Research Article: (Z)-1-(2-Chloro­phen­yl)-3-methyl-4-[2-(4-nitro­phen­yl)hydrazin-1-yl­idene]-1H-pyrazol-5(4H)-one

Date Published: August 01, 2012

Publisher: International Union of Crystallography

Author(s): Carlos Bustos, Andrés Escobar-Fuentealba, Luis Alvarez-Thon, Rodrigo Faundez-Gutierrez, Maria Teresa Garland.

http://doi.org/10.1107/S1600536812029790

Abstract

There are two independent mol­ecules, A and B, in the asymmetric unit of the title compound, C16H12ClN5O3. The relative orientations of the chloro­phenyl ring with respect to the pyrazole ring in the two crystallographically independent mol­ecules are different, and their corresponding dihedral angles are −53.3 (2) and 114.09 (18)° in mol­ecules A and B, respectively. There are two strong intramolecular N—H⋯O hydrogen bonds, and two weak intramolecular C—H⋯O and C—H⋯Cl hydrogen bonds. The crystal packing is constructed by weak C—H⋯O and N—H⋯O inter­actions, and two π–π stacking inter­actions [centroid–centroid distances = 3.7894 (9) and 3.5719 (10) Å], forming a mol­ecular ladder along the a axis.

Partial Text

For synthesis and related literature, see: Abdel-Aziz et al. (2009 ▶); Bustos et al. (2006 ▶, 2007 ▶, 2009 ▶, 2012 ▶). For the biological activity of this class of compounds, see: Castagnolo et al. (2009 ▶); Chauhan et al. (1993 ▶); El-Hawash et al. (2006 ▶); Gunasekaran et al. (2011 ▶); Himly et al. (2003 ▶); Jolly et al. (1991 ▶); Kalluraya et al. (2007 ▶); Kawai et al. (1997 ▶); Moreau et al. (2008 ▶); Pasha et al. (2009 ▶); Radi et al. (2009 ▶); Singh (1991 ▶); Wu et al. (2002 ▶).

 

Source:

http://doi.org/10.1107/S1600536812029790

 

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