2-[(E)-(2-Chloro-phen-yl)imino-meth-yl]-6-methyl-phenol

Area of Science:

• Chemical Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Schiff bases are versatile organic compounds with diverse applications.
• Understanding the solid-state structure of Schiff bases is crucial for predicting their properties.
• Tautomerism and hydrogen bonding significantly influence molecular conformation and reactivity.

Purpose of the Study:

• To elucidate the crystal structure of a Schiff base derived from 3-methyl-salicyl-aldehyde.
• To investigate the tautomeric form, molecular geometry, and hydrogen bonding interactions.
• To characterize the compound C(14)H(12)ClNO in the solid state.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed.
• The crystallographic data were collected and refined.
• Structural parameters, including bond lengths, angles, and dihedral angles, were determined.

Main Results:

• The compound crystallizes in the phenol-imine tautomeric form.
• An E conformation was observed for the imine functionality.
• The molecule exhibits non-planar geometry with a dihedral angle of 36.38(5)° between aromatic rings.
• A strong intramolecular O-H⋯N hydrogen bond forms an S(6) ring.

Conclusions:

• The crystal structure confirms the phenol-imine tautomerism and E-imine conformation.
• Intramolecular hydrogen bonding plays a key role in stabilizing the observed molecular structure.
• The non-planar conformation is attributed to steric and electronic factors, including the hydrogen bond.