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

The configuration about each C=N bond in the title compound, C22H20N4O3S, 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 hydrazide–sulfonyl 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 b-axis direction are of the π–π type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid–centroid separation = 3.7425 (9) Å].

The configuration about each C N bond in the title compound, C 22 H 20 N 4 O 3 S, 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-HÁ Á ÁN hydrogen bond, significant twists are evident in the orientations of the hydrazine [N-N-C-C torsion angle = À170.74 (11) ] and benzoyl benzene [N-C-C-C = À21.72 (18) ] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the molecule [C-S-C-N = À92.28 (10) ]. Centrosymmetric aggregates mediated by pairs of hydrazide-sulfonyl N-HÁ Á ÁO hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supramolecular chains via C-HÁ Á ÁO interactions which are, in turn, linked into layers in the ac plane via C-HÁ Á Á interactions. Connections between layers along the b-axis direction are of thetype and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid-centroid separation = 3.7425 (9) Å ].   Table 1 Hydrogen-bond geometry (Å , ).

Related literature
Cg1 and Cg2 are the centroids of the C1-C6 and C17-C22 rings, respectively.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6353).
In the crystal packing, N-H···O hydrogen bonding between hydrazide-H and a sulfonyl-O leads to the formation of centrosymmetric aggregates via a 14-membered {···HNNC 2 SO} 2 synthon, Table 1. These are connected into a linear supramolecular chain via C-H···O interactions, Table 1 and Fig. 2. The chains are connected into layers in the ac plane via C-H···π interactions, Table 1. Layers are connected along the b direction via π-π interactions occurring between centrosymmetrically related hydrazine-bound benzene rings [3.7425 (9) Å for symmetry operation: -x, -y, -z].

Experimental
The title compound was prepared by the literature procedure (Abdel-Aziz et al., 2010) and yellow prisms were isolated from its solution in EtOH/DMF (v/v = 5/1) by slow evaporation at room temperature.

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H 0.95 to 0.98 Å, U iso (H) 1.2 to 1.5U eq (C)] and were included in the refinement in the riding model approximation. The amino-H atoms were located in a difference Fourier map, and subsequently refined freely. Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level. Fig. 2. Supramolecular chain in (I) mediated by N-H···O hydrogen bonds (blue dashed lines), leading to centrosymmetric aggregates, and C-H···O interactions, shown as orange lines. Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The N-H···O, C-H···O, C-H···π and π-π interactions are shown as blue, orange, purple and pink dashed lines, respectively. as those based on F, and R-factors based on ALL data will be even larger.