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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1171.
Published online 2010 April 24. doi:  10.1107/S1600536810014534
PMCID: PMC2979123

1-{2-[2-(1H-Benzimidazol-1-yl)eth­oxy]eth­yl}-1H-benzimidazol-3-ium hexa­fluoro­phosphate

Abstract

In the title salt, C18H19N4O+·PF6 , the dihedral angle between the benzimidazolium and benzimidazole ring systems is 16.24 (2)°. In the cation, a π–π inter­action is observed between the imidazolium ring and the benzene ring of the benzimidazole ring system [centroid–centroid distance = 3.5713 (11) Å]. The PF6 ion is disordered over two sites, with occupancies of 0.895 (2) and 0.105 (2). In the crystal structure, pairs of N—H(...)N hydrogen bonds link the cations, forming centrosymmetric dimers. The dimers are linked via π–π inter­actions [centroid–centroid distance = 3.5606 (11) Å]. In addition, C—H(...)F hydrogen bonds are observed.

Related literature

For the synthesis, see: Zeng et al. (2008 [triangle]). For general background to benzimidazole derivatives, see: Pal et al. (2007 [triangle]); Murru et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1171-scheme1.jpg

Experimental

Crystal data

  • C18H19N4O+·PF6
  • M r = 452.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1171-efi1.jpg
  • a = 10.5347 (18) Å
  • b = 13.771 (2) Å
  • c = 13.353 (2) Å
  • β = 92.507 (2)°
  • V = 1935.3 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 93 K
  • 0.37 × 0.33 × 0.27 mm

Data collection

  • Rigaku SPIDER diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.923, T max = 0.943
  • 11885 measured reflections
  • 3959 independent reflections
  • 3445 reflections with I > 2σ(I)
  • R int = 0.026
  • Standard reflections: 0

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.080
  • S = 1.00
  • 3959 reflections
  • 303 parameters
  • 21 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.28 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014534/ci5075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014534/ci5075Isup2.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) for financial support.

supplementary crystallographic information

Comment

Benzimidazole derivatives are an important class of heterocycles that are present in a number of biologically active compounds. These derivatives are also used as cyclic N-heterocyclic carbene (NHC) precursors (Murru et al., 2009). A benzimidazole N-donor dinuclear palladacycle complex is used as an efficient Suzuki coupling catalyst (Pal et al., 2007).

Bond lengths and angles in the ionic pairs (Fig. 1) are within normal ranges. The benzimidazolium and benzimidazole ring systems make a dihedral angle of 16.24 (2)°. In the cation, a π–π interaction is observed between N1/C1/C6/N2C7 and C12-C17 rings, with the ring centroids being separated by 3.5713 (11) Å.

In the crystal structure, pairs of N—H···N hydrogen bonds link cations to form centrosymmetric dimers. The dimers are linked via π–π interactions between the N1/C1/C6/N2C7 ring at (x, y, z) and the C12-C17 ring at (1-x, y-1/2, 1/2-z), with their centroids separated by 3.5606 (11) Å. In addition, C—H···F hydrogen bonds are observed (Table 1).

Experimental

The title compound was prepared according to the reported procedure of Zeng et al.. (2008). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile and ethyl ether.

Refinement

The PF6- ion is disordered over two sites with occupancies of 0.895 (2) and 0.105 (2). The Uij values of atom pairs F1/F1', F2/F2', F3/F3, F4/F4', F5/F5' and F6/F6' were constrained to be equal. The corresponding distances in the two disorder components were restrained to be the same. Atom H1N was located in a difference map and refined freely. All other H atoms were placed in calculated positions [C–H = 0.95–0.99 Å] and refined in riding mode with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. C-bound H atoms have been omitted. For clarity, only the major disorder component is shown.

Crystal data

C18H19N4O+·PF6F(000) = 928
Mr = 452.34Dx = 1.553 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5714 reflections
a = 10.5347 (18) Åθ = 3.1–27.5°
b = 13.771 (2) ŵ = 0.22 mm1
c = 13.353 (2) ÅT = 93 K
β = 92.507 (2)°Block, colourless
V = 1935.3 (6) Å30.37 × 0.33 × 0.27 mm
Z = 4

Data collection

Rigaku SPIDER diffractometer3959 independent reflections
Radiation source: Rotating Anode3445 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −13→10
Tmin = 0.923, Tmax = 0.943k = −13→17
11885 measured reflectionsl = −15→16

