Crystal structure and characterization of the sulfamethazine–piperidine salt. Issue 3 (10th February 2023)

• Record Type: Journal Article
• Authors: González-González, Juan Saulo; Pérez-Espinoza, Salvador; Martínez-Martínez, Francisco Javier; Pineda-Contreras, Armando; Canseco-Martínez, Miguel Ángel; Flores-Alamo, Marcos; García-Ortega, Héctor
• Is Part Of: Acta crystallographica. Volume 79:Issue 3(2023)
• Page Start: 71
• Page End: 76
• Publication Date: 2023-02-10
• Subjects: sulfamethazine -- piperidine -- IR spectroscopy -- crystal structure -- solid‐state 13C NMR -- thermal analysis -- proton transfer -- solvent‐assisted grinding; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229622012050
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : The piperidinium–sulfamethazinate salt was prepared by the solvent‐assisted grinding method. The ions are connected by N—H + …O and N—H + …N interactions. The self‐assembly of sulfamethazinate anions displays the amine–sulfa C (8) motif. The supramolecular architecture of the salt revealed the formation of interconnected supramolecular sheets. Abstract : Sulfamethazine [ N 1 ‐(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 −, C5 H12 N + ·C12 H13 N4 O2 S − ) (I ). The salt was obtained by the solvent‐assisted grinding method and was characterized by IR spectroscopy, powder X‐ray diffraction, solid‐state 13 C NMR spectroscopy and thermal analysis [differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA)]. Salt I crystallized in the monoclinic space group P 21 / 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.