2-Vinyl­pyridine–tris­(penta­fluoro­phen­yl)borane hexane monosolvate

Klahn, M.; Spannenberg, A.; Rosenthal, U.

doi:10.1107/S1600536812013153

organic compounds

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Volume 68| Part 4| April 2012| Page o1261

doi:10.1107/S1600536812013153

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2-Vinylpyridine–tris(pentafluorophenyl)borane hexane monosolvate

Marcus Klahn,^a ^* Anke Spannenberg ^a and Uwe Rosenthal ^a

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: marcus.klahn@catalysis.de

(Received 14 March 2012; accepted 26 March 2012; online 31 March 2012)

The title compound, C₇H₇N·B(C₆F₅)₃·C₆H₁₄, was obtained by the stoichiometric reaction of 2-vinylpyridine and tris(pentafluorophenyl)borane in toluene. The formed adduct exhibits a restricted rotation along the B—N bond resulting in an asymmetry, which can be also observed in the ¹⁹F NMR spectra. The B—N distance is equivalent to the distances found for 2-methylpyridine and 2-ethylpyridine B(C₆F₅)₃ adducts. For the final refinement, the contributions of disordered solvent molecules were removed from the diffraction data with SQUEEZE in PLATON [van der Sluis & Spek (1990). Acta Cryst. A46, 194–201; Spek (2009). Acta Cryst. D65, 148–155].

Related literature

For general aspects of related compounds, see: Focante et al. (2006 ); Stephan & Erker (2010 ); Welch et al. (2007 ). For related structures, see: Geier et al. (2009 ). For the use of SQUEEZE in PLATON to remove the contributions of disordered solvent molecules, see: van der Sluis & Spek (1990 ); Spek (2009 ).

Experimental

Crystal data

C₂₅H₇BF₁₅N·C₆H₁₄
M_r = 730.30
Monoclinic, P 2₁ /n
a = 12.4173 (2) Å
b = 17.1269 (3) Å
c = 13.9211 (2) Å
β = 100.889 (1)°
V = 2907.29 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 150 K
0.35 × 0.33 × 0.25 mm

Data collection

Bruker Kappa APEXII DUO diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.695, T_max = 0.746
55747 measured reflections
6929 independent reflections
5324 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.113
S = 1.04
6929 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2009 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812013153/vm2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013153/vm2164Isup2.hkl

checkCIF report

Comment top

The concept of "Frustrated Lewis pairs" has been put forth and coined by Welch et al. (2007). The key feature is the sterical hindrance between the Lewis acids and bases preventing the formation of a classical adduct which gives rise to a unique reactivity due to the interaction of the basic and acidic centers. This characteristic facilitates a lot of reactions with a wide variety of reagents, as it has been overviewed by Stephan & Erker (2010). The substrates can be either small molecules like H₂, CO₂, and N₂O, or larger ones like terminal olefins, alkynes, dienes, B–H bonds, disulfides and the C–O bonds of cyclic ethers. The conversion of 2-vinylpyridine with tris(pentafluorophenyl)borane proceeds similar to the general formation of Lewis acid base adducts presented before by Focante et al. (2006) and Geier et al. (2009). The nature of the adduct (figure 1) is confirmed by the precluded activation of dihydrogen. As found for other pyridine derivatives, the compound gives ¹⁹F-NMR spectra with 15 signals, one for each fluorine atom at the borane. This asymmetry results from a restricted rotation of the B–N bond. The B–N distance of the title compound (1.637 (3) Å) is found to be the same as for the analogous compounds 2-methylvinylpyridine/B(C₆F₅)₃ 1.639 (2) Å and 2-ethylpyridine/B(C₆F₅)₃ 1.638 (2) Å, respectively (Geier et al., 2009). This finding corroborates the assumption that the vinyl group in ortho-position to the nitrogen has no influence on the bonding situation. The boron center exhibits a distorted tetrahedral coordination geometry.

