Abstract
In the title compound, [Zr(C5H5)(C13H9)2Cl]·C7H8, the ZrIV atom is coordinated by a Cl atom, a cyclopentadienyl (Cp) ligand [Zr–centroid (Cp) = 2.199 (3) Å] and two fluorenyl ligands (Fl) [Zr–centroid (Fl) = 2.273 (2) Å and Zr—CH from fluorenyl = 2.355 (2) Å] in a distorted tetragonal geometry. The dihedral angles between the mean planes of the fluorenyl ring systems and the Cp ring are 36.62 (6)° for the η1-coordinated fluorenyl and 52.85 (6)° for the η5-coordinated fluorenyl, while the dihedral angle between the mean planes of the two fluorenyl ring systems is 76.18 (7)°.
Related literature
Unbridged metallocene complexes with fluorenyl ligands constitute precursors of catalysts for homogeneous polymerization of α-olefins, see: Schmid et al. (1995) ▶; Alt & Samuel (1998 ▶). Fluorenyl ligands can reduce the stability of complexes, see: Samuel & Setton (1965 ▶). For the preparation of CpZrCl3·DME (DME = 1,2-dimethoxyethane), see: Lund & Livinghouse (1990 ▶).
Experimental
Crystal data
[Zr(C5H5)(C13H9)2Cl]·C7H8
M r = 614.3
Triclinic,
a = 9.3091 (4) Å
b = 10.7937 (4) Å
c = 15.1219 (8) Å
α = 77.231 (4)°
β = 81.966 (4)°
γ = 74.135 (4)°
V = 1420.31 (11) Å3
Z = 2
Mo Kα radiation
μ = 0.51 mm−1
T = 150 K
0.35 × 0.16 × 0.07 mm
Data collection
Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.894, T max = 0.97
8923 measured reflections
5572 independent reflections
4680 reflections with I > 2σ(I)
R int = 0.022
Refinement
R[F 2 > 2σ(F 2)] = 0.031
wR(F 2) = 0.076
S = 1.05
5572 reflections
362 parameters
H-atom parameters constrained
Δρmax = 0.59 e Å−3
Δρmin = −0.33 e Å−3
Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX32 (Farrugia, 1999 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050816/kp2294sup1.cif
e-67-00m54-sup1.cif (39.7KB, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050816/kp2294Isup2.hkl
e-67-00m54-Isup2.hkl (267.3KB, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Selected bond lengths (Å).
| Cl1—Zr1 | 2.4537 (5) |
| Zr1—C1 | 2.521 (2) |
| Zr1—C2 | 2.515 (2) |
| Zr1—C3 | 2.490 (2) |
| Zr1—C4 | 2.467 (2) |
| Zr1—C5 | 2.499 (2) |
| Zr1—C6 | 2.355 (2) |
| Zr1—C19 | 2.468 (2) |
| Zr1—C28 | 2.6434 (19) |
| Zr1—C29 | 2.617 (2) |
| Zr1—C30 | 2.601 (2) |
| Zr1—C31 | 2.565 (2) |
Acknowledgments
AŁ-K and JP thank the Polish State Committee of Scientific Research (project No. N N204 145038) for financial support.
supplementary crystallographic information
Comment
The unbridged metallocene complexes with fluorenyl ligand constitute precursors of catalysts for homogeneous polymerization of α-olefins (Scmid et al. 1995; Alt et al. 1998). The fluorenyl ligands facile changes in hapticity η5→η1 (ring-slippage). This property influences the catalytic activity of this type of compounds, however it also hampers to syntheses and lowers the stability of the complexes, for example Flu2ZrCl2 is stable in donor solvent (THF) for only a short time (Samuel et al. 1965).
The structure exhibits an η5 ,η1 fluorenyl coordination to the zirconium mononuclear centre, completing the coordinations sphere of a chloride atom and cyclopentadienyl ligand (Fig. 1 and Table 1). The fluorenyl groups are not exactly planar, r.m.s. deviations of a best least-squares plane of the fluorenyl units are: for η1– coordinated is 0.042 (6) Å and for η5– coordinated is 0.132 (6) Å (the values were found for carbon atoms). The dihedral angles between the mean planes of the fluorenyl ring systems and the cyclopentadienyl ring are: η1– coordinated fluorenyl and Cp 36.62 (6)° and η5– coordinated fluorenyl and Cp 52.85 (6)°, however the dihedral angle between the mean planes of the two fluorenyl system ring system is 103.82 (7)°.
Experimental
All reactions and manipulations were carried aot under an atmosphere of ultra-high purified argon employing standard Schlenk techniques. Solvents were purified, dried and distilled prior to use from dark blue potassium or sodium diphenyl ketyl solution.
CpZrCl3.DME was prepared according to the literature (Lund et al. 1990). Fluorene is commercial product and was used without further purification.
A solution of fluorene in Et2O was treated with n-BuLi (1,6M in hexane). After the evolution of gas completes, an equimolar amount of CpZrCl3.DME was added. The mixture was stirred for 2 h. The solvent was removed in vaccum. The residue was extracted with toluene and the suspension was filtered through magnesium sulfate. The filtrated was concetrated and crystallised at 251 K (Schmid et al. 1995).
Refinement
All H atoms were fixed geometrically and treated as riding with C—H = 0.95 Å (aromatic), 0.98 Å (methyl) and 1.00 Å (methine) with Uiso(H) = 1.2 Ueq (aromatic, methine, methylene) and Uiso(H) = 1.5Ueq (methyl).
Figures
Fig. 1.
The molecular structure of the title molecule with the atom-numbering. Displacement ellipsoids are drawn at the 30% probability level. The H atoms bonded to C atoms (except H6A) were omitted for clarity.
