metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages m71-m72

Crystal structure of bis­­(η5-cyclo­penta­dien­yl)(1,4-di-tert-butyl­buta-1-en-3-yn-1-yl)zirconium(IV) μ2-hydroxido-bis­­[tris­(penta­fluoro­phen­yl)borate]

CROSSMARK_Color_square_no_text.svg

aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St. 28, 119991 Moscow, Russian Federation, and bLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: uwe.rosenthal@catalysis.de

Edited by M. Nieger, University of Helsinki, Finland (Received 15 December 2014; accepted 23 February 2015; online 28 February 2015)

Alkyl zirconocene cations have been of considerable inter­est as reactive species in many polymerization processes. In the crystal structure of the title compound, [Zr(C12H19)(C5H5)2](C36HB2F30O), the [Zr(C5H5)2((t-Bu)C=C(H)—C2(t-Bu))]+ cation displays a buta-1-en-3-yne ligand side-on coordinated to a typical bent zirconocene [centroid(cp)—Zr—centroid(cp) = 131.4 (3)°, Zr—C(buta-1-en-3-yne) = 2.255 (3), 2.597 (3) and 2.452 (2) Å]. In the [HO(B(C6F5)3)2] anion, intra­molecular O—H⋯F hydrogen bonds are observed. One tert-butyl group in the complex cation is disordered over two sets of sites with occupancies 0.701(4):0.299(4).

1. Related literature

For examples of the coordination of a buta-en-yne ligand to a group IV transition metal atom, see: Erker et al. (2004[Erker, G., Venne-Dunker, S., Kehr, G., Kleigrewe, N., Fröhlich, R., Mück-Lichtenfeld, C. & Grimme, S. (2004). Organometallics, 23, 4391-4395.]); Ahlers, Temme, Erker, Fröhlich & Fox (1997[Ahlers, W., Temme, B., Erker, G., Fröhlich, R. & Fox, T. (1997). J. Organomet. Chem. 527, 191-201.]). For complexation of a buta-1-en-3-yne as a bridging ligand between two metallocenes, see: Ahlers, Temme, Erker, Fröhlich & Zippel (1997[Ahlers, W., Temme, B., Erker, G., Fröhlich, R. & Zippel, F. (1997). Organometallics, 16, 1440-1444.]); Burlakov et al. (2010[Burlakov, V. V., Beweries, T., Kaleta, K., Bogdanov, V. S., Arndt, P., Baumann, W., Spannenberg, A., Shur, V. B. & Rosenthal, U. (2010). Organometallics, 29, 2367-2371.]). For an example of the structure of the hydroxyl borate anion and its formation, see: Liptau et al. (2004[Liptau, P., Neumann, M., Erker, G., Kehr, G., Fröhlich, R. & Grimme, S. (2004). Organometallics, 23, 21-25.]). Stoichimetric reactions of alkyl­zirconocene complexes with B(C6F5)3 have been investigated and different reaction modes (e.g. C—C bond coupling or cleavage) and compounds exhibiting inter­esting structural features have been obtained, see: Ahlers, Temme, Erker, Fröhlich & Zippel (1997[Ahlers, W., Temme, B., Erker, G., Fröhlich, R. & Zippel, F. (1997). Organometallics, 16, 1440-1444.]); Burlakov et al. (2004[Burlakov, V. V., Arndt, P., Baumann, W., Spannenberg, A. & Rosenthal, U. (2004). Organometallics, 23, 5188-5192.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Zr(C12H19)(C5H5)2](C36HB2F30O)

  • Mr = 1425.66

  • Triclinic, [P \overline 1]

  • a = 12.8896 (5) Å

  • b = 13.6334 (5) Å

  • c = 16.5466 (6) Å

  • α = 86.730 (3)°

  • β = 75.389 (3)°

  • γ = 77.581 (3)°

  • V = 2747.84 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.35 mm−1

  • T = 200 K

  • 0.25 × 0.25 × 0.17 mm

2.2. Data collection

  • Stoe IPDS II diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.810, Tmax = 0.966

  • 47172 measured reflections

  • 13119 independent reflections

  • 8407 reflections with I > 2σ(I)

  • Rint = 0.040

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.083

  • S = 0.84

  • 13119 reflections

  • 820 parameters

  • 27 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯F1 0.76 (3) 2.10 (3) 2.722 (2) 139 (2)
O1—H1⋯F30 0.76 (3) 2.08 (3) 2.723 (2) 142 (2)

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2014.

Supporting information


Synthesis and crystallization top

B(C6F5)3 (0.376 g, 0.73 mmol) was dissolved in 20 ml of warm (60°C) n-hexane under Ar, and the obtained solution was added to Cp2Zr[(t-Bu)C4(t-Bu] (0.282 g, 0.73 mmol) in 10 ml of n-hexane. At once an orange precipitate was formed, which was separated from the mother liquor by filtration, washed with n-hexane, and dried in vacuum. Benzene (5 ml) was added and after one day at RT yellow crystals of the title complex had formed. Yield : 0.187 g (18%); m.p. 150-152°C (dec.) under Ar. Anal. Calcd for C58H30B2F30OZr: C, 48.86; H, 2.21%. Found: C, 47.66; H, 2.23%. 1H NMR (300 MHz, C6D6, 297 K): δ = 0.84 (s, 9H, t-Bu); 1.25 (s, 9H, t-Bu); 5.63 (s, 5H, Cp); 5.63 (s, 5H, Cp) ppm; the signals of C=CH and OH were not detected. 13C NMR (75 MHz, C6D6, 297 K): δ = 29.0, 31.3 (t-Bu); 113.7, 114.8 (Cp) ppm; other signals have not been found because of poor solubility. Crystals suitable for X–ray crystal structure analysis were obtained from a saturated n-hexane solution at RT after one day.

Refinement top

H1 and H2 could be found from the difference Fourier map and were refined freely. All other H atoms were placed in idealized positions with d(C—H) = 0.95 Å (CH), 0.98 Å (CH3) and refined using a riding model with Uiso(H) fixed at 1.2 Ueq(C) for CH and 1.5 Ueq(C) for CH3. One t-butyl group is disordered over two sites with occupancies 0.701 (4):0.299 (4). SADI and DANG instructions were used to improve the geometry of the disordered t-butyl group. Additionally, the isotropic displacement parameters of C10A, C11A, C12A, C10B, C11B and C12B were restrained to be equal (SIMU). SADI restraint was also used for the ordered t-butyl group and AFIX 56 for the Cp rings.

