9,10-Bis{2-[1-(2-pyridylmeth­yl)imidazolium-3-yl]eth­oxy}anthracene bis(hexa­fluoridophosphate)

Guo, L.-H.; Qin, D.-B.; Gu, S.-J.; Wang, G.-Y.; Luo, J.-W.

doi:10.1107/S1600536807063842

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o189

https://doi.org/10.1107/S1600536807063842

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9,10-Bis{2-[1-(2-pyridylmethyl)imidazolium-3-yl]ethoxy}anthracene bis(hexafluoridophosphate)

Li-Hui Guo,^a Da-Bin Qin,^a ^* Shao-Jin Gu,^a Gui-Yu Wang ^a and Jie-Wei Luo ^a

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 13 November 2007; accepted 27 November 2007; online 6 December 2007)

The cation of the title compound, C₃₆H₃₄N₆O₂²⁺·2PF₆⁻, lies across a crystallographic inversion centre. The imidazole and pyridine rings form dihedral angles of 82.28 (5)° and 11.87 (7)°, respectively, with the anthracene ring system. The crystal packing is stabilized by π–π interactions between the pyridine ring and the central ring of anthracene, with a ring centroid–centroid distance of 3.684 (3) Å. The PF₆⁻ anion is disordered over three different positions with occupancies of 0.284 (6), 0.354 (8) and 0.362 (9).

Related literature

For the synthesis, see: Liu et al. (2003 ). For related structures, see: Liu et al. (2007 ); Pei et al. (2005 ); Qin et al. (2006 ).

Experimental

Crystal data

C₃₆H₃₄N₆O₂²⁺·2PF₆⁻
M_r = 872.63
Triclinic, $[P \overline 1]$
a = 8.829 (4) Å
b = 9.811 (4) Å
c = 12.586 (5) Å
α = 72.382 (7)°
β = 78.759 (7)°
γ = 65.598 (7)°
V = 943.2 (7) Å³
Z = 1
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 294 (2) K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.950, T_max = 0.962
4911 measured reflections
3307 independent reflections
1792 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.159
S = 1.01
3307 reflections
373 parameters
319 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063842/ci2523sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063842/ci2523Isup2.hkl

checkCIF report

Comment top

Imidazolium salts or its derivatives or analogs are used as ionic liquids, and as catalysts in many organic transformation processes. They are also used to obtain N-heterocyclic carbene complexes. We report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains one-half of the organic cation and a PF₆ counter ion. The cation lies on a crystallographic inversion center. Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges. The imidazole ring is almost perpendicular to the anthracene ring system, with a dihedral angle of 82.28 (5)°, and the pyridine ring is almost parallel to the anthracene ring system, with a dihedral angle of 11.87 (7)°. The crystal packing is stabilized by π-π interactions between pyridine ring and central ring of anthracene [centroid-centroid distance is 3.684 (3) %A.

Related literature top

For thesynthesis, see: Liu et al. (2003). For related structures, see: Liu et al. (2007); Pei et al. (2005); Qin et al. (2006).

Experimental top

The title compound was prepared according to the reported procedure of Liu et al. (2003). Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile.

Structure description top

For thesynthesis, see: Liu et al. (2003). For related structures, see: Liu et al. (2007); Pei et al. (2005); Qin et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top

Fig. 1. View of the cationic unit in the title compound. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are related to labelled atoms by the symmetry operation (1 - x, 1 - y, 2 - z).

9,10-Bis{2-[1-(2-pyridylmethyl)imidazolium-3-yl]ethoxy}anthracene bis(hexafluoridophosphate) top