Crystal data
| [Zr(C5H5)(C13H9)2Cl]·C7H8 | Z = 2 |
| Mr = 614.3 | F(000) = 632 |
| Triclinic, P1 | Dx = 1.436 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.3091 (4) Å | Cell parameters from 6309 reflections |
| b = 10.7937 (4) Å | θ = 2.6–28.7° |
| c = 15.1219 (8) Å | µ = 0.51 mm−1 |
| α = 77.231 (4)° | T = 150 K |
| β = 81.966 (4)° | Block, yellow |
| γ = 74.135 (4)° | 0.35 × 0.16 × 0.07 mm |
| V = 1420.31 (11) Å3 |
Data collection
| Oxford Diffraction Xcalibur Sapphire2 large Be window diffractometer | 5572 independent reflections |
| graphite | 4680 reflections with I > 2σ(I) |
| Detector resolution: 8.1883 pixels mm-1 | Rint = 0.022 |
| ω scans | θmax = 26°, θmin = 2.6° |
| Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010) | h = −10→11 |
| Tmin = 0.894, Tmax = 0.97 | k = −13→12 |
| 8923 measured reflections | l = −13→18 |
Refinement
| 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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.076 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0473P)2] where P = (Fo2 + 2Fc2)/3 |
| 5572 reflections | (Δ/σ)max = 0.001 |
| 362 parameters | Δρmax = 0.59 e Å−3 |
| 0 restraints | Δρmin = −0.33 e Å−3 |
Special details
| Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) |
| Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.63228 (6) | 0.47339 (5) | 0.60738 (4) | 0.02355 (13) | |
| Zr1 | 0.60062 (2) | 0.637778 (18) | 0.702371 (14) | 0.01694 (7) | |
| C1 | 0.6240 (3) | 0.6138 (3) | 0.86975 (16) | 0.0380 (6) | |
| H1A | 0.5588 | 0.6722 | 0.9104 | 0.046* | |
| C2 | 0.6023 (3) | 0.4959 (3) | 0.85859 (17) | 0.0372 (7) | |
| H2A | 0.5201 | 0.4548 | 0.8903 | 0.045* | |
| C3 | 0.7277 (3) | 0.4361 (2) | 0.80616 (17) | 0.0325 (6) | |
| H3A | 0.7511 | 0.3445 | 0.795 | 0.039* | |
| C4 | 0.8250 (3) | 0.5197 (2) | 0.78403 (16) | 0.0301 (5) | |
| H4A | 0.9301 | 0.4969 | 0.7556 | 0.036* | |
| C5 | 0.7600 (3) | 0.6282 (2) | 0.82490 (16) | 0.0328 (6) | |
| H5A | 0.81 | 0.6977 | 0.8287 | 0.039* | |
| C6 | 0.3404 (2) | 0.6697 (2) | 0.73870 (14) | 0.0191 (4) | |
| H6A | 0.2874 | 0.7264 | 0.6852 | 0.023* | |
| C7 | 0.2992 (2) | 0.8535 (2) | 0.83522 (16) | 0.0245 (5) | |
| H7A | 0.3413 | 0.9115 | 0.7887 | 0.029* | |
| C8 | 0.2488 (3) | 0.8869 (2) | 0.91958 (16) | 0.0280 (5) | |
| H8A | 0.2561 | 0.9685 | 0.93 | 0.034* | |
| C9 | 0.1876 (3) | 0.8034 (2) | 0.98953 (16) | 0.0302 (5) | |
| H9A | 0.1543 | 0.8281 | 1.0469 | 0.036* | |
| C10 | 0.1755 (2) | 0.6844 (2) | 0.97514 (15) | 0.0273 (5) | |
| H10A | 0.1344 | 0.6268 | 1.0225 | 0.033* | |
| C11 | 0.1724 (2) | 0.4232 (2) | 0.89921 (16) | 0.0259 (5) | |
| H11A | 0.1333 | 0.4136 | 0.9611 | 0.031* | |
| C12 | 0.1788 (2) | 0.3280 (2) | 0.84944 (17) | 0.0286 (5) | |
| H12A | 0.1444 | 0.2523 | 0.8775 | 0.034* | |
| C13 | 0.2356 (2) | 0.3428 (2) | 0.75838 (17) | 0.0273 (5) | |
| H13A | 0.2368 | 0.2779 | 0.7247 | 0.033* | |
| C14 | 0.2905 (2) | 0.4511 (2) | 0.71600 (16) | 0.0239 (5) | |
| H14A | 0.3297 | 0.4598 | 0.6541 | 0.029* | |
| C15 | 0.2880 (2) | 0.7342 (2) | 0.81871 (15) | 0.0203 (4) | |
| C16 | 0.2244 (2) | 0.6503 (2) | 0.89033 (15) | 0.0220 (5) | |
| C17 | 0.2242 (2) | 0.5333 (2) | 0.85688 (15) | 0.0222 (5) | |
| C18 | 0.2872 (2) | 0.5465 (2) | 0.76560 (15) | 0.0210 (5) | |
| C19 | 0.6192 (2) | 0.86760 (19) | 0.66605 (15) | 0.0224 (5) | |
| H19A | 0.6112 | 0.9236 | 0.712 | 0.027* | |
| C20 | 0.3519 (2) | 0.9527 (2) | 0.60587 (16) | 0.0248 (5) | |
| H20A | 0.3105 | 1.0121 | 0.6461 | 0.03* | |
| C21 | 0.2667 (3) | 0.9381 (2) | 0.54421 (17) | 0.0298 (5) | |
| H21A | 0.1659 | 0.9889 | 0.5416 | 0.036* | |
| C22 | 0.3247 (3) | 0.8497 (2) | 0.48431 (16) | 0.0287 (5) | |
| H22A | 0.2611 | 0.839 | 0.4441 | 0.034* | |
| C23 | 0.4706 (2) | 0.7793 (2) | 0.48319 (15) | 0.0235 (5) | |
| H23A | 0.5094 | 0.7205 | 0.4422 | 0.028* | |
| C24 | 0.8395 (2) | 0.6781 (2) | 0.49803 (15) | 0.0241 (5) | |
| H24A | 0.8172 | 0.6418 | 0.4513 | 0.029* | |
| C25 | 0.9851 (3) | 0.6621 (2) | 0.51474 (18) | 0.0312 (6) | |
| H25A | 1.0645 | 0.6159 | 0.4784 | 0.037* | |
| C26 | 1.0185 (3) | 0.7137 (2) | 0.58524 (18) | 0.0326 (6) | |
| H26A | 1.1204 | 0.7021 | 0.5949 | 0.039* | |
