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Zeitschrift für Kristallographie - Crystalline Materials

Editor-in-Chief: Pöttgen, Rainer

Ed. by Antipov, Evgeny / Boldyreva, Elena V. / Friese, Karen / Huppertz, Hubert / Jahn, Sandro / Tiekink, E. R. T.

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Volume 225, Issue 9

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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

Sandor L. Bekö / Silke D. Thoms
  • 1 Goethe University, Institute of Inorganic and Analytical Chemistry, Frankfurt am Main, Deutschland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Jürgen Brüning
  • 2 Goethe University, Institute of Inorganic and Analytical Chemistry, Frankfurt, Deutschland
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  • De Gruyter OnlineGoogle Scholar
/ Edith Alig
  • 3 Goethe University, Institute of Inorganic and Analytical Chemistry, Frankfurt, Deutschland
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/ Jacco van de Streek / Andrea Lakatos / Clemens Glaubitz / Martin U. Schmidt
  • 7 Goethe University, Institute of Inorganic and Analytical Chemistry, Frankfurt am Main, Deutschland
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  • De Gruyter OnlineGoogle Scholar
Published Online: 2010-08-04 | DOI: https://doi.org/10.1524/zkri.2010.1259

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, β = 93.5011(7)° 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.

Keywords: Solid-state NMR; Dispersion-corrected DFT calculations; Tautomerism; Organic molecule; Powder diffraction structure analysis

About the article

* Correspondence address: Goethe University, Institute of Inorganic and Analytical Chemistry, Max-von-Laue-Str. 7, 60438 Frankfurt am Main, Deutschland,


Published Online: 2010-08-04

Published in Print: 2010-09-01


Citation Information: Zeitschrift für Kristallographie International journal for structural, physical, and chemical aspects of crystalline materials, Volume 225, Issue 9, Pages 382–387, ISSN (Print) 0044-2968, DOI: https://doi.org/10.1524/zkri.2010.1259.

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