Effects of the [OC₆F₅] moiety upon structural geometry: crystal structures of half-sandwich tantalum(V) aryloxide complexes from reaction of Cp*Ta(N^tBu)(CH₂R)₂ with pentafluorophenol

The synthesis, chemical and structural characterization of a series of pentamethylcyclopentadienyl (Cp*) tantalum imido complexes and aryloxide derivatives are presented. Specifically, the imido complexes Cp*Ta(N^tBu)(CH₂R)₂, where R = Ph [dibenzyl(tert-butylamido) (η⁵-pentamethylcyclopentadienyl)tantalum(IV) (1)], Me₂Ph [tert-butylamido)bis(2-methyl-2-phenylpropyl) (η⁵-pentamethylcyclopentadienyl)tantalum(IV) (2)], CMe₃ [(tert-butylamido)bis(2,2-dimethylpropyl) (η⁵-pentamethylcyclopentadienyl)tantalum(IV) (3)], are reported. The crystal structure of (3) reveals α-agostic interactions with the Ta atom. The resulting increase in the tantalum core coordination improves electronic stability. As such it does not react with pentafluorophenol, in contrast to the other two reported imido complexes [(1) and (2)]. Addition of C₆F₅OH to (1) yields a dimeric aryl-oxide derivative, [Cp*Ta(CH₂Ph)(OC₆H₅)(μ-O)]₂ [di-μ-oxido-bis[benzyl(pentafluorophenolato) (η⁵-pentamethylcyclopentadienyl)tantalum(V)] (4)]. Its crystal structure reveals long Ta—O(C₆H₅) bonds but short oxo-bridging Ta—O bonds. This is explained by accounting for the fierce electronic competition for the vacant d_π orbitals of the electrophilic Ta^V centre. Steric congestion around each metal is alleviated by a large twist angle (77.1°) between the benzyl and pentafluorophenyl ligands and the ordering of each of these groups into stacked pairs. The imido complex (2) reacts with C₆F₅OH to produce a mixture of Cp*Ta(OC₆F₅)₄ [tetrakis(pentafluorophenolato)(η⁵-pentamethylcyclopentadienyl)tantalum(V) (5)] and [Cp*Ta(OC₆F₅)₂(μ-O)]₂ [di-μ-oxido-bis[bis(pentafluorophenolato)(η⁵-pentamethylcyclopentadienyl)tantalum(V)] (6)]. Steric congestion is offset in both cases by the twisting of its pentafluorophenyl ligands. Particularly strong electronic competition for the empty d_π metal orbitals in (6) is reflected in its bond geometry, and owes itself to the more numerous electron-withdrawing pentafluorophenyl ligands. The balance of steric and electronic factors affecting the reactivity of Cp* tantalum imido based complexes with pentafluorophenol is therefore addressed.

Computing details

Data collection: Siemens XSCANS for final, combined, xmas1; Siemens SMART for 95srv082. Cell refinement: Siemens XSCANS for final, combined, xmas1; Siemens SMART for 95srv082. Data reduction: Siemens XSCANS for final, combined, xmas1; Siemens SAINT for 95srv082. For all compounds, program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXL93.

Figures

(final)

Crystal data

C23H22F5O2Ta	Z = 2
Mr = 606.36	F(000) = 588
Triclinic, P1	Dx = 1.941 Mg m^−3
Hall symbol: p 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.239 (2) Å	Cell parameters from 50 reflections
b = 11.647 (2) Å	θ = 4.7–12.3°
c = 11.803 (2) Å	µ = 5.36 mm^−1
α = 117.25 (3)°	T = 150 K
β = 96.37 (3)°	Irregular block, yellow
γ = 106.63 (3)°	0.80 × 0.64 × 0.44 mm
V = 1037.3 (3) Å^3

Data collection

Siemens P4 diffractometer	2985 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.145
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω scans	h = −1→10
Absorption correction: empirical (using intensity measurements) ?	k = −11→11
Tmin = 0.261, Tmax = 1.000	l = −14→14
3942 measured reflections	3 standard reflections every 97 reflections
3310 independent reflections	intensity decay: none

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Calculated w = 1/[σ^2(Fo^2) + (0.1572P)^2] where P = (Fo^2 + 2Fc^2)/3
3309 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 5.30 e Å^−3
0 restraints	Δρmin = −3.77 e Å^−3

Special details

Experimental. Empirical absorption program: DIFABS.

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 on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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
Ta	0.07331 (4)	0.14666 (4)	0.02121 (3)	0.0227 (3)
F2	0.0398 (9)	0.3517 (9)	0.3795 (7)	0.043 (2)
F3	0.1504 (11)	0.4073 (10)	0.6275 (8)	0.053 (2)
F4	0.4415 (11)	0.4098 (9)	0.7073 (7)	0.051 (2)
F5	0.6121 (9)	0.3448 (9)	0.5299 (8)	0.047 (2)
F6	0.5032 (8)	0.2935 (8)	0.2836 (7)	0.037 (2)
O1	0.2143 (10)	0.2989 (9)	0.2031 (8)	0.031 (2)
O2	0.0221 (9)	0.0498 (8)	0.1188 (7)	0.026 (2)
C1	0.2678 (15)	0.3175 (12)	0.3217 (10)	0.029 (3)
C2	0.1807 (15)	0.3467 (15)	0.4138 (14)	0.039 (3)
C3	0.2366 (17)	0.3758 (15)	0.5418 (13)	0.044 (4)
C4	0.3809 (18)	0.3750 (16)	0.5798 (12)	0.043 (4)
C5	0.4719 (16)	0.3455 (14)	0.4918 (12)	0.036 (3)
C6	0.4124 (14)	0.3173 (13)	0.3641 (11)	0.029 (3)
C7	0.2984 (14)	0.1553 (14)	−0.0272 (11)	0.032 (3)
H7A	0.3681	0.2554	0.0214	0.039*
H7B	0.3445	0.1119	0.0144	0.039*
C8	0.3170 (14)	0.0951 (13)	−0.1647 (11)	0.029 (3)
C9	0.4144 (15)	0.1776 (14)	−0.2021 (12)	0.032 (3)
H9A	0.4747 (15)	0.2744 (14)	−0.1376 (12)	0.039*
C10	0.4270 (16)	0.1223 (18)	−0.3333 (14)	0.047 (4)
H10A	0.4942 (16)	0.1819 (18)	−0.3574 (14)	0.056*
C11	0.3455 (16)	−0.0128 (17)	−0.4242 (12)	0.043 (3)
H11A	0.3518 (16)	−0.0497 (17)	−0.5140 (12)	0.051*
C12	0.2506 (15)	−0.0997 (16)	−0.3875 (12)	0.039 (3)
H12A	0.1947 (15)	−0.1971 (16)	−0.4522 (12)	0.046*
C13	0.2365 (14)	−0.0487 (14)	−0.2611 (12)	0.034 (3)
H13A	0.1720 (14)	−0.1104 (14)	−0.2377 (12)	0.040*
C14	0.1002 (15)	0.3316 (15)	−0.0438 (12)	0.0361 (9)*
C15	−0.0041 (15)	0.1989 (15)	−0.1569 (12)	0.0361 (9)*
C16	−0.1400 (15)	0.1532 (15)	−0.1155 (12)	0.0361 (9)*
C17	−0.1136 (15)	0.2512 (14)	0.0187 (12)	0.0361 (9)*
C18	0.0309 (15)	0.3613 (15)	0.0610 (12)	0.0361 (9)*
C14A	0.2501 (14)	0.4282 (14)	−0.0396 (12)	0.0361 (9)*
H14A	0.2266 (14)	0.4868 (14)	−0.0693 (12)	0.043*
H14B	0.3182 (14)	0.4852 (14)	0.0497 (12)	0.043*
H14C	0.3015 (14)	0.3750 (14)	−0.0968 (12)	0.043*
C15A	0.0125 (15)	0.1263 (15)	−0.2925 (12)	0.0361 (9)*
H15A	−0.0240 (15)	0.1627 (15)	−0.3432 (12)	0.043*
H15B	0.1212 (15)	0.1407 (15)	−0.2872 (12)	0.043*
H15C	−0.0491 (15)	0.0281 (15)	−0.3350 (12)	0.043*
C16A	−0.2844 (15)	0.0233 (15)	−0.2066 (12)	0.0361 (9)*
H16A	−0.3553 (15)	0.0450 (15)	−0.2521 (12)	0.043*
H16B	−0.2544 (15)	−0.0467 (15)	−0.2704 (12)	0.043*
H16C	−0.3356 (15)	−0.0111 (15)	−0.1557 (12)	0.043*
C17A	−0.2362 (15)	0.2485 (15)	0.0926 (12)	0.0361 (9)*
H17A	−0.2988 (15)	0.2964 (15)	0.0784 (12)	0.043*
H17B	−0.3029 (15)	0.1535 (15)	0.0606 (12)	0.043*
H17C	−0.1852 (15)	0.2943 (15)	0.1858 (12)	0.043*
C18A	0.1005 (15)	0.4993 (14)	0.1920 (12)	0.0361 (9)*
H18A	0.0674 (15)	0.5666 (14)	0.1834 (12)	0.043*
H18B	0.0650 (15)	0.4869 (14)	0.2605 (12)	0.043*
H18C	0.2133 (15)	0.5318 (14)	0.2147 (12)	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ta	0.0252 (3)	0.0181 (4)	0.0243 (3)	0.0069 (2)	0.0030 (2)	0.0122 (2)
F2	0.038 (4)	0.043 (5)	0.048 (4)	0.015 (4)	0.012 (3)	0.024 (4)
F3	0.066 (5)	0.055 (6)	0.042 (4)	0.026 (4)	0.029 (4)	0.022 (4)
F4	0.071 (6)	0.042 (5)	0.033 (4)	0.011 (4)	0.002 (4)	0.023 (4)
F5	0.044 (4)	0.042 (5)	0.050 (4)	0.016 (4)	−0.003 (4)	0.024 (4)
F6	0.036 (4)	0.033 (4)	0.034 (4)	0.011 (3)	0.008 (3)	0.015 (3)
O1	0.035 (4)	0.021 (4)	0.032 (4)	0.006 (4)	0.000 (3)	0.013 (4)
O2	0.033 (4)	0.020 (4)	0.027 (4)	0.007 (3)	0.004 (3)	0.017 (3)
C1	0.048 (7)	0.009 (6)	0.025 (5)	0.003 (5)	0.002 (5)	0.009 (5)
C2	0.035 (7)	0.024 (7)	0.043 (7)	0.005 (5)	0.007 (5)	0.010 (6)
C3	0.056 (8)	0.032 (8)	0.036 (7)	0.003 (6)	0.011 (6)	0.020 (6)
C4	0.059 (9)	0.035 (8)	0.026 (6)	0.003 (7)	−0.001 (6)	0.020 (6)
C5	0.039 (6)	0.029 (7)	0.038 (6)	0.008 (5)	0.003 (5)	0.020 (6)
C6	0.039 (6)	0.017 (6)	0.026 (5)	0.004 (5)	0.001 (5)	0.012 (5)
C7	0.033 (6)	0.034 (7)	0.030 (6)	0.010 (5)	0.004 (4)	0.020 (5)
C8	0.033 (6)	0.023 (6)	0.029 (5)	0.013 (5)	0.005 (4)	0.012 (5)
C9	0.040 (6)	0.025 (7)	0.040 (6)	0.013 (5)	0.014 (5)	0.022 (6)
C10	0.038 (7)	0.069 (11)	0.051 (8)	0.022 (7)	0.016 (6)	0.043 (8)
C11	0.040 (7)	0.061 (10)	0.033 (6)	0.027 (7)	0.012 (5)	0.024 (7)
C12	0.034 (6)	0.042 (8)	0.038 (6)	0.016 (6)	0.012 (5)	0.018 (6)
C13	0.033 (6)	0.036 (8)	0.038 (6)	0.015 (6)	0.009 (5)	0.022 (6)

Geometric parameters (Å, º)

