Three tetrahydro-1,4-epoxy-1-benzazepines carrying pendent heterocyclic substituents: supramolecular structures in zero, one or two dimensions

(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 P2(1)/c. A combination of three C-H center dot center dot center dot O hydrogen bonds and one C-H center dot center dot center dot 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 center dot center dot center dot pi(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 center dot center dot center dot O hydrogen bonds and one C-H center dot center dot center dot pi(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.