Acta Cryst. (2007). E63, o479-o481  [ doi:10.1107/S160053680605478X ]

(±)-(cis-8a-Hydroxy-2-oxoperhydronaphthalen-4a-yl)propanenitrile: hydrogen bonding in a Robinson-annulation intermediate

D. Zewge, M. H. Malak, H. W. Thompson, R. A. Lalancette and A. P. J. Brunskill

Abstract: The title racemate, C₁₃H₁₉NO₂, is a pre-dehydration intermediate isolated from the base-catalysed Robinson annulation of (+/-)-2-(2-cyanoethyl)cyclohexanone. Centrosymmetric dimers are formed by reciprocal hydroxyl-to-ketone hydrogen bonding [OO = 2.7902 (13) Å and O-HO = 176°]. One intermolecular C-HO close contact is found to the hydroxyl group.

Online 10 January 2007

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