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Acta Cryst. (2009). E65, m602    [ doi:10.1107/S1600536809015268 ]

1,1-Bis[4-(trifluoromethyl)phenyl]germetane

L. A. Huck, G. D. Potter, H. A. Jenkins, J. F. Britten and W. J. Leigh

Abstract top

The internal C-Ge-C bond angle in the germacyclobutane ring of the title compound, C17H14F6Ge or [Ge(C3H6)(C7H4F3)2], is 77.8 (3)°. The -CF3 groups display rotational disorder [occupancies 0.604 (14):0.396 (14) and 0.410 (6):0.411 (6):0.179 (3)] and the germacyclobutane ring also shows disorder [occupancies 0.604 (14):0.396 (14)].

Comment top

Photolysis of 1,1-diarylgermetanes results in two competing modes of cycloreversion: (2 + 2) to yield the corresponding 1,1-diarylgermene (R2Ge=CH2) and ethylene, and (3 + 1) to yield the corresponding diarylgermylene (R2Ge) and cyclopropane (Leigh et al., 2008). While the quantum yield for decomposition of the germetane remains roughly constant regardless of aromatic substitutent (Φ ca 0.10), decreasing the electron density at germanium by aromatic ring substitution favors formation of the germylene and cyclopropane (Leigh et al., 2008). The molecular structure of (I) is shown in Figure 1. The internal C—Ge—C bond angle is 77.8 (3)°.

To our knowledge, there are no other reported crystal structures of germacyclobutanes (i.e. those in which the three carbon atoms of the four membered ring are all saturated) with which to compare these data. There are, however, several reported crystal structures of germacyclobutenes to which limited comparisons can be made (Tokitoh et al., 1995; Eichler et al., 1999; Meiners et al., 2002; Tajima et al., 2005). The endocyclic Ge—C bond distances are quite similar, despite the carbon-carbon double bond within the ring, and the endocyclic C—Ge—C angle is slightly smaller in these germacyclobutene molecules, which is to be expected. The 4-membered germacyclobutane ring of the title compound is not planar. The angle between the plane made by the carbon atoms in the ring (C15—C17) and the plane containing the germanium and two adjacent carbon atoms in the ring (C15, C17) is 24 (2)°. The aromatic rings are nearly perpendicular, with an angle of 85.8 (1)° between them.

The trifluoromethyl groups are disordered and have been refined as such (see refinement details). The two CF3 groups interact with each other and the germacyclobutane ring of neighbouring molecules (see the packing diagram - Figure 2). The non-planarity of the germacyclobutane ring results in disorder that has been refined over two occupancy sites.

The crystal structure of an analogue of (I) in which the aromatic rings are substituted at the 3 and 5 positions with CF3 groups [i.e. 1,1-bis(3,5-bis(trifluoromethyl)phenyl)germetane] exhibits similar structural features (Potter, et al., 2009).

Related literature top

For the synthesis of the title compound, see: Leigh et al. (2008). For related compounds see: Tokitoh et al. (1995); Eichler et al. (1999); Meiners et al. (2002); Tajima et al. (2005). For 1,1-bis(3,5-bis(trifluoromethyl)phenyl)germetane], which exhibits similar structural features, see: Potter et al. (2009).

Experimental top

Compound (I) was synthesized as described elsewhere (Leigh et al., 2008). Single crystals for x-ray diffraction were obtained via repeated recrystallizations from methanol.

