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In the title centrosymmetric compound, C34H30N62+·2PF6, the planes through the pyridine and anthracene ring systems form dihedral angles of 78.8 (1) and 73.5 (1)°, respectively, with the imidazole ring. The crystal packing is stabilized by π–π stacking inter­actions between the anthracene ring system and pyridine rings of adjacent mol­ecules, and also by C—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023196/ci6612sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023196/ci6612Isup2.hkl
Contains datablock I

CCDC reference: 283770

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in solvent or counterion
  • R factor = 0.065
  • wR factor = 0.219
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 46.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

9,10-Bis[3-(2-pyridylmethyl)imidazolium-1-ylmethyl]anthracene bis(hexafluorophosphate) top
Crystal data top
C34H30N62+·2PF6Z = 1
Mr = 812.58F(000) = 414
Triclinic, P1Dx = 1.493 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2564 (15) ÅCell parameters from 1905 reflections
b = 9.7534 (15) Åθ = 2.3–25.0°
c = 11.4425 (18) ŵ = 0.22 mm1
α = 65.621 (2)°T = 294 K
β = 75.971 (3)°Block, yellow
γ = 76.993 (2)°0.32 × 0.22 × 0.20 mm
V = 903.7 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3594 independent reflections
Radiation source: fine-focus sealed tube2248 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 26.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1011
Tmin = 0.934, Tmax = 0.958k = 1211
5051 measured reflectionsl = 147
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1121P)2 + 0.4256P]
where P = (Fo2 + 2Fc2)/3
3594 reflections(Δ/σ)max = 0.001
299 parametersΔρmax = 0.39 e Å3
36 restraintsΔρmin = 0.31 e Å3
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
xyzUiso*/UeqOcc. (<1)
C120.0541 (4)0.5881 (4)0.2586 (3)0.0594 (9)
H12A0.04540.48640.32520.071*
H12B0.09500.58540.18920.071*
C10.1915 (4)0.6274 (4)0.2788 (3)0.0560 (9)
H10.17830.58210.36910.067*
C20.2874 (5)0.7442 (6)0.0785 (4)0.0970 (16)
H20.35290.79430.00460.116*
C30.1537 (5)0.7115 (7)0.0810 (4)0.0978 (17)
H30.10900.73500.00920.117*
C40.4390 (4)0.7153 (4)0.2433 (3)0.0655 (10)
H4A0.42100.81700.24360.079*
H4B0.52870.70830.18010.079*
C80.4664 (3)0.6013 (4)0.3769 (3)0.0533 (8)