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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0259P)2 + 0.968P] where P = (Fo2 + 2Fc2)/3
3959 reflections(Δ/σ)max = 0.001
303 parametersΔρmax = 0.34 e Å3
21 restraintsΔρmin = −0.28 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)
O10.20360 (11)0.51931 (8)0.18156 (8)0.0247 (3)
N10.53426 (13)0.40531 (10)0.31178 (10)0.0243 (3)
N20.41920 (13)0.39824 (9)0.17089 (10)0.0218 (3)
N30.26475 (13)0.62988 (10)0.35541 (10)0.0253 (3)
N40.39492 (14)0.60700 (10)0.48994 (10)0.0294 (3)
C10.61864 (16)0.39760 (11)0.23507 (12)0.0229 (3)
C20.75022 (16)0.39314 (12)0.23627 (13)0.0285 (4)
H20.80050.39640.29700.034*
C30.80419 (17)0.38372 (13)0.14435 (14)0.0319 (4)
H30.89410.38010.14200.038*
C40.73059 (17)0.37927 (13)0.05438 (13)0.0311 (4)
H40.77180.3730−0.00720.037*
C50.60018 (16)0.38377 (12)0.05330 (12)0.0262 (4)
H50.54990.3808−0.00750.031*
C60.54567 (15)0.39293 (11)0.14572 (12)0.0218 (3)
C70.41753 (16)0.40521 (11)0.27069 (12)0.0245 (4)
H70.34240.40950.30730.029*
C80.31129 (15)0.39532 (12)0.09736 (12)0.0242 (4)
H8A0.30300.32880.06980.029*
H8B0.32860.43970.04120.029*
C90.18818 (16)0.42403 (12)0.14171 (13)0.0262 (4)
H9A0.11850.42310.08950.031*
H9B0.16680.37800.19540.031*
C100.10406 (16)0.54786 (12)0.24439 (12)0.0272 (4)
H10A0.08900.49680.29470.033*
H10B0.02430.55840.20390.033*
C110.14574 (16)0.64079 (13)0.29557 (12)0.0277 (4)
H11A0.15680.69160.24420.033*
H11B0.07830.66270.33970.033*
C120.38716 (16)0.64002 (11)0.32253 (12)0.0231 (3)
C130.43309 (16)0.65920 (12)0.22830 (12)0.0262 (4)
H130.37750.66870.17120.031*
C140.56322 (17)0.66369 (12)0.22204 (13)0.0295 (4)
H140.59820.67640.15900.035*
C150.64530 (18)0.64993 (12)0.30653 (14)0.0314 (4)
H150.73450.65390.29940.038*
C160.59940 (17)0.63079 (12)0.39979 (13)0.0294 (4)
H160.65530.62140.45670.035*
C170.46803 (17)0.62576 (11)0.40726 (12)0.0249 (4)
C180.27606 (18)0.61067 (13)0.45479 (12)0.0299 (4)
H180.20530.60080.49530.036*
P1−0.07196 (5)0.71567 (4)0.57610 (4)0.02117 (17)0.8952 (16)
F1−0.10379 (15)0.71525 (12)0.45828 (8)0.0350 (3)0.8952 (16)
F2−0.03912 (12)0.71374 (11)0.69440 (8)0.0393 (4)0.8952 (16)
F30.05729 (13)0.77151 (12)0.55925 (10)0.0540 (4)0.8952 (16)
F4−0.19885 (12)0.65494 (12)0.59425 (9)0.0479 (4)0.8952 (16)
F5−0.14535 (18)0.81437 (11)0.58739 (10)0.0589 (5)0.8952 (16)
F60.00255 (14)0.61439 (10)0.56578 (10)0.0509 (4)0.8952 (16)
P1'−0.0834 (6)0.7250 (5)0.5725 (5)0.141 (8)0.1048 (16)
F1'−0.0918 (11)0.7157 (9)0.4533 (4)0.0350 (3)0.1048 (16)
F2'−0.0730 (10)0.7334 (8)0.6921 (5)0.0393 (4)0.1048 (16)
F3'−0.0180 (10)0.8283 (6)0.5636 (8)0.0540 (4)0.1048 (16)
F4'−0.1434 (9)0.6186 (6)0.5824 (8)0.0479 (4)0.1048 (16)
