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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 7| Part 11| November 2022| x221049
https://doi.org/10.1107/S2414314622010495

2,5,8,11-Tetra­methyl-2,5,8,11-tetra­aza­do­decane-2,11-diium bis­­[hy­dr­oxy­tris­­(penta­fluoro­phen­yl)borate] benzene 2.5-solvate

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Ray J. Butchera* and Andrew P. Purdyb

aDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, and bChemistry Division, Code 6123, Naval Research Laboratory, 4555 Overlook Av, SW, Washington DC 20375-5342, USA
*Correspondence e-mail: rbutcher99@yahoo.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 26 October 2022; accepted 31 October 2022; online 4 November 2022)

The title compound of overall stoichiometry, C12H32N42+·2C18HBF15O−·2.5C6H6, crystallizes in the triclinic space group P[\overline{1}] and the stoichiometry of the asymmetric unit consists of two [C12H32N4]2+ dications, two [C18HBF15O]− anions, and 2.5 mol­ecules of benzene as solvate. The dications are both at half occupancy and located on a center of inversion, as is one of the benzene solvate mol­ecules. In the two anions the O—H groups participate in different hydrogen-bonding schemes. In anion A, the OH group participates in a bifurcated 2R22(6) scheme with F atoms on different rings of an adjacent hy­droxy[tris­(penta­fluoro­phen­yl)]borate moiety with an additional N—H⋯O hydrogen bond with a dication. For anion B, the OH group participates in a single O—H⋯F R22(6) scheme. In addition, there are both O—H⋯N and N—H⋯O hydrogen bonds involving dication D and anion B in an R22(7) motif. There are numerous C—H⋯π inter­actions between the dications and all the three benzene solvate mol­ecules. For solvate 3, the C—H⋯π inter­actions are on both sides of the benzene ring and link both dications and solvate into a linear chain in the c-axis direction.

CCDC reference: 2216677

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound crystallizes in the triclinic space group P[\overline{1}] and the stoichiometry of the asymmetric unit consists of two half [C12H32N4]2+ dications, two [C18HBF15O]− anions, and 2.5 mol­ecules of benzene as solvate (see Fig. 1[link]). Both dications are located on a center of inversion, as is one of the benzene solvate mol­ecules. Tris(penta­fluoro­phen­yl)borane is a well-known strong Lewis acid and is used extensively to promote the formation of highly active cationic catalysts for olefin polymerization (Chen & Marks, 2000[Chen, E. Y. X. & Marks, T. J. (2000). Chem. Rev. 100, 1391-1434.]) as well as a Lewis acid partner for making frustrated Lewis pairs (FLPs) (Berkefeld et al., 2010[Berkefeld, A., Piers, W. E. & Parvez, M. (2010). J. Am. Chem. Soc. 132, 10660-10661.]). As a strong Lewis acid, it readily forms salts with bases such as amines. A search of the Cambridge Structural Database (CSD version 5.41, November 2019; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for structures containing amine salts of hy­droxy[tris(penta­fluoro­phen­yl)]borate gave 13 hits [DOJSAX (Peters et al., 2008[Peters, A., Wild, U., Hübner, O., Kaifer, E. & Himmel, H.-J. (2008). Chem. Eur. J. 14, 7813-7821.]); GIZZIZ (Focante, Mercandelli et al., 2006[Focante, F., Mercandelli, P., Sironi, A. & Resconi, L. (2006). Coord. Chem. Rev. 250, 170-188.]); ITULOA (Tao et al., 2016[Tao, X., Kehr, G., Wang, X., Daniliuc, C. G., Grimme, S. & Erker, G. (2016). Chem. Eur. J. 22, 9504-9507.]); KERLUO (Duchateau et al., 2000[Duchateau, R., van Santen, R. A. & Yap, G. P. A. (2000). Organometallics, 19, 809-816.]); MUQMUG (Drewitt et al., 2002[Drewitt, M. J., Niedermann, M. & Baird, M. C. (2002). Inorg. Chim. Acta, 340, 207-210.]); OFAFUZ (Schneider et al., 2018[Schneider, C., LaFortune, J. H. W., Melen, R. L. & Stephan, D. W. (2018). Dalton Trans. 47, 12742-12749.]); OZUBUH (Kelsen et al., 2011[Kelsen, V., Vallée, C., Jeanneau, E., Bibal, C., Santini, C. C., Chauvin, Y. & Olivier-Bourbigou, H. (2011). Organometallics, 30, 4284-4291.]); PEGCUA (Focante, Camurati et al., 2006[Focante, F., Camurati, I., Resconi, L., Guidotti, S., Beringhelli, T., D'Alfonso, G., Donghi, D., Maggioni, D., Mercandelli, P. & Sironi, A. (2006). Inorg. Chem. 45, 1683-1692.]); QIMKUS (Stibrany & Brant, 2001[Stibrany, R. T. & Brant, P. (2001). Acta Cryst. C57, 644-645.]); RAQWAI (Saverio et al., 2005[Di Saverio, A., Focante, F., Camurati, I., Resconi, L., Beringhelli, T., D'Alfonso, G., Donghi, D., Maggioni, D., Mercandelli, P. & Sironi, A. (2005). Inorg. Chem. 44, 5030-5041.]); SEFDIR (Hewavitharanage et al., 2005[Hewavitharanage, P., Danilov, E. O. & Neckers, D. C. (2005). J. Org. Chem. 70, 10653-10659.]); UXIJIW, UXIJUI (Thakur et al., 2016[Thakur, A., Vardhanapu, P. K., Vijaykumar, G. & Bhatta, S. R. (2016). J. Chem. Sci. 128, 613-620.])]. However, there were no hits for the dication.

[Figure 1]
Figure 1
Diagram showing the structure of the [C12H32N4]2+ dication (C) and two [C18HBF15O]+ anions (A). Only symmetry-independent atoms are labelled. Benzene solvate mol­ecules are omitted for clarity. Hydrogen bonds are shown with dashed lines. Atomic displacement parameters are at the 30% probability level.

In the present structure, the metrical parameters of both the 2-[(2-{[2-(di­methyl­ammonio)­eth­yl]amino}­eth­yl)amino]-N,N,N-tri­methyl­ethan-1-aminium dications and hy­droxy[tris­(penta­fluoro­phen­yl)]borate anions are in their usual ranges. The B—O distances for the two anions are 1.484 (5) and 1.487 (5) Å, which are in the normal range observed. In the two anions, the O—H groups participate in different hydrogen-bonding schemes (Table 1[link]). In anion A, the OH group participates in a bifurcated R22(6) (Etter et al., 1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]) scheme with F atoms on different rings of an adjacent hy­droxy[tris­(penta­fluoro­phen­yl)]borate moiety with an additional N—H⋯O hydrogen bond with a dication (see Fig. 1[link]). For anion B, the OH group participates in a single O—H⋯F R22(6) scheme (see Fig. 2[link]). In addition, there are both O—H⋯N and N—H⋯O hydrogen bonds involving cation D and anion B in a R22(7) motif.

Table 1
Hydrogen-bond geometry (Å, °)

Cg4, Cg7–Cg9 are the centroids of the C1B–C6B, C11S–C16S, C21S–C26S and C31S–C33S/C31S′–C31S′ rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1A—H1A⋯F8A 0.84 2.16 2.731 (3) 125
O1B—H1B⋯N1D 0.84 2.12 2.846 (4) 144
N2C—H2C⋯O1A 1.05 (4) 1.60 (4) 2.632 (4) 169 (3)
N2D—H2D⋯O1B 0.80 (4) 1.76 (4) 2.554 (5) 171 (4)
C2C—H2CB⋯F8Ai 0.99 2.46 3.435 (5) 168
C4C—H4CA⋯F6Aii 0.99 2.40 3.191 (5) 137
C5D—H5DC⋯F14B 0.98 2.54 3.284 (5) 133
C32S—H32A⋯F10Biii 0.95 2.52 3.133 (5) 123
C14S—H14A⋯Cg4iv 0.95 2.95 3.779 (5) 147
C4D—H4DA⋯Cg7 0.99 2.73 3.620 (4) 150
C6C—H6CB⋯Cg9 0.98 2.74 3.689 (4) 163
C6C—H6CB⋯Cg9v 0.98 2.74 3.689 (4) 163
Symmetry codes: (i) [-x+2, -y+2, -z]; (ii) x+1, y, z; (iii) x, y+1, z; (iv) [x-1, y, z]; (v) [-x+2, -y+2, -z+1].
[Figure 2]
Figure 2
Diagram showing the structure of the [C12H32N4]2+ dication (D) and two [C18HBF15O]+ anions (B). Only symmetry-independent atoms are labelled. Benzene solvate mol­ecules are omitted for clarity. Hydrogen bonds are shown with dashed lines. Atomic displacement parameters are at the 30% probability level.

