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In the title compound, C16H36N+·C24BF20-, the geometric parameters do not show any unusual values. The four n-butyl chains adopt an all-trans conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040134/at6058sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040134/at6058Isup2.hkl
Contains datablock I

CCDC reference: 296509

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.033
  • wR factor = 0.075
  • Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact F54 .. F66 .. 2.57 Ang.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.88 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.61 From the CIF: _reflns_number_total 3854 Count of symmetry unique reflns 3898 Completeness (_total/calc) 98.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL006_ALERT_1_A _publ_requested_journal is missing e.g. 'Acta Crystallographica Section C'
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Very strong cationic Lewis acids are only available in the presence of weakly coordinating counter-ions such as [B(C6F5)4]. These anions also play an important role in electrochemistry. The salt [nBu4N]+·[B(C6F5)4] possesses a low reactivity towards reducing and oxidizing agents. Moreover, conductance measurements show that the dissociation constant of [nBu4N]+·[B(C6F5)4] solutions in solvents with low polarity are greater than those of smaller traditional anions (LeSuer et al., 2004). Therefore, we are convinced that tetra-n-butylammonium tetrakis(pentafluorophenyl)borate, (I), is an ideal supporting electrolyte. According to a literature procedure (LeSuer et al., 2004), we have synthesized (I) and we report here the crystal structure.

Perspective views of the cation and anion of (I) are shown in Figs. 1 and 2, respectively. Bond lengths and angles can be regarded as normal (Cambridge Crystallographic Database; Version 1.6 plus three updates; Mogul Version 1.0; Allen, 2002). Compound (I) consists of discrete tetrakis(pentafluorophenyl)borate anions and tetra-nbutylammonium cations. The four n-butyl chains adopt an all-trans conformation.

Experimental top

Compound (I) was synthesized according to a literature procedure. Colourless crystals of the title compound suitable for X-ray diffraction were grown from a methanol solution at 253 K.

Refinement top

H atoms were located in a difference map, but refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(Cmethylene) or Uiso(H) = 1.5Ueq(Cmethyl)] using a riding model, with C—H = 0.98 and 0.99 Å for Cmethyl and Cmethylene, respectively. In the absence of anomalous scatterers Friedel pairs were merged.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Perspective view of the cation of the title compound (I), with the atom-numbering scheme; displacement ellipsoids are at the 50% probability level.
