Influence of aromatic substituents on the supramolecular architectures of monoorganooxotin drums

Abstract

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.