C70.3958 (3)0.6344 (4)0.4869 (3)0.0531 (8)
C60.2848 (4)0.7640 (4)0.4814 (4)0.0709 (10)
H60.25840.83000.40130.085*
C50.2171 (5)0.7940 (6)0.5883 (5)0.0886 (13)
H50.14300.87770.58200.106*
C90.5675 (3)0.4676 (4)0.3875 (3)0.0545 (8)
C100.6374 (4)0.4268 (5)0.2785 (4)0.0727 (11)
H100.61120.48760.19720.087*
C110.7407 (5)0.3019 (6)0.2911 (5)0.0907 (14)
H110.78510.27890.21800.109*
C130.1572 (3)0.6957 (4)0.3152 (3)0.0510 (8)
C140.2304 (4)0.8303 (5)0.2382 (4)0.0758 (11)
H140.22070.85610.14920.091*
C150.3186 (5)0.9262 (6)0.2975 (7)0.1065 (18)
H150.37111.01760.24910.128*
C160.3272 (6)0.8843 (7)0.4272 (7)0.1062 (19)
H160.38280.94880.46850.127*
C170.2548 (6)0.7491 (6)0.4961 (5)0.0936 (15)
H170.26480.72090.58560.112*
N10.3100 (3)0.6911 (3)0.2029 (2)0.0556 (7)
N20.0953 (3)0.6380 (3)0.2070 (2)0.0526 (7)
N30.1699 (4)0.6540 (4)0.4426 (3)0.0682 (8)
P10.23998 (11)0.20890 (12)0.13911 (9)0.0657 (4)
F10.1500 (9)0.2917 (9)0.2240 (8)0.150 (4)0.589 (12)
F20.3426 (8)0.3376 (8)0.0658 (10)0.167 (5)0.589 (12)
F30.3513 (7)0.1258 (9)0.2385 (7)0.135 (4)0.589 (12)
F40.1501 (8)0.0731 (8)0.2081 (10)0.159 (4)0.589 (12)
F50.1334 (11)0.2873 (11)0.0409 (9)0.195 (5)0.589 (12)
F60.3432 (10)0.1268 (11)0.0496 (9)0.196 (6)0.589 (12)
F1'0.1092 (12)0.3219 (12)0.1774 (13)0.205 (10)0.411 (12)
F2'0.3541 (14)0.2868 (15)0.1601 (13)0.207 (8)0.411 (12)
F3'0.225 (2)0.0980 (11)0.2812 (6)0.199 (9)0.411 (12)
F4'0.1207 (13)0.1351 (16)0.1167 (12)0.193 (8)0.411 (12)
F5'0.2522 (15)0.3191 (12)0.0053 (6)0.154 (6)0.411 (12)
F6'0.3669 (13)0.0959 (12)0.0991 (14)0.205 (9)0.411 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.0536 (19)0.072 (2)0.061 (2)0.0156 (17)0.0111 (16)0.0294 (18)
C10.0557 (18)0.070 (2)0.0360 (16)0.0158 (16)0.0113 (14)0.0088 (15)
C20.073 (3)0.163 (5)0.037 (2)0.042 (3)0.0069 (18)0.009 (2)
C30.076 (3)0.173 (5)0.0386 (19)0.036 (3)0.0142 (18)0.023 (2)
C40.0564 (19)0.077 (2)0.0497 (19)0.0254 (18)0.0173 (15)0.0015 (17)
C80.0465 (16)0.063 (2)0.0431 (16)0.0232 (15)0.0148 (13)0.0006 (14)
C70.0444 (16)0.0572 (19)0.0532 (18)0.0197 (15)0.0115 (14)0.0081 (15)
C60.065 (2)0.061 (2)0.082 (3)0.0152 (19)0.022 (2)0.014 (2)
C50.078 (3)0.084 (3)0.110 (4)0.009 (2)0.016 (3)0.044 (3)
C90.0487 (17)0.069 (2)0.0448 (17)0.0269 (16)0.0081 (14)0.0110 (16)
C100.067 (2)0.097 (3)0.058 (2)0.031 (2)0.0055 (18)0.026 (2)
C110.083 (3)0.113 (4)0.091 (3)0.030 (3)0.007 (3)0.057 (3)
