3-[(8-But­oxy­quinolin-2-yl)meth­yl]-1-(pyridin-2-ylmeth­yl)-1H-imidazol-3-ium hexa­fluoridophosphate

Zhang, P.; Jing, J.; Qin, D.-B.

doi:10.1107/S1600536812013414

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1278

doi:10.1107/S1600536812013414

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3-[(8-Butoxyquinolin-2-yl)methyl]-1-(pyridin-2-ylmethyl)-1H-imidazol-3-ium hexafluoridophosphate

Ping Zhang,^a Jing Jing ^a and Da-Bin Qin ^a ^*

^aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, School of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabin2005@yahoo.com.cn

(Received 6 March 2012; accepted 28 March 2012; online 4 April 2012)

In the cation of the title compound, C₂₃H₂₅N₄O⁺·PF₆⁻, the imidazolium ring make dihedral angles of 87.20 (6) and 79.89 (5)° with the pyridine ring and the quinoline system, respectively. In the crystal, C—H⋯F and C—H⋯N hydrogen bonds are observed.

Related literature

For the first stable N-heterocyclic carbene, see: Arduengo et al. (1991 ). For the synthesis of 8-butoxy-quinoline-2-carbaldehyde, see: Maffeo et al. (2003 ), of 8-butoxy-2-chloromethyl-quinoline, see: Fowelin et al. (2007 ) and of 2-((1H-imidazol-1-yl)methyl)pyridine, see: Chiu et al. (2005 ). For ionic liquids from imidazolium salts, see: Heller et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₂₅N₄O⁺·PF₆⁻
M_r = 518.44
Triclinic, $[P \overline 1]$
a = 9.975 (3) Å
b = 11.056 (4) Å
c = 12.382 (4) Å
α = 99.010 (4)°
β = 103.527 (3)°
γ = 112.734 (3)°
V = 1177.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.956, T_max = 0.967
12352 measured reflections
5531 independent reflections
2844 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.01
5531 reflections
317 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N4ⁱ	0.95	2.58	3.343 (2)	138
C14—H14B⋯F1ⁱⁱ	0.99	2.50	3.425 (2)	156
C16—H16⋯F4ⁱ	0.95	2.46	3.361 (2)	159
C17—H17⋯F6ⁱⁱ	0.95	2.32	3.223 (2)	158
C23—H23⋯F4ⁱⁱⁱ	0.95	2.52	3.355 (2)	147
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1; (iii) x, y+1, z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013414/fj2531sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013414/fj2531Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013414/fj2531Isup3.cml

checkCIF report

Comment top

since the isolation of the first stable derivative of N-heterocyclic carbenes (Arduengo et al., 1991), the chemistry of N-heterocyclic carbenes has been studied intensely, so numerous stable NHC ligands has been prepared. Imidazolium salts are considerable good precursor for the synthesis of N-heterocyclic carbenes. In addition, the study of ionic liquids of imidazolium salts (Heller et al., 2010) have been reported during these years.

We report herein the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles in the cation are normal. The imidazolium ring make dihedral angles with the pyridine ring and the quinoline ring of 87.20 (6)° and 79.89 (5)°, respectively. In the crystal there are weak π···π interactions involving the pyridine ring with centroid-centroid distances, Cg2···Cg4ⁱ of 3.692 (9). [symmetry codes: (i) 1 - x, 2 - y, 1 - z] In addition, extensive C—H···F and C—H···N hydrogen bonds which contribute to the stability of molecular structure are observed (Table 1 and Fig. 2).

