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Crystal structure of 2-chloro-1,3-(2,6-diiso­propyl­phen­yl)-4,5-di­hydro-1H-imidazol-3-ium tetra­kis­(3,5-tri­fluoro­methyl­phen­yl)borate

CROSSMARK_Color_square_no_text.svg

aThe Atlantic Centre for Green Chemistry and the Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3, Canada
*Correspondence e-mail: jason.masuda@smu.ca

Edited by A. J. Lough, University of Toronto, Canada (Received 10 August 2016; accepted 13 September 2016; online 23 September 2016)

The title compound, C27H38ClN2+·C32H12BF24, was synthesized by reacting the product formed from a previous reaction between 1,3-bis­(2,6-diiso­propyl­phen­yl)imidazolinium-2-carboxyl­ate (SIPrCO2), and SOCl2, with sodium tetra­kis­[3,5-bis­(tri­fluoro­meth­yl)phen­yl]borate (NaBARF). In the cation, the imidazole ring is in a half-chair conformation and the formerly carbene carbon atom is bonded in a distorted trigonal–planar geometry with N—C—Cl angles of 122.96 (16) and 122.21 (16)° and an N—C—N angle of 114.83 (18)°. In the crystal, weak C—H⋯F hydrogen bonds link the cations and anions, forming a three-dimensional network. In addition, a short Cl⋯F contact of 3.213 Å and several short F⋯F contacts less than the sum of the van der Waals radii [1.47 Å + 1.47 Å = 2.94 Å] are observed. The F atoms of two of the CF3 groups were refined as disordered over four sets of sites.

1. Chemical context

The use of main group elements as a way to stabilize singlet carbenes was first investigated in-depth by Bertrand & Reed (1994[Bertrand, G. & Reed, R. (1994). Coord. Chem. Rev. 137, 323-355.]), leading to the discovery of the first phosphino silyl carbenes (Igau et al., 1988[Igau, A., Grutzmacher, H., Baceiredo, A. & Bertrand, G. (1988). J. Am. Chem. Soc. 110, 6463-6466.]) followed by other novel singlet carbenes (Lavallo et al., 2005[Lavallo, V., Canac, Y., Präsang, C., Donnadieu, B. & Bertrand, G. (2005). Angew. Chem. 117, 5851-5855.]; Frey et al., 2007[Frey, G. D., Lavallo, V., Donnadieu, B., Schoeller, W. W. & Bertrand, G. (2007). Science, 316, 439-441.]; Aldeco-Perez et al., 2009[Aldeco-Perez, E., Rosenthal, A. J., Donnadieu, B., Parameswaran, P., Frenking, G. & Bertrand, G. (2009). Science, 326, 556-559.]). However, the report of the first `bottleable' crystalline N-heterocyclic carbene (NHC) (Arduengo et al., 1991[Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.]) initiated a new paradigm in synthetic chemistry (Bourissou et al., 2000[Bourissou, D., Guerret, O., Gabbaï, F. P. & Bertrand, G. (2000). Chem. Rev. 100, 39-92.]). In particular, NHCs are favoured due to their stability and ease of synthesis. The ability of these stable carbenes to activate small mol­ecules and to help stabilize highly reactive inter­mediates makes this an increasingly desirable area of research. The crystal structure of the compound under investigation incorporates a popular five-membered saturated NHC (known as SIPr) coordinated with a Cl atom attached at the formally carbene atom as a borate salt.

[Scheme 1]

2. Structural commentary

The mol­ecular structure of the title salt compound is shown in Fig. 1[link]. The formerly carbene carbon has a distorted trigonal–planar geometry and is flanked by the two sterically bulky N-diiso­propyl­phenyl groups of the heterocycle. The imidazolidinium ring is in a half-chair conformation having approximate C2 symmetry. The dihedral angle between the mean planes of the benzene rings is 36.7 (1)°. The isopropyl groups containing C12 and C27 are essentially bis­ected by the plane of the benzene ring to which they are attached, subtending dihedral angles of 116.0 (2)° (C16/C21/C25/C27) and 112.4 (2)° (C4/C9/C10/C12), relative to the ipso carbon atoms C4 and C16 while the isopropyl groups containing C15 and C23 deviate significantly from this bis­ected geometry with dihedral angles of 26.1 (2)° (C4/C5/C13/C15) and 46.7 (2)° (C16/C17/C22/C23) relative to the ipso carbon atoms C4 and C16. The C1—Cl1 bond length of 1.681 (2) Å is slightly less than the average value of 1.73 Å for a Csp2⋯Cl bond length.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing the atom labelling. Fluorine atom labels and hydrogen atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

