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The crystal structures of two chromone derivatives, viz. ethyl 6-(4-methyl-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate, C19H16O4, (1), and ethyl 6-(4-fluoro-phen-yl)-4-oxo-4H-chromene-2-carboxyl-ate C18H13FO4, (2), have been determined: (1) crystallizes with two mol-ecules 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 mol-ecule differs significantly from the others, even the two independent mol-ecules (a and b) of (1). In all three mol-ecules, the carbonyl groups of the chromone and the carboxyl-ate are trans-related. The supra-molecular structure of (1) involves only weak C-H⋯π inter-actions between H atoms of the substituent phenyl group and the phenyl group, which link mol-ecules into a chain of alternating mol-ecules a and b, and weak π-π stacking inter-actions between the chromone units. The packing in (2) involves C-H⋯O inter-actions, which form a network of two inter-secting ladders involving the carbonyl atom of the carboxyl-ate 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 inter-actions stack the mol-ecules by unit translation along the a axis.

acta crystallographica. section e, crystallographic communications

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

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