Tri­benzyl{[eta]⁵-[2-(p-tolyl)­prop-2-yl]­cyclo­penta­dienyl}­zirconium

The title compound, [Zr(C₇H₇)₃(C₁₅H₁₇)], (I), crystallizes from light petroleum with two independent mol­ecules in the asymmetric unit. Whereas in the parent mol­ecule, Zr([eta]⁵-C₅H₅)(CH₂Ph)₃, all three Zr-CH₂Ph angles are equal, in (I), they differ significantly. In spite of their different environments, both independent mol­ecules in (I) exhibit a small, an expected, and a large Zr-CH₂Ph angle. The angles are similar to those of the closely related tri­benzyl­[[eta]⁵-(benzyl­di­methyl­silyl)­cyclo­penta­dienyl]­zirconium complex. The smallest Zr-CH₂Ph angle and the consequently relatively short Zr...C_ipso distance are indicative of [eta]²-bonding of the benzyl group.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(η⁵-(2-(p-tolyl)prop-2-yl)cyclopentadienyl)-tribenzylzirconium

Crystal data

[Zr(C7H7)3(C15H17)]	F(000) = 2352
Mr = 561.88	Dx = 1.313 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.0892 (18) Å	Cell parameters from 14107 reflections
b = 11.0572 (8) Å	θ = 1.9–28.0°
c = 22.0033 (15) Å	µ = 0.41 mm^−1
β = 111.395 (2)°	T = 100 K
V = 5683.4 (7) Å^3	Prism, yellow
Z = 8	0.53 × 0.42 × 0.11 mm

Data collection

Siemens SMART diffractometer	13434 independent reflections
Radiation source: fine-focus sealed tube	9028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.128
CCD ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: ψ scan (XPREP; Siemens, 1995)	h = −21→33
Tmin = 0.844, Tmax = 0.956	k = −14→14
49130 measured reflections	l = −28→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: mixed
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0403P)^2] where P = (Fo^2 + 2Fc^2)/3
13434 reflections	(Δ/σ)max = 0.001
715 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −1.15 e Å^−3

Special details

Experimental. The crystal was mounted on a glass rod and cooled by a cold N₂ gas stream. R_int of 0.128 is probably due to the fact that the data was collected with a CCD detector with a correspondingly high redundancy.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.00458 (9)	0.8090 (2)	0.40595 (12)	0.0180 (5)
C1'	−0.47419 (9)	0.7212 (2)	0.41298 (13)	0.0206 (6)
C2	0.00522 (9)	0.8255 (2)	0.34239 (13)	0.0189 (5)
H2	−0.0238	0.8030	0.3037	0.023*
C2'	−0.48298 (10)	0.7037 (2)	0.34595 (13)	0.0225 (6)
H2'	−0.5154	0.7264	0.3107	0.027*
C3	0.05691 (10)	0.8813 (2)	0.34729 (13)	0.0223 (6)
H3	0.0675	0.9038	0.3126	0.027*
C3'	−0.43415 (10)	0.6461 (2)	0.34201 (14)	0.0236 (6)
H3'	−0.4292	0.6223	0.3039	0.028*
C4	0.08977 (10)	0.8970 (2)	0.41395 (13)	0.0246 (6)
H4	0.1262	0.9305	0.4312	0.029*
C4'	−0.39428 (10)	0.6309 (2)	0.40586 (14)	0.0263 (6)
H4'	−0.3580	0.5968	0.4173	0.032*
C5	0.05748 (10)	0.8530 (2)	0.44995 (13)	0.0220 (6)
H5	0.0691	0.8529	0.4952	0.026*
C5'	−0.41889 (10)	0.6764 (2)	0.44960 (13)	0.0233 (6)
H5'	−0.4017	0.6769	0.4949	0.028*
C6	−0.04800 (10)	0.7679 (2)	0.42002 (13)	0.0221 (6)
C6'	−0.52008 (10)	0.7671 (2)	0.43763 (13)	0.0217 (6)
C7	−0.03706 (11)	0.7730 (3)	0.49349 (13)	0.0278 (6)
H7A	−0.0067	0.7182	0.5165	0.042*
H7B	−0.0713	0.7503	0.5006	0.042*
H7C	−0.0264	0.8538	0.5093	0.042*
C7'	−0.49796 (10)	0.7676 (3)	0.51239 (12)	0.0279 (6)
