metal-organic compounds
[N-(2-Anilinoethyl)-N′-(trimethylsilyl)benzenecarboximidamidato-κ3N,N′,N′′](benzonitrile-κN)trichloridozirconium(IV)
aInstitute of Molecular Science, Shanxi University, Taiyuan 030006, People's Republic of China, bResearch Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China, and cDepartment of Chemistry, Changzhi University, Changzhi 046011, People's Republic of China
*Correspondence e-mail: dsliu@sxu.edu.cn
There are two independent molecules in the 18H24N3Si)Cl3(C7H5N)], which are connected by an N—H⋯Cl hydrogen bond. The Zr atoms are seven-coordinate and possess a distorted pentagonal–bipyramidal geometry. In the crystal, molecules are connected by N—H⋯Cl hydrogen bonds, forming ribbons along [010].
of the title compound, [Zr(CKeywords: crystal structure; zirconium complex; mononuclear structure; mixed ligands.
CCDC reference: 1536806
Structure description
Nitrogen-based ligands have attracted much interest in organometallic chemistry and catalysis chemistry (Edelmann, 1995; Mack & Eisen, 1996). As the closest relatives of nitrogen-based ligands, amidinate ligands have attracted considerable attention due to their relatively simple synthesis and easy modification of steric and electronic requirements by varying the substituents on the nitrogen atom. A more sterically hindered amidinate is required, or amidinates that can give additional electronic stabilization to the highly electronically unsaturated metal atom are required. In the course of extending amidinate chemistry, we have explored a practical synthetic pathway to alkyl-ended amidinate and ansa-bis(amidinate) ligands (Bai et al., 2013). They have been applied in the synthesis of Group 4 complexes, which are good catalysts for ethylene polymerization (Bai et al., 2010). In our recent work, we have reported the synthesis and characterization of carbon chain-linked mixed amidinate-amido chelate complexes, and have described the different catalytic activities of the zirconium and titanium compounds toward ethylene polymerization (Li et al., 2016, 2017).
There are two independent molecules in the et al., 2016, 2017). Intramolecular N3—H3A⋯Cl1 and N7—H7A⋯Cl4 hydrogen bonds occur and the two independent molecules are linked by N7—H7A⋯Cl2 hydrogen bonds (Table 1 and Fig. 1). Weak intramolecular C–H⋯Cl interactions further stabilize the molecular structure.
of the title compound. The Zr atoms are seven-coordinate and possess a distorted pentagonal–bipyramidal geometry. The four non-bridging chloride ions (Cl1 and Cl3, Cl4 and Cl6) occupy the axial positions and form a near straight angle [Cl1—Zr1—Cl3 = 165.62 (13)°, Cl4—Zr2—Cl6 = 165.14 (12)°]. Atoms N1–N4/Cl2 and N5–N8/Cl5 form the equatorial planes, with r.m.s. deviations of 0.044 and 0.0508 Å, respectively. The Zr1—N1 and Zr1—N2 bond lengths compare well with those reported for amidinate zirconium complexes (LiIn the crystal, the molecules are linked by N3—H3A⋯Cl5 interactions, forming ribbons along [010] (Table 1 and Fig. 2).
Synthesis and crystallization
The title compound was obtained unexpectedly during an attempt to synthesize a zirconium complex based on the ethylene-linked amidinate-amido ligand To a solution of PhNH(CH2)2NHSiMe3 (0.625 g, 3.00 mmol) in Et2O (30 ml) at 273 K was added one equivalent of LiBun and the reaction mixture was warmed to room temperature and stirred for a further 4 h. One equivalent PhCN was added at 195 K. The resulting mixture was warmed to room temperature and stirred for 12 h. Then one equivalent ZrCl4 (0.699 g, 3 mmol) was added at 195 K. The resulting mixture was warmed to room temperature and stirred for 12 h. The volatiles were removed in vacuo, and the residue was extracted with 15 ml of dichloromethane and filtered. The filtrate was concentrated in vacuo to ca 10 ml and left at room temperature for one month to give colorless block-shaped crystals of the title compound in 36% yield.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1536806
