7-Hydroxy-5-methoxy-6,8-dimethylflavanone: a natural flavonoid

• Published in: Acta crystallographica. Section C, Crystal structure communications Vol. 64; no. 6; pp. o353 - o356
• Main Authors: Dacunha-Marinho, Bruno, Martínez, Ana, Estévez, Ramón J.
• Format: Journal Article
• Language: English
• Published: 5 Abbey Square, Chester, Cheshire CH1 2HU, England International Union of Crystallography 01.06.2008; Wiley Subscription Services, Inc
• Subjects: Chemical compounds; Crystal structure; Crystallography; Electrons; Flavanones - chemistry; Flavonoids - chemistry; Hydrogen Bonding; Hydrogen bonds; Molecular Conformation
• ISSN: 0108-2701; 1600-5759
• DOI: 10.1107/S0108270108014959

The title flavonoid [systematic name: (2S)‐7‐hydroxy‐5‐methoxy‐6,8‐dimethyl‐2‐phenyl‐3,4‐dihydrochromen‐4(2H)‐one], C18H18O4, displays statistical conformational disorder, with three conformations of the molecule involving three orientations of the phenyl ring and two orientations of the fused heterocyclic ring. The conformational disorder is correlated with the isomerization equilibrium between the flavanone and chalcone forms. The conformational behaviour has a potential impact on the biological activity of this class of compounds. Moreover, π stacking interactions at van der Waals distances are present between the aromatic rings of chroman‐4‐one groups of symmetry‐related molecules. Apart from these π–π interactions, molecules are linked by strong O—H...O hydrogen bonds between hydroxy and carbonyl groups.