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

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

doi:10.1107/S1600536808005291

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o721

doi:10.1107/S1600536808005291

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

Wen Pei,^a ^* Xiaoyang Si,^a Dengxiang Ji ^a and Jianbing Ji ^a

^aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: pei_wen58@hotmail.com

(Received 22 January 2008; accepted 25 February 2008; online 20 March 2008)

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 ).

Experimental

Crystal data

C₁₃H₁₆N₃O⁺·PF₆⁻
M_r = 375.26
Monoclinic, P 2₁ /c
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 ) T_min = 0.879, T_max = 0.937
3677 measured reflections
3677 independent reflections
2362 reflections with F² > 2σ(F²)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.145
S = 1.01
3677 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.23	3.119 (3)	160
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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.

Supporting information

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

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

checkCIF report

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.

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

	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.

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

Crystal data top

C₁₃H₁₆N₃O⁺·PF₆⁻	F(000) = 768.00
M_r = 375.26	D_x = 1.544 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 9621 reflections
a = 9.6414 (4) Å	θ = 3.0–27.4°
b = 19.4934 (10) Å	µ = 0.24 mm⁻¹
c = 8.8402 (4) Å	T = 296 K
β = 103.6880 (11)°	Block, colourless
V = 1614.27 (13) Å³	0.40 × 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^-1	R_int = 0.037
ω–scan	θ_max = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.879, T_max = 0.937	k = −25→0
3677 measured reflections	l = 0→11
3677 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[0.0013F_o² + 5.0000σ(F_o²)]/(4F_o²)
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.50 e Å⁻³
3677 reflections	Δρ_min = −0.38 e Å⁻³
218 parameters	Extinction correction: Larson (1970)
0 restraints	Extinction coefficient: 192 (26)

Crystal data top

C₁₃H₁₆N₃O⁺·PF₆⁻	V = 1614.27 (13) Å³
M_r = 375.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6414 (4) Å	µ = 0.24 mm⁻¹
b = 19.4934 (10) Å	T = 296 K
c = 8.8402 (4) Å	0.40 × 0.30 × 0.27 mm
β = 103.6880 (11)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3677 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2362 reflections with F² > 2σ(F²)
T_min = 0.879, T_max = 0.937	R_int = 0.037
3677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.01	Δρ_max = 0.50 e Å⁻³
3677 reflections	Δρ_min = −0.38 e Å⁻³
218 parameters

