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Solid-state structure by X-ray and 13C CP/MAS NMR of new 6-acetyl-8-bromo-5-O-alkylamino-4,7-dimethylcoumarins

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Abstract

6-Acetyl-8-bromo-5-[2-(N,N-dimethylamino)ethoxy)-4,7-dimethylcoumarin (1) and 6-acetyl-8-bromo-5-[2-(N,N-diethylamino)ethoxy)-4,7-dimethylcoumarin (2) were synthesized using microwave conditions. Crystal of 1 was investigated using single-crystal X-ray diffraction at 296 K and 100 K. The crystal undergoes reversible order-disorder, temperature-driven phase transition. The high-temperature form contains two molecules in the asymmetric unit of which one moiety is disordered over two sites. The low-temperature phase is fully ordered and contains four molecules in the asymmetric unit. A complexity of the solid form of 1 is with an agreement with recorded C13 CP/MAS NMR spectrum indicating split of signals. The solid-state structures of 1 and 2 derived from 13C CP/MAS NMR spectra were also proposed.

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Acknowledgements

The X-ray structure was determined in the Advanced Crystal Engineering Laboratory (aceLAB) at the Chemistry Department of the University of Warsaw. Theoretical calculations were carried out with the support of the Interdisciplinary Centre for Mathematical and Computational Modelling (ICM) University of Warsaw under grant no G33-17 and G26-10.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Str., 02 097, Warsaw, Poland

    Kinga Ostrowska & Dorota Maciejewska

  2. The Czochralski Laboratory of Advanced Crystal Engineering, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02 089, Warsaw, Poland

    Grzegorz Cichowicz & Łukasz Dobrzycki

Authors
  1. Kinga Ostrowska
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  2. Dorota Maciejewska
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  3. Grzegorz Cichowicz
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  4. Łukasz Dobrzycki
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Correspondence to Kinga Ostrowska.

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The authors declare that they have no conflict of interest.

Electronic Supplementary material

The deposition numbers CCDC-1542353 CCDC-1854981 and CCDC-1854982 for different polymorphs of 1 contain the supplementary crystallographic data for this paper. These data can be obtained free of chargé via www.ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax 44 1223 336,033

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Ostrowska, K., Maciejewska, D., Cichowicz, G. et al. Solid-state structure by X-ray and 13C CP/MAS NMR of new 6-acetyl-8-bromo-5-O-alkylamino-4,7-dimethylcoumarins. Struct Chem 29, 1903–1915 (2018). https://doi.org/10.1007/s11224-018-1167-4

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  • DOI: https://doi.org/10.1007/s11224-018-1167-4

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