Novel neo-confused octaphyrin(1.1.1.1.1.1.1.0) (1) was synthesized by oxidative ring closure of an octapyrrane bearing two terminal 鈥渃onfused鈥?pyrroles. Crystal structures of its Zn(II) and Cu(II) complexes (2 and 3) show a figure-of-eight conformation with unique mononuclear coordination structures. Photophysical data and theoretical calculations suggest that the neo-confused octaphyrin 1 is a 34蟺 electron conjugated species showing nonaromaticity. Coordination of copper and zinc ions results in the further narrowing of the HOMO鈥揕UMO gaps.