1-Adamantylmethyl 2-amino-benzoate

Area of Science:

• Crystallography
• Organic Chemistry
• Materials Science

Background:

• Adamantane derivatives are known for their unique structural properties and diverse applications.
• Understanding the solid-state structure of novel organic compounds is crucial for predicting their physical and chemical behavior.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(18)H(23)NO(2).
• To analyze the molecular conformation, including the adamantane cage and aryl rings.
• To investigate the intermolecular and intramolecular interactions, particularly hydrogen bonding, that stabilize the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.
• Identification and analysis of hydrogen bonding networks (N-H⋯O, N-H⋯N) were performed.

Main Results:

• The asymmetric unit contains two crystallographically independent molecules of C(18)H(23)NO(2).
• Both molecules feature an adamantane cage with near-ideal chair conformations of the fused cyclohexane rings.
• Aryl rings exhibit near-planarity.
• One conformer forms chains via N-H⋯O hydrogen bonds along the b-axis; the other displays an intramolecular N-H⋯O hydrogen bond.
• The crystal structure is further stabilized by weak N-H⋯O and N-H⋯N interactions.

Conclusions:

• The study provides a detailed structural characterization of C(18)H(23)NO(2) at the molecular and crystal level.
• The presence of two independent conformers highlights conformational flexibility within the crystal structure.
• The identified hydrogen bonding patterns are key to the overall crystal packing and stability.