Three aryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: hydrogen-bonded structures in two or three dimensions.
In (2SR,4RS)-7-chloro-2-exo-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(16)H(13)Cl(2)NO, (I), the molecules are linked by a combination of C-H...O and C-H...N hydrogen bonds into a chain of edge-fused R(3)(3)(12) rings. The isomeric compound (2S,4R)-7-chloro-2-exo-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (II), crystallizes as a single 2S,4R enantiomer and the molecules are linked into a three-dimensional framework structure by two C-H...O hydrogen bonds and one C-H...pi(arene) hydrogen bond. The molecules of (2S,4R)-7-chloro-2-exo-(1-naphthyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(20)H(16)ClNO, (III), are also linked into a three-dimensional framework structure, here by one C-H...O hydrogen bond and two C-H...pi(arene) hydrogen bonds. The significance of this study lies in its observation of the variations in molecular configuration and conformation, and in the variation in the patterns of supramolecular aggregation, consequent upon modest changes in the peripheral substituents.
Gómez
Sandra L
SL
Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
Raysth
Walter
W
Palma
Alirio
A
Cobo
Justo
J
Low
John N
JN
Glidewell
Christopher
C