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In the title compound, [(CH3)2(C7H7)NH][(C6F5)3B(OH)] or C9H14N+·C18HBF15O, the distorted tetrahedral borate anions are strongly hydrogen bonded to the substituted ammonium cations. The N...O separation in the N—H...O hydrogen bond is 2.728 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101003328/da1161sup1.cif
Contains datablocks I, boram

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101003328/da1161Isup2.hkl
Contains datablock I

CCDC reference: 164686

Comment top

A review of the history of pentafluorophenylboranes, which have been known for over 35 years, shows that these compounds were given little attention until approximately 10 years ago (Piers & Chivers, 1997). Since the discovery of these compounds as highly effective activators for polymerization catalysts, a great deal of both academic and industrial research has been devoted to the understanding and improvement of these compounds (Turner & Hlatky, 1988; Hlatky et al., 1989; Turner, 1997). The first reports of Lewis-acid activation of polymerization catalysts with tris(perfluorophenyl)borate also accelerated the research on these compounds (Ewen & Elder, 1995; Yang et al., 1991). Recently, the nature of the ion pair found in these compounds has also become an active research topic. Such ion pairs are being examined by both experimental and theoretical techniques (Lanza et al., 2000). The exact nature of the ion-pair separation has taken on added importance. Until now, many of these interactions have not been suitably characterized in order to compare results obtained experimentally with those obtained theoretically. Ammonium hydroxyborates have also been investigated as activators (Siedle et al., 1993). Specifically, the reaction of [Et3NH][(C6F5)3BOH] with Cp2ZrMe2 (Cp is cyclopentadienyl) did produce an active polymerization catalyst for 1-hexene. Ultimately, the catalyst decomposed to generate the [(C6F5)3BO-] anion coordinated to a metal center through the O and one of the F atoms.

No unusual bond distances or angles are observed in the perfluorophenyl moieties of the title compound, (I). The F—C bonds vary from 1.339 (3) to 1.360 (3) Å, the C—C bonds vary from 1.366 (4) to 1.393 (3) Å, and the B—C bonds vary from 1.651 (3) to 1.663 (3) Å. Similar bond lengths can be found in compounds containing the (C6F5)3B moiety (Danopoulos et al., 1998; Janiak et al., 1998).

Two compounds that are most comparable to the title compound are [Et3NH][(C6H5)3BOH] and [Et3NH][(C6F5)3BOH]. Unfortunately both reports are inadequate. A B—O bond length of 1.487 (3) Å is reported for [Et3NH][(C6H5)3BOH] (Siedle et al., 1993). Others have taken this report to refer to the fluorinated compound [Et3NH][(C6F5)3BOH] (Hill et al., 1997). Regardless, to the authors knowledge, a full crystal structure report has never been published or deposited. A structure for [Et3NH][(C6F5)3BOH] has been reported recently (Duchateau et al., 2000). Unfortunately, this structure was refined with an incorrect formula. While giving the correct formula in the text, the O—H H atom is ignored by the authors in the refinement. No discussion of this discrepancy is offered either in the text or in the Crystallographic Information File. While this error will have little contribution to the overall refinement, it does affect the structural area of interest. The exact nature of the hydrogen bonding between the ion pairs is not revealed. The O—N distance in the reported compound is 2.734 (6) Å, comparable to the distance of 2.728 (3) Å in (I). The B—O—N angle of 134.6 (3)° in the above compound is also comparable to the value of 123.48 (3)° in (I). The O—N bond distances are the same within one s.u., while the B—O—N angle is compressed for (I). This compression most likely arises from cofacial accommodation of the C2 phenyl ring of the borate anion with the C4 phenyl ring of the ammonium cation.

Two structures have been reported with transition metal interactions with the [(C6F5)3BOH] anion. A [Ta(Cp*)2(OH)(CH3)][(C6F5)3BOH] complex (where Cp* is pentamethylcyclopentadienyl) has a B—O distance of 1.490 (10) Å (Schaefer et al., 1993). Neither the H atom of the anion nor the H atom of the OH group of the cation could be located in difference Fourier maps, but a likely hydrogen-bonding scheme is proposed. A platinum complex is reported in which the anion forms a Pt—O bond. In this complex, the B—O distance is 1.526 (3) Å (Hill et al., 1997). The H atom of the anion was located in a difference Fourier map, with some imprecision, and is found to be hydrogen bonded to two F atoms on two of the phenyl rings.

