Crystal structures of ethyl 6-(4-methylphenyl)-4-oxo-4H-chromene-2-carboxylate and ethyl 6-(4-fluorophenyl)-4-oxo-4H-chromene-2-carboxylate

Abstract

The crystal structures of two chromone derivatives, viz. ethyl 6-(4-methylphenyl)-4-oxo-4H-chromene-2-carboxylate, C19H16O4, (1), and ethyl 6-(4-fluorophenyl)-4-oxo-4H-chromene-2-carboxylate C18H13FO4, (2), have been determined: (1) crystallizes with two molecules in the asymmetric unit. A comparison of the dihedral angles beween the mean planes of the central chromone core with those of the substituents, an ethyl ester moiety at the 2-position and a para-substituted phenyl ring at the 6-position shows that each molecule differs significantly from the others, even the two independent molecules (a and b) of (1). In all three molecules, the carbonyl groups of the chromone and the carboxylate are trans-related. The supramolecular structure of (1) involves only weak C - H⋯π interactions between H atoms of the substituent phenyl group and the phenyl group, which link molecules into a chain of alternating molecules a and b, and weak π-π stacking interactions between the chromone units. The packing in (2) involves C - H⋯O interactions, which form a network of two intersecting ladders involving the carbonyl atom of the carboxylate group as the acceptor for H atoms at the 7-position of the chromone ring and from an ortho-H atom of the exocyclic benzene ring. The carbonyl atom of the chromone acts as an acceptor from a meta-H atom of the exocyclic benzene ring. π-π interactions stack the molecules by unit translation along the a axis.