1-{2-[(4-Hydr­oxy-3-methoxy­benzyl­idene)amino]eth­yl}-3-methylimid­azolium hexa­fluoro­phosphate

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

doi:10.1107/S160053680901928X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1427

doi:10.1107/S160053680901928X

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1-{2-[(4-Hydroxy-3-methoxybenzylidene)amino]ethyl}-3-methylimidazolium hexafluorophosphate

Bin Li,^a Yi-Qun Li,^a ^* Jie Liu ^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 29 April 2009; accepted 21 May 2009; online 29 May 2009)

In the title Schiff base salt, C₁₄H₁₈N₃O₂⁺·PF₆⁻, the dihedral angle between the planes of the aromatic and imidazole rings is 24.84 (8)°. The molecular structure exhibits an intramolecular O—H⋯O hydrogen bond, which generates an S(5) ring motif. In the crystal structure, the cations and anions are connected via O—H⋯N and O—H⋯F hydrogen bonds, resulting in a trifurcated interaction for the phenolic H atom.

Related literature

For bond-length data, see: Allen et al. (1987 ). For the synthesis of Schiff bases, see: Pradeep (2005 ); Butcher et al. (2005 ). For information on ionic liquids and their applications, see: Xiao et al. (2004 ); Welton (1999 ); Wilkes (2002 ).

Experimental

Crystal data

C₁₄H₁₈N₃O₂⁺·PF₆⁻
M_r = 405.28
Monoclinic, P 2₁ /n
a = 7.5285 (10) Å
b = 12.6850 (16) Å
c = 17.827 (2) Å
β = 96.245 (2)°
V = 1692.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.48 × 0.43 × 0.38 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.894, T_max = 0.914
8519 measured reflections
3635 independent reflections
2904 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.099
S = 1.07
3635 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.26 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
O2—H2A⋯O1	0.84	2.20	2.6589 (16)	114
O2—H2A⋯N1ⁱ	0.84	2.48	3.1584 (18)	139
O2—H2A⋯F2ⁱⁱ	0.84	2.49	3.0487 (18)	125
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 I, global. DOI: 10.1107/S160053680901928X/su2112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901928X/su2112Isup2.hkl

checkCIF report

Comment top

Ionic liquids have aroused considerable interest over the past decade due to their wide variety of properties such as high thermal and chemical stability, no measurable vapor pressure, non-flammability, friction reduction, and high loading capacity, etc (Xiao et al., 2004; Welton, 1999; Wilkes, 2002). Schiff base compounds are one of the most prevalent mixed-donor ligands in the field of coordination chemistry (Pradeep, 2005; Butcher et al., 2005). Our interest in this field of research lead us to synthesis the title compound, and we report here on the crystal structure of this novel ionic liquid-supported Schiff base.

The title compound is a Schiff base derived from the condensation of 4-hydroxy-3-methoxybenzaldehyde with the ionic liquid 1-(2-aminoethyl)-3- methylimidazolium hexafluorophosphate, under solvent-free conditions. The molecular structure of the title compound is illustrated in Fig. 1. The asymmetric unit comprises one cation and one PF₆ anion. The bond lengths (Allen et al., 1987) and angles are generally within normal ranges. The aromatic ring and imidazole ring are not coplanar but are inclined to one another by an angle of 24.84 (8)°. In the molecular structure, the intramolocular O2—H2A···O1 hydrogen bonds form a pseudo five membered ring [S(5) motif], thus locking the molecular conformation and eliminating any flexibility (Table 1).

In the crystal structure symmetry related cations and anions are connected via O-H···N and O-H···F hydrogen bonds (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For the synthesis of Schiff bases, see: Pradeep (2005); Butcher et al. (2005). For information on ionic liquids and their applications, see: Xiao et al. (2004); Welton (1999); Wilkes (2002).

Experimental top

A mixture of the ionic liquid 1-(2-aminoethyl)-3-methylimidazolium hexafluorophosphate (4 mmol) and 4-hydroxy-3- methoxybenzaldehyde (3 mmol) was stirred for 4 h at rt, under solvent-free conditions. After completion of the reaction, ethanol (30 ml) was added to the reaction mixture. The solid product was then filtered off 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 analysis, were obtained by slow evaporation of an ethyl acetate solution of the complex at rt.