In the crystal, short-contact H⋯F inter­actions between the isopropyl groups of the NHC and the tri­fluoro­methyl groups of the anion are observed. These are due to weak C—H⋯F hydrogen bonds (Table 1[link]), which link the cations and anions, forming a three-dimensional network (Fig. 2[link]). There is one short Cl1⋯F20([{3\over 2}] − x, −[{1\over 2}] + y, [{3\over 2}] − z) contact with a distance of 3.213 (2) Å as well as multiple short F⋯F contacts with lengths less than 2.94 Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3A⋯F15i 0.99 2.43 3.256 (3) 141
C12—H12A⋯F17Cii 0.98 2.53 3.269 (12) 132
C19—H19⋯F8Diii 0.95 2.48 3.297 (18) 144
C29—H29⋯F9Diii 0.95 2.35 3.180 (14) 146
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
Part of the crystal structure with weak C—H⋯F hydrogen bonds shown as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (CSD; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) revealed two hits for structures which are imidazolidinium salts with N-methyl groups in place of the N-diiso­propyl­phenyl groups of the title compound. One of the structures contains a tetra­chloro­nickel counter-anion and the other is that of a chloride [XAMQAE (Kremzow et al., 2005[Kremzow, D., Seidel, G., Lehmann, C. W. & Fürstner, A. (2005). Chem. Eur. J. 11, 1833-1853.]) and SISVUN (Böttcher et al., 2014[Böttcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H. G., Bassil, B. S., Winter, M., Mitzel, N. W. & Röschenthaler, G. V. (2014). Dalton Trans. 43, 2979-2987.])]. The CSD also contains two structures of unsaturated five-membered NHC compounds that contain C—Cl bonds in the C2 position [NUXPOL (Arduengo et al., 1997[Arduengo, A. J., Davidson, F., Dias, H. V. R., Goerlich, J. R., Khasnis, D., Marshall, W. J. & Prakasha, T. K. (1997). J. Am. Chem. Soc. 119, 12742-12749.]) and XOMMER (Kuhn et al., 2002[Kuhn, N., Abu-Rayyan, A., Göhner, M. & Steimann, M. (2002). Z. Anorg. Allg. Chem. 628, 1721-1723.])].

5. Synthesis and crystallization

In a glovebox, prior to the synthesis of the title compound, SIPrCO2 (Zhou et al., 2008[Zhou, H., Zhang, W. Z., Liu, C. H., Qu, J. P. & Lu, X. B. (2008). J. Org. Chem. 73, 8039-8044.]) was reacted with SOCl2 in an attempt to synthesize SIPrCOCl2. The exact composition of the product was unconfirmed; however, the decision was made to take a portion of this product and move forward to test its chemistry. This product is the primary reagent for the synthesis of the title salt. In a vial equipped with a magnetic stirring bar was placed the resulting product from the SIPrCO2/SOCl2 reaction (0.0478 g, 9.745 × 10−2 mmol), NaBARF (0.0863 g, 9.738 × 10−2 mmol) and 5 mL of di­chloro­methane. The mixture was left to stir overnight (18 h) after which the insol­uble solids were removed by filtering the solution into a pre-weighed vial. This was done using a glass pipette containing a small layer of diatomaceous earth. Volatiles were removed in vacuo, leaving behind a pale-yellow-coloured solid (0.0596 g, 4.623 × 10−2 mmol). The purity of the sample was confirmed using 1H NMR spectroscopy in deuterated chloro­form (CDCl3). The recrystallization was carried out by evaporation of CDCl3, followed by cooling in the freezer overnight, to afford colourless needle-shaped crystals. 1H NMR (300 MHz, 298 K, C6D6): δ 1.26 (d, CH(CH3)2, 12H), 1.33 (d, CH(CH3)2, 12H), 3.84 (sept., CH(CH3)2, 4H), 4.52 (s, CH2, 4H), 7.34 (d, m-Ar-H, 4H), 7.50 (s, p-Ar-H, 4H), 7.56 (t, p-Ar-H, 2H), 7.68 ppm (t, m-Ar-H, 8H). 19F NMR (282.5 MHz, 298 K, C6D6): δ −63.1 ppm (s). 11B NMR (96.3 MHz, 298 K, C6D6): δ −6.18 ppm (s). Tri­fluoro­toluene was used as an external reference for the 19F NMR spectrum and boron trifluoride diethyl etherate was used as the external reference for the 11B NMR spectrum.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Hydrogen atoms were included at geometrically idealized positions and were included in a riding-motion approximation. For the methyl groups, the dihedral angle of the idealized tetra­hedral CH3 fragment was allowed to refine.

Table 2
Experimental details

Crystal data
Chemical formula C17H38ClN2+·C32H12BF24
Mr 1289.27
Crystal system, space group Monoclinic, P21/n
Temperature (K) 125
a, b, c (Å) 18.5025 (12), 17.8739 (12), 19.7857 (13)
β (°) 116.428 (1)
V3) 5859.5 (7)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.18
Crystal size (mm) 0.39 × 0.38 × 0.08
 
Data collection
Diffractometer Siemens/Bruker APEXII
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.660, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 40063, 10921, 8363
Rint 0.033
(sin θ/λ)max−1) 0.606
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.113, 1.02
No. of reflections 10921
No. of parameters 830
No. of restraints 38
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.52, −0.45
Computer programs: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), XS in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014/7 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Prior to final refinement, there was significant disorder associated with one of the CF3 groups attached to each of C34 and C58. After trying to assess whether the groups had two components of a disorder, it became clear that each of these CF3 groups actually had four components of disorder that needed to be resolved. In order to do this, the SUMP command was applied to all of the fluorine atoms involved. This involved grouping the four components into PART 1, PART 2, PART 3, and PART 4, respectively, and assigning a free variable to each of the individual parts, where the weighted sum of the free variables was set to equal 1.0 (C58: 0.5: 0.3: 0.1: 0.1 and C34: 0.4: 0.3: 0.2: 0.1). Following refinement using the SUMP command, the EADP command was applied, which allowed for all of the anisotropic parameters of the fluorine ellipsoids to be similar in size. Lastly, the SADI command was applied to each of the affected C—F bonds in the disordered CF3 groups in order to have similar bond lengths for each of the disordered F atoms (i.e. the bond lengths were approximately equal for C58—F16AD, C58—F17AD, etc). The combination of these commands allowed for complete refinement of the CF3 disorder.