While this structure contains numerous phenyl rings, there does not appear to be any π–π stacking. The closest is for the ring C7A–C12A with itself (symmetry code 1 − x, 2 − y, −z) where the CgI_Perp distance is 2.8921 (15) Å but the slippage is 4.685 Å so there appears to be no stacking. However, there are numerous C—H⋯π inter­actions between the cations and all the three benzene solvate mol­ecules (see Fig. 3[link]). For solvate 3, the C—H⋯π inter­actions are on both sides of the benzene ring and link both cation and solvate into a linear chain in the c-axis direction (see Fig. 4[link]). The packing is shown in Fig. 5[link].

[Figure 3]
Figure 3
Diagram showing the numerous C—H⋯π inter­actions between the [C12H32N4]2+ dications and all the three benzene solvate mol­ecules, also including the [C18HBF15O]− anions.
[Figure 4]
Figure 4
Diagram showing how the C—H⋯π inter­actions between the third benzene solvate mol­ecule and cation C.
[Figure 5]
Figure 5
Packing diagram of the title compound.

Synthesis and crystallization

In a reaction bulb, hexa­methyl­tri­ethyl­ene­tetra­mine (0.050 g, 0.22 mmol) was mixed with tris­(penta­fluoro­phen­yl)borane (0.44 g, 0.86 mmol) in ∼10 mL dry toluene in an argon-filled drybox. A yellowish brown mixture with two liquid phases resulted. On a vacuum line, the mixture was frozen and 1.72 mmol CO2 was condensed in. After a day, solids began to form and the reaction was continued for several weeks. Some of the solids were flame sealed in an NMR tube with C6D6, but it was not soluble enough to obtain a spectrum. When the NMR tube was opened, crystals of the title compound were isolated. The oxygen atom must have come from the CO2 and the proton must have come from either the toluene or the amine.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C12H32N42+·2C18HBF15O−·2.5C6H6
Mr 1485.68
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 10.4436 (5), 17.3961 (9), 17.8229 (9)
α, β, γ (°) 79.729 (3), 77.923 (3), 83.103 (3)
V (Å3) 3104.1 (3)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.16
Crystal size (mm) 0.28 × 0.10 × 0.08
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.591, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 29409, 11027, 6339
Rint 0.097
(sin θ/λ)max (Å−1) 0.600
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.132, 1.00
No. of reflections 11027
No. of parameters 922
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.30, −0.39
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and SHELXTL (Sheldrick 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data

CCDC reference: 2216677

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622010495/bt4128sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622010495/bt4128Isup2.hkl

checkCIF report


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

2,5,8,11-Tetramethyl-2,5,8,11-tetraazadodecane-2,11-diium bis[hydroxytris(pentafluorophenyl)borate] benzene 2.5-solvate top
Crystal data top
C12H32N42+·2C18HBF15O−·2.5C6H6Z = 2
Mr = 1485.68F(000) = 1502
Triclinic, P1Dx = 1.590 Mg m−3
a = 10.4436 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.3961 (9) ÅCell parameters from 5245 reflections
c = 17.8229 (9) Åθ = 2.8–28.3°
α = 79.729 (3)°µ = 0.16 mm−1
β = 77.923 (3)°T = 100 K
γ = 83.103 (3)°Needle, colourless
V = 3104.1 (3) Å30.28 × 0.10 × 0.08 mm
Data collection top
Bruker APEXII CCD
diffractometer		6339 reflections with I > 2σ(I)
φ and ω scansRint = 0.097
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		θmax = 25.3°, θmin = 2.5°
Tmin = 0.591, Tmax = 0.746h = −12→12
29409 measured reflectionsk = −20→20
11027 independent reflectionsl = −21→21
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0515P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
11027 reflectionsΔρmax = 0.30 e Å−3
922 parametersΔρmin = −0.39 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.

Refinement. The structure was solved using SHELXT (Sheldrick, 2015a) and refined with SHELXL2018/3 (Sheldrick, 2015b). All hydrogen atoms were located in difference Fourier maps and the coordinates of those attached to N were refined with Uiso(H) = 1.2Ueq(N). For H atoms bonded to O the H—O—B—C torsion angles were refined with Uiso(H) = 1.2Ueq(O). Those attached to carbons were refined in idealized geometry using a riding model with with atomic displacement parameters of Uiso(H) = 1.2Ueq(C) [for CH3, 1.5Ueq(C)] with C—H distances of 0.95 to 0.99 Å

