Polymorphism and H-bonding of 2-[1(2H)-oxo-2-phthalazinyl]methylbenzoic acid

The three crystalline and one amorphous forms of the title compound, so far isolated, have been characterized by differential scanning calorimetry, thermomicroscopy, infrared spectroscopy and X-ray powder diffraction. From I was obtained by solidification of the melt at 200 degrees; form II by crystallization from water/ethanol 1/1; form III by grinding of II; the amorphous form by rapid cooling of the melt or by evaporation to dryness of a chloroform solution. From II melts of about 200 degrees and immediately crystallizes into form I, which melts at 210 degrees. Form III transforms into I at 165 degrees. The infrared spectra of form I is different from that of forms II and III, while each form has a different X-ray powder diffraction. From consideration of the infrared functional absorption bands, it can be derived that form I is a dimer with H-bonds between the carboxylic groups, forms II and III are monomers with intramolecular H-bond between the carboxylic group and the hydrazide carbonyl, displaying different crystal packings, and the amorphous form is a mixture of both monomers and dimers, the latters in greater amount.