Related literature top

For examples of the coordination of a butaenyne ligand to a group IV transition metal atom, see: Erker et al. (2004); Ahlers, Temme, Erker, Fröhlich & Fox (1997). For complexation of a buta-1-en-3-yne as a bridging ligand between two metallocenes, see: Ahlers, Temme, Erker, Fröhlich & Zippel (1997); Burlakov et al. (2010). For an example of the structure of the hydroxyl borate anion and its formation, see: Liptau et al. (2004). Stoichimetric reactions of alkylzirconocene complexes with B(C6F5)3 have been investigated and different reaction modes (e.g. C—C bond coupling or cleavage) and compounds exhibiting interesting structural features have been obtained, see: Ahlers, Temme, Erker, Fröhlich & Zippel (1997); Burlakov et al. (2004).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. : Ball and stick representation of the molecular structure of the title compound. Zr, B, F, O atoms and C1—C4 are labelled. The minor occupied part of the disordered t-butyl group is shown with open lines. Hydrogen atoms of the cyclopentadienyl ligands and the t-butyl groups are omitted for clarity.
[Figure 2] Fig. 2. : Molecular structure of the cation with labelling and displacement ellipsoids drawn at 30% probability level. Hydrogen atoms (except H2) and the minor occupied atoms of the disordered t-butyl group are omitted for clarity.
[Figure 3] Fig. 3. : Molecular structure of the anion with labelling of all non-carbon atoms and displacement ellipsoids drawn at 30% probability level. Hydrogen bonds are shown with dotted lines.
Bis(η5-cyclopentadienyl)(1,4-di-tert-butylbuta-1-en-3-yn-1-yl)zirconium(IV) µ2-hydroxido-bis[tris(pentafluorophenyl)borate] top
Crystal data top
[Zr(C12H19)(C5H5)2](C36HB2F30O)Z = 2
Mr = 1425.66F(000) = 1412
Triclinic, P1Dx = 1.723 Mg m3
a = 12.8896 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.6334 (5) ÅCell parameters from 6318 reflections
c = 16.5466 (6) Åθ = 1.6–28.4°
α = 86.730 (3)°µ = 0.35 mm1
β = 75.389 (3)°T = 200 K
γ = 77.581 (3)°Prism, yellow
V = 2747.84 (18) Å30.25 × 0.25 × 0.17 mm
Data collection top
Stoe IPDS II
diffractometer
13119 independent reflections
Radiation source: fine-focus sealed tube8407 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 28.0°, θmin = 1.5°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
h = 1616
Tmin = 0.810, Tmax = 0.966k = 1717
47172 measured reflectionsl = 2119
Refinement top
Refinement on F227 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0453P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max = 0.001
13119 reflectionsΔρmax = 0.62 e Å3
820 parametersΔρmin = 0.41 e Å3
Crystal data top
[Zr(C12H19)(C5H5)2](C36HB2F30O)γ = 77.581 (3)°
Mr = 1425.66V = 2747.84 (18) Å3
Triclinic, P1Z = 2
a = 12.8896 (5) ÅMo Kα radiation
b = 13.6334 (5) ŵ = 0.35 mm1
c = 16.5466 (6) ÅT = 200 K
α = 86.730 (3)°0.25 × 0.25 × 0.17 mm
β = 75.389 (3)°
Data collection top
Stoe IPDS II
diffractometer
13119 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2005)
8407 reflections with I > 2σ(I)
Tmin = 0.810, Tmax = 0.966Rint = 0.040
47172 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03727 restraints
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.62 e Å3
13119 reflectionsΔρmin = 0.41 e Å3
820 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
B10.62689 (19)0.20536 (17)0.29996 (15)0.0268 (5)
B20.79348 (19)0.29432 (18)0.18106 (15)0.0272 (5)
C10.9852 (2)0.27187 (19)0.74447 (15)0.0425 (6)
C20.9592 (2)0.18318 (19)0.75685 (17)0.0409 (6)
C30.8706 (2)0.15060 (19)0.73591 (16)0.0422 (6)
C40.7936 (2)0.1297 (2)0.71818 (18)0.0510 (7)
C51.0792 (2)0.30077 (18)0.77204 (15)0.0408 (6)
C61.0966 (3)0.4026 (3)0.7357 (3)0.0824 (12)
H6A1.15720.42060.75340.124*
H6B1.02960.45340.75570.124*
H6C1.11430.39960.67460.124*
C71.0480 (3)0.3083 (3)0.86594 (19)0.0805 (11)
H7A1.03160.24440.89020.121*
H7B0.98310.36210.88350.121*
H7C1.10890.32320.88510.121*
C81.1847 (3)0.2256 (3)0.7420 (3)0.1003 (15)
H8A1.24320.24550.76100.150*
H8B1.20390.22320.68080.150*
H8C1.17550.15910.76460.150*
C90.7083 (2)0.0823 (2)0.70203 (19)0.0591 (8)
C10A0.6103 (4)0.0946 (4)0.7771 (3)0.0799 (14)*0.701 (4)
H10A0.55420.06280.76560.120*0.701 (4)
H10B0.63350.06280.82600.120*0.701 (4)
H10C0.57990.16630.78810.120*0.701 (4)
C11A0.6625 (5)0.1351 (4)0.6285 (3)0.0829 (15)*0.701 (4)
H11A0.60610.10210.61910.124*0.701 (4)
