Acta Cryst. (2004). E60, o173-o175  [ doi:10.1107/S160053680302796X ]

cis-8-Azabicyclo[5.2.0]nonan-9-one

Gy. Argay, A. Kálmán, Gy. Bernáth and Zs. Cs. Gyarmati

Abstract: The title compound, C₈H₁₃NO, with two chiral centres in the cis-junction between the -lactam and cycloheptane rings, crystallizes with an orthorhombic unit cell. The strain of the -lactam moiety forces the cycloheptane ring to assume a chair conformation characterized by C_s symmetry, which is less stable by 1.4  kcal  mol^-1 than the twist-chair form, built up around a twofold axis. The homochiral helices, maintained by N-HO=C hydrogen bonds, are organized in antiparallel mode around the respective screw axes of the non-centrosymmetric space group P2₁2₁2₁, which means that the enantiomers resolve in crystal conglomerates.

Online 10 January 2004

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