| C27 | 0.9089 (3) | 0.7794 (2) | 0.63988 (17) | 0.0282 (5) | |
| H27A | 0.9339 | 0.811 | 0.6881 | 0.034* | |
| C28 | 0.5030 (2) | 0.87790 (19) | 0.60909 (15) | 0.0200 (4) | |
| C29 | 0.5631 (2) | 0.79551 (19) | 0.54418 (14) | 0.0185 (4) | |
| C30 | 0.7233 (2) | 0.74927 (19) | 0.55153 (14) | 0.0190 (4) | |
| C31 | 0.7566 (2) | 0.80007 (19) | 0.62379 (14) | 0.0203 (4) | |
| C32 | 0.8254 (3) | 1.0698 (2) | 0.77764 (16) | 0.0279 (5) | |
| C33 | 0.6720 (3) | 1.1262 (2) | 0.77990 (17) | 0.0301 (5) | |
| H33A | 0.6339 | 1.2032 | 0.737 | 0.036* | |
| C34 | 0.5739 (3) | 1.0711 (2) | 0.84437 (19) | 0.0356 (6) | |
| H34A | 0.4694 | 1.1113 | 0.8459 | 0.043* | |
| C35 | 0.6277 (3) | 0.9582 (2) | 0.90619 (18) | 0.0363 (6) | |
| H35A | 0.5604 | 0.9194 | 0.9495 | 0.044* | |
| C36 | 0.7790 (3) | 0.9024 (2) | 0.90458 (17) | 0.0352 (6) | |
| H36A | 0.8165 | 0.8254 | 0.9476 | 0.042* | |
| C37 | 0.8768 (3) | 0.9567 (2) | 0.84148 (17) | 0.0318 (6) | |
| H37A | 0.9812 | 0.9164 | 0.8413 | 0.038* | |
| C38 | 0.9341 (3) | 1.1292 (3) | 0.7093 (2) | 0.0481 (7) | |
| H38A | 1.0108 | 1.144 | 0.7412 | 0.072* | |
| H38B | 0.8802 | 1.213 | 0.6747 | 0.072* | |
| H38C | 0.9821 | 1.0691 | 0.6676 | 0.072* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0294 (3) | 0.0187 (3) | 0.0243 (3) | −0.0091 (2) | 0.0016 (2) | −0.0063 (2) |
| Zr1 | 0.01916 (11) | 0.01453 (11) | 0.01689 (12) | −0.00478 (8) | −0.00162 (8) | −0.00174 (8) |
| C1 | 0.0457 (15) | 0.0388 (14) | 0.0186 (12) | 0.0117 (13) | −0.0128 (11) | −0.0042 (11) |
| C2 | 0.0289 (13) | 0.0523 (16) | 0.0242 (13) | −0.0176 (12) | −0.0132 (11) | 0.0214 (12) |
| C3 | 0.0466 (15) | 0.0167 (11) | 0.0339 (14) | −0.0034 (11) | −0.0220 (12) | 0.0015 (10) |
| C4 | 0.0216 (11) | 0.0386 (13) | 0.0254 (13) | −0.0013 (10) | −0.0077 (10) | −0.0007 (10) |
| C5 | 0.0491 (15) | 0.0287 (12) | 0.0262 (13) | −0.0144 (12) | −0.0207 (12) | −0.0002 (10) |
| C6 | 0.0175 (10) | 0.0193 (10) | 0.0193 (11) | −0.0051 (9) | −0.0007 (8) | −0.0012 (8) |
| C7 | 0.0220 (11) | 0.0239 (11) | 0.0265 (12) | −0.0056 (9) | −0.0016 (9) | −0.0036 (9) |
| C8 | 0.0292 (12) | 0.0284 (12) | 0.0280 (13) | −0.0052 (10) | −0.0063 (10) | −0.0085 (10) |
| C9 | 0.0310 (13) | 0.0362 (13) | 0.0225 (12) | −0.0028 (11) | −0.0046 (10) | −0.0092 (10) |
| C10 | 0.0234 (11) | 0.0345 (13) | 0.0218 (12) | −0.0067 (10) | −0.0022 (9) | −0.0014 (10) |
| C11 | 0.0215 (11) | 0.0263 (12) | 0.0258 (12) | −0.0062 (9) | −0.0028 (9) | 0.0042 (10) |
| C12 | 0.0249 (11) | 0.0232 (11) | 0.0362 (14) | −0.0096 (10) | −0.0053 (10) | 0.0034 (10) |
| C13 | 0.0247 (11) | 0.0213 (11) | 0.0368 (14) | −0.0060 (10) | −0.0050 (10) | −0.0060 (10) |
| C14 | 0.0219 (11) | 0.0243 (11) | 0.0250 (12) | −0.0059 (9) | −0.0022 (9) | −0.0032 (9) |
| C15 | 0.0152 (10) | 0.0212 (10) | 0.0226 (11) | −0.0020 (9) | −0.0059 (9) | −0.0010 (9) |
| C16 | 0.0178 (10) | 0.0256 (11) | 0.0211 (11) | −0.0038 (9) | −0.0043 (9) | −0.0013 (9) |
| C17 | 0.0174 (10) | 0.0232 (11) | 0.0239 (12) | −0.0037 (9) | −0.0039 (9) | −0.0004 (9) |
| C18 | 0.0171 (10) | 0.0206 (10) | 0.0239 (12) | −0.0042 (9) | −0.0052 (9) | −0.0002 (9) |
| C19 | 0.0312 (12) | 0.0148 (10) | 0.0226 (12) | −0.0083 (9) | −0.0019 (9) | −0.0034 (9) |
| C20 | 0.0271 (11) | 0.0163 (10) | 0.0244 (12) | −0.0031 (9) | 0.0050 (9) | 0.0022 (9) |
| C21 | 0.0212 (11) | 0.0235 (11) | 0.0355 (14) | −0.0036 (10) | −0.0020 (10) | 0.0103 (10) |
| C22 | 0.0260 (12) | 0.0322 (13) | 0.0279 (13) | −0.0142 (10) | −0.0083 (10) | 0.0062 (10) |
| C23 | 0.0292 (12) | 0.0224 (11) | 0.0201 (11) | −0.0112 (10) | −0.0038 (9) | 0.0004 (9) |
| C24 | 0.0281 (11) | 0.0201 (11) | 0.0222 (12) | −0.0071 (9) | 0.0029 (9) | −0.0022 (9) |
| C25 | 0.0239 (12) | 0.0235 (12) | 0.0387 (14) | −0.0042 (10) | 0.0068 (10) | 0.0018 (10) |
| C26 | 0.0204 (11) | 0.0300 (12) | 0.0439 (15) | −0.0125 (10) | −0.0059 (11) | 0.0101 (11) |
| C27 | 0.0280 (12) | 0.0269 (12) | 0.0320 (13) | −0.0145 (10) | −0.0106 (10) | 0.0038 (10) |
| C28 | 0.0238 (11) | 0.0130 (9) | 0.0217 (11) | −0.0068 (9) | 0.0001 (9) | 0.0012 (8) |
| C29 | 0.0209 (10) | 0.0160 (10) | 0.0173 (11) | −0.0073 (8) | −0.0005 (8) | 0.0024 (8) |