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F2A0.7105 (2)1.11156 (12)0.17203 (14)0.0324 (6)
F2B0.5387 (2)0.62060 (14)0.75957 (12)0.0414 (7)
F3A0.5993 (2)1.25327 (12)0.13367 (13)0.0291 (5)
F3B0.5888 (3)0.76050 (14)0.67718 (13)0.0449 (7)
F4A0.3319 (2)1.28043 (12)0.15297 (13)0.0330 (6)
F4B0.7778 (2)0.77305 (13)0.54644 (14)0.0405 (6)
F5A0.1813 (2)1.15904 (12)0.21360 (14)0.0357 (6)
F5B0.9170 (3)0.64057 (14)0.50088 (15)0.0538 (8)
F6A0.2911 (2)1.01481 (11)0.25229 (12)0.0244 (5)
F6B0.8696 (2)0.50149 (13)0.58037 (14)0.0438 (7)
F8A0.6442 (2)0.97021 (12)0.05773 (11)0.0238 (5)
F8B0.5578 (2)0.35383 (13)0.63917 (13)0.0316 (6)
F9A0.5476 (2)0.89899 (13)−0.03480 (11)0.0318 (6)
F9B0.7125 (2)0.24269 (12)0.57213 (12)0.0341 (6)
F10A0.3411 (2)0.80871 (13)0.02350 (13)0.0384 (6)
F10B0.9676 (2)0.21649 (12)0.58371 (14)0.0379 (6)
F11A0.2427 (2)0.78790 (13)0.17925 (13)0.0386 (6)
F11B1.0673 (2)0.30024 (14)0.67035 (14)0.0388 (6)
F12A0.3429 (2)0.85375 (12)0.27384 (12)0.0269 (5)
F12B0.9160 (2)0.41616 (13)0.73518 (13)0.0320 (6)
F14A0.6558 (2)0.80080 (12)0.27730 (11)0.0247 (5)
F14B0.4976 (2)0.35871 (13)0.84276 (13)0.0350 (6)
F15A0.6257 (2)0.72352 (12)0.42236 (12)0.0291 (5)
F15B0.4775 (2)0.33929 (14)0.99533 (13)0.0403 (6)
F16A0.4870 (2)0.79401 (13)0.54272 (12)0.0317 (6)
F16B0.6233 (3)0.42111 (14)1.05999 (12)0.0425 (7)
F17A0.3939 (2)0.94697 (13)0.51587 (11)0.0292 (6)
F17B0.7857 (3)0.52384 (13)0.96620 (13)0.0431 (7)
F18A0.4322 (2)1.02808 (12)0.37335 (11)0.0249 (5)
F18B0.8016 (2)0.54823 (13)0.81312 (12)0.0324 (6)
O1A0.7149 (2)0.95384 (14)0.19924 (13)0.0177 (6)
H1A0.7351660.9786920.1541030.021*
O1B0.5064 (3)0.4770 (2)0.71571 (16)0.0441 (8)
H1B0.5029300.4862100.6682440.053*
N1C0.9782 (3)1.03371 (19)0.09770 (17)0.0252 (8)
N1D0.3776 (3)0.52751 (17)0.58736 (17)0.0222 (8)
N2C0.8851 (3)0.98584 (18)0.27692 (19)0.0236 (8)
H2C0.821 (4)0.979 (2)0.241 (2)0.028*
N2D0.2596 (3)0.4640 (2)0.7571 (2)0.0286 (9)
H2D0.335 (4)0.473 (2)0.745 (2)0.034*
C1A0.5071 (4)1.0538 (2)0.21085 (19)0.0161 (8)
C1B0.7007 (4)0.5520 (2)0.6760 (2)0.0211 (9)
C1C0.9686 (5)1.1192 (2)0.0720 (2)0.0424 (12)
H1CA0.9140791.1323220.0321370.064*
H1CB0.9285821.1457170.1163990.064*
H1CC1.0566641.1362720.0502970.064*
C1D0.3899 (4)0.6127 (2)0.5776 (2)0.0285 (10)
H1DA0.3563950.6312340.6274210.043*
H1DB0.4825980.6227850.5598640.043*
H1DC0.3390310.6404050.5390670.043*
C2A0.5773 (4)1.1184 (2)0.1820 (2)0.0190 (9)
C2B0.6337 (4)0.6222 (3)0.6959 (2)0.0286 (10)
C2C1.0396 (4)0.9929 (3)0.0316 (2)0.0310 (10)
H2CA1.0501340.9358360.0505610.037*
H2CB1.1282121.0107680.0099300.037*
C2D0.4266 (3)0.4965 (2)0.5142 (2)0.0216 (9)
H2DA0.3786580.5255920.4739740.026*
H2DB0.4090500.4406800.5219060.026*
C3A0.5223 (4)1.1940 (2)0.1618 (2)0.0201 (9)
C3B0.6588 (4)0.6955 (2)0.6541 (2)0.0292 (10)
C3C1.0591 (4)1.0147 (3)0.1568 (2)0.0389 (12)
H3CA1.1402051.0422820.1384140.047*
H3CB1.0853360.9576500.1636510.047*
C3D0.2396 (4)0.5108 (2)0.6169 (2)0.0298 (10)
H3DA0.2299140.4564060.6110450.036*
H3DB0.1836390.5464040.5847780.036*
C4A0.3897 (4)1.2077 (2)0.1709 (2)0.0209 (9)
C4B0.7529 (4)0.7022 (2)0.5885 (2)0.0283 (10)
C4C0.9902 (4)1.0370 (3)0.2352 (2)0.0292 (10)
H4CA1.0563391.0343580.2682930.035*
H4CB0.9513381.0918780.2270260.035*
C4D0.1909 (4)0.5203 (2)0.7008 (2)0.0272 (10)
H4DA0.2019190.5744660.7067400.033*
H4DB0.0957280.5131500.7146180.033*
C5A0.3139 (4)1.1462 (2)0.2016 (2)0.0195 (9)
C5B0.8222 (4)0.6353 (2)0.5657 (2)0.0329 (11)
C5C0.9390 (5)0.9046 (3)0.3016 (3)0.0479 (13)
H5CA0.9746560.8794990.2556310.072*
H5CB0.8688910.8747950.3351600.072*
H5CC1.0090910.9058020.3301940.072*
C5D0.2446 (4)0.3805 (2)0.7559 (3)0.0389 (12)
H5DA0.2829300.3676350.7040790.058*
H5DB0.1510830.3716050.7684390.058*
H5DC0.2899570.3470290.7943720.058*
C6A0.3731 (4)1.0723 (2)0.2208 (2)0.0175 (8)
C6B0.7953 (4)0.5634 (2)0.6091 (2)0.0270 (10)
C6C0.8078 (4)1.0198 (3)0.3449 (2)0.0362 (11)
H6CA0.7664121.0715440.3271950.054*
H6CB0.8662891.0249510.3798520.054*
H6CC0.7397740.9852280.3726790.054*
C6D0.2130 (5)0.4841 (3)0.8370 (3)0.0516 (14)
H6DA0.2379180.5363740.8383030.077*
H6DB0.2533220.4453970.8742150.077*
H6DC0.1171270.4838520.8509910.077*
C7A0.5026 (3)0.9146 (2)0.17160 (19)0.0144 (8)
C7B0.7300 (4)0.3920 (2)0.6903 (2)0.0185 (9)
C8A0.5459 (4)0.9237 (2)0.0917 (2)0.0178 (9)
C8B0.6841 (4)0.3441 (2)0.6493 (2)0.0226 (9)
C9A0.4964 (4)0.8883 (2)0.0418 (2)0.0218 (9)
C9B0.7614 (4)0.2858 (2)0.6137 (2)0.0256 (10)
C10A0.3933 (4)0.8429 (2)0.0713 (2)0.0240 (9)
C10B0.8899 (4)0.2720 (2)0.6202 (2)0.0255 (10)
C11A0.3446 (4)0.8325 (2)0.1497 (2)0.0233 (9)
C11B0.9399 (4)0.3145 (2)0.6636 (2)0.0266 (10)
C11S0.2153 (5)0.7509 (2)0.7240 (3)0.0428 (13)
H11A0.2974170.7691950.7239670.051*
