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Of the two independent ferrocenyl­tri­fluoro­borate anions in the asymmetric unit of the title compound, (C16H36N)[Fe(C5H5)(C5H4BF3)], one has the BF3 group nearly eclipsed and the other has the BF3 group staggered, with respect to the plane of a cyclo­penta­dienyl ring. The compound is the first structure determination of a ferrocenyltri­fluoro­borate anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010261/cf6088sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010261/cf6088Isup2.hkl
Contains datablock I

CCDC reference: 170749

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.123
  • Data-to-parameter ratio = 21.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

In an attempt to synthesize organodifluoroboranes by treating the corresponding boronic acids with hydrofluoric acid (Kinder & Katzenellenbogen, 1985), it was discovered that the organodifluoroborane species would readily pick up a third fluoride anion to form the organotrifluoroborate species (confirmed by 11B NMR). It was hypothesized that the species formed was the hydronium organotrifluoroborate salt; however, all attempts to isolate these compounds were unsuccessful, and they were observable only in solution via 11B and 19F NMR. Treatment of the intermediate with the base tetra-n-butylammonium hydroxide effected a counter-ion exchange to produce the organotrifluoroborate species with an organic counter-ion. These new compounds were found to have the same reactivity as their potassium organotrifluoroborate counterparts with the added bonus of increased solubility in organic media.

The title compound, (I), was synthesized to demonstrate the versatility of the counter-ion exchange reaction, and its tolerance for a variety of functional groups. The base used in the reaction can also be varied. Other examples generated in our group include sodium, potassium, caesium, and tetra-n-butylphosphonium counter-ions (Batey & Quach, 2001).

In space group P1 with Z = 4, the asymmetric unit must contain two molecules. In the asymmetric unit of (I), there are two ionic pairs (A and B in Fig.1), each pair consists of a ferrocenyltrifluoroborate anion and a tetrabutylammonium cation and the anions have different conformations. In anion A, the BF3 group is almost eclipsed to the bonded cyclopentadienyl ring [defined by the torsion angle C2A—C1A—B1A—F2A of -5.5 (4)°] and in anion B, the BF3 group is staggered with respect to the bonded cyclopendadienyl ring [defined by the torsion angle C2B—C1B—B1B—F1B of 90.5 (3)°]. See Table 1 for other torsion angles relating to the BF3 geometry.

A search of the April 2001 release of the Cambridge Structural Database (Allen & Kennard, 1993) revealed that this is the first structure determination of a ferrocenetrifluoroborate anion.

Experimental top

Compound (I) was synthesized by treatment of ferroceneboronic acid (0.52 g, 4.27 mmol), dissolved in a minimum amount of methanol (ca 1 ml), with a 5.0 M solution of hydrofluoric acid (2.65 ml, 13.25 mmol), added dropwise with vigorous stirring over a period of 1 min at room temperature. The reaction mixture was then cooled to 273 K, and a 1.54 M solution of tetra-n-butylammonium hydroxide (2.76 ml, 4.27 mmol) was added dropwise over a period of 5 min. The reaction mixture was then warmed to room temperature and stirred for another hour. Dichloromethane (10 ml) was added to dilute the biphasic reaction mixture, the layers were separated, and the aqueous layer was further extracted with dichloromethane (3 × 10 ml). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to afford the dark green crystalline solid (I). Subsequent recrystallization in ethyl acetate and hexanes yielded the desired crystals.

Refinement top

H atoms were included in calculated positions with C—H distances ranging from 0.98 to 1.00 Å.

