Spectroscopic properties of N-n-hexyltetrachlorophthalimide and supramolecular interactions in its crystals

N-n-hexyltetrachlorophthalimide has been characterized by X-ray diffraction, FTIR, Raman and NMR spectroscopy. Also B3LYP and DFT calculations have been carried out. The optimized bond lengths, bond angles and torsion angles calculated by B3LYP/6-31G(d,p) approach have been compared with the X-ray data. The screening constants for 13C and 1H atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants confirm the optimized geometry. The supramolecular structure is organized into hydrophilic and hydrophobic segments. The tetrachlorophthalimide moieties of the hydrophilic segments form infinite chains via halogen bonds CO⋯Cl. These bonds as well as weak intermolecular hydrogen bonds CH⋯O contribute to the parallel orientation of the chains and to the stabilization of their flat conformation. The intermolecular Cl⋯Cl interactions stabilize the organization of the hydrophilic segments.