3-(8-Methoxy­quinolin-2-ylmeth­yl)-1-methyl-3H-1-imidazolium hexa­fluoro­phosphate

Zhu, Y.-L.; Zhong, Z.-F.; Yin, Q.-F.; Liu, W.

doi:10.1107/S1600536807026955

3-(8-Methoxyquinolin-2-ylmethyl)-1-methyl-3H-1-imidazolium hexafluorophosphate

Y.-L. Zhu, Z.-F. Zhong, Q.-F. Yin and W. Liu

In the cation of the title compound, C₁₅H₁₇N₃O⁺·PF₆⁻, the dihedral angle between the mean planes of the quinoline and imidazole groups is 78.02 (7)°. In the crystal structure, π–π stacking interactions, with a ring centroid separation of 3.752 (2) Å, link the molecules into centrosymmetric dimers. In addition, weak intermolecular C—H

F and C—H

O interactions help to stabilize the crystal structure. The F atoms of the anion are disordered over two sites in a ratio of approximately 0.86:0.14.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026955/lh2402sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026955/lh2402Isup2.hkl Contains datablock I

CCDC reference: 654973

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.058
wR factor = 0.170
Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H2     ..  H3      ..       2.05 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.108
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT214_ALERT_2_C Atom F6'     (Anion/Solvent) ADP max/min Ratio         4.90 oblat
PLAT221_ALERT_4_C Large Solvent/Anion  F     Ueq(max)/Ueq(min) ...       3.11 Ratio
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  F3     ..  N1      ..       2.90 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F3     ..  C3      ..       2.96 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        108

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

Comment top

Room-temperature ionic liquids are attracting significant interest owing to their chemical characteristics and potentially useful solvent properties (Dibrov & Kochi, 2006) and imidazolium salts, which are regarded as a type of ionic liquids, have an extensive application in organic synthesis (Pretti et al., 2006).

The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the quinoline plane and imidazole plane is 78.02 (7) °. In the crystal structure, π-π stacking internactions link molecules into centrosymmetric dimers. In addtion, weak intermolecular C—H···F and C—H···O interactions help stabilize the crystal structure.

Related literature top

For related literature, see: Bortolini et al. (2003); Dibrov & Kochi (2006); Pretti et al. (2006).

Experimental top

The title compound was synthesized according to the literature procedure (Bortolini et al., 2003).

Structure description top

For related literature, see: Bortolini et al. (2003); Dibrov & Kochi (2006); Pretti et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. Hydrogen atoms and the minor component of disorder have been omitted.
	Fig. 2. : The packing of the title compound, viewed down the b axis.

3-(8-Methoxyquinolin-2-ylmethyl)-1-methyl-3H-1-imidazolium hexafluorophosphate top

Crystal data top

C₁₅H₁₇N₃O⁺·F₆P⁻	Z = 8
M_r = 400.29	F(000) = 1640
Monoclinic, C2/c	D_x = 1.527 Mg m⁻³
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.2183 (11) Å	µ = 0.23 mm⁻¹
b = 21.3444 (19) Å	T = 291 K
c = 14.4056 (13) Å	Block, colourless
β = 112.059 (1)°	0.24 × 0.18 × 0.16 mm
V = 3481.9 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 independent reflections
Radiation source: fine-focus sealed tube	2808 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.108
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.947, T_max = 0.964	k = −25→25
12564 measured reflections	l = −16→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.170	w = 1/[σ²(F_o²) + (0.0848P)² + 6.8821P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3087 reflections	Δρ_max = 1.13 e Å⁻³
293 parameters	Δρ_min = −0.67 e Å⁻³
108 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0026 (5)