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Chloro-1,3-(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium tetrakis(3,5-trifluoromethylphenyl)borate top
Crystal data top
C17H38ClN2+·C32H12BF24F(000) = 2624
Mr = 1289.27Dx = 1.461 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 18.5025 (12) ÅCell parameters from 9997 reflections
b = 17.8739 (12) Åθ = 2.3–27.8°
c = 19.7857 (13) ŵ = 0.18 mm1
β = 116.428 (1)°T = 125 K
V = 5859.5 (7) Å3Needle, colourless
Z = 40.39 × 0.38 × 0.08 mm
Data collection top
Siemens/Bruker APEXII
diffractometer
8363 reflections with I > 2σ(I)
φ and ω scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 25.5°, θmin = 2.0°
Tmin = 0.660, Tmax = 0.746h = 2222
40063 measured reflectionsk = 2121
10921 independent reflectionsl = 2323
Refinement top
Refinement on F238 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0464P)2 + 4.6564P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
10921 reflectionsΔρmax = 0.52 e Å3
830 parametersΔρmin = 0.45 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.57779 (3)0.07669 (3)0.80176 (3)0.03051 (14)
F10.71125 (9)0.20864 (8)0.39608 (8)0.0499 (4)
F20.76498 (9)0.31577 (9)0.43499 (10)0.0592 (5)
F30.71913 (9)0.25293 (9)0.49856 (8)0.0469 (4)
F40.38941 (10)0.28263 (11)0.39231 (9)0.0641 (5)
F50.41659 (10)0.18771 (9)0.34260 (12)0.0690 (5)
F60.34175 (9)0.27432 (9)0.27269 (8)0.0507 (4)
F100.33308 (9)0.78402 (7)0.23647 (8)0.0459 (4)
F110.26822 (9)0.70653 (8)0.14865 (9)0.0537 (4)
F120.38410 (10)0.74577 (8)0.16469 (9)0.0497 (4)
F130.25354 (8)0.41455 (8)0.01425 (8)0.0445 (4)
F140.27430 (8)0.52975 (8)0.00069 (8)0.0385 (3)
F150.28655 (8)0.44738 (9)0.07256 (7)0.0470 (4)
F190.82744 (9)0.65439 (9)0.51987 (8)0.0488 (4)
F200.81541 (11)0.53617 (9)0.52327 (8)0.0657 (5)
F210.72766 (10)0.60866 (10)0.53192 (8)0.0561 (5)
F220.67492 (8)0.67563 (8)0.16727 (7)0.0426 (4)
F230.75829 (10)0.73793 (8)0.26143 (9)0.0490 (4)
F240.79387 (9)0.63343 (9)0.23298 (9)0.0492 (4)
N10.49006 (10)0.03298 (9)0.66179 (9)0.0219 (4)
N20.47084 (10)0.03195 (9)0.74765 (9)0.0225 (4)
C10.50909 (12)0.02306 (11)0.73361 (11)0.0219 (4)
C20.43398 (13)0.02710 (12)0.61751 (12)0.0273 (5)
H2A0.46160.06470.60040.033*
H2B0.38710.00660.57310.033*
C30.40817 (13)0.06074 (13)0.67455 (11)0.0275 (5)
H3A0.35370.04330.66510.033*
H3B0.40850.11610.67310.033*
C40.46845 (12)0.04819 (12)0.81830 (11)0.0239 (5)
C50.50674 (13)0.11362 (12)0.85634 (12)0.0262 (5)
C60.49935 (14)0.13078 (13)0.92158 (12)0.0308 (5)
H60.52460.17450.94930.037*
C70.45600 (14)0.08535 (13)0.94660 (12)0.0317 (5)
H70.45150.09840.99110.038*
C80.41908 (14)0.02121 (13)0.90777 (12)0.0311 (5)
H80.38980.00950.92610.037*
C90.42415 (13)0.00086 (12)0.84220 (12)0.0261 (5)
C100.38168 (13)0.06998 (13)0.80057 (13)0.0304 (5)
H100.39330.07620.75610.037*
C110.41371 (15)0.13920 (13)0.85073 (14)0.0378 (6)
H11A0.38860.18420.82130.057*
H11B0.47240.14210.86950.057*
H11C0.40060.13560.89350.057*
C120.29009 (14)0.06342 (15)0.77105 (15)0.0431 (6)
H12A0.26430.10970.74500.065*
H12B0.27730.05500.81350.065*
H12C0.27010.02130.73580.065*
C130.55597 (14)0.16215 (13)0.82903 (13)0.0312 (5)
H130.52920.16050.77260.037*
C140.64129 (15)0.13026 (15)0.85628 (15)0.0419 (6)
H14A0.67180.16140.83720.063*
H14B0.66860.13000.91160.063*
H14C0.63800.07900.83750.063*
C150.56033 (19)0.24404 (14)0.85261 (16)0.0466 (7)
H15A0.50560.26420.83430.070*
H15B0.58830.24770.90780.070*
H15C0.59000.27280.83090.070*
C160.52057 (13)0.08945 (11)0.62913 (11)0.0228 (4)