Crystal data top

C₃₆H₃₄N₆O₂²⁺·2PF₆⁻	Z = 1
M_r = 872.63	F(000) = 446
Triclinic, P1	D_x = 1.536 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.829 (4) Å	Cell parameters from 1209 reflections
b = 9.811 (4) Å	θ = 2.7–21.5°
c = 12.586 (5) Å	µ = 0.22 mm⁻¹
α = 72.382 (7)°	T = 294 K
β = 78.759 (7)°	Block, yellow
γ = 65.598 (7)°	0.24 × 0.20 × 0.18 mm
V = 943.2 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3307 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.950, T_max = 0.962	k = −11→6
4911 measured reflections	l = −14→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0713P)² + 0.3109P] where P = (F_o² + 2F_c²)/3
3307 reflections	(Δ/σ)_max = 0.015
373 parameters	Δρ_max = 0.33 e Å⁻³
319 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₃₆H₃₄N₆O₂²⁺·2PF₆⁻	γ = 65.598 (7)°
M_r = 872.63	V = 943.2 (7) Å³
Triclinic, P1	Z = 1
a = 8.829 (4) Å	Mo Kα radiation
b = 9.811 (4) Å	µ = 0.22 mm⁻¹
c = 12.586 (5) Å	T = 294 K
α = 72.382 (7)°	0.24 × 0.20 × 0.18 mm
β = 78.759 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3307 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1792 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.962	R_int = 0.027
4911 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	319 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.01	Δρ_max = 0.33 e Å⁻³
3307 reflections	Δρ_min = −0.24 e Å⁻³
373 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)
O1	0.3505 (3)	0.6951 (3)	0.80589 (19)	0.0542 (7)
N1	−0.1667 (4)	1.0465 (4)	0.9161 (3)	0.0759 (11)
N2	−0.1181 (4)	1.0404 (4)	0.6845 (3)	0.0594 (9)
N3	0.0945 (4)	0.8468 (4)	0.6444 (2)	0.0537 (9)
C1	−0.2180 (7)	1.0165 (6)	1.0243 (4)	0.0824 (14)
H1	−0.1385	0.9512	1.0749	0.099*
C2	−0.3809 (7)	1.0760 (6)	1.0655 (4)	0.0786 (14)
H2	−0.4105	1.0523	1.1420	0.094*
C3	−0.4988 (6)	1.1708 (5)	0.9918 (5)	0.0741 (13)
H3	−0.6107	1.2126	1.0168	0.089*
C4	−0.4483 (5)	1.2030 (5)	0.8795 (4)	0.0665 (12)
H4	−0.5260	1.2661	0.8273	0.080*
C5	−0.2824 (5)	1.1410 (5)	0.8457 (4)	0.0623 (11)
C6	−0.2179 (5)	1.1793 (5)	0.7253 (4)	0.0747 (13)
H6A	−0.3115	1.2428	0.6799	0.090*
H6B	−0.1501	1.2389	0.7172	0.090*
C7	−0.1765 (6)	0.9587 (6)	0.6444 (4)	0.0714 (13)
H7	−0.2876	0.9820	0.6362	0.086*
C8	−0.0454 (6)	0.8389 (6)	0.6192 (3)	0.0690 (13)
H8	−0.0484	0.7637	0.5899	0.083*
C9	0.0470 (5)	0.9692 (5)	0.6840 (3)	0.0571 (11)
