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Related Experiment Videos

3-Iodo-1H-pyrazolo-[3,4-b]pyridine.

Ping-Hsin Huang1, Yuh-Sheng Wen2, Jiun-Yi Shen3

  • 1Cardinal Tien College of Healthcare & Management, Taipei, 231, Taiwan.

Acta Crystallographica. Section E, Structure Reports Online
|June 19, 2014
PubMed
Summary

This study details the crystal structure of C6H4IN3, revealing a nearly planar molecule. It highlights N-H⋯N hydrogen bonds forming dimers and C-I⋯N halogen bonds creating zigzag chains, with significant π-π stacking interactions.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding the solid-state structure of heterocyclic compounds is crucial for predicting their chemical behavior and material properties.
  • The interplay of non-covalent interactions, such as hydrogen bonds and halogen bonds, dictates crystal packing and molecular assembly.
  • Planarity and dihedral angles in organic molecules influence their electronic properties and intermolecular interactions.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C6H4IN3.
  • To investigate the intermolecular interactions, including hydrogen bonding, halogen bonding, and π-π stacking, present in the crystal lattice.
  • To analyze the molecular geometry, specifically the planarity and dihedral angle between the pyridine and pyrazole rings.

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Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
  • Analysis of the crystal structure involved identifying hydrogen bonds (N-H⋯N) and halogen bonds (C-I⋯N).
  • Intermolecular interactions, including π-π stacking, were quantified by measuring inter-planar and centroid-centroid distances.

Main Results:

  • The title compound, C6H4IN3, exhibits a nearly planar conformation with a dihedral angle of 0.82(3)° between the pyridine and pyrazole rings.
  • Inversion dimers formed through N-H⋯N hydrogen bonds are observed, linking molecules in pairs.
  • Zigzag chains are formed along the b-axis direction via C-I⋯N halogen bonds, with additional π-π stacking interactions present.

Conclusions:

  • The crystal structure of C6H4IN3 is characterized by a combination of hydrogen bonding, halogen bonding, and π-π stacking, leading to a well-defined supramolecular architecture.
  • The observed planarity and specific intermolecular interactions provide insights into the solid-state behavior and potential applications of this heterocyclic compound.
  • The study demonstrates the importance of non-covalent interactions in directing the self-assembly of organic molecules in the crystalline state.