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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1274.
Published online 2009 May 14. doi:  10.1107/S1600536809017140
PMCID: PMC2969606

3-(9-Anthrylmethyl)-1-benzylperimi­dinium hexa­fluoro­phosphate

Abstract

In the title compound, C33H25N2 +·PF6 , the naphthalene ring system is twisted with respect to the anthracene and benzene rings, making dihedral angles of 72.40 (3) and 71.39 (4)°, respectively. The crystal structure is stabilized by intermolecular C—H(...)F hydrogen bonding. Four F atoms of the hexa­fluoro­phosphate anion are disordered over two sets of sites in a 0.645 (4):0.355 (4) ratio.

Related literature

For the synthesis, see: Özdemir et al.. (2004 [triangle]); Aksenov et al. (2008 [triangle]). For related structures, see: Bazinet et al. (2007 [triangle]).

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Object name is e-65-o1274-scheme1.jpg

Experimental

Crystal data

  • C33H25N2 +·F6P
  • M r = 594.52
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1274-efi1.jpg
  • a = 9.9596 (13) Å
  • b = 11.8644 (17) Å
  • c = 11.8994 (12) Å
  • α = 94.436 (4)°
  • β = 95.159 (3)°
  • γ = 110.399 (6)°
  • V = 1303.6 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 113 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: none
  • 9272 measured reflections
  • 4823 independent reflections
  • 3619 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.113
  • S = 1.01
  • 4823 reflections
  • 416 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.49 e Å−3

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: ORTEP-3 for Windows (Farrugia, 1997 [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/S1600536809017140/xu2514sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017140/xu2514Isup2.hkl

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

Acknowledgments

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, China (grant No. 2006B039).

supplementary crystallographic information

Comment

In recent years, numerous cyclic N-heterocyclic carbene (NHC) precursors have been synthesized and structurally investigated. They have been recognized as powerfit ligands owing to their ability to coordinate very strongly to transition metals and main-group elements and an increasing use in organometallic chemistry, homogeneous catalysis. In addition, a number of biological activities of imidazolium salts have been reported including antimicrobial, antifungal, antitumor. We report here crystal structure of NHC precursor, the title compound.

The molecular structure is shown in Fig. 1. The naphthalene ring system is twisted with the anthracene ring and benzene ring with the dihedral angles of 72.40 (3)° and 71.39 (4)°. The crystal structure is stabilized by C—H···F hydrogen bonds (Table 1).

Experimental

The title compound was prepared according to the procedure reported by Özdemir et al. (2004) and Aksenov et al. (2008). Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile.

Refinement

H atoms were placed in calculated positions with C—H = 0.95–0.99 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C). The four equatorial F atoms (F2–F5) in the anion PF6 were disordered at two palces, occupancies were refined to a 0.645 (4):0.355 (4) ratio.

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. The minor component of disordered PF6- has been omitted for clarity.

Crystal data

C33H25N2+·F6PZ = 2
Mr = 594.52F(000) = 612
Triclinic, P1Dx = 1.515 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 9.9596 (13) ÅCell parameters from 3227 reflections
b = 11.8644 (17) Åθ = 2.2–28.0°
c = 11.8994 (12) ŵ = 0.18 mm1
α = 94.436 (4)°T = 113 K
β = 95.159 (3)°Prism, yellow
γ = 110.399 (6)°0.22 × 0.20 × 0.18 mm
V = 1303.6 (3) Å3

