Abstract
The crystal structure of 2-(N,N-dimethylaminomethyl)-4-nitrophenol, C9H12N2O3 has been determined by X-ray diffraction methods. The crystals are monoclinic;C2/c (No. 15),a=23.437(6),b=5.334(2),c=17.444(4) Å,β=119.90(5)°,Z=8. The structure was solved by direct methods, and refined to anR value of 0.032 for 1095 nonzero independent amplitudes. Molecules of the title compound are found to exist in a zwitterionic form. Differences in hydrogen bonding in solution and in the solid phase are discussed. In nonpolar and weakly polar solvents, intramolecular O-H⋯N hydrogen bonding is predominating. In the solid state, two N+-H⋯O− bonds related through an inversion center form a cyclic dimer.
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References
Anderson, E. K., and Anderson, I. K. G. (1975)Acta Cryst. B 31, 387–390.
Coppens, P., and Schmidt, G. M. J. (1965)Acta Cryst. 18, 62–67, 654–659.
Germain, G., Main, P. and Woolfson, M. M. (1971)Acta Cryst. A 27, 368–376.
Haslinger, E., and Wolschann, P. (1980)Monatsh. Chem. 111, 563–573.
Higashi, T., and Osaki, K. (1977)Acta Cryst. B 33, 607–609.
Hughes, D. L. (1975)J. Chem. Soc. Dalton Trans., 2374–2378.
International Tables for X-ray Crystallography (1974) Vol. IV (Kynoch Press, Birmingham).
Iwasaki, F., and Kawano, Y. (1977)Acta Cryst. B 33, 2455–2459.
Julia, M., and Tchernoff, G. (1955)Bull. Soc. Chim. Fr. 830–837.
Kagawa, T., Kawai, R., Kashino, S., and Haisa, M. (1976)Acta Cryst. B 32, 3171–3175.
Kawai, R., Kashino, S., and Haisa, M. (1976)Acta Cryst. B 32, 1972–1975.
Kim, H. S., and Jeffrey, G. A. (1971)Acta Cryst. B 27, 1123–1131.
Koll, A. (1983)Bull. Soc. Chim. Belg. 92, 313–328.
Koll, A., Rospenk, M., and Sobczyk, L. (1981)J. Chem. Soc. Faraday Trans. I 2309–2314.
Lautie, A., Froment, F., and Novak, A. (1976)Spectrosc. Lett. 9, 289–299.
Novak, A. (1974)Struct. Bond.,18, 177–216.
Odinokov, S. E., Mashkovsky, A. A., Glazunov, V. P., Iogansen, A. V., and Rassadin, B. V. (1976)Spectrochim. Acta A 32, 1355–1363.
Piliugin, W. S., and Wasin, S. W. (1979)Zh. Obshch. Khim. 49, 2056–2064.
Richards, J. P. G. (1961)Z. Kristallogr. 116, 468–473.
Robien, W., Völlenkle, H., and Wolschann, P. (1981), private communication.
Robien, W., Völlenkle, H., and Wolschann, P. (1982)Z. Phys. Chem. N.F. 130, 123–128.
Rospenk, M., and Koll, A. (1983)Bull. Soc. Chim. Belg. 92, 329–335.
Saitoh, T., Mori, K., and Itoch, R. (1981)Chem. Phys. 60, 161–180.
Sobczyk, L., and Rospenk, M. (1980) inProceedings of the Conference Analytiktreffen 1980, Schwingungsspektroskopie, Karl Marx University, Leipzig, pp. 34–60.
Sucharda-Sobczyk, A., and Sobczyk, L. (1978)Bull. Acad. Pol. Sci., Ser Sci. Chim. 24, 651–657.
Syntex (1976)Xtl/xtle Structure Determination System, Syntex Analytical Instruments, Cuperino, California.
Talberg, H. J. (1975)Acta Chem. Scand. A 29, 919–926.
Trotter, J. (1961)Can. J. Chem. 39, 1638–1644.
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Koll, A., Głowiak, T. Structure and spectroscopic properties of 2-(N,N-dimethylaminomethyl)-4-nitrophenol. Journal of Crystallographic and Spectroscopic Research 15, 411–421 (1985). https://doi.org/10.1007/BF01171045
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DOI: https://doi.org/10.1007/BF01171045