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

G. Argay, A. Kálmán, G. Bernáth, Zsuzsanna Cs Gyarmati

Research output: Contribution to journalArticle

3 Citations (Scopus)

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
JournalActa Crystallographica Section E: Structure Reports Online
Volume60
Issue number2
DOIs
Publication statusPublished - Feb 2004

Fingerprint

Cycloheptanes
Lactams
seats
Enantiomers
rings
enantiomers
screws
helices
Conformations
Hydrogen
Hydrogen bonds
hydrogen bonds
Crystals
symmetry
cells
crystals

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

Cite this

Cis-8-Azabicyclo[5.2.0]nonan-9-one. / Argay, G.; Kálmán, A.; Bernáth, G.; Gyarmati, Zsuzsanna Cs.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 60, No. 2, 02.2004.

Research output: Contribution to journalArticle

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