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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2202–o2203.
Published online 2010 August 4. doi:  10.1107/S1600536810029727
PMCID: PMC3007944

3,3′-Dimethyl-1,1′-(methyl­enedi-p-phenyl­ene)diimidazolium bis­(hexa­fluoro­phosphate)

Abstract

The title N-heterocyclic carbene compound, C21H22N4 2+·2PF6 , crystallizes as an inversion twin. There are two independent N-heterocyclic carbene dications (A and B) and four independent hexa­fluoro­phosphate anions in the asymmetric unit. The cations are L-shaped with the benzene rings being inclined to one another by 88.82 (16)° in cation A and 87.03 (16)° in cation B. The imidazole rings make dihedral angles of 35.7 (2) and 32.83 (18)° with the attached benzene rings in cation A, and 30.14 (19) and 31.96 (18)° in cation B. In the crystal, the cations are linked via C—H(...)F hydrogen bonds, forming a three-dimensional network. π–π inter­actions involving the benzene and imidazole rings [centroid–centroid distances = 3.602 (2) and 3.723 (2) Å] and C—H(...)π inter­actions are also present.

Related literature

For details of the first free carbenes isolated, see: Arduengo et al. (1991 [triangle]). For the role of N-heterocyclic carbene ligands in organometallic chemistry, see: Lin et al. (2009 [triangle]). For the synthesis of the title compound, see: Austin et al. (1981 [triangle]); Wei et al. (2008 [triangle]). For a related structure, see: Pinto et al. (2009 [triangle]). For standard bond lengths, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2202-scheme1.jpg

Experimental

Crystal data

  • C21H22N4 2+·2PF6
  • M r = 620.37
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2202-efi1.jpg
  • a = 11.5645 (19) Å
  • b = 13.690 (2) Å
  • c = 31.188 (5) Å
  • V = 4937.6 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 113 K
  • 0.20 × 0.18 × 0.12 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 [triangle] T min = 0.945, T max = 0.966
  • 42536 measured reflections
  • 11808 independent reflections
  • 10632 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.142
  • S = 1.08
  • 11808 reflections
  • 708 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.53 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 5268 Friedel pairs
  • Flack parameter: 0.50 (9)

Data collection: CrystalClear (Rigaku/MSC, 2004 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029727/su2188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029727/su2188Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

Since the first free carbene was isolated by (Arduengo et al., 1991), N-heterocyclic carbene (NHC) ligands have gradually take up important roles in organometallic chemistry (Lin et al., 2009). Herein we report on the crystal structure of the title N-heterocyclic carbene compound.

The molecular structures of the two independent N-heterocyclic carbene dications (cation A and cation B) are illustrated in Fig. 1. The bond lengths (Allen et al., 1987) and angles are within normal ranges. In the cations the benzene rings make dihedral angles of 88.82 (16) ° in cation A and 87.03 (16) ° in cation B. The imidazole rings are twisted with respect to the attached benzene rings being inclined to one another by 35.7 (2)° and 32.83 (18)° in cation A and 30.14 (19)° and 31.96 (18)° in cation B.

In the crystal there is an extensive arrangement of C—H···F hydrogen bonds, which not only stabilizes the molecular structure but also link the cations (Table 1 and Fig. 2) to form a three-dimensional network. There are also π–π interactions involving rings N3/C18/N4/C19/C20 and C26—C31 [symmetry code: x, y, z], with the ring centroids being separated by 3.602 (2) Å, and rings C5-C10 and N7/C39/N8/C40/C41 [symmetry code: x, y+1, z] with ring centroids separated by 3.723 (2) Å. In addition C—H···π interactions, involving the imidazole and benzene rings, are also present (Table 1).

Experimental

The title compound was prepared according to the reported procedures (Austin et al., 1981; Wei et al., 2008). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile and ethyl ether (v:v = 1:1).

Refinement

The structure was refined as an inversion twin with the final refined Flack factor being 0.50 (9). H-atoms were placed in calculated positions with C—H = 0.95–0.99 Å, and refined in the riding mode with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
A view of the molecular structures of the two independent cations (A and B) of the title compound. The displacement ellipsoids are drawn at 30% probability level. C-bound H atoms and hexafluorophosphate anions have been omitted for clarity.
Fig. 2.
Crystal packing of the title compound, view along the a axis, showing the cations and anions linked via C-H···F interactions (dashed lines), so forming a three-dimensional network.

Crystal data

C21H22N42+·2PF6F(000) = 2512
Mr = 620.37Dx = 1.669 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 17727 reflections
a = 11.5645 (19) Åθ = 1.6–27.9°
b = 13.690 (2) ŵ = 0.29 mm1
c = 31.188 (5) ÅT = 113 K
V = 4937.6 (13) Å3Prism, colourless
Z = 80.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer11808 independent reflections
Radiation source: fine-focus sealed tube10632 reflections with I > 2σ(I)
multilayerRint = 0.064
Detector resolution: 14.63 pixels mm-1θmax = 27.9°, θmin = 1.6°
ω and [var phi] scansh = −11→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004k = −16→18
Tmin = 0.945, Tmax = 0.966l = −41→38
42536 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.142w = 1/[σ2(Fo2) + (0.0571P)2 + 1.7414P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
11808 reflectionsΔρmax = 0.49 e Å3
708 parametersΔρmin = −0.53 e Å3
0 restraintsAbsolute structure: Flack (1983), 5268 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.50 (9)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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 > 2sigma(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)

