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.
I03055-1.png
I03055-2.png
Source:
PAC, 1996, 68, 2193. 'Basic terminology of stereochemistry (IUPAC Recommendations 1996)' on page 2210 (https://doi.org/10.1351/pac199668122193)