[Figure 2] Fig. 2. Perspective view of the anion of the title compound (I), with the atom-numbering scheme; displacement ellipsoids are at the 50% probability level.
Tetra-n-butylammonium tetrakis(pentafluorophenyl)borate top
Crystal data top
C16H36N+·C24BF20F(000) = 1872
Mr = 921.51Dx = 1.480 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 10062 reflections
a = 24.104 (2) Åθ = 3.6–25.6°
b = 12.8925 (12) ŵ = 0.15 mm1
c = 17.5363 (15) ÅT = 173 K
β = 130.629 (5)°Plate, colourless
V = 4135.9 (7) Å30.42 × 0.37 × 0.21 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
3371 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 25.6°, θmin = 3.6°
ω scansh = 2929
10176 measured reflectionsk = 1514
3854 independent reflectionsl = 2117
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0476P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3854 reflectionsΔρmax = 0.25 e Å3
560 parametersΔρmin = 0.19 e Å3
2 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (4)
Crystal data top
C16H36N+·C24BF20V = 4135.9 (7) Å3
Mr = 921.51Z = 4
Monoclinic, CcMo Kα radiation
a = 24.104 (2) ŵ = 0.15 mm1
b = 12.8925 (12) ÅT = 173 K
c = 17.5363 (15) Å0.42 × 0.37 × 0.21 mm
β = 130.629 (5)°
Data collection top
Stoe IPDS-II two-circle
diffractometer
3371 reflections with I > 2σ(I)
10176 measured reflectionsRint = 0.035
3854 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0332 restraints
wR(F2) = 0.075H-atom parameters constrained
S = 1.00Δρmax = 0.25 e Å3
3854 reflectionsΔρmin = 0.19 e Å3
560 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
N10.61054 (12)0.60402 (18)0.24676 (17)0.0256 (5)
C110.64394 (15)0.6044 (2)0.1969 (2)0.0310 (6)
H11A0.67330.54040.21730.037*
H11B0.60360.60080.12320.037*
C120.69200 (16)0.6962 (3)0.2193 (2)0.0361 (7)
H12A0.73200.70320.29280.043*
H12B0.66280.76080.19390.043*
C130.7240 (2)0.6789 (3)0.1681 (3)0.0481 (9)
H13A0.75250.61360.19350.058*
H13B0.68350.67100.09480.058*
C140.7728 (2)0.7668 (4)0.1864 (3)0.0617 (11)
H14A0.79170.75210.15210.093*
H14B0.81370.77380.25870.093*
H14C0.74460.83150.16020.093*
C210.56444 (14)0.7012 (2)0.2191 (2)0.0295 (6)
H21A0.59620.76280.24140.035*
H21B0.54690.70040.25680.035*
C220.49841 (16)0.7129 (3)0.1072 (2)0.0369 (7)
H22A0.46190.65870.08640.044*
H22B0.51400.70380.06760.044*
C230.46363 (17)0.8210 (3)0.0862 (3)0.0422 (8)
H23A0.44890.83040.12700.051*
H23B0.50010.87510.10620.051*
C240.3969 (2)0.8333 (4)0.0249 (3)0.0704 (13)
H24A0.37570.90240.03650.106*
H24B0.36050.78040.04440.106*
H24C0.41160.82500.06510.106*
C310.56402 (14)0.5057 (2)0.2091 (2)0.0304 (6)
H31A0.52390.51240.13570.036*
H31B0.59480.44650.22040.036*
