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Conformational polymorphism VI: the crystal and molecular structures of form II, form III, and form V of 4-amino-N-2-pyridinylbenzenesulfonamide (sulfapyridine).

The crystal structures of three crystalline forms of 4-amino-N-pyridinylbenzenesulfonamide (sulfapyridine) have been determined by X-ray single crystal structure analysis. Form II crystallizes in space group P2(1)/c with four molecules in the unit cell: a = 0.6722(1) nm, b = 2.0593(5) nm, c = 0.8505(1) nm, beta = 101.14(1) degrees; Form III crystallizes in space group C2/c with eight molecules in the unit cell: a = 1.2830(2) nm, b = 1.1714(3) nm, c = 1.5400(3) nm, beta = 94.12(1) degrees; Form V crystallizes in the orthorhombic space group Pbca with 16 molecules in the unit cell: a = 2.4722(10) nm, b = 1.5710(15) nm, c = 1.2147(7) nm. The three structures were solved by direct methods and refined anisotropically to R factors of 0.045, 0.052, and 0.063, respectively. Bond lengths and bond angles agree well among the molecules in these structures; however, the system exhibits conformational polymorphism since the molecular conformation, as measured by torsion angles, differs significantly among the three forms. Sulfapyridine exhibits the imide configuration in all three structures rather than the amide form present in other sulfonamide compounds. Using the structural data, the powder patterns of the three forms have been computer generated to provide standard diffraction patterns for comparison with the variety of polymorphic forms reported in the literature.