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

Abstract

The title menthol-derived ester, C₁₉H₂₆O₄, was synthesized by chloro­acetyl­ation of menthol followed by reaction with sodium benzoate. It crystallizes in the Sohncke space group P2₁ 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—CH₂ bond and an anti conformation about the CH₂—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.