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Di­chloro­[(η5-cyclo­penta­dien­yl)dimeth­yl(η5-3-phenyl­inden­yl)silane]hafnium(IV): a powder study

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aUniversity Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, England, bCambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England, cDepartment of Organic Chemistry, University of Helsinki, PO Box 55, FIN-00014, Finland, and dMCAT GmbH, Hermann-von-Vicari-Strasse 23, D-78464, Konstanz, Germany
*Correspondence e-mail: jburley@dmu.ac.uk

(Received 3 November 2006; accepted 27 November 2006; online 15 December 2006)

The title compound, [Hf(C22H20Si)Cl2], was solved by simulated annealing from laboratory X-ray powder diffraction data collected at room temperature. The mol­ecular structure comprises a hafnium dichloride centre, coordinated by a η5-cyclo­penta­dienyl and a η5-3-phenyl­indenyl unit, which are connected through a shared dimethyl­silicon linkage.

Comment

For approximately two decades, there has been substantial inter­est in group 4 metallocenes, driven by their ability, in combination with methyl­alumoxane, to catalyse the isotactic polymerization of propyl­ene [for a recent review see Resconi et al. (2000[Resconi, L., Cavallo, A., Fait, A. & Piemontesi, F. (2000). Chem. Rev. 100, 1253-1345.])] and ethyl­ene [for reviews see Alt & Köppl (2000[Alt, H. G. & Köppl, A. (2000). Chem. Rev. 100, 1205-1221.]) and Möhring & Coville (2006[Möhring, P. C. & Coville, N. J. (2006). Coord. Chem. Rev. 250, 18-35.])]. For ansa-bridged indenyl-derived mol­ecules, the stereoselectivity and regioselectivity of the propyl­ene monomer are strongly influenced by substitution at the indenyl ring system. Characterization of these mol­ecules through crystallography is clearly desirable in order to elucidate fully the relationship between the structure of the catalyst and both the stereoregularity and the mol­ecular weight of the polymer it produces. For many of these compounds, growth of single crystals suitable for diffraction analysis can be difficult or impossible. Here we employed laboratory X-ray powder diffraction to solve and refine the crystal structure of an Hf-containing cyclo­penta­dien­yl–indenyl catalyst, (I)[link], in which the ligand presents heterotopic faces to the active Hf site.

[Scheme 1]

The Hf ion in (I)[link] is linked to two Cl ions at distances of 2.305 (3) and 2.303 (3) Å (this distance was restrained in the Rietveld refinement to be 2.3 Å) (Fig. 1[link]). The coordination of Hf is completed by an η5-cyclo­penta­dienyl and an η5-phenyl­indenyl unit, which are connected through a dimethyl­silicon linkage at an angle φ of 100.3 (1)° through the Si atom, which can be compared with 94.6 (1)° in the bis­indenyl zirconocene analogue. The Si atom is bonded to the indenyl unit in the 1-position. The distances between the Hf and the cyclo­penta­dienyl centroid are 2.26 (3) Å for the indenyl residue and 2.170 (3) Å for the cyclo­penta­dienyl; these distances were not constrained at the refinement stage. The indenyl and cyclo­penta­dienyl rings are tilted at an angle β of 55 (2)° with respect to each other, which can be compared with an angle of 61.8° in the bis-indenyl zirconocene analogue (Dang et al., 1999[Dang, V. U., Lin-Chen, Y., Balboni, D., Dall'Occo, T., Resconi, L., Merchandelli, P., Moret, M. & Sironi, A. (1999). Organometallics, 18, 3781-3791.]). The angles δ (hafnium–cyclo­penta­dienyl centroid–carbon α to silicon) are 92.4 (2) and 87.3 (2)° for the cyclo­penta­dienyl and indenyl rings, respectively. The phenyl residue is twisted out of plane with respect to the indenyl residue by a torsion angle of 24.1 (2)°.

