1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate

Li, B.; Li, Y.-Q.; Cai, Y.-P.; Zhou, M.-Y.

doi:10.1107/S1600536808037124

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2365

doi:10.1107/S1600536808037124

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1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate

Bin Li,^a Yi-Qun Li,^a ^* Yue-Peng Cai ^b and Mei-Yun Zhou ^a

^aDepartment of Chemistry, Jinan University, Guangzhou, Guangdong 510632, People's Republic of China, and ^bSchool of Chemistry and the Environment, South China Normal University, Guangzhou, Guangdong 510631, People's Republic of China
^*Correspondence e-mail: tlyq@jnu.edu.cn

(Received 29 October 2008; accepted 10 November 2008; online 13 November 2008)

The title Schiff base compound, C₁₃H₁₆N₃O⁺·PF₆⁻, was derived from the condensation of 2-hydroxybenaldehyde with the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate in an ethanol solution. The asymmetric unit comprises one cation and two PF₆⁻ anions. The dihedral angle between the aromatic and imidazole rings is 15.2 (2)°. An intramolecular O—H⋯N hydrogen bond is found which generates an S(6) ring motif.

Related literature

For the synthesis of Schiff bases, see: Pradeep (2005 ); Butcher et al. (2005 ). For background on ionic liquids and their applications, see: Cai et al. (2006 ); Peng & Song (2006 ).

Experimental

Crystal data

C₁₃H₁₆N₃O⁺·PF₆⁻
M_r = 375.26
Monoclinic, C 2/c
a = 28.239 (15) Å
b = 7.134 (4) Å
c = 18.017 (9) Å
β = 118.342 (6)°
V = 3194 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.32 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.926, T_max = 0.965
8091 measured reflections
2969 independent reflections
1965 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.215
S = 1.01
2969 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.572 (5)	147

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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 I, global. DOI: 10.1107/S1600536808037124/tk2322sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037124/tk2322Isup2.hkl

checkCIF report

Comment top

The use of functionalized ionic liquids continues to receive attention in chemical synthesis and engineering, including as catalysts in organic synthesis (Cai et al., 2006; Peng & Song, 2006). Schiff base compounds are one of most prevalent mixed-donor ligands in the field of coordination chemistry (Pradeep, 2005; Butcher et al., 2005). Herein, we report the crystal structure of the title salt, (I).

Compound (I) is a Schiff base formed from the reaciton of 2-hydroxybenaldehyde and ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate. The molecular structure of the cation is shown in Fig. 1. The aromatic and imidazole rings form a dihedral angle of 15.2 (2)°. In the cation, an intramolecular O1—H1···N1 hydrogen bond leads to a six-membered ring S(6) motif, Table 1.

Related literature top

For the synthesis of Schiff bases, see: Pradeep (2005); Butcher et al. (2005). For background on ionic liquids and their applications, see: Cai et al. (2006); Peng & Song (2006).

Experimental top

A mixture of the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate (5 mmol) and 2-hydroxybenzaldehyde (5 mmol) in ethanol was stirred for 4 h. After the completion of the reaction, the excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of (I) at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); 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 cation in (I) showing the atom numbering Scheme. Displacement ellipsoids are drawn at the 50% probability level.

1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate top

Crystal data top

C₁₃H₁₆N₃O⁺·PF₆⁻	F(000) = 1536
M_r = 375.26	D_x = 1.561 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2060 reflections
a = 28.239 (15) Å	θ = 2.9–22.9°
b = 7.134 (4) Å	µ = 0.24 mm⁻¹
c = 18.017 (9) Å	T = 298 K
β = 118.342 (6)°	Prism, yellow
V = 3194 (3) Å³	0.32 × 0.25 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2969 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→34
T_min = 0.926, T_max = 0.965	k = −8→8
8091 measured reflections	l = −21→19

