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X-ray mapping in heterocyclic design: XI. X-ray diffraction study of 1-benzoyl-3-(pyridin-2-yl)-thiocarbamide and the product of its reaction with oxidants

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Abstract

The structures of 1-benzoyl-3-(pyridin-2-yl)-thiocarbamide C13H11N3O1S1 (I) and 2-benzoylimino-1,2,4-thiadiazole[2,3-a]pyridine C13H9N3O1S1 (II) are studied by X-ray diffraction. Structures I [a = 5.342(4) Å, b = 20.428(5) Å, c = 11.784(4) Å, β = 90.55(2)°, Z = 4, space group P21/n) and II [a = 6.258(6) Å, b = 18.068(14) Å, c = 10.185(10) tA, β = 95.45(8)°, Z = 4, space group P21/n) are determined by direct methods and refined to R 1 = 0.0673 and 0.0802, respectively. In structure I, both intramolecular (involving the O atom) and intermolecular (involving the N and S atoms) hydrogen bonds are observed. The latter bonds are responsible for the formation of centrosymmetric molecular dimers. In structure II, a short intramolecular contact (2.168 Å) is observed between the S and O atoms.

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References

  1. V. B. Rybakov, S. G. Zhukov, E. V. Babaev, et al., Kristallografiya 44(6), 1067 (1999) [Crystallogr. Rep. 44, 997 (1999)].

    Google Scholar 

  2. V. B. Rybakov, S. G. Zhukov, E. V. Babaev, et al., Kristallografiya 45(1), 108 (2000) [Crystallogr. Rep. 45, 103 (2000)].

    Google Scholar 

  3. V. B. Rybakov, S. G. Zhukov, E. V. Babaev, et al., Kristallografiya 45(2), 292 (2000) [Crystallogr. Rep. 45, 261 (2000)].

    Google Scholar 

  4. V. B. Rybakov, S. G. Zhukov, K. Yu. Pasichnichenko, and E. V. Babaev, Koord. Khim. 26(9), 714 (2000).

    Google Scholar 

  5. V. B. Rybakov, S. G. Zhukov, E. V. Babaev, and E. J. Sonneveld, Kristallografiya 46(3), 435 (2001) [Crystallogr. Rep. 46, 385 (2001)].

    Google Scholar 

  6. V. B. Rybakov, S. I. Troyanov, E. V. Babaev, et al., Kristallografiya 46(5), 1069 (2001) [Crystallogr. Rep. 46, 986 (2001)].

    Google Scholar 

  7. V. B. Rybakov, E. V. Babaev, K. Yu. Pasichnichenko, and E. J. Sonneveld, Kristallografiya 47(1), 76 (2002) [Crystallogr. Rep. 47, 69 (2002)].

    Google Scholar 

  8. V. B. Rybakov, E. V. Babaev, and V. V. Chernyshev, Kristallografiya 47(3), 473 (2002) [Crystallogr. Rep. 47, 428 (2002)].

    Google Scholar 

  9. V. B. Rybakov, E. V. Babaev, and K. Yu. Pasichnichenko, Kristallografiya 47(4), 678 (2002) [Crystallogr. Rep. 47, 622 (2002)].

    Google Scholar 

  10. V. B. Rybakov, E. V. Babaev, A. A. Tsisevich, et al., Kristallografiya 47(6), 1042 (2002) [Crystallogr. Rep. 47, 973 (2002)].

    Google Scholar 

  11. D. V. Al'bov, V. B. Rybakov, E. V. Babaev, and L. A. Aslanov, Kristallografiya 48(2), 315 (2003) [Crystallogr. Rep. 48 (2), 280 (2003)].

    Google Scholar 

  12. F. H. Allen and O. Kennard, Chem. Design Automat. News 8(1), 31 (1993).

    Google Scholar 

  13. A. Preiss, W. Walek, and S. Dietzel, J. Prakt. Chem. 323, 279 (1981).

    Article  Google Scholar 

  14. G. L'abbe, J. Buelens, W. Dehaen, et al., Tetrahedron 50, 7019 (1994).

    Google Scholar 

  15. A. Kasheres and M. Ueno, J. Heterocycl. Chem. 28, 2057 (1991).

    Google Scholar 

  16. L. V. Sudha, D. N. Sathyanarayana, and S. Manogaran, Spectrochim. Acta A 42, 1373 (1986).

    Article  Google Scholar 

  17. J. Jirman and A. Lycka, Collection 52, 2474 (1987).

    Google Scholar 

  18. G. Y. Sarkis and E. D. Faisal, J. Heterocycl. Chem. 22, 137 (1985).

    Google Scholar 

  19. Enraf-Nonius CAD4 Software: Version 5.0 (Enraf-Nonius, Delft, The Netherlands, 1989).

  20. L. J. Farrugia, WinGX98: X-ray Crystallographic Programs for Windows (Univ. of Glasgow, UK, 1998).

    Google Scholar 

  21. G. M. Sheldrick, SHELX97: Program for the Solution and Refinement of Crystal Structures (Univ. of Göttingen, Germany, 1997).