| C30 | 0.0214 (10) | 0.0147 (10) | 0.0204 (11) | −0.0079 (8) | −0.0006 (8) | 0.0015 (8) |
| C31 | 0.0253 (11) | 0.0168 (10) | 0.0207 (11) | −0.0111 (9) | −0.0031 (9) | 0.0007 (8) |
| C32 | 0.0325 (12) | 0.0286 (12) | 0.0262 (13) | −0.0101 (10) | −0.0011 (10) | −0.0103 (10) |
| C33 | 0.0387 (14) | 0.0213 (11) | 0.0325 (14) | −0.0042 (10) | −0.0100 (11) | −0.0093 (10) |
| C34 | 0.0261 (12) | 0.0378 (14) | 0.0484 (17) | −0.0069 (11) | −0.0005 (11) | −0.0232 (12) |
| C35 | 0.0465 (15) | 0.0375 (14) | 0.0322 (14) | −0.0217 (12) | 0.0089 (12) | −0.0155 (11) |
| C36 | 0.0528 (16) | 0.0246 (12) | 0.0286 (14) | −0.0077 (12) | −0.0066 (12) | −0.0066 (10) |
| C37 | 0.0304 (12) | 0.0284 (12) | 0.0355 (14) | −0.0001 (11) | −0.0058 (11) | −0.0114 (11) |
| C38 | 0.0502 (17) | 0.0554 (17) | 0.0418 (17) | −0.0236 (15) | 0.0075 (14) | −0.0098 (14) |
Geometric parameters (Å, °)
| Cl1—Zr1 | 2.4537 (5) | C15—C16 | 1.422 (3) |
| Zr1—C1 | 2.521 (2) | C16—C17 | 1.462 (3) |
| Zr1—C2 | 2.515 (2) | C17—C18 | 1.415 (3) |
| Zr1—C3 | 2.490 (2) | C19—C31 | 1.430 (3) |
| Zr1—C4 | 2.467 (2) | C19—C28 | 1.441 (3) |
| Zr1—C5 | 2.499 (2) | C19—H19A | 1 |
| Zr1—C6 | 2.355 (2) | C20—C21 | 1.364 (3) |
| Zr1—C19 | 2.468 (2) | C20—C28 | 1.419 (3) |
| Zr1—C28 | 2.6434 (19) | C20—H20A | 0.95 |
| Zr1—C29 | 2.617 (2) | C21—C22 | 1.409 (4) |
| Zr1—C30 | 2.601 (2) | C21—H21A | 0.95 |
| Zr1—C31 | 2.565 (2) | C22—C23 | 1.363 (3) |
| C1—C5 | 1.382 (4) | C22—H22A | 0.95 |
| C1—C2 | 1.391 (4) | C23—C29 | 1.413 (3) |
| C1—H1A | 1 | C23—H23A | 0.95 |
| C2—C3 | 1.401 (4) | C24—C25 | 1.372 (3) |
| C2—H2A | 1 | C24—C30 | 1.411 (3) |
| C3—C4 | 1.405 (3) | C24—H24A | 0.95 |
| C3—H3A | 1 | C25—C26 | 1.411 (4) |
| C4—C5 | 1.396 (3) | C25—H25A | 0.95 |
| C4—H4A | 1 | C26—C27 | 1.362 (4) |
| C5—H5A | 1 | C26—H26A | 0.95 |
| C6—C15 | 1.486 (3) | C27—C31 | 1.421 (3) |
| C6—C18 | 1.497 (3) | C27—H27A | 0.95 |
| C6—H6A | 1 | C28—C29 | 1.424 (3) |
| C7—C8 | 1.386 (3) | C29—C30 | 1.449 (3) |
| C7—C15 | 1.398 (3) | C30—C31 | 1.430 (3) |
| C7—H7A | 0.95 | C32—C33 | 1.389 (3) |
| C8—C9 | 1.395 (3) | C32—C37 | 1.393 (3) |
| C8—H8A | 0.95 | C32—C38 | 1.507 (4) |
| C9—C10 | 1.386 (3) | C33—C34 | 1.390 (4) |
| C9—H9A | 0.95 | C33—H33A | 0.95 |
| C10—C16 | 1.393 (3) | C34—C35 | 1.379 (4) |
| C10—H10A | 0.95 | C34—H34A | 0.95 |
| C11—C12 | 1.386 (3) | C35—C36 | 1.371 (4) |
| C11—C17 | 1.395 (3) | C35—H35A | 0.95 |
| C11—H11A | 0.95 | C36—C37 | 1.372 (4) |
| C12—C13 | 1.395 (3) | C36—H36A | 0.95 |
| C12—H12A | 0.95 | C37—H37A | 0.95 |
| C13—C14 | 1.394 (3) | C38—H38A | 0.98 |
| C13—H13A | 0.95 | C38—H38B | 0.98 |
| C14—C18 | 1.394 (3) | C38—H38C | 0.98 |
| C14—H14A | 0.95 | ||
| C6—Zr1—Cl1 | 97.23 (5) | C10—C9—C8 | 119.9 (2) |
| C6—Zr1—C4 | 134.90 (8) | C10—C9—H9A | 120.1 |
| Cl1—Zr1—C4 | 94.36 (6) | C8—C9—H9A | 120.1 |
| C6—Zr1—C19 | 100.25 (7) | C9—C10—C16 | 119.1 (2) |
| Cl1—Zr1—C19 | 132.29 (5) | C9—C10—H10A | 120.4 |
| C4—Zr1—C19 | 103.51 (8) | C16—C10—H10A | 120.4 |
| C6—Zr1—C3 | 107.72 (8) | C12—C11—C17 | 118.9 (2) |
| Cl1—Zr1—C3 | 79.54 (6) | C12—C11—H11A | 120.6 |
| C4—Zr1—C3 | 32.94 (8) | C17—C11—H11A | 120.6 |
| C19—Zr1—C3 | 134.22 (7) | C11—C12—C13 | 120.4 (2) |
| C6—Zr1—C5 | 118.29 (8) | C11—C12—H12A | 119.8 |
| Cl1—Zr1—C5 | 126.93 (6) | C13—C12—H12A | 119.8 |
| C4—Zr1—C5 | 32.65 (8) | C14—C13—C12 | 121.2 (2) |
| C19—Zr1—C5 | 81.20 (7) | C14—C13—H13A | 119.4 |
| C3—Zr1—C5 | 53.79 (8) | C12—C13—H13A | 119.4 |
| C6—Zr1—C2 | 80.83 (8) | C18—C14—C13 | 119.2 (2) |
| Cl1—Zr1—C2 | 100.73 (7) | C18—C14—H14A | 120.4 |
| C4—Zr1—C2 | 54.18 (8) | C13—C14—H14A | 120.4 |
| C19—Zr1—C2 | 125.66 (9) | C7—C15—C16 | 118.1 (2) |
| C3—Zr1—C2 | 32.51 (9) | C7—C15—C6 | 131.6 (2) |
| C5—Zr1—C2 | 53.37 (8) | C16—C15—C6 | 110.13 (18) |
| C6—Zr1—C1 | 87.22 (8) | C10—C16—C15 | 121.5 (2) |
| Cl1—Zr1—C1 | 131.38 (6) | C10—C16—C17 | 130.5 (2) |
| C4—Zr1—C1 | 53.73 (8) | C15—C16—C17 | 107.99 (19) |
| C19—Zr1—C1 | 93.64 (8) | C11—C17—C18 | 121.1 (2) |
| C3—Zr1—C1 | 53.45 (8) | C11—C17—C16 | 130.9 (2) |
| C5—Zr1—C1 | 31.95 (9) | C18—C17—C16 | 108.07 (18) |
| C2—Zr1—C1 | 32.06 (9) | C14—C18—C17 | 119.29 (19) |