Data collection

Rigaku Saturn diffractometer3619 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
graphiteθmax = 25.5°, θmin = 2.2°
Detector resolution: 7.31 pixels mm-1h = −12→12
ω scansk = −14→13
9272 measured reflectionsl = −14→14
4823 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3
4823 reflections(Δ/σ)max < 0.001
416 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.49 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/UeqOcc. (<1)
N10.65525 (14)0.26739 (12)0.34502 (11)0.0171 (3)
N20.76633 (15)0.21452 (12)0.19570 (11)0.0166 (3)
C10.7929 (2)0.54158 (17)0.41449 (17)0.0318 (5)
H10.81040.52390.33910.038*
C20.8809 (2)0.64882 (17)0.47870 (18)0.0370 (5)
H20.95930.70360.44780.044*
C30.8547 (2)0.67608 (17)0.58745 (17)0.0313 (5)
H30.91340.75050.63080.038*
C40.7426 (2)0.59450 (16)0.63322 (16)0.0272 (4)
H40.72540.61220.70870.033*
C50.65546 (19)0.48705 (16)0.56896 (15)0.0243 (4)
H50.57850.43160.60070.029*
C60.67932 (18)0.45972 (15)0.45940 (15)0.0209 (4)
C70.57901 (18)0.34585 (15)0.38640 (15)0.0209 (4)
H7A0.50350.29980.43120.025*
H7B0.53060.36890.32040.025*
C80.68755 (18)0.18549 (14)0.41469 (14)0.0182 (4)
C90.64948 (18)0.17407 (15)0.52252 (14)0.0230 (4)
H90.60240.22350.55500.028*
C100.68127 (19)0.08799 (16)0.58429 (16)0.0264 (4)
H100.65320.07830.65820.032*
C110.75186 (19)0.01810 (16)0.53968 (16)0.0266 (4)
H110.7727−0.03890.58320.032*
C120.79414 (19)0.02947 (15)0.43000 (15)0.0223 (4)
C130.86924 (19)−0.03935 (15)0.38004 (16)0.0254 (4)
H130.8926−0.09690.42130.030*
C140.90839 (19)−0.02426 (15)0.27382 (16)0.0250 (4)
H140.9593−0.07120.24270.030*
C150.87524 (18)0.05926 (14)0.20896 (15)0.0203 (4)
H150.90250.06840.13480.024*
C160.80270 (17)0.12715 (14)0.25529 (14)0.0171 (4)
C170.69340 (17)0.27509 (14)0.24203 (14)0.0168 (4)
H170.66600.32870.19780.020*
C180.76120 (17)0.11481 (14)0.36533 (14)0.0177 (4)
C190.81402 (19)0.23771 (15)0.08085 (14)0.0204 (4)
H19A0.76220.16490.02600.024*
H19B0.91860.25250.08510.024*
C200.78569 (18)0.34486 (15)0.03857 (14)0.0189 (4)
C210.67085 (18)0.32839 (15)−0.04710 (14)0.0198 (4)
C220.58415 (19)0.21358 (15)−0.10874 (15)0.0232 (4)
H220.60330.1432−0.09220.028*
C230.4749 (2)0.20365 (16)−0.19052 (15)0.0276 (4)
