Startseite Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate), C18H24F12N4P2
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Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate), C18H24F12N4P2

  • Wen Zhao , Xin-Ting Liu , Su-Qin Wu EMAIL logo , Wan-Ming Xiong und Xu-Liang Nie ORCID logo EMAIL logo
Veröffentlicht/Copyright: 28. Januar 2021

Abstract

C18H24F12N4P2, monoclinic, P21/n (no. 14), a = 8.3185(9) Å, b = 21.883(2) Å, c = 13.4345(15) Å, β = 103.4730(10)°, V = 2378.3(5) Å3, Z = 4, Rgt(F) = 0.0531, wRref(F2) = 0.1424, T = 296(2) K.

CCDC no.: 2056033

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
Size0.20 × 0.14 × 0.13 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.28 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.5°, 99 %
N(hkl)measured, N(hkl)unique, Rint:12957, 4654, 0.044
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2189
N(param)refined:454
Programs:Bruker [1], SHELX [2], [, 3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
C1−0.2587 (11)0.0640 (5)0.0084 (2)0.191 (3)
H1A−0.14720.0790−0.00810.287*
H1B−0.36530.1015−0.00630.287*
H1C−0.2841−0.00990.00710.287*
C2−0.2277 (8)0.0965 (4)0.05750 (19)0.1330 (19)
H2A−0.12080.05780.07230.160*
H2B−0.33920.07900.07420.160*
C3−0.0359 (6)0.2543 (4)0.08282 (13)0.0770 (11)
H30.06650.21760.09730.092*
C4−0.3035 (6)0.2891 (4)0.04575 (15)0.0909 (13)
H4−0.42230.28120.02960.109*
C5−0.2171 (6)0.3798 (4)0.05631 (14)0.0831 (12)
H5−0.26370.44650.04900.100*
C60.0991 (5)0.4301 (3)0.09713 (13)0.0759 (11)
H6A0.11120.48410.07330.091*
H6B0.21990.39370.10130.091*
C70.0581 (5)0.4814 (3)0.14343 (12)0.0589 (9)
C8−0.0909 (5)0.4497 (3)0.16896 (13)0.0669 (10)
H8−0.16830.39470.15780.080*
C9−0.1266 (5)0.4992 (3)0.21120 (14)0.0748 (11)
H9−0.22870.47760.22800.090*
C10−0.0134 (6)0.5793 (3)0.22832 (13)0.0749 (11)
H10−0.03760.61210.25670.090*
C110.1370 (5)0.6113 (3)0.20330 (13)0.0712 (10)
H110.21480.66560.21500.085*
C120.1736 (4)0.5630 (3)0.16064 (12)0.0619 (9)
C130.3395 (5)0.5978 (3)0.13295 (14)0.0861 (12)
H13A0.44300.54810.13850.103*
H13B0.30070.59650.09930.103*
C140.5630 (5)0.7254(3)0.17234 (14)0.0741 (11)
H140.64940.67710.18600.089*
C150.3200 (6)0.7932 (4)0.13238 (16)0.0922 (13)
H150.20750.80000.11340.111*
C160.4249 (7)0.8706 (4)0.15166 (17)0.0943 (13)
H160.39910.94190.14860.113*
C170.7331 (7)0.8837 (4)0.20233 (16)0.1075 (15)
H17A0.68500.94950.21400.129*
H17B0.77820.84240.22970.129*
C180.8873 (7)0.9050 (5)0.1748 (2)0.161 (3)
H18A0.84120.93590.14510.241*
H18B0.95290.84090.16880.241*
H18C0.97290.95280.19160.241*
N1−0.1893 (5)0.2108 (3)0.06249 (11)0.0823 (10)
N2−0.0468 (4)0.3561 (3)0.07993 (10)0.0682 (8)
N30.4082 (4)0.7021 (3)0.14572 (11)0.0729 (9)
N40.5761 (5)0.8274 (3)0.17660 (11)0.0771 (9)
P1a0.4597 (7)0.2120 (4)0.1793 (2)0.0593 (15)
P2a0.7963 (12)0.7189 (8)0.0430 (3)0.108 (3)
F1a0.5375 (13)0.2689 (8)0.2241 (3)0.121 (4)
F2a0.3941 (19)0.1501 (12)0.1348 (4)0.145 (5)
F3a0.6654 (14)0.1857 (15)0.1722 (6)0.120 (4)
F4a0.266 (2)0.2451 (13)0.1886 (6)0.178 (6)
F5a0.488 (2)0.3069 (10)0.1497 (5)0.126 (4)
F6a0.4387 (19)0.1105 (9)0.2069 (6)0.163 (6)
F7a0.9713 (13)0.7899 (10)0.0442 (4)0.148 (4)
F8a0.6270 (11)0.6403 (8)0.0423 (4)0.127 (4)
F9a0.9218 (18)0.6240 (9)0.0272 (5)0.146 (5)
F10a0.6697 (18)0.8043 (8)0.0610 (4)0.136 (4)
F11a0.7517 (14)0.7496 (11)−0.0088 (3)0.129 (6)
F12a0.8503 (19)0.6903 (10)0.0958 (4)0.129 (4)
P3b0.7935 (7)0.7147 (6)0.04360 (18)0.051 (2)
F13b0.786 (2)0.7824 (12)−0.0036 (5)0.138 (7)
F14b0.722 (2)0.6223 (6)0.0103 (4)0.137 (5)
F15b0.786 (2)0.6421 (13)0.0889 (5)0.144 (7)
F16b0.866 (3)0.8113 (9)0.0731 (5)0.175 (6)
F17b1.0006 (16)0.6802 (16)0.0354 (5)0.150 (7)
F18b0.5795 (13)0.7496 (16)0.0481 (4)0.147 (7)
P4b0.4495 (15)0.2036 (10)0.1771 (4)0.124 (4)
F19b0.2389 (17)0.2502 (9)0.1871 (4)0.084 (3)
F1Ab0.459 (3)0.2895 (17)0.1347 (7)0.172 (10)
F1Bb0.649 (2)0.1511 (18)0.1656 (8)0.156 (9)
F1Cb0.4338 (16)0.1244 (13)0.2212 (5)0.119 (5)
F1Db0.548 (2)0.2884 (13)0.2137 (7)0.190 (9)
F1Eb0.335 (2)0.1257 (13)0.1395 (6)0.163 (8)
  1. aOccupancy: 0.558(12).