Refinement top

The data were collected at -100°C on a single-crystal mounted in a cryoloop. X-ray crystallographic analysis was performed at the McMaster Analytical X-Ray (MAX) Diffraction Facility. Hydrogen atoms were treated as riding upon their parent atoms with C—H distances of 0.95 Å (aromatic) and 0.96 Å (CH2) and with Uiso(H) = 1.2Ueq(C). Fluorine atoms at C7/C7A were split over two positions, with approximately 60:40 occupancy. Fluorine atoms at C14/C14A/C14' were disordered over three positions (41:41:18 occupancy) with one thermal parameter (0.06). The propyl moiety of the germacycle is disordered over two sites (60:40 occupancy) and a restraint is applied so that the groups can twist away from each other but not leave the sphere of germanium.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structures of (I) drawn with 50% probability ellipsoids. H atoms not shown. Both trifluoromethyl groups and the (CH2)3 group are disordered but the disorder is not shown for clarity.
[Figure 2] Fig. 2. Packing diagram of (I) in the space group P 21/n.
1,1-Bis[4-(trifluoromethyl)phenyl]germetane top
Crystal data top
[Ge(C3H6)(C7H4F3)2]F(000) = 808
Mr = 404.87Dx = 1.594 Mg m−3
Monoclinic, P21/nMelting point: 319 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 13.596 (6) ÅCell parameters from 5916 reflections
b = 6.412 (3) Åθ = 3.5–26.6°
c = 20.243 (9) ŵ = 1.87 mm−1
β = 107.081 (7)°T = 173 K
V = 1687 (1) Å3Block, colourless
Z = 40.40 × 0.38 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3867 independent reflections
Radiation source: fine-focus sealed tube2378 reflections with I > 2σ(I)
graphiteRint = 0.053
φ and ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
SADABS		h = −17→17
Tmin = 0.484, Tmax = 0.688k = −8→8
14478 measured reflectionsl = −26→25
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0275P)2 + 2.3419P]
where P = (Fo2 + 2Fc2)/3
3867 reflections(Δ/σ)max = 0.022
258 parametersΔρmax = 0.68 e Å−3
19 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[Ge(C3H6)(C7H4F3)2]V = 1687 (1) Å3
Mr = 404.87Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.596 (6) ŵ = 1.87 mm−1
b = 6.412 (3) ÅT = 173 K
c = 20.243 (9) Å0.40 × 0.38 × 0.20 mm
β = 107.081 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3867 independent reflections
Absorption correction: multi-scan
