3-(2,4,6-Trimethyl-benzo-yl)-2-naphthoic acid

Area of Science:

• Crystallography
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Understanding the solid-state behavior of organic molecules is crucial for materials science.
• Hydrogen bonding and π-π interactions significantly influence crystal packing and molecular assembly.
• Disorder in crystal structures can impact physical properties and requires detailed analysis.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(21)H(18)O(3).
• To investigate the intermolecular interactions, specifically hydrogen bonding and π-π stacking, governing crystal packing.
• To characterize the molecular conformation and identify any instances of disorder within the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of hydrogen bonding (O-H⋯O) and π-π interactions was performed.
• Dihedral angles and disorder in the mesityl ring were quantified.

Main Results:

• The asymmetric unit contains two independent molecules of C(21)H(18)O(3).
• These molecules form cyclic centrosymmetric dimers through O-H⋯O hydrogen bonds.
• Dihedral angles between aromatic systems range from 84.4 to 87.0 degrees, and crystal packing is further stabilized by C-H⋯π and π-π interactions.
• One molecule exhibits disorder in the mesityl ring with an occupancy ratio of approximately 0.69:0.31.

Conclusions:

• The crystal structure of C(21)H(18)O(3) has been successfully determined, showcasing dimer formation via hydrogen bonding.
• The study highlights the interplay of various non-covalent interactions in stabilizing the crystal packing.
• The observed disorder in the mesityl ring provides insights into the conformational flexibility of the molecule in the solid state.