Crystal data top

C₁₅H₁₇N₃O⁺·F₆P⁻	V = 3481.9 (5) Å³
M_r = 400.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 12.2183 (11) Å	µ = 0.23 mm⁻¹
b = 21.3444 (19) Å	T = 291 K
c = 14.4056 (13) Å	0.24 × 0.18 × 0.16 mm
β = 112.059 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3087 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2808 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.964	R_int = 0.108
12564 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	108 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.05	Δρ_max = 1.13 e Å⁻³
3087 reflections	Δρ_min = −0.67 e Å⁻³
293 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	Occ. (<1)
P1	0.01910 (7)	0.33923 (4)	0.99358 (6)	0.0431 (3)
F1	0.0575 (5)	0.3561 (2)	1.1098 (3)	0.092 (2)	0.859 (6)
F2	0.0141 (3)	0.26827 (11)	1.0220 (2)	0.0687 (9)	0.859 (6)
F3	−0.1135 (2)	0.3483 (2)	0.9796 (3)	0.0951 (13)	0.859 (6)
F4	0.0294 (4)	0.41165 (15)	0.9733 (3)	0.1144 (16)	0.859 (6)
F5	0.1552 (2)	0.33103 (19)	1.0130 (3)	0.0916 (12)	0.859 (6)
F6	−0.0185 (5)	0.3223 (3)	0.8809 (3)	0.118 (3)	0.859 (6)
F1'	0.0459 (14)	0.3516 (7)	1.1049 (6)	0.038 (6)	0.141 (6)
F2'	−0.0984 (11)	0.3001 (8)	0.9825 (10)	0.080 (6)	0.141 (6)
F3'	−0.0593 (16)	0.3991 (6)	0.9584 (11)	0.089 (7)	0.141 (6)
F4'	0.1291 (12)	0.3739 (9)	0.9927 (12)	0.113 (9)	0.141 (6)
F5'	0.0894 (16)	0.2751 (6)	1.0179 (12)	0.117 (9)	0.141 (6)
F6'	−0.0142 (12)	0.3222 (7)	0.8752 (7)	0.046 (6)	0.141 (6)
N1	0.35973 (18)	0.67281 (10)	0.14547 (16)	0.0286 (5)
N2	0.51217 (19)	0.55385 (10)	0.12278 (15)	0.0297 (5)
H2	0.5699	0.5799	0.1455	0.036*
N3	0.29978 (19)	0.68579 (10)	0.26701 (16)	0.0324 (5)
O1	0.73297 (16)	0.51432 (9)	0.21731 (16)	0.0406 (5)
C1	0.5310 (2)	0.49095 (12)	0.13432 (18)	0.0302 (6)
C2	0.4026 (2)	0.57384 (13)	0.07571 (19)	0.0326 (6)
C3	0.3228 (2)	0.64369 (12)	0.20928 (19)	0.0305 (6)
H3	0.3143	0.6006	0.2130	0.037*
C4	0.3047 (2)	0.53339 (14)	0.0384 (2)	0.0403 (7)
H4	0.2290	0.5494	0.0063	0.048*
C5	0.6489 (2)	0.46864 (12)	0.1842 (2)	0.0336 (6)
C6	0.3226 (3)	0.47019 (14)	0.0499 (2)	0.0407 (7)
H6	0.2588	0.4429	0.0260	0.049*
C7	0.4631 (3)	0.38144 (13)	0.1118 (2)	0.0410 (7)
H7	0.4025	0.3522	0.0882	0.049*
C8	0.4378 (2)	0.44646 (13)	0.09821 (19)	0.0338 (6)
C9	0.3866 (3)	0.64389 (13)	0.0633 (2)	0.0360 (6)
H9A	0.4582	0.6624	0.0612	0.043*
H9B	0.3229	0.6528	0.0000	0.043*
C10	0.3589 (3)	0.73643 (13)	0.1622 (2)	0.0385 (6)
H10	0.3799	0.7680	0.1275	0.046*
C11	0.6706 (3)	0.40540 (13)	0.1961 (2)	0.0407 (7)
H11	0.7475	0.3910	0.2284	0.049*
C12	0.3219 (3)	0.74401 (13)	0.2382 (2)	0.0401 (7)
H12	0.3130	0.7820	0.2663	0.048*
C13	0.5766 (3)	0.36226 (13)	0.1594 (2)	0.0436 (7)
H13	0.5927	0.3196	0.1680	0.052*