https://doi.org/10.1107/S2414314617003807/zq4018sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003807/zq4018Isup2.hkl
Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Zr(C18H24N3Si)Cl3(C7H5N)] | Dx = 1.434 Mg m−3 Dm = 1.434 Mg m−3 Dm measured by not measured |
Mr = 611.18 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 2629 reflections |
a = 35.830 (2) Å | θ = 2.2–28.5° |
b = 14.292 (9) Å | µ = 0.73 mm−1 |
c = 11.057 (6) Å | T = 194 K |
V = 5662 (5) Å3 | Block, colorless |
Z = 8 | 0.35 × 0.32 × 0.30 mm |
F(000) = 2496 |
Bruker SMART APEX CCD area detector diffractometer | 5601 reflections with I > 2σ(I) |
φ and ω scan | Rint = 0.133 |
Absorption correction: multi-scan SADABS (Bruker, 2012) | θmax = 25.1°, θmin = 1.5° |
Tmin = 0.773, Tmax = 0.802 | h = −42→39 |
29608 measured reflections | k = −13→17 |
9600 independent reflections | l = −13→11 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.0852P)2 + 0.8394P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.194 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 1.02 e Å−3 |
9600 reflections | Δρmin = −0.80 e Å−3 |
571 parameters | Absolute structure: Flack x determined using 1602 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.06 (6) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Zr1 | 0.88588 (3) | 0.41831 (7) | 0.15136 (10) | 0.0389 (3) | |
Zr2 | 0.85844 (3) | 0.91156 (7) | 0.25654 (10) | 0.0372 (3) | |
Cl1 | 0.83935 (9) | 0.3568 (2) | 0.0148 (3) | 0.0586 (9) | |
Cl2 | 0.88440 (9) | 0.5773 (2) | 0.0649 (3) | 0.0547 (9) | |
Cl3 | 0.92042 (9) | 0.4735 (2) | 0.3257 (3) | 0.0626 (10) | |
Cl4 | 0.81962 (9) | 0.8434 (2) | 0.0999 (3) | 0.0575 (9) | |
Cl5 | 0.83063 (9) | 1.0686 (2) | 0.2387 (3) | 0.0549 (9) | |
Cl6 | 0.90977 (9) | 0.9766 (2) | 0.3736 (3) | 0.0544 (9) | |
N1 | 0.9333 (3) | 0.4009 (6) | 0.0270 (10) | 0.049 (3) | |
N2 | 0.9162 (2) | 0.2879 (6) | 0.1474 (9) | 0.046 (3) | |
N3 | 0.8622 (3) | 0.2975 (7) | 0.2951 (9) | 0.051 (3) | |
H3A | 0.8547 | 0.2684 | 0.2293 | 0.061* | |
N4 | 0.8335 (3) | 0.4850 (6) | 0.2414 (11) | 0.052 (3) | |
N5 | 0.8207 (3) | 0.8984 (6) | 0.4144 (9) | 0.047 (3) | |
N6 | 0.8566 (2) | 0.7835 (6) | 0.3559 (8) | 0.036 (2) | |
N7 | 0.9046 (3) | 0.7949 (6) | 0.1871 (8) | 0.043 (3) | |
H7A | 0.8860 | 0.7641 | 0.1535 | 0.051* | |
N8 | 0.8870 (3) | 0.9788 (7) | 0.0859 (10) | 0.052 (3) | |
Si1 | 0.95406 (11) | 0.4573 (3) | −0.0973 (4) | 0.0580 (11) | |
Si2 | 0.78585 (10) | 0.9616 (3) | 0.4884 (4) | 0.0515 (10) | |
C1 | 1.01141 (16) | 0.3356 (4) | 0.1174 (5) | 0.052 (4) | |
H1 | 1.0081 | 0.3989 | 0.1411 | 0.062* | |
C2 | 1.04686 (14) | 0.2961 (5) | 0.1181 (7) | 0.070 (5) | |
H2 | 1.0678 | 0.3325 | 0.1423 | 0.084* | |
C3 | 1.05173 (17) | 0.2034 (5) | 0.0834 (9) | 0.065 (4) | |
H3 | 1.0760 | 0.1764 | 0.0839 | 0.078* | |
C4 | 1.0212 (2) | 0.1502 (4) | 0.0480 (8) | 0.061 (4) | |
H4 | 1.0245 | 0.0869 | 0.0243 | 0.074* | |
C5 | 0.98570 (19) | 0.1897 (5) | 0.0473 (8) | 0.056 (4) | |
H5 | 0.9648 | 0.1533 | 0.0231 | 0.068* | |
C6 | 0.98082 (14) | 0.2824 (5) | 0.0820 (7) | 0.041 (3) | |
C7 | 0.9437 (3) | 0.3241 (8) | 0.0806 (12) | 0.047 (3) | |
C8 | 0.9185 (3) | 0.2158 (8) | 0.2356 (11) | 0.049 (3) | |
H8A | 0.9446 | 0.2072 | 0.2621 | 0.058* | |
H8B | 0.9094 | 0.1559 | 0.2014 | 0.058* | |
C9 | 0.8948 (3) | 0.2443 (9) | 0.3392 (11) | 0.052 (3) | |
H9A | 0.8863 | 0.1882 | 0.3838 | 0.062* | |
H9B | 0.9096 | 0.2837 | 0.3954 | 0.062* | |
C10 | 0.8357 (4) | 0.3151 (8) | 0.3911 (12) | 0.060 (4) | |
C11 | 0.8451 (5) | 0.3583 (12) | 0.4938 (14) | 0.086 (5) | |
H11 | 0.8698 | 0.3809 | 0.5055 | 0.104* | |
C12 | 0.8189 (6) | 0.3694 (13) | 0.5810 (16) | 0.117 (7) | |