H7'1	−0.4843	0.6884	0.5285	0.042*
H7'2	−0.5285	0.7900	0.5267	0.042*
H7'3	−0.4672	0.8248	0.5288	0.042*
C8	−0.06484 (10)	0.6398 (2)	0.39465 (13)	0.0260 (6)
H8A	−0.0732	0.6378	0.3485	0.039*
H8B	−0.0981	0.6153	0.4033	0.039*
H8C	−0.0338	0.5855	0.4162	0.039*
C8'	−0.53848 (10)	0.8946 (2)	0.41174 (14)	0.0274 (6)
H8'1	−0.5056	0.9468	0.4248	0.041*
H8'2	−0.5659	0.9246	0.4292	0.041*
H8'3	−0.5555	0.8926	0.3650	0.041*
C9	−0.09636 (10)	0.8592 (2)	0.38606 (12)	0.0215 (6)
C9'	−0.57162 (10)	0.6779 (2)	0.41393 (13)	0.0225 (6)
C10	−0.15310 (10)	0.8242 (3)	0.35481 (14)	0.0283 (6)
H10	−0.1626	0.7427	0.3529	0.034*
C10'	−0.62687 (10)	0.7165 (3)	0.40445 (14)	0.0316 (7)
H10'	−0.6335	0.7974	0.4109	0.038*
C11	−0.19577 (10)	0.9087 (3)	0.32641 (14)	0.0301 (7)
H11	−0.2333	0.8824	0.3058	0.036*
C11'	−0.67235 (11)	0.6351 (3)	0.38547 (15)	0.0351 (7)
H11'	−0.7090	0.6631	0.3790	0.042*
C12	−0.18390 (10)	1.0315 (3)	0.32788 (13)	0.0270 (6)
C12'	−0.66458 (10)	0.5141 (3)	0.37597 (13)	0.0285 (6)
C13	−0.12721 (10)	1.0666 (2)	0.35971 (13)	0.0249 (6)
H13	−0.1178	1.1482	0.3622	0.030*
C13'	−0.60917 (10)	0.4756 (3)	0.38682 (13)	0.0273 (6)
H13'	−0.6024	0.3943	0.3814	0.033*
C14	−0.08450 (10)	0.9819 (2)	0.38779 (12)	0.0243 (6)
H14	−0.0470	1.0081	0.4083	0.029*
C14'	−0.56355 (10)	0.5564 (2)	0.40560 (13)	0.0251 (6)
H14'	−0.5269	0.5281	0.4127	0.030*
C15	−0.23065 (11)	1.1220 (3)	0.29601 (15)	0.0370 (7)
H15A	−0.2193	1.1999	0.3158	0.056*
H15B	−0.2652	1.0968	0.3016	0.056*
H15C	−0.2372	1.1270	0.2503	0.056*
C15'	−0.71388 (11)	0.4248 (3)	0.35314 (15)	0.0396 (8)
H15D	−0.7154	0.3801	0.3899	0.059*
H15E	−0.7083	0.3700	0.3222	0.059*
H15F	−0.7492	0.4679	0.3329	0.059*
C16	0.16926 (10)	0.7075 (3)	0.37806 (14)	0.0236 (6)
C16'	−0.46204 (11)	0.9524 (3)	0.29623 (14)	0.0255 (6)
C17	0.17362 (9)	0.8054 (2)	0.33404 (13)	0.0216 (6)
C17'	−0.43788 (9)	1.0762 (2)	0.30560 (12)	0.0225 (6)
C18	0.14364 (10)	0.7996 (3)	0.26632 (13)	0.0284 (6)
H18	0.1224	0.7308	0.2484	0.034*
C18'	−0.45638 (10)	1.1635 (2)	0.33950 (13)	0.0262 (6)
H18'	−0.4846	1.1431	0.3558	0.031*
C19	0.14501 (11)	0.8942 (3)	0.22551 (14)	0.0321 (7)
H19	0.1243	0.8887	0.1809	0.039*
C19'	−0.43385 (11)	1.2798 (3)	0.34944 (14)	0.0309 (7)
H19'	−0.4467	1.3357	0.3726	0.037*
C20	0.17688 (11)	0.9965 (3)	0.25055 (14)	0.0332 (7)
H20	0.1778	1.0602	0.2233	0.040*
C20'	−0.39220 (10)	1.3127 (2)	0.32492 (14)	0.0290 (7)
H20'	−0.3772	1.3907	0.3311	0.035*
C21	0.20784 (10)	1.0026 (2)	0.31762 (15)	0.0311 (7)
H21	0.2299	1.0707	0.3351	0.037*
C21'	−0.37328 (10)	1.2280 (2)	0.29120 (13)	0.0275 (6)
H21'	−0.3453	1.2491	0.2747	0.033*
C22	0.20609 (10)	0.9090 (2)	0.35808 (13)	0.0246 (6)
H22	0.2271	0.9150	0.4026	0.029*
C22'	−0.39563 (10)	1.1119 (2)	0.28172 (13)	0.0243 (6)
H22'	−0.3822	1.0563	0.2589	0.029*
C23	0.03338 (11)	0.5757 (3)	0.30084 (14)	0.0249 (6)
C23'	−0.38497 (11)	0.9626 (3)	0.47763 (14)	0.0255 (6)
C24	0.05762 (10)	0.4522 (2)	0.31210 (12)	0.0214 (6)
C24'	−0.32456 (10)	0.9563 (2)	0.48570 (12)	0.0233 (6)
C25	0.10615 (9)	0.4200 (2)	0.29851 (12)	0.0228 (6)
H25	0.1234	0.4776	0.2809	0.027*
C25'	−0.30070 (10)	1.0363 (2)	0.45273 (13)	0.0248 (6)
H25'	−0.3221	1.1019	0.4302	0.030*
C26	0.12923 (10)	0.3043 (2)	0.31068 (13)	0.0258 (6)