H230.42100.1267−0.23160.033*
C240.4395 (2)0.30512 (17)−0.21595 (16)0.0295 (4)
H240.36050.2955−0.27160.035*
C250.51861 (19)0.41642 (17)−0.16064 (15)0.0265 (4)
H250.49440.4843−0.17800.032*
C260.63810 (19)0.43274 (15)−0.07648 (14)0.0205 (4)
C270.72088 (18)0.54694 (15)−0.02117 (14)0.0221 (4)
H270.69690.6148−0.03930.026*
C280.83807 (18)0.56432 (15)0.06025 (14)0.0204 (4)
C290.92430 (19)0.68278 (15)0.11489 (15)0.0244 (4)
H290.90210.75080.09480.029*
C301.0374 (2)0.69881 (16)0.19508 (16)0.0264 (4)
H301.09400.77790.23040.032*
C311.07145 (19)0.59810 (16)0.22627 (15)0.0249 (4)
H311.15080.61040.28250.030*
C320.99184 (18)0.48391 (15)0.17669 (14)0.0208 (4)
H321.01610.41770.19940.025*
C330.87223 (18)0.46190 (15)0.09092 (14)0.0192 (4)
F10.40915 (11)0.24779 (9)0.12667 (9)0.0327 (3)
F20.2510 (4)0.1531 (2)0.2443 (3)0.0547 (10)0.645 (4)
F30.1733 (2)0.1364 (2)0.0581 (3)0.0549 (11)0.645 (4)
F40.3399 (3)0.05825 (18)0.01761 (18)0.0455 (8)0.645 (4)
F50.4188 (2)0.07577 (17)0.2026 (2)0.0432 (8)0.645 (4)
F2'0.3311 (7)0.1323 (6)0.2590 (4)0.075 (3)0.355 (4)
F3'0.1746 (4)0.1825 (3)0.1473 (5)0.0555 (17)0.355 (4)
F4'0.2570 (6)0.1275 (4)−0.0041 (3)0.066 (2)0.355 (4)
F5'0.4147 (6)0.0736 (4)0.1032 (8)0.087 (3)0.355 (4)
F60.18320 (13)−0.02144 (10)0.13375 (11)0.0468 (3)
P10.29507 (5)0.11278 (4)0.12934 (4)0.02730 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0184 (7)0.0182 (7)0.0149 (8)0.0068 (6)0.0022 (6)0.0015 (6)
N20.0189 (7)0.0162 (7)0.0146 (8)0.0065 (6)0.0007 (6)0.0022 (5)
C10.0358 (11)0.0290 (11)0.0294 (11)0.0094 (9)0.0118 (9)−0.0018 (8)
C20.0348 (12)0.0277 (11)0.0437 (14)0.0042 (9)0.0139 (10)−0.0022 (9)
C30.0293 (11)0.0254 (10)0.0358 (12)0.0089 (8)−0.0007 (9)−0.0068 (8)
C40.0307 (11)0.0321 (11)0.0208 (10)0.0162 (8)−0.0003 (8)−0.0044 (8)
C50.0252 (10)0.0271 (10)0.0236 (10)0.0129 (8)0.0031 (8)0.0030 (7)
C60.0220 (9)0.0238 (9)0.0207 (10)0.0129 (7)0.0035 (7)0.0024 (7)
C70.0216 (9)0.0240 (9)0.0200 (10)0.0119 (7)0.0034 (7)0.0013 (7)
C80.0180 (9)0.0176 (9)0.0161 (9)0.0033 (7)−0.0022 (7)0.0036 (7)
C90.0241 (10)0.0243 (10)0.0199 (10)0.0074 (8)0.0033 (8)0.0041 (7)
C100.0275 (10)0.0285 (10)0.0180 (10)0.0024 (8)0.0025 (8)0.0078 (7)
C110.0271 (10)0.0245 (10)0.0254 (11)0.0060 (8)−0.0033 (8)0.0096 (8)
