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

Stack, D.L.; Masuda, J.D.

doi:10.1107/S2056989016014584

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ISSN: 2056-9890

Volume 72| Part 10| October 2016| Pages 1471-1474

https://doi.org/10.1107/S2056989016014584

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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

Darcie L. Stack ^a and Jason D. Masuda ^a ^*

^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.

Keywords: crystal structure; N-heterocyclic carbene; NHC; 2-chloro imidazolidinium; borate.

CCDC reference: 1504219

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 ), leading to the discovery of the first phosphino silyl carbenes (Igau et al., 1988 ) followed by other novel singlet carbenes (Lavallo et al., 2005 ; Frey et al., 2007 ; Aldeco-Perez et al., 2009 ). However, the report of the first `bottleable' crystalline N-heterocyclic carbene (NHC) (Arduengo et al., 1991 ) initiated a new paradigm in synthetic chemistry (Bourissou et al., 2000 ). 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.

2. Structural commentary

The molecular structure of the title salt compound is shown in Fig. 1. 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
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), which link the cations and anions, forming a three-dimensional network (Fig. 2). 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	D⋯A	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
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 ) 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 ) and SISVUN (Böttcher et al., 2014 )]. 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 ) and XOMMER (Kuhn et al., 2002 )].

5. Synthesis and crystallization

In a glovebox, prior to the synthesis of the title compound, SIPrCO₂ (Zhou et al., 2008 ) 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. 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
M_r	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)
V (Å³)	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 )
T_min, T_max	0.660, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	40063, 10921, 8363
R_int	0.033
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.45
Computer programs: APEX2 and SAINT (Bruker, 2008), XS in SHELXTL (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

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—F16A–D, C58—F17A–D, etc). The combination of these commands allowed for complete refinement of the CF₃ disorder.

Supporting information

CCDC reference: 1504219

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989016014584/lh5822sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016014584/lh5822Isup2.hkl

checkCIF report

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⁺·C₃₂H₁₂BF₂₄	F(000) = 2624
M_r = 1289.27	D_x = 1.461 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 18.5025 (12) Å	Cell parameters from 9997 reflections
b = 17.8739 (12) Å	θ = 2.3–27.8°
c = 19.7857 (13) Å	µ = 0.18 mm⁻¹
β = 116.428 (1)°	T = 125 K
V = 5859.5 (7) Å³	Needle, colourless
Z = 4	0.39 × 0.38 × 0.08 mm

Data collection top

Siemens/Bruker APEXII diffractometer	8363 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 25.5°, θ_min = 2.0°
T_min = 0.660, T_max = 0.746	h = −22→22
40063 measured reflections	k = −21→21
10921 independent reflections	l = −23→23