Ta—O2^i	1.950 (8)	C10—H10A	0.96
Ta—O2	1.957 (7)	C11—C12	1.40 (2)
Ta—O1	2.005 (8)	C11—H11A	0.96
Ta—C7	2.204 (12)	C12—C13	1.37 (2)
Ta—C17	2.385 (14)	C12—H12A	0.96
Ta—C16	2.446 (13)	C13—H13A	0.96
Ta—C18	2.480 (15)	C14—C18	1.40 (2)
Ta—C15	2.528 (13)	C14—C15	1.44 (2)
Ta—C14	2.558 (14)	C14—C14A	1.49 (2)
Ta—Ta^i	3.0644 (13)	C15—C16	1.45 (2)
F2—C2	1.35 (2)	C15—C15A	1.48 (2)
F3—C3	1.34 (2)	C16—C17	1.40 (2)
F4—C4	1.367 (14)	C16—C16A	1.50 (2)
F5—C5	1.33 (2)	C17—C18	1.40 (2)
F6—C6	1.324 (15)	C17—C17A	1.51 (2)
O1—C1	1.326 (13)	C18—C18A	1.52 (2)
O2—Ta^i	1.950 (8)	C14A—H14A	0.96
C1—C6	1.37 (2)	C14A—H14B	0.96
C1—C2	1.40 (2)	C14A—H14C	0.96
C2—C3	1.39 (2)	C15A—H15A	0.96
C3—C4	1.36 (2)	C15A—H15B	0.96
C4—C5	1.39 (2)	C15A—H15C	0.96
C5—C6	1.39 (2)	C16A—H16A	0.96
C7—C8	1.50 (2)	C16A—H16B	0.96
C7—H7A	0.990 (13)	C16A—H16C	0.96
C7—H7B	0.990 (13)	C17A—H17A	0.96
C8—C9	1.38 (2)	C17A—H17B	0.96
C8—C13	1.42 (2)	C17A—H17C	0.96
C9—C10	1.41 (2)	C18A—H18A	0.96
C9—H9A	0.96	C18A—H18B	0.96
C10—C11	1.34 (2)	C18A—H18C	0.96
O2^i—Ta—O2	76.7 (3)	C8—C9—H9A	119.4 (7)
O2^i—Ta—O1	150.8 (4)	C10—C9—H9A	119.3 (9)
O2—Ta—O1	80.7 (3)	C11—C10—C9	120.2 (13)
O2^i—Ta—C7	89.1 (4)	C11—C10—H10A	119.9 (8)
O2—Ta—C7	113.4 (4)	C9—C10—H10A	119.9 (9)
O1—Ta—C7	83.2 (4)	C10—C11—C12	119.5 (12)
O2^i—Ta—C17	108.4 (4)	C10—C11—H11A	120.2 (8)
O2—Ta—C17	107.7 (4)	C12—C11—H11A	120.3 (8)
O1—Ta—C17	95.9 (4)	C13—C12—C11	121.3 (13)
C7—Ta—C17	138.1 (5)	C13—C12—H12A	119.3 (8)
O2^i—Ta—C16	80.3 (4)	C11—C12—H12A	119.3 (8)
O2—Ta—C16	119.3 (4)	C12—C13—C8	120.1 (12)
O1—Ta—C16	127.5 (4)	C12—C13—H13A	120.0 (8)
C7—Ta—C16	121.5 (4)	C8—C13—H13A	119.9 (7)
C17—Ta—C16	33.7 (4)	C18—C14—C15	108.3 (11)
O2^i—Ta—C18	135.0 (4)	C18—C14—C14A	124.9 (12)
O2—Ta—C18	126.5 (4)	C15—C14—C14A	126.6 (11)
O1—Ta—C18	73.8 (4)	C18—C14—Ta	70.8 (8)
C7—Ta—C18	109.3 (5)	C15—C14—Ta	72.4 (8)
C17—Ta—C18	33.4 (4)	C14A—C14—Ta	126.3 (9)
C16—Ta—C18	54.9 (4)	C14—C15—C16	105.7 (11)
O2^i—Ta—C15	86.3 (4)	C14—C15—C15A	128.8 (12)
O2—Ta—C15	151.5 (4)	C16—C15—C15A	125.3 (12)
O1—Ta—C15	121.5 (4)	C14—C15—Ta	74.7 (7)
C7—Ta—C15	88.7 (4)	C16—C15—Ta	70.0 (7)
C17—Ta—C15	56.1 (4)	C15A—C15—Ta	123.8 (10)
C16—Ta—C15	33.7 (4)	C17—C16—C15	108.6 (11)
C18—Ta—C15	54.8 (4)	C17—C16—C16A	127.7 (11)
O2^i—Ta—C14	118.5 (4)	C15—C16—C16A	123.7 (11)
O2—Ta—C14	158.8 (4)	C17—C16—Ta	70.7 (7)
O1—Ta—C14	88.6 (4)	C15—C16—Ta	76.2 (8)
C7—Ta—C14	83.2 (5)	C16A—C16—Ta	120.6 (10)
C17—Ta—C14	54.9 (4)	C18—C17—C16	108.2 (11)
C16—Ta—C14	54.7 (4)	C18—C17—C17A	126.7 (12)
C18—Ta—C14	32.3 (4)	C16—C17—C17A	124.1 (11)
C15—Ta—C14	32.9 (4)	C18—C17—Ta	77.0 (8)
O2^i—Ta—Ta^i	38.4 (2)	C16—C17—Ta	75.5 (8)
O2—Ta—Ta^i	38.3 (2)	C17A—C17—Ta	122.9 (9)
O1—Ta—Ta^i	116.9 (3)	C17—C18—C14	109.1 (11)
C7—Ta—Ta^i	104.1 (4)	C17—C18—C18A	127.8 (11)
C17—Ta—Ta^i	113.3 (3)	C14—C18—C18A	122.8 (12)
C16—Ta—Ta^i	101.8 (3)	C17—C18—Ta	69.6 (8)
C18—Ta—Ta^i	146.0 (3)	C14—C18—Ta	76.9 (9)
C15—Ta—Ta^i	121.3 (3)	C18A—C18—Ta	124.5 (9)
C14—Ta—Ta^i	154.0 (3)	C14—C14A—H14A	109.1 (8)
C1—O1—Ta	139.8 (8)	C14—C14A—H14B	109.6 (7)
Ta^i—O2—Ta	103.3 (3)	H14A—C14A—H14B	109.5
O1—C1—C6	123.0 (12)	C14—C14A—H14C	109.7 (8)
O1—C1—C2	120.4 (12)	H14A—C14A—H14C	109.5
C6—C1—C2	116.4 (11)	H14B—C14A—H14C	109.5
F2—C2—C3	118.3 (13)	C15—C15A—H15A	109.6 (8)
F2—C2—C1	119.3 (12)	C15—C15A—H15B	109.5 (7)
C3—C2—C1	122.4 (13)	H15A—C15A—H15B	109.5
F3—C3—C4	120.8 (12)	C15—C15A—H15C	109.4 (8)
F3—C3—C2	119.9 (14)	H15A—C15A—H15C	109.5
C4—C3—C2	119.3 (13)	H15B—C15A—H15C	109.5
C3—C4—F4	120.2 (14)	C16—C16A—H16A	109.3 (8)
C3—C4—C5	120.7 (12)	C16—C16A—H16B	109.5 (7)
F4—C4—C5	118.9 (14)	H16A—C16A—H16B	109.5
F5—C5—C4	120.2 (12)	C16—C16A—H16C	109.6 (7)
F5—C5—C6	121.3 (12)	H16A—C16A—H16C	109.5
C4—C5—C6	118.5 (13)	H16B—C16A—H16C	109.5
F6—C6—C1	120.0 (10)	C17—C17A—H17A	109.3 (8)
F6—C6—C5	117.3 (11)	C17—C17A—H17B	109.7 (8)
C1—C6—C5	122.7 (12)	H17A—C17A—H17B	109.5
C8—C7—Ta	125.2 (8)	C17—C17A—H17C	109.4 (7)
C8—C7—H7A	106.0 (10)	H17A—C17A—H17C	109.5
Ta—C7—H7A	106.0 (9)	H17B—C17A—H17C	109.5
C8—C7—H7B	106.0 (12)	C18—C18A—H18A	109.4 (7)
Ta—C7—H7B	106.0 (8)	C18—C18A—H18B	109.7 (7)
H7A—C7—H7B	106.3 (10)	H18A—C18A—H18B	109.5
C9—C8—C13	117.4 (11)	C18—C18A—H18C	109.3 (7)
C9—C8—C7	121.2 (11)	H18A—C18A—H18C	109.5
C13—C8—C7	121.3 (11)	H18B—C18A—H18C	109.5
C8—C9—C10	121.3 (12)

Symmetry code: (i) −x, −y, −z.

(combined)

Crystal data

C24H46NTa	F(000) = 1080
Mr = 529.57	Dx = 1.436 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 32 reflections
a = 9.083 (2) Å	θ = 12.4–12.5°
b = 16.216 (3) Å	µ = 4.50 mm^−1
c = 16.872 (3) Å	T = 150 K
β = 99.76 (3)°	Cube, yellow
V = 2449.1 (8) Å^3	0.26 × 0.24 × 0.20 mm
Z = 4

Data collection

Siemens P4 diffractometer	7822 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 35.0°, θmin = 2.3°
2τ/ω scans	h = −1→14
Absorption correction: empirical (using intensity measurements) ?	k = −1→26
Tmin = 0.267, Tmax = 0.365	l = −85→27
13104 measured reflections	3 standard reflections every 97 reflections
10777 independent reflections	intensity decay: none

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0192P)^2 + 0.0105P] where P = (Fo^2 + 2Fc^2)/3
10777 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 1.10 e Å^−3
0 restraints	Δρmin = −0.79 e Å^−3