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, showing the atom numbering Scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data top

C₁₄H₁₈N₃O₂⁺·PF₆⁻	F(000) = 832
M_r = 405.28	D_x = 1.591 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4600 reflections
a = 7.5285 (10) Å	θ = 2.3–27.1°
b = 12.6850 (16) Å	µ = 0.24 mm⁻¹
c = 17.827 (2) Å	T = 173 K
β = 96.245 (2)°	Block, colorless
V = 1692.3 (4) Å³	0.48 × 0.43 × 0.38 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3635 independent reflections
Radiation source: fine-focus sealed tube	2904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 27.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
T_min = 0.894, T_max = 0.914	k = −16→13
8519 measured reflections	l = −22→22

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0489P)² + 0.5604P] where P = (F_o² + 2F_c²)/3
3635 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₈N₃O₂⁺·PF₆⁻	V = 1692.3 (4) Å³
M_r = 405.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5285 (10) Å	µ = 0.24 mm⁻¹
b = 12.6850 (16) Å	T = 173 K
c = 17.827 (2) Å	0.48 × 0.43 × 0.38 mm
β = 96.245 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3635 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2904 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.914	R_int = 0.019
8519 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 0.26 e Å⁻³
3635 reflections	Δρ_min = −0.29 e Å⁻³
238 parameters

