Directed formation of an organotin sulfide cavitand and its transformation into a rugby-ball-like capsule.

We report the systematic synthesis and thorough characterization of a discrete organotin sulfide cavitand, [R(B)(4)Sn(12)S(20)] {1, R(B) = 1,5-bis[(E)-2-(4-methylpentan-2-ylidene)hydrazinyl]naphthalene}, which readily undergoes a unique transformation into a stable, rugby-ball-like capsule, [R(B)(3)Sn(6)S(8)][(SnCl(3))(2)] (2), upon addition of a protic acid. DMF molecules are embedded within the cavities of both compounds by hydrogen-bonding interactions, spotlighting the title compounds with respect to molecular containment.