Trichlorido(tetra-hydro-furan){(1,2,3,3a,7a-η)-1-[2-(1-trimethyl-silyl-1H-imidazol-2-yl-κN)-1-methyl-prop-yl]inden-yl}zirconium(IV).

The title compound, [ZrCl(3)(C(19)H(25)N(2)Si)(C(4)H(8)O)], was prepared from bis-(N,N-dimethyl-amido-κN)(2-{2-[(1,2,3,3a,7a-η)-inden-yl]-2-methyl-prop-yl}-1H-imidazolido-κN(1))zirconium(IV) [(C(16)H(16)N(2))Zr(NMe(2))] by reaction with excess Me(3)SiCl in tetra-hydro-furan (THF) at elevated temperature. The crystal studied contained a minor non-merohedral twin contaminant [6.3 (4)%] which was taken into account during the refinement. The coordination polyhedron of the Zr(IV) atom is a distorted octa-hedron [assuming that the five-membered ring of the indenyl group (Cp) occupies one coordination site], with the Cp group and a THF O atom at the apical positions and the three Cl and ligating N atoms at the equatorial positions. The Zr, Si and the methyl-ene C atoms deviate noticeably from the imidazole ring plane [by -0.197 (5), -0.207 (5) and 0.119 (6) Å, respectively]. The THF ligand adopts an envelope conformation.

Related literature

For general practical utility of geometry-constrained complexes, including those derived from group 4 transition metals, see: Erker (2006 ▶); Braunschweig & Breitling (2006 ▶). For the geometric parameters of similar ZrIV complexes, see: Nifant’ev et al. (1998 ▶); Paolucci et al. (2003 ▶); Krut’ko et al. (2004 ▶, 2007 ▶); Enders et al. (1996 ▶); Nie et al. (2008 ▶). For TiIV analogues of the title compound, see: Ge et al. (2010 ▶) and references cited therein. For procedures used in the preparation, see: Curtis & Brown (1980 ▶); Chisholm et al. (1988 ▶); Diamond et al. (1996 ▶); Weizmann et al. (1950 ▶); Armarego & Perrin (1997 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[ZrCl3(C19H25N2Si)(C4H8O)]

M = 579.17

Triclinic,

a = 10.6274 (8) Å

b = 10.9496 (7) Å

c = 13.1397 (9) Å

α = 102.720 (1)°

β = 101.416 (1)°

γ = 110.456 (1)°

V = 1332.73 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.78 mm−1

T = 296 K

0.35 × 0.24 × 0.14 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 2006 ▶) T min = 0.773, T max = 0.899

4871 measured reflections

4871 independent reflections

3757 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.093

S = 1.00

4871 reflections

286 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012037/dn2668sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012037/dn2668Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZrCl3(C19H25N2Si)(C4H8O)]	Z = 2
Mr = 579.17	F(000) = 596
Triclinic, P1	Dx = 1.443 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6274 (8) Å	Cell parameters from 7558 reflections
b = 10.9496 (7) Å	θ = 2.2–30.5°
c = 13.1397 (9) Å	µ = 0.78 mm−1
α = 102.720 (1)°	T = 296 K
β = 101.416 (1)°	Block, yellow
γ = 110.456 (1)°	0.35 × 0.24 × 0.14 mm
V = 1332.73 (16) Å3

Bruker SMART APEXII diffractometer	4871 independent reflections
Radiation source: fine-focus sealed tube	3757 reflections with I > 2σ(I)
graphite	Rint = 0.000
Detector resolution: 8.333 pixels mm-1	θmax = 25.5°, θmin = 1.7°
phi and ω scans	h = −12→12
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996)	k = −13→12
Tmin = 0.773, Tmax = 0.899	l = 0→15
4871 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0479P)2] where P = (Fo2 + 2Fc2)/3
4871 reflections	(Δ/σ)max = 0.001
286 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Experimental. 28 0.09700 1.02798].