C320.53067 (15)0.4794 (2)0.2558 (2)0.0338 (7)
H32A0.50420.54040.25240.041*
H32B0.56970.46070.32730.041*
C330.47727 (17)0.3875 (3)0.1987 (3)0.0430 (8)
H33A0.43720.40820.12810.052*
H33B0.50350.32860.19840.052*
C340.44466 (19)0.3520 (3)0.2450 (3)0.0514 (9)
H34A0.41140.29370.20610.077*
H34B0.41760.40950.24410.077*
H34C0.48400.33000.31450.077*
C410.67008 (14)0.6039 (2)0.3612 (2)0.0289 (6)
H41A0.64610.60310.39040.035*
H41B0.69770.66970.38200.035*
C420.72461 (15)0.5140 (2)0.4067 (2)0.0352 (7)
H42A0.69810.44730.38660.042*
H42B0.75100.51550.38110.042*
C430.77918 (19)0.5229 (3)0.5212 (3)0.0533 (10)
H43A0.80340.59150.54050.064*
H43B0.75250.51860.54630.064*
C440.8373 (2)0.4380 (4)0.5708 (3)0.0707 (13)
H44A0.87110.44700.64390.106*
H44B0.86440.44260.54700.106*
H44C0.81370.37000.55340.106*
B10.66892 (15)0.8245 (2)0.6377 (2)0.0267 (7)
C510.69289 (14)0.8611 (2)0.7464 (2)0.0307 (6)
C520.67714 (15)0.8076 (2)0.7994 (2)0.0318 (7)
C530.70806 (16)0.8299 (3)0.8975 (2)0.0395 (8)
C540.75644 (17)0.9112 (3)0.9473 (2)0.0450 (9)
C550.77308 (16)0.9691 (3)0.8986 (3)0.0456 (9)
C560.74230 (15)0.9430 (2)0.8013 (2)0.0355 (7)
F520.63068 (9)0.72564 (14)0.75808 (13)0.0382 (4)
F530.69128 (11)0.77175 (18)0.94440 (15)0.0530 (5)
F540.78745 (12)0.9329 (2)1.04277 (16)0.0678 (7)
F550.81979 (12)1.05024 (18)0.94517 (18)0.0671 (7)
F560.76299 (9)0.99921 (15)0.75826 (15)0.0470 (5)
C610.74742 (13)0.7703 (2)0.6779 (2)0.0265 (6)
C620.77319 (14)0.6790 (2)0.7340 (2)0.0290 (6)
C630.83933 (16)0.6326 (2)0.7764 (2)0.0360 (7)
C640.88533 (15)0.6792 (3)0.7655 (3)0.0389 (8)
C650.86395 (16)0.7705 (3)0.7136 (3)0.0393 (8)
C660.79684 (15)0.8148 (2)0.6713 (2)0.0340 (7)
F620.73175 (9)0.62986 (13)0.75040 (13)0.0367 (4)
F630.85944 (11)0.54327 (16)0.82907 (17)0.0560 (6)
F640.95076 (10)0.63638 (18)0.80680 (17)0.0598 (6)
F650.90943 (10)0.81897 (19)0.70413 (19)0.0612 (6)
F660.78207 (10)0.90545 (15)0.62323 (17)0.0523 (5)
C710.59821 (14)0.7430 (2)0.5742 (2)0.0295 (6)
C720.53329 (15)0.7732 (3)0.5523 (2)0.0354 (7)
C730.47022 (15)0.7150 (3)0.4972 (2)0.0419 (8)
C740.46859 (16)0.6204 (3)0.4592 (2)0.0486 (10)
C750.53079 (17)0.5859 (3)0.4778 (2)0.0404 (8)
C760.59300 (15)0.6479 (2)0.5325 (2)0.0303 (6)
F720.53057 (9)0.86540 (16)0.58706 (15)0.0465 (5)
F730.40965 (9)0.7483 (2)0.48013 (16)0.0627 (7)
F740.40851 (11)0.5594 (2)0.40697 (16)0.0744 (8)
F750.53156 (12)0.49197 (17)0.44367 (16)0.0597 (6)
F760.65056 (9)0.60800 (13)0.54421 (14)0.0388 (4)
C810.63873 (14)0.9184 (2)0.5543 (2)0.0278 (6)
C820.61177 (14)1.0149 (2)0.5527 (2)0.0320 (7)
C830.58003 (15)1.0861 (2)0.4744 (3)0.0379 (8)
C840.57319 (16)1.0626 (2)0.3925 (2)0.0378 (8)
C850.59861 (16)0.9677 (3)0.3893 (2)0.0350 (7)
C860.62890 (14)0.8988 (2)0.4680 (2)0.0307 (6)
F820.61493 (9)1.04563 (15)0.62939 (14)0.0421 (5)