Related literature top

For general aspects of related compounds, see: Focante et al. (2006); Stephan & Erker (2010); Welch et al. (2007). For related structures, see: Geier et al. (2009). For the final refinement the contributions of disordered solvent molecules were removed from the diffraction data with SQUEEZE in PLATON (van der Sluis & Spek, 1990; Spek, 2009).

Experimental top

Solid tris(pentafluorophenyl)borane (0.512 g, 1.0 mmol) and vinylpyridine (0.11 ml, 1.0 mmol) were dissolved in 25 ml of toluene resulting in a colorless solution. The reaction was allowed to stir for 2 h at 40 °C. The solvent was removed in vaccuo and the residue was extracted with n-hexane. Slow evaporation of the solvent resulted in the formation of colorless prisms. Isolated yield for pure crystalline material 0.380 g (62%).

Structure description top

For general aspects of related compounds, see: Focante et al. (2006); Stephan & Erker (2010); Welch et al. (2007). For related structures, see: Geier et al. (2009). For the final refinement the contributions of disordered solvent molecules were removed from the diffraction data with SQUEEZE in PLATON (van der Sluis & Spek, 1990; Spek, 2009).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom labels and 30% displacement ellipsoids. Hydrogen atoms are omitted for clarity.

2-Vinylpyridine–tris(pentafluorophenyl)borane hexane monosolvate top

Crystal data top

C₂₅H₇BF₁₅N·C₆H₁₄	F(000) = 1416
M_r = 703.30	D_x = 1.607 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.4173 (2) Å	Cell parameters from 9876 reflections
b = 17.1269 (3) Å	θ = 2.3–26.3°
c = 13.9211 (2) Å	µ = 0.16 mm⁻¹
β = 100.889 (1)°	T = 150 K
V = 2907.29 (8) Å³	Prism, colourless
Z = 4	0.35 × 0.33 × 0.25 mm

Data collection top

Bruker Kappa APEXII DUO diffractometer	6929 independent reflections
Radiation source: fine-focus sealed tube	5324 reflections with I > 2σ(I)
Curved graphite monochromator	R_int = 0.030
Detector resolution: 8.3333 pixels mm^-1	θ_max = 27.9°, θ_min = 1.9°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = 0→22
T_min = 0.695, T_max = 0.746	l = 0→18
55747 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0312P)² + 2.2216P] where P = (F_o² + 2F_c²)/3
6929 reflections	(Δ/σ)_max < 0.001
379 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₅H₇BF₁₅N·C₆H₁₄	V = 2907.29 (8) Å³
M_r = 703.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4173 (2) Å	µ = 0.16 mm⁻¹
b = 17.1269 (3) Å	T = 150 K
c = 13.9211 (2) Å	0.35 × 0.33 × 0.25 mm
β = 100.889 (1)°

Data collection top

Bruker Kappa APEXII DUO diffractometer	6929 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5324 reflections with I > 2σ(I)
T_min = 0.695, T_max = 0.746	R_int = 0.030
55747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
6929 reflections	Δρ_min = −0.25 e Å⁻³
379 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.90231 (17)	0.13181 (12)	0.38660 (15)	0.0434 (5)
H1	0.8263	0.1383	0.3864	0.052*
C2	0.9757 (2)	0.16041 (15)	0.46482 (18)	0.0578 (6)
H2	0.9512	0.1865	0.5169	0.069*
C3	1.0860 (2)	0.15025 (18)	0.4657 (2)	0.0713 (8)
H3	1.1392	0.1673	0.5200	0.086*
C4	1.11785 (19)	0.11521 (16)	0.3873 (2)	0.0668 (8)
H4	1.1938	0.1084	0.3874	0.080*
C5	1.04135 (16)	0.08929 (12)	0.30710 (19)	0.0493 (5)
C6	1.07643 (17)	0.05611 (14)	0.2212 (2)	0.0565 (6)
H6	1.0328	0.0165	0.1853	0.068*
C7	1.1666 (2)	0.07912 (17)	0.1916 (3)	0.0765 (9)
H7A	1.2114	0.1187	0.2265	0.092*
H7B	1.1865	0.0561	0.1353	0.092*
C8	0.84554 (14)	−0.02844 (11)	0.19742 (13)	0.0334 (4)
C9	0.90655 (14)	−0.08385 (11)	0.25654 (13)	0.0343 (4)
C10	0.90397 (16)	−0.16275 (11)	0.23593 (14)	0.0375 (4)
C11	0.83804 (18)	−0.18957 (11)	0.15249 (15)	0.0415 (4)
C12	0.77312 (18)	−0.13771 (13)	0.09240 (15)	0.0449 (5)
C13	0.77700 (16)	−0.05962 (12)	0.11631 (14)	0.0391 (4)
C14	0.71442 (14)	0.07074 (10)	0.25130 (13)	0.0313 (4)
C15	0.69487 (15)	0.02992 (11)	0.33276 (13)	0.0346 (4)
C16	0.59468 (16)	0.02570 (11)	0.36130 (15)	0.0389 (4)
C17	0.50623 (15)	0.06250 (11)	0.30572 (15)	0.0396 (4)
C18	0.51920 (15)	0.10188 (11)	0.22336 (15)	0.0385 (4)
C19	0.62162 (15)	0.10543 (10)	0.19769 (13)	0.0334 (4)
C20	0.85181 (15)	0.12444 (12)	0.13074 (16)	0.0412 (5)
C21	0.83817 (15)	0.20401 (12)	0.14261 (17)	0.0454 (5)
C22	0.85464 (18)	0.25980 (14)	0.0756 (2)	0.0596 (7)
C23	0.8865 (2)	0.23690 (17)	−0.0090 (2)	0.0714 (8)
C24	0.9022 (2)	0.15996 (17)	−0.0244 (2)	0.0709 (8)
C25	0.88500 (18)	0.10540 (14)	0.04498 (18)	0.0539 (6)
N1	0.93177 (12)	0.09495 (9)	0.30993 (13)	0.0385 (4)
B1	0.83605 (16)	0.06510 (12)	0.22003 (16)	0.0332 (4)
F1	0.97508 (9)	−0.06271 (7)	0.33938 (8)	0.0438 (3)
F2	0.96667 (11)	−0.21289 (7)	0.29565 (9)	0.0499 (3)
F3	0.83723 (12)	−0.26568 (7)	0.12948 (9)	0.0543 (3)
F4	0.70812 (13)	−0.16365 (9)	0.01098 (9)	0.0679 (4)
F5	0.70978 (11)	−0.01194 (7)	0.05566 (8)	0.0511 (3)
F6	0.77858 (9)	−0.00810 (7)	0.38990 (8)	0.0424 (3)
F7	0.58340 (11)	−0.01383 (7)	0.44164 (9)	0.0528 (3)
F8	0.40755 (10)	0.05864 (7)	0.33126 (10)	0.0553 (3)
F9	0.43240 (9)	0.13657 (7)	0.16772 (10)	0.0515 (3)
F10	0.62556 (9)	0.14561 (7)	0.11527 (8)	0.0405 (3)
F11	0.80562 (10)	0.23048 (7)	0.22390 (10)	0.0492 (3)
F12	0.83828 (12)	0.33561 (8)	0.09278 (14)	0.0760 (5)
F13	0.90227 (15)	0.29033 (11)	−0.07537 (15)	0.1035 (7)
F14	0.93402 (17)	0.13562 (12)	−0.10669 (14)	0.1034 (7)
F15	0.90590 (12)	0.03096 (8)	0.02312 (10)	0.0670 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0383 (10)	0.0435 (11)	0.0467 (11)	0.0014 (8)	0.0031 (9)	0.0103 (9)