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

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

	x	y	z	Uiso*/Ueq
Zr1	0.61824 (3)	0.79166 (3)	0.25770 (2)	0.03334 (11)
Cl1	0.58498 (10)	0.81107 (9)	0.07182 (6)	0.0502 (2)
Cl2	0.41444 (10)	0.56691 (9)	0.19730 (8)	0.0583 (3)
Cl3	0.72883 (11)	0.73742 (10)	0.41743 (7)	0.0576 (3)
Si1	1.16456 (10)	1.26377 (10)	0.27386 (8)	0.0435 (2)
O1	0.7140 (2)	0.6414 (2)	0.17924 (17)	0.0433 (6)
N1	1.0468 (3)	1.1115 (2)	0.2942 (2)	0.0372 (6)
N2	0.8520 (3)	0.9395 (2)	0.2879 (2)	0.0374 (6)
C1	0.9063 (3)	1.0650 (3)	0.2797 (2)	0.0359 (7)
C2	1.0824 (4)	1.0052 (3)	0.3115 (3)	0.0446 (8)
H2	1.1715	1.0049	0.3227	0.054*
C3	0.9655 (4)	0.9038 (3)	0.3092 (3)	0.0441 (8)
H3	0.9608	0.8215	0.3202	0.053*
C4	0.8250 (3)	1.1502 (3)	0.2676 (3)	0.0394 (8)
H4A	0.7514	1.1065	0.1979	0.047*
H4B	0.8872	1.2394	0.2675	0.047*
C5	0.7574 (3)	1.1697 (3)	0.3619 (3)	0.0396 (8)
C6	0.7087 (4)	1.2867 (3)	0.3612 (3)	0.0550 (10)
H6A	0.7895	1.3723	0.3820	0.083*
H6B	0.6558	1.2915	0.4122	0.083*
H6C	0.6506	1.2692	0.2892	0.083*
C7	0.8677 (4)	1.2122 (4)	0.4726 (3)	0.0531 (9)
H7A	0.9000	1.1409	0.4751	0.080*
H7B	0.8264	1.2266	0.5304	0.080*
H7C	0.9459	1.2957	0.4817	0.080*
C8	0.6332 (3)	1.0379 (3)	0.3445 (3)	0.0386 (8)
C9	0.6119 (4)	0.9614 (3)	0.4176 (3)	0.0443 (8)
H9	0.6769	0.9818	0.4845	0.053*
C10	0.4812 (4)	0.8516 (4)	0.3765 (3)	0.0474 (9)
H10	0.4471	0.7835	0.4080	0.057*
C11	0.4082 (4)	0.8617 (3)	0.2776 (3)	0.0454 (8)
C12	0.5011 (4)	0.9761 (3)	0.2561 (3)	0.0398 (8)
C13	0.4532 (4)	1.0101 (3)	0.1619 (3)	0.0476 (9)
H13	0.5130	1.0835	0.1458	0.057*
C14	0.3188 (4)	0.9340 (4)	0.0952 (3)	0.0600 (10)
H14	0.2864	0.9571	0.0343	0.072*
C15	0.2277 (4)	0.8205 (4)	0.1171 (3)	0.0663 (11)
H15	0.1364	0.7703	0.0701	0.080*
C16	0.2693 (4)	0.7831 (4)	0.2038 (3)	0.0576 (10)
H16	0.2083	0.7066	0.2158	0.069*
C17	1.1715 (4)	1.4208 (4)	0.3664 (3)	0.0639 (11)
H17A	1.0850	1.4302	0.3421	0.096*
H17B	1.2488	1.4992	0.3660	0.096*
H17C	1.1844	1.4149	0.4393	0.096*
C18	1.3399 (4)	1.2627 (4)	0.3076 (4)	0.0705 (12)
H18A	1.3647	1.2576	0.3804	0.106*
H18B	1.4075	1.3453	0.3034	0.106*
H18C	1.3392	1.1845	0.2566	0.106*
C19	1.0933 (5)	1.2434 (5)	0.1285 (3)	0.0937 (17)
H19A	1.1033	1.1674	0.0837	0.141*
H19B	1.1440	1.3258	0.1136	0.141*
H19C	0.9954	1.2265	0.1124	0.141*
C20	0.6892 (6)	0.5070 (4)	0.1915 (4)	0.0815 (15)
H20A	0.7063	0.5130	0.2682	0.098*
H20B	0.5925	0.4431	0.1522	0.098*
C21	0.7848 (6)	0.4608 (5)	0.1475 (5)	0.0927 (17)
H21A	0.7346	0.3666	0.0995	0.111*
H21B	0.8587	0.4645	0.2064	0.111*
C22	0.8460 (5)	0.5506 (4)	0.0862 (4)	0.0704 (12)
H22A	0.8309	0.4973	0.0120	0.085*
H22B	0.9464	0.6030	0.1213	0.085*
C23	0.7710 (4)	0.6442 (4)	0.0868 (3)	0.0541 (10)
H23A	0.8359	0.7368	0.0961	0.065*
H23B	0.6958	0.6117	0.0188	0.065*

