(E)-2-[(4-Fluoro-phen-yl)imino-meth-yl]-5-methoxy-phenol

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding molecular interactions and tautomerism is crucial in organic chemistry.
• Crystal structure analysis provides insights into intermolecular forces and molecular conformation.
• Phenol-imine tautomerism influences chemical properties and reactivity.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of the title compound C14H12FNO2.
• To investigate the presence and implications of phenol-imine tautomerism in the solid state.
• To characterize the hydrogen bonding and pi-stacking interactions within the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular structure.
• Analysis of bond lengths (C-O, C-N, C-C) provided evidence for tautomerism.
• Identification of intra-molecular O-H⋯N hydrogen bonds and inter-molecular C-H⋯π interactions.

Main Results:

• The crystal structure of C14H12FNO2 was determined, showing a dihedral angle of 48.17(1)° between aromatic rings.
• An intra-molecular O-H⋯N hydrogen bond formed a six-membered ring, indicating phenol-imine tautomerism.
• Short bond lengths (C-O: 1.351(3) Å, C-N: 1.282(3) Å) confirmed the tautomeric form.
• Inter-molecular C-H⋯π interactions were observed, linking molecules in the crystal.

Conclusions:

• The title compound exists as a phenol-imine tautomer in the solid state.
• Intra-molecular hydrogen bonding plays a significant role in stabilizing this tautomeric form.
• Inter-molecular C-H⋯π interactions contribute to the overall crystal packing.