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

	x	y	z	U_iso*/U_eq
P1	0.66835 (6)	0.13474 (4)	0.87558 (8)	0.0527 (2)
F1	0.80918 (19)	0.10215 (11)	0.8443 (2)	0.0979 (7)
F2	0.57794 (19)	0.09494 (9)	0.7276 (2)	0.0832 (5)
F3	0.5293 (2)	0.16754 (12)	0.9074 (2)	0.1199 (8)
F4	0.7630 (2)	0.17460 (10)	1.0203 (2)	0.0966 (6)
F5	0.6809 (2)	0.19681 (9)	0.7656 (2)	0.0946 (6)
F6	0.6574 (2)	0.07272 (11)	0.9846 (2)	0.1142 (8)
O1	0.78438 (18)	0.06145 (9)	0.4653 (2)	0.0562 (5)
N1	0.8257 (2)	0.17224 (11)	0.4113 (2)	0.0540 (6)
N2	0.3528 (2)	0.07578 (10)	0.2310 (2)	0.0486 (5)
N3	0.1253 (2)	0.06435 (10)	0.1961 (2)	0.0461 (5)
C1	0.9762 (2)	0.17472 (12)	0.4617 (2)	0.0477 (6)
C2	1.0511 (2)	0.13719 (13)	0.5867 (3)	0.0604 (8)
C3	1.1984 (3)	0.14078 (16)	0.6293 (3)	0.0685 (9)
C4	1.2713 (3)	0.18264 (16)	0.5499 (3)	0.0659 (9)
C5	1.1969 (3)	0.22013 (14)	0.4270 (3)	0.0671 (9)
C6	1.0501 (2)	0.21689 (12)	0.3810 (3)	0.0589 (8)
C7	0.7400 (2)	0.11745 (12)	0.4140 (2)	0.0467 (7)
C8	0.5835 (2)	0.13090 (12)	0.3475 (3)	0.0536 (7)
C9	0.5065 (2)	0.06525 (12)	0.2934 (3)	0.0587 (8)
C10	0.2893 (2)	0.11482 (13)	0.1046 (2)	0.0606 (8)
C11	0.1480 (2)	0.10802 (14)	0.0839 (2)	0.0596 (8)
C12	0.2500 (2)	0.04552 (12)	0.2837 (2)	0.0469 (6)
C13	−0.0136 (2)	0.03930 (13)	0.2138 (3)	0.0607 (8)
H1	0.7839	0.2098	0.3749	0.065*
H2	1.0024	0.1094	0.6424	0.072*
H3	1.2486	0.1147	0.7124	0.082*
H4	1.3703	0.1854	0.5795	0.079*
H5	1.2462	0.2485	0.3732	0.081*
H6	1.0010	0.2427	0.2967	0.071*
H10	0.3359	0.1412	0.0442	0.073*
H11	0.0783	0.1291	0.0073	0.071*
H12	0.2638	0.0159	0.3685	0.056*
H81	0.5726	0.1621	0.2600	0.064*
H82	0.5427	0.1515	0.4270	0.064*
H91	0.5201	0.0338	0.3808	0.070*
H92	0.5466	0.0454	0.2126	0.070*
H131	−0.0048	0.0238	0.3187	0.073*
H132	−0.0446	0.0020	0.1430	0.073*
H133	−0.0823	0.0758	0.1912	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0535 (4)	0.0500 (4)	0.0539 (4)	−0.0018 (3)	0.0113 (3)	0.0002 (3)
F1	0.0664 (11)	0.1231 (17)	0.1046 (14)	0.0181 (11)	0.0211 (10)	−0.0216 (12)
F2	0.0852 (12)	0.0635 (11)	0.0860 (11)	−0.0082 (8)	−0.0097 (9)	−0.0124 (9)
F3	0.0853 (14)	0.162 (2)	0.1203 (17)	0.0382 (14)	0.0409 (13)	−0.0086 (15)
F4	0.1166 (15)	0.0890 (14)	0.0679 (11)	0.0010 (11)	−0.0106 (10)	−0.0213 (10)
F5	0.1389 (17)	0.0636 (11)	0.0753 (11)	−0.0261 (11)	0.0136 (11)	0.0114 (9)
F6	0.1306 (18)	0.1012 (16)	0.1067 (15)	−0.0211 (13)	0.0199 (13)	0.0490 (12)
O1	0.0532 (10)	0.0470 (10)	0.0682 (11)	0.0004 (8)	0.0141 (8)	0.0127 (8)
N1	0.0485 (11)	0.0400 (12)	0.0690 (14)	0.0004 (9)	0.0050 (10)	0.0066 (10)
N2	0.0452 (11)	0.0438 (11)	0.0566 (12)	−0.0013 (9)	0.0114 (9)	0.0057 (9)
N3	0.0449 (11)	0.0423 (11)	0.0513 (11)	−0.0017 (9)	0.0115 (9)	−0.0019 (9)
C1	0.0485 (13)	0.0406 (13)	0.0524 (14)	−0.0029 (11)	0.0086 (11)	−0.0069 (11)
C2	0.0622 (17)	0.0636 (17)	0.0514 (15)	−0.0057 (13)	0.0059 (13)	0.0049 (13)
C3	0.0626 (18)	0.073 (2)	0.0603 (17)	0.0050 (15)	−0.0033 (14)	−0.0012 (15)
C4	0.0497 (15)	0.076 (2)	0.0702 (18)	0.0004 (14)	0.0102 (15)	−0.0162 (16)
C5	0.0625 (18)	0.0656 (19)	0.0763 (19)	−0.0155 (14)	0.0227 (16)	−0.0096 (16)
C6	0.0641 (17)	0.0466 (15)	0.0630 (16)	−0.0047 (12)	0.0093 (14)	0.0008 (13)
C7	0.0483 (14)	0.0455 (14)	0.0477 (14)	0.0031 (11)	0.0141 (11)	−0.0002 (11)
C8	0.0479 (14)	0.0491 (15)	0.0623 (16)	0.0013 (11)	0.0099 (12)	0.0012 (12)
C9	0.0437 (13)	0.0504 (15)	0.0793 (19)	−0.0014 (11)	0.0091 (12)	0.0053 (13)
C10	0.0631 (17)	0.0627 (17)	0.0556 (15)	−0.0049 (13)	0.0133 (13)	0.0175 (13)
C11	0.0589 (17)	0.0611 (17)	0.0529 (15)	0.0034 (13)	0.0016 (13)	0.0161 (13)
C12	0.0503 (14)	0.0405 (13)	0.0489 (13)	0.0002 (10)	0.0100 (11)	0.0024 (10)
C13	0.0470 (14)	0.0621 (17)	0.0745 (18)	−0.0067 (12)	0.0172 (13)	−0.0082 (14)

Geometric parameters (Å, º) top

P1—F1	1.581 (2)	C5—C6	1.378 (3)
P1—F2	1.5920 (18)	C7—C8	1.508 (3)
P1—F3	1.569 (2)	C8—C9	1.500 (3)
P1—F4	1.5878 (18)	C10—C11	1.337 (4)
P1—F5	1.5745 (19)	N1—H1	0.860
P1—F6	1.565 (2)	C2—H2	0.930
O1—C7	1.220 (2)	C3—H3	0.930
N1—C1	1.414 (3)	C4—H4	0.930
N1—C7	1.354 (3)	C5—H5	0.930
N2—C9	1.469 (3)	C6—H6	0.930
N2—C10	1.371 (3)	C8—H81	0.970
N2—C12	1.329 (3)	C8—H82	0.970
N3—C11	1.363 (3)	C9—H91	0.970
N3—C12	1.319 (2)	C9—H92	0.970
N3—C13	1.468 (3)	C10—H10	0.930
C1—C2	1.378 (3)	C11—H11	0.930
C1—C6	1.391 (3)	C12—H12	0.930
C2—C3	1.383 (4)	C13—H131	0.960
C3—C4	1.373 (4)	C13—H132	0.960
C4—C5	1.363 (3)	C13—H133	0.960