H12 | 0.8250 | 0.4002 | 0.6545 | 0.141* | |
C13 | 0.7826 (5) | 0.3351 (13) | 0.5624 (18) | 0.114 (6) | |
H13 | 0.7646 | 0.3401 | 0.6251 | 0.136* | |
C14 | 0.7733 (4) | 0.2958 (11) | 0.4582 (18) | 0.097 (6) | |
H14 | 0.7482 | 0.2768 | 0.4454 | 0.117* | |
C15 | 0.7990 (3) | 0.2821 (9) | 0.3685 (15) | 0.063 (4) | |
H15 | 0.7926 | 0.2519 | 0.2948 | 0.076* | |
C16 | 0.8083 (3) | 0.5232 (8) | 0.2749 (11) | 0.046 (3) | |
C17 | 0.77775 (18) | 0.5721 (5) | 0.3193 (7) | 0.049 (3) | |
C18 | 0.7530 (2) | 0.5264 (5) | 0.3961 (8) | 0.077 (5) | |
H18 | 0.7565 | 0.4621 | 0.4144 | 0.092* | |
C19 | 0.7231 (2) | 0.5749 (8) | 0.4459 (10) | 0.107 (7) | |
H19 | 0.7062 | 0.5437 | 0.4983 | 0.129* | |
C20 | 0.7179 (3) | 0.6690 (8) | 0.4190 (11) | 0.099 (6) | |
H20 | 0.6975 | 0.7021 | 0.4531 | 0.119* | |
C21 | 0.7427 (3) | 0.7147 (5) | 0.3423 (11) | 0.093 (6) | |
H21 | 0.7391 | 0.7790 | 0.3240 | 0.112* | |
C22 | 0.7726 (2) | 0.6662 (5) | 0.2925 (8) | 0.059 (4) | |
H22 | 0.7895 | 0.6975 | 0.2400 | 0.070* | |
C23 | 0.9156 (5) | 0.4887 (12) | −0.2023 (14) | 0.092 (6) | |
H23A | 0.8976 | 0.4372 | −0.2061 | 0.138* | |
H23B | 0.9259 | 0.5002 | −0.2831 | 0.138* | |
H23C | 0.9031 | 0.5454 | −0.1731 | 0.138* | |
C24 | 0.9847 (4) | 0.3759 (11) | −0.1819 (13) | 0.079 (5) | |
H24A | 1.0080 | 0.3667 | −0.1371 | 0.119* | |
H24B | 0.9903 | 0.4022 | −0.2617 | 0.119* | |
H24C | 0.9720 | 0.3156 | −0.1917 | 0.119* | |
C25 | 0.9795 (4) | 0.5593 (10) | −0.0452 (13) | 0.075 (5) | |
H25A | 0.9653 | 0.5905 | 0.0188 | 0.113* | |
H25B | 0.9832 | 0.6027 | −0.1129 | 0.113* | |
H25C | 1.0039 | 0.5399 | −0.0136 | 0.113* | |
C26 | 0.82672 (16) | 0.6878 (4) | 0.5896 (6) | 0.065 (4) | |
H26 | 0.8197 | 0.6488 | 0.5238 | 0.078* | |
C27 | 0.8262 (2) | 0.6529 (5) | 0.7069 (7) | 0.079 (5) | |
H27 | 0.8188 | 0.5901 | 0.7214 | 0.095* | |
C28 | 0.8365 (2) | 0.7100 (7) | 0.8031 (6) | 0.078 (5) | |
H28 | 0.8361 | 0.6862 | 0.8833 | 0.093* | |
C29 | 0.8473 (2) | 0.8020 (6) | 0.7819 (7) | 0.063 (4) | |
H29 | 0.8543 | 0.8410 | 0.8476 | 0.075* | |
C30 | 0.8478 (2) | 0.8369 (5) | 0.6645 (8) | 0.053 (4) | |
H30 | 0.8552 | 0.8997 | 0.6501 | 0.064* | |
C31 | 0.83752 (18) | 0.7798 (5) | 0.5684 (6) | 0.043 (3) | |
C32 | 0.8372 (3) | 0.8207 (8) | 0.4468 (10) | 0.039 (3) | |
C33 | 0.8826 (3) | 0.7077 (8) | 0.3604 (10) | 0.044 (3) | |
H33A | 0.8717 | 0.6510 | 0.3230 | 0.052* | |
H33B | 0.8892 | 0.6932 | 0.4453 | 0.052* | |
C34 | 0.9161 (3) | 0.7387 (8) | 0.2920 (11) | 0.052 (4) | |
H34A | 0.9324 | 0.7764 | 0.3453 | 0.062* | |
H34B | 0.9304 | 0.6834 | 0.2643 | 0.062* | |
C35 | 0.9367 (3) | 0.8201 (8) | 0.1140 (12) | 0.050 (4) | |
C36 | 0.9352 (4) | 0.7984 (9) | −0.0099 (12) | 0.060 (4) | |
H36 | 0.9146 | 0.7664 | −0.0443 | 0.073* | |
C37 | 0.9656 (5) | 0.8262 (11) | −0.0799 (16) | 0.092 (6) | |
H37 | 0.9660 | 0.8094 | −0.1630 | 0.110* | |
C38 | 0.9941 (5) | 0.8751 (12) | −0.0358 (17) | 0.095 (6) | |
H38 | 1.0135 | 0.8969 | −0.0874 | 0.115* | |
C39 | 0.9948 (5) | 0.8938 (12) | 0.088 (2) | 0.111 (7) | |
H39 | 1.0156 | 0.9255 | 0.1223 | 0.133* | |
C40 | 0.9661 (4) | 0.8671 (10) | 0.1616 (16) | 0.069 (4) | |
H40 | 0.9667 | 0.8814 | 0.2455 | 0.082* | |
C41 | 0.8919 (3) | 1.0162 (8) | −0.0021 (13) | 0.050 (3) | |
C42 | 0.89633 (19) | 1.0673 (5) | −0.1091 (6) | 0.043 (3) | |
C43 | 0.9081 (2) | 1.0260 (5) | −0.2163 (7) | 0.066 (4) | |
H43 | 0.9152 | 0.9620 | −0.2173 | 0.079* | |
C44 | 0.9096 (3) | 1.0785 (8) | −0.3221 (6) | 0.091 (6) | |
H44 | 0.9177 | 1.0503 | −0.3953 | 0.110* | |
C45 | 0.8993 (3) | 1.1722 (7) | −0.3206 (7) | 0.098 (6) | |
H45 | 0.9003 | 1.2081 | −0.3929 | 0.118* | |
C46 | 0.8875 (3) | 1.2135 (5) | −0.2134 (9) | 0.096 (6) | |
H46 | 0.8804 | 1.2776 | −0.2124 | 0.115* | |
C47 | 0.8860 (3) | 1.1611 (5) | −0.1077 (7) | 0.070 (5) | |
H47 | 0.8779 | 1.1893 | −0.0344 | 0.084* | |