Related literature top

For related literature, see: Danopoulos et al. (1998); Duchateau et al. (2000); Ewen & Elder (1995); Hill et al. (1997); Hlatky et al. (1989); Janiak et al. (1998); Lanza et al. (2000); Piers & Chivers (1997); Schaefer et al. (1993); Siedle et al. (1993); Turner (1997); Turner & Hlatky (1988); Yang et al. (1991).

Experimental top

Compound (I) was obtained as a decomposition product of a metallocene reacted with tris(pentafluorophenyl)borate in tetrahydrofuran followed by vapor diffusion of pentane at 276 K.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: local programs; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97-2 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXL97-2 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsiods.
(I) top
Crystal data top
C9H14N+·C18HBF15OF(000) = 1328
Mr = 665.21Dx = 1.716 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
a = 10.552 (5) ÅCell parameters from 25 reflections
b = 15.287 (2) Åθ = 28.2–42.4°
c = 16.072 (9) ŵ = 1.62 mm1
β = 96.60 (5)°T = 153 K
V = 2575.4 (19) Å3Spike, yellow–brown
Z = 40.20 × 0.07 × 0.05 mm
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.022
Radiation source: fine-focus sealed tubeθmax = 69.9°, θmin = 4.0°
Graphite monochromatorh = 1211
ω scansk = 018
5131 measured reflectionsl = 019
4762 independent reflections3 standard reflections every 300 reflections
3592 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.06P)2 + 1.1P]
where P = (Fo2 + 2Fc2)/3
4762 reflections(Δ/σ)max < 0.001
466 parametersΔρmax = 0.33 e Å3
672 restraintsΔρmin = 0.33 e Å3
Crystal data top
C9H14N+·C18HBF15OV = 2575.4 (19) Å3
Mr = 665.21Z = 4
Monoclinic, P21/cCu Kα radiation
a = 10.552 (5) ŵ = 1.62 mm1
b = 15.287 (2) ÅT = 153 K
c = 16.072 (9) Å0.20 × 0.07 × 0.05 mm
β = 96.60 (5)°
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.022
5131 measured reflections3 standard reflections every 300 reflections
4762 independent reflections intensity decay: 2%
3592 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.044672 restraints
wR(F2) = 0.118All H-atom parameters refined
S = 1.05Δρmax = 0.33 e Å3
4762 reflectionsΔρmin = 0.33 e Å3
466 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
xyzUiso*/Ueq
B10.7676 (2)0.26146 (16)0.09911 (16)0.0265 (5)
O10.76857 (15)0.22469 (10)0.18455 (10)0.0301 (4)
F260.97760 (12)0.35969 (8)0.18269 (8)0.0322 (3)
F220.88751 (13)0.13419 (9)0.01857 (10)0.0415 (4)
F120.74213 (13)0.30101 (9)0.07745 (8)0.0383 (3)
