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Polymorphism of oxindole as the core structure in bioactive compounds

Abstract

A new polymorph of oxindole (termed as “δ–form”) has been found and characterized by single-crystal X-ray diffraction. Its structural properties were compared with those of the previously reported polymorphs (the α-, β- and δ-forms). This polymorphic form was crystallized for the first time but could not be obtained reproduceably later. Thus, the δ–form can serve as an example of the “disappearing polymorphs”. As a result, the three previously reported α-, β- and γ–forms have now been identified by powder X-ray diffraction, vibrational spectroscopy (infrared and Raman) and calorimetry (differential scanning calorimetry). In the structures of the earlier known α- and β-forms, N—H⋯O hydrogen bonds connect the molecules into dimers, while the crystals of the γ- and δ-forms contain hydrogen-bonded chains of associated molecules. An analysis of Hirshfeld surfaces and fingerprint plots have been also performed to study intermolecular interactions in the crystal network of each polymorph. The spectroscopic and thermal investigations showed that the polymorphs convert into α-form what indicates that α-form is the most stable at ambient temperature. Additionally, the α- and β-forms are enantiotropically-related phases, whereas the γ-form is monotropically related to the α-form. Unexpectedly, the β- and γ- forms were found to be unstable under Cu Kα radiation and both gradually transformed into the α-form with the γ-phase being more stable.

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Publication details

The article was received on 04 Jul 2017, accepted on 09 Feb 2018 and first published on 09 Feb 2018


Article type: Paper
DOI: 10.1039/C7CE01237C
Citation: CrystEngComm, 2018, Accepted Manuscript
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    Polymorphism of oxindole as the core structure in bioactive compounds

    B. Hachuła, M. Zubko, P. Zajdel, M. Książek, J. Kusz, O. Starczewska, J. Janek and W. A. Pisarski, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C7CE01237C

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