Two nitrates of dapsone: New candidates for non-linear optical materials

Non-linear optical properties (NLO) and hyperpolarizability calculations of two new hybrid organic-inorganic compounds were investigated. Compound (4-amino, 4ʹ-azaniumyldiphenyl) sulfone nitrate (1) and [(4,4ʹ-diazaniumylphenyl) sulfone] dinitrate (2) were prepared from dapsone (DDS) and characterized. Their structures were established by X-ray single-crystal analysis. While [4-amino, 4ʹ-azaniumyldiphenyl) sulfone nitrate] is mono-protonated, [(4,4ʹ-diazaniumylphenyl) sulfone] dinitrate is di-protonated. The crystals were stabilized by a three-dimensional network of intermolecular hydrogen bonds. The Hirshfeld surface analysis with 2D Fingerprint plots have revealed that the O/H, C/H, H/H and N/H contacts in 1 and the O/H, C/H, H/H, N/H and C/C contacts in 2 are the main intermolecular interactions.