Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010261/cf6088sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010261/cf6088Isup2.hkl |
CCDC reference: 170749
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
H atoms were included in calculated positions with C—H distances ranging from 0.98 to 1.00 Å.
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.
Fig. 1. View of (I) showing the atom-labelling scheme. Ellipsoids are at the 50% probability level. |
(C16H36N)[Fe(C5H5)(C5H4BF3)] | Z = 4 |
Mr = 495.29 | F(000) = 1064 |
Triclinic, P1 | Dx = 1.231 Mg m−3 |
a = 9.9310 (2) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 15.5450 (4) Å | Cell parameters from 33767 reflections |
c = 17.9230 (5) Å | θ = 2.6–27.5° |
α = 87.4990 (14)° | µ = 0.60 mm−1 |
β = 87.9350 (17)° | T = 150 K |
γ = 75.3340 (16)° | Needle, orange |
V = 2673.31 (11) Å3 | 0.25 × 0.15 × 0.15 mm |
Nonius KappaCCD diffractometer | 12237 independent reflections |
Radiation source: fine-focus sealed tube | 8213 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.041 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.6° |
ϕ scans, and ω scans with κ offsets | h = −12→12 |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | k = −19→20 |
Tmin = 0.865, Tmax = 0.916 | l = −23→23 |
50155 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
(C16H36N)[Fe(C5H5)(C5H4BF3)] | γ = 75.3340 (16)° |
Mr = 495.29 | V = 2673.31 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.9310 (2) Å | Mo Kα radiation |
b = 15.5450 (4) Å | µ = 0.60 mm−1 |
c = 17.9230 (5) Å | T = 150 K |
α = 87.4990 (14)° | 0.25 × 0.15 × 0.15 mm |
β = 87.9350 (17)° |
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 = 0.916 | Rint = 0.041 |
50155 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.37 e Å−3 |
12237 reflections | Δρmin = −0.45 e Å−3 |
578 parameters |
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 | ||
Fe1A | 0.35925 (4) | 0.31266 (2) | 0.524013 (18) | 0.03047 (11) | |
F1A | 0.37221 (18) | 0.36812 (10) | 0.27882 (8) | 0.0525 (4) | |
F2A | 0.25554 (15) | 0.26711 (10) | 0.32243 (9) | 0.0473 (4) | |
F3A | 0.48736 (15) | 0.24349 (10) | 0.34416 (8) | 0.0459 (4) | |
C1A | 0.3216 (3) | 0.36268 (15) | 0.41567 (13) | 0.0319 (5) | |
C2A | 0.1957 (3) | 0.37610 (16) | 0.45995 (13) | 0.0355 (6) | |
H2AA | 0.1146 | 0.3519 | 0.4491 | 0.043* | |
C3A | 0.2043 (3) | 0.42739 (17) | 0.52237 (15) | 0.0454 (7) | |
H3AA | 0.1304 | 0.4463 | 0.5620 | 0.054* | |
C4A | 0.3358 (4) | 0.44699 (18) | 0.51841 (16) | 0.0529 (8) | |
H4AA | 0.3720 | 0.4824 | 0.5545 | 0.063* | |
C5A | 0.4072 (3) | 0.40725 (17) | 0.45299 (16) | 0.0447 (7) | |
H5AA | 0.5036 | 0.4093 | 0.4364 | 0.054* | |
C6A | 0.4452 (3) | 0.18056 (17) | 0.51254 (15) | 0.0411 (6) | |
H6AA | 0.4581 | 0.1486 | 0.4646 | 0.049* | |
C7A | 0.3261 (3) | 0.19398 (17) | 0.56061 (15) | 0.0402 (6) | |
H7AA | 0.2407 | 0.1730 | 0.5526 | 0.048* | |
C8A | 0.3489 (3) | 0.24250 (18) | 0.62218 (14) | 0.0426 (7) | |
H8AA | 0.2824 | 0.2620 | 0.6650 | 0.051* | |
C9A | 0.4823 (3) | 0.2590 (2) | 0.61173 (15) | 0.0479 (7) | |
H9AA | 0.5264 | 0.2925 | 0.6459 | 0.058* | |
C10A | 0.5422 (3) | 0.22073 (19) | 0.54347 (16) | 0.0458 (7) | |
H10A | 0.6357 | 0.2220 | 0.5215 | 0.055* | |
B1A | 0.3601 (3) | 0.30939 (19) | 0.33970 (16) | 0.0329 (6) | |
N1A | 0.53793 (18) | 0.00946 (12) | 0.25034 (10) | 0.0253 (4) | |
C11A | 0.4056 (2) | 0.05637 (15) | 0.29234 (13) | 0.0288 (5) | |
H11A | 0.4151 | 0.1155 | 0.3061 | 0.035* | |
H11B | 0.3269 | 0.0664 | 0.2579 | 0.035* | |
C12A | 0.3686 (2) | 0.00812 (16) | 0.36266 (13) | 0.0319 (6) | |
H12A | 0.4429 | 0.0013 | 0.3995 | 0.038* | |
H12B | 0.3611 | −0.0520 | 0.3504 | 0.038* | |
C13A | 0.2303 (2) | 0.06112 (17) | 0.39601 (14) | 0.0364 (6) | |
H13A | 0.2385 | 0.1212 | 0.4078 | 0.044* | |
H13B | 0.1568 | 0.0682 | 0.3586 | 0.044* | |
C14A | 0.1877 (3) | 0.0156 (2) | 0.46674 (16) | 0.0523 (8) | |
H14A | 0.0988 | 0.0515 | 0.4864 | 0.078* | |
H14B | 0.2594 | 0.0095 | 0.5042 | 0.078* | |
