1-Methylphenanthro[3,4-b]thiophene was prepared by the photocyclization of 1-(4′-methyl-2′-thienyl)-2-(2″-naphthyl)ethene. The 1H and 13C-nmr spectra were assigned using two-dimensional 1H/13C heteronuclear chemical shift correlation and relayed coherence transfer (RELAY) experiments. From nuclear Overhauser difference spectra, the H11-C1 methyl-H intramolecular distance was determined to be 2.10 Å. The molecule crystallized from chloroform in the monoclinic system, space group P21/c. A total of 3536 unique reflections were measured and the structure was solved by direct methods and refined to a final R = 0.049. The molecule is helical with both chiral forms observed in the crystal. The H11-C1 methyl-H distance in the crystal was 2.12(3)Å in excellent agreement with the distance measured in solution by NOE techniques.
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1-Methylphenanthro[3,4-b]Thiophene_Determination_of_the_Tertiary_Structure_in_Solution_and_in_the_Crystalline_State_by_NMR_Spectroscopy_and_X-ray_Diffraction.pdf | 2.39 MB |