Studies in crystal engineering: structure–reactivity correlations of substituted styrylcoumarins and related systems

Abstract

The solid state photochemical behaviour of 7-hydroxy-4-styrylcoumarin 1 and several of its derivatives and analogues has been investigated. All the compounds with the exception of 7-methoxy-4-styrylcoumarin 2 are photolabile and yield anti-HT dimers. It has been observed that chloro substitution in the systems studied does not lead to the expected β-packing mode. The photobehaviour of 1 and 2 has been correlated with their crystal structures. Reasons for α-packing have been examined. The systematics in the arrangement of the carbonyl group and phenyl group of the close neighbours in the crystals of 1, 2 and a few other cases are presented.