Abstract
Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.003 Å; R factor = 0.050; wR factor = 0.154; data-to-parameter ratio = 21.2.
In the title compound, C 22 H 16 N 4 O 4 S, the dihedral angles between the pyrazole ring and the pendant aromatic rings are 26.2 (1), 41.1 (1) and 89.5 (1) . In the crystal structure, an intermolecular C-HÁ Á ÁN bond helps to establish the packing. A short CÁ Á ÁC contact of 3.110 (12) Å is observed between the C atom of the pyrazole CH group and one of the -C atoms of the 4-methylphenyl ring.
Experimental
C 22 H 16 N 4 O 4 S M r = 432.45 Monoclinic, P2 1 =c a = 7.3802 (3) Å b = 26.6996 (11) Å c = 10.6691 (4) Å = 106.733 (2) V = 2013.31 (14) Å 3 Z = 4 Mo K radiation = 0.20 mm À1 T = 293 (2) K 0.25 Â 0.21 Â 0.19 mm Data collection Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T min = 0.951, T max = 0.963 26409 measured reflections 5987 independent reflections 4104 reflections with I > 2(I) R int = 0.030

In the title compound, C 22 H 16 N 4 O 4 S, the dihedral angles between the pyrazole ring and the pendant aromatic rings are 26.2 (1), 41.1 (1) and 89.5 (1) . In the crystal structure, an intermolecular C-HÁ Á ÁN bond helps to establish the packing. A short CÁ Á ÁC contact of 3.110 (12) Å is observed between the C atom of the pyrazole CH group and one of the -C atoms of the 4-methylphenyl ring.
Related literature
For related literature, see: Baraldi et al. (1998) ; Beddoes et al. (1986) ; Bruno et al. (1990) ; Cottineau et al. (2002) ; Londershausen (1996) ; Bernstein et al. (1995) ; Chen & Li (1998) ; Cordell (1981) ; Jin et al. (2004) ; Smith et al. (2001) .
Experimental
Crystal data 
A mixture of 1-(4-Methylphenyl)-2-(phenylsulfanyl)-1-ethanone 1-(2,4-dinitrophenyl)hydrazone (0.001 mole) dissolved in dimethylforamide (5 ml) in a 30 ml conical flask was allowed to cool in ice with stirring. To this stirred solution, phosphorus oxychloride (0.008 mole) was added dropwise and the mixture was subjected to microwave irritation for 60 sec. under 40% power with pulse rate 15 sec. The reaction was monitored by TLC and after completion of the reaction, the reaction mixture was poured onto crushed ice. The solid was suction filtered and washed with plenty of water. The final product 1-(2,4-Dinitrophenyl)-3-(4-methylphenyl)-1H-4-pyrazolyl phenyl sulfide was purified by column chromatography silica gel (60-120 mesh) using petroleum ether-ethyl acetate as eluent.
Data collection
Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T min = 0.951, T max = 0.963 26409 measured reflections 5987 independent reflections 4104 reflections with I > 2(I) R int = 0.030 Refinement R[F 2 > 2(F 2 )] = 0.050 wR(F 2 ) = 0.154 S = 1.05 5987 reflections 282 parameters 1 restraint H-atom parameters constrained Á max = 0.38 e Å À3 Á min = À0.27 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). Data collection: APEX2 (Bruker, 2004) ; cell refinement: SAINT (Bruker, 2004) ; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) ; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) ; molecular graphics: ORTEP (Farrugia, 1997) ; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003) .
1-(2,4-Dinitrophenyl)-3-(4-methylphenyl)-4-phenylsulfanyl-1H-pyrazole P. Ramesh, R. Venkatesan, R. Manikannan, S. Muthusubramanian and M. N. Ponnuswamy
Comment
Pyrazole derivatives have been reported to possess significant antiarrhythmic and sedative (Bruno et al., 1990) , hypoglycemic (Cottineau et al., 2002) , antiviral (Baraldi et al., 1998) , and pesticidal (Londershausen,1996) activities.
The ORTEP plot of the structure is shown in Fig. 1 . The pyrazole ring adopts planar conformation. The sum of the angles at N1 of the pyrazole ring (359.55°) is in accordance with sp 2 hybridization (Beddoes et al., 1986 ). The C-N bond lengths in the pyrazole ring are 1.319 (2) and 1.352 (2) Å, which are shorter than a C-N single bond length of 1.443 Å, but longer than a double bond length of 1.269 Å (Jin et al., 2004) , indicating electron delocalization. The pyrazole ring A and phenyl sulfide ring D are orthogonal with the inter-ring dihedral angle of 89.54 (10)°, whereas the dinitrophenyl and methylphenyl rings are twisted from the pyrazole ring as can be seen from the dihedral angles of 26.18 (10)° and 41.12 (10)°, respectively.
The crystal structure is stabilized by C-H···N types of intra and intermolecular interactions in addition to van der Waals forces. Atom C5 in the molecule at (x, y, z) donates a proton to atom N2 at (x, -1/2 -y, 1/2 + z) to form a one dimensional C4 chain running along c axis (Fig. 2. ). Short intermolecular contacts are observed between the atoms C5 and C15 (3.11 Å).
Refinement
H atoms were positioned geometrically (C-H=0.93-0.96 Å) and allowed to ride on their parent atoms, with U iso (H) = 1.5 U eq (C) for methyl H and U iso (H) = 1.2 U eq (C) other H atoms. The components of the anisotropic displacement parameters of C24 and C25 in the direction of the bond between them were restrained to be equal within an effective standard deviation of 0.01. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.24305 (7) 0.133863 (17) (7) −0.0019 (7) 0.0101 (6) −0.0009 (6) C15 0.0389 (9) 0.0377 (9) 0.0380 (8) 0.0011 (7) 0.0104 (7) 0.0057 (6) C16 0.0433 (10) 0.0562 (11) 0.0336 (7) −0.0003 (8) 0.0043 (7) 0.0085 (7) C17 0.0450 (10) 0.0574 (11) 0.0337 (7) −0.0060 (9) 0.0079 (7) −0.0058 (7) C18 0.0543 (11) 0.0395 (9) 0.0419 (8) −0.0010 (8) 0.0101 (8) −0.0079 (7) C19 0.0490 (10) 0.0371 (9) 0.0331 (7) 0.0037 (7) 0.0064 (7) 0.0001 (6) 

{'paper_id': '208930781', 'title': '1-(2,4-Dinitrophenyl)-3-(4-methylphenyl)-4-phenylsulfanyl-1H-pyrazole', 's2_url': 'https://api.semanticscholar.org/CorpusID:208930781', 'source': 'S2ORC'}