C170.47416 (13)0.15411 (12)0.60097 (11)0.0252 (5)
C180.50294 (15)0.20684 (12)0.56719 (12)0.0313 (5)
H180.47330.25160.54760.038*
C190.57381 (15)0.19514 (13)0.56161 (13)0.0335 (5)
H190.59220.23170.53800.040*
C200.61821 (14)0.13085 (13)0.59001 (12)0.0307 (5)
H200.66690.12380.58580.037*
C210.59283 (13)0.07586 (12)0.62487 (11)0.0253 (5)
C220.39771 (14)0.16936 (13)0.60966 (13)0.0310 (5)
H220.38130.12130.62470.037*
C230.32750 (15)0.19532 (16)0.53670 (14)0.0439 (6)
H23A0.34060.24390.52190.066*
H23B0.27900.20020.54450.066*
H23C0.31780.15860.49680.066*
C240.41498 (16)0.22592 (16)0.67338 (14)0.0432 (6)
H24A0.43000.27420.65970.065*
H24B0.45940.20750.72000.065*
H24C0.36660.23220.68110.065*
C250.64282 (14)0.00569 (13)0.65617 (13)0.0318 (5)
H250.61750.02370.68300.038*
C260.72921 (16)0.02464 (17)0.71340 (17)0.0543 (8)
H26A0.75610.05220.68810.081*
H26B0.75890.02170.73490.081*
H26C0.72800.05560.75380.081*
C270.64207 (18)0.04305 (14)0.59237 (15)0.0442 (7)
H27A0.58620.05550.55730.066*
H27B0.67240.08920.61350.066*
H27C0.66710.01570.56530.066*
C280.46452 (12)0.54706 (11)0.28500 (11)0.0214 (4)
C290.44991 (12)0.54002 (12)0.34834 (11)0.0236 (4)
H290.47360.49940.38190.028*
C300.40201 (13)0.59036 (12)0.36383 (12)0.0251 (5)
C310.36629 (13)0.65038 (12)0.31637 (12)0.0271 (5)
H310.33260.68430.32630.033*
C320.38103 (12)0.65968 (12)0.25381 (12)0.0240 (5)
C330.42937 (12)0.60951 (11)0.23918 (12)0.0228 (4)
H330.43910.61770.19650.027*
C340.39268 (15)0.58098 (14)0.43418 (14)0.0357 (6)
C350.34218 (14)0.72339 (13)0.20124 (13)0.0305 (5)
C360.53982 (12)0.41235 (11)0.31391 (11)0.0215 (4)
C370.47298 (13)0.37166 (12)0.30880 (11)0.0248 (5)
H370.42070.39280.28230.030*
C380.48060 (13)0.30127 (12)0.34134 (12)0.0274 (5)
C390.55582 (13)0.26877 (12)0.38019 (12)0.0270 (5)
H390.56120.22080.40260.032*
C400.62297 (13)0.30745 (12)0.38578 (11)0.0243 (5)
C410.61488 (13)0.37765 (12)0.35287 (11)0.0230 (4)
H410.66190.40280.35700.028*
C420.70419 (14)0.27203 (12)0.42822 (13)0.0299 (5)
C430.40729 (15)0.26223 (14)0.33705 (14)0.0367 (6)
C440.61133 (12)0.54189 (11)0.30350 (11)0.0207 (4)
C450.65695 (13)0.55098 (12)0.38128 (12)0.0235 (4)
H450.64070.52530.41430.028*
C460.72526 (13)0.59620 (12)0.41220 (12)0.0249 (5)
C470.75007 (13)0.63552 (12)0.36600 (12)0.0252 (5)
H470.79660.66650.38670.030*
C480.70505 (12)0.62841 (11)0.28859 (12)0.0226 (4)
C490.63740 (12)0.58233 (11)0.25804 (11)0.0220 (4)
H490.60810.57830.20470.026*
C500.77279 (15)0.59941 (14)0.49580 (13)0.0351 (6)
C510.73266 (13)0.66856 (12)0.23798 (12)0.0267 (5)
C520.49542 (12)0.46987 (11)0.18099 (11)0.0215 (4)
C530.54765 (12)0.43508 (12)0.15634 (12)0.0235 (4)
H530.60280.42890.19120.028*
C540.52144 (13)0.40933 (12)0.08269 (12)0.0248 (5)
C550.44147 (13)0.41754 (12)0.03016 (12)0.0259 (5)
H550.42330.40040.02020.031*
C560.38899 (13)0.45129 (11)0.05310 (11)0.0233 (4)
C570.41534 (12)0.47617 (11)0.12721 (11)0.0224 (4)
H570.37740.49810.14140.027*
C590.30216 (14)0.46077 (13)0.00085 (12)0.0305 (5)
B10.52749 (14)0.49284 (13)0.27032 (13)0.0212 (5)
C580.57881 (14)0.36974 (13)0.06062 (12)0.0334 (5)
F16A0.5578 (3)0.3839 (2)0.01354 (12)0.0362 (4)0.457 (3)
F17A0.5790 (3)0.29508 (11)0.0682 (3)0.0362 (4)0.457 (3)
F18A0.65707 (14)0.3914 (3)0.0972 (3)0.0362 (4)0.457 (3)
F16B0.5558 (5)0.3618 (4)0.01471 (13)0.0362 (4)0.315 (3)
F17B0.5990 (4)0.30242 (19)0.0940 (3)0.0362 (4)0.315 (3)
F18B0.6470 (2)0.4117 (3)0.0875 (4)0.0362 (4)0.315 (3)
F16C0.5496 (8)0.2997 (4)0.0363 (9)0.0362 (4)0.118 (3)
