Advertisement

Research on Chemical Intermediates

, Volume 42, Issue 4, pp 3157–3168 | Cite as

Crystals of 4-(2-benzimidazole)-1,2,4-triazole and its hydrate: preparations, crystal structure and Hirshfeld surfaces analysis

  • Wei Wang
  • Yang Ling
  • Li-Jing Yang
  • Qing-Ling Liu
  • Yang-Hui Luo
  • Bai-Wang Sun
Article

Abstract

Single crystals of compound L (C9H7N5): 4-(2-benzimidazole)-1,2,4-triazole and its hydrate were obtained via slow evaporation. The structures of the crystals were characterized by IR, TGA/DSC and X-ray diffraction analysis. Molecules in crystal 1 are linked by a combination of N–H···N and C–H···N hydrogen bonds into 2D layers, and further stacked into a 3D structure by π···π stacking interactions. Compared to crystal 1, the water molecules play a key role in the construction of the crystal structure of hydrate 2. The 2D layers were formed via O–H···N, O–H···O, N–H···N hydrogen bonds, and further stacked by O–H···O hydrogen bonds and π···π stacking interactions in crystal 2. A detailed analysis of the intermolecular interactions and crystal packing via Hirshfeld surface analysis and fingerprint plots reveals that the structures are stabilized mainly by N···H/H···N, C···H/H···C hydrogen bonds, H···H weak interactions and π···π stacking interactions.

Keywords

4-(2-Benzimidazole)-1,2,4-triazole Hydrate Crystal structure Hirshfeld surface 

Notes

Acknowledgments

We are very grateful for the financial support from the National Natural Science Foundation of China (Nos. 21241009, 21371031), and the Technological Program Foundation of Jiangsu Province (No. BY2012193).

Supplementary material

11164_2015_2203_MOESM1_ESM.doc (64 kb)
Supplementary material 1 (DOC 64 kb)