| C6—Zr1—C31 | 130.91 (7) | C14—C18—C6 | 130.6 (2) |
| Cl1—Zr1—C31 | 108.22 (5) | C17—C18—C6 | 110.08 (19) |
| C4—Zr1—C31 | 85.07 (7) | C31—C19—C28 | 106.77 (19) |
| C19—Zr1—C31 | 32.94 (7) | C31—C19—Zr1 | 77.25 (11) |
| C3—Zr1—C31 | 117.58 (8) | C28—C19—Zr1 | 80.45 (12) |
| C5—Zr1—C31 | 78.16 (8) | C31—C19—H19A | 125 |
| C2—Zr1—C31 | 131.50 (7) | C28—C19—H19A | 125 |
| C1—Zr1—C31 | 104.49 (8) | Zr1—C19—H19A | 125 |
| C6—Zr1—C30 | 124.42 (7) | C21—C20—C28 | 119.2 (2) |
| Cl1—Zr1—C30 | 79.07 (5) | C21—C20—H20A | 120.4 |
| C4—Zr1—C30 | 100.54 (7) | C28—C20—H20A | 120.4 |
| C19—Zr1—C30 | 54.50 (7) | C20—C21—C22 | 121.6 (2) |
| C3—Zr1—C30 | 125.39 (8) | C20—C21—H21A | 119.2 |
| C5—Zr1—C30 | 106.38 (8) | C22—C21—H21A | 119.2 |
| C2—Zr1—C30 | 154.72 (7) | C23—C22—C21 | 121.0 (2) |
| C1—Zr1—C30 | 135.89 (8) | C23—C22—H22A | 119.5 |
| C31—Zr1—C30 | 32.12 (7) | C21—C22—H22A | 119.5 |
| C6—Zr1—C29 | 92.19 (7) | C22—C23—C29 | 118.7 (2) |
| Cl1—Zr1—C29 | 81.15 (5) | C22—C23—H23A | 120.7 |
| C4—Zr1—C29 | 132.72 (7) | C29—C23—H23A | 120.7 |
| C19—Zr1—C29 | 54.28 (7) | C25—C24—C30 | 118.8 (2) |
| C3—Zr1—C29 | 153.75 (8) | C25—C24—H24A | 120.6 |
| C5—Zr1—C29 | 130.64 (7) | C30—C24—H24A | 120.6 |
| C2—Zr1—C29 | 172.92 (7) | C24—C25—C26 | 120.8 (2) |
| C1—Zr1—C29 | 147.29 (8) | C24—C25—H25A | 119.6 |
| C31—Zr1—C29 | 53.15 (6) | C26—C25—H25A | 119.6 |
| C30—Zr1—C29 | 32.23 (6) | C27—C26—C25 | 121.9 (2) |
| C6—Zr1—C28 | 79.51 (7) | C27—C26—H26A | 119 |
| Cl1—Zr1—C28 | 111.11 (5) | C25—C26—H26A | 119 |
| C4—Zr1—C28 | 135.02 (7) | C26—C27—C31 | 119.1 (2) |
| C19—Zr1—C28 | 32.52 (7) | C26—C27—H27A | 120.5 |
| C3—Zr1—C28 | 166.71 (7) | C31—C27—H27A | 120.5 |
| C5—Zr1—C28 | 113.06 (7) | C20—C28—C29 | 118.6 (2) |
| C2—Zr1—C28 | 144.26 (8) | C20—C28—C19 | 133.0 (2) |
| C1—Zr1—C28 | 117.27 (8) | C29—C28—C19 | 108.38 (18) |
| C31—Zr1—C28 | 52.49 (6) | C20—C28—Zr1 | 126.77 (14) |
| C30—Zr1—C28 | 52.44 (6) | C29—C28—Zr1 | 73.29 (11) |
| C29—Zr1—C28 | 31.41 (7) | C19—C28—Zr1 | 67.03 (11) |
| C5—C1—C2 | 108.6 (2) | C23—C29—C28 | 120.66 (19) |
| C5—C1—Zr1 | 73.16 (14) | C23—C29—C30 | 131.6 (2) |
| C2—C1—Zr1 | 73.72 (14) | C28—C29—C30 | 107.53 (18) |
| C5—C1—H1A | 125.4 | C23—C29—Zr1 | 120.95 (14) |
| C2—C1—H1A | 125.4 | C28—C29—Zr1 | 75.30 (11) |
| Zr1—C1—H1A | 125.4 | C30—C29—Zr1 | 73.25 (11) |
| C1—C2—C3 | 107.7 (2) | C24—C30—C31 | 120.6 (2) |
| C1—C2—Zr1 | 74.21 (13) | C24—C30—C29 | 131.9 (2) |
| C3—C2—Zr1 | 72.78 (13) | C31—C30—C29 | 107.33 (19) |
| C1—C2—H2A | 125.9 | C24—C30—Zr1 | 122.46 (13) |
| C3—C2—H2A | 125.9 | C31—C30—Zr1 | 72.55 (12) |
| Zr1—C2—H2A | 125.9 | C29—C30—Zr1 | 74.51 (11) |
| C2—C3—C4 | 107.9 (2) | C27—C31—C30 | 118.9 (2) |
| C2—C3—Zr1 | 74.71 (12) | C27—C31—C19 | 132.4 (2) |
| C4—C3—Zr1 | 72.61 (12) | C30—C31—C19 | 108.75 (18) |
| C2—C3—H3A | 125.7 | C27—C31—Zr1 | 122.10 (14) |
| C4—C3—H3A | 125.7 | C30—C31—Zr1 | 75.33 (12) |
| Zr1—C3—H3A | 125.7 | C19—C31—Zr1 | 69.81 (11) |
| C5—C4—C3 | 107.3 (2) | C33—C32—C37 | 117.9 (2) |
| C5—C4—Zr1 | 74.96 (13) | C33—C32—C38 | 121.5 (2) |
| C3—C4—Zr1 | 74.45 (12) | C37—C32—C38 | 120.5 (2) |
| C5—C4—H4A | 125.8 | C32—C33—C34 | 120.6 (2) |
| C3—C4—H4A | 125.8 | C32—C33—H33A | 119.7 |
| Zr1—C4—H4A | 125.8 | C34—C33—H33A | 119.7 |
| C1—C5—C4 | 108.5 (2) | C35—C34—C33 | 120.3 (2) |
| C1—C5—Zr1 | 74.89 (14) | C35—C34—H34A | 119.9 |
| C4—C5—Zr1 | 72.39 (13) | C33—C34—H34A | 119.9 |
| C1—C5—H5A | 125.5 | C36—C35—C34 | 119.4 (2) |
| C4—C5—H5A | 125.5 | C36—C35—H35A | 120.3 |
| Zr1—C5—H5A | 125.5 | C34—C35—H35A | 120.3 |
| C15—C6—C18 | 103.35 (17) | C35—C36—C37 | 120.7 (2) |
| C15—C6—Zr1 | 111.95 (13) | C35—C36—H36A | 119.6 |
| C18—C6—Zr1 | 115.03 (13) | C37—C36—H36A | 119.6 |
| C15—C6—H6A | 108.8 | C36—C37—C32 | 121.1 (2) |
| C18—C6—H6A | 108.8 | C36—C37—H37A | 119.5 |
| Zr1—C6—H6A | 108.8 | C32—C37—H37A | 119.5 |
| C8—C7—C15 | 119.8 (2) | C32—C38—H38A | 109.5 |
| C8—C7—H7A | 120.1 | C32—C38—H38B | 109.5 |
| C15—C7—H7A | 120.1 | H38A—C38—H38B | 109.5 |
| C7—C8—C9 | 121.5 (2) | C32—C38—H38C | 109.5 |
| C7—C8—H8A | 119.2 | H38A—C38—H38C | 109.5 |
| C9—C8—H8A | 119.2 | H38B—C38—H38C | 109.5 |