Refinement top

Refinement on F²	38 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0464P)² + 4.6564P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
10921 reflections	Δρ_max = 0.52 e Å⁻³
830 parameters	Δρ_min = −0.45 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.57779 (3)	0.07669 (3)	0.80176 (3)	0.03051 (14)
F1	0.71125 (9)	0.20864 (8)	0.39608 (8)	0.0499 (4)
F2	0.76498 (9)	0.31577 (9)	0.43499 (10)	0.0592 (5)
F3	0.71913 (9)	0.25293 (9)	0.49856 (8)	0.0469 (4)
F4	0.38941 (10)	0.28263 (11)	0.39231 (9)	0.0641 (5)
F5	0.41659 (10)	0.18771 (9)	0.34260 (12)	0.0690 (5)
F6	0.34175 (9)	0.27432 (9)	0.27269 (8)	0.0507 (4)
F10	0.33308 (9)	0.78402 (7)	0.23647 (8)	0.0459 (4)
F11	0.26822 (9)	0.70653 (8)	0.14865 (9)	0.0537 (4)
F12	0.38410 (10)	0.74577 (8)	0.16469 (9)	0.0497 (4)
F13	0.25354 (8)	0.41455 (8)	0.01425 (8)	0.0445 (4)
F14	0.27430 (8)	0.52975 (8)	0.00069 (8)	0.0385 (3)
F15	0.28655 (8)	0.44738 (9)	−0.07256 (7)	0.0470 (4)
F19	0.82744 (9)	0.65439 (9)	0.51987 (8)	0.0488 (4)
F20	0.81541 (11)	0.53617 (9)	0.52327 (8)	0.0657 (5)
F21	0.72766 (10)	0.60866 (10)	0.53192 (8)	0.0561 (5)
F22	0.67492 (8)	0.67563 (8)	0.16727 (7)	0.0426 (4)
F23	0.75829 (10)	0.73793 (8)	0.26143 (9)	0.0490 (4)
F24	0.79387 (9)	0.63343 (9)	0.23298 (9)	0.0492 (4)
N1	0.49006 (10)	0.03298 (9)	0.66179 (9)	0.0219 (4)
N2	0.47084 (10)	−0.03195 (9)	0.74765 (9)	0.0225 (4)
C1	0.50909 (12)	0.02306 (11)	0.73361 (11)	0.0219 (4)
C2	0.43398 (13)	−0.02710 (12)	0.61751 (12)	0.0273 (5)
H2A	0.4616	−0.0647	0.6004	0.033*
H2B	0.3871	−0.0066	0.5731	0.033*
C3	0.40817 (13)	−0.06074 (13)	0.67455 (11)	0.0275 (5)
H3A	0.3537	−0.0433	0.6651	0.033*
H3B	0.4085	−0.1161	0.6731	0.033*
C4	0.46845 (12)	−0.04819 (12)	0.81830 (11)	0.0239 (5)
C5	0.50674 (13)	−0.11362 (12)	0.85634 (12)	0.0262 (5)
C6	0.49935 (14)	−0.13078 (13)	0.92158 (12)	0.0308 (5)
H6	0.5246	−0.1745	0.9493	0.037*
C7	0.45600 (14)	−0.08535 (13)	0.94660 (12)	0.0317 (5)
H7	0.4515	−0.0984	0.9911	0.038*
C8	0.41908 (14)	−0.02121 (13)	0.90777 (12)	0.0311 (5)
H8	0.3898	0.0095	0.9261	0.037*
C9	0.42415 (13)	−0.00086 (12)	0.84220 (12)	0.0261 (5)
C10	0.38168 (13)	0.06998 (13)	0.80057 (13)	0.0304 (5)
H10	0.3933	0.0762	0.7561	0.037*
C11	0.41371 (15)	0.13920 (13)	0.85073 (14)	0.0378 (6)
H11A	0.3886	0.1842	0.8213	0.057*
H11B	0.4724	0.1421	0.8695	0.057*
H11C	0.4006	0.1356	0.8935	0.057*
C12	0.29009 (14)	0.06342 (15)	0.77105 (15)	0.0431 (6)
H12A	0.2643	0.1097	0.7450	0.065*
H12B	0.2773	0.0550	0.8135	0.065*
H12C	0.2701	0.0213	0.7358	0.065*
C13	0.55597 (14)	−0.16215 (13)	0.82903 (13)	0.0312 (5)
H13	0.5292	−0.1605	0.7726	0.037*
C14	0.64129 (15)	−0.13026 (15)	0.85628 (15)	0.0419 (6)
H14A	0.6718	−0.1614	0.8372	0.063*
H14B	0.6686	−0.1300	0.9116	0.063*
H14C	0.6380	−0.0790	0.8375	0.063*
C15	0.56033 (19)	−0.24404 (14)	0.85261 (16)	0.0466 (7)
H15A	0.5056	−0.2642	0.8343	0.070*
H15B	0.5883	−0.2477	0.9078	0.070*
H15C	0.5900	−0.2728	0.8309	0.070*
C16	0.52057 (13)	0.08945 (11)	0.62913 (11)	0.0228 (4)
C17	0.47416 (13)	0.15411 (12)	0.60097 (11)	0.0252 (5)
C18	0.50294 (15)	0.20684 (12)	0.56719 (12)	0.0313 (5)