xyzUiso*/Ueq
N1−0.0473 (3)0.6747 (3)0.28054 (10)0.0401 (10)
N20.0564 (3)0.7088 (2)0.22569 (9)0.0292 (8)
N30.5528 (2)0.32968 (19)0.05976 (8)0.0254 (8)
N40.6505 (2)0.21221 (19)0.08809 (9)0.0285 (8)
C1−0.1278 (4)0.6224 (4)0.30890 (13)0.0533 (14)
C2−0.0293 (3)0.6515 (3)0.23960 (12)0.0333 (11)
C30.0923 (4)0.7690 (3)0.25863 (12)0.0383 (11)
C40.0270 (4)0.7479 (3)0.29267 (12)0.0406 (11)
C50.1090 (3)0.7018 (2)0.18380 (10)0.0259 (9)
C60.1196 (3)0.6104 (2)0.16471 (11)0.0309 (10)
C70.1750 (3)0.6042 (2)0.12554 (11)0.0333 (10)
C80.2194 (3)0.6858 (2)0.10487 (11)0.0273 (9)
C90.2088 (3)0.7760 (2)0.12527 (11)0.0291 (10)
C100.1522 (3)0.7850 (3)0.16437 (11)0.0323 (10)
C110.2783 (3)0.6772 (3)0.06154 (11)0.0318 (10)
C120.3544 (3)0.5880 (2)0.05757 (10)0.0267 (9)
C130.3195 (3)0.5064 (2)0.03432 (10)0.0310 (10)
C140.3854 (3)0.4226 (2)0.03363 (11)0.0296 (10)
C150.4886 (3)0.4192 (2)0.05605 (10)0.0240 (8)
C160.5287 (3)0.5010 (2)0.07769 (12)0.0328 (10)
C170.4601 (3)0.5841 (3)0.07841 (12)0.0324 (10)
C180.6112 (3)0.3015 (2)0.09451 (11)0.0279 (9)
C190.6158 (3)0.1818 (2)0.04820 (11)0.0314 (10)
C200.5551 (3)0.2539 (2)0.03025 (10)0.0294 (10)
C210.7228 (4)0.1568 (3)0.11954 (13)0.0406 (11)
N50.5227 (3)0.2547 (2)0.28123 (9)0.0338 (9)
N60.4818 (2)0.21150 (19)0.21667 (9)0.0266 (8)
N7−0.0206 (2)−0.17354 (18)0.05923 (8)0.0237 (8)
N8−0.1168 (3)−0.29169 (19)0.08910 (9)0.0276 (8)
C220.5202 (4)0.3061 (4)0.32176 (12)0.0528 (15)
C230.4504 (3)0.2705 (3)0.24893 (10)0.0287 (10)
C240.5762 (3)0.1566 (3)0.22969 (12)0.0326 (10)
C250.6009 (3)0.1841 (3)0.26999 (12)0.0350 (10)
C260.4238 (3)0.2047 (2)0.17611 (10)0.0259 (9)
C270.3690 (3)0.2853 (2)0.15914 (11)0.0280 (9)
C280.3108 (3)0.2758 (2)0.12021 (10)0.0256 (9)
C290.3095 (3)0.1870 (2)0.09819 (10)0.0250 (9)
C300.3663 (3)0.1080 (2)0.11633 (11)0.0315 (10)
C310.4231 (3)0.1153 (3)0.15498 (12)0.0326 (10)
C320.2481 (3)0.1767 (2)0.05534 (11)0.0283 (10)
C330.1731 (3)0.0865 (2)0.05303 (10)0.0245 (9)
C340.0685 (3)0.0825 (2)0.07502 (11)0.0271 (9)
C350.0022 (3)−0.0010 (2)0.07627 (11)0.0269 (9)
C360.0411 (3)−0.0836 (2)0.05510 (10)0.0229 (8)
C370.1420 (3)−0.0816 (2)0.03128 (10)0.0274 (9)
C380.2076 (3)0.0044 (2)0.03039 (11)0.0298 (10)
C39−0.0779 (3)−0.2017 (2)0.09465 (10)0.0249 (9)
C40−0.0822 (3)−0.3235 (2)0.04900 (11)0.0307 (10)
C41−0.0228 (3)−0.2503 (2)0.03027 (10)0.0276 (9)
C42−0.1874 (3)−0.3460 (2)0.12033 (13)0.0372 (11)
P10.61677 (8)0.88387 (6)0.06933 (3)0.0279 (2)
F10.6708 (2)0.83513 (17)0.11089 (7)0.0439 (7)
F20.6730 (2)0.79921 (17)0.04033 (7)0.0499 (8)
F30.5659 (2)0.93295 (16)0.02705 (7)0.0432 (7)
F40.5614 (2)0.96690 (17)0.09819 (7)0.0460 (7)
F50.7322 (2)0.94752 (19)0.06358 (8)0.0515 (8)
F60.5023 (2)0.82036 (17)0.07381 (8)0.0504 (8)
P20.66813 (9)0.47668 (7)0.21334 (3)0.0338 (3)
F70.5352 (2)0.4707 (2)0.22527 (11)0.0721 (12)
F80.7010 (3)0.4328 (2)0.25867 (8)0.0656 (10)
F90.8030 (2)0.48195 (17)0.20214 (8)0.0499 (8)
F100.6398 (3)0.5190 (2)0.16774 (9)0.0785 (11)
F110.6758 (3)0.58452 (17)0.23195 (9)0.0603 (9)
F120.6634 (2)0.36775 (17)0.19490 (8)0.0557 (9)
P30.83051 (8)0.94635 (7)0.21464 (3)0.0294 (3)
F130.7940 (3)0.8980 (2)0.25859 (8)0.0721 (11)
F140.8124 (2)1.05208 (17)0.23341 (9)0.0559 (9)
F150.8668 (3)0.9915 (2)0.16996 (8)0.0726 (10)
F160.8492 (3)0.84028 (19)0.19490 (10)0.0685 (10)
F170.6998 (2)0.94487 (17)0.19868 (8)0.0465 (8)
F180.9615 (2)0.94825 (18)0.23005 (9)0.0502 (8)
P40.93255 (9)0.37704 (7)0.07805 (3)0.0339 (3)
F190.8584 (2)0.34663 (19)0.11796 (7)0.0562 (9)
F200.8867 (2)0.28285 (16)0.05298 (7)0.0530 (8)
F211.0041 (4)0.4072 (3)0.03809 (11)0.135 (2)
