Skip to main content
SpringerLink
Log in

Structural Conformation of a Novel 1-Benzhydrylpiperazine Derivative: 1-Benzhydryl-4-(toluene-4-sulfonyl)-piperazine

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

Abstract

The title compound 1-benzhydryl-4-(toluene-4-sulfonyl)-piperazine was synthesized and the structure was investigated by X-ray crystallography. The title compound, C24H26N2O2S crystallizes in the monoclinic crystal class in the space group P21/c with cell parameters a = 13.5800(10) Å, b = 8.9630(7) Å, c = 18.9040(10) Å, β = 106.851(3)°, Z = 4 and V = 2202.1(3) Å3. The structure has been solved by direct methods and refined to R 1 = 0.0468 for 3174 observed reflections I > 2σ(I). The structure reveals that the piperazine ring is in a chair conformation. The geometry around the S atom is a distorted tetrahedron.

Graphical Abstract

The title compound 1-benzhydryl-4-(toluene-4-sulfonyl)-piperazine was synthesized and the structure was investigated by X-ray crystallography. The title compound, C24H26N2O2S crystallizes in the monoclinic crystal class in the space group P21/c with cell parameters a = 13.5800(10) Å, b = 8.9630(7) Å, c = 18.9040(10) Å, β = 106.851(3)°, Z = 4 and V = 2202.1(3) Å3. The structure has been solved by direct methods and refined to R 1 = 0.0468 for 3174 observed reflections I > 2σ(I). The structure reveals that the piperazine ring is in a chair conformation. The geometry around the S atom is a distorted tetrahedron.

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

Fig. 1
Fig. 2

Similar content being viewed by others

Notes

  1. CCDC 673346 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033.

References

  1. Berkheij M, Vander Sluis L, Sewing C, Den Boer DJ, Terpstra JW, Hiemstra H, Iwema Bakker WI, Van Den Hoogenband A, Van Maarseveen JH (2005) Tetrahedron Lett 46:2369

    Article  CAS  Google Scholar 

  2. Haga N, Ishibashi T, Hara A, Abiko Y (1985) Pharmacology 31:208

    Article  CAS  Google Scholar 

  3. Sashida H, Abiko Y (1985) Biochem Pharmacol 34:3875

    Article  CAS  Google Scholar 

  4. Toyo-oka T, Kamishiro T, Masaki M, Masaki T (1982) Jpn Heart J 23:829

    CAS  Google Scholar 

  5. Wilson WD, Barton HJ, Tanious FA, Kong SB, Strekowski L (1990) Biophys Chem 35:227

    Article  CAS  Google Scholar 

  6. Hulme C, Cherrier MP (1999) Tetrahedron Lett 40:5295

    Article  CAS  Google Scholar 

  7. Yoshida M, Maehara Y, Sugimachi K (1999) Clin Cancer Res 5:4295

    CAS  Google Scholar 

  8. Guo CC, Li HP, Zhang XB (2003) Bioorg Med Chem 11:1745

    Article  CAS  Google Scholar 

  9. Guo CC, Tong RB, Li KL (2004) Bioorg Med Chem 12:2469

    Article  CAS  Google Scholar 

  10. Foroumadi A, Ghodsi S, Emami S, Najjari S, Samadi N, Faramarzi MA, Beikmohammadi L, Shirazi FH, Shafiee A (2006) Bioorg Med Chem Lett 16:3499

    Article  CAS  Google Scholar 

  11. Foroumadi A, Emami S, Mansouri S, Javidnia A, Saeid-Adeli N, Farshad HS, Shafiee A (2007) Eur J Med Chem 42:985

    Article  CAS  Google Scholar 

  12. Elizabeth Amin A, Welsh WJ (2001) J Med Chem 44:3849

    Article  Google Scholar 

  13. Upadhayaya RS, Sinha N, Jain S, Kishore N, Chandra R, Arora SK (2004) Bioorg Med Chem 12:2225

    Article  CAS  Google Scholar 

  14. Choudhary P, Kumar R, Verma K (2006) Bioorg Med Chem 14:1819

    Article  Google Scholar 

  15. Vacca JP, Dorsey BD, Schleif WA, Levine RB, McDaniel SL, Darke PL, Zugay J, Quintero JC, Blahy OM, Sardana BB, Schlabach AJ, Graham PI, Condra JH, Gotalib L, Holloway MK, Lin J, Chen IW, Vastag K, Ostovic D, Anderson PS, Emini EA, Hu JR (1994) J Med Chem 37:3443

    Article  Google Scholar 

  16. Askin D, Eng KK, Rossen K, Purick RM, Wells KM, Volante RP, Reider P (1994) J Tetrahedron Lett 35:673

    Article  CAS  Google Scholar 

  17. Rossen K, Weissman SA, Sagar J, Reamer A, Askin DA, Volante RP, Reider P (1995) J Tetrahedron Lett 36:6419

    Article  CAS  Google Scholar 

  18. Hutchison Peterson AJ, Doller JM, Pringle D, Yin WC (1975) EGYT US-3865828

  19. Mark A, Matulenko Ahmed A, Hakeem Kolasa T, Nakane M, Marc A, Terranova Marie E, Uchic Loan N, Chang MR, Diana L, Roberts M, Marian T, Namovic Robert B, Moreland Jorge D, Brioni Andrew O (2004) Stewart Bioorg Med Chem 12:3471