SADABS		2378 reflections with I > 2σ(I)
Tmin = 0.484, Tmax = 0.688Rint = 0.053
14478 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.097Δρmax = 0.68 e Å−3
S = 0.99Δρmin = −0.61 e Å−3
3867 reflectionsAbsolute structure: ?
258 parametersFlack parameter: ?
19 restraintsRogers parameter: ?
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)
Ge1A0.88719 (3)0.20119 (6)0.19017 (2)0.03626 (13)0.396 (14)
C15A0.7582 (7)0.347 (4)0.1861 (18)0.049 (3)0.396 (14)
H15C0.74830.37380.23190.058*0.396 (14)
H15D0.74660.47550.15760.058*0.396 (14)
C16A0.6994 (5)0.152 (3)0.1482 (9)0.058 (3)0.396 (14)
H16C0.64020.19310.10860.070*0.396 (14)
H16D0.67450.06380.18010.070*0.396 (14)
C17A0.7845 (7)0.034 (4)0.1227 (15)0.0493 (15)0.396 (14)
H17C0.78110.06240.07400.059*0.396 (14)
H17D0.7889−0.11770.13250.059*0.396 (14)
Ge10.88719 (3)0.20119 (6)0.19017 (2)0.03626 (13)0.604 (14)
C150.7486 (5)0.302 (3)0.1857 (11)0.049 (3)0.604 (14)
H15A0.72320.25250.22400.058*0.604 (14)
H15B0.74000.45510.17960.058*0.604 (14)
C160.7073 (5)0.1749 (18)0.1173 (6)0.058 (3)0.604 (14)
H16A0.69580.26600.07630.070*0.604 (14)
H16B0.64240.10220.11560.070*0.604 (14)
C170.7979 (11)0.013 (6)0.122 (2)0.0493 (15)0.604 (14)
H17A0.8172−0.00080.07860.059*0.604 (14)
H17B0.7874−0.12490.14070.059*0.604 (14)
C10.9675 (3)0.0705 (5)0.27568 (18)0.0341 (8)
C21.0113 (3)−0.1241 (6)0.2752 (2)0.0445 (9)
H2A1.0030−0.19360.23240.053*
C31.0670 (3)−0.2189 (6)0.3359 (2)0.0485 (10)
H3A1.0965−0.35260.33460.058*
C41.0799 (3)−0.1212 (6)0.39821 (19)0.0407 (9)
C51.0369 (3)0.0734 (6)0.3998 (2)0.0471 (10)
H5A1.04560.14240.44270.056*
C60.9812 (3)0.1671 (5)0.3389 (2)0.0444 (9)
H6A0.95170.30060.34040.053*
C80.9769 (3)0.3844 (5)0.15718 (18)0.0379 (8)
C91.0823 (3)0.3923 (6)0.1889 (2)0.0470 (10)
H9A1.11260.30070.22620.056*
C101.1437 (3)0.5314 (6)0.1669 (2)0.0510 (10)
H10A1.21580.53450.18890.061*
C111.1000 (3)0.6659 (6)0.1130 (2)0.0448 (9)
C120.9955 (3)0.6588 (6)0.0806 (2)0.0512 (10)
H12A0.96530.75060.04330.061*
C130.9352 (3)0.5183 (6)0.1024 (2)0.0471 (10)
H13A0.86350.51300.07950.057*
C71.1400 (4)−0.2268 (7)0.4628 (2)0.0561 (11)0.604 (14)
F11.1175 (11)−0.4307 (12)0.4626 (7)0.083 (3)0.604 (14)
F21.1343 (13)−0.146 (2)0.5219 (6)0.078 (4)0.604 (14)
F31.2396 (5)−0.227 (3)0.4671 (8)0.072 (3)0.604 (14)
C7A1.1400 (4)−0.2268 (7)0.4628 (2)0.0561 (11)0.396 (14)