F220.9790 (2)0.47003 (16)0.10268 (8)0.0504 (8)
F230.8254 (3)0.4369 (2)0.06109 (11)0.0879 (13)
F241.0361 (3)0.3159 (2)0.09699 (15)0.1033 (16)
H1A−0.179500.581500.291600.0800*
H1B−0.173700.669700.325200.0800*
H1C−0.084000.581100.328800.0800*
H2−0.069500.603600.223400.0400*
H30.152100.816400.257300.0460*
H40.031300.777800.320100.0490*
H60.089600.553700.178300.0370*
H70.182900.542000.112300.0400*
H90.240900.832500.112200.0350*
H100.143300.847100.177500.0390*
H11A0.218400.675000.038900.0380*
H11B0.326000.736300.056600.0380*
H130.249100.508500.018700.0370*
H140.360100.367300.017800.0360*
H160.601600.500200.091700.0390*
H170.486300.639900.093600.0390*
H180.622700.339500.119700.0330*
H190.632100.120200.035600.0380*
H200.520300.253400.002700.0350*
H21A0.798900.143700.107000.0610*
H21B0.684700.094800.126500.0610*
H21C0.732100.195600.145700.0610*
H22A0.576900.359300.321300.0790*
H22B0.539100.260700.345000.0790*
H22C0.442800.333200.326500.0790*
H230.387800.315500.248700.0340*
H240.615900.108800.213300.0390*
H250.661300.159200.287500.0420*
H270.370800.346300.173700.0340*
H280.271400.330500.108500.0310*
H300.365900.047100.101700.0380*
H310.461100.060200.167000.0390*
H32A0.199300.235100.050500.0340*
H32B0.306500.174000.032200.0340*
H340.041900.139200.089600.0330*
H35−0.06910−0.002000.091400.0320*
H370.16630−0.137600.015800.0330*
H380.276900.006400.014000.0360*
H39−0.08880−0.163100.119700.0300*
H40−0.09760−0.385800.036800.0370*
H410.01110−0.251200.002500.0330*
H42A−0.19200−0.309000.147200.0560*
H42B−0.15190−0.409800.125900.0560*
H42C−0.26540−0.355500.108700.0560*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0387 (18)0.0517 (19)0.0299 (16)0.0071 (16)0.0049 (14)−0.0031 (14)
N20.0317 (15)0.0268 (14)0.0290 (14)0.0056 (12)−0.0030 (12)0.0008 (11)
N30.0267 (14)0.0252 (13)0.0243 (13)−0.0063 (11)0.0018 (11)−0.0015 (11)
N40.0267 (14)0.0260 (13)0.0327 (15)−0.0042 (12)0.0036 (12)0.0027 (11)
C10.037 (2)0.081 (3)0.042 (2)0.004 (2)0.0100 (19)−0.005 (2)
C20.0322 (19)0.0355 (19)0.0321 (18)0.0028 (15)0.0038 (15)−0.0028 (15)
C30.051 (2)0.0305 (18)0.0335 (18)0.0037 (17)−0.0063 (18)−0.0087 (15)
C40.052 (2)0.0357 (19)0.034 (2)0.0068 (18)−0.0059 (18)−0.0081 (16)
C50.0233 (15)0.0279 (16)0.0264 (16)0.0013 (13)−0.0064 (13)0.0003 (13)
C60.0323 (18)0.0275 (16)0.0328 (18)−0.0049 (15)0.0035 (15)−0.0030 (14)
C70.0334 (18)0.0265 (16)0.0400 (19)−0.0024 (15)0.0042 (16)−0.0084 (14)
C80.0189 (14)0.0313 (17)0.0316 (17)0.0000 (13)−0.0040 (13)0.0008 (14)
C90.0278 (16)0.0271 (16)0.0323 (18)−0.0016 (14)−0.0061 (14)0.0054 (13)
C100.037 (2)0.0276 (16)0.0322 (18)0.0003 (15)−0.0059 (15)−0.0002 (14)
C110.0296 (17)0.0332 (18)0.0326 (18)0.0020 (14)−0.0005 (15)0.0044 (14)
C120.0261 (16)0.0307 (16)0.0234 (15)−0.0005 (13)0.0022 (13)0.0010 (12)
C130.0295 (17)0.0360 (18)0.0275 (17)−0.0035 (15)−0.0078 (15)0.0045 (14)
C140.0359 (18)0.0278 (16)0.0251 (16)−0.0052 (14)−0.0060 (15)−0.0001 (13)
C150.0209 (14)0.0272 (15)0.0240 (15)−0.0014 (12)0.0018 (12)−0.0010 (12)
C160.0232 (16)0.0313 (18)0.044 (2)−0.0024 (14)−0.0066 (15)−0.0101 (15)
C170.0256 (17)0.0305 (17)0.041 (2)0.0017 (14)−0.0055 (15)−0.0092 (15)
C180.0239 (16)0.0267 (16)0.0330 (17)−0.0037 (14)0.0000 (14)−0.0018 (13)
C190.0352 (18)0.0268 (16)0.0322 (18)−0.0050 (15)0.0065 (15)−0.0046 (14)
C200.0380 (19)0.0280 (16)0.0222 (15)−0.0055 (15)0.0032 (14)−0.0032 (13)
C210.038 (2)0.0358 (19)0.048 (2)−0.0050 (17)−0.0032 (18)0.0009 (17)
N50.0298 (15)0.0404 (16)0.0311 (15)0.0025 (13)−0.0066 (13)0.0010 (13)
N60.0216 (13)0.0226 (13)0.0357 (15)0.0023 (11)−0.0047 (12)0.0011 (12)