H9	0.1176	1.0009	0.7079	0.069*
C10	0.2667 (5)	0.7415 (5)	0.6272 (3)	0.0697 (13)
H10A	0.3375	0.8007	0.6007	0.084*
H10B	0.2736	0.6916	0.5697	0.084*
C11	0.3307 (5)	0.6199 (5)	0.7318 (3)	0.0616 (11)
H11A	0.2521	0.5702	0.7660	0.074*
H11B	0.4368	0.5418	0.7143	0.074*
C12	0.4252 (4)	0.5939 (4)	0.9027 (3)	0.0440 (9)
C13	0.5991 (4)	0.5322 (4)	0.9005 (3)	0.0449 (9)
C14	0.6758 (4)	0.4338 (4)	1.0009 (3)	0.0438 (9)
C15	0.8534 (4)	0.3686 (5)	0.9977 (4)	0.0590 (11)
H15	0.9055	0.3045	1.0623	0.071*
C16	0.9462 (5)	0.3990 (5)	0.9021 (4)	0.0722 (13)
H16	1.0620	0.3538	0.9010	0.087*
C17	0.8715 (5)	0.4974 (5)	0.8043 (4)	0.0749 (14)
H17	0.9382	0.5187	0.7396	0.090*
C18	0.7031 (5)	0.5624 (5)	0.8023 (3)	0.0592 (11)
H18	0.6555	0.6269	0.7363	0.071*
P1	0.71210 (13)	0.71357 (15)	0.41845 (9)	0.0645 (4)
F1	0.551 (2)	0.702 (3)	0.3935 (19)	0.114 (6)	0.284 (6)
F2	0.789 (2)	0.5628 (17)	0.3757 (17)	0.092 (4)	0.284 (6)
F3	0.758 (2)	0.811 (2)	0.3001 (11)	0.111 (4)	0.284 (6)
F4	0.6560 (19)	0.8681 (17)	0.4551 (19)	0.134 (5)	0.284 (6)
F5	0.662 (2)	0.615 (2)	0.5320 (11)	0.130 (5)	0.284 (6)
F6	0.8857 (15)	0.655 (2)	0.4618 (15)	0.115 (5)	0.284 (6)
F1A	0.5497 (16)	0.672 (2)	0.4454 (14)	0.119 (5)	0.354 (8)
F2A	0.7523 (17)	0.631 (2)	0.3229 (13)	0.093 (4)	0.354 (8)
F3A	0.590 (2)	0.8701 (16)	0.3574 (15)	0.144 (5)	0.354 (8)
F4A	0.6405 (16)	0.7923 (18)	0.5218 (10)	0.097 (4)	0.354 (8)
F5A	0.761 (2)	0.5581 (15)	0.5135 (13)	0.130 (4)	0.354 (8)
F6A	0.8703 (15)	0.7530 (19)	0.3841 (15)	0.114 (5)	0.354 (8)
F1B	0.5218 (10)	0.776 (2)	0.4093 (15)	0.112 (4)	0.362 (9)
F2B	0.7395 (16)	0.722 (2)	0.2880 (7)	0.101 (4)	0.362 (9)
F3B	0.661 (2)	0.8926 (11)	0.3589 (17)	0.123 (4)	0.362 (9)
F4B	0.6951 (19)	0.712 (2)	0.5411 (7)	0.108 (4)	0.362 (9)
F5B	0.8139 (15)	0.5346 (9)	0.4402 (17)	0.109 (4)	0.362 (9)
F6B	0.8931 (11)	0.7078 (15)	0.4201 (10)	0.066 (3)	0.362 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0699 (16)	0.0451 (16)	0.0411 (14)	−0.0139 (13)	−0.0158 (12)	−0.0056 (12)
N1	0.070 (2)	0.078 (3)	0.075 (3)	−0.015 (2)	−0.029 (2)	−0.016 (2)
N2	0.062 (2)	0.056 (2)	0.057 (2)	−0.0193 (19)	−0.0174 (16)	−0.0072 (18)
N3	0.066 (2)	0.055 (2)	0.0356 (17)	−0.0213 (18)	−0.0148 (15)	−0.0023 (16)
C1	0.093 (4)	0.076 (3)	0.079 (4)	−0.022 (3)	−0.036 (3)	−0.016 (3)
C2	0.112 (4)	0.070 (3)	0.071 (3)	−0.047 (3)	−0.011 (3)	−0.023 (3)
C3	0.078 (3)	0.061 (3)	0.097 (4)	−0.032 (3)	−0.008 (3)	−0.032 (3)
