K. Kranjc, Amadej Juranovič, M. Kočevar
Jan 10, 2012
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Journal
Journal of Chemical Crystallography
Abstract
The compounds methyl 3-(benzoylamino)-6-methyl-2-oxo-2H-pyran-5-carboxylate (1), C15H13NO5, and N-[5-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-2H-pyran-3-yl]benzamide (2), C21H19NO5, crystallize as a centrosymmetric hydrogen-bonded dimer facilitated by N–H···O interactions involving the amide and carbonyl moiety of the lactone group of adjacent molecules. Supramolecular aggregation in 1 is controlled by a combination of π–π interactions [centroid–centroid distance = 4.0745(11) Å] and weak C–H···O hydrogen bonding between the phenyl ring of the benzoylamino group and the carbonyl atom of the methoxycarbonyl group and in 2 by a combination of π–π interactions [centroid–centroid distance = 4.0699(8) and 4.1556(10) Å], weak C–H···O interactions between the methoxy substituents of the adjacent dimethoxyphenyl group and weak C–H··· π interactions.Graphical Abstract2H-Pyran-2-ones represent an important class of compounds useful for various ring transformations, the titled compounds crystallize as a centrosymmetric hydrogen-bonded dimers.