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

Ramesh, P.; Subbiahpandi, A.; Manikannan, R.; Muthusubramanian, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536808031231

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages o2054-o2055

doi:10.1107/S1600536808031231

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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 and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 13 September 2008; accepted 26 September 2008; online 4 October 2008)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.050
wR(F²) = 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

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
Symmetry code: (i) $[x, {1 \over 2}-y, {1 \over 2}+z]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atomic numbering and 50% probability displacement ellipsoids.

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

Crystal data top

C₂₉H₂₀Cl₂N₂S₂	F(000) = 1096
M_r = 531.49	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4538 reflections
a = 12.3808 (4) Å	θ = 1.9–28.4°
b = 21.4667 (7) Å	µ = 0.43 mm⁻¹
c = 10.4281 (4) Å	T = 293 K
β = 108.181 (2)°	Block, colorless
V = 2633.16 (16) Å³	0.30 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	6594 independent reflections
Radiation source: fine-focus sealed tube	4292 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→16
T_min = 0.883, T_max = 0.927	k = −28→28
31420 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0499P)² + 1.5769P] where P = (F_o² + 2F_c²)/3
6594 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.58 e Å⁻³
6 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₂₉H₂₀Cl₂N₂S₂	V = 2633.16 (16) Å³
M_r = 531.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3808 (4) Å	µ = 0.43 mm⁻¹
b = 21.4667 (7) Å	T = 293 K
c = 10.4281 (4) Å	0.30 × 0.20 × 0.18 mm
β = 108.181 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	6594 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	4292 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.927	R_int = 0.027
31420 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	6 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.58 e Å⁻³
6594 reflections	Δρ_min = −0.56 e Å⁻³
316 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.05360 (11)	0.97426 (6)	1.29295 (10)	0.1304 (4)
Cl2	0.49992 (8)	0.55063 (4)	0.67733 (9)	0.0936 (3)
S1	−0.22821 (6)	0.89305 (5)	0.68804 (10)	0.0988 (3)
S2	0.13985 (5)	0.72882 (3)	0.29751 (6)	0.05543 (17)
N2	−0.03047 (14)	0.82027 (8)	0.48954 (18)	0.0442 (4)
N1	0.06227 (14)	0.85803 (8)	0.52541 (18)	0.0458 (4)
C4	0.08940 (18)	0.77699 (10)	0.4007 (2)	0.0457 (5)
C5	0.13504 (17)	0.83241 (10)	0.4710 (2)	0.0432 (5)
C3	−0.01665 (18)	0.77170 (10)	0.4154 (2)	0.0474 (5)
H3	−0.0692	0.7402	0.3804	0.057*
C6	−0.12269 (18)	0.83142 (11)	0.5402 (2)	0.0487 (5)
C7	−0.1128 (2)	0.87324 (13)	0.6357 (3)	0.0660 (7)
H7	−0.0430	0.8924	0.6756	0.079*
C8	−0.1672 (2)	0.91670 (13)	0.8564 (3)	0.0708 (7)
C9	−0.0600 (2)	0.90247 (14)	0.9387 (3)	0.0749 (8)
H9	−0.0108	0.8804	0.9040	0.090*
C10	−0.0243 (3)	0.92044 (15)	1.0718 (4)	0.0844 (9)
H10	0.0490	0.9110	1.1262	0.101*
C11	−0.0963 (3)	0.95220 (14)	1.1244 (3)	0.0815 (9)
C12	−0.2020 (3)	0.96751 (19)	1.0443 (4)	0.1049 (12)
H12	−0.2504	0.9899	1.0797	0.126*
C13	−0.2377 (3)	0.95004 (19)	0.9112 (4)	0.1074 (13)
H13	−0.3104	0.9608	0.8570	0.129*
C14	−0.22593 (18)	0.79358 (11)	0.4766 (2)	0.0521 (5)
C15	−0.3037 (2)	0.81280 (15)	0.3589 (3)	0.0748 (8)
H15	−0.2918	0.8497	0.3186	0.090*
C16	−0.4000 (3)	0.7778 (2)	0.2995 (4)	0.0977 (11)
H16	−0.4524	0.7911	0.2192	0.117*
C17	−0.4182 (3)	0.7247 (2)	0.3572 (4)	0.1013 (13)
H17	−0.4834	0.7014	0.3171	0.122*