| C6—Zr1—C1—C5 | −167.02 (15) | C1—Zr1—C19—C28 | −138.95 (13) |
| Cl1—Zr1—C1—C5 | 95.79 (15) | C31—Zr1—C19—C28 | 109.75 (18) |
| C4—Zr1—C1—C5 | 37.18 (14) | C30—Zr1—C19—C28 | 74.09 (13) |
| C19—Zr1—C1—C5 | −66.94 (15) | C29—Zr1—C19—C28 | 34.14 (11) |
| C3—Zr1—C1—C5 | 78.42 (16) | C28—C20—C21—C22 | 0.7 (3) |
| C2—Zr1—C1—C5 | 115.8 (2) | C20—C21—C22—C23 | −2.9 (3) |
| C31—Zr1—C1—C5 | −35.38 (16) | C21—C22—C23—C29 | 0.6 (3) |
| C30—Zr1—C1—C5 | −27.30 (19) | C30—C24—C25—C26 | 1.3 (3) |
| C29—Zr1—C1—C5 | −77.34 (19) | C24—C25—C26—C27 | 0.7 (3) |
| C28—Zr1—C1—C5 | −90.34 (15) | C25—C26—C27—C31 | −1.8 (3) |
| C6—Zr1—C1—C2 | 77.13 (15) | C21—C20—C28—C29 | 3.5 (3) |
| Cl1—Zr1—C1—C2 | −20.06 (19) | C21—C20—C28—C19 | −178.2 (2) |
| C4—Zr1—C1—C2 | −78.67 (16) | C21—C20—C28—Zr1 | −86.5 (2) |
| C19—Zr1—C1—C2 | 177.22 (15) | C31—C19—C28—C20 | −167.0 (2) |
| C3—Zr1—C1—C2 | −37.42 (14) | Zr1—C19—C28—C20 | 119.6 (2) |
| C5—Zr1—C1—C2 | −115.8 (2) | C31—C19—C28—C29 | 11.5 (2) |
| C31—Zr1—C1—C2 | −151.22 (14) | Zr1—C19—C28—C29 | −61.97 (14) |
| C30—Zr1—C1—C2 | −143.15 (14) | C31—C19—C28—Zr1 | 73.46 (13) |
| C29—Zr1—C1—C2 | 166.81 (14) | C6—Zr1—C28—C20 | 1.41 (19) |
| C28—Zr1—C1—C2 | 153.82 (14) | Cl1—Zr1—C28—C20 | 95.19 (19) |
| C5—C1—C2—C3 | 0.3 (3) | C4—Zr1—C28—C20 | −144.70 (18) |
| Zr1—C1—C2—C3 | 65.63 (15) | C19—Zr1—C28—C20 | −127.4 (3) |
| C5—C1—C2—Zr1 | −65.38 (16) | C3—Zr1—C28—C20 | −122.8 (3) |
| C6—Zr1—C2—C1 | −99.48 (16) | C5—Zr1—C28—C20 | −115.01 (19) |
| Cl1—Zr1—C2—C1 | 164.82 (14) | C2—Zr1—C28—C20 | −56.2 (2) |
| C4—Zr1—C2—C1 | 77.19 (16) | C1—Zr1—C28—C20 | −79.9 (2) |
| C19—Zr1—C2—C1 | −3.41 (19) | C31—Zr1—C28—C20 | −167.6 (2) |
| C3—Zr1—C2—C1 | 114.7 (2) | C30—Zr1—C28—C20 | 151.6 (2) |
| C5—Zr1—C2—C1 | 36.41 (14) | C29—Zr1—C28—C20 | 113.6 (2) |
| C31—Zr1—C2—C1 | 38.50 (19) | C6—Zr1—C28—C29 | −112.19 (12) |
| C30—Zr1—C2—C1 | 77.7 (3) | Cl1—Zr1—C28—C29 | −18.41 (12) |
| C28—Zr1—C2—C1 | −42.2 (2) | C4—Zr1—C28—C29 | 101.70 (14) |
| C6—Zr1—C2—C3 | 145.82 (15) | C19—Zr1—C28—C29 | 119.00 (18) |
| Cl1—Zr1—C2—C3 | 50.11 (14) | C3—Zr1—C28—C29 | 123.5 (3) |
| C4—Zr1—C2—C3 | −37.51 (14) | C5—Zr1—C28—C29 | 131.39 (13) |
| C19—Zr1—C2—C3 | −118.12 (15) | C2—Zr1—C28—C29 | −169.84 (13) |
| C5—Zr1—C2—C3 | −78.29 (15) | C1—Zr1—C28—C29 | 166.51 (12) |
| C1—Zr1—C2—C3 | −114.7 (2) | C31—Zr1—C28—C29 | 78.83 (13) |
| C31—Zr1—C2—C3 | −76.21 (18) | C30—Zr1—C28—C29 | 38.00 (11) |
| C30—Zr1—C2—C3 | −37.0 (3) | C6—Zr1—C28—C19 | 128.81 (14) |
| C28—Zr1—C2—C3 | −156.90 (13) | Cl1—Zr1—C28—C19 | −137.42 (12) |
| C1—C2—C3—C4 | −1.0 (2) | C4—Zr1—C28—C19 | −17.31 (17) |
| Zr1—C2—C3—C4 | 65.55 (15) | C3—Zr1—C28—C19 | 4.5 (4) |
| C1—C2—C3—Zr1 | −66.56 (15) | C5—Zr1—C28—C19 | 12.39 (15) |
| C6—Zr1—C3—C2 | −35.61 (16) | C2—Zr1—C28—C19 | 71.16 (17) |
| Cl1—Zr1—C3—C2 | −129.94 (15) | C1—Zr1—C28—C19 | 47.51 (15) |
| C4—Zr1—C3—C2 | 114.8 (2) | C31—Zr1—C28—C19 | −40.18 (12) |
| C19—Zr1—C3—C2 | 89.24 (17) | C30—Zr1—C28—C19 | −81.01 (13) |
| C5—Zr1—C3—C2 | 76.88 (16) | C29—Zr1—C28—C19 | −119.00 (18) |
| C1—Zr1—C3—C2 | 36.89 (14) | C22—C23—C29—C28 | 3.6 (3) |
| C31—Zr1—C3—C2 | 124.87 (15) | C22—C23—C29—C30 | −170.9 (2) |
| C30—Zr1—C3—C2 | 161.63 (14) | C22—C23—C29—Zr1 | 94.3 (2) |
| C29—Zr1—C3—C2 | −173.21 (15) | C20—C28—C29—C23 | −5.7 (3) |
| C28—Zr1—C3—C2 | 85.8 (4) | C19—C28—C29—C23 | 175.60 (18) |
| C6—Zr1—C3—C4 | −150.38 (14) | Zr1—C28—C29—C23 | 117.56 (18) |
| Cl1—Zr1—C3—C4 | 115.29 (15) | C20—C28—C29—C30 | 170.04 (17) |
| C19—Zr1—C3—C4 | −25.5 (2) | C19—C28—C29—C30 | −8.7 (2) |
| C5—Zr1—C3—C4 | −37.89 (14) | Zr1—C28—C29—C30 | −66.71 (13) |
| C2—Zr1—C3—C4 | −114.8 (2) | C20—C28—C29—Zr1 | −123.25 (17) |
| C1—Zr1—C3—C4 | −77.87 (16) | C19—C28—C29—Zr1 | 58.04 (14) |
| C31—Zr1—C3—C4 | 10.10 (17) | C6—Zr1—C29—C23 | −51.57 (17) |
| C30—Zr1—C3—C4 | 46.87 (17) | Cl1—Zr1—C29—C23 | 45.42 (16) |
| C29—Zr1—C3—C4 | 72.0 (2) | C4—Zr1—C29—C23 | 133.18 (17) |
| C28—Zr1—C3—C4 | −28.9 (4) | C19—Zr1—C29—C23 | −152.6 (2) |
| C2—C3—C4—C5 | 1.4 (2) | C3—Zr1—C29—C23 | 88.4 (2) |
| Zr1—C3—C4—C5 | 68.33 (15) | C5—Zr1—C29—C23 | 177.32 (16) |
| C2—C3—C4—Zr1 | −66.94 (15) | C1—Zr1—C29—C23 | −139.79 (18) |
