Abstract
The crystal structure of the derivative of tetrahydronaphthalene with substituent epoxy, hydroxyl, and methyl groups in the more saturated ring (r-1-hydroxy-t-2-methyl-t,t-3,4-epoxy-1,2,3,4-tetrahydronaphthalene) has been determined. The hydroxyl and methyl groups are both found to beequatorial. The crystal structure is characterized by chains of molecules linked by O-H ⋯ O hydrogen bonds involving the hydroxyl groups; these hydrogen bonds lie approximately parallel to theb axis. The conformations of the epoxide-bearing rings in various hydroxy epoxides are compared and shown to be similar.
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Sims, P.; Grover, P. L.; Swaisland, A.; Pal, K.; Hewer, A.Nature (London) 1974,252, 326–328.
Thakker, D. R.; Yagi, H.; Akagi, M.; Koreeda, M.; Lu, A. Y. H.; Levin, W.; Wood, A. W.; Conney, A. H.; Jerina, D. M.Chem.-Biol. Interact. 1977,16, 281–300.
Jerina, D. M.; Daly, J. W.Science 1974,185, 573–582.
Jeffrey, A. M.; Blobstein, S. H.; Weinstein, I. B.; Beland, F. A.; Harvey, R. G.; Kasai, H.; Nakanishi, K.Proc. Natl. Acad. Sci. USA 1976,73, 2311–2315.
Glusker, J. P.; Carrell, H. L.; Zacharias, D. E.; Harvey, R. G.Cancer Biochem. Biophys. 1974,1, 43–52.
Glusker, J. P.; Zacharias, D. E.; Carrell, H. L.; Fu, P. P.; Harvey, R. G.Cancer Res 1976,36, 3951–3957.
Kuroda, R.; Neidle, S.Carcinogenesis 1983,4, 217–219.
Neidle, S.; Subbiah, A.; Cooper, C. S.; Ribeiro, O.Carcinogenesis 1980,1, 249–254.
Neidle, S.; Cutbush, S. D.Carcinogenesis 1983,4, 415–418.
Glusker, J. P.; Zacharias, D. E.; Whalen, D. L.; Friedman, S.; Pohl, T. M.Science 1982,215, 695–696.
Klein, C. L.; Stevens, E. D.Cancer Res 1984,44, 1523–1526.
Klein, C. L.; Stevens, E. D.Acta Crystallogr. Sec. C 1984,40, 315–317.
Klein, C. L.; Stevens, E. D.Acta Crystallogr. Soc. B 1988,44, 50–55.
Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; Declercq, J. P.; Woolfson, M. M.MULTAN78, Programs from the University of York, England, and University of Louvain, Belgium, 1977.
Ibers, J. A.; Hamilton, W. C. (Eds.).International Tables for X-ray Crystallography. Vol. IV. Revised and Supplementary Tables to Volumes II and III; Kynoch Press: Birmingham, 1974.
Carrell, H. L.VIEW. Program from the Institute for Cancer Research, The Fox Chase Cancer Center, Philadelphia, PA 1976.
Carrell, H. L.; Shieh, H.-S.; Takusagawa, F. (1981) The Crystallographic Program Library of the Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, PA, 1981.
Erlebacher, J., Carrell, H. L.ICRVIEW, Program from the In- stitute for Cancer Research, The Fox Chase Cancer Center, Philadelphia, PA, 1992.
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Zacharias, D.E., Glusker, J.P., Whalen, D.L. et al. Ring pucker in dihydroaromatic epoxides: The molecular structure ofr-1-hydroxy-t-2-methyl-t,t-3,4-epoxy-1,2,3,4-tetrahydronaphthalene. Struct Chem 6, 89–97 (1995). https://doi.org/10.1007/BF02281734
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DOI: https://doi.org/10.1007/BF02281734