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Supramolecular architecture in the crystals of polyfluorinated homophthalic acids

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Abstract

X-ray diffraction analysis of four perfluorinated homophthalic (2-carboxymethylbenzoic) acids is carried out. In the crystals of 2-carboxymethyl-3,4,5,6-tetrafluorobenzoic acid (1) the chains (1D architecture) form with the usual dimeric carboxylic C(O)OH

O(HO)C synthon. The aromatic carboxylic group is disordered in the ratio 0.58:0.42 over two positions. In the crystals of 2-(carboxydifluoromethyl)-3,4,5,6-tetrafluorobenzoic (2) and 2-(1-carboxy-2,2,2-trifluoroethyl)-3,4,5,6-tetrafluorobenzoic acids (3) the layers (2D architecture) with dimeric and chain-like synthons C(O)OH...O(HO)C are found. In the crystals of 2-[methoxycarbonyl(difluoromethyl)]-3,4,5,6-tetrafluorobenzoic acid (4) only dimers (0D architecture) form with the chain synthon that incorporates both an ester and a carboxylic group. In the crystals of 1 and 2 intermolecular H-O...π interactions, in the crystals of 4 C-F...π interactions, and in 3 both types of interactions are observed.

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References

  1. T. Steiner, Angew. Chem. Int. Ed. Engl., 41, 48–76 (2002).

    Article  CAS  Google Scholar 

  2. G. R. Desiraju, Acc. Chem. Res., 35, 565–573 (2002).

    Article  CAS  Google Scholar 

  3. G. R. Desiraju, Chem. Commun., 1475–1482 (1997).

  4. F. H. Allen, W. D. S. Motherwell, P. R. Raithby, et al., New J. Chem., 23, No. 1, 25–34 (1999).

    Article  CAS  Google Scholar 

  5. K. Reichenbacher, H. I. Suss, and J. Hulliger, Chem. Soc. Rev., 34, 22–30 (2005).

    Article  Google Scholar 

  6. Cambridge Structural Database, Version 5.28, Univ. Cambridge, UK.

  7. V. M. Karpov, T. V. Mezhenkov, V. E. Platonov, and G. G. Yakobson, Izv. Akad. Nauk SSSR. Ser. Khim., 745/746 (1991).

  8. V. M. Karpov, V. E. Platonov, and G. G. Yakobson, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, Vyp. 2, 124–129 (1974).

  9. G. M. Sheldrick, SHELX-97, release 97-2, Univ. Göttingen, Germany (1998).

    Google Scholar 

  10. F. H. Allen, O. Kennard, D. G. Watson, et al., J. Chem. Soc. Perkin Trans. II, No. 12, S1–S19 (1987).

  11. D. Britton, Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 62, o510 (2006).

    Article  Google Scholar 

  12. D. Das and G. R. Desiraju, Chem. Asian J., 1, 231–244 (2006).

    Article  CAS  Google Scholar 

  13. C. C. Wilson and A. E. Goeta, Angew. Chem., Int. Ed., 43, 2095–2099 (2004).

    Article  CAS  Google Scholar 

  14. G. Qadeer, N. H. Rama, and Q.-S. Li, Acta Crystallogr., Sect. E: Struct. Rep. Online, 62, o906/o907 (2006).

    Google Scholar 

  15. G. S. Khan, N. H. Rama, A. Noor, et al., Z. Kristallogr.-New Cryst. Struct., 221, 153/154 (2006).

    Google Scholar 

  16. M. P. Gupta and M. Sahu, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 27, 2469–2473 (1971).

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia

    T. V. Rybalova, Yu. V. Gatilov, Ya. V. Zonov & V. M. Karpov

Authors
  1. T. V. Rybalova
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  2. Yu. V. Gatilov
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  3. Ya. V. Zonov
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  4. V. M. Karpov
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Corresponding author

Correspondence to Yu. V. Gatilov.

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Original Russian Text Copyright © 2008 by T. V. Rybalova, Yu. V. Gatilov, Ya. V. Zonov, and V. M. Karpov

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Translated from Zhurnal Strukturnoi Khimii, Vol. 49, No. 4, pp. 769–774, May–June, 2008.

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Rybalova, T.V., Gatilov, Y.V., Zonov, Y.V. et al. Supramolecular architecture in the crystals of polyfluorinated homophthalic acids. J Struct Chem 49, 742–747 (2008). https://doi.org/10.1007/s10947-008-0104-6

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  • DOI: https://doi.org/10.1007/s10947-008-0104-6

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