Related literature top

For the first stable N-heterocyclic carbene, see: Arduengo et al. (1991). For the synthesis of 8-butoxy-quinoline-2-carbaldehyde, see: Maffeo et al. (2003), of 8-butoxy-2-chloromethyl-quinoline, see: Fowelin et al. (2007) and of 2-((1H-imidazol-1-yl)methyl)pyridine, see: Chiu et al. (2005). For ionic liquids from imidazolium salts, see: Heller et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

8-Butoxy-2-chloromethyl-quinoline (Maffeo et al., 2003 and Fowelin et al., 2007) (2.49 g, 10 mmol) was added to a solution of 2-((1H-imidazol-1-yl)methyl)pyridine (Chiu et al., 2005) (1.59 g, 10 mmol) in 50 ml of THF. The mixture was refluxed for 48 h. The resulting precipitate was isolated and washed with THF(2 × 5 ml) and was then dissolved in methanol (20 ml). Adding an excess of NH₄PF₆ to the aqueous solution yielded the title compound. Colorless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile and diethyl ether(v/v=1/4).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: CrystalStructure (Rigaku, 2005).

Figures top

	Fig. 1. A view of the molecular structure of the title compound with atom numbering. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, showing the cations and anions linked via C—H···F interactions (dashed lines). H atoms not involved in these interactions have been omitted for clarity. [symmetry codes: (i) 1 - x,1 - y,1 - z; (ii) 2 - x,1 - y,1 - z; (iii) x,1 + y,1 + z].

3-[(8-Butoxyquinolin-2-yl)methyl]-1-(pyridin-2-ylmethyl)- 1H-imidazol-3-ium hexafluoridophosphate top

