N-[4-(Ethyl-sulfamo-yl)phen-yl]acetamide

Area of Science:

• Crystallography and Molecular Structure
• Supramolecular Chemistry
• Organic Chemistry

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and designing new materials.
• Crystal structure analysis provides detailed insights into molecular conformations, intermolecular interactions, and packing arrangements in the solid state.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(10)H(14)N(2)O(3)S.
• To characterize the conformations of the two crystallographically independent molecules (A and B) and analyze their dihedral and torsion angles.
• To investigate the hydrogen bonding networks formed by sulfonamide and amide groups in the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of crystallographic data included identifying molecular conformations, measuring key bond and dihedral angles, and characterizing hydrogen bonds.
• Disorder in the ethyl-sulfonamide moiety of molecule B was modeled.

Main Results:

• The asymmetric unit contains two molecules (A and B) with L-shaped conformations.
• Molecule B exhibits disorder in the terminal methyl group of the ethyl-sulfonamide moiety.
• Distinct dihedral angles were observed between the benzene ring and substituents in molecules A and B.
• Similar but oppositely sensed twists about the S-N bonds were found (C-S-N-C torsion angles: 66.5° for A, -64.4° for B).
• Molecule A forms inversion dimers via sulfonamide N-H···O hydrogen bonds, while molecule B forms chains via similar interactions.
• Amide N-H···O hydrogen bonds link these dimers and chains into a 3D network.

Conclusions:

• The crystal structure reveals specific molecular conformations and a complex three-dimensional hydrogen bonding network.
• The observed hydrogen bonding patterns, involving both sulfonamide and amide groups, dictate the supramolecular architecture in the solid state.
• This detailed structural information is valuable for understanding structure-property relationships and for crystal engineering applications.