2-(1,5-Diphenyl-1H-pyrazol-3-yl­oxy)-1-(2-sulfanyl­idene-1,3-thia­zolidin-3-yl)­ethanone

Li, Y.; Liu, Y.-Y.; Xiong, X.-H.; Wei, P.

doi:10.1107/S1600536812029959

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2419

https://doi.org/10.1107/S1600536812029959

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2-(1,5-Diphenyl-1H-pyrazol-3-yloxy)-1-(2-sulfanylidene-1,3-thiazolidin-3-yl)ethanone

Yi Li,^a ^* Yuan-Yuan Liu,^b Xiao-Hui Xiong ^c and Ping Wei ^a

^aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, ^bDepartment of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, People's Republic of China, and ^cCollege of Food Science and Light Industry, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: liynj2012@gmail.com

(Received 25 June 2012; accepted 1 July 2012; online 10 July 2012)

The title compound, C₂₀H₁₇N₃O₂S₂, was synthesized by the reaction of 2-(1,5-diphenyl-1H-pyrazol-3-yloxy)acetic acid and thiazolidine-2-thione. The C-linked benzene ring, N-linked benzene ring and thiazolidine-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_r = 395.49
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.149
S = 1.08
3391 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029959/bq2369sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029959/bq2369Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029959/bq2369Isup3.cml

checkCIF report

Comment top

Since the discovery of the strobilurin fungicide pyraclostrobin by BASF scientists, 1H-pyrazol-3-oxy derivatives have attracted considerable attention in chemical and medicinal research due to their low mammalian toxicity and diverse bioactivities such as fungicidal (Aly, 2009), insecticidal (Meegalla et al., 2004) and herbicidal (Morimoto et al., 1990) activities. However, very few representatives of biologically active 2-(1,5-diaryl-1H-pyrazol-3-yloxy)-1-(2-thioxothiazolidin-3-yl)ethanone derivatives have hitherto been described in the literature. We report here the crystal structure of the title compound, (I).

In the molecule of (I), (Fig.1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The bond length of N1—C4 (1.409 (5) Å) is longer than normal N—C amide bond (1.325–1.352 Å) (Goodman et al., 1971). The C-linked benzene ring A (C9—C14), N-linked benzene ring B (C15—C20), and thiazolidine-2-thione ring (N1/S1/C1—C3) are twisted 31.33 °, 62.87 °, and 82.71 ° from the plane of the bridge 1H-pyrazol ring (N2/N3/C6—C8), respectively. Rings A and B are, of course, planar and the dihedral angle between them is 72.16 °.

Related literature top

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 top

The title compound, (I) was prepared by the literature method (Liu et al., 2011). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in ethyl acetate (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Structure description top

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).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

2-(1,5-Diphenyl-1H-pyrazol-3-yloxy)-1-(2-sulfanylidene-1,3- thiazolidin-3-yl)ethanone top

Crystal data top

C₂₀H₁₇N₃O₂S₂	F(000) = 824
M_r = 395.49	D_x = 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

Data collection top

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

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0324P)² + 2.7384P] where P = (F_o² + 2F_c²)/3
3391 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.65 e Å⁻³
2 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₂₀H₁₇N₃O₂S₂	V = 1869.2 (7) Å³
M_r = 395.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.813 (3) Å	µ = 0.31 mm⁻¹
b = 16.453 (3) Å	T = 293 K
c = 8.9470 (18) Å	0.30 × 0.20 × 0.10 mm
β = 97.68 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2202 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.024
T_min = 0.914, T_max = 0.970	3 standard reflections every 200 reflections
3625 measured reflections	intensity decay: 1%
3391 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	2 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.08	Δρ_max = 0.65 e Å⁻³
3391 reflections	Δρ_min = −0.68 e Å⁻³
244 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃O₂S₂
M_r	395.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.813 (3), 16.453 (3), 8.9470 (18)
β (°)	97.68 (3)
V (Å³)	1869.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.914, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	3625, 3391, 2202
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.149, 1.08
No. of reflections	3391
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.68

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Center of Test and Analysis, Nanjing University, for support.

References

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