Crystallographic and NMR analysis of 9-phenylthiophenanthrene and 9-tert-butylthiophenanthrene

The crystal structures of 9-phenylthiophenanthrene (C20H14S) and 9-tert-but ylthiophenanthrene (C18H18S) were determined at 193 K. The former crystalli zes in orthorhombic space group P2(1)2(1)2(1) (No. 19) with cell dimensions a = 5.602(2), b = 9.247(3), and c = 27.508(12) Angstrom and the latter in orthorhombic space group Pbcn (No. 60) with cell parameters a = 21.335(4), b = 7.540(2), and c = 18.197(4) Angstrom. In both compounds the substituent s at sulfur are nearly perpendicular to the phenanthrene plane. NMR spectra of the compounds were recorded in CDCl3. The H-1 NMR spectral parameters w ere analyzed in detail by using an iterative spectral analysis program. The C-13{H-1} resonances were fully assigned with the aid of two-dimensional h eteronuclear chemical shift correlation spectra. On the basis of the NOE di fference spectra the orientation of the side chain was concluded to be simi lar to that in the solid state.