C18	−0.3416 (4)	0.7046 (2)	0.4741 (4)	0.1147 (15)
H18	−0.3544	0.6677	0.5137	0.138*
C19	−0.2445 (3)	0.73921 (16)	0.5344 (3)	0.0901 (10)
H19	−0.1919	0.7254	0.6141	0.108*
C20	0.23637 (18)	0.67789 (10)	0.4109 (2)	0.0465 (5)
C21	0.3060 (2)	0.64266 (12)	0.3584 (3)	0.0584 (6)
H21	0.2985	0.6456	0.2670	0.070*
C22	0.3863 (2)	0.60336 (12)	0.4394 (3)	0.0656 (7)
H22	0.4333	0.5801	0.4035	0.079*
C23	0.3961 (2)	0.59894 (11)	0.5732 (3)	0.0615 (6)
C24	0.3265 (2)	0.63248 (13)	0.6277 (3)	0.0653 (7)
H24	0.3333	0.6286	0.7187	0.078*
C25	0.2463 (2)	0.67213 (12)	0.5457 (2)	0.0571 (6)
H25	0.1989	0.6950	0.5817	0.069*
C26	0.24546 (18)	0.86348 (11)	0.4912 (2)	0.0471 (5)
C27	0.34364 (19)	0.83066 (12)	0.5004 (2)	0.0544 (6)
H27	0.3402	0.7878	0.4864	0.065*
C28	0.4473 (2)	0.86127 (14)	0.5304 (3)	0.0653 (7)
H28	0.5130	0.8389	0.5364	0.078*
C29	0.4531 (2)	0.92423 (15)	0.5512 (3)	0.0738 (8)
H29	0.5228	0.9445	0.5725	0.089*
C30	0.3564 (2)	0.95734 (14)	0.5405 (3)	0.0780 (8)
H30	0.3604	1.0003	0.5534	0.094*
C31	0.2524 (2)	0.92733 (12)	0.5107 (3)	0.0637 (7)
H31	0.1870	0.9502	0.5039	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1506 (10)	0.1492 (10)	0.0782 (6)	0.0227 (8)	0.0167 (6)	−0.0108 (6)
Cl2	0.0875 (6)	0.0736 (5)	0.1054 (6)	0.0208 (4)	0.0094 (5)	0.0060 (4)
S1	0.0426 (4)	0.1458 (8)	0.1049 (6)	0.0127 (4)	0.0184 (4)	−0.0526 (6)
S2	0.0496 (3)	0.0730 (4)	0.0426 (3)	0.0013 (3)	0.0128 (2)	−0.0085 (3)
N2	0.0340 (9)	0.0478 (10)	0.0491 (10)	−0.0018 (7)	0.0103 (7)	0.0014 (8)
N1	0.0401 (9)	0.0447 (9)	0.0511 (10)	−0.0051 (7)	0.0119 (8)	0.0017 (8)
C4	0.0388 (11)	0.0537 (12)	0.0425 (11)	−0.0019 (9)	0.0097 (9)	−0.0018 (9)
C5	0.0382 (11)	0.0498 (12)	0.0404 (10)	−0.0024 (9)	0.0103 (8)	0.0055 (9)
C3	0.0373 (11)	0.0513 (12)	0.0504 (12)	−0.0036 (9)	0.0089 (9)	−0.0035 (10)
C6	0.0351 (11)	0.0543 (13)	0.0546 (13)	0.0051 (9)	0.0109 (9)	0.0013 (10)
C7	0.0375 (12)	0.0774 (17)	0.0822 (18)	0.0019 (11)	0.0173 (12)	−0.0179 (15)
C8	0.0533 (15)	0.0706 (17)	0.089 (2)	0.0111 (13)	0.0222 (14)	−0.0161 (15)
C9	0.0548 (16)	0.0710 (18)	0.099 (2)	0.0148 (13)	0.0241 (15)	−0.0101 (16)
C10	0.0685 (19)	0.084 (2)	0.092 (2)	0.0161 (16)	0.0113 (16)	0.0015 (18)
C11	0.091 (2)	0.0686 (18)	0.080 (2)	0.0153 (16)	0.0203 (17)	−0.0020 (15)
C12	0.103 (3)	0.118 (3)	0.092 (2)	0.049 (2)	0.028 (2)	−0.021 (2)
C13	0.074 (2)	0.142 (3)	0.098 (3)	0.051 (2)	0.0150 (18)	−0.031 (2)
C14	0.0384 (11)	0.0631 (14)	0.0565 (13)	−0.0014 (10)	0.0175 (10)	−0.0032 (11)
C15	0.0466 (14)	0.087 (2)	0.0811 (19)	−0.0006 (13)	0.0055 (13)	0.0086 (16)
C16	0.0480 (16)	0.140 (3)	0.090 (2)	−0.0098 (19)	−0.0007 (15)	−0.009 (2)
C17	0.072 (2)	0.147 (4)	0.092 (3)	−0.055 (2)	0.0362 (19)	−0.042 (2)
C18	0.135 (4)	0.118 (3)	0.096 (3)	−0.071 (3)	0.043 (3)	−0.011 (2)
C19	0.099 (2)	0.091 (2)	0.0697 (19)	−0.0358 (19)	0.0118 (17)	0.0075 (17)
C20	0.0432 (11)	0.0498 (12)	0.0489 (12)	−0.0083 (9)	0.0177 (9)	−0.0106 (10)
C21	0.0645 (15)	0.0629 (15)	0.0545 (14)	−0.0016 (12)	0.0283 (12)	−0.0093 (12)
C22	0.0661 (16)	0.0593 (15)	0.0797 (18)	0.0048 (13)	0.0347 (14)	−0.0102 (13)
C23	0.0583 (15)	0.0484 (13)	0.0731 (17)	−0.0009 (11)	0.0136 (13)	−0.0042 (12)
C24	0.0750 (18)	0.0684 (16)	0.0510 (14)	0.0034 (14)	0.0175 (12)	−0.0034 (12)
C25	0.0569 (14)	0.0674 (15)	0.0510 (13)	0.0055 (12)	0.0227 (11)	−0.0067 (11)
C26	0.0421 (11)	0.0585 (13)	0.0391 (11)	−0.0097 (10)	0.0103 (9)	0.0051 (9)
C27	0.0453 (12)	0.0629 (14)	0.0555 (13)	−0.0062 (11)	0.0164 (10)	−0.0006 (11)
C28	0.0421 (13)	0.0853 (19)	0.0682 (16)	−0.0075 (12)	0.0167 (11)	0.0051 (14)
C29	0.0478 (15)	0.085 (2)	0.0841 (19)	−0.0233 (14)	0.0140 (13)	0.0101 (16)
C30	0.0644 (18)	0.0612 (16)	0.102 (2)	−0.0207 (14)	0.0169 (16)	0.0073 (15)
C31	0.0503 (14)	0.0570 (15)	0.0802 (18)	−0.0086 (11)	0.0150 (12)	0.0087 (13)

