The title compound, [Zr(C5H5)2Cl(C20H24N)], is the second example of an enamido zirconocene to be crystallographically characterized. The geometry about nitrogen is planar, but the orientation of the aryl and vinyl substituents indicates that the nitrogen lone pair is not conjugated with their π-systems. These features are attributed to the steric bulk of the complex.
Supporting information
CCDC reference: 608540
Key indicators
- Single-crystal X-ray study
- T = 161 K
- Mean (C-C) = 0.008 Å
- R factor = 0.039
- wR factor = 0.039
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.70 Deg.
| Author Response: The structure was integrated to 0.850 angstroms, which was standard
proceedure in our lab at the time the data was collected.
|
Alert level C
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5880
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.70 Deg.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 24.70
From the CIF: _reflns_number_total 4287
Count of symmetry unique reflns 2524
Completeness (_total/calc) 169.85%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1763
Fraction of Friedel pairs measured 0.698
Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.
Chloro[
N-(2,6-diisopropylphenyl)-
N-(1-
phenylvinyl)amide]bis(
η5-cyclopentadienyl)zirconium
top
Crystal data top
[ZrCl(C5H5)2(C20H24N)] | F(000) = 1112 |
Mr = 535.28 | Dx = 1.366 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2777 reflections |
a = 9.5134 (8) Å | θ = 2.4–22.6° |
b = 14.718 (1) Å | µ = 0.54 mm−1 |
c = 18.591 (2) Å | T = 161 K |
V = 2603.2 (4) Å3 | Column, yellow |
Z = 4 | 0.20 × 0.10 × 0.08 mm |
Data collection top
Bruker SMART 1000 diffractometer | 3249 reflections with I > 3σ(I) |
ω scans | Rint = 0.055 |
Absorption correction: multi-scan (Blessing, 1995) | θmax = 24.7° |
Tmin = 0.870, Tmax = 0.958 | h = 0→11 |
11464 measured reflections | k = 0→17 |
4287 independent reflections | l = −21→21 |
Refinement top
Refinement on F | w = 1/[σ2(Fo) + 0.00022|Fo|2] |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max = 0.001 |
wR(F2) = 0.039 | Δρmax = 0.46 e Å−3 |
S = 1.09 | Δρmin = −0.68 e Å−3 |
3249 reflections | Absolute structure: Flack (1983), 1807 Friedel pairs |
298 parameters | Absolute structure parameter: 0.06 (5) |
H-atom parameters constrained | |
Special details top
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The
weighted R-factor (wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zr1 | 0.37674 (5) | 0.59853 (3) | 0.06610 (3) | 0.0138 (1) | |
Cl1 | 0.2811 (1) | 0.69364 (9) | −0.03190 (7) | 0.0237 (4) | |