N70.0234 (13)0.0201 (12)0.0276 (14)0.0002 (10)−0.0012 (11)−0.0002 (10)
N80.0278 (14)0.0200 (12)0.0350 (15)−0.0027 (11)−0.0009 (12)0.0013 (11)
C220.053 (3)0.081 (3)0.0245 (18)0.030 (3)−0.0045 (18)−0.008 (2)
C230.0208 (15)0.0330 (18)0.0324 (18)0.0016 (14)−0.0024 (13)0.0061 (14)
C240.0242 (17)0.0306 (17)0.043 (2)0.0036 (14)−0.0054 (15)0.0038 (15)
C250.0282 (17)0.0308 (17)0.046 (2)0.0071 (15)−0.0043 (16)0.0059 (15)
C260.0196 (14)0.0282 (16)0.0298 (16)−0.0004 (13)0.0005 (13)−0.0001 (13)
C270.0286 (16)0.0208 (14)0.0347 (18)0.0020 (13)0.0013 (14)0.0012 (13)
C280.0228 (15)0.0221 (14)0.0318 (17)−0.0005 (12)0.0022 (13)0.0031 (13)
C290.0216 (15)0.0238 (15)0.0296 (16)−0.0029 (12)0.0025 (13)0.0023 (12)
C300.0273 (16)0.0273 (16)0.0400 (19)0.0033 (14)−0.0035 (15)−0.0070 (14)
C310.0254 (16)0.0263 (16)0.046 (2)0.0038 (14)0.0003 (15)0.0003 (15)
C320.0289 (17)0.0275 (16)0.0285 (17)−0.0055 (14)0.0039 (13)0.0043 (13)
C330.0244 (15)0.0254 (15)0.0237 (15)−0.0035 (13)−0.0014 (13)0.0028 (12)
C340.0226 (15)0.0246 (15)0.0342 (17)0.0015 (13)0.0024 (14)−0.0042 (13)
C350.0224 (15)0.0280 (16)0.0303 (17)−0.0010 (13)0.0041 (14)−0.0016 (13)
C360.0230 (15)0.0204 (14)0.0253 (15)−0.0004 (12)−0.0021 (12)0.0012 (12)
C370.0324 (18)0.0252 (15)0.0246 (16)0.0021 (13)0.0054 (14)−0.0028 (13)
C380.0283 (16)0.0330 (17)0.0281 (17)−0.0017 (14)0.0109 (14)0.0025 (14)
C390.0263 (16)0.0230 (15)0.0255 (16)0.0005 (13)−0.0001 (13)0.0009 (12)
C400.0353 (18)0.0208 (15)0.0361 (18)0.0002 (14)−0.0075 (15)−0.0026 (13)
C410.0281 (17)0.0278 (15)0.0268 (16)0.0020 (13)−0.0003 (13)−0.0036 (13)
C420.036 (2)0.0256 (16)0.050 (2)−0.0040 (15)0.0042 (18)0.0070 (16)
P10.0262 (4)0.0264 (4)0.0311 (4)0.0022 (3)−0.0024 (4)−0.0035 (3)
F10.0430 (13)0.0567 (14)0.0320 (11)0.0184 (12)−0.0023 (10)0.0039 (10)
F20.0575 (15)0.0510 (13)0.0412 (12)0.0228 (13)−0.0112 (12)−0.0173 (10)
F30.0463 (13)0.0426 (12)0.0408 (12)0.0060 (11)−0.0069 (11)0.0115 (10)
F40.0437 (13)0.0427 (12)0.0515 (13)0.0132 (11)−0.0026 (11)−0.0172 (10)
F50.0348 (12)0.0648 (16)0.0550 (15)−0.0143 (12)−0.0005 (11)0.0035 (13)
F60.0426 (13)0.0490 (14)0.0597 (15)−0.0191 (12)−0.0013 (12)0.0055 (12)
P20.0397 (5)0.0299 (4)0.0318 (5)−0.0024 (4)−0.0004 (4)0.0008 (4)
F70.0439 (15)0.0474 (15)0.125 (3)0.0012 (13)0.0260 (17)0.0104 (16)
F80.099 (2)0.0623 (17)0.0356 (13)0.0115 (17)−0.0007 (15)0.0086 (12)
F90.0412 (13)0.0437 (13)0.0649 (16)−0.0062 (11)0.0007 (12)−0.0083 (12)
F100.085 (2)0.097 (2)0.0535 (16)−0.0338 (19)−0.0342 (16)0.0383 (16)
F110.0624 (17)0.0314 (12)0.0872 (19)0.0051 (13)0.0032 (16)−0.0113 (12)
F120.0585 (16)0.0430 (13)0.0657 (16)−0.0132 (13)0.0097 (14)−0.0210 (12)
P30.0247 (4)0.0306 (4)0.0328 (5)0.0004 (4)−0.0003 (4)−0.0032 (4)
F130.073 (2)0.099 (2)0.0444 (14)−0.0320 (18)0.0006 (14)0.0211 (15)
F140.0338 (12)0.0390 (12)0.095 (2)0.0037 (11)−0.0180 (13)−0.0300 (13)
F150.0578 (18)0.111 (2)0.0489 (15)−0.0018 (18)0.0069 (14)0.0258 (16)
F160.0642 (19)0.0473 (15)0.094 (2)0.0192 (14)−0.0251 (16)−0.0309 (14)
F170.0307 (11)0.0501 (14)0.0586 (15)−0.0030 (10)−0.0098 (11)−0.0166 (11)
F180.0314 (12)0.0417 (13)0.0774 (18)0.0047 (10)−0.0163 (12)0.0051 (12)
P40.0371 (5)0.0230 (4)0.0416 (5)−0.0049 (4)0.0082 (4)−0.0034 (4)
F190.0601 (17)0.0684 (16)0.0401 (13)−0.0261 (14)0.0056 (12)−0.0041 (12)
F200.0705 (17)0.0399 (12)0.0487 (13)−0.0230 (13)0.0196 (13)−0.0164 (10)
F210.211 (5)0.102 (3)0.093 (2)−0.112 (3)0.104 (3)−0.052 (2)
F220.0496 (14)0.0349 (12)0.0668 (16)−0.0081 (11)0.0000 (13)−0.0161 (11)
F230.115 (3)0.0518 (16)0.097 (2)0.0150 (18)−0.068 (2)0.0036 (16)
F240.0421 (17)0.0489 (17)0.219 (4)0.0170 (14)−0.029 (2)−0.032 (2)