C120.0216 (9)0.0166 (9)0.0234 (10)0.0020 (7)−0.0052 (7)0.0035 (7)
C130.0280 (10)0.0199 (9)0.0280 (11)0.0101 (8)−0.0058 (8)0.0046 (7)
C140.0251 (10)0.0184 (9)0.0317 (11)0.0100 (8)−0.0018 (8)−0.0001 (7)
C150.0215 (9)0.0173 (9)0.0203 (10)0.0058 (7)0.0001 (7)0.0000 (7)
C160.0154 (8)0.0145 (8)0.0185 (9)0.0031 (6)−0.0031 (7)0.0020 (6)
C170.0171 (9)0.0174 (8)0.0152 (9)0.0057 (7)0.0001 (7)0.0023 (6)
C180.0152 (8)0.0150 (8)0.0185 (9)0.0016 (6)−0.0032 (7)0.0005 (7)
C190.0273 (10)0.0218 (9)0.0148 (9)0.0113 (7)0.0053 (7)0.0029 (7)
C200.0241 (9)0.0204 (9)0.0156 (9)0.0105 (7)0.0080 (7)0.0040 (7)
C210.0230 (9)0.0228 (9)0.0157 (9)0.0086 (7)0.0080 (7)0.0060 (7)
C220.0281 (10)0.0210 (9)0.0200 (10)0.0068 (7)0.0080 (8)0.0039 (7)
C230.0279 (10)0.0262 (10)0.0225 (10)0.0026 (8)0.0030 (8)0.0001 (8)
C240.0246 (10)0.0376 (11)0.0235 (11)0.0076 (8)0.0001 (8)0.0059 (8)
C250.0267 (10)0.0318 (11)0.0239 (10)0.0127 (8)0.0052 (8)0.0088 (8)
C260.0235 (9)0.0246 (9)0.0160 (9)0.0104 (7)0.0072 (7)0.0049 (7)
C270.0285 (10)0.0231 (9)0.0199 (10)0.0139 (8)0.0068 (8)0.0073 (7)
C280.0230 (9)0.0206 (9)0.0199 (10)0.0094 (7)0.0059 (7)0.0040 (7)
C290.0314 (10)0.0200 (9)0.0236 (10)0.0109 (8)0.0065 (8)0.0028 (7)
C300.0289 (10)0.0207 (10)0.0267 (11)0.0056 (8)0.0052 (8)−0.0013 (7)
C310.0230 (9)0.0294 (10)0.0211 (10)0.0080 (8)0.0031 (7)0.0024 (8)
C320.0238 (9)0.0227 (9)0.0191 (10)0.0108 (7)0.0062 (7)0.0058 (7)
C330.0222 (9)0.0224 (9)0.0153 (9)0.0091 (7)0.0070 (7)0.0046 (7)
F10.0280 (6)0.0320 (6)0.0335 (7)0.0037 (5)0.0002 (5)0.0139 (5)
F20.085 (2)0.0287 (12)0.047 (2)0.0098 (14)0.0414 (19)−0.0042 (11)
F30.0300 (12)0.0377 (13)0.089 (3)0.0041 (10)−0.0160 (14)0.0271 (14)
F40.0612 (18)0.0338 (12)0.0269 (12)−0.0031 (11)0.0200 (11)−0.0041 (9)
F50.0394 (13)0.0247 (10)0.0576 (17)0.0043 (8)−0.0149 (12)0.0163 (10)
F2'0.083 (5)0.074 (4)0.029 (3)−0.024 (3)−0.008 (3)0.031 (3)
F3'0.030 (2)0.031 (2)0.099 (5)0.0025 (16)0.022 (2)−0.005 (2)
F4'0.072 (4)0.065 (3)0.026 (2)−0.016 (3)0.000 (2)−0.0096 (19)
F5'0.062 (3)0.031 (2)0.192 (10)0.033 (2)0.064 (5)0.029 (4)
F60.0406 (7)0.0306 (7)0.0563 (9)−0.0037 (5)0.0159 (6)−0.0043 (6)
P10.0263 (3)0.0282 (3)0.0224 (3)0.0036 (2)0.0047 (2)0.0008 (2)