Geometric parameters (Å, º) top

Cl1—C11	1.735 (3)	C15—H15	0.9300
Cl2—C23	1.742 (3)	C16—C17	1.340 (5)
S1—C7	1.734 (3)	C16—H16	0.9300
S1—C8	1.756 (3)	C17—C18	1.360 (6)
S2—C4	1.742 (2)	C17—H17	0.9300
S2—C20	1.772 (2)	C18—C19	1.386 (5)
N2—C3	1.340 (3)	C18—H18	0.9300
N2—N1	1.359 (2)	C19—H19	0.9300
N2—C6	1.420 (3)	C20—C25	1.378 (3)
N1—C5	1.325 (3)	C20—C21	1.382 (3)
C4—C3	1.373 (3)	C21—C22	1.375 (4)
C4—C5	1.419 (3)	C21—H21	0.9300
C5—C26	1.476 (3)	C22—C23	1.366 (4)
C3—H3	0.9300	C22—H22	0.9300
C6—C7	1.318 (3)	C23—C24	1.374 (4)
C6—C14	1.485 (3)	C24—C25	1.383 (4)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.371 (4)	C25—H25	0.9300
C8—C13	1.383 (4)	C26—C27	1.382 (3)
C9—C10	1.374 (4)	C26—C31	1.384 (3)
C9—H9	0.9300	C27—C28	1.388 (3)
C10—C11	1.366 (4)	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.367 (4)
C11—C12	1.355 (5)	C28—H28	0.9300
C12—C13	1.371 (5)	C29—C30	1.367 (4)
C12—H12	0.9300	C29—H29	0.9300
C13—H13	0.9300	C30—C31	1.386 (3)
C14—C19	1.365 (4)	C30—H30	0.9300
C14—C15	1.366 (4)	C31—H31	0.9300
C15—C16	1.382 (4)

