Ring conformations and intermolecular interactions in two fused dibenzoazocines.
5-Acetyl-2-chloro-8,11-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f]azocine, C(19)H(20)ClNO, (I), crystallizes as a single fully ordered isomer, but 14-acetyl-8,11-dimethyl-7,8,13,14-tetrahydrobenzo[f]naphtho[1,2-b]azocine-14-acetyl-8,9-dimethyl-7,8,13,14-tetrahydrobenzo[f]naphtho[1,2-b]azocine (74/26), C(23)H(23)NO, (II), exhibits threefold whole-molecule disorder involving both configurational and structural isomers. In (I) and in the predominant form of (II), the azocine rings adopt very similar conformations, forming boat-shaped rings having approximate twofold rotational symmetry. There are no direction-specific intermolecular interactions in the crystal structure of (I), but the molecules of (II) are weakly linked into chains by an aromatic pi-pi stacking interaction. The compounds were made under green conditions using an acid-catalysed cyclization process having very high atom utilization.
Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
Andrés F
AF
Yepes
Ederson
E
Jaimes
Ali
A
Bahsas
Alirio
A
Palma
Michael B
MB
Hursthouse
Justo
J
Cobo
Christopher
C
Glidewell