	U11	U22	U33	U12	U13	U23
Zr1	0.03764 (19)	0.03099 (18)	0.03008 (17)	0.01108 (14)	0.01052 (13)	0.01184 (13)
Cl1	0.0690 (6)	0.0556 (5)	0.0356 (4)	0.0332 (5)	0.0162 (4)	0.0191 (4)
Cl2	0.0513 (6)	0.0393 (5)	0.0695 (6)	0.0047 (4)	0.0176 (5)	0.0127 (5)
Cl3	0.0765 (7)	0.0664 (6)	0.0411 (5)	0.0357 (5)	0.0168 (5)	0.0286 (5)
Si1	0.0380 (5)	0.0431 (5)	0.0452 (5)	0.0107 (4)	0.0134 (4)	0.0151 (4)
O1	0.0578 (15)	0.0310 (12)	0.0447 (13)	0.0179 (11)	0.0201 (11)	0.0155 (10)
N1	0.0359 (15)	0.0346 (14)	0.0433 (15)	0.0148 (12)	0.0134 (12)	0.0144 (12)
N2	0.0402 (16)	0.0342 (15)	0.0379 (15)	0.0158 (13)	0.0088 (12)	0.0130 (12)
C1	0.0377 (19)	0.0373 (18)	0.0351 (17)	0.0167 (15)	0.0120 (15)	0.0133 (14)
C2	0.0365 (19)	0.042 (2)	0.056 (2)	0.0199 (17)	0.0105 (16)	0.0130 (17)
C3	0.046 (2)	0.0373 (19)	0.049 (2)	0.0212 (17)	0.0092 (17)	0.0112 (16)
C4	0.0344 (18)	0.0351 (18)	0.0488 (19)	0.0127 (15)	0.0122 (15)	0.0164 (15)
C5	0.0403 (19)	0.0336 (17)	0.0412 (18)	0.0164 (15)	0.0087 (15)	0.0061 (15)
C6	0.053 (2)	0.043 (2)	0.072 (3)	0.0251 (18)	0.020 (2)	0.0125 (19)
C7	0.048 (2)	0.048 (2)	0.045 (2)	0.0122 (18)	0.0049 (17)	0.0010 (17)
C8	0.0371 (19)	0.0379 (18)	0.0396 (18)	0.0159 (15)	0.0128 (15)	0.0080 (15)
C9	0.051 (2)	0.047 (2)	0.0324 (17)	0.0199 (18)	0.0137 (16)	0.0091 (15)
C10	0.051 (2)	0.048 (2)	0.049 (2)	0.0180 (18)	0.0258 (18)	0.0198 (17)
C11	0.041 (2)	0.045 (2)	0.053 (2)	0.0183 (17)	0.0202 (17)	0.0128 (17)
C12	0.0380 (19)	0.0416 (19)	0.0428 (18)	0.0204 (16)	0.0141 (15)	0.0107 (15)
C13	0.048 (2)	0.043 (2)	0.052 (2)	0.0216 (18)	0.0114 (18)	0.0143 (17)
C14	0.056 (3)	0.063 (3)	0.057 (2)	0.031 (2)	0.001 (2)	0.016 (2)
C15	0.043 (2)	0.067 (3)	0.072 (3)	0.019 (2)	0.001 (2)	0.013 (2)
C16	0.039 (2)	0.055 (2)	0.072 (3)	0.0133 (19)	0.015 (2)	0.017 (2)
C17	0.061 (3)	0.040 (2)	0.086 (3)	0.0140 (19)	0.024 (2)	0.019 (2)
C18	0.049 (2)	0.066 (3)	0.099 (3)	0.020 (2)	0.035 (2)	0.028 (3)
C19	0.084 (4)	0.101 (4)	0.060 (3)	−0.005 (3)	0.013 (2)	0.039 (3)
C20	0.118 (4)	0.047 (2)	0.117 (4)	0.047 (3)	0.069 (3)	0.045 (3)
C21	0.116 (4)	0.080 (3)	0.138 (5)	0.069 (3)	0.076 (4)	0.057 (3)
C22	0.080 (3)	0.081 (3)	0.078 (3)	0.052 (3)	0.035 (3)	0.035 (3)
C23	0.073 (3)	0.053 (2)	0.043 (2)	0.029 (2)	0.0262 (19)	0.0146 (17)

