Abstract: | (2SR,4RS)‐7‐Fluoro‐2‐exo‐(2‐furyl)‐2,3,4,5‐tetrahydro‐1H‐1,4‐epoxy‐1‐benzazepine, C14H12FNO2, (I), crystallizes with Z′ = 2 in the space group P21/c. A combination of three C—H...O hydrogen bonds and one C—H...N hydrogen bond links the molecules into a complex chain of rings, and pairs of such chains are linked into a tube‐like structure by two C—H...π(arene) hydrogen bonds. There are no hydrogen bonds in the structure of racemic (2SR,4RS)‐2‐exo‐(5‐bromo‐2‐thienyl)‐7‐fluoro‐2,3,4,5‐tetrahydro‐1H‐1,4‐epoxy‐1‐benzazepine, C14H11BrFNOS, (II), while the molecules of (2S,4R)‐2‐exo‐(5‐bromo‐2‐thienyl)‐7‐trifluoromethoxy‐2,3,4,5‐tetrahydro‐1H‐1,4‐epoxy‐1‐benzazepine, C15H14BrF3NO2S, (III), are linked into sheets by a combination of two C—H...O hydrogen bonds and one C—H...π(arene) hydrogen bond. The significance of this study lies in its observation of the wide variation in the patterns of supramolecular aggregation, consequent upon modest changes in the peripheral substituents. |