Abstract
The molecular and crystal structures of chiral 1R,4S-2-(4-carbomethoxy)benzylidene-n-menthan-3-one (I) are determined by X-ray diffraction analysis. Crystals I are orthorhombic; at 20°C: a = 11.961(3) A, b = 26.453(8) A, c = 5.400(2) A, space group P212121, and Z = 4 (C19H25O3). In molecule I, the cyclohexanone ring with the axial methyl and isopropyl substituents adopts a chair conformation. It is found that the enone and arylidene fragments of compound I have a substantially nonplanar structure. The shortened intramolecular contacts between atoms of the arylidene grouping and the α fragment of the cyclohexanone ring and their associated distortions of bond angles at the sp2 carbon atoms are the common structural features of 2-arylidene-n-menthan-3-ones irrespective of the stereochemical configuration of the C(4) chiral center.
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