F360.53468 (13)0.32063 (9)0.15356 (9)0.0403 (3)
F320.88763 (12)0.42776 (8)0.02673 (9)0.0362 (3)
F251.22435 (13)0.34473 (9)0.16631 (10)0.0414 (3)
F160.56626 (13)0.11987 (10)0.11923 (10)0.0454 (4)
F150.39692 (13)0.06029 (9)0.00273 (12)0.0517 (4)
F231.13288 (14)0.12262 (10)0.03435 (10)0.0446 (4)
F330.78381 (16)0.58460 (9)0.01824 (10)0.0512 (4)
F241.30571 (12)0.22867 (10)0.05604 (10)0.0448 (4)
F350.43315 (14)0.48080 (11)0.14527 (11)0.0523 (4)
F140.38830 (16)0.12457 (12)0.16146 (12)0.0630 (5)
F340.55443 (16)0.61444 (10)0.07570 (11)0.0552 (4)
F130.56033 (16)0.24919 (14)0.19560 (10)0.0601 (5)
N10.90065 (18)0.07797 (12)0.23794 (13)0.0312 (4)
H1O0.701 (3)0.234 (2)0.207 (2)0.060 (10)*
H1N0.864 (3)0.1337 (19)0.2264 (17)0.042 (7)*
H820.923 (3)0.099 (2)0.369 (2)0.065 (10)*
H930.844 (3)0.0323 (18)0.1217 (18)0.039 (8)*
H730.967 (3)0.2366 (19)0.3006 (18)0.049 (8)*
H910.851 (3)0.044 (2)0.193 (2)0.061 (9)*
H461.033 (3)0.0372 (19)0.1538 (18)0.050 (8)*
H810.905 (3)0.006 (2)0.3369 (19)0.060 (9)*
H721.115 (4)0.272 (3)0.316 (2)0.082 (12)*
H920.730 (4)0.031 (2)0.182 (2)0.080 (11)*
H451.261 (3)0.031 (2)0.145 (2)0.068 (10)*
H711.057 (3)0.201 (2)0.382 (2)0.071 (10)*
H431.283 (3)0.196 (2)0.291 (2)0.071 (11)*
H830.776 (4)0.060 (3)0.320 (3)0.108 (15)*
H441.390 (4)0.084 (3)0.209 (2)0.088 (12)*
C110.6657 (2)0.21298 (14)0.02712 (15)0.0273 (5)
C120.6571 (2)0.24089 (15)0.05540 (15)0.0322 (5)
C130.5663 (2)0.21406 (17)0.11859 (16)0.0391 (6)
C140.4787 (2)0.15166 (17)0.10106 (18)0.0421 (6)
C150.4837 (2)0.12036 (15)0.02113 (19)0.0388 (6)
C160.5739 (2)0.15170 (14)0.04091 (16)0.0323 (5)
C210.9176 (2)0.25014 (14)0.08097 (14)0.0263 (4)
C220.9657 (2)0.19036 (14)0.02823 (14)0.0291 (5)
C231.0940 (2)0.18212 (15)0.01922 (15)0.0317 (5)
C241.1813 (2)0.23486 (15)0.06453 (15)0.0316 (5)
C251.1402 (2)0.29399 (15)0.11932 (15)0.0313 (5)
C261.0114 (2)0.30007 (14)0.12694 (14)0.0271 (5)
C310.7193 (2)0.36509 (14)0.09423 (14)0.0268 (5)
C320.7746 (2)0.43608 (15)0.05899 (14)0.0301 (5)
C330.7219 (2)0.51897 (15)0.05266 (15)0.0359 (5)
C340.6069 (2)0.53422 (15)0.08132 (16)0.0387 (6)
C350.5462 (2)0.46636 (17)0.11652 (16)0.0368 (5)
C360.6024 (2)0.38507 (15)0.12119 (14)0.0301 (5)
C411.0402 (2)0.07940 (15)0.23077 (15)0.0322 (5)
C421.1129 (2)0.14711 (17)0.26974 (16)0.0396 (6)
C431.2439 (3)0.1455 (2)0.2595 (2)0.0537 (8)
C441.2967 (3)0.0814 (2)0.2151 (2)0.0591 (8)
C451.2227 (3)0.0154 (2)0.1782 (2)0.0577 (8)
C461.0931 (3)0.01400 (19)0.18599 (17)0.0437 (6)
C471.0602 (3)0.2187 (2)0.3202 (2)0.0517 (7)
