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.
Highlights
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 hydrazone Schiff bases of aroyl, acyl and heteroaroyl compounds are more versatile and flexible due to the presence of the C O group, an additional donor site
Antiviral activity has been shown for acylhydrazone derivatives which contain an amino acid moiety and an electron-donating substituent in the sulfonyl phenyl ring (Tian et al, 2009)
Summary
In a continuation of our studies of substituent effects on the structures of such compounds, for example N-(aryl)-amides (Gowda et al, 2006; Rodrigues et al, 2011), N-chloroarylamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), we report on the synthesis and crystal structure of the title compound. This acylhydrazone derivative contains a glycine moiety and elecdoi:10.1107/S2056989015009330.
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