1-{2-[(2,4-Dichloro­benzyl­idene)amino]eth­yl}-3-methyl­imidazolium hexa­fluoro­phosphate

Liu, J.; Li, B.; Li, Y.-Q.; Zheng, W.-J.

doi:10.1107/S1600536809045115

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2972

doi:10.1107/S1600536809045115

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1-{2-[(2,4-Dichlorobenzylidene)amino]ethyl}-3-methylimidazolium hexafluorophosphate

Jie Liu,^a Bin Li,^a Yi-Qun Li ^a ^* and Wen-Jie Zheng ^a

^aDepartment of Chemistry, Jinan University, Guangzhou 510632, People's Republic of China
^*Correspondence e-mail: tlyq@jnu.edu.cn

(Received 26 September 2009; accepted 28 October 2009; online 4 November 2009)

In the title Schiff base compound, C₁₃H₁₄Cl₂N₃⁺·PF₆⁻, the dihedral angle between the aromatic ring and imidazole ring in the cation is 6.10 (2)°. Intermolecular C—H⋯F hydrogen-bonding interactions and π–π stacking interactions [centoid–centroid distance = 3.7203 (12) Å] help stabilize the crystal packing.

Related literature

For bound-length data, see: Allen et al. (1987 ). For related structures, see: Pradeep (2005 ); Li et al. (2009 ). For ionic liquids and their applications, see: Wasserscheid & Keim (2000 ); Singh & Sekhon (2005 ); Noda & Watanabe (2000 ).

Experimental

Crystal data

C₁₃H₁₄Cl₂N₃⁺·PF₆⁻
M_r = 428.14
Triclinic, $[P \overline 1]$
a = 8.3465 (13) Å
b = 10.1419 (16) Å
c = 11.0310 (17) Å
α = 78.899 (2)°
β = 76.523 (2)°
γ = 67.834 (2)°
V = 835.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 173 K
0.32 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.844, T_max = 0.894
3566 measured reflections
3566 independent reflections
3151 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.093
S = 1.10
3566 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F3	0.95	2.51	3.324 (2)	143
C10—H10⋯F3ⁱ	0.95	2.33	3.203 (2)	152
C10—H10⋯F5ⁱ	0.95	2.54	3.373 (2)	147
C11—H11⋯F6	0.95	2.46	3.275 (2)	143
C12—H12⋯F2	0.95	2.48	3.239 (2)	137
C13—H13C⋯F5ⁱⁱ	0.98	2.54	3.464 (2)	158
Symmetry codes: (i) x-1, y+1, z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045115/jj2012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045115/jj2012Isup2.hkl

checkCIF report

Comment top

Ionic liquids are attracting much interest in many fields of chemistry and industry, due to their potential as green solvents for a wide range of applications in synthesis, catalysis, electrochemistry, and liquid-liquid extractions (Wasserscheid et al., 2000; Singh, 2005; Noda, 2000). Schiff base compounds are one of most prevalent mixed-donor ligands in the field of coordination chemistry (Li et al., 2009). As part of our program aimed at developing a novel functionalized ionic liquid, we now report the crystal structure of a novel ionic liquid-supported Schiff base (I).

The asymmetric unit of the title compond, (I), a Schiff base derived ionic liquid, is comprised of an organic cation and a PF₆ counter anion, Fig. 1. Bond lengths and angels are generally within normal ranges (Allen et al., 1987). The dihedral angle between the mean planes of the imidazole and benzene rings in the cation is 6.10°. The crystal structure exhibits weak C–H···Cl intramolecular and C–H···F intermolecular hydrogen bonding interactions as well as aromatic π–π stacking interactions between the imidazole and benzene rings of neighbouring cations [Cg1···Cg2 = 3.7203 (12)Å; 1-x, 1-y, 1-z, where Cg1 and Cg2 are centroids of the imidazole (N1/C10/N2/C11/C12) and benzene (C1–C6) rings, respectively, Fig. 2].

Related literature top

For bound-length data, see: Allen et al. (1987). For related structures, see: Pradeep (2005); Li et al. (2009). For ionic liquids and their applications, see: Wasserscheid & Keim (2000); Singh & Sekhon (2005); Noda & Watanabe (2000).