Geometric parameters (Å, °)

P1—F21.608 (2)C16—C171.387 (5)
P1—F31.593 (2)C19—C201.334 (4)
P1—F41.585 (2)C1—H1C0.9800
P1—F51.604 (3)C1—H1B0.9800
P1—F61.590 (2)C1—H1A0.9800
P1—F11.586 (2)C2—H20.9500
P2—F71.584 (3)C3—H30.9500
P2—F101.570 (3)C4—H40.9500
P2—F111.589 (3)C6—H60.9500
P2—F121.599 (3)C7—H70.9500
P2—F81.582 (3)C9—H90.9500
P2—F91.600 (3)C10—H100.9500
P3—F151.581 (3)C11—H11A0.9900
P3—F131.580 (3)C11—H11B0.9900
P3—F141.575 (3)C13—H130.9500
P3—F171.592 (3)C14—H140.9500
P3—F181.590 (3)C16—H160.9500
P3—F161.592 (3)C17—H170.9500
P4—F191.568 (2)C18—H180.9500
P4—F211.552 (4)C19—H190.9500
P4—F221.581 (2)C20—H200.9500
P4—F201.599 (2)C21—H21C0.9800
P4—F241.576 (4)C21—H21A0.9800
P4—F231.577 (3)C21—H21B0.9800
N1—C21.332 (5)C24—C251.343 (5)
N1—C41.373 (6)C26—C311.390 (5)
N1—C11.470 (6)C26—C271.378 (4)
N2—C51.444 (4)C27—C281.394 (5)
N2—C21.336 (5)C28—C291.396 (4)
N2—C31.381 (5)C29—C321.520 (5)
N3—C151.438 (4)C29—C301.386 (4)
N3—C181.334 (4)C30—C311.376 (5)
N3—C201.387 (4)C32—C331.511 (4)
N4—C181.319 (4)C33—C341.392 (5)
N4—C191.372 (4)C33—C381.386 (4)
N4—C211.496 (5)C34—C351.377 (4)
N5—C221.447 (5)C35—C361.385 (4)
N5—C231.327 (5)C36—C371.384 (5)
N5—C251.369 (5)C37—C381.401 (4)
N6—C231.340 (4)C40—C411.348 (4)
N6—C241.386 (4)C22—H22B0.9800
N6—C261.435 (4)C22—H22C0.9800
N7—C411.386 (4)C22—H22A0.9800
N7—C391.345 (4)C23—H230.9500
N7—C361.429 (4)C24—H240.9500
N8—C401.383 (4)C25—H250.9500
N8—C391.323 (4)C27—H270.9500
N8—C421.472 (5)C28—H280.9500
C3—C41.335 (6)C30—H300.9500
C5—C101.384 (5)C31—H310.9500
C5—C61.391 (4)C32—H32A0.9900
C6—C71.382 (5)C32—H32B0.9900
C7—C81.388 (4)C34—H340.9500
C8—C111.518 (5)C35—H350.9500
C8—C91.395 (4)C37—H370.9500
C9—C101.390 (5)C38—H380.9500
C11—C121.510 (5)C39—H390.9500
C12—C131.392 (4)C40—H400.9500
C12—C171.386 (5)C41—H410.9500
C13—C141.378 (4)C42—H42C0.9800
C14—C151.384 (5)C42—H42A0.9800
C15—C161.387 (4)C42—H42B0.9800
F2—P1—F389.30 (12)H1A—C1—H1B109.00
F2—P1—F4179.63 (13)H1B—C1—H1C109.00
F2—P1—F589.55 (13)N1—C1—H1C110.00
F2—P1—F689.54 (13)N2—C2—H2127.00
F3—P1—F491.05 (12)N1—C2—H2127.00
F3—P1—F589.18 (13)C4—C3—H3127.00
F3—P1—F689.77 (13)N2—C3—H3126.00
F4—P1—F590.58 (13)C3—C4—H4126.00
F4—P1—F690.34 (13)N1—C4—H4127.00
F5—P1—F6178.61 (14)C7—C6—H6121.00
F1—P1—F289.84 (12)C5—C6—H6121.00
F1—P1—F3178.46 (13)C8—C7—H7119.00
F1—P1—F489.82 (12)C6—C7—H7119.00
F1—P1—F589.55 (13)C10—C9—H9119.00
F1—P1—F691.50 (13)C8—C9—H9119.00
F8—P2—F1190.74 (15)C9—C10—H10121.00
F8—P2—F1288.60 (14)C5—C10—H10121.00
F9—P2—F1089.37 (16)C8—C11—H11B109.00
F9—P2—F1189.05 (16)C12—C11—H11A109.00
F9—P2—F1289.82 (13)H11A—C11—H11B108.00
F10—P2—F1189.98 (15)C8—C11—H11A109.00
F10—P2—F1290.64 (14)C12—C11—H11B109.00
F11—P2—F12178.71 (17)C14—C13—H13119.00
F8—P2—F988.74 (16)C12—C13—H13119.00
F8—P2—F10177.97 (19)C15—C14—H14120.00
F7—P2—F890.21 (18)C13—C14—H14120.00
