Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013988/om6042sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013988/om6042Isup2.hkl |
CCDC reference: 172196
2,4,6-Tris(1'-phenylthio-1-ferrocenyl)boroxin, (I), was prepared by treating a cold (195 K) tetrahydrofuran (10 ml) solution of 1,1'-bis(tri-n-butylstannyl)ferrocene (1.56 g, 2.0 mmol) (Wright, 1990) under argon with n-BuLi (in hexane, 2.0 mmol) for 30 min, followed by the addition of diphenyl disulfide (0.436 g, 2.0 mmol). After the solution was stirred at 195 K for 1 h and 273 K for 3 h, the reaction was quenched with aqueous ammonium chloride, and extracted with diethyl ether, and the ether extract was dried (MgSO4), concentrated, and column chromatographed on silica gel to give an 89% yield of 1-(tri-n-butylstannyl)-1'-(phenylthio)ferrocene. The resulting sulfenylferrocene (0.60 g, 1.0 mmol) in 10 ml of tetrahydrofuran under argon was treated with n-BuLi (in hexane, 1.2 mmol) at 195 K for 30 min, followed by trimethyl borate (0.13 ml, 1.2 mmol). After the solution was stirred at 195 K for 1 h and 273 K for 1 h, 0.5 N HCl (10 ml) was added, and the solution was stirred at 248 K for 1 h and extracted with ether. The ether extract was dried (MgSO4), concentrated, and triturated with cold hexane twice, and the remaining yellow solids were dried under vacuo to give (I) (74% yield). Recrystallization of (I) from ether gave yellow crystals (m.p. 404–406 K) suitable for X-ray analysis.
Although the crystal diffracted strongly at low angle and was of good quality judging by its peak shapes, it diffracted poorly at higher angles. Thus only about 30% of the approximately 15 000 possible diffraction maxima were observed at the 2σ level, despite three weeks of data collection. Certainly low-temperature data would have improved the data set considerably but our laboratory does not currently have that capability.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965) in TEXSAN; software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2000).
[Fe3(C15H12B3O3)(C11H9S)3] | F(000) = 1968 |
Mr = 959.98 | Dx = 1.463 Mg m−3 |
Triclinic, P1 | Melting point = 404–406 K |
a = 17.501 (4) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 18.875 (5) Å | Cell parameters from 25 reflections |
c = 14.999 (4) Å | θ = 10.1–13.1° |
α = 113.137 (19)° | µ = 1.17 mm−1 |
β = 101.89 (2)° | T = 296 K |
γ = 74.30 (2)° | Prism, brown |
V = 4358.4 (19) Å3 | 0.43 × 0.17 × 0.13 mm |
Z = 4 |
Rigaku AFC-5S diffractometer | 4619 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.079 |
Graphite monochromator | θmax = 25.1°, θmin = 1.8° |
ω scans | h = 0→20 |
Absorption correction: ψ scan (North et al., 1968) | k = −21→22 |
Tmin = 0.791, Tmax = 0.859 | l = −17→17 |
16062 measured reflections | 3 standard reflections every 100 reflections |
15452 independent reflections | intensity decay: 0.9% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0438P)2] where P = (Fo2 + 2Fc2)/3 |
15452 reflections | (Δ/σ)max = 0.001 |
1081 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
[Fe3(C15H12B3O3)(C11H9S)3] | γ = 74.30 (2)° |
Mr = 959.98 | V = 4358.4 (19) Å3 |
Triclinic, P1 | Z = 4 |
a = 17.501 (4) Å | Mo Kα radiation |
b = 18.875 (5) Å | µ = 1.17 mm−1 |
c = 14.999 (4) Å | T = 296 K |
α = 113.137 (19)° | 0.43 × 0.17 × 0.13 mm |
β = 101.89 (2)° |
Rigaku AFC-5S diffractometer | 4619 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.079 |
Tmin = 0.791, Tmax = 0.859 | 3 standard reflections every 100 reflections |
16062 measured reflections | intensity decay: 0.9% |
15452 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.40 e Å−3 |
15452 reflections | Δρmin = −0.49 e Å−3 |
1081 parameters |
Geometry. FERROCENE GROUP CENTROIDS Ferrocene Name Fractional Coordinates Fe1 (bottom) Cg1 0.3659 (2) 1.0827 (2) 0.9680 (3) Fe1 (top) Cg2 0.2254 (2) 1.0619 (2) 0.7820 (3) Fe2 (bottom) Cg3 0.5496 (2) 0.6678 (2) 0.8118 (3) Fe2 (top) Cg4 0.3964 (2) 0.6438 (3) 0.6434 (3) Fe3 (bottom) Cg5 0.6717 (2) 0.9288 (2) 0.6565 (3) Fe3 (top) Cg6 0.5741 (3) 0.8381 (2) 0.4475 (3) Fe1a (bottom) Cg7 0.1365 (2) 0.9727 (2) 0.0910 (3) Fe1a (top) Cg8 0.2946 (2) 0.8243 (2) 0.0582 (3) Fe2a (bottom) Cg9 - 0.0175 (2) 0.8674 (3) -0.4184 (3) Fe2a (top) Cg10 0.1456 (3) 0.7296 (2) -0.4633 (4) Fe3a (bottom) Cg11 - 0.1489 (3) 0.7239 (3) -0.1176 (4) Fe3a (top) Cg12 - 0.0181 (3) 0.5559 (3) -0.1879 (5) FERROCENE TORSION ANGLES Fe1 Ferrocene C1—Cg1—Cg2—C6 - 6.5 (7) C2—Cg1—Cg2—C7 - 6.9 (7) C3—Cg1—Cg2—C8 - 7.1 (7) C4—Cg1—Cg2—C9 - 6.9 (8) C5—Cg1—Cg2—C10 - 6.5 (6) ————————— Fe2 Ferrocene C11—Cg3—Cg4—C16 - 7.0 (6) C12—Cg3—Cg4—C17 - 6.4 (8) C13—Cg3—Cg4—C18 - 6.0 (8) C14—Cg3—Cg4—C19 - 6.1 (7) C15—Cg3—Cg4—C20 - 6.8 (7) ————————— Fe3 Ferrocene C21—Cg5—Cg6—C26 2.2 (8) C22—Cg5—Cg6—C27 4.0 (7) C23—Cg5—Cg6—C28 3.6 (8) C24—Cg5—Cg6—C29 2.5 (8) C25—Cg5—Cg6—C30 2.6 (7) ————————— Fe1a Ferrocene C1a—Cg7—Cg8—C6a -5.1 (7) C2a—Cg7—Cg8—C7a -5.4 (6) C3a—Cg7—Cg8—C8a -5.7 (7) C4a—Cg7—Cg8—C9a -5.7 (7) C5a—Cg7—Cg8—C10a - 4.9 (7) —————————- Fe2a Ferrocene C11a—Cg9—Cg10—C16a - 12.2 (7) C12a—Cg9—Cg10—C17a - 11.5 (8) C13a—Cg9—Cg10—C18a - 10.4 (9) C14a—Cg9—Cg10—C19a - 12.3 (9) C15a—Cg9—Cg10—C20a - 11.2 (7) —————————— Fe3a C21a—Cg11—Cg12—C26a - 41.8 (11) C22a—Cg11—Cg12—C27a - 40.9 (9) C23a—Cg11—Cg12—C28a - 41.6 (9) C24a—Cg11—Cg12—C29a - 42.2 (9) C25a—Cg11—Cg12—C30a - 41.3 (11) ——————————— |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.29685 (7) | 1.06919 (6) | 0.87315 (8) | 0.0471 (3) | |
Fe2 | 0.47392 (7) | 0.65657 (6) | 0.72540 (9) | 0.0492 (3) | |
Fe3 | 0.62170 (7) | 0.88341 (7) | 0.55256 (9) | 0.0497 (3) | |
S1 | 0.33682 (15) | 0.93442 (14) | 0.65159 (16) | 0.0696 (7) | |
S2 | 0.49139 (14) | 0.65204 (14) | 0.50676 (18) | 0.0638 (7) | |
S3 | 0.73295 (16) | 0.77355 (15) | 0.37595 (18) | 0.0737 (7) | |
O1 | 0.5161 (3) | 0.9637 (3) | 0.8049 (4) | 0.0507 (14) | |
O2 | 0.4739 (3) | 0.8787 (3) | 0.8586 (3) | 0.0491 (14) | |
O3 | 0.5778 (3) | 0.8279 (3) | 0.7552 (4) | 0.0519 (15) | |
B1 | 0.4684 (6) | 0.9526 (6) | 0.8588 (7) | 0.044 (2) | |
B2 | 0.5312 (6) | 0.8160 (5) | 0.8096 (7) | 0.046 (3) | |
B3 | 0.5721 (6) | 0.9014 (6) | 0.7544 (7) | 0.048 (3) | |
C1 | 0.4118 (5) | 1.0249 (5) | 0.9210 (5) | 0.046 (2) | |
C2 | 0.4030 (5) | 1.1039 (5) | 0.9291 (6) | 0.054 (2) | |
C3 | 0.3443 (5) | 1.1524 (5) | 0.9898 (6) | 0.061 (3) | |
C4 | 0.3147 (5) | 1.1056 (5) | 1.0217 (6) | 0.062 (3) | |
C5 | 0.3559 (5) | 1.0269 (5) | 0.9783 (5) | 0.052 (2) | |
C6 | 0.2704 (5) | 1.0093 (5) | 0.7288 (5) | 0.050 (2) | |
C7 | 0.2581 (5) | 1.0910 (5) | 0.7472 (6) | 0.061 (3) | |
