4-Nitro-phthalamide.

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding the spatial arrangement of substituents on aromatic rings is crucial in organic chemistry.
• Benzene derivatives with multiple functional groups often exhibit complex conformational behaviors.

Purpose of the Study:

• To elucidate the three-dimensional molecular structure of 4-nitro-benzene-1,2-dicarboxamide.
• To analyze the conformational deviations of nitro and amide groups from the benzene ring plane.
• To investigate the intermolecular interactions governing crystal packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of dihedral angles to quantify substituent twisting.
• Identification of hydrogen bonding networks (N-H⋯O) in the crystal lattice.

Main Results:

• The nitro group shows a dihedral angle of 11.36° relative to the benzene ring.
• The two amide groups display significant twisting, with dihedral angles of 60.89° and 34.39°.
• Amide groups are oriented on opposite sides of the benzene ring plane, with amine functionalities directed outwards.
• A 3D crystal architecture is formed through an extensive network of N-H⋯O hydrogen bonds.

Conclusions:

• The molecule 4-nitro-benzene-1,2-dicarboxamide exhibits substantial non-planarity due to substituent twisting.
• Intermolecular hydrogen bonding plays a key role in stabilizing the observed crystal structure.
• The findings provide insights into the structure-property relationships of substituted aromatic compounds.