C2	0.0560 (14)	0.0589 (14)	0.0517 (13)	−0.0058 (11)	−0.0068 (11)	0.0084 (11)
C3	0.0509 (14)	0.0776 (19)	0.0741 (18)	−0.0134 (13)	−0.0170 (13)	0.0157 (15)
C4	0.0320 (11)	0.0657 (16)	0.096 (2)	−0.0033 (11)	−0.0044 (12)	0.0250 (15)
C5	0.0305 (9)	0.0393 (11)	0.0777 (16)	0.0015 (8)	0.0091 (10)	0.0185 (10)
C6	0.0337 (10)	0.0484 (12)	0.0917 (18)	0.0077 (9)	0.0227 (11)	0.0178 (12)
C7	0.0389 (12)	0.0733 (18)	0.124 (3)	0.0028 (12)	0.0322 (15)	0.0183 (17)
C8	0.0294 (8)	0.0379 (9)	0.0360 (9)	0.0069 (7)	0.0145 (7)	0.0077 (8)
C9	0.0307 (9)	0.0378 (9)	0.0365 (10)	0.0022 (7)	0.0119 (7)	0.0071 (8)
C10	0.0409 (10)	0.0377 (10)	0.0375 (10)	0.0086 (8)	0.0165 (8)	0.0123 (8)
C11	0.0534 (12)	0.0357 (10)	0.0400 (10)	0.0042 (9)	0.0207 (9)	0.0020 (8)
C12	0.0511 (12)	0.0507 (12)	0.0336 (10)	0.0081 (9)	0.0096 (9)	−0.0024 (9)
C13	0.0413 (10)	0.0449 (11)	0.0332 (9)	0.0138 (8)	0.0123 (8)	0.0080 (8)
C14	0.0296 (8)	0.0315 (9)	0.0343 (9)	0.0015 (7)	0.0101 (7)	0.0002 (7)
C15	0.0338 (9)	0.0348 (9)	0.0368 (10)	0.0047 (7)	0.0111 (7)	0.0005 (7)
C16	0.0441 (10)	0.0348 (9)	0.0437 (11)	−0.0004 (8)	0.0230 (9)	−0.0002 (8)
C17	0.0302 (9)	0.0402 (10)	0.0530 (12)	−0.0028 (8)	0.0194 (8)	−0.0107 (9)
C18	0.0281 (9)	0.0361 (10)	0.0503 (11)	0.0018 (7)	0.0049 (8)	−0.0075 (8)
C19	0.0331 (9)	0.0334 (9)	0.0336 (9)	−0.0001 (7)	0.0060 (7)	−0.0043 (7)
C20	0.0300 (9)	0.0426 (10)	0.0546 (12)	0.0111 (8)	0.0174 (8)	0.0184 (9)
C21	0.0282 (9)	0.0458 (11)	0.0643 (14)	0.0062 (8)	0.0141 (9)	0.0174 (10)
C22	0.0381 (11)	0.0483 (13)	0.0928 (19)	0.0064 (9)	0.0130 (12)	0.0346 (13)
C23	0.0501 (14)	0.0793 (18)	0.092 (2)	0.0110 (13)	0.0333 (14)	0.0541 (16)
C24	0.0630 (15)	0.0844 (19)	0.0793 (18)	0.0288 (14)	0.0497 (14)	0.0443 (15)
C25	0.0466 (12)	0.0598 (14)	0.0642 (14)	0.0221 (10)	0.0332 (11)	0.0265 (11)
N1	0.0287 (7)	0.0349 (8)	0.0510 (10)	0.0023 (6)	0.0047 (7)	0.0121 (7)
B1	0.0282 (9)	0.0343 (10)	0.0386 (11)	0.0050 (8)	0.0101 (8)	0.0059 (8)
F1	0.0396 (6)	0.0386 (6)	0.0494 (7)	0.0036 (5)	−0.0013 (5)	0.0087 (5)
F2	0.0609 (8)	0.0361 (6)	0.0505 (7)	0.0103 (5)	0.0047 (6)	0.0115 (5)
F3	0.0768 (9)	0.0390 (6)	0.0494 (7)	0.0074 (6)	0.0176 (6)	−0.0017 (5)
F4	0.0918 (11)	0.0615 (9)	0.0424 (7)	0.0167 (8)	−0.0072 (7)	−0.0129 (6)
F5	0.0592 (7)	0.0535 (7)	0.0374 (6)	0.0205 (6)	0.0008 (5)	0.0042 (5)
F6	0.0417 (6)	0.0454 (6)	0.0428 (6)	0.0078 (5)	0.0148 (5)	0.0121 (5)
F7	0.0601 (8)	0.0505 (7)	0.0585 (8)	0.0043 (6)	0.0387 (6)	0.0083 (6)
F8	0.0366 (6)	0.0537 (7)	0.0840 (9)	−0.0013 (5)	0.0326 (6)	−0.0045 (7)
F9	0.0266 (5)	0.0561 (7)	0.0684 (8)	0.0036 (5)	0.0001 (5)	−0.0037 (6)
F10	0.0353 (6)	0.0488 (6)	0.0367 (6)	0.0071 (5)	0.0047 (4)	0.0059 (5)
F11	0.0452 (7)	0.0373 (6)	0.0649 (8)	0.0040 (5)	0.0100 (6)	0.0052 (6)
F12	0.0589 (9)	0.0427 (7)	0.1227 (14)	0.0026 (6)	0.0078 (9)	0.0343 (8)
F13	0.0922 (12)	0.1019 (13)	0.1287 (16)	0.0164 (10)	0.0526 (12)	0.0824 (12)
F14	0.1180 (15)	0.1220 (15)	0.0956 (13)	0.0472 (12)	0.0845 (12)	0.0574 (11)
F15	0.0828 (10)	0.0677 (9)	0.0652 (9)	0.0380 (8)	0.0518 (8)	0.0245 (7)