C14	0.2529 (3)	0.67183 (15)	0.3445 (2)	0.0460 (7)
H14A	0.1684	0.6752	0.3166	0.069*
H14B	0.2846	0.7011	0.3987	0.069*
H14C	0.2750	0.6300	0.3690	0.069*
C15	0.8535 (3)	0.49475 (17)	0.2664 (3)	0.0613 (10)
H15A	0.8622	0.4725	0.3266	0.092*
H15B	0.9040	0.5309	0.2827	0.092*
H15C	0.8749	0.4678	0.2226	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0324 (5)	0.0473 (5)	0.0488 (5)	−0.0030 (3)	0.0140 (3)	0.0112 (3)
F1	0.112 (4)	0.076 (3)	0.066 (3)	0.004 (3)	0.009 (2)	−0.017 (2)
F2	0.092 (2)	0.0408 (13)	0.0805 (18)	−0.0165 (13)	0.0406 (16)	−0.0023 (12)
F3	0.0347 (14)	0.126 (3)	0.115 (3)	0.0141 (16)	0.0167 (14)	−0.015 (2)
F4	0.113 (3)	0.068 (2)	0.128 (3)	−0.0150 (19)	0.006 (2)	0.0528 (19)
F5	0.0423 (15)	0.118 (3)	0.122 (3)	−0.0103 (16)	0.0385 (16)	0.007 (2)
F6	0.125 (5)	0.168 (5)	0.057 (3)	−0.007 (4)	0.029 (3)	0.003 (3)
F1'	0.047 (8)	0.035 (9)	0.034 (9)	0.004 (6)	0.019 (7)	0.015 (7)
F2'	0.082 (10)	0.101 (11)	0.067 (8)	−0.024 (8)	0.039 (7)	0.009 (7)
F3'	0.102 (11)	0.073 (9)	0.094 (10)	0.033 (8)	0.039 (8)	0.015 (7)
F4'	0.100 (12)	0.111 (12)	0.134 (13)	−0.018 (9)	0.052 (9)	0.002 (9)
F5'	0.114 (12)	0.101 (12)	0.116 (12)	0.033 (9)	0.021 (9)	−0.005 (9)
F6'	0.037 (8)	0.083 (11)	0.033 (9)	−0.009 (7)	0.032 (7)	0.002 (7)
N1	0.0253 (10)	0.0285 (11)	0.0319 (11)	0.0030 (8)	0.0105 (8)	0.0018 (8)
N2	0.0319 (11)	0.0288 (11)	0.0321 (11)	−0.0008 (9)	0.0165 (9)	−0.0039 (9)
N3	0.0322 (11)	0.0332 (11)	0.0325 (11)	0.0028 (9)	0.0130 (9)	−0.0019 (9)
O1	0.0328 (10)	0.0339 (10)	0.0514 (12)	0.0035 (8)	0.0113 (9)	−0.0043 (9)
C1	0.0380 (14)	0.0310 (13)	0.0274 (12)	0.0017 (10)	0.0190 (11)	−0.0021 (10)
C2	0.0354 (13)	0.0364 (14)	0.0305 (13)	0.0051 (11)	0.0174 (11)	−0.0016 (11)
C3	0.0335 (13)	0.0269 (12)	0.0314 (13)	0.0033 (10)	0.0124 (10)	0.0017 (10)
C4	0.0318 (14)	0.0500 (17)	0.0410 (15)	0.0025 (12)	0.0159 (12)	−0.0058 (13)
C5	0.0377 (14)	0.0323 (14)	0.0337 (13)	0.0018 (11)	0.0166 (11)	−0.0033 (10)
C6	0.0378 (15)	0.0461 (17)	0.0433 (15)	−0.0078 (12)	0.0210 (12)	−0.0107 (13)
C7	0.0544 (18)	0.0345 (14)	0.0419 (15)	−0.0075 (12)	0.0270 (14)	−0.0057 (12)
C8	0.0418 (14)	0.0340 (14)	0.0323 (13)	−0.0042 (11)	0.0215 (11)	−0.0052 (11)
C9	0.0391 (14)	0.0381 (15)	0.0357 (14)	0.0082 (11)	0.0195 (12)	0.0039 (11)
C10	0.0421 (15)	0.0278 (13)	0.0478 (16)	−0.0030 (11)	0.0193 (13)	0.0012 (12)
C11	0.0483 (16)	0.0335 (14)	0.0420 (15)	0.0088 (12)	0.0190 (13)	0.0016 (12)
C12	0.0465 (16)	0.0276 (13)	0.0471 (16)	0.0012 (11)	0.0183 (13)	−0.0052 (12)
C13	0.0627 (19)	0.0275 (13)	0.0463 (16)	0.0018 (13)	0.0271 (15)	0.0005 (12)
C14	0.0552 (18)	0.0516 (18)	0.0409 (16)	0.0011 (14)	0.0290 (14)	−0.0024 (13)
C15	0.0341 (16)	0.051 (2)	0.084 (3)	0.0072 (14)	0.0059 (16)	−0.0075 (18)