N1 | 0.1950 (4) | 0.5168 (3) | 0.0870 (2) | 0.015 (1) | |
C1 | 0.4485 (6) | 0.4799 (4) | −0.0263 (3) | 0.034 (2) | |
C2 | 0.4955 (6) | 0.4489 (4) | 0.0410 (3) | 0.031 (2) | |
C3 | 0.6001 (5) | 0.5085 (4) | 0.0659 (3) | 0.029 (2) | |
C4 | 0.6185 (6) | 0.5760 (3) | 0.0123 (3) | 0.028 (2) | |
C5 | 0.5272 (6) | 0.5577 (4) | −0.0436 (3) | 0.029 (2) | |
C6 | 0.3241 (6) | 0.6577 (4) | 0.1911 (3) | 0.023 (2) | |
C7 | 0.4658 (6) | 0.6313 (4) | 0.1908 (3) | 0.027 (2) | |
C8 | 0.5391 (6) | 0.6921 (4) | 0.1452 (3) | 0.026 (2) | |
C9 | 0.4409 (7) | 0.7531 (4) | 0.1164 (3) | 0.030 (2) | |
C10 | 0.3072 (7) | 0.7309 (4) | 0.1457 (3) | 0.030 (2) | |
C11 | 0.0655 (5) | 0.5562 (4) | 0.1128 (3) | 0.017 (1) | |
C12 | 0.0223 (6) | 0.6369 (4) | 0.0880 (3) | 0.028 (2) | |
C13 | −0.0233 (5) | 0.5120 (4) | 0.1684 (3) | 0.019 (2) | |
C14 | −0.0918 (5) | 0.4291 (4) | 0.1584 (3) | 0.023 (2) | |
C15 | −0.1835 (5) | 0.3953 (4) | 0.2103 (3) | 0.027 (2) | |
C16 | −0.2089 (6) | 0.4425 (4) | 0.2730 (3) | 0.031 (2) | |
C17 | −0.1417 (6) | 0.5242 (4) | 0.2848 (3) | 0.031 (2) | |
C18 | −0.0509 (6) | 0.5591 (4) | 0.2327 (3) | 0.026 (2) | |
C19 | 0.1845 (5) | 0.4183 (3) | 0.0791 (3) | 0.018 (2) | |
C20 | 0.2222 (5) | 0.3605 (3) | 0.1366 (3) | 0.018 (2) | |
C21 | 0.2079 (6) | 0.2677 (4) | 0.1264 (3) | 0.027 (2) | |
C22 | 0.1538 (6) | 0.2328 (3) | 0.0632 (4) | 0.034 (2) | |
C23 | 0.1153 (7) | 0.2895 (4) | 0.0085 (3) | 0.031 (2) | |
C24 | 0.1314 (6) | 0.3834 (3) | 0.0146 (3) | 0.020 (1) | |
C25 | 0.2767 (5) | 0.3956 (4) | 0.2082 (3) | 0.025 (2) | |
C26 | 0.4312 (6) | 0.3697 (4) | 0.2206 (3) | 0.033 (2) | |
C27 | 0.1871 (6) | 0.3608 (4) | 0.2717 (3) | 0.032 (2) | |
C28 | 0.0853 (5) | 0.4441 (4) | −0.0473 (3) | 0.027 (2) | |
C29 | 0.1236 (8) | 0.4068 (4) | −0.1217 (3) | 0.044 (2) | |
C30 | −0.0732 (6) | 0.4621 (4) | −0.0456 (3) | 0.041 (2) | |
H1 | 0.3763 | 0.4534 | −0.0548 | 0.0395* | |
H2 | 0.4622 | 0.3964 | 0.0654 | 0.0363* | |
H3 | 0.6489 | 0.5043 | 0.1103 | 0.0336* | |
H4 | 0.6828 | 0.6252 | 0.0145 | 0.0336* | |
H5 | 0.5189 | 0.5920 | −0.0866 | 0.0361* | |
H6 | 0.2516 | 0.6297 | 0.2183 | 0.0279* | |
H7 | 0.5055 | 0.5815 | 0.2162 | 0.0317* | |
H8 | 0.6374 | 0.6919 | 0.1359 | 0.0327* | |
H9 | 0.4604 | 0.8008 | 0.0833 | 0.0350* | |
H10 | 0.2213 | 0.7612 | 0.1357 | 0.0364* | |
H11 | −0.0620 | 0.6633 | 0.1058 | 0.0329* | |
H12 | 0.0757 | 0.6679 | 0.0524 | 0.0329* | |
H13 | −0.0760 | 0.3950 | 0.1158 | 0.0281* | |
H14 | −0.2296 | 0.3390 | 0.2025 | 0.0330* | |
H15 | −0.2722 | 0.4192 | 0.3080 | 0.0369* | |
H16 | −0.1567 | 0.5568 | 0.3282 | 0.0330* | |
H17 | −0.0062 | 0.6161 | 0.2409 | 0.0316* | |
H18 | 0.2357 | 0.2272 | 0.1635 | 0.0321* | |
