Conformational studies on heteroleptic tri­fluoro­methyl-substituted phenyl­boranes

Samigullin, K.; Soltani, Y.; Lerner, H.-W.; Wagner, M.; Bolte, M.

doi:10.1107/S2053229616002242

Buy article online - an online subscription or single-article purchase is required to access this article.

Conformational studies on heteroleptic trifluoromethyl-substituted phenylboranes

K. Samigullin, Y. Soltani, H.-W. Lerner, M. Wagner and M. Bolte

Organoboranes carrying electron-withdrawing substituents are commonly used as Lewis acidic catalysts or cocatalysts in a variety of organic processes. These Lewis acids also became popular through their application in `frustrated Lewis pairs', i.e. combinations of Lewis acids and bases that are unable to fully neutralize each other due to steric or electronic effects. We have determined the crystal and molecular structures of four heteroleptic arylboranes carrying 2-(trifluoromethyl)phenyl, 2,6-bis(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl or mesityl substituents. [3,5-Bis(trifluoromethyl)phenyl]bis[2-(trifluoromethyl)phenyl]borane, C₂₂H₁₁BF₁₂, (I), crystallizes with two molecules in the asymmetric unit which show very similar geometric parameters. In one of the two molecules, both trifluoromethyl groups of the 3,5-bis(trifluoromethyl)phenyl substituent are disordered over two positions. In [3,5-bis(trifluoromethyl)phenyl]bis[2,6-bis(trifluoromethyl)phenyl]borane, C₂₄H₉BF₁₈, (II), only one of the two meta-trifluoromethyl groups is disordered. In [2,6-bis(trifluoromethyl)phenyl]bis[3,5-bis(trifluoromethyl)phenyl]borane, C₂₄H₉BF₁₈, (III), both meta-trifluoromethyl groups of only one 3,5-bis(trifluoromethyl)phenyl ring are disordered. [3,5-Bis(trifluoromethyl)phenyl]dimesitylborane, C₂₆H₂₅BF₆, (IV), carries only one meta-trifluoromethyl-substituted phenyl ring, with one of the two trifluoromethyl groups disordered over two positions. In addition to compounds (I)–(IV), the structure of bis[2,6-bis(trifluoromethyl)phenyl]fluoroborane, C₁₆H₆BF₁₃, (V), is presented. None of the ortho-trifluoromethyl groups is disordered in any of the five compounds. In all the structures, the boron centre is in a trigonal planar coordination. Nevertheless, the bond angles around this atom vary according to the bulkiness and mutual repulsion of the substituents of the phenyl rings. Also, the ortho-trifluoromethyl-substituted phenyl rings usually show longer B—C bonds and tend to be tilted out of the BC₃ plane by a higher degree than the phenyl rings carrying ortho H atoms. A comparison with related structures corroborates the conclusions regarding the geometric parameters of the boron centre drawn from the five structures in this paper. On the other hand, CF₃ groups in meta positions do not seem to have a marked effect on the geometry involving the boron centre. Furthermore, it has been observed for the structures reported here and those reported previously that for CF₃ groups in ortho positions of the aromatic ring, disorder of the F atoms is less probable than for CF₃ groups in meta or para positions of the ring.

Keywords: frustrated Lewis pairs; FLP; triarylboranes; disorder; crystal structure; conformational studies; heteroleptic.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616002242/sk3617sup1.cif Contains datablocks I, II, III, IV, V, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616002242/sk3617Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616002242/sk3617IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616002242/sk3617IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616002242/sk3617IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616002242/sk3617Vsup6.hkl Contains datablock V

CCDC references: 1451950; 1451949; 1451948; 1451947; 1451946

Introduction top

Organoboranes carrying electron-withdrawing substituents are commonly used as Lewis acidic catalysts or cocatalysts in a variety of organic processes, among them hydrosilylation, Diels–Alder and polymerization reactions (Piers & Chivers, 1997; Ishihara & Yamamoto, 1999). During the last decade, these Lewis acids also became popular through their application in `frustrated Lewis pairs' (FLPs), combinations of Lewis acids and bases that are unable to fully neutralize each other due to steric or electronic effects. The unquenched reactivity allows FLPs to activate small molecules, such as H₂ or CO₂, by cleaving single bonds or adding themselves to multiple bonds (Stephan & Erker, 2015).

Most FLPs are composed of bulky bases (e.g. tBu₃P) and rather unhindered acids, such as (C₆F₅)₃B (Stephan & Erker, 2015), whereas combinations of smaller bases with sterically encumbered acids (Lu et al. 2011; Scott et al., 2014) are much more seldom. In the latter case, the acids have to be equipped with substituents that maintain reasonable electron-withdrawing properties, while being sterically demanding. Both attributes are combined in o-CF₃-substituted phenyl groups, which makes boranes such as bis[2,4,6-tris(trifluoromethyl)phenyl]borane convenient Lewis acids for the application in FLPs with sterically unhindered Lewis bases (Lu et al., 2011).

Recently, two homoleptic triarylboranes carrying 2,4- or 2,5-CF₃-substituted phenyl rings have been introduced as FLP components (Blagg et al., 2016). In combination with Lewis bases, both these compounds do not exhibit any reactivity towards H₂, which is due to both electronic and steric effects (Blagg et al., 2016).

In the course of our research, we have prepared a number of heteroleptic arylboranes, some of which may be useful components in FLPs. These boranes are equipped with 2-(trifluoromethyl)phenyl (2-Ar^F), 2,6-bis(trifluoromethyl)phenyl (2,6-Ar^F), 3,5-bis(trifluoromethyl)phenyl (3,5-Ar^F) or 2,4,6-trimethylphenyl (Mes) substituents, thereby varying in the number and distribution of the CF₃ groups on the aryl rings. Thus, they experience different degrees of steric encumbrance at their reactive centres, which is important for tuning their reactivities. We have synthesized the four triaryl boranes (2-Ar^F)₂(3,5-Ar^F)B, (I), (2,6-Ar^F)₂(3,5-Ar^F)B, (II), (2,6-Ar^F)(3,5-Ar^F)₂B, (III), and (Mes)₂(3,5-Ar^F)B, (IV), by treating either easily accessible potassium fluoroborates, i.e. K[(3,5-Ar^F)BF₃] (Vedejs et al., 1995) and K[(3,5-Ar^F)₂BF₂] (Samigullin et al., 2014) or the fluoroboranes Mes₂BF and (2,6-Ar^F)₂BF, (V), with the appropriate lithium organyls. Herein we present the synthesis protocols and characterization of boranes (I), (II), (III) (IV) and (V), discuss their solid-state structures and compare them with selected known literature molecules.

Experimental top

Synthesis and crystallization top

General techniques top

All reactions and manipulations were carried out by applying standard Schlenk techniques under a nitrogen atmosphere. K[(3,5-Ar^F)₂BF₂] (Samigullin et al., 2014) and K[(3,5-Ar^F)BF₃] (Vedejs et al., 1995) were prepared using literature procedures. Me₃SiCl was stirred with CaH₂ to remove HCl and then left standing until the solid sedimented. Et₂O was dried with Na/benzophenone and distilled prior to use. BF₃·OEt₂ (Sigma–Aldrich) was distilled prior to use. Mes₂BF (abcr), (2-Ar^F)Br (Apollo Scientific), (2,6-Ar^F)Br (Manchester Organics), (3,5-Ar^F)Br (Apollo Scientific), and nBuLi (1.6 M in n-hexane; Rockwood Lithium) were used as received. NMR spectra were recorded at 298 K on Bruker Avance II 300 or Avance III HD 500 spectrometers. Chemical shifts are referenced to (residual) solvent signals (¹H and ¹³C{¹H}; C₆D₆: δ 7.16/128.06) or BF₃·OEt₂ (¹¹B) and CFCl₃ (¹⁹F) as external standards. Abbreviations: s = singlet, d = doublet, t = triplet, q = quartet, spt = septet, m = multiplet, br = broad, nr = not resolved and no = not observed. Combustion analyses were performed by the Microanalytical Laboratory of the Goethe University Frankfurt.

Synthesis of (V) top

A solution of (2,6-Ar^F)Br (0.33 g, 1.1 mmol) in Et₂O (5 ml) was cooled to 195 K. nBuLi (0.70 ml, 1.6 M in n-hexane, 1.1 mmol) was added and the reaction mixture was stirred at 195 K for 1 h. BF₃·OEt₂ (0.07 ml, 0.6 mmol) was added, the reaction mixture was allowed to warm to room temperature and was then stirred for 2 h. The resulting slurry was filtered and the filter cake was extracted into Et₂O (2 × 5 ml). The combined organic phases were evaporated to dryness and the product was purified by sublimation (353 K, 2 × 10⁻³ mbar), giving colourless crystals of (V). They were contaminated with a colourless oil (yield: 0.13 g, 0.29 mmol, 53%). ¹H NMR (500.2 MHz, C₆D₆): δ 7.29 (d, ³J_HH = 8.0 Hz, 4H; H-m), 6.69 (t, ³J_HH = 8.0 Hz, 2H; H-p). ¹¹B NMR (160.5 MHz, C₆D₆): δ 47.8 (s). ¹³C{¹H} NMR (125.8 MHz, C₆D₆): δ no (C-i), 136.1 (br q, ²J_CF = 33 Hz; C-o), 132.0 (s; C-p), 129.6 (nr; C-m), 124.3 (q, ¹J_CF = 275 Hz). ¹⁹F{¹¹B} NMR (470.6 MHz, C₆D₆): δ −11.2 (nr, 1 F; BF), −56.6 (d, J_FF = 15 Hz, 12 F; CF₃).

Synthesis of (I) top

A solution of (2-Ar^F)Br (0.96 ml, 7.1 mmol) in Et₂O (10 ml) was cooled to 195 K. nBuLi (4.4 ml, 1.6 M in n-hexane, 7.0 mmol) was added and the reaction mixture was stirred at 195 K for 10 min. Solid K[(3,5-(CF₃)₂C₆H₃)BF₃] (1.13 g, 3.53 mmol) was added, the reaction mixture was allowed to warm to room temperature and was then stirred for 2 h, during which it turned dark brown. Me₃SiCl (1.0 ml, 7.9 mmol) was added and the reaction mixture was stirred for 4 h. The resulting slurry was filtered and the filter cake was extracted into Et₂O (3 × 10 ml). The combined organic phases were evaporated to dryness, the product was purified by sublimation (403 K, 2×10⁻³ mbar) and recrystallization from n-hexane (10 ml), giving colourless crystals of (I) (yield: 0.61 g, 1.2 mmol, 34%). ¹H NMR (500.2 MHz, C₆D₆): δ 8.02 (s, 2H; (3,5-Ar^F)-H-o), 7.88 [s, 1H; (3,5-Ar^F)-H-p], 7.37 [d, ³J_HH = 7.6 Hz, 2H; (2-Ar^F)-H-3], 7.09 [d, ³J_HH = 7.3 Hz, 2H; (2-Ar^F)-H-6], 6.97–6.94 [m, 2H; (2-Ar^F)-H-4], 6.93–6.90 [m, 2H; (2-Ar^F)-H-5]. ¹¹B NMR (160.5 MHz, C₆D₆): δ 70 (h_1/2 = 1050 Hz). ¹³C{¹H} NMR (125.8 MHz, C₆D₆): δ 143.7 [nr; (3,5-Ar^F)-C-i], 140.1 [nr; (2-Ar^F)-C-1], 137.7 [nr; (3,5-Ar^F)-C-o], 133.2 [s; (2-Ar^F)-C-6], 132.9 [q, ²J_CF = 31 Hz; (2-Ar^F)-C-2], 131.5 [q, ²J_CF = 33 Hz; (3,5-Ar^F)-H-m], 130.9 [s; (2-Ar^F)-C-5], 130.6 [s; (2-Ar^F)-C-4], 126.7 [spt, ³J_CF = 4 Hz; (3,5-Ar^F)-C-p], 126.3 [m; (2-Ar^F)-C-3], 125.2 [q, ¹J_CF = 274 Hz; (2-Ar^F)-CF₃], 123.8 [q, ¹J_CF = 273 Hz; (3,5-Ar^F)-CF₃]. ¹⁹F NMR (282.3 MHz, C₆D₆): δ −55.2 [s, 6 F; (2-Ar^F)-CF₃], −62.9 [s, 6 F; (3,5-Ar^F)-CF₃]. Elemental analysis found: C 51.38, H 2.05%; calculated for C₂₂H₁₁BF₁₂: C 51.40, H 2.16%.

Synthesis of (II) top

A solution of (V) (0.145 g, 0.318 mmol) in Et₂O (4 ml) was cooled to 195 K. (3,5-Ar^F)Br (0.06 ml, 0.3 mmol) and nBuLi (0.20 ml, 1.6 M in n-hexane, 0.32 mmol) were added, the reaction mixture was allowed to warm to room temperature and was then stirred for 16 h. The resulting slurry was filtered and the filter cake was extracted into Et₂O (2 × 5 ml). The combined organic phases were evaporated to dryness and the product was purified by sublimation (423 K, 2 × 10⁻³ mbar), giving colourless crystals of (II) (yield: 73 mg, 0.11 mmol, 37%). ¹H NMR (500.2 MHz, C₆D₆): δ 7.9 [s, 1H; (3,5-Ar^F)-H-p], 7.88 [s, 2H; (3,5-Ar^F)-H-o], 7.35–7.33 [m, 4H; (2,6-Ar^F)-H-m], 6.74–6.70 [m, 2H; (2,6-Ar^F)-H-p]. ¹¹B NMR (160.5 MHz, C₆D₆): δ 70 (h_1/2 = 1100 Hz). ¹³C{¹H} NMR (125.8 MHz, C₆D₆): δ 147.4 [nr; (3,5-Ar^F)-C-i], 137.0 [nr; (2,6-Ar^F)-C-i], 135.8 [nr, (3,5-Ar^F)-C-o], 135.8 [q, ²J_CF = 31 Hz; (2,6-Ar^F)-C-o], 131.8 [s; (2,6-Ar^F)-C-p], 131.2 [q, ²J_CF = 33 Hz; (3,5-Ar^F)-C-m], 130.3 [nr; (2,6-Ar^F)-C-m], 126.1 [spt, ³J_CF = 4 Hz; (3,5-Ar^F)-C-p], 124.2 [q, ¹J_CF = 275 Hz; (2,6-Ar^F)-CF₃], 123.8 [q, ¹J_CF = 273 Hz; (3,5-Ar^F)-CF₃]. ¹⁹F NMR (470.6 MHz, C₆D₆): δ −52.8 [s, 12 F; (2,6-Ar^F)-CF₃], −63.1 [m, 6 F; (3,5-Ar^F)-CF₃]. Elemental analysis found: C 43.99, H 1.21%; calculated for C₂₄H₉BF₁₈: C 44.34, H 1.40%.

Synthesis of (III) top

A solution of (2,6-Ar^F)Br (1.0 g, 3.4 mmol) in Et₂O (50 ml) was cooled to 195 K. nBuLi (2.1 ml, 1.6 M in n-hexane, 3.4 mmol) was added and the reaction mixture was stirred for 3 h at 195 K. Solid K[(3,5-Ar^F)₂BF₂] (1.75 g, 3.40 mmol) was added, the reaction mixture was allowed to warm to room temperature and was then stirred for 12 h. After that, Me₃SiCl (0.45 ml, 3.6 mmol) was added at 273 K and the reaction mixture was stirred for 2 h. The resulting slurry was filtered and the filter cake was extracted into Et₂O (3 × 10 ml). The combined organic phases were evaporated to dryness and the product was purified by sublimation (413 K, 2 × 10⁻³ mbar), giving colourless crystals of (III) (yield: 1.1 g, 1.7 mmol, 50%). ¹H NMR (500.2 MHz, C₆D₆): δ 8.03 [s, 4H; (3,5-Ar^F)-H-o], 7.81 [s, 2H; (3,5-Ar^F)-H-p], 7.14 [d, ³J_HH = 7.9 Hz, 2H; (2,6-Ar^F)-H-m], 6.62 [t, ³J_HH = 7.9 Hz, 1H; (2,6-Ar^F)-H-p]. ¹¹B NMR (160.5 MHz, C₆D₆): δ 68 (h_1/2 = 1500 Hz). ¹³C{¹H} NMR (125.8 MHz, C₆D₆): δ 140.2 [nr; (3,5-Ar^F)-C-i], 137.2 [nr; (2,6-Ar^F)-C-i], 136.8 [nr; (3,5-Ar^F)-C-o], 132.1 [q, ²J_CF = 33 Hz; (3,5-Ar^F)-C-m], 131.9 [q, ²J_CF = 32 Hz; (2,6-Ar^F)-C-o], 130.7 [s; (2,6-Ar^F)-C-p], 129.6 [nr; (2,6-Ar^F)-C-m], 126.6 [spt, ³J_CF = 4 Hz; (3,5-Ar^F)-C-p], 124.8 [q, ¹J_CF = 274 Hz; (2,6-Ar^F)-CF₃], 123.6 [q, ¹J_CF = 273 Hz; (3,5-Ar^F)-CF₃]. ¹⁹F NMR (470.6 MHz, C₆D₆): δ −55.5 [s, 6 F; (2,6-Ar^F)-CF₃], −63.0 [s, 12 F; (3,5-Ar^F)-CF₃]. Elemental analysis found: C 44.50, H 1.42%; calculated for C₂₄H₉BF₁₈: C 44.34, H 1.40%.

Synthesis of (IV) top

A solution of Mes₂BF (0.216 g, 0.805 mmol) in Et₂O (6 ml) was cooled to 195 K. (3,5-Ar^F)Br (0.14 ml, 0.81 mmol) and nBuLi (0.5 ml, 1.6 M in n-hexane, 0.8 mmol) were added, the reaction mixture was allowed to warm to room temperature and was then stirred for 16 h. The resulting slurry was filtered and the filter cake was extracted into Et₂O (2 × 5 ml). The combined organic phases were evaporated to dryness and the product was purified by sublimation (423 K, 2 × 10⁻³ mbar), giving colourless crystals of (IV) (yield: 0.19 g, 0.41 mmol, 51%). ¹H NMR (500.2 MHz, C₆D₆): δ 8.19 [s, 2H; (3,5-Ar^F)-H-o], 7.91 [s, 1H; (3,5-Ar^F)-H-p], 6.70 (s, 4H; Mes-H-m), 2.11 (s, 6H; CH₃-p), 1.92 (s; 12H; CH₃-o). ¹¹B NMR (160.5 MHz, C₆D₆): δ 74 (h_1/2 = 1300 Hz). ¹³C{¹H} NMR (125.8 MHz, C₆D₆): δ 148.6 [nr; (3,5-Ar^F)-C-i], 141.1 (s; Mes-C-o), 140.8 (nr; Mes-C-i), 140.4 (s; Mes-C-p), 136.0 [nr; (3,5-Ar^F)-C-o], 131.9 [q, ²J_CF = 33 Hz; (3,5-Ar^F)-C-m], 129.3 (s; Mes-H-m), 125.3 [spt, ³J_CF = 4 Hz; (3,5-Ar^F)-C-p], 124.0 (q, ¹J_CF =273 Hz; CF₃), 23.7 (s; CH₃-o), 21.3 (s; CH₃-p). ¹⁹F NMR (470.6 MHz, C₆D₆): δ −62.6 (s). Elemental analysis found: C 67.84, H 5.60%; calculated for C₂₆H₂₅BF₆: C 67.55, H 5.45%.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were found in difference maps. Nevertheless, they were geometrically positioned and refined using a riding model, with methyl C—H = 0.98 Å or aromatic C—H = 0.95 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms or 1.2U_eq(C) for aromatic H atoms. For the H atoms of the methyl groups in (IV) free rotation about their local threefold axis was allowed.

In (I), two trifluoromethyl groups are disordered over two positions with site occupation factors of 0.331 (14) and 0.17 (2) for the minor occupied sites. The displacement ellipsoids of the disordered F atoms were restrained to an isotropic behaviour. Due to the absence of significant anomalous scatterers, the absolute structure could not be determined riliably and any reference to the Flack parameter value (Parsons et al., 2013) has been removed.

In (II), one trifluoromethyl group is disordered over two positions with a site-occupation factor of 0.725 (6) for the major-occupied site. The displacement ellipsoids of the disordered F atoms were restrained to an isotropic behaviour.

In (III), two trifluoromethyl groups are disordered over two positions with site-occupation factors of 0.871 (5) and 0.895 (6) for the major-occupied sites. The displacement ellipsoids of the minor-occupied sites of the disordered F atoms were restrained to an isotropic behaviour.

In (IV), one trifluoromethyl group is disordered over two positions with a site-occupation factor of 0.543 (12) for the major-occupied site. The displacement ellipsoids of the disordered F atoms were restrained to an isotropic behaviour.

Results and discussion top

The two molecules in the asymmetric unit of (I) (Fig. 1) are very similar. A least-squares fit of the boron centres and the C atoms bonded directly to them gives an r.m.s. deviation of 0.021 Å (Fig. 2). Even the o-CF₃ groups have essentially the same orientation in both molecules. Since there is disorder in the m-CF₃ groups, their orientations cannot be compared. The o-CF₃ groups of the two rings are located on opposite sides of the BC₃ plane, which is probably due to their steric repulsion. The boron centre has a trigonal planar geometry with the sum of the bond angles at this atom amounting to 360°. Nevertheless, the steric demand of the o-CF₃ groups leads to a widening of the C—B—C bond angles between the two ortho-substituted rings [C1—B1—C11 = 121.4 (5)° and C1A—B1A—C11A = 123.6 (5)°] compared to the remaining angles around the B atom [C1—B1— C21 = 119.4 (5)°, C11—B1—C21 = 119.2 (5)° and C1A—B1A—C21A = 119.7 (5)° and C11A—B1A—C21A 116.7 (5)°]. In accord with that, the 2-Ar^F rings are forced out of the BC₃ plane by a higher degree than the 3,5-Ar^F rings, leading to wider dihedral angles [59.3 (2)/54.2 (2) and 57.8 (2)/53.9 (2)° for 2-Ar^F versus 12.5 (3)/20.7 (3)° for 3,5-Ar^F]. The effect on the B—C bond lengths is not very diagnostic, since in only one of the two molecules are the B—C(2—Ar^F) bonds [B1—C1 = 1.594 (9) Å and B1—C11 = 1.582 (9) Å] significantly longer than the B—C(3,5-Ar^F) bond [B1—C21 = 1.555 (9) Å]. In the second molecule, the B—C bond lengths to all three substituents are rather similar [B1A—C1A = 1.557 (9) Å, B1A—C11A = 1.573 (9) Å and B1A—C21A = 1.566 (9) Å].

Compared to the 2-Ar^F substituents in (I), which have only one o-CF₃ group each, the 2,6-Ar^F rings in (II) both have two o-CF₃ groups (Fig. 3). Nevertheless, we made similar observations concerning the molecular conformations of (I) and (II). Again, the sum of the bond angles at the planar B centre is 360° and the C—B—C angle between the two ortho-substituted rings [C11—B1—C21 = 124.89 (17)°] is significantly wider than the remaining two angles at B [C1—B1—C11 = 116.00 (18)° and C1—B1 —C21 119.09 (18)°]. As anticipated, the presence of a second o-CF₃ group on both sterically demanding 2,6-Ar^F rings in (II) leads to stronger repulsion than that between the 2-Ar^F rings in (I), and thus to an even wider angle between the planes of these rings [121.4 (5) and 123.6 (5)° in (I) versus 124.89 (17)° in (II)]. In agreement with this, the B—C(2,6-Ar^F) bonds are longer [B1—C11 = 1.603 (3) Å and B1—C21 = 1.598 (3) Å] than the B—C(3,5-Ar^F) bond [B1—C1 = 1.568 (3) Å]. Once more, the dihedral angles between the BC₃ plane and those of the ortho-substituted aryl rings [46.23 (10) and 53.68 (8)°, respectively, for the rings containing atoms C21 and C11] are wider than between the BC₃ plane and that of the meta-substituted ring [30.83 (10)°]. Interestingly, this effect is stronger in (I) than in (II). This is probably due to the fact that the o-CF₃ groups of the 2-Ar^F substituents in (I) can evade each other by turning to the opposite sides of the tricoordinated B atom, whereas the o-CF₃ groups in (II) would collide on both sides, if the 2,6-Ar^F rings were tilted further out of the BC₃ plane.

In (III) (Fig. 4), we inverted the substitution pattern of (II) by introducing one 2,6-Ar^F ring and two 3,5-Ar^F rings instead of two 2,6-Ar^F rings and one 3,5-Ar^F ring. Again, the boron centre is in a trigonal planar coordination mode (the sum of the bond angles at this atom is 360°) and the B—C(2,6-Ar^F) bond [B1—C1 = 1.595 (3) Å] is markedly longer than the B—C(3,5-Ar^F) bonds [B1—C11 = 1.564 (3) Å and B1—C21 = 1.569 (3) Å]. However, the bond angles are not significantly affected by steric effects as it is the case in (I) and (II), since the 2,6-Ar^F ring fully evades collision with the 3,5-Ar^F substituents through an almost perpendicular orientation to the BC₃ plane [dihedral angle = 75.16 (7)°]. The planes of the 3,5-Ar^F rings display dihedral angles of 24.61 (8) and 34.71 (8)° with the BC₃ plane for the rings containing atoms C11 and C21, respectively.

The boron centre in (IV) (Fig. 5) carries only one CF₃-substituted ring (3,5-Ar^F), whereas the other two substituents at the B atom are mesityl rings, which may have a slightly lower steric demand than the 2,6-Ar^F substituents. Thus, (IV) might show similar structural properties to (II). In (IV), the boron centre is also coordinated in a trigonal planar manner, with the sum of the bond angles around this atom being 360°. The C—B—C bond angle between the two mesityl rings is markedly widened [C11—B1—C21 = 124.9 (2)°] compared to the other two C—B—C bond angles [C1—B1—C11 = 117.7 (2)° and C1—B1—C21 = 117.4 (2)°], which resembles the situation in (II). In this structure, however, the three B—C bonds have almost the same length. The B—C(3,5-Ar^F) bond is even slightly longer [B1—C1 = 1.581 (4) Å] than the two B—C(Mes) bonds [B1—C11 = 1.574 (4) Å and B1—C21 = 1.577 (4) Å], which contradicts the observations made for (II). This suggests that the repulsion between the CH₃ groups of the mesityl rings is weaker than that between the CF₃ groups of the 2,6-Ar^F substituents, which is in good agreement with the larger size of the latter. The tilting of the two mesityl rings is more pronounced [47.37 (11) and 56.66 (10)°, respectively, for the rings containing atoms C11 and C21] out of the BC₃ plane than the tilting of the 3,5-Ar^F ring [27.97 (13)°]. These angles, again, resemble those in (II) [46.23 (10) and 53.68 (8)° in 2,6-Ar^F versus 30.83 (10)° in 3,5-Ar^F]. The lower steric demand of the CH₃ groups on either side of the BC₃ plane in (IV) enables them to approach each other more closely than the CF₃ groups in (II), thus allowing slightly wider dihedral angles.

In the case of fluoroborane (V) (Fig. 6), which has two 2,6-Ar^F substituents like (II) but an F atom instead of the 3,5-Ar^F ring, the sum of bond angles at the B atom is 360°, as in all previous cases. The compact F-containing substituent in (V) grants the 2,6-Ar^F groups more space to avoid each other than the larger 3,5-Ar^F ring in (II). Thus, the C—B—C bond angle between the two aryl rings is expanded even more to 128.9 (3)°. Accordingly, the F1—B1—C1 and F1—B1—C11 angles are compressed to 114.9 (3) and 116.2 (3)°, respectively. The dihedral angles between the planes of the aromatic rings and the BC₂F plane differ markedly, viz. 54.00 (15) and 40.96 (11)°, respectively, for the rings containing atoms C1 and C11. The B—C bond lengths in (V) [B1—C1 = 1.586 (5) Å and B1—C11 = 1.589 (5) Å] are in the same range as those in (II) and (III).

In order to obtain more information about the molecular conformation of the compounds reported here, we compared them with similar structures retrieved from the Cambridge Structural Database (CSD, Version ???; Groom & Allen, 2014). Triphenylborane (CSD refcode TPHBOR; Zettler et al., 1974) is the simplest comparable structure, with just three phenyl rings connected to the boron centre. The sum of the bond angles at this atom is 360°, with essentially equal C—B—C bond angles (120.2 and twice 119.6°; the molecule is located on a twofold rotation axis) and C—B bond lengths [1.589 (5) and twice 1.571 (3) Å]. The dihedral angles between the BC₃ plane and those of the the phenyl rings are 35.0 and twice 28.6°. Since there are only H atoms in the ortho positions of all the phenyl rings, the repulsion between them is not very pronounced and they are not tilted very much out of the BC₃ plane. The dihedral angles of the 3,5-Ar^F rings in (II), (III) and (IV) lie in a similar range [24.61 (8)–34.71 (8)°], which excludes any significant effect of the m-CF₃ groups on the steric repulsion of the aryl rings.

A structure which fits neatly with the molecules presented here is (3,5-Ar^F)₃B [DAQDAA (Konze et al., 1999) and DAQDAA01 (Fronczek, 2008)]. Since the two published structure determinations give essentially the same results, only DAQDAA will referred to in the following discussion. The borane (the sum of the bond angles at the B atom is 360°) shows C—B—C bond angles (119.6, 119.9 and 120.5°) and B—C bond lengths (1.553, 1.562 and 1.569 Å) that are essentially equal. Since the boron centre carries three identical substituents, it is not surprising that the geometric parameters involving the substituents are very similar. Also, the dihedral angles between the BC₃ plane and those of the aromatic rings show no strongly pronounced variation (33.8, 36.3 and 39.3°). However, these angles are in average wider than the dihedral angles between the BC₃ plane and those of the 3,5-Ar^F rings in (I), (II), (III) and (IV), suggesting that the bulky ortho substituents of the 2-Ar^F, 2,6-Ar^F and Mes rings slightly force the 3,5-Ar^F groups into the BC₃ plane.

Two other interesting examples with similar structures are (2,4-Ar^F)₃B (UMUHIT; Cornet et al., 2003) and (2,5-Ar^F)₃B (AJAGID; Blagg et al., 2016), which feature boron centres with three aryl rings carrying one o-CF₃ group and one p-CF₃ (UMUHIT) or m-CF₃ group (AJAGID) each. The three B—C bonds are exactly equal in UMUHIT [1.582 (4) Å], and are similar in AJAGID [1.568 (3), 1.582 (3) and 1.583 (3) Å], but, astonishingly, the C—B—C bond angles show quite a variation [117.0 (2), 117.6 (2) and 124.7 (2)° in UMUHIT, and 116.98 (17), 119.12 (17) and 123.60 (17)° in AJAGID]. This goes along with three largely differing dihedral angles between the BC₃ plane and those of the three aromatic rings (46.4, 52.9 and 68.8° in UMUHIT, and 43.3, 56.8 and 61.5° in AJAGID). A closer inspection of the molecular conformations can explain these findings. In both molecules, two of the three o-CF₃ groups are on one side, whereas the third CF₃ group is located on the opposite side of the BC₃ plane. As a result, the distances between the C atoms of the three o-CF₃ groups are significantly different (4.299, 4.560 and 6.255 Å in UMUHIT, and 4.227, 4.587 and 6.248 Å in AJAGID). The widest C—B—C bond angle is between the aryl rings having the shortest distance between their o-CF₃ groups, which are on opposite sides of the BC₃ plane. The asymmetric nature of the molecules slightly, but not significantly, distorts the boron center from a trigonal planar coordination. The sums of the bond angles at the B atoms are 359 (UMUHIT) and 360° (AJAGID).

Compared with the preceeding examples (i.e. UMUHIT and AJAGID), the phenyl rings of (2-Ar^F)₃B (WOTTOO; Toyota et al., 2000) lack the CF₃ groups in the para or meta positions, but the o-CF₃ groups on each of the aryl rings are still present. But although the chemical surroundings of the B atoms are almost the same in all three molecules, the structure of WOTTOO shows significant differences compared to UMUHIT and AJAGID. All three o-CF₃ groups are located on the same side of the BC₃ plane, resulting in distortion from the trigonal planar coordination of the B atom (the sum of the bond angles is 358°), which is due to the repulsion of the CF₃ groups. The B—C bond lengths (1.575, 1.577 and 1.582 Å) are almost the same. The dihedral angles between the planes of the 2-Ar^F rings and the BC₃ plane (45.4, 49.3 and 53.1°) are also very similar to each other.

All these previously reported structures (i.e. TPHBOR, DAQDAA, UMUHIT, AJAGID and WOTTOO) are homoleptic, therefore significantly differing from the present structures (I)–(V) in the chemical surrounding of the B atom and thus cannot be compared directly with them. We therefore also discuss several known literature heteroleptic boranes in the following paragraphs.

(2,4,6-Ar^F)₂(Ph)B (ROLXOH; Zhang et al., 2015) and (2,4,6-Ar^F)₂(4-tBu-C₆H₄)B (ROMGEH; Zhang et al., 2015) can be compared directly to the structure of (II), since they also have two o-CF₃ groups (and an additional p-CF₃ group) on two aryl rings each and a third phenyl ring without any ortho substituents. Both ROLXOH and ROMGEH have planar B atoms (the sums of the bond angles at this atom are both 360°). Again, the C—B—C bond angles between the ortho-substituted phenyl rings [123.5 (2)° in ROLXOH and 125.67 (17)° in ROMGEH] are wider than the other two C—B—C bond angles [116.6 (2) and 119.8 (2)° in ROLXOH, and 115.18 (17) and 119.17 (17)° in ROMGEH]. The B—C (2,4,6-Ar^F) bonds [1.604 (4) and 1.610 (4) Å in ROLXOH, and 1.606 (3) and 1.607 (3) Å in ROMGEH] are significantly longer than the third B—C bond [1.551 (4)° in ROLXOH and 1.546 (3)° in ROMGEH]. Also, the dihedral angles between the ortho-substituted aryl rings and the BC₃ plane (47.1° and 63.3 °) are much larger than those between the (para-substituted) phenyl ring and the BC₃ plane [25.4° in ROLXOH and 29.2° in ROMGEH]. All discussed bond lengths, bond angles and dihedral angles in ROLXOH and ROMGEH are in very good agreement with those in (II).

A similar structure is also found in Mes₂(Ph)B (TAVMIM; Fiedler et al., 1996), which is basically ROLXOH with the CF₃ groups replaced by CH₃ groups or (IV) with the CF₃ groups replaced by H atoms. In TAVMIM, the two mesityl are symmetrically equivalent due to a C₂ axis which runs through the B—C(Ph) bond. The C—B—C bond angle between the mesityl groups [122.8 (2)°] is again larger than the other two C—B—C angles [both 118.61 (10)°]; all three sum up to 360°. The B—C(Mes) bond lengths [1.579 (2) Å] are only slightly larger than the B—C(Ph) bond length [1.569 (3) Å]. The planes of the mesityl rings are tilted out of the BC₃ plane by 60.56°, and the plane of the phenyl group by is tilted by 21.58°. Only the dihedral angles of TAVMIM differ significantly from the angles in (IV), the other values are more or less in agreement.

The diarylfluoroboranes (2,4,6-Ar^F)₂BF and (Mes)₂BF (UMUHEP and UMUHUF; Cornet et al., 2003) both have structural parameters comparable to those of (V), but as expected, CF₃-substituted UMUHEP is much closer to (V) than CH₃-substituted UMUHUF. The B—F bond lengths are 1.312 (3) (UMUHEP) and 1.339 (2) Å (UMUHUF). Thus, the bond length in (V) [1.318 (4) Å] is only slightly longer than that in UMUHEP, but significantly shorter than that in UMUHUF. This is probably due to electronic rather than steric properties of the aryl substituents: The electron-rich mesityl groups in UMUHUF slightly reduce the Lewis acidity of the boron centre, making π-donation of electrons from F to B less favoured than in (V) and UMUHEP, which both have electron-withdrawing substituents. Thus, the double-bond character in UMUHUF is less pronounced and the B—F bond is longer. The B—C bonds in (V) [1.586 (5) and 1.589 (5) Å] and in UMUHEP [1.588 (4) and 1.596 (4) Å], however, are longer than in UMUHUF [1.568 (2) and 1.570 (2) Å], but are still similar to each other, which is probably due to stronger steric repulsion of the CF₃ groups. In all three molecules, the B atom is in a trigonal planar coordination mode, with the sums of bond angles at this atom being 360°. All three molecules have a significantly widened C—B—C angle [128.9 (3)° in (V), 128.4 (2)° in UMUHEP and 125.39 (14)° in UMUHUF] and compressed C—B—F angles [114.9 (3) and 116.2 (3)° in (V), 115.6 (2) and 116.1 (2)° in UMUHEP, and 116.82 (14) and 117.79 (14)° in UMUHUF]. In the boranes containing CF₃ groups, the effect is much more pronounced, which is due to the higher steric demand of the substituents.

All the structures discussed above have a trigonally planar boron centre in common, with the sum of the bond angles at this atom being almost exactly 360°. Nevertheless, repulsion between the substituents at the B atom leads to differing C—B—C angles. As expected, higher repulsion between the substituents at the B atom widens the C—B—C angle. The B—C bonds are affected by the same effect. CF₃ groups in the ortho positions of the aromatic ring tend to result in longer B—C bonds. In addition, the dihedral angle between the aromatic ring and the BC₃ plane varies according to the substituents in the ortho positions of the aromatic ring. The CF₃ groups in the meta positions do not seem to have a marked effect on the geometry involving the boron centre.

To conclude the discussion we will make some remarks about the disorder of the trifluoromethyl groups. There is no preferred orientation for a trifluoromethyl group attached to an sp² or aromatic C atom as there is for a trifluoromethyl group attached to an sp³-hybridized C atom. Thus, there is a reasonably high probability that the F atoms are disordered. In the five structures presented in this paper, disorder occurred in (I) for two of the four CF₃ groups in the meta positions, in (II) for one of the two CF₃ groups in the meta positions, in (III) for two of the six CF₃ groups in the meta positions and in (IV) for one of the two CF₃ groups in the meta positions. For the CF₃ groups in the ortho positions, no disorder was found in any of the five presented structures.

Similar observations were made for the compared structures. In DAQDAA, four of the six (three of the six in DAQDAA01) CF₃ groups in the meta positions are disordered. In UMUHIT, on the other hand, neither the CF₃ groups in the ortho nor those in the para position are disordered. In WOTTOO, none of the CF₃ groups in the ortho positions is disordered. ROLXOH, however, is an exception, because one of the four CF₃ groups in the ortho positions is disordered, whereas the CF₃ groups in the para position do not show disorder. In AJAGID and ROMGEH, none of the CF₃ groups in the ortho positions shows any disorder. However, one of the two p-CF₃ groups in ROMGEH has enlarged displacement parameters. As a result, the probability that a trifluoromethyl group bonded to a phenyl ring shows disorder is higher when the CF₃ is attached to the ring in the meta or para position. If it is located in the ortho position, disorder is not very probable.

Structure description top

Synthesis and crystallization top

Refinement details top

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. (a) Perspective view of one molecule in the asymmetric unit of (I), with displacement ellipsoids drawn at the 50% probability level. Only one set of the disordered F atoms is shown. (b) Perspective view of molecule A in the asymmetric unit of (I), with displacement ellipsoids drawn at the 50% probability level. Only one set of the disordered F atoms is shown.
	Fig. 2. Least-squares fit of the two molecules in the asymmetric unit of (I). B atoms and C atoms bonded to B atoms are superimposed; the r.m.s. deviation is 0.021 Å. H atoms have been omitted for clarity.
	Fig. 3. Perspective view of the structure of (II), with displacement ellipsoids drawn at the 50% probability level. Only one set of the disordered F atoms is shown.
	Fig. 4. Perspective view of the structure of (III), with displacement ellipsoids drawn at the 50% probability level. Only one set of the disordered F atoms is shown.
	Fig. 5. Perspective view of the structure of (IV), with displacement ellipsoids drawn at the 50% probability level. Only one set of the disordered F atoms is shown.
	Fig. 6. Perspective view of the structure of (V), with displacement ellipsoids drawn at the 30% probability level. Only one set of the disordered F atoms is shown.

(I) [3,5-Bis(trifluoromethyl)phenyl]bis[2-(trifluoromethyl)phenyl]borane top

Crystal data top

C₂₂H₁₁BF₁₂	D_x = 1.621 Mg m⁻³
M_r = 514.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 11281 reflections
a = 8.3748 (6) Å	θ = 2.3–24.1°
b = 18.2499 (9) Å	µ = 0.17 mm⁻¹
c = 27.5695 (14) Å	T = 173 K
V = 4213.7 (4) Å³	Needle, colourless
Z = 8	0.18 × 0.11 × 0.08 mm
F(000) = 2048

Data collection top

Stoe IPDS II two-circle diffractometer	4181 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.134
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
T_min = 0.681, T_max = 1.000	k = −21→21
33823 measured reflections	l = −30→32
7431 independent reflections

Refinement top

Refinement on F²	72 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0326P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max < 0.001
7431 reflections	Δρ_max = 0.31 e Å⁻³
687 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₁₁BF₁₂	V = 4213.7 (4) Å³
M_r = 514.12	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.3748 (6) Å	µ = 0.17 mm⁻¹
b = 18.2499 (9) Å	T = 173 K
c = 27.5695 (14) Å	0.18 × 0.11 × 0.08 mm

Data collection top

Stoe IPDS II two-circle diffractometer	7431 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	4181 reflections with I > 2σ(I)
T_min = 0.681, T_max = 1.000	R_int = 0.134
33823 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	72 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 0.82	Δρ_max = 0.31 e Å⁻³
7431 reflections	Δρ_min = −0.21 e Å⁻³
687 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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)
B1	0.5043 (8)	0.5668 (4)	0.5749 (2)	0.0335 (16)
C1	0.6798 (7)	0.5330 (3)	0.57467 (19)	0.0351 (14)
C2	0.8068 (7)	0.5590 (3)	0.6026 (2)	0.0365 (14)
C3	0.9523 (7)	0.5237 (4)	0.6041 (2)	0.0464 (17)
H3	1.0359	0.5423	0.6239	0.056*
C4	0.9760 (8)	0.4611 (4)	0.5768 (3)	0.0547 (19)
H4	1.0756	0.4363	0.5782	0.066*
C5	0.8562 (8)	0.4345 (4)	0.5476 (2)	0.0565 (19)
H5	0.8741	0.3917	0.5288	0.068*
C6	0.7089 (7)	0.4697 (4)	0.5454 (2)	0.0435 (16)
H6	0.6277	0.4516	0.5246	0.052*
C7	0.7873 (7)	0.6282 (4)	0.6299 (2)	0.0430 (16)
C11	0.4046 (6)	0.5735 (3)	0.6235 (2)	0.0308 (13)
C12	0.3723 (6)	0.5162 (3)	0.6560 (2)	0.0351 (15)
C13	0.2909 (7)	0.5284 (4)	0.6990 (2)	0.0434 (16)
H13	0.2702	0.4884	0.7202	0.052*
C14	0.2395 (8)	0.5978 (4)	0.7114 (2)	0.0468 (17)
H14	0.1870	0.6062	0.7415	0.056*
C15	0.2661 (7)	0.6551 (4)	0.6790 (2)	0.0451 (17)
H15	0.2279	0.7028	0.6864	0.054*
C16	0.3477 (7)	0.6430 (3)	0.6362 (2)	0.0353 (14)
H16	0.3658	0.6830	0.6148	0.042*
C17	0.4176 (7)	0.4398 (4)	0.6445 (3)	0.0453 (17)
C21	0.4311 (6)	0.5956 (3)	0.52674 (19)	0.0280 (13)
C22	0.5250 (6)	0.6070 (3)	0.4852 (2)	0.0318 (14)
H22	0.6349	0.5943	0.4860	0.038*
C23	0.4615 (6)	0.6362 (3)	0.4432 (2)	0.0312 (14)
C24	0.3010 (7)	0.6580 (3)	0.4414 (2)	0.0311 (13)
H24	0.2580	0.6800	0.4131	0.037*
C25	0.2069 (6)	0.6467 (3)	0.4819 (2)	0.0299 (13)
C26	0.2697 (7)	0.6164 (3)	0.5234 (2)	0.0318 (13)
H26	0.2020	0.6093	0.5507	0.038*
C27	0.5680 (8)	0.6474 (4)	0.4000 (2)	0.0441 (16)
C28	0.0328 (7)	0.6656 (4)	0.4797 (2)	0.0394 (15)
F71	0.9247 (4)	0.6642 (3)	0.63672 (17)	0.0748 (13)
F72	0.6899 (4)	0.67658 (19)	0.60676 (13)	0.0487 (9)
F73	0.7223 (5)	0.6194 (2)	0.67397 (13)	0.0622 (11)
F171	0.3299 (5)	0.3890 (2)	0.66718 (16)	0.0691 (12)
F172	0.5723 (4)	0.4243 (2)	0.65545 (15)	0.0603 (11)
F173	0.4045 (4)	0.4245 (2)	0.59652 (14)	0.0525 (10)
F271	0.4876 (5)	0.6560 (4)	0.35927 (14)	0.0946 (18)
F272	0.6622 (5)	0.7056 (2)	0.40495 (16)	0.0731 (13)
F273	0.6675 (5)	0.5916 (2)	0.39345 (14)	0.0665 (12)
F281	−0.0558 (5)	0.6091 (2)	0.46648 (19)	0.0801 (15)
F282	−0.0004 (5)	0.7189 (3)	0.44912 (17)	0.0837 (15)
F283	−0.0268 (4)	0.6857 (3)	0.52236 (14)	0.0698 (13)
B1A	0.4828 (8)	0.1765 (4)	0.6557 (2)	0.0326 (15)
C1A	0.3309 (7)	0.1326 (3)	0.67055 (19)	0.0321 (13)
C2A	0.1860 (7)	0.1269 (3)	0.6439 (2)	0.0427 (16)
C3A	0.0652 (8)	0.0807 (4)	0.6580 (3)	0.060 (2)
H3A	−0.0300	0.0783	0.6393	0.072*
C4A	0.0807 (9)	0.0380 (4)	0.6986 (3)	0.062 (2)
H4A	−0.0019	0.0048	0.7074	0.075*
C5A	0.2153 (9)	0.0432 (4)	0.7266 (2)	0.0515 (18)
H5A	0.2252	0.0145	0.7552	0.062*
C6A	0.3371 (8)	0.0905 (3)	0.7132 (2)	0.0440 (16)
H6A	0.4282	0.0945	0.7336	0.053*
C7A	0.1638 (8)	0.1735 (5)	0.5997 (3)	0.0546 (18)
C11A	0.5662 (7)	0.1692 (4)	0.6049 (2)	0.0412 (15)
C12A	0.6237 (7)	0.1050 (4)	0.5848 (2)	0.0440 (16)
C13A	0.6947 (9)	0.1015 (5)	0.5389 (3)	0.067 (2)
H13A	0.7354	0.0566	0.5265	0.080*
C14A	0.7037 (10)	0.1651 (5)	0.5123 (3)	0.071 (2)
H14A	0.7482	0.1637	0.4807	0.086*
C15A	0.6497 (10)	0.2303 (5)	0.5306 (3)	0.069 (2)
H15A	0.6573	0.2735	0.5115	0.082*
C16A	0.5854 (8)	0.2339 (4)	0.5757 (2)	0.0494 (18)
H16A	0.5524	0.2800	0.5882	0.059*
C17A	0.6158 (8)	0.0381 (4)	0.6140 (3)	0.0543 (19)
C21A	0.5600 (7)	0.2312 (3)	0.6926 (2)	0.0303 (13)
C22A	0.7176 (7)	0.2543 (3)	0.6882 (2)	0.0349 (14)
H22A	0.7807	0.2359	0.6623	0.042*
C23A	0.7847 (7)	0.3034 (3)	0.7206 (2)	0.0357 (14)
C24A	0.6943 (7)	0.3317 (3)	0.7587 (2)	0.0369 (14)
H24A	0.7397	0.3657	0.7808	0.044*
C25A	0.5374 (7)	0.3096 (3)	0.76356 (19)	0.0315 (14)
C26A	0.4724 (7)	0.2598 (3)	0.73191 (19)	0.0301 (13)
H26A	0.3654	0.2441	0.7366	0.036*
C27A	0.9560 (8)	0.3247 (5)	0.7149 (3)	0.056 (2)
C28A	0.4418 (8)	0.3405 (4)	0.8038 (2)	0.0419 (16)
F74	0.2225 (6)	0.1411 (3)	0.55924 (14)	0.0775 (13)
F75	0.0094 (5)	0.1872 (3)	0.59039 (18)	0.0917 (16)
F76	0.2366 (5)	0.2385 (2)	0.60244 (14)	0.0641 (11)
F174	0.7222 (6)	−0.0140 (2)	0.6010 (2)	0.0918 (15)
F175	0.6464 (5)	0.0501 (2)	0.66182 (15)	0.0592 (11)
F176	0.4726 (5)	0.0038 (2)	0.61325 (17)	0.0766 (13)
F274	0.962 (2)	0.3899 (13)	0.6857 (9)	0.111 (8)	0.331 (14)
F275	1.021 (2)	0.3508 (14)	0.7524 (6)	0.075 (6)	0.331 (14)
F276	1.0451 (18)	0.2804 (10)	0.6974 (9)	0.074 (6)	0.331 (14)
F277	1.0090 (11)	0.3212 (7)	0.6704 (3)	0.093 (4)	0.669 (14)
F278	0.9931 (12)	0.3878 (5)	0.7333 (5)	0.090 (4)	0.669 (14)
F279	1.0513 (10)	0.2763 (6)	0.7384 (5)	0.117 (4)	0.669 (14)
F284	0.321 (4)	0.382 (2)	0.7883 (15)	0.057 (11)	0.17 (2)
F285	0.383 (6)	0.291 (2)	0.8283 (14)	0.065 (12)	0.17 (2)
F286	0.524 (3)	0.392 (2)	0.8302 (14)	0.058 (11)	0.17 (2)
F287	0.3815 (16)	0.4062 (5)	0.7933 (3)	0.079 (3)	0.83 (2)
F288	0.3133 (11)	0.2990 (5)	0.8151 (3)	0.068 (2)	0.83 (2)
F289	0.5199 (7)	0.3471 (7)	0.8449 (2)	0.069 (3)	0.83 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.033 (4)	0.027 (4)	0.041 (4)	−0.005 (3)	−0.008 (3)	−0.002 (3)
C1	0.030 (3)	0.047 (4)	0.028 (3)	0.001 (3)	−0.004 (3)	0.009 (3)
C2	0.031 (3)	0.045 (4)	0.033 (3)	0.001 (3)	0.003 (3)	0.011 (3)
C3	0.031 (4)	0.060 (5)	0.049 (4)	0.005 (3)	−0.005 (3)	0.013 (4)
C4	0.031 (4)	0.073 (5)	0.060 (5)	0.016 (4)	−0.002 (3)	0.006 (4)
C5	0.047 (4)	0.066 (5)	0.057 (5)	0.014 (4)	0.006 (4)	0.002 (4)
C6	0.030 (3)	0.055 (4)	0.045 (4)	0.008 (3)	0.003 (3)	−0.003 (3)
C7	0.032 (4)	0.055 (4)	0.042 (4)	−0.007 (3)	−0.003 (3)	0.005 (3)
C11	0.022 (3)	0.036 (3)	0.035 (3)	−0.004 (3)	−0.007 (2)	0.001 (3)
C12	0.025 (3)	0.047 (4)	0.033 (3)	−0.003 (3)	−0.003 (3)	0.007 (3)
C13	0.043 (4)	0.050 (4)	0.037 (4)	−0.005 (3)	−0.002 (3)	0.012 (3)
C14	0.046 (4)	0.065 (5)	0.030 (4)	−0.011 (3)	0.002 (3)	0.002 (3)
C15	0.041 (4)	0.054 (4)	0.040 (4)	−0.006 (3)	−0.002 (3)	−0.016 (3)
C16	0.030 (3)	0.035 (4)	0.041 (4)	−0.001 (3)	0.000 (3)	0.000 (3)
C17	0.036 (4)	0.044 (4)	0.056 (5)	−0.004 (3)	0.000 (3)	0.016 (4)
C21	0.022 (3)	0.030 (3)	0.032 (3)	−0.004 (2)	−0.004 (2)	0.000 (3)
C22	0.019 (3)	0.038 (4)	0.038 (3)	0.000 (2)	−0.007 (3)	0.000 (3)
C23	0.031 (4)	0.034 (3)	0.029 (3)	−0.008 (3)	0.001 (3)	−0.002 (3)
C24	0.029 (3)	0.035 (3)	0.029 (3)	−0.004 (3)	−0.004 (3)	0.003 (3)
C25	0.028 (3)	0.030 (3)	0.031 (3)	−0.003 (3)	−0.003 (3)	0.000 (3)
C26	0.030 (3)	0.033 (3)	0.032 (3)	−0.001 (3)	−0.003 (3)	−0.002 (3)
C27	0.034 (3)	0.057 (5)	0.041 (4)	0.001 (3)	−0.004 (3)	0.002 (3)
C28	0.034 (4)	0.051 (4)	0.033 (3)	0.003 (3)	−0.002 (3)	0.000 (3)
F71	0.036 (2)	0.081 (3)	0.107 (4)	−0.008 (2)	−0.016 (2)	−0.028 (3)
F72	0.049 (2)	0.041 (2)	0.056 (2)	−0.0013 (17)	−0.0056 (19)	0.0029 (18)
F73	0.077 (3)	0.071 (3)	0.039 (2)	0.006 (2)	−0.002 (2)	−0.0022 (19)
F171	0.067 (3)	0.044 (2)	0.096 (3)	−0.005 (2)	0.016 (2)	0.028 (2)
F172	0.042 (2)	0.058 (2)	0.082 (3)	0.0151 (19)	−0.009 (2)	0.021 (2)
F173	0.052 (2)	0.039 (2)	0.067 (3)	0.0017 (17)	−0.002 (2)	−0.005 (2)
F271	0.041 (2)	0.207 (6)	0.036 (2)	0.011 (3)	0.001 (2)	0.027 (3)
F272	0.071 (3)	0.069 (3)	0.079 (3)	−0.025 (2)	0.036 (2)	0.002 (2)
F273	0.069 (3)	0.073 (3)	0.057 (3)	0.019 (2)	0.026 (2)	0.001 (2)
F281	0.033 (2)	0.074 (3)	0.133 (4)	−0.004 (2)	−0.011 (2)	−0.041 (3)
F282	0.045 (2)	0.110 (4)	0.096 (3)	0.030 (2)	0.009 (2)	0.066 (3)
F283	0.045 (2)	0.116 (4)	0.049 (2)	0.035 (2)	−0.0005 (19)	−0.017 (2)
B1A	0.037 (4)	0.028 (4)	0.033 (4)	0.008 (3)	−0.006 (3)	0.002 (3)
C1A	0.040 (3)	0.030 (3)	0.026 (3)	−0.002 (3)	0.000 (3)	−0.004 (3)
C2A	0.040 (4)	0.056 (4)	0.033 (3)	−0.004 (3)	0.001 (3)	−0.010 (3)
C3A	0.040 (4)	0.081 (6)	0.059 (5)	−0.016 (4)	−0.003 (4)	−0.019 (4)
C4A	0.058 (5)	0.055 (5)	0.074 (6)	−0.028 (4)	0.026 (4)	−0.015 (4)
C5A	0.065 (5)	0.045 (4)	0.044 (4)	−0.016 (4)	0.016 (4)	−0.009 (3)
C6A	0.049 (4)	0.047 (4)	0.036 (4)	−0.006 (3)	0.000 (3)	−0.009 (3)
C7A	0.040 (4)	0.077 (5)	0.048 (4)	0.007 (4)	−0.005 (3)	−0.011 (4)
C11A	0.035 (3)	0.053 (4)	0.036 (4)	−0.002 (3)	−0.002 (3)	−0.014 (3)
C12A	0.037 (4)	0.052 (4)	0.043 (4)	−0.006 (3)	0.000 (3)	−0.009 (3)
C13A	0.052 (5)	0.092 (6)	0.056 (5)	−0.018 (4)	0.007 (4)	−0.030 (5)
C14A	0.074 (6)	0.094 (7)	0.045 (5)	−0.029 (5)	0.013 (4)	−0.013 (5)
C15A	0.087 (6)	0.071 (6)	0.049 (5)	−0.019 (5)	−0.002 (4)	0.010 (4)
C16A	0.048 (4)	0.068 (5)	0.032 (4)	−0.014 (4)	0.001 (3)	0.001 (3)
C17A	0.040 (4)	0.052 (5)	0.071 (5)	0.001 (4)	0.008 (4)	−0.019 (4)
C21A	0.030 (3)	0.030 (3)	0.031 (3)	0.001 (3)	0.000 (3)	0.005 (3)
C22A	0.036 (3)	0.037 (4)	0.032 (3)	0.002 (3)	0.004 (3)	−0.002 (3)
C23A	0.032 (3)	0.033 (3)	0.043 (4)	−0.003 (3)	0.000 (3)	0.003 (3)
C24A	0.035 (3)	0.042 (4)	0.034 (3)	0.001 (3)	−0.008 (3)	0.003 (3)
C25A	0.037 (4)	0.033 (4)	0.025 (3)	0.003 (3)	−0.001 (3)	0.002 (3)
C26A	0.028 (3)	0.036 (3)	0.027 (3)	0.001 (3)	0.001 (2)	0.001 (3)
C27A	0.042 (4)	0.063 (6)	0.062 (5)	−0.011 (4)	0.004 (4)	−0.014 (4)
C28A	0.049 (4)	0.042 (4)	0.035 (4)	0.002 (3)	−0.002 (3)	−0.003 (3)
F74	0.085 (3)	0.109 (4)	0.038 (2)	0.014 (3)	−0.007 (2)	−0.008 (2)
F75	0.044 (2)	0.142 (5)	0.089 (3)	0.012 (3)	−0.023 (2)	0.011 (3)
F76	0.062 (3)	0.066 (3)	0.064 (3)	0.007 (2)	−0.005 (2)	0.010 (2)
F174	0.090 (4)	0.059 (3)	0.126 (4)	0.021 (3)	0.025 (3)	−0.025 (3)
F175	0.063 (2)	0.050 (3)	0.065 (3)	0.0087 (19)	0.001 (2)	0.004 (2)
F176	0.076 (3)	0.052 (3)	0.102 (4)	−0.017 (2)	0.002 (3)	−0.012 (2)
F274	0.094 (10)	0.110 (12)	0.128 (12)	−0.021 (8)	−0.003 (8)	0.057 (9)
F275	0.055 (8)	0.103 (12)	0.066 (8)	−0.029 (8)	−0.015 (6)	−0.003 (8)
F276	0.049 (8)	0.067 (9)	0.106 (11)	−0.007 (6)	0.022 (8)	−0.028 (8)
F277	0.067 (5)	0.150 (9)	0.061 (5)	−0.056 (5)	0.027 (4)	−0.027 (5)
F278	0.068 (5)	0.065 (5)	0.136 (9)	−0.030 (4)	0.029 (6)	−0.040 (6)
F279	0.050 (5)	0.144 (8)	0.158 (9)	0.014 (5)	−0.019 (5)	0.028 (7)
F284	0.050 (13)	0.066 (15)	0.056 (13)	0.011 (10)	0.017 (9)	−0.003 (10)
F285	0.071 (16)	0.066 (14)	0.059 (14)	0.002 (10)	0.018 (10)	0.009 (9)
F286	0.054 (13)	0.061 (15)	0.059 (13)	−0.008 (9)	0.009 (9)	−0.024 (10)
F287	0.116 (7)	0.057 (5)	0.065 (4)	0.034 (4)	0.021 (4)	0.001 (3)
F288	0.056 (4)	0.082 (4)	0.066 (4)	−0.011 (4)	0.027 (4)	−0.028 (3)
F289	0.063 (4)	0.112 (7)	0.033 (3)	0.009 (4)	−0.006 (2)	−0.019 (4)

Geometric parameters (Å, º) top

B1—C21	1.555 (9)	C1A—C6A	1.406 (8)
B1—C11	1.582 (9)	C1A—C2A	1.422 (8)
B1—C1	1.594 (9)	C2A—C3A	1.372 (9)
C1—C2	1.396 (8)	C2A—C7A	1.498 (9)
C1—C6	1.430 (9)	C3A—C4A	1.372 (11)
C2—C3	1.379 (8)	C3A—H3A	0.9500
C2—C7	1.479 (9)	C4A—C5A	1.370 (10)
C3—C4	1.383 (10)	C4A—H4A	0.9500
C3—H3	0.9500	C5A—C6A	1.386 (9)
C4—C5	1.374 (10)	C5A—H5A	0.9500
C4—H4	0.9500	C6A—H6A	0.9500
C5—C6	1.392 (9)	C7A—F76	1.337 (8)
C5—H5	0.9500	C7A—F75	1.342 (7)
C6—H6	0.9500	C7A—F74	1.356 (8)
C7—F71	1.338 (7)	C11A—C12A	1.383 (9)
C7—F73	1.342 (7)	C11A—C16A	1.438 (9)
C7—F72	1.360 (7)	C12A—C13A	1.400 (9)
C11—C16	1.400 (8)	C12A—C17A	1.463 (9)
C11—C12	1.403 (8)	C13A—C14A	1.375 (11)
C12—C13	1.386 (8)	C13A—H13A	0.9500
C12—C17	1.479 (9)	C14A—C15A	1.370 (12)
C13—C14	1.381 (9)	C14A—H14A	0.9500
C13—H13	0.9500	C15A—C16A	1.356 (10)
C14—C15	1.394 (9)	C15A—H15A	0.9500
C14—H14	0.9500	C16A—H16A	0.9500
C15—C16	1.381 (8)	C17A—F174	1.353 (8)
C15—H15	0.9500	C17A—F176	1.353 (8)
C16—H16	0.9500	C17A—F175	1.360 (8)
C17—F171	1.338 (7)	C21A—C22A	1.390 (8)
C17—F173	1.356 (7)	C21A—C26A	1.408 (8)
C17—F172	1.360 (7)	C22A—C23A	1.386 (8)
C21—C22	1.404 (8)	C22A—H22A	0.9500
C21—C26	1.407 (7)	C23A—C24A	1.393 (8)
C22—C23	1.380 (8)	C23A—C27A	1.495 (9)
C22—H22	0.9500	C24A—C25A	1.381 (8)
C23—C24	1.403 (8)	C24A—H24A	0.9500
C23—C27	1.503 (9)	C25A—C26A	1.373 (8)
C24—C25	1.380 (8)	C25A—C28A	1.478 (9)
C24—H24	0.9500	C26A—H26A	0.9500
C25—C26	1.377 (8)	C27A—F276	1.202 (16)
C25—C28	1.499 (8)	C27A—F275	1.261 (17)
C26—H26	0.9500	C27A—F278	1.295 (10)
C27—F271	1.318 (7)	C27A—F277	1.308 (10)
C27—F273	1.328 (7)	C27A—F279	1.355 (12)
C27—F272	1.331 (7)	C27A—F274	1.438 (19)
C28—F282	1.317 (7)	C28A—F285	1.23 (4)
C28—F281	1.320 (7)	C28A—F289	1.315 (8)
C28—F283	1.329 (7)	C28A—F284	1.33 (4)
B1A—C1A	1.557 (9)	C28A—F287	1.333 (10)
B1A—C21A	1.566 (9)	C28A—F288	1.353 (9)
B1A—C11A	1.573 (9)	C28A—F286	1.38 (3)

C21—B1—C11	119.2 (5)	C3A—C2A—C1A	121.9 (6)
C21—B1—C1	119.4 (5)	C3A—C2A—C7A	119.1 (6)
C11—B1—C1	121.4 (5)	C1A—C2A—C7A	118.9 (6)
C2—C1—C6	117.1 (5)	C2A—C3A—C4A	120.6 (7)
C2—C1—B1	124.6 (5)	C2A—C3A—H3A	119.7
C6—C1—B1	118.2 (5)	C4A—C3A—H3A	119.7
C3—C2—C1	122.1 (6)	C5A—C4A—C3A	119.9 (6)
C3—C2—C7	118.8 (6)	C5A—C4A—H4A	120.0
C1—C2—C7	119.1 (5)	C3A—C4A—H4A	120.0
C2—C3—C4	119.8 (6)	C4A—C5A—C6A	119.9 (7)
C2—C3—H3	120.1	C4A—C5A—H5A	120.1
C4—C3—H3	120.1	C6A—C5A—H5A	120.1
C5—C4—C3	120.4 (6)	C5A—C6A—C1A	122.4 (6)
C5—C4—H4	119.8	C5A—C6A—H6A	118.8
C3—C4—H4	119.8	C1A—C6A—H6A	118.8
C4—C5—C6	120.6 (7)	F76—C7A—F75	106.5 (6)
C4—C5—H5	119.7	F76—C7A—F74	105.6 (6)
C6—C5—H5	119.7	F75—C7A—F74	105.8 (6)
C5—C6—C1	119.9 (6)	F76—C7A—C2A	113.7 (6)
C5—C6—H6	120.0	F75—C7A—C2A	112.4 (6)
C1—C6—H6	120.0	F74—C7A—C2A	112.1 (6)
F71—C7—F73	106.2 (5)	C12A—C11A—C16A	115.7 (6)
F71—C7—F72	105.3 (5)	C12A—C11A—B1A	125.6 (6)
F73—C7—F72	105.0 (5)	C16A—C11A—B1A	118.6 (6)
F71—C7—C2	113.3 (5)	C11A—C12A—C13A	123.2 (7)
F73—C7—C2	113.8 (5)	C11A—C12A—C17A	118.1 (6)
F72—C7—C2	112.5 (5)	C13A—C12A—C17A	118.6 (7)
C16—C11—C12	116.7 (5)	C14A—C13A—C12A	117.8 (8)
C16—C11—B1	117.5 (5)	C14A—C13A—H13A	121.1
C12—C11—B1	125.7 (5)	C12A—C13A—H13A	121.1
C13—C12—C11	121.4 (6)	C15A—C14A—C13A	121.3 (7)
C13—C12—C17	117.4 (6)	C15A—C14A—H14A	119.3
C11—C12—C17	121.1 (5)	C13A—C14A—H14A	119.3
C14—C13—C12	120.9 (6)	C16A—C15A—C14A	120.7 (8)
C14—C13—H13	119.6	C16A—C15A—H15A	119.6
C12—C13—H13	119.6	C14A—C15A—H15A	119.6
C13—C14—C15	118.6 (6)	C15A—C16A—C11A	121.1 (7)
C13—C14—H14	120.7	C15A—C16A—H16A	119.4
C15—C14—H14	120.7	C11A—C16A—H16A	119.4
C16—C15—C14	120.5 (6)	F174—C17A—F176	104.7 (6)
C16—C15—H15	119.8	F174—C17A—F175	104.2 (6)
C14—C15—H15	119.8	F176—C17A—F175	104.8 (6)
C15—C16—C11	121.8 (6)	F174—C17A—C12A	114.2 (6)
C15—C16—H16	119.1	F176—C17A—C12A	114.7 (6)
C11—C16—H16	119.1	F175—C17A—C12A	113.0 (6)
F171—C17—F173	105.6 (5)	C22A—C21A—C26A	116.8 (5)
F171—C17—F172	106.0 (5)	C22A—C21A—B1A	121.9 (5)
F173—C17—F172	104.6 (5)	C26A—C21A—B1A	121.3 (5)
F171—C17—C12	114.4 (5)	C23A—C22A—C21A	121.6 (5)
F173—C17—C12	112.5 (5)	C23A—C22A—H22A	119.2
F172—C17—C12	113.1 (5)	C21A—C22A—H22A	119.2
C22—C21—C26	116.4 (5)	C22A—C23A—C24A	120.4 (5)
C22—C21—B1	121.7 (5)	C22A—C23A—C27A	119.3 (6)
C26—C21—B1	121.7 (5)	C24A—C23A—C27A	120.3 (6)
C23—C22—C21	121.7 (5)	C25A—C24A—C23A	118.8 (5)
C23—C22—H22	119.2	C25A—C24A—H24A	120.6
C21—C22—H22	119.2	C23A—C24A—H24A	120.6
C22—C23—C24	120.5 (5)	C26A—C25A—C24A	120.6 (5)
C22—C23—C27	119.3 (5)	C26A—C25A—C28A	121.0 (5)
C24—C23—C27	120.1 (5)	C24A—C25A—C28A	118.5 (5)
C25—C24—C23	118.4 (5)	C25A—C26A—C21A	121.8 (5)
C25—C24—H24	120.8	C25A—C26A—H26A	119.1
C23—C24—H24	120.8	C21A—C26A—H26A	119.1
C26—C25—C24	120.9 (5)	F276—C27A—F275	108.5 (15)
C26—C25—C28	119.7 (5)	F278—C27A—F277	109.2 (9)
C24—C25—C28	119.3 (5)	F278—C27A—F279	104.6 (9)
C25—C26—C21	121.9 (5)	F277—C27A—F279	102.6 (10)
C25—C26—H26	119.0	F276—C27A—F274	108.0 (15)
C21—C26—H26	119.0	F275—C27A—F274	97.5 (14)
F271—C27—F273	107.2 (6)	F276—C27A—C23A	117.6 (10)
F271—C27—F272	107.2 (6)	F275—C27A—C23A	115.1 (10)
F273—C27—F272	104.8 (5)	F278—C27A—C23A	114.8 (7)
F271—C27—C23	112.9 (5)	F277—C27A—C23A	114.3 (7)
F273—C27—C23	112.1 (5)	F279—C27A—C23A	110.2 (7)
F272—C27—C23	112.2 (5)	F274—C27A—C23A	108.0 (9)
F282—C28—F281	106.3 (5)	F285—C28A—F284	107 (2)
F282—C28—F283	106.4 (5)	F289—C28A—F287	107.0 (7)
F281—C28—F283	104.4 (5)	F289—C28A—F288	104.4 (7)
F282—C28—C25	113.6 (5)	F287—C28A—F288	104.6 (7)
F281—C28—C25	112.2 (5)	F285—C28A—F286	114 (2)
F283—C28—C25	113.2 (5)	F284—C28A—F286	99 (2)
C1A—B1A—C21A	119.7 (5)	F285—C28A—C25A	110.5 (18)
C1A—B1A—C11A	123.6 (5)	F289—C28A—C25A	114.4 (6)
C21A—B1A—C11A	116.7 (5)	F284—C28A—C25A	112.7 (17)
C6A—C1A—C2A	115.0 (5)	F287—C28A—C25A	112.7 (6)
C6A—C1A—B1A	118.1 (5)	F288—C28A—C25A	112.9 (6)
C2A—C1A—B1A	126.8 (5)	F286—C28A—C25A	112.9 (12)

C21—B1—C1—C2	121.8 (6)	C6A—C1A—C2A—C7A	176.0 (5)
C11—B1—C1—C2	−56.6 (8)	B1A—C1A—C2A—C7A	−7.7 (9)
C21—B1—C1—C6	−61.0 (8)	C1A—C2A—C3A—C4A	−0.1 (11)
C11—B1—C1—C6	120.6 (6)	C7A—C2A—C3A—C4A	−179.1 (7)
C6—C1—C2—C3	−3.1 (8)	C2A—C3A—C4A—C5A	2.4 (11)
B1—C1—C2—C3	174.2 (6)	C3A—C4A—C5A—C6A	−1.4 (10)
C6—C1—C2—C7	174.4 (5)	C4A—C5A—C6A—C1A	−2.0 (10)
B1—C1—C2—C7	−8.4 (8)	C2A—C1A—C6A—C5A	4.0 (9)
C1—C2—C3—C4	1.0 (10)	B1A—C1A—C6A—C5A	−172.6 (6)
C7—C2—C3—C4	−176.5 (6)	C3A—C2A—C7A—F76	146.9 (6)
C2—C3—C4—C5	0.9 (10)	C1A—C2A—C7A—F76	−32.1 (8)
C3—C4—C5—C6	−0.6 (11)	C3A—C2A—C7A—F75	25.7 (9)
C4—C5—C6—C1	−1.6 (10)	C1A—C2A—C7A—F75	−153.3 (6)
C2—C1—C6—C5	3.4 (9)	C3A—C2A—C7A—F74	−93.4 (8)
B1—C1—C6—C5	−174.1 (6)	C1A—C2A—C7A—F74	87.6 (7)
C3—C2—C7—F71	25.7 (8)	C1A—B1A—C11A—C12A	−57.0 (9)
C1—C2—C7—F71	−151.9 (5)	C21A—B1A—C11A—C12A	122.9 (6)
C3—C2—C7—F73	−95.8 (7)	C1A—B1A—C11A—C16A	122.7 (6)
C1—C2—C7—F73	86.7 (7)	C21A—B1A—C11A—C16A	−57.4 (7)
C3—C2—C7—F72	145.0 (6)	C16A—C11A—C12A—C13A	−0.8 (9)
C1—C2—C7—F72	−32.5 (7)	B1A—C11A—C12A—C13A	178.9 (6)
C21—B1—C11—C16	−54.3 (7)	C16A—C11A—C12A—C17A	176.5 (6)
C1—B1—C11—C16	124.2 (6)	B1A—C11A—C12A—C17A	−3.8 (9)
C21—B1—C11—C12	128.0 (6)	C11A—C12A—C13A—C14A	−1.6 (11)
C1—B1—C11—C12	−53.6 (8)	C17A—C12A—C13A—C14A	−178.9 (7)
C16—C11—C12—C13	−1.3 (8)	C12A—C13A—C14A—C15A	2.0 (12)
B1—C11—C12—C13	176.5 (5)	C13A—C14A—C15A—C16A	−0.1 (13)
C16—C11—C12—C17	175.9 (5)	C14A—C15A—C16A—C11A	−2.4 (11)
B1—C11—C12—C17	−6.3 (8)	C12A—C11A—C16A—C15A	2.8 (9)
C11—C12—C13—C14	−0.4 (9)	B1A—C11A—C16A—C15A	−176.9 (6)
C17—C12—C13—C14	−177.7 (6)	C11A—C12A—C17A—F174	−156.8 (6)
C12—C13—C14—C15	2.2 (9)	C13A—C12A—C17A—F174	20.7 (9)
C13—C14—C15—C16	−2.4 (9)	C11A—C12A—C17A—F176	82.3 (8)
C14—C15—C16—C11	0.8 (9)	C13A—C12A—C17A—F176	−100.2 (7)
C12—C11—C16—C15	1.1 (8)	C11A—C12A—C17A—F175	−37.8 (8)
B1—C11—C16—C15	−176.9 (5)	C13A—C12A—C17A—F175	139.7 (6)
C13—C12—C17—F171	22.2 (8)	C1A—B1A—C21A—C22A	159.7 (5)
C11—C12—C17—F171	−155.1 (5)	C11A—B1A—C21A—C22A	−20.2 (8)
C13—C12—C17—F173	142.6 (5)	C1A—B1A—C21A—C26A	−20.5 (8)
C11—C12—C17—F173	−34.7 (7)	C11A—B1A—C21A—C26A	159.6 (5)
C13—C12—C17—F172	−99.2 (6)	C26A—C21A—C22A—C23A	−0.5 (8)
C11—C12—C17—F172	83.5 (7)	B1A—C21A—C22A—C23A	179.3 (5)
C11—B1—C21—C22	165.0 (5)	C21A—C22A—C23A—C24A	−0.7 (9)
C1—B1—C21—C22	−13.5 (8)	C21A—C22A—C23A—C27A	178.3 (6)
C11—B1—C21—C26	−10.6 (8)	C22A—C23A—C24A—C25A	0.5 (8)
C1—B1—C21—C26	170.9 (5)	C27A—C23A—C24A—C25A	−178.5 (6)
C26—C21—C22—C23	−0.8 (8)	C23A—C24A—C25A—C26A	0.9 (8)
B1—C21—C22—C23	−176.6 (5)	C23A—C24A—C25A—C28A	−179.5 (5)
C21—C22—C23—C24	2.3 (8)	C24A—C25A—C26A—C21A	−2.1 (8)
C21—C22—C23—C27	179.8 (5)	C28A—C25A—C26A—C21A	178.2 (6)
C22—C23—C24—C25	−2.6 (8)	C22A—C21A—C26A—C25A	1.9 (8)
C27—C23—C24—C25	179.9 (5)	B1A—C21A—C26A—C25A	−177.9 (5)
C23—C24—C25—C26	1.4 (8)	C22A—C23A—C27A—F276	−29.9 (18)
C23—C24—C25—C28	−176.5 (5)	C24A—C23A—C27A—F276	149.1 (16)
C24—C25—C26—C21	0.1 (8)	C22A—C23A—C27A—F275	−159.8 (14)
C28—C25—C26—C21	178.0 (5)	C24A—C23A—C27A—F275	19.2 (16)
C22—C21—C26—C25	−0.4 (8)	C22A—C23A—C27A—F278	155.3 (9)
B1—C21—C26—C25	175.4 (5)	C24A—C23A—C27A—F278	−25.7 (12)
C22—C23—C27—F271	162.5 (6)	C22A—C23A—C27A—F277	27.9 (12)
C24—C23—C27—F271	−20.0 (9)	C24A—C23A—C27A—F277	−153.1 (9)
C22—C23—C27—F273	41.3 (8)	C22A—C23A—C27A—F279	−87.0 (10)
C24—C23—C27—F273	−141.2 (6)	C24A—C23A—C27A—F279	92.0 (10)
C22—C23—C27—F272	−76.3 (7)	C22A—C23A—C27A—F274	92.6 (14)
C24—C23—C27—F272	101.2 (6)	C24A—C23A—C27A—F274	−88.4 (14)
C26—C25—C28—F282	153.5 (6)	C26A—C25A—C28A—F285	54 (3)
C24—C25—C28—F282	−28.6 (8)	C24A—C25A—C28A—F285	−126 (3)
C26—C25—C28—F281	−85.9 (7)	C26A—C25A—C28A—F289	139.5 (8)
C24—C25—C28—F281	92.0 (7)	C24A—C25A—C28A—F289	−40.2 (10)
C26—C25—C28—F283	32.0 (8)	C26A—C25A—C28A—F284	−66 (2)
C24—C25—C28—F283	−150.1 (6)	C24A—C25A—C28A—F284	115 (2)
C21A—B1A—C1A—C6A	−54.8 (8)	C26A—C25A—C28A—F287	−98.0 (9)
C11A—B1A—C1A—C6A	125.2 (6)	C24A—C25A—C28A—F287	82.4 (9)
C21A—B1A—C1A—C2A	129.0 (6)	C26A—C25A—C28A—F288	20.3 (10)
C11A—B1A—C1A—C2A	−51.0 (9)	C24A—C25A—C28A—F288	−159.3 (8)
C6A—C1A—C2A—C3A	−3.0 (9)	C26A—C25A—C28A—F286	−177 (2)
B1A—C1A—C2A—C3A	173.3 (6)	C24A—C25A—C28A—F286	4 (2)

(II) [3,5-Bis(trifluoromethyl)phenyl]bis[2,6-bis(trifluoromethyl)phenyl]borane top

Crystal data top

C₂₄H₉BF₁₈	Z = 2
M_r = 650.12	F(000) = 640
Triclinic, P1	D_x = 1.755 Mg m⁻³
a = 8.2059 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7103 (7) Å	Cell parameters from 23861 reflections
c = 18.0982 (14) Å	θ = 3.5–27.8°
α = 103.491 (6)°	µ = 0.20 mm⁻¹
β = 95.430 (6)°	T = 173 K
γ = 99.093 (6)°	Plate, colourless
V = 1230.38 (17) Å³	0.21 × 0.17 × 0.08 mm

Data collection top

Stoe IPDS II two-circle diffractometer	4520 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.058
ω scans	θ_max = 27.6°, θ_min = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
T_min = 0.434, T_max = 1.000	k = −11→9
25668 measured reflections	l = −23→23
5677 independent reflections

Refinement top

Refinement on F²	36 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0593P)² + 1.1354P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5677 reflections	Δρ_max = 0.58 e Å⁻³
416 parameters	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₄H₉BF₁₈	γ = 99.093 (6)°
M_r = 650.12	V = 1230.38 (17) Å³
Triclinic, P1	Z = 2
a = 8.2059 (6) Å	Mo Kα radiation
b = 8.7103 (7) Å	µ = 0.20 mm⁻¹
c = 18.0982 (14) Å	T = 173 K
α = 103.491 (6)°	0.21 × 0.17 × 0.08 mm
β = 95.430 (6)°

Data collection top

Stoe IPDS II two-circle diffractometer	5677 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	4520 reflections with I > 2σ(I)
T_min = 0.434, T_max = 1.000	R_int = 0.058
25668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	36 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.04	Δρ_max = 0.58 e Å⁻³
5677 reflections	Δρ_min = −0.36 e Å⁻³
416 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
B1	0.1728 (3)	0.3799 (3)	0.23100 (13)	0.0235 (4)
C1	0.2670 (2)	0.3357 (2)	0.30035 (12)	0.0241 (4)
C2	0.4178 (2)	0.2812 (3)	0.29397 (12)	0.0261 (4)
H2	0.4649	0.2746	0.2476	0.031*
C3	0.5002 (3)	0.2365 (3)	0.35398 (13)	0.0280 (4)
C4	0.4325 (3)	0.2417 (3)	0.42187 (12)	0.0291 (4)
H4	0.4881	0.2102	0.4628	0.035*
C5	0.2817 (3)	0.2937 (3)	0.42861 (12)	0.0284 (4)
C6	0.2008 (2)	0.3422 (3)	0.36966 (12)	0.0260 (4)
H6	0.0994	0.3802	0.3761	0.031*
C7	0.6611 (3)	0.1782 (3)	0.34318 (15)	0.0397 (5)
C8	0.2056 (3)	0.2939 (3)	0.50101 (14)	0.0404 (6)
C11	0.1989 (3)	0.2836 (3)	0.14731 (12)	0.0272 (4)
C12	0.1754 (3)	0.1136 (3)	0.12614 (14)	0.0370 (5)
C13	0.2103 (4)	0.0286 (4)	0.05606 (16)	0.0505 (7)
H13	0.1931	−0.0854	0.0441	0.061*
C14	0.2691 (4)	0.1077 (4)	0.00418 (16)	0.0556 (8)
H14	0.2951	0.0489	−0.0430	0.067*
C15	0.2907 (3)	0.2733 (4)	0.02066 (14)	0.0469 (7)
H15	0.3285	0.3283	−0.0159	0.056*
C16	0.2569 (3)	0.3602 (3)	0.09140 (12)	0.0325 (5)
C17	0.1085 (4)	0.0061 (3)	0.17596 (16)	0.0464 (7)
C18	0.2860 (3)	0.5396 (3)	0.10516 (14)	0.0394 (5)
C21	0.0571 (2)	0.5121 (2)	0.24760 (11)	0.0242 (4)
C22	−0.1085 (3)	0.4893 (3)	0.21030 (13)	0.0298 (4)
C23	−0.2119 (3)	0.5999 (3)	0.23061 (16)	0.0406 (6)
H23	−0.3220	0.5799	0.2044	0.049*
C24	−0.1565 (4)	0.7376 (3)	0.28810 (18)	0.0483 (7)
H24	−0.2287	0.8111	0.3027	0.058*
C25	0.0036 (4)	0.7680 (3)	0.32414 (15)	0.0428 (6)
H25	0.0431	0.8647	0.3630	0.051*
C26	0.1097 (3)	0.6588 (3)	0.30464 (12)	0.0306 (4)
C27	−0.1848 (3)	0.3437 (3)	0.14630 (15)	0.0392 (5)
C28	0.2826 (3)	0.7167 (3)	0.35012 (15)	0.0406 (6)
F71	0.7803 (2)	0.2920 (2)	0.33426 (14)	0.0713 (6)
F72	0.7171 (2)	0.1194 (3)	0.39956 (12)	0.0760 (7)
F73	0.6457 (2)	0.0600 (2)	0.27897 (12)	0.0669 (5)
F81	0.0806 (5)	0.3694 (6)	0.50855 (18)	0.0785 (12)	0.725 (6)
F82	0.1472 (7)	0.1468 (4)	0.5053 (2)	0.1009 (15)	0.725 (6)
F83	0.3141 (4)	0.3594 (6)	0.56332 (13)	0.0763 (12)	0.725 (6)
F81'	0.1855 (16)	0.4388 (12)	0.5349 (6)	0.087 (3)	0.275 (6)
F82'	0.0597 (10)	0.2126 (14)	0.4890 (5)	0.071 (3)	0.275 (6)
F83'	0.2876 (11)	0.2312 (14)	0.5477 (5)	0.069 (2)	0.275 (6)
F171	0.2311 (3)	−0.0563 (2)	0.20595 (12)	0.0681 (6)
F172	−0.0045 (3)	−0.12056 (19)	0.13317 (11)	0.0633 (5)
F173	0.0349 (2)	0.07395 (19)	0.23369 (9)	0.0530 (4)
F181	0.3832 (3)	0.5931 (3)	0.05786 (13)	0.0761 (6)
F182	0.1460 (2)	0.5972 (2)	0.09648 (11)	0.0560 (4)
F183	0.3600 (2)	0.61527 (19)	0.17693 (9)	0.0501 (4)
F271	−0.35104 (19)	0.3265 (3)	0.13199 (12)	0.0717 (6)
F272	−0.1578 (2)	0.20576 (19)	0.16169 (10)	0.0521 (4)
F273	−0.1271 (2)	0.3454 (2)	0.08002 (9)	0.0541 (4)
F281	0.3319 (3)	0.87464 (19)	0.35850 (13)	0.0681 (6)
F282	0.2838 (2)	0.6960 (2)	0.42167 (9)	0.0599 (5)
F283	0.40321 (18)	0.64729 (18)	0.32038 (9)	0.0454 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0197 (9)	0.0246 (10)	0.0258 (10)	0.0025 (8)	0.0021 (8)	0.0068 (8)
C1	0.0225 (9)	0.0240 (9)	0.0254 (9)	0.0057 (7)	0.0007 (7)	0.0058 (8)
C2	0.0236 (9)	0.0296 (10)	0.0254 (9)	0.0071 (8)	0.0038 (7)	0.0062 (8)
C3	0.0233 (9)	0.0279 (10)	0.0320 (11)	0.0068 (8)	−0.0007 (8)	0.0065 (8)
C4	0.0269 (10)	0.0313 (11)	0.0282 (10)	0.0045 (8)	−0.0042 (8)	0.0095 (8)
C5	0.0288 (10)	0.0314 (11)	0.0248 (10)	0.0038 (8)	0.0025 (8)	0.0082 (8)
C6	0.0203 (9)	0.0303 (10)	0.0283 (10)	0.0070 (8)	0.0028 (7)	0.0079 (8)
C7	0.0309 (11)	0.0481 (14)	0.0459 (14)	0.0177 (10)	0.0040 (10)	0.0172 (11)
C8	0.0397 (13)	0.0572 (16)	0.0291 (11)	0.0122 (11)	0.0071 (10)	0.0175 (11)
C11	0.0243 (9)	0.0340 (11)	0.0240 (9)	0.0120 (8)	−0.0005 (7)	0.0062 (8)
C12	0.0401 (12)	0.0361 (12)	0.0311 (11)	0.0153 (10)	−0.0059 (9)	0.0004 (9)
C13	0.0570 (17)	0.0476 (15)	0.0385 (14)	0.0220 (13)	−0.0067 (12)	−0.0088 (12)
C14	0.0517 (16)	0.071 (2)	0.0330 (13)	0.0214 (14)	0.0031 (12)	−0.0145 (13)
C15	0.0350 (12)	0.079 (2)	0.0260 (11)	0.0128 (12)	0.0073 (9)	0.0083 (12)
C16	0.0244 (10)	0.0492 (13)	0.0259 (10)	0.0125 (9)	0.0037 (8)	0.0097 (9)
C17	0.0580 (16)	0.0277 (12)	0.0468 (15)	0.0035 (11)	−0.0161 (12)	0.0082 (11)
C18	0.0347 (12)	0.0531 (15)	0.0358 (12)	0.0055 (10)	0.0104 (10)	0.0217 (11)
C21	0.0261 (9)	0.0276 (10)	0.0220 (9)	0.0080 (8)	0.0050 (7)	0.0098 (8)
C22	0.0265 (10)	0.0392 (12)	0.0297 (10)	0.0119 (9)	0.0071 (8)	0.0152 (9)
C23	0.0322 (11)	0.0518 (15)	0.0487 (14)	0.0206 (11)	0.0112 (10)	0.0234 (12)
C24	0.0566 (16)	0.0463 (15)	0.0569 (17)	0.0325 (13)	0.0234 (13)	0.0214 (13)
C25	0.0615 (16)	0.0322 (12)	0.0399 (13)	0.0191 (11)	0.0153 (12)	0.0095 (10)
C26	0.0399 (12)	0.0277 (10)	0.0267 (10)	0.0095 (9)	0.0055 (9)	0.0095 (8)
C27	0.0232 (10)	0.0539 (15)	0.0388 (13)	0.0064 (10)	−0.0011 (9)	0.0107 (11)
C28	0.0523 (15)	0.0267 (11)	0.0370 (12)	0.0001 (10)	−0.0044 (11)	0.0058 (9)
F71	0.0285 (8)	0.0730 (13)	0.1181 (18)	0.0125 (8)	0.0192 (9)	0.0297 (12)
F72	0.0612 (11)	0.1286 (19)	0.0690 (12)	0.0639 (12)	0.0133 (9)	0.0533 (13)
F73	0.0589 (11)	0.0714 (12)	0.0703 (12)	0.0408 (10)	0.0088 (9)	−0.0014 (10)
F81	0.074 (2)	0.141 (3)	0.0527 (16)	0.065 (2)	0.0361 (14)	0.0464 (17)
F82	0.161 (3)	0.0634 (18)	0.092 (2)	0.0052 (19)	0.081 (2)	0.0332 (16)
F83	0.0596 (15)	0.130 (3)	0.0243 (11)	−0.0035 (16)	0.0038 (10)	0.0042 (14)
F81'	0.101 (5)	0.081 (4)	0.077 (4)	0.012 (3)	0.041 (3)	0.008 (3)
F82'	0.055 (3)	0.096 (4)	0.058 (3)	−0.010 (3)	0.022 (3)	0.021 (3)
F83'	0.070 (4)	0.100 (4)	0.053 (3)	0.030 (3)	0.013 (3)	0.042 (3)
F171	0.0820 (13)	0.0443 (9)	0.0746 (13)	0.0144 (9)	−0.0285 (10)	0.0221 (9)
F172	0.0798 (12)	0.0321 (8)	0.0611 (11)	−0.0066 (8)	−0.0246 (9)	0.0034 (7)
F173	0.0697 (11)	0.0397 (8)	0.0437 (9)	−0.0079 (7)	0.0036 (8)	0.0126 (7)
F181	0.0886 (15)	0.0794 (14)	0.0734 (13)	0.0057 (11)	0.0504 (12)	0.0361 (11)
F182	0.0523 (10)	0.0543 (10)	0.0704 (12)	0.0198 (8)	0.0039 (8)	0.0285 (9)
F183	0.0522 (9)	0.0461 (9)	0.0472 (9)	−0.0026 (7)	−0.0010 (7)	0.0134 (7)
F271	0.0233 (7)	0.0952 (15)	0.0786 (13)	0.0074 (8)	−0.0080 (8)	−0.0052 (11)
F272	0.0503 (9)	0.0404 (8)	0.0564 (10)	−0.0021 (7)	−0.0004 (7)	0.0043 (7)
F273	0.0512 (9)	0.0752 (12)	0.0298 (7)	0.0065 (8)	0.0001 (6)	0.0068 (7)
F281	0.0776 (13)	0.0268 (8)	0.0852 (14)	−0.0087 (8)	−0.0163 (10)	0.0080 (8)
F282	0.0724 (12)	0.0670 (11)	0.0311 (8)	0.0055 (9)	−0.0105 (7)	0.0063 (7)
F283	0.0331 (7)	0.0431 (8)	0.0529 (9)	−0.0028 (6)	−0.0048 (6)	0.0090 (7)

Geometric parameters (Å, º) top

B1—C1	1.568 (3)	C14—C15	1.382 (5)
B1—C21	1.598 (3)	C14—H14	0.9500
B1—C11	1.603 (3)	C15—C16	1.404 (3)
C1—C2	1.399 (3)	C15—H15	0.9500
C1—C6	1.406 (3)	C16—C18	1.500 (4)
C2—C3	1.389 (3)	C17—F173	1.323 (4)
C2—H2	0.9500	C17—F171	1.346 (3)
C3—C4	1.390 (3)	C17—F172	1.348 (3)
C3—C7	1.501 (3)	C18—F182	1.335 (3)
C4—C5	1.390 (3)	C18—F181	1.335 (3)
C4—H4	0.9500	C18—F183	1.347 (3)
C5—C6	1.386 (3)	C21—C26	1.418 (3)
C5—C8	1.504 (3)	C21—C22	1.421 (3)
C6—H6	0.9500	C22—C23	1.391 (3)
C7—F72	1.320 (3)	C22—C27	1.506 (3)
C7—F71	1.328 (3)	C23—C24	1.372 (4)
C7—F73	1.341 (3)	C23—H23	0.9500
C8—F82'	1.262 (8)	C24—C25	1.367 (4)
C8—F83'	1.299 (7)	C24—H24	0.9500
C8—F81	1.304 (4)	C25—C26	1.397 (3)
C8—F81'	1.311 (10)	C25—H25	0.9500
C8—F82	1.318 (4)	C26—C28	1.518 (3)
C8—F83	1.319 (4)	C27—F273	1.333 (3)
C11—C16	1.415 (3)	C27—F271	1.342 (3)
C11—C12	1.417 (3)	C27—F272	1.342 (3)
C12—C13	1.391 (4)	C28—F283	1.331 (3)
C12—C17	1.522 (4)	C28—F281	1.339 (3)
C13—C14	1.368 (5)	C28—F282	1.348 (3)
C13—H13	0.9500

C1—B1—C21	119.09 (18)	C15—C14—H14	120.1
C1—B1—C11	116.00 (18)	C14—C15—C16	120.0 (3)
C21—B1—C11	124.89 (17)	C14—C15—H15	120.0
C2—C1—C6	117.52 (18)	C16—C15—H15	120.0
C2—C1—B1	120.66 (18)	C15—C16—C11	122.1 (2)
C6—C1—B1	121.76 (18)	C15—C16—C18	116.6 (2)
C3—C2—C1	121.41 (19)	C11—C16—C18	121.3 (2)
C3—C2—H2	119.3	F173—C17—F171	106.9 (2)
C1—C2—H2	119.3	F173—C17—F172	106.2 (3)
C2—C3—C4	120.54 (19)	F171—C17—F172	105.8 (2)
C2—C3—C7	118.7 (2)	F173—C17—C12	116.3 (2)
C4—C3—C7	120.7 (2)	F171—C17—C12	110.7 (2)
C3—C4—C5	118.62 (19)	F172—C17—C12	110.3 (2)
C3—C4—H4	120.7	F182—C18—F181	106.0 (2)
C5—C4—H4	120.7	F182—C18—F183	105.4 (2)
C6—C5—C4	121.15 (19)	F181—C18—F183	106.4 (2)
C6—C5—C8	120.3 (2)	F182—C18—C16	113.3 (2)
C4—C5—C8	118.59 (19)	F181—C18—C16	112.8 (2)
C5—C6—C1	120.73 (19)	F183—C18—C16	112.3 (2)
C5—C6—H6	119.6	C26—C21—C22	114.65 (19)
C1—C6—H6	119.6	C26—C21—B1	121.89 (18)
F72—C7—F71	108.6 (2)	C22—C21—B1	123.36 (18)
F72—C7—F73	105.8 (2)	C23—C22—C21	122.3 (2)
F71—C7—F73	104.4 (2)	C23—C22—C27	115.2 (2)
F72—C7—C3	113.5 (2)	C21—C22—C27	122.5 (2)
F71—C7—C3	112.3 (2)	C24—C23—C22	120.7 (2)
F73—C7—C3	111.8 (2)	C24—C23—H23	119.6
F82'—C8—F83'	104.4 (7)	C22—C23—H23	119.6
F82'—C8—F81'	103.2 (7)	C25—C24—C23	119.4 (2)
F83'—C8—F81'	111.6 (7)	C25—C24—H24	120.3
F81—C8—F82	105.4 (3)	C23—C24—H24	120.3
F81—C8—F83	106.1 (3)	C24—C25—C26	120.9 (2)
F82—C8—F83	105.9 (3)	C24—C25—H25	119.6
F82'—C8—C5	113.1 (4)	C26—C25—H25	119.6
F83'—C8—C5	113.1 (4)	C25—C26—C21	122.0 (2)
F81—C8—C5	114.7 (2)	C25—C26—C28	112.6 (2)
F81'—C8—C5	110.9 (5)	C21—C26—C28	125.4 (2)
F82—C8—C5	111.6 (3)	F273—C27—F271	106.5 (2)
F83—C8—C5	112.5 (2)	F273—C27—F272	105.6 (2)
C16—C11—C12	115.1 (2)	F271—C27—F272	105.1 (2)
C16—C11—B1	123.2 (2)	F273—C27—C22	113.5 (2)
C12—C11—B1	121.5 (2)	F271—C27—C22	112.6 (2)
C13—C12—C11	122.3 (3)	F272—C27—C22	112.9 (2)
C13—C12—C17	113.4 (2)	F283—C28—F281	105.9 (2)
C11—C12—C17	124.3 (2)	F283—C28—F282	106.5 (2)
C14—C13—C12	120.6 (3)	F281—C28—F282	106.0 (2)
C14—C13—H13	119.7	F283—C28—C26	116.0 (2)
C12—C13—H13	119.7	F281—C28—C26	110.7 (2)
C13—C14—C15	119.8 (2)	F282—C28—C26	111.1 (2)
C13—C14—H14	120.1

C21—B1—C1—C2	−151.65 (19)	C14—C15—C16—C18	179.1 (2)
C11—B1—C1—C2	29.5 (3)	C12—C11—C16—C15	−0.9 (3)
C21—B1—C1—C6	31.2 (3)	B1—C11—C16—C15	175.1 (2)
C11—B1—C1—C6	−147.68 (19)	C12—C11—C16—C18	179.4 (2)
C6—C1—C2—C3	−0.6 (3)	B1—C11—C16—C18	−4.7 (3)
B1—C1—C2—C3	−177.88 (19)	C13—C12—C17—F173	−163.8 (2)
C1—C2—C3—C4	1.4 (3)	C11—C12—C17—F173	15.4 (4)
C1—C2—C3—C7	179.7 (2)	C13—C12—C17—F171	73.9 (3)
C2—C3—C4—C5	−0.6 (3)	C11—C12—C17—F171	−106.9 (3)
C7—C3—C4—C5	−178.8 (2)	C13—C12—C17—F172	−42.9 (3)
C3—C4—C5—C6	−1.0 (3)	C11—C12—C17—F172	136.3 (2)
C3—C4—C5—C8	177.9 (2)	C15—C16—C18—F182	102.7 (2)
C4—C5—C6—C1	1.8 (3)	C11—C16—C18—F182	−77.6 (3)
C8—C5—C6—C1	−177.1 (2)	C15—C16—C18—F181	−17.8 (3)
C2—C1—C6—C5	−1.0 (3)	C11—C16—C18—F181	162.0 (2)
B1—C1—C6—C5	176.28 (19)	C15—C16—C18—F183	−138.0 (2)
C2—C3—C7—F72	−171.6 (2)	C11—C16—C18—F183	41.7 (3)
C4—C3—C7—F72	6.6 (3)	C1—B1—C21—C26	44.8 (3)
C2—C3—C7—F71	64.8 (3)	C11—B1—C21—C26	−136.4 (2)
C4—C3—C7—F71	−116.9 (3)	C1—B1—C21—C22	−131.4 (2)
C2—C3—C7—F73	−52.0 (3)	C11—B1—C21—C22	47.3 (3)
C4—C3—C7—F73	126.2 (2)	C26—C21—C22—C23	−2.4 (3)
C6—C5—C8—F82'	55.4 (7)	B1—C21—C22—C23	174.1 (2)
C4—C5—C8—F82'	−123.6 (7)	C26—C21—C22—C27	177.9 (2)
C6—C5—C8—F83'	173.8 (6)	B1—C21—C22—C27	−5.7 (3)
C4—C5—C8—F83'	−5.1 (7)	C21—C22—C23—C24	0.3 (4)
C6—C5—C8—F81	−12.3 (4)	C27—C22—C23—C24	−179.9 (2)
C4—C5—C8—F81	168.8 (3)	C22—C23—C24—C25	1.9 (4)
C6—C5—C8—F81'	−60.0 (7)	C23—C24—C25—C26	−1.8 (4)
C4—C5—C8—F81'	121.1 (7)	C24—C25—C26—C21	−0.5 (4)
C6—C5—C8—F82	107.4 (4)	C24—C25—C26—C28	178.8 (2)
C4—C5—C8—F82	−71.5 (4)	C22—C21—C26—C25	2.5 (3)
C6—C5—C8—F83	−133.7 (3)	B1—C21—C26—C25	−174.0 (2)
C4—C5—C8—F83	47.3 (4)	C22—C21—C26—C28	−176.7 (2)
C1—B1—C11—C16	−124.6 (2)	B1—C21—C26—C28	6.7 (3)
C21—B1—C11—C16	56.6 (3)	C23—C22—C27—F273	106.2 (2)
C1—B1—C11—C12	51.1 (3)	C21—C22—C27—F273	−74.1 (3)
C21—B1—C11—C12	−127.7 (2)	C23—C22—C27—F271	−14.9 (3)
C16—C11—C12—C13	1.3 (3)	C21—C22—C27—F271	164.9 (2)
B1—C11—C12—C13	−174.7 (2)	C23—C22—C27—F272	−133.7 (2)
C16—C11—C12—C17	−177.8 (2)	C21—C22—C27—F272	46.1 (3)
B1—C11—C12—C17	6.1 (3)	C25—C26—C28—F283	−160.4 (2)
C11—C12—C13—C14	−0.2 (4)	C21—C26—C28—F283	18.9 (3)
C17—C12—C13—C14	179.0 (3)	C25—C26—C28—F281	−39.7 (3)
C12—C13—C14—C15	−1.4 (4)	C21—C26—C28—F281	139.6 (2)
C13—C14—C15—C16	1.8 (4)	C25—C26—C28—F282	77.7 (3)
C14—C15—C16—C11	−0.6 (4)	C21—C26—C28—F282	−103.0 (3)

(III) [2,6-Bis(trifluoromethyl)phenyl]bis[3,5-bis(trifluoromethyl)phenyl]borane top

Crystal data top

C₂₄H₉BF₁₈	Z = 2
M_r = 650.12	F(000) = 640
Triclinic, P1	D_x = 1.752 Mg m⁻³
a = 10.8257 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4704 (13) Å	Cell parameters from 11788 reflections
c = 12.0198 (14) Å	θ = 3.4–25.8°
α = 117.067 (8)°	µ = 0.20 mm⁻¹
β = 101.774 (9)°	T = 173 K
γ = 100.795 (9)°	Block, colourless
V = 1232.1 (3) Å³	0.28 × 0.28 × 0.26 mm

Data collection top

Stoe IPDS II two-circle diffractometer	3599 reflections with I > 2σ(I)
ω scans	R_int = 0.024
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θ_max = 25.6°, θ_min = 3.4°
T_min = 0.627, T_max = 1.000	h = −13→12
9949 measured reflections	k = −13→13
4566 independent reflections	l = −14→14

Refinement top

Refinement on F²	36 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0545P)² + 0.5993P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4566 reflections	Δρ_max = 0.45 e Å⁻³
444 parameters	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₄H₉BF₁₈	γ = 100.795 (9)°
M_r = 650.12	V = 1232.1 (3) Å³
Triclinic, P1	Z = 2
a = 10.8257 (11) Å	Mo Kα radiation
b = 11.4704 (13) Å	µ = 0.20 mm⁻¹
c = 12.0198 (14) Å	T = 173 K
α = 117.067 (8)°	0.28 × 0.28 × 0.26 mm
β = 101.774 (9)°

Data collection top

Stoe IPDS II two-circle diffractometer	4566 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	3599 reflections with I > 2σ(I)
T_min = 0.627, T_max = 1.000	R_int = 0.024
9949 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	36 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.06	Δρ_max = 0.45 e Å⁻³
4566 reflections	Δρ_min = −0.26 e Å⁻³
444 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
B1	0.5262 (2)	0.2224 (2)	0.4262 (2)	0.0223 (5)
C1	0.56941 (18)	0.1715 (2)	0.29700 (19)	0.0214 (4)
C2	0.5499 (2)	0.2273 (2)	0.21419 (19)	0.0254 (4)
C3	0.6023 (2)	0.1946 (2)	0.1116 (2)	0.0331 (5)
H3	0.5889	0.2353	0.0587	0.040*
C4	0.6737 (2)	0.1031 (3)	0.0861 (2)	0.0377 (6)
H4	0.7114	0.0827	0.0173	0.045*
C5	0.6903 (2)	0.0416 (2)	0.1609 (2)	0.0339 (5)
H5	0.7365	−0.0243	0.1414	0.041*
C6	0.63938 (19)	0.0759 (2)	0.2652 (2)	0.0257 (4)
C7	0.4670 (2)	0.3208 (2)	0.2335 (2)	0.0329 (5)
C8	0.6618 (2)	0.0072 (2)	0.3441 (2)	0.0340 (5)
C11	0.3771 (2)	0.1756 (2)	0.41632 (19)	0.0227 (4)
C12	0.3316 (2)	0.2580 (2)	0.5158 (2)	0.0258 (4)
H12	0.3929	0.3415	0.5908	0.031*
C13	0.1994 (2)	0.2210 (2)	0.5078 (2)	0.0299 (5)
C14	0.1082 (2)	0.0987 (2)	0.3997 (2)	0.0319 (5)
H14	0.0177	0.0725	0.3945	0.038*
C15	0.1508 (2)	0.0153 (2)	0.2997 (2)	0.0299 (5)
C16	0.2832 (2)	0.0537 (2)	0.3073 (2)	0.0257 (4)
H16	0.3105	−0.0038	0.2371	0.031*
C17	0.1577 (3)	0.3145 (3)	0.6186 (3)	0.0448 (6)
C18	0.0544 (3)	−0.1163 (3)	0.1814 (3)	0.0518 (8)
C21	0.6378 (2)	0.3241 (2)	0.56405 (19)	0.0232 (4)
C22	0.6306 (2)	0.3189 (2)	0.6765 (2)	0.0251 (4)
H22	0.5570	0.2525	0.6689	0.030*
C23	0.7290 (2)	0.4089 (2)	0.7994 (2)	0.0272 (5)
C24	0.8361 (2)	0.5084 (2)	0.8140 (2)	0.0282 (5)
H24	0.9024	0.5707	0.8982	0.034*
C25	0.8450 (2)	0.5154 (2)	0.7035 (2)	0.0259 (4)
C26	0.74900 (19)	0.4235 (2)	0.5795 (2)	0.0240 (4)
H26	0.7586	0.4279	0.5046	0.029*
C27	0.7153 (2)	0.3991 (3)	0.9168 (2)	0.0371 (5)
C28	0.9594 (2)	0.6269 (2)	0.7219 (2)	0.0324 (5)
F71	0.49464 (17)	0.40522 (16)	0.18732 (15)	0.0518 (4)
F72	0.33610 (14)	0.24944 (16)	0.17273 (16)	0.0498 (4)
F73	0.48280 (15)	0.40247 (14)	0.36250 (13)	0.0414 (3)
F81	0.6458 (2)	−0.12681 (17)	0.26873 (19)	0.0643 (5)
F82	0.78382 (14)	0.0646 (2)	0.43363 (19)	0.0648 (5)
F83	0.57691 (13)	0.01272 (14)	0.41241 (14)	0.0378 (3)
F171	0.2098 (3)	0.3196 (3)	0.7294 (2)	0.0817 (11)	0.871 (5)
F172	0.0319 (4)	0.2901 (5)	0.5902 (5)	0.0911 (17)	0.871 (5)
F173	0.2064 (2)	0.4501 (2)	0.6501 (3)	0.0623 (8)	0.871 (5)
F174	0.0193 (17)	0.2964 (15)	0.5800 (16)	0.010 (3)	0.129 (5)
F175	0.2283 (15)	0.4153 (18)	0.7029 (16)	0.059 (5)	0.129 (5)
F176	0.1050 (18)	0.2177 (19)	0.6667 (18)	0.074 (5)	0.129 (5)
F181	0.0771 (2)	−0.1419 (3)	0.07081 (19)	0.0933 (13)	0.895 (6)
F182	0.0659 (2)	−0.2290 (2)	0.1909 (3)	0.0779 (10)	0.895 (6)
F183	−0.07142 (18)	−0.1245 (3)	0.1674 (3)	0.0785 (10)	0.895 (6)
F184	−0.005 (2)	−0.073 (2)	0.088 (2)	0.081 (7)	0.105 (6)
F185	0.0866 (17)	−0.2036 (19)	0.1295 (18)	0.051 (5)	0.105 (6)
F186	−0.039 (4)	−0.160 (4)	0.199 (4)	0.122 (13)	0.105 (6)
F271	0.6242 (2)	0.4506 (2)	0.96013 (18)	0.0727 (6)
F272	0.82892 (17)	0.4629 (2)	1.01840 (15)	0.0611 (5)
F273	0.67790 (19)	0.26711 (17)	0.88816 (16)	0.0595 (5)
F281	0.97983 (17)	0.60321 (18)	0.60979 (15)	0.0634 (5)
F282	1.07317 (13)	0.64251 (17)	0.80379 (16)	0.0530 (4)
F283	0.94068 (16)	0.75009 (15)	0.77561 (18)	0.0552 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0256 (11)	0.0184 (10)	0.0232 (11)	0.0055 (9)	0.0083 (9)	0.0114 (9)
C1	0.0175 (9)	0.0190 (9)	0.0193 (9)	−0.0008 (7)	0.0044 (7)	0.0064 (8)
C2	0.0257 (10)	0.0220 (10)	0.0204 (10)	−0.0006 (8)	0.0050 (8)	0.0086 (8)
C3	0.0352 (12)	0.0336 (12)	0.0230 (10)	−0.0008 (10)	0.0094 (9)	0.0132 (9)
C4	0.0314 (12)	0.0415 (13)	0.0274 (11)	−0.0008 (10)	0.0168 (10)	0.0095 (10)
C5	0.0248 (11)	0.0340 (12)	0.0342 (12)	0.0068 (9)	0.0143 (9)	0.0099 (10)
C6	0.0185 (9)	0.0238 (10)	0.0269 (10)	0.0026 (8)	0.0065 (8)	0.0088 (9)
C7	0.0419 (13)	0.0283 (11)	0.0284 (11)	0.0080 (10)	0.0091 (10)	0.0168 (10)
C8	0.0274 (11)	0.0342 (12)	0.0428 (13)	0.0132 (9)	0.0135 (10)	0.0196 (11)
C11	0.0261 (10)	0.0225 (10)	0.0200 (9)	0.0070 (8)	0.0085 (8)	0.0113 (8)
C12	0.0283 (11)	0.0235 (10)	0.0224 (10)	0.0071 (8)	0.0081 (8)	0.0098 (9)
C13	0.0306 (11)	0.0360 (12)	0.0287 (11)	0.0159 (9)	0.0145 (9)	0.0170 (10)
C14	0.0239 (10)	0.0385 (12)	0.0342 (12)	0.0090 (9)	0.0125 (9)	0.0185 (10)
C15	0.0256 (11)	0.0293 (11)	0.0298 (11)	0.0059 (9)	0.0080 (9)	0.0128 (10)
C16	0.0251 (10)	0.0269 (11)	0.0220 (10)	0.0075 (8)	0.0094 (8)	0.0098 (9)
C17	0.0386 (14)	0.0547 (17)	0.0378 (14)	0.0222 (13)	0.0199 (12)	0.0154 (13)
C18	0.0257 (13)	0.0451 (16)	0.0540 (17)	0.0013 (11)	0.0124 (12)	0.0057 (14)
C21	0.0242 (10)	0.0222 (10)	0.0221 (10)	0.0070 (8)	0.0085 (8)	0.0104 (8)
C22	0.0247 (10)	0.0250 (10)	0.0251 (10)	0.0060 (8)	0.0089 (8)	0.0128 (9)
C23	0.0322 (11)	0.0288 (11)	0.0223 (10)	0.0126 (9)	0.0092 (9)	0.0134 (9)
C24	0.0284 (11)	0.0281 (11)	0.0198 (10)	0.0070 (9)	0.0030 (8)	0.0087 (9)
C25	0.0241 (10)	0.0249 (10)	0.0256 (10)	0.0069 (8)	0.0071 (8)	0.0113 (9)
C26	0.0244 (10)	0.0250 (10)	0.0210 (10)	0.0053 (8)	0.0079 (8)	0.0113 (8)
C27	0.0416 (13)	0.0452 (14)	0.0257 (11)	0.0127 (11)	0.0115 (10)	0.0193 (11)
C28	0.0296 (11)	0.0320 (12)	0.0262 (11)	0.0018 (9)	0.0062 (9)	0.0120 (10)
F71	0.0776 (11)	0.0467 (9)	0.0523 (9)	0.0242 (8)	0.0258 (8)	0.0385 (8)
F72	0.0355 (8)	0.0479 (9)	0.0576 (9)	0.0156 (7)	0.0057 (7)	0.0237 (8)
F73	0.0629 (9)	0.0333 (7)	0.0330 (7)	0.0238 (7)	0.0200 (7)	0.0162 (6)
F81	0.1004 (14)	0.0431 (9)	0.0754 (12)	0.0451 (9)	0.0482 (11)	0.0346 (9)
F82	0.0299 (8)	0.1001 (14)	0.0803 (12)	0.0132 (8)	0.0045 (8)	0.0672 (12)
F83	0.0416 (7)	0.0403 (8)	0.0493 (8)	0.0182 (6)	0.0243 (6)	0.0311 (7)
F171	0.128 (2)	0.119 (2)	0.0365 (12)	0.091 (2)	0.0500 (14)	0.0409 (14)
F172	0.0473 (19)	0.098 (2)	0.089 (2)	0.0282 (15)	0.0401 (17)	0.0093 (17)
F173	0.0716 (14)	0.0396 (11)	0.0706 (15)	0.0281 (10)	0.0387 (12)	0.0142 (10)
F174	0.010 (4)	0.008 (3)	0.014 (4)	0.005 (2)	0.0038 (19)	0.006 (2)
F175	0.058 (5)	0.060 (5)	0.058 (5)	0.020 (2)	0.020 (3)	0.028 (3)
F176	0.077 (6)	0.075 (6)	0.073 (6)	0.024 (3)	0.030 (3)	0.037 (3)
F181	0.0667 (16)	0.101 (2)	0.0287 (11)	−0.0264 (14)	0.0038 (9)	−0.0066 (11)
F182	0.0613 (13)	0.0315 (11)	0.103 (2)	0.0027 (9)	0.0183 (13)	0.0136 (11)
F183	0.0180 (9)	0.0589 (14)	0.0876 (17)	0.0040 (9)	−0.0030 (9)	−0.0061 (13)
F184	0.082 (8)	0.081 (8)	0.081 (8)	0.025 (3)	0.025 (3)	0.042 (4)
F185	0.050 (5)	0.050 (5)	0.051 (5)	0.016 (3)	0.017 (3)	0.025 (3)
F186	0.122 (13)	0.122 (13)	0.123 (13)	0.038 (5)	0.041 (5)	0.063 (7)
F271	0.0894 (14)	0.1235 (17)	0.0596 (11)	0.0705 (13)	0.0558 (11)	0.0632 (12)
F272	0.0620 (10)	0.0821 (12)	0.0295 (8)	0.0069 (9)	0.0009 (7)	0.0329 (8)
F273	0.0898 (13)	0.0544 (10)	0.0468 (9)	0.0145 (9)	0.0268 (9)	0.0371 (8)
F281	0.0588 (10)	0.0633 (11)	0.0354 (8)	−0.0220 (8)	0.0174 (7)	0.0147 (8)
F282	0.0252 (7)	0.0570 (10)	0.0625 (10)	−0.0027 (6)	−0.0013 (7)	0.0319 (8)
F283	0.0555 (9)	0.0313 (8)	0.0762 (11)	0.0079 (7)	0.0239 (8)	0.0269 (8)

Geometric parameters (Å, º) top

B1—C11	1.564 (3)	C16—H16	0.9500
B1—C21	1.569 (3)	C17—F175	1.111 (16)
B1—C1	1.595 (3)	C17—F174	1.419 (18)
C1—C6	1.404 (3)	C17—F172	1.277 (5)
C1—C2	1.410 (3)	C17—F171	1.305 (3)
C2—C3	1.388 (3)	C17—F173	1.384 (4)
C2—C7	1.494 (3)	C17—F176	1.541 (17)
C3—C4	1.378 (4)	C18—F185	1.079 (18)
C3—H3	0.9500	C18—F186	1.15 (4)
C4—C5	1.378 (4)	C18—F183	1.318 (4)
C4—H4	0.9500	C18—F181	1.311 (4)
C5—C6	1.395 (3)	C18—F182	1.375 (4)
C5—H5	0.9500	C18—F184	1.50 (2)
C6—C8	1.495 (3)	C21—C22	1.397 (3)
C7—F71	1.336 (3)	C21—C26	1.409 (3)
C7—F72	1.346 (3)	C22—C23	1.394 (3)
C7—F73	1.349 (3)	C22—H22	0.9500
C8—F81	1.335 (3)	C23—C24	1.385 (3)
C8—F82	1.337 (3)	C23—C27	1.500 (3)
C8—F83	1.344 (3)	C24—C25	1.389 (3)
C11—C12	1.397 (3)	C24—H24	0.9500
C11—C16	1.401 (3)	C25—C26	1.392 (3)
C12—C13	1.385 (3)	C25—C28	1.501 (3)
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.389 (3)	C27—F271	1.319 (3)
C13—C17	1.501 (3)	C27—F272	1.333 (3)
C14—C15	1.385 (3)	C27—F273	1.347 (3)
C14—H14	0.9500	C28—F281	1.323 (3)
C15—C16	1.389 (3)	C28—F282	1.334 (3)
C15—C18	1.497 (3)	C28—F283	1.336 (3)

C11—B1—C21	120.79 (18)	F172—C17—F173	104.0 (3)
C11—B1—C1	121.32 (17)	F171—C17—F173	103.4 (3)
C21—B1—C1	117.87 (17)	F175—C17—C13	121.9 (8)
C6—C1—C2	115.86 (18)	F174—C17—C13	113.1 (7)
C6—C1—B1	121.37 (18)	F172—C17—C13	114.1 (3)
C2—C1—B1	122.57 (18)	F171—C17—C13	112.7 (2)
C3—C2—C1	121.9 (2)	F173—C17—C13	110.4 (2)
C3—C2—C7	118.4 (2)	F175—C17—F176	111.1 (11)
C1—C2—C7	119.59 (18)	F174—C17—F176	78.7 (8)
C4—C3—C2	120.3 (2)	C13—C17—F176	101.4 (7)
C4—C3—H3	119.8	F185—C18—F186	105 (2)
C2—C3—H3	119.8	F183—C18—F181	110.2 (3)
C5—C4—C3	119.7 (2)	F183—C18—F182	104.4 (3)
C5—C4—H4	120.1	F181—C18—F182	103.3 (3)
C3—C4—H4	120.1	F185—C18—F184	109.8 (13)
C4—C5—C6	120.0 (2)	F186—C18—F184	100 (2)
C4—C5—H5	120.0	F185—C18—C15	120.9 (9)
C6—C5—H5	120.0	F186—C18—C15	114.2 (19)
C5—C6—C1	122.1 (2)	F183—C18—C15	113.7 (2)
C5—C6—C8	117.7 (2)	F181—C18—C15	113.2 (2)
C1—C6—C8	120.21 (19)	F182—C18—C15	111.2 (3)
F71—C7—F72	106.46 (18)	F184—C18—C15	104.4 (8)
F71—C7—F73	106.39 (18)	C22—C21—C26	117.42 (18)
F72—C7—F73	106.15 (19)	C22—C21—B1	120.89 (18)
F71—C7—C2	113.51 (19)	C26—C21—B1	121.69 (18)
F72—C7—C2	111.84 (18)	C23—C22—C21	121.37 (19)
F73—C7—C2	112.00 (18)	C23—C22—H22	119.3
F81—C8—F82	106.5 (2)	C21—C22—H22	119.3
F81—C8—F83	105.64 (19)	C24—C23—C22	120.66 (19)
F82—C8—F83	105.7 (2)	C24—C23—C27	120.32 (19)
F81—C8—C6	112.8 (2)	C22—C23—C27	119.0 (2)
F82—C8—C6	113.00 (19)	C23—C24—C25	118.81 (19)
F83—C8—C6	112.60 (18)	C23—C24—H24	120.6
C12—C11—C16	117.25 (18)	C25—C24—H24	120.6
C12—C11—B1	120.42 (18)	C24—C25—C26	120.95 (19)
C16—C11—B1	122.30 (18)	C24—C25—C28	118.09 (19)
C13—C12—C11	121.62 (19)	C26—C25—C28	120.95 (19)
C13—C12—H12	119.2	C25—C26—C21	120.74 (19)
C11—C12—H12	119.2	C25—C26—H26	119.6
C12—C13—C14	120.2 (2)	C21—C26—H26	119.6
C12—C13—C17	118.7 (2)	F271—C27—F272	107.7 (2)
C14—C13—C17	121.1 (2)	F271—C27—F273	105.8 (2)
C15—C14—C13	119.3 (2)	F272—C27—F273	105.5 (2)
C15—C14—H14	120.4	F271—C27—C23	112.5 (2)
C13—C14—H14	120.4	F272—C27—C23	113.0 (2)
C14—C15—C16	120.4 (2)	F273—C27—C23	111.91 (19)
C14—C15—C18	120.4 (2)	F281—C28—F282	107.16 (19)
C16—C15—C18	119.3 (2)	F281—C28—F283	106.6 (2)
C15—C16—C11	121.3 (2)	F282—C28—F283	105.86 (18)
C15—C16—H16	119.4	F281—C28—C25	113.13 (18)
C11—C16—H16	119.4	F282—C28—C25	111.74 (19)
F175—C17—F174	119.6 (11)	F283—C28—C25	111.91 (19)
F172—C17—F171	111.3 (3)

C11—B1—C1—C6	−108.6 (2)	C14—C13—C17—F174	−22.9 (6)
C21—B1—C1—C6	72.9 (2)	C12—C13—C17—F172	164.8 (3)
C11—B1—C1—C2	76.8 (2)	C14—C13—C17—F172	−15.9 (4)
C21—B1—C1—C2	−101.8 (2)	C12—C13—C17—F171	−66.9 (3)
C6—C1—C2—C3	−3.0 (3)	C14—C13—C17—F171	112.4 (3)
B1—C1—C2—C3	171.96 (18)	C12—C13—C17—F173	48.2 (3)
C6—C1—C2—C7	174.99 (17)	C14—C13—C17—F173	−132.6 (3)
B1—C1—C2—C7	−10.1 (3)	C12—C13—C17—F176	−119.7 (7)
C1—C2—C3—C4	1.3 (3)	C14—C13—C17—F176	59.5 (8)
C7—C2—C3—C4	−176.72 (19)	C14—C15—C18—F185	−149.5 (14)
C2—C3—C4—C5	1.6 (3)	C16—C15—C18—F185	31.2 (15)
C3—C4—C5—C6	−2.5 (3)	C14—C15—C18—F186	−22 (2)
C4—C5—C6—C1	0.6 (3)	C16—C15—C18—F186	159 (2)
C4—C5—C6—C8	−179.26 (19)	C14—C15—C18—F183	16.1 (4)
C2—C1—C6—C5	2.0 (3)	C16—C15—C18—F183	−163.2 (3)
B1—C1—C6—C5	−172.98 (18)	C14—C15—C18—F181	142.8 (3)
C2—C1—C6—C8	−178.07 (18)	C16—C15—C18—F181	−36.5 (4)
B1—C1—C6—C8	6.9 (3)	C14—C15—C18—F182	−101.4 (3)
C3—C2—C7—F71	−25.5 (3)	C16—C15—C18—F182	79.3 (3)
C1—C2—C7—F71	156.50 (18)	C14—C15—C18—F184	86.3 (10)
C3—C2—C7—F72	95.0 (2)	C16—C15—C18—F184	−92.9 (10)
C1—C2—C7—F72	−83.0 (2)	C11—B1—C21—C22	35.2 (3)
C3—C2—C7—F73	−145.98 (19)	C1—B1—C21—C22	−146.3 (2)
C1—C2—C7—F73	36.0 (3)	C11—B1—C21—C26	−145.1 (2)
C5—C6—C8—F81	−41.2 (3)	C1—B1—C21—C26	33.4 (3)
C1—C6—C8—F81	138.9 (2)	C26—C21—C22—C23	0.4 (3)
C5—C6—C8—F82	79.7 (3)	B1—C21—C22—C23	−179.89 (19)
C1—C6—C8—F82	−100.3 (2)	C21—C22—C23—C24	1.2 (3)
C5—C6—C8—F83	−160.63 (18)	C21—C22—C23—C27	179.5 (2)
C1—C6—C8—F83	19.5 (3)	C22—C23—C24—C25	−1.1 (3)
C21—B1—C11—C12	24.7 (3)	C27—C23—C24—C25	−179.4 (2)
C1—B1—C11—C12	−153.81 (19)	C23—C24—C25—C26	−0.7 (3)
C21—B1—C11—C16	−157.56 (19)	C23—C24—C25—C28	178.0 (2)
C1—B1—C11—C16	24.0 (3)	C24—C25—C26—C21	2.3 (3)
C16—C11—C12—C13	0.3 (3)	C28—C25—C26—C21	−176.4 (2)
B1—C11—C12—C13	178.17 (19)	C22—C21—C26—C25	−2.1 (3)
C11—C12—C13—C14	0.6 (3)	B1—C21—C26—C25	178.18 (19)
C11—C12—C13—C17	179.9 (2)	C24—C23—C27—F271	103.8 (3)
C12—C13—C14—C15	−0.8 (3)	C22—C23—C27—F271	−74.5 (3)
C17—C13—C14—C15	−180.0 (2)	C24—C23—C27—F272	−18.3 (3)
C13—C14—C15—C16	−0.1 (3)	C22—C23—C27—F272	163.4 (2)
C13—C14—C15—C18	−179.3 (2)	C24—C23—C27—F273	−137.2 (2)
C14—C15—C16—C11	1.0 (3)	C22—C23—C27—F273	44.5 (3)
C18—C15—C16—C11	−179.7 (2)	C24—C25—C28—F281	162.8 (2)
C12—C11—C16—C15	−1.1 (3)	C26—C25—C28—F281	−18.5 (3)
B1—C11—C16—C15	−179.0 (2)	C24—C25—C28—F282	41.7 (3)
C12—C13—C17—F175	4.2 (13)	C26—C25—C28—F282	−139.6 (2)
C14—C13—C17—F175	−176.6 (13)	C24—C25—C28—F283	−76.8 (3)
C12—C13—C17—F174	157.8 (6)	C26—C25—C28—F283	101.9 (2)

(IV) [3,5-Bis(trifluoromethyl)phenyl]dimesitylborane top

Crystal data top

C₂₆H₂₅BF₆	F(000) = 960
M_r = 462.27	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3500 (12) Å	Cell parameters from 5716 reflections
b = 34.370 (4) Å	θ = 3.2–25.9°
c = 8.5512 (13) Å	µ = 0.11 mm⁻¹
β = 107.062 (11)°	T = 173 K
V = 2346.1 (6) Å³	Block, colourless
Z = 4	0.27 × 0.27 × 0.24 mm

Data collection top

Stoe IPDS II two-circle diffractometer	2565 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.109
ω scans	θ_max = 25.6°, θ_min = 3.1°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
T_min = 0.448, T_max = 1.000	k = −41→38
9711 measured reflections	l = −10→6
4294 independent reflections

Refinement top

Refinement on F²	36 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.066	H-atom parameters constrained
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.102P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
4294 reflections	Δρ_max = 0.38 e Å⁻³
332 parameters	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₂₅BF₆	V = 2346.1 (6) Å³
M_r = 462.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3500 (12) Å	µ = 0.11 mm⁻¹
b = 34.370 (4) Å	T = 173 K
c = 8.5512 (13) Å	0.27 × 0.27 × 0.24 mm
β = 107.062 (11)°

Data collection top

Stoe IPDS II two-circle diffractometer	4294 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	2565 reflections with I > 2σ(I)
T_min = 0.448, T_max = 1.000	R_int = 0.109
9711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	36 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 0.93	Δρ_max = 0.38 e Å⁻³
4294 reflections	Δρ_min = −0.27 e Å⁻³
332 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
B1	0.6901 (3)	0.61171 (9)	0.5101 (4)	0.0300 (6)
C1	0.7672 (3)	0.65021 (7)	0.4612 (3)	0.0301 (6)
C2	0.7957 (3)	0.65473 (8)	0.3094 (3)	0.0351 (6)
H2	0.7631	0.6346	0.2301	0.042*
C3	0.8711 (3)	0.68813 (9)	0.2722 (4)	0.0383 (7)
C4	0.9224 (3)	0.71777 (9)	0.3864 (4)	0.0408 (7)
H4	0.9759	0.7403	0.3615	0.049*
C5	0.8939 (3)	0.71376 (8)	0.5368 (4)	0.0364 (6)
C6	0.8163 (3)	0.68071 (8)	0.5734 (3)	0.0326 (6)
H6	0.7962	0.6788	0.6768	0.039*
C7	0.8980 (4)	0.69247 (13)	0.1082 (5)	0.0603 (10)
C8	0.9482 (4)	0.74476 (9)	0.6641 (5)	0.0514 (8)
C11	0.7177 (3)	0.57272 (7)	0.4250 (3)	0.0297 (6)
C12	0.5835 (3)	0.54702 (8)	0.3539 (3)	0.0309 (6)
C13	0.6064 (3)	0.51588 (8)	0.2597 (4)	0.0336 (6)
H13	0.5138	0.4994	0.2111	0.040*
C14	0.7602 (3)	0.50788 (8)	0.2340 (3)	0.0344 (6)
C15	0.8944 (3)	0.53144 (8)	0.3133 (4)	0.0360 (6)
H15	1.0022	0.5255	0.3036	0.043*
C16	0.8774 (3)	0.56330 (8)	0.4060 (3)	0.0318 (6)
C17	0.4110 (3)	0.55229 (9)	0.3761 (4)	0.0391 (7)
H17A	0.3318	0.5345	0.3030	0.059*
H17B	0.3737	0.5792	0.3497	0.059*
H17C	0.4161	0.5466	0.4898	0.059*
C18	0.7802 (4)	0.47468 (9)	0.1259 (4)	0.0468 (8)
H18A	0.8753	0.4799	0.0838	0.070*
H18B	0.6778	0.4720	0.0341	0.070*
H18C	0.8004	0.4505	0.1895	0.070*
C19	1.0362 (3)	0.58555 (9)	0.4915 (4)	0.0437 (7)
H19A	1.1302	0.5673	0.5266	0.066*
H19B	1.0213	0.5990	0.5873	0.066*
H19C	1.0595	0.6046	0.4158	0.066*
C21	0.5928 (3)	0.61523 (7)	0.6422 (3)	0.0275 (5)
C22	0.4560 (3)	0.64135 (7)	0.6205 (3)	0.0317 (6)
C23	0.3776 (3)	0.64438 (8)	0.7437 (4)	0.0366 (6)
H23	0.2861	0.6619	0.7284	0.044*
C24	0.4272 (3)	0.62311 (8)	0.8859 (4)	0.0358 (6)
C25	0.5622 (3)	0.59779 (8)	0.9069 (4)	0.0369 (6)
H25	0.5998	0.5832	1.0052	0.044*
C26	0.6430 (3)	0.59340 (8)	0.7874 (3)	0.0323 (6)
C27	0.7924 (4)	0.56614 (9)	0.8226 (4)	0.0458 (7)
H27A	0.8925	0.5809	0.8212	0.069*
H27B	0.7710	0.5458	0.7388	0.069*
H27C	0.8102	0.5542	0.9304	0.069*
C28	0.3885 (3)	0.66523 (10)	0.4683 (4)	0.0453 (7)
H28A	0.2722	0.6725	0.4572	0.068*
H28B	0.3928	0.6500	0.3728	0.068*
H28C	0.4564	0.6888	0.4756	0.068*
C29	0.3397 (4)	0.62729 (10)	1.0161 (5)	0.0541 (8)
H29A	0.3914	0.6485	1.0905	0.081*
H29B	0.3497	0.6029	1.0779	0.081*
H29C	0.2210	0.6332	0.9646	0.081*
F71	0.7591 (14)	0.6973 (3)	−0.0137 (14)	0.088 (3)	0.543 (12)
F72	1.0159 (10)	0.7137 (3)	0.0989 (7)	0.095 (3)	0.543 (12)
F73	0.9507 (11)	0.6553 (2)	0.0547 (9)	0.098 (2)	0.543 (12)
F71'	0.7752 (14)	0.6818 (3)	−0.0074 (13)	0.068 (3)	0.457 (12)
F72'	0.9167 (15)	0.73274 (19)	0.0782 (8)	0.087 (3)	0.457 (12)
F73'	1.0318 (10)	0.6777 (4)	0.1020 (10)	0.098 (3)	0.457 (12)
F81	0.9853 (4)	0.77830 (6)	0.6049 (4)	0.0942 (9)
F82	0.8313 (3)	0.75275 (7)	0.7373 (3)	0.0783 (7)
F83	1.0818 (3)	0.73463 (8)	0.7842 (3)	0.0869 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0229 (11)	0.0399 (16)	0.0279 (15)	−0.0006 (10)	0.0086 (10)	0.0018 (13)
C1	0.0286 (11)	0.0348 (13)	0.0306 (14)	0.0003 (10)	0.0144 (10)	−0.0001 (11)
C2	0.0327 (12)	0.0459 (16)	0.0305 (15)	−0.0040 (11)	0.0150 (11)	−0.0026 (12)
C3	0.0315 (12)	0.0550 (18)	0.0318 (15)	−0.0040 (12)	0.0144 (11)	0.0065 (14)
C4	0.0319 (12)	0.0475 (16)	0.0441 (18)	−0.0063 (11)	0.0131 (11)	0.0114 (14)
C5	0.0357 (12)	0.0363 (15)	0.0371 (16)	−0.0032 (10)	0.0107 (11)	0.0034 (12)
C6	0.0342 (12)	0.0377 (14)	0.0291 (14)	−0.0019 (10)	0.0145 (10)	−0.0007 (11)
C7	0.0538 (18)	0.091 (3)	0.043 (2)	−0.0131 (19)	0.0254 (16)	0.014 (2)
C8	0.0589 (17)	0.0412 (17)	0.054 (2)	−0.0128 (14)	0.0164 (16)	−0.0023 (15)
C11	0.0258 (11)	0.0366 (14)	0.0301 (14)	0.0013 (10)	0.0135 (10)	0.0035 (11)
C12	0.0276 (11)	0.0333 (13)	0.0352 (15)	0.0028 (9)	0.0144 (10)	0.0047 (11)
C13	0.0312 (11)	0.0320 (14)	0.0379 (16)	−0.0013 (10)	0.0104 (11)	0.0008 (12)
C14	0.0376 (12)	0.0349 (14)	0.0327 (15)	0.0065 (10)	0.0134 (11)	0.0021 (12)
C15	0.0275 (11)	0.0426 (15)	0.0419 (17)	0.0083 (10)	0.0162 (11)	0.0023 (12)
C16	0.0254 (11)	0.0393 (14)	0.0336 (15)	0.0017 (10)	0.0131 (10)	0.0004 (12)
C17	0.0256 (11)	0.0489 (16)	0.0473 (18)	−0.0045 (11)	0.0178 (11)	−0.0035 (14)
C18	0.0477 (15)	0.0410 (16)	0.053 (2)	0.0107 (12)	0.0170 (14)	−0.0067 (14)
C19	0.0263 (12)	0.0543 (18)	0.0520 (19)	−0.0017 (11)	0.0136 (12)	−0.0061 (15)
C21	0.0278 (11)	0.0289 (12)	0.0289 (14)	−0.0033 (9)	0.0131 (9)	−0.0006 (11)
C22	0.0308 (11)	0.0327 (13)	0.0346 (15)	−0.0028 (10)	0.0145 (10)	−0.0033 (11)
C23	0.0319 (12)	0.0402 (15)	0.0431 (17)	−0.0004 (10)	0.0194 (12)	−0.0067 (13)
C24	0.0453 (13)	0.0348 (13)	0.0352 (16)	−0.0114 (11)	0.0243 (12)	−0.0085 (12)
C25	0.0459 (14)	0.0384 (15)	0.0311 (15)	−0.0051 (11)	0.0186 (11)	0.0036 (12)
C26	0.0348 (12)	0.0336 (13)	0.0318 (15)	−0.0038 (10)	0.0150 (10)	0.0006 (11)
C27	0.0475 (15)	0.0504 (18)	0.0414 (18)	0.0110 (13)	0.0160 (13)	0.0126 (14)
C28	0.0407 (14)	0.0552 (18)	0.0432 (18)	0.0137 (12)	0.0172 (13)	0.0103 (15)
C29	0.070 (2)	0.0547 (19)	0.053 (2)	−0.0095 (15)	0.0435 (17)	−0.0103 (16)
F71	0.089 (4)	0.137 (7)	0.046 (3)	0.015 (5)	0.030 (3)	0.020 (5)
F72	0.105 (4)	0.129 (6)	0.069 (3)	−0.069 (4)	0.055 (3)	−0.003 (3)
F73	0.131 (5)	0.114 (4)	0.082 (4)	−0.001 (4)	0.084 (3)	−0.009 (3)
F71'	0.084 (5)	0.092 (5)	0.030 (3)	−0.048 (4)	0.020 (3)	−0.014 (4)
F72'	0.159 (6)	0.062 (4)	0.058 (3)	−0.021 (4)	0.059 (4)	0.013 (3)
F73'	0.089 (5)	0.149 (7)	0.085 (4)	0.035 (4)	0.068 (4)	0.016 (4)
F81	0.155 (2)	0.0454 (12)	0.0905 (19)	−0.0423 (14)	0.0496 (17)	−0.0077 (12)
F82	0.0932 (15)	0.0673 (14)	0.0854 (18)	−0.0134 (11)	0.0432 (13)	−0.0335 (13)
F83	0.0798 (14)	0.0863 (17)	0.0726 (17)	−0.0155 (12)	−0.0120 (12)	−0.0184 (13)

Geometric parameters (Å, º) top

B1—C11	1.574 (4)	C15—H15	0.9500
B1—C21	1.577 (4)	C16—C19	1.519 (4)
B1—C1	1.581 (4)	C17—H17A	0.9800
C1—C2	1.396 (4)	C17—H17B	0.9800
C1—C6	1.399 (4)	C17—H17C	0.9800
C2—C3	1.390 (4)	C18—H18A	0.9800
C2—H2	0.9500	C18—H18B	0.9800
C3—C4	1.388 (4)	C18—H18C	0.9800
C3—C7	1.492 (5)	C19—H19A	0.9800
C4—C5	1.382 (4)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.388 (4)	C21—C26	1.406 (4)
C5—C8	1.496 (5)	C21—C22	1.421 (3)
C6—H6	0.9500	C22—C23	1.398 (4)
C7—F73'	1.242 (7)	C22—C28	1.501 (4)
C7—F72	1.246 (5)	C23—C24	1.375 (4)
C7—F71'	1.252 (10)	C23—H23	0.9500
C7—F71	1.323 (11)	C24—C25	1.393 (4)
C7—F72'	1.425 (7)	C24—C29	1.507 (4)
C7—F73	1.466 (8)	C25—C26	1.387 (4)
C8—F83	1.322 (4)	C25—H25	0.9500
C8—F81	1.331 (4)	C26—C27	1.518 (4)
C8—F82	1.333 (4)	C27—H27A	0.9800
C11—C12	1.416 (4)	C27—H27B	0.9800
C11—C16	1.427 (3)	C27—H27C	0.9800
C12—C13	1.386 (4)	C28—H28A	0.9800
C12—C17	1.518 (3)	C28—H28B	0.9800
C13—C14	1.393 (4)	C28—H28C	0.9800
C13—H13	0.9500	C29—H29A	0.9800
C14—C15	1.388 (4)	C29—H29B	0.9800
C14—C18	1.508 (4)	C29—H29C	0.9800
C15—C16	1.384 (4)

C11—B1—C21	124.9 (2)	C11—C16—C19	123.0 (2)
C11—B1—C1	117.7 (2)	C12—C17—H17A	109.5
C21—B1—C1	117.4 (2)	C12—C17—H17B	109.5
C2—C1—C6	117.3 (2)	H17A—C17—H17B	109.5
C2—C1—B1	122.2 (2)	C12—C17—H17C	109.5
C6—C1—B1	120.4 (2)	H17A—C17—H17C	109.5
C3—C2—C1	121.1 (3)	H17B—C17—H17C	109.5
C3—C2—H2	119.4	C14—C18—H18A	109.5
C1—C2—H2	119.4	C14—C18—H18B	109.5
C4—C3—C2	120.8 (3)	H18A—C18—H18B	109.5
C4—C3—C7	119.2 (3)	C14—C18—H18C	109.5
C2—C3—C7	120.0 (3)	H18A—C18—H18C	109.5
C5—C4—C3	118.6 (3)	H18B—C18—H18C	109.5
C5—C4—H4	120.7	C16—C19—H19A	109.5
C3—C4—H4	120.7	C16—C19—H19B	109.5
C4—C5—C6	120.7 (3)	H19A—C19—H19B	109.5
C4—C5—C8	120.6 (3)	C16—C19—H19C	109.5
C6—C5—C8	118.7 (3)	H19A—C19—H19C	109.5
C5—C6—C1	121.4 (3)	H19B—C19—H19C	109.5
C5—C6—H6	119.3	C26—C21—C22	118.2 (2)
C1—C6—H6	119.3	C26—C21—B1	120.6 (2)
F73'—C7—F71'	112.7 (8)	C22—C21—B1	121.2 (2)
F72—C7—F71	113.8 (7)	C23—C22—C21	119.0 (2)
F73'—C7—F72'	103.9 (6)	C23—C22—C28	118.2 (2)
F71'—C7—F72'	104.4 (6)	C21—C22—C28	122.8 (2)
F72—C7—F73	100.1 (5)	C24—C23—C22	122.7 (2)
F71—C7—F73	97.8 (6)	C24—C23—H23	118.6
F73'—C7—C3	112.6 (4)	C22—C23—H23	118.6
F72—C7—C3	117.2 (4)	C23—C24—C25	117.9 (2)
F71'—C7—C3	113.5 (6)	C23—C24—C29	121.1 (3)
F71—C7—C3	114.5 (6)	C25—C24—C29	120.9 (3)
F72'—C7—C3	108.7 (4)	C26—C25—C24	121.5 (3)
F73—C7—C3	110.4 (4)	C26—C25—H25	119.2
F83—C8—F81	106.6 (3)	C24—C25—H25	119.2
F83—C8—F82	104.9 (3)	C25—C26—C21	120.6 (2)
F81—C8—F82	106.5 (3)	C25—C26—C27	118.0 (2)
F83—C8—C5	112.6 (3)	C21—C26—C27	121.3 (2)
F81—C8—C5	113.3 (3)	C26—C27—H27A	109.5
F82—C8—C5	112.4 (2)	C26—C27—H27B	109.5
C12—C11—C16	117.2 (2)	H27A—C27—H27B	109.5
C12—C11—B1	121.6 (2)	C26—C27—H27C	109.5
C16—C11—B1	121.0 (2)	H27A—C27—H27C	109.5
C13—C12—C11	120.3 (2)	H27B—C27—H27C	109.5
C13—C12—C17	117.5 (2)	C22—C28—H28A	109.5
C11—C12—C17	122.2 (2)	C22—C28—H28B	109.5
C12—C13—C14	122.3 (2)	H28A—C28—H28B	109.5
C12—C13—H13	118.8	C22—C28—H28C	109.5
C14—C13—H13	118.8	H28A—C28—H28C	109.5
C15—C14—C13	117.2 (2)	H28B—C28—H28C	109.5
C15—C14—C18	121.5 (2)	C24—C29—H29A	109.5
C13—C14—C18	121.3 (2)	C24—C29—H29B	109.5
C16—C15—C14	122.5 (2)	H29A—C29—H29B	109.5
C16—C15—H15	118.7	C24—C29—H29C	109.5
C14—C15—H15	118.7	H29A—C29—H29C	109.5
C15—C16—C11	120.1 (2)	H29B—C29—H29C	109.5
C15—C16—C19	116.9 (2)