Geometric parameters (Å, º) top

P1—F1'	1.534 (8)	C2—C4	1.409 (4)
P1—F4'	1.539 (8)	C2—C9	1.510 (4)
P1—F6	1.555 (4)	C3—H3	0.9300
P1—F3'	1.563 (8)	C4—C6	1.367 (4)
P1—F3	1.568 (3)	C4—H4	0.9300
P1—F2	1.576 (2)	C5—C11	1.374 (4)
P1—F5'	1.584 (8)	C6—C8	1.409 (4)
P1—F4	1.587 (3)	C6—H6	0.9300
P1—F5	1.589 (3)	C7—C13	1.358 (5)
P1—F1	1.601 (4)	C7—C8	1.420 (4)
P1—F2'	1.616 (8)	C7—H7	0.9300
P1—F6'	1.639 (8)	C9—H9A	0.9700
N1—C3	1.322 (3)	C9—H9B	0.9700
N1—C10	1.380 (3)	C10—C12	1.343 (4)
N1—C9	1.478 (3)	C10—H10	0.9300
N2—C2	1.323 (3)	C11—C13	1.411 (4)
N2—C1	1.362 (3)	C11—H11	0.9300
N2—H2	0.8600	C12—H12	0.9300
N3—C3	1.324 (3)	C13—H13	0.9300
N3—C12	1.369 (4)	C14—H14A	0.9600
N3—C14	1.464 (3)	C14—H14B	0.9600
O1—C5	1.366 (3)	C14—H14C	0.9600
O1—C15	1.436 (4)	C15—H15A	0.9600
C1—C8	1.423 (4)	C15—H15B	0.9600
C1—C5	1.429 (4)	C15—H15C	0.9600

F1'—P1—F4'	94.7 (6)	C10—N1—C9	124.7 (2)
F1'—P1—F6	174.1 (6)	C2—N2—C1	118.2 (2)
F4'—P1—F6	91.2 (7)	C2—N2—H2	120.9
F1'—P1—F3'	93.6 (5)	C1—N2—H2	120.9
F4'—P1—F3'	92.0 (6)	C3—N3—C12	108.3 (2)
F6—P1—F3'	87.0 (7)	C3—N3—C14	125.2 (2)
F1'—P1—F3	85.3 (6)	C12—N3—C14	126.5 (2)
F4'—P1—F3	143.4 (8)	C5—O1—C15	117.5 (2)
F6—P1—F3	90.5 (2)	N2—C1—C8	122.6 (2)
F3'—P1—F3	51.7 (7)	N2—C1—C5	118.8 (2)
F1'—P1—F2	84.7 (6)	C8—C1—C5	118.6 (2)
F4'—P1—F2	125.7 (8)	N2—C2—C4	123.3 (3)
F6—P1—F2	91.3 (2)	N2—C2—C9	116.2 (2)
F3'—P1—F2	142.3 (7)	C4—C2—C9	120.5 (2)
F3—P1—F2	90.74 (19)	N1—C3—N3	109.0 (2)
F1'—P1—F5'	91.8 (5)	N1—C3—H3	125.5
F4'—P1—F5'	90.9 (6)	N3—C3—H3	125.5
F6—P1—F5'	87.3 (7)	C6—C4—C2	118.9 (3)
F3'—P1—F5'	173.7 (7)	C6—C4—H4	120.5
F3—P1—F5'	125.7 (8)	C2—C4—H4	120.5
F1'—P1—F4	91.4 (6)	O1—C5—C11	125.0 (3)
F4'—P1—F4	53.1 (8)	O1—C5—C1	114.9 (2)
F6—P1—F4	92.7 (3)	C11—C5—C1	120.1 (3)
F3—P1—F4	90.3 (2)	C4—C6—C8	120.0 (3)
F2—P1—F4	175.85 (18)	C4—C6—H6	120.0
F5'—P1—F4	144.0 (8)	C8—C6—H6	120.0
F1'—P1—F5	92.1 (6)	C13—C7—C8	119.5 (3)
F6—P1—F5	92.2 (2)	C13—C7—H7	120.2
F3'—P1—F5	128.4 (7)	C8—C7—H7	120.2
F3—P1—F5	177.34 (19)	C6—C8—C7	123.0 (3)
F2—P1—F5	89.34 (17)	C6—C8—C1	117.0 (3)
F5'—P1—F5	54.7 (8)	C7—C8—C1	119.9 (3)
F4—P1—F5	89.4 (2)	N1—C9—C2	112.1 (2)
F4'—P1—F1	89.2 (7)	N1—C9—H9A	109.2
F6—P1—F1	179.5 (3)	C2—C9—H9A	109.2
F3'—P1—F1	93.3 (6)	N1—C9—H9B	109.2
F3—P1—F1	89.4 (2)	C2—C9—H9B	109.2
F2—P1—F1	88.2 (2)	H9A—C9—H9B	107.9
F5'—P1—F1	92.4 (7)	C12—C10—N1	106.7 (2)
F4—P1—F1	87.8 (2)	C12—C10—H10	126.6
F5—P1—F1	88.0 (2)	N1—C10—H10	126.6
F1'—P1—F2'	91.4 (5)	C5—C11—C13	120.2 (3)
F4'—P1—F2'	173.8 (6)	C5—C11—H11	119.9
F6—P1—F2'	82.7 (6)	C13—C11—H11	119.9
F3'—P1—F2'	88.6 (5)	C10—C12—N3	107.6 (2)
F2—P1—F2'	53.8 (7)	C10—C12—H12	126.2
F5'—P1—F2'	87.9 (5)	N3—C12—H12	126.2
F4—P1—F2'	127.9 (7)	C7—C13—C11	121.7 (3)
F5—P1—F2'	142.5 (7)	C7—C13—H13	119.2
F1—P1—F2'	96.9 (6)	C11—C13—H13	119.2
F1'—P1—F6'	176.4 (6)	N3—C14—H14A	109.5
F4'—P1—F6'	88.6 (5)	N3—C14—H14B	109.5
F3'—P1—F6'	87.8 (5)	H14A—C14—H14B	109.5
F3—P1—F6'	93.0 (5)	N3—C14—H14C	109.5
F2—P1—F6'	92.2 (6)	H14A—C14—H14C	109.5
F5'—P1—F6'	86.6 (5)	H14B—C14—H14C	109.5
F4—P1—F6'	91.8 (6)	O1—C15—H15A	109.5
F5—P1—F6'	89.6 (5)	O1—C15—H15B	109.5
F1—P1—F6'	177.5 (6)	H15A—C15—H15B	109.5
F2'—P1—F6'	85.3 (5)	O1—C15—H15C	109.5
C3—N1—C10	108.4 (2)	H15A—C15—H15C	109.5
C3—N1—C9	126.7 (2)	H15B—C15—H15C	109.5