H18	0.4733	0.2516	0.5476	0.038*
C19	0.57381 (15)	0.19514 (13)	0.56161 (13)	0.0335 (5)
H19	0.5922	0.2317	0.5380	0.040*
C20	0.61821 (14)	0.13085 (13)	0.59001 (12)	0.0307 (5)
H20	0.6669	0.1238	0.5858	0.037*
C21	0.59283 (13)	0.07586 (12)	0.62487 (11)	0.0253 (5)
C22	0.39771 (14)	0.16936 (13)	0.60966 (13)	0.0310 (5)
H22	0.3813	0.1213	0.6247	0.037*
C23	0.32750 (15)	0.19532 (16)	0.53670 (14)	0.0439 (6)
H23A	0.3406	0.2439	0.5219	0.066*
H23B	0.2790	0.2002	0.5445	0.066*
H23C	0.3178	0.1586	0.4968	0.066*
C24	0.41498 (16)	0.22592 (16)	0.67338 (14)	0.0432 (6)
H24A	0.4300	0.2742	0.6597	0.065*
H24B	0.4594	0.2075	0.7200	0.065*
H24C	0.3666	0.2322	0.6811	0.065*
C25	0.64282 (14)	0.00569 (13)	0.65617 (13)	0.0318 (5)
H25	0.6175	−0.0237	0.6830	0.038*
C26	0.72921 (16)	0.02464 (17)	0.71340 (17)	0.0543 (8)
H26A	0.7561	0.0522	0.6881	0.081*
H26B	0.7589	−0.0217	0.7349	0.081*
H26C	0.7280	0.0556	0.7538	0.081*
C27	0.64207 (18)	−0.04305 (14)	0.59237 (15)	0.0442 (7)
H27A	0.5862	−0.0555	0.5573	0.066*
H27B	0.6724	−0.0892	0.6135	0.066*
H27C	0.6671	−0.0157	0.5653	0.066*
C28	0.46452 (12)	0.54706 (11)	0.28500 (11)	0.0214 (4)
C29	0.44991 (12)	0.54002 (12)	0.34834 (11)	0.0236 (4)
H29	0.4736	0.4994	0.3819	0.028*
C30	0.40201 (13)	0.59036 (12)	0.36383 (12)	0.0251 (5)
C31	0.36629 (13)	0.65038 (12)	0.31637 (12)	0.0271 (5)
H31	0.3326	0.6843	0.3263	0.033*
C32	0.38103 (12)	0.65968 (12)	0.25381 (12)	0.0240 (5)
C33	0.42937 (12)	0.60951 (11)	0.23918 (12)	0.0228 (4)
H33	0.4391	0.6177	0.1965	0.027*
C34	0.39268 (15)	0.58098 (14)	0.43418 (14)	0.0357 (6)
C35	0.34218 (14)	0.72339 (13)	0.20124 (13)	0.0305 (5)
C36	0.53982 (12)	0.41235 (11)	0.31391 (11)	0.0215 (4)
C37	0.47298 (13)	0.37166 (12)	0.30880 (11)	0.0248 (5)
H37	0.4207	0.3928	0.2823	0.030*
C38	0.48060 (13)	0.30127 (12)	0.34134 (12)	0.0274 (5)
C39	0.55582 (13)	0.26877 (12)	0.38019 (12)	0.0270 (5)
H39	0.5612	0.2208	0.4026	0.032*
C40	0.62297 (13)	0.30745 (12)	0.38578 (11)	0.0243 (5)
C41	0.61488 (13)	0.37765 (12)	0.35287 (11)	0.0230 (4)
H41	0.6619	0.4028	0.3570	0.028*
C42	0.70419 (14)	0.27203 (12)	0.42822 (13)	0.0299 (5)
C43	0.40729 (15)	0.26223 (14)	0.33705 (14)	0.0367 (6)
C44	0.61133 (12)	0.54189 (11)	0.30350 (11)	0.0207 (4)
C45	0.65695 (13)	0.55098 (12)	0.38128 (12)	0.0235 (4)
H45	0.6407	0.5253	0.4143	0.028*
C46	0.72526 (13)	0.59620 (12)	0.41220 (12)	0.0249 (5)
C47	0.75007 (13)	0.63552 (12)	0.36600 (12)	0.0252 (5)
H47	0.7966	0.6665	0.3867	0.030*
C48	0.70505 (12)	0.62841 (11)	0.28859 (12)	0.0226 (4)
C49	0.63740 (12)	0.58233 (11)	0.25804 (11)	0.0220 (4)
H49	0.6081	0.5783	0.2047	0.026*
C50	0.77279 (15)	0.59941 (14)	0.49580 (13)	0.0351 (6)
C51	0.73266 (13)	0.66856 (12)	0.23798 (12)	0.0267 (5)
C52	0.49542 (12)	0.46987 (11)	0.18099 (11)	0.0215 (4)
C53	0.54765 (12)	0.43508 (12)	0.15634 (12)	0.0235 (4)
H53	0.6028	0.4289	0.1912	0.028*
C54	0.52144 (13)	0.40933 (12)	0.08269 (12)	0.0248 (5)
C55	0.44147 (13)	0.41754 (12)	0.03016 (12)	0.0259 (5)
H55	0.4233	0.4004	−0.0202	0.031*
C56	0.38899 (13)	0.45129 (11)	0.05310 (11)	0.0233 (4)
C57	0.41534 (12)	0.47617 (11)	0.12721 (11)	0.0224 (4)