C48 | 0.7505 (4) | 0.9971 (11) | 0.3784 (14) | 0.080 (5) | |
H48A | 0.7627 | 1.0167 | 0.3033 | 0.119* | |
H48B | 0.7359 | 1.0493 | 0.4112 | 0.119* | |
H48C | 0.7338 | 0.9442 | 0.3617 | 0.119* | |
C49 | 0.7612 (3) | 0.8871 (10) | 0.6011 (13) | 0.063 (4) | |
H49A | 0.7581 | 0.8238 | 0.5684 | 0.094* | |
H49B | 0.7366 | 0.9139 | 0.6184 | 0.094* | |
H49C | 0.7758 | 0.8843 | 0.6759 | 0.094* | |
C50 | 0.8055 (4) | 1.0640 (9) | 0.5622 (14) | 0.072 (5) | |
H50A | 0.8268 | 1.0452 | 0.6120 | 0.108* | |
H50B | 0.7864 | 1.0931 | 0.6135 | 0.108* | |
H50C | 0.8137 | 1.1089 | 0.5008 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zr1 | 0.0321 (5) | 0.0383 (5) | 0.0464 (6) | 0.0035 (5) | 0.0039 (6) | −0.0009 (6) |
Zr2 | 0.0410 (5) | 0.0378 (5) | 0.0327 (5) | 0.0036 (5) | −0.0003 (6) | 0.0024 (6) |
Cl1 | 0.0488 (17) | 0.0609 (19) | 0.066 (2) | −0.0017 (16) | −0.0101 (18) | −0.0124 (17) |
Cl2 | 0.0609 (19) | 0.0439 (16) | 0.059 (2) | 0.0061 (15) | 0.0060 (18) | 0.0056 (15) |
Cl3 | 0.056 (2) | 0.062 (2) | 0.069 (2) | −0.0013 (16) | −0.0176 (18) | −0.0050 (18) |
Cl4 | 0.0555 (18) | 0.069 (2) | 0.0484 (19) | −0.0065 (16) | −0.0116 (17) | −0.0003 (16) |
Cl5 | 0.0594 (18) | 0.0466 (16) | 0.059 (2) | 0.0138 (14) | 0.0064 (18) | 0.0068 (16) |
Cl6 | 0.0568 (18) | 0.0536 (18) | 0.0528 (19) | 0.0002 (15) | −0.0157 (17) | −0.0079 (15) |
N1 | 0.048 (6) | 0.042 (6) | 0.058 (7) | 0.013 (5) | 0.010 (5) | 0.009 (5) |
N2 | 0.036 (5) | 0.048 (5) | 0.054 (6) | −0.001 (4) | 0.018 (6) | 0.005 (5) |
N3 | 0.046 (6) | 0.048 (6) | 0.059 (7) | 0.004 (5) | 0.003 (6) | 0.000 (5) |
N4 | 0.034 (5) | 0.049 (5) | 0.074 (7) | 0.013 (4) | 0.006 (6) | −0.010 (6) |
N5 | 0.049 (6) | 0.044 (6) | 0.049 (6) | 0.011 (5) | 0.003 (5) | 0.003 (5) |
N6 | 0.038 (5) | 0.045 (5) | 0.025 (5) | 0.000 (4) | −0.004 (4) | 0.000 (4) |
N7 | 0.046 (5) | 0.037 (5) | 0.045 (6) | −0.001 (4) | 0.007 (5) | 0.001 (4) |
N8 | 0.055 (6) | 0.043 (6) | 0.057 (7) | −0.001 (5) | 0.006 (6) | 0.005 (5) |
Si1 | 0.054 (2) | 0.059 (2) | 0.060 (2) | 0.0059 (19) | 0.015 (2) | 0.011 (2) |
Si2 | 0.0444 (19) | 0.058 (2) | 0.052 (2) | 0.0124 (17) | 0.0070 (19) | −0.0024 (18) |
C1 | 0.046 (7) | 0.059 (7) | 0.051 (8) | 0.003 (6) | 0.015 (6) | −0.016 (6) |
C2 | 0.042 (7) | 0.085 (10) | 0.082 (11) | 0.000 (7) | 0.001 (8) | −0.007 (8) |
C3 | 0.044 (7) | 0.089 (10) | 0.062 (9) | 0.018 (7) | 0.009 (7) | 0.007 (8) |
C4 | 0.054 (8) | 0.060 (8) | 0.069 (9) | 0.019 (7) | 0.020 (8) | 0.002 (7) |
C5 | 0.044 (7) | 0.063 (8) | 0.062 (9) | 0.018 (6) | −0.004 (7) | 0.011 (7) |
C6 | 0.033 (6) | 0.043 (6) | 0.047 (7) | 0.007 (5) | 0.020 (6) | 0.003 (6) |
C7 | 0.049 (7) | 0.038 (6) | 0.055 (8) | 0.000 (6) | 0.000 (7) | −0.006 (6) |
C8 | 0.039 (6) | 0.046 (6) | 0.060 (8) | 0.012 (5) | 0.016 (6) | 0.023 (6) |
C9 | 0.055 (7) | 0.053 (7) | 0.048 (7) | 0.009 (6) | 0.019 (7) | 0.009 (6) |
C10 | 0.080 (9) | 0.035 (6) | 0.064 (8) | 0.017 (6) | 0.033 (8) | 0.024 (6) |
C11 | 0.085 (11) | 0.121 (13) | 0.053 (10) | 0.027 (10) | 0.023 (9) | 0.002 (10) |
C12 | 0.163 (17) | 0.133 (15) | 0.055 (10) | 0.068 (13) | 0.030 (12) | 0.026 (10) |
C13 | 0.103 (12) | 0.133 (14) | 0.104 (13) | 0.049 (11) | 0.072 (11) | 0.050 (11) |
C14 | 0.074 (11) | 0.085 (11) | 0.133 (15) | 0.032 (8) | 0.047 (11) | 0.037 (11) |
C15 | 0.044 (7) | 0.049 (8) | 0.096 (11) | 0.008 (6) | 0.035 (8) | 0.001 (7) |
C16 | 0.049 (7) | 0.041 (6) | 0.049 (8) | −0.001 (5) | 0.005 (7) | −0.001 (6) |
C17 | 0.039 (6) | 0.042 (7) | 0.064 (8) | 0.001 (5) | 0.011 (7) | −0.001 (6) |
C18 | 0.064 (9) | 0.067 (9) | 0.100 (12) | 0.018 (8) | 0.024 (9) | 0.020 (9) |
C19 | 0.075 (11) | 0.153 (17) | 0.094 (13) | 0.018 (11) | 0.050 (10) | 0.016 (12) |
C20 | 0.062 (9) | 0.101 (12) | 0.134 (16) | 0.046 (9) | −0.017 (11) | −0.022 (12) |
C21 | 0.090 (11) | 0.065 (9) | 0.124 (15) | 0.036 (8) | −0.017 (12) | −0.016 (10) |