Zr1—N2	2.338 (3)	C8—C9	1.408 (4)
Zr1—O1	2.375 (2)	C8—C12	1.457 (4)
Zr1—Cl1	2.4647 (8)	C9—C10	1.384 (5)
Zr1—C10	2.472 (3)	C9—H9	0.9300
Zr1—Cl2	2.4720 (9)	C10—C11	1.424 (5)
Zr1—Cl3	2.4898 (9)	C10—H10	0.9300
Zr1—C9	2.509 (3)	C11—C12	1.424 (5)
Zr1—C8	2.622 (3)	C11—C16	1.427 (5)
Zr1—C11	2.642 (3)	C12—C13	1.420 (5)
Zr1—C12	2.720 (3)	C13—C14	1.361 (5)
Si1—N1	1.814 (3)	C13—H13	0.9300
Si1—C18	1.833 (4)	C14—C15	1.411 (6)
Si1—C19	1.842 (4)	C14—H14	0.9300
Si1—C17	1.843 (4)	C15—C16	1.339 (5)
O1—C20	1.453 (4)	C15—H15	0.9300
O1—C23	1.462 (4)	C16—H16	0.9300
N1—C1	1.356 (4)	C17—H17A	0.9600
N1—C2	1.392 (4)	C17—H17B	0.9600
N2—C1	1.329 (4)	C17—H17C	0.9600
N2—C3	1.390 (4)	C18—H18A	0.9600
C1—C4	1.488 (4)	C18—H18B	0.9600
C2—C3	1.335 (5)	C18—H18C	0.9600
C2—H2	0.9300	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.563 (4)	C19—H19C	0.9600
C4—H4A	0.9700	C20—C21	1.445 (6)
C4—H4B	0.9700	C20—H20A	0.9700
C5—C8	1.511 (4)	C20—H20B	0.9700
C5—C7	1.534 (5)	C21—C22	1.465 (6)
C5—C6	1.541 (4)	C21—H21A	0.9700
C6—H6A	0.9600	C21—H21B	0.9700
C6—H6B	0.9600	C22—C23	1.503 (5)
C6—H6C	0.9600	C22—H22A	0.9700
C7—H7A	0.9600	C22—H22B	0.9700
C7—H7B	0.9600	C23—H23A	0.9700
C7—H7C	0.9600	C23—H23B	0.9700
N2—Zr1—O1	77.04 (8)	H7A—C7—H7B	109.5
N2—Zr1—Cl1	84.08 (6)	C5—C7—H7C	109.5
O1—Zr1—Cl1	79.04 (6)	H7A—C7—H7C	109.5
N2—Zr1—C10	120.70 (10)	H7B—C7—H7C	109.5
O1—Zr1—C10	151.10 (10)	C9—C8—C12	105.6 (3)
Cl1—Zr1—C10	122.63 (9)	C9—C8—C5	127.4 (3)
N2—Zr1—Cl2	155.51 (7)	C12—C8—C5	126.4 (3)
O1—Zr1—Cl2	78.56 (6)	C9—C8—Zr1	69.73 (17)
Cl1—Zr1—Cl2	93.30 (3)	C12—C8—Zr1	77.94 (18)
C10—Zr1—Cl2	81.10 (8)	C5—C8—Zr1	124.3 (2)
N2—Zr1—Cl3	81.90 (7)	C10—C9—C8	110.9 (3)
O1—Zr1—Cl3	76.92 (6)	C10—C9—Zr1	72.37 (18)
Cl1—Zr1—Cl3	154.33 (3)	C8—C9—Zr1	78.51 (18)
C10—Zr1—Cl3	83.04 (9)	C10—C9—H9	124.5
Cl2—Zr1—Cl3	90.66 (3)	C8—C9—H9	124.5
N2—Zr1—C9	88.44 (10)	Zr1—C9—H9	116.3
O1—Zr1—C9	151.65 (10)	C9—C10—C11	107.8 (3)
Cl1—Zr1—C9	124.05 (8)	C9—C10—Zr1	75.37 (19)
C10—Zr1—C9	32.26 (11)	C11—C10—Zr1	80.5 (2)
Cl2—Zr1—C9	112.69 (8)	C9—C10—H10	126.1
Cl3—Zr1—C9	77.01 (8)	C11—C10—H10	126.1
