Crystal structure of (E)-N-{2-[2-(4-methylbenzylidene)hydrazin-1-yl]-2-oxoethyl}-p-toluenesulfonamide

The title acylhydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent molecules (A and B) in the asymmetric unit. The molecules are bent at the S atom, with C—SO2—NH—CH2 torsion angles...

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Bibliographic Details
Main Authors: H. Purandara, Sabine Foro, B. Thimme Gowda
Format: Article
Language:English
Published: International Union of Crystallography 2015-06-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989015009330
Description
Summary:The title acylhydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent molecules (A and B) in the asymmetric unit. The molecules are bent at the S atom, with C—SO2—NH—CH2 torsion angles of −67.3 (2) and 67.7 (3)° in molecules A and B, respectively. Further, the dihedral angles between the sulfonylglycine segments and the p-toluenesulfonyl rings are 76.1 (1) and 85.8 (1)° in molecules 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) (molecule A) and 2.9 (2)° (molecule B). The dihedral angles between the benzene rings are 86.83 (12) (molecule A) and 74.00 (14)° (molecule B). In the crystal, the A molecules are linked by a pair of N—H...O hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked via three N—H...O hydrogen bonds involving the B molecules, forming chains along [100] and enclosing R22(12) and R44(16) ring motifs. The chains are linked via C—H...O hydrogen bonds and a C—H...π interaction, forming sheets parallel to (010). There is a further C—H...π interaction and a slipped parallel π–π interaction [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.
ISSN:2056-9890