C22 | 0.056 (8) | 0.060 (8) | 0.060 (9) | −0.004 (7) | −0.009 (7) | 0.006 (7) |
C23 | 0.098 (12) | 0.107 (13) | 0.072 (11) | 0.030 (10) | −0.001 (10) | 0.016 (10) |
C24 | 0.086 (11) | 0.089 (11) | 0.062 (9) | 0.015 (9) | 0.036 (8) | 0.005 (8) |
C25 | 0.085 (11) | 0.078 (10) | 0.064 (10) | 0.003 (8) | 0.012 (9) | 0.023 (8) |
C26 | 0.085 (10) | 0.062 (8) | 0.049 (8) | −0.002 (7) | −0.002 (8) | 0.014 (7) |
C27 | 0.098 (11) | 0.076 (10) | 0.063 (9) | −0.001 (9) | 0.016 (9) | 0.024 (8) |
C28 | 0.083 (11) | 0.103 (12) | 0.047 (9) | 0.007 (9) | 0.002 (9) | 0.027 (8) |
C29 | 0.053 (8) | 0.099 (10) | 0.036 (8) | 0.007 (7) | −0.004 (7) | 0.006 (7) |
C30 | 0.043 (6) | 0.061 (8) | 0.055 (8) | 0.000 (6) | −0.002 (7) | −0.008 (7) |
C31 | 0.034 (6) | 0.042 (6) | 0.053 (8) | 0.005 (5) | 0.004 (6) | 0.001 (6) |
C32 | 0.040 (6) | 0.045 (6) | 0.032 (6) | 0.005 (5) | −0.007 (6) | −0.003 (5) |
C33 | 0.059 (7) | 0.044 (6) | 0.027 (6) | 0.015 (6) | 0.005 (6) | 0.000 (5) |
C34 | 0.055 (7) | 0.045 (7) | 0.056 (8) | 0.007 (6) | 0.008 (7) | 0.005 (6) |
C35 | 0.050 (7) | 0.038 (6) | 0.062 (9) | 0.005 (6) | 0.012 (7) | 0.001 (6) |
C36 | 0.072 (9) | 0.061 (8) | 0.048 (8) | 0.009 (7) | 0.014 (8) | −0.007 (7) |
C37 | 0.119 (13) | 0.082 (11) | 0.073 (11) | −0.010 (10) | 0.042 (10) | −0.017 (9) |
C38 | 0.079 (11) | 0.098 (13) | 0.109 (14) | 0.002 (9) | 0.057 (10) | 0.015 (10) |
C39 | 0.067 (10) | 0.118 (14) | 0.147 (18) | −0.035 (9) | 0.032 (12) | 0.006 (13) |
C40 | 0.053 (8) | 0.069 (8) | 0.084 (10) | −0.005 (7) | 0.004 (9) | −0.003 (9) |
C41 | 0.044 (7) | 0.040 (6) | 0.067 (8) | −0.011 (5) | 0.012 (7) | −0.004 (6) |
C42 | 0.045 (7) | 0.050 (7) | 0.034 (6) | −0.013 (5) | −0.005 (6) | 0.003 (6) |
C43 | 0.080 (10) | 0.075 (9) | 0.041 (8) | −0.009 (8) | 0.000 (8) | −0.010 (7) |
C44 | 0.117 (13) | 0.122 (14) | 0.035 (9) | −0.028 (11) | 0.012 (9) | 0.004 (9) |
C45 | 0.132 (15) | 0.105 (13) | 0.057 (10) | −0.015 (11) | 0.001 (11) | 0.034 (9) |
C46 | 0.166 (18) | 0.059 (9) | 0.063 (11) | 0.015 (10) | −0.010 (11) | 0.019 (8) |
C47 | 0.106 (12) | 0.055 (8) | 0.048 (8) | 0.010 (8) | −0.007 (9) | 0.001 (7) |
C48 | 0.047 (8) | 0.115 (13) | 0.076 (10) | 0.022 (8) | 0.005 (8) | 0.027 (9) |
C49 | 0.038 (7) | 0.090 (10) | 0.061 (9) | 0.010 (7) | 0.016 (7) | 0.003 (8) |
C50 | 0.081 (10) | 0.066 (9) | 0.070 (10) | 0.014 (8) | 0.012 (9) | −0.009 (8) |
Zr1—N2 | 2.159 (9) | C17—C22 | 1.3900 |
Zr1—N1 | 2.200 (10) | C18—C19 | 1.3900 |
Zr1—N4 | 2.328 (9) | C18—H18 | 0.9500 |
Zr1—Cl1 | 2.415 (4) | C19—C20 | 1.3900 |
Zr1—Cl3 | 2.422 (4) | C19—H19 | 0.9500 |
Zr1—Cl2 | 2.466 (3) | C20—C21 | 1.3900 |
Zr1—N3 | 2.496 (10) | C20—H20 | 0.9500 |
Zr1—C7 | 2.592 (12) | C21—C22 | 1.3900 |
Zr2—N6 | 2.135 (9) | C21—H21 | 0.9500 |
Zr2—N5 | 2.216 (10) | C22—H22 | 0.9500 |
Zr2—N8 | 2.351 (11) | C23—H23A | 0.9800 |
Zr2—Cl4 | 2.426 (3) | C23—H23B | 0.9800 |
Zr2—Cl6 | 2.433 (3) | C23—H23C | 0.9800 |
Zr2—Cl5 | 2.464 (3) | C24—H24A | 0.9800 |
Zr2—N7 | 2.470 (9) | C24—H24B | 0.9800 |
Zr2—C32 | 2.587 (12) | C24—H24C | 0.9800 |
N1—C7 | 1.303 (14) | C25—H25A | 0.9800 |
N1—Si1 | 1.758 (11) | C25—H25B | 0.9800 |
N2—C7 | 1.334 (14) | C25—H25C | 0.9800 |
N2—C8 | 1.421 (14) | C26—C27 | 1.3900 |
N3—C10 | 1.446 (16) | C26—C31 | 1.3900 |
N3—C9 | 1.477 (15) | C26—H26 | 0.9500 |
N3—H3A | 0.8800 | C27—C28 | 1.3900 |
N4—C16 | 1.118 (14) | C27—H27 | 0.9500 |
N5—C32 | 1.309 (14) | C28—C29 | 1.3900 |
N5—Si2 | 1.744 (10) | C28—H28 | 0.9500 |
N6—C32 | 1.332 (14) | C29—C30 | 1.3900 |
N6—C33 | 1.430 (14) | C29—H29 | 0.9500 |
N7—C35 | 1.451 (15) | C30—C31 | 1.3900 |
N7—C34 | 1.471 (15) | C30—H30 | 0.9500 |
N7—H7A | 0.8800 | C31—C32 | 1.466 (13) |
N8—C41 | 1.125 (16) | C33—C34 | 1.487 (16) |
Si1—C25 | 1.814 (15) | C33—H33A | 0.9900 |
Si1—C24 | 1.854 (15) | C33—H33B | 0.9900 |
Si1—C23 | 1.856 (16) | C34—H34A | 0.9900 |
Si2—C50 | 1.817 (15) | C34—H34B | 0.9900 |
