Home Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-vinyl-1H-imidazol-3-ium hexafluoridophosphate(V), C9H13F6N2O2P
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Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-vinyl-1H-imidazol-3-ium hexafluoridophosphate(V), C9H13F6N2O2P

  • Wan-Ming Xiong , Ting Huang , Sheng Liao , Jing Chen and Xu-Liang Nie ORCID logo EMAIL logo
Published/Copyright: June 18, 2020

Abstract

[C9H13F6N2O2P], monoclinic, P21/c (no. 14), a = 6.5994(13) Å, b = 10.754(2) Å, c = 19.754(4) Å, β = 96.267(2)°, V = 1393.6(5) Å3, Z = 4, Rgt(F) = 0.0674, wRref(F2) = 0.2124, T = 296(2) K.

CCDC no.: 1995297

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:Colorless block
Size:0.17 × 0.15 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.27 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:10447, 2581, 0.024
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1975
N(param)refined:182
Programs:Bruker [1], SHELX [2], Diamond [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.4641(5)0.4161(3)0.32926(18)0.0576(9)
H10.53840.40840.29210.069*
C20.2287(6)0.4694(4)0.39382(19)0.0668(10)
H20.11290.50540.40840.080*
C30.3647(7)0.3977(4)0.43031(19)0.0731(11)
H30.36010.37400.47540.088*
C40.1975(5)0.5525(3)0.27341(17)0.0562(8)
H4A0.28820.55750.23810.067*
H4B0.17390.63630.28890.067*
C5−0.0020(5)0.4963(3)0.24428(16)0.0535(8)
C6−0.2553(7)0.5105(5)0.1514(2)0.0871(14)
H6A−0.36700.55430.16890.104*
H6B−0.27300.42210.15840.104*
C7−0.2523(9)0.5372(6)0.0789(2)0.1058(18)
H7A−0.24480.62540.07230.159*
H7B−0.37450.50560.05400.159*
H7C−0.13580.49800.06290.159*
C80.6983(7)0.2944(5)0.4067(3)0.0912(14)
H80.78570.28320.37340.109*
C90.7454(11)0.2487(7)0.4635(4)0.135(3)
H9A0.66010.25880.49760.162*
H9B0.86610.20410.47220.162*
N10.2942(4)0.4796(3)0.33003(13)0.0518(7)
N20.5126(5)0.3648(3)0.38984(16)0.0654(8)
O1−0.0914(4)0.4150(3)0.27039(12)0.0670(7)
O2−0.0610(4)0.5519(3)0.18650(12)0.0658(7)
F10.3214(5)0.3723(3)0.16320(19)0.1172(12)
F20.2410(5)0.1083(3)0.0975(2)0.1219(12)
F30.3295(7)0.1731(4)0.20014(16)0.1454(15)
F40.0493(4)0.2525(3)0.1422(2)0.1179(12)
F50.5079(4)0.2277(3)0.11570(19)0.1144(11)
F60.2335(6)0.3031(4)0.05893(16)0.1362(14)
P10.27887(15)0.24236(9)0.12951(5)0.0555(4)

Source of material

To a stirred solution of l-vinylimidazole (2.0 g, 1.95 mL) in THF (50 mL) at −5 °C under a nitrogen atmosphere was added dropwise ethyl bromoacetate (7.84 g, 5.21 mL). The mixture was stirred vigorously at −5 °C for 1 h, then at room temperature for 3 h. After the reaction has been completed (monitored by TLC), the THF top phase was decanted and the product was washed with ethyl acetate and diethyl ether 3 times respectively. Then residual solvent was removed, and the product was dried in vacuo at 60 °C for 1 h to give a white powder solid in 96% yield. The intermediate (3-(2-ethoxy-2-oxoethyl)-1-vinyl-H-imidazol-3-ium bromide) (1 g, 3.8 mmol) and KPF6 (0.70 g, 3.8 mmol) were dissolved in water (40 mL). The mixture stirred for 6 h at 80 °C and then cooled slowly. The crystals of the title compound were obtained in 64.2% yield.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms.