Crystal data top

C₂₃H₂₅N₄O⁺·PF₆⁻	Z = 2
M_r = 518.44	F(000) = 536
Triclinic, P1	D_x = 1.463 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.975 (3) Å	Cell parameters from 3783 reflections
b = 11.056 (4) Å	θ = 1.8–27.9°
c = 12.382 (4) Å	µ = 0.19 mm⁻¹
α = 99.010 (4)°	T = 113 K
β = 103.527 (3)°	Prism, colourless
γ = 112.734 (3)°	0.24 × 0.20 × 0.18 mm
V = 1177.1 (7) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5531 independent reflections
Radiation source: rotating anode	2844 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.037
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.8°
ω and ϕ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→14
T_min = 0.956, T_max = 0.967	l = −15→16
12352 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0259P)²] where P = (F_o² + 2F_c²)/3
5531 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₃H₂₅N₄O⁺·PF₆⁻	γ = 112.734 (3)°
M_r = 518.44	V = 1177.1 (7) Å³
Triclinic, P1	Z = 2
a = 9.975 (3) Å	Mo Kα radiation
b = 11.056 (4) Å	µ = 0.19 mm⁻¹
c = 12.382 (4) Å	T = 113 K
α = 99.010 (4)°	0.24 × 0.20 × 0.18 mm
β = 103.527 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5531 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2844 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.967	R_int = 0.037
12352 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.01	Δρ_max = 0.58 e Å⁻³
5531 reflections	Δρ_min = −0.24 e Å⁻³
317 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
O1	0.18574 (14)	−0.05015 (11)	0.50857 (9)	0.0261 (3)
N1	0.46828 (17)	0.15399 (13)	0.59818 (11)	0.0207 (3)
N2	0.67464 (17)	0.44123 (14)	0.81155 (11)	0.0222 (3)
N3	0.76044 (18)	0.65447 (14)	0.89753 (11)	0.0243 (3)
N4	0.7840 (2)	0.96366 (16)	1.02355 (13)	0.0430 (5)
C1	0.4087 (2)	0.10204 (16)	0.48018 (13)	0.0199 (4)
C2	0.2576 (2)	−0.00743 (17)	0.43121 (14)	0.0230 (4)
C3	0.1955 (2)	−0.06110 (18)	0.31350 (14)	0.0266 (4)
H3	0.0950	−0.1341	0.2805	0.032*
C4	0.2801 (2)	−0.00833 (18)	0.24126 (14)	0.0272 (4)
H4	0.2356	−0.0472	0.1600	0.033*
C5	0.4231 (2)	0.09621 (17)	0.28470 (14)	0.0258 (4)
H5	0.4769	0.1310	0.2341	0.031*
C6	0.4921 (2)	0.15361 (17)	0.40557 (14)	0.0229 (4)
C7	0.6411 (2)	0.26183 (17)	0.45754 (15)	0.0266 (4)
H7	0.7005	0.2993	0.4109	0.032*
C8	0.6998 (2)	0.31251 (17)	0.57488 (15)	0.0275 (4)
H8	0.8000	0.3854	0.6107	0.033*
C9	0.6087 (2)	0.25439 (17)	0.64230 (14)	0.0233 (4)
C10	0.0333 (2)	−0.15994 (17)	0.46166 (14)	0.0256 (4)
H10A	0.0348	−0.2408	0.4154	0.031*
H10B	−0.0352	−0.1324	0.4105	0.031*
C11	−0.0249 (2)	−0.19441 (17)	0.55992 (14)	0.0263 (4)
H11A	−0.0195	−0.1114	0.6084	0.032*
H11B	0.0421	−0.2253	0.6087	0.032*
C12	−0.1897 (2)	−0.30559 (18)	0.51700 (14)	0.0288 (4)
H12A	−0.2554	−0.2771	0.4642	0.035*
H12B	−0.1937	−0.3902	0.4725	0.035*
C13	−0.2529 (2)	−0.33511 (18)	0.61483 (15)	0.0319 (5)
H13A	−0.1896	−0.3654	0.6664	0.048*
H13B	−0.3588	−0.4069	0.5831	0.048*
H13C	−0.2512	−0.2521	0.6583	0.048*
C14	0.6703 (2)	0.30680 (16)	0.77246 (14)	0.0252 (4)
H14A	0.6045	0.2414	0.8059	0.030*
H14B	0.7753	0.3138	0.8003	0.030*
C15	0.5510 (2)	0.47198 (18)	0.79151 (14)	0.0265 (4)
H15	0.4474	0.4105	0.7479	0.032*
C16	0.6041 (2)	0.60457 (18)	0.84485 (14)	0.0267 (4)
H16	0.5454	0.6547	0.8462	0.032*
C17	0.7995 (2)	0.55370 (17)	0.87609 (13)	0.0237 (4)
H17	0.9003	0.5608	0.9026	0.028*
C18	0.8687 (2)	0.79717 (18)	0.96022 (16)	0.0376 (5)
H18A	0.8857	0.8516	0.9042	0.045*