C8 | 0.2011 (5) | 1.1319 (5) | 0.8138 (6) | 0.064 (3) | |
C9 | 0.1777 (5) | 1.0766 (6) | 0.8359 (6) | 0.066 (3) | |
C10 | 0.2195 (5) | 1.0006 (5) | 0.7844 (6) | 0.057 (2) | |
C11 | 0.5439 (5) | 0.7343 (5) | 0.8138 (6) | 0.049 (2) | |
C12 | 0.5046 (5) | 0.7108 (5) | 0.8694 (6) | 0.058 (2) | |
C13 | 0.5274 (5) | 0.6289 (6) | 0.8462 (7) | 0.067 (3) | |
C14 | 0.5804 (6) | 0.6010 (5) | 0.7745 (7) | 0.071 (3) | |
C15 | 0.5917 (5) | 0.6638 (5) | 0.7550 (6) | 0.061 (3) | |
C16 | 0.3848 (5) | 0.7114 (5) | 0.6521 (6) | 0.063 (3) | |
C17 | 0.3520 (5) | 0.6808 (7) | 0.7042 (7) | 0.071 (3) | |
C18 | 0.3811 (6) | 0.6008 (6) | 0.6733 (7) | 0.076 (3) | |
C19 | 0.4308 (5) | 0.5782 (5) | 0.6004 (6) | 0.061 (2) | |
C20 | 0.4333 (5) | 0.6477 (5) | 0.5870 (6) | 0.050 (2) | |
C21 | 0.6291 (5) | 0.9165 (5) | 0.7024 (6) | 0.048 (2) | |
C22 | 0.7025 (5) | 0.8660 (5) | 0.6638 (6) | 0.058 (2) | |
C23 | 0.7320 (5) | 0.9029 (6) | 0.6177 (7) | 0.073 (3) | |
C24 | 0.6787 (6) | 0.9750 (6) | 0.6230 (7) | 0.068 (3) | |
C25 | 0.6163 (5) | 0.9834 (5) | 0.6754 (6) | 0.056 (2) | |
C26 | 0.5291 (6) | 0.8267 (6) | 0.4877 (7) | 0.071 (3) | |
C27 | 0.6018 (6) | 0.7765 (5) | 0.4592 (6) | 0.063 (3) | |
C28 | 0.6372 (5) | 0.8107 (5) | 0.4149 (6) | 0.060 (3) | |
C29 | 0.5849 (6) | 0.8836 (5) | 0.4148 (6) | 0.061 (2) | |
C30 | 0.5177 (5) | 0.8929 (5) | 0.4609 (7) | 0.066 (3) | |
C31 | 0.2800 (5) | 0.9146 (5) | 0.5358 (5) | 0.044 (2) | |
C32 | 0.2083 (5) | 0.9625 (5) | 0.5155 (6) | 0.060 (2) | |
C33 | 0.1703 (5) | 0.9420 (5) | 0.4225 (7) | 0.065 (3) | |
C34 | 0.2012 (6) | 0.8764 (5) | 0.3485 (6) | 0.061 (3) | |
C35 | 0.2715 (6) | 0.8285 (5) | 0.3683 (6) | 0.058 (2) | |
C36 | 0.3098 (5) | 0.8478 (5) | 0.4615 (7) | 0.054 (2) | |
C37 | 0.4305 (6) | 0.6323 (5) | 0.3932 (7) | 0.059 (2) | |
C38 | 0.3526 (6) | 0.6268 (5) | 0.3835 (7) | 0.070 (3) | |
C39 | 0.3072 (6) | 0.6124 (6) | 0.2929 (10) | 0.085 (3) | |
C40 | 0.3407 (9) | 0.6035 (6) | 0.2138 (9) | 0.103 (4) | |
C41 | 0.4155 (8) | 0.6105 (7) | 0.2232 (9) | 0.104 (4) | |
C42 | 0.4625 (7) | 0.6238 (6) | 0.3127 (9) | 0.093 (4) | |
C43 | 0.7170 (8) | 0.7175 (6) | 0.2492 (7) | 0.073 (3) | |
C44 | 0.6455 (9) | 0.7292 (6) | 0.1949 (8) | 0.101 (4) | |
C45 | 0.6370 (10) | 0.6869 (8) | 0.0938 (10) | 0.127 (5) | |
C46 | 0.6988 (14) | 0.6334 (10) | 0.0525 (12) | 0.144 (8) | |
C47 | 0.7687 (12) | 0.6188 (10) | 0.1065 (13) | 0.145 (7) | |
C48 | 0.7792 (8) | 0.6616 (7) | 0.2061 (10) | 0.106 (4) | |
H2 | 0.4319 | 1.1208 | 0.8987 | 0.065* | |
H3 | 0.3277 | 1.2067 | 1.0063 | 0.074* | |
H4 | 0.2754 | 1.1229 | 1.0634 | 0.075* | |
H5 | 0.3475 | 0.9833 | 0.9863 | 0.062* | |
H7 | 0.2835 | 1.1137 | 0.7199 | 0.074* | |
H8 | 0.1823 | 1.1862 | 0.8385 | 0.077* | |
H9 | 0.1403 | 1.0879 | 0.8782 | 0.079* | |
H10 | 0.2146 | 0.9534 | 0.7864 | 0.068* | |
H12 | 0.4693 | 0.7448 | 0.9143 | 0.070* | |
H13 | 0.5110 | 0.5992 | 0.8726 | 0.081* | |
H14 | 0.6043 | 0.5483 | 0.7446 | 0.085* | |
H15 | 0.6247 | 0.6601 | 0.7113 | 0.074* | |
H16 | 0.3760 | 0.7642 | 0.6595 | 0.075* | |
H17 | 0.3170 | 0.7097 | 0.7511 | 0.086* | |
H18 | 0.3696 | 0.5668 | 0.6972 | 0.091* | |
H19 | 0.4571 | 0.5272 | 0.5671 | 0.073* | |
H22 | 0.7261 | 0.8171 | 0.6689 | 0.070* | |
H23 | 0.7790 | 0.8832 | 0.5884 | 0.087* | |
H24 | 0.6837 | 1.0106 | 0.5968 | 0.082* | |
H25 | 0.5733 | 1.0262 | 0.6899 | 0.068* | |
H26 | 0.4939 | 0.8179 | 0.5191 | 0.086* | |
H27 | 0.6230 | 0.7287 | 0.4681 | 0.076* | |
H29 | 0.5933 | 0.9182 | 0.3893 | 0.073* | |
H30 | 0.4741 | 0.9352 | 0.4715 | 0.080* | |
H32 | 0.1865 | 1.0079 | 0.5645 | 0.072* | |
H33 | 0.1219 | 0.9738 | 0.4092 | 0.078* | |
H34 | 0.1748 | 0.8643 | 0.2855 | 0.073* | |
H35 | 0.2932 | 0.7833 | 0.3189 | 0.069* | |
H36 | 0.3572 | 0.8148 | 0.4746 | 0.064* | |
H38 | 0.3300 | 0.6327 | 0.4376 | 0.084* | |
H39 | 0.2542 | 0.6088 | 0.2863 | 0.101* | |
H40 | 0.3108 | 0.5925 | 0.1528 | 0.123* | |
H41 | 0.4369 | 0.6064 | 0.1691 | 0.125* | |
H42 | 0.5154 | 0.6270 | 0.3179 | 0.112* | |
H44 | 0.6020 | 0.7654 | 0.2248 | 0.121* | |
H45 | 0.5886 | 0.6961 | 0.0563 | 0.152* | |
H46 | 0.6937 | 0.6058 | −0.0144 | 0.173* | |
H47 | 0.8106 | 0.5795 | 0.0769 | 0.174* | |
H48 | 0.8281 | 0.6522 | 0.2426 | 0.127* | |
Fe1a | 0.21424 (7) | 0.89679 (7) | 0.07239 (8) | 0.0534 (4) | |
Fe2a | 0.06336 (7) | 0.79691 (7) | −0.44042 (9) | 0.0537 (4) | |
Fe3a | −0.08267 (8) | 0.64032 (8) | −0.15273 (9) | 0.0637 (4) | |
S1a | 0.19960 (15) | 0.72321 (14) | −0.10513 (18) | 0.0751 (8) | |
S2a | 0.07081 (15) | 0.61748 (15) | −0.4399 (2) | 0.0797 (8) | |
S3a | −0.12791 (17) | 0.48871 (17) | −0.1357 (2) | 0.1007 (10) | |
O1a | 0.0028 (3) | 0.8410 (3) | −0.0604 (4) | 0.0597 (16) | |
O2a | 0.0468 (3) | 0.8913 (3) | −0.1604 (4) | 0.0583 (16) | |
O3a | −0.0458 (3) | 0.8063 (3) | −0.2291 (4) | 0.0612 (16) | |
B1a | 0.0488 (6) | 0.8856 (6) | −0.0709 (8) | 0.056 (3) | |
B2a | −0.0015 (7) | 0.8533 (6) | −0.2389 (8) | 0.058 (3) | |
B3a | −0.0469 (6) | 0.8024 (6) | −0.1388 (9) | 0.059 (3) | |
C1a | 0.0971 (5) | 0.9348 (5) | 0.0193 (6) | 0.054 (2) | |
C2a | 0.1016 (5) | 0.9393 (5) | 0.1176 (6) | 0.056 (2) | |
C3a | 0.1536 (6) | 0.9886 (5) | 0.1778 (6) | 0.064 (3) | |
C4a | 0.1824 (5) | 1.0170 (5) | 0.1196 (7) | 0.065 (3) | |
C5a | 0.1477 (5) | 0.9838 (5) | 0.0209 (6) | 0.061 (3) | |
C6a | 0.2568 (5) | 0.7813 (5) | −0.0092 (6) | 0.052 (2) | |
C7a | 0.2635 (5) | 0.7925 (5) | 0.0925 (6) | 0.062 (3) | |
C8a | 0.3134 (5) | 0.8465 (5) | 0.1451 (6) | 0.061 (2) | |
C9a | 0.3370 (5) | 0.8702 (5) | 0.0788 (7) | 0.060 (2) | |
C10a | 0.3025 (5) | 0.8312 (5) | −0.0161 (7) | 0.064 (3) | |
C11a | −0.0144 (5) | 0.8648 (5) | −0.3380 (6) | 0.050 (2) | |
C12a | 0.0232 (5) | 0.9123 (5) | −0.3624 (7) | 0.062 (3) | |
C13a | 0.0036 (6) | 0.8972 (6) | −0.4631 (8) | 0.080 (3) | |
C14a | −0.0450 (6) | 0.8426 (7) | −0.5024 (7) | 0.076 (3) | |
C15a | −0.0551 (5) | 0.8203 (5) | −0.4260 (7) | 0.065 (3) | |
C16a | 0.1589 (5) | 0.7358 (5) | −0.3798 (7) | 0.063 (3) | |
C17a | 0.1842 (5) | 0.7786 (5) | −0.4213 (9) | 0.072 (3) | |
C18a | 0.1570 (7) | 0.7544 (6) | −0.5191 (9) | 0.088 (4) | |
C19a | 0.1139 (6) | 0.6952 (6) | −0.5416 (7) | 0.067 (3) | |
C20a | 0.1139 (5) | 0.6840 (5) | −0.4547 (7) | 0.051 (2) | |
C21a | −0.1035 (5) | 0.7593 (5) | −0.1258 (7) | 0.060 (2) | |
C22a | −0.1625 (7) | 0.7241 (5) | −0.1984 (8) | 0.082 (3) | |
C23a | −0.2021 (6) | 0.6890 (7) | −0.1594 (11) | 0.099 (4) | |
C24a | −0.1686 (7) | 0.7015 (6) | −0.0622 (10) | 0.097 (4) | |
C25a | −0.1079 (6) | 0.7454 (5) | −0.0420 (7) | 0.072 (3) | |
C26a | −0.0020 (11) | 0.5721 (9) | −0.2494 (13) | 0.133 (6) | |