Experimental top

A mixture of the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate (4 mmol) and 2,4-dichlorobenzaldehyde (3 mmol) was stirred for 4 h at room temperature under solvent-free conditions. After completion ofthe reaction, ethanol (30 ml) was added to the reaction mixture, filtered off the solid product and washed with cold ethanol. The crude product was purified by recrystallization in ethanol/ethyl acetate(3:1 v/v). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of the complex at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound in (I) showing the atom numbering Scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of (I) viewed down the b axis. Weak C–H···Cl intramolecular and C–H···F intermolecular hydrogen bonding interactions are shown as dashed lines.

1-{2-[(2,4-Dichlorobenzylidene)amino]ethyl}-3-methylimidazolium hexafluorophosphate top

Crystal data top

C₁₃H₁₄Cl₂N₃⁺·PF₆⁻	Z = 2
M_r = 428.14	F(000) = 432
Triclinic, P1	D_x = 1.702 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3465 (13) Å	Cell parameters from 5376 reflections
b = 10.1419 (16) Å	θ = 2.7–27.0°
c = 11.0310 (17) Å	µ = 0.55 mm⁻¹
α = 78.899 (2)°	T = 173 K
β = 76.523 (2)°	Block, colorless
γ = 67.834 (2)°	0.32 × 0.24 × 0.21 mm
V = 835.3 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3566 independent reflections
Radiation source: fine-focus sealed tube	3151 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.844, T_max = 0.894	k = −12→12
3566 measured reflections	l = −14→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.047P)² + 0.3955P] where P = (F_o² + 2F_c²)/3
3566 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₃H₁₄Cl₂N₃⁺·PF₆⁻	γ = 67.834 (2)°
M_r = 428.14	V = 835.3 (2) Å³
Triclinic, P1	Z = 2
a = 8.3465 (13) Å	Mo Kα radiation
b = 10.1419 (16) Å	µ = 0.55 mm⁻¹
c = 11.0310 (17) Å	T = 173 K
α = 78.899 (2)°	0.32 × 0.24 × 0.21 mm
β = 76.523 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3566 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3151 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.894	R_int = 0.000
3566 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.10	Δρ_max = 0.25 e Å⁻³
3566 reflections	Δρ_min = −0.34 e Å⁻³
227 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.3066 (2)	0.34376 (17)	0.75848 (15)	0.0220 (3)
C2	0.3555 (2)	0.30042 (17)	0.87666 (15)	0.0227 (3)
C3	0.4986 (2)	0.17904 (17)	0.90058 (15)	0.0241 (3)
H3	0.5296	0.1513	0.9817	0.029*
C4	0.5944 (2)	0.09983 (17)	0.80205 (16)	0.0240 (3)
C5	0.5499 (2)	0.13684 (18)	0.68374 (16)	0.0270 (3)
H5	0.6167	0.0796	0.6180	0.032*
C6	0.4071 (2)	0.25808 (18)	0.66287 (15)	0.0257 (3)
H6	0.3761	0.2841	0.5818	0.031*
C7	0.1562 (2)	0.47512 (17)	0.73301 (15)	0.0237 (3)
H7	0.0901	0.5323	0.7989	0.028*
C8	−0.0351 (2)	0.64629 (18)	0.61084 (16)	0.0283 (4)
H8A	−0.0911	0.6807	0.6939	0.034*
H8B	−0.1235	0.6282	0.5765	0.034*
C9	0.0251 (2)	0.76060 (18)	0.52316 (16)	0.0297 (4)
H9A	−0.0739	0.8533	0.5247	0.036*