F830.55578 (11)1.17893 (15)0.47944 (16)0.0543 (6)
F840.54181 (11)1.13036 (16)0.31562 (15)0.0533 (5)
F850.59221 (11)0.94263 (16)0.30900 (14)0.0493 (5)
F860.65015 (10)0.80543 (13)0.45761 (14)0.0395 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0257 (10)0.0280 (12)0.0245 (12)0.0030 (9)0.0169 (10)0.0012 (9)
C110.0320 (13)0.0377 (16)0.0297 (15)0.0049 (12)0.0230 (12)0.0015 (13)
C120.0378 (15)0.0408 (18)0.0337 (16)0.0017 (13)0.0251 (14)0.0001 (14)
C130.0519 (19)0.053 (2)0.057 (2)0.0025 (16)0.0433 (18)0.0000 (18)
C140.060 (2)0.082 (3)0.057 (2)0.018 (2)0.044 (2)0.004 (2)
C210.0291 (13)0.0300 (15)0.0291 (15)0.0057 (11)0.0189 (12)0.0007 (12)
C220.0331 (14)0.0422 (18)0.0290 (16)0.0087 (13)0.0173 (13)0.0045 (13)
C230.0367 (15)0.045 (2)0.0399 (18)0.0108 (14)0.0230 (15)0.0114 (15)
C240.059 (2)0.080 (3)0.046 (2)0.032 (2)0.023 (2)0.022 (2)
C310.0300 (13)0.0265 (15)0.0316 (15)0.0005 (11)0.0187 (12)0.0039 (12)
C320.0305 (13)0.0348 (17)0.0358 (16)0.0008 (12)0.0215 (13)0.0014 (13)
C330.0339 (15)0.047 (2)0.0465 (19)0.0048 (13)0.0253 (14)0.0084 (16)
C340.0435 (17)0.050 (2)0.064 (2)0.0177 (16)0.0368 (18)0.0121 (19)
C410.0262 (13)0.0343 (16)0.0226 (13)0.0002 (11)0.0143 (11)0.0023 (12)
C420.0299 (13)0.0355 (16)0.0323 (16)0.0037 (12)0.0167 (12)0.0014 (13)
C430.0413 (17)0.069 (3)0.0348 (18)0.0152 (17)0.0181 (15)0.0096 (17)
C440.049 (2)0.071 (3)0.055 (3)0.016 (2)0.0180 (19)0.019 (2)
B10.0219 (13)0.0237 (16)0.0325 (17)0.0010 (11)0.0168 (13)0.0010 (13)
C510.0252 (12)0.0284 (15)0.0334 (15)0.0027 (11)0.0168 (12)0.0020 (13)
C520.0300 (13)0.0314 (16)0.0323 (16)0.0042 (12)0.0196 (13)0.0025 (13)
C530.0378 (16)0.0423 (19)0.0366 (17)0.0125 (13)0.0234 (15)0.0006 (14)
C540.0442 (17)0.051 (2)0.0335 (17)0.0105 (15)0.0225 (15)0.0113 (16)
C550.0319 (15)0.0325 (17)0.050 (2)0.0003 (12)0.0169 (15)0.0172 (15)
C560.0297 (13)0.0274 (16)0.0416 (18)0.0017 (12)0.0198 (13)0.0001 (14)
F520.0409 (9)0.0414 (10)0.0371 (9)0.0065 (8)0.0276 (8)0.0020 (8)
F530.0601 (11)0.0694 (15)0.0405 (11)0.0124 (10)0.0377 (10)0.0064 (10)
F540.0681 (13)0.0817 (17)0.0405 (12)0.0040 (12)0.0295 (11)0.0237 (11)
F550.0563 (12)0.0520 (13)0.0639 (15)0.0142 (10)0.0262 (11)0.0311 (11)
F560.0350 (9)0.0360 (10)0.0538 (12)0.0068 (8)0.0217 (8)0.0011 (9)
C610.0231 (12)0.0229 (13)0.0289 (14)0.0024 (10)0.0149 (11)0.0017 (11)
C620.0267 (12)0.0309 (15)0.0283 (15)0.0036 (11)0.0175 (12)0.0010 (12)
C630.0351 (14)0.0303 (16)0.0296 (15)0.0056 (13)0.0153 (13)0.0021 (13)
C640.0243 (13)0.0443 (19)0.0391 (17)0.0092 (13)0.0166 (13)0.0057 (15)
C650.0279 (14)0.0448 (19)0.0479 (19)0.0072 (13)0.0259 (14)0.0073 (16)
C660.0288 (13)0.0313 (16)0.0428 (17)0.0005 (12)0.0237 (13)0.0035 (14)
F620.0403 (9)0.0310 (9)0.0413 (10)0.0016 (7)0.0276 (8)0.0071 (8)
F630.0524 (11)0.0414 (11)0.0569 (12)0.0214 (9)0.0279 (10)0.0220 (10)