H11B0.63050.20590.64230.124*0.701 (4)
H11C0.72220.13050.57770.124*0.701 (4)
C12A0.7591 (5)0.0252 (4)0.6773 (4)0.1011 (17)*0.701 (4)
H12A0.70350.05800.66630.152*0.701 (4)
H12B0.81880.02710.62670.152*0.701 (4)
H12C0.78830.06050.72270.152*0.701 (4)
C10B0.5924 (7)0.1386 (9)0.7394 (8)0.083 (2)*0.299 (4)
H10D0.54010.10310.72630.124*0.299 (4)
H10E0.58030.14260.80010.124*0.299 (4)
H10F0.58190.20660.71590.124*0.299 (4)
C11B0.7348 (12)0.0506 (11)0.6129 (5)0.098 (3)*0.299 (4)
H11D0.67690.01940.60400.147*0.299 (4)
H11E0.74020.10950.57650.147*0.299 (4)
H11F0.80490.00210.59980.147*0.299 (4)
C12B0.7181 (11)0.0169 (7)0.7545 (8)0.089 (2)*0.299 (4)
H12D0.66370.05390.74750.134*0.299 (4)
H12E0.79180.05840.73530.134*0.299 (4)
H12F0.70490.00050.81360.134*0.299 (4)
C130.66787 (14)0.36548 (12)0.79695 (12)0.0517 (7)
H130.62720.31450.81510.062*
C140.74940 (15)0.38772 (13)0.83266 (10)0.0475 (7)
H140.77280.35420.87890.057*
C150.78976 (13)0.46886 (13)0.78714 (12)0.0479 (7)
H150.84490.49910.79760.058*
C160.73318 (15)0.49676 (12)0.72329 (11)0.0496 (7)
H160.74390.54900.68350.060*
C170.65784 (14)0.43287 (15)0.72935 (11)0.0517 (7)
H170.60930.43490.69430.062*
C180.9270 (2)0.41749 (15)0.56372 (13)0.0699 (10)
H180.93890.48190.57300.084*
C190.83144 (17)0.39720 (14)0.54610 (13)0.0617 (8)
H190.76810.44570.54150.074*
C200.84714 (16)0.29177 (15)0.53661 (13)0.0552 (7)
H200.79620.25730.52450.066*
C210.95243 (17)0.24689 (14)0.54838 (12)0.0585 (8)
H210.98420.17710.54550.070*
C221.00180 (14)0.3246 (2)0.56513 (12)0.0743 (11)
H221.07240.31590.57550.089*
C230.53417 (16)0.27195 (15)0.37623 (13)0.0259 (4)
C240.56643 (17)0.31399 (16)0.43748 (13)0.0293 (5)
C250.49734 (19)0.36692 (17)0.50575 (14)0.0351 (5)
C260.38647 (19)0.37978 (17)0.51604 (14)0.0369 (5)
C270.34887 (17)0.33839 (16)0.45860 (14)0.0328 (5)
C280.42095 (17)0.28547 (15)0.39120 (13)0.0283 (5)
C290.67605 (17)0.10434 (15)0.34827 (13)0.0290 (5)
C300.77542 (18)0.08198 (16)0.36996 (14)0.0322 (5)
C310.8078 (2)0.00110 (18)0.41655 (16)0.0416 (6)
C320.7388 (2)0.06633 (17)0.44457 (16)0.0440 (6)
C330.6386 (2)0.04764 (17)0.42578 (15)0.0394 (6)
C340.60956 (18)0.03622 (16)0.37984 (14)0.0314 (5)
C350.57823 (16)0.18643 (16)0.22220 (13)0.0286 (5)
C360.59296 (18)0.09457 (16)0.18300 (14)0.0333 (5)
C370.5508 (2)0.08297 (19)0.11677 (15)0.0409 (6)
C380.4893 (2)0.1647 (2)0.08566 (16)0.0435 (6)
C390.47201 (19)0.25690 (19)0.12106 (15)0.0388 (5)
C400.51676 (17)0.26529 (16)0.18678 (14)0.0306 (5)
C410.79519 (17)0.21253 (16)0.11253 (13)0.0292 (5)
C420.84955 (18)0.11357 (16)0.11741 (14)0.0324 (5)
C430.8606 (2)0.04069 (17)0.06001 (16)0.0400 (6)
C440.8142 (2)0.06373 (19)0.00607 (16)0.0455 (6)
C450.7565 (2)0.15938 (19)0.01305 (14)0.0400 (6)
C460.74802 (18)0.23080 (16)0.04529 (14)0.0327 (5)
C470.74840 (17)0.41262 (16)0.15988 (13)0.0291 (5)
C480.67159 (18)0.48323 (16)0.21216 (14)0.0325 (5)
C490.64114 (19)0.58268 (17)0.19104 (17)0.0398 (6)
C500.6879 (2)0.61662 (17)0.11353 (19)0.0467 (6)
C510.7663 (2)0.55051 (19)0.05963 (16)0.0452 (6)
C520.79564 (19)0.45291 (17)0.08375 (15)0.0366 (5)
C530.91714 (17)0.28909 (15)0.19566 (13)0.0281 (4)
C541.01596 (18)0.25210 (16)0.13889 (14)0.0335 (5)
C551.11764 (18)0.24930 (17)0.15358 (17)0.0395 (6)
C561.12492 (19)0.28574 (18)0.22648 (17)0.0405 (6)
C571.0302 (2)0.32661 (18)0.28417 (16)0.0385 (5)
C580.93044 (17)0.32780 (16)0.26670 (14)0.0312 (5)
F10.67535 (10)0.30374 (11)0.43197 (8)0.0391 (3)
F20.53833 (13)0.40589 (12)0.56093 (9)0.0520 (4)
F30.31647 (13)0.43285 (12)0.58047 (9)0.0563 (4)
F40.23980 (10)0.35074 (10)0.46769 (9)0.0447 (4)
F50.37404 (10)0.24591 (10)0.34052 (8)0.0384 (3)
F60.84787 (10)0.14335 (10)0.34862 (9)0.0401 (3)
F70.90530 (13)0.01638 (12)0.43567 (11)0.0603 (4)
F80.76925 (15)0.14715 (11)0.48968 (11)0.0651 (5)
F90.57076 (13)0.11164 (11)0.45179 (10)0.0538 (4)
F100.50912 (11)0.05135 (10)0.36506 (9)0.0403 (3)
F110.65509 (11)0.01120 (9)0.20768 (9)0.0411 (3)
F120.57139 (15)0.00692 (12)0.08071 (10)0.0599 (4)
F130.44963 (15)0.15406 (14)0.02003 (10)0.0652 (5)
F140.41377 (13)0.33750 (12)0.09076 (10)0.0556 (4)
F150.49879 (11)0.35877 (9)0.21779 (8)0.0370 (3)
F160.89746 (11)0.08421 (9)0.18083 (9)0.0406 (3)
F170.91750 (13)0.05302 (10)0.06875 (10)0.0570 (4)
F180.82371 (17)0.00562 (13)0.06316 (11)0.0703 (5)
F190.70551 (15)0.18250 (12)0.07546 (9)0.0591 (4)
F200.68685 (11)0.32214 (10)0.03376 (8)0.0402 (3)
F210.62084 (11)0.45871 (9)0.29049 (8)0.0379 (3)