N2—Zr1—C8	75.20 (9)	Zr1—C10—H10	110.7
O1—Zr1—C8	151.85 (9)	C10—C11—C12	107.7 (3)
Cl1—Zr1—C8	93.50 (7)	C10—C11—C16	132.9 (3)
C10—Zr1—C8	53.60 (11)	C12—C11—C16	119.4 (3)
Cl2—Zr1—C8	129.29 (8)	C10—C11—Zr1	67.36 (19)
Cl3—Zr1—C8	103.50 (7)	C12—C11—Zr1	77.67 (19)
C9—Zr1—C8	31.77 (10)	C16—C11—Zr1	121.4 (2)
N2—Zr1—C11	127.00 (10)	C13—C12—C11	119.2 (3)
O1—Zr1—C11	153.12 (10)	C13—C12—C8	133.1 (3)
Cl1—Zr1—C11	90.77 (8)	C11—C12—C8	107.7 (3)
C10—Zr1—C11	32.11 (11)	C13—C12—Zr1	124.3 (2)
Cl2—Zr1—C11	77.27 (8)	C11—C12—Zr1	71.58 (19)
Cl3—Zr1—C11	114.83 (8)	C8—C12—Zr1	70.47 (18)
C9—Zr1—C11	52.20 (11)	C14—C13—C12	119.3 (3)
C8—Zr1—C11	52.45 (10)	C14—C13—H13	120.4
N2—Zr1—C12	98.51 (9)	C12—C13—H13	120.4
O1—Zr1—C12	153.90 (9)	C13—C14—C15	121.1 (4)
Cl1—Zr1—C12	74.91 (7)	C13—C14—H14	119.5
C10—Zr1—C12	52.31 (11)	C15—C14—H14	119.5
Cl2—Zr1—C12	104.31 (8)	C16—C15—C14	121.7 (4)
Cl3—Zr1—C12	128.42 (7)	C16—C15—H15	119.2
C9—Zr1—C12	51.57 (10)	C14—C15—H15	119.2
C8—Zr1—C12	31.59 (9)	C15—C16—C11	119.4 (4)
C11—Zr1—C12	30.75 (10)	C15—C16—H16	120.3
N1—Si1—C18	106.39 (16)	C11—C16—H16	120.3
N1—Si1—C19	104.76 (17)	Si1—C17—H17A	109.5
C18—Si1—C19	113.1 (2)	Si1—C17—H17B	109.5
N1—Si1—C17	111.00 (15)	H17A—C17—H17B	109.5
C18—Si1—C17	108.7 (2)	Si1—C17—H17C	109.5
C19—Si1—C17	112.6 (2)	H17A—C17—H17C	109.5
C20—O1—C23	105.4 (3)	H17B—C17—H17C	109.5
C20—O1—Zr1	125.3 (2)	Si1—C18—H18A	109.5
C23—O1—Zr1	126.99 (18)	Si1—C18—H18B	109.5
C1—N1—C2	105.3 (3)	H18A—C18—H18B	109.5
C1—N1—Si1	129.6 (2)	Si1—C18—H18C	109.5
C2—N1—Si1	124.4 (2)	H18A—C18—H18C	109.5
C1—N2—C3	104.8 (3)	H18B—C18—H18C	109.5
C1—N2—Zr1	130.6 (2)	Si1—C19—H19A	109.5
C3—N2—Zr1	124.4 (2)	Si1—C19—H19B	109.5
N2—C1—N1	112.3 (3)	H19A—C19—H19B	109.5
N2—C1—C4	123.7 (3)	Si1—C19—H19C	109.5
N1—C1—C4	123.7 (3)	H19A—C19—H19C	109.5
C3—C2—N1	107.6 (3)	H19B—C19—H19C	109.5
C3—C2—H2	126.2	C21—C20—O1	107.4 (3)
N1—C2—H2	126.2	C21—C20—H20A	110.2
C2—C3—N2	109.9 (3)	O1—C20—H20A	110.2
C2—C3—H3	125.0	C21—C20—H20B	110.2
N2—C3—H3	125.0	O1—C20—H20B	110.2
C1—C4—C5	111.8 (3)	H20A—C20—H20B	108.5
