(RS)-1-[5-(2-Chloro-prop-yl)indolin-1-yl]ethanone

Area of Science:

• Crystallography
• Organic Chemistry
• Structural Chemistry

Background:

• The study focuses on the molecular structure and crystal packing of a specific organic compound.
• Understanding the three-dimensional arrangement of atoms is crucial for predicting chemical properties and reactivity.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(13)H(16)ClNO.
• To analyze the molecular conformation, including planarity and disorder.
• To identify intermolecular interactions stabilizing the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
• Analysis of bond lengths, bond angles, and deviations from planarity.
• Identification of hydrogen bonding networks and other intermolecular forces.

Main Results:

• The acetyl-indoline moiety was found to be nearly planar, with a root-mean-square deviation of 0.0048 Å.
• The chloro-propyl group attached to the stereogenic carbon is statistically disordered over two positions, with chlorine and methyl groups exchanging places.
• The compound crystallizes as a racemate.
• Non-classical C-H⋯O hydrogen bonds between benzene rings of symmetry-related molecules were identified as the primary stabilizing force for the crystal structure.

Conclusions:

• The crystal structure of C(13)H(16)ClNO has been successfully determined.
• The observed disorder and racemic nature provide insights into the molecule's behavior in the solid state.
• The identified hydrogen bonding network highlights specific intermolecular interactions crucial for crystal stabilization.