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The crystal structures of o-toluidinium chloride (1), o-toluidinium bromide (2) and two polymorphs of bicifadine hydrochloride (3) have been determined. The polymorphs of 3 differ in their molecular conformation and in their mode of packing. Crystallisation studies and quantum mechanical calculations show that the more readily crystallisable polymorph grows from the thermodynamically most stable conformer. On heating, conversion to the second polymorph takes place just below the melting point. The crystal structures of 1, 2 and the first polymorph of 3 have been successfully predicted using a procedure that is suitable for simple ionic organics.
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