C1—C4—H4A	109.3	C20—C21—C22	108.4 (4)
C5—C4—H4A	109.3	C20—C21—H21A	110.0
C1—C4—H4B	109.3	C22—C21—H21A	110.0
C5—C4—H4B	109.3	C20—C21—H21B	110.0
H4A—C4—H4B	107.9	C22—C21—H21B	110.0
C8—C5—C7	110.9 (3)	H21A—C21—H21B	108.4
C8—C5—C6	110.0 (3)	C21—C22—C23	105.2 (3)
C7—C5—C6	107.8 (3)	C21—C22—H22A	110.7
C8—C5—C4	109.5 (2)	C23—C22—H22A	110.7
C7—C5—C4	109.8 (3)	C21—C22—H22B	110.7
C6—C5—C4	108.7 (3)	C23—C22—H22B	110.7
C5—C6—H6A	109.5	H22A—C22—H22B	108.8
C5—C6—H6B	109.5	O1—C23—C22	105.5 (3)
H6A—C6—H6B	109.5	O1—C23—H23A	110.6
C5—C6—H6C	109.5	C22—C23—H23A	110.6
H6A—C6—H6C	109.5	O1—C23—H23B	110.6
H6B—C6—H6C	109.5	C22—C23—H23B	110.6
C5—C7—H7A	109.5	H23A—C23—H23B	108.8
C5—C7—H7B	109.5
N2—Zr1—O1—C20	137.0 (3)	Cl2—Zr1—C9—C8	−128.95 (18)
Cl1—Zr1—O1—C20	−136.6 (3)	Cl3—Zr1—C9—C8	145.9 (2)
C10—Zr1—O1—C20	5.1 (4)	C11—Zr1—C9—C8	−77.7 (2)
Cl2—Zr1—O1—C20	−41.0 (3)	C12—Zr1—C9—C8	−38.36 (19)
Cl3—Zr1—O1—C20	52.4 (3)	C8—C9—C10—C11	−5.0 (4)
C9—Zr1—O1—C20	76.0 (4)	Zr1—C9—C10—C11	−74.8 (2)
C8—Zr1—O1—C20	146.7 (3)	C8—C9—C10—Zr1	69.8 (2)
C11—Zr1—O1—C20	−67.2 (4)	N2—Zr1—C10—C9	0.4 (2)
C12—Zr1—O1—C20	−140.2 (3)	O1—Zr1—C10—C9	122.8 (2)
N2—Zr1—O1—C23	−62.6 (3)	Cl1—Zr1—C10—C9	−103.4 (2)
Cl1—Zr1—O1—C23	23.7 (3)	Cl2—Zr1—C10—C9	168.4 (2)
C10—Zr1—O1—C23	165.5 (3)	Cl3—Zr1—C10—C9	76.6 (2)
Cl2—Zr1—O1—C23	119.4 (3)	C8—Zr1—C10—C9	−35.82 (19)
Cl3—Zr1—O1—C23	−147.2 (3)	C11—Zr1—C10—C9	−111.4 (3)
C9—Zr1—O1—C23	−123.6 (3)	C12—Zr1—C10—C9	−75.7 (2)
C8—Zr1—O1—C23	−53.0 (4)	N2—Zr1—C10—C11	111.8 (2)
C11—Zr1—O1—C23	93.1 (3)	O1—Zr1—C10—C11	−125.8 (2)
C12—Zr1—O1—C23	20.2 (4)	Cl1—Zr1—C10—C11	8.0 (2)
C18—Si1—N1—C1	−179.5 (3)	Cl2—Zr1—C10—C11	−80.22 (19)
C19—Si1—N1—C1	−59.5 (3)	Cl3—Zr1—C10—C11	−172.0 (2)
C17—Si1—N1—C1	62.4 (3)	C9—Zr1—C10—C11	111.4 (3)
C18—Si1—N1—C2	−10.9 (3)	C8—Zr1—C10—C11	75.5 (2)
C19—Si1—N1—C2	109.2 (3)	C12—Zr1—C10—C11	35.71 (19)
C17—Si1—N1—C2	−129.0 (3)	C9—C10—C11—C12	3.3 (4)
O1—Zr1—N2—C1	139.2 (3)	Zr1—C10—C11—C12	−67.9 (2)
Cl1—Zr1—N2—C1	59.1 (3)	C9—C10—C11—C16	−176.3 (4)
C10—Zr1—N2—C1	−65.6 (3)	Zr1—C10—C11—C16	112.6 (4)