F1A1.0871 (16)−0.380 (3)0.4803 (12)0.106 (7)0.396 (14)
F2A1.1506 (18)−0.091 (3)0.5158 (8)0.070 (5)0.396 (14)
F3A1.2337 (11)−0.281 (4)0.4667 (12)0.091 (8)0.396 (14)
C141.1663 (3)0.8216 (7)0.0908 (2)0.0589 (11)0.410 (6)
F41.1154 (5)1.0064 (10)0.0742 (5)0.0613 (7)*0.410 (6)
F51.1939 (6)0.7630 (11)0.0372 (4)0.0613 (7)*0.410 (6)
F61.2236 (6)0.9328 (12)0.1444 (3)0.0613 (7)*0.410 (6)
C14'1.1663 (3)0.8216 (7)0.0908 (2)0.0589 (11)0.411 (6)
F4'1.1110 (5)0.9575 (12)0.0424 (5)0.0613 (7)*0.411 (6)
F5'1.2282 (6)0.7196 (11)0.0569 (4)0.0613 (7)*0.411 (6)
F6'1.2569 (6)0.8560 (12)0.1386 (4)0.0613 (7)*0.411 (6)
C14A1.1663 (3)0.8216 (7)0.0908 (2)0.0589 (11)0.179 (3)
F4A1.1322 (12)0.867 (2)0.0240 (6)0.0613 (7)*0.179 (3)
F5A1.2639 (10)0.769 (2)0.1061 (9)0.0613 (7)*0.179 (3)
F6A1.1623 (13)1.0042 (19)0.1205 (9)0.0613 (7)*0.179 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge1A0.0323 (2)0.03686 (19)0.0365 (2)0.00216 (19)0.00519 (16)0.0002 (2)
C15A0.042 (3)0.046 (7)0.062 (3)0.005 (3)0.021 (3)0.017 (4)
C16A0.032 (3)0.065 (4)0.072 (7)−0.005 (3)0.006 (4)0.022 (6)
C17A0.042 (3)0.052 (5)0.045 (3)−0.009 (4)−0.002 (4)0.003 (3)
Ge10.0323 (2)0.03686 (19)0.0365 (2)0.00216 (19)0.00519 (16)0.0002 (2)
C150.042 (3)0.046 (7)0.062 (3)0.005 (3)0.021 (3)0.017 (4)
C160.032 (3)0.065 (4)0.072 (7)−0.005 (3)0.006 (4)0.022 (6)
C170.042 (3)0.052 (5)0.045 (3)−0.009 (4)−0.002 (4)0.003 (3)
C10.0292 (19)0.0364 (17)0.034 (2)−0.0018 (15)0.0055 (16)−0.0001 (16)
C20.048 (2)0.045 (2)0.037 (2)0.0075 (18)0.0078 (19)−0.0067 (17)
C30.051 (2)0.0427 (19)0.047 (2)0.0167 (19)0.007 (2)0.0012 (19)
C40.036 (2)0.0454 (19)0.039 (2)0.0012 (17)0.0077 (18)0.0022 (18)
C50.049 (2)0.051 (2)0.035 (2)0.0023 (19)0.0048 (19)−0.0080 (19)
C60.043 (2)0.037 (2)0.047 (2)0.0069 (17)0.0042 (19)−0.0044 (18)
C80.037 (2)0.0359 (17)0.035 (2)0.0027 (16)0.0030 (17)−0.0011 (16)
C90.039 (2)0.048 (2)0.050 (2)0.0036 (18)0.006 (2)0.0091 (19)
C100.034 (2)0.056 (2)0.059 (3)0.0020 (19)0.007 (2)0.006 (2)
C110.044 (2)0.046 (2)0.045 (2)−0.0039 (18)0.0148 (19)−0.0005 (18)
C120.048 (2)0.055 (3)0.045 (2)−0.004 (2)0.006 (2)0.0112 (19)
C130.035 (2)0.057 (2)0.041 (2)−0.0023 (19)−0.0019 (18)0.0086 (19)
C70.058 (3)0.063 (3)0.041 (2)0.009 (3)0.004 (2)0.006 (2)
F10.110 (8)0.054 (3)0.061 (6)−0.009 (4)−0.013 (4)0.019 (3)
F20.110 (8)0.089 (7)0.042 (4)0.048 (6)0.034 (4)0.022 (4)