F17C0.6562 (3)0.3652 (9)0.1125 (6)0.0362 (4)0.118 (3)
F18C0.5837 (9)0.3942 (8)0.0020 (5)0.0362 (4)0.118 (3)
F16D0.5391 (7)0.3310 (8)0.0051 (6)0.0362 (4)0.110 (3)
F17D0.6205 (9)0.3188 (6)0.1136 (6)0.0362 (4)0.110 (3)
F18D0.6404 (6)0.4108 (7)0.0606 (9)0.0362 (4)0.110 (3)
F7A0.3939 (5)0.51089 (14)0.4606 (3)0.0351 (5)0.398 (3)
F8A0.3370 (4)0.6223 (4)0.4436 (4)0.0351 (5)0.398 (3)
F9A0.4609 (2)0.6116 (3)0.49079 (19)0.0351 (5)0.398 (3)
F7B0.3620 (4)0.51232 (18)0.4344 (3)0.0351 (5)0.338 (3)
F8B0.3334 (5)0.6281 (5)0.4284 (4)0.0351 (5)0.338 (3)
F9B0.4625 (2)0.5889 (3)0.4999 (2)0.0351 (5)0.338 (3)
F7C0.3999 (9)0.50701 (19)0.4506 (7)0.0351 (5)0.190 (3)
F8C0.3188 (3)0.5964 (6)0.4282 (5)0.0351 (5)0.190 (3)
F9C0.4455 (4)0.6156 (6)0.4995 (4)0.0351 (5)0.190 (3)
F7D0.3279 (8)0.5350 (9)0.4112 (10)0.0351 (5)0.0734 (19)
F8D0.3577 (12)0.6383 (9)0.4527 (14)0.0351 (5)0.0734 (19)
F9D0.4442 (10)0.5377 (10)0.4934 (7)0.0351 (5)0.0734 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0307 (3)0.0299 (3)0.0250 (3)0.0082 (2)0.0070 (2)0.0015 (2)
F10.0515 (9)0.0446 (9)0.0496 (9)0.0195 (7)0.0189 (8)0.0124 (7)
F20.0289 (8)0.0459 (9)0.0903 (13)0.0045 (7)0.0153 (8)0.0269 (9)
F30.0488 (9)0.0569 (10)0.0318 (8)0.0221 (7)0.0149 (7)0.0079 (7)
F40.0546 (10)0.1007 (14)0.0528 (10)0.0322 (10)0.0381 (9)0.0135 (9)
F50.0544 (10)0.0349 (9)0.1155 (16)0.0146 (8)0.0357 (11)0.0160 (9)
F60.0337 (8)0.0657 (11)0.0449 (9)0.0190 (7)0.0105 (7)0.0062 (8)
F100.0632 (10)0.0234 (7)0.0480 (9)0.0094 (7)0.0220 (8)0.0000 (6)
F110.0391 (9)0.0390 (9)0.0491 (9)0.0009 (7)0.0108 (7)0.0055 (7)
F120.0595 (10)0.0430 (9)0.0576 (10)0.0171 (7)0.0360 (8)0.0254 (7)
F130.0288 (7)0.0461 (9)0.0550 (9)0.0129 (6)0.0153 (7)0.0047 (7)
F140.0290 (7)0.0378 (8)0.0402 (8)0.0058 (6)0.0077 (6)0.0012 (6)
F150.0330 (8)0.0726 (11)0.0245 (7)0.0039 (7)0.0029 (6)0.0126 (7)
F190.0449 (9)0.0591 (10)0.0325 (8)0.0212 (8)0.0082 (7)0.0156 (7)
F200.0818 (12)0.0504 (10)0.0300 (8)0.0155 (9)0.0065 (8)0.0039 (7)
F210.0561 (10)0.0880 (13)0.0281 (7)0.0215 (9)0.0221 (7)0.0141 (8)
F220.0393 (8)0.0531 (9)0.0333 (7)0.0058 (7)0.0143 (6)0.0144 (7)
F230.0696 (11)0.0312 (8)0.0549 (9)0.0185 (7)0.0354 (8)0.0028 (7)
F240.0502 (9)0.0524 (9)0.0659 (10)0.0230 (8)0.0448 (8)0.0260 (8)
N10.0216 (9)0.0207 (9)0.0201 (9)0.0012 (7)0.0064 (7)0.0005 (7)
N20.0224 (9)0.0213 (9)0.0202 (9)0.0041 (7)0.0061 (7)0.0003 (7)
C10.0210 (10)0.0185 (10)0.0231 (11)0.0029 (8)0.0070 (9)0.0003 (8)
C20.0288 (12)0.0262 (12)0.0228 (11)0.0052 (9)0.0078 (9)0.0034 (9)
C30.0264 (11)0.0291 (12)0.0218 (11)0.0070 (9)0.0061 (9)0.0016 (9)
C40.0224 (11)0.0266 (11)0.0196 (10)0.0074 (9)0.0068 (9)0.0004 (8)
C50.0264 (11)0.0242 (11)0.0241 (11)0.0069 (9)0.0077 (9)0.0014 (9)
C60.0353 (13)0.0272 (12)0.0253 (11)0.0045 (10)0.0093 (10)0.0037 (9)
C70.0353 (13)0.0363 (13)0.0229 (11)0.0113 (10)0.0126 (10)0.0006 (10)
C80.0296 (12)0.0358 (13)0.0286 (12)0.0073 (10)0.0137 (10)0.0054 (10)
C90.0225 (11)0.0273 (12)0.0251 (11)0.0069 (9)0.0074 (9)0.0021 (9)
C100.0290 (12)0.0307 (12)0.0305 (12)0.0018 (10)0.0123 (10)0.0011 (10)
C110.0399 (14)0.0297 (13)0.0384 (14)0.0023 (11)0.0124 (11)0.0016 (10)
C120.0302 (13)0.0440 (15)0.0480 (15)0.0028 (11)0.0110 (12)0.0026 (12)
C130.0363 (13)0.0264 (12)0.0274 (12)0.0007 (10)0.0112 (10)0.0032 (9)
C140.0324 (13)0.0399 (15)0.0492 (15)0.0057 (11)0.0142 (12)0.0022 (12)
C150.0691 (19)0.0267 (13)0.0488 (16)0.0030 (13)0.0305 (15)0.0038 (11)
C160.0262 (11)0.0220 (11)0.0179 (10)0.0025 (9)0.0077 (9)0.0009 (8)