F220.56761 (12)0.64748 (10)0.24648 (11)0.0551 (4)
F230.65937 (16)0.71307 (11)0.09263 (12)0.0713 (5)
F240.81554 (16)0.58198 (12)0.01608 (11)0.0698 (5)
F250.87523 (12)0.39252 (10)0.02851 (9)0.0485 (4)
F261.01811 (11)0.21525 (11)0.06457 (8)0.0436 (3)
F271.20962 (11)0.21015 (11)0.09655 (11)0.0557 (4)
F281.22255 (12)0.28281 (12)0.24214 (11)0.0591 (4)
F291.03531 (13)0.36563 (13)0.35548 (10)0.0558 (4)
F300.84025 (11)0.37121 (10)0.32578 (8)0.0401 (3)
O10.71908 (12)0.26558 (11)0.26572 (10)0.0268 (3)
Zr10.84257 (2)0.32484 (2)0.68602 (2)0.03081 (6)
H10.733 (2)0.2889 (19)0.3016 (16)0.034 (8)*
H21.002 (3)0.128 (2)0.782 (2)0.076 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0244 (11)0.0262 (11)0.0289 (12)0.0044 (9)0.0053 (9)0.0019 (10)
B20.0282 (12)0.0297 (12)0.0230 (11)0.0063 (9)0.0046 (9)0.0017 (9)
C10.0434 (14)0.0499 (14)0.0320 (13)0.0175 (11)0.0031 (11)0.0078 (11)
C20.0413 (13)0.0364 (13)0.0460 (15)0.0085 (11)0.0133 (11)0.0039 (11)
C30.0459 (14)0.0430 (14)0.0399 (14)0.0163 (11)0.0089 (11)0.0001 (11)
C40.0512 (16)0.0533 (16)0.0495 (16)0.0141 (13)0.0085 (13)0.0127 (13)
C50.0407 (13)0.0459 (14)0.0378 (13)0.0111 (11)0.0106 (11)0.0049 (11)
C60.076 (2)0.082 (2)0.116 (3)0.050 (2)0.051 (2)0.029 (2)
C70.092 (3)0.120 (3)0.0457 (18)0.055 (2)0.0184 (18)0.0064 (19)
C80.0468 (19)0.108 (3)0.148 (4)0.0011 (19)0.025 (2)0.065 (3)
C90.0671 (19)0.0606 (18)0.0601 (19)0.0289 (15)0.0185 (15)0.0140 (15)
C130.0380 (14)0.0508 (16)0.0553 (17)0.0099 (12)0.0110 (12)0.0091 (13)
C140.0481 (15)0.0481 (15)0.0373 (14)0.0008 (12)0.0005 (12)0.0056 (12)
C150.0457 (14)0.0425 (14)0.0514 (16)0.0101 (11)0.0007 (13)0.0124 (12)
C160.0521 (15)0.0378 (14)0.0507 (16)0.0008 (12)0.0061 (13)0.0016 (12)
C170.0350 (13)0.0566 (16)0.0587 (18)0.0051 (12)0.0119 (12)0.0148 (14)
C180.107 (3)0.068 (2)0.0350 (15)0.046 (2)0.0052 (17)0.0036 (14)
C190.074 (2)0.0589 (18)0.0399 (15)0.0079 (15)0.0128 (15)0.0104 (13)
C200.0660 (19)0.0672 (19)0.0375 (14)0.0172 (15)0.0198 (13)0.0026 (13)
C210.0674 (19)0.0608 (18)0.0311 (14)0.0161 (15)0.0073 (13)0.0004 (13)
C220.0392 (15)0.161 (4)0.0248 (13)0.034 (2)0.0023 (12)0.0045 (18)
C230.0281 (10)0.0251 (10)0.0259 (10)0.0073 (8)0.0078 (8)0.0020 (8)
C240.0273 (10)0.0323 (11)0.0275 (11)0.0065 (8)0.0047 (9)0.0009 (9)
C250.0433 (13)0.0378 (12)0.0262 (11)0.0128 (10)0.0075 (10)0.0047 (9)
C260.0396 (13)0.0321 (11)0.0304 (12)0.0040 (10)0.0051 (10)0.0048 (9)
C270.0247 (10)0.0315 (11)0.0371 (12)0.0041 (9)0.0007 (9)0.0048 (9)
C280.0285 (10)0.0284 (11)0.0295 (11)0.0069 (8)0.0092 (9)0.0016 (9)
C290.0314 (11)0.0277 (11)0.0259 (11)0.0039 (8)0.0044 (9)0.0038 (9)
C300.0324 (11)0.0310 (11)0.0317 (11)0.0044 (9)0.0068 (9)0.0001 (9)
C310.0402 (13)0.0392 (13)0.0438 (14)0.0023 (10)0.0164 (11)0.0015 (11)
C320.0561 (16)0.0296 (12)0.0404 (14)0.0006 (11)0.0114 (12)0.0091 (10)
C330.0508 (15)0.0296 (11)0.0340 (12)0.0104 (10)0.0021 (11)0.0012 (10)
C340.0316 (11)0.0322 (11)0.0296 (11)0.0057 (9)0.0060 (9)0.0036 (9)
C350.0259 (10)0.0310 (11)0.0286 (11)0.0072 (8)0.0043 (9)0.0033 (9)
C360.0358 (12)0.0303 (11)0.0338 (12)0.0085 (9)0.0066 (10)0.0031 (9)
C370.0457 (14)0.0435 (14)0.0365 (13)0.0166 (11)0.0066 (11)0.0139 (11)
C380.0430 (14)0.0616 (17)0.0336 (13)0.0150 (12)0.0178 (11)0.0094 (12)
C390.0348 (12)0.0491 (14)0.0335 (12)0.0054 (10)0.0133 (10)0.0003 (11)
C400.0291 (11)0.0318 (11)0.0308 (11)0.0061 (9)0.0062 (9)0.0052 (9)
C410.0288 (10)0.0303 (11)0.0270 (11)0.0066 (8)0.0027 (9)0.0035 (9)
C420.0332 (11)0.0341 (12)0.0288 (11)0.0080 (9)0.0040 (9)0.0040 (9)
C430.0400 (13)0.0323 (12)0.0415 (14)0.0039 (10)0.0005 (11)0.0099 (10)
C440.0559 (16)0.0429 (14)0.0360 (14)0.0139 (12)0.0011 (12)0.0174 (11)
C450.0505 (14)0.0475 (14)0.0263 (12)0.0170 (11)0.0105 (11)0.0048 (10)
C460.0370 (12)0.0319 (11)0.0283 (11)0.0087 (9)0.0048 (9)0.0011 (9)
C470.0309 (11)0.0293 (11)0.0299 (11)0.0089 (9)0.0102 (9)0.0015 (9)
C480.0334 (11)0.0311 (11)0.0357 (12)0.0081 (9)0.0121 (10)0.0021 (9)
C490.0354 (12)0.0297 (12)0.0558 (16)0.0027 (9)0.0159 (11)0.0053 (11)
C500.0530 (15)0.0264 (12)0.0660 (18)0.0074 (11)0.0272 (14)0.0097 (12)
C510.0579 (16)0.0403 (13)0.0418 (14)0.0178 (12)0.0168 (12)0.0135 (11)
C520.0402 (13)0.0342 (12)0.0351 (12)0.0090 (10)0.0071 (10)0.0007 (10)
C530.0307 (10)0.0251 (10)0.0289 (11)0.0082 (8)0.0064 (9)0.0007 (8)
C540.0347 (12)0.0308 (11)0.0345 (12)0.0091 (9)0.0052 (10)0.0017 (9)
C550.0275 (11)0.0348 (12)0.0523 (15)0.0063 (9)0.0029 (10)0.0013 (11)