H14C | 0.1776 | −0.0434 | 0.4551 | 0.078* | |
C15A | 0.6609 (2) | 0.00342 (16) | 0.30032 (12) | 0.0280 (5) | |
H15A | 0.6536 | −0.0370 | 0.3437 | 0.034* | |
H15B | 0.6541 | 0.0631 | 0.3197 | 0.034* | |
C16A | 0.8042 (2) | −0.02959 (17) | 0.26256 (13) | 0.0317 (5) | |
H16A | 0.8023 | −0.0784 | 0.2292 | 0.038* | |
H16B | 0.8263 | 0.0195 | 0.2315 | 0.038* | |
C17A | 0.9166 (2) | −0.06267 (18) | 0.31923 (14) | 0.0371 (6) | |
H17A | 0.8957 | −0.1128 | 0.3494 | 0.044* | |
H17B | 0.9167 | −0.0143 | 0.3534 | 0.044* | |
C18A | 1.0599 (3) | −0.09330 (19) | 0.28221 (16) | 0.0460 (7) | |
H18A | 1.1296 | −0.1142 | 0.3206 | 0.069* | |
H18B | 1.0818 | −0.0435 | 0.2531 | 0.069* | |
H18C | 1.0607 | −0.1419 | 0.2490 | 0.069* | |
C19A | 0.5352 (2) | −0.08478 (15) | 0.23216 (13) | 0.0272 (5) | |
H19A | 0.6244 | −0.1132 | 0.2067 | 0.033* | |
H19B | 0.5300 | −0.1187 | 0.2798 | 0.033* | |
C20A | 0.4179 (2) | −0.09327 (16) | 0.18402 (14) | 0.0319 (5) | |
H20A | 0.4249 | −0.0631 | 0.1348 | 0.038* | |
H20B | 0.3275 | −0.0639 | 0.2080 | 0.038* | |
C21A | 0.4240 (3) | −0.19078 (16) | 0.17319 (14) | 0.0360 (6) | |
H21A | 0.5201 | −0.2221 | 0.1580 | 0.043* | |
H21B | 0.4015 | −0.2180 | 0.2215 | 0.043* | |
C22A | 0.3248 (3) | −0.20417 (19) | 0.11508 (16) | 0.0457 (7) | |
H22A | 0.3336 | −0.2680 | 0.1105 | 0.069* | |
H22B | 0.3477 | −0.1785 | 0.0668 | 0.069* | |
H22C | 0.2291 | −0.1747 | 0.1303 | 0.069* | |
C23A | 0.5511 (2) | 0.06192 (15) | 0.17790 (12) | 0.0276 (5) | |
H23A | 0.6312 | 0.0275 | 0.1483 | 0.033* | |
H23B | 0.4663 | 0.0670 | 0.1488 | 0.033* | |
C24A | 0.5704 (3) | 0.15474 (16) | 0.18647 (13) | 0.0332 (6) | |
H24A | 0.6596 | 0.1507 | 0.2111 | 0.040* | |
H24B | 0.4941 | 0.1892 | 0.2185 | 0.040* | |
C25A | 0.5707 (3) | 0.20223 (16) | 0.11038 (13) | 0.0327 (6) | |
H25A | 0.4810 | 0.2066 | 0.0862 | 0.039* | |
H25B | 0.6460 | 0.1670 | 0.0783 | 0.039* | |
C26A | 0.5920 (3) | 0.29547 (16) | 0.11726 (15) | 0.0413 (7) | |
H26A | 0.5916 | 0.3242 | 0.0675 | 0.062* | |
H26B | 0.6815 | 0.2912 | 0.1404 | 0.062* | |
H26C | 0.5166 | 0.3308 | 0.1483 | 0.062* | |
Fe1B | 0.13191 (3) | 0.13869 (2) | 0.029700 (17) | 0.02532 (10) | |
F1B | 0.18902 (18) | 0.23721 (10) | −0.20448 (8) | 0.0571 (5) | |
F2B | 0.18386 (18) | 0.31633 (10) | −0.10084 (9) | 0.0551 (4) | |
F3B | −0.01003 (15) | 0.27638 (10) | −0.13471 (9) | 0.0489 (4) | |
C1B | 0.1833 (2) | 0.15640 (15) | −0.08136 (12) | 0.0271 (5) | |
C2B | 0.3055 (2) | 0.12776 (16) | −0.03747 (13) | 0.0296 (5) | |
H2BA | 0.3773 | 0.1619 | −0.0323 | 0.036* | |
C3B | 0.3072 (2) | 0.04420 (16) | −0.00075 (13) | 0.0321 (6) | |
H3BA | 0.3803 | 0.0096 | 0.0336 | 0.039* | |
C4B | 0.1855 (2) | 0.01941 (15) | −0.02131 (13) | 0.0313 (5) | |
H4BA | 0.1577 | −0.0359 | −0.0044 | 0.038* | |
C5B | 0.1109 (2) | 0.08799 (15) | −0.07083 (12) | 0.0289 (5) | |
H5BA | 0.0201 | 0.0888 | −0.0937 | 0.035* | |
C6B | 0.0442 (3) | 0.26379 (17) | 0.06377 (15) | 0.0408 (7) | |
H6BA | 0.0476 | 0.3204 | 0.0360 | 0.049* | |
C7B | 0.1410 (3) | 0.21698 (18) | 0.11690 (15) | 0.0406 (7) | |
H7BA | 0.2256 | 0.2345 | 0.1327 | 0.049* | |
C8B | 0.0975 (3) | 0.14102 (18) | 0.14360 (13) | 0.0383 (6) | |
H8BA | 0.1460 | 0.0953 | 0.1812 | 0.046* | |
C9B | −0.0260 (3) | 0.14108 (18) | 0.10685 (14) | 0.0371 (6) | |
H9BA | −0.0801 | 0.0950 | 0.1140 | 0.045* | |
C10B | −0.0593 (2) | 0.21630 (18) | 0.05791 (14) | 0.0386 (6) | |
H10B | −0.1416 | 0.2333 | 0.0249 | 0.046* | |
B1B | 0.1348 (3) | 0.24756 (19) | −0.13000 (16) | 0.0340 (7) | |
N1B | −0.06031 (19) | 0.47897 (12) | 0.24076 (10) | 0.0258 (4) | |
C11B | −0.0680 (2) | 0.41285 (15) | 0.30510 (13) | 0.0296 (5) | |
H11C | 0.0233 | 0.3968 | 0.3296 | 0.036* | |
H11D | −0.1379 | 0.4435 | 0.3423 | 0.036* | |
C12B | −0.1041 (3) | 0.32785 (16) | 0.28615 (14) | 0.0361 (6) | |
H12C | −0.0352 | 0.2953 | 0.2493 | 0.043* | |
H12D | −0.1973 | 0.3417 | 0.2639 | 0.043* | |
C13B | −0.1033 (3) | 0.27022 (18) | 0.35788 (17) | 0.0474 (7) | |
H13C | −0.0075 | 0.2526 | 0.3770 | 0.057* | |
