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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Crystal structure of 4,4'-diethynylbiphen-yl.

Tei Tagg1, C John McAdam2, Brian H Robinson2

  • 1School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia.

Acta Crystallographica. Section E, Crystallographic Communications
|August 18, 2015
PubMed
Summary

This study details the crystal structure of C16H10, revealing four non-planar molecules. These molecules form a 3D network via weak C-H⋯π interactions, creating linked columns in the crystal lattice.

Keywords:
4,4′-diethynyl­biphen­ylC C—H⋯π contactsC—H⋯π(ring) inter­actionscrystal structure

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Organic chemistry

Background:

  • Understanding molecular packing and interactions is crucial for predicting material properties.
  • The C16H10 compound presents an interesting case for studying non-planar molecular arrangements in crystals.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C16H10.
  • To investigate the intermolecular interactions governing the molecular assembly in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of the crystal packing revealed the presence of specific intermolecular interactions.

Main Results:

  • The asymmetric unit contains four unique, non-planar C16H10 molecules.
  • Benzene rings within the molecules exhibit varying dihedral angles (42.41°, 24.07°, 42.59°, 46.88°).
  • A three-dimensional network is formed through weak C-H⋯π(ring) and C-H⋯π(alkyne) interactions, leading to molecular columns along the c-axis.

Conclusions:

  • The crystal structure of C16H10 is characterized by non-planar molecular conformations.
  • Weak hydrogen bonding and π-π stacking interactions play a significant role in directing the self-assembly of molecules in the solid state.
  • The observed network structure provides insights into structure-property relationships for related organic compounds.