The mol­ecules pack so that the indenyl rings on neighbouring mol­ecules are parallel and in contact (Fig. 2[link]). Excluding H⋯H contacts, two short contacts (less than the sum of the van der Waals radii) exist. Between the indenyl ring systems, the C7⋯C10 distance of 3.37 (3) Å is only slightly shorter than the value of 3.4 Å derived from the sum of the carbon van der Waals radii (Bondi, 1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-452.]). There also exists a contact C5⋯C21 of 3.35 (3) Å between the cyclo­penta­dienyl residue and a phenyl ring on a neighbouring mol­ecule. Both of these contacts are only marginally shorter than expected and it is not clear that they indicate the presence of any strong directional inter­actions between mol­ecules or that the crystal structure adopted can be rationally based on the close packing of mol­ecules.

[Figure 1]
Figure 1
The asymmetric unit of (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level. H atoms are not shown for clarity. Hf green, Cl yellow, Si blue and C grey.
[Figure 2]
Figure 2
Crystal packing in (I)[link], viewed parallel to the a axis. Hf green, Cl yellow, Si blue and C grey. H atoms have been omitted.
[Figure 3]
Figure 3
Final observed (points), calculated (line), difference [(yobsycalc)] and weighted difference [(yobsycalc)/σ] profiles for the Rietveld refinement of (I)[link].

Experimental

All manipulations were performed under argon using conventional Schlenk techniques. Solvents were dried and distilled under argon prior to use. 1-Phenyl­indenyl lithium, cyclo­penta­dienyl lithium and hafnium tetra­chloride (zirconium content < 0.5%) are commercial products from https://www.mcat.de.

(Cyclo­penta­dien­yl)(3-phenyl­inden-1-yl)dimethyl­silane: To a solution of dichloro­dimethyl­silane (6.80 g, 6.4 ml, 52.68 mmol) in 200 ml of diethyl ether, 1-phenyl­indenyl lithium (3.48 g, 17.56 mmol) was added at 195 K. The mixture was slowly warmed to ambient temperature and stirred for 1 h. The solvent was removed under vacuum and the oily residue extracted with pentane. The combined extracts were filtered through celite, the solvent removed and the residual oil dried under high vacuum to obtain 17.51 mmol (99.7%) of crude product as a red oil. The crude product was used without further purification in the next step. The red oil was dissolved in toluene (30 ml) and cyclo­penta­dienyl lithium (1.32 g) was added. After 2 d the reaction was complete (determined by 1H NMR). Water and saturated NH4Cl were added and the mixture extracted several times with diethyl ether. The combined organic fractions were dried over Na2SO4 and the solvent was removed under vacuum. (Cyclo­penta­dien­yl)(3-phenyl­inden-1-yl)dimethyl­silane was obtained as a yellow oil as a mixture of isomers which was used directly in the next step.

(η5-Cyclo­penta­dien­yl)(η5-3-phenyl­inden­yl)dimethyl­silane­hafnium(IV) dichloride: To a solution of (cyclo­penta­dien­yl)(3-phenyl­inden-1-yl)­dimethyl­silane (4.91 g, 15.61 mmol) in 150 ml of diethyl ether, 2.5 M n-butyl ­lithium (12.5 ml, 31.25 mmol) in hexane was added at 195 K. The mixture was slowly warmed to ambient temperature and stirred overnight. The dark-yellow mixture was then cooled to 195 K and HfCl4 (5.00 g, 31.25 mmol) was added over a period of 1 h. The mixture was then warmed to ambient temperature and stirred for 1 h. The solvent was removed and the oily residue extracted twice with dichloro­methane. The combined extracts were filtered through celite, the solvent removed and the residual oil dried under high vacuum to obtain 14.62 mmol (93.7%) of crude product. Analytically pure product was obtained by recrystallization from toluene/hexane (1:2).

Crystal data
  • [Hf(C22H20Si)Cl2]

  • Mr = 561.88

  • Triclinic, [P \overline 1]