Cl2—Zr1—N2—C1	144.0 (2)	C9—C10—C11—Zr1	71.2 (2)
Cl3—Zr1—N2—C1	−142.5 (3)	N2—Zr1—C11—C10	−90.1 (2)
C9—Zr1—N2—C1	−65.4 (3)	O1—Zr1—C11—C10	119.9 (2)
C8—Zr1—N2—C1	−36.1 (3)	Cl1—Zr1—C11—C10	−173.27 (19)
C11—Zr1—N2—C1	−27.4 (3)	Cl2—Zr1—C11—C10	93.5 (2)
C12—Zr1—N2—C1	−14.6 (3)	Cl3—Zr1—C11—C10	8.8 (2)
O1—Zr1—N2—C3	−34.1 (2)	C9—Zr1—C11—C10	−38.98 (19)
Cl1—Zr1—N2—C3	−114.2 (2)	C8—Zr1—C11—C10	−79.4 (2)
C10—Zr1—N2—C3	121.2 (2)	C12—Zr1—C11—C10	−115.4 (3)
Cl2—Zr1—N2—C3	−29.2 (3)	N2—Zr1—C11—C12	25.3 (2)
Cl3—Zr1—N2—C3	44.3 (2)	O1—Zr1—C11—C12	−124.7 (2)
C9—Zr1—N2—C3	121.4 (2)	Cl1—Zr1—C11—C12	−57.87 (19)
C8—Zr1—N2—C3	150.6 (3)	C10—Zr1—C11—C12	115.4 (3)
C11—Zr1—N2—C3	159.3 (2)	Cl2—Zr1—C11—C12	−151.1 (2)
C12—Zr1—N2—C3	172.1 (2)	Cl3—Zr1—C11—C12	124.17 (18)
C3—N2—C1—N1	0.1 (3)	C9—Zr1—C11—C12	76.4 (2)
Zr1—N2—C1—N1	−174.11 (19)	C8—Zr1—C11—C12	35.96 (18)
C3—N2—C1—C4	−174.0 (3)	N2—Zr1—C11—C16	142.3 (3)
Zr1—N2—C1—C4	11.8 (4)	O1—Zr1—C11—C16	−7.6 (4)
C2—N1—C1—N2	0.7 (3)	Cl1—Zr1—C11—C16	59.2 (3)
Si1—N1—C1—N2	171.1 (2)	C10—Zr1—C11—C16	−127.5 (4)
C2—N1—C1—C4	174.8 (3)	Cl2—Zr1—C11—C16	−34.0 (3)
Si1—N1—C1—C4	−14.8 (4)	Cl3—Zr1—C11—C16	−118.8 (3)
C1—N1—C2—C3	−1.3 (4)	C9—Zr1—C11—C16	−166.5 (4)
Si1—N1—C2—C3	−172.3 (2)	C8—Zr1—C11—C16	153.0 (3)
N1—C2—C3—N2	1.5 (4)	C12—Zr1—C11—C16	117.1 (4)
C1—N2—C3—C2	−1.0 (4)	C10—C11—C12—C13	−179.3 (3)
Zr1—N2—C3—C2	173.7 (2)	C16—C11—C12—C13	0.3 (5)
N2—C1—C4—C5	55.6 (4)	Zr1—C11—C12—C13	119.6 (3)
N1—C1—C4—C5	−117.8 (3)	C10—C11—C12—C8	−0.5 (4)
C1—C4—C5—C8	−74.1 (3)	C16—C11—C12—C8	179.1 (3)
C1—C4—C5—C7	47.9 (4)	Zr1—C11—C12—C8	−61.6 (2)
C1—C4—C5—C6	165.6 (3)	C10—C11—C12—Zr1	61.1 (2)
C7—C5—C8—C9	2.0 (4)	C16—C11—C12—Zr1	−119.3 (3)
C6—C5—C8—C9	−117.1 (4)	C9—C8—C12—C13	176.2 (3)
C4—C5—C8—C9	123.5 (3)	C5—C8—C12—C13	4.8 (6)
C7—C5—C8—C12	171.5 (3)	Zr1—C8—C12—C13	−119.1 (4)
C6—C5—C8—C12	52.4 (4)	C9—C8—C12—C11	−2.4 (4)
C4—C5—C8—C12	−67.1 (4)	C5—C8—C12—C11	−173.7 (3)
C7—C5—C8—Zr1	−87.6 (3)	Zr1—C8—C12—C11	62.3 (2)
C6—C5—C8—Zr1	153.3 (2)	C9—C8—C12—Zr1	−64.7 (2)
C4—C5—C8—Zr1	33.8 (3)	C5—C8—C12—Zr1	124.0 (3)