Geometric parameters (Å, º) top

C1—N1	1.349 (3)	C13—F5	1.345 (2)
C1—C2	1.372 (3)	C14—C19	1.383 (2)
C1—H1	0.9500	C14—C15	1.392 (2)
C2—C3	1.379 (4)	C14—B1	1.652 (3)
C2—H2	0.9500	C15—F6	1.351 (2)
C3—C4	1.368 (4)	C15—C16	1.377 (2)
C3—H3	0.9500	C16—F7	1.337 (2)
C4—C5	1.395 (4)	C16—C17	1.372 (3)
C4—H4	0.9500	C17—F8	1.340 (2)
C5—N1	1.372 (2)	C17—C18	1.366 (3)
C5—C6	1.462 (4)	C18—F9	1.341 (2)
C6—C7	1.325 (3)	C18—C19	1.386 (3)
C6—H6	0.9500	C19—F10	1.347 (2)
C7—H7A	0.9500	C20—C25	1.374 (3)
C7—H7B	0.9500	C20—C21	1.387 (3)
C8—C9	1.384 (2)	C20—B1	1.646 (3)
C8—C13	1.386 (3)	C21—F11	1.350 (3)
C8—B1	1.641 (3)	C21—C22	1.378 (3)
C9—F1	1.347 (2)	C22—F12	1.343 (3)
C9—C10	1.380 (3)	C22—C23	1.368 (4)
C10—F2	1.338 (2)	C23—F13	1.341 (3)
C10—C11	1.368 (3)	C23—C24	1.355 (4)
C11—F3	1.342 (2)	C24—F14	1.346 (3)
C11—C12	1.373 (3)	C24—C25	1.390 (3)
C12—F4	1.337 (2)	C25—F15	1.347 (3)
C12—C13	1.377 (3)	N1—B1	1.637 (3)

