Home Crystal structure of 1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C13H22F12N4P2
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Crystal structure of 1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C13H22F12N4P2

  • Xiong Wan-Ming , Zhou Long , Lv Shen-Ming , Nie Xu-Liang EMAIL logo , Chen Jing and Huang Chang-Gan EMAIL logo
Published/Copyright: May 22, 2018

Abstract

C13H22F12N4P2, monoclinic, P21/c, a = 12.9171(13) Å, b = 13.3953(13) Å, c = 12.5808(12) Å, β = 97.766(1)°, V = 2156.9(4) Å3, Z = 4,Rgt(F) = 0.0583, wRref(F2) = 0.1557, T = 296(2) K.

CCDC no.: 1841197

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.21 × 0.20 × 0.19 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.31 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:16239, 4010, 0.033
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2890
N(param)refined:338
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
N1−0.1664(2)0.2727(2)0.4032(2)0.0650(7)
N2−0.02379(19)0.28810(19)0.5099(2)0.0575(7)
N30.3493(2)0.4298(2)0.2098(2)0.0652(7)
N40.4863(2)0.5092(2)0.1792(2)0.0686(8)
P10.52608(7)0.20209(6)0.07292(7)0.0603(3)
P30.07664(8)0.51739(8)0.81503(8)0.0724(3)
F10.4346(2)0.2733(2)0.0285(3)0.1443(12)
F20.61817(18)0.13149(18)0.1215(2)0.0992(8)
F30.5080(2)0.2244(2)0.1927(2)0.1141(9)
F40.44853(19)0.11101(19)0.0688(2)0.1060(8)
F50.6052(2)0.2914(2)0.0786(2)0.1276(11)
F60.5471(2)0.1799(3)−0.04392(19)0.1306(11)
F7a0.1675(11)0.5845(8)0.8689(11)0.190(5)
F8a0.0986(13)0.4094(5)0.8066(12)0.189(5)
F9 a0.1122(9)0.4474(10)0.9202(10)0.152(4)
F10a−0.0404(5)0.4992(14)0.8311(12)0.173(6)
F11a0.1830(7)0.5365(10)0.7795(16)0.179(6)
F12a0.0365(11)0.5282(6)0.6908(5)0.134(4)
F7’b0.0548(10)0.6326(6)0.8133(8)0.132(4)
F8’b0.0027(13)0.4322(12)0.7749(6)0.165(6)
F9’b0.1056(12)0.5216(16)0.9296(7)0.192(6)
F10’b−0.0001(12)0.5584(13)0.8789(12)0.200(6)
F11’b0.1527(12)0.476(2)0.7517(12)0.272(11)
F12’b0.0396(11)0.590(3)0.733(3)0.337(14)
C1−0.0707(3)0.2384(2)0.4278(3)0.0645(8)
H1−0.0411810.1869150.3923400.077*
C2−0.1801(3)0.3470(3)0.4727(3)0.0782(10)
H2−0.2405100.3845540.4736940.094*
C3−0.0921(3)0.3568(3)0.5389(3)0.0747(10)
H3−0.0793580.4022780.5950400.090*
C4−0.2423(3)0.2406(4)0.3117(3)0.0999(14)
H4A−0.2481210.2910450.2570870.150*
H4B−0.3092080.2304000.3351900.150*
H4C−0.2190750.1792650.2832330.150*
C50.0838(3)0.2752(3)0.5611(3)0.0737(10)
H5A0.1058750.2071340.5501450.088*
H5B0.0868220.2858360.6377390.088*
C60.1583(3)0.3466(3)0.5171(3)0.0739(10)
H6A0.1293060.4134060.5166200.089*
H6B0.2238740.3470000.5649120.089*
C70.1801(3)0.3216(3)0.4062(3)0.0704(9)
H7A0.1142450.3175840.3591150.085*
H7B0.2128180.2564110.4074540.085*
C80.2501(3)0.3968(3)0.3602(3)0.0650(8)
H8A0.2130240.4595620.3476920.078*
H8B0.3116720.4086740.4118690.078*
C90.2822(4)0.3611(3)0.2589(4)0.0971(14)
H9A0.3188170.2981910.2722980.117*
H9B0.2200720.3484240.2083270.117*
C100.4486(3)0.4454(2)0.2431(3)0.0641(8)
H100.4864800.4157820.3029640.077*
C110.4081(4)0.5357(3)0.1021(3)0.0852(12)
H110.4128620.5804380.0464740.102*
C120.3230(4)0.4863(3)0.1200(3)0.0849(12)
H120.2575830.4895750.0789310.102*
C130.5941(4)0.5428(4)0.1882(4)0.1133(17)
H13A0.6328320.4992300.1475630.170*
H13B0.6244740.5417940.2621660.170*
H13C0.5961540.6095550.1608110.170*
  1. aOccupancies: a = 526(7), b = 0.474(7).