F7—P2—F9178.95 (16)C17—C16—H16121.00
F7—P2—F1091.68 (18)C15—C16—H16121.00
F7—P2—F1190.94 (17)C12—C17—H17119.00
F7—P2—F1290.18 (14)C16—C17—H17119.00
F13—P3—F1491.55 (15)N4—C18—H18126.00
F13—P3—F15178.21 (15)N3—C18—H18126.00
F14—P3—F1889.96 (13)C20—C19—H19126.00
F15—P3—F1688.84 (16)N4—C19—H19126.00
F15—P3—F1788.94 (16)C19—C20—H20127.00
F15—P3—F1890.41 (16)N3—C20—H20127.00
F16—P3—F1789.79 (16)H21B—C21—H21C110.00
F16—P3—F1890.14 (16)N4—C21—H21A109.00
F17—P3—F18179.34 (15)H21A—C21—H21B109.00
F14—P3—F1790.10 (13)H21A—C21—H21C109.00
F13—P3—F1889.96 (16)N4—C21—H21B109.00
F13—P3—F1689.41 (16)N4—C21—H21C109.00
F13—P3—F1790.70 (16)N5—C23—N6107.5 (3)
F14—P3—F1590.21 (15)N6—C24—C25106.8 (3)
F14—P3—F16179.04 (16)N5—C25—C24107.3 (3)
F19—P4—F21179.05 (19)N6—C26—C27120.1 (3)
F19—P4—F2089.58 (13)N6—C26—C31118.5 (3)
F21—P4—F2289.70 (18)C27—C26—C31121.4 (3)
F21—P4—F2390.7 (2)C26—C27—C28118.8 (3)
F21—P4—F2492.1 (2)C27—C28—C29121.0 (3)
F22—P4—F2390.66 (15)C28—C29—C30118.3 (3)
F22—P4—F2489.28 (16)C28—C29—C32121.2 (3)
F23—P4—F24177.2 (2)C30—C29—C32120.5 (3)
F20—P4—F22179.50 (14)C29—C30—C31121.8 (3)
F20—P4—F2389.68 (15)C26—C31—C30118.8 (3)
F20—P4—F2490.40 (16)C29—C32—C33112.7 (3)
F19—P4—F2290.80 (14)C32—C33—C34120.5 (3)
F19—P4—F2388.54 (16)C32—C33—C38121.5 (3)
F19—P4—F2488.68 (18)C34—C33—C38118.0 (3)
F20—P4—F2189.92 (18)C33—C34—C35122.1 (3)
C1—N1—C2124.0 (4)C34—C35—C36118.9 (3)
C1—N1—C4125.9 (3)C35—C36—C37120.9 (3)
C2—N1—C4109.9 (3)N7—C36—C37119.1 (3)
C3—N2—C5125.9 (3)N7—C36—C35119.9 (3)
C2—N2—C5124.6 (3)C36—C37—C38119.0 (3)
C2—N2—C3109.4 (3)C33—C38—C37121.0 (3)
C18—N3—C20108.2 (2)N7—C39—N8109.1 (3)
C15—N3—C20126.5 (3)N8—C40—C41107.8 (3)
C15—N3—C18125.0 (3)N7—C41—C40106.9 (3)
C18—N4—C19108.5 (3)N5—C22—H22B109.00
C18—N4—C21124.3 (3)N5—C22—H22C110.00
C19—N4—C21127.2 (3)H22A—C22—H22B109.00
C22—N5—C23124.8 (3)N5—C22—H22A110.00
C22—N5—C25125.5 (3)H22A—C22—H22C109.00
C23—N5—C25109.7 (3)H22B—C22—H22C109.00
C24—N6—C26126.2 (3)N5—C23—H23126.00
C23—N6—C24108.7 (3)N6—C23—H23126.00
C23—N6—C26125.1 (3)N6—C24—H24127.00
C36—N7—C39124.6 (3)C25—C24—H24126.00
C36—N7—C41127.1 (3)N5—C25—H25126.00
C39—N7—C41108.0 (2)C24—C25—H25126.00
C39—N8—C40108.2 (3)C26—C27—H27121.00
C40—N8—C42126.8 (3)C28—C27—H27121.00
C39—N8—C42124.9 (3)C27—C28—H28120.00
N1—C2—N2106.7 (3)C29—C28—H28119.00
N2—C3—C4107.0 (4)C31—C30—H30119.00
N1—C4—C3107.0 (3)C29—C30—H30119.00
N2—C5—C6118.9 (3)C26—C31—H31121.00
C6—C5—C10121.4 (3)C30—C31—H31121.00
N2—C5—C10119.6 (3)H32A—C32—H32B108.00
C5—C6—C7118.3 (3)C29—C32—H32B109.00
C6—C7—C8122.2 (3)C33—C32—H32A109.00
C7—C8—C11121.1 (3)C29—C32—H32A109.00
C7—C8—C9117.9 (3)C33—C32—H32B109.00
C9—C8—C11121.0 (3)C35—C34—H34119.00
C8—C9—C10121.4 (3)C33—C34—H34119.00
C5—C10—C9118.8 (3)C34—C35—H35121.00
C8—C11—C12113.4 (3)C36—C35—H35120.00
C11—C12—C13121.5 (3)C36—C37—H37120.00
