in-out isomerism

https://doi.org/10.1351/goldbook.I03055
Isomerism found in bicyclic systems having long enough bridges to allow the bridgehead exocyclic bond or lone pair of electrons to point either inside the structure or outside.
molecule
molecule
Source:
PAC, 1996, 68, 2193. (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2210 [Terms] [Paper]