C27a | −0.0621 (8) | 0.5334 (6) | −0.2595 (8) | 0.095 (4) | |
C28a | −0.0619 (5) | 0.5257 (5) | −0.1695 (7) | 0.059 (2) | |
C29a | −0.0002 (6) | 0.5593 (6) | −0.1063 (8) | 0.083 (3) | |
C30a | 0.0358 (7) | 0.5891 (8) | −0.1549 (13) | 0.120 (5) | |
C31a | 0.2615 (6) | 0.6279 (5) | −0.1316 (7) | 0.066 (3) | |
C32a | 0.3302 (7) | 0.6100 (6) | −0.0753 (7) | 0.082 (3) | |
C33a | 0.3732 (7) | 0.5315 (7) | −0.1019 (9) | 0.102 (4) | |
C34a | 0.3475 (8) | 0.4737 (7) | −0.1823 (10) | 0.097 (4) | |
C35a | 0.2785 (8) | 0.4929 (6) | −0.2394 (9) | 0.093 (4) | |
C36a | 0.2362 (6) | 0.5702 (6) | −0.2138 (7) | 0.071 (3) | |
C37a | 0.1431 (6) | 0.5295 (5) | −0.4759 (6) | 0.061 (2) | |
C38a | 0.2161 (6) | 0.5239 (5) | −0.5024 (7) | 0.073 (3) | |
C39a | 0.2694 (7) | 0.4529 (8) | −0.5316 (8) | 0.103 (4) | |
C40a | 0.2489 (10) | 0.3857 (8) | −0.5382 (10) | 0.124 (6) | |
C41a | 0.1785 (11) | 0.3897 (9) | −0.5104 (10) | 0.121 (5) | |
C42a | 0.1252 (8) | 0.4614 (7) | −0.4796 (8) | 0.099 (4) | |
C43a | −0.0796 (6) | 0.3872 (6) | −0.1592 (7) | 0.073 (3) | |
C44a | −0.0130 (7) | 0.3513 (7) | −0.2068 (7) | 0.091 (3) | |
C45a | 0.0185 (8) | 0.2727 (8) | −0.2232 (8) | 0.112 (4) | |
C46a | −0.0146 (9) | 0.2291 (8) | −0.1954 (11) | 0.118 (5) | |
C47a | −0.0805 (9) | 0.2673 (9) | −0.1431 (12) | 0.126 (5) | |
C48a | −0.1146 (6) | 0.3452 (8) | −0.1260 (9) | 0.105 (4) | |
H2a | 0.0744 | 0.9135 | 0.1384 | 0.067* | |
H3a | 0.1668 | 1.0006 | 0.2446 | 0.076* | |
H4a | 0.2175 | 1.0511 | 0.1414 | 0.078* | |
H5a | 0.1565 | 0.9925 | −0.0327 | 0.073* | |
H7a | 0.2391 | 0.7683 | 0.1190 | 0.074* | |
H8a | 0.3281 | 0.8635 | 0.2121 | 0.073* | |
H9a | 0.3699 | 0.9058 | 0.0948 | 0.072* | |
H10a | 0.3084 | 0.8369 | −0.0731 | 0.077* | |
H12a | 0.0548 | 0.9469 | −0.3195 | 0.075* | |
H13a | 0.0206 | 0.9203 | −0.4980 | 0.096* | |
H14a | −0.0669 | 0.8238 | −0.5671 | 0.091* | |
H15a | −0.0835 | 0.7831 | −0.4325 | 0.078* | |
H16a | 0.1696 | 0.7402 | −0.3146 | 0.076* | |
H17a | 0.2142 | 0.8170 | −0.3885 | 0.086* | |
H18a | 0.1657 | 0.7739 | −0.5634 | 0.106* | |
H19a | 0.0899 | 0.6685 | −0.6028 | 0.081* | |
H22a | −0.1733 | 0.7243 | −0.2617 | 0.098* | |
H23a | −0.2430 | 0.6623 | −0.1921 | 0.119* | |
H24a | −0.1831 | 0.6845 | −0.0190 | 0.116* | |
H25a | −0.0765 | 0.7620 | 0.0172 | 0.087* | |
H26a | 0.0108 | 0.5846 | −0.2979 | 0.159* | |
H27a | −0.0965 | 0.5156 | −0.3158 | 0.114* | |
H29a | 0.0145 | 0.5615 | −0.0422 | 0.100* | |
H30a | 0.0776 | 0.6155 | −0.1286 | 0.144* | |
H32a | 0.3483 | 0.6491 | −0.0203 | 0.098* | |
H33a | 0.4201 | 0.5188 | −0.0639 | 0.123* | |
H34a | 0.3761 | 0.4219 | −0.1985 | 0.116* | |
H35a | 0.2606 | 0.4541 | −0.2948 | 0.111* | |
H36a | 0.1900 | 0.5832 | −0.2528 | 0.086* | |
H38a | 0.2295 | 0.5690 | −0.5004 | 0.087* | |
H39a | 0.3191 | 0.4504 | −0.5470 | 0.124* | |
H40a | 0.2835 | 0.3371 | −0.5618 | 0.149* | |
H41a | 0.1660 | 0.3443 | −0.5120 | 0.145* | |
H42a | 0.0768 | 0.4637 | −0.4611 | 0.119* | |
H44a | 0.0107 | 0.3796 | −0.2278 | 0.109* | |
H45a | 0.0644 | 0.2488 | −0.2548 | 0.134* | |
H46a | 0.0058 | 0.1754 | −0.2106 | 0.141* | |
H47a | −0.1019 | 0.2391 | −0.1192 | 0.152* | |
H48a | −0.1598 | 0.3695 | −0.0931 | 0.126* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0559 (8) | 0.0412 (7) | 0.0398 (7) | −0.0057 (6) | 0.0064 (6) | 0.0124 (6) |
Fe2 | 0.0457 (8) | 0.0422 (7) | 0.0564 (8) | −0.0077 (6) | 0.0063 (6) | 0.0148 (6) |
Fe3 | 0.0428 (8) | 0.0503 (8) | 0.0567 (8) | −0.0127 (6) | 0.0033 (6) | 0.0192 (7) |
S1 | 0.0683 (17) | 0.0643 (16) | 0.0463 (15) | 0.0032 (13) | −0.0060 (13) | 0.0060 (12) |
S2 | 0.0603 (16) | 0.0706 (17) | 0.0690 (17) | −0.0254 (13) | 0.0076 (13) | 0.0262 (14) |
S3 | 0.0779 (19) | 0.0713 (17) | 0.0688 (18) | −0.0087 (14) | 0.0163 (15) | 0.0226 (14) |
O1 | 0.052 (4) | 0.044 (3) | 0.055 (4) | −0.006 (3) | 0.002 (3) | 0.021 (3) |
O2 | 0.059 (4) | 0.041 (3) | 0.045 (3) | −0.004 (3) | 0.009 (3) | 0.016 (3) |
O3 | 0.068 (4) | 0.040 (4) | 0.048 (4) | −0.013 (3) | 0.012 (3) | 0.013 (3) |
B1 | 0.042 (6) | 0.044 (6) | 0.044 (6) | −0.012 (5) | −0.011 (5) | 0.020 (5) |
B2 | 0.063 (7) | 0.039 (6) | 0.030 (6) | −0.016 (6) | −0.010 (5) | 0.011 (5) |
B3 | 0.050 (7) | 0.046 (7) | 0.039 (6) | −0.006 (5) | −0.017 (5) | 0.020 (5) |
C1 | 0.054 (6) | 0.051 (6) | 0.036 (5) | −0.010 (5) | 0.010 (4) | 0.017 (4) |
C2 | 0.056 (6) | 0.045 (6) | 0.062 (6) | −0.009 (5) | 0.007 (5) | 0.021 (5) |
C3 | 0.067 (7) | 0.046 (6) | 0.056 (6) | −0.011 (5) | −0.001 (5) | 0.007 (5) |
C4 | 0.068 (7) | 0.069 (7) | 0.040 (6) | −0.012 (6) | 0.007 (5) | 0.010 (5) |
C5 | 0.083 (7) | 0.039 (5) | 0.035 (5) | −0.018 (5) | −0.007 (5) | 0.018 (4) |
C6 | 0.058 (6) | 0.051 (6) | 0.036 (5) | −0.012 (5) | −0.003 (4) | 0.016 (4) |
C7 | 0.078 (7) | 0.062 (7) | 0.041 (6) | −0.003 (5) | 0.001 (5) | 0.026 (5) |
C8 | 0.066 (7) | 0.047 (6) | 0.058 (7) | 0.011 (5) | 0.003 (5) | 0.015 (5) |
C9 | 0.054 (6) | 0.076 (7) | 0.054 (6) | −0.006 (6) | 0.009 (5) | 0.013 (6) |
C10 | 0.072 (7) | 0.063 (7) | 0.043 (6) | −0.031 (6) | −0.012 (5) | 0.024 (5) |
C11 | 0.048 (6) | 0.049 (6) | 0.046 (5) | −0.015 (5) | −0.006 (4) | 0.014 (5) |
C12 | 0.072 (7) | 0.042 (6) | 0.055 (6) | −0.006 (5) | −0.001 (5) | 0.020 (5) |
C13 | 0.059 (7) | 0.076 (8) | 0.073 (7) | −0.014 (6) | 0.005 (6) | 0.034 (6) |
C14 | 0.075 (7) | 0.023 (5) | 0.103 (8) | 0.000 (5) | −0.013 (6) | 0.027 (5) |
C15 | 0.041 (6) | 0.055 (6) | 0.074 (7) | −0.001 (5) | 0.002 (5) | 0.017 (5) |
C16 | 0.045 (6) | 0.060 (6) | 0.059 (6) | −0.001 (5) | −0.007 (5) | 0.010 (5) |
C17 | 0.034 (6) | 0.118 (10) | 0.056 (7) | −0.006 (6) | 0.007 (5) | 0.030 (7) |
C18 | 0.082 (8) | 0.080 (8) | 0.072 (8) | −0.036 (7) | 0.008 (6) | 0.022 (7) |
C19 | 0.071 (7) | 0.052 (6) | 0.054 (6) | −0.020 (5) | 0.015 (5) | 0.004 (5) |
C20 | 0.053 (6) | 0.053 (6) | 0.044 (5) | −0.020 (5) | 0.002 (4) | 0.014 (5) |
C21 | 0.055 (6) | 0.038 (5) | 0.043 (5) | −0.011 (5) | −0.002 (4) | 0.009 (4) |
C22 | 0.043 (6) | 0.046 (6) | 0.066 (6) | −0.005 (5) | −0.006 (5) | 0.010 (5) |
C23 | 0.042 (6) | 0.088 (8) | 0.072 (7) | −0.030 (6) | 0.004 (5) | 0.002 (6) |
C24 | 0.060 (7) | 0.062 (7) | 0.086 (8) | −0.029 (6) | 0.014 (6) | 0.016 (6) |
C25 | 0.052 (6) | 0.053 (6) | 0.062 (6) | −0.012 (5) | 0.003 (5) | 0.018 (5) |
C26 | 0.057 (7) | 0.072 (7) | 0.097 (8) | −0.034 (6) | −0.014 (6) | 0.041 (6) |
C27 | 0.066 (7) | 0.061 (6) | 0.070 (7) | −0.022 (6) | −0.013 (5) | 0.035 (5) |
C28 | 0.071 (7) | 0.058 (6) | 0.056 (6) | −0.021 (6) | −0.007 (5) | 0.028 (5) |
C29 | 0.068 (7) | 0.058 (6) | 0.063 (6) | −0.020 (5) | −0.004 (5) | 0.029 (5) |
C30 | 0.049 (6) | 0.063 (7) | 0.076 (7) | −0.005 (5) | −0.010 (5) | 0.027 (6) |