F640.0298 (9)0.0715 (15)0.0656 (14)0.0190 (9)0.0255 (9)0.0037 (11)
F650.0399 (10)0.0694 (15)0.0888 (17)0.0036 (10)0.0483 (12)0.0058 (12)
F660.0408 (10)0.0423 (11)0.0792 (14)0.0023 (8)0.0415 (10)0.0228 (11)
C710.0263 (13)0.0369 (16)0.0229 (13)0.0053 (12)0.0150 (11)0.0025 (12)
C720.0283 (13)0.0485 (19)0.0282 (15)0.0022 (13)0.0179 (12)0.0087 (14)
C730.0223 (13)0.066 (2)0.0303 (16)0.0000 (14)0.0142 (12)0.0163 (16)
C740.0268 (15)0.077 (3)0.0238 (16)0.0220 (16)0.0084 (13)0.0050 (17)
C750.0489 (18)0.0433 (19)0.0227 (15)0.0170 (14)0.0205 (14)0.0050 (14)
C760.0312 (13)0.0357 (17)0.0237 (14)0.0064 (12)0.0179 (12)0.0004 (12)
F720.0340 (9)0.0542 (13)0.0543 (12)0.0081 (8)0.0300 (9)0.0046 (10)
F730.0238 (8)0.1052 (19)0.0526 (12)0.0020 (10)0.0220 (8)0.0192 (12)
F740.0425 (11)0.105 (2)0.0475 (13)0.0463 (12)0.0167 (10)0.0137 (13)
F750.0745 (14)0.0550 (13)0.0430 (11)0.0352 (11)0.0353 (11)0.0229 (10)
F760.0446 (9)0.0337 (9)0.0428 (10)0.0068 (8)0.0305 (8)0.0097 (8)
C810.0219 (12)0.0265 (15)0.0323 (15)0.0004 (10)0.0164 (11)0.0004 (12)
C820.0282 (13)0.0310 (16)0.0330 (15)0.0015 (12)0.0182 (12)0.0010 (13)
C830.0309 (14)0.0267 (16)0.0443 (18)0.0035 (12)0.0192 (14)0.0023 (13)
C840.0301 (13)0.0331 (16)0.0350 (17)0.0002 (12)0.0145 (13)0.0098 (14)
C850.0321 (14)0.0369 (18)0.0305 (15)0.0049 (12)0.0179 (12)0.0005 (13)
C860.0295 (13)0.0254 (15)0.0337 (15)0.0009 (11)0.0190 (12)0.0001 (12)
F820.0450 (10)0.0368 (10)0.0447 (10)0.0112 (8)0.0293 (9)0.0003 (8)
F830.0603 (12)0.0352 (11)0.0572 (13)0.0208 (9)0.0337 (10)0.0102 (9)
F840.0525 (11)0.0430 (11)0.0440 (11)0.0101 (9)0.0225 (9)0.0180 (9)
F850.0624 (11)0.0476 (12)0.0373 (10)0.0012 (9)0.0321 (9)0.0044 (9)
F860.0536 (10)0.0292 (9)0.0442 (10)0.0040 (8)0.0356 (9)0.0006 (8)
Geometric parameters (Å, º) top
N1—C111.527 (4)C44—H44B0.9800
N1—C311.528 (4)C44—H44C0.9800
N1—C411.529 (3)B1—C811.657 (4)
N1—C211.529 (3)B1—C511.660 (5)
C11—C121.518 (4)B1—C711.666 (4)
C11—H11A0.9900B1—C611.681 (4)
C11—H11B0.9900C51—C521.394 (5)
C12—C131.535 (5)C51—C561.403 (4)
C12—H12A0.9900C52—F521.356 (4)
C12—H12B0.9900C52—C531.389 (5)
C13—C141.509 (5)C53—F531.354 (4)
C13—H13A0.9900C53—C541.377 (5)
C13—H13B0.9900C54—F541.345 (4)
C14—H14A0.9800C54—C551.376 (6)
C14—H14B0.9800C55—F551.354 (4)
C14—H14C0.9800C55—C561.388 (5)
C21—C221.529 (4)C56—F561.354 (4)
C21—H21A0.9900C61—C621.393 (4)
C21—H21B0.9900C61—C661.393 (4)
C22—C231.542 (5)C62—F621.363 (3)
C22—H22A0.9900C62—C631.382 (4)
C22—H22B0.9900C63—F631.352 (4)
C23—C241.526 (5)C63—C641.380 (5)
C23—H23A0.9900C64—F641.352 (3)
C23—H23B0.9900C64—C651.368 (5)
C24—H24A0.9800C65—F651.362 (4)
C24—H24B0.9800C65—C661.389 (4)
C24—H24C0.9800C66—F661.347 (4)
C31—C321.512 (4)C71—C761.390 (4)
C31—H31A0.9900C71—C721.402 (4)
