1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chloro-phen-yl)urea

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
• Imidazopyridine derivatives are a class of heterocyclic compounds with diverse biological activities.
• Intermolecular interactions, such as hydrogen bonding and pi-pi stacking, play a significant role in crystal engineering and material properties.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C14H11Cl2N5O.
• To analyze the molecular conformation and the nature of intermolecular interactions in the solid state.
• To provide insights into the structural features that influence the packing and stability of this heterocyclic system.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the atomic arrangement of the compound.
• Analysis of bond lengths, bond angles, and dihedral angles to describe the molecular geometry.
• Identification and quantification of intra- and intermolecular hydrogen bonds and pi-pi interactions.

Main Results:

• The crystal structure reveals a 1H-imidazo[4,5-c]pyridine ring system with a dihedral angle of 4.87° relative to the terminal phenyl ring.
• An intramolecular N-H⋯N hydrogen bond was observed, stabilizing the molecular conformation.
• In the crystal lattice, molecules form inversion dimers linked by N-H⋯O hydrogen bonds, further stabilized by pi-pi interactions between imidazole rings (shortest centroid-centroid distance = 3.4443 Å).

Conclusions:

• The crystal structure of C14H11Cl2N5O has been successfully determined.
• The molecular conformation is influenced by intramolecular hydrogen bonding, while crystal packing is governed by intermolecular hydrogen bonds and pi-pi stacking.
• These findings contribute to the understanding of structure-property relationships in imidazopyridine derivatives.