C31 | 0.051 (6) | 0.041 (5) | 0.040 (5) | −0.004 (4) | 0.014 (4) | 0.014 (4) |
C32 | 0.064 (7) | 0.051 (6) | 0.048 (6) | 0.004 (5) | 0.009 (5) | 0.010 (5) |
C33 | 0.053 (6) | 0.074 (7) | 0.055 (6) | 0.009 (5) | 0.002 (5) | 0.026 (6) |
C34 | 0.073 (7) | 0.066 (7) | 0.045 (6) | −0.017 (6) | −0.002 (5) | 0.024 (5) |
C35 | 0.084 (8) | 0.049 (6) | 0.043 (6) | −0.021 (6) | 0.017 (5) | 0.010 (5) |
C36 | 0.050 (6) | 0.044 (6) | 0.065 (7) | −0.006 (5) | 0.007 (5) | 0.020 (5) |
C37 | 0.062 (7) | 0.038 (5) | 0.074 (7) | −0.012 (5) | 0.005 (6) | 0.016 (5) |
C38 | 0.075 (8) | 0.058 (6) | 0.069 (8) | −0.005 (6) | 0.005 (6) | 0.021 (6) |
C39 | 0.074 (8) | 0.065 (7) | 0.109 (10) | −0.003 (6) | −0.002 (8) | 0.038 (7) |
C40 | 0.123 (12) | 0.090 (9) | 0.069 (9) | −0.010 (9) | −0.002 (9) | 0.017 (7) |
C41 | 0.090 (10) | 0.142 (12) | 0.082 (10) | −0.014 (9) | 0.020 (8) | 0.044 (8) |
C42 | 0.075 (8) | 0.144 (11) | 0.076 (8) | −0.036 (7) | 0.018 (7) | 0.040 (8) |
C43 | 0.122 (10) | 0.053 (7) | 0.058 (7) | −0.031 (7) | 0.011 (7) | 0.024 (6) |
C44 | 0.178 (14) | 0.062 (7) | 0.057 (8) | −0.020 (8) | 0.001 (8) | 0.024 (7) |
C45 | 0.213 (18) | 0.093 (11) | 0.071 (11) | −0.049 (11) | 0.002 (10) | 0.021 (8) |
C46 | 0.28 (3) | 0.099 (13) | 0.066 (12) | −0.078 (17) | 0.033 (13) | 0.012 (10) |
C47 | 0.22 (2) | 0.120 (13) | 0.113 (15) | −0.046 (14) | 0.113 (14) | 0.010 (12) |
C48 | 0.132 (11) | 0.077 (9) | 0.118 (12) | −0.026 (8) | 0.074 (9) | 0.011 (8) |
Fe1a | 0.0607 (9) | 0.0521 (8) | 0.0439 (8) | −0.0121 (7) | 0.0069 (7) | 0.0128 (6) |
Fe2a | 0.0447 (8) | 0.0607 (8) | 0.0546 (8) | 0.0019 (6) | 0.0104 (6) | 0.0257 (7) |
Fe3a | 0.0587 (9) | 0.0677 (9) | 0.0637 (9) | −0.0080 (7) | 0.0161 (7) | 0.0216 (7) |
S1a | 0.0721 (18) | 0.0639 (17) | 0.0622 (17) | −0.0081 (14) | 0.0031 (14) | 0.0005 (13) |
S2a | 0.0637 (17) | 0.0685 (18) | 0.117 (2) | −0.0134 (14) | 0.0320 (16) | 0.0330 (17) |
S3a | 0.082 (2) | 0.084 (2) | 0.142 (3) | −0.0203 (17) | 0.035 (2) | 0.034 (2) |
O1a | 0.059 (4) | 0.074 (4) | 0.051 (4) | −0.022 (3) | 0.002 (3) | 0.025 (3) |
O2a | 0.061 (4) | 0.068 (4) | 0.044 (4) | −0.015 (3) | −0.002 (3) | 0.022 (3) |
O3a | 0.067 (4) | 0.071 (4) | 0.044 (4) | −0.013 (3) | 0.005 (3) | 0.019 (3) |
B1a | 0.046 (7) | 0.052 (7) | 0.060 (8) | 0.004 (6) | 0.007 (6) | 0.018 (6) |
B2a | 0.052 (7) | 0.057 (7) | 0.058 (8) | 0.005 (6) | 0.011 (6) | 0.022 (6) |
B3a | 0.046 (7) | 0.048 (7) | 0.070 (9) | 0.007 (6) | 0.012 (6) | 0.016 (6) |
C1a | 0.066 (6) | 0.052 (6) | 0.041 (6) | −0.015 (5) | 0.001 (5) | 0.014 (5) |
C2a | 0.048 (6) | 0.052 (6) | 0.059 (6) | −0.005 (5) | 0.011 (5) | 0.012 (5) |
C3a | 0.082 (7) | 0.061 (6) | 0.042 (6) | −0.018 (6) | 0.006 (5) | 0.010 (5) |
C4a | 0.059 (6) | 0.056 (6) | 0.068 (7) | −0.012 (5) | 0.000 (5) | 0.012 (6) |
C5a | 0.081 (7) | 0.056 (6) | 0.051 (6) | −0.011 (5) | 0.007 (5) | 0.027 (5) |
C6a | 0.060 (6) | 0.056 (6) | 0.041 (6) | −0.015 (5) | 0.005 (4) | 0.016 (5) |
C7a | 0.071 (7) | 0.065 (6) | 0.053 (6) | −0.015 (5) | 0.017 (5) | 0.019 (5) |
C8a | 0.058 (6) | 0.065 (7) | 0.053 (6) | −0.011 (5) | 0.001 (5) | 0.019 (5) |
C9a | 0.052 (6) | 0.067 (6) | 0.066 (7) | −0.025 (5) | 0.007 (5) | 0.021 (6) |
C10a | 0.063 (7) | 0.072 (7) | 0.054 (7) | −0.015 (5) | 0.015 (5) | 0.014 (5) |
C11a | 0.034 (5) | 0.057 (6) | 0.059 (6) | −0.002 (4) | 0.013 (5) | 0.023 (5) |
C12a | 0.056 (6) | 0.047 (6) | 0.071 (7) | 0.005 (5) | 0.005 (5) | 0.018 (5) |
C13a | 0.074 (8) | 0.080 (8) | 0.083 (9) | 0.023 (6) | 0.026 (7) | 0.042 (7) |
C14a | 0.057 (7) | 0.108 (9) | 0.056 (7) | 0.010 (6) | 0.003 (6) | 0.042 (7) |
C15a | 0.044 (6) | 0.078 (7) | 0.066 (7) | −0.008 (5) | 0.009 (5) | 0.023 (6) |
C16a | 0.049 (6) | 0.061 (6) | 0.075 (7) | 0.007 (5) | 0.005 (6) | 0.034 (6) |
C17a | 0.061 (7) | 0.055 (7) | 0.103 (9) | −0.015 (5) | 0.015 (7) | 0.030 (7) |
C18a | 0.088 (9) | 0.081 (8) | 0.113 (10) | 0.026 (7) | 0.063 (8) | 0.057 (8) |
C19a | 0.076 (7) | 0.068 (7) | 0.046 (6) | −0.001 (6) | 0.018 (5) | 0.013 (5) |
C20a | 0.033 (5) | 0.060 (6) | 0.057 (6) | −0.001 (4) | 0.013 (5) | 0.021 (5) |
C21a | 0.056 (6) | 0.073 (7) | 0.046 (6) | −0.024 (5) | 0.004 (5) | 0.012 (5) |
C22a | 0.099 (9) | 0.057 (7) | 0.078 (8) | −0.017 (6) | −0.018 (7) | 0.026 (6) |
C23a | 0.056 (8) | 0.084 (9) | 0.151 (13) | −0.006 (6) | 0.006 (8) | 0.044 (9) |
C24a | 0.068 (9) | 0.087 (9) | 0.136 (12) | 0.013 (7) | 0.058 (8) | 0.037 (8) |
C25a | 0.065 (7) | 0.074 (7) | 0.076 (8) | −0.009 (6) | 0.020 (6) | 0.024 (6) |
C26a | 0.162 (17) | 0.100 (12) | 0.160 (16) | 0.018 (11) | 0.105 (14) | 0.058 (12) |
C27a | 0.143 (12) | 0.071 (8) | 0.055 (8) | 0.002 (8) | 0.016 (8) | 0.019 (6) |
C28a | 0.050 (6) | 0.062 (6) | 0.059 (6) | −0.012 (5) | −0.006 (5) | 0.022 (5) |
C29a | 0.055 (7) | 0.099 (9) | 0.099 (9) | −0.013 (6) | −0.003 (7) | 0.047 (7) |
C30a | 0.061 (9) | 0.093 (10) | 0.213 (17) | 0.005 (7) | 0.064 (11) | 0.052 (12) |
C31a | 0.075 (8) | 0.065 (7) | 0.054 (7) | −0.024 (6) | 0.019 (6) | 0.007 (6) |
C32a | 0.087 (8) | 0.074 (8) | 0.071 (8) | −0.002 (7) | 0.022 (7) | 0.015 (6) |
C33a | 0.108 (10) | 0.078 (9) | 0.113 (11) | −0.003 (8) | 0.016 (8) | 0.035 (8) |
C34a | 0.107 (11) | 0.061 (8) | 0.130 (12) | −0.007 (8) | 0.051 (9) | 0.030 (9) |
C35a | 0.134 (12) | 0.055 (8) | 0.093 (9) | −0.029 (8) | 0.045 (9) | 0.008 (7) |
C36a | 0.079 (7) | 0.067 (7) | 0.068 (7) | −0.023 (6) | 0.025 (6) | 0.011 (6) |
C37a | 0.072 (7) | 0.061 (7) | 0.055 (6) | −0.025 (6) | −0.006 (5) | 0.026 (5) |
C38a | 0.069 (7) | 0.052 (7) | 0.085 (8) | −0.001 (6) | 0.008 (6) | 0.020 (6) |
C39a | 0.079 (9) | 0.096 (10) | 0.094 (9) | 0.007 (8) | 0.004 (7) | 0.010 (8) |
C40a | 0.152 (15) | 0.065 (10) | 0.100 (11) | 0.002 (11) | −0.035 (11) | 0.012 (8) |
C41a | 0.180 (17) | 0.069 (10) | 0.114 (12) | −0.051 (12) | −0.030 (12) | 0.039 (9) |
C42a | 0.122 (11) | 0.079 (9) | 0.100 (9) | −0.045 (9) | −0.014 (8) | 0.033 (8) |
C43a | 0.060 (7) | 0.062 (7) | 0.070 (7) | −0.015 (6) | −0.015 (6) | 0.007 (6) |
C44a | 0.102 (10) | 0.093 (10) | 0.067 (8) | 0.006 (8) | 0.005 (7) | 0.037 (7) |
C45a | 0.139 (13) | 0.084 (10) | 0.088 (9) | −0.002 (10) | −0.012 (8) | 0.032 (8) |
C46a | 0.097 (12) | 0.080 (10) | 0.147 (13) | −0.020 (9) | −0.033 (10) | 0.032 (10) |
C47a | 0.096 (11) | 0.092 (11) | 0.214 (17) | −0.042 (9) | −0.044 (11) | 0.095 (11) |
C48a | 0.061 (8) | 0.123 (12) | 0.145 (11) | −0.047 (8) | −0.026 (7) | 0.063 (10) |
O1—B1 | 1.378 (10) | C23—C24 | 1.409 (11) |
O1a—B1a | 1.380 (11) | C24—C25 | 1.413 (11) |
B1—O2 | 1.372 (10) | C21—C25 | 1.420 (10) |
B1a—O2a | 1.381 (11) | C26—C27 | 1.398 (11) |