Special details

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 on F² for ALL reflections except for 3 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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
Ta1	0.146374 (13)	0.241189 (6)	0.429226 (7)	0.01498 (3)
N1	0.3194 (2)	0.24441 (15)	0.49784 (13)	0.0180 (4)
C11	0.1719 (4)	0.33799 (19)	0.3413 (2)	0.0216 (6)
H11A	0.071 (4)	0.353 (2)	0.312 (2)	0.026*
H11B	0.210 (4)	0.295 (2)	0.307 (2)	0.026*
C16	0.1583 (4)	0.12800 (19)	0.3578 (2)	0.0233 (6)
H16A	0.098 (4)	0.088 (2)	0.372 (2)	0.028*
H16B	0.094 (4)	0.146 (2)	0.306 (2)	0.028*
C1	−0.1038 (4)	0.17678 (18)	0.4379 (2)	0.0214 (6)
C2	−0.1378 (3)	0.24885 (19)	0.39201 (17)	0.0220 (5)
C3	−0.0886 (4)	0.31756 (18)	0.4410 (2)	0.0203 (6)
C4	−0.0203 (4)	0.28812 (18)	0.51792 (18)	0.0189 (6)
C5	−0.0289 (4)	0.20026 (18)	0.5159 (2)	0.0207 (6)
C6	−0.1573 (4)	0.0910 (2)	0.4152 (2)	0.0309 (8)
H6A	−0.2576	0.0844	0.4253	0.046*
H6B	−0.0932	0.0518	0.4467	0.046*
H6C	−0.1554	0.0819	0.3591	0.046*
C7	−0.2176 (4)	0.2526 (2)	0.30631 (19)	0.0324 (7)
H7A	−0.3234	0.2553	0.3055	0.049*
H7B	−0.1944	0.2042	0.2781	0.049*
H7C	−0.1859	0.3007	0.2807	0.049*
C8	−0.1257 (4)	0.40565 (19)	0.4198 (2)	0.0286 (7)
H8A	−0.2237	0.4181	0.4307	0.043*
H8B	−0.1234	0.4143	0.3638	0.043*
H8C	−0.0539	0.4410	0.4515	0.043*
C9	0.0322 (4)	0.3397 (2)	0.5906 (2)	0.0296 (8)
H9A	−0.0506	0.3517	0.6174	0.044*
H9B	0.0733	0.3904	0.5746	0.044*
H9C	0.1074	0.3103	0.6265	0.044*
C10	0.0123 (4)	0.1426 (2)	0.5862 (2)	0.0284 (7)
H10A	−0.0726	0.1346	0.6123	0.043*
H10B	0.0928	0.1660	0.6237	0.043*
H10C	0.0431	0.0905	0.5675	0.043*
C12	0.2765 (4)	0.41433 (19)	0.3516 (2)	0.0220 (6)
C13	0.4401 (4)	0.3875 (2)	0.3630 (2)	0.0289 (7)
H13A	0.5032	0.4353	0.3693	0.043*
H13B	0.4572	0.3567	0.3168	0.043*
H13C	0.4625	0.3535	0.4101	0.043*
C14	0.2440 (5)	0.4678 (2)	0.2756 (2)	0.0351 (9)
H14A	0.3085	0.5151	0.2817	0.053*
H14B	0.1418	0.4856	0.2674	0.053*
H14C	0.2615	0.4361	0.2300	0.053*
C15	0.2503 (4)	0.4662 (2)	0.4235 (2)	0.0307 (7)
H15A	0.3159	0.5130	0.4289	0.046*
H15B	0.2701	0.4334	0.4715	0.046*
H15C	0.1485	0.4847	0.4153	0.046*
C17	0.3004 (4)	0.08473 (18)	0.3418 (2)	0.0210 (6)
C18	0.3708 (5)	0.0383 (2)	0.4175 (2)	0.0331 (8)
H18A	0.3968	0.0767	0.4609	0.050*
H18B	0.4591	0.0103	0.4077	0.050*
H18C	0.3008	−0.0013	0.4314	0.050*
C19	0.2602 (5)	0.0218 (2)	0.2731 (2)	0.0329 (8)
H19A	0.3493	−0.0052	0.2633	0.049*
H19B	0.2138	0.0499	0.2252	0.049*
H19C	0.1923	−0.0184	0.2881	0.049*
C20	0.4124 (4)	0.1464 (2)	0.3179 (2)	0.0311 (7)
H20A	0.4386	0.1860	0.3602	0.047*
H20B	0.3684	0.1743	0.2694	0.047*
H20C	0.5005	0.1176	0.3090	0.047*
C21	0.4452 (3)	0.2476 (2)	0.56384 (16)	0.0228 (6)
C22	0.5898 (4)	0.2210 (2)	0.5342 (2)	0.0321 (8)
H22A	0.6089	0.2577	0.4925	0.048*
H22B	0.5784	0.1658	0.5135	0.048*
H22D	0.6720	0.2229	0.5782	0.048*
C23	0.4173 (4)	0.1880 (2)	0.6303 (2)	0.0302 (7)
H23A	0.3276	0.2036	0.6494	0.045*
H23D	0.5002	0.1900	0.6739	0.045*
H23B	0.4068	0.1329	0.6092	0.045*
C24	0.4657 (4)	0.3353 (2)	0.5971 (2)	0.0316 (7)
H24D	0.3764	0.3525	0.6157	0.047*
H24A	0.4855	0.3719	0.5555	0.047*
H24B	0.5481	0.3365	0.6410	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ta1	0.01440 (4)	0.01465 (4)	0.01567 (4)	0.00049 (5)	0.00195 (3)	−0.00093 (5)
N1	0.0168 (9)	0.0187 (11)	0.0187 (10)	0.0002 (9)	0.0036 (8)	0.0004 (9)
C11	0.0217 (15)	0.0211 (13)	0.0217 (15)	−0.0010 (11)	0.0028 (12)	−0.0004 (11)
C16	0.0198 (15)	0.0210 (14)	0.0287 (17)	0.0013 (12)	0.0029 (13)	−0.0055 (12)
C1	0.0183 (15)	0.0195 (13)	0.0270 (17)	−0.0012 (11)	0.0052 (13)	−0.0040 (11)
C2	0.0133 (10)	0.0275 (15)	0.0241 (12)	0.0004 (12)	0.0006 (9)	−0.0012 (12)
C3	0.0141 (14)	0.0198 (13)	0.0275 (17)	0.0042 (10)	0.0049 (12)	0.0004 (11)
C4	0.0170 (14)	0.0198 (12)	0.0200 (14)	0.0026 (10)	0.0032 (12)	−0.0012 (10)
C5	0.0190 (15)	0.0185 (13)	0.0253 (16)	0.0005 (11)	0.0057 (13)	0.0037 (11)
C6	0.0269 (18)	0.0226 (15)	0.044 (2)	−0.0059 (13)	0.0093 (16)	−0.0097 (14)
C7	0.0228 (14)	0.048 (2)	0.0244 (13)	−0.0024 (17)	−0.0025 (11)	0.0005 (16)
C8	0.0250 (18)	0.0227 (15)	0.038 (2)	0.0058 (13)	0.0061 (15)	0.0035 (13)
C9	0.0306 (19)	0.0294 (17)	0.0294 (19)	0.0046 (14)	0.0068 (15)	−0.0090 (13)
C10	0.0270 (18)	0.0296 (16)	0.0288 (18)	−0.0011 (13)	0.0053 (15)	0.0105 (13)
C12	0.0223 (16)	0.0224 (14)	0.0220 (15)	−0.0009 (11)	0.0059 (13)	0.0031 (11)
C13	0.0238 (16)	0.0319 (17)	0.0315 (18)	−0.0019 (13)	0.0059 (14)	0.0021 (14)
C14	0.039 (2)	0.0292 (17)	0.038 (2)	−0.0023 (15)	0.0080 (19)	0.0114 (15)
C15	0.0328 (19)	0.0270 (16)	0.0335 (19)	−0.0060 (14)	0.0092 (16)	−0.0043 (13)
C17	0.0243 (16)	0.0187 (13)	0.0205 (15)	0.0030 (11)	0.0054 (13)	−0.0007 (10)
C18	0.041 (2)	0.0264 (16)	0.0306 (18)	0.0079 (15)	0.0021 (16)	0.0043 (13)
C19	0.040 (2)	0.0284 (17)	0.030 (2)	0.0045 (15)	0.0049 (17)	−0.0098 (14)
C20	0.0330 (19)	0.0306 (17)	0.0326 (19)	0.0000 (15)	0.0136 (16)	−0.0022 (14)
C21	0.0195 (12)	0.0315 (16)	0.0170 (11)	−0.0033 (13)	0.0016 (9)	−0.0002 (12)
C22	0.0194 (14)	0.046 (2)	0.0295 (16)	0.0045 (14)	0.0002 (13)	0.0028 (15)
C23	0.0282 (17)	0.0379 (18)	0.0227 (15)	−0.0009 (15)	−0.0010 (14)	0.0053 (13)
C24	0.0289 (18)	0.0355 (18)	0.0278 (17)	−0.0079 (15)	−0.0025 (15)	−0.0038 (14)

Geometric parameters (Å, º)

Ta1—N1	1.788 (2)	C10—H10A	0.9600
Ta1—C11	2.199 (3)	C10—H10B	0.9600
Ta1—C16	2.208 (3)	C10—H10C	0.9600
Ta1—H11B	2.40 (3)	C12—C13	1.529 (5)
Ta1—C4	2.425 (3)	C12—C15	1.527 (5)
Ta1—C5	2.429 (3)	C12—C14	1.534 (5)
Ta1—C3	2.504 (3)	C13—H13A	0.9600
Ta1—C1	2.527 (3)	C13—H13B	0.9600
Ta1—C2	2.554 (3)	C13—H13C	0.9600
Ta1—H16B	2.57 (4)	C14—H14A	0.9600
N1—C21	1.455 (3)	C14—H14B	0.9600
C11—C12	1.552 (4)	C14—H14C	0.9600
C11—H11A	0.99 (4)	C15—H15A	0.9600
C11—H11B	1.01 (4)	C15—H15B	0.9600
C16—C17	1.533 (5)	C15—H15C	0.9600
C16—H16A	0.91 (4)	C17—C18	1.526 (5)
C16—H16B	1.01 (4)	C17—C20	1.529 (5)
C1—C2	1.407 (4)	C17—C19	1.541 (5)
C1—C5	1.427 (5)	C18—H18A	0.9600
C1—C6	1.502 (4)	C18—H18B	0.9600
C2—C3	1.414 (4)	C18—H18C	0.9600
C2—C7	1.505 (4)	C19—H19A	0.9600
C3—C4	1.422 (4)	C19—H19B	0.9600
C3—C8	1.497 (4)	C19—H19C	0.9600
C4—C5	1.427 (4)	C20—H20A	0.9600
C4—C9	1.495 (4)	C20—H20B	0.9600
C5—C10	1.508 (4)	C20—H20C	0.9600
C6—H6A	0.9600	C21—C24	1.528 (4)
C6—H6B	0.9600	C21—C23	1.534 (4)
C6—H6C	0.9600	C21—C22	1.544 (4)
C7—H7A	0.9600	C22—H22A	0.9600
C7—H7B	0.9600	C22—H22B	0.9600
C7—H7C	0.9600	C22—H22D	0.9600
C8—H8A	0.9600	C23—H23A	0.9600
C8—H8B	0.9600	C23—H23D	0.9600
C8—H8C	0.9600	C23—H23B	0.9600
C9—H9A	0.9600	C24—H24D	0.9600
C9—H9B	0.9600	C24—H24A	0.9600
C9—H9C	0.9600	C24—H24B	0.9600
N1—Ta1—C11	103.55 (12)	C2—C7—H7B	109.5
N1—Ta1—C16	104.98 (12)	H7A—C7—H7B	109.5
C11—Ta1—C16	101.82 (13)	C2—C7—H7C	109.5
N1—Ta1—H11B	103.4 (9)	H7A—C7—H7C	109.5
C11—Ta1—H11B	24.7 (9)	H7B—C7—H7C	109.5
C16—Ta1—H11B	78.0 (9)	C3—C8—H8A	109.5
N1—Ta1—C4	99.41 (10)	C3—C8—H8B	109.5
C11—Ta1—C4	109.91 (11)	H8A—C8—H8B	109.5
C16—Ta1—C4	133.72 (12)	C3—C8—H8C	109.5
H11B—Ta1—C4	133.1 (9)	H8A—C8—H8C	109.5
N1—Ta1—C5	102.24 (11)	H8B—C8—H8C	109.5
C11—Ta1—C5	139.10 (12)	C4—C9—H9A	109.5
C16—Ta1—C5	101.48 (12)	C4—C9—H9B	109.5
H11B—Ta1—C5	153.5 (9)	H9A—C9—H9B	109.5
C4—Ta1—C5	34.20 (9)	C4—C9—H9C	109.5
N1—Ta1—C3	126.98 (11)	H9A—C9—H9C	109.5
C11—Ta1—C3	83.64 (12)	H9B—C9—H9C	109.5
C16—Ta1—C3	125.15 (12)	C5—C10—H10A	109.5
H11B—Ta1—C3	102.8 (9)	C5—C10—H10B	109.5
C4—Ta1—C3	33.49 (10)	H10A—C10—H10B	109.5
C5—Ta1—C3	55.47 (10)	C5—C10—H10C	109.5
N1—Ta1—C1	132.46 (11)	H10A—C10—H10C	109.5
C11—Ta1—C1	122.18 (12)	H10B—C10—H10C	109.5
C16—Ta1—C1	79.38 (11)	C13—C12—C15	109.6 (3)
H11B—Ta1—C1	123.4 (9)	C13—C12—C14	108.1 (3)
C4—Ta1—C1	55.43 (10)	C15—C12—C14	108.6 (3)
C5—Ta1—C1	33.40 (11)	C13—C12—C11	110.5 (3)
C3—Ta1—C1	54.07 (10)	C15—C12—C11	110.7 (3)
N1—Ta1—C2	153.98 (9)	C14—C12—C11	109.3 (3)
C11—Ta1—C2	90.99 (11)	C12—C13—H13A	109.5
C16—Ta1—C2	92.72 (11)	C12—C13—H13B	109.5
H11B—Ta1—C2	98.7 (9)	H13A—C13—H13B	109.5
C4—Ta1—C2	54.95 (10)	C12—C13—H13C	109.5
C5—Ta1—C2	54.77 (10)	H13A—C13—H13C	109.5
C3—Ta1—C2	32.45 (10)	H13B—C13—H13C	109.5
C1—Ta1—C2	32.13 (10)	C12—C14—H14A	109.5
N1—Ta1—H16B	124.2 (9)	C12—C14—H14B	109.5
C11—Ta1—H16B	84.7 (8)	H14A—C14—H14B	109.5
C16—Ta1—H16B	22.8 (9)	C12—C14—H14C	109.5
H11B—Ta1—H16B	63.9 (12)	H14A—C14—H14C	109.5
C4—Ta1—H16B	129.8 (9)	H14B—C14—H14C	109.5
C5—Ta1—H16B	105.9 (9)	C12—C15—H15A	109.5
C3—Ta1—H16B	108.6 (9)	C12—C15—H15B	109.5
C1—Ta1—H16B	75.8 (9)	H15A—C15—H15B	109.5
C2—Ta1—H16B	77.9 (9)	C12—C15—H15C	109.5
C21—N1—Ta1	170.68 (19)	H15A—C15—H15C	109.5
C12—C11—Ta1	128.8 (2)	H15B—C15—H15C	109.5
C12—C11—H11A	111 (2)	C18—C17—C20	109.9 (3)
Ta1—C11—H11A	108 (2)	C18—C17—C16	108.9 (3)
C12—C11—H11B	110 (2)	C20—C17—C16	111.4 (3)
Ta1—C11—H11B	89 (2)	C18—C17—C19	108.4 (3)
H11A—C11—H11B	105 (3)	C20—C17—C19	108.6 (3)
C17—C16—Ta1	126.7 (2)	C16—C17—C19	109.7 (3)
C17—C16—H16A	107 (2)	C17—C18—H18A	109.5
Ta1—C16—H16A	111 (2)	C17—C18—H18B	109.5
C17—C16—H16B	111 (2)	H18A—C18—H18B	109.5
Ta1—C16—H16B	99 (2)	C17—C18—H18C	109.5
H16A—C16—H16B	99 (3)	H18A—C18—H18C	109.5
C2—C1—C5	108.1 (3)	H18B—C18—H18C	109.5
C2—C1—C6	126.8 (3)	C17—C19—H19A	109.5
C5—C1—C6	124.4 (3)	C17—C19—H19B	109.5
C2—C1—Ta1	74.98 (17)	H19A—C19—H19B	109.5
C5—C1—Ta1	69.50 (18)	C17—C19—H19C	109.5
C6—C1—Ta1	128.6 (2)	H19A—C19—H19C	109.5
C1—C2—C3	108.4 (2)	H19B—C19—H19C	109.5
C1—C2—C7	126.0 (3)	C17—C20—H20A	109.5
C3—C2—C7	125.7 (3)	C17—C20—H20B	109.5
C1—C2—Ta1	72.89 (18)	H20A—C20—H20B	109.5
C3—C2—Ta1	71.83 (17)	C17—C20—H20C	109.5
C7—C2—Ta1	122.70 (19)	H20A—C20—H20C	109.5
C2—C3—C4	108.3 (3)	H20B—C20—H20C	109.5
C2—C3—C8	125.2 (3)	N1—C21—C24	110.2 (3)
C4—C3—C8	125.7 (3)	N1—C21—C23	109.3 (2)
C2—C3—Ta1	75.72 (16)	C24—C21—C23	110.1 (3)
C4—C3—Ta1	70.19 (17)	N1—C21—C22	110.1 (2)
C8—C3—Ta1	127.9 (2)	C24—C21—C22	108.8 (3)
C3—C4—C5	107.4 (3)	C23—C21—C22	108.4 (3)
C3—C4—C9	126.2 (3)	C21—C22—H22A	109.5
C5—C4—C9	126.0 (3)	C21—C22—H22B	109.5
C3—C4—Ta1	76.32 (18)	H22A—C22—H22B	109.5
C5—C4—Ta1	73.06 (19)	C21—C22—H22D	109.5
C9—C4—Ta1	122.5 (2)	H22A—C22—H22D	109.5
C1—C5—C4	107.7 (3)	H22B—C22—H22D	109.5
C1—C5—C10	125.2 (3)	C21—C23—H23A	109.5
C4—C5—C10	126.5 (3)	C21—C23—H23D	109.5
C1—C5—Ta1	77.10 (19)	H23A—C23—H23D	109.5
C4—C5—Ta1	72.7 (2)	C21—C23—H23B	109.5
C10—C5—Ta1	122.9 (2)	H23A—C23—H23B	109.5
C1—C6—H6A	109.5	H23D—C23—H23B	109.5
C1—C6—H6B	109.5	C21—C24—H24D	109.5
H6A—C6—H6B	109.5	C21—C24—H24A	109.5
C1—C6—H6C	109.5	H24D—C24—H24A	109.5
H6A—C6—H6C	109.5	C21—C24—H24B	109.5
H6B—C6—H6C	109.5	H24D—C24—H24B	109.5
C2—C7—H7A	109.5	H24A—C24—H24B	109.5

