Abstract
Tetrabenzo-18-crown-6 (1) shows distinct solid-state inclusion properties towards a number of OH-acidic, CH-acidic and low-polar uncharged organic molecules. The single crystal X-ray analysis of the inclusion complex between1 and EtNO2 (1∶1) is reported. Crystals are monoclinic,P21/c, witha=12.887(1),b=19.365(2),c=10.776(1) Å, β=96.33(2)o,D c=1.321g cm−1,Z=4. The host macroring has a conformation similar to a ‘dentist's-chair’. The complex is stabilized mainly by C−H...O type interactions involving the methyl group of the EtNO2 guest molecule which is highly disordered. The nitroethane guests are trapped in channels formed by the host macrocycles.
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C.J. Pedersen:Angew. Chem. 100, 1053 (1988);Angew. Chem., Int. Ed. Engl. 27, 1021 (1988).
Reviews: E. Weber: inSynthesis of Macrocycles: The Design of Selective Complexing Agents: Progress in Macrocyclic Chemistry, Vol. 3 (eds. R.M. Izatt and J.J. Christensen), p. 337, Wiley, New York (1987).
I. Goldberg: inCrown Ethers and Analogs (eds. S. Patai and Z. Rappoport), p. 399, Wiley, Chichester (1989).
More recent examples: G.W. Buchanan, C. Morat, J.P. Charland, C.I. Ratcliffe, and J.A. Ripmeester:Can. J. Chem. 67, 1212 (1989).
B. Belarmi, C. Bavoux, and A. Thozet:J. Incl. Phenom. 8, 383 (1990).
M. Perrin, E. Mahdar, S. Lecocq, and C. Bavoux:J. Incl. Phenom. 9, 153 (1990).
G.W. Gokel, D.J. Cram, C.L. Liotta, H.P. Harris, and F.L. Cook:J. Org. Chem. 39, 2445 (1974).
G.W. Gokel, D.J. Cram, C.L. Liotta, H.P. Harris, and F.L. Cook:Org. Synth. 57, 30 (1977).
F. Vögtle and W.M. Müller:Chem. Ber. 113, 2081 (1980).
F. Vögtle and W.M. Müller:Chem. Ber. 114 3179 (1981).
C.J. Pedersen:J. Org. Chem. 36, 1690 (1971).
A. van Zon, F. de Jong, D.N. Reinhoudt, G.J. Torny, and Y. Onwezen:Recl. Trav. Chim. Pay-Bas 100, 449 (1981).
R.D. Rogers:J. Incl. Phenom. 6, 629 (1988).
E. Weber:Chem. Ber. 118 4439 (1985).
E. Weber, S. Franken, J. Ahrendt, and H. Puff:J. Org. Chem. 52, 5291 (1987).
E. Weber, H.J. Köhler, and H. Reuter:Chem. Ber. 122, 959 (1989).
E. Weber, H.J. Köhler, K. Panneerselvam, and K.K. Chacko:J. Chem. Soc., Perkin Trans. 2 1599 (1990).
E. Weber, H.J. Köhler, and H. Reuter:J. Org. Chem. 56, 1236 (1991).
G.H. Stout and L.H. Jensen: inX-Ray Structure Determination. A Practical Guide, p. 454, MacMillan, New York (1968).
G.M. Sheldrick:SHELX 86. Program for the Solution of Crystal Structures from Diffractometer Data, University of Göttingen, Germany (1986).
G.M. Sheldrick:SHELX 76. Program for Crystal Structure Determination, University of Cambridge, England (1976).
D.T. Cromer and J.B. Mann:Acta Crystallogr., Sect. A. 24, 321 (1968).
R.F. Stewart, E.R. Davidson, and W.T. Simpson:J. Chem. Phys. 42, 3175 (1965).
E. Weber: inMolecular Inclusion and Molecular Recognition-Clathrates I; Topics in Current Chemistry, Vol. 140 (ed. E. Weber), p. 1, Springer-Verlag, Berlin-Heidelberg (1987).
E. Weber: inInclusion Compounds, Vol. 4 (eds. J.L. Atwood, J.E.D. Davies, and D.D. MacNicol), p. 188, Oxford University Press, Oxford (1991).