    Google Scholar 

  20. Glase SA, Akunne HC, Georgic LM, Heffner TG, Mackenzie RG, Manley PJ, Pugsley TA, Wise LD (1997) J Med Chem 40:1771

    Article  CAS  Google Scholar 

  21. Perrone R, Berardi F, Colabufo NA, Leopoldo M, Tortorella V (2000) J med Chem 43:270

    Article  CAS  Google Scholar 

  22. Chern JH, Shia KS, Hsu TA, Tai CL, Lee CC, Lee YC, Chang CS, Tseng SN, Shih SR (2004) Bioorg Med Chem Lett 14:2519

    Article  CAS  Google Scholar 

  23. Kimura M, Masuda T, Yamada K, Mitani M, Kubota N, Kawakatsu N, Kishii K, Inazu M, Kiuchi Y, Oguchi K, Namiki T (2003) Bioorg Med Chem 11:1621

    Article  CAS  Google Scholar 

  24. Mura M, Masuda T, Yamada K, Mitani M, Kubota N, Kawakatsu N, Kishii K, Inazu M, Kiuchi Y, Oguchi K, Namiki T (2003) Bioorg Med Chem 11:3953

    Article  Google Scholar 

  25. Mura M, Masuda T, Yamada K, Mitani M, Kubota N, Kawakatsu N, Kishii K, Inazu M, Kiuchi Y, Oguchi K, Namiki T (2004) Bioorg Med Chem 13:3069

    Google Scholar 

  26. Guo CC, Tong RB, Li KL (2004) Bioorg Med Chem 12:2469

    Article  CAS  Google Scholar 

  27. Kimura M, Masuda T, Yamada K, Mitani M, Kubota N, Kawakatsu N, Kishii K, Inazu M, Kiuchi Y, Oguchi K, Namiki T (2004) Bioorg Med Chem 14:4287

    Article  CAS  Google Scholar 

  28. Ananda Kumar CS, Nanjunda Swamy S, Thimme Gowda NR, Benaka Prasad SB, Yip GW, Rangappa KS (2007) Med Chem Res doi:10.1007/s00044-007-9022-y:

  29. Otwinowski Z, Minor W (1997) In: Carter CW Jr, Sweet RM (eds) Methods in enzymology: macromolecular crystallography, vol 276. Academic Press, New York, p 307

  30. Mackay S, Gillmore CJ, Edwards C, Shankland K (1999) maXus, Computer program for the solution and refinement of crystal structures. Bruker Nonius/MacScience/The University of Glasgow, The Netherlands/Japan/UK

  31. Sheldrick GM (1997) SHELXS-97 Program for crystal structure Solution. University of Göttingen, Germany

    Google Scholar 

  32. Sheldrick GM (1997) SHELXL-97. Program for crystal structure Solution. University of Göttingen, Germany

    Google Scholar 

  33. Spek AL (1998) Acta Cryst A46:C34

    Google Scholar 

  34. Cremer D, Pople JA (1975) Acta Cryst 97:1354

    CAS  Google Scholar 

  35. Naveen S, Nanjundaswamy S, Basappa Prabhuswamy B, Sridhar MA, Prasad JS, Rangappa KS (2006) Anal Sci 22:x41

    Article  CAS  Google Scholar 

  36. Perales A, Cano FH, Garcia-Blanco S (1977) Acta Cryst B33:3172

    Article  Google Scholar 

  37. Bassindale A (1984) The third dimension in organic chemistry. John Wiley and Sons, New York

    Google Scholar 

Download references

Acknowledgements

The authors are grateful to Department of Science and Technology and Government of India for financial assistance under the projects SP/I2/FOO/93 and UGC-SAP(Phase-I)No.F.540/10/DRS/2004(SAP-I). One of the author K. Vinaya, would like to thank CSIR, Government of India for the award of Senior Research Fellowship.

Author information

Authors and Affiliations

  1. Department of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India

    S. Naveen, M. A. Sridhar & J. Shashidhara Prasad

  2. Department of Studies in Chemistry, University of Mysore, Mysore, 570 006, India

    C. S. Ananda Kumar, S. B. Benaka Prasad, K. Vinaya & K. S. Rangappa

Authors
  1. S. Naveen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. C. S. Ananda Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. B. Benaka Prasad
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. Vinaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. A. Sridhar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. J. Shashidhara Prasad
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. K. S. Rangappa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. A. Sridhar.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Naveen, S., Ananda Kumar, C.S., Benaka Prasad, S.B. et al. Structural Conformation of a Novel 1-Benzhydrylpiperazine Derivative: 1-Benzhydryl-4-(toluene-4-sulfonyl)-piperazine. J Chem Crystallogr 39, 395–398 (2009). https://doi.org/10.1007/s10870-008-9490-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-008-9490-z

Keywords

Search

Navigation