C12A0.3994 (4)0.8671 (2)0.1976 (2)0.0198 (9)
C12B0.8586 (4)0.3721 (2)0.6971 (2)0.0221 (9)
C12S0.1699 (4)0.7591 (2)0.6553 (3)0.0378 (11)
H12A0.2190790.7843270.6082140.045*
C13A0.5449 (3)0.9188 (2)0.3166 (2)0.0157 (8)
C13B0.6458 (4)0.4561 (2)0.8193 (2)0.0215 (9)
C13S0.0512 (4)0.7299 (2)0.6560 (3)0.0372 (11)
H13A0.0194260.7343480.6090730.045*
C14A0.5924 (4)0.8407 (2)0.3351 (2)0.0176 (8)
C14B0.5693 (4)0.4032 (2)0.8704 (2)0.0238 (9)
C14S−0.0198 (4)0.6948 (2)0.7243 (3)0.0337 (11)
H14A−0.1008960.6750210.7246180.040*
C15A0.5772 (4)0.7994 (2)0.4091 (2)0.0199 (9)
C15B0.5596 (4)0.3908 (2)0.9500 (2)0.0271 (10)
C15S0.0255 (4)0.6878 (2)0.7925 (3)0.0380 (11)
H15A−0.0239300.6632230.8398350.046*
C16A0.5090 (4)0.8345 (2)0.4701 (2)0.0212 (9)
C16B0.6309 (4)0.4318 (2)0.9827 (2)0.0279 (10)
C16S0.1428 (5)0.7166 (3)0.7920 (3)0.0426 (12)
H16A0.1734950.7126870.8391900.051*
C17A0.4607 (4)0.9114 (2)0.4561 (2)0.0198 (9)
C17B0.7123 (4)0.4842 (2)0.9345 (2)0.0273 (10)
C18A0.4806 (4)0.9515 (2)0.3808 (2)0.0180 (9)
C18B0.7181 (4)0.4955 (2)0.8556 (2)0.0238 (9)
C21S0.9916 (5)0.6712 (3)0.0254 (3)0.0466 (13)
H21A1.0438610.633966−0.0036930.056*
C22S1.0436 (5)0.7020 (3)0.0769 (3)0.0436 (12)
H22A1.1307740.6852670.0842460.052*
C23S0.9694 (5)0.7570 (2)0.1179 (2)0.0357 (11)
H23A1.0058130.7790910.1529680.043*
C24S0.8423 (5)0.7803 (2)0.1083 (2)0.0350 (11)
H24A0.7910580.8184700.1366060.042*
C25S0.7897 (4)0.7483 (2)0.0575 (3)0.0364 (11)
H25A0.7015810.7638180.0514320.044*
C26S0.8645 (5)0.6936 (3)0.0153 (3)0.0399 (12)
H26A0.8286360.671768−0.0201170.048*
C31S1.1011 (4)1.0345 (3)0.4477 (2)0.0347 (11)
H31A1.1711951.0584540.4116300.042*
C32S1.0012 (5)1.0798 (2)0.4862 (3)0.0359 (11)
H32A1.0016031.1352570.4765540.043*
C33S0.9005 (4)1.0453 (3)0.5385 (2)0.0338 (11)
H33A0.8316881.0769250.5652970.041*
B1A0.5700 (4)0.9616 (2)0.2250 (2)0.0164 (10)
B1B0.6459 (4)0.4690 (3)0.7248 (3)0.0215 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F2A0.0216 (14)0.0231 (13)0.0543 (16)−0.0061 (10)−0.0116 (12)−0.0030 (12)
F2B0.0527 (17)0.0439 (16)0.0188 (12)0.0177 (13)0.0006 (12)−0.0050 (12)
F3A0.0334 (14)0.0165 (12)0.0396 (14)−0.0089 (10)−0.0093 (11)−0.0031 (11)
F3B0.072 (2)0.0369 (15)0.0274 (13)0.0209 (14)−0.0196 (13)−0.0149 (12)
F4A0.0381 (15)0.0153 (12)0.0440 (15)0.0055 (11)−0.0093 (12)−0.0040 (11)
F4B0.0545 (18)0.0217 (13)0.0486 (16)−0.0116 (12)−0.0171 (13)−0.0006 (12)
F5A0.0229 (14)0.0249 (13)0.0584 (16)0.0036 (11)−0.0071 (12)−0.0086 (12)
F5B0.0494 (18)0.0358 (16)0.0578 (18)−0.0131 (13)0.0263 (15)0.0042 (14)
F6A0.0201 (13)0.0188 (12)0.0334 (13)−0.0060 (10)−0.0008 (10)−0.0042 (10)
F6B0.0478 (17)0.0227 (13)0.0479 (16)−0.0039 (12)0.0210 (13)−0.0056 (12)
F8A0.0242 (13)0.0330 (13)0.0142 (11)−0.0096 (10)−0.0012 (9)−0.0022 (10)
F8B0.0308 (15)0.0355 (14)0.0360 (14)−0.0142 (11)−0.0152 (11)−0.0071 (11)
F9A0.0380 (15)0.0448 (15)0.0152 (11)0.0000 (12)−0.0059 (10)−0.0128 (11)
F9B0.0516 (17)0.0271 (13)0.0321 (13)−0.0177 (12)−0.0145 (12)−0.0106 (11)
F10A0.0533 (17)0.0383 (15)0.0359 (14)−0.0112 (12)−0.0227 (13)−0.0170 (12)
F10B0.0492 (17)0.0233 (13)0.0425 (15)−0.0007 (12)−0.0052 (13)−0.0142 (12)
F11A0.0491 (17)0.0366 (14)0.0382 (14)−0.0311 (13)−0.0164 (12)0.0000 (12)
F11B0.0276 (15)0.0470 (16)0.0452 (15)0.0021 (12)−0.0094 (12)−0.0173 (13)
F12A0.0315 (14)0.0309 (13)0.0205 (12)−0.0192 (11)−0.0040 (10)0.0003 (10)
F12B0.0241 (14)0.0440 (15)0.0365 (13)−0.0115 (11)−0.0081 (11)−0.0207 (12)
F14A0.0344 (14)0.0200 (12)0.0193 (11)0.0006 (10)−0.0021 (10)−0.0078 (10)
F14B0.0359 (15)0.0414 (15)0.0305 (13)−0.0208 (12)−0.0063 (11)−0.0014 (12)
F15A0.0407 (15)0.0198 (13)0.0279 (12)−0.0043 (11)−0.0140 (11)0.0035 (10)
F15B0.0389 (16)0.0458 (16)0.0302 (13)−0.0126 (13)0.0021 (12)0.0057 (12)
F16A0.0360 (15)0.0407 (14)0.0183 (12)−0.0123 (12)−0.0083 (10)0.0050 (11)
F16B0.0685 (19)0.0398 (15)0.0178 (12)0.0000 (13)−0.0095 (12)−0.0029 (11)
F17A0.0310 (14)0.0430 (14)0.0147 (11)−0.0028 (11)−0.0025 (10)−0.0098 (11)
F17B0.073 (2)0.0325 (14)0.0346 (14)−0.0135 (13)−0.0267 (14)−0.0077 (12)
F18A0.0327 (14)0.0239 (13)0.0183 (11)0.0040 (10)−0.0062 (10)−0.0065 (10)
F18B0.0429 (16)0.0320 (14)0.0271 (12)−0.0199 (12)−0.0102 (11)−0.0021 (11)
O1A0.0194 (15)0.0213 (15)0.0120 (13)−0.0067 (11)−0.0021 (11)0.0006 (11)
O1B0.044 (2)0.061 (2)0.0281 (17)−0.0146 (17)−0.0045 (15)−0.0067 (18)
N1C0.027 (2)0.031 (2)0.0174 (17)−0.0041 (16)−0.0011 (15)−0.0063 (15)
N1D0.030 (2)0.0195 (18)0.0173 (17)−0.0076 (15)−0.0021 (15)−0.0024 (14)
N2C0.023 (2)0.0220 (19)0.0302 (19)−0.0009 (15)−0.0112 (16)−0.0089 (16)
N2D0.023 (2)0.026 (2)0.041 (2)−0.0028 (17)−0.0111 (18)−0.0087 (17)
C1A0.021 (2)0.018 (2)0.0109 (18)−0.0033 (17)−0.0063 (16)−0.0032 (16)
