2-{2-[(2,6-Dichloro-phen-yl)amino]-phen-yl}ethanol

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure Analysis

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is fundamental to predicting their chemical behavior and properties.
• Dichloro-anilino derivatives are important scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

• To elucidate the precise molecular conformation and intermolecular interactions of the title compound, C(14)H(13)Cl(2)NO.
• To provide detailed crystallographic data for this specific dichloro-anilino derivative.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular structure.
• Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (hydrogen bonding, pi-pi stacking) was performed.

Main Results:

• The 2,6-dichloro-anilino unit is nearly planar, with a dihedral angle of 67.71° relative to the ethanol-substituted benzene ring.
• The C-C-O fragment exhibits a dihedral angle of 64.94° with its parent benzene ring.
• The crystal structure is stabilized by a bifurcated N-H⋯(O,Cl) hydrogen bond, along with C-H⋯π, O-H⋯π, and π-π interactions (centroid-centroid distance of 3.5706 Å).

Conclusions:

• The molecular conformation is significantly influenced by the steric bulk of the dichloro-anilino group and the presence of the ethanol substituent.
• Intermolecular forces, particularly hydrogen bonding and pi-pi stacking, play a critical role in the overall crystal packing and stability.