C560.0302 (12)0.0384 (13)0.0593 (17)0.0121 (10)0.0196 (11)0.0052 (12)
C570.0418 (13)0.0424 (13)0.0398 (13)0.0182 (11)0.0180 (11)0.0023 (11)
C580.0305 (11)0.0322 (11)0.0317 (12)0.0112 (9)0.0053 (9)0.0005 (9)
F10.0294 (7)0.0595 (8)0.0317 (7)0.0124 (6)0.0090 (5)0.0080 (6)
F20.0571 (9)0.0655 (10)0.0360 (8)0.0182 (8)0.0071 (7)0.0207 (7)
F30.0502 (9)0.0613 (10)0.0441 (8)0.0036 (7)0.0105 (7)0.0217 (7)
F40.0251 (6)0.0481 (8)0.0534 (9)0.0038 (6)0.0001 (6)0.0027 (7)
F50.0288 (6)0.0502 (8)0.0395 (7)0.0119 (6)0.0101 (6)0.0055 (6)
F60.0315 (7)0.0410 (7)0.0508 (8)0.0096 (6)0.0156 (6)0.0071 (6)
F70.0478 (9)0.0584 (10)0.0765 (12)0.0018 (7)0.0328 (8)0.0160 (8)
F80.0813 (12)0.0402 (8)0.0711 (11)0.0026 (8)0.0275 (9)0.0239 (8)
F90.0671 (10)0.0394 (8)0.0545 (9)0.0230 (7)0.0066 (8)0.0117 (7)
F100.0374 (7)0.0407 (7)0.0463 (8)0.0156 (6)0.0110 (6)0.0044 (6)
F110.0515 (8)0.0279 (7)0.0414 (8)0.0040 (6)0.0095 (6)0.0060 (6)
F120.0816 (12)0.0508 (9)0.0539 (10)0.0201 (8)0.0184 (9)0.0239 (8)
F130.0729 (11)0.0857 (12)0.0507 (10)0.0167 (9)0.0363 (9)0.0176 (9)
F140.0563 (9)0.0646 (10)0.0487 (9)0.0023 (8)0.0310 (8)0.0012 (8)
F150.0427 (7)0.0303 (7)0.0386 (7)0.0013 (6)0.0155 (6)0.0034 (6)
F160.0434 (8)0.0339 (7)0.0436 (8)0.0021 (6)0.0137 (6)0.0019 (6)
F170.0633 (10)0.0335 (8)0.0652 (11)0.0039 (7)0.0079 (8)0.0169 (7)
F180.1024 (14)0.0572 (10)0.0512 (10)0.0145 (10)0.0137 (10)0.0310 (8)
F190.0895 (12)0.0646 (10)0.0352 (8)0.0253 (9)0.0287 (8)0.0044 (7)
F200.0495 (8)0.0391 (7)0.0352 (7)0.0069 (6)0.0183 (6)0.0004 (6)
F210.0392 (7)0.0352 (7)0.0349 (7)0.0058 (6)0.0008 (6)0.0078 (6)
F220.0471 (8)0.0335 (7)0.0785 (11)0.0037 (6)0.0113 (8)0.0148 (7)
F230.0904 (13)0.0339 (8)0.0910 (14)0.0052 (8)0.0359 (11)0.0204 (8)
F240.0966 (14)0.0562 (10)0.0526 (10)0.0241 (9)0.0099 (9)0.0259 (8)
F250.0550 (9)0.0454 (8)0.0354 (8)0.0113 (7)0.0071 (7)0.0018 (6)
F260.0355 (7)0.0539 (8)0.0371 (8)0.0088 (6)0.0011 (6)0.0134 (6)
F270.0276 (7)0.0553 (9)0.0757 (11)0.0061 (6)0.0032 (7)0.0135 (8)
F280.0360 (8)0.0666 (10)0.0839 (12)0.0153 (7)0.0278 (8)0.0012 (9)
F290.0571 (9)0.0772 (11)0.0469 (9)0.0301 (8)0.0231 (8)0.0057 (8)
F300.0365 (7)0.0507 (8)0.0343 (7)0.0152 (6)0.0026 (6)0.0134 (6)
O10.0281 (8)0.0298 (8)0.0243 (8)0.0091 (6)0.0065 (6)0.0033 (6)
Zr10.02742 (11)0.03248 (11)0.03073 (12)0.00538 (8)0.00494 (8)0.00140 (9)
Geometric parameters (Å, º) top
B1—O11.560 (3)C20—C211.4200
B1—C351.622 (3)C20—Zr12.522 (2)
B1—C291.641 (3)C20—H200.9500
B1—C231.658 (3)C21—C221.4200
B2—O11.567 (3)C21—Zr12.5147 (19)
B2—C411.628 (3)C21—H210.9500
B2—C471.642 (3)C22—Zr12.4779 (18)
B2—C531.658 (3)C22—H220.9500
C1—C21.314 (3)C23—C241.382 (3)
C1—C51.529 (4)C23—C281.390 (3)
C1—Zr12.255 (3)C24—F11.361 (2)
C2—C31.434 (4)C24—C251.378 (3)
C2—Zr12.597 (3)C25—F21.347 (3)
C2—H20.96 (3)C25—C261.369 (3)
C3—C41.197 (4)C26—F31.340 (2)
C3—Zr12.452 (2)C26—C271.367 (4)
C4—C91.473 (4)C27—F41.350 (2)
C4—Zr12.855 (3)C27—C281.381 (3)
C5—C81.504 (4)C28—F51.344 (3)
C5—C71.507 (4)C29—C301.383 (3)
C5—C61.520 (4)C29—C341.390 (3)
C6—H6A0.9800C30—F61.354 (3)
C6—H6B0.9800C30—C311.382 (3)
C6—H6C0.9800C31—F71.342 (3)
C7—H7A0.9800C31—C321.372 (4)
C7—H7B0.9800C32—F81.339 (3)
C7—H7C0.9800C32—C331.371 (4)
C8—H8A0.9800C33—F91.344 (3)
C8—H8B0.9800C33—C341.373 (3)
C8—H8C0.9800C34—F101.348 (3)
C9—C11B1.494 (7)C35—C401.387 (3)
C9—C12A1.505 (5)C35—C361.398 (3)
C9—C10B1.516 (7)C36—F111.349 (3)
C9—C10A1.519 (5)C36—C371.370 (3)
C9—C11A1.558 (5)C37—F121.339 (3)
C9—C12B1.564 (7)C37—C381.377 (4)
C10A—H10A0.9800C38—F131.339 (3)
C10A—H10B0.9800C38—C391.367 (4)
C10A—H10C0.9800C39—F141.340 (3)
C11A—H11A0.9800C39—C401.374 (3)
C11A—H11B0.9800C40—F151.352 (2)
C11A—H11C0.9800C41—C461.384 (3)
C12A—H12A0.9800C41—C421.388 (3)
C12A—H12B0.9800C42—F161.347 (3)
C12A—H12C0.9800C42—C431.374 (3)
C10B—H10D0.9800C43—F171.349 (3)
C10B—H10E0.9800C43—C441.364 (4)
C10B—H10F0.9800C44—F181.340 (3)
C11B—H11D0.9800C44—C451.370 (4)
C11B—H11E0.9800C45—F191.347 (3)
C11B—H11F0.9800C45—C461.378 (3)
C12B—H12D0.9800C46—F201.355 (3)
C12B—H12E0.9800C47—C481.381 (3)
C12B—H12F0.9800C47—C521.392 (3)
C13—C171.4200C48—F211.355 (3)
C13—C141.4200C48—C491.379 (3)
C13—Zr12.4982 (17)C49—F221.347 (3)
C13—H130.9500C49—C501.373 (4)
C14—C151.4200C50—F231.337 (3)
C14—Zr12.5277 (17)C50—C511.369 (4)
C14—H140.9500C51—F241.346 (3)
C15—C161.4200C51—C521.368 (3)
C15—Zr12.5186 (18)C52—F251.347 (3)
C15—H150.9500C53—C581.379 (3)