Comment

Ionic liquids (ILs) are organic salts usually consisting of an organic cation and an inorganic or organic anion. ILs have negligible vapour pressure, high thermal stability, a large electrochemical window and high solvent power, and can be easily recycled [4]. These properties offer a potential implementation of ILs in industrial processes, to decrease the environmental footprint [5]. Exciting applications of ionic liquids have been developed continuously [6], [7], [8], [9], [10]. A series of novel ionic liquids which possess thermoresponsive properties in organic or water [11], [12], and they provided a convenient way to reuse and avoid the leaching of catalysts from the solvents. Catalysts can achieve the catalytic process named as thermoregulated phase-separable catalysis with the characteristic of homogeneous reaction at higher temperature and phase-separation at lower temperature [13], [14]. In order to find the ionic liquid catalyst with better catalytic and recycled utilization efficiency, our group were engaged in synthesizing the novel thermoregulated ionic liquid of [RMIM] PF6 [15], [16], which are responsible for the thermomorphic properties of the ionic liquid in water or toluene.

In the title compound bond lengths and angles within 3-(2-ethoxy-2-oxoethyl)-1-vinyl-1H-imidazol-3-ium hexafluoridophosphate(V) are very similar to those given in the literature [17]. The atoms of imidazole ring are coplanar, and the dihedral angle of imidazole ring, the vinyl group and the carboxlate group C10-O1-O2 plane are 3.0(1)°, 64.3(3)° and 61.7(3)°, respectively. The torsion angles of C3-N2-C8-C9, C1-N1-C4-C5, N1-C4-C5-O2, C4-C5-O2-C6 and C5-O2-C6-C7 are 2.6(9)°, −112.1(4)°, −168.2(3)°, −178.9(3)° and −154.9(4)°, respectively.

Acknowledgements

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, China. This work was supported by the National Natural Science Foundation of China (no. 31760193) and the Key Research Foundation of Educational Department of Jiangxi Province of China [GJJ190181].

References

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Received: 2020-03-17
Accepted: 2020-04-07
Published Online: 2020-06-18
Published in Print: 2020-08-26

©2020 Wan-Ming Xiong et al., published by De Gruyter, Berlin/Boston

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

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  69. The crystal structure of (6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-10-(4-acetoxy-3-methylbutyl)-6a,8a,9-trimethyl-3,4,5,6,6a,6b,7,8,8a,8b,9,10,11a,12,12a,12b-hexadecahydro-1H-naphtho[2′,1′:4,5]indeno[2,1-b]furan-4-yl acetate, C31H48O5
  70. Crystal structure of 4,4′-(oxybis(methylene))bis(bromobenzene), C14H12Br2O
  71. Crystal structure of (N,N-dimethylsulphoxide)-[N-(3-ethoxy-2-(oxide)benzylidene)-3-methoxybenzenecarbohydrazonato-κ3N,O,O′]-dioxo-molybdenum(VI), C19H22MoN2O7S
  72. Crystal structure of dichlorido-bis(dimethyl sulphoxide-κO)-bis(4-methylbenzyl-κC1)tin(IV), C20H30Cl2O2S2Sn
  73. Crystal structure of (E)-2-amino-N′-(2-hydroxy-4-(2-(piperidin-1-yl)ethoxy)benzylidene)benzohydrazide monohydrate, C21H26N4O3 ⋅ H2O
  74. Crystal structure of chloridotris(4-chlorophenyl)(dimethyl sulfoxide-κO)tin(IV), C20H18Cl4OSSn
  75. Crystal structure of catena{di-aqua-sodium-[N-(hydroxyethyl), N-isopropyl-dithiocarbamato]}n, [C6H16NNaO2S2]n
  76. Crystal structure of 2,2,4,4,6,6-hexakis(4-chlorophenyl)-1,3,5,2,4,6-trithiatristanninane, C36H24Cl6S3Sn3
  77. Crystal structure of 6-methoxy-3-(5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-4H-chromen-4-one-methanol (1/1), C20H18N2O6
  78. Crystal structure of hexanedihydrazide, C6H14N4O2
  79. Crystal structure of tert-butyl 2-(hydroxymethyl)-5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1-carboxylate, C18H24N2O5
  80. Crystal structure of [(Z)-O-isopropyl N-(4-nitrophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuN2O3PS
  81. Crystal structure of [O-ethyl N-(4-nitrophenyl)thiocarbamato-κS](tri-4-tolylphosphine-κP)gold(I) tetrahydrofuran solvate, C30H30AuN2O3PS, C4H8O
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