| C6—Zr1—C4—C5 | −71.66 (18) | C31—Zr1—C29—C23 | 166.2 (2) |
| Cl1—Zr1—C4—C5 | −176.38 (14) | C30—Zr1—C29—C23 | 128.9 (2) |
| C19—Zr1—C4—C5 | 48.18 (16) | C28—Zr1—C29—C23 | −117.2 (2) |
| C3—Zr1—C4—C5 | −113.3 (2) | C6—Zr1—C29—C28 | 65.66 (12) |
| C2—Zr1—C4—C5 | −76.30 (16) | Cl1—Zr1—C29—C28 | 162.65 (12) |
| C1—Zr1—C4—C5 | −36.36 (14) | C4—Zr1—C29—C28 | −109.60 (14) |
| C31—Zr1—C4—C5 | 75.67 (15) | C19—Zr1—C29—C28 | −35.39 (12) |
| C30—Zr1—C4—C5 | 103.94 (15) | C3—Zr1—C29—C28 | −154.35 (15) |
| C29—Zr1—C4—C5 | 101.64 (16) | C5—Zr1—C29—C28 | −65.46 (15) |
| C28—Zr1—C4—C5 | 57.65 (18) | C1—Zr1—C29—C28 | −22.6 (2) |
| C6—Zr1—C4—C3 | 41.64 (19) | C31—Zr1—C29—C28 | −76.56 (13) |
| Cl1—Zr1—C4—C3 | −63.08 (14) | C30—Zr1—C29—C28 | −113.83 (17) |
| C19—Zr1—C4—C3 | 161.48 (14) | C6—Zr1—C29—C30 | 179.49 (12) |
| C5—Zr1—C4—C3 | 113.3 (2) | Cl1—Zr1—C29—C30 | −83.52 (11) |
| C2—Zr1—C4—C3 | 37.00 (15) | C4—Zr1—C29—C30 | 4.24 (16) |
| C1—Zr1—C4—C3 | 76.95 (16) | C19—Zr1—C29—C30 | 78.44 (13) |
| C31—Zr1—C4—C3 | −171.02 (15) | C3—Zr1—C29—C30 | −40.5 (2) |
| C30—Zr1—C4—C3 | −142.76 (14) | C5—Zr1—C29—C30 | 48.38 (16) |
| C29—Zr1—C4—C3 | −145.06 (14) | C1—Zr1—C29—C30 | 91.27 (18) |
| C28—Zr1—C4—C3 | 170.95 (13) | C31—Zr1—C29—C30 | 37.27 (12) |
| C2—C1—C5—C4 | 0.6 (3) | C28—Zr1—C29—C30 | 113.83 (17) |
| Zr1—C1—C5—C4 | −65.13 (15) | C25—C24—C30—C31 | −2.1 (3) |
| C2—C1—C5—Zr1 | 65.75 (16) | C25—C24—C30—C29 | 171.7 (2) |
| C3—C4—C5—C1 | −1.2 (2) | C25—C24—C30—Zr1 | −90.0 (2) |
| Zr1—C4—C5—C1 | 66.76 (16) | C23—C29—C30—C24 | 3.1 (4) |
| C3—C4—C5—Zr1 | −68.00 (15) | C28—C29—C30—C24 | −171.9 (2) |
| C6—Zr1—C5—C1 | 14.76 (17) | Zr1—C29—C30—C24 | 119.9 (2) |
| Cl1—Zr1—C5—C1 | −110.94 (14) | C23—C29—C30—C31 | 177.6 (2) |
| C4—Zr1—C5—C1 | −115.5 (2) | C28—C29—C30—C31 | 2.5 (2) |
| C19—Zr1—C5—C1 | 111.70 (15) | Zr1—C29—C30—C31 | −65.62 (14) |
| C3—Zr1—C5—C1 | −77.23 (16) | C23—C29—C30—Zr1 | −116.8 (2) |
| C2—Zr1—C5—C1 | −36.53 (15) | C28—C29—C30—Zr1 | 68.11 (13) |
| C31—Zr1—C5—C1 | 145.06 (16) | C6—Zr1—C30—C24 | −130.72 (17) |
| C30—Zr1—C5—C1 | 160.57 (14) | Cl1—Zr1—C30—C24 | −39.38 (16) |
| C29—Zr1—C5—C1 | 136.00 (14) | C4—Zr1—C30—C24 | 53.06 (18) |
| C28—Zr1—C5—C1 | 105.00 (15) | C19—Zr1—C30—C24 | 152.2 (2) |
| C6—Zr1—C5—C4 | 130.21 (14) | C3—Zr1—C30—C24 | 29.3 (2) |
| Cl1—Zr1—C5—C4 | 4.51 (17) | C5—Zr1—C30—C24 | 86.14 (18) |
| C19—Zr1—C5—C4 | −132.85 (15) | C2—Zr1—C30—C24 | 52.6 (3) |
| C3—Zr1—C5—C4 | 38.22 (14) | C1—Zr1—C30—C24 | 100.80 (19) |
| C2—Zr1—C5—C4 | 78.92 (15) | C31—Zr1—C30—C24 | 115.6 (2) |
| C1—Zr1—C5—C4 | 115.5 (2) | C29—Zr1—C30—C24 | −130.1 (2) |
| C31—Zr1—C5—C4 | −99.48 (15) | C28—Zr1—C30—C24 | −167.1 (2) |
| C30—Zr1—C5—C4 | −83.98 (15) | C6—Zr1—C30—C31 | 113.67 (12) |
| C29—Zr1—C5—C4 | −108.55 (14) | Cl1—Zr1—C30—C31 | −155.00 (12) |
| C28—Zr1—C5—C4 | −139.55 (13) | C4—Zr1—C30—C31 | −62.55 (13) |
| Cl1—Zr1—C6—C15 | 162.55 (13) | C19—Zr1—C30—C31 | 36.62 (12) |
| C4—Zr1—C6—C15 | 58.99 (18) | C3—Zr1—C30—C31 | −86.36 (14) |
| C19—Zr1—C6—C15 | −62.03 (15) | C5—Zr1—C30—C31 | −29.47 (14) |
| C3—Zr1—C6—C15 | 81.28 (15) | C2—Zr1—C30—C31 | −63.0 (2) |
| C5—Zr1—C6—C15 | 23.42 (16) | C1—Zr1—C30—C31 | −14.81 (17) |
| C2—Zr1—C6—C15 | 62.80 (15) | C29—Zr1—C30—C31 | 114.28 (17) |
| C1—Zr1—C6—C15 | 31.18 (14) | C28—Zr1—C30—C31 | 77.33 (13) |
| C31—Zr1—C6—C15 | −75.65 (16) | C6—Zr1—C30—C29 | −0.61 (15) |
| C30—Zr1—C6—C15 | −115.76 (14) | Cl1—Zr1—C30—C29 | 90.72 (11) |
| C29—Zr1—C6—C15 | −116.09 (14) | C4—Zr1—C30—C29 | −176.83 (12) |
| C28—Zr1—C6—C15 | −87.23 (14) | C19—Zr1—C30—C29 | −77.66 (13) |
| Cl1—Zr1—C6—C18 | 44.97 (15) | C3—Zr1—C30—C29 | 159.36 (12) |
| C4—Zr1—C6—C18 | −58.59 (19) | C5—Zr1—C30—C29 | −143.75 (12) |
| C19—Zr1—C6—C18 | −179.61 (15) | C2—Zr1—C30—C29 | −177.28 (18) |
| C3—Zr1—C6—C18 | −36.31 (16) | C1—Zr1—C30—C29 | −129.09 (13) |
| C5—Zr1—C6—C18 | −94.16 (16) | C31—Zr1—C30—C29 | −114.28 (17) |
| C2—Zr1—C6—C18 | −54.78 (16) | C28—Zr1—C30—C29 | −36.95 (11) |
| C1—Zr1—C6—C18 | −86.40 (16) | C26—C27—C31—C30 | 0.9 (3) |
| C31—Zr1—C6—C18 | 166.76 (13) | C26—C27—C31—C19 | −177.6 (2) |
| C30—Zr1—C6—C18 | 126.66 (14) | C26—C27—C31—Zr1 | 91.2 (2) |