C16—C171.4200C53—C541.391 (3)
C16—Zr12.4832 (18)C54—F261.346 (3)
C16—H160.9500C54—C551.384 (3)
C17—Zr12.4705 (18)C55—F271.342 (3)
C17—H170.9500C55—C561.362 (4)
C18—C221.4200C56—F281.339 (3)
C18—C191.4200C56—C571.375 (4)
C18—Zr12.4624 (19)C57—F291.343 (3)
C18—H180.9500C57—C581.384 (3)
C19—C201.4200C58—F301.362 (2)
C19—Zr12.4900 (19)O1—H10.76 (3)
C19—H190.9500
O1—B1—C35107.31 (17)F3—C26—C27120.8 (2)
O1—B1—C29109.15 (17)F3—C26—C25120.7 (2)
C35—B1—C29115.91 (18)C27—C26—C25118.5 (2)
O1—B1—C23107.78 (16)F4—C27—C26119.25 (19)
C35—B1—C23113.25 (17)F4—C27—C28119.9 (2)
C29—B1—C23103.14 (17)C26—C27—C28120.8 (2)
O1—B2—C41106.53 (16)F5—C28—C27115.20 (19)
O1—B2—C47108.88 (16)F5—C28—C23121.45 (18)
C41—B2—C47116.31 (19)C27—C28—C23123.3 (2)
O1—B2—C53107.65 (17)C30—C29—C34113.41 (19)
C41—B2—C53111.91 (17)C30—C29—B1127.16 (19)
C47—B2—C53105.27 (17)C34—C29—B1119.08 (19)
C2—C1—C5124.4 (3)F6—C30—C31114.6 (2)
C2—C1—Zr189.37 (18)F6—C30—C29121.46 (19)
C5—C1—Zr1146.15 (18)C31—C30—C29123.9 (2)
C1—C2—C3128.2 (3)F7—C31—C32120.4 (2)
C1—C2—Zr160.23 (16)F7—C31—C30120.0 (2)
C3—C2—Zr168.00 (15)C32—C31—C30119.6 (2)
C1—C2—H2122 (2)F8—C32—C33120.6 (2)
C3—C2—H2109 (2)F8—C32—C31120.2 (2)
Zr1—C2—H2177 (2)C33—C32—C31119.2 (2)
C4—C3—C2175.8 (3)F9—C33—C32119.9 (2)
C4—C3—Zr196.9 (2)F9—C33—C34120.9 (2)
C2—C3—Zr179.16 (15)C32—C33—C34119.2 (2)
C3—C4—C9167.8 (3)F10—C34—C33116.2 (2)
C3—C4—Zr158.49 (17)F10—C34—C29119.13 (19)
C9—C4—Zr1133.6 (2)C33—C34—C29124.6 (2)
C8—C5—C7111.1 (3)C40—C35—C36112.9 (2)
C8—C5—C6107.9 (3)C40—C35—B1120.82 (18)
C7—C5—C6108.6 (3)C36—C35—B1126.22 (19)
C8—C5—C1111.2 (2)F11—C36—C37115.9 (2)
C7—C5—C1108.2 (2)F11—C36—C35120.2 (2)
C6—C5—C1109.9 (2)C37—C36—C35123.8 (2)
C5—C6—H6A109.5F12—C37—C36120.4 (2)
C5—C6—H6B109.5F12—C37—C38119.7 (2)
H6A—C6—H6B109.5C36—C37—C38119.9 (2)
C5—C6—H6C109.5F13—C38—C39120.7 (2)
H6A—C6—H6C109.5F13—C38—C37120.0 (2)
H6B—C6—H6C109.5C39—C38—C37119.3 (2)
C5—C7—H7A109.5F14—C39—C38120.0 (2)
C5—C7—H7B109.5F14—C39—C40121.0 (2)
H7A—C7—H7B109.5C38—C39—C40118.9 (2)
C5—C7—H7C109.5F15—C40—C39116.06 (19)
H7A—C7—H7C109.5F15—C40—C35118.8 (2)
H7B—C7—H7C109.5C39—C40—C35125.2 (2)
C5—C8—H8A109.5C46—C41—C42113.3 (2)
C5—C8—H8B109.5C46—C41—B2126.49 (19)
H8A—C8—H8B109.5C42—C41—B2120.2 (2)
C5—C8—H8C109.5F16—C42—C43115.7 (2)
H8A—C8—H8C109.5F16—C42—C41119.9 (2)
H8B—C8—H8C109.5C43—C42—C41124.3 (2)
C4—C9—C11B111.2 (6)F17—C43—C44120.2 (2)
C4—C9—C12A108.3 (3)F17—C43—C42120.1 (2)
C4—C9—C10B113.8 (6)C44—C43—C42119.7 (2)
C11B—C9—C10B117.1 (7)F18—C44—C43121.1 (2)
C4—C9—C10A110.3 (3)F18—C44—C45120.1 (3)
C12A—C9—C10A114.1 (4)C43—C44—C45118.9 (2)
C4—C9—C11A111.2 (3)F19—C45—C44119.9 (2)
C12A—C9—C11A107.6 (4)F19—C45—C46120.2 (2)
C10A—C9—C11A105.2 (4)C44—C45—C46119.9 (2)
C4—C9—C12B103.7 (6)F20—C46—C45115.1 (2)
C11B—C9—C12B106.0 (7)F20—C46—C41121.0 (2)
C10B—C9—C12B103.5 (7)C45—C46—C41123.9 (2)
C9—C10A—H10A109.5C48—C47—C52112.9 (2)
C9—C10A—H10B109.5C48—C47—B2127.54 (19)
H10A—C10A—H10B109.5C52—C47—B2119.34 (19)
C9—C10A—H10C109.5F21—C48—C49114.5 (2)
H10A—C10A—H10C109.5F21—C48—C47121.25 (19)
H10B—C10A—H10C109.5C49—C48—C47124.2 (2)
C9—C11A—H11A109.5F22—C49—C50119.6 (2)
C9—C11A—H11B109.5F22—C49—C48120.6 (2)
H11A—C11A—H11B109.5C50—C49—C48119.8 (2)
C9—C11A—H11C109.5F23—C50—C51121.1 (2)
H11A—C11A—H11C109.5F23—C50—C49120.3 (2)
H11B—C11A—H11C109.5C51—C50—C49118.6 (2)
C9—C12A—H12A109.5F24—C51—C52120.3 (2)
C9—C12A—H12B109.5F24—C51—C50120.0 (2)
H12A—C12A—H12B109.5C52—C51—C50119.7 (2)
C9—C12A—H12C109.5F25—C52—C51116.6 (2)
H12A—C12A—H12C109.5F25—C52—C47118.73 (19)
H12B—C12A—H12C109.5C51—C52—C47124.7 (2)
C9—C10B—H10D109.5C58—C53—C54113.1 (2)
C9—C10B—H10E109.5C58—C53—B2121.19 (18)
H10D—C10B—H10E109.5C54—C53—B2125.7 (2)
C9—C10B—H10F109.5F26—C54—C55115.2 (2)
H10D—C10B—H10F109.5F26—C54—C53121.0 (2)
H10E—C10B—H10F109.5C55—C54—C53123.8 (2)
C9—C11B—H11D109.5F27—C55—C56119.5 (2)
C9—C11B—H11E109.5F27—C55—C54120.4 (2)
H11D—C11B—H11E109.5C56—C55—C54120.1 (2)
C9—C11B—H11F109.5F28—C56—C55120.9 (2)
H11D—C11B—H11F109.5F28—C56—C57120.0 (2)
H11E—C11B—H11F109.5C55—C56—C57119.1 (2)
C9—C12B—H12D109.5F29—C57—C56120.2 (2)
C9—C12B—H12E109.5F29—C57—C58121.0 (2)
H12D—C12B—H12E109.5C56—C57—C58118.7 (2)
C9—C12B—H12F109.5F30—C58—C53119.30 (19)
H12D—C12B—H12F109.5F30—C58—C57115.6 (2)
H12E—C12B—H12F109.5C53—C58—C57125.1 (2)
C17—C13—C14108.0B1—O1—B2140.58 (18)
C17—C13—Zr172.33 (7)B1—O1—H1110.4 (19)
C14—C13—Zr174.73 (7)B2—O1—H1109.0 (19)
