Three aryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: hydrogen-bonded structures in two or three dimensions

In (2SR,4RS)-7-chloro-2-exo-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H13Cl2NO, (I), the molecules are linked by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds into a chain of edge-fused R-3(3)(12) rings. The isomeric compound (2S,4R)-7-chloro-2-exo(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (II), crystallizes as a single 2S, 4R enantiomer and the molecules are linked into a three-dimensional framework structure by two C-H center dot center dot center dot O hydrogen bonds and one C-H center dot center dot center dot( arene) hydrogen bond. The molecules of (2S,4R)-7chloro-2-exo-(1-naphthyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1benzazepine, C20H16ClNO, (III), are also linked into a three-dimensional framework structure, here by one C-H center dot center dot center dot O hydrogen bond and two C-H center dot center dot center dot pi(arene) hydrogen bonds. The significance of this study lies in its observation of the variations in molecular configuration and conformation, and in the variation in the patterns of supramolecular aggregation, consequent upon modest changes in the peripheral substituents.