Analysis of the topology of the electron density and underlying local orbital interactions of the fully optimized structure of the molecular cage of the in-bicyclo[4.4.4]-1-tetradecyl cation reveals that the inside 3c2e C-(HC)-C-... hydrogen bond is not only unusual but also strong. The inside C-H bond of the unsaturated, neutral precursor bicyclo[4.4.4]-1-tetradecene is involved in an intramolecular C-H/pi interaction with the transannular double bond. Known and calculated H-1 and C-13 NMR properties, including diamagnetic and paramagnetic contributions to shielding tensors, are accounted for in terms of electron density redistributions and the unusual electronic environment within these hydrocarbon cages.