2-(1,5-Diphenyl-1H-pyrazol-3-yl-oxy)-1-(2-sulfanyl-idene-1,3-thia-zolidin-3-yl)-ethanone.

The title compound, C(20)H(17)N(3)O(2)S(2), was synthesized by the reaction of 2-(1,5-diphenyl-1H-pyrazol-3-yl-oxy)acetic acid and thia-zolidine-2-thione. The C-linked benzene ring, N-linked benzene ring and thia-zolidine-2-thione ring are twisted 31.33 (2), 62.87 (1) and 82.71 (2)°, respectively, from the plane of the bridging 1H-pyrazole ring. The phenyl rings are oriented at a dihedral angle of 72.16 (2)°.

Related literature

For pyrazol derivative bioactivities, see: Aly (2009 ▶); Meegalla et al. (2004 ▶); Morimoto et al. (1990 ▶). For a related structure, see: Goodman et al. (1971 ▶). For bond lengths, see: Allen et al. (1987 ▶). For the literature method used for preparation, see: Liu et al. (2011 ▶).

Experimental

Crystal data

C20H17N3O2S2

M = 395.49

Monoclinic,

a = 12.813 (3) Å

b = 16.453 (3) Å

c = 8.9470 (18) Å

β = 97.68 (3)°

V = 1869.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.914, T max = 0.970

3625 measured reflections

3391 independent reflections

2202 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.149

S = 1.08

3391 reflections

244 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.68 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029959/bq2369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029959/bq2369Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029959/bq2369Isup3.cml

