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-(CH
3)
2-C
6H
3 (
1), 4-CH
3-C
6H
4 (
2), 4-NH
2-C
6H
4 (
3) and 2-NH
2-C
6H
4 (
4). The centralstannoxane motif (Sn
6O
6) is similar in all these compounds and is surrounded by six substituted benzoate groups. All the drumsshow an extensive supramolecular organization in the solid state. Accordingly, drum
1 forms a one-dimensional supramolecularassembly mediated by noncovalent interactions such as C-H···O and
···
interactions. Similarly, drums
2-
4 form interestingthree-dimensional supramolecular assemblies mediated by C-H···O, N-H···N, C-H···
, and
···
interactions in the solid state.The role of the peripheral aromatic substituents in determining the final course of the supramolecular assembly is discussed.