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Related Experiment Videos

Cinnamoyl shikonin.

S Sarkhel1, Shefali, V T Mathad

  • 1Molecular and Structural Biology Division, Central Drug Research Institute, Lucknow 226 001, India.

Acta Crystallographica. Section C, Crystal Structure Communications
|October 16, 2001
PubMed
Summary
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This study details the crystal structure of a novel naphthyl cinnamate derivative. The compound forms a unique tetracyclic system stabilized by intramolecular hydrogen bonds and exhibits intermolecular pi-pi stacking.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Naphthyl cinnamate derivatives are of interest due to their potential applications.
  • Understanding the solid-state structure is crucial for predicting chemical properties.

Purpose of the Study:

  • To elucidate the crystal structure of 1-(5,8-dihydro-1,4-dihydroxy-5,8-dioxo-2-naphthyl)-4-methylpent-3-en-1-yl cinnamate.
  • To investigate the intermolecular interactions and overall molecular conformation.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Space group determination (P2(1)).
  • Analysis of bond angles, distances, and hydrogen bonding.

Main Results:

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  • The compound crystallizes in space group P2(1).
  • Intramolecular hydrogen bonds form two six-membered rings, creating a tetracyclic, pyrene-shaped system.
  • The phenyl ring exhibits an anti conformation relative to the carbonyl group and engages in intermolecular pi-pi stacking with the benzoquinone ring.

    • Conclusions:

    • The crystal structure reveals a unique tetracyclic system stabilized by hydrogen bonding.
    • Aromatic pi-pi interactions play a significant role in the crystal packing.
    • The detailed structural information provides a basis for further studies on this class of compounds.