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Structural study on four co-crystals of N-containing heteroaromatics with iodofluorobenzene

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Abstract

N-Containing heteroaromatics 1,2,4,5-tetra(pyridin-3-yl)benzene[1,2,4,5-T(3-PY)B] and 1,2,4,5-tetra-(pyridin-4-yl)benzene[1,2,4,5-T(4-PY)B] were each co-crystallized with 1,2-diiodo-tetrafluoro-benzene(1,2-DITFB), or 1,4-diiodo-tetrafluoro-benzene(1,4-DITFB), respectively, generating four co-crystals, namely, (1,2-DITFB)4·[1,2,4,5-T(3-PY)B](1), (1,2-DITFB)4·[1,2,4,5-T(4-PY)B](2), (1,4-DITFB)2·[1,2,4,5-T(3-PY)B]·CHCl3(3), and (1,4-DITFB)·[1,2,4,5-T(4-PY)B]·2CHCl3(4). This study takes aim at providing an insight into the relative importance of fundamental solid state halogen bonding interactions(i.e., halogen⋯N, halogen⋯halogen, and halogen⋯π) in systems. The effects of the donor and acceptor on supramolecular assembly and the crystal structure determined interactions were discussed. The N⋯I halogen bonds are the main directing interactions responsible for the observed structures. In compounds 1 and 2, the donors exhibited lower-than-expected supramolecular connectivity. In spite of this, co-crystal 2 exhibits polymeric structures consisting of infinite one-dimensional(1D) double-zigzag chains of alternating electron donor and acceptor. The basic structure of co-crystals 3 and 4 is also infinite 1D chain. Therefore, the 1D halogen bonded supramolecular assemblies can be obtained by matching the appropriate donor and acceptor.

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References

  1. Moulton B., Zaworotko M. J., Chem. Rev., 2001, 101, 1629

    Article  CAS  Google Scholar 

  2. Ciesielski A., Palma C. A., Bonini M., Samorì P., Adv. Mater., 2010, 22, 3506

    Article  CAS  Google Scholar 

  3. Muller-Dethlefs K., Hobza P., Chem. Rev., 2000, 100, 143

    Article  Google Scholar 

  4. Ji B. M., Deng D. S., Ma N., Miao S. B., Liu P., Li X. F., Chem. J. Chinese Universities, 2011, 32(9), 2114

    CAS  Google Scholar 

  5. Desiraju G. R., Angew. Chem., Int. Ed., 2010, 49, 2

    Article  Google Scholar 

  6. Ji B. M., Deng D. S., Ma N., Miao S. B., Ji L. G., Liu P., Li X. F., Cryst. Growth Des., 2011, 11, 4090

    Article  CAS  Google Scholar 

  7. Metrangolo P., Neukirch H., Pilati T., Resnati G., Acc. Chem. Res., 2005, 38, 386

    Article  CAS  Google Scholar 

  8. Metrangolo P., Meyer F., Pilati T., Resnati G., Terraneo G., Angew. Chem., Int. Ed., 2008, 47, 6114

    Article  CAS  Google Scholar 

  9. Metrangolo P., Pilati T., Resnati G., CrystEngComm, 2006, 8, 946

    Article  CAS  Google Scholar 

  10. Murray J. S., Riley K. E., Politzer P., Clark T., Aust. J. Chem., 2010, 63, 1598

    Article  CAS  Google Scholar 

  11. Politzer P., Lane P., Concha M. C., Ma Y., Murray J. S., J. Mol. Model., 2007, 13, 305

    Article  CAS  Google Scholar 

  12. Gavezzotti A., Mol. Phys., 2008, 106, 1473

    Article  CAS  Google Scholar 

  13. Carlsson A. C. C., Gräfenstein J., Laurila J. L., Bergquist J., Erdelyi M., Chem. Commun., 2012, 17, 1458

    Article  Google Scholar 

  14. Nguyen H. L., Horton P. N., Hursthouse M. B., Legon A. C., Bruce D. W., J. Am. Chem. Soc., 2004, 126, 16

    Article  CAS  Google Scholar 

  15. Fourmigue M., Batail P., Chem. Rev., 2004, 104, 5379

    Article  CAS  Google Scholar 

  16. Cavallo G., Metrangolo P., Pilati T., Resnati G., Sansotera M., Terraneo G., Chem. Soc. Rev., 2010, 39, 3772

    Article  CAS  Google Scholar 

  17. Ji B. M., Wang W. Z., Deng D. S., Zhang Y., Cryst. Growth Des., 2011, 11, 3622

    Article  CAS  Google Scholar 

  18. Ji B. M., Wang W. Z., Deng D. S., Zhang Y., Cao L., Zhou L., Ruan C. S., Li T. S., CrystEngComm, 2013, 15, 769

    Article  CAS  Google Scholar 

  19. Ji B. M., Zhang Y., Deng D. S., Wang W. Z., CrystEngComm, 2013, 15, 3093

    Article  CAS  Google Scholar 

  20. Perrin C. L., Pure Appl. Chem., 2009, 81, 571

    Article  CAS  Google Scholar 

  21. Carlsson A. C. C., Gräfenstein J., Budnjo A., Laurila J. L., Bergquist J., Karim A., Kleinmaier R., Brath U., Erdélyi M., J. Am. Chem. Soc., 2012, 134, 5706

    Article  CAS  Google Scholar 

  22. Pfrunder M. C., Micallef A. S., Rintoul L., Arnold D. P., Davy K. J., McMurtrie J., Cryst. Growth Des., 2012, 12, 714

    Article  CAS  Google Scholar 

  23. Hans H. W., Wolfram S., Eur. J. Org. Chem., 2002, 3927

    Google Scholar 

  24. Sheldrick G. M., SADABS: Program for Empirical Absorption Correction, University of Göttingen, Göttingen, 1996

    Google Scholar 

  25. Sheldrick G. M., SHELXL-97: Program for the Refinement of Crystal Structure, University of Göttingen, Göttingen, 1997

    Google Scholar 

  26. Parisini E., Metrangolo P., Pilati T., Resnati G., Terraneo G., Chem. Soc. Rev., 2011, 40, 2267

    Article  CAS  Google Scholar 

  27. Bhasikuttan A. C., Pal H., Mohanty J., Chem. Commun., 2011, 47, 9959

    Article  CAS  Google Scholar 

  28. Metrangolo P., Resnati G., Science, 2008, 321

    Google Scholar 

  29. Kumar V. S. S., Pigge F. C., Rath N. P., CrystEngComm, 2004, 6, 102

    Article  CAS  Google Scholar 

  30. Pigge F. C., Vangala V. R., Swenson D. C., Rath N. P., Cryst. Growth Des., 2010, 10, 224

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, 471022, P. R. China

    Baoming Ji, Dongsheng Deng, Weizhou Wang, Ke Wang & Mengli He

Authors
  1. Baoming Ji
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  2. Dongsheng Deng
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  3. Weizhou Wang
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  4. Ke Wang
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  5. Mengli He
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Correspondence to Baoming Ji.

Additional information

Supported by the National Natural Science Foundation of China(Nos.21372112, 21272109) and the Science and Technology Innovation Team Support Programs of Henan Province University, China(No.2012IRTSTHN019).

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Ji, B., Deng, D., Wang, W. et al. Structural study on four co-crystals of N-containing heteroaromatics with iodofluorobenzene. Chem. Res. Chin. Univ. 31, 84–90 (2015). https://doi.org/10.1007/s40242-015-4145-z

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  • DOI: https://doi.org/10.1007/s40242-015-4145-z

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