Si2—C48 | 1.829 (14) | C35—C40 | 1.356 (18) |
Si2—C49 | 1.863 (14) | C35—C36 | 1.406 (18) |
C1—C2 | 1.3900 | C36—C37 | 1.39 (2) |
C1—C6 | 1.3900 | C36—H36 | 0.9500 |
C1—H1 | 0.9500 | C37—C38 | 1.33 (2) |
C2—C3 | 1.3900 | C37—H37 | 0.9500 |
C2—H2 | 0.9500 | C38—C39 | 1.40 (3) |
C3—C4 | 1.3900 | C38—H38 | 0.9500 |
C3—H3 | 0.9500 | C39—C40 | 1.36 (2) |
C4—C5 | 1.3900 | C39—H39 | 0.9500 |
C4—H4 | 0.9500 | C40—H40 | 0.9500 |
C5—C6 | 1.3900 | C41—C42 | 1.399 (15) |
C5—H5 | 0.9500 | C42—C43 | 1.3900 |
C6—C7 | 1.458 (13) | C42—C47 | 1.3900 |
C8—C9 | 1.482 (16) | C43—C44 | 1.3900 |
C8—H8A | 0.9900 | C43—H43 | 0.9500 |
C8—H8B | 0.9900 | C44—C45 | 1.3900 |
C9—H9A | 0.9900 | C44—H44 | 0.9500 |
C9—H9B | 0.9900 | C45—C46 | 1.3900 |
C10—C11 | 1.34 (2) | C45—H45 | 0.9500 |
C10—C15 | 1.420 (18) | C46—C47 | 1.3900 |
C11—C12 | 1.36 (2) | C46—H46 | 0.9500 |
C11—H11 | 0.9500 | C47—H47 | 0.9500 |
C12—C13 | 1.40 (3) | C48—H48A | 0.9800 |
C12—H12 | 0.9500 | C48—H48B | 0.9800 |
C13—C14 | 1.32 (3) | C48—H48C | 0.9800 |
C13—H13 | 0.9500 | C49—H49A | 0.9800 |
C14—C15 | 1.37 (2) | C49—H49B | 0.9800 |
C14—H14 | 0.9500 | C49—H49C | 0.9800 |
C15—H15 | 0.9500 | C50—H50A | 0.9800 |
C16—C17 | 1.389 (13) | C50—H50B | 0.9800 |
C17—C18 | 1.3900 | C50—H50C | 0.9800 |
N2—Zr1—N1 | 60.0 (3) | C13—C12—H12 | 120.1 |
N2—Zr1—N4 | 140.2 (3) | C14—C13—C12 | 120.5 (17) |
N1—Zr1—N4 | 159.4 (4) | C14—C13—H13 | 119.7 |
N2—Zr1—Cl1 | 91.2 (3) | C12—C13—H13 | 119.7 |
N1—Zr1—Cl1 | 95.8 (3) | C13—C14—C15 | 121.5 (17) |
N4—Zr1—Cl1 | 82.0 (3) | C13—C14—H14 | 119.2 |
N2—Zr1—Cl3 | 92.3 (3) | C15—C14—H14 | 119.2 |
N1—Zr1—Cl3 | 98.0 (3) | C14—C15—C10 | 116.7 (15) |
N4—Zr1—Cl3 | 86.4 (3) | C14—C15—H15 | 121.7 |
Cl1—Zr1—Cl3 | 165.62 (13) | C10—C15—H15 | 121.7 |
N2—Zr1—Cl2 | 143.0 (3) | N4—C16—C17 | 178.0 (13) |
N1—Zr1—Cl2 | 83.0 (3) | C16—C17—C18 | 118.8 (7) |
N4—Zr1—Cl2 | 76.8 (3) | C16—C17—C22 | 121.1 (7) |
Cl1—Zr1—Cl2 | 94.48 (12) | C18—C17—C22 | 120.0 |
Cl3—Zr1—Cl2 | 91.12 (12) | C17—C18—C19 | 120.0 |
N2—Zr1—N3 | 65.6 (3) | C17—C18—H18 | 120.0 |
N1—Zr1—N3 | 125.6 (3) | C19—C18—H18 | 120.0 |
N4—Zr1—N3 | 74.7 (3) | C20—C19—C18 | 120.0 |
Cl1—Zr1—N3 | 84.9 (3) | C20—C19—H19 | 120.0 |
Cl3—Zr1—N3 | 83.8 (3) | C18—C19—H19 | 120.0 |
Cl2—Zr1—N3 | 151.3 (2) | C19—C20—C21 | 120.0 |
N2—Zr1—C7 | 31.0 (3) | C19—C20—H20 | 120.0 |
N1—Zr1—C7 | 30.2 (4) | C21—C20—H20 | 120.0 |
N4—Zr1—C7 | 170.4 (4) | C20—C21—C22 | 120.0 |
Cl1—Zr1—C7 | 100.0 (3) | C20—C21—H21 | 120.0 |
Cl3—Zr1—C7 | 90.1 (3) | C22—C21—H21 | 120.0 |
Cl2—Zr1—C7 | 112.3 (3) | C21—C22—C17 | 120.0 |
N3—Zr1—C7 | 96.0 (3) | C21—C22—H22 | 120.0 |
N6—Zr2—N5 | 60.2 (3) | C17—C22—H22 | 120.0 |
N6—Zr2—N8 | 140.9 (3) | Si1—C23—H23A | 109.5 |
N5—Zr2—N8 | 158.8 (3) | Si1—C23—H23B | 109.5 |
N6—Zr2—Cl4 | 90.3 (2) | H23A—C23—H23B | 109.5 |
N5—Zr2—Cl4 | 100.3 (3) | Si1—C23—H23C | 109.5 |
N8—Zr2—Cl4 | 80.8 (3) | H23A—C23—H23C | 109.5 |
N6—Zr2—Cl6 | 94.5 (2) | H23B—C23—H23C | 109.5 |
N5—Zr2—Cl6 | 94.3 (3) | Si1—C24—H24A | 109.5 |
N8—Zr2—Cl6 | 86.7 (3) | Si1—C24—H24B | 109.5 |
Cl4—Zr2—Cl6 | 165.14 (12) | H24A—C24—H24B | 109.5 |
N6—Zr2—Cl5 | 144.0 (3) | Si1—C24—H24C | 109.5 |
N5—Zr2—Cl5 | 83.9 (2) | H24A—C24—H24C | 109.5 |
N8—Zr2—Cl5 | 74.9 (2) | H24B—C24—H24C | 109.5 |
Cl4—Zr2—Cl5 | 94.40 (12) | Si1—C25—H25A | 109.5 |
Cl6—Zr2—Cl5 | 90.02 (12) | Si1—C25—H25B | 109.5 |
N6—Zr2—N7 | 66.6 (3) | H25A—C25—H25B | 109.5 |
N5—Zr2—N7 | 126.6 (3) | Si1—C25—H25C | 109.5 |
N8—Zr2—N7 | 74.6 (3) | H25A—C25—H25C | 109.5 |
Cl4—Zr2—N7 | 83.7 (2) | H25B—C25—H25C | 109.5 |
Cl6—Zr2—N7 | 85.2 (2) | C27—C26—C31 | 120.0 |
Cl5—Zr2—N7 | 149.4 (2) | C27—C26—H26 | 120.0 |
N6—Zr2—C32 | 30.9 (3) | C31—C26—H26 | 120.0 |
N5—Zr2—C32 | 30.4 (3) | C26—C27—C28 | 120.0 |
N8—Zr2—C32 | 170.3 (4) | C26—C27—H27 | 120.0 |
Cl4—Zr2—C32 | 102.2 (3) | C28—C27—H27 | 120.0 |
Cl6—Zr2—C32 | 88.9 (3) | C27—C28—C29 | 120.0 |