C1B0.019 (2)0.028 (2)0.021 (2)−0.0018 (18)−0.0087 (18)−0.0100 (18)
C1C0.060 (3)0.038 (3)0.026 (2)−0.015 (2)0.006 (2)−0.007 (2)
C1D0.040 (3)0.020 (2)0.024 (2)−0.0040 (19)−0.003 (2)−0.0037 (19)
C2A0.017 (2)0.024 (2)0.020 (2)−0.0031 (18)−0.0069 (17)−0.0085 (18)
C2B0.030 (3)0.043 (3)0.016 (2)0.006 (2)−0.0109 (19)−0.012 (2)
C2C0.025 (3)0.046 (3)0.023 (2)0.001 (2)−0.0013 (18)−0.016 (2)
C2D0.025 (2)0.023 (2)0.017 (2)−0.0062 (18)−0.0036 (18)−0.0034 (18)
C3A0.026 (2)0.017 (2)0.019 (2)−0.0078 (18)−0.0076 (18)−0.0010 (17)
C3B0.043 (3)0.025 (2)0.026 (2)0.013 (2)−0.021 (2)−0.013 (2)
C3C0.028 (3)0.069 (3)0.022 (2)0.000 (2)−0.002 (2)−0.016 (2)
C3D0.032 (3)0.030 (2)0.028 (2)−0.005 (2)−0.005 (2)−0.006 (2)
C4A0.031 (3)0.016 (2)0.018 (2)0.0012 (18)−0.0072 (18)−0.0081 (17)
C4B0.038 (3)0.017 (2)0.035 (2)−0.007 (2)−0.019 (2)−0.003 (2)
C4C0.022 (2)0.047 (3)0.022 (2)−0.010 (2)−0.0022 (18)−0.011 (2)
C4D0.024 (2)0.022 (2)0.032 (2)0.0028 (18)−0.0034 (19)−0.0015 (19)
C5A0.017 (2)0.023 (2)0.021 (2)0.0007 (17)−0.0058 (17)−0.0074 (18)
C5B0.029 (3)0.034 (3)0.035 (3)−0.012 (2)0.000 (2)−0.003 (2)
C5C0.043 (3)0.035 (3)0.070 (4)0.003 (2)−0.026 (3)−0.008 (3)
C5D0.041 (3)0.026 (2)0.056 (3)−0.003 (2)−0.026 (2)−0.004 (2)
C6A0.019 (2)0.020 (2)0.0149 (19)−0.0076 (17)−0.0016 (17)−0.0049 (17)
C6B0.026 (2)0.020 (2)0.034 (2)−0.0047 (19)0.002 (2)−0.009 (2)
C6C0.033 (3)0.056 (3)0.022 (2)−0.017 (2)0.002 (2)−0.014 (2)
C6D0.074 (4)0.050 (3)0.036 (3)0.009 (3)−0.023 (3)−0.015 (3)
C7A0.015 (2)0.0149 (19)0.0137 (18)−0.0011 (16)−0.0029 (16)−0.0031 (16)
C7B0.023 (2)0.019 (2)0.0140 (19)−0.0107 (17)−0.0049 (17)0.0018 (17)
C8A0.022 (2)0.014 (2)0.020 (2)−0.0015 (17)−0.0077 (17)−0.0032 (17)
C8B0.022 (2)0.025 (2)0.023 (2)−0.0107 (18)−0.0103 (18)0.0036 (19)
C9A0.031 (2)0.021 (2)0.014 (2)0.0071 (18)−0.0072 (18)−0.0065 (17)
C9B0.034 (3)0.025 (2)0.023 (2)−0.015 (2)−0.0091 (19)−0.0023 (19)
C10A0.034 (3)0.018 (2)0.029 (2)−0.0041 (19)−0.019 (2)−0.0104 (19)
C10B0.040 (3)0.013 (2)0.022 (2)−0.0031 (19)−0.003 (2)−0.0020 (18)
C11A0.025 (2)0.017 (2)0.030 (2)−0.0086 (18)−0.0094 (19)−0.0001 (18)
C11B0.025 (3)0.033 (2)0.026 (2)−0.009 (2)−0.0087 (19)−0.003 (2)
C11S0.034 (3)0.029 (3)0.073 (4)−0.003 (2)−0.013 (3)−0.025 (3)
C12A0.023 (2)0.021 (2)0.017 (2)−0.0059 (18)−0.0051 (18)−0.0025 (17)
C12B0.031 (3)0.020 (2)0.019 (2)−0.0121 (18)−0.0067 (18)−0.0055 (18)
C12S0.038 (3)0.027 (2)0.047 (3)−0.002 (2)0.000 (2)−0.011 (2)
C13A0.015 (2)0.018 (2)0.0161 (19)−0.0057 (16)−0.0063 (16)−0.0013 (16)
C13B0.023 (2)0.022 (2)0.019 (2)−0.0033 (18)−0.0022 (18)−0.0059 (18)
C13S0.037 (3)0.027 (3)0.048 (3)0.003 (2)−0.016 (2)−0.003 (2)
C14A0.019 (2)0.022 (2)0.0139 (19)−0.0064 (17)−0.0032 (16)−0.0055 (17)
C14B0.019 (2)0.030 (2)0.025 (2)−0.0067 (19)−0.0040 (18)−0.008 (2)
C14S0.025 (3)0.025 (2)0.051 (3)0.0007 (19)−0.009 (2)−0.003 (2)
C15A0.021 (2)0.019 (2)0.022 (2)−0.0030 (17)−0.0127 (18)0.0005 (18)
C15B0.024 (2)0.023 (2)0.027 (2)−0.0023 (19)0.0045 (19)0.0024 (19)
C15S0.039 (3)0.034 (3)0.042 (3)−0.001 (2)−0.003 (2)−0.016 (2)
C16A0.026 (2)0.033 (2)0.0075 (18)−0.0131 (19)−0.0080 (17)0.0036 (18)
C16B0.040 (3)0.027 (2)0.018 (2)0.006 (2)−0.008 (2)−0.0091 (19)
C16S0.048 (3)0.041 (3)0.046 (3)0.006 (2)−0.014 (3)−0.026 (3)
C17A0.017 (2)0.033 (2)0.0122 (19)−0.0056 (18)−0.0010 (16)−0.0090 (18)
C17B0.041 (3)0.020 (2)0.027 (2)−0.003 (2)−0.016 (2)−0.0084 (19)
C18A0.018 (2)0.018 (2)0.021 (2)−0.0062 (17)−0.0079 (17)−0.0038 (17)
C18B0.027 (2)0.019 (2)0.026 (2)−0.0075 (18)−0.0038 (19)−0.0030 (18)
C21S0.050 (4)0.034 (3)0.051 (3)0.012 (2)−0.004 (3)−0.012 (2)
C22S0.034 (3)0.041 (3)0.053 (3)−0.002 (2)−0.014 (2)0.005 (3)
C23S0.047 (3)0.033 (3)0.030 (2)−0.014 (2)−0.007 (2)−0.006 (2)
C24S0.044 (3)0.026 (2)0.028 (2)−0.004 (2)0.007 (2)−0.001 (2)
C25S0.032 (3)0.029 (3)0.044 (3)−0.004 (2)−0.007 (2)0.004 (2)
C26S0.048 (3)0.036 (3)0.041 (3)−0.007 (2)−0.015 (2)−0.012 (2)
C31S0.035 (3)0.052 (3)0.022 (2)−0.023 (2)−0.003 (2)−0.007 (2)
C32S0.055 (3)0.023 (2)0.039 (3)−0.008 (2)−0.027 (3)−0.006 (2)
C33S0.030 (3)0.041 (3)0.038 (3)0.007 (2)−0.016 (2)−0.024 (2)
B1A0.019 (3)0.021 (2)0.012 (2)−0.0066 (19)−0.0021 (18)−0.0053 (19)
B1B0.014 (2)0.027 (3)0.024 (2)−0.009 (2)−0.001 (2)−0.004 (2)
Geometric parameters (Å, º) top
F2A—C2A1.359 (4)C4B—C5B1.374 (6)
F2B—C2B1.341 (4)C4C—H4CA0.9900
F3A—C3A1.344 (4)C4C—H4CB0.9900
F3B—C3B1.351 (4)C4D—H4DA0.9900
F4A—C4A1.349 (4)C4D—H4DB0.9900
F4B—C4B1.346 (4)C5A—C6A1.376 (5)
F5A—C5A1.354 (4)C5B—C6B1.376 (5)
F5B—C5B1.352 (5)C5C—H5CA0.9800
F6A—C6A1.361 (4)C5C—H5CB0.9800
F6B—C6B1.362 (4)C5C—H5CC0.9800
F8A—C8A1.357 (4)C5D—H5DA0.9800
F8B—C8B1.356 (4)C5D—H5DB0.9800
F9A—C9A1.346 (4)C5D—H5DC0.9800
F9B—C9B1.350 (4)C6C—H6CA0.9800
F10A—C10A1.353 (4)C6C—H6CB0.9800