F30.044 (5)0.093 (6)0.062 (5)0.014 (4)−0.011 (4)0.014 (4)
C7A0.058 (3)0.063 (3)0.041 (2)0.009 (3)0.004 (2)0.006 (2)
F1A0.110 (12)0.108 (12)0.075 (12)−0.022 (10)−0.012 (7)0.050 (9)
F2A0.078 (7)0.099 (11)0.023 (5)0.012 (7)0.001 (5)0.015 (6)
F3A0.103 (13)0.122 (17)0.053 (8)0.080 (12)0.029 (8)0.013 (8)
C140.055 (3)0.062 (3)0.059 (3)0.005 (2)0.015 (2)0.006 (2)
C14'0.055 (3)0.062 (3)0.059 (3)0.005 (2)0.015 (2)0.006 (2)
C14A0.055 (3)0.062 (3)0.059 (3)0.005 (2)0.015 (2)0.006 (2)
Geometric parameters (Å, °) top
Ge1A—C11.944 (3)C3—C41.372 (5)
Ge1A—C81.947 (4)C3—H3A0.9500
Ge1A—C17A1.961 (4)C4—C51.382 (5)
Ge1A—C15A1.969 (5)C4—C71.486 (5)
Ge1A—C16A2.463 (6)C5—C61.381 (5)
C15A—C16A1.562 (11)C5—H5A0.9500
C15A—H15C0.9900C6—H6A0.9500
C15A—H15D0.9900C8—C131.384 (5)
C16A—C17A1.591 (13)C8—C91.389 (5)
C16A—H16C0.9900C9—C101.381 (5)
C16A—H16D0.9900C9—H9A0.9500
C17A—H17C0.9900C10—C111.382 (5)
C17A—H17D0.9900C10—H10A0.9500
C15—C161.563 (11)C11—C121.379 (5)
C15—H15A0.9900C11—C141.500 (6)
C15—H15B0.9900C12—C131.376 (5)
C16—C171.591 (13)C12—H12A0.9500
C16—H16A0.9900C13—H13A0.9500
C16—H16B0.9900C7—F21.326 (9)
C17—H17A0.9900C7—F31.331 (9)
C17—H17B0.9900C7—F11.342 (9)
C1—C61.383 (5)C14—F51.302 (8)
C1—C21.385 (5)C14—F61.340 (7)
C2—C31.381 (5)C14—F41.363 (7)
C2—H2A0.9500
C1—Ge1A—C8108.72 (15)C3—C2—C1121.0 (3)
C1—Ge1A—C17A118.9 (11)C3—C2—H2A119.5
C8—Ge1A—C17A118.7 (11)C1—C2—H2A119.5
C1—Ge1A—C15A120.2 (12)C4—C3—C2120.4 (3)
C8—Ge1A—C15A109.8 (11)C4—C3—H3A119.8
C17A—Ge1A—C15A77.8 (3)C2—C3—H3A119.8
C1—Ge1A—C16A120.4 (4)C3—C4—C5119.5 (3)
C8—Ge1A—C16A130.5 (4)C3—C4—C7119.3 (3)
C16A—C15A—Ge1A87.7 (4)C5—C4—C7121.2 (4)
C16A—C15A—H15C114.0C6—C5—C4119.8 (3)
Ge1A—C15A—H15C114.0C6—C5—H5A120.1
C16A—C15A—H15D114.0C4—C5—H5A120.1
Ge1A—C15A—H15D114.0C5—C6—C1121.4 (3)
H15C—C15A—H15D111.2C5—C6—H6A119.3
C15A—C16A—C17A103.0 (8)C1—C6—H6A119.3
C15A—C16A—Ge1A53.0 (3)C13—C8—C9118.1 (4)
C17A—C16A—Ge1A52.7 (2)C13—C8—Ge1A119.9 (3)
C15A—C16A—H16C111.2C9—C8—Ge1A121.9 (3)
C17A—C16A—H16C111.2C10—C9—C8120.9 (4)
Ge1A—C16A—H16C139.4C10—C9—H9A119.5
C15A—C16A—H16D111.2C8—C9—H9A119.5
C17A—C16A—H16D111.2C9—C10—C11119.9 (4)
Ge1A—C16A—H16D111.5C9—C10—H10A120.1
H16C—C16A—H16D109.1C11—C10—H10A120.1
C16A—C17A—Ge1A87.1 (5)C12—C11—C10119.8 (4)
C16A—C17A—H17C114.1C12—C11—C14120.4 (4)
Ge1A—C17A—H17C114.1C10—C11—C14119.8 (4)
C16A—C17A—H17D114.1C13—C12—C11119.8 (4)