C31—H31B0.9900C72—F721.358 (4)
C32—C331.544 (4)C72—C731.376 (4)
C32—H32A0.9900C73—F731.355 (4)
C32—H32B0.9900C73—C741.378 (6)
C33—C341.522 (5)C74—F741.352 (4)
C33—H33A0.9900C74—C751.383 (5)
C33—H33B0.9900C75—F751.357 (4)
C34—H34A0.9800C75—C761.391 (4)
C34—H34B0.9800C76—F761.365 (4)
C34—H34C0.9800C81—C861.394 (5)
C41—C421.530 (4)C81—C821.396 (4)
C41—H41A0.9900C82—F821.356 (4)
C41—H41B0.9900C82—C831.394 (5)
C42—C431.528 (5)C83—F831.359 (4)
C42—H42A0.9900C83—C841.370 (5)
C42—H42B0.9900C84—F841.351 (4)
C43—C441.526 (5)C84—C851.386 (5)
C43—H43A0.9900C85—F851.352 (4)
C43—H43B0.9900C85—C861.383 (4)
C44—H44A0.9800C86—F861.366 (3)
C11—N1—C31105.5 (2)C44—C43—C42112.4 (3)
C11—N1—C41111.0 (2)C44—C43—H43A109.1
C31—N1—C41111.3 (2)C42—C43—H43A109.1
C11—N1—C21111.2 (2)C44—C43—H43B109.1
C31—N1—C21111.4 (2)C42—C43—H43B109.1
C41—N1—C21106.5 (2)H43A—C43—H43B107.9
C12—C11—N1116.9 (2)C43—C44—H44A109.5
C12—C11—H11A108.1C43—C44—H44B109.5
N1—C11—H11A108.1H44A—C44—H44B109.5
C12—C11—H11B108.1C43—C44—H44C109.5
N1—C11—H11B108.1H44A—C44—H44C109.5
H11A—C11—H11B107.3H44B—C44—H44C109.5
C11—C12—C13108.9 (3)C81—B1—C51115.4 (2)
C11—C12—H12A109.9C81—B1—C71101.6 (2)
C13—C12—H12A109.9C51—B1—C71112.7 (2)
C11—C12—H12B109.9C81—B1—C61113.7 (2)
C13—C12—H12B109.9C51—B1—C61100.4 (2)
H12A—C12—H12B108.3C71—B1—C61113.6 (2)
C14—C13—C12112.7 (3)C52—C51—C56113.1 (3)
C14—C13—H13A109.1C52—C51—B1125.7 (3)
C12—C13—H13A109.1C56—C51—B1120.5 (3)
C14—C13—H13B109.1F52—C52—C53114.4 (3)
C12—C13—H13B109.1F52—C52—C51121.2 (3)
H13A—C13—H13B107.8C53—C52—C51124.4 (3)
C13—C14—H14A109.5F53—C53—C54120.0 (3)
C13—C14—H14B109.5F53—C53—C52120.5 (3)
H14A—C14—H14B109.5C54—C53—C52119.5 (3)
C13—C14—H14C109.5F54—C54—C55120.6 (3)
H14A—C14—H14C109.5F54—C54—C53120.2 (4)
H14B—C14—H14C109.5C55—C54—C53119.2 (3)
N1—C21—C22115.0 (2)F55—C55—C54120.5 (3)
N1—C21—H21A108.5F55—C55—C56119.9 (4)
C22—C21—H21A108.5C54—C55—C56119.6 (3)
N1—C21—H21B108.5F56—C56—C55117.4 (3)
C22—C21—H21B108.5F56—C56—C51118.5 (3)
H21A—C21—H21B107.5C55—C56—C51124.1 (3)
C21—C22—C23110.2 (3)C62—C61—C66113.2 (2)
C21—C22—H22A109.6C62—C61—B1120.7 (2)
C23—C22—H22A109.6C66—C61—B1125.7 (3)
C21—C22—H22B109.6F62—C62—C63115.6 (3)
C23—C22—H22B109.6F62—C62—C61119.4 (2)
H22A—C22—H22B108.1C63—C62—C61125.1 (3)
C24—C23—C22110.9 (3)F63—C63—C64120.1 (3)
C24—C23—H23A109.5F63—C63—C62120.8 (3)
C22—C23—H23A109.5C64—C63—C62119.1 (3)
C24—C23—H23B109.5F64—C64—C65120.7 (3)
C22—C23—H23B109.5F64—C64—C63120.7 (3)
H23A—C23—H23B108.1C65—C64—C63118.6 (3)
C23—C24—H24A109.5F65—C65—C64119.5 (3)
C23—C24—H24B109.5F65—C65—C66119.8 (3)
H24A—C24—H24B109.5C64—C65—C66120.8 (3)
C23—C24—H24C109.5F66—C66—C65115.6 (3)
H24A—C24—H24C109.5F66—C66—C61121.2 (2)
H24B—C24—H24C109.5C65—C66—C61123.2 (3)
C32—C31—N1116.9 (2)C76—C71—C72113.4 (3)
C32—C31—H31A108.1C76—C71—B1127.6 (2)
N1—C31—H31A108.1C72—C71—B1118.8 (3)
C32—C31—H31B108.1F72—C72—C73116.0 (3)
N1—C31—H31B108.1F72—C72—C71119.5 (3)
H31A—C31—H31B107.3C73—C72—C71124.6 (3)
C31—C32—C33109.6 (3)F73—C73—C72121.4 (4)
C31—C32—H32A109.8F73—C73—C74119.1 (3)
C33—C32—H32A109.8C72—C73—C74119.5 (3)
C31—C32—H32B109.8F74—C74—C73121.5 (3)
C33—C32—H32B109.8F74—C74—C75119.4 (4)
H32A—C32—H32B108.2C73—C74—C75119.0 (3)
C34—C33—C32112.8 (3)F75—C75—C74120.4 (3)
C34—C33—H33A109.0F75—C75—C76119.9 (3)
C32—C33—H33A109.0C74—C75—C76119.6 (3)
C34—C33—H33B109.0F76—C76—C71121.2 (2)
C32—C33—H33B109.0F76—C76—C75114.9 (3)
H33A—C33—H33B107.8C71—C76—C75123.9 (3)
C33—C34—H34A109.5C86—C81—C82113.0 (3)
C33—C34—H34B109.5C86—C81—B1119.5 (3)
H34A—C34—H34B109.5C82—C81—B1126.9 (3)
C33—C34—H34C109.5F82—C82—C83115.1 (3)
H34A—C34—H34C109.5F82—C82—C81121.0 (3)
H34B—C34—H34C109.5C83—C82—C81123.8 (3)
N1—C41—C42116.0 (2)F83—C83—C84120.0 (3)
N1—C41—H41A108.3F83—C83—C82120.0 (3)
C42—C41—H41A108.3C84—C83—C82120.1 (3)
N1—C41—H41B108.3F84—C84—C83120.7 (3)
C42—C41—H41B108.3F84—C84—C85120.4 (3)
H41A—C41—H41B107.4C83—C84—C85118.9 (3)
C43—C42—C41109.9 (3)F85—C85—C86120.9 (3)
C43—C42—H42A109.7F85—C85—C84119.9 (3)
C41—C42—H42A109.7C86—C85—C84119.1 (3)
C43—C42—H42B109.7F86—C86—C85115.6 (3)
C41—C42—H42B109.7F86—C86—C81119.4 (3)
H42A—C42—H42B108.2C85—C86—C81125.0 (3)
C31—N1—C11—C12178.5 (2)F64—C64—C65—C66179.8 (3)
C41—N1—C11—C1260.7 (3)C63—C64—C65—C661.0 (5)
C21—N1—C11—C1257.6 (3)F65—C65—C66—F660.3 (5)
N1—C11—C12—C13176.4 (3)C64—C65—C66—F66179.1 (3)
C11—C12—C13—C14180.0 (3)F65—C65—C66—C61179.8 (3)
C11—N1—C21—C2262.4 (3)C64—C65—C66—C610.4 (5)
C31—N1—C21—C2255.0 (3)C62—C61—C66—F66177.4 (3)
C41—N1—C21—C22176.6 (3)B1—C61—C66—F665.2 (5)
N1—C21—C22—C23170.9 (3)C62—C61—C66—C652.0 (4)
C21—C22—C23—C24179.1 (3)B1—C61—C66—C65174.3 (3)
C11—N1—C31—C32173.5 (2)C81—B1—C71—C76106.6 (3)
C41—N1—C31—C3253.0 (3)C51—B1—C71—C76129.3 (3)
C21—N1—C31—C3265.7 (3)C61—B1—C71—C7615.9 (4)
N1—C31—C32—C33172.1 (2)C81—B1—C71—C7268.7 (3)
C31—C32—C33—C34176.6 (3)C51—B1—C71—C7255.4 (3)
C11—N1—C41—C4257.6 (3)C61—B1—C71—C72168.8 (3)
C31—N1—C41—C4259.6 (3)C76—C71—C72—F72178.9 (3)
C21—N1—C41—C42178.7 (2)B1—C71—C72—F723.1 (4)
N1—C41—C42—C43178.5 (3)C76—C71—C72—C731.5 (4)
C41—C42—C43—C44177.3 (3)B1—C71—C72—C73177.4 (3)
C81—B1—C51—C52138.0 (3)F72—C72—C73—F730.6 (4)
C71—B1—C51—C5221.9 (4)C71—C72—C73—F73179.0 (3)
C61—B1—C51—C5299.4 (3)F72—C72—C73—C74179.9 (3)
C81—B1—C51—C5652.5 (3)C71—C72—C73—C740.5 (5)
C71—B1—C51—C56168.6 (2)F73—C73—C74—F741.3 (5)
C61—B1—C51—C5670.2 (3)C72—C73—C74—F74178.2 (3)
C56—C51—C52—F52179.6 (2)F73—C73—C74—C75179.1 (3)
B1—C51—C52—F529.4 (4)C72—C73—C74—C750.3 (5)
C56—C51—C52—C531.7 (4)F74—C74—C75—F750.4 (5)
B1—C51—C52—C53168.5 (3)C73—C74—C75—F75178.3 (3)
