Abstract
The crystal structure of two complexes of the isomerscis-syn-cis (isomer A) andcis-anti-cis (isomer B) of dicyclohexano-18-crown-6 with 4-methylbenzenesulfamide have been determined by X-ray single crystal diffraction methods. The two structures have been solved by direct methods and refined to agreement values of 0.067 and 0.038 for isomers A and B respectively. The first isomer forms an inclusion compound with a host/guest ratio of 1 : I; the second one of I:2. The amino groups of the guest molecules are connected by N-H...O hydrogen bonds with oxygen atoms of the polyether molecules. The methyl groups of 4-methylbenzenesulfamide do not form hydrogen bonds.[/p]
The host-guest interactions in the molecular complexes, the reciprocal influence of the two molecules on their conformation and the intermolecular contacts between the molecules in the crystal are discussed.
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References
M. Mercer and M. R. Truter:J. Chem. Soc. Dalton Trans. 2215, (1973).
N. F. Krasnova, Yu. A. Simonov, V. K. Bel'skii, B. M. Abaskin, V. V. Yakshin, T. I. Malinowskii and B. N. Laskorin:Dokl. Akad. Nauk. SSSR 276, 607 (1984).
F. R. Fronczek, R. D. Gandour, L. M. B. Gehrig, L. R. Caswell, K. A. McDowell and I. Alam:J. Incl. Phenom. 5, 379 (1987).
A. A. Dvorkin, N. F. Krasnova, Yu. A. Simonov, V. M. Abaskin, V. V. Yakshin and T. I. Malinowskii:Kristallografiya 29, 282 (1984).
A. Elbasyouny, H. J. Brugge, K. von Deuten, M. Dickel, A. Knochel, K. U. Koch, J. Kopf, D. Melzer and G. Rudolph:J. Am. Chem. Soc. 105, 6568 (1983).
G. Bombieri, G. De Paoli and A. Immirzi:J. Inorg. Nucl. Chem. 40, 799 (1978).
M. M. Amini, A. L. Rheingold, R. W. Taylor and J. J. Zuckerman:J. Am. Chem. Soc. 106, 7289 (1984).
N. F. Krasnova, Yu. A. Simonov, V. K. Bel'skii, A. T. Fedorova and V. V. Yakshin:Kristallografiya 31, 650 (1986).
J. M. Lehn:Chemica Scripta 28, 237 (1988).
D. F. Cram:Chemica Scripta 28, 263 (1988).
E. Weber: inSynthesis of Macrocycles. The Design of Selective Complexing Agents: Progress in Macrocyclic Chemistry (Ed. R. M. Izatt and F. F. Christensen) Vol. 3. Wiley, New York (1987).
F. R. Damewood, F. F. Urban, T. C. Williamson and A. L. Rheingold:J. Org. Chem. 53, 167 (1988).
Yu. A. Simonov, T. I. Malinowskii, A. A. Dvorkin, M. S. Fonar, Ed. V. Ganin and S. A. Kotlar:Z. Kristallogr. 185, 249 (1988).
D. R. Rogers, P. D. Richards and E. J. Voss:J. Incl. Phenom. 6, 65 (1988).
Yu. A. Simonov, L. P. Battaglia, A. Bonamartini Corradi, S. Ianelli, G. Pelosi, Ed. V. Ganin, N. G. Lukjanenenko:J. Incl. Phenom. (submitted).
D. Belletti, A. Cantoni and G. Pasquinelli: inGestione on Line di Diffrattometro a Cristallo Singolo Siemens AED con Sistema IBM PS2/30. Centro di Studio per la Strutturistica Diffrattometrica del C.N.R., Parma, Italy. Internal Report I/88 (1988).
M. S. Lehmann and F. K. Larsen:Acta Crystallogr. A30, 580 (1974).
G. M. Sheldrick: inSHELX76, Program for Crystal Structure Determination, University of Cambridge, England (1976).
C. Rizzoli, V. Sangermano, G. Calestani and G. D. Andreetti: in ‘CRYSRULER, An Integrated System of Computer Programs for Crystal Structure Analysis on a Personal Computer’,J. Appl. Crystallogr. 20, 436 (1987).
A. Knochel, J. Kopf, J. Oehler and G. Rudolph:J. Chem. Soc. Chem. Commun. 595 (1978).
F. Seel, N. Klein, B. Krebs, M. Dartmann and G. Henkel:Z. Anorg. Allg. Chem. 524, 95 (1985).
J. Dale:Acta. Chem. Scand. 27, 1115 (1973).
N. K. Dalley, J. S. Smith, S. B. Larson, J. J. Christensen and R. M. Izatt:J. Chem. Soc. Chem. Commun. 43 (1975).
Yu. A. Simonov, N. F. Krasnova, N. A. Charenko, V. K. Bel'skii, V. V. Yakshin and B. N. Laskorin:Dokl. Akad. Nauk SSSR 285, 893 (1985).
Yu. A. Simonov, N. G. Krasnova, A. A. Dvorkin, V. V. Yakshin, V. B. Abashkin and B. V. Laskorin:Dokl. Akad. Nauk SSSR 272, 1129 (1985).
M. S. Fonar, Yu. A. Simonov, A. A. Dvorkin, T. I. Malinowsky, Ed. V. Ganin, S. A. Kotlyar and V. F. Makarov:J. Incl. Phenom. 7, 613 (1989).
G. Weber and G. M. Sheldrick:Acta Crystallog. B37, 2108 (1981).
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Simonov, Y.A., Malinowskii, T.I., Ganin, E.V. et al. Crystal structure of inclusion compounds: The complexes of thecis-syn-cis and thecis-anti-cis isomers of dicyclohexano-18-crown-6 with 4-methylbenzenesulfamide. J Incl Phenom Macrocycl Chem 8, 349–361 (1990). https://doi.org/10.1007/BF01041890
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DOI: https://doi.org/10.1007/BF01041890