4-{[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]carbonyl}-N-(4-cyanophenyl)piperazine-1-carboxamide

In the title compound, C28H22ClFN6O2, the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyanophenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro- and chlorophenyl rings are 34.16 (10) and 73.27 (12)°, respectively. In the crystal, intermolecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds link the molecules into sheets parallel to the ac plane.

In the title compound, C 28 H 22 ClFN 6 O 2 , the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12) , respectively, with the pyrazole and cyanophenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro-and chlorophenyl rings are 34.16 (10) and 73.27 (12) , respectively. In the crystal, intermolecular N-HÁ Á ÁO, C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds link the molecules into sheets parallel to the ac plane.

Comment
The antibacterial and antifungal activities of azoles have been widely studied and some of them are used in clinical practice as antimicrobial agents. However, azole-resistant strains have led to the development of new antimicrobial compounds. In particular, pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazoles form an important class of heterocyclic compound and many pyrazole derivatives are reported to have a broad spectrum of biological activities, such as anti-inflammatory, antifungal, herbicidal, antitumor, cytotoxic and antiviral activities; they are also used in molecular modelling. Pyrazole derivatives also act as anti-angiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists as well as kinase inhibitor for the treatment of type 2 diabetes, hyperlipidemia, obesity and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of drug molecules play an important role in enhancing their biological activity, we are interested in compounds having 4-fluoro-or 4-chloro-substitution in 1,5diaryl pyrazoles. The background to pyrazole derivatives and their microbial activities habe been reported in reccent years (Ragavan et al., 2009. The crystal structure of the title compound is reported here. In the title compound ( Fig. 1) the piperazine ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) of Q = 0.540 (2) Å, Θ = 1.3 (2)°, φ = 235 (21)° and the plane through the coplanar atoms (N4/C19/N3/C17) forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyanophenyl rings. The dihedral angles formed between the pyrazole and attached fluoro-and chlorophenyl rings are 34.16 (10) and 73.27 (12)°, respectively.
Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those in related crystal structures (Fun et al., 2010;Shahani et al., 2010).

Experimental
The compound has been synthesized using a method reported in the literature

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. supplementary materials sup-9