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

C20H17N3O2S2	F(000) = 824
Mr = 395.49	Dx = 1.405 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.813 (3) Å	θ = 9–13°
b = 16.453 (3) Å	µ = 0.31 mm−1
c = 8.9470 (18) Å	T = 293 K
β = 97.68 (3)°	Needle, yellow
V = 1869.2 (7) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.3°, θmin = 1.6°
ω/2θ scans	h = −15→15
Absorption correction: ψ scan (North et al., 1968)	k = −19→0
Tmin = 0.914, Tmax = 0.970	l = 0→10
3625 measured reflections	3 standard reflections every 200 reflections
3391 independent reflections	intensity decay: 1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0324P)2 + 2.7384P] where P = (Fo2 + 2Fc2)/3
3391 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.65 e Å−3
2 restraints	Δρmin = −0.68 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
S1	0.53480 (10)	0.88849 (7)	0.53157 (15)	0.0611 (4)
S2	0.62593 (11)	0.72831 (9)	0.50196 (19)	0.0775 (5)
O1	0.3356 (3)	0.6778 (2)	0.7213 (4)	0.0675 (10)
O2	0.4300 (2)	0.53904 (17)	0.6832 (3)	0.0519 (8)
N1	0.4433 (3)	0.7614 (2)	0.6153 (4)	0.0431 (8)
N2	0.3178 (3)	0.5311 (2)	0.4521 (4)	0.0476 (9)
N3	0.2289 (3)	0.4864 (2)	0.4065 (4)	0.0434 (8)
C1	0.4111 (4)	0.9057 (3)	0.5959 (6)	0.0849 (18)
H1A	0.4193	0.9439	0.6792	0.102*
H1B	0.3617	0.9284	0.5152	0.102*
C2	0.3715 (4)	0.8282 (3)	0.6449 (5)	0.0704 (15)
H2B	0.3019	0.8180	0.5913	0.084*
H2C	0.3660	0.8305	0.7519	0.084*
C3	0.5321 (3)	0.7847 (3)	0.5549 (4)	0.0445 (10)
C4	0.4130 (3)	0.6833 (3)	0.6580 (5)	0.0462 (11)
C5	0.4775 (3)	0.6096 (2)	0.6282 (5)	0.0478 (11)
H5A	0.4802	0.6042	0.5208	0.057*
H5B	0.5489	0.6155	0.6787	0.057*
C6	0.3442 (3)	0.5100 (2)	0.5956 (5)	0.0423 (10)
C7	0.2761 (3)	0.4523 (2)	0.6429 (5)	0.0426 (10)
H7A	0.2798	0.4285	0.7378	0.051*
C8	0.2024 (3)	0.4379 (2)	0.5198 (4)	0.0384 (9)
C9	0.1076 (3)	0.3868 (2)	0.5110 (4)	0.0405 (10)
C10	0.1077 (4)	0.3190 (3)	0.6039 (5)	0.0530 (12)
H10A	0.1695	0.3037	0.6639	0.064*
C11	0.0169 (4)	0.2743 (3)	0.6081 (6)	0.0685 (15)
H11A	0.0176	0.2294	0.6713	0.082*
C12	−0.0750 (4)	0.2962 (3)	0.5185 (7)	0.0693 (15)
H12A	−0.1360	0.2660	0.5213	0.083*
C13	−0.0762 (4)	0.3624 (3)	0.4254 (6)	0.0597 (13)
H13A	−0.1381	0.3770	0.3648	0.072*
C14	0.0137 (3)	0.4070 (3)	0.4214 (5)	0.0492 (11)
H14A	0.0120	0.4518	0.3576	0.059*
C15	0.1921 (3)	0.4838 (3)	0.2477 (4)	0.0418 (10)