N2—Zr1—C8—C9	−111.9 (2)	N2—Zr1—C12—C13	86.9 (3)
O1—Zr1—C8—C9	−121.7 (2)	O1—Zr1—C12—C13	9.0 (4)
Cl1—Zr1—C8—C9	165.2 (2)	Cl1—Zr1—C12—C13	5.4 (3)
C10—Zr1—C8—C9	36.4 (2)	C10—Zr1—C12—C13	−150.7 (3)
Cl2—Zr1—C8—C9	68.0 (2)	Cl2—Zr1—C12—C13	−84.2 (3)
Cl3—Zr1—C8—C9	−34.2 (2)	Cl3—Zr1—C12—C13	173.3 (2)
C11—Zr1—C8—C9	76.9 (2)	C9—Zr1—C12—C13	168.0 (3)
C12—Zr1—C8—C9	111.9 (3)	C8—Zr1—C12—C13	129.4 (4)
N2—Zr1—C8—C12	136.2 (2)	C11—Zr1—C12—C13	−113.3 (4)
O1—Zr1—C8—C12	126.5 (2)	N2—Zr1—C12—C11	−159.8 (2)
Cl1—Zr1—C8—C12	53.30 (18)	O1—Zr1—C12—C11	122.3 (2)
C10—Zr1—C8—C12	−75.5 (2)	Cl1—Zr1—C12—C11	118.7 (2)
Cl2—Zr1—C8—C12	−43.9 (2)	C10—Zr1—C12—C11	−37.4 (2)
Cl3—Zr1—C8—C12	−146.08 (17)	Cl2—Zr1—C12—C11	29.1 (2)
C9—Zr1—C8—C12	−111.9 (3)	Cl3—Zr1—C12—C11	−73.4 (2)
C11—Zr1—C8—C12	−34.97 (18)	C9—Zr1—C12—C11	−78.7 (2)
N2—Zr1—C8—C5	10.2 (2)	C8—Zr1—C12—C11	−117.3 (3)
O1—Zr1—C8—C5	0.4 (4)	N2—Zr1—C12—C8	−42.55 (19)
Cl1—Zr1—C8—C5	−72.7 (2)	O1—Zr1—C12—C8	−120.4 (2)
C10—Zr1—C8—C5	158.5 (3)	Cl1—Zr1—C12—C8	−124.02 (19)
Cl2—Zr1—C8—C5	−169.9 (2)	C10—Zr1—C12—C8	79.9 (2)
Cl3—Zr1—C8—C5	87.9 (2)	Cl2—Zr1—C12—C8	146.39 (17)
C9—Zr1—C8—C5	122.1 (4)	Cl3—Zr1—C12—C8	43.8 (2)
C11—Zr1—C8—C5	−161.0 (3)	C9—Zr1—C12—C8	38.59 (18)
C12—Zr1—C8—C5	−126.0 (3)	C11—Zr1—C12—C8	117.3 (3)
C12—C8—C9—C10	4.6 (4)	C11—C12—C13—C14	1.2 (5)
C5—C8—C9—C10	175.8 (3)	C8—C12—C13—C14	−177.3 (4)
Zr1—C8—C9—C10	−65.9 (2)	Zr1—C12—C13—C14	87.9 (4)
C12—C8—C9—Zr1	70.5 (2)	C12—C13—C14—C15	−1.4 (6)
C5—C8—C9—Zr1	−118.3 (3)	C13—C14—C15—C16	0.0 (6)
N2—Zr1—C9—C10	−179.7 (2)	C14—C15—C16—C11	1.5 (6)
O1—Zr1—C9—C10	−121.2 (2)	C10—C11—C16—C15	177.9 (4)
Cl1—Zr1—C9—C10	98.5 (2)	C12—C11—C16—C15	−1.6 (6)
Cl2—Zr1—C9—C10	−12.4 (2)	Zr1—C11—C16—C15	−94.9 (4)
Cl3—Zr1—C9—C10	−97.6 (2)	C23—O1—C20—C21	25.8 (5)
C8—Zr1—C9—C10	116.5 (3)	Zr1—O1—C20—C21	−170.3 (3)
C11—Zr1—C9—C10	38.8 (2)	O1—C20—C21—C22	−12.5 (6)
C12—Zr1—C9—C10	78.2 (2)	C20—C21—C22—C23	−5.4 (6)
N2—Zr1—C9—C8	63.8 (2)	C20—O1—C23—C22	−28.9 (4)
O1—Zr1—C9—C8	122.3 (2)	Zr1—O1—C23—C22	167.7 (2)
Cl1—Zr1—C9—C8	−18.0 (2)	C21—C22—C23—O1	21.1 (5)
C10—Zr1—C9—C8	−116.5 (3)