1-Vinyl-1H-indole-3-carbaldehyde

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Indole derivatives are important scaffolds in medicinal chemistry.
• Understanding molecular packing is crucial for material properties and drug design.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of a specific indole-containing compound (C11H9NO).
• To analyze the deviation of the carbaldehyde group from the indole ring plane.
• To identify and characterize the stabilizing forces in the molecular packing.

Main Methods:

• Single-crystal X-ray diffraction analysis was performed.
• Analysis of atomic deviations from the mean plane of the indole ring system.
• Identification and analysis of intermolecular interactions, including hydrogen bonds and pi-pi stacking.

Main Results:

• The carbaldehyde group's C and O atoms showed minimal deviation (0.052(2) Å and 0.076(1) Å, respectively) from the indole ring's mean plane.
• Molecular packing is significantly stabilized by C-H⋯O hydrogen bonds, forming a C(7) chain motif.
• π-π interactions between the pyrrole and benzene rings of adjacent indole systems were observed, with a centroid-centroid distance of 3.637 Å.

Conclusions:

• The title compound exhibits a planar indole core with a slightly deviating carbaldehyde group.
• Intermolecular hydrogen bonding and π-π stacking are key factors governing the solid-state structure.
• The detailed structural analysis provides insights into the intermolecular forces governing the packing of indole derivatives.