2,3-Dihydro-1,3-benzothiazol-2-iminium hydrogen oxydiacetate: a combined structural and theoretical study

Acta Crystallogr C. 2009 Jan;65(Pt 1):o19-23. doi: 10.1107/S0108270108038365. Epub 2008 Dec 13.

Abstract

In the title compound, C(7)H(7)N(2)S(+).C(4)H(5)O(5)(-), the ions are connected by N-H...O hydrogen bonds. The hydrogen oxydiacetate residues are linked together by O-H...O hydrogen bonds disordered about centres of inversion into hydrogen-bonded ribbon layers crosslinked by weak C-H...O and stacking interactions. The cation exists mainly in the 2,3-dihydro-1,3-benzothiazol-2-iminium form, with a small participation of the 2-aminobenzothiazolium form, based on the structural data and quantum mechanical calculations. This study provides structural insights relevant to the biochemical activity of benzothiazole molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Acetates / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Benzothiazoles / chemistry*
  • Benzothiazoles / pharmacology
  • Hydrogen Bonding
  • Molecular Structure

Substances

  • 2,3-dihydro-1,3-benzothiazol-2-iminium hydrogen oxydiacetate
  • Acetates
  • Antineoplastic Agents
  • Benzothiazoles