  • a = 10.1894 (4) Å

  • b = 11.0993 (4) Å

  • c = 9.6940 (4) Å

  • α = 91.974 (2)°

  • β = 108.693 (2)°

  • γ = 80.501 (3)°

  • V = 1024.07 (7) Å3

  • Z = 2

  • Dx = 1.822 Mg m−3

  • Co Kα radiation

  • T = 293 K

  • Specimen shape: cylinder

  • 0.7 × 0.1 mm

  • Particle morphology: finely ground powder, yellow

Data collection
  • Stoe Stadi-P diffractometer

  • Specimen mounting: 0.3 mm Lindemann glass capillary

  • Specimen mounted in transmission mode

  • Scan method: step

  • 2θmin = 2.0, 2θmax = 60.0°

  • Increment in 2θ = 0.01°

Refinement
  • Rp = 0.046

  • Rwp = 0.059

  • Rexp = 0.059

  • RB = 0.068

  • S = 1.04

  • Wavelength of incident radiation: 1.78892 Å

  • Excluded region(s): none

  • The GSAS profile function number 3 was employed, which utilizes a pseudo-Voigt description of the peak shape which allows for angle-dependent asymmetry. The function is fully documented in the GSAS technical manual which is distributed with the software package. Peak tails were ignored when the intensity was 0.1 % of the overall peak. Refined parameters were GV (3.996), LX (3.016) and LY (16.261), with S/L and H/L set fixed at 0.013 and 0.035, which are generally suitable values for the diffractometer in question.

  • 169 parameters

  • All H-atom parameters refined subject to stereochemical restraints

  • (Δ/σ)max = 0.03

  • Preferred orientation correction: March–Dollase AXIS 1 Ratio = 1.08679, h = 0.000, k = 0.000, l= 1.000. Prefered orientation correction range: Min = 0.77904, Max = 1.13297

A powder diffraction pattern was collected using a monochromated Stoe Stadi-P instrument operating in Debye–Scherrer geometry with the sample contained in a 0.3 mm Lindemann glass capillary which was spun during the measurement to minimize preferred orientation effects. The pattern was indexed using TREOR (Werner et al., 1985[Werner, P.-E., Eriksson, L. & Westdahl, M. (1985). J. Appl. Cryst. 18, 367-370.]), employing 18 low-angle reflections. A triclinic unit cell of reasonable volume (assuming Z = 2) gave indexing figures of merit M18=84, F18=178. The crystal structure was solved using the simulated annealing algorithms as implemented in both PSSP (Stephens & Huq, 2002[Stephens, P. W. & Huq, A. (2002). Trans. Am. Crystallogr. Assoc. 27, 127-144.]) and DASH (David et al., 2006[David, W. I. F., Shankland, K., van de Streek, J., Pidcock, E., Motherwell, W. D. S. & Cole, J. C. (2006). J. Appl. Cryst. 39, 910-915.]). The crystal structure was assumed to be centrosymmetric (space group P[\overline{1}], Z′= 1), and this approach led to a chemically reasonable starting model for Rietveld refinement. For the refinement, suitable restraints were imposed on bond lengths, angles and planar groups, including bonds to H atoms. The CH and CH3 distances were constrained to be 0.93 and 0.96 Å, respectively. Three independent atomic displacement parameters were employed: one for the Hf, one for the two Cl atoms, one for all C and Si, and one for the H atoms which was was set equal to 1.2 times that for the C and Si atoms. Trials were made employing preferred orientation in directions suggested by a basic BFDH calculation of likely crystal morphology, which indicated that a small degree of preferred orientation existed in the sample [refined ratio=1.09 (4)], with plate-like crystallites being preferentially oriented normal to the diffraction plane. Given the air-sensitive nature of the sample, we did not try to confirm this through visual microscopy. The refinement, using the GSAS software suite (Larson & Von Dreele, 2000[Larson, A. C. & Von Dreele, R. B. (2000). General Structure Analysis System (GSAS). Report LAUR 86-748. Los Alamos National Laboratory, New Mexico, USA.]), converged readily to yield acceptable figures of merit of χ2 = 1.08, Rwp = 0.059, Rp = 0.046, DWd = 1.43 and RBragg = 0.068, and a visually acceptable fit (Fig. 3[link]). Standard deviations are taken from the program employed and represent statistical uncertainties rather than estimates of the absolute error, which are likely to be considerably greater.

