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A new polymorph of methimazole: Single crystal and powder X-ray diffraction study

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Abstract

A new polymorph of 1-methyl-4-imidazoline-2-thione has been first discovered and studied by X-ray diffraction. The crystal of the new polymorph is monoclinic, the asymmetric part of the cell contains three independent molecules. In the crystal, the key compound is in the form of planar hydrogen-bonded dimers due to the interactions of the N-H…S type. The new modification is of an intensely yellow color in contrast to the previously known colorless forms, is characterized by a lower density but stronger hydrogen bonds; it is formed as a minor impurity to main triclinic polymorph.

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References

  1. R. Leurs, H. van der Goot, and H. Timmerman, Adv. Drug Res., 20, 217 (1991).

    CAS  Google Scholar 

  2. P. Goldman, J. Antimicrob. Chemother., 10A, 23 (1982).

    Article  Google Scholar 

  3. K. Nagarajan, V. P. Arya, T. George, et al., Indian J. Chem., 21B, 928 (1982).

    CAS  Google Scholar 

  4. State Pharmacopoeia of USSR [in Russian], Meditsina, Moscow (1968).

  5. M. D. Mashkovskii, Pharmaceuticals [in Russian], Novaya Volna, Moscow (2010).

    Google Scholar 

  6. G. L. Vyshkovskii (ed.), Russian Register of Pharmaceuticals. Encyclopedia of Drugs [in Russian], RLS-MEDIA, Moscow (2010).

    Google Scholar 

  7. A. T. Soldatenkov, N. M. Kolyadina, and I. V. Shendrik (eds.), in: Fundamentals of Organic Chemistry of Medicinal Substances [in Russian], Mir, BINOM, Laboratoriya Znanii, Moscow (2010).

    Google Scholar 

  8. A. V. Arefèv, V. A. Startseva, L. E. Nikitina, et al., Zh. Obshch. Khim., 82, No. 3, 440 (2012).

    Google Scholar 

  9. E. S. Raper, J. R. Creighton, R. E. Oughtred, et al., Acta Crystallogr., B39, 355 (1983).

    CAS  Google Scholar 

  10. G. Vampa, S. Benvenuti, F. Severi, et al., J. Heterocyclic Chem., 32, 227 (1995).

    Article  CAS  Google Scholar 

  11. J. W. Steed, Cryst. Eng. Comm., No. 5, 169 (2003).

    Google Scholar 

  12. G. R. Desiraju, Cryst. Eng. Comm., No. 9, 91 (2007).

    Google Scholar 

  13. K. M. Anderson, A. E. Goeta, K. S. Hancock, and J. W. Steed, Chem. Commun., No. 20, 2138 (2006).

    Google Scholar 

  14. K. M, Anderson and J. W. Steed, Cryst. Eng. Comm., No. 9, 328 (2007).

    Google Scholar 

  15. A. A. Bredikhin, R. M. Eliseenkova, Z. A. Bredikhina, et al., Chirality, No. 21, 37 (2009).

    Google Scholar 

  16. K. M. Anderson, K. Afarinkia, H.-W. Yu, et al., Cryst. Growth Des., No. 6, 2109 (2006).

    Google Scholar 

  17. K. M. Anderson, M. R. Probert, and C. N. Whiteley, Cryst. Growth Des., No. 9, 1082 (2009).

    Google Scholar 

  18. Yu. V. Nelyubina, M. Yu. Antipin, I. A. Cherepanov, et al., Cryst. Eng. Comm., No. 12, 77 (2010).

    Google Scholar 

  19. N. Biswas, S. Thomas, A. Sarkar, et al., Chem. Phys. Lett., 479, Nos. 4–6, 248 (2009).

    Article  CAS  Google Scholar 

  20. M. Garner, D. R. Armstrong, and J. Reglinski, Bioorgan. Medicin. Chem. Lett., 4, No. 11, 1357 (1994).

    Article  CAS  Google Scholar 

  21. R. S. Balestrero, D. M. Forkey, and J. G. Russel, Maqn. Reson. Chem., 24, 651 (1986).

    Article  CAS  Google Scholar 

  22. C. Laurence, M. J. Ghomari, and J.-Y. Questel, J. Chem. Soc. Perkin Trans. 2, 1545 (1998).

    Google Scholar 

  23. Cambrige Structural Database System, Version 1.12, Cambrige Crystallographic Data Centre (2009).

  24. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, New York (1990).

    Google Scholar 

  25. E. Espinosa, E. Mollins, and C. Lecomte, Chem. Phys. Lett., 285, 170 (1998).

    Article  CAS  Google Scholar 

  26. G. M. Sheldrick, SADABS, Univ. Göttingen, Germany (2004).

    Google Scholar 

  27. G. M. Sheldrick, Acta Crystallogr., A64,part 1, 112 (2008).

    CAS  Google Scholar 

  28. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, Univ. Göttingen, Germany (1997).

    Google Scholar 

  29. L. J. Farrugia, J. Appl. Crystallogr., 32, No. 4, 837 (1999).

    Article  CAS  Google Scholar 

  30. APEX (Version 2.1), SAINTPlus, Data Reduction and Correction Program, Version 7.31A, Bruker Advansed X-Ray Solutsions. BrukerXS Inc., Madison, Wisconsin, USA (2006).

  31. A. L. Spek, Acta Crystallogr. (A), 46,part 1, 34 (1990).

    Google Scholar 

  32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammit, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA (1998).

    Google Scholar 

  33. A. D. Becke, Phys. Rev. A, 38, 3098 (1988).

    Article  CAS  Google Scholar 

  34. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).

    Article  CAS  Google Scholar 

  35. F. Biegler-König, J. Schönbohm, and D. Bayles, AIM2000-A Program to Analyze and Visualize Atoms in Molecules, J. Comp. Chem., 22, 545 (2001).

    Google Scholar 

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Correspondence to O. A. Lodochnikova.

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Original Russian Text Copyright © 2013 by O. A. Lodochnikova, A. V. Bodrov, A. F. Saifina, L. E. Nikitina, I. A. Litvinov

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Translated from Zhurnal Strukturnoi Khimii, Vol. 54, No. 1, pp. 146–154, January–February, 2013.

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Lodochnikova, O.A., Bodrov, A.V., Saifina, A.F. et al. A new polymorph of methimazole: Single crystal and powder X-ray diffraction study. J Struct Chem 54, 140–147 (2013). https://doi.org/10.1134/S0022476613010204

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  • DOI: https://doi.org/10.1134/S0022476613010204

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