Cl5—Zr2—C32 | 113.8 (3) | C27—C28—H28 | 120.0 |
N7—Zr2—C32 | 96.4 (3) | C29—C28—H28 | 120.0 |
C7—N1—Si1 | 128.5 (9) | C30—C29—C28 | 120.0 |
C7—N1—Zr1 | 91.8 (8) | C30—C29—H29 | 120.0 |
Si1—N1—Zr1 | 139.8 (5) | C28—C29—H29 | 120.0 |
C7—N2—C8 | 128.2 (9) | C31—C30—C29 | 120.0 |
C7—N2—Zr1 | 92.7 (7) | C31—C30—H30 | 120.0 |
C8—N2—Zr1 | 129.8 (7) | C29—C30—H30 | 120.0 |
C10—N3—C9 | 111.5 (10) | C30—C31—C26 | 120.0 |
C10—N3—Zr1 | 124.8 (7) | C30—C31—C32 | 118.0 (6) |
C9—N3—Zr1 | 107.3 (7) | C26—C31—C32 | 122.0 (6) |
C10—N3—H3A | 119.3 | N5—C32—N6 | 111.5 (10) |
C9—N3—H3A | 105.8 | N5—C32—C31 | 126.4 (10) |
Zr1—N3—H3A | 84.5 | N6—C32—C31 | 121.9 (9) |
C16—N4—Zr1 | 172.9 (11) | N5—C32—Zr2 | 58.9 (6) |
C32—N5—Si2 | 129.4 (9) | N6—C32—Zr2 | 55.5 (6) |
C32—N5—Zr2 | 90.7 (7) | C31—C32—Zr2 | 160.7 (7) |
Si2—N5—Zr2 | 139.7 (5) | N6—C33—C34 | 106.4 (9) |
C32—N6—C33 | 128.0 (9) | N6—C33—H33A | 110.4 |
C32—N6—Zr2 | 93.6 (7) | C34—C33—H33A | 110.4 |
C33—N6—Zr2 | 130.3 (7) | N6—C33—H33B | 110.4 |
C35—N7—C34 | 110.7 (9) | C34—C33—H33B | 110.4 |
C35—N7—Zr2 | 122.4 (7) | H33A—C33—H33B | 108.6 |
C34—N7—Zr2 | 108.1 (7) | N7—C34—C33 | 109.7 (10) |
C35—N7—H7A | 119.2 | N7—C34—H34A | 109.7 |
C34—N7—H7A | 105.7 | C33—C34—H34A | 109.7 |
Zr2—N7—H7A | 87.9 | N7—C34—H34B | 109.7 |
C41—N8—Zr2 | 163.2 (10) | C33—C34—H34B | 109.7 |
N1—Si1—C25 | 109.5 (6) | H34A—C34—H34B | 108.2 |
N1—Si1—C24 | 110.9 (6) | C40—C35—C36 | 121.0 (13) |
C25—Si1—C24 | 111.5 (7) | C40—C35—N7 | 121.5 (12) |
N1—Si1—C23 | 106.6 (6) | C36—C35—N7 | 117.4 (11) |
C25—Si1—C23 | 112.2 (7) | C37—C36—C35 | 116.7 (14) |
C24—Si1—C23 | 106.0 (7) | C37—C36—H36 | 121.6 |
N5—Si2—C50 | 110.5 (6) | C35—C36—H36 | 121.6 |
N5—Si2—C48 | 109.1 (6) | C38—C37—C36 | 123.1 (16) |
C50—Si2—C48 | 110.1 (7) | C38—C37—H37 | 118.4 |
N5—Si2—C49 | 111.0 (5) | C36—C37—H37 | 118.4 |
C50—Si2—C49 | 110.1 (7) | C37—C38—C39 | 118.3 (16) |
C48—Si2—C49 | 105.9 (6) | C37—C38—H38 | 120.9 |
C2—C1—C6 | 120.0 | C39—C38—H38 | 120.9 |
C2—C1—H1 | 120.0 | C40—C39—C38 | 121.0 (17) |
C6—C1—H1 | 120.0 | C40—C39—H39 | 119.5 |
C3—C2—C1 | 120.0 | C38—C39—H39 | 119.5 |
C3—C2—H2 | 120.0 | C35—C40—C39 | 119.7 (16) |
C1—C2—H2 | 120.0 | C35—C40—H40 | 120.2 |
C2—C3—C4 | 120.0 | C39—C40—H40 | 120.2 |
C2—C3—H3 | 120.0 | N8—C41—C42 | 176.2 (13) |
C4—C3—H3 | 120.0 | C43—C42—C47 | 120.0 |
C3—C4—C5 | 120.0 | C43—C42—C41 | 122.3 (7) |
C3—C4—H4 | 120.0 | C47—C42—C41 | 117.6 (7) |
C5—C4—H4 | 120.0 | C42—C43—C44 | 120.0 |
C6—C5—C4 | 120.0 | C42—C43—H43 | 120.0 |
C6—C5—H5 | 120.0 | C44—C43—H43 | 120.0 |
C4—C5—H5 | 120.0 | C45—C44—C43 | 120.0 |
C5—C6—C1 | 120.0 | C45—C44—H44 | 120.0 |
C5—C6—C7 | 120.1 (6) | C43—C44—H44 | 120.0 |
C1—C6—C7 | 119.9 (6) | C46—C45—C44 | 120.0 |
N1—C7—N2 | 111.6 (10) | C46—C45—H45 | 120.0 |
N1—C7—C6 | 127.6 (10) | C44—C45—H45 | 120.0 |
N2—C7—C6 | 120.6 (10) | C47—C46—C45 | 120.0 |
N1—C7—Zr1 | 58.1 (6) | C47—C46—H46 | 120.0 |
N2—C7—Zr1 | 56.3 (6) | C45—C46—H46 | 120.0 |
C6—C7—Zr1 | 159.8 (8) | C46—C47—C42 | 120.0 |
N2—C8—C9 | 107.4 (9) | C46—C47—H47 | 120.0 |
N2—C8—H8A | 110.2 | C42—C47—H47 | 120.0 |
C9—C8—H8A | 110.2 | Si2—C48—H48A | 109.5 |
N2—C8—H8B | 110.2 | Si2—C48—H48B | 109.5 |
C9—C8—H8B | 110.2 | H48A—C48—H48B | 109.5 |
H8A—C8—H8B | 108.5 | Si2—C48—H48C | 109.5 |
N3—C9—C8 | 109.8 (10) | H48A—C48—H48C | 109.5 |
N3—C9—H9A | 109.7 | H48B—C48—H48C | 109.5 |
C8—C9—H9A | 109.7 | Si2—C49—H49A | 109.5 |
N3—C9—H9B | 109.7 | Si2—C49—H49B | 109.5 |
C8—C9—H9B | 109.7 | H49A—C49—H49B | 109.5 |
H9A—C9—H9B | 108.2 | Si2—C49—H49C | 109.5 |
C11—C10—C15 | 122.4 (14) | H49A—C49—H49C | 109.5 |
C11—C10—N3 | 122.6 (13) | H49B—C49—H49C | 109.5 |
C15—C10—N3 | 114.9 (12) | Si2—C50—H50A | 109.5 |
C10—C11—C12 | 119.0 (17) | Si2—C50—H50B | 109.5 |
C10—C11—H11 | 120.5 | H50A—C50—H50B | 109.5 |
C12—C11—H11 | 120.5 | Si2—C50—H50C | 109.5 |
