1-(4-Methyl-phenyl-diazo-nium-yl)-2-naphtholate

Area of Science:

• Organic Chemistry
• Crystallography
• Molecular Structure Analysis

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
• Aromatic systems, such as benzene and naphthalene, are fundamental building blocks in many functional materials and pharmaceuticals.
• Intermolecular forces, like pi-pi interactions and hydrogen bonding, dictate crystal packing and solid-state behavior.

Purpose of the Study:

• To elucidate the precise molecular geometry and crystal packing of the title compound, C(17)H(14)N(2)O.
• To investigate the nature and strength of intramolecular interactions, specifically hydrogen bonding.
• To analyze the intermolecular forces driving the self-assembly of molecules in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
• Analysis of bond lengths, bond angles, and dihedral angles provided detailed geometric information.
• Intermolecular contact analysis was performed to identify and quantify packing forces, including pi-pi interactions and hydrogen bonds.

Main Results:

• The crystal structure revealed a dihedral angle of 11.0(3)° between the benzene and naphthalene ring systems.
• An anti configuration of the azo group was observed.
• A significant intramolecular N-H⋯O hydrogen bond was identified.
• Molecules were found to pack via pi-pi interactions, with the closest centroid approach between aromatic rings measuring 3.501 Å.

Conclusions:

• The determined molecular structure provides a fundamental understanding of this specific organic compound.
• The presence of both intramolecular hydrogen bonding and pi-pi stacking interactions suggests potential for tailored material properties.
• The observed crystal packing offers insights into the design principles for related organic molecules.