Computing details top

Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of (I) showing the atom-labelling scheme. Ellipsoids are at the 50% probability level.
Tetra-n-butylammonium Ferrocenyltrifluoroborate top
Crystal data top
(C16H36N)[Fe(C5H5)(C5H4BF3)]Z = 4
Mr = 495.29F(000) = 1064
Triclinic, P1Dx = 1.231 Mg m3
a = 9.9310 (2) ÅMo Kα radiation, λ = 0.71070 Å
b = 15.5450 (4) ÅCell parameters from 33767 reflections
c = 17.9230 (5) Åθ = 2.6–27.5°
α = 87.4990 (14)°µ = 0.60 mm1
β = 87.9350 (17)°T = 150 K
γ = 75.3340 (16)°Needle, orange
V = 2673.31 (11) Å30.25 × 0.15 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer
12237 independent reflections
Radiation source: fine-focus sealed tube8213 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.041
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.6°
ϕ scans, and ω scans with κ offsetsh = 1212
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
k = 1920
Tmin = 0.865, Tmax = 0.916l = 2323
50155 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1936P]
where P = (Fo2 + 2Fc2)/3
12237 reflections(Δ/σ)max = 0.002
578 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
(C16H36N)[Fe(C5H5)(C5H4BF3)]γ = 75.3340 (16)°
Mr = 495.29V = 2673.31 (11) Å3
Triclinic, P1Z = 4
a = 9.9310 (2) ÅMo Kα radiation
b = 15.5450 (4) ŵ = 0.60 mm1
c = 17.9230 (5) ÅT = 150 K
α = 87.4990 (14)°0.25 × 0.15 × 0.15 mm
β = 87.9350 (17)°
Data collection top
Nonius KappaCCD
diffractometer
12237 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
8213 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.916Rint = 0.041
50155 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.02Δρmax = 0.37 e Å3
12237 reflectionsΔρmin = 0.45 e Å3
578 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
Fe1A0.35925 (4)0.31266 (2)0.524013 (18)0.03047 (11)
F1A0.37221 (18)0.36812 (10)0.27882 (8)0.0525 (4)
F2A0.25554 (15)0.26711 (10)0.32243 (9)0.0473 (4)
F3A0.48736 (15)0.24349 (10)0.34416 (8)0.0459 (4)
C1A0.3216 (3)0.36268 (15)0.41567 (13)0.0319 (5)
C2A0.1957 (3)0.37610 (16)0.45995 (13)0.0355 (6)
H2AA0.11460.35190.44910.043*
C3A0.2043 (3)0.42739 (17)0.52237 (15)0.0454 (7)
H3AA0.13040.44630.56200.054*
C4A0.3358 (4)0.44699 (18)0.51841 (16)0.0529 (8)
H4AA0.37200.48240.55450.063*
C5A0.4072 (3)0.40725 (17)0.45299 (16)0.0447 (7)
H5AA0.50360.40930.43640.054*
C6A0.4452 (3)0.18056 (17)0.51254 (15)0.0411 (6)
H6AA0.45810.14860.46460.049*
C7A0.3261 (3)0.19398 (17)0.56061 (15)0.0402 (6)
H7AA0.24070.17300.55260.048*
C8A0.3489 (3)0.24250 (18)0.62218 (14)0.0426 (7)
H8AA0.28240.26200.66500.051*
C9A0.4823 (3)0.2590 (2)0.61173 (15)0.0479 (7)
H9AA0.52640.29250.64590.058*
C10A0.5422 (3)0.22073 (19)0.54347 (16)0.0458 (7)
H10A0.63570.22200.52150.055*
B1A0.3601 (3)0.30939 (19)0.33970 (16)0.0329 (6)
N1A0.53793 (18)0.00946 (12)0.25034 (10)0.0253 (4)
C11A0.4056 (2)0.05637 (15)0.29234 (13)0.0288 (5)
H11A0.41510.11550.30610.035*
H11B0.32690.06640.25790.035*
C12A0.3686 (2)0.00812 (16)0.36266 (13)0.0319 (6)
H12A0.44290.00130.39950.038*
H12B0.36110.05200.35040.038*
C13A0.2303 (2)0.06112 (17)0.39601 (14)0.0364 (6)
H13A0.23850.12120.40780.044*
H13B0.15680.06820.35860.044*
C14A0.1877 (3)0.0156 (2)0.46674 (16)0.0523 (8)
H14A0.09880.05150.48640.078*
H14B0.25940.00950.50420.078*
H14C0.17760.04340.45510.078*
C15A0.6609 (2)0.00342 (16)0.30032 (12)0.0280 (5)
H15A0.65360.03700.34370.034*
H15B0.65410.06310.31970.034*
C16A0.8042 (2)0.02959 (17)0.26256 (13)0.0317 (5)
H16A0.80230.07840.22920.038*
H16B0.82630.01950.23150.038*
