Skip to main content
SpringerLink
Log in

Synthesis and Structural Characterization of Three Phenylsulfonyl Derivatives: Influence of Halogen Substituents on the Intermolecular Interactions

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

Abstract

Synthesis and X-ray structural determination of three halogenated nitroimidazo[1,2-a]pyridine phenylsulfonyl derivatives are reported. (2) is monoclinic P21/c with a = 9.6679(1), b = 11.3642(2), c = 15.2189(2)Å, β = 105.9053(7)°; (3) is triclinic P −1 with a = 8.5556(2), b = 13.1191(3), c = 15.5132(4)Å, α = 76.0110(8), β = 89.1768(8), γ = 78.953(2)°; (4) is monoclinic P21/c with a = 15.3353(2), b = 8.8621(2), c = 11.4189(3)Å, β = 90.9704(7)°. In the title compounds that differ by the nature and number of halogen substituents, the arylsulfonyl moieties are oriented differently relatively to the nitroimidazopyridine. Moreover non-classical intermolecular interactions are revealed by the X-ray analysis.

Graphical Abstract

The X-ray structures of three halogenated nitroimidazo[1,2-a]pyridine phenylsulfonyl derivatives reveal different intermolecular interactions within the crystals.

C. Castera, M. D. Crozet, M. Giorgi and P. Vanelle

The X-ray structures of three halogenated nitroimidazo[1,2-a]pyridine phenylsulfonyl derivatives reveal different intermolecular interactions within the crystals.

Synthesis and structural characterization of three phenylsulfonyl derivatives: influence of halogen substituents on the intermolecular interactions.

C. Castera,1 M. D. Crozet,1 M. Giorgi,2 and P. Vanelle1*

1Laboratoire de Chimie Organique Pharmaceutique, UMR CNRS 6517, Université de la Méditerranée, Faculté de Pharmacie, 27 Boulevard Jean Moulin, 13385 Marseille cedex 5, France ; 2Spectropôle-RX, Université Paul Cézanne Aix-Marseille III, Faculté des Sciences et Techniques, Avenue Escadrille Normandie-Niemen, 13397 Marseille cedex 20, France.

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
Scheme 2
Scheme 3
Fig. 4

Similar content being viewed by others

References

  1. Nájera C, Yus M (1999) Tetrahedron 55:10547

    Article  Google Scholar 

  2. Castera C, Crozet MD, Vanelle P (2005) Heterocycles 65:2979

    Article  CAS  Google Scholar 

  3. Crozet MD, Perfetti P, Kaafarani M, Crozet MP, Vanelle P (2004) Lett Org Chem 1:326

    Article  CAS  Google Scholar 

  4. Crozet MD, Castera C, Kaafarani M, Crozet MP, Vanelle P (2003) Arkivoc X:273

    Google Scholar 

  5. Otwinowski Z, Minor W (1997) Methods Enzymol 276:307

    Article  CAS  Google Scholar 

  6. Blessing RH (1997) J Appl Cryst 30:421

    Article  CAS  Google Scholar 

  7. Altomare A, Cascarano G, Giacovazzo C, Guagliardi A, Burla MC, Polidori G, Camalli M (1994) J Appl Cryst 27:435

    Article  Google Scholar 

  8. Sheldrick GM (1997) Shelxl97, Program for Crystal Refinement Structures. University of Göttingen, Germany

  9. Farrugia, LJ (1997) J Appl Cryst, 30:565; Johnson, CK (1976) OrtepII. Oak Ridge National Laboratory, Tenessee

  10. Paulini R, Müller K, Diederich F (2005) Angew. Chem Int Ed 44:1788

    Article  CAS  Google Scholar 

  11. Meyer E, Castellano RK, Diederich F (2003) Angew Chem Int Ed 42:1210

    Article  CAS  Google Scholar 

  12. Nishio M (2005) Tetrahedron 61:6923

    Article  CAS  Google Scholar 

  13. Tatko CD, Waters ML (2004) Org Lett 6:3969

    Article  CAS  Google Scholar 

  14. Gromiha MM (2003) Biophys Chemist 103:251

    Article  CAS  Google Scholar 

  15. Nishio N (2004) Cryst Eng Comm 6:130

    CAS  Google Scholar 

  16. Metrangolo P, Neukirch H, Pilati T, Resnati G (2005) Acc Chem Res 38:386

    Article  CAS  Google Scholar 

  17. Fourmigué M, Batail P (2004) Chem Rev 104:5379

    Article  CAS  Google Scholar 

  18. Parthasarathy R, Desiraju GR (1989) J Am Chem Soc 111:8725

    Article  Google Scholar 

  19. Reddy CM, Kirchner MT, Gundakaram RC, Padmanabhan KA, Desiraju GR (2006) Chem Eur J 12:2222

    Article  CAS  Google Scholar 

  20. Bondi A (1964) J Phys Chem 68:441

    Article  CAS  Google Scholar 

  21. Metrangolo P, Neukirch H, Pilati T, Resnati G (2005) Acc Chem Res 38:386 and references therein

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie Organique Pharmaceutique, UMR CNRS 6517, Faculté de Pharmacie, Université de la Méditerranée, 27 Boulevard Jean Moulin, Marseille Cedex 5, 13385, France

    C. Castera, M. D. Crozet & P. Vanelle

  2. Spectropôle-RX, Faculté des Sciences et Techniques, Université Paul Cézanne Aix-Marseille III, Avenue Escadrille Normandie-Niemen, Marseille Cedex 20, 13397, France

    M. Giorgi

Authors
  1. C. Castera
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. D. Crozet
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Giorgi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. P. Vanelle
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to P. Vanelle.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Castera, C., Crozet, M.D., Giorgi, M. et al. Synthesis and Structural Characterization of Three Phenylsulfonyl Derivatives: Influence of Halogen Substituents on the Intermolecular Interactions. J Chem Crystallogr 37, 831–836 (2007). https://doi.org/10.1007/s10870-007-9256-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-007-9256-z

Keywords

Search

Navigation