Five 2-aryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: isolated molecules and hydrogen-bonded chains and sheets.

(2SR,4RS)-2-exo-Phenyl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(15)NO, (I), (2SR,4RS)-2-exo-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(14)ClNO, (II), and (2SR,4RS)-2-exo-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(17)H(17)NO, (III), all crystallize with Z' = 2, in the space groups Cc, P2(1)/n and P2(1)/c, respectively. In each of (II) and (III), the conformations of the two independent molecules are significantly different. The molecules in (I) are linked by C-H...pi(arene) hydrogen bonds to form two independent chains, each containing only one type of molecule. The molecules in (II) are linked into sheets by a combination of C-H...O, C-H...(N,O) and C-H...pi(arene) hydrogen bonds, all of which link pairs of molecules related by inversion, while in (III), the molecules are linked into sheets by a combination of C-H...N, C-H...O and C-H...pi(arene) hydrogen bonds. There are no direction-specific intermolecular interactions of any kind in the structure of (2SR,4RS)-7-bromo-2-exo-phenyl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(14)BrNO, (IV), but in the structure of (2SR,4RS)-2-exo-(4-bromophenyl)-7-chloro-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(13)BrClNO, (V), a combination of one C-H...N hydrogen bond and one C-H...O hydrogen bond links the molecules into sheets of alternating centrosymmetric R(2)(2)(14) and R(6)(6)(22) rings. Comparisons are made with the structures of a number of related compounds.