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
C1	0.4931 (2)	0.59395 (12)	0.15334 (9)	0.0254 (3)
C2	0.5820 (2)	0.59443 (12)	0.22669 (9)	0.0245 (3)
H2	0.5929	0.6582	0.2548	0.029*
C3	0.6536 (2)	0.50227 (12)	0.25801 (9)	0.0246 (3)
C4	0.6351 (2)	0.40751 (12)	0.21695 (9)	0.0277 (3)
C5	0.5435 (2)	0.40639 (13)	0.14557 (9)	0.0302 (4)
H5	0.5282	0.3421	0.1182	0.036*
C6	0.4735 (2)	0.49990 (12)	0.11374 (9)	0.0283 (3)
H6	0.4118	0.4992	0.0644	0.034*
C7	0.7471 (2)	0.58042 (14)	0.37782 (10)	0.0363 (4)
H7A	0.8078	0.6402	0.3568	0.054*
H7B	0.8098	0.5613	0.4270	0.054*
H7C	0.6236	0.6001	0.3839	0.054*
C8	0.4221 (2)	0.69108 (13)	0.11667 (9)	0.0264 (3)
H8	0.3633	0.6859	0.0669	0.032*
C9	0.3561 (2)	0.86914 (13)	0.10164 (9)	0.0286 (3)
H9A	0.2947	0.8417	0.0537	0.034*
H9B	0.4520	0.9176	0.0894	0.034*
C10	0.2231 (2)	0.92900 (14)	0.14407 (10)	0.0324 (4)
H10A	0.1602	0.9819	0.1100	0.039*
H10B	0.1329	0.8792	0.1598	0.039*
C11	0.3670 (2)	0.93695 (13)	0.27651 (9)	0.0281 (3)
H11	0.3487	0.8652	0.2889	0.034*
C12	0.4516 (2)	1.10234 (13)	0.28397 (10)	0.0330 (4)
H12	0.5030	1.1667	0.3031	0.040*
C13	0.3652 (2)	1.08660 (13)	0.21491 (10)	0.0336 (4)
H13	0.3445	1.1377	0.1760	0.040*
C14	0.5274 (3)	0.98980 (16)	0.39957 (10)	0.0420 (4)
H14A	0.4489	1.0207	0.4341	0.063*
H14B	0.6457	1.0226	0.4081	0.063*
H14C	0.5383	0.9138	0.4088	0.063*
F1	−0.02389 (14)	0.28060 (9)	−0.01415 (7)	0.0477 (3)
F2	0.17917 (17)	0.21418 (9)	−0.08507 (6)	0.0500 (3)
F3	0.07180 (16)	0.11320 (8)	0.00376 (7)	0.0503 (3)
F4	0.35699 (15)	0.17051 (10)	0.02179 (7)	0.0536 (3)
F5	0.15258 (16)	0.23765 (10)	0.09197 (6)	0.0485 (3)
F6	0.26139 (15)	0.33750 (8)	0.00272 (6)	0.0474 (3)
N1	0.43423 (18)	0.78152 (10)	0.14719 (7)	0.0288 (3)
N2	0.31202 (17)	0.98250 (10)	0.21108 (8)	0.0279 (3)
N3	0.45170 (18)	1.00816 (11)	0.32170 (8)	0.0291 (3)
O1	0.74720 (16)	0.49223 (9)	0.32760 (6)	0.0325 (3)
O2	0.70614 (18)	0.31595 (9)	0.24688 (7)	0.0409 (3)
H2A	0.7684	0.3288	0.2879	0.061*
P1	0.16710 (6)	0.22501 (3)	0.00298 (2)	0.02858 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0204 (7)	0.0258 (8)	0.0301 (8)	−0.0006 (6)	0.0031 (6)	0.0002 (6)
C2	0.0254 (7)	0.0209 (7)	0.0274 (8)	−0.0027 (6)	0.0036 (6)	−0.0027 (6)
C3	0.0240 (7)	0.0249 (8)	0.0249 (8)	−0.0043 (6)	0.0027 (6)	0.0006 (6)
C4	0.0300 (8)	0.0210 (7)	0.0316 (9)	−0.0009 (6)	0.0011 (6)	0.0015 (6)
C5	0.0332 (9)	0.0234 (8)	0.0334 (9)	−0.0014 (6)	0.0006 (7)	−0.0063 (7)
C6	0.0265 (8)	0.0299 (8)	0.0272 (8)	−0.0018 (6)	−0.0024 (6)	−0.0023 (7)
C7	0.0422 (10)	0.0370 (10)	0.0285 (9)	0.0013 (8)	−0.0018 (7)	−0.0083 (7)
C8	0.0234 (7)	0.0305 (8)	0.0248 (8)	0.0001 (6)	0.0005 (6)	0.0000 (6)
C9	0.0331 (8)	0.0259 (8)	0.0255 (8)	0.0028 (6)	−0.0024 (6)	0.0015 (6)
C10	0.0286 (8)	0.0317 (9)	0.0351 (9)	0.0054 (7)	−0.0052 (7)	−0.0021 (7)
C11	0.0296 (8)	0.0258 (8)	0.0291 (8)	−0.0015 (6)	0.0043 (6)	−0.0003 (7)
C12	0.0326 (9)	0.0247 (8)	0.0429 (10)	−0.0022 (7)	0.0101 (7)	−0.0038 (7)
C13	0.0357 (9)	0.0234 (8)	0.0427 (10)	0.0041 (7)	0.0087 (7)	0.0029 (7)
C14	0.0475 (11)	0.0507 (12)	0.0272 (9)	−0.0067 (9)	0.0018 (8)	−0.0051 (8)
F1	0.0338 (6)	0.0458 (7)	0.0599 (7)	0.0069 (5)	−0.0110 (5)	−0.0037 (5)
F2	0.0641 (8)	0.0555 (7)	0.0306 (6)	−0.0080 (6)	0.0059 (5)	−0.0050 (5)
F3	0.0612 (8)	0.0312 (6)	0.0591 (8)	−0.0099 (5)	0.0093 (6)	0.0020 (5)
F4	0.0404 (6)	0.0603 (8)	0.0592 (7)	0.0186 (6)	0.0011 (5)	0.0041 (6)
F5	0.0596 (7)	0.0563 (7)	0.0293 (6)	0.0083 (6)	0.0042 (5)	0.0001 (5)
F6	0.0505 (7)	0.0366 (6)	0.0513 (7)	−0.0149 (5)	−0.0111 (5)	0.0023 (5)
N1	0.0337 (7)	0.0258 (7)	0.0259 (7)	0.0046 (6)	−0.0006 (5)	0.0016 (6)
N2	0.0263 (7)	0.0256 (7)	0.0317 (7)	0.0044 (5)	0.0033 (5)	−0.0004 (6)
N3	0.0293 (7)	0.0290 (7)	0.0297 (7)	−0.0026 (6)	0.0064 (5)	−0.0031 (6)
O1	0.0436 (7)	0.0250 (6)	0.0267 (6)	0.0000 (5)	−0.0057 (5)	−0.0007 (5)
O2	0.0582 (9)	0.0214 (6)	0.0388 (7)	0.0025 (6)	−0.0149 (6)	−0.0013 (5)
P1	0.0299 (2)	0.0267 (2)	0.0283 (2)	0.00017 (17)	−0.00086 (16)	0.00051 (17)

