N-(2-Oxo-2H-chromen-3-yl)cyclo-hexane-carboxamide

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Coumarin derivatives are known for diverse biological activities.
• Understanding molecular conformation and intermolecular interactions is crucial for structure-activity relationship studies.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C16H17NO3.
• To analyze the planarity, conformation, and hydrogen bonding interactions within the molecule and in the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction analysis was performed.
• Analysis of bond lengths, bond angles, dihedral angles, and intermolecular interactions (hydrogen bonds, C-H···π, π-π stacking).

Main Results:

• The coumarin moiety is essentially planar, with a maximum deviation of 0.0183(12) Å.
• The cyclohexane ring adopts a chair conformation.
• Two intramolecular hydrogen bonds involving the amide group were identified.
• Molecules form inversion dimers linked by N-H···O contacts, further forming chains via C-H···O interactions.
• Observed C-H···π and π-π interactions with a centroid-centroid distance of 3.8654(10) Å.

Conclusions:

• The crystal structure of C16H17NO3 is fully characterized.
• Intramolecular and intermolecular interactions dictate the packing arrangement and stability of the crystal structure.
• The findings provide a basis for understanding the physical and potentially biological properties of this coumarin derivative.