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

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Abstract

The title compound, C8H13NO, with two chiral centres in the cis-junction between the β-lactam and cycloheptane rings, crystallizes with an orthorhombic unit cell. The strain of the β-lactam moiety forces the cycloheptane ring to assume a chair conformation characterized by Cs 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-H⋯O=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.

Original languageEnglish
Pages (from-to)o173-o175
JournalActa Crystallographica Section E: Structure Reports Online
Volume60
Issue number2
DOIs
Publication statusPublished - Feb 1 2004

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ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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