H26	0.1615	0.2856	0.3012	0.031*
C26'	−0.24605 (10)	1.0187 (3)	0.45347 (14)	0.0312 (7)
H26'	−0.2311	1.0728	0.4314	0.037*
C27	0.10458 (10)	0.2170 (2)	0.33669 (13)	0.0270 (6)
H27	0.1201	0.1397	0.3451	0.032*
C27'	−0.21318 (11)	0.9227 (3)	0.48619 (15)	0.0362 (8)
H27'	−0.1767	0.9110	0.4857	0.043*
C28	0.05614 (11)	0.2462 (2)	0.35018 (13)	0.0282 (6)
H28	0.0388	0.1877	0.3671	0.034*
C28'	−0.23511 (11)	0.8439 (3)	0.51985 (15)	0.0385 (8)
H28'	−0.2127	0.7804	0.5434	0.046*
C29	0.03377 (10)	0.3613 (2)	0.33864 (13)	0.0243 (6)
H29	0.0018	0.3794	0.3488	0.029*
C29'	−0.28983 (11)	0.8588 (2)	0.51880 (14)	0.0305 (7)
H29'	−0.3043	0.8031	0.5405	0.037*
C30	0.08257 (11)	0.5656 (3)	0.48134 (14)	0.0258 (6)
C30'	−0.32755 (11)	0.8171 (3)	0.34800 (15)	0.0256 (6)
C31	0.14472 (10)	0.5626 (2)	0.50287 (13)	0.0239 (6)
C31'	−0.32877 (9)	0.7179 (2)	0.30227 (13)	0.0218 (6)
C32	0.17936 (11)	0.6512 (2)	0.54461 (13)	0.0279 (6)
H32	0.1624	0.7071	0.5635	0.033*
C32'	−0.36419 (11)	0.7221 (3)	0.23607 (13)	0.0295 (7)
H32'	−0.3867	0.7901	0.2198	0.035*
C33	0.23750 (11)	0.6583 (2)	0.55854 (14)	0.0323 (7)
H33	0.2593	0.7163	0.5876	0.039*
C33'	−0.36616 (11)	0.6267 (3)	0.19453 (14)	0.0355 (7)
H33'	−0.3901	0.6316	0.1509	0.043*
C34	0.26347 (11)	0.5784 (3)	0.52889 (14)	0.0338 (7)
H34	0.3024	0.5845	0.5368	0.041*
C34'	−0.33338 (11)	0.5246 (3)	0.21670 (15)	0.0361 (7)
H34'	−0.3352	0.4606	0.1886	0.043*
C35	0.23102 (11)	0.4903 (3)	0.48790 (14)	0.0333 (7)
H35	0.2485	0.4357	0.4689	0.040*
C35'	−0.29761 (11)	0.5193 (3)	0.28187 (15)	0.0320 (7)
H35'	−0.2748	0.4514	0.2975	0.038*
C36	0.17261 (11)	0.4816 (2)	0.47443 (13)	0.0283 (6)
H36	0.1515	0.4215	0.4463	0.034*
C36'	−0.29547 (10)	0.6140 (2)	0.32376 (14)	0.0252 (6)
H36'	−0.2713	0.6084	0.3673	0.030*
H16A	0.1736 (12)	0.632 (3)	0.3658 (15)	0.046 (10)*
H16B	0.2009 (9)	0.710 (2)	0.4229 (12)	0.015 (6)*
H16C	−0.4604 (11)	0.912 (3)	0.2610 (14)	0.036 (9)*
H16D	−0.4997 (12)	0.951 (2)	0.2964 (13)	0.040 (8)*
H23A	−0.0038 (11)	0.572 (2)	0.2941 (12)	0.022 (7)*
H23B	0.0407 (10)	0.618 (2)	0.2683 (13)	0.022 (7)*
H23C	−0.4001 (10)	1.037 (3)	0.4652 (13)	0.028 (8)*
H23D	−0.3949 (11)	0.921 (3)	0.5110 (14)	0.036 (8)*
H30A	0.0650 (10)	0.492 (2)	0.4639 (13)	0.029 (7)*
H30B	0.0674 (9)	0.605 (2)	0.5091 (11)	0.009 (6)*
H30C	−0.2902 (11)	0.820 (2)	0.3863 (13)	0.032 (8)*
H30D	−0.3292 (11)	0.889 (3)	0.3277 (13)	0.031 (8)*
Zr1	0.084476 (9)	0.67666 (2)	0.393830 (12)	0.01870 (7)
Zr1'	−0.401236 (9)	0.85037 (2)	0.384167 (12)	0.01936 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0201 (12)	0.0152 (13)	0.0191 (14)	0.0015 (9)	0.0079 (10)	0.0016 (12)
C1'	0.0192 (12)	0.0196 (14)	0.0218 (15)	−0.0024 (9)	0.0059 (10)	0.0010 (12)
C2	0.0178 (12)	0.0167 (13)	0.0212 (14)	0.0036 (9)	0.0058 (10)	0.0017 (12)
C2'	0.0194 (12)	0.0196 (14)	0.0274 (16)	−0.0049 (9)	0.0071 (11)	−0.0026 (13)
C3	0.0266 (13)	0.0168 (14)	0.0268 (16)	0.0052 (10)	0.0135 (11)	0.0068 (13)
C3'	0.0292 (14)	0.0180 (14)	0.0258 (16)	−0.0048 (10)	0.0128 (11)	−0.0072 (13)
C4	0.0217 (13)	0.0193 (14)	0.0317 (16)	−0.0011 (10)	0.0087 (11)	−0.0012 (13)
C4'	0.0235 (13)	0.0186 (14)	0.0379 (18)	0.0052 (10)	0.0126 (12)	0.0021 (13)
C5	0.0261 (13)	0.0203 (14)	0.0172 (14)	0.0003 (10)	0.0052 (10)	−0.0047 (12)
