Abstract
The crystal structures of two 12-membered crown ethers, benzo-12-crown-4 (1) and naphtho-12-crown-4 (2), have been determined by X-ray analysis. Both structures are molecular. Compound1 is monoclonic,P21/b,a=8.466(3),b=8.019(3),c=33.590(10) Å, γ=90.99(3)o. The unit cell contains two crystallographically independent molecules of1 with similar conformations. Compound2 is also monoclinic,P21/a,a=24.148(8),b=14.535(4),c=7.987(5) Å, γ=102.87(2)o. Two independent molecules in the unit cell have significantly different conformations.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
P. Growth:Acta. Chem. Scand. A32, 279 (1978).
J.-P. Charland, G. W. Buchanan and R. A. Kirby:Acta Crystallogr. C45, 165 (1989).
G. W. Buchanan, R. A. Kirby, J.-P. Charland and C. J. Ratcliffe:J. Org. Chem. 56, 203 (1991).
A. Yu. Tsivadse, A. A. Varnek and V. E. Chutorskii:Koordinatsionnye soedineniya metallov s kraun efirami. (Coordination compounds of metals with the crown ethers.) Moscow. Nauka. 397 pp. (1991).
O. A. Raevskii, V. V. Tkachev, L. O. Atovmyan, V. E. Zubareva, I. I. Bulgak and D. G. Batyr:Koord. Chim. (Russ.) 14, 1697 (1988);Chem. Abst. 110, 184779.
V. V. Tkachev, L. O. Atovmyan, V. E. Zubareva and O. A. Raevskii:Koordin. Chim. (Russ.) 16, 443 (1990),Chem. Abst. 113, 125239.
O. A. Raevskii, I. O. Umarova, V. V. Tkachev, L. O. Atovmyan, I. I. Bulgak, V. E. Zubareva, G. I. Van'kin and N. V. Lukoyanov:Izvestiya Akademii Nuak SSSR. Seriya chimicheskaya 5, 1051 (1988),Chem. Abst. 110, 38344.
O. A. Raevskii, V. V. Tkachev, V. P. Kazachenko, A. N. Razdol'sky, V. E. Zubareva and I. I. Bilgak:Izvestiya Akademii Nauk SSSR. Seriya chimicheskaya 20, 20 (1989);Chem. Abst. 112, 157389.
J. Kostrowicki and J. F. Biernat:J. Incl. Phenom. 11, 205 (1991).
B. P. Czech, A. Czech and R. A. Bartsch:J. Heterocyclic Chem. 22, 1297 (1985).
G. M. Sheldrick:SHELXTS — An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, University of Götingen.
C. E. Bugg, J. M. Thomas, M. Sundaralingam and S. T. Rao:Biopolymers 10, 175 (1971).
M. Hiraoka:Kraun-coedineniay. Ih svoistva i primenenie. Moscow. Nauka. 1986. p. 363. M. Hiraoka.Crown Compounds. Their Characteristics and Applications. Kodansha Ltd., Amsterdam-Oxford-New-York.
Em. Maverick, P. Seiler, W. B. Schweizer and J. D. Dunitz:Acta Crystallogr. B36, 615 (1980).
J. Dale:Acta Chem. Scand. 27, 1115 (1973).
J. D. Owen and M. R. Truter:J. Chem. Soc. Dalton Trans. 9, 1831 (1979).
M. A. Bush and M. R. Truter:J. Chem. Soc. B. 1440 (1971).
M. A. Bush and M. R. Truter:J. Chem. Soc. Perkin Trans. 2, 345 (1972).
A. A. Dvorkin, Yu. A. Simonov, K. Suwińska, J. Lipkowski, T. I. Malinowski, E. V. Ganin and S. A. Kotlyar:Kristallografiya (Russ.) 36, 62 (1991);Chem. Abst. 114, 257296.
Yu. A. Simonov, A. A. Dvorkin, T. I. Malinovski, V. I. Kal'chenko, A. P. Kartoflitskaya and V. T. Kolensnikov:Kristallografiya (Russ.) 31, 1120 (1986).
Author information
Authors and Affiliations
Additional information
Supplementary data relating to this publication have been deposited with the British Library as Supplementary Publication No. SUP 82145 (19 pages).
Rights and permissions
About this article
Cite this article
Simonov, Y.A., Dvorkin, A.A., Fonari, M.S. et al. Twelve-membered crown ethers: Crystal structures of benzo-12-crown-4 and naphtho-12-crown-4. Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 15, 79–89 (1993). https://doi.org/10.1007/BF00706476
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00706476