H57	0.3774	0.4981	0.1414	0.027*
C59	0.30216 (14)	0.46077 (13)	−0.00085 (12)	0.0305 (5)
B1	0.52749 (14)	0.49284 (13)	0.27032 (13)	0.0212 (5)
C58	0.57881 (14)	0.36974 (13)	0.06062 (12)	0.0334 (5)
F16A	0.5578 (3)	0.3839 (2)	−0.01354 (12)	0.0362 (4)	0.457 (3)
F17A	0.5790 (3)	0.29508 (11)	0.0682 (3)	0.0362 (4)	0.457 (3)
F18A	0.65707 (14)	0.3914 (3)	0.0972 (3)	0.0362 (4)	0.457 (3)
F16B	0.5558 (5)	0.3618 (4)	−0.01471 (13)	0.0362 (4)	0.315 (3)
F17B	0.5990 (4)	0.30242 (19)	0.0940 (3)	0.0362 (4)	0.315 (3)
F18B	0.6470 (2)	0.4117 (3)	0.0875 (4)	0.0362 (4)	0.315 (3)
F16C	0.5496 (8)	0.2997 (4)	0.0363 (9)	0.0362 (4)	0.118 (3)
F17C	0.6562 (3)	0.3652 (9)	0.1125 (6)	0.0362 (4)	0.118 (3)
F18C	0.5837 (9)	0.3942 (8)	−0.0020 (5)	0.0362 (4)	0.118 (3)
F16D	0.5391 (7)	0.3310 (8)	−0.0051 (6)	0.0362 (4)	0.110 (3)
F17D	0.6205 (9)	0.3188 (6)	0.1136 (6)	0.0362 (4)	0.110 (3)
F18D	0.6404 (6)	0.4108 (7)	0.0606 (9)	0.0362 (4)	0.110 (3)
F7A	0.3939 (5)	0.51089 (14)	0.4606 (3)	0.0351 (5)	0.398 (3)
F8A	0.3370 (4)	0.6223 (4)	0.4436 (4)	0.0351 (5)	0.398 (3)
F9A	0.4609 (2)	0.6116 (3)	0.49079 (19)	0.0351 (5)	0.398 (3)
F7B	0.3620 (4)	0.51232 (18)	0.4344 (3)	0.0351 (5)	0.338 (3)
F8B	0.3334 (5)	0.6281 (5)	0.4284 (4)	0.0351 (5)	0.338 (3)
F9B	0.4625 (2)	0.5889 (3)	0.4999 (2)	0.0351 (5)	0.338 (3)
F7C	0.3999 (9)	0.50701 (19)	0.4506 (7)	0.0351 (5)	0.190 (3)
F8C	0.3188 (3)	0.5964 (6)	0.4282 (5)	0.0351 (5)	0.190 (3)
F9C	0.4455 (4)	0.6156 (6)	0.4995 (4)	0.0351 (5)	0.190 (3)
F7D	0.3279 (8)	0.5350 (9)	0.4112 (10)	0.0351 (5)	0.0734 (19)
F8D	0.3577 (12)	0.6383 (9)	0.4527 (14)	0.0351 (5)	0.0734 (19)
F9D	0.4442 (10)	0.5377 (10)	0.4934 (7)	0.0351 (5)	0.0734 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0307 (3)	0.0299 (3)	0.0250 (3)	−0.0082 (2)	0.0070 (2)	−0.0015 (2)
F1	0.0515 (9)	0.0446 (9)	0.0496 (9)	0.0195 (7)	0.0189 (8)	−0.0124 (7)
F2	0.0289 (8)	0.0459 (9)	0.0903 (13)	0.0045 (7)	0.0153 (8)	0.0269 (9)
F3	0.0488 (9)	0.0569 (10)	0.0318 (8)	0.0221 (7)	0.0149 (7)	0.0079 (7)
F4	0.0546 (10)	0.1007 (14)	0.0528 (10)	−0.0322 (10)	0.0381 (9)	−0.0135 (9)
F5	0.0544 (10)	0.0349 (9)	0.1155 (16)	−0.0146 (8)	0.0357 (11)	0.0160 (9)
F6	0.0337 (8)	0.0657 (11)	0.0449 (9)	−0.0190 (7)	0.0105 (7)	0.0062 (8)
F10	0.0632 (10)	0.0234 (7)	0.0480 (9)	0.0094 (7)	0.0220 (8)	0.0000 (6)
F11	0.0391 (9)	0.0390 (9)	0.0491 (9)	0.0009 (7)	−0.0108 (7)	0.0055 (7)
F12	0.0595 (10)	0.0430 (9)	0.0576 (10)	0.0171 (7)	0.0360 (8)	0.0254 (7)
F13	0.0288 (7)	0.0461 (9)	0.0550 (9)	−0.0129 (6)	0.0153 (7)	−0.0047 (7)
F14	0.0290 (7)	0.0378 (8)	0.0402 (8)	0.0058 (6)	0.0077 (6)	−0.0012 (6)
F15	0.0330 (8)	0.0726 (11)	0.0245 (7)	0.0039 (7)	0.0029 (6)	−0.0126 (7)
F19	0.0449 (9)	0.0591 (10)	0.0325 (8)	−0.0212 (8)	0.0082 (7)	−0.0156 (7)
F20	0.0818 (12)	0.0504 (10)	0.0300 (8)	0.0155 (9)	−0.0065 (8)	0.0039 (7)
F21	0.0561 (10)	0.0880 (13)	0.0281 (7)	−0.0215 (9)	0.0221 (7)	−0.0141 (8)
F22	0.0393 (8)	0.0531 (9)	0.0333 (7)	−0.0058 (7)	0.0143 (6)	0.0144 (7)
F23	0.0696 (11)	0.0312 (8)	0.0549 (9)	−0.0185 (7)	0.0354 (8)	−0.0028 (7)
F24	0.0502 (9)	0.0524 (9)	0.0659 (10)	0.0230 (8)	0.0448 (8)	0.0260 (8)