O2—B2 | 1.387 (10) | C27—C28 | 1.401 (11) |
O2a—B2a | 1.368 (11) | C28—C29 | 1.432 (11) |
B2—O3 | 1.377 (10) | C29—C30 | 1.420 (11) |
B2a—O3a | 1.390 (12) | C26—C30 | 1.411 (11) |
O3—B3 | 1.369 (10) | C21a—C22a | 1.427 (11) |
O3a—B3a | 1.390 (12) | C22a—C23a | 1.406 (13) |
B3—O1 | 1.378 (10) | C23a—C24a | 1.406 (14) |
B3a—O1a | 1.385 (11) | C24a—C25a | 1.432 (13) |
B1—C1 | 1.537 (12) | C21a—C25a | 1.401 (11) |
B1a—C1a | 1.542 (12) | C26a—C27a | 1.388 (16) |
B2—C11 | 1.521 (12) | C27a—C28a | 1.413 (12) |
B2a—C11a | 1.548 (13) | C28a—C29a | 1.393 (11) |
B3—C21 | 1.529 (12) | C29a—C30a | 1.395 (15) |
B3a—C21a | 1.523 (13) | C26a—C30a | 1.386 (17) |
S1—C6 | 1.752 (8) | C31—C32 | 1.389 (10) |
S1a—C6a | 1.742 (8) | C32—C33 | 1.368 (10) |
S1—C31 | 1.768 (8) | C33—C34 | 1.365 (10) |
S1a—C31a | 1.768 (10) | C34—C35 | 1.371 (11) |
S2—C20 | 1.765 (8) | C35—C36 | 1.371 (10) |
S2a—C20a | 1.731 (9) | C31—C36 | 1.372 (10) |
S2—C37 | 1.773 (9) | C31a—C32a | 1.364 (12) |
S2a—C37a | 1.758 (10) | C32a—C33a | 1.406 (13) |
S3—C28 | 1.758 (9) | C33a—C34a | 1.361 (14) |
S3a—C28a | 1.743 (9) | C34a—C35a | 1.379 (14) |
S3—C43 | 1.782 (10) | C35a—C36a | 1.385 (12) |
S3a—C43a | 1.796 (10) | C31a—C36a | 1.372 (11) |
Fe1—C1 | 2.055 (8) | C37—C38 | 1.368 (11) |
Fe1—C2 | 2.042 (8) | C38—C39 | 1.391 (12) |
Fe1—C3 | 2.041 (8) | C39—C40 | 1.363 (13) |
Fe1—C4 | 2.039 (8) | C40—C41 | 1.324 (14) |
Fe1—C5 | 2.016 (7) | C41—C42 | 1.391 (13) |
Fe1—C6 | 2.031 (8) | C37—C42 | 1.370 (12) |
Fe1—C7 | 2.032 (8) | C37a—C38a | 1.380 (11) |
Fe1—C8 | 2.036 (8) | C38a—C39a | 1.374 (12) |
Fe1—C9 | 2.025 (9) | C39a—C40a | 1.372 (16) |
Fe1—C10 | 2.033 (8) | C40a—C41a | 1.354 (17) |
Fe1a—C1a | 2.081 (8) | C41a—C42a | 1.385 (16) |
Fe1a—C2a | 2.064 (8) | C37a—C42a | 1.382 (12) |
Fe1a—C3a | 2.043 (8) | C43—C44 | 1.361 (13) |
Fe1a—C4a | 2.044 (8) | C44—C45 | 1.407 (14) |
Fe1a—C5a | 2.059 (8) | C45—C46 | 1.329 (19) |
Fe1a—C6a | 2.051 (8) | C46—C47 | 1.347 (19) |
Fe1a—C7a | 2.038 (9) | C47—C48 | 1.392 (17) |
Fe1a—C8a | 2.060 (8) | C43—C48 | 1.359 (13) |
Fe1a—C9a | 2.060 (8) | C43a—C44a | 1.364 (12) |
Fe1a—C10a | 2.049 (8) | C44a—C45a | 1.375 (13) |
Fe2—C11 | 2.046 (8) | C45a—C46a | 1.347 (15) |
Fe2—C12 | 2.021 (8) | C46a—C47a | 1.395 (16) |
Fe2—C13 | 2.052 (9) | C47a—C48a | 1.370 (14) |
Fe2—C14 | 2.024 (8) | C43a—C48a | 1.397 (13) |
Fe2—C15 | 2.047 (8) | C2—H2 | 0.9300 |
Fe2—C16 | 2.007 (8) | C2a—H2a | 0.9300 |
Fe2—C17 | 2.041 (8) | C3—H3 | 0.9300 |
Fe2—C18 | 2.027 (9) | C3a—H3a | 0.9300 |
Fe2—C19 | 2.029 (8) | C4—H4 | 0.9300 |
Fe2—C20 | 2.007 (8) | C4a—H4a | 0.9300 |
Fe2a—C11a | 2.055 (8) | C5—H5 | 0.9300 |
Fe2a—C12a | 2.029 (8) | C5a—H5a | 0.9300 |
Fe2a—C13a | 2.020 (9) | C7—H7 | 0.9300 |
Fe2a—C14a | 2.054 (9) | C7a—H7a | 0.9300 |
Fe2a—C15a | 2.038 (8) | C8—H8 | 0.9300 |
Fe2a—C16a | 2.028 (8) | C8a—H8a | 0.9300 |
Fe2a—C17a | 2.026 (9) | C9—H9 | 0.9300 |
Fe2a—C18a | 2.016 (9) | C9a—H9a | 0.9300 |
Fe2a—C19a | 2.029 (8) | C10—H10 | 0.9300 |
Fe2a—C20a | 2.018 (8) | C10a—H10a | 0.9300 |
Fe3—C21 | 2.068 (8) | C12—H12 | 0.9300 |
Fe3—C22 | 2.024 (8) | C12a—H12a | 0.9300 |
Fe3—C23 | 2.034 (9) | C13—H13 | 0.9300 |
Fe3—C24 | 2.040 (8) | C13a—H13a | 0.9300 |
Fe3—C25 | 2.051 (8) | C14—H14 | 0.9300 |
Fe3—C26 | 2.047 (8) | C14a—H14a | 0.9300 |
Fe3—C27 | 2.028 (9) | C15—H15 | 0.9300 |
Fe3—C28 | 2.006 (9) | C15a—H15a | 0.9300 |
Fe3—C29 | 2.035 (8) | C16—H16 | 0.9300 |
Fe3—C30 | 2.054 (8) | C16a—H16a | 0.9300 |
Fe3a—C21a | 2.060 (9) | C17—H17 | 0.9300 |
Fe3a—C22a | 2.046 (9) | C17a—H17a | 0.9300 |
Fe3a—C23a | 2.042 (10) | C18—H18 | 0.9300 |
Fe3a—C24a | 2.027 (10) | C18a—H18a | 0.9300 |
Fe3a—C25a | 2.031 (9) | C19—H19 | 0.9300 |
Fe3a—C26a | 2.036 (13) | C19a—H19a | 0.9300 |
Fe3a—C27a | 2.018 (10) | C22—H22 | 0.9300 |
Fe3a—C28a | 2.015 (8) | C22a—H22a | 0.9300 |
Fe3a—C29a | 2.033 (9) | C23—H23 | 0.9300 |
Fe3a—C30a | 2.038 (12) | C23a—H23a | 0.9300 |
C1—C2 | 1.414 (10) | C24—H24 | 0.9300 |
C2—C3 | 1.394 (10) | C24a—H24a | 0.9300 |
C3—C4 | 1.400 (11) | C25—H25 | 0.9300 |
C4—C5 | 1.415 (10) | C25a—H25a | 0.9300 |
C1—C5 | 1.413 (10) | C26—H26 | 0.9300 |
C6—C7 | 1.419 (10) | C26a—H26a | 0.9300 |
C7—C8 | 1.406 (11) | C27—H27 | 0.9300 |
C8—C9 | 1.388 (11) | C27a—H27a | 0.9300 |
C9—C10 | 1.409 (11) | C29—H29 | 0.9300 |
C6—C10 | 1.417 (10) | C29a—H29a | 0.9300 |
C1a—C2a | 1.431 (10) | C30—H30 | 0.9300 |
C2a—C3a | 1.403 (10) | C30a—H30a | 0.9300 |
C3a—C4a | 1.413 (11) | C32—H32 | 0.9300 |
C4a—C5a | 1.435 (11) | C32a—H32a | 0.9300 |
C1a—C5a | 1.433 (11) | C33—H33 | 0.9300 |
C6a—C7a | 1.439 (10) | C33a—H33a | 0.9300 |
C7a—C8a | 1.410 (11) | C34—H34 | 0.9300 |
C8a—C9a | 1.408 (10) | C34a—H34a | 0.9300 |
C9a—C10a | 1.412 (11) | C35—H35 | 0.9300 |
C6a—C10a | 1.435 (10) | C35a—H35a | 0.9300 |
C11—C12 | 1.434 (10) | C36—H36 | 0.9300 |
C12—C13 | 1.404 (11) | C36a—H36a | 0.9300 |
C13—C14 | 1.413 (11) | C38—H38 | 0.9300 |
C14—C15 | 1.398 (11) | C38a—H38a | 0.9300 |
C11—C15 | 1.425 (10) | C39—H39 | 0.9300 |
C16—C17 | 1.411 (11) | C39a—H39a | 0.9300 |
C17—C18 | 1.373 (12) | C40—H40 | 0.9300 |
C18—C19 | 1.398 (11) | C40a—H40a | 0.9300 |
C19—C20 | 1.417 (10) | C41—H41 | 0.9300 |
C16—C20 | 1.409 (10) | C41a—H41a | 0.9300 |
C11a—C12a | 1.431 (11) | C42—H42 | 0.9300 |
C12a—C13a | 1.408 (11) | C42a—H42a | 0.9300 |
C13a—C14a | 1.386 (12) | C44—H44 | 0.9300 |
C14a—C15a | 1.422 (11) | C44a—H44a | 0.9300 |
C11a—C15a | 1.421 (11) | C45—H45 | 0.9300 |
C16a—C17a | 1.393 (11) | C45a—H45a | 0.9300 |
C17a—C18a | 1.376 (12) | C46—H46 | 0.9300 |
C18a—C19a | 1.409 (12) | C46a—H46a | 0.9300 |
C19a—C20a | 1.399 (11) | C47—H47 | 0.9300 |
C16a—C20a | 1.424 (11) | C47a—H47a | 0.9300 |
C21—C22 | 1.451 (10) | C48—H48 | 0.9300 |
C22—C23 | 1.396 (11) | C48a—H48a | 0.9300 |
O1—B1—O2 | 120.0 (8) | C29a—C28a—S3a | 124.2 (8) |
O1a—B1a—O2a | 120.3 (9) | C48a—C43a—S3a | 115.9 (10) |
B1—O2—B2 | 120.0 (7) | C44a—C43a—S3a | 123.6 (10) |
B1a—O2a—B2a | 120.0 (8) | C3—C2—H2 | 125.2 |
O2—B2—O3 | 119.2 (7) | C1—C2—H2 | 125.2 |
O2a—B2a—O3a | 119.6 (9) | C3a—C2a—H2a | 125.4 |
B2—O3—B3 | 121.0 (7) | C1a—C2a—H2a | 125.4 |
B2a—O3a—B3a | 121.0 (8) | C2—C3—H3 | 125.8 |
O3—B3—O1 | 119.4 (8) | C4—C3—H3 | 125.8 |
O3a—B3a—O1a | 118.2 (9) | C2a—C3a—H3a | 125.7 |
B3—O1—B1 | 120.3 (7) | C4a—C3a—H3a | 125.7 |
B3a—O1a—B1a | 120.7 (8) | C3—C4—H4 | 126.5 |
O2—B1—C1 | 121.4 (8) | C5—C4—H4 | 126.5 |
O2a—B1a—C1a | 119.6 (9) | C3a—C4a—H4a | 126.1 |
O1—B1—C1 | 118.6 (8) | C5a—C4a—H4a | 126.1 |
O1a—B1a—C1a | 119.9 (9) | C1—C5—H5 | 125.2 |
O2—B2—C11 | 121.9 (9) | C4—C5—H5 | 125.2 |
O2a—B2a—C11a | 122.8 (10) | C8—C7—H7 | 125.8 |