H9B	0.1211	0.7719	0.5539	0.036*
C10	0.0061 (2)	0.79621 (17)	0.29722 (15)	0.0244 (3)
H10	−0.1003	0.8765	0.3020	0.029*
C11	0.2433 (2)	0.62263 (18)	0.22472 (17)	0.0295 (4)
H11	0.3313	0.5609	0.1688	0.035*
C12	0.2369 (2)	0.61583 (18)	0.34869 (17)	0.0285 (4)
H12	0.3197	0.5483	0.3968	0.034*
C13	0.0537 (3)	0.7880 (2)	0.06825 (17)	0.0368 (4)
H13A	−0.0631	0.8627	0.0741	0.055*
H13B	0.0539	0.7081	0.0304	0.055*
H13C	0.1410	0.8276	0.0161	0.055*
Cl1	0.23667 (6)	0.39837 (5)	1.00213 (4)	0.03149 (12)
Cl2	0.78059 (6)	−0.04833 (5)	0.82692 (4)	0.03387 (13)
F1	0.44475 (17)	0.19348 (17)	0.31806 (17)	0.0655 (4)
F2	0.58081 (16)	0.32801 (12)	0.36186 (12)	0.0436 (3)
F3	0.70635 (18)	0.08681 (13)	0.38373 (11)	0.0492 (3)
F4	0.82315 (14)	0.21845 (14)	0.22679 (11)	0.0412 (3)
F5	0.68843 (16)	0.08228 (12)	0.18313 (11)	0.0423 (3)
F6	0.56548 (19)	0.32368 (14)	0.15939 (13)	0.0555 (4)
N1	0.08759 (18)	0.72527 (14)	0.39294 (13)	0.0243 (3)
N2	0.09752 (19)	0.73655 (15)	0.19419 (13)	0.0262 (3)
N3	0.11363 (19)	0.51306 (15)	0.62537 (13)	0.0263 (3)
P1	0.63280 (5)	0.20636 (5)	0.27210 (4)	0.02671 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0223 (7)	0.0219 (8)	0.0212 (7)	−0.0075 (6)	−0.0039 (6)	−0.0016 (6)
C2	0.0239 (7)	0.0235 (8)	0.0204 (7)	−0.0080 (6)	−0.0019 (6)	−0.0049 (6)
C3	0.0259 (8)	0.0241 (8)	0.0227 (8)	−0.0088 (6)	−0.0070 (6)	−0.0002 (6)
C4	0.0216 (7)	0.0178 (7)	0.0298 (8)	−0.0042 (6)	−0.0047 (6)	−0.0016 (6)
C5	0.0284 (8)	0.0242 (8)	0.0259 (8)	−0.0062 (7)	−0.0016 (6)	−0.0070 (6)
C6	0.0280 (8)	0.0272 (8)	0.0204 (7)	−0.0075 (7)	−0.0048 (6)	−0.0027 (6)
C7	0.0235 (8)	0.0223 (8)	0.0233 (8)	−0.0057 (6)	−0.0038 (6)	−0.0031 (6)
C8	0.0278 (8)	0.0279 (9)	0.0233 (8)	−0.0011 (7)	−0.0079 (6)	−0.0032 (6)
C9	0.0379 (9)	0.0236 (8)	0.0257 (8)	−0.0038 (7)	−0.0120 (7)	−0.0050 (6)
C10	0.0256 (8)	0.0197 (7)	0.0260 (8)	−0.0053 (6)	−0.0062 (6)	−0.0019 (6)
C11	0.0259 (8)	0.0229 (8)	0.0361 (9)	−0.0073 (7)	0.0005 (7)	−0.0053 (7)
C12	0.0217 (8)	0.0223 (8)	0.0373 (9)	−0.0034 (6)	−0.0060 (7)	−0.0013 (7)
C13	0.0491 (11)	0.0397 (10)	0.0220 (8)	−0.0165 (9)	−0.0065 (8)	−0.0017 (7)
Cl1	0.0345 (2)	0.0313 (2)	0.0223 (2)	−0.00086 (17)	−0.00639 (16)	−0.00879 (16)
Cl2	0.0295 (2)	0.0252 (2)	0.0392 (2)	0.00147 (16)	−0.00988 (17)	−0.00417 (17)
F1	0.0325 (7)	0.0723 (10)	0.0967 (12)	−0.0247 (7)	0.0080 (7)	−0.0315 (9)
F2	0.0411 (6)	0.0347 (6)	0.0488 (7)	−0.0033 (5)	−0.0004 (5)	−0.0202 (5)
F3	0.0676 (9)	0.0348 (6)	0.0269 (6)	−0.0002 (6)	−0.0056 (5)	−0.0010 (5)
F4	0.0279 (6)	0.0566 (7)	0.0404 (6)	−0.0150 (5)	0.0001 (5)	−0.0158 (5)
F5	0.0519 (7)	0.0373 (6)	0.0390 (6)	−0.0120 (5)	−0.0087 (5)	−0.0140 (5)
F6	0.0626 (9)	0.0399 (7)	0.0548 (8)	0.0017 (6)	−0.0332 (7)	0.0033 (6)
N1	0.0253 (7)	0.0194 (6)	0.0269 (7)	−0.0046 (5)	−0.0080 (5)	−0.0027 (5)
N2	0.0282 (7)	0.0245 (7)	0.0249 (7)	−0.0092 (6)	−0.0028 (5)	−0.0028 (5)
N3	0.0277 (7)	0.0235 (7)	0.0244 (7)	−0.0038 (6)	−0.0072 (5)	−0.0024 (5)
P1	0.0213 (2)	0.0254 (2)	0.0292 (2)	−0.00174 (17)	−0.00511 (16)	−0.00594 (17)