F1—P1—F2	89.22 (10)	N3—C11—C10	107.2 (2)
F1—P1—F3	179.54 (12)	N2—C12—N3	108.8 (2)
F1—P1—F4	89.07 (10)	C1—N1—H1	116.3
F1—P1—F5	90.36 (11)	C7—N1—H1	116.4
F1—P1—F6	89.02 (12)	C1—C2—H2	120.0
F2—P1—F3	91.21 (10)	C3—C2—H2	120.0
F2—P1—F4	178.00 (12)	C2—C3—H3	119.8
F2—P1—F5	88.52 (9)	C4—C3—H3	119.8
F2—P1—F6	91.50 (10)	C3—C4—H4	120.3
F3—P1—F4	90.50 (11)	C5—C4—H4	120.3
F3—P1—F5	89.49 (12)	C4—C5—H5	119.3
F3—P1—F6	91.13 (13)	C6—C5—H5	119.3
F4—P1—F5	90.45 (10)	C1—C6—H6	120.3
F4—P1—F6	89.51 (10)	C5—C6—H6	120.3
F5—P1—F6	179.38 (13)	C7—C8—H81	109.2
C1—N1—C7	127.3 (2)	C7—C8—H82	109.2
C9—N2—C10	126.9 (2)	C9—C8—H81	109.2
C9—N2—C12	125.2 (2)	C9—C8—H82	109.2
C10—N2—C12	107.8 (2)	H81—C8—H82	109.5
C11—N3—C12	108.7 (2)	N2—C9—H91	108.8
C11—N3—C13	126.36 (19)	N2—C9—H92	108.8
C12—N3—C13	124.9 (2)	C8—C9—H91	108.8
N1—C1—C2	122.6 (2)	C8—C9—H92	108.8
N1—C1—C6	118.1 (2)	H91—C9—H92	109.5
C2—C1—C6	119.3 (2)	N2—C10—H10	126.3
C1—C2—C3	120.1 (2)	C11—C10—H10	126.3
C2—C3—C4	120.5 (2)	N3—C11—H11	126.4
C3—C4—C5	119.3 (2)	C10—C11—H11	126.4
C4—C5—C6	121.4 (2)	N2—C12—H12	125.6
C1—C6—C5	119.4 (2)	N3—C12—H12	125.6
O1—C7—N1	123.4 (2)	N3—C13—H131	109.5
O1—C7—C8	122.1 (2)	N3—C13—H132	109.5
N1—C7—C8	114.5 (2)	N3—C13—H133	109.5
C7—C8—C9	110.5 (2)	H131—C13—H132	109.5
N2—C9—C8	112.3 (2)	H131—C13—H133	109.5
N2—C10—C11	107.5 (2)	H132—C13—H133	109.5

C1—N1—C7—O1	1.5 (4)	C13—N3—C12—N2	177.3 (2)
C1—N1—C7—C8	−178.3 (2)	N1—C1—C2—C3	179.0 (2)
C7—N1—C1—C2	−34.4 (4)	N1—C1—C6—C5	−179.7 (2)
C7—N1—C1—C6	145.6 (2)	C2—C1—C6—C5	0.3 (3)
C9—N2—C10—C11	177.3 (2)	C6—C1—C2—C3	−1.0 (4)
C10—N2—C9—C8	61.7 (3)	C1—C2—C3—C4	1.3 (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—C1	0.2 (4)
C12—N2—C10—C11	0.7 (2)	O1—C7—C8—C9	−23.5 (3)
C11—N3—C12—N2	−0.1 (2)	N1—C7—C8—C9	156.3 (2)
C12—N3—C11—C10	0.5 (3)	C7—C8—C9—N2	178.7 (2)
C13—N3—C11—C10	−176.8 (2)	N2—C10—C11—N3	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.23	3.119 (3)	160

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₃O⁺·PF₆⁻
M_r	375.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6414 (4), 19.4934 (10), 8.8402 (4)
β (°)	103.6880 (11)
V (Å³)	1614.27 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.40 × 0.30 × 0.27

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.879, 0.937
No. of measured, independent and observed [F² > 2σ(F²)] reflections	3677, 3677, 2362
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.145, 1.01
No. of reflections	3677
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.38

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004) and Larson (1970), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.230	3.119 (3)	160

Symmetry code: (i) −x+1, −y, −z+1.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
Rigaku. (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
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. CAS Google Scholar

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o721

doi:10.1107/S1600536808005291

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