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Acta Cryst. (2008). E64, o721    [ doi:10.1107/S1600536808005291 ]

3-[2-(Anilinocarbonyl)ethyl]-1-methyl-1H-imidazolium hexafluoridophosphate

W. Pei, X. Si, D. Ji and J. Ji

Abstract top

The title compound, C13H16N3O+·PF6-, which has an imide group in the imidazolium cation, is a new ionic liquid above its melting point. Two neighbouring molecules are connected by a weak non-classical C-H...O hydrogen bond with the formation of centrosymmetric 14-membered dimers.

Comment top

The phenol and aniline are two vital infectant in water. We prepared the new ionic liquid with a imide group in the imidazolium cations to extracted and seperate phenol and aniline from the water and achieved good result.

Two neighbour molecules are connected by a weak, non-classical, C12–H12···O1i H-bonds with the formation centrosymmetrical 14-membered dimers (symmetry code: (i) 1 - x, -y, 1 - z).

Related literature top

For the preparation of the compound, see: Yang et al. (2007).

Experimental top

The title compound was prepared according to the procedure of Yang et al. (2007). A mixture of 3-chloro-N-phenylpropanamide (9.18 g, 0.05 mol) and 1-methylimidazole (4.1 g, 0.05 mmol) in 30 ml of acetonitrile was heated with stirring at 353 K for 9 h. The solvent was removed by distillation, and a gray liquid was obtained. Then 50 ml of water and KPF6 (10.15 g, 0.055 mol) was added, the mixture was stirred at ambient temperature for 24 h. On completion, the water were filtered off and the title compound was obtained as a white solid in 61% yield. Diffraction quality crystals were obtained by slow evaporation of an ethylacetate solution at room temperature.