C17—C13—H13126.0C1—Zr1—C363.23 (9)
C14—C13—H13126.0C1—Zr1—C18100.98 (9)
Zr1—C13—H13118.8C3—Zr1—C18136.21 (8)
C15—C14—C13108.0C1—Zr1—C17135.79 (7)
C15—C14—Zr173.30 (6)C3—Zr1—C17118.55 (8)
C13—C14—Zr172.45 (7)C18—Zr1—C17101.29 (8)
C15—C14—H14126.0C1—Zr1—C2277.84 (7)
C13—C14—H14126.0C3—Zr1—C22103.64 (9)
Zr1—C14—H14120.1C18—Zr1—C2233.4
C14—C15—C16108.0C17—Zr1—C22134.23 (7)
C14—C15—Zr174.01 (6)C1—Zr1—C16116.49 (8)
C16—C15—Zr172.14 (7)C3—Zr1—C16143.21 (7)
C14—C15—H15126.0C18—Zr1—C1680.53 (7)
C16—C15—H15126.0C17—Zr1—C1633.3
Zr1—C15—H15119.7C22—Zr1—C16112.32 (8)
C17—C16—C15108.0C1—Zr1—C19132.07 (8)
C17—C16—Zr172.85 (7)C3—Zr1—C19131.40 (8)
C15—C16—Zr174.88 (7)C18—Zr1—C1933.3
C17—C16—H16126.0C17—Zr1—C1982.58 (6)
C15—C16—H16126.0C22—Zr1—C1955.1
Zr1—C16—H16118.2C16—Zr1—C1978.42 (6)
C13—C17—C16108.0C1—Zr1—C13110.14 (7)
C13—C17—Zr174.47 (7)C3—Zr1—C1389.50 (7)
C16—C17—Zr173.84 (7)C18—Zr1—C13133.39 (7)
C13—C17—H17126.0C17—Zr1—C1333.2
C16—C17—H17126.0C22—Zr1—C13166.77 (8)
Zr1—C17—H17117.7C16—Zr1—C1354.9
C22—C18—C19108.0C19—Zr1—C13114.67 (6)
C22—C18—Zr173.89 (7)C1—Zr1—C2191.49 (8)
C19—C18—Zr174.41 (8)C3—Zr1—C2183.51 (7)
C22—C18—H18126.0C18—Zr1—C2155.0
C19—C18—H18126.0C17—Zr1—C21132.38 (6)
Zr1—C18—H18117.7C22—Zr1—C2133.0
C20—C19—C18108.0C16—Zr1—C21131.87 (5)
C20—C19—Zr174.79 (8)C19—Zr1—C2154.7
C18—C19—Zr172.28 (7)C13—Zr1—C21151.26 (7)
C20—C19—H19126.0C1—Zr1—C1585.15 (7)
C18—C19—H19126.0C3—Zr1—C15120.69 (7)
Zr1—C19—H19118.8C18—Zr1—C1596.22 (6)
C19—C20—C21108.0C17—Zr1—C1554.8
C19—C20—Zr172.31 (7)C22—Zr1—C15117.67 (7)
C21—C20—Zr173.34 (7)C16—Zr1—C1533.0
C19—C20—H20126.0C19—Zr1—C15107.37 (6)
C21—C20—H20126.0C13—Zr1—C1554.5
Zr1—C20—H20120.2C21—Zr1—C15149.83 (7)
C20—C21—C22108.0C1—Zr1—C20124.24 (8)
C20—C21—Zr173.91 (7)C3—Zr1—C2098.49 (8)
C22—C21—Zr172.06 (7)C18—Zr1—C2054.9
C20—C21—H21126.0C17—Zr1—C2099.78 (6)
C22—C21—H21126.0C22—Zr1—C2054.7
Zr1—C21—H21119.9C16—Zr1—C20108.20 (6)
C18—C22—C21108.0C19—Zr1—C2032.9
C18—C22—Zr172.70 (7)C13—Zr1—C20122.54 (7)
C21—C22—Zr174.90 (8)C21—Zr1—C2032.8
C18—C22—H22126.0C15—Zr1—C20139.66 (6)
C21—C22—H22126.0C1—Zr1—C1481.68 (7)
Zr1—C22—H22118.3C3—Zr1—C1490.97 (7)
C24—C23—C28112.72 (19)C18—Zr1—C14128.86 (6)
C24—C23—B1120.32 (18)C17—Zr1—C1454.7
C28—C23—B1126.75 (19)C22—Zr1—C14145.77 (7)
F1—C24—C25115.3 (2)C16—Zr1—C1454.6
F1—C24—C23118.95 (18)C19—Zr1—C14132.40 (5)
C25—C24—C23125.7 (2)C13—Zr1—C1432.8
F2—C25—C26120.7 (2)C21—Zr1—C14172.66 (6)
F2—C25—C24120.5 (2)C15—Zr1—C1432.7
C26—C25—C24118.8 (2)C20—Zr1—C14153.94 (6)
C5—C1—C2—C3177.6 (2)B1—C35—C36—F111.9 (3)
Zr1—C1—C2—C30.0 (3)C40—C35—C36—C370.3 (3)
C5—C1—C2—Zr1177.6 (3)B1—C35—C36—C37179.3 (2)
C1—C2—C3—Zr10.0 (3)F11—C36—C37—F120.3 (3)
Zr1—C3—C4—C9174.4 (13)C35—C36—C37—F12177.8 (2)
C2—C1—C5—C851.8 (4)F11—C36—C37—C38178.0 (2)
Zr1—C1—C5—C8132.4 (3)C35—C36—C37—C380.5 (4)
C2—C1—C5—C770.5 (3)F12—C37—C38—F130.5 (4)
Zr1—C1—C5—C7105.3 (3)C36—C37—C38—F13178.8 (2)
C2—C1—C5—C6171.1 (3)F12—C37—C38—C39177.7 (2)
Zr1—C1—C5—C613.1 (4)C36—C37—C38—C390.6 (4)
C3—C4—C9—C11B94.7 (15)F13—C38—C39—F140.8 (4)
Zr1—C4—C9—C11B78.7 (6)C37—C38—C39—F14179.0 (2)
C3—C4—C9—C12A31.3 (15)F13—C38—C39—C40178.1 (2)
Zr1—C4—C9—C12A142.1 (3)C37—C38—C39—C400.1 (4)
C3—C4—C9—C10B130.5 (14)F14—C39—C40—F150.3 (3)
Zr1—C4—C9—C10B56.1 (7)C38—C39—C40—F15178.5 (2)
C3—C4—C9—C10A94.3 (14)F14—C39—C40—C35179.9 (2)
Zr1—C4—C9—C10A92.4 (4)C38—C39—C40—C351.0 (4)
C3—C4—C9—C11A149.4 (13)C36—C35—C40—F15178.45 (18)
Zr1—C4—C9—C11A24.0 (4)B1—C35—C40—F150.6 (3)
C3—C4—C9—C12B18.8 (15)C36—C35—C40—C391.1 (3)
Zr1—C4—C9—C12B167.8 (5)B1—C35—C40—C39179.9 (2)
C17—C13—C14—C150.0O1—B2—C41—C46111.3 (2)
Zr1—C13—C14—C1565.19 (7)C47—B2—C41—C4610.2 (3)
C17—C13—C14—Zr165.19 (7)C53—B2—C41—C46131.3 (2)
C13—C14—C15—C160.0O1—B2—C41—C4269.9 (2)
Zr1—C14—C15—C1664.63 (7)C47—B2—C41—C42168.51 (18)
C13—C14—C15—Zr164.63 (7)C53—B2—C41—C4247.5 (2)
C14—C15—C16—C170.0C46—C41—C42—F16178.54 (18)
Zr1—C15—C16—C1765.86 (6)B2—C41—C42—F162.5 (3)
C14—C15—C16—Zr165.86 (6)C46—C41—C42—C432.7 (3)
C14—C13—C17—C160.0B2—C41—C42—C43176.3 (2)
Zr1—C13—C17—C1666.79 (7)F16—C42—C43—F170.6 (3)
C14—C13—C17—Zr166.79 (7)C41—C42—C43—F17178.2 (2)
C15—C16—C17—C130.0F16—C42—C43—C44179.7 (2)
Zr1—C16—C17—C1367.21 (7)C41—C42—C43—C441.4 (4)
C15—C16—C17—Zr167.21 (7)F17—C43—C44—F180.3 (4)
C22—C18—C19—C200.0C42—C43—C44—F18179.9 (2)
Zr1—C18—C19—C2066.83 (7)F17—C43—C44—C45179.7 (2)
C22—C18—C19—Zr166.83 (7)C42—C43—C44—C450.7 (4)
