N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl) propan-2-ylidene]benzohydrazide

Abstract

The configuration about each C=N bond in the title compound, C 22H 20N 4O 3S, is E. While to a first approximation the phenylhydrazin-1-ylidene and benzohydrazide residues are coplanar, in part due to the presence of an intramolecular N - H⋯N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N - N - C - C torsion angle = -170.74 (11)°] and benzoyl benzene [N - C - C - C = -21.72 (18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the molecule [C - S - C - N = -92.28 (10)°]. Centrosymmetric aggregates mediated by pairs of hydrazidesulfonyl N - H⋯O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supramolecular chains via C - H⋯O interactions which are, in turn, linked into layers in the ac plane via C - H⋯π interactions. Connections between layers along the baxis direction are of the π-π type and occur between centrosymmetrically related hydrazinebound benzene rings [centroidcentroid separation = 3.7425 (9) Å].