C16	0.1999 (4)	0.4125 (3)	0.1711 (5)	0.0528 (12)
H16A	0.2262	0.3659	0.2217	0.063*
C17	0.1679 (4)	0.4109 (3)	0.0157 (5)	0.0610 (13)
H17A	0.1717	0.3629	−0.0382	0.073*
C18	0.1307 (4)	0.4805 (4)	−0.0572 (5)	0.0628 (14)
H18A	0.1095	0.4795	−0.1608	0.075*
C19	0.1246 (4)	0.5515 (3)	0.0212 (5)	0.0593 (13)
H19A	0.1000	0.5985	−0.0295	0.071*
C20	0.1549 (3)	0.5535 (3)	0.1751 (5)	0.0519 (11)
H20A	0.1502	0.6015	0.2288	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0605 (8)	0.0463 (7)	0.0763 (9)	−0.0077 (6)	0.0087 (6)	0.0054 (7)
S2	0.0616 (8)	0.0618 (9)	0.1185 (13)	0.0057 (7)	0.0472 (8)	0.0103 (9)
O1	0.055 (2)	0.063 (2)	0.090 (3)	−0.0044 (17)	0.0316 (19)	0.0053 (19)
O2	0.0529 (18)	0.0451 (17)	0.0544 (19)	−0.0096 (14)	−0.0054 (15)	0.0072 (15)
N1	0.0407 (19)	0.042 (2)	0.048 (2)	0.0003 (16)	0.0080 (16)	−0.0015 (17)
N2	0.048 (2)	0.050 (2)	0.044 (2)	−0.0088 (18)	0.0075 (17)	0.0045 (18)
N3	0.046 (2)	0.048 (2)	0.0357 (19)	−0.0114 (17)	0.0056 (16)	0.0052 (16)
C1	0.077 (4)	0.053 (3)	0.130 (5)	0.006 (3)	0.037 (4)	0.001 (3)
C2	0.067 (3)	0.050 (3)	0.099 (4)	0.009 (3)	0.031 (3)	−0.008 (3)
C3	0.043 (2)	0.048 (3)	0.041 (2)	−0.003 (2)	0.0004 (19)	0.001 (2)
C4	0.041 (2)	0.049 (3)	0.048 (3)	−0.006 (2)	0.004 (2)	−0.001 (2)
C5	0.043 (2)	0.040 (2)	0.060 (3)	−0.007 (2)	0.004 (2)	0.000 (2)
C6	0.044 (2)	0.034 (2)	0.049 (3)	0.0006 (19)	0.005 (2)	0.000 (2)
C7	0.050 (3)	0.042 (2)	0.037 (2)	−0.001 (2)	0.007 (2)	0.0033 (19)
C8	0.042 (2)	0.037 (2)	0.039 (2)	0.0023 (18)	0.0122 (19)	0.0011 (18)
C9	0.045 (2)	0.041 (2)	0.038 (2)	−0.0004 (19)	0.0165 (19)	−0.005 (2)
C10	0.055 (3)	0.047 (3)	0.059 (3)	−0.001 (2)	0.015 (2)	0.006 (2)
C11	0.078 (4)	0.050 (3)	0.084 (4)	−0.009 (3)	0.034 (3)	0.012 (3)
C12	0.055 (3)	0.061 (3)	0.096 (4)	−0.017 (3)	0.027 (3)	−0.010 (3)
C13	0.051 (3)	0.062 (3)	0.068 (3)	−0.004 (2)	0.013 (2)	−0.012 (3)
C14	0.050 (3)	0.048 (3)	0.052 (3)	−0.002 (2)	0.017 (2)	−0.004 (2)
C15	0.043 (2)	0.050 (3)	0.033 (2)	−0.006 (2)	0.0097 (18)	0.003 (2)
C16	0.061 (3)	0.056 (3)	0.043 (3)	0.005 (2)	0.012 (2)	0.007 (2)
C17	0.064 (3)	0.075 (4)	0.044 (3)	0.004 (3)	0.010 (2)	−0.010 (3)
C18	0.053 (3)	0.099 (4)	0.037 (3)	0.005 (3)	0.006 (2)	0.008 (3)
C19	0.058 (3)	0.072 (3)	0.049 (3)	0.009 (3)	0.011 (2)	0.022 (3)
C20	0.056 (3)	0.052 (3)	0.050 (3)	0.002 (2)	0.015 (2)	0.004 (2)

