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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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A chemical symbol is an abbreviation that is used to indicate an element or an atom of an element. For example, the symbol for mercury is Hg. We use the same symbol to indicate one atom of mercury (microscopic domain) or to label a container of many atoms of the element mercury (macroscopic domain).
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Corymbolone.

Stacey Burrett1, Dennis K Taylor1, Edward R T Tiekink2

  • 1School of Agriculture, Food and Wine, The University of Adelaide, Waite Campus, PMB 1, Glen Osmond, SA 5064, Australia.

Acta Crystallographica. Section E, Structure Reports Online
|August 28, 2014
PubMed
Summary

This study details the crystal structure of a novel organic compound, C15H24O2. Its unique molecular conformation and hydrogen bonding patterns influence its crystal packing, forming helical chains.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • The systematic name (4S,4aR,6R,8aR)-4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)octahydro-naphthalen-1(2H)-one describes a complex organic molecule.
  • The compound features a fused ring system with specific stereochemistry.

Purpose of the Study:

  • To elucidate the three-dimensional molecular structure of the title compound.
  • To analyze the conformational preferences of its fused ring system.
  • To investigate the intermolecular interactions and crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
  • Conformational analysis was performed based on the determined atomic coordinates.

Main Results:

  • The molecule exhibits two edge-shared six-membered rings with trans-oriented hydroxyl and methyl substituents at the bridge.
  • One ring adopts a flattened chair conformation, while the other adopts a standard chair conformation.
  • Crystal packing reveals supra-molecular helical chains along the b axis, stabilized by hydroxyl-carbonyl hydrogen bonds.

Conclusions:

  • The study provides a detailed structural characterization of C15H24O2.
  • The observed conformation and crystal packing are influenced by intramolecular and intermolecular forces, particularly hydrogen bonding.
  • The formation of helical chains in the crystal lattice is a key finding.