Geometric parameters (Å, °)

N1—C171.316 (2)C19—C201.507 (2)
N1—C81.425 (2)C19—H19A0.9900
N1—C71.475 (2)C19—H19B0.9900
N2—C171.312 (2)C20—C211.410 (2)
N2—C161.428 (2)C20—C331.412 (2)
N2—C191.501 (2)C21—C221.432 (2)
C1—C21.387 (3)C21—C261.445 (2)
C1—C61.390 (3)C22—C231.359 (2)
C1—H10.9500C22—H220.9500
C2—C31.379 (3)C23—C241.414 (3)
C2—H20.9500C23—H230.9500
C3—C41.385 (3)C24—C251.358 (2)
C3—H30.9500C24—H240.9500
C4—C51.386 (2)C25—C261.432 (2)
C4—H40.9500C25—H250.9500
C5—C61.380 (2)C26—C271.391 (2)
C5—H50.9500C27—C281.393 (2)
C6—C71.516 (2)C27—H270.9500
C7—H7A0.9900C28—C291.433 (2)
C7—H7B0.9900C28—C331.435 (2)
C8—C91.374 (2)C29—C301.359 (3)
C8—C181.420 (2)C29—H290.9500
C9—C101.408 (2)C30—C311.417 (2)
C9—H90.9500C30—H300.9500
C10—C111.367 (3)C31—C321.362 (2)
C10—H100.9500C31—H310.9500
C11—C121.409 (3)C32—C331.433 (2)
C11—H110.9500C32—H320.9500
C12—C131.418 (3)F1—P11.6135 (11)
C12—C181.425 (2)F2—P11.564 (2)
C13—C141.363 (3)F3—P11.5353 (19)
C13—H130.9500F4—P11.600 (2)
C14—C151.410 (2)F5—P11.6477 (19)
C14—H140.9500F2'—P11.533 (5)
C15—C161.372 (2)F3'—P11.697 (4)
C15—H150.9500F4'—P11.636 (4)
C16—C181.411 (2)F5'—P11.471 (4)
C17—H170.9500F6—P11.6021 (12)
C17—N1—C8120.62 (14)C22—C23—C24121.57 (17)
C17—N1—C7118.36 (14)C22—C23—H23119.2
C8—N1—C7121.02 (14)C24—C23—H23119.2
C17—N2—C16120.01 (14)C25—C24—C23119.87 (18)
C17—N2—C19120.46 (14)C25—C24—H24120.1
C16—N2—C19119.52 (13)C23—C24—H24120.1
C2—C1—C6120.56 (18)C24—C25—C26120.87 (17)
C2—C1—H1119.7C24—C25—H25119.6
C6—C1—H1119.7C26—C25—H25119.6
C3—C2—C1120.07 (18)C27—C26—C25120.98 (16)
C3—C2—H2120.0C27—C26—C21119.68 (16)
C1—C2—H2120.0C25—C26—C21119.32 (16)
C2—C3—C4119.72 (17)C26—C27—C28121.61 (16)
C2—C3—H3120.1C26—C27—H27119.2
C4—C3—H3120.1C28—C27—H27119.2
C3—C4—C5119.99 (18)C27—C28—C29121.05 (16)
C3—C4—H4120.0C27—C28—C33119.59 (15)
C5—C4—H4120.0C29—C28—C33119.36 (16)
C6—C5—C4120.76 (17)C30—C29—C28120.69 (16)
C6—C5—H5119.6C30—C29—H29119.7
C4—C5—H5119.6C28—C29—H29119.7
C5—C6—C1118.88 (16)C29—C30—C31120.31 (16)
C5—C6—C7120.93 (16)C29—C30—H30119.8
C1—C6—C7120.11 (16)C31—C30—H30119.8
N1—C7—C6112.65 (13)C32—C31—C30120.85 (17)
N1—C7—H7A109.1C32—C31—H31119.6
C6—C7—H7A109.1C30—C31—H31119.6
N1—C7—H7B109.1C31—C32—C33121.20 (16)
C6—C7—H7B109.1C31—C32—H32119.4
H7A—C7—H7B107.8C33—C32—H32119.4
C9—C8—C18121.59 (16)C20—C33—C32123.01 (16)
C9—C8—N1122.67 (15)C20—C33—C28119.38 (16)
