Sulfonamide-pyridine-N-oxide cocrystals

Abstract

Hydrogen-bond motifs for the supramolecular synthesis of sulfonamide-pyridine-N-oxide complexes were derived from the analysis of cocrystal structures of aryl sulfonamides and pyridine-N-oxides. The sulfonamide NH donor persistently interacts with the N-oxide acceptor via a N-H ··· O hydrogen bond, though the exact geometry of the motif, such as discrete (D), infinite chain C(4), cyclic motifs R 42 (8) or R22 (4), varies from structure to structure. Surprisingly, the two-point R22 (8) cyclic motif of N-H···O and C- H···O hydrogen bonds, analogous to the heterosynthon in carboxamide-pyridine-N-oxide cocrystals, was not observed in sulfonamide-N-oxide cocrystals. The utility of this model study is demonstrated by making cocrystals of Furosemide with 4,4′-bipyridine-N,N′-dioxide and isonicotinamide-N-oxide. © 2011 American Chemical Society.