Polymorphism in a sulfamethoxazole derivative: Coexistence of five polymorphs in methanol at room temperature

Abstract

A Schiff base derived from 2-hydroxy-1-naphthaldehyde and a well-known antibiotic sulfamethoxazole affords seven different conformational isomers which are present in five polymorphic forms in methanol solvent at room temperature. An exclusive preference for one of the four possible pairs of sulfonamide–sulfonimide and phenolimine–ketoenamine tautomeric structures has been observed in the crystal structures of these polymorphs. This represents the first example of coexistence of five polymorphs in solution for any of the known compounds so far.

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