N1	0.0216 (9)	0.0207 (9)	0.0201 (9)	−0.0012 (7)	0.0064 (7)	0.0005 (7)
N2	0.0224 (9)	0.0213 (9)	0.0202 (9)	−0.0041 (7)	0.0061 (7)	0.0003 (7)
C1	0.0210 (10)	0.0185 (10)	0.0231 (11)	0.0029 (8)	0.0070 (9)	0.0003 (8)
C2	0.0288 (12)	0.0262 (12)	0.0228 (11)	−0.0052 (9)	0.0078 (9)	−0.0034 (9)
C3	0.0264 (11)	0.0291 (12)	0.0218 (11)	−0.0070 (9)	0.0061 (9)	−0.0016 (9)
C4	0.0224 (11)	0.0266 (11)	0.0196 (10)	−0.0074 (9)	0.0068 (9)	0.0004 (8)
C5	0.0264 (11)	0.0242 (11)	0.0241 (11)	−0.0069 (9)	0.0077 (9)	−0.0014 (9)
C6	0.0353 (13)	0.0272 (12)	0.0253 (11)	−0.0045 (10)	0.0093 (10)	0.0037 (9)
C7	0.0353 (13)	0.0363 (13)	0.0229 (11)	−0.0113 (10)	0.0126 (10)	0.0006 (10)
C8	0.0296 (12)	0.0358 (13)	0.0286 (12)	−0.0073 (10)	0.0137 (10)	−0.0054 (10)
C9	0.0225 (11)	0.0273 (12)	0.0251 (11)	−0.0069 (9)	0.0074 (9)	−0.0021 (9)
C10	0.0290 (12)	0.0307 (12)	0.0305 (12)	0.0018 (10)	0.0123 (10)	0.0011 (10)
C11	0.0399 (14)	0.0297 (13)	0.0384 (14)	0.0023 (11)	0.0124 (11)	−0.0016 (10)
C12	0.0302 (13)	0.0440 (15)	0.0480 (15)	0.0028 (11)	0.0110 (12)	0.0026 (12)
C13	0.0363 (13)	0.0264 (12)	0.0274 (12)	0.0007 (10)	0.0112 (10)	0.0032 (9)
C14	0.0324 (13)	0.0399 (15)	0.0492 (15)	0.0057 (11)	0.0142 (12)	0.0022 (12)
C15	0.0691 (19)	0.0267 (13)	0.0488 (16)	0.0030 (13)	0.0305 (15)	0.0038 (11)
C16	0.0262 (11)	0.0220 (11)	0.0179 (10)	−0.0025 (9)	0.0077 (9)	0.0009 (8)
C17	0.0287 (12)	0.0231 (11)	0.0194 (10)	0.0014 (9)	0.0067 (9)	−0.0009 (8)
C18	0.0439 (14)	0.0206 (11)	0.0266 (11)	0.0033 (10)	0.0131 (11)	0.0033 (9)
C19	0.0500 (15)	0.0257 (12)	0.0292 (12)	−0.0057 (11)	0.0215 (11)	0.0017 (9)
C20	0.0336 (13)	0.0325 (13)	0.0312 (12)	−0.0034 (10)	0.0191 (10)	−0.0011 (10)
C21	0.0276 (11)	0.0271 (12)	0.0210 (10)	0.0009 (9)	0.0107 (9)	0.0007 (9)
C22	0.0326 (12)	0.0246 (12)	0.0345 (12)	0.0067 (10)	0.0139 (10)	0.0032 (9)
C23	0.0353 (14)	0.0463 (16)	0.0400 (14)	0.0102 (12)	0.0077 (12)	0.0013 (12)
C24	0.0382 (14)	0.0502 (16)	0.0384 (14)	0.0125 (12)	0.0145 (12)	−0.0052 (12)
C25	0.0328 (12)	0.0318 (13)	0.0349 (12)	0.0071 (10)	0.0187 (11)	0.0084 (10)
C26	0.0375 (15)	0.0547 (18)	0.0590 (18)	0.0144 (13)	0.0109 (14)	0.0113 (15)
C27	0.0641 (18)	0.0307 (14)	0.0510 (16)	0.0119 (13)	0.0375 (15)	0.0066 (12)
C28	0.0192 (10)	0.0233 (11)	0.0194 (10)	−0.0035 (8)	0.0066 (8)	−0.0028 (8)
C29	0.0214 (11)	0.0242 (11)	0.0236 (11)	−0.0007 (9)	0.0085 (9)	−0.0014 (9)
C30	0.0232 (11)	0.0271 (12)	0.0244 (11)	−0.0016 (9)	0.0101 (9)	−0.0039 (9)
C31	0.0233 (11)	0.0257 (12)	0.0318 (12)	−0.0004 (9)	0.0119 (10)	−0.0075 (9)
C32	0.0207 (11)	0.0214 (11)	0.0256 (11)	−0.0030 (8)	0.0065 (9)	−0.0024 (8)
C33	0.0219 (10)	0.0232 (11)	0.0231 (10)	−0.0048 (8)	0.0098 (9)	−0.0018 (8)
C34	0.0395 (14)	0.0370 (14)	0.0373 (13)	0.0063 (11)	0.0231 (12)	0.0004 (11)
C35	0.0292 (12)	0.0267 (12)	0.0317 (12)	0.0024 (9)	0.0100 (10)	−0.0010 (10)
C36	0.0253 (11)	0.0221 (11)	0.0191 (10)	−0.0019 (8)	0.0118 (9)	−0.0028 (8)
C37	0.0247 (11)	0.0271 (12)	0.0226 (10)	−0.0011 (9)	0.0105 (9)	−0.0012 (9)
C38	0.0309 (12)	0.0259 (12)	0.0271 (11)	−0.0072 (9)	0.0145 (10)	−0.0025 (9)