Source of materials

1-Methylimidazole (8.21 g, 0.1 mol) was dissolved in methylbenzene (20 mL), 1,5-dibromopentane (11.35 g, 0.05 mol) was quickly added under stirring. The mixture first reacted at 90 °C for 10 min, and then heated to 110 °C for 7–10 hours. After the reaction has completed (monitored by TLC), a white solid was produced. The resulting suspension was filtered, crushed and washed with hexane, ethylacetate and diethyl ether three times respectively. Then the intermediate (C5M—Br)(0.5 g, 0.00127 mol), potassium hexafluorophosphate (0.6 g, 0.0029 mol) was dissolved in deionized water (20 mL). The mixture stirred well for 12 h at 85 °C and then cooled slowly. Colorless crystals were produced and filtered. They were washed with deionized water many times until silver bromide precipitation occurs anymore. The product (0.1 g) was dissolved in ethanol: water (2:1) solution and (7 mL), then the mixture reacted in the microwave synthesizer at 100 °C for 2 min. Crystals suitable for X-ray analysis were obtained after cooled slowly.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.93–0.97 Å with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms. There is a disorder of one of the two hexafluorophosphate anions (cf. the figure).

Discussion

Ionic liquid, as a new type of environmentally friendly solvent and liquid acid base catalyst, owing to the advantages of adjustable structure, high catalytic efficiency, mild conditions, and can be recycled, etc, has been widely used in catalytic science, electrochemistry, environmental science, extraction and separation, biomass energy, resource conversion and other fields [3], [4], [5]. Because of the unique physical and chemical properties of ionic liquids, ionic liquids have the unique potential advantages of biodiesel preparation. In recent years, various functional ionic liquids have been synthesised, and have been used to prepare biodiesel highly efficiently and environmental friendly [6], [7]. It was found that dinuclear alkaline ionic liquid bis-(3-methyl-1-imidazolium-)-ethlyene dihydroxide([MC2]OH) shows excellent catalytic efficiency, the highest conversion rate of cotton seed oil was up to 98.5%, and the stability of and separation effect of the catalyst was very ideal [8].

Recently, our group still focused on the preparation of biodiesel catalyzed by ionic liquid [9], [10] and reported two crystal structures of 1,1′-butanebis(3-methyl-1H-imidazol-3-ium),bis(hexafluorophosphate) and 1,1′-(hexane-1,6-diyl)bis(3-methyl-1H-imidazol-3-ium), bis(hexafluorophosphate) [11], [12]. In order to find the ionic liquid catalyst with better catalytic efficiency, we were engaged in synthesising the novel ionic liquid catalyst with imidazole. Herein, we report the synthesis and structure of the bisimidazoles ionic liquid. Bond lengths and angles within the imidazole ring are very similar to those given in the literature for diimidazole ionic liquid [13]. The title structure consists of one C5M2+ cation(1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)), and two PF6 anions (cf. the figure). Two cationic 1-ethylimidazolium rings were bound to the both sides of pentyl group. The two imidazole rings are almost crystallographically dependent planar and the dihedral angle of two imidazole rings is 89.207°.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 31760193, 31760068) and the Research Foundation of Educational Department of Jiangxi Province[GJJ160382, 160408]. X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China.

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Received: 2018-01-20
Accepted: 2018-05-03
Published Online: 2018-05-22
Published in Print: 2018-07-26

©2018 Xiong Wan-Ming et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  64. Crystal structure of (Z)-N-(4-nitrophenyl)-3-phenyl-3-(phenylamino)acrylamide, C21H17N3O3
  65. Crystal structure of 1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C13H22F12N4P2
  66. Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(μ2-phthalato-κ2O:O′)cobalt(II)], C26H24CoN2O10
  67. Crystal structure of methyl (R)-4-(o-chlorobenzoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylate, C17H20ClNO3S
  68. Crystal structure of 2-[[4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]phenyl] methyl]-1H-isoindole-1,3(2H)-dione, C28H29N3O3
  69. The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C21H19NO8S
  70. Crystal structure of semiconducting potassium poly[(μ2-tetraselenido-κ2Se1:Se4)(μ2-pentaselenido-κ1Se1:Se1)argentate(I)], K3AgSe9
  71. Crystal structure of 2-isopropyl-8-methyl-phenanthrene-3,4-dione, C18H16O2
  72. Crystal structure of 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione, C19H22O2
  73. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4-bromophenol, C14H13BrN2O
  74. Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2
  75. Crystal structure of bis(hydroxylamido-κ2O,N)-oxido(1H-pyrazole-3-carboxylato-κ2O,N)vanadium(V), C4H7N4O5V
  76. The crystal structure of In1.2B3O5.6(OH)1.4
  77. The crystal structure of chlorido(2-(1H-pyrazol-3-yl)phenolato-κ2N,O)(2-(1H-pyrazol-3-yl)phenol-κN)copper(II), C18H15ClCuN4O2
  78. Crystal structure of 1-heptylpyridazin-1-ium iodide, C11H19N2I
  79. The crystal structure of N-butylpyridinium bis(μ2-dichlorido)-tetrachloridodicopper(II), C18H28N2Cu2Cl6
  80. Crystal structure of 6-hydroxy-5-((2-hydroxy-6-oxocyclohex-1-en-1-yl)(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, C20H22N2O6
  81. Crystal structure of bis(acetonitrile)-diaqua-dichloridoiron(II), C4H10Cl2N2O2Fe
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