3β-Acetoxy cholest-5-ene crystals: Catalytic synthesis, structural elucidation, contribution of intermolecular interactions and density functional theory calculations

Abstract

In this work, we present the synthesis of 3β-acetoxy cholest-5-ene using zinc triflate Zn(OTf)2 as a catalyst. The synthesized molecule has been characterized by single crystal XRD, spectroscopic techniques and density functional theory (DFT) calculations. The compound crystallizes in the monoclinic space group P21 with cell dimensions, a = 16.585(2) Ǻ, b = 9.5175(12) Ǻ, c = 17.656(2) Ǻ, α = 90.00, β = 106.369(4), γ = 90.00. The systematic analysis of intermolecular interactions in crystal structure was accomplished by Hirshfeld surface analysis and fingerprint plot. Molecules are linked by a combination of C⋯H, C⋯C, H⋯H and O⋯H contacts, which have clear signatures in the fingerprint plots. The theoretical DFT/B3LYP calculations have been attempted to obtain the optimized geometry, IR/NMR spectra, natural bond orbitals, frontier molecular orbitals and various structure based molecular properties. We compared the conformations of the compound in solid state and in solution by calculation of dihedral angles and coupling constant values.