N-(4-Methyl-phenyl-sulfon-yl)-3-nitro-benzamide

Area of Science:

• Crystallography and Molecular Structure
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
• Intermolecular forces, such as hydrogen bonding and van der Waals interactions, play a significant role in the self-assembly of molecules in the solid state.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C14H12N2O5S.
• To analyze the molecular conformation and identify the types and patterns of intermolecular interactions present in the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the atomic coordinates and unit cell parameters.
• Analysis of bond lengths, bond angles, dihedral angles, and torsion angles to describe the molecular conformation.
• Identification and characterization of intermolecular interactions (hydrogen bonds, C-H···O interactions) using geometric criteria.

Main Results:

• The dihedral angle between the aromatic rings is 86.29(1)°, indicating a near-orthogonal arrangement.
• The molecule adopts an L-shaped conformation with a syn conformation between the amide C=O and meta-NO2 groups.
• Inversion dimers are formed via N-H···O hydrogen bonds and C-H···O interactions, creating R2(2)(8) and R2(2)(14) loops, respectively. These dimers further assemble into (100) sheets through additional C-H···O interactions.

Conclusions:

• The crystal structure of C14H12N2O5S reveals specific conformational preferences and a well-defined network of intermolecular interactions.
• The observed hydrogen bonding and C-H···O interactions are key to the formation of supramolecular assemblies, specifically inversion dimers and extended sheets.
• This detailed structural information provides a foundation for understanding the physical and chemical properties of this compound.