Influence of Aromatic Substituents on the Supramolecular Architectures of Monoorganooxotin Drums

The reaction of <i>n</i>-BuSn(O)(OH) with various substituted benzoic acids affords hexameric organostannoxane drums, [<i>n</i>-BuSn(O)OC(O)R]<sub>6</sub>, where R = 2,6-(CH<sub>3</sub>)<sub>2</sub>−C<sub>6</sub>H<sub>3</sub> (<b>1</b>), 4-CH<sub>3</sub>−C<sub>6</sub>H<sub>4</sub> (<b>2</b>), 4-NH<sub>2</sub>−C<sub>6</sub>H<sub>4</sub> (<b>3</b>) and 2-NH<sub>2</sub>−C<sub>6</sub>H<sub>4</sub> (<b>4</b>). The central stannoxane motif (Sn<sub>6</sub>O<sub>6</sub>) 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 <b>1</b> forms a one-dimensional supramolecular assembly mediated by noncovalent interactions such as C−H···O and π···π interactions. Similarly, drums <b>2</b>−<b>4</b> 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.