Abstract
The title compound 14-hydroxy-14-phenyldibenzo[a,j]xanthene 1 formed a (1:1) complex with diethyl ether. 1,4-Dioxane was also enclathrated, but with a variable stoichiometric ratio. Single crystal X-ray crystallography was used to elucidate the crystal structure of the 1·diethyl ether complex. Crystals are orthorhombic with space group P212121, a = 8.532(3), b = 15.040(4), c = 18.491(5) Å, V = 2373(1) Å3, d c = 1.256 g/cm3, and Z = 4. Host and guest molecules were found to associate via hydrogen bonds, with the guest molecules residing in undulating channels lined by host molecules.
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Weber, E.; Czugler, M. Top. Curr. Chem. 1988, 149, 45; (b) Toda, F. Top. Curr. Chem. 1987, 140, 43; (c) Atwood, J.L.; Davies, J.E.D.; MacNicol, D.D. Inclusion Compounds; Academic Press: London, 1984; Vol. II and Vol. III.
Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
Caira, M.R.; Horne, A.; Nassimbeni, L.R.; Okuda, K.; Toda, F. J. Chem. Soc. Perkin Trans. II, 1995, 1063.
Toda, F. Synlett 1993, 303. (b) Blaser, H-U. Chem. Rev. 1992, 92, 935; (c) Seebach, D. Angew. Chem. Int. Ed. Engl. 1990, 29, 1320; (d) Toda, F.; Shigemasa, T. J. Chem. Soc. Perkin Trans. I, 1989, 209; (e) Toda, F.; Mori, K. J. Chem. Soc. Chem. Comm. 1989, 1245.
Weber, E.; Dörpinghaus, N.; Csöregh, I. J. Chem. Soc. Perkin Trans. II, 1990, 2167.
Glover, S.A.; Goosen, A.; McCleland, C.W.; Taljaard, B.; Vogel, F.R. S. Afr. J. Chem. 1984, 37(4), 164; (b) Glover, S.A.; Goosen, A.; McCleland, C.W.; Staskun, B.; Taljaard, B.; Vogel, F.R. S. Afr. J. Chem. 1985, 38(3), 121; (c) Coombes, P.; Goosen, A.; Taljaard, B. Heterocycles, 1989, 28(2), 559; (d) Glover, S.A.; Goosen, A.; McCleland, C.W.; Taljaard, B.; Vogel, F.R. S. Afr. J. Chem. 1985, 38(4), 163; (e) Glover, S.A.; Goosen, A.; McCleland, C.W.; Taljaard, B.; Vogel, F.R. S. Afr. J. Chem. 1985, 38(4), 203; (f) Goosen, A.; McCleland, C.W.; Taljaard, B. J. Chem. Soc. Perkin Trans. I, 1989, 931; (g) Goosen, A.; McCleland, C.W.; Taljaard, B. J. Chem. Soc. Perkin Trans. II, 1991, 995.
Goosen, A.; McCleland, C.W.; Taljaard, B. S. Afr. J. Chem. 1987, 40, 139.
Sheldrick, G.M. SHELX86, Crystallographic Computing 3; Sheldrick, G.M.; Kruger, C.; Goddard, R., Eds.; Oxford University Press: New York, 1986; p 175.
Sheldrick, G.M. SHELX76, A System of Computer Programs for X-ray Structure Determination; University of Cambridge: Cambridge, UK, 1976.
Nardelli, M. PARST, A System of Fortran Routines for Calculating Molecular Structure Parameters from Results of Crystal Structure Analysis. Computing in Chemistry, Vol. 7(3); 1983; p 95.
Motherwell, S. PLUTO, A Program for Plotting Molecular and Crystal Structures; University of Cambridge: Cambridge, UK, 1979.
Barbour, L.J.; Caira, M.R.; Nassimbeni, L.R. J. Chem. Soc. Perkin Trans. II, 1993, 1413.
Caira, M.R.; Nassimbeni, L.R.; Niven, M.L.; Schubert, W-D.; Weber, E.; Dörpinghaus, N. J. Chem. Soc. Perkin Trans. II, 1990, 2129.
Barbour, L.J., Ph.D. Thesis; University of Cape Town: South Africa, 1994; p 160.
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Barton, B., Caira, M.R., McCleland, C.W. et al. 14-Hydroxy-14-phenyldibenzo[a,j]xanthene as a lattice host: crystal and molecular structure of its (1:1) complex with diethyl ether. Journal of Chemical Crystallography 29, 1179–1186 (1999). https://doi.org/10.1023/A:1009599432277
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DOI: https://doi.org/10.1023/A:1009599432277