H19 | 0.1433 | 0.1690 | 0.0577 | 0.0408* | |
H20 | 0.0764 | 0.2647 | −0.0345 | 0.0361* | |
H21 | 0.2706 | 0.4598 | 0.2077 | 0.0301* | |
H22 | 0.4615 | 0.3930 | 0.2656 | 0.0394* | |
H23 | 0.4872 | 0.3945 | 0.1832 | 0.0394* | |
H24 | 0.4401 | 0.3053 | 0.2207 | 0.0394* | |
H25 | 0.1905 | 0.2962 | 0.2731 | 0.0384* | |
H26 | 0.0925 | 0.3799 | 0.2657 | 0.0384* | |
H27 | 0.2231 | 0.3845 | 0.3155 | 0.0384* | |
H28 | 0.1314 | 0.5008 | −0.0420 | 0.0335* | |
H29 | 0.2224 | 0.3983 | −0.1244 | 0.0532* | |
H30 | 0.0944 | 0.4484 | −0.1576 | 0.0532* | |
H31 | 0.0776 | 0.3501 | −0.1288 | 0.0532* | |
H32 | −0.1227 | 0.4067 | −0.0527 | 0.0485* | |
H33 | −0.0975 | 0.5037 | −0.0826 | 0.0485* | |
H34 | −0.0985 | 0.4871 | −0.0002 | 0.0485* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zr1 | 0.0151 (2) | 0.0141 (2) | 0.0122 (2) | −0.0000 (3) | 0.0006 (2) | −0.0002 (2) |
Cl1 | 0.0273 (8) | 0.0242 (8) | 0.0196 (7) | 0.0030 (7) | 0.0016 (6) | 0.0074 (6) |
N1 | 0.016 (2) | 0.015 (3) | 0.016 (3) | 0.002 (2) | −0.001 (2) | 0.003 (2) |
C1 | 0.026 (3) | 0.040 (4) | 0.037 (4) | 0.005 (3) | 0.005 (3) | −0.022 (3) |
C2 | 0.032 (4) | 0.025 (3) | 0.036 (4) | 0.008 (3) | 0.016 (3) | 0.001 (3) |
C3 | 0.022 (3) | 0.034 (3) | 0.030 (3) | 0.013 (3) | −0.003 (3) | −0.004 (3) |
C4 | 0.021 (3) | 0.025 (4) | 0.038 (3) | −0.003 (3) | 0.010 (3) | 0.001 (2) |
C5 | 0.029 (3) | 0.035 (4) | 0.024 (4) | 0.007 (3) | 0.014 (3) | −0.002 (3) |
C6 | 0.026 (3) | 0.030 (4) | 0.013 (3) | −0.009 (3) | 0.004 (2) | −0.008 (3) |
C7 | 0.035 (4) | 0.037 (4) | 0.009 (3) | −0.006 (3) | −0.002 (3) | −0.004 (2) |
C8 | 0.028 (3) | 0.037 (4) | 0.014 (3) | −0.014 (3) | −0.002 (3) | −0.007 (3) |
C9 | 0.057 (4) | 0.019 (3) | 0.015 (3) | −0.011 (3) | 0.006 (3) | −0.007 (3) |
C10 | 0.045 (4) | 0.018 (3) | 0.027 (4) | 0.006 (3) | 0.003 (3) | −0.010 (3) |
C11 | 0.020 (3) | 0.015 (3) | 0.017 (3) | −0.001 (2) | 0.001 (2) | 0.003 (3) |
C12 | 0.020 (3) | 0.034 (4) | 0.031 (4) | 0.006 (3) | 0.006 (2) | 0.016 (3) |
C13 | 0.015 (3) | 0.019 (3) | 0.023 (3) | 0.004 (2) | 0.001 (2) | 0.004 (2) |
C14 | 0.020 (3) | 0.030 (4) | 0.021 (3) | 0.001 (2) | −0.003 (2) | 0.004 (2) |
C15 | 0.019 (3) | 0.026 (3) | 0.036 (3) | −0.003 (3) | 0.001 (3) | 0.003 (3) |
C16 | 0.017 (3) | 0.037 (4) | 0.039 (4) | 0.005 (3) | 0.008 (3) | 0.017 (3) |
C17 | 0.032 (4) | 0.041 (4) | 0.022 (3) | 0.012 (3) | 0.006 (3) | 0.004 (3) |
C18 | 0.026 (3) | 0.024 (3) | 0.029 (4) | 0.002 (3) | 0.005 (3) | 0.001 (3) |
C19 | 0.011 (2) | 0.017 (3) | 0.025 (3) | −0.001 (2) | −0.001 (2) | −0.003 (2) |
C20 | 0.014 (3) | 0.019 (3) | 0.023 (3) | 0.003 (2) | −0.003 (2) | 0.001 (2) |
