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Related Experiment Videos

(S)-trans-cyclohexane-1,2-dicarboximide.

Maria Gdaniec1, Elzbieta Nowak, Maria J Milewska

  • 1Faculty of Chemistry, Adam Mickiewicz University, 60-780 Poznań, Poland. magdan@amu.edu.pl

Acta Crystallographica. Section C, Crystal Structure Communications
|November 5, 2002
PubMed
Summary

This study reveals a strained bicyclic molecule with a twisted imide group. Molecular analysis shows puckered five-membered and distorted six-membered rings, forming infinite chains via hydrogen bonds.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the conformational flexibility and intermolecular interactions of organic molecules is crucial in chemistry.
  • Bicyclic systems and imide functional groups present unique structural challenges and properties.

Purpose of the Study:

  • To elucidate the detailed molecular structure and conformation of the title compound, C(8)H(11)NO(2).
  • To investigate the intermolecular interactions, specifically hydrogen bonding, that dictate the crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure.
  • Conformational analysis of the bicyclic system and the imide moiety was performed.

Main Results:

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  • The molecule exhibits a strained bicyclic system with a significantly twisted imide chromophore.
  • The five-membered ring adopts a puckered half-chair conformation, while the six-membered ring adopts a distorted chair conformation.
  • Infinite chains are formed through strong N-H···O and weak C-H···O hydrogen bonds.

Conclusions:

  • The study provides a detailed structural characterization of a novel bicyclic imide.
  • The observed conformations and hydrogen bonding patterns are key to understanding the compound's solid-state properties.