Even though  para-methyl benzyl alcohol p-MeBA II and para-chloro benzyl alcohol p-ClBA are quasi-isostructural and share the same hydrogen bond patterns the two crystals are not isomorphous. No new polymorphs could be obtained by conventional polymorph screening based on different solvents and different crystallization conditions. A new polymorph of p-MeBA named p-MeBA I, isomorphous with the crystal of p-ClBA, was induced by hetero-seeding with a small quantity of powdered p-ClBA added to a supersaturated hexane solution of p-MeBA before nucleation occurred. The alternate cross-crystallization, however, failed to give a new phase of p-ClBA isomorphous with known crystalline p-MeBA II. Mixed crystals of p-MeBA and p-ClBA were also prepared with different p-MeBA/p-ClBA ratios to understand the role of different functional groups in the crystal structure. Crystal phases were characterized by a combined used of single crystal and powder X-ray diffraction, DSC and SS NMR spectroscopy.

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