F5'−0.2196 (8)0.7721 (8)0.5714 (8)0.0589 (5)0.1048 (16)
F6'0.0549 (7)0.6755 (8)0.5745 (8)0.0509 (4)0.1048 (16)
H1N0.560 (2)0.4037 (15)0.3887 (16)0.052 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0252 (6)0.0252 (6)0.0238 (6)−0.0009 (5)0.0013 (5)−0.0021 (5)
N10.0294 (8)0.0246 (7)0.0183 (7)0.0024 (6)−0.0043 (6)−0.0007 (6)
N20.0255 (7)0.0219 (7)0.0177 (6)0.0001 (6)−0.0024 (5)−0.0005 (5)
N30.0272 (8)0.0310 (8)0.0175 (7)0.0061 (6)−0.0033 (6)−0.0007 (6)
N40.0360 (9)0.0325 (8)0.0192 (7)0.0027 (6)−0.0050 (6)0.0010 (6)
C10.0294 (9)0.0190 (8)0.0200 (8)0.0016 (6)−0.0023 (7)−0.0006 (6)
C20.0285 (9)0.0297 (9)0.0266 (9)0.0011 (7)−0.0083 (7)0.0012 (7)
C30.0248 (9)0.0350 (10)0.0357 (10)0.0030 (7)0.0004 (8)0.0041 (8)
C40.0323 (10)0.0361 (10)0.0252 (9)0.0054 (8)0.0048 (8)0.0035 (8)
C50.0319 (10)0.0281 (9)0.0184 (8)0.0021 (7)−0.0026 (7)0.0003 (7)
C60.0246 (9)0.0180 (8)0.0225 (8)0.0011 (6)−0.0026 (7)−0.0001 (6)
C70.0301 (9)0.0235 (8)0.0198 (8)0.0017 (7)0.0007 (7)−0.0002 (7)
C80.0261 (9)0.0254 (9)0.0204 (8)−0.0013 (7)−0.0059 (7)−0.0011 (7)
C90.0259 (9)0.0268 (9)0.0255 (9)−0.0024 (7)−0.0030 (7)−0.0015 (7)
C100.0230 (9)0.0346 (10)0.0240 (9)0.0024 (7)0.0012 (7)0.0020 (7)
C110.0249 (9)0.0357 (10)0.0222 (8)0.0076 (7)−0.0027 (7)−0.0003 (7)
C120.0281 (9)0.0199 (8)0.0207 (8)0.0022 (7)−0.0044 (7)−0.0031 (6)
C130.0329 (10)0.0262 (9)0.0189 (8)−0.0019 (7)−0.0055 (7)−0.0033 (7)
C140.0347 (10)0.0285 (9)0.0254 (9)−0.0061 (7)0.0015 (8)−0.0051 (7)
C150.0288 (10)0.0287 (9)0.0362 (10)−0.0045 (7)−0.0039 (8)−0.0048 (8)
C160.0332 (10)0.0246 (9)0.0294 (9)−0.0008 (7)−0.0120 (8)−0.0027 (7)
C170.0325 (9)0.0202 (8)0.0212 (8)0.0013 (7)−0.0056 (7)−0.0019 (6)
C180.0360 (10)0.0346 (10)0.0189 (8)0.0048 (8)−0.0004 (7)0.0013 (7)
P10.0156 (3)0.0302 (3)0.0175 (4)−0.0041 (2)−0.0011 (2)0.0053 (3)
F10.0370 (7)0.0499 (7)0.0182 (5)0.0021 (5)0.0012 (4)0.0020 (5)
F20.0360 (9)0.0587 (9)0.0220 (5)−0.0174 (6)−0.0105 (5)0.0105 (5)
F30.0427 (9)0.0789 (11)0.0405 (8)−0.0350 (8)0.0021 (6)0.0096 (7)
F40.0266 (8)0.0901 (11)0.0269 (6)−0.0273 (7)−0.0006 (6)0.0019 (7)
F50.0895 (13)0.0551 (10)0.0322 (8)0.0370 (9)0.0014 (8)−0.0026 (7)
F60.0558 (9)0.0451 (9)0.0519 (8)0.0174 (7)0.0044 (7)0.0118 (7)
P1'0.167 (16)0.22 (2)0.030 (7)−0.026 (15)−0.032 (8)0.006 (9)
F1'0.0370 (7)0.0499 (7)0.0182 (5)0.0021 (5)0.0012 (4)0.0020 (5)
F2'0.0360 (9)0.0587 (9)0.0220 (5)−0.0174 (6)−0.0105 (5)0.0105 (5)
F3'0.0427 (9)0.0789 (11)0.0405 (8)−0.0350 (8)0.0021 (6)0.0096 (7)
F4'0.0266 (8)0.0901 (11)0.0269 (6)−0.0273 (7)−0.0006 (6)0.0019 (7)
F5'0.0895 (13)0.0551 (10)0.0322 (8)0.0370 (9)0.0014 (8)−0.0026 (7)
F6'0.0558 (9)0.0451 (9)0.0519 (8)0.0174 (7)0.0044 (7)0.0118 (7)