(xmas1)

Crystal data

C34H15F20O4Ta	F(000) = 2016
Mr = 1048.41	Dx = 2.089 Mg m^−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2c2b	Cell parameters from 57 reflections
a = 8.341 (2) Å	θ = 5.3–12.1°
b = 26.389 (5) Å	µ = 3.45 mm^−1
c = 15.145 (3) Å	T = 150 K
V = 3333.6 (12) Å^3	Needle, yellow
Z = 4	0.46 × 0.12 × 0.08 mm

Data collection

Siemens P4 diffractometer	2150 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω scans	h = −1→9
Absorption correction: empirical (using intensity measurements) ?	k = −31→1
Tmin = 0.674, Tmax = 0.770	l = −1→18
3749 measured reflections	3 standard reflections every 97 reflections
3043 independent reflections	intensity decay: none

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	Riding
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0378P)^2] where P = (Fo^2 + 2Fc^2)/3
3043 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.85 e Å^−3
0 restraints	Δρmin = −1.09 e Å^−3

Special details

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 on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	Occ. (<1)
Ta1	0.18380 (5)	0.133175 (19)	0.2500	0.01544 (14)
C1	−0.1055 (13)	0.1426 (4)	0.2500	0.023 (3)
C2	−0.0501 (9)	0.1690 (3)	0.1742 (5)	0.0214 (17)
C3	0.0490 (9)	0.2096 (3)	0.2029 (5)	0.0173 (16)
C4	−0.2235 (12)	0.1004 (5)	0.2500	0.028 (3)
H4A	−0.3303	0.1140	0.2500	0.042*
H4B	−0.2082	0.0800	0.3018	0.042*	0.50
H4BA	−0.2082	0.0800	0.1982	0.042*	0.50
C5	−0.0922 (10)	0.1553 (4)	0.0805 (5)	0.033 (2)
H5A	−0.1871	0.1733	0.0631	0.049*
H5B	−0.1111	0.1195	0.0766	0.049*
H5C	−0.0051	0.1644	0.0422	0.049*
C6	0.1279 (10)	0.2474 (3)	0.1439 (6)	0.031 (2)
H6A	0.0555	0.2750	0.1328	0.047*
H6B	0.1561	0.2315	0.0891	0.047*
H6C	0.2230	0.2601	0.1720	0.047*
O1	0.2321 (6)	0.1232 (2)	0.1229 (3)	0.0285 (14)
C7	0.3464 (9)	0.1091 (3)	0.0680 (5)	0.0203 (18)
C8	0.3589 (9)	0.1303 (3)	−0.0164 (5)	0.0231 (17)
F8	0.2576 (6)	0.16855 (19)	−0.0373 (3)	0.0353 (12)
C9	0.4754 (11)	0.1159 (3)	−0.0750 (5)	0.030 (2)
F9	0.4794 (6)	0.1386 (2)	−0.1551 (3)	0.0476 (14)
C10	0.5845 (11)	0.0787 (4)	−0.0527 (6)	0.037 (2)
F10	0.6961 (7)	0.0656 (3)	−0.1124 (4)	0.0598 (17)
C11	0.5746 (10)	0.0569 (3)	0.0282 (6)	0.028 (2)
F11	0.6825 (7)	0.0210 (2)	0.0511 (4)	0.0507 (14)
C12	0.4577 (11)	0.0716 (3)	0.0860 (5)	0.0268 (19)
F12	0.4528 (6)	0.04799 (19)	0.1659 (3)	0.0376 (12)
O2	0.3890 (9)	0.1690 (3)	0.2500	0.0298 (19)
C13	0.4961 (13)	0.2073 (4)	0.2500	0.024 (3)
C14	0.5538 (10)	0.2275 (3)	0.1719 (5)	0.0232 (18)
F14	0.5028 (6)	0.20997 (18)	0.0941 (3)	0.0376 (13)
C15	0.6670 (10)	0.2657 (3)	0.1724 (5)	0.0289 (19)
F15	0.7199 (6)	0.2849 (2)	0.0943 (3)	0.0438 (15)
C16	0.7245 (13)	0.2856 (4)	0.2500	0.025 (3)
F16	0.8301 (9)	0.3232 (3)	0.2500	0.0420 (18)
O3	0.1266 (9)	0.0632 (3)	0.2500	0.0270 (19)
C17	0.0591 (13)	0.0175 (4)	0.2500	0.021 (2)
C18	0.0239 (10)	−0.0070 (3)	0.3271 (6)	0.029 (2)
F18	0.0550 (7)	0.0159 (2)	0.4042 (3)	0.0450 (14)
C19	−0.0439 (10)	−0.0544 (3)	0.3290 (7)	0.041 (3)
F19	−0.0749 (8)	−0.0777 (2)	0.4059 (4)	0.069 (2)
C20	−0.0771 (15)	−0.0792 (4)	0.2500	0.043 (4)
F20	−0.1422 (10)	−0.1249 (3)	0.2500	0.082 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ta1	0.0128 (2)	0.0158 (2)	0.0177 (2)	0.0006 (3)	0.000	0.000
C1	0.005 (5)	0.017 (7)	0.047 (7)	0.002 (5)	0.000	0.000
C2	0.009 (4)	0.027 (4)	0.028 (4)	0.000 (3)	−0.004 (4)	0.003 (3)
C3	0.011 (4)	0.018 (4)	0.022 (4)	0.006 (3)	0.002 (4)	0.006 (3)
C4	0.009 (6)	0.023 (6)	0.051 (8)	0.000 (5)	0.000	0.000
C5	0.024 (5)	0.054 (6)	0.021 (4)	0.007 (4)	−0.011 (4)	−0.004 (4)
C6	0.026 (4)	0.031 (5)	0.037 (5)	0.005 (4)	0.003 (4)	0.017 (4)
O1	0.027 (3)	0.039 (4)	0.020 (3)	0.011 (3)	0.005 (2)	−0.003 (3)
C7	0.019 (5)	0.029 (4)	0.013 (3)	0.000 (4)	0.003 (3)	−0.001 (3)
C8	0.024 (4)	0.020 (4)	0.025 (4)	−0.004 (4)	−0.008 (3)	0.007 (4)
F8	0.038 (3)	0.039 (3)	0.029 (3)	0.001 (2)	−0.003 (2)	0.005 (2)
C9	0.037 (6)	0.037 (5)	0.015 (4)	−0.017 (4)	0.014 (4)	−0.003 (4)
F9	0.046 (3)	0.077 (4)	0.019 (2)	−0.017 (3)	0.007 (2)	0.007 (3)
C10	0.031 (5)	0.047 (6)	0.033 (5)	−0.002 (5)	0.008 (5)	−0.016 (5)
F10	0.040 (3)	0.091 (5)	0.049 (3)	0.010 (4)	0.023 (3)	−0.021 (3)
C11	0.014 (4)	0.026 (5)	0.045 (5)	0.006 (4)	0.004 (4)	−0.007 (4)
F11	0.033 (3)	0.058 (4)	0.061 (3)	0.013 (3)	0.004 (3)	−0.012 (3)
C12	0.029 (5)	0.025 (4)	0.027 (5)	0.005 (4)	−0.006 (4)	−0.003 (4)
F12	0.030 (3)	0.050 (3)	0.033 (3)	0.007 (3)	0.003 (3)	0.015 (2)
O2	0.013 (4)	0.030 (5)	0.046 (5)	−0.003 (4)	0.000	0.000
C13	0.015 (6)	0.017 (6)	0.041 (7)	0.010 (5)	0.000	0.000
C14	0.015 (4)	0.024 (4)	0.031 (4)	0.001 (4)	−0.003 (4)	−0.007 (4)
F14	0.036 (3)	0.043 (3)	0.034 (3)	−0.011 (3)	0.003 (2)	−0.010 (2)
C15	0.024 (5)	0.025 (4)	0.037 (5)	−0.003 (4)	0.017 (4)	0.006 (4)
F15	0.043 (4)	0.053 (3)	0.035 (3)	−0.015 (3)	0.012 (3)	0.002 (3)
C16	0.013 (7)	0.032 (7)	0.029 (6)	0.000 (5)	0.000	0.000
F16	0.034 (4)	0.037 (4)	0.055 (4)	−0.018 (4)	0.000	0.000
O3	0.018 (4)	0.020 (4)	0.043 (5)	−0.011 (3)	0.000	0.000
C17	0.005 (5)	0.023 (6)	0.034 (6)	−0.001 (5)	0.000	0.000
C18	0.022 (4)	0.025 (4)	0.039 (5)	0.005 (4)	0.010 (4)	−0.005 (4)
F18	0.054 (4)	0.049 (3)	0.031 (3)	0.000 (3)	0.010 (3)	0.009 (3)
C19	0.019 (4)	0.029 (5)	0.074 (7)	0.000 (4)	0.006 (5)	0.026 (5)
F19	0.061 (4)	0.058 (4)	0.086 (5)	−0.002 (3)	0.020 (4)	0.044 (4)
C20	0.021 (7)	0.011 (6)	0.098 (12)	−0.001 (6)	0.000	0.000
F20	0.041 (5)	0.021 (5)	0.185 (11)	−0.020 (4)	0.000	0.000

Geometric parameters (Å, º)