H13D | −0.1641 | 0.3061 | 0.3962 | 0.057* | |
C14B | −0.1521 (3) | 0.18788 (19) | 0.34643 (19) | 0.0556 (8) | |
H14D | −0.1494 | 0.1537 | 0.3938 | 0.083* | |
H14E | −0.0911 | 0.1514 | 0.3093 | 0.083* | |
H14F | −0.2477 | 0.2049 | 0.3286 | 0.083* | |
C15B | 0.0675 (2) | 0.43954 (15) | 0.19210 (13) | 0.0310 (5) | |
H15C | 0.1502 | 0.4249 | 0.2240 | 0.037* | |
H15D | 0.0570 | 0.3831 | 0.1725 | 0.037* | |
C16B | 0.0951 (2) | 0.49859 (17) | 0.12664 (14) | 0.0358 (6) | |
H16C | 0.0991 | 0.5571 | 0.1448 | 0.043* | |
H16D | 0.0182 | 0.5084 | 0.0911 | 0.043* | |
C17B | 0.2321 (3) | 0.45522 (18) | 0.08716 (15) | 0.0446 (7) | |
H17C | 0.2258 | 0.3982 | 0.0669 | 0.053* | |
H17D | 0.3076 | 0.4420 | 0.1237 | 0.053* | |
C18B | 0.2680 (3) | 0.5147 (2) | 0.02379 (17) | 0.0614 (9) | |
H18D | 0.3567 | 0.4847 | −0.0002 | 0.092* | |
H18E | 0.2760 | 0.5708 | 0.0438 | 0.092* | |
H18F | 0.1944 | 0.5270 | −0.0131 | 0.092* | |
C19B | −0.1900 (2) | 0.49754 (16) | 0.19364 (13) | 0.0296 (5) | |
H19C | −0.1833 | 0.5439 | 0.1550 | 0.036* | |
H19D | −0.1896 | 0.4427 | 0.1674 | 0.036* | |
C20B | −0.3284 (2) | 0.52744 (17) | 0.23502 (13) | 0.0359 (6) | |
H20C | −0.3299 | 0.5813 | 0.2629 | 0.043* | |
H20D | −0.3401 | 0.4801 | 0.2715 | 0.043* | |
C21B | −0.4472 (2) | 0.54786 (17) | 0.18113 (15) | 0.0376 (6) | |
H21C | −0.4419 | 0.4950 | 0.1512 | 0.045* | |
H21D | −0.4378 | 0.5974 | 0.1464 | 0.045* | |
C22B | −0.5887 (3) | 0.57321 (18) | 0.22166 (16) | 0.0440 (7) | |
H22D | −0.6627 | 0.5859 | 0.1850 | 0.066* | |
H22E | −0.5951 | 0.6262 | 0.2506 | 0.066* | |
H22F | −0.5992 | 0.5238 | 0.2554 | 0.066* | |
C23B | −0.0507 (2) | 0.56642 (15) | 0.27296 (13) | 0.0290 (5) | |
H23C | −0.0502 | 0.6098 | 0.2309 | 0.035* | |
H23D | −0.1361 | 0.5897 | 0.3036 | 0.035* | |
C24B | 0.0740 (2) | 0.56280 (16) | 0.32042 (14) | 0.0328 (6) | |
H24C | 0.1611 | 0.5406 | 0.2908 | 0.039* | |
H24D | 0.0740 | 0.5216 | 0.3641 | 0.039* | |
C25B | 0.0668 (3) | 0.65558 (18) | 0.34659 (16) | 0.0453 (7) | |
H25C | 0.0781 | 0.6943 | 0.3027 | 0.054* | |
H25D | −0.0265 | 0.6804 | 0.3694 | 0.054* | |
C26B | 0.1758 (3) | 0.6575 (2) | 0.40249 (18) | 0.0585 (8) | |
H26D | 0.1656 | 0.7189 | 0.4172 | 0.088* | |
H26E | 0.2686 | 0.6345 | 0.3799 | 0.088* | |
H26F | 0.1640 | 0.6205 | 0.4467 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1A | 0.0380 (2) | 0.0303 (2) | 0.02439 (19) | −0.01055 (15) | −0.00209 (15) | −0.00209 (14) |
F1A | 0.0791 (12) | 0.0441 (9) | 0.0283 (8) | −0.0075 (8) | 0.0123 (8) | 0.0035 (7) |
F2A | 0.0481 (9) | 0.0458 (9) | 0.0479 (9) | −0.0092 (7) | −0.0029 (7) | −0.0146 (7) |
F3A | 0.0408 (8) | 0.0514 (10) | 0.0356 (8) | 0.0082 (7) | 0.0005 (7) | −0.0114 (7) |
C1A | 0.0405 (14) | 0.0253 (13) | 0.0282 (13) | −0.0061 (10) | 0.0020 (11) | 0.0005 (10) |
C2A | 0.0408 (14) | 0.0303 (14) | 0.0299 (13) | −0.0001 (11) | 0.0008 (11) | 0.0051 (11) |
C3A | 0.0677 (19) | 0.0320 (15) | 0.0293 (14) | 0.0001 (13) | 0.0064 (13) | −0.0042 (11) |
C4A | 0.093 (2) | 0.0339 (16) | 0.0364 (16) | −0.0244 (16) | 0.0015 (16) | −0.0093 (12) |
C5A | 0.0595 (18) | 0.0345 (15) | 0.0460 (16) | −0.0238 (13) | 0.0091 (14) | −0.0031 (12) |
C6A | 0.0526 (16) | 0.0316 (14) | 0.0342 (14) | −0.0012 (12) | −0.0067 (12) | 0.0011 (11) |
C7A | 0.0485 (16) | 0.0343 (15) | 0.0392 (15) | −0.0132 (12) | −0.0072 (12) | 0.0068 (12) |
C8A | 0.0505 (16) | 0.0429 (16) | 0.0295 (14) | −0.0041 (13) | −0.0005 (12) | 0.0060 (12) |
C9A | 0.0533 (17) | 0.0579 (19) | 0.0340 (15) | −0.0147 (14) | −0.0170 (13) | 0.0002 (13) |
C10A | 0.0360 (14) | 0.0566 (19) | 0.0409 (16) | −0.0041 (13) | −0.0046 (12) | 0.0011 (13) |
B1A | 0.0394 (15) | 0.0289 (15) | 0.0269 (14) | −0.0023 (12) | 0.0024 (12) | −0.0019 (12) |
N1A | 0.0294 (10) | 0.0262 (10) | 0.0189 (9) | −0.0041 (8) | −0.0001 (8) | −0.0022 (8) |
C11A | 0.0272 (12) | 0.0292 (13) | 0.0263 (12) | −0.0002 (9) | 0.0028 (10) | −0.0043 (10) |
C12A | 0.0332 (13) | 0.0321 (13) | 0.0304 (13) | −0.0085 (10) | 0.0053 (11) | −0.0031 (10) |