C5'	0.0230 (13)	0.0208 (14)	0.0242 (15)	0.0015 (10)	0.0064 (11)	0.0038 (13)
C6	0.0245 (13)	0.0237 (15)	0.0200 (15)	−0.0019 (10)	0.0103 (11)	−0.0007 (13)
C6'	0.0219 (12)	0.0196 (14)	0.0237 (15)	0.0026 (10)	0.0082 (11)	0.0005 (12)
C7	0.0327 (14)	0.0305 (16)	0.0225 (16)	−0.0024 (11)	0.0128 (12)	0.0017 (14)
C7'	0.0241 (13)	0.0337 (17)	0.0272 (16)	−0.0006 (11)	0.0108 (11)	−0.0029 (14)
C8	0.0291 (14)	0.0238 (15)	0.0260 (16)	−0.0043 (11)	0.0112 (12)	0.0004 (13)
C8'	0.0260 (13)	0.0237 (15)	0.0341 (17)	0.0021 (11)	0.0127 (12)	−0.0031 (14)
C9	0.0237 (13)	0.0273 (15)	0.0159 (14)	0.0004 (10)	0.0101 (10)	−0.0023 (12)
C9'	0.0239 (13)	0.0253 (15)	0.0185 (14)	0.0025 (10)	0.0078 (10)	0.0033 (13)
C10	0.0282 (14)	0.0280 (16)	0.0330 (17)	−0.0047 (11)	0.0163 (12)	−0.0036 (14)
C10'	0.0287 (14)	0.0294 (16)	0.0381 (18)	0.0032 (11)	0.0137 (13)	0.0004 (15)
C11	0.0175 (13)	0.0384 (18)	0.0357 (18)	−0.0020 (11)	0.0113 (12)	−0.0014 (15)
C11'	0.0194 (13)	0.0426 (19)	0.044 (2)	0.0021 (12)	0.0127 (12)	0.0005 (16)
C12	0.0261 (14)	0.0366 (17)	0.0218 (15)	0.0053 (11)	0.0129 (11)	0.0024 (14)
C12'	0.0244 (14)	0.0351 (17)	0.0238 (15)	−0.0041 (11)	0.0063 (11)	0.0058 (14)
C13	0.0294 (14)	0.0243 (15)	0.0230 (15)	0.0005 (11)	0.0118 (11)	−0.0012 (13)
C13'	0.0320 (14)	0.0262 (16)	0.0229 (16)	−0.0011 (11)	0.0092 (12)	0.0040 (13)
C14	0.0240 (13)	0.0282 (16)	0.0198 (15)	0.0001 (10)	0.0070 (11)	−0.0036 (13)
C14'	0.0249 (13)	0.0272 (16)	0.0249 (16)	0.0024 (10)	0.0112 (11)	0.0021 (13)
C15	0.0276 (15)	0.0426 (19)	0.0405 (19)	0.0051 (12)	0.0119 (13)	−0.0001 (16)
C15'	0.0320 (16)	0.043 (2)	0.043 (2)	−0.0074 (13)	0.0132 (14)	0.0040 (17)
C16	0.0217 (13)	0.0217 (16)	0.0246 (16)	0.0026 (10)	0.0053 (11)	0.0023 (14)
C16'	0.0232 (14)	0.0255 (16)	0.0253 (17)	−0.0011 (10)	0.0056 (12)	−0.0004 (14)
C17	0.0178 (12)	0.0234 (15)	0.0254 (15)	0.0056 (10)	0.0100 (10)	0.0043 (13)
C17'	0.0168 (12)	0.0282 (15)	0.0181 (14)	0.0031 (10)	0.0013 (10)	0.0051 (13)
C18	0.0220 (13)	0.0330 (17)	0.0303 (17)	0.0001 (11)	0.0096 (12)	0.0003 (14)
C18'	0.0241 (13)	0.0308 (16)	0.0245 (16)	0.0037 (11)	0.0096 (11)	0.0055 (13)
C19	0.0298 (15)	0.0432 (19)	0.0254 (16)	0.0062 (12)	0.0125 (12)	0.0076 (15)
C19'	0.0315 (15)	0.0283 (16)	0.0327 (18)	0.0067 (11)	0.0115 (13)	−0.0018 (14)
C20	0.0334 (15)	0.0346 (18)	0.0365 (19)	0.0090 (12)	0.0186 (13)	0.0140 (16)
C20'	0.0271 (14)	0.0219 (15)	0.0305 (17)	0.0005 (11)	0.0015 (12)	0.0007 (14)
C21	0.0280 (14)	0.0246 (16)	0.0437 (19)	−0.0006 (11)	0.0166 (13)	0.0011 (15)
C21'	0.0151 (12)	0.0335 (16)	0.0308 (17)	0.0019 (10)	0.0047 (11)	0.0051 (14)
C22	0.0191 (12)	0.0287 (16)	0.0255 (16)	0.0012 (10)	0.0076 (11)	−0.0003 (13)
C22'	0.0230 (13)	0.0271 (15)	0.0185 (15)	0.0060 (10)	0.0024 (10)	0.0020 (13)
C23	0.0238 (15)	0.0259 (16)	0.0240 (16)	−0.0007 (11)	0.0076 (12)	−0.0038 (14)
C23'	0.0260 (14)	0.0246 (16)	0.0243 (16)	−0.0004 (11)	0.0072 (12)	−0.0001 (14)
C24	0.0237 (13)	0.0226 (14)	0.0131 (14)	−0.0034 (10)	0.0009 (10)	−0.0056 (12)
C24'	0.0254 (13)	0.0214 (14)	0.0172 (14)	−0.0011 (10)	0.0008 (10)	−0.0089 (12)
C25	0.0211 (13)	0.0261 (15)	0.0180 (14)	−0.0037 (10)	0.0032 (10)	−0.0025 (12)
C25'	0.0228 (13)	0.0238 (15)	0.0233 (15)	−0.0006 (10)	0.0031 (11)	−0.0046 (13)