C170.0287 (12)0.0231 (11)0.0194 (10)0.0014 (9)0.0067 (9)0.0009 (8)
C180.0439 (14)0.0206 (11)0.0266 (11)0.0033 (10)0.0131 (11)0.0033 (9)
C190.0500 (15)0.0257 (12)0.0292 (12)0.0057 (11)0.0215 (11)0.0017 (9)
C200.0336 (13)0.0325 (13)0.0312 (12)0.0034 (10)0.0191 (10)0.0011 (10)
C210.0276 (11)0.0271 (12)0.0210 (10)0.0009 (9)0.0107 (9)0.0007 (9)
C220.0326 (12)0.0246 (12)0.0345 (12)0.0067 (10)0.0139 (10)0.0032 (9)
C230.0353 (14)0.0463 (16)0.0400 (14)0.0102 (12)0.0077 (12)0.0013 (12)
C240.0382 (14)0.0502 (16)0.0384 (14)0.0125 (12)0.0145 (12)0.0052 (12)
C250.0328 (12)0.0318 (13)0.0349 (12)0.0071 (10)0.0187 (11)0.0084 (10)
C260.0375 (15)0.0547 (18)0.0590 (18)0.0144 (13)0.0109 (14)0.0113 (15)
C270.0641 (18)0.0307 (14)0.0510 (16)0.0119 (13)0.0375 (15)0.0066 (12)
C280.0192 (10)0.0233 (11)0.0194 (10)0.0035 (8)0.0066 (8)0.0028 (8)
C290.0214 (11)0.0242 (11)0.0236 (11)0.0007 (9)0.0085 (9)0.0014 (9)
C300.0232 (11)0.0271 (12)0.0244 (11)0.0016 (9)0.0101 (9)0.0039 (9)
C310.0233 (11)0.0257 (12)0.0318 (12)0.0004 (9)0.0119 (10)0.0075 (9)
C320.0207 (11)0.0214 (11)0.0256 (11)0.0030 (8)0.0065 (9)0.0024 (8)
C330.0219 (10)0.0232 (11)0.0231 (10)0.0048 (8)0.0098 (9)0.0018 (8)
C340.0395 (14)0.0370 (14)0.0373 (13)0.0063 (11)0.0231 (12)0.0004 (11)
C350.0292 (12)0.0267 (12)0.0317 (12)0.0024 (9)0.0100 (10)0.0010 (10)
C360.0253 (11)0.0221 (11)0.0191 (10)0.0019 (8)0.0118 (9)0.0028 (8)
C370.0247 (11)0.0271 (12)0.0226 (10)0.0011 (9)0.0105 (9)0.0012 (9)
C380.0309 (12)0.0259 (12)0.0271 (11)0.0072 (9)0.0145 (10)0.0025 (9)
C390.0373 (13)0.0209 (11)0.0251 (11)0.0007 (9)0.0159 (10)0.0001 (9)
C400.0304 (12)0.0223 (11)0.0219 (10)0.0002 (9)0.0132 (9)0.0023 (8)
C410.0247 (11)0.0231 (11)0.0242 (10)0.0019 (9)0.0137 (9)0.0029 (8)
C420.0341 (13)0.0235 (12)0.0338 (13)0.0042 (10)0.0167 (11)0.0006 (9)
C430.0362 (14)0.0363 (14)0.0369 (13)0.0082 (11)0.0157 (12)0.0017 (11)
C440.0225 (10)0.0192 (10)0.0222 (10)0.0037 (8)0.0115 (9)0.0001 (8)
C450.0263 (11)0.0214 (11)0.0256 (11)0.0013 (9)0.0140 (9)0.0008 (8)
C460.0249 (11)0.0233 (11)0.0244 (11)0.0026 (9)0.0092 (9)0.0028 (9)
C470.0216 (11)0.0216 (11)0.0309 (12)0.0003 (9)0.0103 (9)0.0027 (9)
C480.0229 (11)0.0177 (10)0.0290 (11)0.0035 (8)0.0131 (9)0.0009 (8)
C490.0224 (10)0.0220 (11)0.0213 (10)0.0038 (8)0.0096 (9)0.0014 (8)
C500.0372 (13)0.0352 (13)0.0271 (12)0.0042 (11)0.0089 (11)0.0037 (10)
C510.0259 (12)0.0230 (11)0.0334 (12)0.0007 (9)0.0152 (10)0.0015 (9)
C520.0248 (11)0.0172 (10)0.0228 (10)0.0021 (8)0.0109 (9)0.0018 (8)
C530.0209 (10)0.0244 (11)0.0239 (10)0.0009 (8)0.0088 (9)0.0005 (8)
C540.0280 (11)0.0222 (11)0.0270 (11)0.0015 (9)0.0148 (9)0.0002 (9)
C550.0310 (12)0.0240 (11)0.0232 (11)0.0033 (9)0.0126 (10)0.0038 (9)
C560.0250 (11)0.0200 (11)0.0244 (11)0.0027 (8)0.0104 (9)0.0004 (8)
C570.0231 (11)0.0204 (11)0.0255 (11)0.0019 (8)0.0125 (9)0.0007 (8)
C590.0274 (12)0.0338 (13)0.0284 (12)0.0036 (10)0.0107 (10)0.0062 (10)
B10.0208 (12)0.0223 (12)0.0199 (11)0.0010 (9)0.0085 (10)0.0010 (9)
C580.0317 (13)0.0377 (14)0.0305 (12)0.0009 (10)0.0136 (10)0.0048 (10)
F16A0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F17A0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F18A0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F16B0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F17B0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F18B0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F16C0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F17C0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F18C0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F16D0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F17D0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F18D0.0396 (8)0.0351 (10)0.0406 (8)0.0062 (7)0.0239 (7)0.0056 (7)
