Different N-H⋯π inter-actions in two indole derivatives

Area of Science:

• Organic Chemistry
• Crystallography
• Supramolecular Chemistry

Background:

• Indole derivatives are important scaffolds in medicinal chemistry.
• Understanding intermolecular interactions is crucial for crystal engineering and material design.

Purpose of the Study:

• To synthesize and characterize two novel indole derivatives.
• To elucidate the crystal structures and dominant intermolecular interactions of these compounds.

Main Methods:

• Single-crystal X-ray diffraction analysis.
• Structural analysis of intermolecular interactions (N-H⋯π, C-H⋯π, π-π stacking).

Main Results:

• The crystal structures of 6-isopropyl-3-(2-nitro-1-phenyl-eth-yl)-1H-indole and 2-(4-meth-oxy-phen-yl)-3-(2-nitro-1-phenyl-eth-yl)-1H-indole were determined.
• N-H⋯π bonds were identified as the dominant intermolecular interactions, leading to distinct packing motifs (chains and inversion dimers).
• C-H⋯π interactions contribute to crystal consolidation, while π-π stacking interactions are absent.

Conclusions:

• The study highlights the significant role of N-H⋯π interactions in the crystal packing of these indole derivatives.
• The findings provide insights into the structure-property relationships of indole-based compounds and inform crystal engineering strategies.