C11—C12—C13 | 119.8 (19) | H50A—C50—H50C | 109.5 |
C11—C12—H12 | 120.1 | H50B—C50—H50C | 109.5 |
C7—N1—Si1—C25 | −104.3 (12) | C17—C18—C19—C20 | 0.0 |
Zr1—N1—Si1—C25 | 75.2 (10) | C18—C19—C20—C21 | 0.0 |
C7—N1—Si1—C24 | 19.2 (13) | C19—C20—C21—C22 | 0.0 |
Zr1—N1—Si1—C24 | −161.3 (9) | C20—C21—C22—C17 | 0.0 |
C7—N1—Si1—C23 | 134.2 (12) | C16—C17—C22—C21 | −177.2 (8) |
Zr1—N1—Si1—C23 | −46.3 (11) | C18—C17—C22—C21 | 0.0 |
C32—N5—Si2—C50 | 103.1 (12) | C31—C26—C27—C28 | 0.0 |
Zr2—N5—Si2—C50 | −68.9 (10) | C26—C27—C28—C29 | 0.0 |
C32—N5—Si2—C48 | −135.7 (11) | C27—C28—C29—C30 | 0.0 |
Zr2—N5—Si2—C48 | 52.3 (10) | C28—C29—C30—C31 | 0.0 |
C32—N5—Si2—C49 | −19.4 (13) | C29—C30—C31—C26 | 0.0 |
Zr2—N5—Si2—C49 | 168.7 (8) | C29—C30—C31—C32 | 177.8 (7) |
C6—C1—C2—C3 | 0.0 | C27—C26—C31—C30 | 0.0 |
C1—C2—C3—C4 | 0.0 | C27—C26—C31—C32 | −177.7 (7) |
C2—C3—C4—C5 | 0.0 | Si2—N5—C32—N6 | 166.8 (8) |
C3—C4—C5—C6 | 0.0 | Zr2—N5—C32—N6 | −18.3 (9) |
C4—C5—C6—C1 | 0.0 | Si2—N5—C32—C31 | −17.2 (17) |
C4—C5—C6—C7 | 179.7 (9) | Zr2—N5—C32—C31 | 157.6 (10) |
C2—C1—C6—C5 | 0.0 | Si2—N5—C32—Zr2 | −174.8 (11) |
C2—C1—C6—C7 | −179.7 (9) | C33—N6—C32—N5 | 169.7 (10) |
Si1—N1—C7—N2 | −162.1 (9) | Zr2—N6—C32—N5 | 19.1 (10) |
Zr1—N1—C7—N2 | 18.2 (10) | C33—N6—C32—C31 | −6.5 (17) |
Si1—N1—C7—C6 | 23.3 (19) | Zr2—N6—C32—C31 | −157.1 (9) |
Zr1—N1—C7—C6 | −156.4 (11) | C33—N6—C32—Zr2 | 150.6 (12) |
Si1—N1—C7—Zr1 | 179.7 (12) | C30—C31—C32—N5 | −51.0 (13) |
C8—N2—C7—N1 | −167.3 (11) | C26—C31—C32—N5 | 126.8 (10) |
Zr1—N2—C7—N1 | −18.6 (11) | C30—C31—C32—N6 | 124.6 (9) |
C8—N2—C7—C6 | 7.7 (18) | C26—C31—C32—N6 | −57.7 (12) |
Zr1—N2—C7—C6 | 156.4 (9) | C30—C31—C32—Zr2 | 49 (2) |
C8—N2—C7—Zr1 | −148.7 (14) | C26—C31—C32—Zr2 | −133.7 (19) |
C5—C6—C7—N1 | −126.5 (11) | C32—N6—C33—C34 | −132.6 (11) |
C1—C6—C7—N1 | 53.2 (15) | Zr2—N6—C33—C34 | 7.4 (13) |
C5—C6—C7—N2 | 59.4 (13) | C35—N7—C34—C33 | −175.8 (9) |
C1—C6—C7—N2 | −121.0 (10) | Zr2—N7—C34—C33 | 47.6 (10) |
C5—C6—C7—Zr1 | 134.3 (19) | N6—C33—C34—N7 | −37.1 (12) |
C1—C6—C7—Zr1 | −46 (3) | C34—N7—C35—C40 | −56.7 (14) |
C7—N2—C8—C9 | 138.0 (12) | Zr2—N7—C35—C40 | 72.6 (14) |
Zr1—N2—C8—C9 | 0.5 (14) | C34—N7—C35—C36 | 126.7 (12) |
C10—N3—C9—C8 | 171.7 (10) | Zr2—N7—C35—C36 | −104.0 (11) |
Zr1—N3—C9—C8 | −48.4 (11) | C40—C35—C36—C37 | 1 (2) |
N2—C8—C9—N3 | 33.9 (13) | N7—C35—C36—C37 | 177.6 (12) |
C9—N3—C10—C11 | 55.8 (16) | C35—C36—C37—C38 | −3 (2) |
Zr1—N3—C10—C11 | −75.6 (15) | C36—C37—C38—C39 | 5 (3) |
C9—N3—C10—C15 | −123.5 (12) | C37—C38—C39—C40 | −4 (3) |
Zr1—N3—C10—C15 | 105.0 (11) | C36—C35—C40—C39 | 0 (2) |
C15—C10—C11—C12 | 1 (2) | N7—C35—C40—C39 | −176.6 (13) |
N3—C10—C11—C12 | −177.9 (13) | C38—C39—C40—C35 | 1 (3) |
C10—C11—C12—C13 | 0 (3) | C47—C42—C43—C44 | 0.0 |
C11—C12—C13—C14 | −3 (3) | C41—C42—C43—C44 | 175.6 (8) |
C12—C13—C14—C15 | 4 (3) | C42—C43—C44—C45 | 0.0 |
C13—C14—C15—C10 | −2 (2) | C43—C44—C45—C46 | 0.0 |
C11—C10—C15—C14 | −1 (2) | C44—C45—C46—C47 | 0.0 |
N3—C10—C15—C14 | 178.8 (11) | C45—C46—C47—C42 | 0.0 |
C16—C17—C18—C19 | 177.3 (8) | C43—C42—C47—C46 | 0.0 |
C22—C17—C18—C19 | 0.0 | C41—C42—C47—C46 | −175.8 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C40—H40···Cl6 | 0.95 | 2.83 | 3.466 (16) | 125 |
C34—H34A···Cl6 | 0.99 | 2.99 | 3.525 (13) | 115 |
C9—H9B···Cl3 | 0.99 | 2.85 | 3.404 (13) | 116 |
N7—H7A···Cl4 | 0.88 | 2.70 | 3.267 (10) | 123 |
N7—H7A···Cl2 | 0.88 | 2.84 | 3.467 (10) | 129 |
N3—H3A···Cl5i | 0.88 | 2.98 | 3.516 (10) | 121 |
N3—H3A···Cl1 | 0.88 | 2.74 | 3.316 (11) | 124 |
Symmetry code: (i) x, y−1, z. |
Funding information
Funding for this research was provided by: National Natural Science Foundation of Chinahttps://doi.org/10.13039/501100001809 (award No. 21272142); the Natural Science Foundation of Shanxi Province (award No. 2015011015).
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