1-Phenyl-1H-naphtho-[1,2-e][1,3]oxazin-3(2H)-one

Area of Science:

• Organic Chemistry
• Crystallography
• Supramolecular Chemistry

Background:

• Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties.
• Crystal packing influences material characteristics and reactivity.
• Intermolecular forces, such as hydrogen bonding and pi-pi stacking, play a significant role in stabilizing crystal lattices.

Purpose of the Study:

• To elucidate the crystal structure of the title compound C(18)H(13)NO(2).
• To analyze the spatial arrangement and interactions between the naphthalene, benzaldehyde, and oxazine moieties.
• To investigate the intermolecular forces governing the crystal packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular conformation.
• Identification and analysis of hydrogen bonds (C-H⋯O, N-H⋯O) and pi-pi stacking interactions were performed.

Main Results:

• The naphthalene and benzaldehyde groups exhibit a dihedral angle of 89.48°.
• The oxazine group is oriented at dihedral angles of 13.36° and 85.08° relative to the naphthalene and benzaldehyde fragments, respectively.
• The crystal structure is stabilized by inversion dimers linked by C-H⋯O hydrogen bonds, forming R(2)(2)(8) loops, and further extended into [010] chains via N-H⋯O hydrogen bonds. Aromatic pi-pi stacking between naphthalene rings (3.5977 Å separation) also contributes to packing.

Conclusions:

• The study provides a detailed structural characterization of the title compound.
• The specific orientation of functional groups and the identified intermolecular interactions dictate the observed crystal packing.
• This structural information is valuable for understanding structure-property relationships in related organic materials.