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Issue 39, 2014
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Influence of fluorine side-group substitution on the crystal structure formation of benzene-1,3,5-trisamides

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Abstract

By a combination of powder X-ray diffraction, multidimensional and multinuclear solid-state NMR spectroscopy and quantum chemical calculations, we were able to determine the crystal structure of 1,3,5-tris(2-fluoro-2-methylpropionylamino)benzene. Solid-state NMR experiments guided the structure solution by predicting the content of the asymmetric unit and the presence of a NH⋯OC hydrogen bond network. In addition to real-space structure solution and Rietveld refinement, quantitative symmetry-based 19F19F double-quantum recoupling experiments provided a cost function to determine the positions of the methyl groups and fluorine atoms. The structure solution of this particular fluorine-substituted trisamide illustrates the impact of fluorine side-group substitution on the common columnar packing motif of benzene-1,3,5-tricarboxamides. As also in the case 1,3,5-tris(2,2-dimethylpropionylamino)benzene, the supramolecular aggregation is then guided by the formation of triple helical NH⋯OC hydrogen bond networks within the individual columns. In contrast, the substitution of one methyl group by a fluorine atom in each side chain results in a two-dimensional NH⋯OC hydrogen bond pattern, leading to a lamellar crystal structure with only van der Waals interactions between the layers. Since fluorine is not involved in the hydrogen bond network and both chemical units exhibit a similar steric demand, the fundamental differences of the packing are most probably caused by changes in the molecular polarity.

Graphical abstract: Influence of fluorine side-group substitution on the crystal structure formation of benzene-1,3,5-trisamides

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Supplementary files

Article information


Submitted
25 May 2014
Accepted
11 Aug 2014
First published
12 Aug 2014

CrystEngComm, 2014,16, 9273-9283
Article type
Paper
Author version available

Influence of fluorine side-group substitution on the crystal structure formation of benzene-1,3,5-trisamides

C. Zehe, M. Schmidt, R. Siegel, K. Kreger, V. Daebel, S. Ganzleben, H. Schmidt and J. Senker, CrystEngComm, 2014, 16, 9273
DOI: 10.1039/C4CE01077A

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