Home Crystal structure of N-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ6-sulfanylidene)cyanamide, C10H10F3N3OS
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Crystal structure of N-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ6-sulfanylidene)cyanamide, C10H10F3N3OS

  • Xu Ning , Yun-Lian Shi , Xu-Gen Shi , Wen-Li Yang EMAIL logo and Da-Yong Peng ORCID logo EMAIL logo
Published/Copyright: March 18, 2020

Abstract

[C10H10F3N3OS], monoclinic, P21/c (no. 14), a = 18.555(10) Å, b = 6.785(4) Å, c = 10.139(5) Å, β = 105.86°, V = 1227.9(11) Å3, Z = 4, Rgt(F) = 0.0571, wRref(F2) = 0.1785, T = 296(2) K.

CCDC no.: 1986677

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.17 × 0.15 × 0.13 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.29 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:8810, 2281, 0.031
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1978
N(param)refined:165
Programs:Bruker [1], SHELX [2]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C10.36996(17)1.0306(5)1.0228(3)0.0536(8)
C20.37549(19)0.8294(5)1.0327(4)0.0626(9)
H20.41600.77051.09520.075*
C30.32012(18)0.7159(5)0.9486(4)0.0556(8)
H30.32250.57910.95320.067*
C40.26132(16)0.8091(4)0.8577(3)0.0420(7)
C50.26111(18)1.0135(5)0.8571(3)0.0547(8)
H50.22121.07680.79610.066*
C60.19847(16)0.7000(4)0.7587(3)0.0410(6)
H60.17920.78730.68000.049*
C70.22099(19)0.5094(5)0.7032(4)0.0531(8)
H7A0.25690.53680.65310.080*
H7B0.17750.44850.64330.080*
H7C0.24280.42200.77790.080*
C80.4264(2)1.1649(7)1.1121(5)0.0740(11)
C90.10955(16)0.4215(4)1.0105(3)0.0443(7)
C100.04478(17)0.6009(5)0.7066(3)0.0500(7)
H10A0.00230.58850.74270.075*
H10B0.05370.47750.66750.075*
H10C0.03510.70110.63720.075*
N10.31390(16)1.1252(4)0.9374(3)0.0572(7)
N20.15227(15)0.4864(4)0.9348(3)0.0554(7)
N30.07752(19)0.3587(5)1.0833(3)0.0650(8)
O10.10801(12)0.8458(3)0.9005(2)0.0521(6)
S10.12346(4)0.66558(10)0.83841(7)0.0377(3)
F10.4836(2)1.0772(6)1.1837(6)0.202(3)
F20.4536(2)1.2948(6)1.0421(4)0.1454(15)
F30.3980(2)1.2778(8)1.1862(5)0.167(2)

Source of material

The synthesis process of the title compound was carried out using (Z)-N-(methyl(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-λ4-sulfanylidene)cyanamide for start material, using an oxidation reaction [3], [4], [5], [6]. A solution of (Z)-N-(methyl(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-sulfanylidene)cyanamide (5.75 g, 22 mmol) in acetonitrile (50 mL) was cooled in an ice bath at 5 °C. To the well stirred solution was added (8.0 g, 22 mmol) of a 40% aqueous solution of NaMnO4 over 0.5 h. During the addition the reaction temperature increased to about 20 °C. The resulting brown reaction slurry was allowed to stir for about 0.5 h and then cooled to about 5 °C. A 30% aqueous solution of sodium metabisulfite (29.8 g, 47 mmol) was added to the vigorously stired reaction mixture in one portion. The temperature increased by 15 to 20 °C during the course of the addition, and then the reaction mixture slurry thickened. Additional acetonitrile (15 mL) and water (15 mL) were added to facilitate mixing. The collected grey solids were rinsed with acetonitrile (15 mL). The combined filtrate and wash was transferred to a separatory funnel. The lower aqueous phase was removed. The organic phase was concentrated in vacuo; the residue was purified by column chromatography (ethyl acetate/hexane = 1/1) to give the title compound (5.2 g), Yield 83.38%. The product was recrystallized from isopropyl alcohol. m.p. 139 °C–141 °C. Elemental Anal. Calcd. (%) for C10H10F3N3OS: C, 43.32; H, 3.64; N, 15.16; Found(%): C, 41.96; H, 3.87; N, 14.68.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.93 Å with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

Comment

Sulfoxaflor a new insecticide from Dow Agrosciences was sold for the first time in 2012, and the first product from this new class (the sulfoximines) of insect control agents, exhibits broad-spectrum efficacy against many sap-feeding insect pests, including aphids, white flies, hoppers, and lygus, with levels of activity that are comparable to those of other classes of insecticides [7], [8], [9], [10]. Herein we report the crystal structure of Sulfoxaflor. The crystal structure may lead to a better understanding of mechanisms, which makes this kind of compound better understood and paves the way for the development of more novel sulfoximine compounds.

In the molecule of the title compound, bond lengths and angles are very similar to those given in the literature [11], [12], [13]. The molecular conformation is characterized by the C5—C4—C6—C7, C5—C4—C6—S1, C4—C6—S1—C8, and C4—C6—S1—N2 torsion angles of −144.8°, 88.2°, −164.6°, and 79.5°, respectively.

Award Identifier / Grant number: 21562022

Award Identifier / Grant number: 20181BAB203015

Funding statement: X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China. This research has been supported by The “13th Five-Year” National Key Research Program of China (2017YFD0301604), the National Natural Science Foundation of China (21562022), Science & Technology Transformation Program for Universities in Jiangxi Province (KJLD14095), The Natural Science Foundation of Jiangxi Province (Grant No. 20181BAB203015).

References

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Received: 2020-01-30
Accepted: 2020-02-27
Published Online: 2020-03-18
Published in Print: 2020-06-25

©2020 Xu Ning et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
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