Four differently substituted 2-aryl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepines: hydrogen-bonded structures in one, two and three dimensions

In (2RS, 4SR)-7-chloro-2-exo-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H12Cl2FNO, (I), molecules are linked into chains by a single C-H center dot center dot center dot pi(arene) hydrogen bond. (2RS, 4SR)-2-exo-(2-Chloro-6-fluorophenyl)2,3,4,5- tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H13ClFNO, (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, C18H19NO, (III), are linked into sheets by a combination of C-H center dot center dot center dot N and C-H center dot center dot center dot(arene) hydrogen bonds. (2S, 4R)-2-exo-(2-Chlorophenyl)- 2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H14ClNO, (IV), crystallizes as a single enantiomer and the molecules are linked into a three-dimensional framework structure by a combination of one C-H center dot center dot center dot O hydrogen bond and three C-H center dot center dot center dot pi(arene) hydrogen bonds.