C26	0.0207 (13)	0.0304 (16)	0.0233 (15)	0.0009 (10)	0.0045 (11)	−0.0041 (13)
C26'	0.0268 (14)	0.0301 (17)	0.0345 (18)	−0.0078 (11)	0.0086 (12)	−0.0123 (15)
C27	0.0283 (14)	0.0249 (15)	0.0226 (15)	0.0023 (11)	0.0030 (11)	−0.0023 (13)
C27'	0.0207 (14)	0.0352 (18)	0.046 (2)	−0.0022 (12)	0.0047 (13)	−0.0208 (16)
C28	0.0349 (15)	0.0259 (16)	0.0211 (15)	−0.0082 (11)	0.0072 (12)	0.0001 (14)
C28'	0.0306 (15)	0.0247 (16)	0.040 (2)	0.0073 (11)	−0.0110 (13)	−0.0102 (15)
C29	0.0222 (13)	0.0320 (16)	0.0191 (15)	−0.0032 (10)	0.0082 (10)	−0.0074 (13)
C29'	0.0315 (15)	0.0228 (15)	0.0268 (17)	−0.0018 (11)	−0.0019 (12)	−0.0026 (14)
C30	0.0319 (15)	0.0234 (16)	0.0198 (16)	0.0013 (12)	0.0070 (12)	0.0038 (14)
C30'	0.0239 (14)	0.0220 (16)	0.0291 (17)	−0.0041 (11)	0.0075 (12)	−0.0023 (14)
C31	0.0317 (14)	0.0196 (14)	0.0155 (14)	0.0010 (10)	0.0027 (11)	0.0086 (12)
C31'	0.0190 (12)	0.0259 (15)	0.0233 (15)	−0.0052 (10)	0.0110 (11)	−0.0048 (13)
C32	0.0337 (15)	0.0234 (15)	0.0209 (15)	0.0056 (11)	0.0034 (11)	0.0021 (13)
C32'	0.0285 (14)	0.0342 (17)	0.0256 (16)	−0.0010 (11)	0.0094 (12)	−0.0018 (14)
C33	0.0351 (15)	0.0236 (16)	0.0260 (17)	0.0005 (11)	−0.0033 (12)	−0.0006 (14)
C33'	0.0310 (15)	0.053 (2)	0.0217 (16)	−0.0092 (13)	0.0086 (12)	−0.0105 (16)
C34	0.0257 (14)	0.0320 (17)	0.0342 (18)	0.0042 (11)	−0.0003 (12)	0.0069 (15)
C34'	0.0334 (15)	0.0389 (19)	0.0393 (19)	−0.0101 (13)	0.0171 (14)	−0.0203 (16)
C35	0.0375 (16)	0.0279 (16)	0.0292 (17)	0.0118 (12)	0.0060 (13)	0.0061 (15)
C35'	0.0291 (14)	0.0275 (16)	0.045 (2)	−0.0017 (11)	0.0206 (13)	−0.0028 (15)
C36	0.0342 (15)	0.0210 (15)	0.0231 (16)	0.0021 (11)	0.0027 (12)	0.0031 (13)
C36'	0.0224 (13)	0.0305 (16)	0.0258 (16)	−0.0010 (10)	0.0125 (11)	−0.0011 (14)
Zr1	0.01835 (12)	0.01805 (14)	0.01742 (14)	0.00055 (9)	0.00382 (9)	0.00170 (11)
Zr1'	0.01684 (12)	0.01983 (14)	0.01948 (14)	−0.00036 (9)	0.00431 (9)	−0.00150 (11)

Geometric parameters (Å, º)

C1—C5	1.413 (3)	C17—C22	1.393 (3)
C1—C2	1.416 (3)	C17—C18	1.404 (4)
C1—C6	1.530 (3)	C17'—C18'	1.399 (4)
C1—Zr1	2.573 (2)	C17'—C22'	1.401 (3)
C1'—C5'	1.416 (3)	C18—C19	1.388 (4)
C1'—C2'	1.423 (4)	C18—H18	0.9300
C1'—C6'	1.527 (3)	C18'—C19'	1.389 (4)
C1'—Zr1'	2.576 (2)	C18'—H18'	0.9300
C2—C3	1.404 (3)	C19—C20	1.378 (4)
C2—Zr1	2.510 (2)	C19—H19	0.9300
C2—H2	0.9300	C19'—C20'	1.388 (4)
C2'—C3'	1.411 (3)	C19'—H19'	0.9300
C2'—Zr1'	2.507 (2)	C20—C21	1.396 (4)
C2'—H2'	0.9300	C20—H20	0.9300
C3—C4	1.407 (4)	C20'—C21'	1.382 (4)
C3—Zr1	2.476 (2)	C20'—H20'	0.9300
C3—H3	0.9300	C21—C22	1.377 (4)
C3'—C4'	1.406 (4)	C21—H21	0.9300
C3'—Zr1'	2.467 (2)	C21'—C22'	1.386 (4)
C3'—H3'	0.9300	C21'—H21'	0.9300
C4—C5	1.410 (3)	C22—H22	0.9300
C4—Zr1	2.471 (3)	C22'—H22'	0.9300
C4—H4	0.9300	C23—C24	1.478 (4)
C4'—C5'	1.412 (3)	C23—Zr1	2.272 (3)
C4'—Zr1'	2.467 (3)	C23—H23A	0.89 (2)
C4'—H4'	0.9300	C23—H23B	0.93 (3)
C5—Zr1	2.529 (2)	C23'—C24'	1.462 (4)
C5—H5	0.9300	C23'—Zr1'	2.307 (3)
C5'—Zr1'	2.536 (3)	C23'—H23C	0.90 (3)
C5'—H5'	0.9300	C23'—H23D	0.97 (3)
C6—C8	1.525 (3)	C24—C25	1.402 (3)
C6—C7	1.539 (3)	C24—C29	1.402 (3)
C6—C9	1.545 (3)	C24'—C25'	1.408 (4)
C6'—C8'	1.528 (3)	C24'—C29'	1.410 (3)
C6'—C7'	1.532 (4)	C24'—Zr1'	2.632 (2)
C6'—C9'	1.557 (3)	C25—C26	1.389 (4)
C7—H7A	0.9600	C25—H25	0.9300
