2,3-Dimethyl-1-[2-(4-pyrid­yloxy)eth­yl]imidazol-1-ium hexa­fluoro­phosphate

The title compound, C₁₂H₁₆N₃O⁺·PF₆⁻, contains an imidazolium cation with PF₆⁻ as counter-anion. The structure is stablized by a weak inter­molecular C—H...N inter­action.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.075
• wR factor = 0.198
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT214_ALERT_2_C Atom F3      (Anion/Solvent) ADP max/min Ratio         4.10 prola
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      46.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1'    ..  N1      ..       2.95 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997; molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

2,3-Dimethyl-1-[2-(4-pyridyloxy)ethyl]imidazol-1-ium hexafluorophosphate

Crystal data

C12H16N3O^+·F6P^−	F(000) = 744
Mr = 363.25	Dx = 1.544 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.469 (5) Å	Cell parameters from 831 reflections
b = 16.470 (7) Å	θ = 3.0–25.4°
c = 7.943 (3) Å	µ = 0.25 mm^−1
β = 106.691 (5)°	T = 293 K
V = 1562.5 (11) Å^3	Block, colourless
Z = 4	0.35 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3321 independent reflections
Radiation source: fine-focus sealed tube	2292 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
φ and ω scans	θmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick,2001)	h = −15→10
Tmin = 0.919, Tmax = 0.930	k = −18→20
7576 measured reflections	l = −8→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.198	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1042P)^2 + 0.4283P] where P = (Fo^2 + 2Fc^2)/3
3321 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

