Crystal structure of 12-benzyl­sulfanyl-2,9-di­bromo-6H-dibenzo[b,g][1,8]naphthyridin-11-one

Abstract

The hetero­tetra­cene skeleton of the title mol­ecule, C23H14Br2N2OS, is defined by linear annulation of four six-membered rings, including two N heteroatoms. This moiety is nearly planar (r.m.s. deviation = 0.055 Å), with a slight twist of 4.1 (2)° between the two halves of the aromatic system. The dihedral angle between the least-squares plane of the skeleton and the benzyl group is 24.5 (3)°; the C-S-C angle involving the benzyl­sulfanyl group is 99.2 (4)°. In the crystal, mol­ecules are [pi]-stacked in an anti­parallel fashion along [110], with a distance between the aromatic planes of 3.47 (2) Å. Inter­molecular N-H...O hydrogen bonds form chains extending parallel to [001] and bridge the anti­parallel inter­digitated stacks of mol­ecules.