title: Two stereoisomers of the rat toxicant norbormide.
abstract: The structures of two diastereoisomers of norbormide [systematic name: 5-[hydroxy(phenyl)(2-pyridyl)methyl]-8-[phenyl(2-pyridyl)methylene]-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione], viz. the unsolvated molecule, C(33)H(25)N(3)O(3), and the ethyl acetate hemisolvate, C(33)H(25)N(3)O(3).0.5C(4)H(8)O(2), have been determined unambiguously. They differ in the relative stereochemistry about the exocyclic double bond and the relative conformations of the aryl rings. Each compound exhibits both intra- and intermolecular hydrogen bonding.
authors.affiliation: Department of Chemistry, University of Canterbury, Christchurch, New Zealand. peter.steele@canterbury.ac.nz
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Steel
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
authors.forename: Brian
authors.initials: B
authors.lastname: Hopkins
authors.forename: David
authors.initials: D
authors.lastname: Rennison
mesh_terms: D000818:Animals; D006860:Hydrogen Bonding; D008956:Models, Chemical; D009636:Norbornanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D051381:Rats; D013237:Stereoisomerism
chemical_list: D009636:Norbornanes; C005321:norbormide