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

The title compound, C(16)H(22)O(2), 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.