C7—S1—C8	104.26 (13)	C15—C16—H16	119.9
C4—S2—C20	104.53 (10)	C16—C17—C18	120.2 (3)
C3—N2—N1	111.96 (17)	C16—C17—H17	119.9
C3—N2—C6	127.43 (18)	C18—C17—H17	119.9
N1—N2—C6	120.35 (17)	C17—C18—C19	120.0 (4)
C5—N1—N2	105.27 (17)	C17—C18—H18	120.0
C3—C4—C5	104.59 (19)	C19—C18—H18	120.0
C3—C4—S2	124.02 (17)	C14—C19—C18	120.0 (3)
C5—C4—S2	130.90 (16)	C14—C19—H19	120.0
N1—C5—C4	110.79 (18)	C18—C19—H19	120.0
N1—C5—C26	118.32 (19)	C25—C20—C21	119.2 (2)
C4—C5—C26	130.9 (2)	C25—C20—S2	124.29 (17)
N2—C3—C4	107.39 (19)	C21—C20—S2	116.56 (18)
N2—C3—H3	126.3	C22—C21—C20	120.9 (2)
C4—C3—H3	126.3	C22—C21—H21	119.6
C7—C6—N2	120.0 (2)	C20—C21—H21	119.6
C7—C6—C14	125.0 (2)	C23—C22—C21	119.2 (2)
N2—C6—C14	114.93 (19)	C23—C22—H22	120.4
C6—C7—S1	120.9 (2)	C21—C22—H22	120.4
C6—C7—H7	119.5	C22—C23—C24	121.3 (2)
S1—C7—H7	119.5	C22—C23—Cl2	119.4 (2)
C9—C8—C13	117.9 (3)	C24—C23—Cl2	119.3 (2)
C9—C8—S1	126.3 (2)	C23—C24—C25	119.2 (2)
C13—C8—S1	115.7 (2)	C23—C24—H24	120.4
C8—C9—C10	120.9 (3)	C25—C24—H24	120.4
C8—C9—H9	119.6	C20—C25—C24	120.3 (2)
C10—C9—H9	119.6	C20—C25—H25	119.8
C11—C10—C9	120.1 (3)	C24—C25—H25	119.8
C11—C10—H10	120.0	C27—C26—C31	118.8 (2)
C9—C10—H10	120.0	C27—C26—C5	122.3 (2)
C12—C11—C10	119.9 (3)	C31—C26—C5	118.7 (2)
C12—C11—Cl1	119.3 (3)	C26—C27—C28	120.4 (2)
C10—C11—Cl1	120.8 (3)	C26—C27—H27	119.8
C11—C12—C13	120.1 (3)	C28—C27—H27	119.8
C11—C12—H12	119.9	C29—C28—C27	120.2 (3)
C13—C12—H12	119.9	C29—C28—H28	119.9
C12—C13—C8	121.0 (3)	C27—C28—H28	119.9
C12—C13—H13	119.5	C30—C29—C28	120.0 (2)
C8—C13—H13	119.5	C30—C29—H29	120.0
C19—C14—C15	119.1 (3)	C28—C29—H29	120.0
C19—C14—C6	120.7 (2)	C29—C30—C31	120.4 (3)
C15—C14—C6	120.2 (2)	C29—C30—H30	119.8
C14—C15—C16	120.4 (3)	C31—C30—H30	119.8
C14—C15—H15	119.8	C26—C31—C30	120.2 (3)
C16—C15—H15	119.8	C26—C31—H31	119.9
C17—C16—C15	120.2 (3)	C30—C31—H31	119.9
C17—C16—H16	119.9

