7-Hydroxy-5-methoxy-6,8-dimethylflavanone: a natural flavonoid
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 heter...
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Published in | Acta crystallographica. Section C, Crystal structure communications Vol. 64; no. 6; pp. o353 - o356 |
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Main Authors | , , |
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 | |
Online Access | Get full text |
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Summary: | 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. |
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Bibliography: | ArticleID:AYCSQ3134 istex:950350676B6C440A82100789CE5BDE6F121EF1F1 ark:/67375/WNG-XL2MQ2N5-D ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 ObjectType-Article-1 ObjectType-Feature-2 |
ISSN: | 0108-2701 1600-5759 |
DOI: | 10.1107/S0108270108014959 |