2-Vinyl-pyridine-tris-(penta-fluoro-phen-yl)borane hexane monosolvate.

The title compound, C(7)H(7)N·B(C(6)F(5))(3)·C(6)H(14), was obtained by the stoichiometric reaction of 2-vinyl-pyridine and tris-(penta-fluoro-phen-yl)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 (19)F NMR spectra. The B-N distance is equivalent to the distances found for 2-methyl-pyridine and 2-ethyl-pyridine B(C(6)F(5))(3) adducts. For the final refinement, the contributions of disordered solvent mol-ecules 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 = 730.30

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 1.04

6929 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013153/vm2164sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H7BF15N·C6H14	F(000) = 1416
Mr = 703.30	Dx = 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

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

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(Fo2) + (0.0312P)2 + 2.2216P] where P = (Fo2 + 2Fc2)/3
6929 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)