4-(4-Chloro-phenyl-sulfan-yl)-1-[(E)-2-(4-chloro-phenyl-sulfan-yl)-1-phenyl-ethen-yl]-3-phenyl-1H-pyrazole.

In the title compound, C(29)H(20)Cl(2)N(2)S(2), 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 inter-actions.

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 = 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

Δρmax = 0.58 e Å−3

Δρmin = −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 ▶).

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

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

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

C29H20Cl2N2S2	F(000) = 1096
Mr = 531.49	Dx = 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

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

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(Fo2) + (0.0499P)2 + 1.5769P] where P = (Fo2 + 2Fc2)/3
6594 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.58 e Å−3
6 restraints	Δρmin = −0.56 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .