[Se(CH2C(O)CH3)3][B12F11NH3]: The first selenium cation with three β-ketone substituents

Jenne, C.; Nierstenhöfer, M.C.

doi:10.1107/S2056989020000481

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ISSN: 2056-9890

Volume 76| Part 2| February 2020| Pages 221-224

https://doi.org/10.1107/S2056989020000481

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[Se(CH₂C(O)CH₃)₃][B₁₂F₁₁NH₃]: The first selenium cation with three β-ketone substituents

Carsten Jenne ^a ^* and Marc C. Nierstenhöfer ^a

^aAnorganische Chemie, Fakultät für Mathematik und Naturwissenschaften, Bergische Universität Wuppertal, Gaussstr. 20, 42119 Wuppertal, Germany
^*Correspondence e-mail: carsten.jenne@uni-wuppertal.de

Edited by S. Parkin, University of Kentucky, USA (Received 10 January 2020; accepted 14 January 2020; online 17 January 2020)

The reaction of [Se₈][B₁₂F₁₁NH₃]₂ with acetone and subsequent crystallization from acetone/diethyl ether yielded the selenium cation [Se(CH₂C(O)CH₃)₃]⁺ as a by-product, which is stabilized by the weakly coordinating undecafluorinated anion [B₁₂F₁₁NH₃]⁻. While attempting to crystallize pure [Se₈][B₁₂F₁₁NH₃]₂, the structure of the isolated product, namely, tris(2-oxopropyl)selenium 1-ammonioundecafluorododecaborate, was surprising. The cation [Se(CH₂C(O)CH₃)₃]⁺ represents the first example for a cationic selenium compound with three ketone functional groups located in the β-position with respect to the selenium atom. The cation possesses almost trigonal–pyramidal C₃ symmetry and forms hydrogen bonds to the ammonio group of the anion.

Keywords: crystal structure; selenium cation; weakly coordinating anion; dodecaborates; boron cluster; C—H activation.

CCDC reference: 1977644

1. Chemical context

Homopolyatomic chalcogen cations are of fundamental importance in main-group chemistry because of their unusual structures and bonding situations (Brownridge et al., 2000 ). Only a few examples for homopolyatomic selenium cations are known today, e.g. [Se₄]²⁺ (Minkwitz et al., 1991 ), [Se₈]²⁺ (McMullan et al., 1969 ), [Se₁₀]²⁺ (Beck & Hilbert, 2000 ) and [Se₁₇]²⁺ (Beck & Wetterau, 1995 ). These chalcogen cations are all dicationic and are all stabilized in the solid state by small perfluorinated or perchlorinated complex anions such as [SbF₆]⁻ (Minkwitz et al., 1991), [ReCl₆]²⁻ (Beck et al., 2002 ), or [AlCl₄]⁻ (McMullan et al., 1969). Recently, we were able to isolate the first homopolyatomic chalcogen radical cation, the sulfur cation [S₈]⁺, and to determine its crystal structure (Derendorf et al., 2017 ). The [S₈]⁺ cation was stabilized in the solid state by the chlorinated closo-dodecaborate anion [B₁₂Cl₁₂]²⁻. Consequently, the experimentally and theoretically unknown corresponding radical cations of the chalcogen elements sulfur, selenium, and tellurium [Ch_x]⁺ (Ch = S, Se, Te, x = 2–10) became of interest. In a very recent theoretical account, we have shown that some radical cations of the heavier chalcogens selenium and tellurium should also be experimentally accessible in condensed phases (Jenne & Nierstenhöfer, 2020 ). Modern weakly coordinating anions such as perhalogenated closo-dodecaborates (Knapp, 2013 ) are expected to be suitable counter-anions for homopolyatomic chalcogen radical cations in solution and the solid state. For this purpose, the synthesis of [Se₈][B₁₂F₁₁NH₃]₂ was attempted by a salt metathesis reaction of Na[B₁₂F₁₁NH₃] and [Se₈][AsF₆]₂ in liquid sulfur dioxide. The salt [Se₈][B₁₂F₁₁NH₃]₂ was assumed to be a suitable precursor on the way to related open-shell radical cations. From an attempt to generate single crystals of this compound from acetone/diethyl ether solution, the organoselenium cation [Se(CH₂C(O)CH₃)₃]⁺ was isolated as the [B₁₂F₁₁NH₃]⁻ salt.

Homopolyatomic selenium cations have not been considered before for addition or substitution reactions on ketones or enols. However, the reaction of homopolyatomic sulfur cations with acetonitrile under C—H activation has been reported (Cameron et al., 1999 ). Typically, alkyl selenium halides (RSeX) such as C₆H₅SeAlR₂ (Reich et al., 1975 ), C₅H₄NSeCl (Kozikowski & Ames, 1978 ), or dialkyl selenium compounds R₂Se such as (C₆H₅)₂Se₂ (Toshimitsu et al., 1984 ) have been used for electrophilic selenylation of functionalized olefins or enolisable ketones such as acetone. After a subsequent oxidation, α,β-unsaturated or 1,2 diketones can be obtained (Reich et al., 1979 ; Marshall & Royce 1982 ; Schreiber & Santini, 1984 ). Organoselenium cations are well known. The most simple representatives are trialkyl- or triaryl-substituted cations such as [Me₃Se]⁺ (Hope, 1966 ) and [Ph₃Se]⁺ (Leicester & Bergstrom, 1929 ), but mixed derivatives such as [Ph₂MeSe]⁺ (Dumont et al., 1974 ) are known as well. Furthermore, selenium cations with a single keto group {[PhC(O)CH₂SeMe₂]⁺; Lotz & Gosselck, 1973 } or a carbonic acid {[Me₂SeCH₂COOH]⁺; Ip & Ganther, 1990 } in the β-position have been reported. A symmetrically substituted selenium cation with three β-keto groups is reported herein for the first time.

2. Structural commentary

The salt [Se(CH₂C(O)CH₃)₃][B₁₂F₁₁NH₃] crystallizes solvent-free in the orthorhombic crystal system in space group Pbca (Fig. 1). The cation is close to being C₃ symmetric and the selenium atom is bonded to three chemically equivalent methylene groups with essentially identical bond lengths of 1.947 (2) to 1.951 (2) Å (Table 1). These distances are in the expected range when compared to the simple [SeMe₃]⁺ cation (Hope, 1966) with Se—C bond lengths from 1.94 (2) to 1.96 (2) Å. This indicates that the electron-withdrawing effect of the ketone groups has no influence on the Se—C bond lengths.

Table 1
Selected geometric parameters (Å, °)

Se1—C1	1.9511 (19)	O2—C5	1.211 (3)
Se1—C4	1.951 (2)	C2—C1	1.508 (3)
Se1—C7	1.947 (2)	C5—C4	1.509 (3)
O1—C2	1.212 (2)	C8—C7	1.507 (3)
O3—C8	1.205 (3)

C4—Se1—C1	98.17 (9)	C7—Se1—C4	97.67 (9)
C7—Se1—C1	98.26 (9)

Figure 1
Part of the crystal structure of [Se(CH₂C(O)CH₃)₃][B₁₂F₁₁NH₃]. Displacement ellipsoids are drawn at the 50% probability level and hydrogen atoms are shown with arbitrary radii.

Furthermore, there are additional contacts between the central selenium cation and the three oxygen atoms of the ketone groups (Fig. 2a). The oxygen–selenium contacts (2.810 Å on average) are much shorter than the sum of the van der Waals radii of selenium and oxygen (3.42 Å; Bondi, 1964 ). This interaction can be considered as mainly electrostatic, since the oxygen atoms are partially negatively charged and the selenium cation carries a positive charge. Thus, the selenium atom forms six short contacts, i.e. it is covalently bonded to three carbon atoms and forms three ionic interactions to the three oxygen atoms. The carbon atoms span a small triangular face, which is essentially parallel to a larger triangular face formed by the oxygen atoms (Fig. 2b). This results in a flat distorted trigonal prism surrounding the selenium atom.

Figure 2
(a) The [Se(CH₂C(O)CH₃)₃]⁺ cation shows intramolecular contacts of the selenium atom to the three oxygen atoms of the ketone groups. Selected intramolecular contacts are drawn using dashed lines [O1⋯Se1 = 2.794 (3), O2⋯Se1 = 2.788 (3) and O3—Se1 = 2.847 (3) Å]. (b) Coordination sphere around the Se atom forming a distorted trigonal prism. Displacement ellipsoids are drawn at the 50% probability level and hydrogen atoms are omitted for clarity.

The structure of the anion [B₁₂F₁₁NH₃]⁻ is less interesting and reveals bond distances in the expected range. The boron–boron bond lengths in the anion are in the range 1.777 (3) to 1.803 (4) Å and the average boron–fluorine bond length is 1.38 Å, which are very similar to those in other fluorinated dodecaborates such as [B₁₂F₁₁NMe₃]⁻ (Strauss et al., 2003 ) or [B₁₂F₁₂]²⁻ (Ivanov et al., 2003 ). The B—N bond length of 1.538 (3) Å is essentially equal to that in [B₁₂H₁₁NH₃]⁻ (Nachtigal et al., 1997 ) but slightly shorter than in [B₁₂F₁₁NMe₃]⁻ (Strauss et al., 2003) and in [B₁₂Cl₁₁NMe₃]⁻ (Bolli et al., 2014 ).

3. Supramolecular features

The [Se(CH₂C(O)CH₃)₃]⁺ cations and the [B₁₂F₁₁NH₃]⁻ anions are connected by intermolecular hydrogen-bonding interactions, resulting in a polymeric network. The hydrogen atoms of the positively charged ammonio group of the cation interact with the partially negatively charged oxygen atoms of the ketone groups of the cation (Fig. 3a). The oxygen–nitrogen distances are between 2.841 (2) and 2.865 (2) Å (Table 2), which is in the range of typical N—H⋯O hydrogen bonds (Huheey, 1988 ). Every ketone group of the cation is coordinated to an ammonio group of a different boron cluster anion. Likewise every ammonio group is coordinated threefold by the ketone groups of three different cations, as shown in Fig. 3b.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H⋯O2ⁱ	0.91	2.20	2.865 (2)	129
N1—HA⋯O1ⁱⁱ	0.91	1.94	2.836 (2)	168
N1—HB⋯O3ⁱⁱⁱ	0.91	1.94	2.841 (2)	171
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 3
Intermolecular hydrogen-bonding interactions (dashed lines) between the hydrogen atoms of the ammonio group of the boron cluster anions and the oxygen atoms of the ketone functions. Displacement ellipsoids are drawn at the 50% probability level and hydrogen atoms are shown with arbitrary radii. Symmetry codes: (a) x, $[{3\over 2}]$ − y, z; (b) 1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; (c) − $[{1\over 2}]$ + x, y, $[{3\over 2}]$ − z.

4. Database survey

The weakly coordinating anion [B₁₂F₁₁NH₃]⁻ was first reported in 2003 and was further functionalized by methylation yielding the [B₁₂F₁₁NMe₃]⁻ anion (Ivanov et al., 2003). Only two crystal structures of the non-alkylated ammonio-functionalized, undecafluoro dodecaborate are known, i.e. the sodium tetraaqua complex [Na(H₂O)₄]⁺ (Strauss et al., 2017 ) and the solvent-free K[B₁₂F₁₁NH₃] salt (Jenne & Nierstenhöfer, 2019 ). The crystal structures of simple organoselenium cations with three alkyl or aryl substituents, e.g. [Ph₂MeSe]⁺ (Dumont et al., 1974), [Me₃Se]⁺ (Hope, 1966), or [Ph₃Se]⁺ (Leicester & Bergstrom, 1929), and a selenium cation with one β-ketone substituent and two methyl groups {[Me₂SeCH₂COOH]⁺; Ip & Ganther, 1990} have been previously reported.

5. Synthesis and crystallization

[Se₈][B₁₂F₁₁NH₃]₂ was prepared by a salt metathesis reaction of Na[B₁₂F₁₁NH₃] with [Se₈][AsF₆]₂ in liquid sulfur dioxide as a solvent in an H-shaped glass vessel with an incorporated frit. The insoluble by-product Na[AsF₆] was removed by filtration. The soluble black residue was dissolved in acetone in order to obtain single crystals of the intended compound [Se₈][B₁₂F₁₁NH₃]₂. The title compound was obtained as a by-product from the reaction of [Se₈][B₁₂F₁₁NH₃]₂ with acetone. Single crystals were grown by slow diffusion of diethyl ether into a saturated solution of acetone at room temperature. During crystallization a red precipitate formed, which hints at the formation of elemental red selenium. We assume that the formation of the title cation is the result of a C—H activation of acetone by the [Se₈]²⁺ cation.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms were positioned geometrically (N—H = 0.91 or C—H = 0.95–0.99 °) and refined using a riding model with U_iso(H) = 1.2U_eq(C, N) or 1.5U_eq(C-methyl).

Table 3
Experimental details

Crystal data
Chemical formula	C₉H₁₅O₃Se⁺·B₁₂F₁₁H₃N⁻
M_r	605.92
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	150
a, b, c (Å)	12.6157 (3), 16.9629 (4), 22.2759 (6)
V (Å³)	4767.0 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	1.68
Crystal size (mm)	0.17 × 0.11 × 0.06

Data collection
Diffractometer	Rigaku Oxford Diffraction Xcalibur, Eos, Gemini ultra
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.758, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17080, 5719, 4622
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.693

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.03
No. of reflections	5719
No. of parameters	338
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.42
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1977644

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989020000481/pk2622sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020000481/pk2622Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Tris(2-oxopropyl)selanium 1-ammonioundecafluorododecaborate top

Crystal data top

C₉H₁₅O₃Se⁺·B₁₂F₁₁H₃N⁻	D_x = 1.689 Mg m⁻³
M_r = 605.92	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5874 reflections
a = 12.6157 (3) Å	θ = 3.0–29.2°
b = 16.9629 (4) Å	µ = 1.68 mm⁻¹
c = 22.2759 (6) Å	T = 150 K
V = 4767.0 (2) Å³	Block, clear light colourless
Z = 8	0.17 × 0.11 × 0.06 mm
F(000) = 2368

Data collection top

Rigaku Oxford Diffraction Xcalibur, Eos, Gemini ultra diffractometer	5719 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	4622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 16.2705 pixels mm^-1	θ_max = 29.5°, θ_min = 2.7°
ω scans	h = −17→14
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	k = −23→14
T_min = 0.758, T_max = 1.000	l = −30→26
17080 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0441P)² + 2.0302P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
5719 reflections	Δρ_max = 0.45 e Å⁻³
338 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

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
Se1	0.48873 (2)	0.60776 (2)	0.89752 (2)	0.02430 (7)
F11	0.42902 (10)	0.72825 (7)	0.75079 (5)	0.0307 (3)
F5	0.67805 (10)	0.73550 (8)	0.71785 (6)	0.0336 (3)
F6	0.51832 (10)	0.87887 (7)	0.68324 (6)	0.0313 (3)
F2	0.46146 (10)	0.86422 (9)	0.54175 (6)	0.0383 (3)
F3	0.58351 (11)	0.71123 (9)	0.48901 (6)	0.0407 (3)
F4	0.71576 (10)	0.63101 (7)	0.59821 (6)	0.0373 (3)
F10	0.54740 (11)	0.57225 (7)	0.69968 (7)	0.0402 (3)
F12	0.31082 (10)	0.61473 (8)	0.65310 (7)	0.0424 (3)
F7	0.29441 (9)	0.80596 (8)	0.64224 (6)	0.0414 (3)
O1	0.40468 (11)	0.75890 (9)	0.88266 (7)	0.0324 (3)
O3	0.34256 (12)	0.48099 (9)	0.88486 (8)	0.0347 (4)
F8	0.33176 (11)	0.70261 (11)	0.52287 (7)	0.0569 (4)
F9	0.48962 (12)	0.55469 (9)	0.55813 (8)	0.0560 (5)
O2	0.65887 (13)	0.58953 (10)	0.97614 (7)	0.0402 (4)
N1	0.70624 (12)	0.82307 (9)	0.58287 (7)	0.0203 (3)
H	0.712266	0.822528	0.542164	0.024*
HA	0.766087	0.802626	0.599535	0.024*
HB	0.697272	0.873550	0.595723	0.024*
C2	0.49612 (15)	0.76780 (13)	0.86736 (10)	0.0261 (4)
C1	0.56931 (15)	0.69751 (11)	0.86722 (10)	0.0255 (4)
H1A	0.631476	0.707672	0.893214	0.031*
H1B	0.594761	0.686763	0.825987	0.031*
C5	0.67037 (16)	0.53359 (13)	0.94298 (10)	0.0303 (5)
C8	0.34198 (16)	0.51183 (12)	0.83614 (11)	0.0301 (5)
C4	0.59842 (17)	0.52743 (12)	0.88906 (10)	0.0298 (5)
H4A	0.565919	0.474365	0.887190	0.036*
H4B	0.639274	0.536213	0.851705	0.036*
C7	0.40988 (17)	0.58340 (13)	0.82470 (9)	0.0289 (4)
H7A	0.364670	0.628733	0.813401	0.035*
H7B	0.459606	0.572818	0.791277	0.035*
C3	0.54099 (18)	0.84483 (13)	0.84772 (12)	0.0370 (5)
H3A	0.483168	0.880480	0.836498	0.056*
H3B	0.587517	0.836547	0.813056	0.056*
H3C	0.581813	0.868127	0.880676	0.056*
B1	0.61004 (16)	0.77319 (13)	0.60178 (10)	0.0197 (4)
B5	0.60007 (17)	0.72730 (13)	0.67335 (10)	0.0218 (4)
B7	0.38811 (18)	0.76623 (15)	0.63220 (11)	0.0273 (5)
C6	0.75232 (19)	0.47173 (14)	0.95177 (14)	0.0460 (6)
H6A	0.789968	0.462767	0.913900	0.069*
H6B	0.718250	0.422654	0.964678	0.069*
H6C	0.802785	0.488972	0.982531	0.069*
C9	0.2774 (2)	0.48398 (15)	0.78432 (13)	0.0484 (7)
H9A	0.247527	0.432053	0.793526	0.073*
H9B	0.322503	0.480121	0.748599	0.073*
H9C	0.219847	0.521441	0.776727	0.073*
B11	0.46184 (17)	0.72269 (13)	0.69204 (10)	0.0229 (4)
B4	0.62094 (18)	0.66877 (13)	0.60733 (11)	0.0248 (5)
B3	0.54671 (19)	0.71304 (15)	0.54721 (11)	0.0287 (5)
B6	0.51274 (16)	0.80691 (13)	0.65415 (10)	0.0210 (4)
B8	0.40916 (19)	0.70841 (18)	0.56625 (11)	0.0346 (6)
B12	0.39774 (18)	0.66108 (15)	0.63797 (11)	0.0297 (5)
B10	0.52843 (18)	0.63720 (14)	0.66360 (12)	0.0266 (5)
B2	0.48040 (17)	0.79836 (16)	0.57652 (10)	0.0265 (5)
B9	0.4957 (2)	0.62763 (17)	0.58525 (13)	0.0345 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.02537 (11)	0.02575 (12)	0.02179 (11)	−0.00251 (8)	0.00435 (8)	−0.00125 (8)
F11	0.0338 (6)	0.0364 (7)	0.0220 (6)	0.0001 (5)	0.0069 (5)	0.0056 (5)
F5	0.0289 (6)	0.0450 (7)	0.0269 (6)	0.0002 (6)	−0.0052 (5)	0.0055 (6)
F6	0.0354 (7)	0.0240 (6)	0.0344 (7)	0.0013 (5)	0.0103 (5)	−0.0022 (5)
F2	0.0287 (6)	0.0525 (8)	0.0335 (7)	0.0104 (6)	0.0019 (5)	0.0215 (6)
F3	0.0429 (7)	0.0585 (9)	0.0208 (6)	−0.0120 (7)	0.0056 (6)	−0.0084 (6)
F4	0.0304 (6)	0.0282 (6)	0.0533 (9)	0.0073 (5)	0.0105 (6)	−0.0017 (6)
F10	0.0412 (7)	0.0284 (6)	0.0509 (9)	0.0057 (6)	0.0125 (7)	0.0147 (6)
F12	0.0295 (7)	0.0503 (8)	0.0475 (8)	−0.0186 (6)	0.0048 (6)	−0.0008 (7)
F7	0.0183 (6)	0.0579 (9)	0.0480 (8)	0.0104 (6)	0.0064 (5)	0.0182 (7)
O1	0.0223 (7)	0.0366 (8)	0.0383 (9)	0.0016 (6)	0.0042 (6)	−0.0074 (7)
O3	0.0341 (8)	0.0224 (7)	0.0476 (10)	−0.0006 (6)	0.0103 (7)	0.0050 (7)
F8	0.0358 (7)	0.0992 (13)	0.0357 (8)	−0.0223 (8)	−0.0166 (6)	0.0007 (8)
F9	0.0596 (10)	0.0477 (9)	0.0608 (10)	−0.0261 (7)	0.0160 (8)	−0.0285 (8)
O2	0.0400 (9)	0.0458 (10)	0.0347 (9)	−0.0003 (8)	−0.0040 (7)	−0.0113 (8)
N1	0.0174 (7)	0.0226 (8)	0.0209 (8)	0.0032 (6)	0.0019 (6)	0.0011 (7)
C2	0.0240 (10)	0.0285 (10)	0.0258 (10)	0.0009 (8)	−0.0029 (8)	−0.0038 (8)
C1	0.0214 (9)	0.0239 (10)	0.0314 (11)	−0.0034 (8)	0.0055 (8)	−0.0025 (8)
C5	0.0267 (10)	0.0297 (11)	0.0345 (12)	−0.0060 (9)	0.0017 (9)	0.0017 (9)
C8	0.0243 (10)	0.0242 (10)	0.0417 (13)	0.0035 (8)	0.0008 (9)	−0.0022 (9)
C4	0.0314 (11)	0.0237 (10)	0.0343 (12)	−0.0015 (9)	0.0006 (9)	−0.0032 (9)
C7	0.0297 (11)	0.0330 (11)	0.0239 (10)	−0.0049 (9)	0.0012 (8)	0.0004 (9)
C3	0.0310 (11)	0.0283 (11)	0.0517 (15)	−0.0009 (10)	−0.0049 (10)	0.0026 (11)
B1	0.0159 (9)	0.0226 (10)	0.0204 (10)	0.0021 (8)	0.0009 (8)	0.0018 (8)
B5	0.0184 (10)	0.0265 (11)	0.0204 (10)	0.0018 (9)	−0.0026 (8)	0.0023 (9)
B7	0.0178 (10)	0.0385 (13)	0.0255 (12)	0.0011 (10)	−0.0007 (9)	0.0058 (10)
C6	0.0332 (12)	0.0346 (12)	0.0700 (19)	−0.0007 (10)	−0.0079 (12)	0.0005 (13)
C9	0.0381 (13)	0.0408 (13)	0.0664 (19)	−0.0030 (11)	−0.0167 (13)	−0.0051 (13)
B11	0.0203 (10)	0.0259 (11)	0.0226 (11)	0.0005 (9)	0.0025 (9)	0.0042 (9)
B4	0.0229 (10)	0.0217 (10)	0.0297 (12)	0.0000 (9)	0.0040 (9)	−0.0023 (9)
B3	0.0265 (11)	0.0383 (13)	0.0213 (11)	−0.0075 (10)	0.0007 (9)	−0.0052 (10)
B6	0.0186 (10)	0.0236 (10)	0.0207 (10)	0.0024 (8)	0.0020 (8)	0.0038 (9)
B8	0.0235 (11)	0.0546 (16)	0.0257 (12)	−0.0107 (11)	−0.0066 (10)	−0.0014 (11)
B12	0.0223 (11)	0.0358 (13)	0.0309 (13)	−0.0100 (10)	0.0012 (9)	0.0010 (11)
B10	0.0257 (11)	0.0228 (11)	0.0313 (12)	−0.0006 (9)	0.0039 (9)	0.0023 (10)
B2	0.0184 (10)	0.0408 (13)	0.0204 (11)	0.0017 (10)	−0.0011 (8)	0.0073 (10)
B9	0.0344 (13)	0.0347 (13)	0.0344 (13)	−0.0116 (11)	0.0052 (11)	−0.0099 (11)

Geometric parameters (Å, º) top

Se1—C1	1.9511 (19)	B1—B5	1.779 (3)
Se1—C4	1.951 (2)	B1—B4	1.781 (3)
Se1—C7	1.947 (2)	B1—B3	1.777 (3)
F11—B11	1.376 (3)	B1—B6	1.787 (3)
F5—B5	1.404 (2)	B1—B2	1.781 (3)
F6—B6	1.384 (3)	B5—B11	1.795 (3)
F2—B2	1.380 (3)	B5—B4	1.794 (3)
F3—B3	1.378 (3)	B5—B6	1.794 (3)
F4—B4	1.372 (3)	B5—B10	1.789 (3)
F10—B10	1.384 (3)	B7—B11	1.785 (3)
F12—B12	1.391 (3)	B7—B6	1.785 (3)
F7—B7	1.379 (3)	B7—B8	1.786 (4)
O1—C2	1.212 (2)	B7—B12	1.792 (4)
O3—C8	1.205 (3)	B7—B2	1.786 (3)
F8—B8	1.377 (3)	C6—H6A	0.9800
F9—B9	1.379 (3)	C6—H6B	0.9800
O2—C5	1.211 (3)	C6—H6C	0.9800
N1—H	0.9100	C9—H9A	0.9800
N1—HA	0.9100	C9—H9B	0.9800
N1—HB	0.9100	C9—H9C	0.9800
N1—B1	1.538 (3)	B11—B6	1.779 (3)
C2—C1	1.508 (3)	B11—B12	1.788 (3)
C2—C3	1.490 (3)	B11—B10	1.792 (3)
C1—H1A	0.9900	B4—B3	1.798 (4)
C1—H1B	0.9900	B4—B10	1.794 (3)
C5—C4	1.509 (3)	B4—B9	1.795 (3)
C5—C6	1.486 (3)	B3—B8	1.788 (3)
C8—C7	1.507 (3)	B3—B2	1.795 (4)
C8—C9	1.489 (3)	B3—B9	1.797 (4)
C4—H4A	0.9900	B6—B2	1.783 (3)
C4—H4B	0.9900	B8—B12	1.794 (4)
C7—H7A	0.9900	B8—B2	1.786 (4)
C7—H7B	0.9900	B8—B9	1.803 (4)
C3—H3A	0.9800	B12—B10	1.791 (3)
C3—H3B	0.9800	B12—B9	1.797 (4)
C3—H3C	0.9800	B10—B9	1.801 (4)

C4—Se1—C1	98.17 (9)	F4—B4—B10	122.08 (18)
C7—Se1—C1	98.26 (9)	F4—B4—B9	123.03 (18)
C7—Se1—C4	97.67 (9)	B1—B4—B5	59.67 (12)
H—N1—HA	109.5	B1—B4—B3	59.52 (13)
H—N1—HB	109.5	B1—B4—B10	107.16 (15)
HA—N1—HB	109.5	B1—B4—B9	107.43 (17)
B1—N1—H	109.5	B5—B4—B3	107.63 (16)
B1—N1—HA	109.5	B5—B4—B10	59.81 (13)
B1—N1—HB	109.5	B5—B4—B9	108.09 (16)
O1—C2—C1	118.99 (19)	B10—B4—B3	107.82 (16)
O1—C2—C3	123.6 (2)	B10—B4—B9	60.21 (14)
C3—C2—C1	117.40 (17)	B9—B4—B3	60.01 (15)
Se1—C1—H1A	110.3	F3—B3—B1	120.35 (18)
Se1—C1—H1B	110.3	F3—B3—B4	121.07 (19)
C2—C1—Se1	107.29 (13)	F3—B3—B8	123.31 (19)
C2—C1—H1A	110.3	F3—B3—B2	121.2 (2)
C2—C1—H1B	110.3	F3—B3—B9	123.1 (2)
H1A—C1—H1B	108.5	B1—B3—B4	59.75 (13)
O2—C5—C4	117.9 (2)	B1—B3—B8	107.42 (16)
O2—C5—C6	123.8 (2)	B1—B3—B2	59.84 (12)
C6—C5—C4	118.3 (2)	B1—B3—B9	107.53 (17)
O3—C8—C7	119.9 (2)	B8—B3—B4	108.09 (17)
O3—C8—C9	124.3 (2)	B8—B3—B2	59.79 (14)
C9—C8—C7	115.8 (2)	B8—B3—B9	60.37 (15)
Se1—C4—H4A	110.2	B2—B3—B4	107.98 (16)
Se1—C4—H4B	110.2	B2—B3—B9	108.17 (17)
C5—C4—Se1	107.53 (14)	B9—B3—B4	59.91 (14)
C5—C4—H4A	110.2	F6—B6—B1	123.57 (16)
C5—C4—H4B	110.2	F6—B6—B5	121.40 (17)
H4A—C4—H4B	108.5	F6—B6—B7	120.93 (16)
Se1—C7—H7A	110.0	F6—B6—B11	120.30 (17)
Se1—C7—H7B	110.0	F6—B6—B2	122.52 (17)
C8—C7—Se1	108.69 (15)	B1—B6—B5	59.55 (12)
C8—C7—H7A	110.0	B7—B6—B1	107.61 (16)
C8—C7—H7B	110.0	B7—B6—B5	108.37 (16)
H7A—C7—H7B	108.3	B11—B6—B1	107.49 (15)
C2—C3—H3A	109.5	B11—B6—B5	60.29 (12)
C2—C3—H3B	109.5	B11—B6—B7	60.11 (13)
C2—C3—H3C	109.5	B11—B6—B2	108.19 (16)
H3A—C3—H3B	109.5	B2—B6—B1	59.87 (12)
H3A—C3—H3C	109.5	B2—B6—B5	108.09 (16)
H3B—C3—H3C	109.5	B2—B6—B7	60.09 (13)
N1—B1—B5	122.82 (16)	F8—B8—B7	120.7 (2)
N1—B1—B4	120.34 (16)	F8—B8—B3	121.66 (19)
N1—B1—B3	118.90 (16)	F8—B8—B12	122.41 (19)
N1—B1—B6	123.00 (16)	F8—B8—B2	120.5 (2)
N1—B1—B2	120.40 (16)	F8—B8—B9	122.7 (2)
B5—B1—B4	60.53 (13)	B7—B8—B3	108.37 (16)
B5—B1—B6	60.43 (12)	B7—B8—B12	60.08 (14)
B5—B1—B2	108.85 (15)	B7—B8—B9	108.32 (18)
B4—B1—B6	109.03 (15)	B3—B8—B12	107.98 (17)
B4—B1—B2	109.34 (16)	B3—B8—B9	60.07 (14)
B3—B1—B5	109.28 (16)	B12—B8—B9	59.96 (15)
B3—B1—B4	60.73 (14)	B2—B8—B7	60.01 (14)
B3—B1—B6	108.75 (15)	B2—B8—B3	60.29 (14)
B3—B1—B2	60.58 (14)	B2—B8—B12	107.98 (17)
B2—B1—B6	59.93 (12)	B2—B8—B9	108.32 (16)
F5—B5—B1	122.70 (17)	F12—B12—B7	121.77 (19)
F5—B5—B11	121.44 (17)	F12—B12—B11	121.59 (18)
F5—B5—B4	122.07 (17)	F12—B12—B8	122.15 (18)
F5—B5—B6	121.61 (17)	F12—B12—B10	121.38 (19)
F5—B5—B10	121.63 (17)	F12—B12—B9	121.48 (19)
B1—B5—B11	107.20 (15)	B7—B12—B8	59.75 (15)
B1—B5—B4	59.80 (12)	B7—B12—B9	108.29 (17)
B1—B5—B6	60.03 (12)	B11—B12—B7	59.82 (13)
B1—B5—B10	107.51 (16)	B11—B12—B8	107.58 (17)
B4—B5—B11	107.98 (15)	B11—B12—B10	60.08 (13)
B4—B5—B6	108.13 (15)	B11—B12—B9	108.28 (16)
B6—B5—B11	59.44 (12)	B8—B12—B9	60.26 (16)
B10—B5—B11	60.00 (12)	B10—B12—B7	108.08 (16)
B10—B5—B4	60.11 (13)	B10—B12—B8	108.13 (16)
B10—B5—B6	107.69 (15)	B10—B12—B9	60.24 (15)
F7—B7—B11	121.85 (18)	F10—B10—B5	121.47 (19)
F7—B7—B6	121.44 (19)	F10—B10—B11	121.32 (19)
F7—B7—B8	121.95 (18)	F10—B10—B4	122.04 (18)
F7—B7—B12	122.20 (18)	F10—B10—B12	121.60 (18)
F7—B7—B2	121.48 (18)	F10—B10—B9	122.0 (2)
B11—B7—B8	108.03 (17)	B5—B10—B11	60.16 (13)
B11—B7—B12	59.96 (13)	B5—B10—B4	60.08 (13)
B11—B7—B2	107.76 (15)	B5—B10—B12	108.09 (16)
B6—B7—B11	59.77 (12)	B5—B10—B9	108.08 (17)
B6—B7—B8	107.85 (16)	B11—B10—B4	108.08 (16)
B6—B7—B12	107.77 (16)	B11—B10—B9	107.95 (17)
B6—B7—B2	59.88 (13)	B4—B10—B9	59.92 (14)
B8—B7—B12	60.17 (15)	B12—B10—B11	59.87 (13)
B8—B7—B2	59.97 (14)	B12—B10—B4	107.97 (17)
B2—B7—B12	108.01 (17)	B12—B10—B9	60.04 (14)
C5—C6—H6A	109.5	F2—B2—B1	122.02 (17)
C5—C6—H6B	109.5	F2—B2—B7	121.58 (17)
C5—C6—H6C	109.5	F2—B2—B3	121.96 (18)
H6A—C6—H6B	109.5	F2—B2—B6	121.21 (19)
H6A—C6—H6C	109.5	F2—B2—B8	122.18 (18)
H6B—C6—H6C	109.5	B1—B2—B7	107.82 (16)
C8—C9—H9A	109.5	B1—B2—B3	59.58 (13)
C8—C9—H9B	109.5	B1—B2—B6	60.20 (12)
C8—C9—H9C	109.5	B1—B2—B8	107.33 (17)
H9A—C9—H9B	109.5	B7—B2—B3	108.08 (17)
H9A—C9—H9C	109.5	B6—B2—B7	60.03 (13)
H9B—C9—H9C	109.5	B6—B2—B3	108.17 (16)
F11—B11—B5	120.67 (17)	B6—B2—B8	108.01 (16)
F11—B11—B7	121.67 (17)	B8—B2—B7	60.02 (14)
F11—B11—B6	120.32 (18)	B8—B2—B3	59.93 (14)
F11—B11—B12	123.00 (17)	F9—B9—B4	121.2 (2)
F11—B11—B10	122.20 (17)	F9—B9—B3	122.5 (2)
B7—B11—B5	108.36 (15)	F9—B9—B8	123.0 (2)
B7—B11—B12	60.22 (14)	F9—B9—B12	122.07 (19)
B7—B11—B10	108.37 (17)	F9—B9—B10	121.2 (2)
B6—B11—B5	60.28 (12)	B4—B9—B3	60.07 (14)
B6—B11—B7	60.11 (12)	B4—B9—B8	107.58 (18)
B6—B11—B12	108.24 (16)	B4—B9—B12	107.67 (18)
B6—B11—B10	108.23 (15)	B4—B9—B10	59.86 (14)
B12—B11—B5	107.98 (16)	B3—B9—B8	59.56 (15)
B12—B11—B10	60.05 (14)	B3—B9—B10	107.60 (17)
B10—B11—B5	59.84 (13)	B12—B9—B3	107.44 (19)
F4—B4—B1	121.42 (17)	B12—B9—B8	59.78 (15)
F4—B4—B5	120.51 (18)	B12—B9—B10	59.72 (14)
F4—B4—B3	122.59 (18)	B10—B9—B8	107.33 (18)

F11—B11—B6—F6	−0.9 (3)	B11—B10—B9—B3	63.0 (2)
F11—B11—B6—B1	147.93 (18)	B11—B10—B9—B8	0.3 (2)
F11—B11—B6—B5	110.3 (2)	B11—B10—B9—B12	−37.27 (16)
F11—B11—B6—B7	−111.4 (2)	B4—B1—B5—F5	110.9 (2)
F11—B11—B6—B2	−148.84 (18)	B4—B1—B5—B11	−101.17 (17)
F11—B11—B12—F12	−0.5 (3)	B4—B1—B5—B6	−138.70 (16)
F11—B11—B12—B7	110.5 (2)	B4—B1—B5—B10	−37.99 (15)
F11—B11—B12—B8	147.75 (19)	B4—B1—B3—F3	−110.5 (2)
F11—B11—B12—B10	−111.0 (2)	B4—B1—B3—B8	101.17 (19)
F11—B11—B12—B9	−148.6 (2)	B4—B1—B3—B2	138.77 (16)
F11—B11—B10—F10	1.5 (3)	B4—B1—B3—B9	37.55 (16)
F11—B11—B10—B5	−109.3 (2)	B4—B1—B6—F6	147.01 (18)
F11—B11—B10—B4	−146.95 (19)	B4—B1—B6—B5	37.43 (15)
F11—B11—B10—B12	112.3 (2)	B4—B1—B6—B7	−63.93 (19)
F11—B11—B10—B9	149.69 (19)	B4—B1—B6—B11	−0.6 (2)
F5—B5—B11—F11	0.9 (3)	B4—B1—B6—B2	−101.84 (18)
F5—B5—B11—B7	148.07 (19)	B4—B1—B2—F2	−148.4 (2)
F5—B5—B11—B6	110.6 (2)	B4—B1—B2—B7	63.4 (2)
F5—B5—B11—B12	−148.19 (18)	B4—B1—B2—B3	−37.54 (15)
F5—B5—B11—B10	−110.9 (2)	B4—B1—B2—B6	101.31 (17)
F5—B5—B4—F4	−1.0 (3)	B4—B1—B2—B8	0.1 (2)
F5—B5—B4—B1	−111.9 (2)	B4—B5—B11—F11	149.43 (18)
F5—B5—B4—B3	−148.52 (18)	B4—B5—B11—B7	−63.42 (19)
F5—B5—B4—B10	110.7 (2)	B4—B5—B11—B6	−100.86 (17)
F5—B5—B4—B9	148.08 (19)	B4—B5—B11—B12	0.3 (2)
F5—B5—B6—F6	−1.0 (3)	B4—B5—B11—B10	37.60 (15)
F5—B5—B6—B1	112.2 (2)	B4—B5—B6—F6	−150.00 (17)
F5—B5—B6—B7	−147.79 (18)	B4—B5—B6—B1	−36.88 (14)
F5—B5—B6—B11	−110.4 (2)	B4—B5—B6—B7	63.16 (19)
F5—B5—B6—B2	148.59 (18)	B4—B5—B6—B11	100.60 (17)
F5—B5—B10—F10	0.0 (3)	B4—B5—B6—B2	−0.5 (2)
F5—B5—B10—B11	110.6 (2)	B4—B5—B10—F10	111.4 (2)
F5—B5—B10—B4	−111.4 (2)	B4—B5—B10—B11	−137.98 (16)
F5—B5—B10—B12	147.83 (18)	B4—B5—B10—B12	−100.75 (18)
F5—B5—B10—B9	−148.66 (19)	B4—B5—B10—B9	−37.24 (16)
F6—B6—B2—F2	1.3 (3)	B4—B3—B8—F8	−149.7 (2)
F6—B6—B2—B1	112.8 (2)	B4—B3—B8—B7	63.4 (2)
F6—B6—B2—B7	−109.7 (2)	B4—B3—B8—B12	−0.2 (2)
F6—B6—B2—B3	149.52 (18)	B4—B3—B8—B2	100.69 (18)
F6—B6—B2—B8	−147.10 (18)	B4—B3—B8—B9	−37.58 (17)
F3—B3—B8—F8	0.1 (4)	B4—B3—B2—F2	147.77 (19)
F3—B3—B8—B7	−146.8 (2)	B4—B3—B2—B1	36.77 (15)
F3—B3—B8—B12	149.6 (2)	B4—B3—B2—B7	−63.7 (2)
F3—B3—B8—B2	−109.5 (2)	B4—B3—B2—B6	−0.2 (2)
F3—B3—B8—B9	112.2 (3)	B4—B3—B2—B8	−100.88 (18)
F3—B3—B2—F2	1.6 (3)	B4—B3—B9—F9	−110.0 (3)
F3—B3—B2—B1	−109.4 (2)	B4—B3—B9—B8	137.93 (18)
F3—B3—B2—B7	150.18 (19)	B4—B3—B9—B12	100.73 (19)
F3—B3—B2—B6	−146.30 (19)	B4—B3—B9—B10	37.79 (16)
F3—B3—B2—B8	113.0 (2)	B4—B10—B9—F9	110.4 (2)
F3—B3—B9—F9	−0.5 (4)	B4—B10—B9—B3	−37.88 (16)
F3—B3—B9—B4	109.5 (2)	B4—B10—B9—B8	−100.64 (18)
F3—B3—B9—B8	−112.5 (2)	B4—B10—B9—B12	−138.19 (18)
F3—B3—B9—B12	−149.7 (2)	B3—B1—B5—F5	148.45 (18)
F3—B3—B9—B10	147.3 (2)	B3—B1—B5—B11	−63.60 (19)
F4—B4—B3—F3	−0.6 (3)	B3—B1—B5—B4	37.57 (15)
F4—B4—B3—B1	−110.0 (2)	B3—B1—B5—B6	−101.14 (17)
F4—B4—B3—B8	149.99 (19)	B3—B1—B5—B10	−0.4 (2)
F4—B4—B3—B2	−146.79 (18)	B3—B1—B4—F4	111.9 (2)
F4—B4—B3—B9	112.2 (2)	B3—B1—B4—B5	−138.72 (16)
F4—B4—B10—F10	−1.3 (3)	B3—B1—B4—B10	−100.95 (18)
F4—B4—B10—B5	109.2 (2)	B3—B1—B4—B9	−37.57 (16)
F4—B4—B10—B11	146.82 (19)	B3—B1—B6—F6	−148.40 (19)
F4—B4—B10—B12	−149.87 (19)	B3—B1—B6—B5	102.02 (17)
F4—B4—B10—B9	−112.5 (2)	B3—B1—B6—B7	0.7 (2)
F4—B4—B9—F9	0.5 (4)	B3—B1—B6—B11	64.03 (19)
F4—B4—B9—B3	−111.5 (2)	B3—B1—B6—B2	−37.25 (16)
F4—B4—B9—B8	−148.8 (2)	B3—B1—B2—F2	−110.9 (2)
F4—B4—B9—B12	148.1 (2)	B3—B1—B2—B7	100.92 (19)
F4—B4—B9—B10	111.0 (2)	B3—B1—B2—B6	138.85 (17)
F10—B10—B9—F9	−0.8 (3)	B3—B1—B2—B8	37.64 (16)
F10—B10—B9—B4	−111.2 (2)	B3—B4—B10—F10	149.1 (2)
F10—B10—B9—B3	−149.03 (19)	B3—B4—B10—B5	−100.43 (17)
F10—B10—B9—B8	148.21 (19)	B3—B4—B10—B11	−62.8 (2)
F10—B10—B9—B12	110.7 (2)	B3—B4—B10—B12	0.5 (2)
F12—B12—B10—F10	−0.5 (3)	B3—B4—B10—B9	37.91 (17)
F12—B12—B10—B5	−148.3 (2)	B3—B4—B9—F9	112.1 (3)
F12—B12—B10—B11	−110.9 (2)	B3—B4—B9—B8	−37.30 (17)
F12—B12—B10—B4	148.19 (19)	B3—B4—B9—B12	−100.3 (2)
F12—B12—B10—B9	110.9 (2)	B3—B4—B9—B10	−137.52 (18)
F12—B12—B9—F9	−0.7 (4)	B3—B8—B12—F12	−148.0 (2)
F12—B12—B9—B4	−147.9 (2)	B3—B8—B12—B7	101.27 (19)
F12—B12—B9—B3	148.7 (2)	B3—B8—B12—B11	64.0 (2)
F12—B12—B9—B8	111.6 (2)	B3—B8—B12—B10	0.5 (2)
F12—B12—B9—B10	−110.7 (2)	B3—B8—B12—B9	−37.46 (17)
F7—B7—B11—F11	−1.2 (3)	B3—B8—B2—F2	111.0 (2)
F7—B7—B11—B5	−147.9 (2)	B3—B8—B2—B1	−37.48 (15)
F7—B7—B11—B6	−110.4 (2)	B3—B8—B2—B7	−138.44 (17)
F7—B7—B11—B12	111.4 (2)	B3—B8—B2—B6	−100.99 (17)
F7—B7—B11—B10	148.7 (2)	B3—B8—B9—F9	−111.1 (3)
F7—B7—B6—F6	1.6 (3)	B3—B8—B9—B4	37.52 (16)
F7—B7—B6—B1	−148.48 (19)	B3—B8—B9—B12	138.12 (18)
F7—B7—B6—B5	148.58 (19)	B3—B8—B9—B10	100.60 (18)
F7—B7—B6—B11	111.1 (2)	B6—B1—B5—F5	−110.4 (2)
F7—B7—B6—B2	−110.7 (2)	B6—B1—B5—B11	37.53 (15)
F7—B7—B8—F8	0.7 (3)	B6—B1—B5—B4	138.70 (16)
F7—B7—B8—B3	147.9 (2)	B6—B1—B5—B10	100.72 (16)
F7—B7—B8—B12	−111.5 (2)	B6—B1—B4—F4	−146.77 (19)
F7—B7—B8—B2	110.5 (2)	B6—B1—B4—B5	−37.38 (14)
F7—B7—B8—B9	−148.5 (2)	B6—B1—B4—B3	101.33 (17)
F7—B7—B12—F12	−0.2 (3)	B6—B1—B4—B10	0.4 (2)
F7—B7—B12—B11	−110.9 (2)	B6—B1—B4—B9	63.8 (2)
F7—B7—B12—B8	111.1 (2)	B6—B1—B3—F3	147.7 (2)
F7—B7—B12—B10	−148.0 (2)	B6—B1—B3—B4	−101.80 (17)
F7—B7—B12—B9	148.2 (2)	B6—B1—B3—B8	−0.6 (2)
F7—B7—B2—F2	0.3 (3)	B6—B1—B3—B2	36.97 (15)
F7—B7—B2—B1	148.6 (2)	B6—B1—B3—B9	−64.3 (2)
F7—B7—B2—B3	−148.4 (2)	B6—B1—B2—F2	110.3 (2)
F7—B7—B2—B6	110.6 (2)	B6—B1—B2—B7	−37.93 (16)
F7—B7—B2—B8	−111.3 (2)	B6—B1—B2—B3	−138.85 (17)
O1—C2—C1—Se1	−2.6 (2)	B6—B1—B2—B8	−101.21 (17)
O3—C8—C7—Se1	1.0 (2)	B6—B5—B11—F11	−109.7 (2)
F8—B8—B12—F12	1.3 (4)	B6—B5—B11—B7	37.43 (15)
F8—B8—B12—B7	−109.4 (3)	B6—B5—B11—B12	101.17 (17)
F8—B8—B12—B11	−146.8 (2)	B6—B5—B11—B10	138.45 (17)
F8—B8—B12—B10	149.8 (2)	B6—B5—B4—F4	147.86 (18)
F8—B8—B12—B9	111.8 (3)	B6—B5—B4—B1	36.98 (14)
F8—B8—B2—F2	−0.4 (3)	B6—B5—B4—B3	0.4 (2)
F8—B8—B2—B1	−148.9 (2)	B6—B5—B4—B10	−100.41 (16)
F8—B8—B2—B7	110.1 (2)	B6—B5—B4—B9	−63.0 (2)
F8—B8—B2—B3	−111.4 (2)	B6—B5—B10—F10	−147.41 (19)
F8—B8—B2—B6	147.6 (2)	B6—B5—B10—B11	−36.83 (15)
F8—B8—B9—F9	−0.6 (4)	B6—B5—B10—B4	101.15 (17)
F8—B8—B9—B4	148.0 (2)	B6—B5—B10—B12	0.4 (2)
F8—B8—B9—B3	110.5 (2)	B6—B5—B10—B9	63.9 (2)
F8—B8—B9—B12	−111.4 (2)	B6—B7—B11—F11	109.2 (2)
F8—B8—B9—B10	−148.9 (2)	B6—B7—B11—B5	−37.50 (15)
O2—C5—C4—Se1	−9.3 (2)	B6—B7—B11—B12	−138.15 (17)
N1—B1—B5—F5	1.9 (3)	B6—B7—B11—B10	−100.92 (17)
N1—B1—B5—B11	149.81 (17)	B6—B7—B8—F8	−147.2 (2)
N1—B1—B5—B4	−109.0 (2)	B6—B7—B8—B3	0.0 (2)
N1—B1—B5—B6	112.3 (2)	B6—B7—B8—B12	100.66 (17)
N1—B1—B5—B10	−147.01 (17)	B6—B7—B8—B2	−37.34 (16)
N1—B1—B4—F4	3.6 (3)	B6—B7—B8—B9	63.7 (2)
N1—B1—B4—B5	113.0 (2)	B6—B7—B12—F12	147.91 (19)
N1—B1—B4—B3	−108.3 (2)	B6—B7—B12—B11	37.25 (15)
N1—B1—B4—B10	150.76 (17)	B6—B7—B12—B8	−100.79 (17)
N1—B1—B4—B9	−145.85 (18)	B6—B7—B12—B10	0.1 (2)
N1—B1—B3—F3	0.1 (3)	B6—B7—B12—B9	−63.7 (2)
N1—B1—B3—B4	110.61 (19)	B6—B7—B2—F2	−110.3 (2)
N1—B1—B3—B8	−148.22 (18)	B6—B7—B2—B1	38.01 (16)
N1—B1—B3—B2	−110.62 (19)	B6—B7—B2—B3	100.97 (17)
N1—B1—B3—B9	148.16 (17)	B6—B7—B2—B8	138.13 (17)
N1—B1—B6—F6	−2.4 (3)	B6—B11—B12—F12	−148.5 (2)
N1—B1—B6—B5	−112.0 (2)	B6—B11—B12—B7	−37.52 (15)
N1—B1—B6—B7	146.64 (17)	B6—B11—B12—B8	−0.2 (2)
N1—B1—B6—B11	−149.98 (17)	B6—B11—B12—B10	100.97 (17)
N1—B1—B6—B2	108.7 (2)	B6—B11—B12—B9	63.5 (2)
N1—B1—B2—F2	−2.7 (3)	B6—B11—B10—F10	148.15 (19)
N1—B1—B2—B7	−150.88 (18)	B6—B11—B10—B5	37.33 (15)
N1—B1—B2—B3	108.2 (2)	B6—B11—B10—B4	−0.3 (2)
N1—B1—B2—B6	−112.9 (2)	B6—B11—B10—B12	−100.99 (17)
N1—B1—B2—B8	145.84 (18)	B6—B11—B10—B9	−63.6 (2)
C3—C2—C1—Se1	178.11 (17)	B8—B7—B11—F11	−150.19 (19)
B1—B5—B11—F11	−147.51 (18)	B8—B7—B11—B5	63.1 (2)
B1—B5—B11—B7	−0.4 (2)	B8—B7—B11—B6	100.57 (17)
B1—B5—B11—B6	−37.80 (15)	B8—B7—B11—B12	−37.58 (16)
B1—B5—B11—B12	63.4 (2)	B8—B7—B11—B10	−0.3 (2)
B1—B5—B11—B10	100.66 (17)	B8—B7—B6—F6	149.62 (19)
B1—B5—B4—F4	110.9 (2)	B8—B7—B6—B1	−0.4 (2)
B1—B5—B4—B3	−36.63 (15)	B8—B7—B6—B5	−63.4 (2)
B1—B5—B4—B10	−137.39 (16)	B8—B7—B6—B11	−100.87 (19)
B1—B5—B4—B9	−100.02 (18)	B8—B7—B6—B2	37.38 (17)
B1—B5—B6—F6	−113.1 (2)	B8—B7—B12—F12	−111.3 (2)
B1—B5—B6—B7	100.05 (17)	B8—B7—B12—B11	138.04 (16)
B1—B5—B6—B11	137.48 (16)	B8—B7—B12—B10	100.87 (18)
B1—B5—B6—B2	36.42 (14)	B8—B7—B12—B9	37.10 (17)
B1—B5—B10—F10	149.29 (18)	B8—B7—B2—F2	111.5 (2)
B1—B5—B10—B11	−100.14 (16)	B8—B7—B2—B1	−100.12 (19)
B1—B5—B10—B4	37.85 (15)	B8—B7—B2—B3	−37.15 (16)
B1—B5—B10—B12	−62.9 (2)	B8—B7—B2—B6	−138.13 (17)
B1—B5—B10—B9	0.6 (2)	B8—B3—B2—F2	−111.3 (2)
B1—B4—B3—F3	109.4 (2)	B8—B3—B2—B1	137.65 (17)
B1—B4—B3—B8	−100.03 (18)	B8—B3—B2—B7	37.19 (16)
B1—B4—B3—B2	−36.81 (15)	B8—B3—B2—B6	100.71 (18)
B1—B4—B3—B9	−137.81 (17)	B8—B3—B9—F9	112.1 (3)
B1—B4—B10—F10	−148.2 (2)	B8—B3—B9—B4	−137.93 (18)
B1—B4—B10—B5	−37.70 (15)	B8—B3—B9—B12	−37.20 (16)
B1—B4—B10—B11	−0.1 (2)	B8—B3—B9—B10	−100.15 (19)
B1—B4—B10—B12	63.2 (2)	B8—B12—B10—F10	−149.3 (2)
B1—B4—B10—B9	100.63 (19)	B8—B12—B10—B5	62.9 (2)
B1—B4—B9—F9	149.4 (2)	B8—B12—B10—B11	100.27 (19)
B1—B4—B9—B3	37.35 (16)	B8—B12—B10—B4	−0.6 (2)
B1—B4—B9—B8	0.0 (2)	B8—B12—B10—B9	−37.96 (18)
B1—B4—B9—B12	−63.0 (2)	B8—B12—B9—F9	−112.3 (3)
B1—B4—B9—B10	−100.17 (17)	B8—B12—B9—B4	100.4 (2)
B1—B3—B8—F8	147.2 (2)	B8—B12—B9—B3	37.11 (17)
B1—B3—B8—B7	0.4 (2)	B8—B12—B9—B10	137.68 (18)
B1—B3—B8—B12	−63.2 (2)	B12—B7—B11—F11	−112.6 (2)
B1—B3—B8—B2	37.62 (16)	B12—B7—B11—B5	100.65 (17)
B1—B3—B8—B9	−100.65 (19)	B12—B7—B11—B6	138.15 (17)
B1—B3—B2—F2	111.0 (2)	B12—B7—B11—B10	37.24 (15)
B1—B3—B2—B7	−100.46 (17)	B12—B7—B6—F6	−146.85 (18)
B1—B3—B2—B6	−36.94 (15)	B12—B7—B6—B1	63.1 (2)
B1—B3—B2—B8	−137.65 (17)	B12—B7—B6—B5	0.2 (2)
B1—B3—B9—F9	−147.5 (2)	B12—B7—B6—B11	−37.34 (15)
B1—B3—B9—B4	−37.47 (15)	B12—B7—B6—B2	100.92 (18)
B1—B3—B9—B8	100.46 (18)	B12—B7—B8—F8	112.2 (2)
B1—B3—B9—B12	63.3 (2)	B12—B7—B8—B3	−100.62 (19)
B1—B3—B9—B10	0.3 (2)	B12—B7—B8—B2	−138.00 (17)
B1—B6—B2—F2	−111.6 (2)	B12—B7—B8—B9	−36.97 (16)
B1—B6—B2—B7	137.50 (17)	B12—B7—B2—F2	149.1 (2)
B1—B6—B2—B3	36.67 (15)	B12—B7—B2—B1	−62.5 (2)
B1—B6—B2—B8	100.06 (18)	B12—B7—B2—B3	0.5 (2)
B5—B1—B4—F4	−109.4 (2)	B12—B7—B2—B6	−100.51 (17)
B5—B1—B4—B3	138.72 (16)	B12—B7—B2—B8	37.62 (16)
B5—B1—B4—B10	37.77 (15)	B12—B11—B6—F6	148.10 (18)
B5—B1—B4—B9	101.15 (17)	B12—B11—B6—B1	−63.08 (19)
B5—B1—B3—F3	−148.0 (2)	B12—B11—B6—B5	−100.73 (17)
B5—B1—B3—B4	−37.48 (15)	B12—B11—B6—B7	37.57 (16)
B5—B1—B3—B8	63.7 (2)	B12—B11—B6—B2	0.2 (2)
B5—B1—B3—B2	101.28 (16)	B12—B11—B10—F10	−110.9 (2)
B5—B1—B3—B9	0.1 (2)	B12—B11—B10—B5	138.32 (17)
B5—B1—B6—F6	109.6 (2)	B12—B11—B10—B4	100.71 (18)
B5—B1—B6—B7	−101.36 (17)	B12—B11—B10—B9	37.35 (16)
B5—B1—B6—B11	−37.98 (15)	B12—B8—B2—F2	−148.1 (2)
B5—B1—B6—B2	−139.27 (17)	B12—B8—B2—B1	63.4 (2)
B5—B1—B2—F2	147.1 (2)	B12—B8—B2—B7	−37.57 (16)
B5—B1—B2—B7	−1.1 (2)	B12—B8—B2—B3	100.87 (19)
B5—B1—B2—B3	−102.00 (17)	B12—B8—B2—B6	−0.1 (2)
B5—B1—B2—B6	36.85 (15)	B12—B8—B9—F9	110.7 (2)
B5—B1—B2—B8	−64.4 (2)	B12—B8—B9—B4	−100.60 (19)
B5—B11—B6—F6	−111.2 (2)	B12—B8—B9—B3	−138.12 (18)
B5—B11—B6—B1	37.65 (14)	B12—B8—B9—B10	−37.52 (16)
B5—B11—B6—B7	138.29 (16)	B12—B10—B9—F9	−111.4 (2)
B5—B11—B6—B2	100.88 (16)	B12—B10—B9—B4	138.19 (18)
B5—B11—B12—F12	147.8 (2)	B12—B10—B9—B3	100.3 (2)
B5—B11—B12—B7	−101.30 (17)	B12—B10—B9—B8	37.55 (16)
B5—B11—B12—B8	−64.0 (2)	B10—B5—B11—F11	111.8 (2)
B5—B11—B12—B10	37.19 (15)	B10—B5—B11—B7	−101.02 (18)
B5—B11—B12—B9	−0.3 (2)	B10—B5—B11—B6	−138.45 (17)
B5—B11—B10—F10	110.8 (2)	B10—B5—B11—B12	−37.29 (16)
B5—B11—B10—B4	−37.61 (15)	B10—B5—B4—F4	−111.7 (2)
B5—B11—B10—B12	−138.32 (17)	B10—B5—B4—B1	137.39 (16)
B5—B11—B10—B9	−100.97 (17)	B10—B5—B4—B3	100.76 (17)
B5—B4—B3—F3	146.05 (19)	B10—B5—B4—B9	37.37 (17)
B5—B4—B3—B1	36.69 (14)	B10—B5—B6—F6	146.48 (18)
B5—B4—B3—B8	−63.3 (2)	B10—B5—B6—B1	−100.40 (17)
B5—B4—B3—B2	−0.1 (2)	B10—B5—B6—B7	−0.4 (2)
B5—B4—B3—B9	−101.12 (17)	B10—B5—B6—B11	37.08 (15)
B5—B4—B10—F10	−110.5 (2)	B10—B5—B6—B2	−63.98 (19)
B5—B4—B10—B11	37.64 (15)	B10—B11—B6—F6	−148.32 (18)
B5—B4—B10—B12	100.95 (18)	B10—B11—B6—B1	0.5 (2)
B5—B4—B10—B9	138.34 (18)	B10—B11—B6—B5	−37.14 (15)
B5—B4—B9—F9	−147.6 (2)	B10—B11—B6—B7	101.15 (18)
B5—B4—B9—B3	100.33 (18)	B10—B11—B6—B2	63.74 (19)
B5—B4—B9—B8	63.0 (2)	B10—B11—B12—F12	110.6 (2)
B5—B4—B9—B12	0.0 (2)	B10—B11—B12—B7	−138.49 (17)
B5—B4—B9—B10	−37.19 (16)	B10—B11—B12—B8	−101.20 (18)
B5—B6—B2—F2	−147.83 (17)	B10—B11—B12—B9	−37.52 (17)
B5—B6—B2—B1	−36.28 (15)	B10—B4—B3—F3	−150.83 (19)
B5—B6—B2—B7	101.22 (17)	B10—B4—B3—B1	99.81 (17)
B5—B6—B2—B3	0.4 (2)	B10—B4—B3—B8	−0.2 (2)
B5—B6—B2—B8	63.8 (2)	B10—B4—B3—B2	63.0 (2)
B5—B10—B9—F9	147.71 (19)	B10—B4—B3—B9	−38.00 (16)
B5—B10—B9—B4	37.31 (16)	B10—B4—B9—F9	−110.4 (3)
B5—B10—B9—B3	−0.6 (2)	B10—B4—B9—B3	137.52 (18)
B5—B10—B9—B8	−63.3 (2)	B10—B4—B9—B8	100.22 (19)
B5—B10—B9—B12	−100.88 (18)	B10—B4—B9—B12	37.17 (17)
B7—B11—B6—F6	110.5 (2)	B10—B12—B9—F9	110.0 (3)
B7—B11—B6—B1	−100.64 (17)	B10—B12—B9—B4	−37.24 (17)
B7—B11—B6—B5	−138.29 (16)	B10—B12—B9—B3	−100.57 (19)
B7—B11—B6—B2	−37.41 (15)	B10—B12—B9—B8	−137.68 (18)
B7—B11—B12—F12	−110.9 (2)	B2—B1—B5—F5	−147.05 (19)
B7—B11—B12—B8	37.29 (16)	B2—B1—B5—B11	0.9 (2)
B7—B11—B12—B10	138.49 (17)	B2—B1—B5—B4	102.07 (18)
B7—B11—B12—B9	100.97 (19)	B2—B1—B5—B6	−36.64 (15)
B7—B11—B10—F10	−148.17 (19)	B2—B1—B5—B10	64.1 (2)
B7—B11—B10—B5	101.01 (16)	B2—B1—B4—F4	149.37 (19)
B7—B11—B10—B4	63.4 (2)	B2—B1—B4—B5	−101.24 (16)
B7—B11—B10—B12	−37.31 (15)	B2—B1—B4—B3	37.48 (15)
B7—B11—B10—B9	0.0 (2)	B2—B1—B4—B10	−63.5 (2)
B7—B6—B2—F2	110.9 (2)	B2—B1—B4—B9	−0.1 (2)
B7—B6—B2—B1	−137.50 (17)	B2—B1—B3—F3	110.7 (2)
B7—B6—B2—B3	−100.83 (18)	B2—B1—B3—B4	−138.77 (16)
B7—B6—B2—B8	−37.44 (16)	B2—B1—B3—B8	−37.60 (17)
B7—B8—B12—F12	110.7 (2)	B2—B1—B3—B9	−101.22 (18)
B7—B8—B12—B11	−37.32 (15)	B2—B1—B6—F6	−111.2 (2)
B7—B8—B12—B10	−100.78 (18)	B2—B1—B6—B5	139.27 (17)
B7—B8—B12—B9	−138.73 (17)	B2—B1—B6—B7	37.91 (16)
B7—B8—B2—F2	−110.6 (2)	B2—B1—B6—B11	101.28 (17)
B7—B8—B2—B1	100.96 (17)	B2—B7—B11—F11	146.45 (19)
B7—B8—B2—B3	138.44 (17)	B2—B7—B11—B5	−0.3 (2)
B7—B8—B2—B6	37.45 (15)	B2—B7—B11—B6	37.21 (16)
B7—B8—B9—F9	147.8 (2)	B2—B7—B11—B12	−100.95 (19)
B7—B8—B9—B4	−63.6 (2)	B2—B7—B11—B10	−63.7 (2)
B7—B8—B9—B3	−101.09 (18)	B2—B7—B6—F6	112.2 (2)
B7—B8—B9—B12	37.03 (16)	B2—B7—B6—B1	−37.81 (16)
B7—B8—B9—B10	−0.5 (2)	B2—B7—B6—B5	−100.75 (17)
B7—B12—B10—F10	147.5 (2)	B2—B7—B6—B11	−138.26 (17)
B7—B12—B10—B5	−0.3 (2)	B2—B7—B8—F8	−109.8 (3)
B7—B12—B10—B11	37.06 (16)	B2—B7—B8—B3	37.38 (16)
B7—B12—B10—B4	−63.8 (2)	B2—B7—B8—B12	138.00 (17)
B7—B12—B10—B9	−101.17 (19)	B2—B7—B8—B9	101.03 (18)
B7—B12—B9—F9	−149.2 (2)	B2—B7—B12—F12	−148.83 (19)
B7—B12—B9—B4	63.6 (2)	B2—B7—B12—B11	100.51 (17)
B7—B12—B9—B3	0.2 (2)	B2—B7—B12—B8	−37.53 (15)
B7—B12—B9—B8	−36.87 (16)	B2—B7—B12—B10	63.3 (2)
B7—B12—B9—B10	100.81 (18)	B2—B7—B12—B9	−0.4 (2)
C6—C5—C4—Se1	171.83 (17)	B2—B3—B8—F8	109.6 (3)
C9—C8—C7—Se1	−178.89 (16)	B2—B3—B8—B7	−37.26 (17)
B11—B5—B4—F4	−149.29 (18)	B2—B3—B8—B12	−100.86 (19)
B11—B5—B4—B1	99.84 (16)	B2—B3—B8—B9	−138.27 (18)
B11—B5—B4—B3	63.21 (19)	B2—B3—B9—F9	149.3 (2)
B11—B5—B4—B10	−37.55 (15)	B2—B3—B9—B4	−100.68 (17)
B11—B5—B4—B9	−0.2 (2)	B2—B3—B9—B8	37.26 (16)
B11—B5—B6—F6	109.4 (2)	B2—B3—B9—B12	0.1 (2)
B11—B5—B6—B1	−137.48 (16)	B2—B3—B9—B10	−62.9 (2)
B11—B5—B6—B7	−37.43 (15)	B2—B8—B12—F12	148.2 (2)
B11—B5—B6—B2	−101.06 (17)	B2—B8—B12—B7	37.54 (16)
B11—B5—B10—F10	−110.6 (2)	B2—B8—B12—B11	0.2 (2)
B11—B5—B10—B4	137.98 (16)	B2—B8—B12—B10	−63.2 (2)
B11—B5—B10—B12	37.23 (15)	B2—B8—B12—B9	−101.20 (18)
B11—B5—B10—B9	100.75 (18)	B2—B8—B9—F9	−148.7 (2)
B11—B7—B6—F6	−109.5 (2)	B2—B8—B9—B4	0.0 (2)
B11—B7—B6—B1	100.45 (16)	B2—B8—B9—B3	−37.52 (16)
B11—B7—B6—B5	37.51 (15)	B2—B8—B9—B12	100.60 (18)
B11—B7—B6—B2	138.26 (17)	B2—B8—B9—B10	63.1 (2)
B11—B7—B8—F8	149.7 (2)	B9—B4—B3—F3	−112.8 (2)
B11—B7—B8—B3	−63.1 (2)	B9—B4—B3—B1	137.81 (17)
B11—B7—B8—B12	37.49 (15)	B9—B4—B3—B8	37.78 (17)
B11—B7—B8—B2	−100.51 (17)	B9—B4—B3—B2	101.00 (18)
B11—B7—B8—B9	0.5 (2)	B9—B4—B10—F10	111.1 (2)
B11—B7—B12—F12	110.7 (2)	B9—B4—B10—B5	−138.34 (18)
B11—B7—B12—B8	−138.04 (16)	B9—B4—B10—B11	−100.69 (19)
B11—B7—B12—B10	−37.18 (16)	B9—B4—B10—B12	−37.39 (17)
B11—B7—B12—B9	−100.94 (18)	B9—B3—B8—F8	−112.2 (3)
B11—B7—B2—F2	−147.5 (2)	B9—B3—B8—B7	101.0 (2)
B11—B7—B2—B1	0.8 (2)	B9—B3—B8—B12	37.41 (18)
B11—B7—B2—B3	63.8 (2)	B9—B3—B8—B2	138.27 (18)
B11—B7—B2—B6	−37.16 (15)	B9—B3—B2—F2	−148.9 (2)
B11—B7—B2—B8	100.96 (19)	B9—B3—B2—B1	100.14 (18)
B11—B6—B2—F2	148.37 (17)	B9—B3—B2—B7	−0.3 (2)
B11—B6—B2—B1	−100.08 (16)	B9—B3—B2—B6	63.2 (2)
B11—B6—B2—B7	37.42 (15)	B9—B3—B2—B8	−37.51 (17)
B11—B6—B2—B3	−63.41 (19)	B9—B8—B12—F12	−110.6 (2)
B11—B6—B2—B8	0.0 (2)	B9—B8—B12—B7	138.73 (17)
B11—B12—B10—F10	110.4 (2)	B9—B8—B12—B11	101.41 (18)
B11—B12—B10—B5	−37.36 (15)	B9—B8—B12—B10	37.95 (17)
B11—B12—B10—B4	−100.89 (17)	B9—B8—B2—F2	148.4 (2)
B11—B12—B10—B9	−138.23 (18)	B9—B8—B2—B1	−0.1 (2)
B11—B12—B9—F9	147.5 (2)	B9—B8—B2—B7	−101.02 (19)
B11—B12—B9—B4	0.2 (2)	B9—B8—B2—B3	37.42 (17)
B11—B12—B9—B3	−63.1 (2)	B9—B8—B2—B6	−63.6 (2)
B11—B12—B9—B8	−100.23 (19)	B9—B12—B10—F10	−111.4 (2)
B11—B12—B9—B10	37.45 (16)	B9—B12—B10—B5	100.87 (19)
B11—B10—B9—F9	−148.7 (2)	B9—B12—B10—B11	138.23 (18)
B11—B10—B9—B4	100.92 (17)	B9—B12—B10—B4	37.34 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H···F8ⁱ	0.91	2.13	2.871 (2)	138
N1—H···O2ⁱⁱ	0.91	2.20	2.865 (2)	129
N1—HA···O1ⁱⁱⁱ	0.91	1.94	2.836 (2)	168
N1—HB···O3^iv	0.91	1.94	2.841 (2)	171

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x+1/2, y, −z+3/2; (iv) −x+1, y+1/2, −z+3/2.

Acknowledgements

MCN thanks the Fonds der Chemischen Industrie for a fellowship.

Funding information

Funding for this research was provided by: Deutsche Forschungsgemeinschaft (grant No. JE 714/6-1 to C. Jenne).

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