Prohens López, RafaelPortell Bueso, AnnaFont Bardia, Ma. MercedesBauzá, AntonioFrontera, Antonio2017-12-222017-12-222016-07-111466-8033https://hdl.handle.net/2445/118854We report the X-ray solid state structures of two tertiary squaramides, i.e. 3-(diethylamino)-4-ethoxy-cyclobutene-1,2-dione (1) and bis-3,4-(diethylamino)-cyclobutene-1,2-dione (2). Compound 1 forms electrostatically compressed dimers in the solid state. Moreover, compound 2 exhibits a remarkable solid state architecture resembling a lipid bilayer. This supramolecular assembly has been analyzed using high level DFT calculations and Bader's theory of "atoms-in-molecules". The antiparallel CO⋯CO interactions of the cyclobutenedione rings and hydrophobic interactions involving the ethyl chains are crucial for the formation of the bilayer assembly in the solid state7 p.application/pdfengcc-by (c) Prohens López, Rafael et al., 2016http://creativecommons.org/licenses/by/3.0/esPolimorfisme (Cristal·lografia)Química supramolecularPolymorphism (Crystallography)Supramolecular chemistryinfo:eu-repo/semantics/article6680992017-12-22info:eu-repo/semantics/openAccess