C13—C12—C17118.0 (3)C38—C37—H37121.00
C11—C12—C17120.5 (3)C37—C38—H38119.00
C12—C13—C14121.1 (3)C33—C38—H38120.00
C13—C14—C15119.8 (3)N7—C39—H39125.00
N3—C15—C14121.0 (3)N8—C39—H39125.00
N3—C15—C16118.5 (3)N8—C40—H40126.00
C14—C15—C16120.5 (3)C41—C40—H40126.00
C15—C16—C17118.6 (3)N7—C41—H41127.00
C12—C17—C16121.9 (3)C40—C41—H41127.00
N3—C18—N4108.6 (3)H42A—C42—H42C110.00
N4—C19—C20108.1 (3)H42B—C42—H42C109.00
N3—C20—C19106.6 (3)H42A—C42—H42B109.00
H1A—C1—H1C110.00N8—C42—H42A110.00
N1—C1—H1B109.00N8—C42—H42B110.00
N1—C1—H1A109.00N8—C42—H42C109.00
C1—N1—C2—N2−174.4 (4)N2—C5—C10—C9176.1 (3)
C4—N1—C2—N20.5 (5)C6—C5—C10—C9−1.0 (5)
C1—N1—C4—C3174.1 (4)C10—C5—C6—C70.1 (5)
C2—N1—C4—C3−0.6 (5)C5—C6—C7—C8−0.3 (5)
C3—N2—C2—N1−0.1 (4)C6—C7—C8—C91.3 (5)
C5—N2—C2—N1174.9 (3)C6—C7—C8—C11−179.1 (3)
C2—N2—C3—C4−0.3 (5)C7—C8—C9—C10−2.2 (5)
C5—N2—C3—C4−175.2 (3)C11—C8—C9—C10178.2 (3)
C2—N2—C5—C6−33.9 (5)C7—C8—C11—C12−39.9 (5)
C2—N2—C5—C10148.9 (4)C9—C8—C11—C12139.7 (3)
C3—N2—C5—C6140.2 (4)C8—C9—C10—C52.0 (5)
C3—N2—C5—C10−36.9 (5)C8—C11—C12—C13103.9 (4)
C18—N3—C15—C14−143.1 (3)C8—C11—C12—C17−73.9 (4)
C18—N3—C15—C1633.0 (5)C11—C12—C13—C14−174.9 (3)
C20—N3—C15—C1429.7 (5)C17—C12—C13—C143.0 (5)
C20—N3—C15—C16−154.3 (3)C13—C12—C17—C16−2.1 (5)
C15—N3—C18—N4174.3 (3)C11—C12—C17—C16175.8 (3)
C20—N3—C18—N40.4 (4)C12—C13—C14—C15−0.6 (5)
C15—N3—C20—C19−174.0 (3)C13—C14—C15—C16−2.8 (5)
C18—N3—C20—C19−0.3 (4)C13—C14—C15—N3173.2 (3)
C19—N4—C18—N3−0.4 (4)N3—C15—C16—C17−172.4 (3)
C21—N4—C18—N3178.4 (3)C14—C15—C16—C173.7 (5)
C18—N4—C19—C200.2 (4)C15—C16—C17—C12−1.2 (5)
C21—N4—C19—C20−178.5 (3)N4—C19—C20—N30.0 (4)
C23—N5—C25—C240.4 (4)N6—C24—C25—N5−0.1 (4)
C22—N5—C23—N6178.2 (3)N6—C26—C27—C28−178.3 (3)
C25—N5—C23—N6−0.7 (4)C31—C26—C27—C280.8 (5)
C22—N5—C25—C24−178.4 (4)N6—C26—C31—C30179.2 (3)
C23—N6—C24—C25−0.3 (4)C27—C26—C31—C300.0 (5)
C26—N6—C24—C25−178.3 (3)C26—C27—C28—C29−1.2 (5)
C23—N6—C26—C2731.0 (5)C27—C28—C29—C300.9 (5)
C26—N6—C23—N5178.6 (3)C27—C28—C29—C32−178.9 (3)
C24—N6—C23—N50.6 (4)C28—C29—C30—C31−0.1 (5)
C24—N6—C26—C27−151.3 (3)C32—C29—C30—C31179.7 (3)
C24—N6—C26—C3129.5 (5)C28—C29—C32—C33−133.3 (3)
C23—N6—C26—C31−148.1 (3)C30—C29—C32—C3347.0 (4)
C41—N7—C36—C35154.4 (3)C29—C30—C31—C26−0.4 (5)
C41—N7—C36—C37−28.3 (5)C29—C32—C33—C3474.0 (4)
C39—N7—C36—C35−32.7 (5)C29—C32—C33—C38−103.8 (4)
C39—N7—C36—C37144.6 (3)C32—C33—C34—C35−175.0 (3)
C36—N7—C39—N8−174.7 (3)C38—C33—C34—C352.8 (5)
C41—N7—C39—N8−0.7 (4)C32—C33—C38—C37174.8 (3)
C36—N7—C41—C40174.0 (3)C34—C33—C38—C37−3.0 (5)
C39—N7—C41—C400.2 (4)C33—C34—C35—C360.2 (5)
C39—N8—C40—C41−0.7 (4)C34—C35—C36—N7174.2 (3)
C42—N8—C40—C41177.7 (3)C34—C35—C36—C37−3.1 (5)
C42—N8—C39—N7−177.6 (3)N7—C36—C37—C38−174.5 (3)
C40—N8—C39—N70.9 (4)C35—C36—C37—C382.9 (5)
N2—C3—C4—N10.6 (5)C36—C37—C38—C330.3 (5)
N2—C5—C6—C7−177.0 (3)N8—C40—C41—N70.3 (4)