I. Csöregh, M. Czugler, E. Weber, and J. Ahrendt:J. Incl. Phenom. 8, 309 (1990).
E. Weber and H.P. Josel:J. Incl. Phenom. 1, 79 (1983).
E. Weber:J. Mol. Graphics 7, 12 (1989).
J.A.A. Boer, D.N. Reinhoudt, S. Harkema, G.J. van Hummel and F. de Jong:J. Am. Chem. Soc. 104, 4073 (1982).
R.D. Rogers and L.M. Green:J. Incl. Phenom. 4, 77 (1986).
R.D. Rogers and P.D. Richards:J. Incl. Phenom. 5, 631 (1987).
R.D. Rogers, L.K. Kurihara, and P.D. Richards:J. Chem. Soc., Chem. Commun., 604 (1987).
D. Bright and M.R. Truter:J. Chem. Soc. B., 1544 (1970).
W. Xu, K. Clinger, M.L. Hackert, and N.S. Poonia:J. Incl. Phenom. 3, 163 (1985).
P.J. Reddy, K.K. Chacko, I.H. Suh, E. Weber, H.J. Köhler, and M. Piel:Inorg. Chim. Acta 207, 31 (1993).
Tables of Interatomic Distances and Configurations in Molecules and Ions, The Chemical Society, London (1960).
G. Weber and P.G. Jones:Acta Crystallogr. Sect. C 39, 1577 (1983).
M. Dobler:Ionophores and their Structure, Wiley, New York (1981).
R. Hilgenfeld and W. Saenger:Top. Curr. Chem. 101, 1 (1982).
F. Vögtle, W.M. Müller, and W.H. Watson:Top. Curr. Chem. 125, 131 (1984).
M. Mercer and M.R. Truter:J. Chem. Soc., Dalton Trans., 2469 (1973).
D.L. Hughes, C.L. Mortimer and M.R. Truter:Inorg. Chim. Acta 29, 43 (1978).
R. Taylor and O. Kennard:J. Am. Chem. Soc. 104, 5063 (1982).
G.R. Desiraju:Acc. Chem. Res. 24, 290 (1991).
L. Pauling: inThe Nature of the Chemical Bond, 3rd. ed., p. 260, Cornell Universitiy Press, Ithaca (1960).
I. Goldberg:Acta Crystallogr. Sect. B. 31, 754 (1975).
R. Kaufmann, A. Knöchel, J. Kopf, J. Oehler, G. Rudolph:Chem. Ber. 110, 2249 (1977).
R. Gerdil: inMolecular Inclusion and Molecular Recognition-Clathrates I; Topics in Current Chemistry, Vol. 140 (ed. E. Weber), p. 71, Springer-Verlag, Berlin-Heidelberg (1987).
W.D. Ollis and J.F. Stoddart: inInclusion Compounds, Vol. 2 (eds. J.L. Atwood, J.E.D. Davies, and D.D. MacNicol), p. 169, Academic Press, London (1984).
E. Giglio: inInclusion Compounds, Vol. 2 (eds. J.L. Atwood, J.E.D. Davies, and D.D. MacNicol), p. 207, Academic Press, London (1984).
R.E. Koeppe, K.O. Hodgson, and L. Stryer:J. Mol. Biol. 121, 41 (1978).
R.E. Koeppe, K.O. Hodgson, and L. Stryer:Nature 279, 723 (1979).
O. Heitzsch, K. Gloe, A. Sabela, J. Koryta, and E. Weber:J. Incl. Phenom. 13, 311 (1992).
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Supplementary Data relating to this article are deposited with the British Library as Supplementary Publication No. SUP 82150 (11 pages)
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Weber, E., Ahrendt, J., Lohner, A. et al. Crystalline inclusion compounds of tetrabenzo-18-crown-6 with uncharged organic molecules. Solid-state structure of the nitroethane complex. J Incl Phenom Macrocycl Chem 15, 231–245 (1994). https://doi.org/10.1007/BF00709069
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DOI: https://doi.org/10.1007/BF00709069