SCHEDULED MAINTENANCE
1,6-Diazabicyclo[4.4.4]tetradecane (1) and its inside-protonated ion (4) are essentially isostructural with effective D3 symmetry; the N,N′ distance contracts by 0.28 Å on protonated, giving the shortest known N–H:N hydrogen bond (2.53 Å).
R. W. Alder, A. G. Orpen and R. B. Sessions, J. Chem. Soc., Chem. Commun., 1983, 999 DOI: 10.1039/C39830000999
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