C18—C8—N1115.74 (15)C32—C33—C28117.59 (15)
C8—C9—C10119.04 (17)F5'—P1—F2'97.4 (5)
C8—C9—H9120.5F5'—P1—F3134.8 (4)
C10—C9—H9120.5F2'—P1—F3127.7 (3)
C11—C10—C9121.11 (17)F5'—P1—F2132.0 (4)
C11—C10—H10119.4F2'—P1—F234.6 (3)
C9—C10—H10119.4F3—P1—F293.12 (18)
C10—C11—C12120.93 (17)F5'—P1—F444.5 (3)
C10—C11—H11119.5F2'—P1—F4141.3 (4)
C12—C11—H11119.5F3—P1—F490.88 (17)
C11—C12—C13123.40 (16)F2—P1—F4173.66 (14)
C11—C12—C18118.90 (16)F5'—P1—F694.76 (17)
C13—C12—C18117.71 (16)F2'—P1—F691.31 (19)
C14—C13—C12121.02 (16)F3—P1—F687.39 (9)
C14—C13—H13119.5F2—P1—F688.91 (11)
C12—C13—H13119.5F4—P1—F686.36 (8)
C13—C14—C15121.62 (17)F5'—P1—F184.92 (17)
C13—C14—H14119.2F2'—P1—F187.91 (19)
C15—C14—H14119.2F3—P1—F193.42 (9)
C16—C15—C14118.59 (17)F2—P1—F190.69 (11)
C16—C15—H15120.7F4—P1—F193.98 (8)
C14—C15—H15120.7F6—P1—F1179.11 (7)
C15—C16—C18121.50 (16)F5'—P1—F4'91.6 (4)
C15—C16—N2122.08 (16)F2'—P1—F4'165.3 (3)
C18—C16—N2116.42 (15)F3—P1—F4'43.9 (2)
N2—C17—N1125.09 (15)F2—P1—F4'135.0 (3)
N2—C17—H17117.5F4—P1—F4'50.3 (2)
N1—C17—H17117.5F6—P1—F4'99.54 (15)
C16—C18—C8122.03 (15)F1—P1—F4'81.30 (15)
C16—C18—C12119.56 (16)F5'—P1—F543.9 (3)
C8—C18—C12118.41 (16)F2'—P1—F554.1 (3)
N2—C19—C20112.12 (13)F3—P1—F5175.39 (11)
N2—C19—H19A109.2F2—P1—F588.54 (16)
C20—C19—H19A109.2F4—P1—F587.11 (15)
N2—C19—H19B109.2F6—P1—F588.35 (9)
C20—C19—H19B109.2F1—P1—F590.85 (8)
H19A—C19—H19B107.9F4'—P1—F5135.5 (3)
C21—C20—C33120.73 (15)F5'—P1—F3'168.7 (2)
C21—C20—C19120.84 (15)F2'—P1—F3'86.9 (3)
C33—C20—C19118.35 (15)F3—P1—F3'41.43 (18)
C20—C21—C22123.91 (16)F2—P1—F3'52.9 (2)
C20—C21—C26118.90 (15)F4—P1—F3'131.8 (2)
C22—C21—C26117.19 (16)F6—P1—F3'95.57 (13)
C23—C22—C21121.10 (17)F1—P1—F3'84.82 (13)
C23—C22—H22119.5F4'—P1—F3'82.2 (3)
C21—C22—H22119.5F5—P1—F3'141.0 (2)
C6—C1—C2—C3−1.1 (3)N1—C8—C18—C12−178.82 (14)
C1—C2—C3—C41.7 (3)C11—C12—C18—C16−179.93 (15)
C2—C3—C4—C5−1.3 (3)C13—C12—C18—C160.5 (2)
C3—C4—C5—C60.3 (3)C11—C12—C18—C80.3 (2)
C4—C5—C6—C10.3 (3)C13—C12—C18—C8−179.26 (14)
C4—C5—C6—C7−176.36 (16)C17—N2—C19—C207.6 (2)
C2—C1—C6—C50.1 (3)C16—N2—C19—C20−171.50 (14)
C2—C1—C6—C7176.79 (17)N2—C19—C20—C21−104.92 (18)
C17—N1—C7—C6−97.27 (17)N2—C19—C20—C3371.8 (2)
C8—N1—C7—C682.48 (19)C33—C20—C21—C22176.07 (16)
C5—C6—C7—N1−123.00 (17)C19—C20—C21—C22−7.2 (3)
C1—C6—C7—N160.4 (2)C33—C20—C21—C26−3.2 (2)