C17A0.9166 (2)0.06267 (18)0.31923 (14)0.0371 (6)
H17A0.89570.11280.34940.044*
H17B0.91670.01430.35340.044*
C18A1.0599 (3)0.09330 (19)0.28221 (16)0.0460 (7)
H18A1.12960.11420.32060.069*
H18B1.08180.04350.25310.069*
H18C1.06070.14190.24900.069*
C19A0.5352 (2)0.08478 (15)0.23216 (13)0.0272 (5)
H19A0.62440.11320.20670.033*
H19B0.53000.11870.27980.033*
C20A0.4179 (2)0.09327 (16)0.18402 (14)0.0319 (5)
H20A0.42490.06310.13480.038*
H20B0.32750.06390.20800.038*
C21A0.4240 (3)0.19078 (16)0.17319 (14)0.0360 (6)
H21A0.52010.22210.15800.043*
H21B0.40150.21800.22150.043*
C22A0.3248 (3)0.20417 (19)0.11508 (16)0.0457 (7)
H22A0.33360.26800.11050.069*
H22B0.34770.17850.06680.069*
H22C0.22910.17470.13030.069*
C23A0.5511 (2)0.06192 (15)0.17790 (12)0.0276 (5)
H23A0.63120.02750.14830.033*
H23B0.46630.06700.14880.033*
C24A0.5704 (3)0.15474 (16)0.18647 (13)0.0332 (6)
H24A0.65960.15070.21110.040*
H24B0.49410.18920.21850.040*
C25A0.5707 (3)0.20223 (16)0.11038 (13)0.0327 (6)
H25A0.48100.20660.08620.039*
H25B0.64600.16700.07830.039*
C26A0.5920 (3)0.29547 (16)0.11726 (15)0.0413 (7)
H26A0.59160.32420.06750.062*
H26B0.68150.29120.14040.062*
H26C0.51660.33080.14830.062*
Fe1B0.13191 (3)0.13869 (2)0.029700 (17)0.02532 (10)
F1B0.18902 (18)0.23721 (10)0.20448 (8)0.0571 (5)
F2B0.18386 (18)0.31633 (10)0.10084 (9)0.0551 (4)
F3B0.01003 (15)0.27638 (10)0.13471 (9)0.0489 (4)
C1B0.1833 (2)0.15640 (15)0.08136 (12)0.0271 (5)
C2B0.3055 (2)0.12776 (16)0.03747 (13)0.0296 (5)
H2BA0.37730.16190.03230.036*
C3B0.3072 (2)0.04420 (16)0.00075 (13)0.0321 (6)
H3BA0.38030.00960.03360.039*
C4B0.1855 (2)0.01941 (15)0.02131 (13)0.0313 (5)
H4BA0.15770.03590.00440.038*
C5B0.1109 (2)0.08799 (15)0.07083 (12)0.0289 (5)
H5BA0.02010.08880.09370.035*
C6B0.0442 (3)0.26379 (17)0.06377 (15)0.0408 (7)
H6BA0.04760.32040.03600.049*
C7B0.1410 (3)0.21698 (18)0.11690 (15)0.0406 (7)
H7BA0.22560.23450.13270.049*
C8B0.0975 (3)0.14102 (18)0.14360 (13)0.0383 (6)
H8BA0.14600.09530.18120.046*
C9B0.0260 (3)0.14108 (18)0.10685 (14)0.0371 (6)
H9BA0.08010.09500.11400.045*
C10B0.0593 (2)0.21630 (18)0.05791 (14)0.0386 (6)
H10B0.14160.23330.02490.046*
B1B0.1348 (3)0.24756 (19)0.13000 (16)0.0340 (7)
N1B0.06031 (19)0.47897 (12)0.24076 (10)0.0258 (4)
C11B0.0680 (2)0.41285 (15)0.30510 (13)0.0296 (5)
H11C0.02330.39680.32960.036*
H11D0.13790.44350.34230.036*
C12B0.1041 (3)0.32785 (16)0.28615 (14)0.0361 (6)
H12C0.03520.29530.24930.043*
H12D0.19730.34170.26390.043*
C13B0.1033 (3)0.27022 (18)0.35788 (17)0.0474 (7)
H13C0.00750.25260.37700.057*
H13D0.16410.30610.39620.057*
C14B0.1521 (3)0.18788 (19)0.34643 (19)0.0556 (8)
H14D0.14940.15370.39380.083*
H14E0.09110.15140.30930.083*
H14F0.24770.20490.32860.083*
C15B0.0675 (2)0.43954 (15)0.19210 (13)0.0310 (5)
H15C0.15020.42490.22400.037*
H15D0.05700.38310.17250.037*
C16B0.0951 (2)0.49859 (17)0.12664 (14)0.0358 (6)
H16C0.09910.55710.14480.043*
H16D0.01820.50840.09110.043*
C17B0.2321 (3)0.45522 (18)0.08716 (15)0.0446 (7)
H17C0.22580.39820.06690.053*
H17D0.30760.44200.12370.053*
C18B0.2680 (3)0.5147 (2)0.02379 (17)0.0614 (9)
H18D0.35670.48470.00020.092*
H18E0.27600.57080.04380.092*
H18F0.19440.52700.01310.092*
C19B0.1900 (2)0.49754 (16)0.19364 (13)0.0296 (5)
H19C0.18330.54390.15500.036*
H19D0.18960.44270.16740.036*
C20B0.3284 (2)0.52744 (17)0.23502 (13)0.0359 (6)
H20C0.32990.58130.26290.043*
H20D0.34010.48010.27150.043*
C21B0.4472 (2)0.54786 (17)0.18113 (15)0.0376 (6)
H21C0.44190.49500.15120.045*
H21D0.43780.59740.14640.045*
