Table of Contents
Journal of Crystallography
Volume 2016 (2016), Article ID 8129210, 6 pages
Research Article

Structure and Properties of 9,14,15,16,17,18,19,20-Octahydro-9,14[1′,4′]-benzenobenzo[b]triphenylene

1Department of Chemistry, Cleveland State University, Cleveland, OH 44115, USA
2Department of Chemistry, Youngstown State University, Youngstown, OH 44555, USA

Received 17 March 2016; Accepted 24 April 2016

Academic Editor: Takashi Mino

Copyright © 2016 Michelle E. Masnovi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


The compound 9,14,15,16,17,18,19,20-octahydro-9,14[1′,4′]-benzenobenzo[b]triphenylene, C28H24, was prepared by hydrogenation of the photocycloadduct of dibenz[a,c]anthracene and 1,3-cyclohexadiene with Pt/C in ethyl acetate. The X-ray diffraction analysis shows that the compound crystallizes in the monoclinic space group with the geometric parameters of = 11.0090(17) Å, = 13.733(2) Å, = 13.091(2) Å, and = 109.583(13)°. In addition to several close intramolecular contacts involving hydrogens derived from the dibenzanthracene moiety, long interannular C–C single bonds of about 1.593 Å are present. These bonds are shorter by about 0.18 Å than the corresponding bonds in the unsaturated precursor, which can be attributed to reduced strain in the more saturated polycyclic ring system. Anisotropic shielding of the four endo-methylene hydrogens in the 1H NMR spectrum is larger for the two hydrogens lying above the phenanthrene unit, which resonate at 1.03 ppm, than those above the benzenoid ring, which resonate at 1.24 ppm. Theoretical calculations reproduce the geometry with good agreement.