Abstract
Reaction of thecis-anti-cis isomer of dicyclohexano-18-crown-6 with a mixture of 2-chloro-5-methylbenzenesulphamide and 3-chloro-6-methylbenzenesulphamide gives a crystalline product which has been characterized using X-ray crystallography. The complex (I) contains both isomers in a 83.0 (0.6):17.0 (0.6) ratio in favour of the 3-chloro-6-methyl-isomer. The joint crystallization of the crown ether with the mixture of the guest isomers might serve as a route for the partial extraction of one of them. The complex with host: guest ratio 1:2 crystallizes in a triclinic space group\(P\bar 1\),a=13.087(4),b=9.217(2),c=8.120(2) Å, α=92.05(3),β=100.52(3), γ=80.64(2)°, withZ=1. The structure was refined toR=0.041. Each of two equivalent guest molecules interacts with the macrocyclic ring by two NH...O hydrogen bonds, with N...O distances of 2.912(5) and 3.040(5) Å.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
M. Hiraoka:Kraun-soedineniya. Ih svoiatva i primenenie. Moscow, Nauka, p. 363 (1986).
M. Hiraoka:Crown Compounds. Their Characteristics and Applications. Kodansha Ltd., Amsterdam-Oxford-New York.
N.P. Strel'tsova, A.A. Varnek, A.S. Glebov and V.K. Bel'skii: inProblems of Crystal Chemistry (Russian), A collection of papers, Moscow, Nauka, p. 47 (1989).
D.J. Cram:Chemica Scripta 28, 263 (1988).
J.S. Bradshaw, P. Huszthy, T. Wang, Ch. Zhu, A.Y. Nazarenko and R.M. Izatt:Supramol. Chem. 1, 267 (1993).
Yu.A. Simonov, M.S. Fonari, A.A. Dvorkin and T.J. Malinowski: inProblems of Modern Crystallography (Russian), A collection of papers, Moscow, Nauka, p. 221 (1992).
E.V. Ganin, V.F. Makarov, S.A. Kotlyar, N.G. Luk'yanenko, M.S. Fonari, A.A. Dvorkin and Yu.A. Simonov:Khim. Geterocycl. Soed. (Russian)9, 1190 (1988).
A.A. Dvorkin, M.S. Fonari, S.T. Malinowski, E.V. Ganin, Yu.A. Simonov, V.F. Makarov, S.A. Kotlyar and N.G. Luk'yanenko:Zh. Strukt. Khim. (Russian)30, 96 (1989).
Yu.A. Simonov, E.V. Ganin, M.S. Fonari, A.A. Dvorkin and S.A. Kotlyar:Zh. Strukt. Khim. (Russian)31, 106 (1990).
A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori and M. Camalli:SIR92 Program for Crystal Structure Determination. Personal communication.
G.M. Sheldrick:SHELX76, Program for Crystal Structure Determination, University of Cambridge, England (1976).
G.M. Sheldrick:SHELXL-93, Program for Crystal Structure Determination, University of Göttingen, Germany (1993).
C. Rizzoli, V. Sangermano, G. Calestaniand and G.D. Andreetti: “CRYSRULER, an Intergrated System of Computer Programs for Crystal Structure Analysis on a Personal Computer”,J. Appl. Crystallogr. 20, 436 (1987).
C.K. Johnson: ORTEP II. Report ORNL-5138. Oak Ridge National Lab. Tennessee, U.S.A. (1976).
Y.A. Simonov, M.S. Fonari, E.V. Ganin, A.A. Dvorkin, G.S. Musienko, E.N. Krylov and T.I. Malinowski:Zh. Strukt. Khim., (Russian)33, 138 (1992).
N. Ramasubbu, R. Parthasarathy and P. Murray-Rust:J. Am. Chem. Soc. 108, 4308 (1986).
B.S. Goud, S.S. Pathaneni and G.R. Desiraju:Acta Crystallogr. C 49, 1107 (1993).
J. Dale:Acta Chem. Scand. 27, 1115 (1973).
A. Kalman, M. Czugler and G. Argay:Acta Crystallogr. B 37, 868 (1981).
Author information
Authors and Affiliations
Additional information
Supplementary Data relevant to this paper have been deposited with the British Libary as Supplementary Publication No. SUP 82180 (30 pp.).
Rights and permissions
About this article
Cite this article
Bocelli, G., Cantoni, A., Simonov, Y.A. et al. Crystal structure of the 1:2 molecular complex between thecis-anti-cis isomer of dicyclohexano-18-crown-6 and 3-chloro-6-methylbenzenesulphamide. J Incl Phenom Macrocycl Chem 20, 105–114 (1994). https://doi.org/10.1007/BF00709334
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00709334