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Polymorphs and pseudopolymorphs of N,N'-dithiobisphthalimide.

Dorcas M M Farrell1, Christopher Glidewell, John N Low

  • 1School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland, UK.

Acta Crystallographica. Section B, Structural Science
|March 23, 2002
PubMed
Summary

N,N'-Dithiobisphthalimide forms diverse polymorphs and solvates. Crystallization conditions dictate molecular arrangements, including chains, ladders, and frameworks, influenced by hydrogen bonding and pi-pi stacking interactions.

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Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Supramolecular chemistry

Background:

  • N,N -Dithiobisphthalimide (I) is known to exhibit polymorphism and form solvates.
  • Understanding the crystal structures of these forms is crucial for predicting and controlling their solid-state properties.

Purpose of the Study:

  • To investigate the diverse crystalline forms of N,N -Dithiobisphthalimide obtained from various solvents.
  • To characterize the crystal structures, including polymorphs and solvates, and analyze the intermolecular interactions governing their formation.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structures of various polymorphs and solvates.
  • Analysis of hydrogen bonding, pi-pi stacking, and other non-covalent interactions was performed.

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Main Results:

  • Crystallization from methanol yielded a solvent-free polymorph (4) with molecules arranged in chains via C-H.O hydrogen bonds.
  • Crystallization from acetonitrile or dimethylformamide produced a solvent-free polymorph (5) with molecules forming molecular ladders.
  • Solvates were formed with nitromethane (monosolvate 6), chlorobenzene (hemisolvate 7), ethylbenzene (hemisolvate 8), tetrahydrofuran (solvate 9), tert-butanol (solvate 10), p-xylene (hemisolvate 11), and toluene (hemisolvate 12), each exhibiting distinct crystal packing and intermolecular interactions.

Conclusions:

  • The crystallization solvent significantly influences the solid-state form of N,N -Dithiobisphthalimide, leading to a wide array of polymorphs and solvates.
  • Intermolecular interactions, including hydrogen bonding and pi-pi stacking, play a critical role in stabilizing these different crystalline structures.
  • The study highlights the rich structural diversity of N,N -Dithiobisphthalimide and provides insights into crystal engineering.