C22B0.5887 (3)0.57321 (18)0.22166 (16)0.0440 (7)
H22D0.66270.58590.18500.066*
H22E0.59510.62620.25060.066*
H22F0.59920.52380.25540.066*
C23B0.0507 (2)0.56642 (15)0.27296 (13)0.0290 (5)
H23C0.05020.60980.23090.035*
H23D0.13610.58970.30360.035*
C24B0.0740 (2)0.56280 (16)0.32042 (14)0.0328 (6)
H24C0.16110.54060.29080.039*
H24D0.07400.52160.36410.039*
C25B0.0668 (3)0.65558 (18)0.34659 (16)0.0453 (7)
H25C0.07810.69430.30270.054*
H25D0.02650.68040.36940.054*
C26B0.1758 (3)0.6575 (2)0.40249 (18)0.0585 (8)
H26D0.16560.71890.41720.088*
H26E0.26860.63450.37990.088*
H26F0.16400.62050.44670.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe1A0.0380 (2)0.0303 (2)0.02439 (19)0.01055 (15)0.00209 (15)0.00209 (14)
F1A0.0791 (12)0.0441 (9)0.0283 (8)0.0075 (8)0.0123 (8)0.0035 (7)
F2A0.0481 (9)0.0458 (9)0.0479 (9)0.0092 (7)0.0029 (7)0.0146 (7)
F3A0.0408 (8)0.0514 (10)0.0356 (8)0.0082 (7)0.0005 (7)0.0114 (7)
C1A0.0405 (14)0.0253 (13)0.0282 (13)0.0061 (10)0.0020 (11)0.0005 (10)
C2A0.0408 (14)0.0303 (14)0.0299 (13)0.0001 (11)0.0008 (11)0.0051 (11)
C3A0.0677 (19)0.0320 (15)0.0293 (14)0.0001 (13)0.0064 (13)0.0042 (11)
C4A0.093 (2)0.0339 (16)0.0364 (16)0.0244 (16)0.0015 (16)0.0093 (12)
C5A0.0595 (18)0.0345 (15)0.0460 (16)0.0238 (13)0.0091 (14)0.0031 (12)
C6A0.0526 (16)0.0316 (14)0.0342 (14)0.0012 (12)0.0067 (12)0.0011 (11)
C7A0.0485 (16)0.0343 (15)0.0392 (15)0.0132 (12)0.0072 (12)0.0068 (12)
C8A0.0505 (16)0.0429 (16)0.0295 (14)0.0041 (13)0.0005 (12)0.0060 (12)
C9A0.0533 (17)0.0579 (19)0.0340 (15)0.0147 (14)0.0170 (13)0.0002 (13)
C10A0.0360 (14)0.0566 (19)0.0409 (16)0.0041 (13)0.0046 (12)0.0011 (13)
B1A0.0394 (15)0.0289 (15)0.0269 (14)0.0023 (12)0.0024 (12)0.0019 (12)
N1A0.0294 (10)0.0262 (10)0.0189 (9)0.0041 (8)0.0001 (8)0.0022 (8)
C11A0.0272 (12)0.0292 (13)0.0263 (12)0.0002 (9)0.0028 (10)0.0043 (10)
C12A0.0332 (13)0.0321 (13)0.0304 (13)0.0085 (10)0.0053 (11)0.0031 (10)
C13A0.0305 (13)0.0440 (15)0.0342 (14)0.0088 (11)0.0050 (11)0.0055 (12)
C14A0.0517 (17)0.061 (2)0.0459 (17)0.0191 (15)0.0228 (15)0.0068 (15)
C15A0.0320 (12)0.0326 (13)0.0204 (11)0.0094 (10)0.0023 (10)0.0024 (10)
C16A0.0289 (12)0.0408 (15)0.0257 (12)0.0089 (10)0.0011 (10)0.0036 (11)
C17A0.0332 (13)0.0443 (16)0.0334 (14)0.0092 (11)0.0018 (11)0.0010 (12)
C18A0.0318 (14)0.0534 (18)0.0522 (18)0.0100 (12)0.0010 (13)0.0001 (14)
C19A0.0294 (12)0.0241 (12)0.0268 (12)0.0039 (9)0.0008 (10)0.0034 (9)
C20A0.0330 (13)0.0289 (13)0.0335 (13)0.0069 (10)0.0052 (10)0.0002 (10)
C21A0.0438 (15)0.0317 (14)0.0350 (14)0.0130 (11)0.0078 (11)0.0009 (11)
C22A0.0572 (17)0.0421 (16)0.0433 (16)0.0211 (14)0.0116 (13)0.0025 (13)
C23A0.0325 (12)0.0283 (13)0.0214 (11)0.0065 (10)0.0009 (10)0.0012 (9)
C24A0.0453 (15)0.0306 (13)0.0251 (12)0.0122 (11)0.0027 (11)0.0026 (10)
C25A0.0327 (13)0.0363 (14)0.0279 (13)0.0076 (10)0.0014 (10)0.0032 (10)
C26A0.0429 (15)0.0304 (14)0.0465 (16)0.0041 (11)0.0095 (13)0.0045 (12)
Fe1B0.02638 (18)0.02622 (19)0.02237 (18)0.00445 (13)0.00212 (13)0.00529 (13)
F1B0.0739 (11)0.0427 (10)0.0359 (9)0.0153 (8)0.0175 (8)0.0121 (7)
F2B0.0742 (11)0.0344 (9)0.0603 (11)0.0205 (8)0.0092 (9)0.0077 (8)
F3B0.0380 (8)0.0402 (9)0.0592 (10)0.0048 (7)0.0009 (7)0.0120 (8)
C1B0.0296 (12)0.0268 (12)0.0233 (12)0.0042 (9)0.0031 (10)0.0047 (9)
C2B0.0263 (12)0.0353 (14)0.0266 (12)0.0066 (10)0.0043 (10)0.0047 (10)
C3B0.0325 (13)0.0341 (14)0.0235 (12)0.0030 (10)0.0014 (10)0.0017 (10)
C4B0.0434 (14)0.0253 (13)0.0237 (12)0.0062 (10)0.0056 (11)0.0038 (10)