C11—B1—C1—C2	26.4 (3)	C1—B1—C11—C16	44.1 (4)
C21—B1—C1—C2	−154.2 (2)	C16—C11—C12—C13	−4.8 (4)
C11—B1—C1—C6	−150.8 (2)	B1—C11—C12—C13	170.7 (3)
C21—B1—C1—C6	28.5 (3)	C16—C11—C12—C17	175.5 (3)
C6—C1—C2—C3	0.5 (4)	B1—C11—C12—C17	−9.0 (4)
B1—C1—C2—C3	−176.9 (2)	C11—C12—C13—C14	1.5 (4)
C1—C2—C3—C4	0.9 (4)	C17—C12—C13—C14	−178.8 (3)
C1—C2—C3—C7	−179.2 (3)	C12—C13—C14—C15	3.0 (4)
C2—C3—C4—C5	−1.3 (4)	C12—C13—C14—C18	−177.7 (3)
C7—C3—C4—C5	178.8 (3)	C13—C14—C15—C16	−4.2 (4)
C3—C4—C5—C6	0.3 (4)	C18—C14—C15—C16	176.5 (3)
C3—C4—C5—C8	179.5 (3)	C14—C15—C16—C11	0.9 (4)
C4—C5—C6—C1	1.1 (4)	C14—C15—C16—C19	177.7 (3)
C8—C5—C6—C1	−178.1 (2)	C12—C11—C16—C15	3.6 (4)
C2—C1—C6—C5	−1.5 (4)	B1—C11—C16—C15	−171.9 (3)
B1—C1—C6—C5	175.9 (2)	C12—C11—C16—C19	−172.9 (3)
C4—C3—C7—F73'	93.2 (8)	B1—C11—C16—C19	11.6 (4)
C2—C3—C7—F73'	−86.7 (8)	C11—B1—C21—C26	57.1 (3)
C4—C3—C7—F72	26.6 (8)	C1—B1—C21—C26	−122.2 (3)
C2—C3—C7—F72	−153.3 (7)	C11—B1—C21—C22	−125.0 (3)
C4—C3—C7—F71'	−137.1 (7)	C1—B1—C21—C22	55.7 (3)
C2—C3—C7—F71'	42.9 (8)	C26—C21—C22—C23	0.2 (3)
C4—C3—C7—F71	−110.6 (7)	B1—C21—C22—C23	−177.8 (2)
C2—C3—C7—F71	69.5 (7)	C26—C21—C22—C28	−178.2 (2)
C4—C3—C7—F72'	−21.4 (6)	B1—C21—C22—C28	3.9 (4)
C2—C3—C7—F72'	158.7 (6)	C21—C22—C23—C24	0.1 (4)
C4—C3—C7—F73	140.2 (5)	C28—C22—C23—C24	178.5 (3)
C2—C3—C7—F73	−39.7 (5)	C22—C23—C24—C25	0.4 (4)
C4—C5—C8—F83	−105.9 (3)	C22—C23—C24—C29	179.8 (3)
C6—C5—C8—F83	73.3 (4)	C23—C24—C25—C26	−1.2 (4)
C4—C5—C8—F81	15.2 (4)	C29—C24—C25—C26	179.4 (3)
C6—C5—C8—F81	−165.6 (3)	C24—C25—C26—C21	1.5 (4)
C4—C5—C8—F82	135.9 (3)	C24—C25—C26—C27	178.1 (3)
C6—C5—C8—F82	−44.9 (4)	C22—C21—C26—C25	−0.9 (4)
C21—B1—C11—C12	49.4 (4)	B1—C21—C26—C25	177.1 (2)
C1—B1—C11—C12	−131.3 (3)	C22—C21—C26—C27	−177.4 (2)
C21—B1—C11—C16	−135.2 (3)	B1—C21—C26—C27	0.5 (4)

(V) Bis[2,6-bis(trifluoromethyl)phenyl]fluoroborane top

Crystal data top

C₁₆H₆BF₁₃	F(000) = 896
M_r = 456.02	D_x = 1.797 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.9807 (15) Å	Cell parameters from 9028 reflections
b = 9.2709 (9) Å	θ = 3.5–25.7°
c = 15.269 (2) Å	µ = 0.21 mm⁻¹
β = 113.455 (9)°	T = 173 K
V = 1685.7 (4) Å³	Plate, colourless
Z = 4	0.26 × 0.22 × 0.06 mm

Data collection top

Stoe IPDS II two-circle diffractometer	1959 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.086
ω scans	θ_max = 25.7°, θ_min = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −15→15
T_min = 0.360, T_max = 1.000	k = −11→11
20206 measured reflections	l = −18→18
3179 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0713P)² + 0.2873P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3179 reflections	Δρ_max = 0.62 e Å⁻³
271 parameters	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₆BF₁₃	V = 1685.7 (4) Å³
M_r = 456.02	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.9807 (15) Å	µ = 0.21 mm⁻¹
b = 9.2709 (9) Å	T = 173 K
c = 15.269 (2) Å	0.26 × 0.22 × 0.06 mm
β = 113.455 (9)°

Data collection top

Stoe IPDS II two-circle diffractometer	3179 independent reflections
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	1959 reflections with I > 2σ(I)
T_min = 0.360, T_max = 1.000	R_int = 0.086
20206 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.05	Δρ_max = 0.62 e Å⁻³
3179 reflections	Δρ_min = −0.42 e Å⁻³
271 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	0.2307 (3)	0.2081 (4)	0.5538 (3)	0.0339 (9)
F1	0.13770 (19)	0.1319 (2)	0.51534 (14)	0.0531 (6)
C1	0.2845 (3)	0.2567 (4)	0.4817 (2)	0.0365 (8)
C2	0.3087 (3)	0.4010 (4)	0.4700 (3)	0.0451 (9)
C3	0.3576 (4)	0.4403 (5)	0.4074 (3)	0.0642 (13)
H3	0.3735	0.5389	0.4012	0.077*
C4	0.3830 (4)	0.3378 (5)	0.3545 (3)	0.0627 (12)
H4	0.4177	0.3648	0.3127	0.075*
C5	0.3580 (4)	0.1964 (5)	0.3623 (3)	0.0538 (11)
H5	0.3740	0.1254	0.3247	0.065*
C6	0.3096 (3)	0.1556 (4)	0.4245 (2)	0.0406 (8)
C7	0.2797 (5)	0.5199 (4)	0.5230 (4)	0.0670 (13)
F71	0.1859 (2)	0.4927 (3)	0.5355 (2)	0.0737 (8)
F72	0.3574 (3)	0.5382 (3)	0.6123 (2)	0.0930 (10)
F73	0.2645 (4)	0.6445 (3)	0.4789 (3)	0.1287 (15)
C8	0.2804 (4)	−0.0008 (4)	0.4237 (3)	0.0541 (11)
F81	0.2844 (2)	−0.0508 (2)	0.50546 (17)	0.0632 (7)
F82	0.3396 (4)	−0.0837 (3)	0.3936 (4)	0.1427 (19)
F83	0.1730 (3)	−0.0239 (3)	0.36198 (19)	0.0932 (11)
C11	0.2726 (3)	0.2409 (3)	0.6648 (2)	0.0334 (8)
C12	0.3858 (3)	0.2381 (3)	0.7280 (2)	0.0371 (8)
C13	0.4201 (4)	0.2739 (4)	0.8237 (3)	0.0495 (10)
H13	0.4976	0.2704	0.8646	0.059*
C14	0.3435 (4)	0.3142 (5)	0.8597 (3)	0.0574 (11)
H14	0.3676	0.3416	0.9248	0.069*
C15	0.2323 (4)	0.3147 (4)	0.8014 (3)	0.0502 (10)
H15	0.1788	0.3406	0.8266	0.060*
C16	0.1957 (3)	0.2780 (4)	0.7056 (2)	0.0394 (8)
C17	0.4775 (3)	0.1925 (4)	0.6974 (2)	0.0421 (9)
F171	0.44763 (18)	0.0800 (2)	0.63771 (14)	0.0485 (6)
F172	0.5070 (2)	0.2973 (3)	0.65109 (18)	0.0642 (7)
F173	0.57065 (19)	0.1529 (3)	0.77013 (16)	0.0668 (7)
C18	0.0712 (4)	0.2762 (5)	0.6505 (3)	0.0539 (11)
F181	0.0298 (2)	0.1433 (3)	0.6351 (2)	0.0741 (8)
F182	0.0373 (2)	0.3392 (3)	0.56510 (19)	0.0710 (7)
F183	0.0172 (2)	0.3442 (4)	0.6972 (2)	0.1019 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.031 (2)	0.0294 (18)	0.042 (2)	0.0002 (16)	0.0151 (17)	−0.0012 (16)
F1	0.0500 (14)	0.0699 (14)	0.0435 (11)	−0.0240 (11)	0.0228 (10)	−0.0162 (10)
C1	0.033 (2)	0.0387 (18)	0.0363 (17)	−0.0018 (15)	0.0121 (15)	0.0046 (14)
C2	0.040 (2)	0.0414 (19)	0.050 (2)	−0.0018 (17)	0.0140 (17)	0.0133 (16)
C3	0.058 (3)	0.059 (3)	0.073 (3)	−0.006 (2)	0.023 (2)	0.031 (2)
C4	0.054 (3)	0.089 (3)	0.051 (2)	−0.004 (2)	0.026 (2)	0.029 (2)
C5	0.050 (3)	0.076 (3)	0.041 (2)	−0.003 (2)	0.0238 (19)	0.0035 (19)
C6	0.038 (2)	0.049 (2)	0.0374 (18)	−0.0037 (17)	0.0171 (16)	0.0017 (15)
C7	0.072 (4)	0.033 (2)	0.094 (4)	−0.002 (2)	0.031 (3)	0.007 (2)
F71	0.0656 (19)	0.0477 (13)	0.111 (2)	0.0148 (12)	0.0379 (16)	0.0067 (13)
F72	0.079 (2)	0.0783 (19)	0.114 (2)	−0.0132 (16)	0.0311 (19)	−0.0457 (17)
F73	0.203 (4)	0.0365 (14)	0.190 (4)	0.0202 (19)	0.124 (3)	0.0377 (19)
C8	0.058 (3)	0.053 (2)	0.070 (3)	−0.013 (2)	0.046 (2)	−0.022 (2)
F81	0.088 (2)	0.0409 (12)	0.0614 (14)	−0.0129 (12)	0.0302 (13)	0.0039 (10)
F82	0.188 (4)	0.0625 (18)	0.277 (5)	−0.024 (2)	0.198 (4)	−0.049 (2)
F83	0.105 (3)	0.105 (2)	0.0619 (16)	−0.0611 (19)	0.0256 (16)	−0.0251 (15)
C11	0.034 (2)	0.0275 (16)	0.0402 (18)	0.0001 (14)	0.0164 (16)	−0.0004 (13)
C12	0.036 (2)	0.0351 (17)	0.0373 (18)	−0.0017 (15)	0.0115 (16)	−0.0017 (14)
C13	0.044 (2)	0.058 (2)	0.039 (2)	−0.0015 (19)	0.0084 (18)	−0.0091 (17)
C14	0.067 (3)	0.067 (3)	0.037 (2)	0.005 (2)	0.019 (2)	−0.0115 (18)
C15	0.057 (3)	0.054 (2)	0.046 (2)	0.006 (2)	0.027 (2)	−0.0083 (17)
C16	0.042 (2)	0.0368 (19)	0.0412 (19)	0.0023 (15)	0.0182 (17)	−0.0034 (14)
C17	0.035 (2)	0.053 (2)	0.0361 (18)	−0.0018 (17)	0.0122 (16)	0.0016 (16)
F171	0.0401 (13)	0.0557 (13)	0.0512 (12)	0.0069 (10)	0.0196 (10)	−0.0053 (10)
F172	0.0584 (16)	0.0653 (15)	0.0824 (16)	−0.0100 (12)	0.0423 (13)	0.0097 (13)
F173	0.0353 (13)	0.1022 (19)	0.0528 (14)	0.0135 (13)	0.0070 (11)	0.0029 (12)
C18	0.045 (3)	0.065 (3)	0.057 (2)	0.004 (2)	0.025 (2)	−0.017 (2)
F181	0.0511 (16)	0.0867 (19)	0.0935 (19)	−0.0241 (14)	0.0383 (14)	−0.0148 (15)
F182	0.0447 (15)	0.0799 (17)	0.0733 (17)	0.0132 (13)	0.0074 (12)	0.0022 (14)
F183	0.0522 (18)	0.152 (3)	0.106 (2)	0.0179 (18)	0.0365 (16)	−0.056 (2)

Geometric parameters (Å, º) top

B1—F1	1.318 (4)	C8—F83	1.353 (5)
B1—C1	1.586 (5)	C11—C12	1.401 (5)
B1—C11	1.589 (5)	C11—C16	1.413 (5)
C1—C2	1.402 (5)	C12—C13	1.388 (5)
C1—C6	1.405 (5)	C12—C17	1.501 (5)
C2—C3	1.390 (6)	C13—C14	1.366 (6)
C2—C7	1.501 (6)	C13—H13	0.9500
C3—C4	1.369 (7)	C14—C15	1.362 (6)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.367 (6)	C15—C16	1.388 (5)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.383 (5)	C16—C18	1.496 (6)
C5—H5	0.9500	C17—F173	1.327 (4)
C6—C8	1.497 (5)	C17—F171	1.336 (4)
C7—F73	1.312 (5)	C17—F172	1.345 (4)
C7—F71	1.330 (6)	C18—F181	1.327 (5)
C7—F72	1.346 (6)	C18—F182	1.334 (5)
C8—F82	1.294 (5)	C18—F183	1.340 (5)
C8—F81	1.313 (5)

F1—B1—C1	114.9 (3)	F83—C8—C6	110.3 (4)
F1—B1—C11	116.2 (3)	C12—C11—C16	115.6 (3)
C1—B1—C11	128.9 (3)	C12—C11—B1	123.4 (3)
C2—C1—C6	116.0 (3)	C16—C11—B1	121.0 (3)
C2—C1—B1	122.8 (3)	C13—C12—C11	121.9 (3)
C6—C1—B1	121.2 (3)	C13—C12—C17	115.7 (3)
C3—C2—C1	121.6 (4)	C11—C12—C17	122.4 (3)
C3—C2—C7	117.3 (4)	C14—C13—C12	120.7 (4)
C1—C2—C7	121.0 (3)	C14—C13—H13	119.7
C4—C3—C2	120.4 (4)	C12—C13—H13	119.7
C4—C3—H3	119.8	C15—C14—C13	119.3 (4)
C2—C3—H3	119.8	C15—C14—H14	120.4
C5—C4—C3	119.5 (4)	C13—C14—H14	120.4
C5—C4—H4	120.2	C14—C15—C16	121.2 (4)
C3—C4—H4	120.2	C14—C15—H15	119.4
C4—C5—C6	120.7 (4)	C16—C15—H15	119.4
C4—C5—H5	119.7	C15—C16—C11	121.2 (3)
C6—C5—H5	119.7	C15—C16—C18	115.8 (3)
C5—C6—C1	121.7 (3)	C11—C16—C18	123.0 (3)
C5—C6—C8	116.2 (3)	F173—C17—F171	106.0 (3)
C1—C6—C8	122.1 (3)	F173—C17—F172	106.5 (3)
F73—C7—F71	106.4 (4)	F171—C17—F172	105.8 (3)
F73—C7—F72	108.0 (4)	F173—C17—C12	112.9 (3)
F71—C7—F72	103.8 (4)	F171—C17—C12	112.4 (3)
F73—C7—C2	112.8 (4)	F172—C17—C12	112.8 (3)
F71—C7—C2	112.3 (4)	F181—C18—F182	106.3 (3)
F72—C7—C2	113.0 (4)	F181—C18—F183	105.7 (4)
F82—C8—F81	108.8 (4)	F182—C18—F183	106.0 (4)
F82—C8—F83	104.6 (4)	F181—C18—C16	112.4 (3)
F81—C8—F83	104.3 (3)	F182—C18—C16	114.0 (4)
F82—C8—C6	113.2 (3)	F183—C18—C16	111.9 (3)
F81—C8—C6	114.8 (3)

F1—B1—C1—C2	125.1 (4)	F1—B1—C11—C12	140.5 (3)
C11—B1—C1—C2	−53.8 (5)	C1—B1—C11—C12	−40.6 (5)
F1—B1—C1—C6	−54.2 (4)	F1—B1—C11—C16	−40.7 (4)
C11—B1—C1—C6	126.9 (4)	C1—B1—C11—C16	138.2 (4)
C6—C1—C2—C3	−1.8 (5)	C16—C11—C12—C13	−2.0 (5)
B1—C1—C2—C3	178.9 (4)	B1—C11—C12—C13	176.9 (3)
C6—C1—C2—C7	176.5 (4)	C16—C11—C12—C17	176.4 (3)
B1—C1—C2—C7	−2.8 (6)	B1—C11—C12—C17	−4.8 (5)
C1—C2—C3—C4	0.4 (6)	C11—C12—C13—C14	−0.3 (6)
C7—C2—C3—C4	−178.0 (4)	C17—C12—C13—C14	−178.7 (4)
C2—C3—C4—C5	1.2 (7)	C12—C13—C14—C15	2.0 (6)
C3—C4—C5—C6	−1.4 (6)	C13—C14—C15—C16	−1.4 (6)
C4—C5—C6—C1	0.0 (6)	C14—C15—C16—C11	−1.0 (6)
C4—C5—C6—C8	176.9 (4)	C14—C15—C16—C18	177.2 (4)
C2—C1—C6—C5	1.6 (5)	C12—C11—C16—C15	2.6 (5)
B1—C1—C6—C5	−179.1 (3)	B1—C11—C16—C15	−176.3 (3)
C2—C1—C6—C8	−175.2 (4)	C12—C11—C16—C18	−175.5 (3)
B1—C1—C6—C8	4.1 (5)	B1—C11—C16—C18	5.6 (5)
C3—C2—C7—F73	24.3 (6)	C13—C12—C17—F173	18.7 (5)
C1—C2—C7—F73	−154.1 (4)	C11—C12—C17—F173	−159.8 (3)
C3—C2—C7—F71	144.5 (4)	C13—C12—C17—F171	138.5 (3)
C1—C2—C7—F71	−33.9 (6)	C11—C12—C17—F171	−40.0 (4)
C3—C2—C7—F72	−98.5 (5)	C13—C12—C17—F172	−102.1 (4)
C1—C2—C7—F72	83.1 (5)	C11—C12—C17—F172	79.5 (4)
C5—C6—C8—F82	24.4 (6)	C15—C16—C18—F181	−103.4 (4)
C1—C6—C8—F82	−158.6 (4)	C11—C16—C18—F181	74.8 (5)
C5—C6—C8—F81	150.2 (4)	C15—C16—C18—F182	135.5 (4)
C1—C6—C8—F81	−32.8 (6)	C11—C16—C18—F182	−46.3 (5)
C5—C6—C8—F83	−92.4 (4)	C15—C16—C18—F183	15.3 (5)
C1—C6—C8—F83	84.6 (4)	C11—C16—C18—F183	−166.5 (4)

Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C₂₂H₁₁BF₁₂	C₂₄H₉BF₁₈	C₂₄H₉BF₁₈
M_r	514.12	650.12	650.12
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Triclinic, P1	Triclinic, P1
Temperature (K)	173	173	173
a, b, c (Å)	8.3748 (6), 18.2499 (9), 27.5695 (14)	8.2059 (6), 8.7103 (7), 18.0982 (14)	10.8257 (11), 11.4704 (13), 12.0198 (14)
α, β, γ (°)	90, 90, 90	103.491 (6), 95.430 (6), 99.093 (6)	117.067 (8), 101.774 (9), 100.795 (9)
V (Å³)	4213.7 (4)	1230.38 (17)	1232.1 (3)
Z	8	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.17	0.20	0.20
Crystal size (mm)	0.18 × 0.11 × 0.08	0.21 × 0.17 × 0.08	0.28 × 0.28 × 0.26

Data collection
Diffractometer	Stoe IPDS II two-circle	Stoe IPDS II two-circle	Stoe IPDS II two-circle
Absorption correction	Multi-scan (X-AREA; Stoe & Cie, 2001)	Multi-scan (X-AREA; Stoe & Cie, 2001)	Multi-scan (X-AREA; Stoe & Cie, 2001)
T_min, T_max	0.681, 1.000	0.434, 1.000	0.627, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	33823, 7431, 4181	25668, 5677, 4520	9949, 4566, 3599
R_int	0.134	0.058	0.024
(sin θ/λ)_max (Å⁻¹)	0.595	0.653	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.105, 0.82	0.057, 0.148, 1.04	0.046, 0.115, 1.06
No. of reflections	7431	5677	4566
No. of parameters	687	416	444
No. of restraints	72	36	36
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.21	0.58, −0.36	0.45, −0.26

	(IV)	(V)
Crystal data
Chemical formula	C₂₆H₂₅BF₆	C₁₆H₆BF₁₃
M_r	462.27	456.02
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n
Temperature (K)	173	173
a, b, c (Å)	8.3500 (12), 34.370 (4), 8.5512 (13)	12.9807 (15), 9.2709 (9), 15.269 (2)
α, β, γ (°)	90, 107.062 (11), 90	90, 113.455 (9), 90
V (Å³)	2346.1 (6)	1685.7 (4)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.11	0.21
Crystal size (mm)	0.27 × 0.27 × 0.24	0.26 × 0.22 × 0.06

Data collection
Diffractometer	Stoe IPDS II two-circle	Stoe IPDS II two-circle
Absorption correction	Multi-scan (X-AREA; Stoe & Cie, 2001)	Multi-scan (X-AREA; Stoe & Cie, 2001)
T_min, T_max	0.448, 1.000	0.360, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9711, 4294, 2565	20206, 3179, 1959
R_int	0.109	0.086
(sin θ/λ)_max (Å⁻¹)	0.608	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.172, 0.93	0.061, 0.155, 1.05
No. of reflections	4294	3179
No. of parameters	332	271
No. of restraints	36	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.27	0.62, −0.42

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Subscribe to Acta Crystallographica Section C: Structural Chemistry

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Conformational studies on heteroleptic tri­fluoro­methyl-substituted phenyl­boranes

Supporting information

Subscribe to Acta Crystallographica Section C: Structural Chemistry

Buy online

Conformational studies on heteroleptic trifluoromethyl-substituted phenylboranes