Refinement top

All H atoms were placed in calculated posistion for N–H = 0.86 Å, C–H = 0.97Å (for CH2), C–H = 0.96Å (for CH3), C–H = 0.93Å (for aromatic) and included in the final cycles of refinement as riding mode with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004) and Larson (1970); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top
[Figure 1] Fig. 1. View of the title molecule with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. View of a hydrogen-bonded (dashed lines) dimers with the symmetry code: (i) 1 - x, -y, 1 - z.
3-[2-(Anilinocarbonyl)ethyl]-1-methyl-1H-imidazolium hexafluorophosphate top
Crystal data top
C13H16N3O+·P1F6–F000 = 768.00
Mr = 375.26Dx = 1.544 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 9621 reflections
a = 9.6414 (4) Åθ = 3.0–27.4º
b = 19.4934 (10) ŵ = 0.24 mm−1
c = 8.8402 (4) ÅT = 296 (1) K
β = 103.6880 (11)ºBlock, colourless
V = 1614.27 (13) Å30.40 × 0.30 × 0.27 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2362 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.037
ω–scanθmax = 27.4º
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −12→12
Tmin = 0.879, Tmax = 0.937k = −25→0
3677 measured reflectionsl = 0→11
3677 independent reflections
Refinement top
Refinement on F2  w = 1/[0.0013Fo2 + 5.0000σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.056(Δ/σ)max < 0.001
wR(F2) = 0.145Δρmax = 0.50 e Å−3
S = 1.01Δρmin = −0.38 e Å−3
3677 reflectionsExtinction correction: Larson (1970)
218 parametersExtinction coefficient: 192 (26)
H-atom parameters constrained
Crystal data top
C13H16N3O+·P1F6–V = 1614.27 (13) Å3
Mr = 375.26Z = 4
Monoclinic, P21/cMo Kα
a = 9.6414 (4) ŵ = 0.24 mm−1
b = 19.4934 (10) ÅT = 296 (1) K
c = 8.8402 (4) Å0.40 × 0.30 × 0.27 mm
β = 103.6880 (11)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3677 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2362 reflections with F2 > 2σ(F2)
Tmin = 0.879, Tmax = 0.937Rint = 0.037
3677 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056218 parameters
wR(F2) = 0.145H-atom parameters constrained
S = 1.01Δρmax = 0.50 e Å−3
3677 reflectionsΔρmin = −0.38 e Å−3
Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.66835 (6)0.13474 (4)0.87558 (8)0.0527 (2)
F10.80918 (19)0.10215 (11)0.8443 (2)0.0979 (7)
F20.57794 (19)0.09494 (9)0.7276 (2)0.0832 (5)
F30.5293 (2)0.16754 (12)0.9074 (2)0.1199 (8)
F40.7630 (2)0.17460 (10)1.0203 (2)0.0966 (6)
F50.6809 (2)0.19681 (9)0.7656 (2)0.0946 (6)
F60.6574 (2)0.07272 (11)0.9846 (2)0.1142 (8)
O10.78438 (18)0.06145 (9)0.4653 (2)0.0562 (5)
N10.8257 (2)0.17224 (11)0.4113 (2)0.0540 (6)
N20.3528 (2)0.07578 (10)0.2310 (2)0.0486 (5)
N30.1253 (2)0.06435 (10)0.1961 (2)0.0461 (5)
C10.9762 (2)0.17472 (12)0.4617 (2)0.0477 (6)
C21.0511 (2)0.13719 (13)0.5867 (3)0.0604 (8)
C31.1984 (3)0.14078 (16)0.6293 (3)0.0685 (9)
C41.2713 (3)0.18264 (16)0.5499 (3)0.0659 (9)
C51.1969 (3)0.22013 (14)0.4270 (3)0.0671 (9)
C61.0501 (2)0.21689 (12)0.3810 (3)0.0589 (8)
C70.7400 (2)0.11745 (12)0.4140 (2)0.0467 (7)
C80.5835 (2)0.13090 (12)0.3475 (3)0.0536 (7)
C90.5065 (2)0.06525 (12)0.2934 (3)0.0587 (8)
C100.2893 (2)0.11482 (13)0.1046 (2)0.0606 (8)
C110.1480 (2)0.10802 (14)0.0839 (2)0.0596 (8)
C120.2500 (2)0.04552 (12)0.2837 (2)0.0469 (6)
C13−0.0136 (2)0.03930 (13)0.2138 (3)0.0607 (8)
H10.78390.20980.37490.065*
H21.00240.10940.64240.072*
H31.24860.11470.71240.082*
H41.37030.18540.57950.079*
H51.24620.24850.37320.081*
H61.00100.24270.29670.071*
H100.33590.14120.04420.073*
H110.07830.12910.00730.071*
H120.26380.01590.36850.056*
H810.57260.16210.26000.064*
H820.54270.15150.42700.064*
H910.52010.03380.38080.070*
H920.54660.04540.21260.070*
H131−0.00480.02380.31870.073*
H132−0.04460.00200.14300.073*
H133−0.08230.07580.19120.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0535 (4)0.0500 (4)0.0539 (4)−0.0018 (3)0.0113 (3)0.0002 (3)
F10.0664 (11)0.1231 (17)0.1046 (14)0.0181 (11)0.0211 (10)−0.0216 (12)
F20.0852 (12)0.0635 (11)0.0860 (11)−0.0082 (8)−0.0097 (9)−0.0124 (9)
F30.0853 (14)0.162 (2)0.1203 (17)0.0382 (14)0.0409 (13)−0.0086 (15)
