Publication Date:
2014-12-21
Description:
Four N-(4-halophenyl)-4-oxo-4H-chromene-3-carboxamides (halo = F, Cl, Br and I), N-(4-fluorophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10FNO3, N-(4-chlorophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10ClNO3, N-(4-bromophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10BrNO3, N-(4-iodophenyl)-4-oxo-4H-chromene-3-carboxamide, C16H10INO3, have been structurally characterized. The molecules are essentially planar and each exhibits an anti conformation with respect to the C—N rotamer of the amide and a cis geometry with respect to the relative positions of the Carom—Carom bond of the chromone ring and the carbonyl group of the amide. The structures each exhibit an intramolecular hydrogen-bonding network comprising an N—H...O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak Carom—H...O interaction with the O atom of the carbonyl group of the amide as acceptor, which forms another S(6) ring. All four compounds have the same supramolecular structure, consisting of R22(13) rings that are propagated along the a-axis direction by unit translation. There is π–π stacking involving inversion-related molecules in each structure.
Keywords:
crystal structuredrug designchromonesconformationsupramolecular structure
Electronic ISSN:
1600-5368
Topics:
Chemistry and Pharmacology
,
Geosciences
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