4-Oxocyclohexaneacetic acid: catemeric hydrogen bonding and spontaneous resolution of a single conformational enantiomer in an achiral ∊-keto acid

Abstract

The asymmetric unit of the title compound, C8H12O3, consists of a single conformational enantiomer, which aggregates in the catemeric acid-to-ketone hydrogen-bonding mode [O...O = 2.682 (4) Å and O—H...O = 172 (6)°]. Four hydrogen-bonding chains of translationally related molecules pass through the cell orthogonal to the 43 screw axis along c, alternating in the 110 and the overline{1}10 direction, with alignment with respect to this axis of + + − −. Successive chains are rotated by 90° around the c axis. One C—H...O=C close contact, involving the carboxyl group, exists.