Supra­molecular assembly of mebendazolium and di­hydrogen phosphate ions in a new anthelmintic salt

Abstract

A new mebendazolium di­hydrogen phosphate phospho­ric acid solid compound was obtained. As expected, the mebendazolium cation and the di­hydrogen phosphate anion assemble in the solid state in an R₂²(8) hydrogen-bond-driven supra­molecular motif.

A new mebendazolium di­hydrogen phosphate phospho­ric acid solid material was obtained and characterized by single-crystal X-ray diffraction and complementary solid-state techniques {systematic name: 5-benzoyl-2-[(meth­oxy­carbon­yl)amino]-1H-1,3-benzo­diazol-3-ium di­hydrogen phosphate–phos­pho­ric acid (1/1), C₁₆H₁₄N₃O₃⁺·H₂PO₄⁻·H₃PO₄}. Structure solution confirmed proton transfer from phospho­ric acid towards the basic imidazole ring of mebendazole. The mebendazolium cation and the di­hydrogen phosphate anion assemble in the solid state in a cyclic hydrogen-bond-driven supra­molecular motif, as observed in all mebendazolium/oxyanions structures reported in the literature. This salt crystallizes in the monoclinic P2₁/c (No. 14) space group. A detailed study of the crystal structure performed by atom-to-atom and global Hirshfeld surface analysis indicates that several hydrogen bonds act as the main inter­molecular inter­actions stabillizing the material. The new material is stable up to 458 K.