N-Benzoyl-2-nitro-benzene-sulfonamide

Area of Science:

• Crystallography
• Molecular Chemistry
• Organic Chemistry

Background:

• Understanding molecular conformation and intermolecular interactions is crucial for predicting material properties.
• Crystal structure analysis provides fundamental insights into the spatial arrangement of atoms and molecules.
• Sulfonyl compounds with nitro and benzoyl groups exhibit diverse chemical behaviors and applications.

Purpose of the Study:

• To elucidate the detailed molecular structure and conformation of the title compound (C(13)H(10)N(2)O(5)S).
• To investigate the intermolecular interactions, including hydrogen bonding and other weak forces, governing the crystal packing.
• To provide a comprehensive crystallographic analysis of this specific organic molecule.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of bond lengths, bond angles, and torsion angles was performed.
• Identification and analysis of intermolecular interactions such as hydrogen bonds (N-H⋯O) and C-H⋯O/π interactions were conducted.

Main Results:

• The molecule exhibits specific gauche torsion angles around the N-C bond and a syn conformation between the N-H bond and the ortho-nitro group.
• A significant twist (torsion angle of -63.4°) was observed at the S-N bond, indicating non-planarity.
• The sulfonyl benzene ring is tilted at 77.1° relative to the -SO(2)-NH-C-O segment, and the dihedral angle between the sulfonyl and benzoyl rings is 88.6°.
• Molecules form inversion dimers through N-H⋯O(S) hydrogen bonds, further linked by C-H⋯O and C-H⋯π interactions along the b axis.

Conclusions:

• The crystal structure is stabilized by a combination of strong N-H⋯O(S) hydrogen bonds forming dimers and weaker C-H⋯O/π interactions.
• The observed conformational features, including twisted S-N bond and ring tilts, are key characteristics of this molecule in the solid state.
• This detailed structural information serves as a foundation for further studies on the chemical reactivity and potential applications of this compound.