H18B	0.9686	0.8015	1.0025	0.045*
C19	0.8087 (2)	0.85781 (17)	1.04502 (15)	0.0274 (4)
C20	0.7801 (2)	0.80741 (19)	1.13636 (15)	0.0317 (5)
H20	0.7968	0.7308	1.1481	0.038*
C21	0.7279 (2)	0.86810 (18)	1.20933 (15)	0.0320 (5)
H21	0.7099	0.8355	1.2736	0.038*
C22	0.7014 (2)	0.97635 (19)	1.18994 (16)	0.0366 (5)
H22	0.6644	1.0200	1.2399	0.044*
C23	0.7295 (3)	1.0200 (2)	1.09668 (18)	0.0528 (7)
H23	0.7096	1.0944	1.0825	0.063*
P1	0.80855 (6)	0.43611 (5)	0.15376 (4)	0.02658 (13)
F1	0.93828 (12)	0.57111 (10)	0.14046 (9)	0.0424 (3)
F2	0.93902 (13)	0.42366 (12)	0.24704 (9)	0.0496 (3)
F3	0.78373 (14)	0.52848 (11)	0.25236 (8)	0.0464 (3)
F4	0.68142 (13)	0.30267 (10)	0.16650 (9)	0.0427 (3)
F5	0.68041 (12)	0.45015 (10)	0.05947 (8)	0.0379 (3)
F6	0.83460 (13)	0.34588 (10)	0.05310 (9)	0.0395 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0258 (8)	0.0272 (7)	0.0218 (6)	0.0064 (6)	0.0117 (6)	0.0048 (5)
N1	0.0231 (9)	0.0193 (8)	0.0218 (8)	0.0122 (7)	0.0083 (7)	0.0022 (6)
N2	0.0215 (9)	0.0244 (8)	0.0206 (8)	0.0109 (7)	0.0075 (7)	0.0034 (7)
N3	0.0233 (9)	0.0214 (8)	0.0245 (8)	0.0071 (7)	0.0104 (7)	−0.0007 (7)
N4	0.0672 (14)	0.0345 (10)	0.0355 (10)	0.0252 (10)	0.0244 (10)	0.0121 (8)
C1	0.0242 (11)	0.0191 (9)	0.0205 (9)	0.0134 (8)	0.0083 (8)	0.0048 (8)
C2	0.0277 (11)	0.0234 (10)	0.0254 (10)	0.0151 (9)	0.0135 (9)	0.0089 (8)
C3	0.0263 (11)	0.0277 (10)	0.0235 (10)	0.0108 (9)	0.0073 (9)	0.0049 (8)
C4	0.0346 (12)	0.0320 (11)	0.0180 (10)	0.0186 (10)	0.0077 (9)	0.0060 (8)
C5	0.0356 (12)	0.0277 (10)	0.0244 (10)	0.0180 (10)	0.0173 (9)	0.0125 (8)
C6	0.0290 (11)	0.0213 (10)	0.0262 (10)	0.0162 (9)	0.0122 (9)	0.0080 (8)
C7	0.0308 (12)	0.0242 (10)	0.0340 (11)	0.0149 (9)	0.0191 (9)	0.0121 (9)
C8	0.0246 (11)	0.0208 (10)	0.0342 (11)	0.0085 (9)	0.0093 (9)	0.0045 (8)
C9	0.0281 (11)	0.0200 (9)	0.0240 (10)	0.0141 (9)	0.0079 (9)	0.0033 (8)
C10	0.0221 (11)	0.0237 (10)	0.0257 (10)	0.0057 (9)	0.0081 (9)	0.0035 (8)
C11	0.0292 (12)	0.0269 (10)	0.0257 (10)	0.0138 (9)	0.0120 (9)	0.0067 (8)
C12	0.0290 (12)	0.0283 (10)	0.0267 (10)	0.0091 (9)	0.0121 (9)	0.0056 (8)
C13	0.0351 (13)	0.0314 (11)	0.0372 (11)	0.0160 (10)	0.0203 (10)	0.0136 (9)
C14	0.0261 (11)	0.0226 (9)	0.0259 (10)	0.0119 (9)	0.0068 (9)	0.0033 (8)
C15	0.0181 (10)	0.0295 (11)	0.0293 (10)	0.0102 (9)	0.0063 (9)	0.0036 (9)
C16	0.0243 (11)	0.0305 (11)	0.0308 (11)	0.0154 (9)	0.0130 (9)	0.0078 (9)
C17	0.0212 (11)	0.0310 (10)	0.0193 (9)	0.0119 (9)	0.0085 (8)	0.0040 (8)
C18	0.0336 (13)	0.0292 (11)	0.0411 (12)	0.0054 (10)	0.0185 (10)	−0.0015 (9)
C19	0.0282 (12)	0.0216 (10)	0.0280 (10)	0.0082 (9)	0.0103 (9)	0.0007 (8)
C20	0.0339 (13)	0.0289 (11)	0.0357 (11)	0.0158 (10)	0.0114 (10)	0.0125 (9)
C21	0.0320 (12)	0.0333 (11)	0.0232 (10)	0.0074 (10)	0.0092 (9)	0.0063 (9)
C22	0.0427 (14)	0.0368 (12)	0.0326 (11)	0.0203 (11)	0.0174 (10)	0.0002 (10)
C23	0.090 (2)	0.0404 (13)	0.0560 (15)	0.0466 (14)	0.0362 (14)	0.0196 (12)
P1	0.0242 (3)	0.0309 (3)	0.0284 (3)	0.0139 (2)	0.0126 (2)	0.0076 (2)
F1	0.0294 (7)	0.0331 (6)	0.0621 (8)	0.0080 (6)	0.0193 (6)	0.0145 (6)
F2	0.0400 (8)	0.0768 (9)	0.0428 (7)	0.0351 (7)	0.0096 (6)	0.0261 (7)
F3	0.0481 (8)	0.0562 (8)	0.0369 (7)	0.0280 (7)	0.0181 (6)	−0.0014 (6)
F4	0.0401 (8)	0.0363 (6)	0.0662 (8)	0.0170 (6)	0.0334 (6)	0.0272 (6)
F5	0.0286 (7)	0.0558 (7)	0.0359 (6)	0.0209 (6)	0.0123 (5)	0.0211 (6)
F6	0.0346 (7)	0.0393 (6)	0.0431 (6)	0.0149 (6)	0.0204 (6)	−0.0012 (5)