C18—C19—C20—C210.0F18—C44—C45—F192.7 (4)
Zr1—C19—C20—C2165.16 (7)C43—C44—C45—F19176.7 (2)
C18—C19—C20—Zr165.16 (7)F18—C44—C45—C46179.2 (2)
C19—C20—C21—C220.0C43—C44—C45—C461.3 (4)
Zr1—C20—C21—C2264.48 (7)F19—C45—C46—F200.3 (3)
C19—C20—C21—Zr164.48 (7)C44—C45—C46—F20178.4 (2)
C19—C18—C22—C210.0F19—C45—C46—C41178.1 (2)
Zr1—C18—C22—C2167.17 (8)C44—C45—C46—C410.1 (4)
C19—C18—C22—Zr167.17 (8)C42—C41—C46—F20176.43 (18)
C20—C21—C22—C180.0B2—C41—C46—F204.7 (3)
Zr1—C21—C22—C1865.70 (7)C42—C41—C46—C452.0 (3)
C20—C21—C22—Zr165.70 (7)B2—C41—C46—C45176.9 (2)
O1—B1—C23—C2446.7 (2)O1—B2—C47—C4811.0 (3)
C35—B1—C23—C24165.22 (18)C41—B2—C47—C48131.4 (2)
C29—B1—C23—C2468.7 (2)C53—B2—C47—C48104.1 (2)
O1—B1—C23—C28139.0 (2)O1—B2—C47—C52174.3 (2)
C35—B1—C23—C2820.5 (3)C41—B2—C47—C5254.0 (3)
C29—B1—C23—C28105.6 (2)C53—B2—C47—C5270.5 (3)
C28—C23—C24—F1178.08 (18)C52—C47—C48—F21176.8 (2)
B1—C23—C24—F13.0 (3)B2—C47—C48—F211.9 (4)
C28—C23—C24—C251.9 (3)C52—C47—C48—C492.2 (3)
B1—C23—C24—C25177.0 (2)B2—C47—C48—C49177.1 (2)
F1—C24—C25—F21.0 (3)F21—C48—C49—F220.8 (3)
C23—C24—C25—F2179.0 (2)C47—C48—C49—F22178.2 (2)
F1—C24—C25—C26179.50 (19)F21—C48—C49—C50179.3 (2)
C23—C24—C25—C260.5 (3)C47—C48—C49—C500.3 (4)
F2—C25—C26—F31.1 (3)F22—C49—C50—F231.1 (4)
C24—C25—C26—F3178.4 (2)C48—C49—C50—F23179.6 (2)
F2—C25—C26—C27179.7 (2)F22—C49—C50—C51176.9 (2)
C24—C25—C26—C270.8 (3)C48—C49—C50—C511.6 (4)
F3—C26—C27—F40.6 (3)F23—C50—C51—F240.5 (4)
C25—C26—C27—F4179.7 (2)C49—C50—C51—F24178.5 (2)
F3—C26—C27—C28178.6 (2)F23—C50—C51—C52178.4 (3)
C25—C26—C27—C280.6 (3)C49—C50—C51—C520.3 (4)
F4—C27—C28—F52.7 (3)F24—C51—C52—F250.5 (4)
C26—C27—C28—F5178.11 (19)C50—C51—C52—F25178.4 (2)
F4—C27—C28—C23178.12 (18)F24—C51—C52—C47178.7 (2)
C26—C27—C28—C231.1 (3)C50—C51—C52—C472.4 (4)
C24—C23—C28—F5176.94 (18)C48—C47—C52—F25177.3 (2)
B1—C23—C28—F52.3 (3)B2—C47—C52—F251.9 (3)
C24—C23—C28—C272.2 (3)C48—C47—C52—C513.5 (4)
B1—C23—C28—C27176.85 (19)B2—C47—C52—C51178.9 (2)
O1—B1—C29—C3010.9 (3)O1—B2—C53—C5843.2 (2)
C35—B1—C29—C30132.2 (2)C41—B2—C53—C58159.96 (19)
C23—B1—C29—C30103.5 (2)C47—B2—C53—C5872.8 (2)
O1—B1—C29—C34176.40 (18)O1—B2—C53—C54140.4 (2)
C35—B1—C29—C3455.1 (3)C41—B2—C53—C5423.6 (3)
C23—B1—C29—C3469.2 (2)C47—B2—C53—C54103.6 (2)
C34—C29—C30—F6176.21 (19)C58—C53—C54—F26177.27 (19)
B1—C29—C30—F63.2 (3)B2—C53—C54—F260.6 (3)
C34—C29—C30—C311.6 (3)C58—C53—C54—C553.2 (3)
B1—C29—C30—C31174.7 (2)B2—C53—C54—C55179.9 (2)
F6—C30—C31—F71.2 (3)F26—C54—C55—F271.2 (3)
C29—C30—C31—F7179.2 (2)C53—C54—C55—F27178.3 (2)
F6—C30—C31—C32177.4 (2)F26—C54—C55—C56179.3 (2)
C29—C30—C31—C320.6 (4)C53—C54—C55—C561.2 (4)
F7—C31—C32—F81.5 (4)F27—C55—C56—F280.2 (3)
C30—C31—C32—F8179.9 (2)C54—C55—C56—F28179.4 (2)
F7—C31—C32—C33178.5 (2)F27—C55—C56—C57179.4 (2)
C30—C31—C32—C330.1 (4)C54—C55—C56—C571.1 (4)
F8—C32—C33—F90.9 (4)F28—C56—C57—F291.4 (3)
C31—C32—C33—F9179.1 (2)C55—C56—C57—F29178.1 (2)
F8—C32—C33—C34179.6 (2)F28—C56—C57—C58179.4 (2)
C31—C32—C33—C340.4 (4)C55—C56—C57—C581.1 (3)
F9—C33—C34—F101.9 (3)C54—C53—C58—F30176.71 (18)
C32—C33—C34—F10178.6 (2)B2—C53—C58—F300.1 (3)
F9—C33—C34—C29177.8 (2)C54—C53—C58—C573.3 (3)
C32—C33—C34—C291.6 (4)B2—C53—C58—C57179.9 (2)
C30—C29—C34—F10178.12 (19)F29—C57—C58—F300.5 (3)
B1—C29—C34—F104.5 (3)C56—C57—C58—F30178.7 (2)
C30—C29—C34—C332.2 (3)F29—C57—C58—C53179.5 (2)
B1—C29—C34—C33175.8 (2)C56—C57—C58—C531.3 (4)
O1—B1—C35—C4069.8 (2)C35—B1—O1—B216.1 (3)
C29—B1—C35—C40167.98 (18)C29—B1—O1—B2110.2 (3)
C23—B1—C35—C4049.0 (3)C23—B1—O1—B2138.4 (2)
O1—B1—C35—C36109.1 (2)C41—B2—O1—B120.7 (3)
C29—B1—C35—C3613.1 (3)C47—B2—O1—B1105.5 (3)
C23—B1—C35—C36132.1 (2)C53—B2—O1—B1140.9 (2)
C40—C35—C36—F11177.04 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···F10.76 (3)2.10 (3)2.722 (2)139 (2)
O1—H1···F300.76 (3)2.08 (3)2.723 (2)142 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···F10.76 (3)2.10 (3)2.722 (2)139 (2)
O1—H1···F300.76 (3)2.08 (3)2.723 (2)142 (2)
 

Acknowledgements

We would like to thank our technical and analytical staff for assistance. Financial support by the Deutsche Forschungsgemeinschaft (RO 1269/9-1) and the Russian Foundation for Basic Research (project code 15-03-03485) is gratefully acknowledged.

References

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Volume 71| Part 3| March 2015| Pages m71-m72
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