F7A0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F8A0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F9A0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F7B0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F8B0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F9B0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F7C0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F8C0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F9C0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F7D0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F8D0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
F9D0.0448 (8)0.0450 (9)0.0241 (9)0.0091 (6)0.0230 (7)0.0062 (6)
Geometric parameters (Å, º) top
Cl1—C11.681 (2)C30—C341.486 (3)
F1—C421.334 (3)C31—C321.391 (3)
F2—C421.327 (3)C32—C331.385 (3)
F3—C421.337 (3)C32—C351.493 (3)
F4—C431.327 (3)C34—F8C1.346 (3)
F5—C431.341 (3)C34—F8A1.347 (3)
F6—C431.328 (3)C34—F8D1.347 (3)
F10—C351.339 (3)C34—F8B1.347 (3)
F11—C351.334 (3)C34—F7B1.353 (3)
F12—C351.336 (3)C34—F7A1.354 (3)
F13—C591.349 (3)C34—F7C1.354 (3)
F14—C591.342 (3)C34—F7D1.354 (3)
F15—C591.337 (3)C34—F9B1.372 (3)
F19—C501.337 (3)C34—F9D1.373 (3)
F20—C501.347 (3)C34—F9C1.373 (3)
F21—C501.329 (3)C34—F9A1.374 (3)
F22—C511.336 (3)C36—C411.398 (3)
F23—C511.335 (3)C36—C371.399 (3)
F24—C511.337 (3)C36—B11.640 (3)
N1—C11.315 (3)C37—C381.392 (3)
N1—C161.442 (3)C38—C391.383 (3)
N1—C21.479 (3)C38—C431.494 (3)
N2—C11.311 (3)C39—C401.383 (3)
N2—C41.448 (3)C40—C411.391 (3)
N2—C31.486 (3)C40—C421.497 (3)
C2—C31.531 (3)C44—C491.397 (3)
C4—C91.399 (3)C44—C451.397 (3)
C4—C51.400 (3)C44—B11.643 (3)
C5—C61.391 (3)C45—C461.392 (3)
C5—C131.521 (3)C46—C471.383 (3)
C6—C71.379 (3)C46—C501.489 (3)
C7—C81.380 (3)C47—C481.386 (3)
C8—C91.390 (3)C48—C491.392 (3)
C9—C101.524 (3)C48—C511.495 (3)
C10—C111.531 (3)C52—C571.392 (3)
C10—C121.532 (3)C52—C531.406 (3)
C13—C151.527 (3)C52—B11.646 (3)
C13—C141.533 (3)C53—C541.393 (3)
C16—C211.398 (3)C54—C551.386 (3)
C16—C171.399 (3)C54—C581.494 (3)
C17—C181.391 (3)C55—C561.380 (3)
C17—C221.524 (3)C56—C571.396 (3)
C18—C191.380 (3)C56—C591.491 (3)
C19—C201.378 (3)C58—F17A1.343 (3)
C20—C211.397 (3)C58—F17C1.343 (3)
C21—C251.517 (3)C58—F17B1.343 (3)
C22—C231.522 (3)C58—F17D1.343 (3)
C22—C241.535 (3)C58—F18D1.355 (3)
C25—C271.529 (3)C58—F18A1.356 (3)
C25—C261.530 (4)C58—F18C1.356 (3)
C28—C291.400 (3)C58—F18B1.356 (3)
C28—C331.402 (3)C58—F16B1.363 (3)
C28—B11.638 (3)C58—F16D1.363 (3)
C29—C301.390 (3)C58—F16C1.364 (3)
C30—C311.385 (3)C58—F16A1.364 (3)
C1—N1—C16127.50 (17)C39—C38—C37120.4 (2)
C1—N1—C2108.78 (17)C39—C38—C43119.9 (2)
C16—N1—C2123.64 (16)C37—C38—C43119.6 (2)
C1—N2—C4127.33 (17)C40—C39—C38118.7 (2)
C1—N2—C3108.32 (16)C39—C40—C41120.5 (2)
C4—N2—C3121.63 (16)C39—C40—C42118.38 (19)
N2—C1—N1114.83 (18)C41—C40—C42121.1 (2)
N2—C1—Cl1122.96 (16)C40—C41—C36122.1 (2)
N1—C1—Cl1122.21 (16)F2—C42—F1106.87 (19)
N1—C2—C3102.43 (16)F2—C42—F3105.79 (19)
N2—C3—C2102.55 (16)F1—C42—F3105.11 (18)
C9—C4—C5123.8 (2)F2—C42—C40113.68 (18)
C9—C4—N2118.65 (19)F1—C42—C40112.25 (19)
C5—C4—N2117.44 (19)F3—C42—C40112.51 (18)
C6—C5—C4116.6 (2)F4—C43—F6106.8 (2)
