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Quinoline-8-sulfonamide.

Krzysztof Marciniec1, Andrzej Maślankiewicz, Maria Nowak

  • 1Department of Organic Chemistry, The Medical University of Silesia, Jagiellońska 4, 41-200 Sosnowiec, Poland.

Acta Crystallographica. Section E, Structure Reports Online
|November 6, 2012
PubMed
Summary

This study details the crystal structure of a novel compound, C(9)H(8)N(2)O(2)S. It reveals how hydrogen bonding and pi-pi stacking interactions form a unique one-dimensional polymer.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding intermolecular forces is crucial for predicting material properties.
  • Hydrogen bonding and pi-pi stacking are key non-covalent interactions in crystal engineering.
  • The quinoline scaffold is a common motif in medicinal chemistry and materials science.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(9)H(8)N(2)O(2)S.
  • To investigate the role of hydrogen bonding and pi-pi stacking in the self-assembly of this molecule.
  • To characterize the resulting one-dimensional polymeric structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding networks (N-H...N and N-H...O) was performed.
  • Intermolecular interactions, including pi-pi stacking, were quantified and analyzed.

Main Results:

  • The crystal structure of C(9)H(8)N(2)O(2)S was successfully determined.
  • Intra-molecular N-H...N and inter-molecular N-H...O hydrogen bonds involving the sulfamoyl group were identified.
  • Molecules form inversion dimers through N-H...O hydrogen bonds, further assembling into a 1D polymer via pi-pi stacking of quinoline rings (centroid-centroid distance = 3.649 Å).

Conclusions:

  • The crystal packing is governed by a combination of hydrogen bonding and pi-pi stacking interactions.
  • The formation of a one-dimensional polymer is a direct consequence of these specific intermolecular forces.
  • This structural insight contributes to the understanding of crystal engineering principles for organic molecules containing quinoline and sulfamoyl moieties.