2-[(2-Acet-oxy-benzo-yl)-oxy]benzoic acid.

Area of Science:

• Organic Chemistry
• Crystallography
• Pharmaceutical Analysis

Background:

• Ortho-acetyl-salicylic acid, commonly known as aspirin, is a widely used medication.
• Impurities in pharmaceutical compounds can affect drug safety and efficacy.
• Characterizing common impurities like C(16)H(12)O(6) is crucial for quality control.

Purpose of the Study:

• To elucidate the crystal structure of the compound C(16)H(12)O(6).
• To understand the molecular conformation and intermolecular interactions of this aspirin impurity.
• To provide crystallographic data for the identification and quantification of this impurity.

Main Methods:

• Single-crystal X-ray diffraction analysis was performed.
• The molecular geometry, including dihedral angles between ring systems and functional groups, was determined.
• Intermolecular interactions, specifically hydrogen bonding, were analyzed.

Main Results:

• The crystal structure of C(16)H(12)O(6) was determined, revealing a dihedral angle of 81.9° between its benzene rings.
• Acetyl and carboxyl groups exhibited dihedral angles of 74.0° and 26.4°, respectively, with their bound benzene rings.
• Molecules were observed to form inversion dimers via O-H⋯O hydrogen bonds between carboxyl groups in the crystal lattice.

Conclusions:

• The detailed crystal structure provides a reference for identifying C(16)H(12)O(6) as an aspirin impurity.
• The observed hydrogen bonding pattern highlights the self-assembly behavior of the molecule in the solid state.
• This structural information aids in the quality control and impurity profiling of aspirin.