4-Methyl-1-phenyl-quinolin-2(1H)-one

Area of Science:

• Crystal Engineering
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Understanding intermolecular forces is key to designing novel materials.
• Non-classical hydrogen bonds play a significant role in crystal packing and material properties.
• The quinolin-2(1H)-one scaffold is a prevalent motif in medicinal chemistry and materials science.

Purpose of the Study:

• To elucidate the three-dimensional molecular arrangement of the title compound, C16H13NO.
• To identify and characterize the intermolecular interactions governing the crystal structure.
• To investigate the role of non-classical interactions in stabilizing the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular structure and crystal packing.
• Analysis of intermolecular distances and angles to identify non-classical C-H⋯O and C-H⋯π interactions.
• Calculation of the dihedral angle between the benzyl and quinolin-2(1H)-one ring systems.

Main Results:

• The crystal structure is stabilized by a network of non-classical C-H⋯O and C-H⋯π interactions.
• Observed C-H⋯O interactions with distances of 3.272(3) Å and C-H⋯π interactions with distances of 3.380(3) and 3.382(4) Å.
• A significant dihedral angle of 87.15(7)° was found between the benzyl and quinolin-2(1H)-one mean planes, indicating a near-orthogonal orientation.

Conclusions:

• The crystal structure of C16H13NO is primarily governed by non-classical intermolecular interactions, not classical hydrogen bonds.
• These non-classical interactions dictate the three-dimensional assembly of molecules in the solid state.
• The observed molecular conformation and packing provide insights into the structure-property relationships of related quinolin-2(1H)-one derivatives.