Geometric parameters (Å, º) top

C1—C6	1.386 (2)	C10—N2	1.470 (2)
C1—C2	1.403 (2)	C10—H10A	0.9900
C1—C8	1.468 (2)	C10—H10B	0.9900
C2—C3	1.380 (2)	C11—N3	1.327 (2)
C2—H2	0.9500	C11—N2	1.327 (2)
C3—O1	1.3644 (18)	C11—H11	0.9500
C3—C4	1.406 (2)	C12—C13	1.343 (3)
C4—O2	1.3629 (19)	C12—N3	1.371 (2)
C4—C5	1.380 (2)	C12—H12	0.9500
C5—C6	1.393 (2)	C13—N2	1.379 (2)
C5—H5	0.9500	C13—H13	0.9500
C6—H6	0.9500	C14—N3	1.461 (2)
C7—O1	1.433 (2)	C14—H14A	0.9800
C7—H7A	0.9800	C14—H14B	0.9800
C7—H7B	0.9800	C14—H14C	0.9800
C7—H7C	0.9800	F1—P1	1.6008 (11)
C8—N1	1.269 (2)	F2—P1	1.5880 (11)
C8—H8	0.9500	F3—P1	1.5902 (11)
C9—N1	1.4618 (19)	F4—P1	1.5905 (11)
C9—C10	1.521 (2)	F5—P1	1.6101 (11)
C9—H9A	0.9900	F6—P1	1.5941 (11)
C9—H9B	0.9900	O2—H2A	0.8400

C6—C1—C2	119.47 (14)	N3—C11—N2	108.71 (15)
C6—C1—C8	118.84 (14)	N3—C11—H11	125.6
C2—C1—C8	121.68 (14)	N2—C11—H11	125.6
C3—C2—C1	119.96 (14)	C13—C12—N3	107.13 (15)
C3—C2—H2	120.0	C13—C12—H12	126.4
C1—C2—H2	120.0	N3—C12—H12	126.4
O1—C3—C2	125.97 (14)	C12—C13—N2	107.25 (15)
O1—C3—C4	113.93 (13)	C12—C13—H13	126.4
C2—C3—C4	120.09 (14)	N2—C13—H13	126.4
O2—C4—C5	119.19 (14)	N3—C14—H14A	109.5
O2—C4—C3	120.81 (14)	N3—C14—H14B	109.5
C5—C4—C3	120.00 (14)	H14A—C14—H14B	109.5
C4—C5—C6	119.71 (15)	N3—C14—H14C	109.5
C4—C5—H5	120.1	H14A—C14—H14C	109.5
C6—C5—H5	120.1	H14B—C14—H14C	109.5
C1—C6—C5	120.73 (14)	C8—N1—C9	116.33 (14)
C1—C6—H6	119.6	C11—N2—C13	108.20 (14)
C5—C6—H6	119.6	C11—N2—C10	125.74 (14)
O1—C7—H7A	109.5	C13—N2—C10	125.87 (14)
O1—C7—H7B	109.5	C11—N3—C12	108.71 (14)
H7A—C7—H7B	109.5	C11—N3—C14	125.50 (15)
O1—C7—H7C	109.5	C12—N3—C14	125.77 (14)
H7A—C7—H7C	109.5	C3—O1—C7	117.38 (12)
H7B—C7—H7C	109.5	C4—O2—H2A	109.5
N1—C8—C1	124.21 (14)	F2—P1—F3	90.34 (6)
N1—C8—H8	117.9	F2—P1—F4	91.38 (7)
C1—C8—H8	117.9	F3—P1—F4	90.37 (7)
N1—C9—C10	110.50 (14)	F2—P1—F6	90.07 (6)
N1—C9—H9A	109.6	F3—P1—F6	179.46 (7)
C10—C9—H9A	109.6	F4—P1—F6	89.96 (7)
N1—C9—H9B	109.6	F2—P1—F1	89.80 (7)
C10—C9—H9B	109.6	F3—P1—F1	89.88 (6)
H9A—C9—H9B	108.1	F4—P1—F1	178.80 (7)
N2—C10—C9	111.62 (13)	F6—P1—F1	89.78 (6)
N2—C10—H10A	109.3	F2—P1—F5	179.03 (7)
C9—C10—H10A	109.3	F3—P1—F5	90.06 (7)
N2—C10—H10B	109.3	F4—P1—F5	89.50 (6)
C9—C10—H10B	109.3	F6—P1—F5	89.52 (6)
H10A—C10—H10B	108.0	F1—P1—F5	89.32 (6)