Geometric parameters (Å, °)

O1—C91.4224 (19)C10—C111.507 (2)
O1—C101.4266 (19)C10—H10A0.99
N1—C71.325 (2)C10—H10B0.99
N1—C11.389 (2)C11—H11A0.99
N1—H1N1.05 (2)C11—H11B0.99
N2—C71.337 (2)C12—C131.393 (2)
N2—C61.390 (2)C12—C171.400 (2)
N2—C81.470 (2)C13—C141.378 (2)
N3—C181.353 (2)C13—H130.95
N3—C121.387 (2)C14—C151.404 (2)
N3—C111.465 (2)C14—H140.95
N4—C181.319 (2)C15—C161.381 (3)
N4—C171.398 (2)C15—H150.95
C1—C21.387 (2)C16—C171.394 (2)
C1—C61.392 (2)C16—H160.95
C2—C31.381 (2)C18—H180.95
C2—H20.95P1—F51.5742 (14)
C3—C41.402 (3)P1—F31.5883 (13)
C3—H30.95P1—F11.5942 (12)
C4—C51.375 (2)P1—F21.6025 (12)
C4—H40.95P1—F41.6041 (12)
C5—C61.389 (2)P1—F61.6092 (14)
C5—H50.95P1'—F5'1.574 (3)
C7—H70.95P1'—F3'1.588 (3)
C8—C91.502 (2)P1'—F1'1.595 (3)
C8—H8A0.99P1'—F2'1.601 (3)
C8—H8B0.99P1'—F4'1.603 (3)
C9—H9A0.99P1'—F6'1.608 (3)
C9—H9B0.99
C9—O1—C10113.54 (12)C10—C11—H11B109.1
C7—N1—C1107.87 (14)H11A—C11—H11B107.8
C7—N1—H1N126.9 (11)N3—C12—C13132.02 (15)
C1—N1—H1N125.0 (11)N3—C12—C17105.74 (14)
C7—N2—C6107.41 (13)C13—C12—C17122.24 (16)
C7—N2—C8128.63 (14)C14—C13—C12116.68 (16)
C6—N2—C8123.95 (13)C14—C13—H13121.7
C18—N3—C12106.67 (14)C12—C13—H13121.7
C18—N3—C11126.26 (15)C13—C14—C15121.63 (16)
C12—N3—C11127.04 (13)C13—C14—H14119.2
C18—N4—C17105.03 (14)C15—C14—H14119.2
C2—C1—N1131.78 (15)C16—C15—C14121.52 (17)
C2—C1—C6121.47 (15)C16—C15—H15119.2
N1—C1—C6106.75 (14)C14—C15—H15119.2
C3—C2—C1116.36 (16)C15—C16—C17117.52 (16)
C3—C2—H2121.8C15—C16—H16121.2
C1—C2—H2121.8C17—C16—H16121.2
C2—C3—C4122.12 (17)C16—C17—N4130.48 (16)
C2—C3—H3118.9C16—C17—C12120.41 (16)
C4—C3—H3118.9N4—C17—C12109.11 (15)
C5—C4—C3121.46 (16)N4—C18—N3113.45 (16)
C5—C4—H4119.3N4—C18—H18123.3
C3—C4—H4119.3N3—C18—H18123.3
C4—C5—C6116.52 (16)F5—P1—F391.33 (10)
C4—C5—H5121.7F5—P1—F190.84 (8)
C6—C5—H5121.7F3—P1—F190.37 (7)
C5—C6—N2131.09 (15)F5—P1—F290.33 (7)
C5—C6—C1122.08 (15)F3—P1—F289.90 (7)
N2—C6—C1106.83 (14)F1—P1—F2178.79 (8)
N1—C7—N2111.14 (15)F5—P1—F491.13 (10)
N1—C7—H7124.4F3—P1—F4177.42 (10)
N2—C7—H7124.4F1—P1—F490.37 (7)
N2—C8—C9112.67 (13)F2—P1—F489.30 (6)
N2—C8—H8A109.1F5—P1—F6179.35 (8)
C9—C8—H8A109.1F3—P1—F689.03 (8)
N2—C8—H8B109.1F1—P1—F689.69 (8)
C9—C8—H8B109.1F2—P1—F689.14 (8)
H8A—C8—H8B107.8F4—P1—F688.51 (9)
O1—C9—C8107.68 (13)F5'—P1'—F3'91.6 (3)
O1—C9—H9A110.2F5'—P1'—F1'90.8 (3)