Geometric parameters (Å, º) top

O1—C2	1.3621 (19)	C11—H11A	0.9900
O1—C10	1.436 (2)	C11—H11B	0.9900
N1—C9	1.320 (2)	C12—C13	1.514 (2)
N1—C1	1.3729 (19)	C12—H12A	0.9900
N2—C17	1.327 (2)	C12—H12B	0.9900
N2—C15	1.380 (2)	C13—H13A	0.9800
N2—C14	1.470 (2)	C13—H13B	0.9800
N3—C17	1.324 (2)	C13—H13C	0.9800
N3—C16	1.381 (2)	C14—H14A	0.9900
N3—C18	1.471 (2)	C14—H14B	0.9900
N4—C19	1.338 (2)	C15—C16	1.341 (2)
N4—C23	1.348 (2)	C15—H15	0.9500
C1—C6	1.425 (2)	C16—H16	0.9500
C1—C2	1.427 (2)	C17—H17	0.9500
C2—C3	1.372 (2)	C18—C19	1.515 (2)
C3—C4	1.410 (2)	C18—H18A	0.9900
C3—H3	0.9500	C18—H18B	0.9900
C4—C5	1.353 (2)	C19—C20	1.377 (2)
C4—H4	0.9500	C20—C21	1.355 (2)
C5—C6	1.414 (2)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.366 (2)
C6—C7	1.411 (2)	C21—H21	0.9500
C7—C8	1.364 (2)	C22—C23	1.366 (3)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.417 (2)	C23—H23	0.9500
C8—H8	0.9500	P1—F4	1.5906 (12)
C9—C14	1.510 (2)	P1—F2	1.5911 (12)
C10—C11	1.506 (2)	P1—F5	1.5916 (11)
C10—H10A	0.9900	P1—F3	1.5941 (11)
C10—H10B	0.9900	P1—F6	1.6058 (11)
C11—C12	1.524 (2)	P1—F1	1.6165 (12)