C5B0.0332 (12)0.0310 (13)0.0212 (11)0.0051 (10)0.0015 (10)0.0079 (10)
C6B0.0474 (16)0.0290 (14)0.0426 (16)0.0032 (12)0.0102 (13)0.0105 (12)
C7B0.0340 (13)0.0508 (17)0.0385 (15)0.0103 (12)0.0041 (12)0.0248 (13)
C8B0.0423 (15)0.0449 (16)0.0216 (12)0.0011 (12)0.0019 (11)0.0085 (11)
C9B0.0352 (14)0.0478 (16)0.0308 (14)0.0145 (12)0.0087 (11)0.0102 (12)
C10B0.0271 (12)0.0520 (17)0.0316 (14)0.0008 (11)0.0050 (11)0.0145 (12)
B1B0.0383 (16)0.0307 (15)0.0305 (15)0.0050 (12)0.0065 (12)0.0012 (12)
N1B0.0314 (10)0.0227 (10)0.0226 (10)0.0049 (8)0.0001 (8)0.0029 (8)
C11B0.0347 (13)0.0269 (13)0.0263 (12)0.0061 (10)0.0022 (10)0.0019 (10)
C12B0.0392 (14)0.0287 (14)0.0412 (15)0.0097 (11)0.0008 (12)0.0018 (11)
C13B0.0541 (17)0.0350 (15)0.0551 (18)0.0149 (13)0.0140 (14)0.0072 (13)
C14B0.0571 (18)0.0425 (18)0.070 (2)0.0189 (14)0.0103 (16)0.0056 (16)
C15B0.0335 (13)0.0270 (13)0.0309 (13)0.0040 (10)0.0039 (10)0.0082 (10)
C16B0.0319 (13)0.0448 (16)0.0297 (13)0.0080 (11)0.0017 (11)0.0028 (11)
C17B0.0435 (15)0.0474 (17)0.0435 (16)0.0129 (13)0.0133 (13)0.0136 (13)
C18B0.0509 (18)0.091 (3)0.0433 (18)0.0215 (17)0.0140 (15)0.0017 (17)
C19B0.0321 (12)0.0299 (13)0.0266 (12)0.0066 (10)0.0048 (10)0.0022 (10)
C20B0.0367 (13)0.0390 (15)0.0300 (13)0.0058 (11)0.0011 (11)0.0036 (11)
C21B0.0350 (13)0.0373 (15)0.0412 (15)0.0095 (11)0.0018 (12)0.0058 (12)
C22B0.0368 (14)0.0411 (16)0.0554 (18)0.0118 (12)0.0024 (13)0.0032 (13)
C23B0.0395 (13)0.0210 (12)0.0252 (12)0.0048 (10)0.0011 (10)0.0043 (9)
C24B0.0330 (13)0.0325 (14)0.0336 (13)0.0090 (10)0.0025 (11)0.0072 (11)
C25B0.0601 (18)0.0351 (15)0.0454 (16)0.0190 (13)0.0093 (14)0.0045 (13)
C26B0.061 (2)0.058 (2)0.063 (2)0.0237 (16)0.0097 (16)0.0145 (16)
Geometric parameters (Å, º) top
Fe1A—C6A2.031 (3)Fe1B—C6B2.030 (2)
Fe1A—C7A2.032 (3)Fe1B—C10B2.035 (2)
Fe1A—C10A2.037 (3)Fe1B—C5B2.036 (2)
Fe1A—C2A2.038 (3)Fe1B—C7B2.041 (2)
Fe1A—C5A2.039 (3)Fe1B—C2B2.042 (2)
Fe1A—C3A2.039 (3)Fe1B—C4B2.042 (2)
Fe1A—C4A2.040 (3)Fe1B—C9B2.047 (2)
Fe1A—C9A2.042 (3)Fe1B—C3B2.047 (2)
Fe1A—C8A2.043 (3)Fe1B—C8B2.058 (2)
Fe1A—C1A2.071 (2)Fe1B—C1B2.061 (2)
F1A—B1A1.414 (3)F1B—B1B1.422 (3)
F2A—B1A1.411 (3)F2B—B1B1.409 (3)
F3A—B1A1.414 (3)F3B—B1B1.399 (3)
C1A—C5A1.425 (4)C1B—C5B1.430 (3)
C1A—C2A1.431 (3)C1B—C2B1.433 (3)
C1A—B1A1.608 (3)C1B—B1B1.605 (4)
C2A—C3A1.419 (4)C2B—C3B1.427 (3)
C2A—H2AA1.000C2B—H2BA1.000
C3A—C4A1.414 (4)C3B—C4B1.423 (3)
C3A—H3AA1.000C3B—H3BA1.000
C4A—C5A1.429 (4)C4B—C5B1.428 (3)
C4A—H4AA1.000C4B—H4BA1.000
C5A—H5AA1.000C5B—H5BA1.000
C6A—C10A1.413 (4)C6B—C10B1.418 (4)
C6A—C7A1.414 (4)C6B—C7B1.419 (4)
C6A—H6AA1.000C6B—H6BA1.000
C7A—C8A1.420 (4)C7B—C8B1.416 (4)
C7A—H7AA1.000C7B—H7BA1.000
C8A—C9A1.416 (4)C8B—C9B1.413 (4)
C8A—H8AA1.000C8B—H8BA1.000
C9A—C10A1.427 (4)C9B—C10B1.408 (4)
C9A—H9AA1.000C9B—H9BA1.000
C10A—H10A1.000C10B—H10B1.000
N1A—C15A1.522 (3)N1B—C15B1.523 (3)
N1A—C19A1.522 (3)N1B—C11B1.524 (3)
N1A—C23A1.522 (3)N1B—C19B1.525 (3)
N1A—C11A1.522 (3)N1B—C23B1.526 (3)
C11A—C12A1.520 (3)C11B—C12B1.509 (3)
C11A—H11A0.990C11B—H11C0.990
C11A—H11B0.990C11B—H11D0.990
C12A—C13A1.528 (3)C12B—C13B1.534 (4)
C12A—H12A0.990C12B—H12C0.990
C12A—H12B0.990C12B—H12D0.990
C13A—C14A1.523 (3)C13B—C14B1.504 (4)
C13A—H13A0.990C13B—H13C0.990
C13A—H13B0.990C13B—H13D0.990
C14A—H14A0.980C14B—H14D0.980
C14A—H14B0.980C14B—H14E0.980
C14A—H14C0.980C14B—H14F0.980
C15A—C16A1.529 (3)C15B—C16B1.518 (3)
C15A—H15A0.990C15B—H15C0.990
C15A—H15B0.990C15B—H15D0.990
C16A—C17A1.512 (3)C16B—C17B1.521 (3)
C16A—H16A0.990C16B—H16C0.990
