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Polymorphism in 3-acetyl-4-hydroxy-2H-chromen-2-one.

Afef Ghouili1, Ameni Brahmia1, Rached Ben Hassen1

  • 1Unité de chimie des matériaux et de l'environnement, UR11ES25, ISSBAT, Université de Tunis El Manar, 9 Avenue Dr Zoheir Safi, 1006 Tunis, Tunisia.

Acta Crystallographica. Section C, Structural Chemistry
|October 1, 2015
PubMed
Summary

A new polymorph of 3-acetyl-4-hydroxy-2H-chromen-2-one was discovered. Both polymorphs exhibit strong intramolecular hydrogen bonds, but differ in intermolecular stabilization, with π-π stacking in polymorph I and α-pyrone ring interactions in polymorph II.

Keywords:
3-acetyl-4-hydroxy-2H-chromen-2-oneactive pharmaceutical ingredients (APIs)crystal structurehydrogen bondingpharmaceutical compoundspolymorphismweak interactionsα-pyrone

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Polymorphism in organic compounds influences material properties.
  • Understanding crystal packing is crucial for material design.
  • 3-acetyl-4-hydroxy-2H-chromen-2-one exhibits known polymorphic forms.

Purpose of the Study:

  • To characterize a newly discovered polymorph (polymorph II) of 3-acetyl-4-hydroxy-2H-chromen-2-one.
  • To compare the crystal structure and intermolecular interactions of polymorph II with the original polymorph (polymorph I).

Main Methods:

  • Recrystallization from salt-melted ice to obtain polymorph II.
  • Single-crystal X-ray diffraction to determine crystal structures.
  • Analysis of hydrogen bonding and π-π stacking interactions.

Main Results:

  • A new polymorph (polymorph II) of 3-acetyl-4-hydroxy-2H-chromen-2-one was successfully synthesized and characterized.
  • Both polymorphs feature strong intramolecular O-H...O hydrogen bonds, with slightly greater H atom delocalization in polymorph II.
  • Polymorph I is stabilized by π-π stacking, while polymorph II is stabilized by parallel α-pyrone ring interactions.

Conclusions:

  • The discovery of a new polymorph highlights the complex crystallographic behavior of 3-acetyl-4-hydroxy-2H-chromen-2-one.
  • Differences in intermolecular interactions dictate the distinct crystal packing and stabilization mechanisms of the two polymorphs.
  • Further studies on the solid-state properties of these polymorphs are warranted.