Data collection: WinXpow (Stoe & Cie, 1999[Stoe & Cie (1999). WinXpow. Stoe & Cie, Darmstadt, Germany.]); data reduction: WinXpow; program(s) used to solve structure: DASH (David et al., 2006[David, W. I. F., Shankland, K., van de Streek, J., Pidcock, E., Motherwell, W. D. S. & Cole, J. C. (2006). J. Appl. Cryst. 39, 910-915.]) and PSSP (Stephens & Huq, 2002[Stephens, P. W. & Huq, A. (2002). Trans. Am. Crystallogr. Assoc. 27, 127-144.]); program(s) used to refine structure: GSAS (Larson & Von Dreele, 2000[Larson, A. C. & Von Dreele, R. B. (2000). General Structure Analysis System (GSAS). Report LAUR 86-748. Los Alamos National Laboratory, New Mexico, USA.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Computing details top

Data collection: Stoe software; data reduction: Stoe software; program(s) used to solve structure: please supply; program(s) used to refine structure: GSAS; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: please supply.

Dichloro[(η5-cyclopentadienyl)dimethyl(η5-3- phenylindenyl)silane]hafnium(IV) top
Crystal data top
[Hf(C22H20Si)Cl2]γ = 80.501 (3)°
Mr = 561.88V = 1024.07 (7) Å3
Triclinic, P1Z = 2
Hall symbol: -P 1F(000) = 544
a = 10.1894 (4) ÅDx = 1.822 Mg m3
b = 11.0993 (4) ÅCo Kα radiation, λ = 1.78892 Å
c = 9.6940 (4) ÅT = 293 K
α = 91.974 (2)°yellow
β = 108.693 (2)°cylinder, 0.7 mm × 0.1 mm mm
Data collection top
Stoe Stadi-P
diffractometer
Data collection mode: transmission
Primary focussing, Ge 111 monochromatorScan method: step
Specimen mounting: 0.3 mm Lindemann glass capillary2θmin = 2.0°, 2θmax = 60.0°, 2θstep = 0.01°
Refinement top
Least-squares matrix: full169 parameters
Rp = 0.046166 restraints
Rwp = 0.059All H-atom parameters refined
Rexp = 0.059(Δ/σ)max = 0.03
R(F2) = 0.068Background function: GSAS Background function number 1 with 10 terms. Shifted Chebyshev function of 1st kind 1: 248.915 2: -209.686 3: 57.0023 4: -4.01480 5: 6.91473 6: -5.10485 7: -2.21704 8: 2.85278 9: 1.09751 10: -3.29532
Excluded region(s): nonePreferred orientation correction: March-Dollase AXIS 1 Ratio= 1.08679 h= 0.000 k= 0.000 l= 1.000 Prefered orientation correction range: Min= 0.77904, Max= 1.13297
Profile function: The GSAS profile function number 3 was employed, which utilises a pseudo-Voigt description of the peak shape which allows for angle-dependent asymmetry. The function is fully documented in the GSAS technical manual which is distributed with the software package. Peak tails were ignored when the intensity was 0.1 % of the overall peak. Refined parameters were GV (3.996), LX (3.016) and LY (16.261), with S/L and H/L set fixed at 0.013 and 0.035, which are generally suitable values for the diffractometer in question.
Special details top

Experimental. The nuclear magnetic resonance spectra were recorded on a Jeol 400 MHz s pectrometer.

