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Published on: April 27, 2017
4-Fluoro-2-[(3-methyl-phen-yl)imino-meth-yl]phenol
Alice Brink1, Hendrik G Visser, Andreas Roodt
1Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa.
Summary
This study reveals the crystal structure of a C(14)H(12)FNO compound, highlighting its trans phenol-imine tautomer stabilized by intramolecular hydrogen bonding and weak intermolecular interactions for a 3D network.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the solid-state structure of organic compounds is crucial for predicting their properties.
- Phenol-imine tautomerism influences molecular conformation and intermolecular interactions.
- Crystal engineering relies on identifying and utilizing non-covalent interactions.
Purpose of the Study:
- To determine the precise crystal structure of the title compound, C(14)H(12)FNO.
- To investigate the tautomeric form and conformational preferences in the solid state.
- To identify and analyze the intermolecular interactions stabilizing the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to elucidate the three-dimensional molecular arrangement.
- Analysis of bond lengths, bond angles, and torsion angles provided conformational information.
- Intermolecular interactions, including hydrogen bonds and van der Waals forces, were systematically identified.
Main Results:
- The title compound crystallizes as the trans phenol-imine tautomer.
- The two benzene rings exhibit near-coplanarity, with a dihedral angle of 9.28(7)°.
- An intramolecular O-H⋯N hydrogen bond dictates the conformation, and weak C-H⋯O and C-H⋯F interactions stabilize the 3D crystal network.
Conclusions:
- The crystal structure confirms the prevalence of the trans phenol-imine tautomer in the solid state.
- Intramolecular hydrogen bonding plays a significant role in defining the molecular conformation.
- The observed weak C-H⋯O and C-H⋯F interactions are key to forming a stable, three-dimensional supramolecular architecture.
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