N-(6-Methylpyridin-2-yl)mesitylenesulfonamide and acetic acid--a salt, a cocrystal or both?

Acta Crystallogr C Struct Chem. 2015 Aug;71(Pt 8):653-7. doi: 10.1107/S2053229615012826. Epub 2015 Jul 7.

Abstract

In the solid obtained from N-(6-methylpyridin-2-yl)mesitylenesulfonamide and acetic acid, the constituents interact via two N-H···O hydrogen bonds. The H atom situated in one of these short contacts is disordered over two positions: one of these positions is formally associated with an adduct of the neutral sulfonamide molecule and the neutral acetic acid molecule, and corresponds to a cocrystal, while the alternative site is associated with salt formation between a protonated sulfonamide molecule and deprotonated acetic acid molecule. Site-occupancy refinements and electron densities from difference Fourier maps suggest a trend with temperature, albeit of limited significance; the cocrystal is more relevant at 100 K, whereas the intensity data collected at room temperature match the description as cocrystal and salt equally well.

Keywords: IR spectroscopy; benzenesulfonamide; cocrystal; crystal structure; mesitylenesulfonamide; pharmaceutically active ingredients; salt; salt–cocrystal continuum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Molecular Structure
  • Pyridines / chemistry*
  • Salts / chemistry*
  • Sulfonamides / chemistry*

Substances

  • N-(6-methylpyridin-2-yl)mesitylenesulfonamide
  • Pyridines
  • Salts
  • Sulfonamides
  • Acetic Acid