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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o721.
Published online 2008 March 20. doi:  10.1107/S1600536808005291
PMCID: PMC2961036

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

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0o721-scheme1.jpg

Experimental

Crystal data

  • C13H16N3O+·PF6
  • M r = 375.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o721-efi1.jpg
  • a = 9.6414 (4) Å
  • b = 19.4934 (10) Å
  • c = 8.8402 (4) Å
  • β = 103.6880 (11)°
  • V = 1614.27 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 296 (1) K
  • 0.40 × 0.30 × 0.27 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.879, T max = 0.937
  • 3677 measured reflections
  • 3677 independent reflections
  • 2362 reflections with F 2 > 2σ(F 2)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.145
  • S = 1.01
  • 3677 reflections
  • 218 parameters
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.38 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005291/rk2076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005291/rk2076Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

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.
Fig. 2.
View of a hydrogen-bonded (dashed lines) dimers with the symmetry code: (i) 1 - x, -y, 1 - z.

Crystal data

C13H16N3O+·P1F6F000 = 768.00
Mr = 375.26Dx = 1.544 Mg m3
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 mm1
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

Rigaku R-AXIS RAPID diffractometer2362 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

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 Å3
S = 1.01Δρmin = −0.38 e Å3
3677 reflectionsExtinction correction: Larson (1970)
218 parametersExtinction coefficient: 192 (26)
H-atom parameters constrained

Special details

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)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.233.119 (3)160

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2076).

References

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  • Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst.36, 1487.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard.
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