Molecular compounds and complexes. X. The crystal structure of the π-molecular compound benzo[c]phenanthrene–2,3-dichloro-5,6-dicyanobenzoquinone

Abstract

The influence of rr-molecular compound formation on the deviations from planarity of the overcrowded aromatic molecule benzo[clphenanthrene has been studied by determining the crystal structure of benzolclphenanthrene-2,3-dichloro-5,6-dicyanobenzoquinone l a = 10.953 (2), b = 16.090 (3), c -13. 827 (3) A, fl = 122.63 (1)°: space group P2t/c; Z = 4]. The structure was solved by direct methods and refined to R = 0.065 for 3385 observed reflexions. Stacks with alternating donor and acceptor molecules extend in the e direction. The acceptor molecule takes on two orientations, with population ratio'-'4:1. Comparison of the structures of the benzo[clphenanthrene molecule here and in its pure crystals shows that it is significantly less distorted from planarity in the present molecular compound, but that bond lengths and angles remain practically unchanged. The diminished distortion from planarity may be due to the donor-acceptor interaction.

MOLECULAR GEOMETRY,CYP1AGENE INDUCTION AND CLASTOGENIC ACTIVITY OF CYCLOPENTA[c]PHENANTHRENE IN RAINBOW TROUT

“…Standard PCR reaction conditions and thermal cycling protocol were described in the papers cited in Table 1. In order to adopt a more semi-quantitative approach for analysis of the gene expression, both CYP1A and ß-actin gene (external standard) were amplified using a series of cycle numbers (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30). Following this procedure the optimal cycle number was determined and subsequently employed in the expression studies.…”

Molecular compounds and complexes. XI. The crystal structure of the π-molecular compound phenanthrene-2,3-dichloro-5,6-dicyano-p-benzoquinone

“…Crystal data in Table 1 extend (and correct) preliminary results (Herbstein, Kaftory & Regev, 1976). Intensities of 1671 reflections were measured with a Stoe Weissenberg diffractometer (Mo Ka radiation, graphite monochromator) and reduced to a set of structure factors by standard methods (absorption * Part x: Bernstein, Regev & Herbstein (1977). t Undergraduate research participant.…”

“…In the crystal structure of benzo [c]phenanthrene-2,3-dichloro-5,6-dicyano-p-benzoquinone (BPH-DDQ) (Bernstein, Regev & Herbstein, 1977), the DDQ molecules are positioned above and below 'phenanthrene' portions of the BPH molecules, with alignment of polar carbonyl groups above polarizable 'benzene' rings. Such an arrangement, which is common but not universal in appropriate ~z-molecular compounds (Prout & WaUwork, 1966), might also be anticipated in phenanthrene-DDQ (PH-DDQ).…”