    bOccupancy: 0.442(12).

Source of material

To a stirred solution of 1-ethylimidazole (1.92 g, 0.02 mol) in acetonitrile (25 mL) at 75 °C was added dropwise α,α′-dibromo-o-xylene (2.64 g, 0.01 mol). The mixture was vigorously stirred at 75 °C for about 24 h. After the reaction has been completed (monitored by TLC), the acetonitrile 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 98.68% yield. The intermediate compound (1.14 g, 2.5 mmol) and KPF6 (0.92 g, 5 mmol) were dissolved in distilled water (25 mL). The mixture stirred for 6–8 h at 95 °C and then cooled slowly. The crystals of the target compound were obtained in 94.36% yield.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.90–0.97 Å with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.

Comment

Ionic liquids (ILs) generally refer to a class of low-melting compounds composed of adjustable organic cations and inorganic or organic anions, and have different functions [5], [, 6]. ILs as a new type of environmentally friendly solvent, owing high catalytic efficiency at mild conditions, and can be recycled, etc., has been widely used in catalytic science, extraction and separation, biomass energy, resource conversion and other fields [7], [8], [9]. It is worth mentioning that various functional ionic liquids have been used to produce biodiesel highly efficiently and environmental friendly [10], [11], [12]. Our group is still focusing on the preparation of ionic liquid that are able to catalyze the reaction to biodiesel [13], [, 14]. We have demonstrated that diimidazole-based hexafluorophosphate exhibits the temperature-controlled characteristics in methanol and water [15]. In order to find an ionic liquid to catalyze the reaction with better catalytic and recycled utilization efficiency, we were engaged in synthesizing the novel ionic liquid catalyst with imidazole.

