in-out isomerism

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
I03055-2
Source:
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2210