Skip to main content
Log in

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

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. S. Moitra, S.K. Seth, T. Kar, J. Cryst. Growth 312, 1977 (2010)

    Article  CAS  Google Scholar 

  2. S. Adhikari, S.K. Seth, T. Kar, CrystEngComm 15, 7372 (2013)

    Article  CAS  Google Scholar 

  3. S.K. Seth, N.C. Saha, S. Ghosh, T. Kar, Chem. Phys. Lett. 506, 309 (2011)

    Article  CAS  Google Scholar 

  4. N. Blagden, M. Matas, P.T. Gavan, P. York, Adv. Drug Deliv. Rev. 59, 617 (2007)

    Article  CAS  Google Scholar 

  5. L. Wang, L.Y. Xu, R.F. Xue, X.F. Lu, R.X. Chen, X.T. Tao, Sci. China Chem. 55, 138 (2012)

    Article  CAS  Google Scholar 

  6. T. Miyahira, H. Hasegawa, Y. Takahashi, T. Inabe, Cryst. Growth Des. 13, 1995 (2013)

    Article  Google Scholar 

  7. K. Fatemeh, S. Ali, J. Abolghasem, J. Pharm. Sci. (2015). doi:10.1002/jps.24525

    Google Scholar 

  8. J.W. Steed, Trends Pharmacol. Sci. 34, 185 (2013)

    Article  CAS  Google Scholar 

  9. P. Manna, S.K. Seth, M. Mitra, S.R. Choudhury, A. Bauzá, A. Frontera, S. Mukhopadhyay, Cryst. Growth Des. 14, 5812 (2014)

    Article  CAS  Google Scholar 

  10. S.K. Seth, N.K. Das, K. Aich, D. Sen, H.K. Fun, S. Goswami, J. Mol. Struct. 1048, 157 (2013)

    Article  CAS  Google Scholar 

  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)

    CAS  Google Scholar 

  12. S.R. Vippagunta, H.G. Brittain, D.J.W. Grant, Adv. Drug Deliv. Rev. 48, 3 (2001)

    Article  CAS  Google Scholar 

  13. D.E. Braun, T. Gelbrich, V. Kahlenberg, U.J. Griesser, Mol. Pharm. 11, 3145 (2014)

    Article  CAS  Google Scholar 

  14. D.E. Braun, L.H. Koztecki, J.A. Reutzel-Edens, Mol. Pharm. doi:10.1021/acs.5b00357

  15. P. Manna, S.K. Seth, A. Bauzá, M. Mitra, S.R. Choudhury, A. Frontera, S. Mukhopadhyay, Cryst. Growth Des. 14, 747 (2014)

    Article  CAS  Google Scholar 

  16. S.K. Seth, Inorg. Chem. Commun. 43, 60 (2014)

    Article  CAS  Google Scholar 

  17. N. Demirbas, R. Ugurluoglu, A. Demirbas, Bioorg. Med. Chem. 10, 3717 (2002)

    Article  CAS  Google Scholar 

  18. P. Zoumpoulakis, C. Camoutsis, G. Pairas et al., Bioorg. Med. Chem. 20, 1569 (2012)

    Article  CAS  Google Scholar 

  19. Y.H. Luo, D.E. Wu, S.W. Ge, Y. Li, B.W. Sun, RSC Adv. 4, 11698 (2014)

    Article  CAS  Google Scholar 

  20. Y. Bansal, O. Silakari, Bioorg. Med. Chem. 20, 6208 (2012)

    Article  CAS  Google Scholar 

  21. I. Briguglio, S. Piras, P. Corona, E. Gavini, M. Nieddu, G. Boatto, A. Carta, Eur. J. Med. Chem. 97, 612 (2015)

    Article  CAS  Google Scholar 

  22. J. Krober, E. Codjovi, O. Kahn, F. Grolibre, C. Jay, J. Am. Chem. Soc. 115, 9810 (1993)

    Article  CAS  Google Scholar 

  23. P. Manna, S.K. Seth, M. Mitra, A. Das, N.J. Singh, S.R. Choudhury, T. Kar, S. Mukhopadhyay, CrystEngComm 15, 7879 (2013)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  25. J.A. Kitchen, J. Olguín, R. Kulmaczewski, S. Brooker et al., Inorg. Chem. 52, 11185 (2013)

    Article  CAS  Google Scholar 

  26. Rigaku, CrystalClear, Version 14.0, Rigaku Corporation, Tokyo, Japan, 2005

  27. G.M. Sheldrick, SHELXS97: Programs for Crystal Structure Analysis (University of Göttingen, Germany, 1997)

    Google Scholar 

  28. S.K. Seth, I. Saha, C. Estarellas, A. Frontera, T. Kar, S. Mukhopadhyay, Cryst. Growth Des. 11, 3250 (2011)

    Article  CAS  Google Scholar 

  29. S.K. Seth, D. Sarkar, T. Kar, CrystEngComm 13, 4528 (2011)

    Article  CAS  Google Scholar 

  30. S.K. Seth, CrystEngComm 15, 1772 (2013)

    Article  CAS  Google Scholar 

  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, 2007

  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)

    Article  CAS  Google Scholar 

  33. S.K. Seth, D. Sarkar, A.D. Jana, T. Kar, Cryst. Growth Des. 11, 4837 (2011)

    Article  CAS  Google Scholar 

  34. S.K. Seth, D. Sarkar, A. Roy, T. Kar, CrystEngComm 13, 6728 (2011)

    Article  CAS  Google Scholar 

  35. S.K. Seth, J. Mol. Struct. 1070, 65 (2014)

    Article  CAS  Google Scholar 

Download references

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).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Bai-Wang Sun.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 64 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, W., Ling, Y., Yang, LJ. et al. Crystals of 4-(2-benzimidazole)-1,2,4-triazole and its hydrate: preparations, crystal structure and Hirshfeld surfaces analysis. Res Chem Intermed 42, 3157–3168 (2016). https://doi.org/10.1007/s11164-015-2203-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2203-2

Keywords

Navigation