C2—N2—C1—C8	−0.2 (3)	C13—C7—C8—C6	−179.8 (3)
C2—N2—C1—C5	179.5 (2)	C13—C7—C8—C1	0.1 (4)
C1—N2—C2—C4	0.9 (4)	N2—C1—C8—C6	−0.7 (4)
C1—N2—C2—C9	−179.0 (2)	C5—C1—C8—C6	179.6 (2)
C10—N1—C3—N3	−0.8 (3)	N2—C1—C8—C7	179.4 (2)
C9—N1—C3—N3	−175.3 (2)	C5—C1—C8—C7	−0.2 (4)
C12—N3—C3—N1	0.6 (3)	C3—N1—C9—C2	−16.9 (4)
C14—N3—C3—N1	177.7 (2)	C10—N1—C9—C2	169.4 (2)
N2—C2—C4—C6	−0.7 (4)	N2—C2—C9—N1	−93.1 (3)
C9—C2—C4—C6	179.3 (2)	C4—C2—C9—N1	87.0 (3)
C15—O1—C5—C11	1.4 (4)	C3—N1—C10—C12	0.7 (3)
C15—O1—C5—C1	−178.8 (3)	C9—N1—C10—C12	175.4 (2)
N2—C1—C5—O1	0.8 (3)	O1—C5—C11—C13	179.5 (2)
C8—C1—C5—O1	−179.4 (2)	C1—C5—C11—C13	−0.2 (4)
N2—C1—C5—C11	−179.4 (2)	N1—C10—C12—N3	−0.4 (3)
C8—C1—C5—C11	0.3 (4)	C3—N3—C12—C10	−0.1 (3)
C2—C4—C6—C8	−0.3 (4)	C14—N3—C12—C10	−177.2 (3)
C4—C6—C8—C7	−179.2 (3)	C8—C7—C13—C11	0.1 (4)
C4—C6—C8—C1	0.9 (4)	C5—C11—C13—C7	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1ⁱ	0.93	2.46	3.204 (5)	137
C9—H9A···F2ⁱⁱ	0.97	2.49	3.244 (4)	135
C3—H3···O1ⁱⁱⁱ	0.93	2.27	3.122 (3)	152

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇N₃O⁺·F₆P⁻
M_r	400.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	291
a, b, c (Å)	12.2183 (11), 21.3444 (19), 14.4056 (13)
β (°)	112.059 (1)
V (Å³)	3481.9 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.24 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	12564, 3087, 2808
R_int	0.108
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.170, 1.05
No. of reflections	3087
No. of parameters	293
No. of restraints	108
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.67

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Putz, 2005), SHELXTL (Bruker, 1998).