Unless there is a 7-endo substituent, 3-azabicyclo[3.3.1]nonanes exist as twin-chair conformation in which the lone pair of electrons on N(3) strongly repels the C(7)H group, leading to considerable distortion of the cyclohexane ring.
P. J. Cox, P. H. McCabe, N. J. Milne and G. A. Sim, J. Chem. Soc., Chem. Commun., 1985, 626 DOI: 10.1039/C39850000626
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