One methylene too far: The solid state structure of the para-sulfonatomethylcalix[4]arene

We report here, the first crystallographic structure of the new water soluble calixarene, para-sulfonatomethylcalix[4]arene. Anchoring a methylene group between the aromatic core of the calixarene and sulfonate groups extended the hydrophobic cavity but led to a more flexible macromolecule allowing formation of hydrogen bonds between vicinal sulfonate groups, causing the groups to point towards the cavity and effectively close it, with S  S distances of 9.7 Å × 7.9 Å. The packing motif consists of bilayers of para-sulfonatomethylcalix[4]arene along both the a and b axis.