C480.8748 (3)0.05480 (18)0.32566 (19)0.0434 (6)
C490.8254 (3)0.01846 (18)0.1770 (2)0.0456 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0227 (11)0.0245 (11)0.0332 (12)0.0006 (9)0.0076 (10)0.0009 (10)
O10.0250 (8)0.0297 (8)0.0373 (9)0.0046 (6)0.0110 (7)0.0069 (7)
F260.0275 (7)0.0304 (7)0.0390 (7)0.0009 (5)0.0049 (5)0.0078 (6)
F220.0291 (7)0.0384 (8)0.0567 (9)0.0007 (6)0.0041 (6)0.0199 (7)
F120.0336 (7)0.0463 (8)0.0360 (7)0.0126 (6)0.0084 (6)0.0007 (6)
F360.0280 (7)0.0439 (8)0.0514 (9)0.0054 (6)0.0141 (6)0.0092 (7)
F320.0331 (7)0.0319 (7)0.0450 (8)0.0038 (6)0.0111 (6)0.0059 (6)
F250.0254 (7)0.0384 (8)0.0593 (9)0.0056 (6)0.0002 (6)0.0082 (7)
F160.0268 (7)0.0438 (8)0.0663 (10)0.0041 (6)0.0079 (7)0.0218 (7)
F150.0223 (7)0.0303 (7)0.1028 (13)0.0069 (6)0.0087 (7)0.0017 (8)
F230.0354 (8)0.0465 (8)0.0540 (9)0.0104 (6)0.0143 (7)0.0148 (7)
F330.0635 (11)0.0282 (7)0.0604 (10)0.0057 (7)0.0006 (8)0.0114 (7)
F240.0205 (7)0.0490 (9)0.0669 (10)0.0045 (6)0.0135 (6)0.0025 (7)
F350.0362 (8)0.0567 (10)0.0651 (10)0.0230 (7)0.0102 (7)0.0038 (8)
F140.0391 (9)0.0744 (12)0.0728 (12)0.0167 (8)0.0046 (8)0.0299 (10)
F340.0622 (11)0.0306 (8)0.0686 (11)0.0219 (7)0.0106 (8)0.0049 (7)
F130.0475 (9)0.0975 (14)0.0349 (8)0.0124 (9)0.0034 (7)0.0097 (9)
N10.0267 (10)0.0242 (9)0.0437 (11)0.0024 (8)0.0083 (8)0.0014 (8)
C110.0186 (10)0.0233 (10)0.0411 (12)0.0016 (8)0.0073 (9)0.0009 (9)
C120.0221 (11)0.0307 (11)0.0446 (13)0.0042 (9)0.0075 (9)0.0064 (10)
C130.0307 (13)0.0471 (14)0.0400 (13)0.0001 (10)0.0062 (10)0.0133 (11)
C140.0238 (12)0.0431 (14)0.0585 (16)0.0036 (10)0.0009 (11)0.0217 (12)
C150.0192 (11)0.0260 (11)0.0718 (17)0.0014 (8)0.0081 (11)0.0067 (11)
C160.0206 (11)0.0247 (11)0.0527 (14)0.0035 (8)0.0085 (10)0.0027 (10)
C210.0228 (10)0.0235 (10)0.0334 (11)0.0004 (8)0.0056 (9)0.0021 (9)
C220.0254 (11)0.0277 (11)0.0345 (12)0.0002 (9)0.0049 (9)0.0019 (9)
C230.0303 (12)0.0292 (11)0.0374 (12)0.0066 (9)0.0108 (10)0.0022 (9)
C240.0208 (11)0.0306 (11)0.0446 (13)0.0042 (9)0.0085 (9)0.0070 (10)
C250.0246 (11)0.0285 (11)0.0404 (13)0.0023 (9)0.0026 (9)0.0012 (9)
C260.0265 (11)0.0230 (10)0.0328 (11)0.0009 (8)0.0069 (9)0.0002 (9)
C310.0248 (11)0.0270 (10)0.0283 (11)0.0015 (8)0.0020 (9)0.0008 (8)
C320.0294 (12)0.0291 (11)0.0319 (12)0.0005 (9)0.0032 (9)0.0001 (9)
C330.0448 (14)0.0249 (11)0.0365 (12)0.0012 (10)0.0017 (10)0.0038 (10)
C340.0433 (14)0.0277 (11)0.0422 (14)0.0139 (10)0.0078 (11)0.0061 (10)
C350.0320 (13)0.0407 (13)0.0369 (13)0.0122 (10)0.0010 (10)0.0055 (10)