C16A—H16B0.990C16B—H16D0.990
C17A—C18A1.520 (3)C17B—C18B1.523 (4)
C17A—H17A0.990C17B—H17C0.990
C17A—H17B0.990C17B—H17D0.990
C18A—H18A0.980C18B—H18D0.980
C18A—H18B0.980C18B—H18E0.980
C18A—H18C0.980C18B—H18F0.980
C19A—C20A1.510 (3)C19B—C20B1.512 (3)
C19A—H19A0.990C19B—H19C0.990
C19A—H19B0.990C19B—H19D0.990
C20A—C21A1.522 (3)C20B—C21B1.514 (3)
C20A—H20A0.990C20B—H20C0.990
C20A—H20B0.990C20B—H20D0.990
C21A—C22A1.515 (4)C21B—C22B1.526 (3)
C21A—H21A0.990C21B—H21C0.990
C21A—H21B0.990C21B—H21D0.990
C22A—H22A0.980C22B—H22D0.980
C22A—H22B0.980C22B—H22E0.980
C22A—H22C0.980C22B—H22F0.980
C23A—C24A1.518 (3)C23B—C24B1.516 (3)
C23A—H23A0.990C23B—H23C0.990
C23A—H23B0.990C23B—H23D0.990
C24A—C25A1.522 (3)C24B—C25B1.520 (3)
C24A—H24A0.990C24B—H24C0.990
C24A—H24B0.990C24B—H24D0.990
C25A—C26A1.528 (3)C25B—C26B1.508 (4)
C25A—H25A0.990C25B—H25C0.990
C25A—H25B0.990C25B—H25D0.990
C26A—H26A0.980C26B—H26D0.980
C26A—H26B0.980C26B—H26E0.980
C26A—H26C0.980C26B—H26F0.980
C7A—Fe1A—C10A68.63 (11)C6B—Fe1B—C5B127.24 (11)
C6A—Fe1A—C2A119.64 (11)C10B—Fe1B—C5B106.00 (10)
C7A—Fe1A—C2A107.81 (11)C10B—Fe1B—C7B68.33 (10)
C10A—Fe1A—C2A153.86 (11)C5B—Fe1B—C7B166.71 (11)
C6A—Fe1A—C5A122.47 (11)C6B—Fe1B—C2B114.40 (10)
C7A—Fe1A—C5A159.43 (11)C10B—Fe1B—C2B145.68 (10)
C10A—Fe1A—C5A106.09 (12)C5B—Fe1B—C2B67.97 (9)
C2A—Fe1A—C5A67.67 (11)C7B—Fe1B—C2B109.46 (10)
C6A—Fe1A—C3A156.11 (12)C6B—Fe1B—C4B167.24 (11)
C7A—Fe1A—C3A122.32 (12)C10B—Fe1B—C4B130.02 (10)
C10A—Fe1A—C3A162.83 (12)C7B—Fe1B—C4B151.55 (11)
C5A—Fe1A—C3A68.30 (11)C2B—Fe1B—C4B68.54 (9)
C6A—Fe1A—C4A160.47 (12)C6B—Fe1B—C9B68.20 (10)
C7A—Fe1A—C4A158.01 (11)C5B—Fe1B—C9B116.21 (10)
C10A—Fe1A—C4A124.74 (13)C7B—Fe1B—C9B67.86 (10)
C2A—Fe1A—C4A68.23 (12)C2B—Fe1B—C9B172.95 (10)
C6A—Fe1A—C9A68.45 (11)C4B—Fe1B—C9B110.47 (10)
C7A—Fe1A—C9A68.41 (12)C6B—Fe1B—C3B148.80 (11)
C2A—Fe1A—C9A163.90 (10)C10B—Fe1B—C3B170.35 (11)
C5A—Fe1A—C9A121.45 (12)C5B—Fe1B—C3B68.43 (10)
C3A—Fe1A—C9A126.96 (11)C7B—Fe1B—C3B118.81 (10)
C4A—Fe1A—C9A109.05 (13)C9B—Fe1B—C3B133.99 (10)
C6A—Fe1A—C8A68.58 (11)C6B—Fe1B—C8B68.35 (11)
C10A—Fe1A—C8A68.74 (11)C10B—Fe1B—C8B68.05 (10)
C2A—Fe1A—C8A126.49 (11)C5B—Fe1B—C8B150.17 (10)
C5A—Fe1A—C8A157.71 (12)C2B—Fe1B—C8B133.60 (10)
C3A—Fe1A—C8A109.93 (11)C4B—Fe1B—C8B119.45 (10)
C4A—Fe1A—C8A123.00 (11)C3B—Fe1B—C8B112.56 (10)
C6A—Fe1A—C1A104.37 (10)C6B—Fe1B—C1B104.13 (10)
C7A—Fe1A—C1A122.85 (10)C10B—Fe1B—C1B112.02 (10)
C10A—Fe1A—C1A117.89 (10)C7B—Fe1B—C1B128.72 (10)
C3A—Fe1A—C1A69.14 (10)C4B—Fe1B—C1B69.51 (9)
C4A—Fe1A—C1A69.21 (11)C9B—Fe1B—C1B145.92 (10)
C9A—Fe1A—C1A154.66 (11)C3B—Fe1B—C1B69.36 (9)
C8A—Fe1A—C1A161.35 (11)C8B—Fe1B—C1B168.98 (10)
C5A—C1A—C2A105.3 (2)C5B—C1B—C2B105.5 (2)
C5A—C1A—B1A126.7 (2)C5B—C1B—B1B127.0 (2)
C2A—C1A—B1A128.0 (2)C2B—C1B—B1B127.4 (2)
C5A—C1A—Fe1A68.52 (15)C5B—C1B—Fe1B68.64 (12)
C2A—C1A—Fe1A68.39 (13)C2B—C1B—Fe1B68.83 (12)
B1A—C1A—Fe1A127.47 (17)B1B—C1B—Fe1B125.36 (15)
C3A—C2A—C1A109.9 (2)C3B—C2B—C1B109.7 (2)
C3A—C2A—Fe1A69.70 (16)C3B—C2B—Fe1B69.79 (12)
C1A—C2A—Fe1A70.87 (14)C1B—C2B—Fe1B70.28 (12)
C3A—C2A—H2AA125.1C3B—C2B—H2BA125.2
C1A—C2A—H2AA125.1C1B—C2B—H2BA125.2
Fe1A—C2A—H2AA125.1Fe1B—C2B—H2BA125.2
C4A—C3A—C2A107.7 (2)C4B—C3B—C2B107.6 (2)
C4A—C3A—Fe1A69.76 (16)C4B—C3B—Fe1B69.44 (13)
C2A—C3A—Fe1A69.57 (14)C2B—C3B—Fe1B69.37 (12)
C4A—C3A—H3AA126.2C4B—C3B—H3BA126.2
C2A—C3A—H3AA126.2C2B—C3B—H3BA126.2
Fe1A—C3A—H3AA126.2Fe1B—C3B—H3BA126.2
C3A—C4A—C5A107.3 (3)C3B—C4B—C5B107.3 (2)
C3A—C4A—Fe1A69.70 (16)C3B—C4B—Fe1B69.84 (13)
C5A—C4A—Fe1A69.46 (15)C5B—C4B—Fe1B69.28 (13)
