Crystal structure of 5,7,12,14-tetra­hydro-5,14:7,12-bis­([1,2]benzeno)­penta­cene-6,13-dione

The lattice of 5,7,12,14-tetra­hydro-5,14:7,12-bis­([1,2]benzeno)­penta­cene-6,13-dione, C(34)H(20)O(2), at 173 K has triclinic (P-1) symmetry and crystallizes with four independent half-mol­ecules in the asymmetric unit. Each mol­ecule is generated from a C(17)H(10)O substructure through an inversion center at the centroid of the central quinone ring, generating a wide H-shaped mol­ecule, with a dihedral angle between the mean planes of the terminal benzene rings in each of the two symmetry-related pairs over the four mol­ecules of 68.6 (1) (A), 65.5 (4) (B), 62.3 (9) (C), and 65.8 (8)° (D), an average of 65.6 (1)°. This compound has applications in gas-separation membranes constructed from polymers of intrinsic microporosity (PIM). The title compound is a product of a double Diels–Alder reaction between anthracene and p-benzo­quinone followed by de­hydrogenation. It has also been characterized by cyclic voltammetry and rotating disc electrode polarography, FT–IR, high resolution mass spectrometry, elemental analysis, and (1)H NMR.