Ta1—O3	1.907 (7)	C8—F8	1.355 (9)
Ta1—O2	1.955 (8)	C8—C9	1.370 (11)
Ta1—O1^i	1.985 (5)	C9—F9	1.354 (9)
Ta1—O1	1.985 (5)	C9—C10	1.380 (13)
Ta1—C3^i	2.417 (7)	C10—F10	1.343 (10)
Ta1—C3	2.417 (7)	C10—C11	1.355 (12)
Ta1—C1	2.426 (11)	C11—F11	1.351 (10)
Ta1—C2^i	2.453 (7)	C11—C12	1.367 (11)
Ta1—C2	2.453 (7)	C12—F12	1.361 (9)
C1—C2^i	1.420 (10)	O2—C13	1.349 (13)
C1—C2	1.420 (10)	C13—C14^i	1.383 (10)
C1—C4	1.487 (15)	C13—C14	1.383 (10)
C2—C3	1.423 (10)	C14—F14	1.335 (9)
C2—C5	1.504 (10)	C14—C15	1.383 (11)
C3—C3^i	1.426 (14)	C15—F15	1.360 (9)
C3—C6	1.492 (10)	C15—C16	1.373 (10)
C4—H4A	0.9600	C16—F16	1.328 (13)
C4—H4B	0.9600	C16—C15^i	1.373 (10)
C4—H4BA	0.9600	O3—C17	1.330 (13)
C5—H5A	0.9600	C17—C18	1.368 (10)
C5—H5B	0.9600	C17—C18^i	1.368 (10)
C5—H5C	0.9600	C18—F18	1.341 (9)
C6—H6A	0.9600	C18—C19	1.373 (12)
C6—H6B	0.9600	C19—F19	1.343 (10)
C6—H6C	0.9600	C19—C20	1.391 (12)
O1—C7	1.318 (9)	C20—F20	1.322 (14)
C7—C12	1.384 (11)	C20—C19^i	1.391 (12)
C7—C8	1.398 (10)
O3—Ta1—O2	133.4 (3)	H4B—C4—H4BA	109.5
O3—Ta1—O1^i	85.57 (17)	C2—C5—H5A	109.5
O2—Ta1—O1^i	83.46 (17)	C2—C5—H5B	109.5
O3—Ta1—O1	85.57 (17)	H5A—C5—H5B	109.5
O2—Ta1—O1	83.46 (17)	C2—C5—H5C	109.5
O1^i—Ta1—O1	151.9 (3)	H5A—C5—H5C	109.5
O3—Ta1—C3^i	133.8 (3)	H5B—C5—H5C	109.5
O2—Ta1—C3^i	90.2 (3)	C3—C6—H6A	109.5
O1^i—Ta1—C3^i	85.3 (2)	C3—C6—H6B	109.5
O1—Ta1—C3^i	119.4 (2)	H6A—C6—H6B	109.5
O3—Ta1—C3	133.8 (3)	C3—C6—H6C	109.5
O2—Ta1—C3	90.2 (3)	H6A—C6—H6C	109.5
O1^i—Ta1—C3	119.4 (2)	H6B—C6—H6C	109.5
O1—Ta1—C3	85.3 (2)	C7—O1—Ta1	142.8 (5)
C3^i—Ta1—C3	34.3 (3)	O1—C7—C12	124.2 (7)
O3—Ta1—C1	81.4 (3)	O1—C7—C8	121.2 (7)
O2—Ta1—C1	145.2 (4)	C12—C7—C8	114.6 (7)
O1^i—Ta1—C1	102.45 (16)	F8—C8—C9	119.8 (7)
O1—Ta1—C1	102.45 (16)	F8—C8—C7	117.7 (7)
C3^i—Ta1—C1	56.7 (3)	C9—C8—C7	122.3 (8)
C3—Ta1—C1	56.7 (3)	F9—C9—C8	118.4 (8)
O3—Ta1—C2^i	100.0 (3)	F9—C9—C10	121.3 (8)
O2—Ta1—C2^i	120.7 (3)	C8—C9—C10	120.3 (7)
O1^i—Ta1—C2^i	76.0 (2)	F10—C10—C11	122.8 (9)
O1—Ta1—C2^i	131.8 (2)	F10—C10—C9	118.3 (8)
C3^i—Ta1—C2^i	34.0 (2)	C11—C10—C9	118.9 (8)
C3—Ta1—C2^i	56.4 (2)	F11—C11—C10	119.3 (8)
C1—Ta1—C2^i	33.8 (2)	F11—C11—C12	120.7 (8)
O3—Ta1—C2	100.0 (3)	C10—C11—C12	120.1 (8)
O2—Ta1—C2	120.7 (3)	F12—C12—C11	117.4 (7)
O1^i—Ta1—C2	131.8 (2)	F12—C12—C7	118.9 (7)
O1—Ta1—C2	76.0 (2)	C11—C12—C7	123.7 (8)
C3^i—Ta1—C2	56.4 (2)	C13—O2—Ta1	160.3 (7)
C3—Ta1—C2	34.0 (2)	O2—C13—C14^i	121.2 (5)
C1—Ta1—C2	33.8 (2)	O2—C13—C14	121.2 (5)
C2^i—Ta1—C2	55.8 (4)	C14^i—C13—C14	117.5 (10)
C2^i—C1—C2	108.0 (9)	F14—C14—C15	118.4 (7)
C2^i—C1—C4	125.6 (5)	F14—C14—C13	120.7 (7)
C2—C1—C4	125.6 (5)	C15—C14—C13	120.9 (8)
C2^i—C1—Ta1	74.1 (5)	F15—C15—C16	119.3 (7)
C2—C1—Ta1	74.1 (5)	F15—C15—C14	119.2 (8)
C4—C1—Ta1	125.5 (8)	C16—C15—C14	121.5 (8)
C1—C2—C3	108.1 (7)	F16—C16—C15	121.2 (5)
C1—C2—C5	124.7 (7)	F16—C16—C15^i	121.2 (5)
C3—C2—C5	127.2 (7)	C15—C16—C15^i	117.7 (10)
C1—C2—Ta1	72.0 (5)	C17—O3—Ta1	169.5 (7)
C3—C2—Ta1	71.6 (4)	O3—C17—C18	121.4 (5)
C5—C2—Ta1	122.3 (5)	O3—C17—C18^i	121.4 (5)
C2—C3—C3^i	107.8 (4)	C18—C17—C18^i	117.2 (10)
C2—C3—C6	125.3 (7)	F18—C18—C19	118.3 (8)
C3^i—C3—C6	126.8 (5)	F18—C18—C17	119.2 (7)
C2—C3—Ta1	74.4 (4)	C19—C18—C17	122.6 (9)
C3^i—C3—Ta1	72.84 (17)	F19—C19—C18	120.9 (9)
C6—C3—Ta1	122.0 (5)	F19—C19—C20	119.5 (8)
C1—C4—H4A	109.5	C18—C19—C20	119.5 (9)
C1—C4—H4B	109.5	F20—C20—C19	120.7 (6)
H4A—C4—H4B	109.5	F20—C20—C19^i	120.7 (6)
C1—C4—H4BA	109.5	C19—C20—C19^i	118.6 (11)
H4A—C4—H4BA	109.5

Symmetry code: (i) x, y, −z+1/2.

(95srv082)

Crystal data

C44H30F20O6Ta2.C7H8	F(000) = 2872
Mr = 1488.71	Dx = 2.004 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 429 reflections
a = 12.793 (2) Å	θ = 3.6–19.2°
b = 15.242 (2) Å	µ = 4.56 mm^−1
c = 25.708 (3) Å	T = 150 K
β = 100.178 (5)°	Irregular shape, yellow
V = 4933.9 (12) Å^3	0.8 × 0.45 × 0.3 mm
Z = 4

Data collection

Siemens SMART CCD diffractometer	6926 independent reflections
Radiation source: fine-focus sealed tube	6101 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω scans	θmax = 23.3°, θmin = 1.6°
Absorption correction: empirical (using intensity measurements) ?	h = −14→10
Tmin = 0.343, Tmax = 0.447	k = −16→16
17825 measured reflections	l = −18→28

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	Riding
S = 2.26	w = 1/[σ^2(Fo^2) + (0.010P)^2] where P = (Fo^2 + 2Fc^2)/3
6922 reflections	(Δ/σ)max < 0.001
619 parameters	Δρmax = 1.32 e Å^−3
0 restraints	Δρmin = −0.96 e Å^−3

Special details

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 on F² for ALL reflections except for 3 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	Occ. (<1)
Ta1	0.27368 (3)	0.20981 (3)	0.083963 (16)	0.02718 (13)
Ta2	0.19551 (3)	0.12229 (3)	0.176869 (16)	0.02686 (12)
O10	0.3210 (5)	0.1322 (4)	0.1449 (2)	0.0277 (15)
O11	0.1480 (5)	0.1951 (4)	0.1143 (2)	0.0292 (15)
C1	0.3251 (8)	0.0881 (6)	0.0313 (3)	0.029 (2)
C1A	0.3956 (8)	0.0134 (6)	0.0543 (4)	0.043 (3)
H1AA	0.4055	−0.0263	0.0266	0.065*
H1AB	0.3631	−0.0171	0.0799	0.065*
H1AC	0.4632	0.0361	0.0710	0.065*
C2	0.3552 (8)	0.1645 (7)	0.0075 (4)	0.033 (2)
C2A	0.4653 (7)	0.1919 (7)	0.0016 (4)	0.042 (3)
H2AA	0.4818	0.1677	−0.0305	0.062*
H2AB	0.5154	0.1707	0.0312	0.062*
H2AC	0.4689	0.2547	0.0003	0.062*
C3	0.2600 (8)	0.2123 (6)	−0.0128 (4)	0.034 (2)
C3A	0.2566 (9)	0.2945 (7)	−0.0439 (4)	0.053 (3)
H3AA	0.2515	0.2805	−0.0807	0.079*
H3AB	0.3203	0.3276	−0.0322	0.079*
H3AC	0.1960	0.3286	−0.0390	0.079*
C4	0.1716 (8)	0.1646 (6)	−0.0003 (4)	0.033 (2)
C4A	0.0567 (8)	0.1904 (7)	−0.0155 (5)	0.053 (3)
H4AA	0.0286	0.1672	−0.0499	0.080*
H4AB	0.0510	0.2532	−0.0163	0.080*
H4AC	0.0173	0.1672	0.0099	0.080*
C5	0.2112 (7)	0.0876 (6)	0.0268 (4)	0.029 (2)
C5A	0.1476 (7)	0.0133 (6)	0.0427 (4)	0.035 (3)
H5AA	0.1313	−0.0273	0.0139	0.053*
H5AB	0.0828	0.0355	0.0516	0.053*
H5AC	0.1878	−0.0160	0.0728	0.053*
O1	0.4151 (5)	0.2633 (4)	0.1058 (3)	0.0372 (17)
C6	0.5039 (7)	0.2647 (6)	0.1429 (4)	0.029 (2)
C7	0.5345 (8)	0.3402 (6)	0.1706 (4)	0.036 (3)
F7	0.4697 (4)	0.4120 (3)	0.1633 (2)	0.0431 (15)
C8	0.6257 (8)	0.3450 (6)	0.2089 (4)	0.032 (2)
F8	0.6509 (4)	0.4215 (4)	0.2351 (2)	0.0477 (16)
C9	0.6919 (8)	0.2726 (7)	0.2178 (4)	0.045 (3)
F9	0.7831 (5)	0.2786 (4)	0.2527 (3)	0.0593 (18)
C10	0.6655 (8)	0.1970 (7)	0.1896 (4)	0.040 (3)
F10	0.7296 (5)	0.1287 (4)	0.1980 (3)	0.0590 (18)
C11	0.5714 (8)	0.1935 (6)	0.1531 (4)	0.033 (2)
F11	0.5498 (4)	0.1179 (3)	0.1265 (2)	0.0416 (14)
O2	0.0696 (5)	0.0516 (4)	0.1551 (3)	0.0350 (17)
C12	−0.0293 (8)	0.0268 (6)	0.1394 (4)	0.032 (2)
C13	−0.0675 (7)	−0.0534 (7)	0.1533 (4)	0.034 (2)
F13	0.0010 (4)	−0.1057 (3)	0.1863 (3)	0.0502 (17)
C14	−0.1700 (9)	−0.0814 (7)	0.1385 (5)	0.045 (3)
F14	−0.1999 (5)	−0.1605 (4)	0.1536 (3)	0.0570 (18)
C15	−0.2437 (8)	−0.0298 (8)	0.1054 (4)	0.041 (3)
F15	−0.3441 (4)	−0.0559 (4)	0.0901 (2)	0.0568 (18)
C16	−0.2105 (9)	0.0485 (8)	0.0904 (4)	0.047 (3)
F16	−0.2784 (5)	0.1022 (5)	0.0596 (3)	0.0637 (19)
C17	−0.1054 (8)	0.0777 (7)	0.1065 (4)	0.039 (3)
F17	−0.0779 (5)	0.1562 (4)	0.0897 (3)	0.0574 (18)
O3	0.2644 (5)	0.0088 (4)	0.2046 (3)	0.0353 (17)
C18	0.3346 (8)	−0.0448 (6)	0.1891 (4)	0.030 (2)
C19	0.4449 (8)	−0.0278 (6)	0.2012 (3)	0.030 (2)
F19	0.4797 (4)	0.0449 (4)	0.2282 (2)	0.0419 (14)
C20	0.5194 (8)	−0.0843 (7)	0.1865 (4)	0.037 (3)
F20	0.6222 (4)	−0.0632 (4)	0.1984 (2)	0.0503 (17)
C21	0.4867 (8)	−0.1606 (7)	0.1601 (4)	0.034 (3)
F21	0.5580 (5)	−0.2162 (4)	0.1458 (2)	0.0512 (16)
C22	0.3789 (9)	−0.1795 (6)	0.1483 (4)	0.036 (3)
F22	0.3483 (5)	−0.2545 (4)	0.1233 (2)	0.0543 (17)
C23	0.3063 (8)	−0.1228 (6)	0.1627 (4)	0.035 (2)
F23	0.2024 (4)	−0.1429 (3)	0.1501 (2)	0.0473 (16)
O4	0.2274 (5)	0.3301 (4)	0.0675 (3)	0.047 (2)
C24	0.2154 (8)	0.4150 (7)	0.0610 (4)	0.036 (3)
C25	0.1166 (8)	0.4557 (7)	0.0618 (4)	0.038 (3)
F25	0.0341 (5)	0.4065 (4)	0.0692 (3)	0.0537 (17)
C26	0.1009 (9)	0.5450 (7)	0.0546 (4)	0.046 (3)
F26	0.0069 (5)	0.5807 (4)	0.0562 (3)	0.067 (2)
C27	0.1837 (9)	0.5971 (6)	0.0454 (4)	0.040 (3)
F27	0.1699 (5)	0.6845 (3)	0.0393 (3)	0.067 (2)
C28	0.2805 (8)	0.5601 (6)	0.0455 (4)	0.036 (3)
F28	0.3644 (5)	0.6108 (4)	0.0383 (3)	0.0630 (19)
C29	0.2959 (9)	0.4704 (6)	0.0522 (4)	0.041 (3)
F29	0.3905 (5)	0.4358 (4)	0.0479 (3)	0.0531 (17)
C30	0.2738 (9)	0.1960 (7)	0.2583 (5)	0.050 (3)*
C30A	0.3974 (18)	0.2201 (15)	0.2649 (9)	0.016 (5)*	0.37
H30A	0.4228	0.2748	0.2810	0.023*	0.37
H30B	0.3289	0.2287	0.2434	0.023*	0.37
H30C	0.4462	0.1991	0.2434	0.023*	0.37
C30B	0.3928 (18)	0.1848 (15)	0.2876 (10)	0.088 (8)*	0.63
H30D	0.4031	0.2135	0.3213	0.132*	0.63
H30E	0.4461	0.1404	0.2878	0.132*	0.63
H30F	0.3237	0.1582	0.2808	0.132*	0.63
C31	0.2053 (9)	0.1373 (7)	0.2734 (5)	0.051 (3)*
C31A	0.2790 (18)	0.0688 (15)	0.3125 (9)	0.019 (6)*	0.37
H31A	0.3122	0.0885	0.3470	0.028*	0.37
H31B	0.2829	0.1144	0.2872	0.028*	0.37
H31C	0.3149	0.0175	0.3031	0.028*	0.37
C31B	0.2149 (16)	0.0567 (14)	0.3128 (9)	0.076 (7)*	0.63
H31D	0.1972	0.0737	0.3462	0.114*	0.63
H31E	0.2040	−0.0052	0.3078	0.114*	0.63
H31F	0.1705	0.0879	0.2848	0.114*	0.63
C32	0.1047 (9)	0.1605 (7)	0.2507 (5)	0.051 (3)*
C32A	−0.028 (3)	0.144 (2)	0.2486 (14)	0.065 (10)*	0.37
H32A	−0.0595	0.1759	0.2741	0.098*	0.37
H32B	−0.0832	0.1206	0.2220	0.098*	0.37
H32C	0.0160	0.1826	0.2324	0.098*	0.37
C32B	0.0119 (13)	0.0992 (11)	0.2649 (7)	0.042 (5)*	0.63
H32D	0.0081	0.0993	0.3019	0.063*	0.63
H32E	0.0844	0.1067	0.2606	0.063*	0.63
H32F	−0.0146	0.0444	0.2496	0.063*	0.63
C33	0.1077 (9)	0.2352 (7)	0.2209 (5)	0.050 (3)*
C33A	0.052 (2)	0.3169 (18)	0.1856 (11)	0.041 (8)*	0.37
H33A	0.0398	0.3692	0.2044	0.062*	0.37
H33B	0.0479	0.3304	0.1488	0.062*	0.37
H33C	0.1217	0.2945	0.1995	0.062*	0.37
C33B	−0.0031 (14)	0.2712 (12)	0.1898 (8)	0.055 (5)*	0.63
H33D	−0.0505	0.2945	0.2115	0.083*	0.63
H33E	0.0313	0.2198	0.2063	0.083*	0.63
H33F	−0.0427	0.2560	0.1557	0.083*	0.63
C34	0.2158 (9)	0.2568 (7)	0.2247 (4)	0.047 (3)*
C34A	0.2942 (18)	0.3315 (15)	0.2135 (9)	0.024 (6)*	0.37
H34A	0.3107	0.3740	0.2412	0.036*	0.37
H34B	0.3469	0.3339	0.1911	0.036*	0.37
H34C	0.2936	0.2739	0.2286	0.036*	0.37
C34B	0.2346 (6)	0.3424 (5)	0.1956 (3)	0.067 (6)*	0.63
H34D	0.2061	0.3942	0.2092	0.100*	0.63
H34E	0.1878	0.2938	0.1977	0.100*	0.63
H34F	0.2413	0.3519	0.1594	0.100*	0.63
C35	0.7545 (6)	0.4299 (5)	0.1099 (3)	0.086*
C36	0.6550 (6)	0.4680 (5)	0.0949 (3)	0.086*
H36A	0.6035	0.4399	0.0705	0.103*
C37	0.6326 (6)	0.5480 (5)	0.1164 (3)	0.086*
H37A	0.5658	0.5728	0.1061	0.103*
C38	0.7081	0.5919	0.1532	0.086*
H38A	0.6921	0.6454	0.1674	0.103*
C39	0.8076	0.5538	0.1682	0.086*
H39A	0.8591	0.5819	0.1926	0.103*
C40	0.8301	0.4738	0.1467	0.086*
H40A	0.8969	0.4490	0.1570	0.103*
C41	0.7659	0.3476	0.0862	0.086*
H41A	0.7014	0.3332	0.0625	0.129*
H41B	0.7804	0.3034	0.1131	0.129*
H41C	0.8235	0.3501	0.0669	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ta1	0.0319 (2)	0.0235 (2)	0.0268 (2)	0.00272 (19)	0.00705 (18)	0.00278 (19)
Ta2	0.0304 (2)	0.0232 (2)	0.0282 (2)	0.00268 (19)	0.00850 (18)	0.00188 (19)
O10	0.032 (4)	0.028 (4)	0.025 (4)	0.009 (3)	0.011 (3)	0.008 (3)
O11	0.034 (4)	0.024 (4)	0.031 (4)	0.003 (3)	0.009 (3)	0.004 (3)
C1	0.054 (7)	0.017 (5)	0.012 (5)	0.013 (5)	0.000 (5)	−0.004 (4)
C1A	0.052 (7)	0.046 (7)	0.030 (6)	0.008 (6)	0.000 (5)	−0.006 (5)
C2	0.040 (6)	0.044 (6)	0.020 (6)	−0.004 (5)	0.020 (5)	−0.011 (5)
C2A	0.038 (6)	0.055 (7)	0.034 (7)	−0.002 (5)	0.010 (5)	0.005 (6)
C3	0.060 (7)	0.031 (6)	0.011 (5)	0.004 (5)	0.005 (5)	0.001 (5)
C3A	0.077 (9)	0.050 (7)	0.034 (7)	0.009 (7)	0.017 (6)	0.015 (6)
C4	0.033 (6)	0.038 (6)	0.027 (6)	0.000 (5)	0.000 (5)	0.005 (5)
C4A	0.035 (7)	0.062 (8)	0.059 (8)	0.007 (6)	−0.003 (6)	0.009 (6)
C5	0.022 (5)	0.038 (6)	0.028 (6)	−0.004 (5)	0.002 (4)	0.001 (5)
C5A	0.033 (6)	0.038 (6)	0.034 (6)	0.006 (5)	0.005 (5)	−0.006 (5)
O1	0.038 (4)	0.035 (4)	0.037 (4)	−0.012 (3)	0.001 (3)	0.005 (3)
C6	0.025 (6)	0.035 (6)	0.028 (6)	−0.010 (5)	0.008 (5)	0.004 (5)
C7	0.042 (7)	0.027 (6)	0.042 (7)	−0.007 (5)	0.019 (6)	−0.008 (5)
F7	0.046 (4)	0.039 (3)	0.047 (4)	−0.001 (3)	0.013 (3)	0.000 (3)
C8	0.047 (7)	0.033 (6)	0.021 (6)	−0.010 (5)	0.017 (5)	−0.005 (5)
F8	0.056 (4)	0.041 (4)	0.044 (4)	−0.014 (3)	0.002 (3)	−0.017 (3)
C9	0.036 (7)	0.055 (8)	0.042 (7)	0.001 (6)	0.002 (5)	−0.020 (6)
F9	0.045 (4)	0.069 (5)	0.059 (5)	−0.003 (4)	−0.004 (3)	−0.024 (4)
C10	0.030 (6)	0.050 (7)	0.040 (7)	−0.005 (6)	0.003 (5)	−0.015 (6)
F10	0.047 (4)	0.063 (4)	0.061 (5)	0.016 (4)	−0.006 (3)	−0.022 (4)
C11	0.030 (6)	0.033 (6)	0.038 (6)	−0.011 (5)	0.016 (5)	−0.017 (5)
F11	0.052 (4)	0.034 (3)	0.039 (4)	0.001 (3)	0.007 (3)	−0.011 (3)
O2	0.023 (4)	0.036 (4)	0.045 (5)	−0.005 (3)	0.004 (3)	−0.002 (3)
C12	0.039 (7)	0.027 (6)	0.032 (6)	−0.005 (5)	0.016 (5)	0.002 (5)
C13	0.024 (6)	0.039 (6)	0.040 (7)	0.006 (5)	0.006 (5)	0.005 (5)
F13	0.045 (4)	0.037 (4)	0.070 (5)	−0.002 (3)	0.014 (3)	0.010 (3)
C14	0.046 (7)	0.041 (7)	0.050 (8)	−0.012 (6)	0.016 (6)	−0.017 (6)
F14	0.048 (4)	0.046 (4)	0.081 (5)	−0.019 (3)	0.020 (4)	−0.007 (4)
C15	0.036 (7)	0.053 (8)	0.036 (7)	−0.015 (6)	0.011 (5)	−0.024 (6)
F15	0.032 (4)	0.091 (5)	0.047 (4)	−0.015 (4)	0.004 (3)	−0.024 (4)
C16	0.044 (7)	0.066 (8)	0.028 (7)	0.019 (7)	0.002 (6)	−0.002 (6)
F16	0.044 (4)	0.097 (5)	0.046 (4)	0.011 (4)	−0.001 (3)	0.019 (4)
C17	0.047 (7)	0.034 (6)	0.041 (7)	0.003 (6)	0.020 (6)	0.006 (5)
F17	0.049 (4)	0.052 (4)	0.071 (5)	0.011 (3)	0.012 (4)	0.022 (4)
O3	0.037 (4)	0.032 (4)	0.041 (4)	0.004 (3)	0.018 (4)	0.003 (3)
C18	0.034 (6)	0.031 (6)	0.025 (6)	0.010 (5)	0.005 (5)	0.017 (5)
C19	0.052 (7)	0.022 (5)	0.014 (5)	0.002 (5)	0.003 (5)	0.008 (4)
F19	0.044 (4)	0.038 (3)	0.039 (4)	0.002 (3)	−0.005 (3)	−0.010 (3)
C20	0.037 (7)	0.044 (7)	0.031 (6)	0.014 (5)	0.007 (5)	0.002 (5)
F20	0.033 (4)	0.062 (4)	0.054 (4)	0.012 (3)	0.000 (3)	0.003 (3)
C21	0.035 (6)	0.048 (7)	0.020 (6)	0.019 (6)	0.004 (5)	−0.001 (5)
F21	0.056 (4)	0.046 (4)	0.053 (4)	0.023 (3)	0.014 (3)	−0.005 (3)
C22	0.056 (8)	0.021 (6)	0.030 (6)	0.011 (5)	0.008 (5)	0.003 (5)
F22	0.070 (5)	0.035 (4)	0.056 (4)	−0.001 (3)	0.005 (3)	−0.012 (3)
C23	0.040 (7)	0.028 (6)	0.039 (7)	−0.004 (5)	0.011 (5)	0.006 (5)
F23	0.037 (4)	0.040 (4)	0.065 (4)	−0.007 (3)	0.012 (3)	0.007 (3)
O4	0.051 (5)	0.023 (4)	0.068 (6)	0.004 (3)	0.015 (4)	0.016 (4)
C24	0.047 (7)	0.030 (6)	0.030 (6)	−0.001 (5)	0.002 (5)	0.001 (5)
C25	0.036 (6)	0.053 (7)	0.025 (6)	−0.007 (6)	0.006 (5)	0.002 (5)
F25	0.047 (4)	0.050 (4)	0.066 (5)	0.003 (3)	0.015 (3)	0.011 (3)
C26	0.051 (8)	0.044 (7)	0.039 (7)	0.024 (6)	0.001 (6)	−0.001 (6)
F26	0.066 (5)	0.055 (4)	0.077 (5)	0.027 (4)	0.005 (4)	−0.004 (4)
C27	0.059 (8)	0.026 (6)	0.028 (6)	0.004 (6)	−0.009 (6)	−0.001 (5)
F27	0.093 (5)	0.018 (3)	0.083 (5)	0.010 (3)	−0.001 (4)	0.002 (3)
C28	0.043 (7)	0.025 (6)	0.033 (6)	−0.006 (5)	−0.010 (5)	0.009 (5)
F28	0.077 (5)	0.041 (4)	0.068 (5)	−0.020 (4)	0.004 (4)	0.017 (3)
C29	0.062 (8)	0.023 (6)	0.038 (7)	0.010 (6)	0.007 (6)	0.006 (5)
F29	0.045 (4)	0.049 (4)	0.068 (5)	0.004 (3)	0.018 (3)	0.011 (3)