C2—O1—C10	116.58 (13)	H13A—C13—H13B	109.5
C9—N1—C1	117.78 (15)	C12—C13—H13C	109.5
C17—N2—C15	108.25 (14)	H13A—C13—H13C	109.5
C17—N2—C14	125.14 (15)	H13B—C13—H13C	109.5
C15—N2—C14	126.58 (15)	N2—C14—C9	111.12 (13)
C17—N3—C16	108.55 (15)	N2—C14—H14A	109.4
C17—N3—C18	125.01 (17)	C9—C14—H14A	109.4
C16—N3—C18	126.31 (15)	N2—C14—H14B	109.4
C19—N4—C23	116.48 (16)	C9—C14—H14B	109.4
N1—C1—C6	122.35 (16)	H14A—C14—H14B	108.0
N1—C1—C2	118.46 (15)	C16—C15—N2	107.39 (16)
C6—C1—C2	119.20 (15)	C16—C15—H15	126.3
O1—C2—C3	125.06 (17)	N2—C15—H15	126.3
O1—C2—C1	115.38 (15)	C15—C16—N3	106.97 (16)
C3—C2—C1	119.56 (16)	C15—C16—H16	126.5
C2—C3—C4	120.29 (18)	N3—C16—H16	126.5
C2—C3—H3	119.9	N3—C17—N2	108.84 (16)
C4—C3—H3	119.9	N3—C17—H17	125.6
C5—C4—C3	121.72 (17)	N2—C17—H17	125.6
C5—C4—H4	119.1	N3—C18—C19	111.41 (15)
C3—C4—H4	119.1	N3—C18—H18A	109.3
C4—C5—C6	119.87 (17)	C19—C18—H18A	109.3
C4—C5—H5	120.1	N3—C18—H18B	109.3
C6—C5—H5	120.1	C19—C18—H18B	109.3
C7—C6—C5	123.27 (16)	H18A—C18—H18B	108.0
C7—C6—C1	117.37 (16)	N4—C19—C20	122.50 (17)
C5—C6—C1	119.36 (17)	N4—C19—C18	114.66 (16)
C8—C7—C6	119.95 (17)	C20—C19—C18	122.83 (16)
C8—C7—H7	120.0	C21—C20—C19	119.39 (17)
C6—C7—H7	120.0	C21—C20—H20	120.3
C7—C8—C9	118.76 (17)	C19—C20—H20	120.3
C7—C8—H8	120.6	C20—C21—C22	119.65 (17)
C9—C8—H8	120.6	C20—C21—H21	120.2
N1—C9—C8	123.78 (16)	C22—C21—H21	120.2
N1—C9—C14	115.93 (16)	C21—C22—C23	118.07 (18)
C8—C9—C14	120.29 (17)	C21—C22—H22	121.0
O1—C10—C11	108.68 (13)	C23—C22—H22	121.0
O1—C10—H10A	110.0	N4—C23—C22	123.88 (18)
C11—C10—H10A	110.0	N4—C23—H23	118.1
O1—C10—H10B	110.0	C22—C23—H23	118.1
C11—C10—H10B	110.0	F4—P1—F2	90.58 (7)
H10A—C10—H10B	108.3	F4—P1—F5	90.40 (7)
C10—C11—C12	111.93 (14)	F2—P1—F5	178.92 (7)
C10—C11—H11A	109.2	F4—P1—F3	90.28 (7)
C12—C11—H11A	109.2	F2—P1—F3	90.96 (7)
C10—C11—H11B	109.2	F5—P1—F3	89.48 (6)
C12—C11—H11B	109.2	F4—P1—F6	90.85 (6)
H11A—C11—H11B	107.9	F2—P1—F6	89.68 (7)
C13—C12—C11	112.43 (15)	F5—P1—F6	89.86 (6)
C13—C12—H12A	109.1	F3—P1—F6	178.69 (6)
C11—C12—H12A	109.1	F4—P1—F1	179.61 (7)
C13—C12—H12B	109.1	F2—P1—F1	89.25 (7)
C11—C12—H12B	109.1	F5—P1—F1	89.76 (6)
H12A—C12—H12B	107.8	F3—P1—F1	90.07 (7)
C12—C13—H13A	109.5	F6—P1—F1	88.80 (6)
C12—C13—H13B	109.5