| C29—Zr1—C6—C18 | 126.33 (15) | C24—C30—C31—C27 | 1.0 (3) |
| C28—Zr1—C6—C18 | 155.19 (16) | C29—C30—C31—C27 | −174.14 (17) |
| C15—C7—C8—C9 | 0.5 (3) | Zr1—C30—C31—C27 | 118.90 (18) |
| C7—C8—C9—C10 | −0.3 (3) | C24—C30—C31—C19 | 179.87 (18) |
| C8—C9—C10—C16 | −0.3 (3) | C29—C30—C31—C19 | 4.7 (2) |
| C17—C11—C12—C13 | −0.3 (3) | Zr1—C30—C31—C19 | −62.27 (14) |
| C11—C12—C13—C14 | 1.6 (3) | C24—C30—C31—Zr1 | −117.86 (18) |
| C12—C13—C14—C18 | −0.5 (3) | C29—C30—C31—Zr1 | 66.96 (13) |
| C8—C7—C15—C16 | 0.0 (3) | C28—C19—C31—C27 | 168.7 (2) |
| C8—C7—C15—C6 | −175.5 (2) | Zr1—C19—C31—C27 | −115.6 (2) |
| C18—C6—C15—C7 | −178.3 (2) | C28—C19—C31—C30 | −9.9 (2) |
| Zr1—C6—C15—C7 | 57.3 (3) | Zr1—C19—C31—C30 | 65.83 (14) |
| C18—C6—C15—C16 | 5.9 (2) | C28—C19—C31—Zr1 | −75.78 (13) |
| Zr1—C6—C15—C16 | −118.47 (15) | C6—Zr1—C31—C27 | 153.34 (17) |
| C9—C10—C16—C15 | 0.8 (3) | Cl1—Zr1—C31—C27 | −89.24 (18) |
| C9—C10—C16—C17 | −179.7 (2) | C4—Zr1—C31—C27 | 3.73 (19) |
| C7—C15—C16—C10 | −0.6 (3) | C19—Zr1—C31—C27 | 128.1 (2) |
| C6—C15—C16—C10 | 175.82 (18) | C3—Zr1—C31—C27 | −1.8 (2) |
| C7—C15—C16—C17 | 179.76 (18) | C5—Zr1—C31—C27 | 36.02 (19) |
| C6—C15—C16—C17 | −3.8 (2) | C2—Zr1—C31—C27 | 34.3 (2) |
| C12—C11—C17—C18 | −2.1 (3) | C1—Zr1—C31—C27 | 54.3 (2) |
| C12—C11—C17—C16 | 176.5 (2) | C30—Zr1—C31—C27 | −115.1 (2) |
| C10—C16—C17—C11 | 1.6 (4) | C29—Zr1—C31—C27 | −152.6 (2) |
| C15—C16—C17—C11 | −178.8 (2) | C28—Zr1—C31—C27 | 167.7 (2) |
| C10—C16—C17—C18 | −179.6 (2) | C6—Zr1—C31—C30 | −91.52 (14) |
| C15—C16—C17—C18 | −0.1 (2) | Cl1—Zr1—C31—C30 | 25.90 (12) |
| C13—C14—C18—C17 | −1.9 (3) | C4—Zr1—C31—C30 | 118.88 (13) |
| C13—C14—C18—C6 | 178.66 (19) | C19—Zr1—C31—C30 | −116.76 (17) |
| C11—C17—C18—C14 | 3.2 (3) | C3—Zr1—C31—C30 | 113.38 (13) |
| C16—C17—C18—C14 | −175.69 (18) | C5—Zr1—C31—C30 | 151.16 (13) |
| C11—C17—C18—C6 | −177.20 (18) | C2—Zr1—C31—C30 | 149.45 (13) |
| C16—C17—C18—C6 | 3.9 (2) | C1—Zr1—C31—C30 | 169.41 (12) |
| C15—C6—C18—C14 | 173.6 (2) | C29—Zr1—C31—C30 | −37.43 (11) |
| Zr1—C6—C18—C14 | −64.1 (3) | C28—Zr1—C31—C30 | −77.13 (13) |
| C15—C6—C18—C17 | −5.9 (2) | C6—Zr1—C31—C19 | 25.23 (16) |
| Zr1—C6—C18—C17 | 116.40 (16) | Cl1—Zr1—C31—C19 | 142.66 (11) |
| C6—Zr1—C19—C31 | −160.89 (12) | C4—Zr1—C31—C19 | −124.37 (13) |
| Cl1—Zr1—C19—C31 | −51.17 (14) | C3—Zr1—C31—C19 | −129.86 (13) |
| C4—Zr1—C19—C31 | 57.76 (13) | C5—Zr1—C31—C19 | −92.08 (13) |
| C3—Zr1—C19—C31 | 71.70 (16) | C2—Zr1—C31—C19 | −93.79 (15) |
| C5—Zr1—C19—C31 | 81.77 (13) | C1—Zr1—C31—C19 | −73.83 (13) |
| C2—Zr1—C19—C31 | 113.11 (13) | C30—Zr1—C31—C19 | 116.76 (17) |
| C1—Zr1—C19—C31 | 111.30 (13) | C29—Zr1—C31—C19 | 79.33 (13) |
| C30—Zr1—C19—C31 | −35.67 (11) | C28—Zr1—C31—C19 | 39.63 (12) |
| C29—Zr1—C19—C31 | −75.61 (13) | C37—C32—C33—C34 | 0.3 (3) |
| C28—Zr1—C19—C31 | −109.75 (18) | C38—C32—C33—C34 | −179.0 (2) |
| C6—Zr1—C19—C28 | −51.14 (13) | C32—C33—C34—C35 | −1.0 (4) |
| Cl1—Zr1—C19—C28 | 58.58 (14) | C33—C34—C35—C36 | 1.3 (4) |
| C4—Zr1—C19—C28 | 167.51 (12) | C34—C35—C36—C37 | −1.0 (4) |
| C3—Zr1—C19—C28 | −178.54 (13) | C35—C36—C37—C32 | 0.3 (4) |
| C5—Zr1—C19—C28 | −168.48 (14) | C33—C32—C37—C36 | 0.1 (3) |
| C2—Zr1—C19—C28 | −137.14 (12) | C38—C32—C37—C36 | 179.4 (2) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2294).
References
- Alt, H. G. & Samuel, E. (1998). Chem. Soc. Rev. 27, 323–329.
- Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
- Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
- Lund, E. C. & Livinghouse, T. (1990). Organometallics, 9, 2426–2427.
- Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
- Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.
- Samuel, E. & Setton, R. (1965). J. Organomet. Chem. 4, 156–158.
- Schmid, M. A., Alt, H. G. & Milius, W. (1995). J. Organomet. Chem. 501, 101–106.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050816/kp2294sup1.cif
e-67-00m54-sup1.cif (39.7KB, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050816/kp2294Isup2.hkl
e-67-00m54-Isup2.hkl (267.3KB, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report