In (2RS,4SR)-7-chloro-2-exo-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(12)Cl(2)FNO, (I), molecules are linked into chains by a single C-H...pi(arene) hydrogen bond. (2RS,4SR)-2-exo-(2-Chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(13)ClFNO, (II), is isomorphous with compound (I) but not strictly isostructural with it, as the hydrogen-bonded chains in (II) are linked into sheets by an aromatic pi-pi stacking interaction. The molecules of (2RS,4SR)-7-methyl-2-exo-(4-methylphenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(18)H(19)NO, (III), are linked into sheets by a combination of C-H...N and C-H...pi(arene) hydrogen bonds. (2S,4R)-2-exo-(2-Chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(14)ClNO, (IV), crystallizes as a single enantiomer and the molecules are linked into a three-dimensional framework structure by a combination of one C-H...O hydrogen bond and three C-H...pi(arene) hydrogen bonds.