O3—B2—C11 | 119.0 (8) | C6—C7—H7 | 125.8 |
O3a—B2a—C11a | 117.4 (9) | C1a—C5a—H5a | 126.0 |
O1—B3—C21 | 119.2 (8) | C4a—C5a—H5a | 126.0 |
O1a—B3a—C21a | 121.0 (10) | C8a—C7a—H7a | 125.9 |
O3—B3—C21 | 121.3 (8) | C6a—C7a—H7a | 125.9 |
O3a—B3a—C21a | 120.8 (9) | C9—C8—H8 | 126.2 |
C2—C1—B1 | 126.3 (8) | C7—C8—H8 | 126.2 |
C2a—C1a—B1a | 126.6 (9) | C9a—C8a—H8a | 125.8 |
C5—C1—B1 | 128.1 (8) | C7a—C8a—H8a | 125.8 |
C5a—C1a—B1a | 126.8 (9) | C8—C9—H9 | 125.3 |
C12—C11—B2 | 127.6 (8) | C10—C9—H9 | 125.3 |
C12a—C11a—B2a | 126.4 (9) | C8a—C9a—H9a | 125.6 |
C15—C11—B2 | 126.3 (9) | C10a—C9a—H9a | 125.6 |
C15a—C11a—B2a | 126.0 (9) | C9—C10—H10 | 126.3 |
C22—C21—B3 | 129.2 (8) | C6—C10—H10 | 126.3 |
C22a—C21a—B3a | 126.1 (10) | C9a—C10a—H10a | 126.1 |
C25—C21—B3 | 125.3 (8) | C6a—C10a—H10a | 126.1 |
C25a—C21a—B3a | 127.6 (9) | C13—C12—H12 | 125.0 |
C6—S1—C31 | 102.9 (4) | C11—C12—H12 | 125.0 |
C6a—S1a—C31a | 102.7 (5) | C13a—C12a—H12a | 126.2 |
C20—S2—C37 | 104.4 (4) | C11a—C12a—H12a | 126.2 |
C20a—S2a—C37a | 102.4 (4) | C12—C13—H13 | 127.0 |
C28—S3—C43 | 105.1 (5) | C14—C13—H13 | 127.0 |
C28a—S3a—C43a | 103.5 (5) | C14a—C13a—H13a | 125.2 |
C3—C2—C1 | 109.6 (8) | C12a—C13a—H13a | 125.2 |
C2—C3—C4 | 108.4 (8) | C15—C14—H14 | 124.9 |
C3—C4—C5 | 106.9 (8) | C13—C14—H14 | 124.9 |
C1—C5—C4 | 109.5 (7) | C15a—C14a—H14a | 126.1 |
C5—C1—C2 | 105.6 (7) | C14—C15—H15 | 126.0 |
C3a—C2a—C1a | 109.2 (8) | C11—C15—H15 | 126.0 |
C2a—C3a—C4a | 108.5 (8) | C11a—C15a—H15a | 125.9 |
C3a—C4a—C5a | 107.7 (8) | C14a—C15a—H15a | 125.9 |
C1a—C5a—C4a | 108.0 (8) | C20—C16—H16 | 126.1 |
C2a—C1a—C5a | 106.6 (7) | C17—C16—H16 | 126.1 |
C8—C7—C6 | 108.5 (8) | C17a—C16a—H16a | 126.1 |
C9—C8—C7 | 107.6 (8) | C20a—C16a—H16a | 126.1 |
C8—C9—C10 | 109.4 (8) | C18—C17—H17 | 126.1 |
C9—C10—C6 | 107.3 (8) | C16—C17—H17 | 126.1 |
C10—C6—C7 | 107.2 (7) | C17—C18—H18 | 125.1 |
C8a—C7a—C6a | 108.2 (8) | C19—C18—H18 | 125.1 |
C9a—C8a—C7a | 108.3 (8) | C17a—C18a—H18a | 125.4 |
C8a—C9a—C10a | 108.8 (8) | C19a—C18a—H18a | 125.4 |
C9a—C10a—C6a | 107.9 (8) | C13a—C14a—H14a | 126.1 |
C10a—C6a—C7a | 106.8 (7) | C18a—C17a—H17a | 125.8 |
C13—C12—C11 | 110.1 (8) | C16a—C17a—H17a | 125.8 |
C12—C13—C14 | 105.9 (8) | C18—C19—H19 | 126.5 |
C15—C14—C13 | 110.2 (8) | C20—C19—H19 | 126.5 |
C14—C15—C11 | 107.9 (8) | C20a—C19a—H19a | 126.3 |
C15—C11—C12 | 105.9 (7) | C18a—C19a—H19a | 126.3 |
C13a—C12a—C11a | 107.5 (9) | C23—C22—H22 | 125.6 |
C14a—C13a—C12a | 109.6 (10) | C21—C22—H22 | 125.6 |
C13a—C14a—C15a | 107.7 (9) | C23a—C22a—H22a | 125.3 |
C11a—C15a—C14a | 108.2 (9) | C21a—C22a—H22a | 125.3 |
C15a—C11a—C12a | 106.9 (8) | C22—C23—H23 | 125.6 |
C18—C17—C16 | 107.8 (8) | C24—C23—H23 | 125.6 |
C17—C18—C19 | 109.9 (9) | C24a—C23a—H23a | 126.1 |
C18—C19—C20 | 106.9 (8) | C22a—C23a—H23a | 126.1 |
C16—C20—C19 | 107.6 (8) | C23—C24—H24 | 126.3 |
C20—C16—C17 | 107.7 (8) | C25—C24—H24 | 126.3 |
C18a—C17a—C16a | 108.3 (9) | C23a—C24a—H24a | 126.3 |
C17a—C18a—C19a | 109.2 (9) | C25a—C24a—H24a | 126.3 |
C20a—C19a—C18a | 107.3 (9) | C24—C25—H25 | 125.2 |
C19a—C20a—C16a | 107.4 (8) | C21—C25—H25 | 125.2 |
C17a—C16a—C20a | 107.9 (9) | C21a—C25a—H25a | 125.4 |
C23—C22—C21 | 108.8 (8) | C24a—C25a—H25a | 125.4 |
C22—C23—C24 | 108.8 (8) | C27—C26—H26 | 125.6 |
C23—C24—C25 | 107.5 (9) | C30—C26—H26 | 125.6 |
C24—C25—C21 | 109.7 (8) | C30a—C26a—H26a | 125.7 |
C25—C21—C22 | 105.3 (8) | C27a—C26a—H26a | 125.7 |
C23a—C22a—C21a | 109.4 (10) | C26—C27—H27 | 125.9 |
C24a—C23a—C22a | 107.8 (11) | C28—C27—H27 | 125.9 |
C23a—C24a—C25a | 107.3 (11) | C26a—C27a—H27a | 125.9 |
C21a—C25a—C24a | 109.2 (10) | C28a—C27a—H27a | 125.9 |
C25a—C21a—C22a | 106.3 (9) | C28—C29—H29 | 126.5 |
C26—C27—C28 | 108.3 (8) | C28a—C29a—H29a | 125.5 |
C27—C28—C29 | 108.2 (8) | C30a—C29a—H29a | 125.5 |
C30—C29—C28 | 106.9 (8) | C26—C30—H30 | 126.1 |
C26—C30—C29 | 107.8 (8) | C29—C30—H30 | 126.1 |
C27—C26—C30 | 108.8 (9) | C26a—C30a—H30a | 126.2 |
C26a—C27a—C28a | 108.1 (12) | C29a—C30a—H30a | 126.2 |
C29a—C28a—C27a | 106.7 (9) | C33—C32—H32 | 120.4 |
C28a—C29a—C30a | 108.9 (11) | C31—C32—H32 | 120.4 |
C26a—C30a—C29a | 107.7 (14) | C34—C33—H33 | 119.0 |
C30a—C26a—C27a | 108.6 (14) | C32—C33—H33 | 119.0 |
C33—C32—C31 | 119.1 (8) | C34a—C33a—H33a | 119.4 |
C34—C33—C32 | 122.0 (8) | C32a—C33a—H33a | 119.4 |
C33—C34—C35 | 119.1 (8) | C31a—C32a—H32a | 120.6 |
C36—C35—C34 | 119.5 (8) | C33a—C32a—H32a | 120.6 |
C35—C36—C31 | 121.7 (8) | C33—C34—H34 | 120.5 |
C36—C31—C32 | 118.5 (8) | C35—C34—H34 | 120.5 |
C31a—C32a—C33a | 118.8 (11) | C36—C35—H35 | 120.2 |
C34a—C33a—C32a | 121.3 (12) | C34—C35—H35 | 120.2 |
C33a—C34a—C35a | 119.3 (12) | C33a—C34a—H34a | 120.4 |
C34a—C35a—C36a | 119.7 (11) | C35a—C34a—H34a | 120.4 |
C31a—C36a—C35a | 120.8 (10) | C34a—C35a—H35a | 120.2 |
C32a—C31a—C36a | 120.1 (10) | C36a—C35a—H35a | 120.2 |
C37—C38—C39 | 120.1 (10) | C31a—C36a—H36a | 119.6 |
C40—C39—C38 | 119.7 (11) | C35a—C36a—H36a | 119.6 |
C41—C40—C39 | 120.4 (12) | C35—C36—H36 | 119.1 |
C40—C41—C42 | 121.0 (12) | C31—C36—H36 | 119.1 |
C37—C42—C41 | 119.7 (10) | C37—C38—H38 | 119.9 |
C38—C37—C42 | 119.0 (10) | C39—C38—H38 | 119.9 |
C39a—C38a—C37a | 121.1 (10) | C30—C29—H29 | 126.5 |
C40a—C39a—C38a | 119.8 (13) | C39a—C38a—H38a | 119.4 |
C41a—C40a—C39a | 120.3 (15) | C37a—C38a—H38a | 119.4 |
C40a—C41a—C42a | 120.0 (14) | C40—C39—H39 | 120.2 |
C37a—C42a—C41a | 120.8 (12) | C38—C39—H39 | 120.2 |
C38a—C37a—C42a | 117.9 (10) | C40a—C39a—H39a | 120.1 |
C43—C44—C45 | 120.3 (13) | C38a—C39a—H39a | 120.1 |
C46—C45—C44 | 119.3 (17) | C41—C40—H40 | 119.8 |
C45—C46—C47 | 120.8 (19) | C39—C40—H40 | 119.8 |
C46—C47—C48 | 120.9 (18) | C41a—C40a—H40a | 119.9 |
C43—C48—C47 | 119.1 (14) | C39a—C40a—H40a | 119.9 |
C48—C43—C44 | 119.6 (11) | C40—C41—H41 | 119.5 |
C43a—C44a—C45a | 119.2 (12) | C42—C41—H41 | 119.5 |
C46a—C45a—C44a | 122.4 (14) | C40a—C41a—H41a | 120.0 |
C45a—C46a—C47a | 117.8 (14) | C42a—C41a—H41a | 120.0 |
C48a—C47a—C46a | 121.7 (14) | C37—C42—H42 | 120.1 |
C47a—C48a—C43a | 118.1 (12) | C41—C42—H42 | 120.1 |
C44a—C43a—C48a | 120.6 (10) | C37a—C42a—H42a | 119.6 |
C10—C6—S1 | 127.3 (7) | C41a—C42a—H42a | 119.6 |
C7—C6—S1 | 125.5 (7) | C43—C44—H44 | 119.9 |
C36—C31—S1 | 117.2 (7) | C45—C44—H44 | 119.9 |
C32—C31—S1 | 124.3 (6) | C43a—C44a—H44a | 120.4 |
C10a—C6a—S1a | 126.1 (7) | C45a—C44a—H44a | 120.4 |
C7a—C6a—S1a | 127.0 (7) | C46—C45—H45 | 120.4 |
C36a—C31a—S1a | 116.0 (9) | C44—C45—H45 | 120.4 |
C32a—C31a—S1a | 123.9 (8) | C46a—C45a—H45a | 118.8 |
C16—C20—S2 | 127.3 (7) | C44a—C45a—H45a | 118.8 |
C19—C20—S2 | 125.0 (7) | C45—C46—H46 | 119.6 |