C13A | 0.0305 (13) | 0.0440 (15) | 0.0342 (14) | −0.0088 (11) | 0.0050 (11) | −0.0055 (12) |
C14A | 0.0517 (17) | 0.061 (2) | 0.0459 (17) | −0.0191 (15) | 0.0228 (15) | −0.0068 (15) |
C15A | 0.0320 (12) | 0.0326 (13) | 0.0204 (11) | −0.0094 (10) | −0.0023 (10) | −0.0024 (10) |
C16A | 0.0289 (12) | 0.0408 (15) | 0.0257 (12) | −0.0089 (10) | 0.0011 (10) | −0.0036 (11) |
C17A | 0.0332 (13) | 0.0443 (16) | 0.0334 (14) | −0.0092 (11) | −0.0018 (11) | −0.0010 (12) |
C18A | 0.0318 (14) | 0.0534 (18) | 0.0522 (18) | −0.0100 (12) | −0.0010 (13) | 0.0001 (14) |
C19A | 0.0294 (12) | 0.0241 (12) | 0.0268 (12) | −0.0039 (9) | 0.0008 (10) | −0.0034 (9) |
C20A | 0.0330 (13) | 0.0289 (13) | 0.0335 (13) | −0.0069 (10) | −0.0052 (10) | −0.0002 (10) |
C21A | 0.0438 (15) | 0.0317 (14) | 0.0350 (14) | −0.0130 (11) | −0.0078 (11) | −0.0009 (11) |
C22A | 0.0572 (17) | 0.0421 (16) | 0.0433 (16) | −0.0211 (14) | −0.0116 (13) | −0.0025 (13) |
C23A | 0.0325 (12) | 0.0283 (13) | 0.0214 (11) | −0.0065 (10) | 0.0009 (10) | −0.0012 (9) |
C24A | 0.0453 (15) | 0.0306 (13) | 0.0251 (12) | −0.0122 (11) | 0.0027 (11) | −0.0026 (10) |
C25A | 0.0327 (13) | 0.0363 (14) | 0.0279 (13) | −0.0076 (10) | 0.0014 (10) | 0.0032 (10) |
C26A | 0.0429 (15) | 0.0304 (14) | 0.0465 (16) | −0.0041 (11) | 0.0095 (13) | 0.0045 (12) |
Fe1B | 0.02638 (18) | 0.02622 (19) | 0.02237 (18) | −0.00445 (13) | 0.00212 (13) | −0.00529 (13) |
F1B | 0.0739 (11) | 0.0427 (10) | 0.0359 (9) | 0.0153 (8) | 0.0175 (8) | 0.0121 (7) |
F2B | 0.0742 (11) | 0.0344 (9) | 0.0603 (11) | −0.0205 (8) | −0.0092 (9) | 0.0077 (8) |
F3B | 0.0380 (8) | 0.0402 (9) | 0.0592 (10) | 0.0048 (7) | −0.0009 (7) | 0.0120 (8) |
C1B | 0.0296 (12) | 0.0268 (12) | 0.0233 (12) | −0.0042 (9) | 0.0031 (10) | −0.0047 (9) |
C2B | 0.0263 (12) | 0.0353 (14) | 0.0266 (12) | −0.0066 (10) | 0.0043 (10) | −0.0047 (10) |
C3B | 0.0325 (13) | 0.0341 (14) | 0.0235 (12) | 0.0030 (10) | 0.0014 (10) | −0.0017 (10) |
C4B | 0.0434 (14) | 0.0253 (13) | 0.0237 (12) | −0.0062 (10) | 0.0056 (11) | −0.0038 (10) |
C5B | 0.0332 (12) | 0.0310 (13) | 0.0212 (11) | −0.0051 (10) | 0.0015 (10) | −0.0079 (10) |
C6B | 0.0474 (16) | 0.0290 (14) | 0.0426 (16) | −0.0032 (12) | 0.0102 (13) | −0.0105 (12) |
C7B | 0.0340 (13) | 0.0508 (17) | 0.0385 (15) | −0.0103 (12) | 0.0041 (12) | −0.0248 (13) |
C8B | 0.0423 (15) | 0.0449 (16) | 0.0216 (12) | 0.0011 (12) | 0.0019 (11) | −0.0085 (11) |
C9B | 0.0352 (14) | 0.0478 (16) | 0.0308 (14) | −0.0145 (12) | 0.0087 (11) | −0.0102 (12) |
C10B | 0.0271 (12) | 0.0520 (17) | 0.0316 (14) | 0.0008 (11) | 0.0050 (11) | −0.0145 (12) |
B1B | 0.0383 (16) | 0.0307 (15) | 0.0305 (15) | −0.0050 (12) | 0.0065 (12) | −0.0012 (12) |
N1B | 0.0314 (10) | 0.0227 (10) | 0.0226 (10) | −0.0049 (8) | −0.0001 (8) | −0.0029 (8) |
C11B | 0.0347 (13) | 0.0269 (13) | 0.0263 (12) | −0.0061 (10) | −0.0022 (10) | 0.0019 (10) |
C12B | 0.0392 (14) | 0.0287 (14) | 0.0412 (15) | −0.0097 (11) | −0.0008 (12) | −0.0018 (11) |
C13B | 0.0541 (17) | 0.0350 (15) | 0.0551 (18) | −0.0149 (13) | −0.0140 (14) | 0.0072 (13) |
C14B | 0.0571 (18) | 0.0425 (18) | 0.070 (2) | −0.0189 (14) | −0.0103 (16) | 0.0056 (16) |
C15B | 0.0335 (13) | 0.0270 (13) | 0.0309 (13) | −0.0040 (10) | 0.0039 (10) | −0.0082 (10) |
C16B | 0.0319 (13) | 0.0448 (16) | 0.0297 (13) | −0.0080 (11) | 0.0017 (11) | −0.0028 (11) |
C17B | 0.0435 (15) | 0.0474 (17) | 0.0435 (16) | −0.0129 (13) | 0.0133 (13) | −0.0136 (13) |
C18B | 0.0509 (18) | 0.091 (3) | 0.0433 (18) | −0.0215 (17) | 0.0140 (15) | −0.0017 (17) |
C19B | 0.0321 (12) | 0.0299 (13) | 0.0266 (12) | −0.0066 (10) | −0.0048 (10) | −0.0022 (10) |
C20B | 0.0367 (13) | 0.0390 (15) | 0.0300 (13) | −0.0058 (11) | −0.0011 (11) | −0.0036 (11) |
C21B | 0.0350 (13) | 0.0373 (15) | 0.0412 (15) | −0.0095 (11) | −0.0018 (12) | −0.0058 (12) |
C22B | 0.0368 (14) | 0.0411 (16) | 0.0554 (18) | −0.0118 (12) | −0.0024 (13) | −0.0032 (13) |
C23B | 0.0395 (13) | 0.0210 (12) | 0.0252 (12) | −0.0048 (10) | 0.0011 (10) | −0.0043 (9) |
C24B | 0.0330 (13) | 0.0325 (14) | 0.0336 (13) | −0.0090 (10) | 0.0025 (11) | −0.0072 (11) |
C25B | 0.0601 (18) | 0.0351 (15) | 0.0454 (16) | −0.0190 (13) | −0.0093 (14) | −0.0045 (13) |
C26B | 0.061 (2) | 0.058 (2) | 0.063 (2) | −0.0237 (16) | −0.0097 (16) | −0.0145 (16) |
Fe1A—C6A | 2.031 (3) | Fe1B—C6B | 2.030 (2) |
Fe1A—C7A | 2.032 (3) | Fe1B—C10B | 2.035 (2) |
Fe1A—C10A | 2.037 (3) | Fe1B—C5B | 2.036 (2) |
Fe1A—C2A | 2.038 (3) | Fe1B—C7B | 2.041 (2) |
Fe1A—C5A | 2.039 (3) | Fe1B—C2B | 2.042 (2) |
Fe1A—C3A | 2.039 (3) | Fe1B—C4B | 2.042 (2) |
Fe1A—C4A | 2.040 (3) | Fe1B—C9B | 2.047 (2) |
Fe1A—C9A | 2.042 (3) | Fe1B—C3B | 2.047 (2) |
Fe1A—C8A | 2.043 (3) | Fe1B—C8B | 2.058 (2) |
Fe1A—C1A | 2.071 (2) | Fe1B—C1B | 2.061 (2) |
F1A—B1A | 1.414 (3) | F1B—B1B | 1.422 (3) |
F2A—B1A | 1.411 (3) | F2B—B1B | 1.409 (3) |
F3A—B1A | 1.414 (3) | F3B—B1B | 1.399 (3) |
C1A—C5A | 1.425 (4) | C1B—C5B | 1.430 (3) |
C1A—C2A | 1.431 (3) | C1B—C2B | 1.433 (3) |
C1A—B1A | 1.608 (3) | C1B—B1B | 1.605 (4) |
C2A—C3A | 1.419 (4) | C2B—C3B | 1.427 (3) |
C2A—H2AA | 1.000 | C2B—H2BA | 1.000 |
C3A—C4A | 1.414 (4) | C3B—C4B | 1.423 (3) |
C3A—H3AA | 1.000 | C3B—H3BA | 1.000 |
C4A—C5A | 1.429 (4) | C4B—C5B | 1.428 (3) |
C4A—H4AA | 1.000 | C4B—H4BA | 1.000 |
C5A—H5AA | 1.000 | C5B—H5BA | 1.000 |
C6A—C10A | 1.413 (4) | C6B—C10B | 1.418 (4) |
C6A—C7A | 1.414 (4) | C6B—C7B | 1.419 (4) |
C6A—H6AA | 1.000 | C6B—H6BA | 1.000 |
C7A—C8A | 1.420 (4) | C7B—C8B | 1.416 (4) |
C7A—H7AA | 1.000 | C7B—H7BA | 1.000 |
C8A—C9A | 1.416 (4) | C8B—C9B | 1.413 (4) |
C8A—H8AA | 1.000 | C8B—H8BA | 1.000 |
C9A—C10A | 1.427 (4) | C9B—C10B | 1.408 (4) |
C9A—H9AA | 1.000 | C9B—H9BA | 1.000 |
C10A—H10A | 1.000 | C10B—H10B | 1.000 |
N1A—C15A | 1.522 (3) | N1B—C15B | 1.523 (3) |
N1A—C19A | 1.522 (3) | N1B—C11B | 1.524 (3) |
N1A—C23A | 1.522 (3) | N1B—C19B | 1.525 (3) |
N1A—C11A | 1.522 (3) | N1B—C23B | 1.526 (3) |
C11A—C12A | 1.520 (3) | C11B—C12B | 1.509 (3) |
C11A—H11A | 0.990 | C11B—H11C | 0.990 |
C11A—H11B | 0.990 | C11B—H11D | 0.990 |
C12A—C13A | 1.528 (3) | C12B—C13B | 1.534 (4) |
C12A—H12A | 0.990 | C12B—H12C | 0.990 |
C12A—H12B | 0.990 | C12B—H12D | 0.990 |
C13A—C14A | 1.523 (3) | C13B—C14B | 1.504 (4) |
C13A—H13A | 0.990 | C13B—H13C | 0.990 |
C13A—H13B | 0.990 | C13B—H13D | 0.990 |
C14A—H14A | 0.980 | C14B—H14D | 0.980 |
C14A—H14B | 0.980 | C14B—H14E | 0.980 |
C14A—H14C | 0.980 | C14B—H14F | 0.980 |
C15A—C16A | 1.529 (3) | C15B—C16B | 1.518 (3) |
C15A—H15A | 0.990 | C15B—H15C | 0.990 |
C15A—H15B | 0.990 | C15B—H15D | 0.990 |
C16A—C17A | 1.512 (3) | C16B—C17B | 1.521 (3) |
C16A—H16A | 0.990 | C16B—H16C | 0.990 |
C16A—H16B | 0.990 | C16B—H16D | 0.990 |
C17A—C18A | 1.520 (3) | C17B—C18B | 1.523 (4) |
C17A—H17A | 0.990 | C17B—H17C | 0.990 |
C17A—H17B | 0.990 | C17B—H17D | 0.990 |
C18A—H18A | 0.980 | C18B—H18D | 0.980 |
C18A—H18B | 0.980 | C18B—H18E | 0.980 |
C18A—H18C | 0.980 | C18B—H18F | 0.980 |
C19A—C20A | 1.510 (3) | C19B—C20B | 1.512 (3) |
C19A—H19A | 0.990 | C19B—H19C | 0.990 |
C19A—H19B | 0.990 | C19B—H19D | 0.990 |
C20A—C21A | 1.522 (3) | C20B—C21B | 1.514 (3) |
C20A—H20A | 0.990 | C20B—H20C | 0.990 |
C20A—H20B | 0.990 | C20B—H20D | 0.990 |
C21A—C22A | 1.515 (4) | C21B—C22B | 1.526 (3) |
C21A—H21A | 0.990 | C21B—H21C | 0.990 |
C21A—H21B | 0.990 | C21B—H21D | 0.990 |
C22A—H22A | 0.980 | C22B—H22D | 0.980 |
C22A—H22B | 0.980 | C22B—H22E | 0.980 |
C22A—H22C | 0.980 | C22B—H22F | 0.980 |
C23A—C24A | 1.518 (3) | C23B—C24B | 1.516 (3) |
C23A—H23A | 0.990 | C23B—H23C | 0.990 |
C23A—H23B | 0.990 | C23B—H23D | 0.990 |
C24A—C25A | 1.522 (3) | C24B—C25B | 1.520 (3) |
C24A—H24A | 0.990 | C24B—H24C | 0.990 |
C24A—H24B | 0.990 | C24B—H24D | 0.990 |
C25A—C26A | 1.528 (3) | C25B—C26B | 1.508 (4) |
C25A—H25A | 0.990 | C25B—H25C | 0.990 |
C25A—H25B | 0.990 | C25B—H25D | 0.990 |
C26A—H26A | 0.980 | C26B—H26D | 0.980 |
C26A—H26B | 0.980 | C26B—H26E | 0.980 |
C26A—H26C | 0.980 | C26B—H26F | 0.980 |
C7A—Fe1A—C10A | 68.63 (11) | C6B—Fe1B—C5B | 127.24 (11) |
C6A—Fe1A—C2A | 119.64 (11) | C10B—Fe1B—C5B | 106.00 (10) |
C7A—Fe1A—C2A | 107.81 (11) | C10B—Fe1B—C7B | 68.33 (10) |
C10A—Fe1A—C2A | 153.86 (11) | C5B—Fe1B—C7B | 166.71 (11) |
C6A—Fe1A—C5A | 122.47 (11) | C6B—Fe1B—C2B | 114.40 (10) |
C7A—Fe1A—C5A | 159.43 (11) | C10B—Fe1B—C2B | 145.68 (10) |
C10A—Fe1A—C5A | 106.09 (12) | C5B—Fe1B—C2B | 67.97 (9) |
C2A—Fe1A—C5A | 67.67 (11) | C7B—Fe1B—C2B | 109.46 (10) |
C6A—Fe1A—C3A | 156.11 (12) | C6B—Fe1B—C4B | 167.24 (11) |
C7A—Fe1A—C3A | 122.32 (12) | C10B—Fe1B—C4B | 130.02 (10) |
C10A—Fe1A—C3A | 162.83 (12) | C7B—Fe1B—C4B | 151.55 (11) |
C5A—Fe1A—C3A | 68.30 (11) | C2B—Fe1B—C4B | 68.54 (9) |
C6A—Fe1A—C4A | 160.47 (12) | C6B—Fe1B—C9B | 68.20 (10) |
C7A—Fe1A—C4A | 158.01 (11) | C5B—Fe1B—C9B | 116.21 (10) |
C10A—Fe1A—C4A | 124.74 (13) | C7B—Fe1B—C9B | 67.86 (10) |
C2A—Fe1A—C4A | 68.23 (12) | C2B—Fe1B—C9B | 172.95 (10) |
C6A—Fe1A—C9A | 68.45 (11) | C4B—Fe1B—C9B | 110.47 (10) |
C7A—Fe1A—C9A | 68.41 (12) | C6B—Fe1B—C3B | 148.80 (11) |
C2A—Fe1A—C9A | 163.90 (10) | C10B—Fe1B—C3B | 170.35 (11) |
C5A—Fe1A—C9A | 121.45 (12) | C5B—Fe1B—C3B | 68.43 (10) |
C3A—Fe1A—C9A | 126.96 (11) | C7B—Fe1B—C3B | 118.81 (10) |
C4A—Fe1A—C9A | 109.05 (13) | C9B—Fe1B—C3B | 133.99 (10) |
C6A—Fe1A—C8A | 68.58 (11) | C6B—Fe1B—C8B | 68.35 (11) |
C10A—Fe1A—C8A | 68.74 (11) | C10B—Fe1B—C8B | 68.05 (10) |
C2A—Fe1A—C8A | 126.49 (11) | C5B—Fe1B—C8B | 150.17 (10) |
C5A—Fe1A—C8A | 157.71 (12) | C2B—Fe1B—C8B | 133.60 (10) |
C3A—Fe1A—C8A | 109.93 (11) | C4B—Fe1B—C8B | 119.45 (10) |
C4A—Fe1A—C8A | 123.00 (11) | C3B—Fe1B—C8B | 112.56 (10) |
C6A—Fe1A—C1A | 104.37 (10) | C6B—Fe1B—C1B | 104.13 (10) |
C7A—Fe1A—C1A | 122.85 (10) | C10B—Fe1B—C1B | 112.02 (10) |
C10A—Fe1A—C1A | 117.89 (10) | C7B—Fe1B—C1B | 128.72 (10) |
C3A—Fe1A—C1A | 69.14 (10) | C4B—Fe1B—C1B | 69.51 (9) |
C4A—Fe1A—C1A | 69.21 (11) | C9B—Fe1B—C1B | 145.92 (10) |
C9A—Fe1A—C1A | 154.66 (11) | C3B—Fe1B—C1B | 69.36 (9) |
C8A—Fe1A—C1A | 161.35 (11) | C8B—Fe1B—C1B | 168.98 (10) |
C5A—C1A—C2A | 105.3 (2) | C5B—C1B—C2B | 105.5 (2) |
C5A—C1A—B1A | 126.7 (2) | C5B—C1B—B1B | 127.0 (2) |
C2A—C1A—B1A | 128.0 (2) | C2B—C1B—B1B | 127.4 (2) |
C5A—C1A—Fe1A | 68.52 (15) | C5B—C1B—Fe1B | 68.64 (12) |
C2A—C1A—Fe1A | 68.39 (13) | C2B—C1B—Fe1B | 68.83 (12) |
B1A—C1A—Fe1A | 127.47 (17) | B1B—C1B—Fe1B | 125.36 (15) |
C3A—C2A—C1A | 109.9 (2) | C3B—C2B—C1B | 109.7 (2) |
C3A—C2A—Fe1A | 69.70 (16) | C3B—C2B—Fe1B | 69.79 (12) |
C1A—C2A—Fe1A | 70.87 (14) | C1B—C2B—Fe1B | 70.28 (12) |
C3A—C2A—H2AA | 125.1 | C3B—C2B—H2BA | 125.2 |
C1A—C2A—H2AA | 125.1 | C1B—C2B—H2BA | 125.2 |
Fe1A—C2A—H2AA | 125.1 | Fe1B—C2B—H2BA | 125.2 |
C4A—C3A—C2A | 107.7 (2) | C4B—C3B—C2B | 107.6 (2) |
C4A—C3A—Fe1A | 69.76 (16) | C4B—C3B—Fe1B | 69.44 (13) |
C2A—C3A—Fe1A | 69.57 (14) | C2B—C3B—Fe1B | 69.37 (12) |
C4A—C3A—H3AA | 126.2 | C4B—C3B—H3BA | 126.2 |
C2A—C3A—H3AA | 126.2 | C2B—C3B—H3BA | 126.2 |
Fe1A—C3A—H3AA | 126.2 | Fe1B—C3B—H3BA | 126.2 |
C3A—C4A—C5A | 107.3 (3) | C3B—C4B—C5B | 107.3 (2) |
C3A—C4A—Fe1A | 69.70 (16) | C3B—C4B—Fe1B | 69.84 (13) |
C5A—C4A—Fe1A | 69.46 (15) | C5B—C4B—Fe1B | 69.28 (13) |
C3A—C4A—H4AA | 126.3 | C3B—C4B—H4BA | 126.3 |
C5A—C4A—H4AA | 126.3 | C5B—C4B—H4BA | 126.3 |
Fe1A—C4A—H4AA | 126.3 | Fe1B—C4B—H4BA | 126.3 |
C1A—C5A—C4A | 109.8 (2) | C4B—C5B—C1B | 109.9 (2) |
C1A—C5A—Fe1A | 70.91 (14) | C4B—C5B—Fe1B | 69.73 (13) |
C4A—C5A—Fe1A | 69.54 (15) | C1B—C5B—Fe1B | 70.52 (13) |
C1A—C5A—H5AA | 125.1 | C4B—C5B—H5BA | 125.0 |
C4A—C5A—H5AA | 125.1 | C1B—C5B—H5BA | 125.0 |
Fe1A—C5A—H5AA | 125.1 | Fe1B—C5B—H5BA | 125.0 |
C10A—C6A—C7A | 108.4 (2) | C10B—C6B—C7B | 107.6 (2) |
C10A—C6A—Fe1A | 69.92 (16) | C10B—C6B—Fe1B | 69.77 (14) |
C7A—C6A—Fe1A | 69.66 (14) | C7B—C6B—Fe1B | 70.00 (14) |
C10A—C6A—H6AA | 125.8 | C10B—C6B—H6BA | 126.2 |
C7A—C6A—H6AA | 125.8 | C7B—C6B—H6BA | 126.2 |
Fe1A—C6A—H6AA | 125.8 | Fe1B—C6B—H6BA | 126.2 |
C6A—C7A—C8A | 108.1 (2) | C8B—C7B—C6B | 108.2 (2) |
C6A—C7A—Fe1A | 69.59 (15) | C8B—C7B—Fe1B | 70.45 (14) |
