A new bis-Tröger's base was prepared from a tetraamine precursor as a mixture of two diastereoisomers. One of the isomers has a chair-like geometry, and the other possesses a boat-like geometry, embodying molecular tweezers. A one-pot preparation of bis-TB isomers and their interconversion under acid conditions was also studied. Structures of both isomers were confirmed by single-crystal X-ray diffraction. Extensive spectroscopic data, including 1H and 13C NMR, IR and Raman spectra of the isomers, are given.