Geometric parameters (Å, º) top

C1—C2	1.397 (2)	C9—H9B	0.9900
C1—C6	1.401 (2)	C10—N2	1.324 (2)
C1—C7	1.479 (2)	C10—N1	1.330 (2)
C2—C3	1.387 (2)	C10—H10	0.9500
C2—Cl1	1.7414 (16)	C11—C12	1.345 (3)
C3—C4	1.383 (2)	C11—N2	1.382 (2)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.383 (2)	C12—N1	1.380 (2)
C4—Cl2	1.7394 (16)	C12—H12	0.9500
C5—C6	1.378 (2)	C13—N2	1.466 (2)
C5—H5	0.9500	C13—H13A	0.9800
C6—H6	0.9500	C13—H13B	0.9800
C7—N3	1.266 (2)	C13—H13C	0.9800
C7—H7	0.9500	F1—P1	1.5798 (13)
C8—N3	1.462 (2)	F2—P1	1.5991 (12)
C8—C9	1.521 (3)	F3—P1	1.6059 (12)
C8—H8A	0.9900	F4—P1	1.5945 (12)
C8—H8B	0.9900	F5—P1	1.6077 (12)
C9—N1	1.474 (2)	F6—P1	1.5903 (13)
C9—H9A	0.9900

C2—C1—C6	117.32 (15)	N1—C10—H10	125.6
C2—C1—C7	122.19 (14)	C12—C11—N2	106.95 (15)
C6—C1—C7	120.49 (14)	C12—C11—H11	126.5
C3—C2—C1	122.51 (15)	N2—C11—H11	126.5
C3—C2—Cl1	116.75 (12)	C11—C12—N1	107.24 (15)
C1—C2—Cl1	120.74 (12)	C11—C12—H12	126.4
C4—C3—C2	117.56 (15)	N1—C12—H12	126.4
C4—C3—H3	121.2	N2—C13—H13A	109.5
C2—C3—H3	121.2	N2—C13—H13B	109.5
C3—C4—C5	122.21 (15)	H13A—C13—H13B	109.5
C3—C4—Cl2	118.75 (13)	N2—C13—H13C	109.5
C5—C4—Cl2	119.02 (13)	H13A—C13—H13C	109.5
C6—C5—C4	118.87 (15)	H13B—C13—H13C	109.5
C6—C5—H5	120.6	C10—N1—C12	108.39 (14)
C4—C5—H5	120.6	C10—N1—C9	124.53 (14)
C5—C6—C1	121.51 (15)	C12—N1—C9	127.08 (14)
C5—C6—H6	119.2	C10—N2—C11	108.67 (14)
C1—C6—H6	119.2	C10—N2—C13	125.07 (15)
N3—C7—C1	121.45 (15)	C11—N2—C13	126.20 (15)
N3—C7—H7	119.3	C7—N3—C8	116.53 (14)
C1—C7—H7	119.3	F1—P1—F6	91.02 (9)
N3—C8—C9	110.67 (14)	F1—P1—F4	179.50 (9)
N3—C8—H8A	109.5	F6—P1—F4	89.48 (8)
C9—C8—H8A	109.5	F1—P1—F2	90.12 (7)
N3—C8—H8B	109.5	F6—P1—F2	91.08 (7)
C9—C8—H8B	109.5	F4—P1—F2	89.81 (6)
H8A—C8—H8B	108.1	F1—P1—F3	90.46 (9)
N1—C9—C8	112.47 (14)	F6—P1—F3	178.38 (8)
N1—C9—H9A	109.1	F4—P1—F3	89.04 (7)
C8—C9—H9A	109.1	F2—P1—F3	89.56 (7)
N1—C9—H9B	109.1	F1—P1—F5	90.54 (7)
C8—C9—H9B	109.1	F6—P1—F5	89.83 (7)
H9A—C9—H9B	107.8	F4—P1—F5	89.52 (6)
N2—C10—N1	108.75 (14)	F2—P1—F5	178.86 (7)
N2—C10—H10	125.6	F3—P1—F5	89.51 (7)

