Crystal structure, Hirshfeld surface analysis and DFT study of 2-(2-isopropyl-5-methylcyclohexyloxy)-2-oxoethyl benzoate

The title menthol-derived ester, C 19 H 26 O 4 , was synthesized by chloroacetylation of menthol followed by reaction with sodium benzoate. It crystallizes in the Sohncke space group P 2 1 with one molecule in the asymmetric unit. The cyclohexane ring adopts a chair conformation, and the benzoate fragment is essentially planar. The oxoethyl bridge shows a gauche conformation about the O—CH 2 bond and an anti conformation about the CH 2 —C bond. In the crystal, the packing is mainly consolidated by a weak C—H...O contact linking molecules into chains parallel to [100]. Hirshfeld surface analysis indicates that H...H contacts make the largest contribution to the crystal cohesion, followed by O...H/H...O and C...H/H...C contacts, consistent with the hydrophobic menthyl entity. DFT calculations show reasonable agreement between the refined and optimized structures. Frontier-orbital and electrostatic-potential analyses identify the benzoate ester and carbonyl oxygen atoms as the main electronically active regions.

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