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.215	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.095P)² + 15.5678P] where P = (F_o² + 2F_c²)/3
2969 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₁₆N₃O⁺·PF₆⁻	V = 3194 (3) Å³
M_r = 375.26	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.239 (15) Å	µ = 0.24 mm⁻¹
b = 7.134 (4) Å	T = 298 K
c = 18.017 (9) Å	0.32 × 0.25 × 0.15 mm
β = 118.342 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2969 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1965 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.965	R_int = 0.043
8091 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.215	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.095P)² + 15.5678P] where P = (F_o² + 2F_c²)/3
2969 reflections	Δρ_max = 0.72 e Å⁻³
221 parameters	Δρ_min = −0.29 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
P1	0.7500	0.7500	0.0000	0.0501 (5)
P2	1.0000	0.6525 (3)	0.2500	0.0583 (5)
F1	0.81350 (11)	0.7434 (5)	0.05733 (18)	0.0696 (9)
F2	0.74441 (13)	0.5737 (5)	0.04985 (19)	0.0742 (9)
F3	0.74598 (13)	0.8887 (5)	0.06617 (18)	0.0737 (9)
F4	1.0089 (2)	0.5007 (9)	0.3170 (3)	0.159 (2)
F5	0.93929 (17)	0.6504 (10)	0.2199 (4)	0.162 (2)
F6	1.0081 (3)	0.8057 (8)	0.3156 (3)	0.156 (2)
O1	0.80570 (15)	0.2094 (7)	0.2303 (3)	0.0801 (12)
H1	0.8137	0.1973	0.1923	0.120*
N1	0.86812 (17)	0.1728 (6)	0.1638 (3)	0.0551 (10)
N2	0.86519 (16)	0.3299 (5)	−0.0349 (2)	0.0513 (10)
N3	0.85173 (18)	0.3101 (6)	−0.1622 (3)	0.0591 (11)
C1	0.8504 (2)	0.1958 (7)	0.3054 (3)	0.0566 (12)
C2	0.8461 (3)	0.2063 (8)	0.3792 (4)	0.0671 (15)
H2	0.8126	0.2218	0.3762	0.081*
C3	0.8914 (3)	0.1938 (8)	0.4566 (4)	0.0722 (16)
H3	0.8882	0.2028	0.5055	0.087*
C4	0.9408 (3)	0.1686 (8)	0.4625 (4)	0.0719 (16)
H4	0.9710	0.1597	0.5152	0.086*
C5	0.9460 (2)	0.1563 (7)	0.3911 (3)	0.0626 (13)
H5	0.9799	0.1381	0.3956	0.075*
C6	0.90111 (19)	0.1708 (6)	0.3114 (3)	0.0491 (11)
C7	0.9077 (2)	0.1593 (7)	0.2363 (3)	0.0536 (12)
H7	0.9419	0.1416	0.2420	0.064*
C8	0.8777 (2)	0.1599 (7)	0.0908 (3)	0.0600 (13)
H8A	0.8596	0.0508	0.0571	0.072*
H8B	0.9160	0.1475	0.1095	0.072*
C9	0.8567 (2)	0.3333 (8)	0.0397 (3)	0.0634 (14)