    Google Scholar 

  22. A. L. Spek, PLUTON96: Molecular Graphics Program (Univ. of Utrecht, The Netherlands, 1996).

    Google Scholar 

  23. M. Nardelli, J. Appl. Crystallogr. 28, 659 (1995).

    Article  Google Scholar 

  24. S. S. S. Raj, K. Puviarasan, D. Velmurugan, et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 55, 1318 (1999).

    Google Scholar 

  25. A. Dago, Yu. Shepelev, F. Fajardo, et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 45, 1192 (1989).

    Article  Google Scholar 

  26. Zhang De-Chun, Zhang Yan-Qin, Cao Yang, and Zhao Bo, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 52, 1716 (1996).

    Google Scholar 

  27. Cao Yang, Zhao Bo, Zhang Yan-Qin, and Zhang De-Chun, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 52, 1772 (1996).

    Google Scholar 

  28. A. K. Hermetet, L. J. Ackerman, K. K. Eilts, et al., J. Mol. Struct. 605, 241 (2002).

    Article  Google Scholar 

  29. L. F. Szczepura, K. K. Eilts, A. K. Hermetet, et al., J. Mol. Struct. 607, 101 (2002).

    Article  Google Scholar 

  30. L. F. Szczepura, D. R. Kelman, A. K. Hermetet, et al., J. Mol. Struct. 608, 245 (2002).

    Article  Google Scholar 

  31. J. M. Giesen, K. A. Claborn, K. I. Goldberg, et al., J. Mol. Struct. 613, 223 (2002).

    Article  Google Scholar 

  32. S. S. S. Raj, K. Puviarasan, D. Velmuguran, et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 55, 1318 (1999).

    Google Scholar 

  33. F. M. Uckun and O. D'Cruz, US Patent No. 6376504 (April 23, 2002).

  34. O. Hassel, C. Romming, and T. Tufte, Acta Chem. Scand. 15, 967 (1961).

    Google Scholar 

  35. H. Hope and G. Hung-Yin Lin, J. Chem. Soc. Chem. Commun. 3, 169 (1970).

    Google Scholar 

  36. N. I. Burakov, A. L. Kanibolotskii, G. Yu. Osichenko, et al., Zh. Org. Khim. 37, 1276 (2001).

    Google Scholar 

  37. C. Cohen-Addad, M. S. Lehmann, P. Becker, et al., J. Chem. Soc., Perkin Trans. 2, 191 (1984).

  38. V. V. Chernyshev, K. A. Paseshnichenko, V. A. Makarov, et al., Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 57, 72 (2001).

    Google Scholar 

  39. R. L. N. Harris, Aust. J. Chem. 25, 993 (1972).

    Google Scholar 

  40. K. T. Potts and J. M. Kane, Synthesis, No. 12, 1027 (1986).

Download references

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, 119899, Russia

    V. B. Rybakov

  2. Institute of Physicoorganic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk, Ukraine

    L. G. Boboshko, N. I. Burakov, M. Yu. Zubritskii, V. I. Kovalenko, V. A. Savelova, A. F. Popov & V. A. Mikhailov

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  2. L. G. Boboshko
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__________

Translated from Kristallografiya, Vol. 48, No. 4, 2003, pp. 627–633.

Original Russian Text Copyright © 2003 by Rybakov, Boboshko, Burakov, Zubritski\(\overset{\lower0.5em\hbox{$\smash{\scriptscriptstyle\smile}$}}{l} \), Kovalenko, Savelova, Popov, Mikha\(\overset{\lower0.5em\hbox{$\smash{\scriptscriptstyle\smile}$}}{l} \)lov.

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Rybakov, V.B., Boboshko, L.G., Burakov, N.I. et al. X-ray mapping in heterocyclic design: XI. X-ray diffraction study of 1-benzoyl-3-(pyridin-2-yl)-thiocarbamide and the product of its reaction with oxidants. Crystallogr. Rep. 48, 576–582 (2003). https://doi.org/10.1134/1.1595182

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