C4	0.064 (3)	0.051 (3)	0.086 (3)	−0.015 (2)	−0.024 (2)	−0.017 (2)
C5	0.064 (3)	0.046 (3)	0.073 (3)	−0.013 (2)	−0.021 (2)	−0.012 (2)
C6	0.071 (3)	0.058 (3)	0.084 (3)	−0.014 (2)	−0.019 (2)	−0.009 (3)
C7	0.068 (3)	0.077 (3)	0.075 (3)	−0.032 (3)	−0.027 (2)	−0.006 (3)
C8	0.090 (3)	0.068 (3)	0.060 (3)	−0.038 (3)	−0.032 (2)	−0.004 (2)
C9	0.061 (3)	0.059 (3)	0.053 (2)	−0.022 (2)	−0.0181 (19)	−0.008 (2)
C10	0.076 (3)	0.076 (3)	0.045 (2)	−0.015 (2)	−0.008 (2)	−0.014 (2)
C11	0.078 (3)	0.052 (3)	0.047 (2)	−0.011 (2)	−0.018 (2)	−0.014 (2)
C12	0.057 (2)	0.035 (2)	0.035 (2)	−0.0121 (18)	−0.0091 (17)	−0.0064 (17)
C13	0.053 (2)	0.042 (2)	0.040 (2)	−0.0203 (18)	−0.0008 (17)	−0.0102 (18)
C14	0.047 (2)	0.038 (2)	0.045 (2)	−0.0141 (17)	−0.0026 (17)	−0.0126 (18)
C15	0.051 (2)	0.058 (3)	0.065 (3)	−0.017 (2)	−0.007 (2)	−0.015 (2)
C16	0.046 (2)	0.070 (3)	0.090 (4)	−0.015 (2)	0.001 (2)	−0.018 (3)
C17	0.065 (3)	0.068 (3)	0.077 (3)	−0.027 (2)	0.022 (2)	−0.012 (3)
C18	0.070 (3)	0.058 (3)	0.045 (2)	−0.029 (2)	0.006 (2)	−0.007 (2)
P1	0.0483 (6)	0.0874 (10)	0.0528 (7)	−0.0162 (6)	−0.0078 (5)	−0.0219 (7)
F1	0.084 (7)	0.149 (10)	0.128 (9)	−0.048 (6)	−0.055 (6)	−0.025 (8)
F2	0.114 (7)	0.086 (7)	0.091 (8)	−0.042 (5)	−0.007 (6)	−0.036 (6)
F3	0.134 (7)	0.097 (7)	0.092 (7)	−0.060 (6)	0.002 (6)	0.003 (6)
F4	0.158 (7)	0.100 (7)	0.110 (7)	−0.007 (6)	0.006 (7)	−0.051 (6)
F5	0.126 (7)	0.137 (7)	0.084 (6)	−0.032 (6)	0.017 (6)	−0.008 (6)
F6	0.098 (6)	0.126 (8)	0.114 (8)	−0.037 (6)	−0.050 (6)	−0.003 (6)
F1A	0.070 (5)	0.154 (8)	0.126 (8)	−0.060 (5)	0.011 (5)	−0.010 (7)
F2A	0.109 (6)	0.085 (7)	0.090 (7)	−0.026 (6)	−0.001 (5)	−0.048 (6)
F3A	0.118 (8)	0.121 (7)	0.146 (7)	−0.023 (6)	−0.030 (7)	0.010 (6)
F4A	0.116 (6)	0.101 (7)	0.050 (5)	−0.015 (5)	−0.001 (5)	−0.026 (5)
F5A	0.128 (7)	0.110 (6)	0.099 (6)	−0.020 (5)	−0.011 (6)	0.011 (5)
F6A	0.106 (6)	0.113 (8)	0.127 (9)	−0.072 (6)	−0.002 (6)	0.005 (6)
F1B	0.051 (4)	0.129 (8)	0.128 (7)	−0.016 (5)	−0.009 (4)	−0.019 (7)
F2B	0.122 (6)	0.108 (8)	0.069 (5)	−0.030 (6)	−0.003 (4)	−0.037 (5)
F3B	0.108 (7)	0.093 (6)	0.132 (7)	−0.032 (5)	−0.023 (6)	0.022 (6)
F4B	0.142 (7)	0.131 (8)	0.047 (4)	−0.040 (6)	−0.019 (4)	−0.024 (5)
F5B	0.126 (6)	0.077 (5)	0.113 (7)	−0.029 (4)	−0.015 (6)	−0.020 (5)
F6B	0.061 (4)	0.075 (7)	0.060 (6)	−0.040 (4)	−0.023 (4)	0.019 (5)