H9A	0.8185	0.3450	0.0217	0.076*
H9B	0.8748	0.4416	0.0741	0.076*
C10	0.9137 (2)	0.3503 (8)	−0.0329 (3)	0.0612 (13)
H10	0.9466	0.3686	0.0150	0.073*
C11	0.9053 (2)	0.3392 (8)	−0.1120 (3)	0.0627 (13)
H11	0.9312	0.3494	−0.1297	0.075*
C12	0.8285 (2)	0.3056 (7)	−0.1133 (3)	0.0612 (13)
H12	0.7920	0.2881	−0.1319	0.073*
C13	0.8247 (3)	0.2925 (10)	−0.2541 (3)	0.087 (2)
H13A	0.7873	0.2649	−0.2742	0.131*
H13B	0.8410	0.1930	−0.2699	0.131*
H13C	0.8280	0.4080	−0.2786	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0469 (10)	0.0621 (11)	0.0450 (9)	0.0109 (8)	0.0248 (8)	0.0034 (8)
P2	0.0526 (11)	0.0736 (13)	0.0541 (10)	0.000	0.0296 (9)	0.000
F1	0.0422 (16)	0.088 (2)	0.0708 (19)	0.0081 (15)	0.0202 (14)	−0.0014 (16)
F2	0.084 (2)	0.075 (2)	0.0696 (19)	0.0024 (17)	0.0408 (17)	0.0159 (16)
F3	0.084 (2)	0.082 (2)	0.0611 (18)	0.0150 (17)	0.0393 (17)	−0.0107 (15)
F4	0.181 (5)	0.157 (5)	0.135 (4)	−0.002 (4)	0.073 (4)	0.072 (4)
F5	0.063 (3)	0.243 (7)	0.174 (5)	−0.004 (3)	0.051 (3)	−0.033 (5)
F6	0.209 (6)	0.150 (5)	0.108 (4)	−0.003 (4)	0.076 (4)	−0.052 (3)
O1	0.055 (2)	0.116 (3)	0.080 (3)	−0.006 (2)	0.040 (2)	−0.018 (2)
N1	0.058 (3)	0.061 (2)	0.057 (2)	0.001 (2)	0.035 (2)	−0.002 (2)
N2	0.056 (2)	0.051 (2)	0.046 (2)	0.0114 (18)	0.0238 (19)	0.0029 (17)
N3	0.069 (3)	0.056 (2)	0.051 (2)	0.004 (2)	0.027 (2)	0.0005 (19)
C1	0.062 (3)	0.053 (3)	0.070 (3)	−0.009 (2)	0.043 (3)	−0.004 (2)
C2	0.078 (4)	0.063 (3)	0.089 (4)	−0.009 (3)	0.062 (4)	−0.006 (3)
C3	0.111 (5)	0.056 (3)	0.077 (4)	−0.003 (3)	0.067 (4)	0.005 (3)
C4	0.092 (4)	0.068 (4)	0.060 (3)	0.007 (3)	0.040 (3)	0.009 (3)
C5	0.064 (3)	0.063 (3)	0.063 (3)	0.011 (3)	0.033 (3)	0.010 (3)
C6	0.056 (3)	0.046 (2)	0.053 (3)	0.002 (2)	0.031 (2)	0.003 (2)
C7	0.057 (3)	0.050 (3)	0.069 (3)	0.005 (2)	0.042 (3)	0.005 (2)
C8	0.072 (3)	0.061 (3)	0.062 (3)	0.003 (3)	0.044 (3)	−0.006 (2)
C9	0.079 (4)	0.065 (3)	0.057 (3)	0.016 (3)	0.042 (3)	0.003 (2)
C10	0.049 (3)	0.068 (3)	0.063 (3)	0.003 (2)	0.024 (2)	0.003 (3)
C11	0.065 (3)	0.067 (3)	0.067 (3)	0.006 (3)	0.040 (3)	0.008 (3)
C12	0.056 (3)	0.062 (3)	0.066 (3)	−0.001 (2)	0.029 (3)	−0.005 (3)
C13	0.105 (5)	0.101 (5)	0.047 (3)	0.002 (4)	0.029 (3)	−0.005 (3)

