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Crystal Structure Studies of Two Regioisomers of Bromo-4-Aryloxymethylcoumarins

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Abstract

The 4-(2-bromo-4-methyl-phenoxymethyl)-6-methylcoumarin (1) have been synthesized from bromination of corresponding 4-aryloxymethyl coumarin, which is a regioisomer of 4-(2-bromo-4-methyl-phenoxymethyl)-7-methylcoumarin (2) (CCDC-695895). The compound 1 crystallizes with triclinic space group P-1, a = 8.0943(3) Å, b = 9.3502(3) Å, c = 10.1476(4) Å, α = 90.234(2)°, β = 94.065(2)°, γ = 95.106(2)°, Z = 2 and compound 2 crystallizes with monoclinic space group P21/n, a = 8.465(5) Å, b = 13.649(5) Å, c = 13.304(5) Å, α = 90.000(5)°, β = 90.740(5)°, γ = 90.000(5)°, Z = 4. Both the compounds are planar with variation in their intermolecular hydrogen bonds between C–H···O and C–H···π.

Graphical Abstract

The 4-(2-bromo-4-methyl-phenoxymethyl)-6-methylcoumarin (1) have been synthesized from bromination of corresponding 4-aryloxymethyl coumarin, which is a regioisomer of 4-(2-bromo-4-methyl-phenoxymethyl)-7-methylcoumarin (2) (CCDC-695895). Compared the crystal structure properties of 1 with 2.

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References

  1. Kulkarni MV, Kulkarni GM, Lin CH, Sun CM (2006) Curr Med Chem 13:2795

    Article  CAS  Google Scholar 

  2. Fylaktakidou KC, Hadjpavlou D, Litinas KE, Nicolaides DN (2004) Curr Pharm Design 10:3813

    Article  CAS  Google Scholar 

  3. Neyts J, Clercq ED, Singha R, Chang YH, Das AR, Chakraborty SK, Hong SC, Tsay SC, Hsu MH, Hwu JR (2009) J Med Chem 52:1486

    Article  CAS  Google Scholar 

  4. Gnanaguru K, Ramasubbu N, Venkatesan K, Ramamurthy V (1985) J Org Chem 50:2337

    Article  CAS  Google Scholar 

  5. Munshi P, Row TNG (2005) J Phys Chem A 109:659

    Article  CAS  Google Scholar 

  6. Gavuzzo E, Mazza F (1974) Acta Cryst B30:1351

    Google Scholar 

  7. Murthy JN, Venkatakrishnan P, Singh AS (2003) Cryst Eng Commun 5:507

    Google Scholar 

  8. Katerinopoulos HE (2004) Curr Pharm Des 10:3835

    Article  CAS  Google Scholar 

  9. Gaultier J, Hauw C (1965) Acta Cryst C19:927

    Article  Google Scholar 

  10. Kokila MK, Puttaraja KulkarniMV, Shivaprakash NC (1996) Acta Cryst C52:2078

    CAS  Google Scholar 

  11. Puttaraja, Vasudevan KT, Kulkarni MV (1991) Acta Cryst C47:774

    Google Scholar 

  12. Kempen I, Papapostolou D, Thierry N, Pochet L, Counerotte S, Masereel B, Foidart J-M, Reboud-Ravaux M, Noel A, Pirotte B (2003) Br J Can 88:1111

    Article  CAS  Google Scholar 

  13. Puttaraja, Vasudevan KT, Kulkarni MV (1990) Acta Cryst C46:2129

    Google Scholar 

  14. Basanagouda M, Kulkarni MV, Sharma D, Gupta VK, Pranesha, Sandhyarani P, Rasal VP (2009) J Chem Sci 121:485

    Article  CAS  Google Scholar 

  15. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR (1997) Vogel’s textbook of practical organic chemistry, 5th edn. Addison Wesley Longman, Harlow, England

    Google Scholar 

  16. Bruker, SMART (Version 5.0), SAINT (Version 6.02) Aabd SADABS (Version 2.10). Bruker AXS Inc., Madison, WI

  17. Sheldrick GM, SHELXS-97 (1997) Program for the solution of crystal structures. University of Goettingen, Germany

    Google Scholar 

  18. Sheldrick GM, SHELXL-97 (1997) Program for the refinement of crystal structures. University of Goettingen, Germany

    Google Scholar 

  19. Kulkarni MV, Pujar BG, Patil VD (1981) Arch Pharm 316:15

    Article  Google Scholar 

Download references

Acknowledgments

Authors thank the University sophisticated instrumentation centre (USIC), Karnatak University, Dharwad for the spectral data. One of the authors, Mr. Mahantesha. Basanagouda is grateful to Karnatak University, Dharwad for a University Research Studentship. (D. S and V. K. G) grateful to the Head, SAIF, IIT Madras, Chennai for providing the intensity data collection facility.

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Authors and Affiliations

  1. Post-Graduate Department of Chemistry, Karnatak University, Dharwad, Karnataka, 580 003, India

    Manantesha Basanagouda & Manohar V. Kulkarni

  2. Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, 180 006, India

    Deepak Sharma & Vivek K. Gupta

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  1. Manantesha Basanagouda
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  2. Manohar V. Kulkarni
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  3. Deepak Sharma
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  4. Vivek K. Gupta
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Correspondence to Manohar V. Kulkarni.

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Basanagouda, M., Kulkarni, M.V., Sharma, D. et al. Crystal Structure Studies of Two Regioisomers of Bromo-4-Aryloxymethylcoumarins. J Chem Crystallogr 41, 541–544 (2011). https://doi.org/10.1007/s10870-010-9917-1

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  • DOI: https://doi.org/10.1007/s10870-010-9917-1

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