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Dichloro-diphenoxy-methane.

Richard Betz1, Peter Klüfers, Moritz M Reichvilser

  • 1Ludwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13, 81377 München, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

This study details a mixed orthocarbonic acid derivative, C(13)H(10)Cl(2)O(2), revealing its molecular structure and weak intermolecular interactions. Density functional theory (DFT) calculations support the observed crystal structure, highlighting unique metrical peculiarities.

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Area of Science:

  • Crystallography
  • Computational Chemistry
  • Organic Chemistry

Background:

  • Orthocarbonic acid derivatives are interesting compounds with unique structural properties.
  • Understanding the solid-state structure and bonding of such molecules is crucial for predicting their chemical behavior.

Purpose of the Study:

  • To elucidate the crystal structure and molecular geometry of a mixed orthocarbonic acid derivative, C(13)H(10)Cl(2)O(2).
  • To investigate the role of intermolecular forces in stabilizing the observed crystal packing.
  • To compare experimental findings with theoretical predictions from density functional theory (DFT) calculations.

Main Methods:

  • Single-crystal X-ray diffraction analysis to determine the three-dimensional molecular structure.
  • Analysis of bond lengths, bond angles, and dihedral angles to describe the molecular geometry.
  • Density functional theory (DFT) calculations to model the molecule and assess intermolecular interactions.

Main Results:

  • The compound C(13)H(10)Cl(2)O(2) exhibits a molecular symmetry close to C(2v).
  • Phenyl rings are oriented in a syn conformation relative to chlorine atoms, with a 36.11° inter-ring angle.
  • Short C-O bonds and angles smaller than tetrahedral at the central carbon were observed, consistent with DFT calculations and indicating minimal influence of intermolecular forces.

Conclusions:

  • The crystal structure is primarily governed by intramolecular factors rather than intermolecular forces.
  • Weak C-H⋯O and C-H⋯Cl hydrogen bonds are the only significant intermolecular interactions detected.
  • The study provides valuable insights into the structural characteristics and weak bonding interactions of orthocarbonic acid derivatives.