Geometric parameters (Å, º) top

P1—F1ⁱ	1.589 (3)	C1—C6	1.396 (7)
P1—F1	1.589 (3)	C2—C3	1.377 (8)
P1—F3	1.594 (3)	C2—H2	0.9300
P1—F3ⁱ	1.594 (3)	C3—C4	1.359 (8)
P1—F2ⁱ	1.596 (3)	C3—H3	0.9300
P1—F2	1.596 (3)	C4—C5	1.366 (7)
P2—F5ⁱⁱ	1.533 (4)	C4—H4	0.9300
P2—F5	1.533 (4)	C5—C6	1.398 (7)
P2—F6	1.544 (5)	C5—H5	0.9300
P2—F6ⁱⁱ	1.544 (5)	C6—C7	1.454 (6)
P2—F4ⁱⁱ	1.550 (5)	C7—H7	0.9300
P2—F4	1.550 (5)	C8—C9	1.487 (7)
O1—C1	1.346 (6)	C8—H8A	0.9700
O1—H1	0.8200	C8—H8B	0.9700
N1—C7	1.256 (6)	C9—H9A	0.9700
N1—C8	1.467 (6)	C9—H9B	0.9700
N2—C12	1.308 (6)	C10—C11	1.333 (7)
N2—C10	1.360 (6)	C10—H10	0.9300
N2—C9	1.474 (6)	C11—H11	0.9300
N3—C12	1.324 (6)	C12—H12	0.9300
N3—C11	1.360 (7)	C13—H13A	0.9600
N3—C13	1.464 (6)	C13—H13B	0.9600
C1—C2	1.392 (7)	C13—H13C	0.9600

F1ⁱ—P1—F1	180.00 (12)	C1—C2—H2	119.9
F1ⁱ—P1—F3	90.50 (16)	C4—C3—C2	120.9 (5)
F1—P1—F3	89.50 (16)	C4—C3—H3	119.6
F1ⁱ—P1—F3ⁱ	89.50 (16)	C2—C3—H3	119.6
F1—P1—F3ⁱ	90.50 (16)	C3—C4—C5	120.1 (6)
F3—P1—F3ⁱ	180.0 (2)	C3—C4—H4	120.0
F1ⁱ—P1—F2ⁱ	89.62 (17)	C5—C4—H4	120.0
F1—P1—F2ⁱ	90.38 (17)	C4—C5—C6	120.8 (5)
F3—P1—F2ⁱ	89.60 (17)	C4—C5—H5	119.6
F3ⁱ—P1—F2ⁱ	90.40 (17)	C6—C5—H5	119.6
F1ⁱ—P1—F2	90.38 (17)	C1—C6—C5	119.1 (4)
F1—P1—F2	89.62 (17)	C1—C6—C7	121.1 (5)
F3—P1—F2	90.40 (17)	C5—C6—C7	119.8 (4)
F3ⁱ—P1—F2	89.60 (17)	N1—C7—C6	121.3 (4)
F2ⁱ—P1—F2	180.0 (2)	N1—C7—H7	119.4
F5ⁱⁱ—P2—F5	178.9 (5)	C6—C7—H7	119.4
F5ⁱⁱ—P2—F6	90.1 (4)	N1—C8—C9	108.2 (4)
F5—P2—F6	90.7 (3)	N1—C8—H8A	110.1
F5ⁱⁱ—P2—F6ⁱⁱ	90.7 (3)	C9—C8—H8A	110.1
F5—P2—F6ⁱⁱ	90.1 (3)	N1—C8—H8B	110.1
F6—P2—F6ⁱⁱ	89.9 (5)	C9—C8—H8B	110.1
F5ⁱⁱ—P2—F4ⁱⁱ	90.6 (3)	H8A—C8—H8B	108.4
F5—P2—F4ⁱⁱ	88.6 (3)	N2—C9—C8	111.1 (4)
F6—P2—F4ⁱⁱ	179.0 (4)	N2—C9—H9A	109.4
F6ⁱⁱ—P2—F4ⁱⁱ	89.3 (3)	C8—C9—H9A	109.4
F5ⁱⁱ—P2—F4	88.6 (3)	N2—C9—H9B	109.4
F5—P2—F4	90.6 (3)	C8—C9—H9B	109.4
F6—P2—F4	89.3 (3)	H9A—C9—H9B	108.0
F6ⁱⁱ—P2—F4	179.0 (4)	C11—C10—N2	107.4 (5)
F4ⁱⁱ—P2—F4	91.4 (5)	C11—C10—H10	126.3
C1—O1—H1	109.5	N2—C10—H10	126.3
C7—N1—C8	118.3 (4)	C10—C11—N3	107.3 (5)
C12—N2—C10	108.3 (4)	C10—C11—H11	126.4
C12—N2—C9	126.8 (5)	N3—C11—H11	126.4
C10—N2—C9	124.9 (4)	N2—C12—N3	109.1 (5)
C12—N3—C11	107.9 (4)	N2—C12—H12	125.5
C12—N3—C13	126.4 (5)	N3—C12—H12	125.5
C11—N3—C13	125.7 (5)	N3—C13—H13A	109.5
O1—C1—C2	119.5 (5)	N3—C13—H13B	109.5
O1—C1—C6	121.6 (4)	H13A—C13—H13B	109.5
C2—C1—C6	118.9 (5)	N3—C13—H13C	109.5
C3—C2—C1	120.3 (5)	H13A—C13—H13C	109.5
C3—C2—H2	119.9	H13B—C13—H13C	109.5