F40.1166 (15)0.0890 (14)0.0679 (11)0.0010 (11)−0.0106 (10)−0.0213 (10)
F50.1389 (17)0.0636 (11)0.0753 (11)−0.0261 (11)0.0136 (11)0.0114 (9)
F60.1306 (18)0.1012 (16)0.1067 (15)−0.0211 (13)0.0199 (13)0.0490 (12)
O10.0532 (10)0.0470 (10)0.0682 (11)0.0004 (8)0.0141 (8)0.0127 (8)
N10.0485 (11)0.0400 (12)0.0690 (14)0.0004 (9)0.0050 (10)0.0066 (10)
N20.0452 (11)0.0438 (11)0.0566 (12)−0.0013 (9)0.0114 (9)0.0057 (9)
N30.0449 (11)0.0423 (11)0.0513 (11)−0.0017 (9)0.0115 (9)−0.0019 (9)
C10.0485 (13)0.0406 (13)0.0524 (14)−0.0029 (11)0.0086 (11)−0.0069 (11)
C20.0622 (17)0.0636 (17)0.0514 (15)−0.0057 (13)0.0059 (13)0.0049 (13)
C30.0626 (18)0.073 (2)0.0603 (17)0.0050 (15)−0.0033 (14)−0.0012 (15)
C40.0497 (15)0.076 (2)0.0702 (18)0.0004 (14)0.0102 (15)−0.0162 (16)
C50.0625 (18)0.0656 (19)0.0763 (19)−0.0155 (14)0.0227 (16)−0.0096 (16)
C60.0641 (17)0.0466 (15)0.0630 (16)−0.0047 (12)0.0093 (14)0.0008 (13)
C70.0483 (14)0.0455 (14)0.0477 (14)0.0031 (11)0.0141 (11)−0.0002 (11)
C80.0479 (14)0.0491 (15)0.0623 (16)0.0013 (11)0.0099 (12)0.0012 (12)
C90.0437 (13)0.0504 (15)0.0793 (19)−0.0014 (11)0.0091 (12)0.0053 (13)
C100.0631 (17)0.0627 (17)0.0556 (15)−0.0049 (13)0.0133 (13)0.0175 (13)
C110.0589 (17)0.0611 (17)0.0529 (15)0.0034 (13)0.0016 (13)0.0161 (13)
C120.0503 (14)0.0405 (13)0.0489 (13)0.0002 (10)0.0100 (11)0.0024 (10)
C130.0470 (14)0.0621 (17)0.0745 (18)−0.0067 (12)0.0172 (13)−0.0082 (14)
Geometric parameters (Å, °) top
P1—F11.581 (2)C5—C61.378 (3)
P1—F21.5920 (18)C7—C81.508 (3)
P1—F31.569 (2)C8—C91.500 (3)
P1—F41.5878 (18)C10—C111.337 (4)
P1—F51.5745 (19)N1—H10.860
P1—F61.565 (2)C2—H20.930
O1—C71.220 (2)C3—H30.930
N1—C11.414 (3)C4—H40.930
N1—C71.354 (3)C5—H50.930
N2—C91.469 (3)C6—H60.930
N2—C101.371 (3)C8—H810.970
N2—C121.329 (3)C8—H820.970
N3—C111.363 (3)C9—H910.970
N3—C121.319 (2)C9—H920.970
N3—C131.468 (3)C10—H100.930
C1—C21.378 (3)C11—H110.930
C1—C61.391 (3)C12—H120.930
C2—C31.383 (4)C13—H1310.960
C3—C41.373 (4)C13—H1320.960
C4—C51.363 (3)C13—H1330.960
F1—P1—F289.22 (10)N3—C11—C10107.2 (2)
F1—P1—F3179.54 (12)N2—C12—N3108.8 (2)
F1—P1—F489.07 (10)C1—N1—H1116.3
F1—P1—F590.36 (11)C7—N1—H1116.4
F1—P1—F689.02 (12)C1—C2—H2120.0
F2—P1—F391.21 (10)C3—C2—H2120.0
F2—P1—F4178.00 (12)C2—C3—H3119.8
F2—P1—F588.52 (9)C4—C3—H3119.8
F2—P1—F691.50 (10)C3—C4—H4120.3
F3—P1—F490.50 (11)C5—C4—H4120.3
F3—P1—F589.49 (12)C4—C5—H5119.3
F3—P1—F691.13 (13)C6—C5—H5119.3
F4—P1—F590.45 (10)C1—C6—H6120.3
F4—P1—F689.51 (10)C5—C6—H6120.3
F5—P1—F6179.38 (13)C7—C8—H81109.2
C1—N1—C7127.3 (2)C7—C8—H82109.2
C9—N2—C10126.9 (2)C9—C8—H81109.2
C9—N2—C12125.2 (2)C9—C8—H82109.2
C10—N2—C12107.8 (2)H81—C8—H82109.5
C11—N3—C12108.7 (2)N2—C9—H91108.8
C11—N3—C13126.36 (19)N2—C9—H92108.8
C12—N3—C13124.9 (2)C8—C9—H91108.8
N1—C1—C2122.6 (2)C8—C9—H92108.8
N1—C1—C6118.1 (2)H91—C9—H92109.5
C2—C1—C6119.3 (2)N2—C10—H10126.3
C1—C2—C3120.1 (2)C11—C10—H10126.3
C2—C3—C4120.5 (2)N3—C11—H11126.4
C3—C4—C5119.3 (2)C10—C11—H11126.4
C4—C5—C6121.4 (2)N2—C12—H12125.6
C1—C6—C5119.4 (2)N3—C12—H12125.6
O1—C7—N1123.4 (2)N3—C13—H131109.5
O1—C7—C8122.1 (2)N3—C13—H132109.5
N1—C7—C8114.5 (2)N3—C13—H133109.5
C7—C8—C9110.5 (2)H131—C13—H132109.5
N2—C9—C8112.3 (2)H131—C13—H133109.5
N2—C10—C11107.5 (2)H132—C13—H133109.5
C1—N1—C7—O11.5 (4)C13—N3—C12—N2177.3 (2)
C1—N1—C7—C8−178.3 (2)N1—C1—C2—C3179.0 (2)
C7—N1—C1—C2−34.4 (4)N1—C1—C6—C5−179.7 (2)
C7—N1—C1—C6145.6 (2)C2—C1—C6—C50.3 (3)
C9—N2—C10—C11177.3 (2)C6—C1—C2—C3−1.0 (4)
C10—N2—C9—C861.7 (3)C1—C2—C3—C41.3 (4)
C9—N2—C12—N3−177.1 (2)C2—C3—C4—C5−0.8 (4)
C12—N2—C9—C8−122.1 (2)C3—C4—C5—C6−0.0 (4)
C10—N2—C12—N3−0.3 (2)C4—C5—C6—C10.2 (4)
C12—N2—C10—C110.7 (2)O1—C7—C8—C9−23.5 (3)
C11—N3—C12—N2−0.1 (2)N1—C7—C8—C9156.3 (2)
C12—N3—C11—C100.5 (3)C7—C8—C9—N2178.7 (2)
C13—N3—C11—C10−176.8 (2)N2—C10—C11—N3−0.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.233.119 (3)160
Symmetry codes: (i) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.233.119 (3)160
Symmetry codes: (i) −x+1, −y, −z+1.
references
References top

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Yang, W. L., Xu, D. Q., Liu, B. Y., Luo, S. P., Wang, B. T. & Xu, Z. Y. (2007). J. Fine Chem. 24, 737–742.