Hydrogen-bonded chains in N-(2-nitrophenyl)phenylamine

Area of Science:

• Chemical Crystallography
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
• Non-planar molecular structures can lead to unique packing arrangements and properties.
• Hydrogen bonding plays a key role in directing supramolecular assembly.

Purpose of the Study:

• To investigate the crystal structure and supramolecular aggregation of the title compound, C(12)H(10)N(2)O(2).
• To analyze the role of intramolecular and intermolecular hydrogen bonds in the molecular arrangement.
• To compare the observed supramolecular patterns with related isomeric and N-methylated nitroaniline derivatives.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
• Analysis of hydrogen bonding networks, including N-H...O and C-H...O interactions.
• Comparative analysis of crystal structures with related compounds.

Main Results:

• The title compound, C(12)H(10)N(2)O(2), crystallizes in a markedly non-planar conformation.
• An intramolecular N-H...O hydrogen bond is present within the molecule.
• Molecules are organized into zigzag chains via intermolecular C-H...O hydrogen bonds, influencing crystal packing.

Conclusions:

• The non-planar nature and specific hydrogen bonding patterns dictate the supramolecular architecture of C(12)H(10)N(2)O(2).
• The observed zigzag chain formation is a significant feature of its crystal structure.
• Comparison with isomers and related compounds provides insights into structure-property relationships in nitroaniline derivatives.