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

Abstract

The crystal structures of 9-phenylthiophenanthrene (C₂₀H₁₄S) and 9-tert-butylthiophenanthrene (C₁₈H₁₈S) were determined at 193 K. The former crystallizes in orthorhombic space group P2₁2₁2₁ (No. 19) with cell dimensions a = 5.602(2), b = 9.247(3), and c =  27.508(12) Å 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) Å. In both compounds the substituents at sulfur are nearly perpendicular to the phenanthrene plane. NMR spectra of the compounds were recorded in CDCl₃. The ¹H NMR spectral parameters were analyzed in detail by using an iterative spectral analysis program. The ¹³C{¹H} resonances were fully assigned with the aid of two-dimensional heteronuclear chemical shift correlation spectra. On the basis of the NOE difference spectra the orientation of the side chain was concluded to be similar to that in the solid state.