Ge1A—C17A—H17D114.1C13—C12—H12A120.1
H17C—C17A—H17D111.3C11—C12—H12A120.1
C16—C15—H15A114.1C12—C13—C8121.4 (4)
C16—C15—H15B114.1C12—C13—H13A119.3
H15A—C15—H15B111.2C8—C13—H13A119.3
C15—C16—C17102.6 (8)F2—C7—F3105.6 (9)
C15—C16—H16A111.2F2—C7—F1108.0 (9)
C17—C16—H16A111.2F3—C7—F1103.0 (9)
C15—C16—H16B111.2F2—C7—C4117.0 (7)
C17—C16—H16B111.2F3—C7—C4110.1 (8)
H16A—C16—H16B109.2F1—C7—C4112.0 (7)
C16—C17—H17A114.1F5—C14—F6125.9 (6)
C16—C17—H17B114.1F5—C14—F4107.2 (5)
H17A—C17—H17B111.3F6—C14—F482.5 (6)
C6—C1—C2117.9 (3)F5—C14—C11113.7 (5)
C6—C1—Ge1A121.2 (3)F6—C14—C11111.6 (4)
C2—C1—Ge1A120.8 (3)F4—C14—C11110.2 (4)
C1—Ge1A—C15A—C16A−102.4 (14)Ge1A—C1—C6—C5179.0 (3)
C8—Ge1A—C15A—C16A130.5 (14)C1—Ge1A—C8—C13−170.8 (3)
C17A—Ge1A—C15A—C16A14 (2)C17A—Ge1A—C8—C1349.1 (6)
Ge1A—C15A—C16A—C17A−18 (2)C15A—Ge1A—C8—C13−37.5 (9)
C1—Ge1A—C16A—C15A102 (2)C16A—Ge1A—C8—C131.8 (7)
C8—Ge1A—C16A—C15A−70 (2)C1—Ge1A—C8—C96.4 (4)
C17A—Ge1A—C16A—C15A−158 (3)C17A—Ge1A—C8—C9−133.7 (6)
C1—Ge1A—C16A—C17A−100.0 (19)C15A—Ge1A—C8—C9139.7 (9)
C8—Ge1A—C16A—C17A88.2 (19)C16A—Ge1A—C8—C9179.0 (7)
C15A—Ge1A—C16A—C17A158 (3)C13—C8—C9—C100.7 (6)
C15A—C16A—C17A—Ge1A18 (2)Ge1A—C8—C9—C10−176.5 (3)
C1—Ge1A—C17A—C16A104.0 (13)C8—C9—C10—C110.4 (6)
C8—Ge1A—C17A—C16A−119.9 (14)C9—C10—C11—C12−0.9 (6)
C15A—Ge1A—C17A—C16A−13.9 (19)C9—C10—C11—C14178.0 (4)
C8—Ge1A—C1—C686.7 (3)C10—C11—C12—C130.3 (6)
C17A—Ge1A—C1—C6−133.3 (7)C14—C11—C12—C13−178.6 (4)
C15A—Ge1A—C1—C6−40.9 (8)C11—C12—C13—C80.9 (6)
C16A—Ge1A—C1—C6−86.8 (6)C9—C8—C13—C12−1.4 (6)
C8—Ge1A—C1—C2−94.4 (3)Ge1A—C8—C13—C12175.9 (3)
C17A—Ge1A—C1—C245.6 (7)C3—C4—C7—F2−167.6 (9)
C15A—Ge1A—C1—C2138.0 (8)C5—C4—C7—F212.3 (10)
C16A—Ge1A—C1—C292.1 (6)C3—C4—C7—F371.9 (9)
C6—C1—C2—C30.0 (6)C5—C4—C7—F3−108.2 (9)
Ge1A—C1—C2—C3−178.9 (3)C3—C4—C7—F1−42.2 (8)
C1—C2—C3—C40.0 (6)C5—C4—C7—F1137.8 (7)
C2—C3—C4—C5−0.1 (6)C12—C11—C14—F5−82.7 (6)
C2—C3—C4—C7179.9 (4)C10—C11—C14—F598.4 (6)
C3—C4—C5—C60.2 (6)C12—C11—C14—F6127.5 (6)
C7—C4—C5—C6−179.8 (4)C10—C11—C14—F6−51.4 (7)
C4—C5—C6—C1−0.2 (6)C12—C11—C14—F437.7 (7)
C2—C1—C6—C50.1 (6)C10—C11—C14—F4−141.2 (6)
Acknowledgements top

We thank the Natural Sciences and Engineering Research Council (NSERC) of Canada for financial support and for a postgraduate scholarship to LAH.

references
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