C130.0437 (16)0.0580 (19)0.0535 (18)0.0140 (14)0.0124 (14)0.0174 (15)
C140.069 (2)0.069 (3)0.079 (3)0.005 (2)0.025 (2)0.013 (2)
C150.073 (3)0.064 (3)0.168 (6)0.004 (2)0.033 (3)0.030 (4)
C160.076 (3)0.098 (4)0.154 (6)0.014 (3)0.019 (3)0.076 (4)
C170.098 (3)0.105 (4)0.091 (3)0.022 (3)0.006 (3)0.059 (3)
N10.0499 (14)0.0706 (18)0.0362 (13)0.0153 (13)0.0105 (11)0.0049 (12)
N20.0480 (14)0.0687 (18)0.0429 (14)0.0091 (13)0.0103 (11)0.0211 (13)
N30.074 (2)0.078 (2)0.0560 (18)0.0101 (16)0.0117 (15)0.0285 (16)
P10.0682 (6)0.0738 (7)0.0466 (6)0.0006 (5)0.0114 (4)0.0187 (5)
F10.140 (6)0.196 (9)0.156 (6)0.075 (5)0.055 (5)0.142 (7)
F20.145 (6)0.130 (5)0.179 (10)0.063 (5)0.003 (6)0.004 (6)
F30.105 (5)0.142 (7)0.136 (7)0.031 (4)0.066 (4)0.031 (5)
F40.152 (6)0.139 (6)0.171 (9)0.076 (5)0.012 (6)0.024 (6)
F50.182 (9)0.251 (12)0.140 (8)0.003 (9)0.125 (8)0.021 (8)
F60.205 (10)0.280 (15)0.129 (7)0.043 (9)0.057 (6)0.144 (9)
F1'0.119 (9)0.123 (8)0.26 (2)0.030 (7)0.067 (11)0.042 (10)
F2'0.282 (17)0.230 (18)0.152 (12)0.165 (14)0.068 (12)0.033 (12)
F3'0.40 (3)0.117 (8)0.061 (5)0.074 (13)0.071 (10)0.026 (5)
F4'0.242 (14)0.250 (18)0.129 (10)0.178 (15)0.023 (10)0.044 (11)
F5'0.182 (13)0.186 (10)0.052 (4)0.063 (10)0.003 (6)0.007 (5)
F6'0.208 (13)0.133 (9)0.232 (18)0.122 (10)0.064 (12)0.088 (10)
Geometric parameters (Å, º) top
C12—N21.472 (4)C10—C111.348 (6)
C12—C131.497 (5)C10—H100.93
C12—H12A0.97C11—C5i1.402 (7)
C12—H12B0.97C11—H110.93
C1—N21.313 (4)C13—N31.324 (4)
C1—N11.320 (4)C13—C141.376 (5)
C1—H10.93C14—C151.383 (7)
C2—C31.337 (6)C14—H140.93
C2—N11.351 (4)C15—C161.355 (8)
C2—H20.93C15—H150.93
C3—N21.352 (4)C16—C171.345 (7)
C3—H30.93C16—H160.93
C4—N11.476 (4)C17—N31.327 (5)
C4—C81.515 (4)C17—H170.93
C4—H4A0.97P1—F11.497 (5)
C4—H4B0.97P1—F51.520 (4)
C8—C71.399 (5)P1—F3'1.529 (5)
C8—C91.402 (5)P1—F6'1.542 (6)
C7—C61.427 (5)P1—F41.544 (5)
C7—C9i1.441 (4)P1—F2'1.545 (6)
C6—C51.348 (6)P1—F5'1.548 (5)
C6—H60.93P1—F1'1.554 (7)
C5—C11i1.402 (7)P1—F31.563 (4)
C5—H50.93P1—F4'1.565 (6)
C9—C101.426 (5)P1—F61.569 (5)
C9—C7i1.441 (4)P1—F21.570 (5)
N2—C12—C13109.7 (3)C15—C14—H14121.0
N2—C12—H12A109.7C16—C15—C14118.7 (5)
C13—C12—H12A109.7C16—C15—H15120.7
N2—C12—H12B109.7C14—C15—H15120.7
C13—C12—H12B109.7C17—C16—C15119.7 (5)
H12A—C12—H12B108.2C17—C16—H16120.1
N2—C1—N1109.5 (3)C15—C16—H16120.1
N2—C1—H1125.3N3—C17—C16123.1 (5)
