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, C(14)H(12)FNO(2), (I), crystallizes with Z' = 2 in the space group P2(1)/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...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, C(14)H(11)BrFNOS, (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, C(15)H(14)BrF(3)NO(2)S, (III), are linked into sheets by a combination of two C-H...O hydrogen bonds and one C-H...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.