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Electroantennographic Bioassay as a Screening Tool for Host Plant Volatiles
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5α-Dihydro-vespertilin acetate.

Michael Benn1, Kanwal Nain Vohra, Masood Parvez

  • 1Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a novel cholanoic acid derivative, revealing specific ring conformations and fusion patterns. Non-classical C-H⋯O hydrogen bonds were identified, offering insights into molecular interactions.

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Area of Science:

  • Steroid Chemistry
  • Crystallography
  • Organic Chemistry

Background:

  • Cholanoic acid derivatives are important in biological systems.
  • Understanding their three-dimensional structure is crucial for structure-activity relationship studies.

Purpose of the Study:

  • To elucidate the crystal structure of (20S)-3β-acet-oxy-16α-hydr-oxy-22,23-bis-nor-5α,17β-cholano(22-16)lac-tone.
  • To analyze the conformational preferences and intermolecular interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction analysis.
  • Conformational analysis of the steroid nucleus and fused rings.
  • Identification of hydrogen bonding interactions.

Main Results:

  • The six-membered rings (A, B, C) adopt chair conformations, while the five-membered ring (E) adopts an envelope conformation.
  • The steroid nucleus exhibits trans-fusion for rings A/B, B/C, and C/D, with a cis-fusion between rings D/E.
  • Non-classical intermolecular and intramolecular hydrogen bonds of the C-H⋯O type were observed.

Conclusions:

  • The determined crystal structure provides a detailed stereochemical description of this bis-nor cholanoic acid derivative.
  • The presence of non-classical hydrogen bonds suggests their role in stabilizing the crystal structure and influencing molecular packing.