Geometric parameters (Å, º)

Ta1—O11	1.921 (6)	C23—F23	1.346 (10)
Ta1—O4	1.949 (6)	O4—C24	1.311 (11)
Ta1—O10	1.972 (6)	C24—C29	1.381 (13)
Ta1—O1	1.973 (6)	C24—C25	1.412 (13)
Ta1—C5	2.420 (9)	C25—F25	1.335 (10)
Ta1—C4	2.424 (10)	C25—C26	1.384 (14)
Ta1—C1	2.455 (8)	C26—F26	1.327 (11)
Ta1—C3	2.463 (9)	C26—C27	1.377 (14)
Ta1—C2	2.480 (8)	C27—F27	1.350 (11)
Ta1—Ta2	3.0542 (6)	C27—C28	1.360 (13)
Ta2—O10	1.934 (6)	C28—F28	1.362 (10)
Ta2—O2	1.937 (6)	C28—C29	1.387 (13)
Ta2—O11	1.960 (6)	C29—F29	1.343 (11)
Ta2—O3	2.014 (6)	C30—C31	1.356 (14)
Ta2—C34	2.381 (11)	C30—C34	1.389 (14)
Ta2—C30	2.431 (11)	C30—C30B	1.58 (2)
Ta2—C33	2.441 (11)	C30—C30A	1.60 (2)
Ta2—C32	2.463 (11)	C30A—C30B	0.80 (3)
Ta2—C31	2.473 (11)	C30A—H30A	0.9600
C1—C2	1.400 (12)	C30A—H30B	0.9600
C1—C5	1.442 (12)	C30A—H30C	0.9600
C1—C1A	1.507 (12)	C30B—H30D	0.9600
C1A—H1AA	0.9600	C30B—H30E	0.9600
C1A—H1AB	0.9600	C30B—H30F	0.9600
C1A—H1AC	0.9600	C31—C32	1.362 (14)
C2—C3	1.437 (13)	C31—C31B	1.58 (2)
C2—C2A	1.501 (12)	C31—C31A	1.63 (2)
C2A—H2AA	0.9600	C31A—C31B	0.84 (2)
C2A—H2AB	0.9600	C31A—H31A	0.9600
C2A—H2AC	0.9600	C31A—H31B	0.9600
C3—C4	1.428 (13)	C31A—H31C	0.9600
C3—C3A	1.483 (13)	C31B—H31D	0.9600
C3A—H3AA	0.9600	C31B—H31E	0.9600
C3A—H3AB	0.9600	C31B—H31F	0.9600
C3A—H3AC	0.9600	C32—C33	1.376 (14)
C4—C5	1.413 (12)	C32—C32B	1.603 (19)
C4—C4A	1.504 (12)	C32—C32A	1.71 (3)
C4A—H4AA	0.9600	C32A—C32B	0.91 (3)
C4A—H4AB	0.9600	C32A—H32A	0.9600
C4A—H4AC	0.9600	C32A—H32B	0.9600
C5—C5A	1.492 (12)	C32A—H32C	0.9600
C5A—H5AA	0.9600	C32B—H32D	0.9600
C5A—H5AB	0.9600	C32B—H32E	0.9600
C5A—H5AC	0.9600	C32B—H32F	0.9600
O1—C6	1.349 (10)	C33—C34	1.409 (14)
C6—C7	1.373 (12)	C33—C33B	1.60 (2)
C6—C11	1.382 (12)	C33—C33A	1.63 (3)
C7—F7	1.366 (11)	C33A—C33B	1.01 (3)
C7—C8	1.389 (14)	C33A—H33A	0.9600
C8—F8	1.356 (10)	C33A—H33B	0.9600
C8—C9	1.386 (13)	C33A—H33C	0.9600
C9—F9	1.343 (11)	C33B—H33D	0.9600
C9—C10	1.370 (13)	C33B—H33E	0.9600
C10—F10	1.319 (11)	C33B—H33F	0.9600
C10—C11	1.391 (13)	C34—C34B	1.544 (13)
C11—F11	1.345 (10)	C34—C34A	1.58 (2)
O2—C12	1.313 (10)	C34A—C34B	0.83 (2)
C12—C13	1.387 (12)	C34A—H34A	0.9600
C12—C17	1.405 (13)	C34A—H34B	0.9600
C13—F13	1.364 (10)	C34A—H34C	0.9600
C13—C14	1.367 (13)	C34B—H34D	0.9600
C14—F14	1.345 (12)	C34B—H34E	0.9600
C14—C15	1.395 (15)	C34B—H34F	0.9600
C15—F15	1.336 (11)	C35—C36	1.3900
C15—C16	1.345 (15)	C35—C40	1.398 (8)
C16—F16	1.345 (11)	C35—C41	1.413 (8)
C16—C17	1.407 (14)	C36—C37	1.3901
C17—F17	1.339 (10)	C36—H36A	0.9300
O3—C18	1.326 (10)	C37—C38	1.398 (8)
C18—C23	1.385 (13)	C37—H37A	0.9299
C18—C19	1.414 (13)	C38—C39	1.3900
C19—F19	1.340 (10)	C38—H38A	0.9300
C19—C20	1.386 (13)	C39—C40	1.3900
C20—F20	1.335 (11)	C39—H39A	0.9300
C20—C21	1.375 (13)	C40—H40A	0.9300
C21—F21	1.342 (10)	C41—H41A	0.9600
C21—C22	1.388 (13)	C41—H41B	0.9600
C22—F22	1.336 (10)	C41—H41C	0.9600
C22—C23	1.367 (13)
O11—Ta1—O4	87.3 (3)	F21—C21—C22	120.4 (9)
O11—Ta1—O10	76.6 (2)	C20—C21—C22	119.1 (9)
O4—Ta1—O10	140.8 (3)	F22—C22—C23	121.0 (10)
O11—Ta1—O1	136.3 (3)	F22—C22—C21	118.6 (9)
O4—Ta1—O1	84.3 (3)	C23—C22—C21	120.4 (9)
O10—Ta1—O1	83.3 (3)	F23—C23—C22	118.7 (9)
O11—Ta1—C5	87.0 (3)	F23—C23—C18	118.4 (9)
O4—Ta1—C5	122.5 (3)	C22—C23—C18	122.9 (10)
O10—Ta1—C5	92.5 (3)	C24—O4—Ta1	168.6 (7)
O1—Ta1—C5	132.8 (3)	O4—C24—C29	123.4 (10)
O11—Ta1—C4	88.4 (3)	O4—C24—C25	121.1 (10)
O4—Ta1—C4	88.8 (3)	C29—C24—C25	115.4 (10)
O10—Ta1—C4	125.6 (3)	F25—C25—C26	118.2 (10)
O1—Ta1—C4	134.0 (3)	F25—C25—C24	119.2 (10)
C5—Ta1—C4	33.9 (3)	C26—C25—C24	122.6 (10)
O11—Ta1—C1	117.5 (3)	F26—C26—C27	119.8 (10)
O4—Ta1—C1	133.8 (3)	F26—C26—C25	120.7 (11)
O10—Ta1—C1	84.9 (3)	C27—C26—C25	119.5 (10)
O1—Ta1—C1	98.5 (3)	F27—C27—C28	120.7 (10)
C5—Ta1—C1	34.4 (3)	F27—C27—C26	120.0 (10)
C4—Ta1—C1	56.4 (3)	C28—C27—C26	119.2 (10)
O11—Ta1—C3	119.8 (3)	C27—C28—F28	120.3 (9)
O4—Ta1—C3	78.6 (3)	C27—C28—C29	121.2 (10)
O10—Ta1—C3	140.3 (3)	F28—C28—C29	118.5 (10)
O1—Ta1—C3	100.3 (3)	F29—C29—C24	118.8 (9)
C5—Ta1—C3	56.0 (3)	F29—C29—C28	119.2 (10)
C4—Ta1—C3	34.0 (3)	C24—C29—C28	121.9 (10)
C1—Ta1—C3	55.4 (3)	C31—C30—C34	108.5 (10)
O11—Ta1—C2	142.1 (3)	C31—C30—C30B	114.0 (13)
O4—Ta1—C2	104.1 (3)	C34—C30—C30B	137.0 (13)
O10—Ta1—C2	110.5 (3)	C31—C30—C30A	142.7 (13)
O1—Ta1—C2	81.2 (3)	C34—C30—C30A	108.8 (12)
C5—Ta1—C2	56.3 (3)	C30B—C30—C30A	29.2 (10)
C4—Ta1—C2	56.5 (3)	C31—C30—Ta2	75.7 (7)
C1—Ta1—C2	33.0 (3)	C34—C30—Ta2	71.3 (7)
C3—Ta1—C2	33.8 (3)	C30B—C30—Ta2	125.1 (11)
O11—Ta1—Ta2	38.55 (18)	C30A—C30—Ta2	116.5 (10)
O4—Ta1—Ta2	116.8 (2)	C30B—C30A—C30	74 (3)
O10—Ta1—Ta2	38.12 (16)	C30B—C30A—H30A	109.5
O1—Ta1—Ta2	111.59 (19)	C30—C30A—H30A	119.7
C5—Ta1—Ta2	91.2 (2)	C30B—C30A—H30B	109.5
C4—Ta1—Ta2	112.1 (2)	C30—C30A—H30B	35.5
C1—Ta1—Ta2	105.0 (2)	H30A—C30A—H30B	109.5
C3—Ta1—Ta2	145.3 (2)	C30B—C30A—H30C	109.5
C2—Ta1—Ta2	137.7 (2)	C30—C30A—H30C	126.3
O10—Ta2—O2	129.1 (3)	H30A—C30A—H30C	109.5
O10—Ta2—O11	76.6 (2)	H30B—C30A—H30C	109.5
O2—Ta2—O11	87.5 (3)	C30A—C30B—C30	77 (3)
O10—Ta2—O3	82.7 (2)	C30A—C30B—H30D	109.5
O2—Ta2—O3	85.1 (3)	C30—C30B—H30D	110.3
O11—Ta2—O3	146.1 (2)	C30A—C30B—H30E	109.5
O10—Ta2—C34	97.4 (3)	C30—C30B—H30E	134.5
O2—Ta2—C34	129.6 (3)	H30D—C30B—H30E	109.5
O11—Ta2—C34	85.7 (3)	C30A—C30B—H30F	109.5
O3—Ta2—C34	123.8 (3)	C30—C30B—H30F	35.1
O10—Ta2—C30	94.7 (3)	H30D—C30B—H30F	109.5
O2—Ta2—C30	134.5 (3)	H30E—C30B—H30F	109.5
O11—Ta2—C30	117.7 (3)	C30—C31—C32	108.4 (11)
O3—Ta2—C30	90.3 (3)	C30—C31—C31B	135.6 (13)
C34—Ta2—C30	33.5 (3)	C32—C31—C31B	115.8 (12)
O10—Ta2—C33	128.8 (3)	C30—C31—C31A	105.5 (12)
O2—Ta2—C33	95.7 (3)	C32—C31—C31A	146.1 (13)
O11—Ta2—C33	83.1 (3)	C31B—C31—C31A	30.3 (9)
O3—Ta2—C33	130.5 (3)	C30—C31—Ta2	72.2 (7)
C34—Ta2—C33	33.9 (3)	C32—C31—Ta2	73.6 (7)
C30—Ta2—C33	55.1 (4)	C31B—C31—Ta2	123.7 (10)