F10B—C10B1.353 (4)C6C—H6CC0.9800
F11A—C11A1.353 (4)C6D—H6DA0.9800
F11B—C11B1.351 (4)C6D—H6DB0.9800
F12A—C12A1.353 (4)C6D—H6DC0.9800
F12B—C12B1.369 (4)C7A—C8A1.387 (5)
F14A—C14A1.357 (4)C7A—C12A1.388 (5)
F14B—C14B1.355 (4)C7A—B1A1.663 (5)
F15A—C15A1.354 (4)C7B—C12B1.371 (5)
F15B—C15B1.352 (4)C7B—C8B1.385 (5)
F16A—C16A1.347 (4)C7B—B1B1.650 (6)
F16B—C16B1.344 (4)C8A—C9A1.379 (5)
F17A—C17A1.351 (4)C8B—C9B1.378 (5)
F17B—C17B1.352 (4)C9A—C10A1.371 (5)
F18A—C18A1.360 (4)C9B—C10B1.360 (6)
F18B—C18B1.357 (4)C10A—C11A1.371 (5)
O1A—B1A1.484 (5)C10B—C11B1.372 (5)
O1A—H1A0.8400C11A—C12A1.375 (5)
O1B—B1B1.487 (5)C11B—C12B1.371 (5)
O1B—H1B0.8400C11S—C16S1.365 (6)
N1C—C3C1.454 (5)C11S—C12S1.382 (6)
N1C—C1C1.473 (5)C11S—H11A0.9500
N1C—C2C1.475 (5)C12S—C13S1.393 (6)
N1D—C2D1.470 (4)C12S—H12A0.9500
N1D—C3D1.472 (5)C13A—C18A1.380 (5)
N1D—C1D1.478 (4)C13A—C14A1.395 (5)
N2C—C5C1.483 (5)C13A—B1A1.649 (5)
N2C—C6C1.483 (5)C13B—C14B1.374 (5)
N2C—C4C1.485 (5)C13B—C18B1.395 (5)
N2C—H2C1.04 (4)C13B—B1B1.659 (6)
N2D—C5D1.485 (5)C13S—C14S1.367 (6)
N2D—C6D1.495 (5)C13S—H13A0.9500
N2D—C4D1.503 (5)C14A—C15A1.372 (5)
N2D—H2D0.80 (4)C14B—C15B1.380 (5)
C1A—C6A1.379 (5)C14S—C15S1.376 (6)
C1A—C2A1.379 (5)C14S—H14A0.9500
C1A—B1A1.656 (5)C15A—C16A1.367 (5)
C1B—C6B1.381 (5)C15B—C16B1.364 (5)
C1B—C2B1.397 (5)C15S—C16S1.375 (6)
C1B—B1B1.646 (6)C15S—H15A0.9500
C1C—H1CA0.9800C16A—C17A1.370 (5)
C1C—H1CB0.9800C16B—C17B1.375 (6)
C1C—H1CC0.9800C16S—H16A0.9500
C1D—H1DA0.9800C17A—C18A1.384 (5)
C1D—H1DB0.9800C17B—C18B1.376 (5)
C1D—H1DC0.9800C21S—C22S1.370 (6)
C2A—C3A1.387 (5)C21S—C26S1.378 (6)
C2B—C3B1.382 (6)C21S—H21A0.9500
C2C—C2Ci1.503 (7)C22S—C23S1.373 (6)
C2C—H2CA0.9900C22S—H22A0.9500
C2C—H2CB0.9900C23S—C24S1.378 (6)
C2D—C2Dii1.522 (7)C23S—H23A0.9500
C2D—H2DA0.9900C24S—C25S1.375 (6)
C2D—H2DB0.9900C24S—H24A0.9500
C3A—C4A1.357 (5)C25S—C26S1.383 (6)
C3B—C4B1.359 (6)C25S—H25A0.9500
C3C—C4C1.526 (5)C26S—H26A0.9500
C3C—H3CA0.9900C31S—C33Siii1.369 (6)
C3C—H3CB0.9900C31S—C32S1.369 (6)
C3D—C4D1.507 (5)C31S—H31A0.9500
C3D—H3DA0.9900C32S—C33S1.369 (6)
C3D—H3DB0.9900C32S—H32A0.9500
C4A—C5A1.372 (5)C33S—H33A0.9500
B1A—O1A—H1A109.5C8A—C7A—B1A119.9 (3)
B1B—O1B—H1B109.5C12A—C7A—B1A126.9 (3)
C3C—N1C—C1C109.1 (3)C12B—C7B—C8B113.2 (3)
C3C—N1C—C2C108.8 (3)C12B—C7B—B1B121.3 (3)
C1C—N1C—C2C110.2 (3)C8B—C7B—B1B125.5 (3)
C2D—N1D—C3D109.6 (3)F8A—C8A—C9A115.4 (3)
C2D—N1D—C1D111.8 (3)F8A—C8A—C7A119.7 (3)
C3D—N1D—C1D110.3 (3)C9A—C8A—C7A124.9 (3)
C5C—N2C—C6C110.5 (3)F8B—C8B—C9B114.9 (3)
C5C—N2C—C4C111.9 (3)F8B—C8B—C7B121.1 (4)
C6C—N2C—C4C110.0 (3)C9B—C8B—C7B124.0 (4)
C5C—N2C—H2C104 (2)F9A—C9A—C10A120.5 (3)
C6C—N2C—H2C109 (2)F9A—C9A—C8A120.5 (3)
C4C—N2C—H2C112 (2)C10A—C9A—C8A118.9 (3)
C5D—N2D—C6D111.1 (4)F9B—C9B—C10B119.4 (4)
C5D—N2D—C4D113.5 (3)F9B—C9B—C8B121.4 (4)
C6D—N2D—C4D109.5 (3)C10B—C9B—C8B119.2 (3)
C5D—N2D—H2D111 (3)F10A—C10A—C11A120.7 (3)
C6D—N2D—H2D106 (3)F10A—C10A—C9A120.3 (3)
C4D—N2D—H2D105 (3)C11A—C10A—C9A119.0 (3)
C6A—C1A—C2A112.6 (3)F10B—C10B—C9B119.7 (3)
C6A—C1A—B1A121.2 (3)F10B—C10B—C11B120.4 (4)
C2A—C1A—B1A125.9 (3)C9B—C10B—C11B119.8 (4)
C6B—C1B—C2B112.6 (4)F11A—C11A—C10A119.4 (3)
C6B—C1B—B1B128.4 (3)F11A—C11A—C12A120.5 (3)
C2B—C1B—B1B118.3 (3)C10A—C11A—C12A120.1 (3)
N1C—C1C—H1CA109.5F11B—C11B—C12B122.0 (3)
N1C—C1C—H1CB109.5F11B—C11B—C10B119.7 (4)
H1CA—C1C—H1CB109.5C12B—C11B—C10B118.3 (4)
N1C—C1C—H1CC109.5C16S—C11S—C12S120.4 (4)
H1CA—C1C—H1CC109.5C16S—C11S—H11A119.8
H1CB—C1C—H1CC109.5C12S—C11S—H11A119.8
N1D—C1D—H1DA109.5F12A—C12A—C11A115.2 (3)
N1D—C1D—H1DB109.5F12A—C12A—C7A120.9 (3)
H1DA—C1D—H1DB109.5C11A—C12A—C7A123.9 (3)
N1D—C1D—H1DC109.5F12B—C12B—C7B118.7 (3)
H1DA—C1D—H1DC109.5F12B—C12B—C11B115.7 (3)
H1DB—C1D—H1DC109.5C7B—C12B—C11B125.4 (3)
F2A—C2A—C1A120.6 (3)C11S—C12S—C13S119.0 (5)
F2A—C2A—C3A114.5 (3)C11S—C12S—H12A120.5
C1A—C2A—C3A124.9 (4)C13S—C12S—H12A120.5
F2B—C2B—C3B116.1 (4)C18A—C13A—C14A113.1 (3)
F2B—C2B—C1B119.6 (4)C18A—C13A—B1A127.5 (3)
C3B—C2B—C1B124.3 (4)C14A—C13A—B1A119.4 (3)
N1C—C2C—C2Ci112.7 (4)C14B—C13B—C18B113.1 (3)
N1C—C2C—H2CA109.1C14B—C13B—B1B120.9 (3)
C2Ci—C2C—H2CA109.1C18B—C13B—B1B126.0 (3)
N1C—C2C—H2CB109.1C14S—C13S—C12S120.0 (4)
C2Ci—C2C—H2CB109.1C14S—C13S—H13A120.0
H2CA—C2C—H2CB107.8C12S—C13S—H13A120.0
N1D—C2D—C2Dii111.9 (3)F14A—C14A—C15A116.2 (3)
N1D—C2D—H2DA109.2F14A—C14A—C13A119.4 (3)
C2Dii—C2D—H2DA109.2C15A—C14A—C13A124.4 (3)
N1D—C2D—H2DB109.2F14B—C14B—C13B119.4 (3)
C2Dii—C2D—H2DB109.2F14B—C14B—C15B115.9 (3)
H2DA—C2D—H2DB107.9C13B—C14B—C15B124.7 (3)
F3A—C3A—C4A120.2 (3)C13S—C14S—C15S120.4 (4)
F3A—C3A—C2A120.5 (3)C13S—C14S—H14A119.8
C4A—C3A—C2A119.4 (3)C15S—C14S—H14A119.8
F3B—C3B—C4B119.6 (4)F15A—C15A—C16A119.4 (3)