C6—C1—C2—C3	0.9 (2)	N3—C8—C9—N1	67.10 (18)
C7—C1—C2—C3	−178.59 (15)	N2—C11—C12—N1	0.05 (19)
C6—C1—C2—Cl1	−179.03 (12)	N2—C10—N1—C12	−0.11 (18)
C7—C1—C2—Cl1	1.5 (2)	N2—C10—N1—C9	179.91 (15)
C1—C2—C3—C4	0.0 (2)	C11—C12—N1—C10	0.03 (19)
Cl1—C2—C3—C4	179.95 (12)	C11—C12—N1—C9	−179.99 (16)
C2—C3—C4—C5	−1.1 (2)	C8—C9—N1—C10	111.90 (18)
C2—C3—C4—Cl2	177.09 (12)	C8—C9—N1—C12	−68.1 (2)
C3—C4—C5—C6	1.1 (3)	N1—C10—N2—C11	0.14 (18)
Cl2—C4—C5—C6	−177.02 (13)	N1—C10—N2—C13	−177.43 (15)
C4—C5—C6—C1	−0.1 (3)	C12—C11—N2—C10	−0.12 (19)
C2—C1—C6—C5	−0.8 (2)	C12—C11—N2—C13	177.41 (16)
C7—C1—C6—C5	178.67 (15)	C1—C7—N3—C8	−178.82 (14)
C2—C1—C7—N3	179.95 (16)	C9—C8—N3—C7	113.18 (17)
C6—C1—C7—N3	0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1	0.95	2.69	3.0846 (17)	106
C12—H12···F2	0.95	2.48	3.239 (2)	137
C5—H5···F3	0.95	2.51	3.324 (2)	143
C11—H11···F6	0.95	2.46	3.275 (2)	143
C10—H10···F3ⁱ	0.95	2.33	3.203 (2)	152
C10—H10···F5ⁱ	0.95	2.54	3.373 (2)	147
C13—H13C···F5ⁱⁱ	0.98	2.54	3.464 (2)	158

Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄Cl₂N₃⁺·PF₆⁻
M_r	428.14
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.3465 (13), 10.1419 (16), 11.0310 (17)
α, β, γ (°)	78.899 (2), 76.523 (2), 67.834 (2)
V (Å³)	835.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.32 × 0.24 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.844, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	3566, 3566, 3151
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.093, 1.10
No. of reflections	3566
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.34

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl1	0.95	2.69	3.0846 (17)	105.8
C12—H12···F2	0.95	2.48	3.239 (2)	136.7
C5—H5···F3	0.95	2.51	3.324 (2)	143.4
C11—H11···F6	0.95	2.46	3.275 (2)	143.3
C10—H10···F3ⁱ	0.95	2.33	3.203 (2)	152.4
C10—H10···F5ⁱ	0.95	2.54	3.373 (2)	147.0
C13—H13C···F5ⁱⁱ	0.98	2.54	3.464 (2)	157.7

Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y+1, −z.

Acknowledgements

We are grateful to the National Natural Science Foundation of China (No. 20672046) and the Guangdong Natural Science Foundation (No. 8151063201000016) for financial support.

References

Allen, F. H., Hennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, B., Li, Y.-Q., Liu, J. & Zheng, W.-J. (2009). Acta Cryst. E65, o1427. Web of Science CSD CrossRef IUCr Journals Google Scholar
Noda, A. & Watanabe, M. (2000). Electrochim. Acta, 45, 1265–1270. Web of Science CrossRef CAS Google Scholar
Pradeep, C. P. (2005). Acta Cryst. E61, o3825–o3827. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, B. & Sekhon, S. S. (2005). Chem. Phys. Lett. 414, 34–39. Web of Science CrossRef CAS Google Scholar
Wasserscheid, P. & Keim, W. (2000). Angew Chem. Int. Ed. 39, 3772–3789. CrossRef CAS Google Scholar

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Volume 65| Part 12| December 2009| Page o2972

doi:10.1107/S1600536809045115

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-{2-[(2,4-Di­chloro­benzyl­­idene)amino]eth­yl}-3-methyl­imidazolium hexa­fluoro­phosphate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{2-[(2,4-Dichlorobenzylidene)amino]ethyl}-3-methylimidazolium hexafluorophosphate