In the cation of the title compound bond lengths and angles are very similar to those given in the literature [16]. The atoms of imidazole ring are coplanar, and the dihedral angle of two imidazole rings and the phenyl group are 6.9(1)°, 82.0(1)° and 84.0(1)°, respectively. The torsion angles of C1–C2–N1–C3, C7–C6–N2–C3, C12–C13–N3–C14 and C18–C17–N4–C14 are −120.4(4)°, −102.4(4)°, 103.7(4)° and 86.8(6)°, respectively.


Corresponding author: Su-Qin Wu, Department of Chemistry, Jiangxi Agricultural University, Nanchang330031, People’s Republic of China; and Xu-Liang Nie, Department of Chemistry, Key Laboratory of Chemical Utilization of Plant Resources of Nanchang, Jiangxi Agricultural University, Nanchang330031, People’s Republic of China, E-mail: (S.-Q. Wu), (X.-L. Nie)

Award Identifier / Grant number: 31760193

Funding source: Project of Science and Technology Department of Jiangxi Province

Award Identifier / Grant number: 20192ACB60011

Award Identifier / Grant number: 20202BABL205003

Funding source: Key Research Foundation of Educational Department of Jiangxi Province of China

Award Identifier / Grant number: GJJ200404

Award Identifier / Grant number: GJJ190181

Funding source: Natural Science Foundation of Jiangxi Agriculture University

Award Identifier / Grant number: 202010410027

Acknowledgements

X-ray data were collected at Instrumental Analysis Center Nanchang Hangkong University, Nanchang, 330063, People’s Republic of China

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: National Natural Science Foundation of China (No. 31760193), Project of Science and Technology Department of Jiangxi Province (20192ACB60011 and 20202BABL205003), the Key Research Foundation of Educational Department of Jiangxi Province of China (GJJ200404, GJJ190181) and Natural Science Foundation of Jiangxi Agriculture University (No. 202010410027).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-12-25
Accepted: 2021-01-14
Published Online: 2021-01-28
Published in Print: 2021-05-26

