2-Amino-3-chloro-5-nitro-benzamide

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their chemical behavior and physical properties.
• The presence of amide and nitro groups on a benzene ring can influence molecular conformation and intermolecular interactions.
• Hydrogen bonding plays a significant role in the self-assembly and properties of crystalline solids.

Purpose of the Study:

• To elucidate the detailed molecular structure of the title compound, C(7)H(6)ClN(3)O(3).
• To investigate the conformational preferences of the amide and nitro groups relative to the benzene ring.
• To identify and characterize intra-molecular and inter-molecular hydrogen bonding interactions within the crystal structure.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the precise atomic coordinates and bond parameters.
• Analysis of bond lengths, bond angles, and torsion angles provided insights into the molecular geometry.
• Intermolecular interactions, specifically hydrogen bonds, were identified using geometric criteria.

Main Results:

• The amide group is significantly twisted out of the plane of the benzene ring, with a C-C-C-O torsion angle of 34.2(5)°.
• The nitro group is nearly co-planar with the benzene ring, exhibiting an O-N-C-C torsion angle of 4.0(5)°.
• Intra-molecular hydrogen bonds of the N-H⋯O and N-H⋯Cl types were observed.
• In the crystal lattice, molecules are interconnected by N-H⋯O hydrogen bonds, forming layered structures propagating in the ab plane.

Conclusions:

• The molecular conformation is characterized by a pronounced deviation of the amide group from planarity, while the nitro group remains largely planar.
• Intra-molecular hydrogen bonding contributes to the stabilization of the observed molecular conformation.
• Intermolecular N-H⋯O hydrogen bonds dictate the formation of extended layered networks in the solid state, influencing crystal packing.