Crystal structure and characterization of the sulfamethazine-piperidine salt

Sulfamethazine [N¹-(4,6-dimethylpyrimidin-2-yl)sulfanilamide] is an antimicrobial drug that possesses functional groups capable of acting as hydrogen-bond donors and acceptors, which make it a suitable supramolecular building block for the formation of cocrystals and salts. We report here the crystal structure and solid-state characterization of the 1:1 salt piperidinium sulfamethazinate (PPD⁺·SUL^-, C₅H₁₂N⁺·C₁₂H₁₃N₄O₂S^-) (I). The salt was obtained by the solvent-assisted grinding method and was characterized by IR spectroscopy, powder X-ray diffraction, solid-state ¹³C NMR spectroscopy and thermal analysis [differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA)]. Salt I crystallized in the monoclinic space group P2₁/n and showed a 1:1 stoichiometry revealing proton transfer from SUL to PPD to form salt I. The PPD⁺ and SUL^- ions are connected by N-H⁺...O and N-H⁺...N interactions. The self-assembly of SUL^- anions displays the amine-sulfa C(8) motif. The supramolecular architecture of salt I revealed the formation of interconnected supramolecular sheets.