N1—C1—H1125.3N3—C17—H17118.4
C3—C2—N1107.5 (3)C16—C17—H17118.4
C3—C2—H2126.3C1—N1—C2107.7 (3)
N1—C2—H2126.3C1—N1—C4127.5 (3)
C2—C3—N2107.5 (3)C2—N1—C4124.6 (3)
C2—C3—H3126.3C1—N2—C3107.9 (3)
N2—C3—H3126.3C1—N2—C12124.7 (3)
N1—C4—C8112.9 (3)C3—N2—C12127.3 (3)
N1—C4—H4A109.0C13—N3—C17117.7 (4)
C8—C4—H4A109.0F1—P1—F591.2 (4)
N1—C4—H4B109.0F3'—P1—F6'90.6 (5)
C8—C4—H4B109.0F1—P1—F493.4 (4)
H4A—C4—H4B107.8F5—P1—F490.6 (4)
C7—C8—C9121.2 (3)F3'—P1—F2'91.2 (4)
C7—C8—C4119.5 (3)F6'—P1—F2'91.7 (5)
C9—C8—C4119.3 (3)F3'—P1—F5'178.4 (5)
C8—C7—C6122.9 (3)F6'—P1—F5'89.4 (4)
C8—C7—C9i119.3 (3)F2'—P1—F5'90.3 (4)
C6—C7—C9i117.8 (3)F3'—P1—F1'90.0 (5)
C5—C6—C7122.2 (4)F6'—P1—F1'178.4 (6)
C5—C6—H6118.9F2'—P1—F1'89.8 (5)
C7—C6—H6118.9F5'—P1—F1'90.0 (5)
C6—C5—C11i119.4 (5)F1—P1—F390.1 (4)
C6—C5—H5120.3F5—P1—F3178.7 (4)
C11i—C5—H5120.3F4—P1—F389.1 (3)
C8—C9—C10122.9 (3)F3'—P1—F4'89.7 (4)
C8—C9—C7i119.4 (3)F6'—P1—F4'90.0 (5)
C10—C9—C7i117.6 (4)F2'—P1—F4'178.1 (6)
C11—C10—C9121.3 (4)F5'—P1—F4'88.8 (4)
C11—C10—H10119.4F1'—P1—F4'88.5 (5)
C9—C10—H10119.4F1—P1—F6176.3 (4)
C10—C11—C5i121.5 (4)F5—P1—F690.7 (4)
C10—C11—H11119.2F4—P1—F689.7 (4)
C5i—C11—H11119.2F3—P1—F688.0 (4)
N3—C13—C14122.8 (4)F1—P1—F290.9 (4)
N3—C13—C12115.6 (3)F5—P1—F291.3 (4)
C14—C13—C12121.6 (3)F4—P1—F2175.2 (4)
C13—C14—C15117.9 (4)F3—P1—F288.9 (4)
C13—C14—H14121.0F6—P1—F285.9 (4)
N1—C2—C3—N20.2 (6)C12—C13—C14—C15177.3 (3)
N1—C4—C8—C790.4 (4)C13—C14—C15—C160.9 (7)
N1—C4—C8—C992.5 (4)C14—C15—C16—C172.4 (8)
C9—C8—C7—C6175.7 (3)C15—C16—C17—N32.1 (8)
C4—C8—C7—C67.2 (5)N2—C1—N1—C20.2 (5)
C9—C8—C7—C9i2.7 (5)N2—C1—N1—C4174.7 (3)
C4—C8—C7—C9i174.4 (3)C3—C2—N1—C10.0 (6)
C8—C7—C6—C5179.6 (3)C3—C2—N1—C4174.7 (4)
C9i—C7—C6—C51.2 (5)C8—C4—N1—C126.6 (5)
C7—C6—C5—C11i2.0 (6)C8—C4—N1—C2159.8 (4)
C7—C8—C9—C10177.5 (3)N1—C1—N2—C30.3 (5)
C4—C8—C9—C105.4 (5)N1—C1—N2—C12175.9 (3)
C7—C8—C9—C7i2.7 (5)C2—C3—N2—C10.3 (6)
C4—C8—C9—C7i174.4 (3)C2—C3—N2—C12175.8 (4)
C8—C9—C10—C11176.0 (3)C13—C12—N2—C172.3 (4)
C7i—C9—C10—C113.7 (5)C13—C12—N2—C3102.4 (4)
C9—C10—C11—C5i0.6 (6)C14—C13—N3—C171.4 (5)
N2—C12—C13—N396.2 (3)C12—C13—N3—C17177.0 (3)
N2—C12—C13—C1482.2 (4)C16—C17—N3—C130.2 (7)
N3—C13—C14—C151.0 (6)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N3ii0.932.423.233 (5)146
Symmetry code: (ii) x, y+1, z+1.
 

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