2,9-Bis(trichloro-meth-yl)-1,10-phenanthroline

Area of Science:

• Crystallography
• Materials Science
• Supramolecular Chemistry

Background:

• Understanding the crystal packing and intermolecular interactions of organic molecules is crucial for designing materials with specific properties.
• Hexachlorinated aromatic compounds with nitrogen heteroatoms can exhibit unique electronic and structural characteristics due to halogen bonding and π-π stacking.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(14)H(6)Cl(6)N(2).
• To investigate the nature of intermolecular interactions, including halogen bonding and π-π interactions, within the crystal lattice.
• To describe the supramolecular architecture formed by these interactions.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
• Analysis of bond distances, dihedral angles, and intermolecular contacts (C⋯Cl, Cl⋯Cl, Cl⋯N, π-π) was performed.
• The crystal packing and supramolecular assembly were visualized and described.

Main Results:

• The asymmetric unit contains two independent, slightly non-planar molecules of C(14)H(6)Cl(6)N(2).
• Molecules are arranged into sheets parallel to the ac plane through C-Cl⋯Cl interactions.
• These sheets stack in an anti-parallel manner along the b-axis, forming a 3D supramolecular network stabilized by short contacts and π-π interactions.

Conclusions:

• The crystal structure of C(14)H(6)Cl(6)N(2) is characterized by twisted molecular conformations and significant intermolecular interactions.
• C-Cl⋯Cl interactions play a key role in forming layered structures, while other short contacts and π-π interactions contribute to the overall supramolecular network.
• The absence of classical hydrogen bonds emphasizes the importance of halogen bonding and other non-classical interactions in this system.