C3—N2—N1—C5	0.5 (2)	C7—C6—C14—C15	94.6 (3)
C6—N2—N1—C5	175.07 (18)	N2—C6—C14—C15	−84.7 (3)
C20—S2—C4—C3	−104.7 (2)	C19—C14—C15—C16	0.2 (5)
C20—S2—C4—C5	84.6 (2)	C6—C14—C15—C16	−179.9 (3)
N2—N1—C5—C4	−0.8 (2)	C14—C15—C16—C17	0.3 (5)
N2—N1—C5—C26	179.40 (17)	C15—C16—C17—C18	−0.5 (6)
C3—C4—C5—N1	0.8 (2)	C16—C17—C18—C19	0.1 (7)
S2—C4—C5—N1	172.85 (17)	C15—C14—C19—C18	−0.5 (5)
C3—C4—C5—C26	−179.5 (2)	C6—C14—C19—C18	179.6 (3)
S2—C4—C5—C26	−7.4 (4)	C17—C18—C19—C14	0.3 (6)
N1—N2—C3—C4	−0.1 (2)	C4—S2—C20—C25	11.8 (2)
C6—N2—C3—C4	−174.1 (2)	C4—S2—C20—C21	−167.52 (18)
C5—C4—C3—N2	−0.4 (2)	C25—C20—C21—C22	−1.6 (4)
S2—C4—C3—N2	−173.19 (16)	S2—C20—C21—C22	177.8 (2)
C3—N2—C6—C7	164.7 (2)	C20—C21—C22—C23	0.6 (4)
N1—N2—C6—C7	−8.9 (3)	C21—C22—C23—C24	0.7 (4)
C3—N2—C6—C14	−15.9 (3)	C21—C22—C23—Cl2	−178.5 (2)
N1—N2—C6—C14	170.50 (18)	C22—C23—C24—C25	−1.0 (4)
N2—C6—C7—S1	173.84 (18)	Cl2—C23—C24—C25	178.2 (2)
C14—C6—C7—S1	−5.5 (4)	C21—C20—C25—C24	1.2 (4)
C8—S1—C7—C6	152.2 (2)	S2—C20—C25—C24	−178.1 (2)
C7—S1—C8—C9	−19.9 (3)	C23—C24—C25—C20	0.0 (4)
C7—S1—C8—C13	163.8 (3)	N1—C5—C26—C27	147.7 (2)
C13—C8—C9—C10	0.5 (5)	C4—C5—C26—C27	−32.0 (3)
S1—C8—C9—C10	−175.8 (3)	N1—C5—C26—C31	−27.8 (3)
C8—C9—C10—C11	0.9 (5)	C4—C5—C26—C31	152.5 (2)
C9—C10—C11—C12	−1.8 (6)	C31—C26—C27—C28	0.8 (3)
C9—C10—C11—Cl1	179.0 (3)	C5—C26—C27—C28	−174.7 (2)
C10—C11—C12—C13	1.4 (6)	C26—C27—C28—C29	0.0 (4)
Cl1—C11—C12—C13	−179.4 (3)	C27—C28—C29—C30	−0.9 (4)
C11—C12—C13—C8	0.0 (7)	C28—C29—C30—C31	1.0 (5)
C9—C8—C13—C12	−1.0 (6)	C27—C26—C31—C30	−0.7 (4)
S1—C8—C13—C12	175.7 (4)	C5—C26—C31—C30	174.9 (2)
C7—C6—C14—C19	−85.5 (4)	C29—C30—C31—C26	−0.1 (5)
N2—C6—C14—C19	95.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1	0.93	2.44	2.772 (3)	101

Experimental details

Crystal data
Chemical formula	C₂₉H₂₀Cl₂N₂S₂
M_r	531.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.3808 (4), 21.4667 (7), 10.4281 (4)
β (°)	108.181 (2)
V (Å³)	2633.16 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.30 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.883, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	31420, 6594, 4292
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.142, 1.02
No. of reflections	6594
No. of parameters	316
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.56

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1	0.9300	2.4400	2.772 (3)	101.00

Acknowledgements

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

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165–2171. Web of Science CrossRef CAS Google Scholar
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Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
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Volume 64| Part 11| November 2008| Pages o2054-o2055

doi:10.1107/S1600536808031231

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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