(E)-3,3',4,4',7,7',8,8'-Octa-methyl-2H,2'H-1,1'-bi(cyclo-penta-[fg]acenaphthyl-enyl-idene)-2,2',5,5',6,6'-hexa-one dichloro-methane monosolvate.

ABSTRACT: The title compound, C(36)H(24)O(6)·CH(2)Cl(2), is a dimer of two essentially planar (r.m.s., deviations of fitted plane of 14 pyracene C atoms = 0.0539 and 0.0543?Å) tetra-cyclic pyracene frameworks (each with four methyl groups and three carbonyl groups on the peripheral carbon atoms) twisted along a central C=C bond with an angle of 50.78?(3)° at 90?K. There are notably long Csp(2)-Csp(2) bonds associated with the carbonyl groups, the longest being 1.601?(3)?Å between two carbonyl C atoms. There are also intermolecular carbonyl?carbonyl interactions of both parallel and antiparallel types, with C?O distances in the range 3.041?(3) to 3.431?(2)?Å. This compound is of inter-est with respect to the synthesis of fullerene fragments, such as corannulene and semibuckminsterfullerene derivatives (or 'buckybowls'), and is a side product of the previously reported oxidation reaction. Structural details, such as planarity analysis of fused rings, out-of-plane deviation of substituents, inter-molecular inter-actions, and longer than typical bond lengths, will be discussed as well as comparisons to structurally related compounds.

SUBMITTER: McCandless GT 

PROVIDER: S-EPMC3344573 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature