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Sulfonamide drugs are well known antibacterial and antimicrobial molecules for pharmaceutical development. Building a library of suitable supramolecular synthons for the sulfonamide functional group and understanding their crystal structures with partner coformer molecules continues to be a challenge in crystal engineering. Although a few sulfonamide cocrystals with amides and N -oxides have been reported, the body of work on sulfonamide synthons is limited compared with those that have carb-oxy-lic acids and carboxamides. To address this structural gap, the present work is primarily focused on sulfonamide-lactam and sulfonamide- syn -amide synthons with drugs such as celecoxib, hydro-chloro-thia-zide and furosemide. Furthermore, the electrostatic potential of previously reported cocrystals has been recalculated to show that the negative electrostatic potential on the lactam and syn -amide O atom is higher compared with the charge on carboxamide and pyridine N -oxide O atoms. The potential of sulfonamide molecules to form cocrystals with syn -amides and lactams are evaluated in terms of the electrostatic potential energy for the designed supramolecular synthons.

Supramolecular synthon hierarchy in sulfonamide cocrystals with syn-amides and N-oxides