C360.0263 (11)0.0321 (11)0.0320 (11)0.0044 (9)0.0033 (9)0.0004 (9)
C410.0283 (12)0.0321 (11)0.0366 (12)0.0043 (9)0.0062 (9)0.0064 (10)
C420.0382 (14)0.0395 (13)0.0392 (13)0.0056 (10)0.0030 (10)0.0112 (11)
C430.0386 (15)0.0603 (18)0.0586 (17)0.0114 (13)0.0096 (13)0.0269 (15)
C440.0322 (15)0.080 (2)0.0667 (19)0.0115 (14)0.0125 (13)0.0341 (17)
C450.0424 (16)0.074 (2)0.0601 (18)0.0206 (15)0.0197 (14)0.0172 (16)
C460.0385 (14)0.0484 (15)0.0457 (15)0.0130 (12)0.0121 (11)0.0030 (12)
C470.066 (2)0.0386 (14)0.0469 (17)0.0083 (14)0.0086 (14)0.0005 (12)
C480.0477 (16)0.0321 (13)0.0549 (16)0.0073 (12)0.0254 (13)0.0081 (12)
C490.0383 (16)0.0303 (13)0.067 (2)0.0033 (11)0.0004 (13)0.0085 (13)
Geometric parameters (Å, º) top
B1—O11.483 (3)C23—C241.369 (3)
B1—C211.651 (3)C24—C251.367 (3)
B1—C111.661 (3)C25—C261.382 (3)
B1—C311.663 (3)C31—C321.384 (3)
F26—C261.354 (2)C31—C361.387 (3)
F22—C221.357 (3)C32—C331.383 (3)
F12—C121.360 (3)C33—C341.366 (4)
F36—C361.355 (3)C34—C351.375 (4)
F32—C321.360 (3)C35—C361.375 (3)
F25—C251.344 (3)C41—C461.386 (4)
F16—C161.360 (3)C41—C421.393 (3)
F15—C151.353 (3)C42—C431.412 (4)
F23—C231.349 (3)C42—C471.505 (4)
F33—C331.350 (3)C43—C441.368 (5)
F24—C241.339 (3)C44—C451.368 (5)
F35—C351.346 (3)C45—C461.387 (4)
F14—C141.346 (3)O1—H1O0.85 (4)
F34—C341.344 (3)N1—H1N0.92 (3)
F13—C131.344 (3)C43—H430.96 (4)
N1—C411.490 (3)C44—H441.01 (4)
N1—C491.497 (3)C45—H451.00 (4)
N1—C481.509 (3)C46—H461.12 (3)
C11—C161.384 (3)C47—H47C1.04 (3)
C11—C121.386 (3)C47—H47B0.99 (4)
C12—C131.376 (3)C47—H47A1.05 (4)
C13—C141.379 (4)C48—H48A1.02 (4)
C14—C151.366 (4)C48—H48B0.99 (3)
C15—C161.382 (4)C48—H48C1.05 (5)
C21—C221.382 (3)C49—H49A0.94 (3)
C21—C261.393 (3)C49—H49B1.05 (3)
C22—C231.384 (3)C49—H49C1.00 (4)
O1—B1—C21102.67 (18)F33—C33—C34120.1 (2)
O1—B1—C11114.25 (18)F33—C33—C32120.1 (2)
C21—B1—C11112.80 (18)C34—C33—C32119.8 (2)
O1—B1—C31111.96 (18)F34—C34—C33120.5 (2)
C21—B1—C31112.75 (18)F34—C34—C35120.5 (2)
C11—B1—C31102.80 (18)C33—C34—C35118.9 (2)
C41—N1—C49114.4 (2)F35—C35—C34119.4 (2)
C41—N1—C48111.2 (2)F35—C35—C36121.5 (2)
C49—N1—C48109.2 (2)C34—C35—C36119.1 (2)
C16—C11—C12113.1 (2)F36—C36—C35115.8 (2)
C16—C11—B1126.9 (2)F36—C36—C31119.1 (2)
C12—C11—B1119.67 (19)C35—C36—C31125.1 (2)
F12—C12—C13115.7 (2)C46—C41—C42122.4 (2)
F12—C12—C11119.0 (2)C46—C41—N1119.4 (2)
C13—C12—C11125.3 (2)C42—C41—N1118.3 (2)
F13—C13—C12121.0 (2)C41—C42—C43115.5 (3)
F13—C13—C14120.2 (2)C41—C42—C47124.3 (3)
C12—C13—C14118.8 (3)C43—C42—C47120.2 (3)
