Crystal and Molecular Structure of 1-Azabicyclo[3.3.3]undecane Hydrochloride. Correlation of Some Molecular Dimensions with Spectroscopic Properties

Andrew H.J. Wang, Roger J. Missavage, Stephen R. Byrn, Iain C. Paul

Research output: Contribution to journalArticlepeer-review

53 Citations (Scopus)

Abstract

The crystal structure of the hydrochloride salt of 1-azabicyclo[3.3.3]undecane has been determined on the basis of 1664 nonzeoo intensities measured on a diffractometer. The crystals are triclinic with a = 10.830 (8) Å, b = 7.122 (6) Å, c = 7.014 (3) Å, a = 97° 58′ (4′), β =90° 24′(4′), and γ = 96° 17′(4′). The space group is and there are two molecules of C10H20NCl in the unit cell. The structure, including hydrogen atoms, has been refined by full-matrix least-squares methods to an R factor of 0.047. The cation has effective but noncrystallographic C3 symmetry. The three constituent eightmembered rings are in the boat-chair (BC) conformation with the detailed geometry being a compromise between torsional, bond angle, and transannular H—H nonbonded effects. The C–C–C, C–N–C, and N–C–C bond angles are all increased above tetrahedral values. The large angles in the cation can be correlated with the uv spectrum and J13C–H coupling constant at the methine carbon atom of the free base. There is an N+–H—Cl hydrogen bond of length 2.978 (3) Å.

Original languageEnglish
Pages (from-to)7100-7104
Number of pages5
JournalJournal of the American Chemical Society
Volume94
Issue number20
DOIs
Publication statusPublished - Oct 1 1972
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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