© 2021 Wen Zhao et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxidoethylidene)benzohydrazonato-κ5N,O,O′:N′,O′′)hexkis(pyridine-κ1N)trinickel(II) - pyridine (1/1), C63H57Cl2N13Ni3O6
  4. Crystal structure of [(μ2-succinato κ3O,O′:O′′)-bis-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane)]dinickel(II)] diperchlorate, dihydrate C36H82Cl2N8Ni2O15
  5. Crystal structure of catena-poly[aquabis(3-nitrobenzoato-κ2O:O′)-(μ2-pyrazine-N: N′)cadmium(II)], C18H14N4O9Cd
  6. Crystal structure of 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione, C14H15F2NO2
  7. The crystal structure of thioxanthen-9-one-10,10-dioxide, C13H8O3S – a second polymorph
  8. Crystal structure of (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  9. The crystal structure of diaquahydrogen 2,5-dimethylbenzenesulphonate, C8H14O5S
  10. The crystal structure of N-(4-(cyclohexylimino)pent-2-en-2-yl)cyclohexanamine, C17H30N2
  11. The twinned crystal structure of 1,3-phenylenedimethanaminium dibromide, C8H14Br2N2
  12. Crystal structure of 2,4,7,9-tetranitro-10H-benzofuro[3,2-b]indole – dimethyl sulfoxide (1/1), C16H11N5O10S
  13. Crystal structure of 2,6-bis(2-(pyridin-3-yl)ethyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone, C24H18N4O4
  14. The crystal structure of 3,4-dichlorobenzoic acid chloride, C7H3Cl3O
  15. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-k2S:S)zinc(II), C26H18N6ZnS4
  16. Crystal structure of tetrakis(μ-naphthalene-1-carboxylato-κ2O,O′)bis(methanol)copper(II), C46H36Cu2O10
  17. Crystal structure of 9-methyl-3-methylene-1,2,3,9-tetrahydro-4H-carbazol-4-one, C14H13NO
  18. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 3-nitrophthalate monohydrate, C12H19N9O7S2
  19. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate), C18H24F12N4P2
  20. The crystal structure of 5-hydroxy-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one– rubrofusarin B, C16H14O5
  21. The crystal structure of bis(ethanol-kO)- bis(6-aminopicolinato-k2N,O)manganese(II), C16H22O6N4Mn
  22. The crystal structure of 3,3′-((carbonylbis(azanediyl))bis(ethane-2,1-diyl)) bis(1-methyl-1H-benzo[d]imidazol-3-ium) tetrafluoroborate monohydrate, C21H28N6O3B2F8
  23. Crystal structure of dimethanol-dichlorido-bis( μ2-2-(((1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato- κ4O:O,O′,N)dinickel (II), C20H24ClNiN3O4
  24. The crystal structure of methyl 5-(trifluoromethyl)-1H-pyrrole-2-carboxylate, C7H6F3NO2
  25. Crystal structure of (OC‐6‐13)‐aqua‐tris (3‐bromopyridine‐κ1N)‐bis(trifluoroacetato‐κ1O)cadmium(II) C19H14Br3CdF6N3O5
  26. Crystal structure of methyl (E)-3-(4-(2-ethoxy-2-oxoethoxy)phenyl) acrylate, C14H16O5
  27. Crystal structure of methyl 4-acetoxy-3,5-dimethoxybenzoate, C12H14O6
  28. The crystal structure of 2-(1H-benzimidazol-2-yl)-3-bromo-5-chlorophenol, C13H8BrClN2O
  29. The crystal structure of bis(μ2-5-chloro-N-(2-methyl-1-oxidopropylidene)-2-oxidobenzohydrazonate-κ5N,O,O′:N′,O′′)pentakis(pyridine-κ1N)tricopper(II), C47H45Cl2N9Cu3O6
  30. Synthesis and crystal structure of catena-poly[aqua-bis(nitrato-κ2O:O′)- (μ2-((1 H-imidazol-1-yl)methyl)benzene-κ2 N,N′)-H2O-κ2O]cadmium(II), C14H16N6O7Cd
  31. The crystal structure of pentakis(carbonyl)-{μ-[2,3-bis(sulfanyl)propan-1-olato]}-(triphenylphosphane)diiron (FeFe)C26H21Fe2O6PS2
  32. Crystal structure of ethyl-2-(3-benzoylthioureido)propanoate, C13H16N2O3S
  33. Crystal structure of 2-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino[2′,1′:1,6] pyrazino[2,3-b]quinoxaline, C19H18N4O
  34. Crystal structure of 2,2′-[ethane-1,2-diylbis(azanylylidenemethylylidene)]bis(6-chlorophenol), C16H14Cl2N2O2
  35. The crystal structure of (Z)-3-((2-(2-(2-aminophenoxy)ethoxy)phenyl)amino)-1-phenylbut-2-en-1-one, C24H24N2O3
