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Crystal Structure of 1,7-Bis(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)-1,6-heptadiene-3,5-dione

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Abstract

The synthesis and crystal structure of 1,7-bis(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)-1,6-heptadiene-3,5-dione is described. This compound is a curcuminoid analogue, configurationally symmetric about the C4–C5 atoms and also retains the two fold axis in the crystal phase. This compound crystallizes in the space group C2/c with unit cell parameters a = 19.203(1) Å, b = 13.147(1) Å, c = 8.801(1) Å, β = 112.99(1)°, with half a molecule in the asymmetric unit. The ketenedithioacetal functionality present between the carbonyl groups prevents the possibility of keto-enol tautomerization in this compound. The push-pull nature of the ketenedithioacetal functionality organizes the cinnamoyl groups parallel to each other.

Index Abstract

The details regarding synthesis and crystal structure of the title compound which is a curcuminoid analogue is reported in this paper.

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References

  1. Ramsewek RS, Dewitt DL, Nair MG (2000) Phytomedicine 7:303

    Google Scholar 

  2. Ruby Anto J, Dineshbabu KV, Rajasekharan KN, Kuttan R (1995) Cancer Lett 94:74

    Article  Google Scholar 

  3. Kunchandy E, Rao MNA (1990) Int J Pharm 58:237

    Article  CAS  Google Scholar 

  4. John VD, Krishnankutty K (2005) Transition Metal Chem 30:229–233

    Article  CAS  Google Scholar 

  5. Anto RJ, George J, Dineshbabu KV, Rajasekharan KN, Kuttan R (1996) Mutat Res 370:127

    Article  CAS  Google Scholar 

  6. Nagabushan M, Bhide SV (1992) J Am Cell Nutr 11:192

    Google Scholar 

  7. John VD, Krishnankutty K (2006) Appl Organomet Chem 20:477–482

    Article  CAS  Google Scholar 

  8. Tonnesen HH, Karlsen J, Mostad A (1982) Acta Chem Scand B36:475–479

    Article  Google Scholar 

  9. Gorbitz CH, Mostad A (1993) Acta Chem Scand 47:509–513

    Article  CAS  Google Scholar 

  10. Mostad A, Pedersen U, Rasmussen PB, Lawesson SO (1984) Acta Chem Scand B38:479–484

    Article  CAS  Google Scholar 

  11. Hollander FJ, Templeton DH, Zalken A (1973) Acta Crystallogr B29:1552

    Google Scholar 

  12. Williams DE, Dumke WL, Rundle RE (1962) Acta Crystallogr 15:627

    Article  CAS  Google Scholar 

  13. Williams DE (1966) Acta Crystallogr 21:340

    Article  CAS  Google Scholar 

  14. Sheldrick GM (1997) SHELX-97, University of Gottingen, Germany

  15. Bubbly KJ, Verghese B, Sudarsanakumar C, Deepa S, Dhanya V, Prakash C, Asokan CV (2002) J Chem Soc Chem Commun 736–737

  16. Karlsen J, Mostad A, Tonnesen HH (1988) Acta Chem Scand B42:23–27

    Article  CAS  Google Scholar 

  17. North ACT, Phillips DC, Mathews FS (1968) Acta Crystallogr A24:351–359

    Google Scholar 

  18. Zsolnai L (1997) ZORTEP 1997, University of Heidelberg

  19. Brahde LB (1954) Acta Chem Scand 8:1145

    Article  CAS  Google Scholar 

  20. Schmidt WH, Tulinsky (1967) Tetrahedron Lett 5311

  21. Deepak C, Mohan TP, Rao KS, Guru Row TN (2005) Acta Crystallogr E61:o3–o5

    Google Scholar 

  22. Spek AL (1990) Acta Crystallogr A46:C-34

    Google Scholar 

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Acknowledgements

The authors are indebted to (the late) Dr. C. V. Asokan, School of Chemical Sciences, Mahatma Gandhi University, Kottayam, Kerala, for all the help received, especially in the synthesis of this compound.

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Authors and Affiliations

  1. Post Graduate Department of Physics, Christ College (Autonomous), Hosur Road, Bangalore, 560 029, Karnataka, India

    S. G. Bubbly & S. B. Gudennavar

  2. Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Chennai, 600 036, India

    Babu Verghese

  3. School of Chemical Sciences, Mahatma Gandhi University, Kottayam, 686 560, Kerala, India

    Dhanya Viswam

  4. School of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, 686 560, Kerala, India

    C. Sudarsanakumar

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  1. S. G. Bubbly
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  2. S. B. Gudennavar
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  3. Babu Verghese
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  5. C. Sudarsanakumar
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Correspondence to S. G. Bubbly.

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Bubbly, S.G., Gudennavar, S.B., Verghese, B. et al. Crystal Structure of 1,7-Bis(4-chlorophenyl)-4-(1,3-dithiolan-2-ylidene)-1,6-heptadiene-3,5-dione. J Chem Crystallogr 38, 641–644 (2008). https://doi.org/10.1007/s10870-008-9362-6

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  • DOI: https://doi.org/10.1007/s10870-008-9362-6

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