C39	0.0373 (13)	0.0209 (11)	0.0251 (11)	−0.0007 (9)	0.0159 (10)	−0.0001 (9)
C40	0.0304 (12)	0.0223 (11)	0.0219 (10)	0.0002 (9)	0.0132 (9)	−0.0023 (8)
C41	0.0247 (11)	0.0231 (11)	0.0242 (10)	−0.0019 (9)	0.0137 (9)	−0.0029 (8)
C42	0.0341 (13)	0.0235 (12)	0.0338 (13)	0.0042 (10)	0.0167 (11)	0.0006 (9)
C43	0.0362 (14)	0.0363 (14)	0.0369 (13)	−0.0082 (11)	0.0157 (12)	0.0017 (11)
C44	0.0225 (10)	0.0192 (10)	0.0222 (10)	0.0037 (8)	0.0115 (9)	0.0001 (8)
C45	0.0263 (11)	0.0214 (11)	0.0256 (11)	0.0013 (9)	0.0140 (9)	0.0008 (8)
C46	0.0249 (11)	0.0233 (11)	0.0244 (11)	0.0026 (9)	0.0092 (9)	−0.0028 (9)
C47	0.0216 (11)	0.0216 (11)	0.0309 (12)	−0.0003 (9)	0.0103 (9)	−0.0027 (9)
C48	0.0229 (11)	0.0177 (10)	0.0290 (11)	0.0035 (8)	0.0131 (9)	0.0009 (8)
C49	0.0224 (10)	0.0220 (11)	0.0213 (10)	0.0038 (8)	0.0096 (9)	−0.0014 (8)
C50	0.0372 (13)	0.0352 (13)	0.0271 (12)	−0.0042 (11)	0.0089 (11)	−0.0037 (10)
C51	0.0259 (12)	0.0230 (11)	0.0334 (12)	0.0007 (9)	0.0152 (10)	0.0015 (9)
C52	0.0248 (11)	0.0172 (10)	0.0228 (10)	−0.0021 (8)	0.0109 (9)	0.0018 (8)
C53	0.0209 (10)	0.0244 (11)	0.0239 (10)	−0.0009 (8)	0.0088 (9)	0.0005 (8)
C54	0.0280 (11)	0.0222 (11)	0.0270 (11)	−0.0015 (9)	0.0148 (9)	−0.0002 (9)
C55	0.0310 (12)	0.0240 (11)	0.0232 (11)	−0.0033 (9)	0.0126 (10)	−0.0038 (9)
C56	0.0250 (11)	0.0200 (11)	0.0244 (11)	−0.0027 (8)	0.0104 (9)	−0.0004 (8)
C57	0.0231 (11)	0.0204 (11)	0.0255 (11)	−0.0019 (8)	0.0125 (9)	0.0007 (8)
C59	0.0274 (12)	0.0338 (13)	0.0284 (12)	−0.0036 (10)	0.0107 (10)	−0.0062 (10)
B1	0.0208 (12)	0.0223 (12)	0.0199 (11)	0.0010 (9)	0.0085 (10)	0.0010 (9)
C58	0.0317 (13)	0.0377 (14)	0.0305 (12)	0.0009 (10)	0.0136 (10)	−0.0048 (10)
F16A	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F17A	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F18A	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F16B	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F17B	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F18B	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F16C	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F17C	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F18C	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F16D	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F17D	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F18D	0.0396 (8)	0.0351 (10)	0.0406 (8)	0.0062 (7)	0.0239 (7)	−0.0056 (7)
F7A	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F8A	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F9A	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F7B	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F8B	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F9B	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F7C	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F8C	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F9C	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F7D	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F8D	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)
F9D	0.0448 (8)	0.0450 (9)	0.0241 (9)	0.0091 (6)	0.0230 (7)	0.0062 (6)

