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Related Experiment Videos

p-Nitrophenyl isocyanide.

Matthias Zeller1, Allen D Hunter

  • 1Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH 44555-3663, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|June 5, 2004
PubMed
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Achiral p-nitrophenyl isocyanide unexpectedly crystallizes in a chiral space group. This study reveals strong intermolecular interactions, specifically a notable nitrogen-oxygen bond, influencing its crystal structure.

Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Supramolecular chemistry

Background:

  • Achiral molecules typically crystallize in achiral space groups.
  • Intermolecular interactions play a crucial role in determining crystal packing and properties.
  • Aromatic nitro compounds exhibit diverse intermolecular interactions.

Purpose of the Study:

  • To investigate the crystal structure of achiral p-nitrophenyl isocyanide.
  • To identify and characterize intermolecular interactions within the crystal lattice.
  • To compare the observed interactions with those in similar aromatic nitro compounds.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Analysis of intermolecular distances and coordination numbers.

Related Experiment Videos

  • Comparison with crystallographic data of related compounds.

    • Main Results:

    • Achiral p-nitrophenyl isocyanide crystallizes in the orthorhombic chiral space group P2(1)2(1)2(1).
    • Significant intermolecular interactions were observed between nitro oxygen atoms and aromatic hydrogen atoms, as well as nitro nitrogen atoms of adjacent molecules.
    • A notably strong nitrogen-oxygen interaction (N...O = 2.869 Å) was identified, exceeding typical strengths in aromatic nitro compounds.

    Conclusions:

    • The crystallization of an achiral molecule in a chiral space group highlights complex packing phenomena.
    • The observed strong intermolecular N...O interaction significantly influences the crystal structure and packing of p-nitrophenyl isocyanide.
    • These findings contribute to understanding structure-property relationships in organic crystalline materials.