One Bicyclic β-Lactam and Two Bicyclic γ-Lactam Compounds

Autor: Kees Goubitz, C. A. Reiss, Henk Schenk, D. J. A. De Ridder, Henk Hiemstra
Rok vydání: 1996
Předmět:
Zdroj: Acta Crystallographica Section C Crystal Structure Communications. 52:1473-1479
ISSN: 0108-2701
DOI: 10.1107/s0108270195014788
Popis: The crystal structures of the bicyclic β-lactam, rac-(2R*,4S*,6S*)-4-chloro-4-methyl-8-oxo-1- azabicyclo­[4.2.0]octane-2-carboxylic acid methyl ester, C10H14ClNO3, (1), and the bicyclic γ-lactams, rac-(5R*,7S*,9S*)-7-chloro-7- methyl-3-oxooctahydroindolizidine-5-carboxylic acid methyl ester, C11H16ClNO3, (2) and rac-(5R*,6S*,10R*)-3-oxo-6-vinyloctahydro-1H-pyrrolo[1,2-a]azepine-5-carboxylic acid methyl ester, C13H19NO3, (3), have been established by X-ray crystallography. In (1) and (2) the α-amino ester function and the Cl atom occupy an axial position in a chair-like piperidine ring. In (3) the methyl ester and the vinyl group are equatorially located on a chair-like seven-membered ring. The criteria defined by Foces-Foces, Cano & Garcia-Blanco [Acta Cryst. (1976), B32, 3029–3033] to determine the conformation of a six-membered ring are compared with those defined by Duax, Weeks & Rohrer [Top. Stereochem. (1976), 9, 271–383]. It can be seen that the former cannot be used to correctly determine the conformation of a six-membered ring in the case of strain imposed by a four-membered fused ring such as in (1).
Databáze: OpenAIRE