1H-NMR (400 MHz, CDCl3. 20°C): d 7.92 (d, 1H), 7.60 (d, 2H), 7.13–7.50 (m, 5H), 6.70 (dd, 2H), 6.16 (s, 1H), 5.94 (dd, 1H), 5.81 (dd, 1H), 1.09 (s, 3H), 0.85 (s, 3H). 13 C-NMR (400 MHz, CDCl3. 20°C): d 134.3 (C), 133.8 (C), 129.3 (Cp), 128.6 (Cp), 127.7 (CH), 127.6 (CH), 125.9 (CH), 124.6 (CH), 124.5 (CH), 123.1 (C) 121.9 (CH), 117.9 (C), 114.7 (CH), 107.7 (CH), 106.6 (C), 89.1 (C) -1.7 (CH3), -4.9 (CH3).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
HF10.0022 (5)0.2027 (3)0.2495 (6)0.175 (3)*
CL10.1623 (16)0.2207 (14)0.138 (2)0.147 (7)*
CL20.1050 (15)0.0123 (8)0.3496 (17)0.147 (7)*
SI10.2918 (15)0.3441 (12)0.3001 (14)0.135 (6)*
C10.2674 (15)0.2374 (11)0.1562 (14)0.135 (6)*
C20.212 (2)0.2703 (18)0.0509 (18)0.135 (6)*
C30.1502 (18)0.163 (2)0.001 (2)0.135 (6)*
C40.156 (3)0.0651 (17)0.085 (3)0.135 (6)*
C50.222 (2)0.1122 (11)0.186 (2)0.135 (6)*
C80.1065 (11)0.359 (2)0.399 (2)0.135 (6)*
C90.0161 (13)0.4173 (17)0.339 (2)0.135 (6)*
C100.0535 (19)0.5118 (19)0.228 (2)0.135 (6)*
C110.050 (2)0.5542 (17)0.191 (2)0.135 (6)*
C120.194 (2)0.5091 (17)0.266 (2)0.135 (6)*
C130.2309 (16)0.4164 (18)0.367 (2)0.135 (6)*
C140.1272 (12)0.3631 (16)0.398 (2)0.135 (6)*
C60.1334 (13)0.2745 (13)0.5056 (18)0.135 (6)*
C70.0019 (15)0.2754 (14)0.5121 (17)0.135 (6)*
C150.369 (2)0.269 (2)0.417 (2)0.135 (6)*
C160.393 (2)0.4926 (16)0.214 (2)0.135 (6)*
C200.507 (2)0.087 (2)0.818 (2)0.135 (6)*
C210.389 (2)0.130 (2)0.859 (2)0.135 (6)*
C220.2678 (19)0.193 (2)0.7583 (17)0.135 (6)*
C170.2656 (15)0.2136 (16)0.6159 (16)0.135 (6)*
C180.3827 (16)0.168 (2)0.5732 (19)0.135 (6)*
C190.5046 (16)0.106 (2)0.675 (2)0.135 (6)*
H100.147 (2)0.544 (3)0.182 (4)0.161 (7)*
H110.026 (3)0.616 (2)0.122 (3)0.161 (7)*
H120.263 (3)0.539 (2)0.240 (3)0.161 (7)*
H140.3253 (15)0.387 (3)0.413 (4)0.161 (7)*
H70.0256 (19)0.212 (2)0.555 (3)0.161 (7)*
H15a0.46 (2)0.316 (16)0.41 (5)0.161 (7)*
H15b0.38 (4)0.188 (18)0.38 (5)0.161 (7)*
H15c0.307 (19)0.26 (4)0.516 (7)0.161 (7)*
H16a0.492 (6)0.493 (17)0.20 (6)0.161 (7)*
H16b0.36 (5)0.558 (6)0.28 (1)0.161 (7)*
H16c0.38 (5)0.504 (16)0.12 (3)0.161 (7)*
H200.588 (2)0.046 (3)0.885 (3)0.161 (7)*
H210.390 (3)0.117 (3)0.954 (2)0.161 (7)*
H220.188 (2)0.220 (3)0.785 (3)0.161 (7)*
H180.381 (2)0.181 (3)0.478 (2)0.161 (7)*
H190.584 (2)0.079 (3)0.647 (3)0.161 (7)*
H20.223 (3)0.349 (2)0.013 (4)0.161 (7)*
H30.108 (5)0.158 (3)0.071 (4)0.161 (7)*
H40.120 (4)0.0165 (19)0.077 (5)0.161 (7)*
H50.242 (4)0.0669 (14)0.254 (4)0.161 (7)*
Geometric parameters (Å, º) top
HF1—CL12.305 (3)C13—C141.407 (3)
HF1—CL22.303 (3)C13—H140.930 (3)
HF1—SI13.279 (16)C14—HF12.522 (19)
HF1—C12.526 (14)C14—C91.421 (3)
HF1—C22.40 (2)C14—C131.407 (3)
HF1—C32.468 (16)C14—C61.438 (3)
HF1—C42.52 (2)C6—HF12.595 (16)
HF1—C52.495 (19)C6—C141.438 (3)
HF1—C82.54 (2)C6—C71.397 (3)
HF1—C92.50 (2)C6—C171.497 (3)
HF1—C142.522 (19)C7—HF12.642 (15)
HF1—C62.595 (16)C7—C81.477 (3)
HF1—C72.642 (15)C7—C61.397 (3)
CL1—HF12.305 (3)C7—H70.930 (3)
CL1—CL23.384 (16)C15—SI11.858 (3)
CL2—HF12.303 (3)C15—H15a0.960 (3)
CL2—CL13.384 (16)C15—H15b0.960 (3)