F14—C14—C15121.2 (2)C44—C43—C42122.4 (3)
F14—C14—C13120.1 (3)C43—C44—C45120.5 (3)
C15—C14—C13118.7 (2)C44—C45—C46119.5 (3)
F15—C15—C14119.3 (2)C41—C46—C45119.7 (3)
F15—C15—C16120.3 (2)C41—N1—H1N110.7 (19)
C14—C15—C16120.4 (2)C49—N1—H1N104.6 (19)
F16—C16—C15115.8 (2)C48—N1—H1N106.1 (19)
F16—C16—C11120.5 (2)C44—C43—H43132 (2)
C15—C16—C11123.8 (2)C42—C43—H43106 (2)
C22—C21—C26113.54 (19)C43—C44—H44118 (2)
C22—C21—B1127.2 (2)C45—C44—H44121 (2)
C26—C21—B1119.08 (19)C44—C45—H45120 (2)
F22—C22—C21121.08 (19)C46—C45—H45121 (2)
F22—C22—C23115.1 (2)C45—C46—H46119.0 (16)
C21—C22—C23123.8 (2)C41—C46—H46121.3 (16)
F23—C23—C24120.1 (2)C42—C47—H47C115.1 (16)
F23—C23—C22120.1 (2)C42—C47—H47B107 (2)
C24—C23—C22119.8 (2)H47C—C47—H47B107 (3)
F24—C24—C25120.0 (2)C42—C47—H47A112 (2)
F24—C24—C23120.8 (2)H47C—C47—H47A102 (3)
C25—C24—C23119.2 (2)H47B—C47—H47A113 (3)
F25—C25—C24120.4 (2)N1—C48—H48A111 (2)
F25—C25—C26120.3 (2)N1—C48—H48B106.2 (18)
C24—C25—C26119.3 (2)H48A—C48—H48B112 (3)
F26—C26—C25116.1 (2)N1—C48—H48C100 (2)
F26—C26—C21119.64 (19)H48A—C48—H48C113 (3)
C25—C26—C21124.2 (2)H48B—C48—H48C113 (3)
C32—C31—C36112.8 (2)N1—C49—H49A108.3 (18)
C32—C31—B1128.7 (2)N1—C49—H49B106.3 (18)
C36—C31—B1118.29 (19)H49A—C49—H49B111 (3)
F32—C32—C33114.9 (2)N1—C49—H49C107 (2)
F32—C32—C31120.8 (2)H49A—C49—H49C111 (3)
C33—C32—C31124.3 (2)H49B—C49—H49C113 (3)
O1—B1—C11—C168.7 (3)C24—C25—C26—F26179.7 (2)
C21—B1—C11—C16125.5 (2)F25—C25—C26—C21179.9 (2)
C31—B1—C11—C16112.8 (2)C24—C25—C26—C211.0 (4)
O1—B1—C11—C12179.26 (19)C22—C21—C26—F26178.31 (19)
C21—B1—C11—C1262.5 (3)B1—C21—C26—F263.0 (3)
C31—B1—C11—C1259.2 (2)C22—C21—C26—C252.4 (3)
C16—C11—C12—F12179.80 (19)B1—C21—C26—C25177.6 (2)
B1—C11—C12—F127.1 (3)O1—B1—C31—C32132.0 (2)
C16—C11—C12—C131.7 (3)C21—B1—C31—C3216.8 (3)
B1—C11—C12—C13171.4 (2)C11—B1—C31—C32104.9 (3)
F12—C12—C13—F133.1 (3)O1—B1—C31—C3654.7 (3)
C11—C12—C13—F13175.5 (2)C21—B1—C31—C36169.92 (19)
F12—C12—C13—C14178.5 (2)C11—B1—C31—C3668.3 (2)
C11—C12—C13—C142.9 (4)C36—C31—C32—F32177.9 (2)
F13—C13—C14—F141.2 (4)B1—C31—C32—F324.3 (4)
C12—C13—C14—F14179.6 (2)C36—C31—C32—C331.5 (3)
F13—C13—C14—C15176.9 (2)B1—C31—C32—C33175.1 (2)
C12—C13—C14—C151.5 (4)F32—C32—C33—F331.5 (3)
F14—C14—C15—F150.8 (4)C31—C32—C33—F33179.1 (2)
C13—C14—C15—F15178.8 (2)F32—C32—C33—C34178.5 (2)
F14—C14—C15—C16177.2 (2)C31—C32—C33—C340.9 (4)
C13—C14—C15—C160.8 (4)F33—C33—C34—F340.1 (4)
F15—C15—C16—F161.5 (3)C32—C33—C34—F34179.9 (2)
C14—C15—C16—F16176.5 (2)F33—C33—C34—C35179.6 (2)
