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Attempted co-crystallization of tolbutamide with p-phenylenediboronic acid and p-nitrophenol in EtOH afforded a modulated high Z′ crystal structure of the known form III of tolbutamide instead of the anticipated co-crystals. A novel form V of tolbutamide was crystallized when a trace of conc. HNO3 was added in MeOH solvent.
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Nath et al. (2010) studied this question.
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