3-(2-Fluoro-phen-oxy)propanoic acid

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the solid-state structure of organic molecules is crucial for predicting their physical and chemical properties.
• Fluorinated organic compounds exhibit unique electronic and steric properties, influencing molecular packing and intermolecular interactions.
• Carboxylic acid functional groups are known to participate in strong hydrogen bonding, dictating crystal architectures.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(9)H(9)FO(3).
• To analyze the intermolecular interactions, including hydrogen bonding and weaker interactions, that govern the crystal packing.
• To investigate the dihedral angle between the carboxyl group and the benzene ring and its influence on molecular conformation.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
• Analysis of the crystal structure involved identifying hydrogen bond donors and acceptors.
• Intermolecular interactions were characterized using geometric parameters and topological analysis.

Main Results:

• The crystal structure of C(9)H(9)FO(3) was successfully determined.
• A significant dihedral angle of 79.4(3)° was observed between the carboxyl group and the benzene ring.
• Molecules self-assemble into centrosymmetric dimers mediated by classical O-H⋯O hydrogen bonds.
• Weaker C-H⋯O interactions further link these dimers, establishing an extended three-dimensional network in the crystal.

Conclusions:

• The crystal packing of C(9)H(9)FO(3) is primarily dictated by strong O-H⋯O hydrogen bonds forming dimers.
• The observed dihedral angle influences the overall molecular conformation and its packing arrangement.
• The interplay of hydrogen bonds and weaker interactions results in a stable three-dimensional supramolecular architecture.