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A New Glycoluril Clip and Its Self-Association in Solid State

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Abstract

A new molecular clip C30H32N6O12 (1) derived from glycoluril has been synthesized and structurally determined by NMR, MS and X-ray diffraction analysis. The crystal belongs to an orthorhombic system, space group P 2(1)2(1)2(1), with unit cell parameters a = 13.868, b = 20.844, c = 22.990 Å, α = 90°, β = 90°, γ = 90°, V = 6,645.6 Å3, Z = 4, D c = 1.456 Mg/m3, μ = 0.228 mm−1, F(000) = 3,032, R 1 = 0.0457, wR 2 = 0.1281.

Graphical Abstract

We report a new glycoluril dimer which forms a double dimeric complex supramolecular building block and then packs in a tape-like fashion forming supramolecular polymers.

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References

  1. Rowan AE, Elemans JAAW, Nolte RJM (1999) Acc Chem Res 32:955

    Article  Google Scholar 

  2. Hof F, Craig SL, Nuckolls C, Rebek J Jr (2002) Angew Chem Int Ed 41:1488

    Article  CAS  Google Scholar 

  3. Lagona J, Fettinger JC, Isaacs L (2003) Org Lett 5:3745

    Article  CAS  Google Scholar 

  4. Kim J, Jung I-S, Kim S-Y, Lee E, Kang J-K, Sakamoto S, Yamaguchi K, Kim KJ (2000) J Am Chem Soc 122:540

    Article  CAS  Google Scholar 

  5. Day A, Arnold AP, Blanch RJ, Snushall BJ (2001) Org Chem 66:8094

    Article  CAS  Google Scholar 

  6. Kang J, Jo J-H, In S (2004) Tetrahedron Lett 45:5225

    Article  CAS  Google Scholar 

  7. Wu AX, Fettinger JC, Isaacs L (2002) Tetrahedron 58:9769

    Article  CAS  Google Scholar 

  8. Wu AX, Chakraborty A, Witt D, Lagona J, Damkaci F, Ofori MA, Chiles JK, Fittinger JC, Isaacs L (2002) J Org Chem 67:5817

    Article  CAS  Google Scholar 

  9. Wu AX, Mukhopadhyay P, Chakraborty A, Fittinger JC, Isaacs LJ (2004) J Am Chem Soc 126:10035

    Article  CAS  Google Scholar 

  10. Wu AX, Chakraborty A, Fettinger JC, Flowers RA, Isaacs L (2002) Angew Chem Int Ed 41:4028

    Article  CAS  Google Scholar 

  11. Wang ZG, Zhou BH, Chen YF, Yin GD, Li YT, Wu AX, Isaacs L (2006) J Org Chem 71:4502

    Article  CAS  Google Scholar 

  12. Yin GD, Wang ZG, Chen YF, Wu AX, Pan YJ (2006) Synlett 1:49

  13. She NF, Meng XG, Gao M, Wu AX, Isaacs L (2008) Chem Commun 27:3133

    Article  Google Scholar 

  14. Cao LP, Meng XG, Gao M, She NF, Wu AX (2008) Acta Crystallogr C 64:o69

    Article  Google Scholar 

  15. Chen YF, She NF, Meng XG, Yin GD, Wu AX, Isaacs L (2007) Org Lett 9:1899

    Article  CAS  Google Scholar 

  16. Cao LP, Meng XG, Ding JY, Xi HL, Wu AX (2011) J Chem Crystallogr 41:425

    Article  CAS  Google Scholar 

  17. Cao LP, Meng XG, Ding JY, Chen YF, Gao M, Wu YD, Li YT, Wu AX, Isaacs L (2010) Chem Commun 46:4508

    Article  CAS  Google Scholar 

  18. She NF, Gao M, Cao LP, Wu AX, Isaacs L (2009) Org Lett 11:2603

    Article  CAS  Google Scholar 

  19. Hu SL, She NF, Yin GD, Guo HZ, Wu AX, Yang CL (2007) Tetrahedron Lett 48:1591

    Article  CAS  Google Scholar 

  20. Ding JY, Chen YF, Wang JG, Wu AX, Cao LP (2010) J Chem Res 5:246

    Article  Google Scholar 

  21. She NF, Gao M, Meng XG, Yang GF, Elemans JAAW, Wu AX, Isaacs L (2009) J Am Chem Soc 131:11695

    Article  CAS  Google Scholar 

  22. Branda N, Grotzfeld RM, Valdbs C, Rebek J Jr (1995) J Am Chem Soc 117:85

    Article  CAS  Google Scholar 

  23. Wood JH, Perry MA, Tung CC (1950) J Am Chem Soc 72:2989

    Article  CAS  Google Scholar 

  24. Sheldrick GM (2001) SADABS. Version 2.10. Bruker AXS Inc., Madison

    Google Scholar 

  25. Sheldrick GM (1997) SHELXL97, program for crystal refinement. University of Gottingen, Gottingen

    Google Scholar 

  26. Sheldrick GM (1997) SHELXTL (version 5.0). Bruker AXS Inc., Madison

    Google Scholar 

  27. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  Google Scholar 

Download references

Acknowledgments

The authors would like to express their thanks to Prof. Anxin Wu and gratefully acknowledge to Xianggao Meng for performing the X-ray crystallographic measurements.

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Correspondence to Jungang Wang.

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Liu, Q., Wang, J. & Zhao, G. A New Glycoluril Clip and Its Self-Association in Solid State. J Chem Crystallogr 42, 727–732 (2012). https://doi.org/10.1007/s10870-012-0307-8

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  • DOI: https://doi.org/10.1007/s10870-012-0307-8

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