Geometric parameters (Å, º) top

O1—C12	1.395 (4)	C11—H11A	0.97
O1—C11	1.425 (4)	C11—H11B	0.97
N1—C5	1.327 (5)	C12—C14ⁱ	1.385 (5)
N1—C1	1.332 (6)	C12—C13	1.397 (5)
N2—C9	1.330 (5)	C13—C18	1.421 (5)
N2—C7	1.361 (5)	C13—C14	1.429 (5)
N2—C6	1.467 (5)	C14—C12ⁱ	1.385 (5)
N3—C9	1.316 (5)	C14—C15	1.425 (5)
N3—C8	1.370 (5)	C15—C16	1.345 (5)
N3—C10	1.461 (5)	C15—H15	0.93
C1—C2	1.370 (6)	C16—C17	1.398 (6)
C1—H1	0.93	C16—H16	0.93
C2—C3	1.366 (6)	C17—C18	1.356 (5)
C2—H2	0.93	C17—H17	0.93
C3—C4	1.377 (6)	C18—H18	0.93
C3—H3	0.93	P1—F4B	1.518 (8)
C4—C5	1.369 (5)	P1—F3A	1.533 (9)
C4—H4	0.93	P1—F6	1.544 (9)
C5—C6	1.502 (6)	P1—F1B	1.547 (8)
C6—H6A	0.97	P1—F6A	1.548 (9)
C6—H6B	0.97	P1—F2A	1.554 (8)
C7—C8	1.335 (5)	P1—F5	1.562 (9)
C7—H7	0.93	P1—F2	1.565 (9)
C8—H8	0.93	P1—F1	1.566 (10)
C9—H9	0.93	P1—F5B	1.571 (8)
C10—C11	1.503 (5)	P1—F4	1.572 (9)
C10—H10A	0.97	P1—F6B	1.579 (8)
C10—H10B	0.97

C12—O1—C11	113.8 (3)	O1—C11—H11A	110.3
C5—N1—C1	116.9 (4)	C10—C11—H11A	110.3
C9—N2—C7	107.9 (4)	O1—C11—H11B	110.3
C9—N2—C6	125.3 (4)	C10—C11—H11B	110.3
C7—N2—C6	126.7 (4)	H11A—C11—H11B	108.5
C9—N3—C8	107.9 (4)	C14ⁱ—C12—O1	118.8 (3)
C9—N3—C10	125.7 (4)	C14ⁱ—C12—C13	122.5 (3)
C8—N3—C10	126.4 (4)	O1—C12—C13	118.6 (3)
N1—C1—C2	123.9 (4)	C12—C13—C18	122.7 (3)
N1—C1—H1	118.0	C12—C13—C14	118.7 (3)
C2—C1—H1	118.0	C18—C13—C14	118.6 (3)
C3—C2—C1	118.5 (5)	C12ⁱ—C14—C15	122.7 (3)
C3—C2—H2	120.8	C12ⁱ—C14—C13	118.8 (3)
C1—C2—H2	120.8	C15—C14—C13	118.5 (3)
C2—C3—C4	118.5 (5)	C16—C15—C14	120.6 (4)
C2—C3—H3	120.8	C16—C15—H15	119.7
C4—C3—H3	120.8	C14—C15—H15	119.7
C5—C4—C3	119.3 (4)	C15—C16—C17	121.0 (4)
C5—C4—H4	120.4	C15—C16—H16	119.5
C3—C4—H4	120.4	C17—C16—H16	119.5
N1—C5—C4	123.0 (4)	C18—C17—C16	121.0 (4)
N1—C5—C6	115.1 (4)	C18—C17—H17	119.5
C4—C5—C6	121.9 (4)	C16—C17—H17	119.5
N2—C6—C5	112.2 (3)	C17—C18—C13	120.3 (4)
N2—C6—H6A	109.2	C17—C18—H18	119.9
C5—C6—H6A	109.2	C13—C18—H18	119.9
N2—C6—H6B	109.2	F4B—P1—F1B	94.3 (8)
C5—C6—H6B	109.2	F3A—P1—F6A	96.6 (10)
H6A—C6—H6B	107.9	F3A—P1—F2A	97.0 (10)
C8—C7—N2	107.5 (4)	F6A—P1—F2A	92.4 (9)
C8—C7—H7	126.3	F6—P1—F5	87.0 (10)
N2—C7—H7	126.3	F6—P1—F2	83.7 (10)
C7—C8—N3	107.5 (4)	F5—P1—F2	87.4 (10)
C7—C8—H8	126.2	F6—P1—F1	156.8 (13)
N3—C8—H8	126.2	F5—P1—F1	77.1 (11)
N3—C9—N2	109.1 (4)	F2—P1—F1	78.9 (12)
N3—C9—H9	125.4	F4B—P1—F5B	93.5 (8)
N2—C9—H9	125.4	F1B—P1—F5B	118.9 (9)
N3—C10—C11	112.8 (3)	F6—P1—F4	91.2 (10)
N3—C10—H10A	109.0	F5—P1—F4	97.5 (10)
C11—C10—H10A	109.0	F2—P1—F4	172.8 (9)
N3—C10—H10B	109.0	F1—P1—F4	107.3 (11)
C11—C10—H10B	109.0	F4B—P1—F6B	84.2 (7)
H10A—C10—H10B	107.8	F1B—P1—F6B	161.1 (9)
O1—C11—C10	107.3 (3)	F5B—P1—F6B	79.9 (7)