F3B—C3B—C2B120.5 (4)F15A—C15A—C14A120.9 (3)
C4B—C3B—C2B119.8 (4)C16A—C15A—C14A119.7 (3)
N1C—C3C—C4C113.4 (3)F15B—C15B—C16B120.2 (4)
N1C—C3C—H3CA108.9F15B—C15B—C14B119.9 (4)
C4C—C3C—H3CA108.9C16B—C15B—C14B119.8 (4)
N1C—C3C—H3CB108.9C16S—C15S—C14S119.7 (5)
C4C—C3C—H3CB108.9C16S—C15S—H15A120.2
H3CA—C3C—H3CB107.7C14S—C15S—H15A120.2
N1D—C3D—C4D113.8 (3)F16A—C16A—C15A120.8 (3)
N1D—C3D—H3DA108.8F16A—C16A—C17A120.1 (3)
C4D—C3D—H3DA108.8C15A—C16A—C17A119.0 (3)
N1D—C3D—H3DB108.8F16B—C16B—C15B121.2 (4)
C4D—C3D—H3DB108.8F16B—C16B—C17B120.4 (3)
H3DA—C3D—H3DB107.7C15B—C16B—C17B118.4 (3)
F4A—C4A—C3A121.4 (3)C11S—C16S—C15S120.4 (5)
F4A—C4A—C5A120.0 (4)C11S—C16S—H16A119.8
C3A—C4A—C5A118.6 (4)C15S—C16S—H16A119.8
F4B—C4B—C3B120.8 (4)F17A—C17A—C16A119.7 (3)
F4B—C4B—C5B120.5 (4)F17A—C17A—C18A120.8 (3)
C3B—C4B—C5B118.7 (4)C16A—C17A—C18A119.5 (3)
N2C—C4C—C3C113.6 (3)F17B—C17B—C16B118.9 (3)
N2C—C4C—H4CA108.8F17B—C17B—C18B121.1 (4)
C3C—C4C—H4CA108.8C16B—C17B—C18B120.0 (3)
N2C—C4C—H4CB108.8F18A—C18A—C13A120.7 (3)
C3C—C4C—H4CB108.8F18A—C18A—C17A115.0 (3)
H4CA—C4C—H4CB107.7C13A—C18A—C17A124.3 (3)
N2D—C4D—C3D114.4 (3)F18B—C18B—C17B115.5 (3)
N2D—C4D—H4DA108.7F18B—C18B—C13B120.6 (3)
C3D—C4D—H4DA108.7C17B—C18B—C13B123.9 (4)
N2D—C4D—H4DB108.7C22S—C21S—C26S120.8 (4)
C3D—C4D—H4DB108.7C22S—C21S—H21A119.6
H4DA—C4D—H4DB107.6C26S—C21S—H21A119.6
F5A—C5A—C4A119.6 (3)C21S—C22S—C23S119.8 (5)
F5A—C5A—C6A120.5 (3)C21S—C22S—H22A120.1
C4A—C5A—C6A119.8 (4)C23S—C22S—H22A120.1
F5B—C5B—C4B119.8 (4)C22S—C23S—C24S120.1 (4)
F5B—C5B—C6B120.4 (4)C22S—C23S—H23A119.9
C4B—C5B—C6B119.8 (4)C24S—C23S—H23A119.9
N2C—C5C—H5CA109.5C25S—C24S—C23S119.9 (4)
N2C—C5C—H5CB109.5C25S—C24S—H24A120.1
H5CA—C5C—H5CB109.5C23S—C24S—H24A120.1
N2C—C5C—H5CC109.5C24S—C25S—C26S120.3 (4)
H5CA—C5C—H5CC109.5C24S—C25S—H25A119.9
H5CB—C5C—H5CC109.5C26S—C25S—H25A119.9
N2D—C5D—H5DA109.5C21S—C26S—C25S119.1 (4)
N2D—C5D—H5DB109.5C21S—C26S—H26A120.4
H5DA—C5D—H5DB109.5C25S—C26S—H26A120.4
N2D—C5D—H5DC109.5C33Siii—C31S—C32S119.6 (4)
H5DA—C5D—H5DC109.5C33Siii—C31S—H31A120.2
H5DB—C5D—H5DC109.5C32S—C31S—H31A120.2
F6A—C6A—C5A116.3 (3)C33S—C32S—C31S120.2 (4)
F6A—C6A—C1A119.1 (3)C33S—C32S—H32A119.9
C5A—C6A—C1A124.6 (3)C31S—C32S—H32A119.9
F6B—C6B—C5B114.4 (3)C31Siii—C33S—C32S120.2 (4)
F6B—C6B—C1B120.9 (3)C31Siii—C33S—H33A119.9
C5B—C6B—C1B124.7 (4)C32S—C33S—H33A119.9
N2C—C6C—H6CA109.5O1A—B1A—C13A104.5 (3)
N2C—C6C—H6CB109.5O1A—B1A—C1A112.3 (3)
H6CA—C6C—H6CB109.5C13A—B1A—C1A114.6 (3)
N2C—C6C—H6CC109.5O1A—B1A—C7A108.9 (3)
H6CA—C6C—H6CC109.5C13A—B1A—C7A110.8 (3)
H6CB—C6C—H6CC109.5C1A—B1A—C7A105.7 (3)
N2D—C6D—H6DA109.5O1B—B1B—C1B103.1 (3)
N2D—C6D—H6DB109.5O1B—B1B—C7B112.5 (3)
H6DA—C6D—H6DB109.5C1B—B1B—C7B112.0 (3)
N2D—C6D—H6DC109.5O1B—B1B—C13B107.2 (3)
H6DA—C6D—H6DC109.5C1B—B1B—C13B114.5 (3)
H6DB—C6D—H6DC109.5C7B—B1B—C13B107.6 (3)
C8A—C7A—C12A113.1 (3)
C6A—C1A—C2A—F2A176.9 (3)C8B—C7B—C12B—C11B4.0 (6)
B1A—C1A—C2A—F2A−9.0 (5)B1B—C7B—C12B—C11B−173.0 (4)
C6A—C1A—C2A—C3A−2.3 (5)F11B—C11B—C12B—F12B2.4 (5)
B1A—C1A—C2A—C3A171.8 (3)C10B—C11B—C12B—F12B−175.6 (3)
C6B—C1B—C2B—F2B179.9 (3)F11B—C11B—C12B—C7B177.3 (3)
B1B—C1B—C2B—F2B8.7 (5)C10B—C11B—C12B—C7B−0.6 (6)
C6B—C1B—C2B—C3B−0.5 (6)C16S—C11S—C12S—C13S−1.9 (6)
B1B—C1B—C2B—C3B−171.8 (4)C11S—C12S—C13S—C14S1.0 (6)
C3C—N1C—C2C—C2Ci178.3 (5)C18A—C13A—C14A—F14A178.9 (3)
C1C—N1C—C2C—C2Ci−62.1 (6)B1A—C13A—C14A—F14A−1.4 (5)
C3D—N1D—C2D—C2Dii−173.2 (4)C18A—C13A—C14A—C15A0.4 (5)
C1D—N1D—C2D—C2Dii64.2 (5)B1A—C13A—C14A—C15A−180.0 (3)
F2A—C2A—C3A—F3A1.1 (5)C18B—C13B—C14B—F14B−177.6 (3)
C1A—C2A—C3A—F3A−179.7 (3)B1B—C13B—C14B—F14B2.8 (6)
F2A—C2A—C3A—C4A−178.7 (3)C18B—C13B—C14B—C15B2.0 (6)
C1A—C2A—C3A—C4A0.6 (6)B1B—C13B—C14B—C15B−177.6 (4)
F2B—C2B—C3B—F3B−0.7 (5)C12S—C13S—C14S—C15S−0.2 (6)
C1B—C2B—C3B—F3B179.7 (3)F14A—C14A—C15A—F15A1.1 (5)
F2B—C2B—C3B—C4B−179.5 (3)C13A—C14A—C15A—F15A179.7 (3)
C1B—C2B—C3B—C4B0.9 (6)F14A—C14A—C15A—C16A−177.0 (3)
C1C—N1C—C3C—C4C73.7 (4)C13A—C14A—C15A—C16A1.6 (6)
C2C—N1C—C3C—C4C−166.0 (4)F14B—C14B—C15B—F15B−2.9 (5)
C2D—N1D—C3D—C4D164.5 (3)C13B—C14B—C15B—F15B177.5 (4)
C1D—N1D—C3D—C4D−72.1 (4)F14B—C14B—C15B—C16B178.5 (4)
F3A—C3A—C4A—F4A−0.7 (5)C13B—C14B—C15B—C16B−1.1 (6)
C2A—C3A—C4A—F4A179.1 (3)C13S—C14S—C15S—C16S0.2 (6)
F3A—C3A—C4A—C5A−178.3 (3)F15A—C15A—C16A—F16A−1.6 (5)
C2A—C3A—C4A—C5A1.5 (5)C14A—C15A—C16A—F16A176.6 (3)
F3B—C3B—C4B—F4B0.5 (6)F15A—C15A—C16A—C17A179.8 (3)
C2B—C3B—C4B—F4B179.3 (3)C14A—C15A—C16A—C17A−2.1 (5)
F3B—C3B—C4B—C5B−179.5 (3)F15B—C15B—C16B—F16B1.2 (6)
C2B—C3B—C4B—C5B−0.7 (6)C14B—C15B—C16B—F16B179.8 (4)
C5C—N2C—C4C—C3C67.0 (4)F15B—C15B—C16B—C17B−179.4 (4)
C6C—N2C—C4C—C3C−169.8 (4)C14B—C15B—C16B—C17B−0.8 (6)
N1C—C3C—C4C—N2C71.9 (5)C12S—C11S—C16S—C15S1.9 (7)