Hydrogen-bond geometry (Å, °)

Cg3 and Cg7 are the centroids of the C5–C10 and C26–C31 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1A···F11i0.982.503.345 (5)144
C2—H2···F9i0.952.323.243 (5)163
C3—H3···F8ii0.952.383.322 (5)170
C4—H4···F19ii0.952.503.369 (5)152
C11—H11B···F60.992.403.271 (4)146
C16—H16···F100.952.433.098 (5)128
C18—H18···F120.952.423.315 (4)156
C20—H20···F20iii0.952.383.284 (4)160
C20—H20···F21iii0.952.553.123 (5)119
C21—H21B···F4iv0.982.423.269 (5)144
C22—H22C···F1v0.982.353.074 (5)130
C22—H22C···F17v0.982.383.239 (5)146
C23—H23···F13v0.952.403.330 (5)167
C24—H24···F14iv0.952.483.086 (4)122
C24—H24···F17iv0.952.493.374 (5)155
C30—H30···F4iv0.952.523.024 (4)114
C34—H34···F24i0.952.433.289 (4)150
C38—H38···F23iii0.952.533.262 (5)134
C39—H39···F16vi0.952.453.289 (4)147
C41—H41···F2iii0.952.393.229 (4)147
C42—H42B···F22vi0.982.353.217 (4)147
C1—H1B···Cg7vii0.982.553.387 (5)144
C25—H25···Cg3v0.952.963.805 (4)149

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y−1, z; (vii) −x, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2188).

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