N1—C1—C2	123.8 (2)	F6—C15—C16	116.19 (16)
N1—C1—H1	118.1	F6—C15—C14	119.25 (15)
C2—C1—H1	118.1	C16—C15—C14	124.56 (17)
C1—C2—C3	118.2 (3)	F7—C16—C17	120.35 (17)
C1—C2—H2	120.9	F7—C16—C15	120.71 (18)
C3—C2—H2	120.9	C17—C16—C15	118.94 (17)
C4—C3—C2	119.0 (2)	F8—C17—C18	120.38 (18)
C4—C3—H3	120.5	F8—C17—C16	120.16 (18)
C2—C3—H3	120.5	C18—C17—C16	119.44 (16)
C3—C4—C5	121.5 (2)	F9—C18—C17	119.61 (17)
C3—C4—H4	119.2	F9—C18—C19	120.54 (18)
C5—C4—H4	119.2	C17—C18—C19	119.85 (17)
N1—C5—C4	118.9 (2)	F10—C19—C14	121.24 (16)
N1—C5—C6	120.1 (2)	F10—C19—C18	115.15 (16)
C4—C5—C6	121.0 (2)	C14—C19—C18	123.61 (17)
C7—C6—C5	122.6 (3)	C25—C20—C21	113.59 (18)
C7—C6—H6	118.7	C25—C20—B1	127.43 (18)
C5—C6—H6	118.7	C21—C20—B1	118.83 (18)
C6—C7—H7A	120.0	F11—C21—C22	116.2 (2)
C6—C7—H7B	120.0	F11—C21—C20	119.50 (17)
H7A—C7—H7B	120.0	C22—C21—C20	124.3 (2)
C9—C8—C13	113.76 (17)	F12—C22—C23	120.6 (2)
C9—C8—B1	127.32 (17)	F12—C22—C21	120.2 (3)
C13—C8—B1	118.49 (16)	C23—C22—C21	119.2 (2)
F1—C9—C10	115.29 (16)	F13—C23—C24	120.7 (3)
F1—C9—C8	120.73 (17)	F13—C23—C22	120.1 (3)
C10—C9—C8	123.98 (18)	C24—C23—C22	119.3 (2)
F2—C10—C11	119.78 (17)	F14—C24—C23	120.7 (2)
F2—C10—C9	120.75 (18)	F14—C24—C25	119.5 (3)
C11—C10—C9	119.46 (17)	C23—C24—C25	119.9 (2)
F3—C11—C10	120.35 (18)	F15—C25—C20	121.54 (18)
F3—C11—C12	120.40 (19)	F15—C25—C24	114.7 (2)
C10—C11—C12	119.25 (18)	C20—C25—C24	123.7 (2)
F4—C12—C11	119.51 (19)	C1—N1—C5	118.33 (18)
F4—C12—C13	121.04 (19)	C1—N1—B1	119.01 (15)
C11—C12—C13	119.44 (19)	C5—N1—B1	122.47 (18)
F5—C13—C12	116.65 (18)	N1—B1—C8	112.56 (14)
F5—C13—C8	119.34 (17)	N1—B1—C20	102.23 (15)
C12—C13—C8	124.01 (18)	C8—B1—C20	115.78 (16)
C19—C14—C15	113.56 (16)	N1—B1—C14	110.38 (15)
C19—C14—B1	126.37 (16)	C8—B1—C14	102.13 (14)
C15—C14—B1	119.61 (15)	C20—B1—C14	114.08 (14)

Experimental details

Crystal data
Chemical formula	C₂₅H₇BF₁₅N·C₆H₁₄
M_r	703.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	12.4173 (2), 17.1269 (3), 13.9211 (2)
β (°)	100.889 (1)
V (Å³)	2907.29 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.35 × 0.33 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII DUO
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.695, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	55747, 6929, 5324
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.113, 1.04
No. of reflections	6929
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Leibniz-Institut für Katalyse e.V. an der Universität Rostock.

References

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