3-{(E)-[(4-Formyl-phen-yl)iminium-yl]meth-yl}naphthalen-2-olate

Area of Science:

• Crystal Engineering
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Schiff base compounds are versatile organic molecules with diverse applications.
• Understanding the solid-state structure of Schiff bases is crucial for designing novel materials.
• Zwitterionic structures within organic compounds can lead to unique electronic and physical properties.

Purpose of the Study:

• To characterize the crystal structure and supramolecular assembly of a novel Schiff base compound.
• To investigate the presence and role of intra- and intermolecular interactions in the solid state.
• To elucidate the zwitterionic nature and stereochemistry of the title compound.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
• Hydrogen bonding interactions (both intramolecular and intermolecular) were identified and analyzed.

Main Results:

• The title compound, C(18)H(13)NO(2), was confirmed to be a zwitterion with a deprotonated naphthol hydroxy group and a protonated imine nitrogen.
• An E configuration around the central C=N double bond was observed.
• An intramolecular N-H⋯O hydrogen bond formed an S(6) ring motif, and intermolecular C-H⋯O hydrogen bonds linked adjacent molecules into a supramolecular ribbon along the b axis.

Conclusions:

• The study successfully characterized the solid-state structure of the zwitterionic Schiff base.
• Intramolecular hydrogen bonding plays a significant role in stabilizing the molecular conformation.
• Intermolecular interactions dictate the formation of a one-dimensional supramolecular architecture in the crystal.