1-(2,4-Dinitro­phen­yl)-3-phenyl-4-phenyl­sulfanyl-1H-pyrazole

V Susindran; S Athimoolam; S Asath Bahadur; R Manikannan; S Muthusubramanian

doi:10.1107/S1600536812036914

. 2012 Sep 5;68(Pt 10):o2845. doi: 10.1107/S1600536812036914

1-(2,4-Dinitrophenyl)-3-phenyl-4-phenylsulfanyl-1H-pyrazole

V Susindran ^a, S Athimoolam ^b,^*, S Asath Bahadur ^a, R Manikannan ^c, S Muthusubramanian ^c

PMCID: PMC3470205 PMID: 23125649

Abstract

In the title molecule, C₂₁H₁₄N₄O₄S, the pyrazole ring forms dihedral angles of 45.6 (1), 87.7 (1) and 27.4 (1)° with the phenyl, sulfur-substituted benzene and nitro-substituted benzene rings, respectively. In the crystal, molecules are connected by weak C—H⋯O and C—H⋯N hydrogen bonds into layers parallel to (010).

Related literature

For the pharmacological and medicinal properties of pyrazole compounds, see: Baraldi et al. (1998 ▶); Bruno et al. (1990 ▶); Chen & Li (1998 ▶); Cottineau et al. (2002 ▶); Londershausen (1996 ▶); Mishra et al. (1998 ▶); Smith et al. (2001 ▶).

Experimental

Crystal data

C₂₁H₁₄N₄O₄S
M _r = 418.42
Monoclinic,
a = 7.3062 (4) Å
b = 26.5212 (13) Å
c = 10.3361 (5) Å
β = 104.012 (1)°
V = 1943.22 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.24 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer
18559 measured reflections
3426 independent reflections
3128 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.091
S = 1.04
3426 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036914/lh5484sup1.cif

e-68-o2845-sup1.cif^{(26.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036914/lh5484Isup2.hkl

e-68-o2845-Isup2.hkl^{(164.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036914/lh5484Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C35—H35⋯O42ⁱ	0.93	2.58	3.452 (2)	157
C5—H5⋯N2ⁱⁱ	0.93	2.52	3.411 (2)	161

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

VS and SAB sincerely thank the Vice Chancellor and Management of the Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement.

supplementary crystallographic information

Comment

Pyrazoles are a class of aromatic ring compounds and of the heterocyclic series characterized by a 5-membered ring structure composed of three carbon atoms and two nitrogen atoms in adjacent positions and to the unsubstituted parent compound. They can have pharmacological effects on humans and are classified as alkaloids although they are rare in nature. Pyrazole and its derivatives have successfully tested for antifungal (Chen & Li, 1998), antihistaminic (Mishra et al.,1998), anti-inflammatory (Smith et al., 2001), antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998) and pesticidal (Londershausen, 1996) activities.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring forms dihedral angles of 27.4 (1)° (with the C11-C16 ring), 45.6 (1)° (with the C31-C36 ring) and 87.7 (1)° (with the C41-C46 ring). In the nitrophenyl group, the nitro substituents are twisted from the benzen ring by 13.9 (2)° and 43.2 (1)°. In the crystal, molecules are connected by weak C—H···O and C—H···N hydrogen bonds into layers parallel to (010) (see Fig. 2).

Experimental

A mixture of 1-phenyl-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 irradiation for 30 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-phenyl-4-(phenylsulfanyl)-1H-pyrazole was purified by column chromatography using petroleum ether-ethyl acetate as eluent. Colourless needles were grown over a period of a week from a solution of the title compound in dichlromethane.