O1—C1—C2—C3	−179.6 (5)	C7—N1—C8—C9	−123.0 (5)
C6—C1—C2—C3	0.6 (8)	C12—N2—C9—C8	107.3 (6)
C1—C2—C3—C4	−0.9 (8)	C10—N2—C9—C8	−72.1 (7)
C2—C3—C4—C5	0.4 (9)	N1—C8—C9—N2	179.9 (4)
C3—C4—C5—C6	0.5 (9)	C12—N2—C10—C11	0.5 (6)
O1—C1—C6—C5	−179.6 (5)	C9—N2—C10—C11	180.0 (5)
C2—C1—C6—C5	0.3 (7)	N2—C10—C11—N3	−0.6 (6)
O1—C1—C6—C7	0.3 (7)	C12—N3—C11—C10	0.5 (6)
C2—C1—C6—C7	−179.9 (5)	C13—N3—C11—C10	178.9 (5)
C4—C5—C6—C1	−0.8 (8)	C10—N2—C12—N3	−0.1 (6)
C4—C5—C6—C7	179.3 (5)	C9—N2—C12—N3	−179.6 (4)
C8—N1—C7—C6	−180.0 (4)	C11—N3—C12—N2	−0.2 (6)
C1—C6—C7—N1	0.5 (7)	C13—N3—C12—N2	−178.6 (5)
C5—C6—C7—N1	−179.7 (5)

Symmetry codes: (i) −x+3/2, −y+3/2, −z; (ii) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.572 (5)	147

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₃O⁺·PF₆⁻
M_r	375.26
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.239 (15), 7.134 (4), 18.017 (9)
β (°)	118.342 (6)
V (Å³)	3194 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.32 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.926, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8091, 2969, 1965
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.215, 1.01
No. of reflections	2969
No. of parameters	221
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.095P)² + 15.5678P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.29

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), 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
O1—H1···N1	0.82	1.85	2.572 (5)	147

Acknowledgements

We are grateful to the National Natural Science Foundation of China (No. 20672046) and the Guangdong Natural Science Foundation (No. 04010458) for financial support.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cai, Y.-Q., Peng, Y.-Q. & Song, G.-H. (2006). Catal. Lett. 109, 61–64. Web of Science CrossRef CAS Google Scholar
Peng, Y.-Q. & Song, G.-H. (2006). Catal. Commun. 8, 111–114. Web of Science CrossRef 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

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Volume 64| Part 12| December 2008| Page o2365

doi:10.1107/S1600536808037124

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

1-{2-[(2-hydroxybenzyl­idene)-amino]-ethyl}-3-methyl-3H-imidazolium hexa­fluorophosphate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{2-[(2-hydroxybenzylidene)-amino]-ethyl}-3-methyl-3H-imidazolium hexafluorophosphate