C7—H7B	0.9600	C25'—C26'	1.379 (3)
C7—H7C	0.9600	C25'—H25'	0.9300
C7'—H7'1	0.9600	C26—C27	1.378 (4)
C7'—H7'2	0.9600	C26—H26	0.9300
C7'—H7'3	0.9600	C26'—C27'	1.375 (4)
C8—H8A	0.9600	C26'—H26'	0.9300
C8—H8B	0.9600	C27—C28	1.390 (4)
C8—H8C	0.9600	C27—H27	0.9300
C8'—H8'1	0.9600	C27'—C28'	1.381 (4)
C8'—H8'2	0.9600	C27'—H27'	0.9300
C8'—H8'3	0.9600	C28—C29	1.377 (4)
C9—C14	1.387 (4)	C28—H28	0.9300
C9—C10	1.391 (3)	C28'—C29'	1.374 (4)
C9'—C14'	1.380 (4)	C28'—H28'	0.9300
C9'—C10'	1.391 (3)	C29—H29	0.9300
C10—C11	1.386 (4)	C29'—H29'	0.9300
C10—H10	0.9300	C30—C31	1.456 (4)
C10'—C11'	1.393 (4)	C30—Zr1	2.299 (3)
C10'—H10'	0.9300	C30—H30A	0.94 (3)
C11—C12	1.388 (4)	C30—H30B	0.94 (2)
C11—H11	0.9300	C30'—C31'	1.480 (4)
C11'—C12'	1.378 (4)	C30'—Zr1'	2.293 (3)
C11'—H11'	0.9300	C30'—H30C	1.01 (3)
C12—C13	1.392 (3)	C30'—H30D	0.90 (3)
C12—C15	1.506 (4)	C31—C32	1.406 (3)
C12'—C13'	1.389 (3)	C31—C36	1.415 (4)
C12'—C15'	1.518 (4)	C31—Zr1	2.643 (2)
C13—C14	1.387 (3)	C31'—C36'	1.398 (3)
C13—H13	0.9300	C31'—C32'	1.403 (4)
C13'—C14'	1.391 (3)	C32—C33	1.379 (4)
C13'—H13'	0.9300	C32—H32	0.9300
C14—H14	0.9300	C32'—C33'	1.385 (4)
C14'—H14'	0.9300	C32'—H32'	0.9300
C15—H15A	0.9600	C33—C34	1.393 (4)
C15—H15B	0.9600	C33—H33	0.9300
C15—H15C	0.9600	C33'—C34'	1.376 (4)
C15'—H15D	0.9600	C33'—H33'	0.9300
C15'—H15E	0.9600	C34—C35	1.374 (4)
C15'—H15F	0.9600	C34—H34	0.9300
C16—C17	1.483 (4)	C34'—C35'	1.388 (4)
C16—Zr1	2.302 (2)	C34'—H34'	0.9300
C16—H16A	0.90 (3)	C35—C36	1.389 (4)
C16—H16B	1.02 (2)	C35—H35	0.9300
C16'—C17'	1.480 (4)	C35'—C36'	1.383 (4)
C16'—Zr1'	2.278 (3)	C35'—H35'	0.9300
C16'—H16C	0.91 (3)	C36—H36	0.9300
C16'—H16D	0.95 (3)	C36'—H36'	0.9300
C5—C1—C2	106.6 (2)	C20'—C21'—C22'	120.6 (3)
C5—C1—C6	128.8 (2)	C20'—C21'—H21'	119.7
C2—C1—C6	124.0 (2)	C22'—C21'—H21'	119.7
C5—C1—Zr1	72.19 (13)	C21—C22—C17	121.7 (3)
C2—C1—Zr1	71.38 (13)	C21—C22—H22	119.2
C6—C1—Zr1	127.85 (16)	C17—C22—H22	119.2
C5'—C1'—C2'	106.9 (2)	C21'—C22'—C17'	121.6 (2)
C5'—C1'—C6'	128.6 (2)	C21'—C22'—H22'	119.2
C2'—C1'—C6'	124.2 (2)	C17'—C22'—H22'	119.2
C5'—C1'—Zr1'	72.38 (14)	C24—C23—Zr1	103.91 (17)
C2'—C1'—Zr1'	71.08 (13)	C24—C23—H23A	109.3 (16)
C6'—C1'—Zr1'	126.79 (17)	Zr1—C23—H23A	112.6 (16)
C3—C2—C1	108.9 (2)	C24—C23—H23B	114.2 (16)
C3—C2—Zr1	72.29 (13)	Zr1—C23—H23B	103.9 (16)
C1—C2—Zr1	76.29 (13)	H23A—C23—H23B	113 (2)
C3—C2—H2	125.6	C24'—C23'—Zr1'	85.48 (16)
C1—C2—H2	125.6	C24'—C23'—H23C	112.6 (16)
Zr1—C2—H2	117.7	Zr1'—C23'—H23C	107.5 (17)
C3'—C2'—C1'	108.4 (2)	C24'—C23'—H23D	115.2 (16)
C3'—C2'—Zr1'	71.97 (13)	Zr1'—C23'—H23D	114.1 (16)
C1'—C2'—Zr1'	76.45 (14)	H23C—C23'—H23D	117 (2)
C3'—C2'—H2'	125.8	C25—C24—C29	116.3 (2)
C1'—C2'—H2'	125.8	C25—C24—C23	122.4 (2)
Zr1'—C2'—H2'	117.7	C29—C24—C23	121.3 (2)
C2—C3—C4	107.9 (2)	C25'—C24'—C29'	116.6 (2)
C2—C3—Zr1	75.00 (14)	C25'—C24'—C23'	121.6 (2)
C4—C3—Zr1	73.31 (15)	C29'—C24'—C23'	121.1 (3)
C2—C3—H3	126.0	C25'—C24'—Zr1'	99.13 (16)
C4—C3—H3	126.0	C29'—C24'—Zr1'	102.73 (16)
Zr1—C3—H3	117.6	C23'—C24'—Zr1'	60.90 (14)
C4'—C3'—C2'	108.0 (2)	C26—C25—C24	121.8 (2)
C4'—C3'—Zr1'	73.46 (15)	C26—C25—H25	119.1
C2'—C3'—Zr1'	75.07 (14)	C24—C25—H25	119.1
C4'—C3'—H3'	126.0	C26'—C25'—C24'	120.8 (2)
C2'—C3'—H3'	126.0	C26'—C25'—H25'	119.6