C3A—C4A—H4AA126.3C3B—C4B—H4BA126.3
C5A—C4A—H4AA126.3C5B—C4B—H4BA126.3
Fe1A—C4A—H4AA126.3Fe1B—C4B—H4BA126.3
C1A—C5A—C4A109.8 (2)C4B—C5B—C1B109.9 (2)
C1A—C5A—Fe1A70.91 (14)C4B—C5B—Fe1B69.73 (13)
C4A—C5A—Fe1A69.54 (15)C1B—C5B—Fe1B70.52 (13)
C1A—C5A—H5AA125.1C4B—C5B—H5BA125.0
C4A—C5A—H5AA125.1C1B—C5B—H5BA125.0
Fe1A—C5A—H5AA125.1Fe1B—C5B—H5BA125.0
C10A—C6A—C7A108.4 (2)C10B—C6B—C7B107.6 (2)
C10A—C6A—Fe1A69.92 (16)C10B—C6B—Fe1B69.77 (14)
C7A—C6A—Fe1A69.66 (14)C7B—C6B—Fe1B70.00 (14)
C10A—C6A—H6AA125.8C10B—C6B—H6BA126.2
C7A—C6A—H6AA125.8C7B—C6B—H6BA126.2
Fe1A—C6A—H6AA125.8Fe1B—C6B—H6BA126.2
C6A—C7A—C8A108.1 (2)C8B—C7B—C6B108.2 (2)
C6A—C7A—Fe1A69.59 (15)C8B—C7B—Fe1B70.45 (14)
C8A—C7A—Fe1A70.02 (15)C6B—C7B—Fe1B69.21 (14)
C6A—C7A—H7AA125.9C8B—C7B—H7BA125.9
C8A—C7A—H7AA125.9C6B—C7B—H7BA125.9
Fe1A—C7A—H7AA125.9Fe1B—C7B—H7BA125.9
C9A—C8A—C7A107.7 (2)C9B—C8B—C7B107.6 (2)
C9A—C8A—Fe1A69.69 (15)C9B—C8B—Fe1B69.47 (14)
C7A—C8A—Fe1A69.20 (15)C7B—C8B—Fe1B69.13 (14)
C9A—C8A—H8AA126.1C9B—C8B—H8BA126.2
C7A—C8A—H8AA126.1C7B—C8B—H8BA126.2
Fe1A—C8A—H8AA126.1Fe1B—C8B—H8BA126.2
C8A—C9A—C10A108.2 (3)C10B—C9B—C8B108.6 (2)
C8A—C9A—Fe1A69.74 (16)C10B—C9B—Fe1B69.37 (13)
C10A—C9A—Fe1A69.36 (16)C8B—C9B—Fe1B70.28 (13)
C8A—C9A—H9AA125.9C10B—C9B—H9BA125.7
C10A—C9A—H9AA125.9C8B—C9B—H9BA125.7
Fe1A—C9A—H9AA125.9Fe1B—C9B—H9BA125.7
C6A—C10A—C9A107.5 (2)C9B—C10B—C6B108.0 (2)
C6A—C10A—Fe1A69.42 (15)C9B—C10B—Fe1B70.30 (14)
C9A—C10A—Fe1A69.70 (15)C6B—C10B—Fe1B69.39 (13)
C6A—C10A—H10A126.2C9B—C10B—H10B126.0
C9A—C10A—H10A126.2C6B—C10B—H10B126.0
Fe1A—C10A—H10A126.2Fe1B—C10B—H10B126.0
F2A—B1A—F1A107.2 (2)F3B—B1B—F2B108.4 (2)
F2A—B1A—F3A107.8 (2)F3B—B1B—F1B106.7 (2)
F1A—B1A—F3A107.7 (2)F2B—B1B—F1B106.3 (2)
F2A—B1A—C1A111.2 (2)F3B—B1B—C1B112.4 (2)
F1A—B1A—C1A110.7 (2)F2B—B1B—C1B111.7 (2)
F3A—B1A—C1A112.1 (2)F1B—B1B—C1B111.0 (2)
C15A—N1A—C19A107.89 (17)C15B—N1B—C11B108.26 (17)
C15A—N1A—C23A111.46 (17)C15B—N1B—C19B109.35 (17)
C19A—N1A—C23A109.11 (16)C11B—N1B—C19B111.24 (17)
C15A—N1A—C11A108.26 (16)C15B—N1B—C23B111.11 (17)
C19A—N1A—C11A111.23 (17)C11B—N1B—C23B108.69 (17)
C23A—N1A—C11A108.91 (16)C19B—N1B—C23B108.20 (17)
C12A—C11A—N1A115.95 (18)C12B—C11B—N1B117.1 (2)
C12A—C11A—H11A108.3C12B—C11B—H11C108.0
N1A—C11A—H11A108.3N1B—C11B—H11C108.0
C12A—C11A—H11B108.3C12B—C11B—H11D108.0
N1A—C11A—H11B108.3N1B—C11B—H11D108.0
H11A—C11A—H11B107.4H11C—C11B—H11D107.3
C11A—C12A—C13A109.62 (19)C11B—C12B—C13B108.8 (2)
C11A—C12A—H12A109.7C11B—C12B—H12C109.9
C13A—C12A—H12A109.7C13B—C12B—H12C109.9
C11A—C12A—H12B109.7C11B—C12B—H12D109.9
C13A—C12A—H12B109.7C13B—C12B—H12D109.9
H12A—C12A—H12B108.2H12C—C12B—H12D108.3
C14A—C13A—C12A111.9 (2)C14B—C13B—C12B113.0 (3)
C14A—C13A—H13A109.2C14B—C13B—H13C109.0
C12A—C13A—H13A109.2C12B—C13B—H13C109.0
C14A—C13A—H13B109.2C14B—C13B—H13D109.0
C12A—C13A—H13B109.2C12B—C13B—H13D109.0
H13A—C13A—H13B107.9H13C—C13B—H13D107.8
C13A—C14A—H14A109.5C13B—C14B—H14D109.5
C13A—C14A—H14B109.5C13B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C13A—C14A—H14C109.5C13B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
N1A—C15A—C16A115.08 (18)C16B—C15B—N1B115.49 (19)
N1A—C15A—H15A108.5C16B—C15B—H15C108.4
C16A—C15A—H15A108.5N1B—C15B—H15C108.4
N1A—C15A—H15B108.5C16B—C15B—H15D108.4
C16A—C15A—H15B108.5N1B—C15B—H15D108.4
H15A—C15A—H15B107.5H15C—C15B—H15D107.5
C17A—C16A—C15A111.61 (19)C15B—C16B—C17B110.1 (2)
C17A—C16A—H16A109.3C15B—C16B—H16C109.6
C15A—C16A—H16A109.3C17B—C16B—H16C109.6
C17A—C16A—H16B109.3C15B—C16B—H16D109.6