C5—N1—C1—C2	0.5 (7)	C9—N3—C10—C11	83.6 (5)
N1—C1—C2—C3	0.6 (8)	C8—N3—C10—C11	−98.5 (4)
C1—C2—C3—C4	−0.4 (7)	C12—O1—C11—C10	−174.0 (3)
C2—C3—C4—C5	−0.8 (6)	N3—C10—C11—O1	−70.3 (4)
C1—N1—C5—C4	−1.9 (7)	C11—O1—C12—C14ⁱ	−96.3 (4)
C1—N1—C5—C6	176.5 (4)	C11—O1—C12—C13	87.7 (4)
C3—C4—C5—N1	2.1 (7)	C14ⁱ—C12—C13—C18	−179.0 (3)
C3—C4—C5—C6	−176.2 (4)	O1—C12—C13—C18	−3.1 (5)
C9—N2—C6—C5	−93.4 (5)	C14ⁱ—C12—C13—C14	1.5 (6)
C7—N2—C6—C5	84.1 (5)	O1—C12—C13—C14	177.3 (3)
N1—C5—C6—N2	55.0 (5)	C12—C13—C14—C12ⁱ	−1.4 (6)
C4—C5—C6—N2	−126.6 (4)	C18—C13—C14—C12ⁱ	179.0 (3)
C9—N2—C7—C8	−0.5 (5)	C12—C13—C14—C15	178.7 (3)
C6—N2—C7—C8	−178.3 (4)	C18—C13—C14—C15	−0.8 (5)
N2—C7—C8—N3	0.3 (5)	C12ⁱ—C14—C15—C16	−180.0 (4)
C9—N3—C8—C7	0.1 (4)	C13—C14—C15—C16	−0.1 (6)
C10—N3—C8—C7	−178.1 (3)	C14—C15—C16—C17	1.3 (7)
C8—N3—C9—N2	−0.4 (4)	C15—C16—C17—C18	−1.5 (7)
C10—N3—C9—N2	177.8 (3)	C16—C17—C18—C13	0.5 (7)
C7—N2—C9—N3	0.5 (4)	C12—C13—C18—C17	−178.9 (4)
C6—N2—C9—N3	178.4 (3)	C14—C13—C18—C17	0.6 (6)

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₃₆H₃₄N₆O₂²⁺·2PF₆⁻
M_r	872.63
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.829 (4), 9.811 (4), 12.586 (5)
α, β, γ (°)	72.382 (7), 78.759 (7), 65.598 (7)
V (Å³)	943.2 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	4911, 3307, 1792
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.159, 1.01
No. of reflections	3307
No. of parameters	373
No. of restraints	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Acknowledgements

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, B., Chen, W. Z. & Jin, S. W. (2007). Organometallics, 26, 3660–3667. Web of Science CSD CrossRef CAS Google Scholar
Liu, Q. X., Xu, F. B., Li, Q. S., Zeng, X. S., Leng, X. B., Chou, Y. L. & Zhang, Z. Z. (2003). Organometallics, 22, 309–314. Web of Science CSD CrossRef CAS Google Scholar
Pei, L. C., Chun, L. L., Chiu, F. C., Ching, H. H. & Hon, M. L. (2005). Organometallics, 24, 6169–6178. Google Scholar
Qin, D. B., Xu, F. B., Wan, X. J., Zhao, Y. J. & Zhang, Z. Z. (2006). Tetrahedron Lett. 47, 5641–5643. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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