SI1—HF13.279 (16)C15—H15c0.960 (3)
SI1—C11.849 (3)C16—SI11.860 (3)
SI1—C81.855 (3)C16—H16a0.960 (3)
SI1—C151.859 (3)C16—H16b0.960 (3)
SI1—C161.8607 (3)C16—H16c0.960 (3)
C1—HF12.526 (14)C20—C211.400 (3)
C1—SI11.849 (3)C20—C191.400 (3)
C1—C21.399 (3)C20—H200.930 (3)
C1—C51.399 (3)C21—C201.400 (3)
C2—HF12.40 (2)C21—C221.400 (3)
C2—C11.399 (3)C21—H210.930 (3)
C2—C31.400 (3)C22—C211.400 (3)
C2—H20.939 (3)C22—C171.400 (3)
C3—HF12.468 (16)C22—H220.930 (3)
C3—C21.401 (3)C17—C61.497 (3)
C3—C41.340 (3)C17—C221.400 (3)
C3—H30.930 (3)C17—C181.398 (3)
C4—HF12.52 (2)C18—C191.400 (3)
C4—C31.401 (3)C18—H180.930 (3)
C4—C51.400 (3)C19—C201.400 (3)
C4—H40.930 (3)C19—C181.400 (3)
C5—HF12.495 (19)C19—H190.930 (3)
C5—C11.399 (3)H10—C100.930 (3)
C5—C41.400 (3)H11—C110.930 (3)
C5—H50.930 (3)H12—C120.930 (3)
C8—HF12.54 (2)H14—C130.930 (3)
C8—SI11.855 (3)H7—C70.930 (3)
C8—C91.480 (3)H15a—C150.960 (3)
C8—C71.477 (3)H15b—C150.960 (3)
C9—HF12.50 (2)H15c—C150.960 (3)
C9—C81.480 (3)H16a—C160.960 (3)
C9—C101.446 (3)H16b—C160.960 (3)
C9—C141.421 (3)H16c—C160.960 (3)
C10—C91.446 (3)H20—C200.930 (3)
C10—C111.362 (3)H21—C210.930 (3)
C10—H100.930 (3)H22—C220.930 (3)
C11—C101.362 (3)H18—C180.930 (3)
C11—C121.425 (3)H19—C190.930 (3)
C11—H110.930 (3)H2—C20.930 (3)
C12—C111.425 (3)H3—C30.930 (3)
C12—C131.363 (3)H4—C40.930 (3)
C12—H120.930 (3)H5—C50.930 (3)
C13—C121.363 (3)
CL1—HF1—CL294.5 (6)C8—C9—C10130.0 (3)
CL1—HF1—C299.1 (7)C8—C9—C14111.2 (2)
CL1—HF1—C384.0 (7)C10—C9—C14118.6 (4)
CL1—HF1—C5135.8 (7)C9—C10—C11119.6 (3)
CL2—HF1—C2132.5 (6)C9—C10—H10120.2 (5)
CL2—HF1—C3104.8 (7)C11—C10—H10120.2 (5)
CL2—HF1—C584.2 (5)C10—C11—C12120.4 (3)
C2—HF1—C333.4 (2)C10—C11—H11119.7 (5)
C2—HF1—C555.0 (3)C12—C11—H11119.7 (4)
C3—HF1—C554.3 (3)C11—C12—C13120.8 (3)
C1—SI1—C8100.3 (11)C11—C12—H12119.5 (3)
C1—SI1—C15108.8 (4)C13—C12—H12119.5 (4)
C1—SI1—C16109.2 (4)C12—C13—C14120.4 (3)
C8—SI1—C15110.9 (4)C12—C13—H14119.8 (6)
C8—SI1—C16110.8 (3)C14—C13—H14119.8 (4)
C15—SI1—C16115.7 (10)C9—C14—C13119.3 (3)
SI1—C1—C2121.3 (3)C9—C14—C6106.5 (2)
SI1—C1—C5121.1 (5)C13—C14—C6132.8 (5)
C2—C1—C5107.9 (2)C14—C6—C7108.9 (2)
HF1—C2—C178.4 (8)C14—C6—C17124.7 (2)
HF1—C2—C375.9 (7)C7—C6—C17124.8 (4)
HF1—C2—H2117 (3)C8—C7—C6110.9 (2)
C1—C2—C3107.8 (2)C8—C7—H7122.7 (2)
C1—C2—H2126.0 (6)C6—C7—H7122.7 (3)
C3—C2—H2126.0 (9)C21—C20—C19120.0 (4)
HF1—C3—C270.7 (7)C21—C20—H20120.0 (5)
HF1—C3—C475.7 (12)C19—C20—H20120.0 (3)
HF1—C3—H3116 (3)C20—C21—C22120.0 (4)
C2—C3—C4107.9 (2)C20—C21—H21120.0 (6)
C2—C3—H3126.0 (6)C22—C21—H21120.0 (4)
C4—C3—H3126.0 (8)C21—C22—C17120.0 (3)
C3—C4—C5107.9 (2)C21—C22—H22120.0 (6)
C3—C4—H4126.0 (14)C17—C22—H22120.0 (7)
C5—C4—H4126.0 (15)C6—C17—C22120.9 (3)
HF1—C5—C175.0 (6)C6—C17—C18119.8 (4)
HF1—C5—C474.8 (9)C22—C17—C18120.0 (3)
HF1—C5—H5121 (3)C17—C18—C19120.0 (4)
C1—C5—C4107.8 (3)C17—C18—H18120.0 (4)
C1—C5—H5125.9 (3)C19—C18—H18120.0 (5)
C4—C5—H5125.9 (4)C20—C19—C18120.0 (3)
SI1—C8—C9124.6 (11)C20—C19—H19120.0 (7)
SI1—C8—C7128.1 (10)C18—C19—H19120.0 (6)
C9—C8—C7101.94 (19)
 

