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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Published on: August 22, 2018

Indizoline.

Hoong-Kun Fun, Wisanu Maneerat, Surat Laphookhieo

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    A natural carbazole, 1-methoxy-2-(3-methyl-but-2-enyl)-9H-carbazole-3-carbaldehyde, was isolated from Clausena lansium. Its crystal structure reveals a planar carbazole core with specific substituent orientations and intermolecular interactions stabilizing the crystal lattice.

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    Area of Science:

    • Natural Product Chemistry
    • Organic Chemistry
    • Crystallography

    Background:

    • Carbazole derivatives are prevalent in natural products with diverse biological activities.
    • Clausena lansium is a known source of various bioactive compounds.
    • Understanding the structural features of natural carbazoles is crucial for structure-activity relationship studies.

    Purpose of the Study:

    • To elucidate the crystal structure of the natural carbazole 1-methoxy-2-(3-methyl-but-2-enyl)-9H-carbazole-3-carbaldehyde.
    • To analyze the molecular geometry and intermolecular interactions of the isolated compound.
    • To provide a detailed structural characterization for future research.

    Main Methods:

    • Single crystal X-ray diffraction was employed to determine the three-dimensional structure.
    • Analysis of bond lengths, bond angles, torsion angles, and intermolecular interactions was performed.
    • The crystal packing and intermolecular forces, including hydrogen bonding and pi-pi interactions, were investigated.

    Main Results:

    • The crystal structure of 1-methoxy-2-(3-methyl-but-2-enyl)-9H-carbazole-3-carbaldehyde (C19H19NO2) was successfully determined.
    • The carbazole ring system was found to be essentially planar.
    • Specific torsion angles described the orientation of the methoxy and prenyl substituents relative to the carbazole core.
    • Intermolecular N-H⋯O hydrogen bonds and C-H⋯O hydrogen bonds, along with π-π stacking interactions, were identified as key stabilizing forces in the crystal lattice.

    Conclusions:

    • The crystal structure provides definitive insights into the solid-state conformation of this natural carbazole.
    • The identified intermolecular interactions highlight the factors contributing to crystal stability.
    • This structural data serves as a valuable reference for synthetic modifications and biological evaluations of related carbazole compounds.