X-Ray powder diffraction, solid-state NMR and dispersion-corrected DFT calculations to investigate the solid-state structure of 2-ammonio-5-chloro-4- methylbenzenesulfonate

Sándor L. Bekö, Silke D. Thoms, Jürgen Brüning, Edith Alig, Jacco Van De Streek, Andrea Lakatos, Clemens Glaubitz, Martin U. Schmidt

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The title compound, also called CLT acid, is an industrial intermediate in the synthesis of laked red azo pigments for newspaper printing. Solid-state NMR and IR experiments revealed the compound to exist as the zwitterionic tautomer in the solid state. The crystal structure was solved from X-ray powder diffraction data by means of real-space methods using the program DASH 3.1. Subsequently the structure was refined by the Rietveld method with TOPAS 4.1. The zwitterionic tautomer gave better confidence values than the non-zwitterionic tautomer. Finally the structure was confirmed by dispersion-corrected density-functional calculations. The compound crystallises in the monoclinic space group Ia, Z = 4 with a = 5.49809(7) Å b = 32.8051(5) Å c = 4.92423(7) Å, b = 93.5011(7)β and V = 886.50(2) Å3. The molecules form a herringbone pattern with a double layer structure consisting of alternating polar and non-polar layers. Within the polar layers hydrogen bonds and ionic interactions are dominant, whereas the fragments in the non-polar layers are connected by van der Waals interactions.

Original languageEnglish
Pages (from-to)382-387
Number of pages6
JournalZeitschrift fur Kristallographie
Volume225
Issue number9
DOIs
Publication statusPublished - Sep 1 2010

Keywords

  • Dispersion-corrected DFT calculations
  • Organic molecule
  • Power diffraction structure analysis
  • Solid-state NMR
  • Tautomerism
  • X-ray diffraction

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Inorganic Chemistry

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