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Crystal and molecular structure of the H-bonded complex between 1-chloro-2-hydroxynaphthalene-3-carboxylic acid and dimethylformamide (1∶1)

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Abstract

Crystal structure determination of the title complex reveals that the dimethylformamide solvent is bound to the carboxylic function of the hydroxy acid, in the form of a 7-membered hydrogen-bonded loop involving both the expected O-H⋯O and an apparently weak C-H⋯O interaction between host and guest. There is a strong intramolecular hydrogen bond between the phenolic OH and the carbonyl oxygen. Close packing of the complex units is afforded by a herringbone type alignment of host molecules.

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References

  • Cromer, D. T. (1974)International Tables for X-Ray Crystallography (Kynoch Press, Birmingham, England), Vol. IV, Table 2.3.1.

    Google Scholar 

  • Cromer, D. T., and Waber, J. T. (1974)International Tables for X-Ray Crystallography, J. A. Ibers, and W. C. Hamilton, eds. (Kynoch Press, Birmingham, England), Vol. IV, Table 2.2B.

    Google Scholar 

  • Csöregh, I., Czugler, M., Weber, E., Sjögren, A., and Cserzö, M. (1986)J. Chem. Soc., Perkin Trans. 2 507.

    Google Scholar 

  • Czugler, M., Stezowski, J. J., and Weber, E. (1983)J. Chem. Soc., Chem. Commun. 154.

  • Enraf-Nonius (1977)CAD4 Operations Manual (Enraf-Nonius, Delft).

    Google Scholar 

  • Etter, M. C. (1990)Acc. Chem. Res. 23, 120.

    Google Scholar 

  • Frenz, B. A. (1978)The Enraf-Nonius CAD4 SDP-A Real-time System for Concurrent X-Ray Data Collection and Crystal Structure Determination, in Computing in Crystallography, H. Schenk, R. Olthof-Hazekamp, H. van Koningsveld, and G. C. Bassi, eds. (Delft University Press, Delft, Holland), pp. 64–71.

    Google Scholar 

  • Gavezzotti, A., and Desiraju, G. R. (1988)Acta Crystallogr. B 44, 427.

    Google Scholar 

  • Ibers, J. A., and Hamilton, W. C. (1964)Acta Crystallogr. 17, 781.

    Google Scholar 

  • Ioffe, I. S., and Smoljanizkaja, I. Z. (1935)Z. Obsc. Chim. 5, 1205.

    Google Scholar 

  • Johnson, C. K., (1976)OrtepII A Fortran Thermal Ellipsoid Plot Program for Crystal Structure Illustrations (Oak Ridge Natl. Laboratory, Report ORNL-5138, Oak Ridge, Tenn.).

  • Taylor, R., and Kennard, O. (1982)J. Am. Chem. Soc. 104, 5063.

    Google Scholar 

  • Weber, E., and Czugler, M. (1988a)Molecular Inclusion and Molecular Recognition-Clathrates-II (Topics in Current Chemistry, Vol. 149), E. Weber, ed. (Springer-Verlag, Berlin-Heidelberg), p. 45.

    Google Scholar 

  • Weber, E., Csöregh, I., Ahrendt, J., Finge, S., and Czugler, M. (1988b)J. Org. Chem. 53, 5831.

    Google Scholar 

  • Weber, E. (1989)J. Mol. Graphics 7, 12.

    Google Scholar 

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Czugler, M., Cserzö, M., Weber, E. et al. Crystal and molecular structure of the H-bonded complex between 1-chloro-2-hydroxynaphthalene-3-carboxylic acid and dimethylformamide (1∶1). Journal of Crystallographic and Spectroscopic Research 21, 501–505 (1991). https://doi.org/10.1007/BF01160666

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  • DOI: https://doi.org/10.1007/BF01160666

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