Zr1'—C3'—H3'	117.5	C24'—C25'—H25'	119.6
C3—C4—C5	107.7 (2)	C27—C26—C25	120.4 (2)
C3—C4—Zr1	73.64 (15)	C27—C26—H26	119.8
C5—C4—Zr1	75.87 (15)	C25—C26—H26	119.8
C3—C4—H4	126.1	C27'—C26'—C25'	121.3 (3)
C5—C4—H4	126.1	C27'—C26'—H26'	119.4
Zr1—C4—H4	116.5	C25'—C26'—H26'	119.4
C3'—C4'—C5'	108.0 (2)	C26—C27—C28	119.1 (2)
C3'—C4'—Zr1'	73.42 (15)	C26—C27—H27	120.5
C5'—C4'—Zr1'	76.31 (15)	C28—C27—H27	120.5
C3'—C4'—H4'	126.0	C26'—C27'—C28'	119.2 (3)
C5'—C4'—H4'	126.0	C26'—C27'—H27'	120.4
Zr1'—C4'—H4'	116.4	C28'—C27'—H27'	120.4
C4—C5—C1	108.8 (2)	C29—C28—C27	120.3 (2)
C4—C5—Zr1	71.39 (14)	C29—C28—H28	119.9
C1—C5—Zr1	75.66 (14)	C27—C28—H28	119.9
C4—C5—H5	125.6	C29'—C28'—C27'	120.4 (3)
C1—C5—H5	125.6	C29'—C28'—H28'	119.8
Zr1—C5—H5	119.1	C27'—C28'—H28'	119.8
C4'—C5'—C1'	108.6 (2)	C28—C29—C24	122.2 (2)
C4'—C5'—Zr1'	70.94 (15)	C28—C29—H29	118.9
C1'—C5'—Zr1'	75.48 (15)	C24—C29—H29	118.9
C4'—C5'—H5'	125.7	C28'—C29'—C24'	121.7 (3)
C1'—C5'—H5'	125.7	C28'—C29'—H29'	119.2
Zr1'—C5'—H5'	119.6	C24'—C29'—H29'	119.2
C8—C6—C1	110.3 (2)	C31—C30—Zr1	86.43 (16)
C8—C6—C7	109.8 (2)	C31—C30—H30A	113.7 (15)
C1—C6—C7	111.4 (2)	Zr1—C30—H30A	105.8 (17)
C8—C6—C9	111.5 (2)	C31—C30—H30B	116.1 (14)
C1—C6—C9	106.9 (2)	Zr1—C30—H30B	115.9 (14)
C7—C6—C9	107.0 (2)	H30A—C30—H30B	115 (2)
C1'—C6'—C8'	109.8 (2)	C31'—C30'—Zr1'	122.36 (17)
C1'—C6'—C7'	110.98 (19)	C31'—C30'—H30C	112.2 (15)
C8'—C6'—C7'	109.8 (2)	Zr1'—C30'—H30C	109.0 (15)
C1'—C6'—C9'	108.2 (2)	C31'—C30'—H30D	109.1 (18)
C8'—C6'—C9'	111.01 (19)	Zr1'—C30'—H30D	97.6 (16)
C7'—C6'—C9'	107.1 (2)	H30C—C30'—H30D	104 (2)
C6—C7—H7A	109.5	C32—C31—C36	116.3 (2)
C6—C7—H7B	109.5	C32—C31—C30	122.0 (2)
H7A—C7—H7B	109.5	C36—C31—C30	121.0 (2)
C6—C7—H7C	109.5	C32—C31—Zr1	105.84 (17)
H7A—C7—H7C	109.5	C36—C31—Zr1	96.43 (16)
H7B—C7—H7C	109.5	C30—C31—Zr1	60.23 (14)
C6'—C7'—H7'1	109.5	C36'—C31'—C32'	116.9 (3)
C6'—C7'—H7'2	109.5	C36'—C31'—C30'	121.1 (2)
H7'1—C7'—H7'2	109.5	C32'—C31'—C30'	122.0 (2)
C6'—C7'—H7'3	109.5	C33—C32—C31	122.5 (3)
H7'1—C7'—H7'3	109.5	C33—C32—H32	118.8
H7'2—C7'—H7'3	109.5	C31—C32—H32	118.8
C6—C8—H8A	109.5	C33'—C32'—C31'	121.1 (3)
C6—C8—H8B	109.5	C33'—C32'—H32'	119.4
H8A—C8—H8B	109.5	C31'—C32'—H32'	119.4
C6—C8—H8C	109.5	C32—C33—C34	119.8 (3)
H8A—C8—H8C	109.5	C32—C33—H33	120.1
H8B—C8—H8C	109.5	C34—C33—H33	120.1
C6'—C8'—H8'1	109.5	C34'—C33'—C32'	121.2 (3)
C6'—C8'—H8'2	109.5	C34'—C33'—H33'	119.4
H8'1—C8'—H8'2	109.5	C32'—C33'—H33'	119.4
C6'—C8'—H8'3	109.5	C35—C34—C33	119.4 (3)
H8'1—C8'—H8'3	109.5	C35—C34—H34	120.3
H8'2—C8'—H8'3	109.5	C33—C34—H34	120.3
C14—C9—C10	117.1 (2)	C33'—C34'—C35'	118.6 (3)
C14—C9—C6	120.2 (2)	C33'—C34'—H34'	120.7
C10—C9—C6	122.6 (2)	C35'—C34'—H34'	120.7
C14'—C9'—C10'	117.7 (2)	C34—C35—C36	121.1 (3)
C14'—C9'—C6'	121.1 (2)	C34—C35—H35	119.5
C10'—C9'—C6'	121.1 (2)	C36—C35—H35	119.5
C11—C10—C9	121.2 (3)	C36'—C35'—C34'	120.7 (3)
C11—C10—H10	119.4	C36'—C35'—H35'	119.7
C9—C10—H10	119.4	C34'—C35'—H35'	119.7
C9'—C10'—C11'	120.6 (3)	C35—C36—C31	121.0 (3)
C9'—C10'—H10'	119.7	C35—C36—H36	119.5
C11'—C10'—H10'	119.7	C31—C36—H36	119.5
C10—C11—C12	121.6 (2)	C35'—C36'—C31'	121.6 (3)
C10—C11—H11	119.2	C35'—C36'—H36'	119.2
C12—C11—H11	119.2	C31'—C36'—H36'	119.2
C12'—C11'—C10'	121.8 (2)	C23—Zr1—C30	108.33 (11)
