Inter-molecular inter-actions in a phenol-substituted benzimidazole

Area of Science:

• Crystal Engineering
• Supramolecular Chemistry
• Materials Science

Background:

• Hydrogen bonding is fundamental in creating solid-state structures and functional gels.
• Benzimidazole derivatives are versatile scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

• To elucidate the intermolecular interactions in a novel benzimidazole derivative crystal.
• To investigate the role of hydrogen bonding and solvate molecules in crystal packing.
• To quantify the strength of interactions using computational methods.

Main Methods:

• Single-crystal X-ray diffraction to determine the crystal structure.
• Hirshfeld surface analysis to visualize and quantify intermolecular interactions.
• Density Functional Theory (DFT) calculations to estimate hydrogen bond energies.

Main Results:

• The crystal structure of 1-(4-Hydroxybenzyl)-2-(4-hydroxyphenyl)-5,6-dimethyl-1H-benzimidazole acetone disolvate was determined.
• O-H⋯N hydrogen bonds form chains, while acetone solvate molecules participate in O-H⋯O hydrogen bonds.
• C-H⋯π interactions contribute to the overall crystal packing.
• DFT calculations provided insights into the energetic contributions of these interactions.

Conclusions:

• The crystal structure is stabilized by a combination of hydrogen bonding and C-H⋯π interactions.
• Solvate molecules play an integral role in the supramolecular assembly.
• Understanding these interactions is key for the rational design of benzimidazole-based materials.