C17—N1—C8—C9−179.79 (15)C19—C20—C21—C26173.47 (15)
C7—N1—C8—C90.5 (2)C20—C21—C22—C23−179.96 (17)
C17—N1—C8—C18−0.3 (2)C26—C21—C22—C23−0.7 (3)
C7—N1—C8—C18179.97 (13)C21—C22—C23—C24−1.8 (3)
C18—C8—C9—C10−1.6 (3)C22—C23—C24—C252.2 (3)
N1—C8—C9—C10177.89 (15)C23—C24—C25—C260.0 (3)
C8—C9—C10—C111.5 (3)C24—C25—C26—C27178.84 (17)
C9—C10—C11—C12−0.5 (3)C24—C25—C26—C21−2.5 (3)
C10—C11—C12—C13179.12 (16)C20—C21—C26—C270.8 (2)
C10—C11—C12—C18−0.4 (3)C22—C21—C26—C27−178.56 (15)
C11—C12—C13—C14−179.60 (16)C20—C21—C26—C25−177.89 (15)
C18—C12—C13—C140.0 (2)C22—C21—C26—C252.8 (2)
C12—C13—C14—C15−0.5 (3)C25—C26—C27—C28−179.52 (16)
C13—C14—C15—C160.5 (3)C21—C26—C27—C281.8 (3)
C14—C15—C16—C180.0 (2)C26—C27—C28—C29178.68 (16)
C14—C15—C16—N2179.37 (15)C26—C27—C28—C33−2.0 (3)
C17—N2—C16—C15178.13 (14)C27—C28—C29—C30179.29 (17)
C19—N2—C16—C15−2.8 (2)C33—C28—C29—C300.0 (3)
C17—N2—C16—C18−2.4 (2)C28—C29—C30—C31−0.3 (3)
C19—N2—C16—C18176.65 (13)C29—C30—C31—C320.0 (3)
C16—N2—C17—N13.9 (2)C30—C31—C32—C330.6 (3)
C19—N2—C17—N1−175.18 (14)C21—C20—C33—C32−178.74 (16)
C8—N1—C17—N2−2.5 (2)C19—C20—C33—C324.5 (3)
C7—N1—C17—N2177.28 (14)C21—C20—C33—C283.1 (3)
C15—C16—C18—C8179.28 (15)C19—C20—C33—C28−173.69 (15)
N2—C16—C18—C8−0.2 (2)C31—C32—C33—C20−179.07 (17)
C15—C16—C18—C12−0.4 (2)C31—C32—C33—C28−0.8 (3)
N2—C16—C18—C12−179.89 (14)C27—C28—C33—C20−0.5 (3)
C9—C8—C18—C16−179.03 (15)C29—C28—C33—C20178.87 (15)
N1—C8—C18—C161.5 (2)C27—C28—C33—C32−178.75 (15)
C9—C8—C18—C120.7 (2)C29—C28—C33—C320.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10···F5i0.952.523.327 (3)142
C11—H11···F2i0.952.533.393 (4)151
C19—H19A···F4ii0.992.483.368 (3)150
C27—H27···F1iii0.952.473.401 (2)165
C29—H29···F3iii0.952.553.400 (3)149

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2514).

References

  • Aksenov, A. V., Lyahovnenko, A. S., Aksenova, I. V. & Nadein, O. N. (2008). Tetrahedron Lett.49, 1808–1811.
  • Bazinet, P., Ong, T. G., O’Brien, J. S., Lavoie, N., Bell, E., Yap, G. P. A., Korobkov, I. & Richeson, D. S. (2007). Organometallics, 26, 2885–2895.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Özdemir, Í., Alici, B., Gürbüz, N., Çetinkaya, E. & Çetinkaya, B. (2004). J. Mol. Catal. A., 217, 37–40.
  • Rigaku/MSC (2004). CrystalStructure and CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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