010), respectively. For the environmental occurrence and estrogenic activity of AHTN, see: Heberer (2003); Bitsch et al. (2002). For puckering parameters, see: Cremer & Pople (1975).
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2346 ).
The authors want to thank Dr Dietmar Pfeifer (BAM, Berlin) for a helpful discussion regarding the interpretation of the NMR data.
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