C38—C37—S2 | 122.6 (8) | C47—C46—H46 | 119.6 |
C42—C37—S2 | 118.4 (9) | C45a—C46a—H46a | 121.1 |
C16a—C20a—S2a | 125.5 (7) | C47a—C46a—H46a | 121.1 |
C19a—C20a—S2a | 127.1 (8) | C46—C47—H47 | 119.6 |
C38a—C37a—S2a | 124.1 (8) | C48—C47—H47 | 119.6 |
C42a—C37a—S2a | 117.9 (9) | C48a—C47a—H47a | 119.1 |
C27—C28—S3 | 125.2 (7) | C46a—C47a—H47a | 119.1 |
C29—C28—S3 | 126.4 (7) | C43—C48—H48 | 120.5 |
C48—C43—S3 | 118.1 (11) | C47—C48—H48 | 120.5 |
C44—C43—S3 | 122.2 (10) | C47a—C48a—H48a | 120.9 |
C27a—C28a—S3a | 128.9 (9) | C43a—C48a—H48a | 120.9 |
C5—C1—C2—C3 | 0.4 (9) | S1—C31—C32—C33 | 178.7 (7) |
C5a—C1a—C2a—C3a | −0.5 (9) | S1a—C31a—C32a—C33a | 177.9 (8) |
B1—C1—C2—C3 | 178.2 (7) | C31—C32—C33—C34 | −0.9 (14) |
B1a—C1a—C2a—C3a | 178.3 (8) | C31a—C32a—C33a—C34a | 0.1 (16) |
C1—C2—C3—C4 | 0.1 (10) | C32—C33—C34—C35 | 1.5 (14) |
C1a—C2a—C3a—C4a | 0.6 (10) | C32a—C33a—C34a—C35a | 1.0 (18) |
C2—C3—C4—C5 | −0.6 (9) | C33—C34—C35—C36 | −0.6 (13) |
C2a—C3a—C4a—C5a | −0.4 (10) | C33a—C34a—C35a—C36a | −0.6 (17) |
C2—C1—C5—C4 | −0.8 (9) | C34—C35—C36—C31 | −0.8 (12) |
C2a—C1a—C5a—C4a | 0.2 (9) | C34a—C35a—C36a—C31a | −0.8 (15) |
B1—C1—C5—C4 | −178.5 (7) | C32—C31—C36—C35 | 1.3 (12) |
B1a—C1a—C5a—C4a | −178.6 (8) | C32a—C31a—C36a—C35a | 1.8 (14) |
C3—C4—C5—C1 | 0.9 (9) | S1—C31—C36—C35 | −177.9 (6) |
C3a—C4a—C5a—C1a | 0.1 (10) | S1a—C31a—C36a—C35a | −177.6 (7) |
C31—S1—C6—C10 | 94.9 (8) | C20—S2—C37—C38 | 7.6 (8) |
C31a—S1a—C6a—C10a | 101.8 (8) | C20a—S2a—C37a—C38a | 3.4 (9) |
C31—S1—C6—C7 | −85.4 (7) | C20—S2—C37—C42 | −173.7 (8) |
C31a—S1a—C6a—C7a | −82.4 (8) | C20a—S2a—C37a—C42a | −175.5 (8) |
C10—C6—C7—C8 | 0.5 (9) | C42—C37—C38—C39 | 0.3 (14) |
C10a—C6a—C7a—C8a | −1.2 (9) | C42a—C37a—C38a—C39a | 0.1 (14) |
S1—C6—C7—C8 | −179.3 (6) | S2—C37—C38—C39 | 179.0 (7) |
S1a—C6a—C7a—C8a | −177.7 (6) | S2a—C37a—C38a—C39a | −178.8 (7) |
C6—C7—C8—C9 | −0.4 (10) | C37—C38—C39—C40 | 0.2 (15) |
C6a—C7a—C8a—C9a | 0.9 (10) | C37a—C38a—C39a—C40a | 2.3 (16) |
C7—C8—C9—C10 | 0.2 (10) | C38—C39—C40—C41 | −1.7 (17) |
C7a—C8a—C9a—C10a | −0.3 (10) | C38a—C39a—C40a—C41a | −4 (2) |
C8—C9—C10—C6 | 0.1 (10) | C39—C40—C41—C42 | 3 (2) |
C8a—C9a—C10a—C6a | −0.5 (10) | C39a—C40a—C41a—C42a | 3 (2) |
C7—C6—C10—C9 | −0.4 (9) | C38—C37—C42—C41 | 0.5 (15) |
C7a—C6a—C10a—C9a | 1.1 (9) | C38a—C37a—C42a—C41a | −1.0 (16) |
S1—C6—C10—C9 | 179.4 (6) | S2—C37—C42—C41 | −178.2 (9) |
S1a—C6a—C10a—C9a | 177.6 (6) | S2a—C37a—C42a—C41a | 177.9 (9) |
C15—C11—C12—C13 | 0.1 (9) | C40—C41—C42—C37 | −2.0 (19) |
C15a—C11a—C12a—C13a | 1.1 (9) | C40a—C41a—C42a—C37a | −1 (2) |
B2—C11—C12—C13 | 174.4 (8) | C28—S3—C43—C48 | −158.9 (8) |
B2a—C11a—C12a—C13a | 171.7 (8) | C28a—S3a—C43a—C48a | 171.6 (8) |
C11—C12—C13—C14 | −0.8 (10) | C28—S3—C43—C44 | 21.5 (10) |
C11a—C12a—C13a—C14a | 0.3 (10) | C28a—S3a—C43a—C44a | −8.7 (10) |
C12—C13—C14—C15 | 1.2 (10) | C48—C43—C44—C45 | −3.4 (16) |
C12a—C13a—C14a—C15a | −1.6 (11) | C48a—C43a—C44a—C45a | 1.2 (15) |
C13—C14—C15—C11 | −1.2 (10) | S3—C43—C44—C45 | 176.2 (8) |
C13a—C14a—C15a—C11a | 2.3 (10) | S3a—C43a—C44a—C45a | −178.5 (8) |
C12—C11—C15—C14 | 0.6 (9) | C43—C44—C45—C46 | 2.2 (19) |
C12a—C11a—C15a—C14a | −2.1 (9) | C43a—C44a—C45a—C46a | 1.0 (18) |
B2—C11—C15—C14 | −173.8 (8) | C44—C45—C46—C47 | 1 (3) |
B2a—C11a—C15a—C14a | −172.7 (8) | C44a—C45a—C46a—C47a | −4 (2) |
C20—C16—C17—C18 | 1.3 (10) | C45—C46—C47—C48 | −3 (3) |
C20a—C16a—C17a—C18a | −0.6 (10) | C45a—C46a—C47a—C48a | 5 (2) |
C16—C17—C18—C19 | −1.4 (11) | C44—C43—C48—C47 | 1.5 (16) |
C16a—C17a—C18a—C19a | −0.1 (11) | C44a—C43a—C48a—C47a | −0.4 (16) |
C17—C18—C19—C20 | 0.9 (11) | S3—C43—C48—C47 | −178.1 (9) |
C17a—C18a—C19a—C20a | 0.9 (11) | S3a—C43a—C48a—C47a | 179.3 (9) |
C17—C16—C20—C19 | −0.7 (9) | C46—C47—C48—C43 | 2 (2) |
C17a—C16a—C20a—C19a | 1.1 (9) | C46a—C47a—C48a—C43a | −2.5 (19) |
C17—C16—C20—S2 | −177.8 (6) | B2—O2—B1—O1 | 4.4 (11) |
C17a—C16a—C20a—S2a | 179.1 (6) | B2a—O2a—B1a—O1a | 0.7 (12) |
C18—C19—C20—C16 | −0.1 (10) | B2—O2—B1—C1 | −173.5 (7) |
C18a—C19a—C20a—C16a | −1.2 (9) | B2a—O2a—B1a—C1a | −174.2 (8) |
C18—C19—C20—S2 | 177.0 (6) | B3—O1—B1—O2 | −3.0 (11) |
C18a—C19a—C20a—S2a | −179.1 (6) | B3a—O1a—B1a—O2a | −1.1 (12) |
C37—S2—C20—C16 | −96.7 (8) | B3—O1—B1—C1 | 174.8 (7) |
C37a—S2a—C20a—C16a | −95.9 (7) | B3a—O1a—B1a—C1a | 173.8 (7) |
C37—S2—C20—C19 | 86.6 (8) | C5—C1—B1—O2 | −4.8 (13) |
C37a—S2a—C20a—C19a | 81.6 (8) | C5a—C1a—B1a—O2a | −5.3 (13) |
C25—C21—C22—C23 | 1.1 (9) | C2—C1—B1—O2 | 177.9 (7) |
C25a—C21a—C22a—C23a | −0.3 (11) | C2a—C1a—B1a—O2a | 176.1 (7) |
B3—C21—C22—C23 | 176.8 (8) | C5—C1—B1—O1 | 177.3 (7) |
B3a—C21a—C22a—C23a | 179.2 (9) | C5a—C1a—B1a—O1a | 179.8 (8) |
C21—C22—C23—C24 | −1.5 (10) | C2—C1—B1—O1 | 0.1 (12) |
C21a—C22a—C23a—C24a | 0.0 (12) | C2a—C1a—B1a—O1a | 1.2 (13) |
C22—C23—C24—C25 | 1.4 (10) | B3—O3—B2—O2 | 4.6 (11) |
C22a—C23a—C24a—C25a | 0.3 (12) | B3a—O3a—B2a—O2a | 5.5 (12) |
C23—C24—C25—C21 | −0.7 (10) | B3—O3—B2—C11 | −175.8 (7) |
C23a—C24a—C25a—C21a | −0.5 (11) | B3a—O3a—B2a—C11a | −170.2 (7) |
C22—C21—C25—C24 | −0.2 (9) | B1—O2—B2—O3 | −5.1 (11) |
C22a—C21a—C25a—C24a | 0.4 (10) | B1a—O2a—B2a—O3a | −2.9 (12) |
B3—C21—C25—C24 | −176.1 (7) | B1—O2—B2—C11 | 175.3 (7) |
B3a—C21a—C25a—C24a | −179.0 (8) | B1a—O2a—B2a—C11a | 172.6 (8) |
C30—C26—C27—C28 | 0.4 (10) | C15—C11—B2—O3 | −10.0 (12) |
C30a—C26a—C27a—C28a | −0.1 (15) | C15a—C11a—B2a—O3a | −13.0 (12) |
C26—C27—C28—C29 | −0.6 (10) | C12—C11—B2—O3 | 176.8 (7) |
C26a—C27a—C28a—C29a | −0.8 (12) | C12a—C11a—B2a—O3a | 178.1 (7) |
C26—C27—C28—S3 | 174.6 (6) | C15—C11—B2—O2 | 169.6 (7) |
C26a—C27a—C28a—S3a | 174.9 (8) | C15a—C11a—B2a—O2a | 171.4 (8) |
C43—S3—C28—C27 | 96.4 (8) | C12—C11—B2—O2 | −3.6 (13) |
C43a—S3a—C28a—C27a | 94.7 (9) | C12a—C11a—B2a—O2a | 2.5 (13) |
C43—S3—C28—C29 | −89.3 (8) | B2—O3—B3—O1 | −3.3 (11) |
C43a—S3a—C28a—C29a | −90.2 (8) | B2a—O3a—B3a—O1a | −5.7 (12) |
C27—C28—C29—C30 | 0.6 (10) | B2—O3—B3—C21 | 173.9 (7) |
C27a—C28a—C29a—C30a | 1.5 (11) | B2a—O3a—B3a—C21a | 172.2 (8) |
S3—C28—C29—C30 | −174.5 (6) | B1—O1—B3—O3 | 2.5 (11) |
S3a—C28a—C29a—C30a | −174.5 (7) | B1a—O1a—B3a—O3a | 3.5 (12) |
C27—C26—C30—C29 | 0.0 (10) | B1—O1—B3—C21 | −174.8 (7) |
C27a—C26a—C30a—C29a | 1.1 (16) | B1a—O1a—B3a—C21a | −174.4 (8) |
C28—C29—C30—C26 | −0.4 (10) | C25—C21—B3—O3 | 162.7 (7) |
C28a—C29a—C30a—C26a | −1.6 (14) | C25a—C21a—B3a—O3a | 175.1 (8) |
C6—S1—C31—C36 | −167.7 (6) | C22—C21—B3—O3 | −12.2 (13) |
C6a—S1a—C31a—C36a | −171.8 (7) | C22a—C21a—B3a—O3a | −4.3 (14) |
C6—S1—C31—C32 | 13.1 (8) | C25—C21—B3—O1 | −20.1 (12) |
