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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 two crystallographically non-equivalent molecules in the title compound have C2 and Ci symmetries. The crystal structure features strong intermolecular O—H⋯O hydrogen bonds, which form eight-membered rings with 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 R44(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.

SUBMITTER: Tirkasheva S

PROVIDER: S-EPMC10439439 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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