F52—C52—C53—F530.1 (4)F74—C74—C75—C76179.2 (3)
C51—C52—C53—F53177.9 (3)C73—C74—C75—C761.3 (5)
F52—C52—C53—C54179.7 (3)C72—C71—C76—F76178.3 (3)
C51—C52—C53—C541.6 (4)B1—C71—C76—F762.8 (4)
F53—C53—C54—F540.3 (4)C72—C71—C76—C752.5 (4)
C52—C53—C54—F54179.2 (3)B1—C71—C76—C75178.0 (3)
F53—C53—C54—C55179.7 (3)F75—C75—C76—F762.2 (4)
C52—C53—C54—C550.1 (4)C74—C75—C76—F76178.2 (3)
F54—C54—C55—F551.4 (5)F75—C75—C76—C71177.0 (3)
C53—C54—C55—F55179.2 (3)C74—C75—C76—C712.5 (5)
F54—C54—C55—C56177.8 (3)C51—B1—C81—C86169.4 (2)
C53—C54—C55—C561.5 (5)C71—B1—C81—C8668.4 (3)
F55—C55—C56—F562.3 (4)C61—B1—C81—C8654.1 (3)
C54—C55—C56—F56177.0 (3)C51—B1—C81—C8219.9 (4)
F55—C55—C56—C51179.4 (3)C71—B1—C81—C82102.4 (3)
C54—C55—C56—C511.4 (5)C61—B1—C81—C82135.2 (3)
C52—C51—C56—F56178.6 (2)C86—C81—C82—F82178.2 (2)
B1—C51—C56—F567.8 (4)B1—C81—C82—F827.0 (4)
C52—C51—C56—C550.2 (4)C86—C81—C82—C831.7 (4)
B1—C51—C56—C55170.5 (3)B1—C81—C82—C83172.9 (3)
C81—B1—C61—C62168.6 (2)F82—C82—C83—F830.7 (4)
C51—B1—C61—C6267.5 (3)C81—C82—C83—F83179.4 (2)
C71—B1—C61—C6253.1 (4)F82—C82—C83—C84179.2 (3)
C81—B1—C61—C6619.7 (4)C81—C82—C83—C840.7 (4)
C51—B1—C61—C66104.2 (3)F83—C83—C84—F840.7 (4)
C71—B1—C61—C66135.2 (3)C82—C83—C84—F84179.2 (3)
C66—C61—C62—F62177.0 (3)F83—C83—C84—C85179.7 (3)
B1—C61—C62—F624.4 (4)C82—C83—C84—C850.4 (4)
C66—C61—C62—C632.5 (4)F84—C84—C85—F850.2 (4)
B1—C61—C62—C63175.2 (3)C83—C84—C85—F85179.8 (3)
F62—C62—C63—F631.0 (4)F84—C84—C85—C86178.5 (3)
C61—C62—C63—F63179.5 (3)C83—C84—C85—C861.1 (4)
F62—C62—C63—C64178.2 (3)F85—C85—C86—F861.0 (4)
C61—C62—C63—C641.3 (5)C84—C85—C86—F86177.6 (2)
F63—C63—C64—F640.2 (5)F85—C85—C86—C81179.0 (3)
C62—C63—C64—F64179.4 (3)C84—C85—C86—C812.4 (4)
F63—C63—C64—C65178.7 (3)C82—C81—C86—F86177.5 (2)
C62—C63—C64—C650.6 (5)B1—C81—C86—F865.5 (4)
F64—C64—C65—F650.5 (5)C82—C81—C86—C852.6 (4)
C63—C64—C65—F65178.4 (3)B1—C81—C86—C85174.5 (2)

Experimental details

Crystal data
Chemical formulaC16H36N+·C24BF20
Mr921.51
Crystal system, space groupMonoclinic, Cc
Temperature (K)173
a, b, c (Å)24.104 (2), 12.8925 (12), 17.5363 (15)
β (°) 130.629 (5)
V3)4135.9 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.15
Crystal size (mm)0.42 × 0.37 × 0.21
Data collection
DiffractometerStoe IPDS-II two-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10176, 3854, 3371
Rint0.035
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.075, 1.00
No. of reflections3854
No. of parameters560
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.19

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).

Selected bond lengths (Å) top
N1—C111.527 (4)B1—C811.657 (4)
N1—C311.528 (4)B1—C511.660 (5)
N1—C411.529 (3)B1—C711.666 (4)
N1—C211.529 (3)B1—C611.681 (4)
 

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