Ethyl 2,2′′-dioxo-2′,3′,5′,6′,7′,7a′-hexahydroacenaphthene-1-spiro-3′-1′H-pyrrolizine-2′spiro-1′′-acenaphthene-1-carboxylate

Abstract

In the title compound, C32H25NO4, the mean plane through the pyrrolizidine system is almost perpendicular [dihedral angle 88.9 (1)°] to that through one of the acenaphthene units, and the dihedral angle between the pyrrolizidine and the second acenaphthene system is 81.6 (1)°. In the pyrrolizidine system, one of the rings is in a half‐chair conformation while the other is in an envelope conformation. The overall conformation is twisted about the fusion bond. The crystal structure is stabilized by a C—H⋯O inter­molecular hydrogen bond.

2′-(2-Chlorophenyl)-1′-nitro-2′,3′,4′,5′,6′,7′-hexahydro-1H-indole-3-spiro-3′-1′H-pyrrolizin-2(3H)-one

“…The overall conformation of the pyrrolizidine nucleus is folded about the bridgehead bond, N1-C5. This observation is consistent with the structure reported by Usha et al (2005).…”

“…The extent of twist about the N1-C5 bond is given by the dihedral angle between the mean planes through the two five-membered rings, which is 51.3 (1)°. This observation is consistent with the structure reported by Usha et al (2005).…”

“…Bond lengths and bond angles of the pyrrolizidine group and the oxindole unit present no unexpected features and are in the same range as observed in reported stuctures (Govind et al, 2004;Usha et al, 2005). The C9═O1 double bond is slightly elongated [1.227 (2) Å] as a result of the hydrogen bonding.…”

“…ISSN 1600-5368 2 0 0 0 -(2-Chlorophenyl)-1 0 0 0 -nitro-2 0 0 0 ,3 0 0 0 ,4 0 0 0 ,5 0 0 0 ,6 0 0 0 ,7 0 0 0hexahydro-1H-indole-3-spiro-3 0 0 0 -1 0 0 0 Hpyrrolizin-2(3H)-one Bond lengths and bond angles of the pyrrolizidine group and the oxindole unit present no unexpected features and are in the same range as observed in reported structures (Govind et al, 2004;Usha et al, 2005). The C9 O1 double bond is slightly elongated [1.227 (2) Å ] as a result of the hydrogen bonding.…”

Hydrogen bonding in 1′-nitro-2′-phenyl-2′,3′,4′,5′,6′,7′-hexahydro-1H-indole-3-spiro-3′-1′H-pyrrolizidin-2(3H)-one: molecular chains built from alternating R_{2}^{2}(18) and R_{2}^{2}(8) rings

“…The bond lengths and angles of the indole and benzene ring systems are normal. The pyrrolizidine ring-fusion distance [N1-C5 = 1.481 (2) Å ] is in the same range as the other two N-C distances and compares quite well with those observed in related structures (Hay et al, 1982;Sussman & Wodak, 1973;Usha et al, 2005). Bond distances and angles around atom C2 are somewhat distorted, which is due to the spiro-atom character.…”