3,3′-Di-2-naphthoyl-1,1′-(o-phenylene)dithiourea

Abstract

In the mol­ecule of the title compound, C30H22N4O2S2, the central benzene ring is oriented at dihedral angles of 63.83 (3) and 1.37 (3)° with respect to the naphthalene ring systems, while the two naphthalene ring systems are oriented at a dihedral angle of 62.78 (3)°. Intra­molecular N—H⋯O and N—H⋯N hydrogen bonds result in the formation of one five- and two six-membered rings. The twisting modes of the two side arms are different [C—N—C—O and C—N—C—N torsion angles = 11.1 (4) and 1.5 (3)°, respectively, in one arm, and −2.2 (4) and 0.8 (3)° in the other arm]. In the crystal structure, inter­molecular N—H⋯S hydrogen bonds link the mol­ecules into centrosymmetric dimers. There is a C—H⋯π contact between the naphthalene rings and π–π contacts between the naphthalene rings and the naphthalene and benzene rings [centroid–centroid distances = 3.651 (1), 3.828 (1), 3.811 (2) and 3.786 (1) Å].