C6—C5—C13121.7 (2)F4—C43—F5106.0 (2)
C4—C5—C13121.67 (19)F6—C43—F5105.6 (2)
C7—C6—C5121.1 (2)F4—C43—C38112.2 (2)
C6—C7—C8120.8 (2)F6—C43—C38113.39 (19)
C7—C8—C9121.0 (2)F5—C43—C38112.3 (2)
C8—C9—C4116.8 (2)C49—C44—C45115.90 (19)
C8—C9—C10119.3 (2)C49—C44—B1123.66 (17)
C4—C9—C10123.96 (19)C45—C44—B1120.16 (18)
C9—C10—C11111.30 (18)C46—C45—C44122.49 (19)
C9—C10—C12111.1 (2)C47—C46—C45120.54 (19)
C11—C10—C12110.6 (2)C47—C46—C50120.6 (2)
C5—C13—C15113.4 (2)C45—C46—C50118.8 (2)
C5—C13—C14110.42 (19)C46—C47—C48118.09 (19)
C15—C13—C14110.0 (2)C47—C48—C49121.08 (19)
C21—C16—C17123.61 (19)C47—C48—C51118.68 (19)
C21—C16—N1118.76 (18)C49—C48—C51120.18 (18)
C17—C16—N1117.60 (19)C48—C49—C44121.89 (19)
C18—C17—C16116.9 (2)F21—C50—F19105.88 (19)
C18—C17—C22120.4 (2)F21—C50—F20106.4 (2)
C16—C17—C22122.61 (19)F19—C50—F20105.0 (2)
C19—C18—C17121.1 (2)F21—C50—C46113.6 (2)
C20—C19—C18120.6 (2)F19—C50—C46113.8 (2)
C19—C20—C21121.2 (2)F20—C50—C46111.48 (19)
C20—C21—C16116.6 (2)F23—C51—F22105.73 (17)
C20—C21—C25120.4 (2)F23—C51—F24106.28 (18)
C16—C21—C25123.01 (19)F22—C51—F24106.02 (18)
C23—C22—C17113.0 (2)F23—C51—C48112.81 (18)
C23—C22—C24110.9 (2)F22—C51—C48113.24 (17)
C17—C22—C24110.26 (19)F24—C51—C48112.18 (17)
C21—C25—C27110.75 (19)C57—C52—C53115.63 (19)
C21—C25—C26111.4 (2)C57—C52—B1123.57 (18)
C27—C25—C26111.1 (2)C53—C52—B1120.50 (18)
C29—C28—C33115.55 (19)C54—C53—C52122.39 (19)
C29—C28—B1122.78 (18)C55—C54—C53120.5 (2)
C33—C28—B1121.23 (18)C55—C54—C58119.43 (19)
C30—C29—C28122.4 (2)C53—C54—C58120.02 (19)
C31—C30—C29120.7 (2)C56—C55—C54118.17 (19)
C31—C30—C34120.2 (2)C55—C56—C57121.10 (19)
C29—C30—C34119.0 (2)C55—C56—C59120.39 (19)
C30—C31—C32118.2 (2)C57—C56—C59118.50 (19)
C33—C32—C31120.6 (2)C52—C57—C56122.2 (2)
C33—C32—C35120.2 (2)F15—C59—F14106.54 (18)
C31—C32—C35119.1 (2)F15—C59—F13105.96 (18)
C32—C33—C28122.5 (2)F14—C59—F13104.88 (18)
F8B—C34—F7B103.9 (5)F15—C59—C56113.22 (19)
F8A—C34—F7A109.7 (4)F14—C59—C56112.99 (18)
F8C—C34—F7C102.1 (7)F13—C59—C56112.58 (19)
F8D—C34—F7D95.3 (12)C28—B1—C36111.67 (17)
F8B—C34—F9B113.8 (5)C28—B1—C44103.48 (16)
F7B—C34—F9B108.1 (3)C36—B1—C44111.86 (16)
F8D—C34—F9D115.6 (13)C28—B1—C52113.14 (16)
F7D—C34—F9D96.9 (12)C36—B1—C52104.19 (16)
F8C—C34—F9C105.0 (5)C44—B1—C52112.77 (17)
F7C—C34—F9C105.2 (8)F17D—C58—F18D100.2 (9)
F8A—C34—F9A98.6 (5)F17A—C58—F18A106.0 (3)
F7A—C34—F9A101.7 (4)F17C—C58—F18C103.6 (8)
F11—C35—F12106.67 (19)F17B—C58—F18B107.2 (4)
F11—C35—F10105.42 (18)F17B—C58—F16B109.1 (3)
F12—C35—F10106.10 (19)F18B—C58—F16B105.7 (4)
F11—C35—C32112.32 (19)F17D—C58—F16D106.2 (9)
F12—C35—C32112.96 (19)F18D—C58—F16D111.7 (9)
F10—C35—C32112.80 (18)F17C—C58—F16C109.5 (8)
C41—C36—C37116.00 (19)F18C—C58—F16C98.7 (8)
C41—C36—B1123.41 (18)F17A—C58—F16A106.8 (3)
C37—C36—B1120.42 (18)F18A—C58—F16A104.3 (3)
C38—C37—C36122.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···F15i0.992.433.256 (3)141
C12—H12A···F17Cii0.982.533.269 (12)132
C19—H19···F8Diii0.952.483.297 (18)144
C29—H29···F9Diii0.952.353.180 (14)146
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1/2, y+1/2, z+1/2; (iii) x+1, y+1, z+1.
 

Acknowledgements

We thank the Natural Sciences and Engineering Research Council of Canada (through the Discovery Grants Program to JDM). JDM acknowledges support from the Canadian Foundation for Innovation, the Nova Scotia Research and Innovation Trust Fund and Saint Mary's University.

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