Influence of Aromatic Substituents on the Supramolecular Architectures of Monoorganooxotin Drums

The reaction of n-BuSn(O)(OH) with various substituted benzoic acids affords hexameric organostannoxane drums,
[n-BuSn(O)OC(O)R]6, where R = 2,6-(CH3)2−C6H3 (1), 4-CH3−C6H4 (2), 4-NH2−C6H4 (3) and 2-NH2−C6H4 (4). The central
stannoxane motif (Sn6O6) is similar in all these compounds and is surrounded by six substituted benzoate groups. All the drums
show an extensive supramolecular organization in the solid state. Accordingly, drum 1 forms a one-dimensional supramolecular
assembly mediated by noncovalent interactions such as C−H···O and π···π interactions. Similarly, drums 2−4 form interesting
three-dimensional supramolecular assemblies mediated by C−H···O, N−H···N, C−H···π, and π···π interactions in the solid state.
The role of the peripheral aromatic substituents in determining the final course of the supramolecular assembly is discussed.