Skip to main content
SpringerLink
Log in

Structures of Two (E)-3-Substituted Cinnamoylbenzotriazole 1-Oxides

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The molecule of (E)-3-(3-MeOC6H4CH=CHCO)-benzotriazole 1-oxide, 2, has a very near planar structure, while the 2-nitrophenyl ring is rotated out of the plane of the remaining atoms in (E)-3-(2-O2NC6H4CH=CHCO)-benzotriazole 1-oxide, 1. The nitrogen oxide bond lengths in 1 and 2 are 1.258 (6) and 1.2683 (15) Å, respectively, and are in the region found for related compounds. There are no strong intermolecular hydrogen-bonds in either compound, instead there are weak C–H···O intermolecular hydrogen-bonds and π···π stacking interactions in 1, and C–H···O, C–H···π, and π···π stacking interactions in 2. Different three-dimensional arrays are generated in each case. Compound 1 crystallises in the orthorhombic space group Pna21, with a = 25.061 (2) Å, b = 3.6997 (2) Å, c = 14.2623 (12) Å and Z = 4. Compound 2 crystallises in the triclinic space group P-1, with a = 5.7297 (3) Å, b = 10.8440 (6) Å, c = 11.4965 (6) Å, α = 89.689 (3)°, β = 76.019 (3)°, γ = 75.047 (3)°, Z = 2.

Graphical Abstract

Different combinations of intermolecular interactions generate different three-dimensional arrangements in the two (E)-3-substituted cinnamoylbenzotriazole 1-oxides

.

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
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Han SY, Kim YA (2004) Tetrahedron 60:2447

    Article  CAS  Google Scholar 

  2. König W, Geiger R (1970) Chem Ber 103:788

    Article  Google Scholar 

  3. Munekata E, Sakakibara S (1973) Yuki Gosei Kagaku Kyokaishi 31:853

    Article  CAS  Google Scholar 

  4. Brink BD, DeFrancisco JR, Hillner JA, Linton BR (2011) J Org Chem 76:5258 (and refs therein)

    Article  CAS  Google Scholar 

  5. Anders E, Katritzky AR, Malhotra N, Stevens J (1992) J Org Chem 57:3698

    Article  CAS  Google Scholar 

  6. Katritzky AR, Malhotra N, Fan WQ, Anders E (1991) J Chem Soc Perkin Trans 2:1545

    Google Scholar 

  7. Barlos K, Papaioannou D, Theodoropoulos D (1984) Int J Pept Protein Res 23:300

    Article  CAS  Google Scholar 

  8. Barlos K, Papaioannou D, Sanida C (1984) Liebigs Ann Chem 1308

  9. Carvahlo SA, da Silva EF, de Souza MVN, Lourenço MCS, Vicente FR (2008) Bioorg Med Chem Lett 18:538

    Article  Google Scholar 

  10. Carvalho SA, da Silva EF, Tiekink ERT, Wardell JL, Wardell SMSV (2009) Acta Crystallogr E65:o3118

    CAS  Google Scholar 

  11. Carvalho SA, da Silva EF, Fraga CAM, Wardell SMSV, Wardell JL, Tiekink ERT (2010) Acta Crystallogr E66:o2410

    CAS  Google Scholar 

  12. Carvalho SA, da Silva EF, de Souza MVN, Tiekink ERT, Wardell JL, Wardell SMSV (2010) Acta Crystallogr E66:o150

    CAS  Google Scholar 

  13. Naz S, Ahmad S, Rasool SA, Sayeed SA, Siddiqi R (2006) Microb Res 161:43

    Article  CAS  Google Scholar 

  14. Rastogi N, Goh KS, Horgen L, Barrow WW (1998) FEMS Immunol Med Microbiol 21:149

    Article  CAS  Google Scholar 

  15. Reddy VM, Nadadhur G, Daneluzzi D, Dimova V, Gangadharam PRJ (1995) Antimicrob Agents Chemother 39:2320

    CAS  Google Scholar 

  16. Bezerra DP, Castro FO, Alves APNN, Pessoa C, Moraes MO, Silveira ER, Lima MS, Elmiro FJM, Costa-Lotufo LV (2006) Braz J Med Biol Res 39:801

    Article  CAS  Google Scholar 

  17. Chung HS, Shin JC (2007) Food Chem 104:1670

    Article  CAS  Google Scholar 

  18. Pardin C, Pelletier JN, Lubell WD, Keillo JW (2008) J Org Chem 73:5766

    Article  CAS  Google Scholar 

  19. Barlos K, Papaioannou D, Voliotis S, Prewo R, Bieri JH (1985) J Org Chem 50:696

    Article  CAS  Google Scholar 

  20. Mamos P, Papaioannou D, Kavounis C, Nastopoulos V (1997) Acta Crystallogr C53:1973

    CAS  Google Scholar 

  21. Li JM, Yong JP (2010) Acta Crystallogr E66:o13

    CAS  Google Scholar 

  22. Nagarajan S, Wilson SR, Rinehart KL Jr (1985) J Org Chem 50:2174

    Article  CAS  Google Scholar 

  23. Vlassi M, Germain G, Barlos K, Mamos P, Refaat LS (1990) Z Kristallogr 192:59

    CAS  Google Scholar 

  24. McCarthy DG, Hegarty AF, Brian J, Hathaway BJ (1977) J Soc Perkin Trans 2:2224

    Google Scholar 

  25. Hooft RWW (1998) COLLECT data collection software. Nonius B.V., The Netherlands

    Google Scholar 

  26. Otwinowski Z, Minor W (1997) In: Carter CW Jr, Sweet RM (eds) Methods in enzymology, Vol. 276, macromolecular crystallography, Part A. Academic Press, New York, pp 307–326

    Google Scholar 

  27. Sheldrick GM (2007) SADABS version 2007/2. Bruker AXS Inc., Madison

    Google Scholar 

  28. Sheldrick GM (2008) Acta Crystallogr A64:112

    CAS  Google Scholar 

  29. McArdle P (2006) OSCAIL for windows, version 1.0.12. Crystallography Centre, Chemistry Department, NUI Galway, Galway

    Google Scholar 

  30. Flack HD (1983) Acta Crystallogr A39:876

    CAS  Google Scholar 

  31. Farrugia L (1997) J Appl Crystallogr 30:65

    Article  Google Scholar 

  32. Spek AL (2003) J Appl Crystallogr 36:7

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The use of the NCS X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there are gratefully acknowledged. JLW thanks CAPES for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland, UK

    R. Alan Howie

  2. Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos—Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos, Rio de Janeiro, RJ, 21041-250, Brazil

    Marcus V. N. de Souza & Camilo H. da Silva Lima

  3. Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, Rio de Janeiro, RJ, 21040-900, Brazil

    James L. Wardell

  4. CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland, UK

    Solange M. S. V. Wardell

Authors
  1. R. Alan Howie
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marcus V. N. de Souza
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Camilo H. da Silva Lima
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. James L. Wardell
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Solange M. S. V. Wardell
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to James L. Wardell.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Howie, R.A., de Souza, M.V.N., da Silva Lima, C.H. et al. Structures of Two (E)-3-Substituted Cinnamoylbenzotriazole 1-Oxides. J Chem Crystallogr 42, 394–400 (2012). https://doi.org/10.1007/s10870-011-0260-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0260-y

Keywords

Search

Navigation