Geometric parameters (Å, º) top

Cl1—C1	1.681 (2)	C30—C34	1.486 (3)
F1—C42	1.334 (3)	C31—C32	1.391 (3)
F2—C42	1.327 (3)	C32—C33	1.385 (3)
F3—C42	1.337 (3)	C32—C35	1.493 (3)
F4—C43	1.327 (3)	C34—F8C	1.346 (3)
F5—C43	1.341 (3)	C34—F8A	1.347 (3)
F6—C43	1.328 (3)	C34—F8D	1.347 (3)
F10—C35	1.339 (3)	C34—F8B	1.347 (3)
F11—C35	1.334 (3)	C34—F7B	1.353 (3)
F12—C35	1.336 (3)	C34—F7A	1.354 (3)
F13—C59	1.349 (3)	C34—F7C	1.354 (3)
F14—C59	1.342 (3)	C34—F7D	1.354 (3)
F15—C59	1.337 (3)	C34—F9B	1.372 (3)
F19—C50	1.337 (3)	C34—F9D	1.373 (3)
F20—C50	1.347 (3)	C34—F9C	1.373 (3)
F21—C50	1.329 (3)	C34—F9A	1.374 (3)
F22—C51	1.336 (3)	C36—C41	1.398 (3)
F23—C51	1.335 (3)	C36—C37	1.399 (3)
F24—C51	1.337 (3)	C36—B1	1.640 (3)
N1—C1	1.315 (3)	C37—C38	1.392 (3)
N1—C16	1.442 (3)	C38—C39	1.383 (3)
N1—C2	1.479 (3)	C38—C43	1.494 (3)
N2—C1	1.311 (3)	C39—C40	1.383 (3)
N2—C4	1.448 (3)	C40—C41	1.391 (3)
N2—C3	1.486 (3)	C40—C42	1.497 (3)
C2—C3	1.531 (3)	C44—C49	1.397 (3)
C4—C9	1.399 (3)	C44—C45	1.397 (3)
C4—C5	1.400 (3)	C44—B1	1.643 (3)
C5—C6	1.391 (3)	C45—C46	1.392 (3)
C5—C13	1.521 (3)	C46—C47	1.383 (3)
C6—C7	1.379 (3)	C46—C50	1.489 (3)
C7—C8	1.380 (3)	C47—C48	1.386 (3)
C8—C9	1.390 (3)	C48—C49	1.392 (3)
C9—C10	1.524 (3)	C48—C51	1.495 (3)
C10—C11	1.531 (3)	C52—C57	1.392 (3)
C10—C12	1.532 (3)	C52—C53	1.406 (3)
C13—C15	1.527 (3)	C52—B1	1.646 (3)
C13—C14	1.533 (3)	C53—C54	1.393 (3)
C16—C21	1.398 (3)	C54—C55	1.386 (3)
C16—C17	1.399 (3)	C54—C58	1.494 (3)
C17—C18	1.391 (3)	C55—C56	1.380 (3)
C17—C22	1.524 (3)	C56—C57	1.396 (3)
C18—C19	1.380 (3)	C56—C59	1.491 (3)
C19—C20	1.378 (3)	C58—F17A	1.343 (3)
C20—C21	1.397 (3)	C58—F17C	1.343 (3)
C21—C25	1.517 (3)	C58—F17B	1.343 (3)
C22—C23	1.522 (3)	C58—F17D	1.343 (3)
C22—C24	1.535 (3)	C58—F18D	1.355 (3)
C25—C27	1.529 (3)	C58—F18A	1.356 (3)
C25—C26	1.530 (4)	C58—F18C	1.356 (3)
C28—C29	1.400 (3)	C58—F18B	1.356 (3)
C28—C33	1.402 (3)	C58—F16B	1.363 (3)
C28—B1	1.638 (3)	C58—F16D	1.363 (3)
C29—C30	1.390 (3)	C58—F16C	1.364 (3)
C30—C31	1.385 (3)	C58—F16A	1.364 (3)