C6—C1—C2—C3	1.8 (2)	N3—C12—C13—N2	0.31 (19)
C8—C1—C2—C3	−177.20 (14)	C1—C8—N1—C9	179.71 (14)
C1—C2—C3—O1	178.08 (14)	C10—C9—N1—C8	125.58 (16)
C1—C2—C3—C4	−1.0 (2)	N3—C11—N2—C13	0.40 (18)
O1—C3—C4—O2	0.3 (2)	N3—C11—N2—C10	175.73 (14)
C2—C3—C4—O2	179.53 (15)	C12—C13—N2—C11	−0.44 (19)
O1—C3—C4—C5	−179.91 (15)	C12—C13—N2—C10	−175.77 (15)
C2—C3—C4—C5	−0.7 (2)	C9—C10—N2—C11	−78.2 (2)
O2—C4—C5—C6	−178.65 (15)	C9—C10—N2—C13	96.36 (19)
C3—C4—C5—C6	1.6 (3)	N2—C11—N3—C12	−0.20 (19)
C2—C1—C6—C5	−1.0 (2)	N2—C11—N3—C14	178.01 (15)
C8—C1—C6—C5	178.10 (15)	C13—C12—N3—C11	−0.08 (19)
C4—C5—C6—C1	−0.8 (3)	C13—C12—N3—C14	−178.29 (16)
C6—C1—C8—N1	−179.14 (16)	C2—C3—O1—C7	10.9 (2)
C2—C1—C8—N1	−0.1 (2)	C4—C3—O1—C7	−169.95 (15)
N1—C9—C10—N2	66.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.84	2.20	2.6589 (16)	114
O2—H2A···N1ⁱ	0.84	2.48	3.1584 (18)	139
O2—H2A···F2ⁱⁱ	0.84	2.49	3.0487 (18)	125

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₃O₂⁺·PF₆⁻
M_r	405.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	7.5285 (10), 12.6850 (16), 17.827 (2)
β (°)	96.245 (2)
V (Å³)	1692.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.48 × 0.43 × 0.38

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.894, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	8519, 3635, 2904
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.099, 1.07
No. of reflections	3635
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.29

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
O2—H2A···O1	0.84	2.20	2.6589 (16)	114
O2—H2A···N1ⁱ	0.84	2.48	3.1584 (18)	139
O2—H2A···F2ⁱⁱ	0.84	2.49	3.0487 (18)	125

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

Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2002). SMART and 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
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
Welton, T. (1999). Chem. Rev. 99, 2071–2083. Web of Science CrossRef PubMed CAS Google Scholar
Wilkes, J. S. (2002). Green Chem. 4, 73–80. Web of Science CrossRef CAS Google Scholar
Xiao, Y. & Malhotra, S. V. (2004). Tetrahedron Lett. 45, 8339–8342. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 6| June 2009| Page o1427

doi:10.1107/S160053680901928X

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

1-{2-[(4-Hydr­­oxy-3-meth­oxy­benzyl­­idene)amino]eth­yl}-3-methylimid­azolium hexa­fluoro­phosphate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{2-[(4-Hydroxy-3-methoxybenzylidene)amino]ethyl}-3-methylimidazolium hexafluorophosphate