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Crystal structure and packing analysis of nitrofurantoin N,N-dimethylformamide solvate

  • Structure of Organic Compounds
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Abstract

The N, N′-dimethylformamide solvated crystal of the drug nitrofurantoin has been prepared and analysed by single-crystal X-ray diffraction. The two co-crystallized molecules, in the 1 : 1 stoichiometric ratio, are linked by a medium/strong N–H···O hydrogen bond (N···O is 2.759 (3) Å) and a weaker C–H···O interaction to form isolated supramolecular adducts, that in turn are packed into the lattice framework mainly through C–H···O hydrogen bonds. Two-dimensional fingerprint plots of Hirshfeld surfaces are used to visualize, analyze and compare intermolecular interactions found in the title compound and in similar structures.

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References

  1. Y. Tu, and D. R. McCalla, Biochem. Biophys. Acta 402, 142 (1975).

    Google Scholar 

  2. V. Bertolasi, P. Gilli, V. Ferretti, and G. Gilli, Acta Crystallogr. B 57, 591 (2001).

    Article  Google Scholar 

  3. V. Bertolasi, L. Pretto, P. Gilli, V. Ferretti, and G. Gilli, New J. Chem. 26, 1559 (2002).

    Article  Google Scholar 

  4. V. Ferretti, A. Dalpiaz, V. Bertolasi, L. Ferraro, S. Beggiato, F. Spizzo, E. Spisni, and B. Pavan, Mol. Pharmaceutics 12, 1501 (2015).

    Article  Google Scholar 

  5. F. L. Hirshfeld, Theor. Chim. Acta, 44, 129 (1977).

    Article  Google Scholar 

  6. Z. Otwinowski and W. Minor, Methods Enzymol. 276, 307 (1997).

    Article  Google Scholar 

  7. A. Altomare, M. C. Burla, M. Cavalli, G. Cascarano, C. Giacovazzo, A. Gagliardi, A. G. Moliterni, G. Polidori, and R. Spagna, J. Appl. Crystallogr. 32, 115 (1999).

    Article  Google Scholar 

  8. G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).

    Article  ADS  Google Scholar 

  9. L. J. Farrugia, J. Appl. Crystallogr. 32, 837 (1999).

    Article  Google Scholar 

  10. M. N. Burnett, and C. K. Johnson, ORTEPIII. Report ORNL-6895 (Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA, 1996).

    Google Scholar 

  11. K. Brandenburg, DIAMOND Version 2.0 (1998).

    Google Scholar 

  12. M. A. Spackman, and J. J. McKinnon, CrystEng-Comm 4, 378 (2002).

    Article  Google Scholar 

  13. J. J. McKinnon, D. Jayatilaka, and M. A. Spackman, Chem. Commun. 3814 (2007).

    Google Scholar 

  14. F. H. Allen, Acta Crystallogr. B 58, 380 (2002).

    Article  Google Scholar 

  15. S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, and M. A. Spackman, CrystalExplorer (Version 3. 0) (Univ. of Western Australia, 2012).

    Google Scholar 

  16. M. Tutughamiarso, M. Bolte, G. Wagner, and E. Egert, Acta Crystallogr. C 67, o18 (2011).

    Article  Google Scholar 

  17. A. Alhalaweh, S. George, S. Basavoju, S. Childs, S. A. A. Rizvi, and S. Velaga, CrystEngComm 14, 5078 (2012).

    Article  Google Scholar 

  18. V. R. Vangala, Pui Shan Chow, R. B. H. Tan, CrystEngComm 13, 759 (2011).

    Article  Google Scholar 

  19. V. R. Vangala, Pui Shan Chow, R. B. H. Tan, CrystEngComm 15, 878 (2013).

    Article  Google Scholar 

  20. S. Cherukuvada, N. J. Babu, A. Nangia, J. Pharm. Sci. 100, 3233 (2011).

    Article  Google Scholar 

  21. M. Spackman, and D. Jayatilaka, CrystEngComm, 11, 19 (2009).

    Article  Google Scholar 

  22. J. J. McKinnon, M. A. Spackman and A. S. Mitchell, Acta Crystallogr. B 60, 627 (2004).

    Article  Google Scholar 

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Correspondence to A. Cvetkovski.

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Cvetkovski, A., Ferretti, V. Crystal structure and packing analysis of nitrofurantoin N,N-dimethylformamide solvate. Crystallogr. Rep. 61, 611–615 (2016). https://doi.org/10.1134/S1063774516040040

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  • DOI: https://doi.org/10.1134/S1063774516040040

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