C9—N1—C1—C6	−0.7 (2)	C10—C11—C12—C13	−176.49 (14)
C9—N1—C1—C2	179.40 (15)	C17—N2—C14—C9	−122.16 (17)
C10—O1—C2—C3	0.0 (2)	C15—N2—C14—C9	60.2 (2)
C10—O1—C2—C1	179.81 (13)	N1—C9—C14—N2	−106.79 (17)
N1—C1—C2—O1	0.2 (2)	C8—C9—C14—N2	73.1 (2)
C6—C1—C2—O1	−179.75 (13)	C17—N2—C15—C16	0.15 (19)
N1—C1—C2—C3	180.00 (14)	C14—N2—C15—C16	178.14 (14)
C6—C1—C2—C3	0.1 (2)	N2—C15—C16—N3	−0.05 (19)
O1—C2—C3—C4	179.65 (15)	C17—N3—C16—C15	−0.07 (19)
C1—C2—C3—C4	−0.2 (2)	C18—N3—C16—C15	175.97 (15)
C2—C3—C4—C5	−0.5 (3)	C16—N3—C17—N2	0.16 (19)
C3—C4—C5—C6	1.1 (3)	C18—N3—C17—N2	−175.93 (14)
C4—C5—C6—C7	179.41 (16)	C15—N2—C17—N3	−0.19 (19)
C4—C5—C6—C1	−1.2 (2)	C14—N2—C17—N3	−178.22 (13)
N1—C1—C6—C7	0.1 (2)	C17—N3—C18—C19	−137.01 (17)
C2—C1—C6—C7	−179.98 (14)	C16—N3—C18—C19	47.6 (2)
N1—C1—C6—C5	−179.33 (14)	C23—N4—C19—C20	0.2 (3)
C2—C1—C6—C5	0.6 (2)	C23—N4—C19—C18	179.58 (19)
C5—C6—C7—C8	179.60 (15)	N3—C18—C19—N4	−117.59 (19)
C1—C6—C7—C8	0.2 (2)	N3—C18—C19—C20	61.8 (2)
C6—C7—C8—C9	0.1 (2)	N4—C19—C20—C21	−1.4 (3)
C1—N1—C9—C8	1.0 (2)	C18—C19—C20—C21	179.30 (18)
C1—N1—C9—C14	−179.09 (13)	C19—C20—C21—C22	1.4 (3)
C7—C8—C9—N1	−0.7 (3)	C20—C21—C22—C23	−0.3 (3)
C7—C8—C9—C14	179.37 (15)	C19—N4—C23—C22	1.0 (4)
C2—O1—C10—C11	178.73 (13)	C21—C22—C23—N4	−0.9 (4)
O1—C10—C11—C12	177.10 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N4ⁱ	0.95	2.58	3.343 (2)	138
C14—H14B···F1ⁱⁱ	0.99	2.50	3.425 (2)	156
C16—H16···F4ⁱ	0.95	2.46	3.361 (2)	159
C17—H17···F6ⁱⁱ	0.95	2.32	3.223 (2)	158
C23—H23···F4ⁱⁱⁱ	0.95	2.52	3.355 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₅N₄O⁺·PF₆⁻
M_r	518.44
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.975 (3), 11.056 (4), 12.382 (4)
α, β, γ (°)	99.010 (4), 103.527 (3), 112.734 (3)
V (Å³)	1177.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.956, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	12352, 5531, 2844
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.087, 1.01
No. of reflections	5531
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.24

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N4ⁱ	0.95	2.58	3.343 (2)	138
C14—H14B···F1ⁱⁱ	0.99	2.50	3.425 (2)	156
C16—H16···F4ⁱ	0.95	2.46	3.361 (2)	159
C17—H17···F6ⁱⁱ	0.95	2.32	3.223 (2)	158
C23—H23···F4ⁱⁱⁱ	0.95	2.52	3.355 (2)	147

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

Acknowledgements

The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003)

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
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361–363. CSD CrossRef CAS Web of Science Google Scholar
Chiu, P. L., Lai, C. L., Chang, C. F., Hu, C. H. & Lee, H. M. (2005). Organometallics, 24, 6169–6178. Web of Science CSD CrossRef CAS Google Scholar
Fowelin, C., Schuepbach, B. & Terfort, A. (2007). Eur. J. Org. Chem. 6, 1013–1017. Web of Science CSD CrossRef Google Scholar
Heller, W. T., Q'Neill, H. M., Zhang, Q. & Baker, G. A. (2010). J. Phys. Chem. B, 114, 13866–13871. Web of Science CrossRef CAS PubMed Google Scholar
Maffeo, D. & Williams, J. A. G. (2003). Inorg. Chim. Acta, 355, 127–136. Web of Science CrossRef CAS Google Scholar
Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. 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 68| Part 5| May 2012| Page o1278

doi:10.1107/S1600536812013414

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3-[(8-But­­oxy­quinolin-2-yl)meth­yl]-1-(pyridin-2-ylmeth­yl)-1H-imidazol-3-ium hexa­fluoridophosphate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

3-[(8-Butoxyquinolin-2-yl)methyl]-1-(pyridin-2-ylmethyl)-1H-imidazol-3-ium hexafluoridophosphate