C6a—S1a—C31a—C32a | 8.8 (9) | C25a—C21a—B3a—O1a | −7.0 (14) |
C36—C31—C32—C33 | −0.5 (12) | C22—C21—B3—O1 | 165.0 (7) |
C36a—C31a—C32a—C33a | −1.4 (15) | C22a—C21a—B3a—O1a | 173.6 (8) |
Experimental details
Crystal data | |
Chemical formula | [Fe3(C15H12B3O3)(C11H9S)3] |
Mr | 959.98 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 17.501 (4), 18.875 (5), 14.999 (4) |
α, β, γ (°) | 113.137 (19), 101.89 (2), 74.30 (2) |
V (Å3) | 4358.4 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.17 |
Crystal size (mm) | 0.43 × 0.17 × 0.13 |
Data collection | |
Diffractometer | Rigaku AFC-5S diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.791, 0.859 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16062, 15452, 4619 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.158, 0.93 |
No. of reflections | 15452 |
No. of parameters | 1081 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.49 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996), MSC/AFC Diffractometer Control Software, PROCESS in TEXSAN (Molecular Structure Corporation, 1997), SHELXS97 (Sheldrick, 1990), LS in TEXSAN and SHELXL97 (Sheldrick, 1997), ORTEP (Johnson, 1965) in TEXSAN, TEXSAN, SHELXL97 and PLATON (Spek, 2000).
O1—B1 | 1.378 (10) | B2a—C11a | 1.548 (13) |
O1a—B1a | 1.380 (11) | B3—C21 | 1.529 (12) |
B1—O2 | 1.372 (10) | B3a—C21a | 1.523 (13) |
B1a—O2a | 1.381 (11) | S1—C6 | 1.752 (8) |
O2—B2 | 1.387 (10) | S1a—C6a | 1.742 (8) |
O2a—B2a | 1.368 (11) | S1—C31 | 1.768 (8) |
B2—O3 | 1.377 (10) | S1a—C31a | 1.768 (10) |
B2a—O3a | 1.390 (12) | S2—C20 | 1.765 (8) |
O3—B3 | 1.369 (10) | S2a—C20a | 1.731 (9) |
O3a—B3a | 1.390 (12) | S2—C37 | 1.773 (9) |
B3—O1 | 1.378 (10) | S2a—C37a | 1.758 (10) |
B3a—O1a | 1.385 (11) | S3—C28 | 1.758 (9) |
B1—C1 | 1.537 (12) | S3a—C28a | 1.743 (9) |
B1a—C1a | 1.542 (12) | S3—C43 | 1.782 (10) |
B2—C11 | 1.521 (12) | S3a—C43a | 1.796 (10) |
O1—B1—O2 | 120.0 (8) | O1a—B3a—C21a | 121.0 (10) |
O1a—B1a—O2a | 120.3 (9) | O3—B3—C21 | 121.3 (8) |
B1—O2—B2 | 120.0 (7) | O3a—B3a—C21a | 120.8 (9) |
B1a—O2a—B2a | 120.0 (8) | C2—C1—B1 | 126.3 (8) |
O2—B2—O3 | 119.2 (7) | C2a—C1a—B1a | 126.6 (9) |
O2a—B2a—O3a | 119.6 (9) | C5—C1—B1 | 128.1 (8) |
B2—O3—B3 | 121.0 (7) | C5a—C1a—B1a | 126.8 (9) |
B2a—O3a—B3a | 121.0 (8) | C12—C11—B2 | 127.6 (8) |
O3—B3—O1 | 119.4 (8) | C12a—C11a—B2a | 126.4 (9) |
O3a—B3a—O1a | 118.2 (9) | C15—C11—B2 | 126.3 (9) |
B3—O1—B1 | 120.3 (7) | C15a—C11a—B2a | 126.0 (9) |
B3a—O1a—B1a | 120.7 (8) | C22—C21—B3 | 129.2 (8) |
O2—B1—C1 | 121.4 (8) | C22a—C21a—B3a | 126.1 (10) |
O2a—B1a—C1a | 119.6 (9) | C25—C21—B3 | 125.3 (8) |
O1—B1—C1 | 118.6 (8) | C25a—C21a—B3a | 127.6 (9) |
O1a—B1a—C1a | 119.9 (9) | C6—S1—C31 | 102.9 (4) |
O2—B2—C11 | 121.9 (9) | C6a—S1a—C31a | 102.7 (5) |
O2a—B2a—C11a | 122.8 (10) | C20—S2—C37 | 104.4 (4) |
O3—B2—C11 | 119.0 (8) | C20a—S2a—C37a | 102.4 (4) |
O3a—B2a—C11a | 117.4 (9) | C28—S3—C43 | 105.1 (5) |
O1—B3—C21 | 119.2 (8) | C28a—S3a—C43a | 103.5 (5) |
In contrast to the identification of 2-(N,N-dimethylaminoalkyl)ferroceneboronic acids by their crystal structures (Norrild & Sotofte, 2001), our attempt to characterize 1'-phenylthio-1-ferroceneboronic acid, (II), by X-ray analysis showed that its structure was exclusively that of the corresponding boroxin, i.e the title compound, (I). In our studies of chiral ferrocenyl phosphine ligands (Hua et al., 2001), (I) was synthesized from the metallation of 1,1'-bis(tri-n-butylstannyl)ferrocene with n-butyllithium, followed by treatment with diphenyl disulfide, and a subsequent second metallation with n-butyllithium, followed by borination with trimethyl borate and acid hydrolysis. The fact that we found that water is needed in the Suzuki coupling reaction (Miyaura, 1998) when we used (I) as a substrate, and that insufficient structural characterization was afforded by spectroscopic methods, made us unsure of the unequivocal identity of the product, and we turned to X-ray analysis. Indeed, the X-ray structure of (I), shown with atom numbering in Fig. 1, indicates that the initial boronic acid product derived from the aforementioned reactions underwent complete dehydration to form the boroxin.
Although ferroceneboronic acid underwent partial dehydration in vacuo after several days to give triferrocenylboroxin (Post et al., 1970), 1'-phenylthio-1-ferroceneboronic acid, (II), apparently exists, at least in its crystalline state, exclusively as the boroxin (I). This anhydro structure explains the need to use water and base (such as sodium carbonate) in Suzuki reactions of (I), i.e. in order to hydrolyze it into boronic acid (II) so that a coupling reaction with an aryl halide may take place in the presence of palladium(0). X-ray structures of triferrocenylboroxins have not been reported previously.
The asymmetric unit of (I) contains two chemically identical but conformationally slightly different molecules, the largest conformational variation involving the ferrocene moieties containing Fe3 and Fe3a, respectively. In molecule 1, the ferrocene moiety containing Fe3 is essentially eclipsed, while in molecule 2 the corresponding ferrocene moiety, Fe3a, is nearly perfectly staggered. In fact, all of the other ferrocene moieties are essentially eclipsed; the actual rotational values for each ferrocene moiety is tabulated in the CIF. A second significant conformational difference involves the dihedral angle between the boroxin ring and the lower cyclopentadienyl ring of the Fe3/Fe3a ferrocene moieties, the values being 16.4 (5) and 6.6 (6)°, respectively. Of course both of these differences produce several associated torsional differences. Other dihedral angles between the boroxin rings and their bonded cyclopentadienyl rings are 3.6 (5), 3.6 (5), 7.3 (5) and 5.9 (5)° for the Fe1, Fe1a, Fe2, and Fe2a ferrocene moieties, respectively. Stabilization from the aromaticity of the boroxin ring (Jug, 1983) is likely the driving force for the formation of (I). Indeed, the boroxin-ring atoms are reasonably coplanar in both molecules, the deviations from planarity ranging from -0.020 (5) to 0.020 (10) Å and -0.027 (6) to 0.021 (12) Å, respectively, for molecules 1 and 2. The sp2-hybridized B—O bond lengths of (I) range from 1.369 (10) to 1.387 (10) Å in molecule 1 and from 1.368 (11) to 1.390 (12) Å in molecule 2. These bond lengths are in marked contrast to that of the sp3-hybridized B—O single bond of 1.505 Å reported by Voloshin et al. (1997), and are consistent with an aromatic ring structure. Selected geometric parameters are listed in Table 1.