Footnotes

Present address: Leicester School of Pharmacy, De Montfort University, Hawthorn Building, The Gateway, Leicester LE1 9BH, England.

§Present address: Borealis Polymer Oy, R&D, PO Box 330, FIN-06101, Porvoo, Finland.

Acknowledgements

JB thanks Jesus College, Cambridge, for supporting this work through a Junior Research Fellowship.

References

First citationAlt, H. G. & Köppl, A. (2000). Chem. Rev. 100, 1205–1221.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBondi, A. (1964). J. Phys. Chem. 68, 441–452.  Web of Science CrossRef CAS Google Scholar
First citationDang, V. U., Lin-Chen, Y., Balboni, D., Dall'Occo, T., Resconi, L., Merchandelli, P., Moret, M. & Sironi, A. (1999). Organometallics, 18, 3781–3791.  Web of Science CSD CrossRef CAS Google Scholar
First citationDavid, W. I. F., Shankland, K., van de Streek, J., Pidcock, E., Motherwell, W. D. S. & Cole, J. C. (2006). J. Appl. Cryst. 39, 910–915.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationLarson, A. C. & Von Dreele, R. B. (2000). General Structure Analysis System (GSAS). Report LAUR 86-748. Los Alamos National Laboratory, New Mexico, USA.  Google Scholar
First citationMöhring, P. C. & Coville, N. J. (2006). Coord. Chem. Rev. 250, 18–35.  Web of Science CrossRef Google Scholar
First citationResconi, L., Cavallo, A., Fait, A. & Piemontesi, F. (2000). Chem. Rev. 100, 1253–1345.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (1999). WinXpow. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationStephens, P. W. & Huq, A. (2002). Trans. Am. Crystallogr. Assoc. 27, 127–144.  Google Scholar
First citationWerner, P.-E., Eriksson, L. & Westdahl, M. (1985). J. Appl. Cryst. 18, 367–370.  CrossRef CAS Web of Science IUCr Journals Google Scholar

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