Crystal structure of (Z)-N'-[1-(3-methyl-5-oxo-1-phenyl-1,5-di-hydro-4H-pyrazol-4-yl-idene)prop-yl]benzene-sulfono-hydrazide.

Chuan-Chuan He,Guan-Cheng Xu

doi:10.1107/s2056989015007094

Chuan-Chuan He, Guan-Cheng Xu

Open Access

https://doi.org/10.1107/s2056989015007094

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Abstract

The title compound, C19H20N4O3S, was synthesized by refluxing equimolar amounts of 1-phenyl-3-methyl-4-propionylpyrazol-5-one and benzene-sulfonyl hydrazide in ethanol. The compound crystallizes in the keto form and the carbonyl O atom forms an intra-molecular N-H⋯O hydrogen bond with the neighbouring NH group. There is also C-H⋯O short contact involving the neighbouring phenyl ring. Probably as a result of this, the phenyl ring is inclined to the pyrazolone ring by only 7.58 (12)°. The dihedral angle between the phenyl ring and the benzene-sulfonyl ring is 22.78 (11)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R (2) 2(14) ring motif. The dimers are linked via pairs of C-H⋯O hydrogen bonds, forming chains propagating along [100].

Highlights

The title compound, C19H20N4O3S, was synthesized by refluxing equimolar amounts of 1-phenyl-3-methyl-4-propionylpyrazol-5-one and benzenesulfonyl hydrazide in ethanol
The compound crystallizes in the keto form and the carbonyl O atom forms an intramolecular N—H O hydrogen bond with the neighbouring NH group
We have devoted our efforts to the design and synthesis of 4-acyl pyrazolone derivatives and their transition metal complexes (Zhang et al, 2004; Xu et al, 2013; Yi et al, 2014; Li et al, 2013)

Summary

Chemical context

Many pyrazolones and their derivatives possess biological and pharmaceutical activities, such as anticancer, antitumor and antifungal activities as well as the inhibition of lipid peroxidation (Wang et al, 1991; Yu et al, 1993; Padhyé & Kauffman, 1985; Yang et al, 1992). We have devoted our efforts to the design and synthesis of 4-acyl pyrazolone derivatives and their transition metal complexes (Zhang et al, 2004; Xu et al, 2013; Yi et al, 2014; Li et al, 2013). Such 4-acyl pyrazolone derivatives can form different types of complexes due to the multiple coordination sites and the tautomeric enol-to-keto effect. May be a promising drug for cancer chemotherapy (Wang et al, 2007) This has encouraged us to investigate more 4-acyl pyrazolone derivatives and we report on the synthesis and crystal structure of the title compound

Structural commentary

Synthesis and crystallization

Refinement