O10—Ta2—C32	148.0 (3)	C31A—C31—Ta2	118.8 (10)
O2—Ta2—C32	82.7 (3)	C31B—C31A—C31	72 (2)
O11—Ta2—C32	112.2 (3)	C31B—C31A—H31A	109.5
O3—Ta2—C32	99.6 (3)	C31—C31A—H31A	118.9
C34—Ta2—C32	54.7 (4)	C31B—C31A—H31B	109.5
C30—Ta2—C32	53.5 (4)	C31—C31A—H31B	37.9
C33—Ta2—C32	32.6 (3)	H31A—C31A—H31B	109.5
O10—Ta2—C31	121.3 (3)	C31B—C31A—H31C	109.5
O2—Ta2—C31	103.5 (3)	C31—C31A—H31C	128.1
O11—Ta2—C31	136.4 (3)	H31A—C31A—H31C	109.5
O3—Ta2—C31	77.5 (3)	H31B—C31A—H31C	109.5
C34—Ta2—C31	54.6 (4)	C31A—C31B—C31	78 (2)
C30—Ta2—C31	32.1 (3)	C31A—C31B—H31D	109.5
C33—Ta2—C31	54.2 (4)	C31—C31B—H31D	111.0
C32—Ta2—C31	32.0 (3)	C31A—C31B—H31E	109.5
O10—Ta2—Ta1	39.00 (17)	C31—C31B—H31E	133.2
O2—Ta2—Ta1	112.80 (19)	H31D—C31B—H31E	109.5
O11—Ta2—Ta1	37.63 (17)	C31A—C31B—H31F	109.5
O3—Ta2—Ta1	117.94 (17)	C31—C31B—H31F	33.7
C34—Ta2—Ta1	90.4 (3)	H31D—C31B—H31F	109.5
C30—Ta2—Ta1	109.2 (3)	H31E—C31B—H31F	109.5
C33—Ta2—Ta1	107.2 (3)	C31—C32—C33	109.6 (11)
C32—Ta2—Ta1	139.8 (3)	C31—C32—C32B	115.7 (11)
C31—Ta2—Ta1	141.1 (3)	C33—C32—C32B	134.7 (12)
Ta2—O10—Ta1	102.9 (3)	C31—C32—C32A	146.5 (15)
Ta1—O11—Ta2	103.8 (3)	C33—C32—C32A	103.2 (14)
C2—C1—C5	108.8 (8)	C32B—C32—C32A	31.7 (11)
C2—C1—C1A	127.4 (9)	C31—C32—Ta2	74.4 (7)
C5—C1—C1A	123.6 (9)	C33—C32—Ta2	72.8 (7)
C2—C1—Ta1	74.5 (5)	C32B—C32—Ta2	120.5 (9)
C5—C1—Ta1	71.5 (5)	C32A—C32—Ta2	122.8 (13)
C1A—C1—Ta1	123.7 (6)	C32B—C32A—C32	68 (2)
C1—C1A—H1AA	109.5	C32B—C32A—H32A	109.5
C1—C1A—H1AB	109.5	C32—C32A—H32A	115.9
H1AA—C1A—H1AB	109.5	C32B—C32A—H32B	109.5
C1—C1A—H1AC	109.5	C32—C32A—H32B	132.7
H1AA—C1A—H1AC	109.5	H32A—C32A—H32B	109.5
H1AB—C1A—H1AC	109.5	C32B—C32A—H32C	109.5
C1—C2—C3	107.4 (8)	C32—C32A—H32C	42.7
C1—C2—C2A	127.7 (9)	H32A—C32A—H32C	109.5
C3—C2—C2A	124.9 (9)	H32B—C32A—H32C	109.5
C1—C2—Ta1	72.5 (5)	C32A—C32B—C32	81 (3)
C3—C2—Ta1	72.5 (5)	C32A—C32B—H32D	109.5
C2A—C2—Ta1	122.4 (6)	C32—C32B—H32D	113.2
C2—C2A—H2AA	109.5	C32A—C32B—H32E	109.5
C2—C2A—H2AB	109.5	C32—C32B—H32E	30.0
H2AA—C2A—H2AB	109.5	H32D—C32B—H32E	109.5
C2—C2A—H2AC	109.5	C32A—C32B—H32F	109.5
H2AA—C2A—H2AC	109.5	C32—C32B—H32F	129.4
H2AB—C2A—H2AC	109.5	H32D—C32B—H32F	109.5
C4—C3—C2	108.3 (8)	H32E—C32B—H32F	109.5
C4—C3—C3A	127.1 (9)	C32—C33—C34	106.2 (10)
C2—C3—C3A	124.5 (9)	C32—C33—C33B	117.0 (11)
C4—C3—Ta1	71.5 (5)	C34—C33—C33B	136.7 (11)
C2—C3—Ta1	73.7 (5)	C32—C33—C33A	153.1 (14)
C3A—C3—Ta1	123.2 (7)	C34—C33—C33A	100.6 (12)
C3—C3A—H3AA	109.5	C33B—C33—C33A	36.6 (10)
C3—C3A—H3AB	109.5	C32—C33—Ta2	74.6 (7)
H3AA—C3A—H3AB	109.5	C34—C33—Ta2	70.7 (6)
C3—C3A—H3AC	109.5	C33B—C33—Ta2	116.8 (9)
H3AA—C3A—H3AC	109.5	C33A—C33—Ta2	118.1 (11)
H3AB—C3A—H3AC	109.5	C33B—C33A—C33	69.9 (19)
C5—C4—C3	107.7 (8)	C33B—C33A—H33A	109.5
C5—C4—C4A	126.4 (9)	C33—C33A—H33A	116.6
C3—C4—C4A	125.8 (9)	C33B—C33A—H33B	109.5
C5—C4—Ta1	72.9 (5)	C33—C33A—H33B	131.2
C3—C4—Ta1	74.5 (5)	H33A—C33A—H33B	109.5
C4A—C4—Ta1	120.4 (7)	C33B—C33A—H33C	109.5
C4—C4A—H4AA	109.5	C33—C33A—H33C	40.3
C4—C4A—H4AB	109.5	H33A—C33A—H33C	109.5
H4AA—C4A—H4AB	109.5	H33B—C33A—H33C	109.5
C4—C4A—H4AC	109.5	C33A—C33B—C33	73 (2)
H4AA—C4A—H4AC	109.5	C33A—C33B—H33D	109.5
H4AB—C4A—H4AC	109.5	C33—C33B—H33D	115.6
C4—C5—C1	107.7 (8)	C33A—C33B—H33E	109.5
C4—C5—C5A	126.9 (8)	C33—C33B—H33E	36.9
C1—C5—C5A	125.0 (8)	H33D—C33B—H33E	109.5
C4—C5—Ta1	73.2 (5)	C33A—C33B—H33F	109.5
C1—C5—Ta1	74.1 (5)	C33—C33B—H33F	130.7
C5A—C5—Ta1	123.7 (6)	H33D—C33B—H33F	109.5
C5—C5A—H5AA	109.5	H33E—C33B—H33F	109.5
C5—C5A—H5AB	109.5	C30—C34—C33	107.3 (10)
H5AA—C5A—H5AB	109.5	C30—C34—C34B	138.9 (10)
C5—C5A—H5AC	109.5	C33—C34—C34B	113.6 (9)
H5AA—C5A—H5AC	109.5	C30—C34—C34A	107.9 (12)
H5AB—C5A—H5AC	109.5	C33—C34—C34A	143.6 (13)
C6—O1—Ta1	145.4 (6)	C34B—C34—C34A	31.0 (9)
O1—C6—C7	120.5 (9)	C30—C34—Ta2	75.2 (7)
O1—C6—C11	122.8 (9)	C33—C34—Ta2	75.3 (6)
C7—C6—C11	116.6 (9)	C34B—C34—Ta2	119.3 (7)
F7—C7—C6	119.3 (9)	C34A—C34—Ta2	122.8 (11)
F7—C7—C8	117.9 (9)	C34B—C34A—C34	72.3 (17)
C6—C7—C8	122.6 (10)	C34B—C34A—H34A	109.5
F8—C8—C9	121.2 (9)	C34—C34A—H34A	114.5
F8—C8—C7	119.6 (9)	C34B—C34A—H34B	109.5
C9—C8—C7	119.1 (9)	C34—C34A—H34B	132.3
F9—C9—C10	121.0 (10)	H34A—C34A—H34B	109.5
F9—C9—C8	119.3 (9)	C34B—C34A—H34C	109.5
C10—C9—C8	119.7 (10)	C34—C34A—H34C	38.3
F10—C10—C9	119.3 (9)	H34A—C34A—H34C	109.5
F10—C10—C11	121.2 (9)	H34B—C34A—H34C	109.5
C9—C10—C11	119.5 (10)	C34A—C34B—C34	76.7 (18)
F11—C11—C6	120.7 (9)	C34A—C34B—H34D	109.5
F11—C11—C10	116.9 (9)	C34—C34B—H34D	114.6
C6—C11—C10	122.4 (9)	C34A—C34B—H34E	109.5
C12—O2—Ta2	162.8 (6)	C34—C34B—H34E	33.8
O2—C12—C13	122.6 (9)	H34D—C34B—H34E	109.5
O2—C12—C17	123.6 (9)	C34A—C34B—H34F	109.5
C13—C12—C17	113.8 (9)	C34—C34B—H34F	130.1
F13—C13—C14	118.1 (9)	H34D—C34B—H34F	109.5
F13—C13—C12	117.3 (9)	H34E—C34B—H34F	109.5
C14—C13—C12	124.6 (10)	C36—C35—C40	118.5 (4)
F14—C14—C13	120.5 (11)	C36—C35—C41	114.2 (3)
F14—C14—C15	119.1 (10)	C40—C35—C41	127.3 (6)
C13—C14—C15	120.4 (10)	C35—C36—C37	120.0
F15—C15—C16	121.0 (11)	C35—C36—H36A	120.0
F15—C15—C14	121.5 (10)	C37—C36—H36A	120.0
C16—C15—C14	117.5 (10)	C36—C37—C38	121.5 (4)
F16—C16—C15	120.3 (11)	C36—C37—H37A	119.2
F16—C16—C17	117.7 (11)	C38—C37—H37A	119.2
C15—C16—C17	122.0 (11)	C39—C38—C37	118.5 (4)
F17—C17—C12	119.5 (9)	C39—C38—H38A	120.8
F17—C17—C16	118.7 (10)	C37—C38—H38A	120.8
C12—C17—C16	121.8 (10)	C38—C39—C40	120.0
C18—O3—Ta2	134.5 (6)	C38—C39—H39A	120.0
O3—C18—C23	122.9 (9)	C40—C39—H39A	120.0
O3—C18—C19	121.5 (9)	C39—C40—C35	121.5 (4)
C23—C18—C19	115.5 (9)	C39—C40—H40A	119.2
F19—C19—C20	118.3 (9)	C35—C40—H40A	119.2
F19—C19—C18	119.5 (8)	C35—C41—H41A	109.5
C20—C19—C18	122.2 (9)	C35—C41—H41B	109.5
F20—C20—C21	121.2 (9)	H41A—C41—H41B	109.5
F20—C20—C19	119.0 (9)	C35—C41—H41C	109.5
C21—C20—C19	119.8 (10)	H41A—C41—H41C	109.5
F21—C21—C20	120.5 (9)	H41B—C41—H41C	109.5