C8A—C7A—Fe1A | 70.02 (15) | C6B—C7B—Fe1B | 69.21 (14) |
C6A—C7A—H7AA | 125.9 | C8B—C7B—H7BA | 125.9 |
C8A—C7A—H7AA | 125.9 | C6B—C7B—H7BA | 125.9 |
Fe1A—C7A—H7AA | 125.9 | Fe1B—C7B—H7BA | 125.9 |
C9A—C8A—C7A | 107.7 (2) | C9B—C8B—C7B | 107.6 (2) |
C9A—C8A—Fe1A | 69.69 (15) | C9B—C8B—Fe1B | 69.47 (14) |
C7A—C8A—Fe1A | 69.20 (15) | C7B—C8B—Fe1B | 69.13 (14) |
C9A—C8A—H8AA | 126.1 | C9B—C8B—H8BA | 126.2 |
C7A—C8A—H8AA | 126.1 | C7B—C8B—H8BA | 126.2 |
Fe1A—C8A—H8AA | 126.1 | Fe1B—C8B—H8BA | 126.2 |
C8A—C9A—C10A | 108.2 (3) | C10B—C9B—C8B | 108.6 (2) |
C8A—C9A—Fe1A | 69.74 (16) | C10B—C9B—Fe1B | 69.37 (13) |
C10A—C9A—Fe1A | 69.36 (16) | C8B—C9B—Fe1B | 70.28 (13) |
C8A—C9A—H9AA | 125.9 | C10B—C9B—H9BA | 125.7 |
C10A—C9A—H9AA | 125.9 | C8B—C9B—H9BA | 125.7 |
Fe1A—C9A—H9AA | 125.9 | Fe1B—C9B—H9BA | 125.7 |
C6A—C10A—C9A | 107.5 (2) | C9B—C10B—C6B | 108.0 (2) |
C6A—C10A—Fe1A | 69.42 (15) | C9B—C10B—Fe1B | 70.30 (14) |
C9A—C10A—Fe1A | 69.70 (15) | C6B—C10B—Fe1B | 69.39 (13) |
C6A—C10A—H10A | 126.2 | C9B—C10B—H10B | 126.0 |
C9A—C10A—H10A | 126.2 | C6B—C10B—H10B | 126.0 |
Fe1A—C10A—H10A | 126.2 | Fe1B—C10B—H10B | 126.0 |
F2A—B1A—F1A | 107.2 (2) | F3B—B1B—F2B | 108.4 (2) |
F2A—B1A—F3A | 107.8 (2) | F3B—B1B—F1B | 106.7 (2) |
F1A—B1A—F3A | 107.7 (2) | F2B—B1B—F1B | 106.3 (2) |
F2A—B1A—C1A | 111.2 (2) | F3B—B1B—C1B | 112.4 (2) |
F1A—B1A—C1A | 110.7 (2) | F2B—B1B—C1B | 111.7 (2) |
F3A—B1A—C1A | 112.1 (2) | F1B—B1B—C1B | 111.0 (2) |
C15A—N1A—C19A | 107.89 (17) | C15B—N1B—C11B | 108.26 (17) |
C15A—N1A—C23A | 111.46 (17) | C15B—N1B—C19B | 109.35 (17) |
C19A—N1A—C23A | 109.11 (16) | C11B—N1B—C19B | 111.24 (17) |
C15A—N1A—C11A | 108.26 (16) | C15B—N1B—C23B | 111.11 (17) |
C19A—N1A—C11A | 111.23 (17) | C11B—N1B—C23B | 108.69 (17) |
C23A—N1A—C11A | 108.91 (16) | C19B—N1B—C23B | 108.20 (17) |
C12A—C11A—N1A | 115.95 (18) | C12B—C11B—N1B | 117.1 (2) |
C12A—C11A—H11A | 108.3 | C12B—C11B—H11C | 108.0 |
N1A—C11A—H11A | 108.3 | N1B—C11B—H11C | 108.0 |
C12A—C11A—H11B | 108.3 | C12B—C11B—H11D | 108.0 |
N1A—C11A—H11B | 108.3 | N1B—C11B—H11D | 108.0 |
H11A—C11A—H11B | 107.4 | H11C—C11B—H11D | 107.3 |
C11A—C12A—C13A | 109.62 (19) | C11B—C12B—C13B | 108.8 (2) |
C11A—C12A—H12A | 109.7 | C11B—C12B—H12C | 109.9 |
C13A—C12A—H12A | 109.7 | C13B—C12B—H12C | 109.9 |
C11A—C12A—H12B | 109.7 | C11B—C12B—H12D | 109.9 |
C13A—C12A—H12B | 109.7 | C13B—C12B—H12D | 109.9 |
H12A—C12A—H12B | 108.2 | H12C—C12B—H12D | 108.3 |
C14A—C13A—C12A | 111.9 (2) | C14B—C13B—C12B | 113.0 (3) |
C14A—C13A—H13A | 109.2 | C14B—C13B—H13C | 109.0 |
C12A—C13A—H13A | 109.2 | C12B—C13B—H13C | 109.0 |
C14A—C13A—H13B | 109.2 | C14B—C13B—H13D | 109.0 |
C12A—C13A—H13B | 109.2 | C12B—C13B—H13D | 109.0 |
H13A—C13A—H13B | 107.9 | H13C—C13B—H13D | 107.8 |
C13A—C14A—H14A | 109.5 | C13B—C14B—H14D | 109.5 |
C13A—C14A—H14B | 109.5 | C13B—C14B—H14E | 109.5 |
H14A—C14A—H14B | 109.5 | H14D—C14B—H14E | 109.5 |
C13A—C14A—H14C | 109.5 | C13B—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H14D—C14B—H14F | 109.5 |
H14B—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
N1A—C15A—C16A | 115.08 (18) | C16B—C15B—N1B | 115.49 (19) |
N1A—C15A—H15A | 108.5 | C16B—C15B—H15C | 108.4 |
C16A—C15A—H15A | 108.5 | N1B—C15B—H15C | 108.4 |
N1A—C15A—H15B | 108.5 | C16B—C15B—H15D | 108.4 |
C16A—C15A—H15B | 108.5 | N1B—C15B—H15D | 108.4 |
H15A—C15A—H15B | 107.5 | H15C—C15B—H15D | 107.5 |
C17A—C16A—C15A | 111.61 (19) | C15B—C16B—C17B | 110.1 (2) |
C17A—C16A—H16A | 109.3 | C15B—C16B—H16C | 109.6 |
C15A—C16A—H16A | 109.3 | C17B—C16B—H16C | 109.6 |
C17A—C16A—H16B | 109.3 | C15B—C16B—H16D | 109.6 |
C15A—C16A—H16B | 109.3 | C17B—C16B—H16D | 109.6 |
H16A—C16A—H16B | 108.0 | H16C—C16B—H16D | 108.1 |
C16A—C17A—C18A | 111.9 (2) | C16B—C17B—C18B | 111.9 (2) |
C16A—C17A—H17A | 109.2 | C16B—C17B—H17C | 109.2 |
C18A—C17A—H17A | 109.2 | C18B—C17B—H17C | 109.2 |
C16A—C17A—H17B | 109.2 | C16B—C17B—H17D | 109.2 |
C18A—C17A—H17B | 109.2 | C18B—C17B—H17D | 109.2 |
H17A—C17A—H17B | 107.9 | H17C—C17B—H17D | 107.9 |