Experimental. ¹H NMR [(CD₃)₂CO, δ]: 8.40 (d, 1H), 8.39 (d, 1H), 7.75 (s, 1H), 7.63 (s, 1H), 6.95 (d, 1H), 6.94 (d, 1H), 4.83 (t, 2H), 4.56 (t, 2H), 3.97 (s, 3H), 2.95 (s, 3H); ¹³C NMR [CD₃)₂CO, δ]: 165.46, 152.63, 147.63, 124.20, 123.21, 111.71, 67.62, 49.02, 36.27, 29.98, 10.70.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.76985 (17)	0.08430 (11)	0.4759 (3)	0.0457 (5)
C2	0.8568 (2)	0.12938 (14)	0.5656 (3)	0.0489 (6)
C21	0.8631 (3)	0.1783 (2)	0.7241 (4)	0.0745 (9)
H21A	0.8009	0.1652	0.7676	0.112*	0.50
H21B	0.8608	0.2350	0.6949	0.112*	0.50
H21C	0.9318	0.1665	0.8129	0.112*	0.50
H21D	0.9281	0.2125	0.7493	0.112*	0.50
H21E	0.8682	0.1428	0.8220	0.112*	0.50
H21F	0.7972	0.2113	0.7040	0.112*	0.50
N3	0.93678 (18)	0.12169 (13)	0.4869 (3)	0.0528 (5)
C31	1.0480 (2)	0.1599 (2)	0.5438 (5)	0.0737 (9)
H31A	1.0899	0.1453	0.4640	0.110*	0.50
H31B	1.0871	0.1416	0.6599	0.110*	0.50
H31C	1.0397	0.2179	0.5444	0.110*	0.50
H31D	1.0545	0.1912	0.6482	0.110*	0.50
H31E	1.0574	0.1949	0.4523	0.110*	0.50
H31F	1.1047	0.1187	0.5678	0.110*	0.50
C4	0.9011 (2)	0.07045 (16)	0.3455 (4)	0.0557 (6)
H4	0.9416	0.0548	0.2691	0.067*
C5	0.7970 (2)	0.04735 (15)	0.3386 (3)	0.0515 (6)
H5	0.7514	0.0127	0.2560	0.062*
C6	0.6632 (2)	0.07494 (16)	0.5143 (4)	0.0546 (6)
H6A	0.6737	0.0849	0.6384	0.066*
H6B	0.6371	0.0195	0.4892	0.066*
C7	0.5759 (2)	0.13227 (15)	0.4081 (4)	0.0531 (6)
H7A	0.5633	0.1227	0.2834	0.064*
H7B	0.5056	0.1249	0.4357	0.064*
O1	0.61819 (16)	0.21263 (10)	0.4538 (3)	0.0599 (5)
C11	0.5522 (2)	0.27651 (14)	0.3848 (3)	0.0480 (6)
C12	0.5965 (2)	0.35248 (16)	0.4319 (4)	0.0558 (6)
H12	0.6686	0.3582	0.5069	0.067*
C13	0.5336 (3)	0.41910 (17)	0.3676 (4)	0.0660 (8)
H13	0.5654	0.4699	0.4001	0.079*
N14	0.4294 (3)	0.41629 (16)	0.2609 (4)	0.0791 (8)
C15	0.3891 (3)	0.3422 (2)	0.2161 (5)	0.0810 (10)
H15	0.3170	0.3384	0.1400	0.097*
C16	0.4445 (2)	0.27070 (18)	0.2724 (4)	0.0617 (7)
H16	0.4113	0.2206	0.2365	0.074*
P1	0.18281 (7)	0.09274 (5)	0.11619 (10)	0.0656 (3)
F1	0.1512 (13)	0.0176 (10)	0.194 (3)	0.254 (11)	0.425 (7)
F1'	0.1477 (8)	0.0447 (5)	0.2602 (12)	0.143 (4)	0.575 (7)
F2	0.2062 (8)	0.1749 (6)	0.0213 (16)	0.116 (3)	0.425 (7)
F2'	0.2227 (9)	0.1275 (8)	−0.0286 (13)	0.191 (5)	0.575 (7)
F3	0.2790 (15)	0.0508 (15)	0.0913 (18)	0.278 (11)	0.425 (7)
F3'	0.1952 (8)	0.0067 (5)	0.0430 (13)	0.177 (5)	0.575 (7)
F4	0.0713 (9)	0.1428 (5)	0.1212 (14)	0.119 (4)	0.425 (7)
