(E)-2-[(2,4-Dichloro-phen-yl)imino-methyl]-6-methyl-phenol

Area of Science:

• 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.
• The phenol-imine tautomerism is a key characteristic influencing molecular interactions.

Purpose of the Study:

• To elucidate the crystal structure of the title Schiff base compound (C14H11Cl2NO).
• To investigate the intermolecular interactions, specifically pi-pi stacking, in the solid state.
• To characterize the formation of supramolecular architectures.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of intermolecular distances and angles to identify key interactions.
• Tautomeric form in the solid state was identified.

Main Results:

• The compound crystallizes with two molecules in the asymmetric unit.
• The Schiff base adopts the phenol-imine tautomeric form.
• Head-to-tail pi-pi interactions between adjacent molecules were observed, with centroid-to-centroid distances ranging from 3.682 to 3.910 Å.
• These interactions lead to the formation of two symmetry-independent infinite chains along the b-axis.

Conclusions:

• The crystal structure confirms the phenol-imine tautomeric form in the solid state.
• Supramolecular chains are formed through significant head-to-tail pi-pi interactions.
• The study provides insights into the self-assembly behavior of this Schiff base.