C17A—C18A—H18A | 109.5 | C17B—C18B—H18D | 109.5 |
C17A—C18A—H18B | 109.5 | C17B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
C17A—C18A—H18C | 109.5 | C17B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
C20A—C19A—N1A | 116.11 (18) | C20B—C19B—N1B | 116.40 (19) |
C20A—C19A—H19A | 108.3 | C20B—C19B—H19C | 108.2 |
N1A—C19A—H19A | 108.3 | N1B—C19B—H19C | 108.2 |
C20A—C19A—H19B | 108.3 | C20B—C19B—H19D | 108.2 |
N1A—C19A—H19B | 108.3 | N1B—C19B—H19D | 108.2 |
H19A—C19A—H19B | 107.4 | H19C—C19B—H19D | 107.3 |
C19A—C20A—C21A | 110.55 (19) | C19B—C20B—C21B | 110.7 (2) |
C19A—C20A—H20A | 109.5 | C19B—C20B—H20C | 109.5 |
C21A—C20A—H20A | 109.5 | C21B—C20B—H20C | 109.5 |
C19A—C20A—H20B | 109.5 | C19B—C20B—H20D | 109.5 |
C21A—C20A—H20B | 109.5 | C21B—C20B—H20D | 109.5 |
H20A—C20A—H20B | 108.1 | H20C—C20B—H20D | 108.1 |
C22A—C21A—C20A | 113.2 (2) | C20B—C21B—C22B | 111.9 (2) |
C22A—C21A—H21A | 108.9 | C20B—C21B—H21C | 109.2 |
C20A—C21A—H21A | 108.9 | C22B—C21B—H21C | 109.2 |
C22A—C21A—H21B | 108.9 | C20B—C21B—H21D | 109.2 |
C20A—C21A—H21B | 108.9 | C22B—C21B—H21D | 109.2 |
H21A—C21A—H21B | 107.8 | H21C—C21B—H21D | 107.9 |
C21A—C22A—H22A | 109.5 | C21B—C22B—H22D | 109.5 |
C21A—C22A—H22B | 109.5 | C21B—C22B—H22E | 109.5 |
H22A—C22A—H22B | 109.5 | H22D—C22B—H22E | 109.5 |
C21A—C22A—H22C | 109.5 | C21B—C22B—H22F | 109.5 |
H22A—C22A—H22C | 109.5 | H22D—C22B—H22F | 109.5 |
H22B—C22A—H22C | 109.5 | H22E—C22B—H22F | 109.5 |
C24A—C23A—N1A | 115.78 (18) | C24B—C23B—N1B | 116.59 (18) |
C24A—C23A—H23A | 108.3 | C24B—C23B—H23C | 108.1 |
N1A—C23A—H23A | 108.3 | N1B—C23B—H23C | 108.1 |
C24A—C23A—H23B | 108.3 | C24B—C23B—H23D | 108.1 |
N1A—C23A—H23B | 108.3 | N1B—C23B—H23D | 108.1 |
H23A—C23A—H23B | 107.4 | H23C—C23B—H23D | 107.3 |
C23A—C24A—C25A | 110.32 (19) | C23B—C24B—C25B | 109.1 (2) |
C23A—C24A—H24A | 109.6 | C23B—C24B—H24C | 109.9 |
C25A—C24A—H24A | 109.6 | C25B—C24B—H24C | 109.9 |
C23A—C24A—H24B | 109.6 | C23B—C24B—H24D | 109.9 |
C25A—C24A—H24B | 109.6 | C25B—C24B—H24D | 109.9 |
H24A—C24A—H24B | 108.1 | H24C—C24B—H24D | 108.3 |
C24A—C25A—C26A | 111.4 (2) | C26B—C25B—C24B | 113.4 (2) |
C24A—C25A—H25A | 109.3 | C26B—C25B—H25C | 108.9 |
C26A—C25A—H25A | 109.3 | C24B—C25B—H25C | 108.9 |
C24A—C25A—H25B | 109.3 | C26B—C25B—H25D | 108.9 |
C26A—C25A—H25B | 109.3 | C24B—C25B—H25D | 108.9 |
H25A—C25A—H25B | 108.0 | H25C—C25B—H25D | 107.7 |
C25A—C26A—H26A | 109.5 | C25B—C26B—H26D | 109.5 |
C25A—C26A—H26B | 109.5 | C25B—C26B—H26E | 109.5 |
H26A—C26A—H26B | 109.5 | H26D—C26B—H26E | 109.5 |
C25A—C26A—H26C | 109.5 | C25B—C26B—H26F | 109.5 |
H26A—C26A—H26C | 109.5 | H26D—C26B—H26F | 109.5 |
H26B—C26A—H26C | 109.5 | H26E—C26B—H26F | 109.5 |
C2A—C1A—B1A—F1A | 113.5 (3) | C2B—C1B—B1B—F1B | 90.5 (3) |
C2A—C1A—B1A—F2A | −5.5 (4) | C2B—C1B—B1B—F2B | −27.9 (3) |
C2A—C1A—B1A—F3A | −126.3 (3) | C2B—C1B—B1B—F3B | −150.0 (2) |
Experimental details
Crystal data | |
Chemical formula | (C16H36N)[Fe(C5H5)(C5H4BF3)] |
Mr | 495.29 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 2673.31 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.60 |
Crystal size (mm) | 0.25 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.865, 0.916 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 50155, 12237, 8213 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.123, 1.02 |
No. of reflections | 12237 |
No. of parameters | 578 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.45 |
Computer programs: COLLECT (Nonius, 1997-2001), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1999), SHELXTL.
C1A—B1A | 1.608 (3) | C1B—B1B | 1.605 (4) |
C5A—C1A—B1A | 126.7 (2) | C5B—C1B—B1B | 127.0 (2) |
C2A—C1A—B1A | 128.0 (2) | C2B—C1B—B1B | 127.4 (2) |
C2A—C1A—B1A—F1A | 113.5 (3) | C2B—C1B—B1B—F1B | 90.5 (3) |
C2A—C1A—B1A—F2A | −5.5 (4) | C2B—C1B—B1B—F2B | −27.9 (3) |
C2A—C1A—B1A—F3A | −126.3 (3) | C2B—C1B—B1B—F3B | −150.0 (2) |
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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.