F4'	0.0615 (5)	0.1023 (7)	0.0364 (17)	0.201 (6)	0.575 (7)
F5	0.2447 (9)	0.1174 (8)	0.2958 (8)	0.161 (5)	0.425 (7)
F5'	0.1910 (6)	0.1775 (3)	0.2026 (16)	0.159 (4)	0.575 (7)
F6	0.1058 (10)	0.0675 (5)	−0.0780 (8)	0.127 (4)	0.425 (7)
F6'	0.3127 (4)	0.0829 (3)	0.2212 (11)	0.108 (2)	0.575 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0454 (12)	0.0417 (10)	0.0459 (11)	0.0032 (8)	0.0064 (9)	0.0025 (8)
C2	0.0490 (14)	0.0431 (12)	0.0449 (13)	0.0045 (10)	−0.0022 (11)	0.0023 (9)
C21	0.077 (2)	0.0752 (19)	0.0572 (17)	0.0045 (16)	−0.0038 (15)	−0.0169 (14)
N3	0.0447 (12)	0.0492 (11)	0.0562 (12)	−0.0009 (9)	0.0009 (10)	0.0028 (9)
C31	0.0483 (16)	0.080 (2)	0.081 (2)	−0.0131 (14)	−0.0014 (14)	0.0001 (16)
C4	0.0532 (16)	0.0580 (14)	0.0553 (15)	0.0035 (11)	0.0146 (12)	−0.0042 (12)
C5	0.0505 (15)	0.0479 (13)	0.0516 (14)	0.0012 (10)	0.0076 (11)	−0.0080 (10)
C6	0.0556 (16)	0.0518 (14)	0.0578 (15)	0.0019 (11)	0.0185 (13)	0.0038 (11)
C7	0.0459 (14)	0.0515 (14)	0.0600 (15)	−0.0017 (10)	0.0124 (12)	−0.0011 (11)
O1	0.0453 (10)	0.0497 (10)	0.0725 (12)	0.0034 (7)	−0.0025 (9)	−0.0020 (8)
C11	0.0397 (13)	0.0526 (13)	0.0519 (13)	0.0052 (10)	0.0133 (10)	0.0038 (10)
C12	0.0515 (15)	0.0576 (15)	0.0570 (15)	0.0008 (11)	0.0136 (12)	−0.0050 (12)
C13	0.070 (2)	0.0542 (15)	0.082 (2)	0.0054 (13)	0.0337 (17)	0.0034 (14)
N14	0.0675 (18)	0.0647 (16)	0.106 (2)	0.0146 (13)	0.0260 (16)	0.0206 (15)
C15	0.0461 (17)	0.087 (2)	0.099 (3)	0.0125 (15)	0.0030 (16)	0.0201 (19)
C16	0.0419 (14)	0.0621 (16)	0.0750 (19)	−0.0003 (12)	0.0068 (13)	0.0053 (13)
P1	0.0572 (5)	0.0764 (6)	0.0568 (5)	0.0022 (4)	0.0063 (4)	0.0098 (3)
F1	0.160 (12)	0.136 (10)	0.37 (2)	−0.043 (8)	−0.078 (12)	0.177 (13)
F1'	0.167 (7)	0.145 (7)	0.166 (6)	0.082 (6)	0.126 (6)	0.099 (5)
F2	0.095 (5)	0.105 (5)	0.148 (9)	−0.021 (4)	0.035 (5)	0.045 (5)
F2'	0.232 (10)	0.240 (11)	0.121 (6)	−0.029 (9)	0.085 (6)	0.071 (8)
F3	0.215 (14)	0.49 (3)	0.147 (10)	0.279 (17)	0.080 (10)	0.091 (14)
F3'	0.184 (8)	0.182 (7)	0.185 (8)	−0.071 (6)	0.085 (7)	−0.130 (7)
F4	0.141 (10)	0.105 (5)	0.132 (6)	0.055 (6)	0.074 (7)	0.039 (4)
F4'	0.040 (3)	0.229 (12)	0.281 (14)	−0.019 (5)	−0.042 (5)	0.130 (10)
F5	0.126 (8)	0.276 (13)	0.055 (3)	−0.073 (9)	−0.014 (4)	−0.028 (5)
F5'	0.124 (5)	0.064 (3)	0.289 (11)	0.027 (3)	0.057 (6)	−0.014 (4)
F6	0.182 (9)	0.107 (5)	0.061 (3)	0.030 (5)	−0.018 (4)	−0.022 (3)
F6'	0.056 (2)	0.085 (3)	0.154 (5)	−0.0072 (19)	−0.013 (3)	0.014 (3)