F15—C15—C16—C11179.9 (2)C32—C33—C34—C350.4 (4)
C14—C15—C16—C112.1 (4)F34—C34—C35—F350.2 (4)
C12—C11—C16—F16177.68 (19)C33—C34—C35—F35179.7 (2)
B1—C11—C16—F165.2 (3)F34—C34—C35—C36179.9 (2)
C12—C11—C16—C150.8 (3)C33—C34—C35—C360.6 (4)
B1—C11—C16—C15173.3 (2)F35—C35—C36—F362.3 (3)
O1—B1—C21—C22106.5 (2)C34—C35—C36—F36177.5 (2)
C11—B1—C21—C2216.9 (3)F35—C35—C36—C31179.0 (2)
C31—B1—C21—C22132.8 (2)C34—C35—C36—C311.3 (4)
O1—B1—C21—C2668.0 (2)C32—C31—C36—F36177.0 (2)
C11—B1—C21—C26168.51 (19)B1—C31—C36—F362.7 (3)
C31—B1—C21—C2652.6 (3)C32—C31—C36—C351.7 (3)
C26—C21—C22—F22177.4 (2)B1—C31—C36—C35176.0 (2)
B1—C21—C22—F222.6 (4)C49—N1—C41—C4615.3 (3)
C26—C21—C22—C232.0 (3)C48—N1—C41—C46109.1 (3)
B1—C21—C22—C23176.9 (2)C49—N1—C41—C42164.7 (2)
F22—C22—C23—F231.2 (3)C48—N1—C41—C4270.9 (3)
C21—C22—C23—F23179.3 (2)C46—C41—C42—C430.9 (4)
F22—C22—C23—C24179.1 (2)N1—C41—C42—C43179.1 (2)
C21—C22—C23—C240.4 (4)C46—C41—C42—C47178.9 (3)
F23—C23—C24—F240.4 (4)N1—C41—C42—C471.1 (4)
C22—C23—C24—F24179.2 (2)C41—C42—C43—C440.6 (4)
F23—C23—C24—C25179.2 (2)C47—C42—C43—C44179.3 (3)
C22—C23—C24—C251.2 (4)C42—C43—C44—C450.1 (5)
F24—C24—C25—F251.5 (3)C43—C44—C45—C460.1 (5)
C23—C24—C25—F25178.1 (2)C42—C41—C46—C450.8 (4)
F24—C24—C25—C26179.5 (2)N1—C41—C46—C45179.2 (2)
C23—C24—C25—C260.9 (3)C44—C45—C46—C410.2 (4)
F25—C25—C26—F260.7 (3)

Experimental details

Crystal data
Chemical formulaC9H14N+·C18HBF15O
Mr665.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)10.552 (5), 15.287 (2), 16.072 (9)
β (°) 96.60 (5)
V3)2575.4 (19)
Z4
Radiation typeCu Kα
µ (mm1)1.62
Crystal size (mm)0.20 × 0.07 × 0.05
Data collection
DiffractometerNonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5131, 4762, 3592
Rint0.022
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.118, 1.05
No. of reflections4762
No. of parameters466
No. of restraints672
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.33, 0.33

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, local programs, SHELXS97 (Sheldrick, 1990), SHELXL97-2 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997).

Selected geometric parameters (Å, º) top
B1—O11.483 (3)N1—C411.490 (3)
B1—C211.651 (3)N1—C491.497 (3)
B1—C111.661 (3)N1—C481.509 (3)
B1—C311.663 (3)
O1—B1—C21102.67 (18)C11—B1—C31102.80 (18)
O1—B1—C11114.25 (18)C41—N1—C49114.4 (2)
C21—B1—C11112.80 (18)C41—N1—C48111.2 (2)
O1—B1—C31111.96 (18)C49—N1—C48109.2 (2)
C21—B1—C31112.75 (18)
 

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