C1—N1—C16	127.50 (17)	C39—C38—C37	120.4 (2)
C1—N1—C2	108.78 (17)	C39—C38—C43	119.9 (2)
C16—N1—C2	123.64 (16)	C37—C38—C43	119.6 (2)
C1—N2—C4	127.33 (17)	C40—C39—C38	118.7 (2)
C1—N2—C3	108.32 (16)	C39—C40—C41	120.5 (2)
C4—N2—C3	121.63 (16)	C39—C40—C42	118.38 (19)
N2—C1—N1	114.83 (18)	C41—C40—C42	121.1 (2)
N2—C1—Cl1	122.96 (16)	C40—C41—C36	122.1 (2)
N1—C1—Cl1	122.21 (16)	F2—C42—F1	106.87 (19)
N1—C2—C3	102.43 (16)	F2—C42—F3	105.79 (19)
N2—C3—C2	102.55 (16)	F1—C42—F3	105.11 (18)
C9—C4—C5	123.8 (2)	F2—C42—C40	113.68 (18)
C9—C4—N2	118.65 (19)	F1—C42—C40	112.25 (19)
C5—C4—N2	117.44 (19)	F3—C42—C40	112.51 (18)
C6—C5—C4	116.6 (2)	F4—C43—F6	106.8 (2)
C6—C5—C13	121.7 (2)	F4—C43—F5	106.0 (2)
C4—C5—C13	121.67 (19)	F6—C43—F5	105.6 (2)
C7—C6—C5	121.1 (2)	F4—C43—C38	112.2 (2)
C6—C7—C8	120.8 (2)	F6—C43—C38	113.39 (19)
C7—C8—C9	121.0 (2)	F5—C43—C38	112.3 (2)
C8—C9—C4	116.8 (2)	C49—C44—C45	115.90 (19)
C8—C9—C10	119.3 (2)	C49—C44—B1	123.66 (17)
C4—C9—C10	123.96 (19)	C45—C44—B1	120.16 (18)
C9—C10—C11	111.30 (18)	C46—C45—C44	122.49 (19)
C9—C10—C12	111.1 (2)	C47—C46—C45	120.54 (19)
C11—C10—C12	110.6 (2)	C47—C46—C50	120.6 (2)
C5—C13—C15	113.4 (2)	C45—C46—C50	118.8 (2)
C5—C13—C14	110.42 (19)	C46—C47—C48	118.09 (19)
C15—C13—C14	110.0 (2)	C47—C48—C49	121.08 (19)
C21—C16—C17	123.61 (19)	C47—C48—C51	118.68 (19)
C21—C16—N1	118.76 (18)	C49—C48—C51	120.18 (18)
C17—C16—N1	117.60 (19)	C48—C49—C44	121.89 (19)
C18—C17—C16	116.9 (2)	F21—C50—F19	105.88 (19)
C18—C17—C22	120.4 (2)	F21—C50—F20	106.4 (2)
C16—C17—C22	122.61 (19)	F19—C50—F20	105.0 (2)
C19—C18—C17	121.1 (2)	F21—C50—C46	113.6 (2)
C20—C19—C18	120.6 (2)	F19—C50—C46	113.8 (2)
C19—C20—C21	121.2 (2)	F20—C50—C46	111.48 (19)
C20—C21—C16	116.6 (2)	F23—C51—F22	105.73 (17)
C20—C21—C25	120.4 (2)	F23—C51—F24	106.28 (18)
C16—C21—C25	123.01 (19)	F22—C51—F24	106.02 (18)
C23—C22—C17	113.0 (2)	F23—C51—C48	112.81 (18)
C23—C22—C24	110.9 (2)	F22—C51—C48	113.24 (17)
C17—C22—C24	110.26 (19)	F24—C51—C48	112.18 (17)
C21—C25—C27	110.75 (19)	C57—C52—C53	115.63 (19)
C21—C25—C26	111.4 (2)	C57—C52—B1	123.57 (18)
C27—C25—C26	111.1 (2)	C53—C52—B1	120.50 (18)
C29—C28—C33	115.55 (19)	C54—C53—C52	122.39 (19)
C29—C28—B1	122.78 (18)	C55—C54—C53	120.5 (2)
C33—C28—B1	121.23 (18)	C55—C54—C58	119.43 (19)
C30—C29—C28	122.4 (2)	C53—C54—C58	120.02 (19)
C31—C30—C29	120.7 (2)	C56—C55—C54	118.17 (19)
C31—C30—C34	120.2 (2)	C55—C56—C57	121.10 (19)
C29—C30—C34	119.0 (2)	C55—C56—C59	120.39 (19)
C30—C31—C32	118.2 (2)	C57—C56—C59	118.50 (19)
C33—C32—C31	120.6 (2)	C52—C57—C56	122.2 (2)
C33—C32—C35	120.2 (2)	F15—C59—F14	106.54 (18)
C31—C32—C35	119.1 (2)	F15—C59—F13	105.96 (18)
C32—C33—C28	122.5 (2)	F14—C59—F13	104.88 (18)
F8B—C34—F7B	103.9 (5)	F15—C59—C56	113.22 (19)
F8A—C34—F7A	109.7 (4)	F14—C59—C56	112.99 (18)
F8C—C34—F7C	102.1 (7)	F13—C59—C56	112.58 (19)
F8D—C34—F7D	95.3 (12)	C28—B1—C36	111.67 (17)
F8B—C34—F9B	113.8 (5)	C28—B1—C44	103.48 (16)
F7B—C34—F9B	108.1 (3)	C36—B1—C44	111.86 (16)
F8D—C34—F9D	115.6 (13)	C28—B1—C52	113.14 (16)
F7D—C34—F9D	96.9 (12)	C36—B1—C52	104.19 (16)
F8C—C34—F9C	105.0 (5)	C44—B1—C52	112.77 (17)
F7C—C34—F9C	105.2 (8)	F17D—C58—F18D	100.2 (9)
F8A—C34—F9A	98.6 (5)	F17A—C58—F18A	106.0 (3)
F7A—C34—F9A	101.7 (4)	F17C—C58—F18C	103.6 (8)
F11—C35—F12	106.67 (19)	F17B—C58—F18B	107.2 (4)
F11—C35—F10	105.42 (18)	F17B—C58—F16B	109.1 (3)
F12—C35—F10	106.10 (19)	F18B—C58—F16B	105.7 (4)
F11—C35—C32	112.32 (19)	F17D—C58—F16D	106.2 (9)
F12—C35—C32	112.96 (19)	F18D—C58—F16D	111.7 (9)
F10—C35—C32	112.80 (18)	F17C—C58—F16C	109.5 (8)
C41—C36—C37	116.00 (19)	F18C—C58—F16C	98.7 (8)
C41—C36—B1	123.41 (18)	F17A—C58—F16A	106.8 (3)
C37—C36—B1	120.42 (18)	F18A—C58—F16A	104.3 (3)
C38—C37—C36	122.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, y−1/2, −z+1/2; (ii) x−1/2, −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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