First X-ray structural characterisation of host–guest interactions in tetra-tetrazole macrocycles

The syntheses of tetra-tetrazole macrocycles, containing two 1,3-bis(tetrazole)benzene units linked by a variety of n-alkyl (n=3, 5, 7 or 9 carbon atoms) chain lengths, are described. The crystal structures of two 1,3-bis(tetrazole)benzenes containing pendant bromoalkyl chains (n=3 or 5) are reported. A tetra-tetrazole macrocycle has also been structurally characterised and contains an unexpected ‘host–guest’ interaction through binding of a chloroform solvent molecule. The resulting deviation of the macrocycle from planarity results from a combination of the ‘host–guest’ interaction and strong intermolecular interactions between adjacent tetrazole and phenylene rings.