Four 1-naphthyl-substituted tetrahydro-1,4-epoxy-1-benzazepines: hydrogen-bonded structures in one, two and three dimensions.
(2S*,4R*)-2-exo-(1-Naphthyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(20)H(17)NO, (I), crystallizes with Z' = 2 in the space group P2(1); the two independent molecules have the same absolute configuration, although this configuration is indeterminate. The molecules of each type are linked by a combination of C-H...O and C-H...π(arene) hydrogen bonds to form two independent sheets, each containing only one type of molecule. (2SR,4RS)-7-Methyl-2-exo-(1-naphthyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(21)H(19)NO, (II), crystallizes as a true racemate in the space group P2(1)/c, and a combination of C-H...N, C-H...O and C-H...π(arene) hydrogen bonds links the molecules into sheets, each containing equal numbers of the two enantiomorphs. (2S*,4R*)-2-exo-(1-Naphthyl)-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(21)H(16)F(3)NO(2), (III), crystallizes as a single enantiomorph, as for (I), but now with Z' = 1 in the space group P2(1)2(1)2(1); again, the absolute configuration is indeterminate. A single C-H...π(arene) hydrogen bond links the molecules of (III) into simple chains. (2S,4R)-8-Chloro-9-methyl-2-exo-(1-naphthyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(21)H(18)ClNO, (IV), crystallizes as a single enantiomorph of well defined configuration, in the space group P2(1)2(1)2(1), where two independent C-H...π(arene) hydrogen bonds link the molecules into a single three-dimensional framework structure.
Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
Carlos M
CM
Sanabria
Sandra L
SL
Gómez
Alirio
A
Palma
Justo
J
Cobo
Christopher
C
Glidewell