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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 226, Issue 5

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The use of dispersion-corrected DFT calculations to prevent an incorrect structure determination from powder data: the case of acetolone, C11H11N3O3

Jürgen Brüning / Edith Alig
  • 1 Goethe University, Institute of Inorganic and Analytical Chemistry, Frankfurt, Deutschland
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/ Jacco van de Streek / Martin U. Schmidt
  • 3 Goethe University, Institute of Inorganic and Analytical Chemistry, Frankfurt am Main, Deutschland
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Published Online: 2011-02-18 | DOI: https://doi.org/10.1524/zkri.2011.1364

Abstract

The crystal structure of acetolone (5-(acetoacetylamino)benzimidazolone, C11H11N3O3), was determined from X-ray powder data. Despite strong preferred orientation effects, the structure could be solved with real-space methods and refined by the Rietveld method using restraints. The resulting structure gave a good Rietveld fit with reasonable confidence values; the structure looked chemically sensible and passed all tests including a CSD check and the checkCIF procedure. But dispersion-corrected density functional theory (DFT) calculations revealed that this structure was actually wrong, and further work showed that the terminal acetyl group had to be rotated by 180°. The correct crystal structure led to a better Rietveld refinement with improved R-values. This structure was confirmed by dispersion-corrected DFT calculations. The compound crystallises in P-1 with two molecules per unit cell. The molecules are connected by a 2-dimensional hydrogen bond network.

Keywords: Powder diffraction structure analysis; X-ray diffraction; DFT-D; Organic compounds; Real-space methods

About the article

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


Published Online: 2011-02-18

Published in Print: 2011-05-01


Citation Information: Zeitschrift für Kristallographie Crystalline Materials, Volume 226, Issue 5, Pages 476–482, ISSN (Print) 0044-2968, DOI: https://doi.org/10.1524/zkri.2011.1364.

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