The compressed conformations and the coiling shapes extent of the 1,-diammonium-(oligo)ethyleneoxyde, OEG guests are determined within the internal space of the crystalline Pyrene Box host capsules. It was observed that the OEG chains have the tendency to fold in on themselves in random or S-shaped intermolecularly H-bonded conformations inside the Pyrene Box confined medium. The phenomenon was observed in solution through NMR spectroscopy and structural proof was provided by single crystal X-ray diffraction. The overall supramolecular spatial arrangement of the "Pyrene box" system present structural and dimensional variations/adaptations in order to accommodate the coiled OEG guests of different sizes and shapes.