C8—C9—H9A110.2F3'—P1'—F1'90.2 (3)
O1—C9—H9B110.2F5'—P1'—F2'90.1 (3)
C8—C9—H9B110.2F3'—P1'—F2'89.9 (3)
H9A—C9—H9B108.5F1'—P1'—F2'179.1 (4)
O1—C10—C11107.08 (13)F5'—P1'—F4'90.8 (3)
O1—C10—H10A110.3F3'—P1'—F4'177.5 (4)
C11—C10—H10A110.3F1'—P1'—F4'90.2 (3)
O1—C10—H10B110.3F2'—P1'—F4'89.6 (3)
C11—C10—H10B110.3F5'—P1'—F6'179.1 (4)
H10A—C10—H10B108.6F3'—P1'—F6'89.2 (3)
N3—C11—C10112.69 (14)F1'—P1'—F6'89.7 (3)
N3—C11—H11A109.1F2'—P1'—F6'89.5 (3)
C10—C11—H11A109.1F4'—P1'—F6'88.4 (3)
N3—C11—H11B109.1
C7—N1—C1—C2−179.03 (17)C9—O1—C10—C11169.54 (13)
C7—N1—C1—C60.03 (17)C18—N3—C11—C10−94.78 (19)
N1—C1—C2—C3178.85 (16)C12—N3—C11—C1087.35 (19)
C6—C1—C2—C3−0.1 (2)O1—C10—C11—N3−58.98 (17)
C1—C2—C3—C40.3 (3)C18—N3—C12—C13179.45 (17)
C2—C3—C4—C5−0.2 (3)C11—N3—C12—C13−2.3 (3)
C3—C4—C5—C60.0 (2)C18—N3—C12—C170.01 (17)
C4—C5—C6—N2−179.17 (16)C11—N3—C12—C17178.22 (15)
C4—C5—C6—C10.2 (2)N3—C12—C13—C14−179.43 (16)
C7—N2—C6—C5179.09 (16)C17—C12—C13—C14−0.1 (2)
C8—N2—C6—C5−0.4 (3)C12—C13—C14—C15−0.2 (2)
C7—N2—C6—C1−0.31 (17)C13—C14—C15—C160.3 (3)
C8—N2—C6—C1−179.76 (13)C14—C15—C16—C17−0.1 (2)
C2—C1—C6—C5−0.1 (2)C15—C16—C17—N4179.34 (16)
N1—C1—C6—C5−179.29 (14)C15—C16—C17—C12−0.2 (2)
C2—C1—C6—N2179.35 (14)C18—N4—C17—C16−179.82 (17)
N1—C1—C6—N20.17 (17)C18—N4—C17—C12−0.29 (18)
C1—N1—C7—N2−0.23 (18)N3—C12—C17—C16179.76 (14)
C6—N2—C7—N10.34 (18)C13—C12—C17—C160.3 (2)
C8—N2—C7—N1179.76 (14)N3—C12—C17—N40.17 (17)
C7—N2—C8—C913.2 (2)C13—C12—C17—N4−179.34 (14)
C6—N2—C8—C9−167.43 (14)C17—N4—C18—N30.31 (19)
C10—O1—C9—C8−167.47 (13)C12—N3—C18—N4−0.21 (19)
N2—C8—C9—O158.10 (17)C11—N3—C18—N4−178.43 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···N4i1.05 (2)1.68 (2)2.724 (2)176 (2)
C4—H4···F3ii0.952.413.130 (2)133
C7—H7···F4iii0.952.233.100 (2)152
C9—H9B···F2iii0.992.403.340 (2)159
C11—H11A···F2iv0.992.513.066 (2)116
C16—H16···F4v0.952.393.300 (2)161
C18—H18···F60.952.383.298 (2)163

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5075).

References

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  • Pal, S., Hwang, W.-S., Lin, I. J. B. & Lee, C.-S. (2007). J. Mol. Catal. A, 269, 197–922.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zeng, A., Phillips, B. S., Xiao, J.-C. & Jean’ne, M. S. (2008). Chem. Mater.20, 2719–2726.

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