C5D—N2D—C4D—C3D−60.9 (5)C14S—C15S—C16S—C11S−1.1 (6)
C6D—N2D—C4D—C3D174.3 (4)F16A—C16A—C17A—F17A1.8 (5)
N1D—C3D—C4D—N2D−63.9 (4)C15A—C16A—C17A—F17A−179.6 (3)
F4A—C4A—C5A—F5A0.2 (5)F16A—C16A—C17A—C18A−178.0 (3)
C3A—C4A—C5A—F5A177.8 (3)C15A—C16A—C17A—C18A0.6 (5)
F4A—C4A—C5A—C6A−179.2 (3)F16B—C16B—C17B—F17B0.9 (6)
C3A—C4A—C5A—C6A−1.5 (5)C15B—C16B—C17B—F17B−178.5 (4)
F4B—C4B—C5B—F5B0.5 (6)F16B—C16B—C17B—C18B−179.1 (4)
C3B—C4B—C5B—F5B−179.5 (4)C15B—C16B—C17B—C18B1.5 (6)
F4B—C4B—C5B—C6B−179.8 (4)C14A—C13A—C18A—F18A177.7 (3)
C3B—C4B—C5B—C6B0.2 (6)B1A—C13A—C18A—F18A−1.9 (5)
F5A—C5A—C6A—F6A−0.5 (5)C14A—C13A—C18A—C17A−1.9 (5)
C4A—C5A—C6A—F6A178.8 (3)B1A—C13A—C18A—C17A178.5 (3)
F5A—C5A—C6A—C1A−179.8 (3)F17A—C17A—C18A—F18A2.0 (5)
C4A—C5A—C6A—C1A−0.5 (5)C16A—C17A—C18A—F18A−178.2 (3)
C2A—C1A—C6A—F6A−177.0 (3)F17A—C17A—C18A—C13A−178.4 (3)
B1A—C1A—C6A—F6A8.5 (5)C16A—C17A—C18A—C13A1.5 (6)
C2A—C1A—C6A—C5A2.3 (5)F17B—C17B—C18B—F18B0.2 (6)
B1A—C1A—C6A—C5A−172.2 (3)C16B—C17B—C18B—F18B−179.8 (4)
F5B—C5B—C6B—F6B−0.8 (6)F17B—C17B—C18B—C13B179.5 (4)
C4B—C5B—C6B—F6B179.5 (4)C16B—C17B—C18B—C13B−0.5 (6)
F5B—C5B—C6B—C1B179.9 (4)C14B—C13B—C18B—F18B178.1 (3)
C4B—C5B—C6B—C1B0.2 (7)B1B—C13B—C18B—F18B−2.3 (6)
C2B—C1B—C6B—F6B−179.4 (3)C14B—C13B—C18B—C17B−1.2 (6)
B1B—C1B—C6B—F6B−9.2 (6)B1B—C13B—C18B—C17B178.4 (4)
C2B—C1B—C6B—C5B0.0 (6)C26S—C21S—C22S—C23S−1.4 (7)
B1B—C1B—C6B—C5B170.1 (4)C21S—C22S—C23S—C24S1.1 (7)
C12A—C7A—C8A—F8A178.3 (3)C22S—C23S—C24S—C25S0.1 (6)
B1A—C7A—C8A—F8A0.7 (5)C23S—C24S—C25S—C26S−0.9 (6)
C12A—C7A—C8A—C9A−1.7 (5)C22S—C21S—C26S—C25S0.5 (7)
B1A—C7A—C8A—C9A−179.3 (3)C24S—C25S—C26S—C21S0.6 (7)
C12B—C7B—C8B—F8B177.9 (3)C33Siii—C31S—C32S—C33S0.4 (7)
B1B—C7B—C8B—F8B−5.2 (6)C31S—C32S—C33S—C31Siii−0.4 (7)
C12B—C7B—C8B—C9B−4.6 (5)C18A—C13A—B1A—O1A122.2 (4)
B1B—C7B—C8B—C9B172.3 (4)C14A—C13A—B1A—O1A−57.4 (4)
F8A—C8A—C9A—F9A1.8 (5)C18A—C13A—B1A—C1A−1.2 (5)
C7A—C8A—C9A—F9A−178.1 (3)C14A—C13A—B1A—C1A179.2 (3)
F8A—C8A—C9A—C10A−177.4 (3)C18A—C13A—B1A—C7A−120.6 (4)
C7A—C8A—C9A—C10A2.7 (6)C14A—C13A—B1A—C7A59.8 (4)
F8B—C8B—C9B—F9B0.1 (5)C6A—C1A—B1A—O1A170.8 (3)
C7B—C8B—C9B—F9B−177.6 (3)C2A—C1A—B1A—O1A−2.8 (5)
F8B—C8B—C9B—C10B179.5 (3)C6A—C1A—B1A—C13A−70.1 (4)
C7B—C8B—C9B—C10B1.9 (6)C2A—C1A—B1A—C13A116.2 (4)
F9A—C9A—C10A—F10A−0.5 (6)C6A—C1A—B1A—C7A52.2 (4)
C8A—C9A—C10A—F10A178.7 (3)C2A—C1A—B1A—C7A−121.5 (4)
F9A—C9A—C10A—C11A179.2 (3)C8A—C7A—B1A—O1A−44.7 (4)
C8A—C9A—C10A—C11A−1.6 (6)C12A—C7A—B1A—O1A138.0 (4)
F9B—C9B—C10B—F10B1.2 (5)C8A—C7A—B1A—C13A−159.2 (3)
C8B—C9B—C10B—F10B−178.2 (3)C12A—C7A—B1A—C13A23.6 (5)
F9B—C9B—C10B—C11B−178.7 (3)C8A—C7A—B1A—C1A76.2 (4)
C8B—C9B—C10B—C11B1.9 (6)C12A—C7A—B1A—C1A−101.1 (4)
F10A—C10A—C11A—F11A−0.4 (6)C6B—C1B—B1B—O1B−114.6 (4)
C9A—C10A—C11A—F11A179.9 (3)C2B—C1B—B1B—O1B55.1 (4)
F10A—C10A—C11A—C12A179.5 (3)C6B—C1B—B1B—C7B6.5 (6)
C9A—C10A—C11A—C12A−0.2 (6)C2B—C1B—B1B—C7B176.2 (3)
F10B—C10B—C11B—F11B−0.4 (6)C6B—C1B—B1B—C13B129.4 (4)
C9B—C10B—C11B—F11B179.5 (4)C2B—C1B—B1B—C13B−60.9 (5)
F10B—C10B—C11B—C12B177.6 (3)C12B—C7B—B1B—O1B−176.4 (3)
C9B—C10B—C11B—C12B−2.5 (6)C8B—C7B—B1B—O1B7.0 (5)
F11A—C11A—C12A—F12A−0.9 (5)C12B—C7B—B1B—C1B68.0 (4)
C10A—C11A—C12A—F12A179.3 (3)C8B—C7B—B1B—C1B−108.6 (4)
F11A—C11A—C12A—C7A−179.0 (3)C12B—C7B—B1B—C13B−58.7 (4)
C10A—C11A—C12A—C7A1.2 (6)C8B—C7B—B1B—C13B124.8 (4)
C8A—C7A—C12A—F12A−178.2 (3)C14B—C13B—B1B—O1B47.0 (5)
B1A—C7A—C12A—F12A−0.8 (6)C18B—C13B—B1B—O1B−132.5 (4)
C8A—C7A—C12A—C11A−0.2 (6)C14B—C13B—B1B—C1B160.6 (4)
B1A—C7A—C12A—C11A177.2 (4)C18B—C13B—B1B—C1B−18.9 (5)
C8B—C7B—C12B—F12B178.8 (3)C14B—C13B—B1B—C7B−74.2 (4)
B1B—C7B—C12B—F12B1.9 (5)C18B—C13B—B1B—C7B106.3 (4)
Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg4, Cg7–Cg9 are the centroids of the C1B–C6B, C11S–C16S, C21S–C26S and C31S–C33S/C31S'–C31S' rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1A—H1A···F8A0.842.162.731 (3)125
O1B—H1B···N1D0.842.122.846 (4)144
N2C—H2C···O1A1.05 (4)1.60 (4)2.632 (4)169 (3)
N2D—H2D···O1B0.80 (4)1.76 (4)2.554 (5)171 (4)
C2C—H2CB···F8Ai0.992.463.435 (5)168
C4C—H4CA···F6Aiv0.992.403.191 (5)137
C5D—H5DC···F14B0.982.543.284 (5)133
C32S—H32A···F10Bv0.952.523.133 (5)123
C14S—H14A···Cg4vi0.952.953.779 (5)147
C4D—H4DA···Cg70.992.733.620 (4)150
C6C—H6CB···Cg90.982.743.689 (4)163
C6C—H6CB···Cg9iii0.982.743.689 (4)163
Symmetry codes: (i) −x+2, −y+2, −z; (iii) −x+2, −y+2, −z+1; (iv) x+1, y, z; (v) x, y+1, z; (vi) x−1, y, z.
 

Acknowledgements

RJB wishes to acknowledge the ONR Summer Faculty Research Program for funding in 2019 and 2020.

Funding information

Funding for this research was provided by: The Office of Naval Research.

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