Synthesis, crystal structure, Hirshfeld surface analysis and DFT study of the 1,1′-(buta-1,3-diyne-1,4-diyl)bis(cyclohexan-1-ol)

Abstract

The title compound, C16H22O2, was synthesized in order to obtain its guest-free form because `wheel-and-axle'-shaped molecules tend to crystallize from solutions as solvates or host–guest molecules. It crystallizes in the monoclinic space group P2/c with two crystallographically non-equivalent molecules, one situated on an inversion center and the other on a twofold axis. The rod-like 1,3-diyne fragments have the usual linear geometry. In the crystal, O—H ... O bonds form eight-membered rings of the R 4 4(8) type, linking molecules into layers. The Hirshfeld surface analysis indicates that the largest contributions are from intermolecular H...H (ca 71%) and H...C/C...H (ca 19%) contacts. The energies of the frontier molecular orbitals were determined by DFT calculations at the B3LYP/def2-TZVP level of theory.