  36. The crystal structure of 10-(3,5-di(pyridin-4-yl)phenyl)-10H-phenoxazine dihydrate, C28H23N3O3
  37. Crystal structure of poly[dipoly[aqua-di(µ2-pyrazin-2-olato-κ2N:N′) zinc(II)], C8H8N4O3Zn
  38. Crystal structure of poly[tetra(μ2-cyanido-κ2N:O)-bis(N,N-dimethylformamide-κO)-manganese(II)-platinum(II)], C10H14MnN6O2Pt
  39. The crystal structure of aqua-chlorido-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dichlorophenolato-κ4N,N′,O,O′)manganese(III), C16H12Cl5MnN2O3
  40. Crystal structure of [di(µ2-cyanido)-dicyanido-bis(dimethyl sulfoxide-κO)- bis(2,2′-(ethane-1,2-diylbis(azanylylidenemethanylylidene))diphenolato-κ4,N,N′,O,O′)- dimanganese(III)-platinum(II)], C40H40Mn2N8O6PtS2
  41. The crystal structure of (azido)-κ1N-6,6′-((cyclohexane-1,2-diylbis(azanylylidene)) bis(methanylylidene))bis(3-bromophenolato-κ4N,N,O,O)-(methanol)-manganese(III)–methanol(1/1), C22H26Br2MnN5O4
  42. Crystal structure of 7-chloro-N-(4-iodobenzyl)-1,2,3,4-tetrahydroacridin-9-amine, C20H18ClIN2
  43. Crystal structure of catena-poly[(1,4,8,11-tetraazacyclotetradecane-κ4N,N,N,N′′′)-bis(μ2-thiocyanato-κ2N:S)-bis(thiocyanato-κS)-nickel(II)palladium(II)], C14H24N8NiPdS4
  44. Crystal structure of 3-chloro-4-(4-ethylpiperazin-1-yl)aniline monohydrate, C12H20ClN3O
  45. Crystal structure of the 2D coordination polymer poly[diaqua-bis(μ2-3- methoxyisonicotinato-κ2N:O)cobalt(II)] — dimethylformamide (1/1), C20H30CoN4O10
  46. Crystal structure of 4-[(5-chloro-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione, C12H13ClN4OS
  47. Crystal structure of N-(5-(2-(benzyl(1-(4-methoxyphenyl)propan-2-yl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide, C33H36N2O4
  48. Crystal structure of 3-(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid, C9H12O5
  49. The crystal structure of 1-((dimethylamino)(3-nitrophenyl)methyl)naphthalen-2-ol, C19H18N2O3
  50. Crystal structure of catena-poly[di(μ2-cyanido-κ2C:N)-dicyanido-tetrakis(dimethyl sulfoxide-κO)-manganese(II)-platinum(II)], C12H24MnN4O4PtS4
  51. Crystal structure of 4-amino-N-(2-pyrimidinyl)benzenesulfonamide–1,4-dioxane (1/1), C14H18N4O4S
  52. Crystal structure of bis{1-[(benzotriazol-1-yl)methyl]-1H-1,3-(2-methyl-imidazol)}di-chloridomercury(II), [Hg(C11H11N5)2Cl2], C22H22N10Cl2Hg
  53. Crystal structure of 2, 3-bis((4-methylbenzoyl)oxy) succinic acid–N, N-dimethylformamide (1/1), C23H25NO9
  54. Crystal structure of catena-poly[bis(4-(4-carboxyphenoxy)benzoato-κ1O)-μ2-(1,4-bis(1-imidazolyl)benzene-κ2N:N′)cobalt(II)], C40H28N4O10Co
  55. Crystal structure of 1H-imidazol-3-ium poly[aqua-(μ4-glutarato-κ6O,O′:O′:O′′,O′′′:O′′′)-(nitrato-κ2O,O′)strontium(II)], C8H13N3O8Sr
  56. Crystal structure of (R)-6-(benzo[b]thiophen-5-yl)-2-methyl-2,6-dihydrobenzo [5,6] silino[4,3,2-cd]indole, C23H17NSSi
  57. Crystal structure of catena-poly[bis(μ2-thiocyanato-κ2N:S)-(2-(5-methyl-1H-pyrazol-3-yl)pyridine-κ2N,N′)cadmium(II)]–dioxane (1/1), C15H17CdN5O2S2
  58. Crystal structure of poly[aqua-(μ2-1,4-bis(2′-carboxylatophenoxy)benzene-κ2O:O′)-(μ2-4,4′-bipyridione-κ2N:N′)cadmium(II)] monhydrate, C30H22CdN2O7⋅H2O
  59. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-bis(μ2-4′-methyl-[1,1′-biphenyl]-3,5-dicarboxylato-k4O,O′:O″,O′″)dicadmium(II)] dihydrate, C20H20NO7Cd
  60. Crystal structure of 1‐tert‐butyl‐3‐(2,6‐diisopropyl‐4‐phenoxyphenyl)‐2-methylisothiourea, C24H34N2OS
  61. Crystal structure of catena-poly[triaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ1O)cobalt(II)] — N,N′-dimethylformamide (1/1), C28H34N8O8Co
  62. Crystal structure of tetraaqua-bis(1,4-di(1H-imidazol-1-yl)benzene-κ1N)manganese(II) 2,3-dihydroxyterephthalate, C32H32MnN8O10
Heruntergeladen am 30.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2020-0639/html
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