Quantum chemistry studies of various tautomeric/rotameric forms of the furanyl analogues of acetyl dihydroxychalcone (FC) and dihydroxydichalcone (FDC) have shown that the thermodynamically most stable molecules are planar. In the crystalline solid phase, both molecules are more (FDC) or less (FC) non-planar. Two relatively strong intramolecular H-bonds, whose existence is evidenced by X-ray, computational, and spectral investigations, stabilize the planar geometry and influence the features of the lowest energy tautomers/rotamers of both compounds. Extending to the visible region, the electronic absorption of FC and FDC is accompanied by an intramolecular electron density shift, a property that could have analytical implications. Keywords Chalcone and dichalcone furanyl analogues Á Crystal and computed structures Á Tautomerism Á Intra-and intermolecular interactions Á Spectral features Electronic supplementary material The online version of this article (
In the crystal structure of the title compound, C15H11FO2, molecules form inversion dimers through pairs of weak C—H⋯O hydrogen bonds. Dimers oriented in parallel, linked by C—H⋯π contacts, are arranged in columns along the b axis. The fluorophenyl ring and the benzene ring of the 2H-chromen-4(3H)-one unit are inclined to one another by 70.41 (16)°. They are respectively parallel in a given column or almost perpendicular [oriented at an angle of 87.8 (1)°] in neighbouring (inversely oriented) columns, forming a herringbone pattern.
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