Geometric parameters (Å, º)

N1—C2	1.338 (3)	C7—H7A	0.9700
N1—C5	1.374 (3)	C7—H7B	0.9700
N1—C6	1.456 (3)	O1—C11	1.351 (3)
C2—N3	1.327 (4)	C11—C12	1.376 (4)
C2—C21	1.478 (4)	C11—C16	1.385 (4)
C21—H21A	0.9600	C12—C13	1.360 (4)
C21—H21B	0.9600	C12—H12	0.9300
C21—H21C	0.9600	C13—N14	1.333 (4)
C21—H21D	0.9600	C13—H13	0.9300
C21—H21E	0.9600	N14—C15	1.329 (4)
C21—H21F	0.9600	C15—C16	1.374 (4)
N3—C4	1.373 (3)	C15—H15	0.9300
N3—C31	1.472 (3)	C16—H16	0.9300
C31—H31A	0.9600	P1—F3	1.446 (7)
C31—H31B	0.9600	P1—F4'	1.471 (5)
C31—H31C	0.9600	P1—F5	1.471 (5)
C31—H31D	0.9600	P1—F1	1.487 (11)
C31—H31E	0.9600	P1—F2'	1.492 (7)
C31—H31F	0.9600	P1—F5'	1.546 (6)
C4—C5	1.339 (4)	P1—F1'	1.554 (5)
C4—H4	0.9300	P1—F3'	1.556 (7)
C5—H5	0.9300	P1—F6'	1.602 (4)
C6—C7	1.504 (4)	P1—F2	1.615 (8)
C6—H6A	0.9700	P1—F6	1.619 (6)
C6—H6B	0.9700	P1—F4	1.627 (8)
C7—O1	1.432 (3)
C2—N1—C5	108.8 (2)	N1—C6—H6A	109.2
C2—N1—C6	126.6 (2)	C7—C6—H6A	109.2
C5—N1—C6	124.6 (2)	N1—C6—H6B	109.2
N3—C2—N1	107.4 (2)	C7—C6—H6B	109.2
N3—C2—C21	126.2 (3)	H6A—C6—H6B	107.9
N1—C2—C21	126.4 (3)	O1—C7—C6	106.5 (2)
C2—C21—H21A	109.5	O1—C7—H7A	110.4
C2—C21—H21B	109.5	C6—C7—H7A	110.4
H21A—C21—H21B	109.5	O1—C7—H7B	110.4
C2—C21—H21C	109.5	C6—C7—H7B	110.4
H21A—C21—H21C	109.5	H7A—C7—H7B	108.6
H21B—C21—H21C	109.5	C11—O1—C7	118.6 (2)
C2—C21—H21D	109.5	O1—C11—C12	116.6 (2)
H21A—C21—H21D	141.1	O1—C11—C16	124.9 (2)
H21B—C21—H21D	56.3	C12—C11—C16	118.5 (2)
H21C—C21—H21D	56.3	C13—C12—C11	119.3 (3)
C2—C21—H21E	109.5	C13—C12—H12	120.4
H21A—C21—H21E	56.3	C11—C12—H12	120.4
H21B—C21—H21E	141.1	N14—C13—C12	124.2 (3)
H21C—C21—H21E	56.3	N14—C13—H13	117.9
H21D—C21—H21E	109.5	C12—C13—H13	117.9
C2—C21—H21F	109.5	C15—N14—C13	115.3 (3)
H21A—C21—H21F	56.3	N14—C15—C16	125.7 (3)
H21B—C21—H21F	56.3	N14—C15—H15	117.1
H21C—C21—H21F	141.1	C16—C15—H15	117.1
H21D—C21—H21F	109.5	C15—C16—C11	117.0 (3)
H21E—C21—H21F	109.5	C15—C16—H16	121.5
C2—N3—C4	109.5 (2)	C11—C16—H16	121.5
C2—N3—C31	125.8 (2)	F3—P1—F5	92.3 (8)
C4—N3—C31	124.7 (2)	F3—P1—F1	89.3 (11)
N3—C31—H31A	109.5	F5—P1—F1	87.3 (9)
N3—C31—H31B	109.5	F4'—P1—F2'	98.9 (6)
H31A—C31—H31B	109.5	F4'—P1—F5'	91.3 (6)
N3—C31—H31C	109.5	F2'—P1—F5'	90.1 (5)
H31A—C31—H31C	109.5	F4'—P1—F1'	84.2 (5)
H31B—C31—H31C	109.5	F2'—P1—F1'	171.8 (6)
N3—C31—H31D	109.5	F5'—P1—F1'	97.4 (5)
H31A—C31—H31D	141.1	F2'—P1—F3'	88.3 (6)
H31B—C31—H31D	56.3	F5'—P1—F3'	170.8 (4)
H31C—C31—H31D	56.3	F1'—P1—F3'	83.7 (4)
N3—C31—H31E	109.5	F4'—P1—F6'	174.5 (6)
H31A—C31—H31E	56.3	F2'—P1—F6'	86.0 (5)
H31B—C31—H31E	141.1	F5'—P1—F6'	86.1 (3)
H31C—C31—H31E	56.3	F1'—P1—F6'	91.2 (4)
H31D—C31—H31E	109.5	F3'—P1—F6'	84.8 (4)
N3—C31—H31F	109.5	F3—P1—F2	94.0 (10)
H31A—C31—H31F	56.3	F5—P1—F2	96.1 (6)
H31B—C31—H31F	56.3	F1—P1—F2	175.1 (6)
H31C—C31—H31F	141.1	F3—P1—F6	92.0 (9)
H31D—C31—H31F	109.5	F5—P1—F6	175.6 (6)
H31E—C31—H31F	109.5	F1—P1—F6	91.6 (9)
C5—C4—N3	106.9 (2)	F2—P1—F6	84.7 (5)
C5—C4—H4	126.6	F3—P1—F4	173.6 (5)
N3—C4—H4	126.6	F5—P1—F4	92.9 (7)
C4—C5—N1	107.4 (2)	F1—P1—F4	94.6 (10)
C4—C5—H5	126.3	F2—P1—F4	81.8 (5)
N1—C5—H5	126.3	F6—P1—F4	82.9 (5)
N1—C6—C7	111.9 (2)
C5—N1—C2—N3	0.3 (3)	C5—N1—C6—C7	−84.3 (3)
C6—N1—C2—N3	−179.6 (2)	N1—C6—C7—O1	−60.1 (3)
C5—N1—C2—C21	−179.2 (2)	C6—C7—O1—C11	−175.7 (2)
C6—N1—C2—C21	0.9 (4)	C7—O1—C11—C12	−179.8 (2)
N1—C2—N3—C4	−0.5 (3)	C7—O1—C11—C16	0.5 (4)
C21—C2—N3—C4	179.1 (2)	O1—C11—C12—C13	−179.6 (2)
N1—C2—N3—C31	−178.9 (2)	C16—C11—C12—C13	0.2 (4)
C21—C2—N3—C31	0.7 (4)	C11—C12—C13—N14	0.6 (5)
C2—N3—C4—C5	0.5 (3)	C12—C13—N14—C15	−1.2 (5)
C31—N3—C4—C5	178.9 (2)	C13—N14—C15—C16	1.1 (6)
N3—C4—C5—N1	−0.2 (3)	N14—C15—C16—C11	−0.4 (6)
C2—N1—C5—C4	−0.1 (3)	O1—C11—C16—C15	179.4 (3)
C6—N1—C5—C4	179.8 (2)	C12—C11—C16—C15	−0.3 (4)
C2—N1—C6—C7	95.6 (3)