C12'—C11'—H11'	119.1	C23—Zr1—C16	100.71 (10)
C10'—C11'—H11'	119.1	C30—Zr1—C16	120.53 (9)
C11—C12—C13	117.1 (2)	C23—Zr1—C4	128.43 (10)
C11—C12—C15	121.0 (2)	C30—Zr1—C4	113.12 (10)
C13—C12—C15	121.9 (3)	C16—Zr1—C4	83.62 (9)
C11'—C12'—C13'	117.4 (2)	C23—Zr1—C3	95.50 (10)
C11'—C12'—C15'	122.6 (2)	C30—Zr1—C3	138.29 (10)
C13'—C12'—C15'	120.1 (3)	C16—Zr1—C3	86.36 (9)
C14—C13—C12	121.2 (3)	C4—Zr1—C3	33.04 (8)
C14—C13—H13	119.4	C23—Zr1—C2	79.76 (9)
C12—C13—H13	119.4	C30—Zr1—C2	118.21 (9)
C12'—C13'—C14'	121.1 (3)	C16—Zr1—C2	117.29 (9)
C12'—C13'—H13'	119.4	C4—Zr1—C2	54.30 (8)
C14'—C13'—H13'	119.4	C3—Zr1—C2	32.70 (8)
C9—C14—C13	121.7 (2)	C23—Zr1—C5	130.91 (9)
C9—C14—H14	119.2	C30—Zr1—C5	84.93 (10)
C13—C14—H14	119.2	C16—Zr1—C5	112.73 (9)
C9'—C14'—C13'	121.3 (2)	C4—Zr1—C5	32.74 (8)
C9'—C14'—H14'	119.3	C3—Zr1—C5	54.07 (9)
C13'—C14'—H14'	119.3	C2—Zr1—C5	53.52 (8)
C12—C15—H15A	109.5	C23—Zr1—C1	99.67 (9)
C12—C15—H15B	109.5	C30—Zr1—C1	87.82 (9)
H15A—C15—H15B	109.5	C16—Zr1—C1	136.80 (9)
C12—C15—H15C	109.5	C4—Zr1—C1	54.10 (7)
H15A—C15—H15C	109.5	C3—Zr1—C1	54.01 (8)
H15B—C15—H15C	109.5	C2—Zr1—C1	32.32 (8)
C12'—C15'—H15D	109.5	C5—Zr1—C1	32.15 (7)
C12'—C15'—H15E	109.5	C23—Zr1—C31	122.06 (9)
H15D—C15'—H15E	109.5	C30—Zr1—C31	33.34 (8)
C12'—C15'—H15F	109.5	C16—Zr1—C31	87.33 (9)
H15D—C15'—H15F	109.5	C4—Zr1—C31	109.41 (9)
H15E—C15'—H15F	109.5	C3—Zr1—C31	142.43 (9)
C17—C16—Zr1	119.93 (16)	C2—Zr1—C31	144.97 (8)
C17—C16—H16A	116 (2)	C5—Zr1—C31	95.23 (8)
Zr1—C16—H16A	97.3 (18)	C1—Zr1—C31	112.74 (8)
C17—C16—H16B	113.3 (13)	C16'—Zr1'—C30'	99.18 (11)
Zr1—C16—H16B	107.1 (13)	C16'—Zr1'—C23'	109.66 (11)
H16A—C16—H16B	100 (2)	C30'—Zr1'—C23'	119.52 (9)
C17'—C16'—Zr1'	103.08 (16)	C16'—Zr1'—C3'	96.06 (9)
C17'—C16'—H16C	115.3 (18)	C30'—Zr1'—C3'	85.65 (9)
Zr1'—C16'—H16C	105.0 (18)	C23'—Zr1'—C3'	138.92 (10)
C17'—C16'—H16D	112.1 (17)	C16'—Zr1'—C4'	129.03 (10)
Zr1'—C16'—H16D	110.3 (17)	C30'—Zr1'—C4'	84.26 (9)
H16C—C16'—H16D	110 (2)	C23'—Zr1'—C4'	112.32 (10)
C22—C17—C18	116.9 (3)	C3'—Zr1'—C4'	33.12 (8)
C22—C17—C16	121.6 (2)	C16'—Zr1'—C2'	79.82 (9)
C18—C17—C16	121.4 (2)	C30'—Zr1'—C2'	116.36 (9)
C18'—C17'—C22'	116.7 (2)	C23'—Zr1'—C2'	120.26 (9)
C18'—C17'—C16'	120.9 (2)	C3'—Zr1'—C2'	32.96 (8)
C22'—C17'—C16'	122.4 (2)	C4'—Zr1'—C2'	54.56 (8)
C19—C18—C17	121.5 (3)	C16'—Zr1'—C5'	131.01 (9)
C19—C18—H18	119.3	C30'—Zr1'—C5'	113.89 (9)
C17—C18—H18	119.3	C23'—Zr1'—C5'	84.99 (10)
C19'—C18'—C17'	121.8 (2)	C3'—Zr1'—C5'	54.22 (9)
C19'—C18'—H18'	119.1	C4'—Zr1'—C5'	32.75 (8)
C17'—C18'—H18'	119.1	C2'—Zr1'—C5'	53.77 (8)
C20—C19—C18	120.5 (3)	C16'—Zr1'—C1'	99.66 (9)
C20—C19—H19	119.7	C30'—Zr1'—C1'	137.00 (9)
C18—C19—H19	119.7	C23'—Zr1'—C1'	89.39 (9)
C20'—C19'—C18'	120.2 (3)	C3'—Zr1'—C1'	54.17 (8)
C20'—C19'—H19'	119.9	C4'—Zr1'—C1'	54.11 (8)
C18'—C19'—H19'	119.9	C2'—Zr1'—C1'	32.47 (8)
C19—C20—C21	118.7 (3)	C5'—Zr1'—C1'	32.14 (7)
C19—C20—H20	120.6	C16'—Zr1'—C24'	123.77 (9)
C21—C20—H20	120.6	C30'—Zr1'—C24'	86.21 (9)
C21'—C20'—C19'	119.0 (3)	C23'—Zr1'—C24'	33.62 (8)
C21'—C20'—H20'	120.5	C3'—Zr1'—C24'	140.12 (8)
C19'—C20'—H20'	120.5	C4'—Zr1'—C24'	107.18 (9)
C22—C21—C20	120.7 (3)	C2'—Zr1'—C24'	145.87 (9)
C22—C21—H21	119.7	C5'—Zr1'—C24'	94.63 (8)
C20—C21—H21	119.7	C1'—Zr1'—C24'	113.75 (8)