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...O and C—H...N hydrogen bonds into a chain of edge‐fused R₃³(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...O hydrogen bonds and one C—H...π(arene) hydrogen bond. The molecules of (2S,4R)‐7‐chloro‐2‐exo‐(1‐naphthyl)‐2,3,4,5‐tetrahydro‐1H‐1,4‐epoxy‐1‐benzazepine, C₂₀H₁₆ClNO, (III), are also linked into a three‐dimensional framework structure, here by one C—H...O hydrogen bond and two C—H...π(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.