(S)-3-(Ammoniomethyl)-5-methylhexanoate (pregabalin)

Area of Science:

• Crystallography
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Understanding molecular self-assembly is crucial for designing advanced materials.
• Zwitterions, with their distinct charge distribution, offer unique properties for self-organization.

Purpose of the Study:

• To elucidate the crystal structure and self-assembly mechanism of the title compound, C(8)H(17)NO(2).
• To investigate the intermolecular interactions driving the formation of layered structures.

Main Methods:

• Single-crystal X-ray diffraction analysis.
• Analysis of hydrogen bonding networks (N+-H...O- and C-H...O-).
• Identification of stabilizing interactions (van der Waals forces).

Main Results:

• The title compound exists as a zwitterion with a propeller conformation.
• Molecules self-assemble into hydrogen-bonded layers parallel to the ab crystallographic plane.
• These layers stack along the c axis, stabilized by van der Waals interactions.

Conclusions:

• The study provides detailed insights into the crystal engineering of zwitterionic compounds.
• The observed self-assembly mechanism highlights the importance of hydrogen bonding and van der Waals forces in supramolecular architecture.
• This work contributes to the fundamental understanding of molecular organization in the solid state.