4-(4-Chloro­phenyl­sulfan­yl)-1-[(E)-2-(4-chloro­phenyl­sulfan­yl)-1-phenyl­ethen­yl]-3-phenyl-1H-pyrazole

P Ramesh; A Subbiahpandi; Ramaiyan Manikannan; S Muthusubramanian; M N Ponnuswamy

doi:10.1107/S1600536808031231

. 2008 Oct 4;64(Pt 11):o2054–o2055. doi: 10.1107/S1600536808031231

4-(4-Chlorophenylsulfanyl)-1-[(E)-2-(4-chlorophenylsulfanyl)-1-phenylethenyl]-3-phenyl-1H-pyrazole

P Ramesh ^a, A Subbiahpandi ^a, Ramaiyan Manikannan ^b, S Muthusubramanian ^b, M N Ponnuswamy ^c,^*

PMCID: PMC2959571 PMID: 21580921

Abstract

In the title compound, C₂₉H₂₀Cl₂N₂S₂, the pyrazole ring adopts a planar conformation. The chlorophenyl rings are twisted from the pyrazole ring at angles of 52.74 (14) and 29.92 (13)°, respectively. The crystal structure is stabilized by C—H⋯N and C—H⋯π interactions.

Related literature

For the pharmacological and medicinal properties of the title compound, see: Baraldi et al. (1998 ▶); Bruno et al. (1990 ▶); Cottineau et al. (2002 ▶); Londershausen (1996 ▶); Chen & Li (1998 ▶); Mishra et al. (1998 ▶); Smith et al. (2001 ▶). For hybridization, see: Beddoes et al. (1986 ▶). For a related structure, see: Jin et al. (2004 ▶).

Experimental

Crystal data

C₂₉H₂₀Cl₂N₂S₂
M _r = 531.49
Monoclinic,
a = 12.3808 (4) Å
b = 21.4667 (7) Å
c = 10.4281 (4) Å
β = 108.181 (2)°
V = 2633.16 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.883, T _max = 0.927
31420 measured reflections
6594 independent reflections
4292 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.142
S = 1.02
6594 reflections
316 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031231/bt2789sup1.cif

e-64-o2054-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031231/bt2789Isup2.hkl

e-64-o2054-Isup2.hkl^{(316.2KB, hkl)}

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

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

Cg is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N1	0.93	2.44	2.772 (3)	101
C21—H21⋯Cgⁱ	0.93	2.96	3.808 (3)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

PR thanks Dr Babu Varghese, SAIF, IIT Madras, Chennai, India, for his help with the data collection.

supplementary crystallographic information

Comment

Pyrazole derivatives possess significant antiarrhythmic and sedative (Bruno et al., 1990), hypoglycemic (Cottineau et al., 2002), antiviral (Baraldi et al., 1998), and pesticidal (Londershausen et al., 1996) properties. Some pyrazole derivatives are successfully tested for their antifungal (Chen & Li, 1998), antihistaminic (Mishra et al., 1998) and anti-inflammatory (Smith et al., 2001) activities.

An ORTEP plot of the molecule is shown in Fig. 1. The pyrazole ring adopts a planar conformation. The sum of the bond angles at N2 of the pyrazole ring (359.34°) is in accordance with sp² hybridization (Beddoes et al., 1986). The C—N bond lengths in the pyrazole ring are 1.340 (3) and 1.325 (3) 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 chlorophenyl rings are twisted from the pyrazole ring at angles of 52.74 (14)° and 29.92 (13), respectively. The crystal packing shows weak C—H···N (Tab. 1) and C—H···π interactions [C21-H21···cogⁱ(C26,C27,C28,C29,C30,C31); symmetry operator (i) x, 1/2-y, 1/2+z: H···cog 2.956Å, C21···cog 3.808Å, C21-H21···cog 152.9°] in addition to van der Waals forces.

Experimental

To a mixture of 2-[(4-chlorophenyl)sulfanyl]-1-phenyl-1-ethanone N-(E)-2- [(4-chlorophenyl)sulfanyl]-1-phenylethylidenehydrazone (0.003 mole) and 3 ml of dimethyl formamide kept in ice bath at 0° C, phosphorus oxycholride (0.024 mole) was added dropwise for 5–10 minutes. The reaction mixture was then kept in a microwave oven at 600 W for 30–60 sec. The process of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and extracted with dichloromethane. The organic layer was dried in anhydrous sodium sulfate. The different compounds present in the mixture were separated by column chromatography using petroleum ether and ethyl acetate mixture as eluent. This isolated compound was recrystallized in dichloromethane to obtain 4-[(4-chlorophenyl)sulfanyl]-1- (E)-2-[(4-chlorophenyl)sulfanyl]-1-phenylethenyl-3-phenyl-1H-pyrazole in 86% yield.