Crystal structure of (E)-N-{2-[2-(4-methyl-benzyl-idene)hydrazin-1-yl]-2-oxoeth-yl}-p-toluene-sulfonamide.

Abstract

The title acyl-hydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The mol-ecules are bent at the S atom, with C-SO2-NH-CH2 torsion angles of -67.3 (2) and 67.7 (3)° in mol-ecules A and B, respectively. Further, the dihedral angles between the sulfonyl-glycine segments and the p-toluene-sulfonyl rings are 76.1 (1) and 85.8 (1)° in mol-ecules A and B, respectively. The central hydrazone segments and the toluene rings attached to them are almost co-planar with their mean planes being inclined to one another by 5.2 (2) (mol-ecule A) and 2.9 (2)° (mol-ecule B). The dihedral angles between the benzene rings are 86.83 (12) (mol-ecule A) and 74.00 (14)° (mol-ecule B). In the crystal, the A mol-ecules are linked by a pair of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via three N-H⋯O hydrogen bonds involving the B mol-ecules, forming chains along [100] and enclosing R 2 (2)(12) and R 4 (4)(16) ring motifs. The chains are linked via C-H⋯O hydrogen bonds and a C-H⋯π inter-action, forming sheets parallel to (010). There is a further C-H⋯π inter-action and a slipped parallel π-π inter-action [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.