References

  1. 1.
    S. Moitra, S.K. Seth, T. Kar, J. Cryst. Growth 312, 1977 (2010)CrossRefGoogle Scholar
  2. 2.
    S. Adhikari, S.K. Seth, T. Kar, CrystEngComm 15, 7372 (2013)CrossRefGoogle Scholar
  3. 3.
    S.K. Seth, N.C. Saha, S. Ghosh, T. Kar, Chem. Phys. Lett. 506, 309 (2011)CrossRefGoogle Scholar
  4. 4.
    N. Blagden, M. Matas, P.T. Gavan, P. York, Adv. Drug Deliv. Rev. 59, 617 (2007)CrossRefGoogle Scholar
  5. 5.
    L. Wang, L.Y. Xu, R.F. Xue, X.F. Lu, R.X. Chen, X.T. Tao, Sci. China Chem. 55, 138 (2012)CrossRefGoogle Scholar
  6. 6.
    T. Miyahira, H. Hasegawa, Y. Takahashi, T. Inabe, Cryst. Growth Des. 13, 1995 (2013)CrossRefGoogle Scholar
  7. 7.
    K. Fatemeh, S. Ali, J. Abolghasem, J. Pharm. Sci. (2015). doi: 10.1002/jps.24525 Google Scholar
  8. 8.
    J.W. Steed, Trends Pharmacol. Sci. 34, 185 (2013)CrossRefGoogle Scholar
  9. 9.
    P. Manna, S.K. Seth, M. Mitra, S.R. Choudhury, A. Bauzá, A. Frontera, S. Mukhopadhyay, Cryst. Growth Des. 14, 5812 (2014)CrossRefGoogle Scholar
  10. 10.
    S.K. Seth, N.K. Das, K. Aich, D. Sen, H.K. Fun, S. Goswami, J. Mol. Struct. 1048, 157 (2013)CrossRefGoogle Scholar
  11. 11.
    H.S. Yin, G.S. Yang, C.B. Liu, A.W. He, Y.B. Zhou, Z.P. Zhang, H.M. Li, Chin. J. Struct. Chem. 34, 650 (2015)Google Scholar
  12. 12.
    S.R. Vippagunta, H.G. Brittain, D.J.W. Grant, Adv. Drug Deliv. Rev. 48, 3 (2001)CrossRefGoogle Scholar
  13. 13.
    D.E. Braun, T. Gelbrich, V. Kahlenberg, U.J. Griesser, Mol. Pharm. 11, 3145 (2014)CrossRefGoogle Scholar
  14. 14.
    D.E. Braun, L.H. Koztecki, J.A. Reutzel-Edens, Mol. Pharm. doi: 10.1021/acs.5b00357
  15. 15.
    P. Manna, S.K. Seth, A. Bauzá, M. Mitra, S.R. Choudhury, A. Frontera, S. Mukhopadhyay, Cryst. Growth Des. 14, 747 (2014)CrossRefGoogle Scholar
  16. 16.
    S.K. Seth, Inorg. Chem. Commun. 43, 60 (2014)CrossRefGoogle Scholar
  17. 17.
    N. Demirbas, R. Ugurluoglu, A. Demirbas, Bioorg. Med. Chem. 10, 3717 (2002)CrossRefGoogle Scholar
  18. 18.
    P. Zoumpoulakis, C. Camoutsis, G. Pairas et al., Bioorg. Med. Chem. 20, 1569 (2012)CrossRefGoogle Scholar
  19. 19.
    Y.H. Luo, D.E. Wu, S.W. Ge, Y. Li, B.W. Sun, RSC Adv. 4, 11698 (2014)CrossRefGoogle Scholar
  20. 20.
    Y. Bansal, O. Silakari, Bioorg. Med. Chem. 20, 6208 (2012)CrossRefGoogle Scholar
  21. 21.
    I. Briguglio, S. Piras, P. Corona, E. Gavini, M. Nieddu, G. Boatto, A. Carta, Eur. J. Med. Chem. 97, 612 (2015)CrossRefGoogle Scholar
  22. 22.
    J. Krober, E. Codjovi, O. Kahn, F. Grolibre, C. Jay, J. Am. Chem. Soc. 115, 9810 (1993)CrossRefGoogle Scholar
  23. 23.
    P. Manna, S.K. Seth, M. Mitra, A. Das, N.J. Singh, S.R. Choudhury, T. Kar, S. Mukhopadhyay, CrystEngComm 15, 7879 (2013)CrossRefGoogle Scholar
  24. 24.
    S.K. Seth, P. Manna, N.J. Singh, M. Mitra, A.D. Jana, A. Das, S.R. Choudhury, T. Kar, S. Mukhopadhyay, K.S. Kim, CrystEngComm 15, 1285 (2013)CrossRefGoogle Scholar
  25. 25.
    J.A. Kitchen, J. Olguín, R. Kulmaczewski, S. Brooker et al., Inorg. Chem. 52, 11185 (2013)CrossRefGoogle Scholar
  26. 26.
    Rigaku, CrystalClear, Version 14.0, Rigaku Corporation, Tokyo, Japan, 2005Google Scholar
  27. 27.
    G.M. Sheldrick, SHELXS97: Programs for Crystal Structure Analysis (University of Göttingen, Germany, 1997)Google Scholar
  28. 28.
    S.K. Seth, I. Saha, C. Estarellas, A. Frontera, T. Kar, S. Mukhopadhyay, Cryst. Growth Des. 11, 3250 (2011)CrossRefGoogle Scholar
  29. 29.
    S.K. Seth, D. Sarkar, T. Kar, CrystEngComm 13, 4528 (2011)CrossRefGoogle Scholar
  30. 30.
    S.K. Seth, CrystEngComm 15, 1772 (2013)CrossRefGoogle Scholar
  31. 31.
    S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M. A. Spackman, Crystal Explorer 2.1, University of Western Australia, Perth, Australia, 2007Google Scholar
  32. 32.
    A. Parkin, G. Barr, W. Dong, C.J. Gilmore, D. Jayatilaka, J.J. McKinnon, M.A. Spackman, C.C. Wilsona, CrystEngComm 9, 648 (2007)CrossRefGoogle Scholar
  33. 33.
    S.K. Seth, D. Sarkar, A.D. Jana, T. Kar, Cryst. Growth Des. 11, 4837 (2011)CrossRefGoogle Scholar
  34. 34.
    S.K. Seth, D. Sarkar, A. Roy, T. Kar, CrystEngComm 13, 6728 (2011)CrossRefGoogle Scholar
  35. 35.
    S.K. Seth, J. Mol. Struct. 1070, 65 (2014)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Wei Wang
    • 1
  • Yang Ling
    • 1
  • Li-Jing Yang
    • 1
  • Qing-Ling Liu
    • 1
  • Yang-Hui Luo
    • 1
  • Bai-Wang Sun
    • 1
  1. 1.School of Chemistry and Chemical EngineeringSoutheast UniversityNanjingPeople’s Republic of China

Personalised recommendations