Skip to main content
SpringerLink
Log in

Methoxy- and methyl-substituted indole-3-acetonitrile (IAN): crystal structure and Hirshfeld surfaces analysis

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

Abstract

Crystal structural investigations and Hirshfeld surface analysis of three methoxy- and methyl-substituted indole-3-acetonitriles (IAN) (4-OCH3-IAN, 5-OCH3-IAN and 7-CH3-IAN) are reported in this work. Their structures were characterized by infrared spectra, elemental analyses, NMR spectra, differential scanning calorimetry, thermogravimetric analyses, and hot stage microscopy. The Hirshfeld surface analysis in terms of intermolecular interactions and π···π stacking motifs of the three substituted IANs was investigated in detail, and the results revealed that the different kinds of substituent groups as well as different substituted positions have a significant effect on the crystal structures, molecular π···π stacking motifs, melting points, and the types of intermolecular interactions.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. T. Blundell, J. Singh, J. Thornton, S.K. Burley, G.A. Petsko, Science 234, 1005 (1986)

    Article  CAS  Google Scholar 

  2. K.M. Brijesh, N. Sathyamurthy, J. Phys. Chem. B 109, 6 (2005)

    Google Scholar 

  3. C. Chipot, R. Jaffe, B. Maigret, D.A. Pearlman, P.A. Kollman, J. Am. Chem. Soc. 118, 11217 (1996)

    Article  CAS  Google Scholar 

  4. C.G. Claessens, J.F. Stoddart, J. Phys. Org. Chem. 10, 254 (1997)

    Article  CAS  Google Scholar 

  5. P. Hobza, J. Sponer, J. Am. Chem. Soc. 124, 11802 (2002)

    Article  CAS  Google Scholar 

  6. P.J. Garrat, Aromaticity (Wiley, New York, 1986)

    Google Scholar 

  7. V.I. Minkin, M.N. Glukhovtsev, B.Y. Simkin, Aromaticity and Antiaromaticity (Wiley, New York, 1994)

    Google Scholar 

  8. K. Jug, A.M. Koester, J. Am. Chem. Soc. 112, 6772 (1990)

    Article  CAS  Google Scholar 

  9. Z. Chen, C.S. Wannere, C. Corminboeuf, R. Puchta, P.V.R. Schleyer, Chem. Rev. 105, 3842 (2005)

    Article  CAS  Google Scholar 

  10. A.W. Woodward, B. Bartel, Ann. Bot. 95, 707 (2005)

    Article  CAS  Google Scholar 

  11. P.J. Davies, Plant Hormones: Biosynthesis, Signal Transduction, Action! (Kluwer Academic Publishers, Dordrecht, 2004), pp 1–15

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

  13. F.P.A. Fabbiani, L.T. Byrne, J.J. McKinnon, M.A. Spackman, CrystEngComm 9, 648 (2007)

    Article  Google Scholar 

  14. Y.H. Luo, C.G. Zhang, B. Xu, B.W. Sun, CrystEngComm 14(20), 6860 (2012)

    Article  CAS  Google Scholar 

  15. Y.H. Luo, B.W. Sun, Cryst. Growth Des. 13(5), 2098 (2013)

    Article  CAS  Google Scholar 

  16. Y.H. Luo, B. Xu, B.W. Sun, J. Cryst. Growth 374, 88 (2013)

    Google Scholar 

  17. M.A. Spackman, J.J. McKinnon, CrystEngComm 4, 378 (2002)

    Article  CAS  Google Scholar 

  18. Y.H. Luo, J. Xu, B.W. Sun, J. Chem. Res. 36, 697 (2012)

    Article  CAS  Google Scholar 

  19. Y.H. Luo, Q. Zhou, B.W. Sun, J. Chem. Res. 36, 506 (2012)

    Article  CAS  Google Scholar 

  20. Y.H. Luo, G.G. Wu, S.L. Mao, B.W. Sun, Inorg. Chim. Acta 397, 1 (2013)

    Article  CAS  Google Scholar 

  21. J.J. McKinnon, M.A. Spackman, A.S. Mitchell, Acta Crystallogr. Sect. B Struct. Sci. 60, 627 (2004)

    Article  Google Scholar 

  22. J.J. McKinnon, F.P.A. Fabbiani, M.A. Spackman, Cryst. Growth Des. 7, 755 (2007)

    Article  CAS  Google Scholar 

  23. Y.H. Ge, J.F. Li, Y.H. Luo, Acta Cryst. Sect. E E68(1), o66 (2012)

  24. Y.H. Ge, M.L. Pan, J. Xu, Y.H. Luo, Acta Cryst. Sect. E E68(1), o141 (2012)

  25. Y.H. Lu, M.L. Pan, Y.H. Luo, Acta Cryst. Sect. E E68(1), o143 (2012)

  26. Rigaku, CrystalClear, Version 14.0 (Rigaku Corporation, Tokyo, 2005)

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

    Google Scholar 

  28. Y.H. Luo, Y.T. Ma, Q.Q. Bao, B.W. Sun, J. Chem. Crystallogr. 42(6), 628 (2012)

    Article  CAS  Google Scholar 

  29. Y. H. Luo, Y. H. Lu, B.W. Sun, Inorganica Chimica Acta 404, 188 (2013)

    Google Scholar 

  30. Y. H. Luo, B.W. Sun, CrystEngComm 15, 7490 (2013)

  31. K. Bandenburg, DIAMOND: Crystal and Molecular Structure Visualization, Version 3.1b. Crystal Impact GbR (Bonn, 2006)

  32. Mercury 2.3 Supplied with Cambridge Structural Database (CCDC, Cambridge, 2003–2004)

  33. S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, CrystalExplorer 2.0 (University of Western Australia, Perth, 2007)

  34. G.R. Desiraju, A. Gavezzotti, Acta Crystallogr. Sect. B: Struct. Sci. 45, 473 (1989)

    Article  Google Scholar 

  35. G.R. Desiraju, A. Gavezzotti, Chem. Commun. 621 (1989)

  36. L. Loots, L.J. Barbour, CrystEngComm 14, 300 (2012)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Southeast University, Nanjing, 210096, People’s Republic of China

    Yu-Hua Ge & Yang-Hui Luo

Authors
  1. Yu-Hua Ge
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yang-Hui Luo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu-Hua Ge.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ge, YH., Luo, YH. Methoxy- and methyl-substituted indole-3-acetonitrile (IAN): crystal structure and Hirshfeld surfaces analysis. Res Chem Intermed 41, 2915–2927 (2015). https://doi.org/10.1007/s11164-013-1400-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1400-0

Keywords

Search

Navigation