On the importance of intermolecular interactions of 3-(2,3-dihydroxy-isopentyl)-4-hydroxyacetophenone: Crystal structure, spectroscopic and hirshfeld surface analysis

GIL, DIEGO M.; LIZARRAGA, EMILIO; ECHEVERRÍA, GUSTAVO A.; PIRO, OSCAR E.; CATALÁN, CÉSAR A.N.

JOURNAL OF MOLECULAR STRUCTURE

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2020 vol. 1217 p. 128393 - 128404

0022-2860

The compound 3-(2,3-dihydroxy-isopentyl)-4-hydroxyacetophenone has been synthesized and characterized by 1H Nuclear Magnetic Resonance (NMR), Infrared (IR) and Raman spectroscopies and its crystal structure was solved by single crystal X-ray diffraction. The molecular geometry of the compound wasinvestigated theoretically by performing density functional theory (DFT) calculations to access reliable results to the experimental data. The substance crystallizes in the triclinic P1 crystal system with Z = 2 molecules per unit cell. The crystal structure of the compound shows the two methyl groups attached to the C11 atom are in a gauche conformation in relation to the C9 methylene group which in turn is antiperiplanar with respect to the C11 hydroxyl group. A similar disposition was observed for the C13 methyl group in relation to the C10 hydroxyl group. The most stable conformer obtained by conformational analysis shows the O3eH3 and O4eH4 hydroxyl groups in an anti-conformation. The differences observed between experimental and calculated results were interpreted in terms of intermolecular interactions in the crystal packing. The structure reveals that the crystal packing is governed by OeH/O hydrogen bonding and weak CeH/O and CeH$$$p non-covalent interactions. A detailed analysis ofHirshfeld surfaces and their associated 2D fingerprint plots allowed quantifying the interactions within the crystal structures.