C15A—C16A—H16B109.3C17B—C16B—H16D109.6
H16A—C16A—H16B108.0H16C—C16B—H16D108.1
C16A—C17A—C18A111.9 (2)C16B—C17B—C18B111.9 (2)
C16A—C17A—H17A109.2C16B—C17B—H17C109.2
C18A—C17A—H17A109.2C18B—C17B—H17C109.2
C16A—C17A—H17B109.2C16B—C17B—H17D109.2
C18A—C17A—H17B109.2C18B—C17B—H17D109.2
H17A—C17A—H17B107.9H17C—C17B—H17D107.9
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C20A—C19A—N1A116.11 (18)C20B—C19B—N1B116.40 (19)
C20A—C19A—H19A108.3C20B—C19B—H19C108.2
N1A—C19A—H19A108.3N1B—C19B—H19C108.2
C20A—C19A—H19B108.3C20B—C19B—H19D108.2
N1A—C19A—H19B108.3N1B—C19B—H19D108.2
H19A—C19A—H19B107.4H19C—C19B—H19D107.3
C19A—C20A—C21A110.55 (19)C19B—C20B—C21B110.7 (2)
C19A—C20A—H20A109.5C19B—C20B—H20C109.5
C21A—C20A—H20A109.5C21B—C20B—H20C109.5
C19A—C20A—H20B109.5C19B—C20B—H20D109.5
C21A—C20A—H20B109.5C21B—C20B—H20D109.5
H20A—C20A—H20B108.1H20C—C20B—H20D108.1
C22A—C21A—C20A113.2 (2)C20B—C21B—C22B111.9 (2)
C22A—C21A—H21A108.9C20B—C21B—H21C109.2
C20A—C21A—H21A108.9C22B—C21B—H21C109.2
C22A—C21A—H21B108.9C20B—C21B—H21D109.2
C20A—C21A—H21B108.9C22B—C21B—H21D109.2
H21A—C21A—H21B107.8H21C—C21B—H21D107.9
C21A—C22A—H22A109.5C21B—C22B—H22D109.5
C21A—C22A—H22B109.5C21B—C22B—H22E109.5
H22A—C22A—H22B109.5H22D—C22B—H22E109.5
C21A—C22A—H22C109.5C21B—C22B—H22F109.5
H22A—C22A—H22C109.5H22D—C22B—H22F109.5
H22B—C22A—H22C109.5H22E—C22B—H22F109.5
C24A—C23A—N1A115.78 (18)C24B—C23B—N1B116.59 (18)
C24A—C23A—H23A108.3C24B—C23B—H23C108.1
N1A—C23A—H23A108.3N1B—C23B—H23C108.1
C24A—C23A—H23B108.3C24B—C23B—H23D108.1
N1A—C23A—H23B108.3N1B—C23B—H23D108.1
H23A—C23A—H23B107.4H23C—C23B—H23D107.3
C23A—C24A—C25A110.32 (19)C23B—C24B—C25B109.1 (2)
C23A—C24A—H24A109.6C23B—C24B—H24C109.9
C25A—C24A—H24A109.6C25B—C24B—H24C109.9
C23A—C24A—H24B109.6C23B—C24B—H24D109.9
C25A—C24A—H24B109.6C25B—C24B—H24D109.9
H24A—C24A—H24B108.1H24C—C24B—H24D108.3
C24A—C25A—C26A111.4 (2)C26B—C25B—C24B113.4 (2)
C24A—C25A—H25A109.3C26B—C25B—H25C108.9
C26A—C25A—H25A109.3C24B—C25B—H25C108.9
C24A—C25A—H25B109.3C26B—C25B—H25D108.9
C26A—C25A—H25B109.3C24B—C25B—H25D108.9
H25A—C25A—H25B108.0H25C—C25B—H25D107.7
C25A—C26A—H26A109.5C25B—C26B—H26D109.5
C25A—C26A—H26B109.5C25B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C25A—C26A—H26C109.5C25B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5
C2A—C1A—B1A—F1A113.5 (3)C2B—C1B—B1B—F1B90.5 (3)
C2A—C1A—B1A—F2A5.5 (4)C2B—C1B—B1B—F2B27.9 (3)
C2A—C1A—B1A—F3A126.3 (3)C2B—C1B—B1B—F3B150.0 (2)

Experimental details

Crystal data
Chemical formula(C16H36N)[Fe(C5H5)(C5H4BF3)]
Mr495.29
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)9.9310 (2), 15.5450 (4), 17.9230 (5)
α, β, γ (°)87.4990 (14), 87.9350 (17), 75.3340 (16)
V3)2673.31 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.60
Crystal size (mm)0.25 × 0.15 × 0.15
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.865, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
50155, 12237, 8213
Rint0.041
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.123, 1.02
No. of reflections12237
No. of parameters578
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.45

Computer programs: COLLECT (Nonius, 1997-2001), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
C1A—B1A1.608 (3)C1B—B1B1.605 (4)
C5A—C1A—B1A126.7 (2)C5B—C1B—B1B127.0 (2)
C2A—C1A—B1A128.0 (2)C2B—C1B—B1B127.4 (2)
C2A—C1A—B1A—F1A113.5 (3)C2B—C1B—B1B—F1B90.5 (3)
C2A—C1A—B1A—F2A5.5 (4)C2B—C1B—B1B—F2B27.9 (3)
C2A—C1A—B1A—F3A126.3 (3)C2B—C1B—B1B—F3B150.0 (2)
 

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