S1—C3	1.721 (4)	C8—C9	1.470 (5)
S1—C1	1.779 (5)	C9—C10	1.391 (6)
S2—C3	1.639 (4)	C9—C14	1.395 (6)
O1—C4	1.209 (5)	C10—C11	1.382 (6)
O2—C6	1.349 (5)	C10—H10A	0.9300
O2—C5	1.428 (5)	C11—C12	1.380 (7)
N1—C3	1.378 (5)	C11—H11A	0.9300
N1—C4	1.409 (5)	C12—C13	1.369 (7)
N1—C2	1.479 (5)	C12—H12A	0.9300
N2—C6	1.330 (5)	C13—C14	1.371 (6)
N2—N3	1.371 (4)	C13—H13A	0.9300
N3—C8	1.369 (5)	C14—H14A	0.9300
N3—C15	1.437 (5)	C15—C16	1.369 (6)
C1—C2	1.461 (7)	C15—C20	1.372 (6)
C1—H1A	0.9700	C16—C17	1.397 (6)
C1—H1B	0.9700	C16—H16A	0.9300
C2—H2B	0.9700	C17—C18	1.371 (7)
C2—H2C	0.9700	C17—H17A	0.9300
C4—C5	1.513 (6)	C18—C19	1.371 (7)
C5—H5A	0.9700	C18—H18A	0.9300
C5—H5B	0.9700	C19—C20	1.380 (6)
C6—C7	1.393 (5)	C19—H19A	0.9300
C7—C8	1.372 (6)	C20—H20A	0.9300
C7—H7A	0.9300
C3—S1—C1	94.9 (2)	N3—C8—C7	106.4 (3)
C6—O2—C5	116.1 (3)	N3—C8—C9	125.4 (4)
C3—N1—C4	129.3 (4)	C7—C8—C9	128.1 (4)
C3—N1—C2	115.3 (4)	C10—C9—C14	117.8 (4)
C4—N1—C2	115.4 (3)	C10—C9—C8	119.4 (4)
C6—N2—N3	103.9 (3)	C14—C9—C8	122.5 (4)
C8—N3—N2	111.8 (3)	C11—C10—C9	120.6 (5)
C8—N3—C15	129.3 (3)	C11—C10—H10A	119.7
N2—N3—C15	117.4 (3)	C9—C10—H10A	119.7
C2—C1—S1	108.6 (4)	C12—C11—C10	120.1 (5)
C2—C1—H1A	110.0	C12—C11—H11A	120.0
S1—C1—H1A	110.0	C10—C11—H11A	120.0
C2—C1—H1B	110.0	C13—C12—C11	120.0 (5)
S1—C1—H1B	110.0	C13—C12—H12A	120.0
H1A—C1—H1B	108.4	C11—C12—H12A	120.0
C1—C2—N1	110.2 (4)	C12—C13—C14	120.0 (5)
C1—C2—H2B	109.6	C12—C13—H13A	120.0
N1—C2—H2B	109.6	C14—C13—H13A	120.0
C1—C2—H2C	109.6	C13—C14—C9	121.4 (4)
N1—C2—H2C	109.6	C13—C14—H14A	119.3
H2B—C2—H2C	108.1	C9—C14—H14A	119.3
N1—C3—S2	129.2 (3)	C16—C15—C20	121.6 (4)
N1—C3—S1	110.9 (3)	C16—C15—N3	118.9 (4)
S2—C3—S1	120.0 (3)	C20—C15—N3	119.4 (4)
O1—C4—N1	117.9 (4)	C15—C16—C17	118.8 (4)
O1—C4—C5	121.6 (4)	C15—C16—H16A	120.6
N1—C4—C5	120.4 (4)	C17—C16—H16A	120.6
O2—C5—C4	108.8 (3)	C18—C17—C16	119.7 (5)
O2—C5—H5A	109.9	C18—C17—H17A	120.1
C4—C5—H5A	109.9	C16—C17—H17A	120.1
O2—C5—H5B	109.9	C19—C18—C17	120.5 (4)
C4—C5—H5B	109.9	C19—C18—H18A	119.7
H5A—C5—H5B	108.3	C17—C18—H18A	119.7
N2—C6—O2	123.4 (4)	C18—C19—C20	120.3 (5)
N2—C6—C7	112.5 (4)	C18—C19—H19A	119.9
O2—C6—C7	124.1 (4)	C20—C19—H19A	119.9
C8—C7—C6	105.4 (4)	C15—C20—C19	119.1 (5)
C8—C7—H7A	127.3	C15—C20—H20A	120.5
C6—C7—H7A	127.3	C19—C20—H20A	120.5
C6—N2—N3—C8	−0.9 (4)	C15—N3—C8—C9	−18.9 (6)
C6—N2—N3—C15	−168.3 (4)	C6—C7—C8—N3	0.0 (4)
C3—S1—C1—C2	3.6 (2)	C6—C7—C8—C9	−174.8 (4)
S1—C1—C2—N1	−3.8 (3)	N3—C8—C9—C10	155.4 (4)
C3—N1—C2—C1	2.3 (4)	C7—C8—C9—C10	−30.7 (6)
C4—N1—C2—C1	−179.9 (3)	N3—C8—C9—C14	−29.9 (6)
C4—N1—C3—S2	5.1 (6)	C7—C8—C9—C14	144.0 (4)
C2—N1—C3—S2	−177.5 (3)	C14—C9—C10—C11	−0.9 (6)
C4—N1—C3—S1	−177.0 (3)	C8—C9—C10—C11	174.0 (4)
C2—N1—C3—S1	0.4 (3)	C9—C10—C11—C12	0.6 (7)
C1—S1—C3—N1	−2.3 (3)	C10—C11—C12—C13	−0.1 (8)
C1—S1—C3—S2	175.8 (3)	C11—C12—C13—C14	−0.2 (8)
C3—N1—C4—O1	173.6 (4)	C12—C13—C14—C9	−0.1 (7)
C2—N1—C4—O1	−3.8 (5)	C10—C9—C14—C13	0.7 (6)
C3—N1—C4—C5	−4.9 (6)	C8—C9—C14—C13	−174.1 (4)
C2—N1—C4—C5	177.7 (4)	C8—N3—C15—C16	−54.4 (6)
C6—O2—C5—C4	77.9 (4)	N2—N3—C15—C16	110.5 (4)
O1—C4—C5—O2	1.1 (6)	C8—N3—C15—C20	128.9 (5)
N1—C4—C5—O2	179.6 (3)	N2—N3—C15—C20	−66.3 (5)
N3—N2—C6—O2	178.4 (4)	C20—C15—C16—C17	−0.9 (7)
N3—N2—C6—C7	0.9 (5)	N3—C15—C16—C17	−177.5 (4)
C5—O2—C6—N2	15.6 (6)	C15—C16—C17—C18	0.9 (7)
C5—O2—C6—C7	−167.1 (4)	C16—C17—C18—C19	−0.1 (7)
N2—C6—C7—C8	−0.6 (5)	C17—C18—C19—C20	−0.7 (7)
O2—C6—C7—C8	−178.1 (4)	C16—C15—C20—C19	0.1 (7)
N2—N3—C8—C7	0.5 (4)	N3—C15—C20—C19	176.7 (4)
C15—N3—C8—C7	166.1 (4)	C18—C19—C20—C15	0.7 (7)
N2—N3—C8—C9	175.6 (4)