C21 | 0.018 (3) | 0.025 (4) | 0.037 (4) | 0.000 (3) | −0.005 (3) | 0.010 (3) |
C22 | 0.037 (4) | 0.016 (3) | 0.050 (4) | −0.003 (2) | −0.007 (4) | −0.003 (3) |
C23 | 0.025 (3) | 0.029 (3) | 0.038 (4) | −0.005 (3) | −0.011 (3) | −0.013 (3) |
C24 | 0.016 (3) | 0.020 (3) | 0.025 (3) | 0.002 (3) | −0.002 (3) | −0.003 (2) |
C25 | 0.027 (3) | 0.023 (3) | 0.026 (3) | 0.008 (3) | −0.006 (2) | 0.006 (3) |
C26 | 0.026 (3) | 0.044 (4) | 0.029 (4) | −0.003 (3) | −0.005 (3) | 0.017 (3) |
C27 | 0.023 (3) | 0.046 (4) | 0.027 (4) | 0.008 (3) | −0.003 (3) | 0.012 (3) |
C28 | 0.029 (4) | 0.031 (3) | 0.021 (4) | −0.006 (3) | −0.005 (2) | −0.003 (2) |
C29 | 0.060 (4) | 0.051 (4) | 0.021 (3) | −0.008 (5) | −0.004 (3) | −0.011 (3) |
C30 | 0.038 (4) | 0.053 (4) | 0.032 (4) | −0.004 (3) | −0.017 (3) | 0.014 (3) |
Geometric parameters (Å, º) top
Zr1—Cl1 | 2.471 (1) | C24—C28 | 1.520 (7) |
Zr1—N1 | 2.141 (4) | C25—C26 | 1.536 (7) |
Zr1—C1 | 2.542 (5) | C25—C27 | 1.544 (8) |
Zr1—C2 | 2.518 (5) | C28—C29 | 1.532 (8) |
Zr1—C3 | 2.504 (5) | C28—C30 | 1.531 (8) |
Zr1—C4 | 2.530 (6) | C1—H1 | 0.951 |
Zr1—C5 | 2.563 (5) | C2—H2 | 0.951 |
Zr1—C6 | 2.531 (5) | C3—H3 | 0.950 |
Zr1—C7 | 2.514 (5) | C4—H4 | 0.949 |
Zr1—C8 | 2.539 (5) | C5—H5 | 0.950 |
Zr1—C9 | 2.534 (6) | C6—H6 | 0.950 |
Zr1—C10 | 2.534 (5) | C7—H7 | 0.951 |
N1—C11 | 1.443 (6) | C8—H8 | 0.951 |
N1—C19 | 1.461 (6) | C9—H9 | 0.951 |
C1—C2 | 1.404 (8) | C10—H10 | 0.949 |
C1—C5 | 1.405 (8) | C12—H11 | 0.951 |
C2—C3 | 1.405 (8) | C12—H12 | 0.951 |
C3—C4 | 1.418 (7) | C14—H13 | 0.950 |
C4—C5 | 1.382 (8) | C15—H14 | 0.948 |
C6—C7 | 1.403 (8) | C16—H15 | 0.950 |
C6—C10 | 1.378 (8) | C17—H16 | 0.951 |
C7—C8 | 1.415 (8) | C18—H17 | 0.953 |
C8—C9 | 1.402 (8) | C21—H18 | 0.949 |
C9—C10 | 1.422 (8) | C22—H19 | 0.951 |
C11—C12 | 1.340 (7) | C23—H20 | 0.953 |
C11—C13 | 1.485 (7) | C25—H21 | 0.948 |
C13—C14 | 1.395 (7) | C26—H22 | 0.949 |
C13—C18 | 1.407 (7) | C26—H23 | 0.949 |
C14—C15 | 1.393 (7) | C26—H24 | 0.951 |
C15—C16 | 1.379 (8) | C27—H25 | 0.952 |
C16—C17 | 1.380 (8) | C27—H26 | 0.949 |
C17—C18 | 1.395 (8) | C27—H27 | 0.950 |
C19—C20 | 1.412 (7) | C28—H28 | 0.949 |
C19—C24 | 1.400 (7) | C29—H29 | 0.950 |
C20—C21 | 1.386 (7) | C29—H30 | 0.948 |
C20—C25 | 1.518 (7) | C29—H31 | 0.952 |
C21—C22 | 1.382 (8) | C30—H32 | 0.951 |
C22—C23 | 1.366 (8) | C30—H33 | 0.950 |
C23—C24 | 1.395 (7) | C30—H34 | 0.951 |
| | | |
Cl1—Zr1—N1 | 98.9 (1) | C14—C13—C18 | 117.1 (5) |
Cl1—Zr1—C1 | 89.4 (2) | C13—C14—C15 | 120.9 (5) |
Cl1—Zr1—C2 | 121.6 (1) | C14—C15—C16 | 121.0 (6) |
Cl1—Zr1—C3 | 127.6 (1) | C15—C16—C17 | 119.5 (5) |
Cl1—Zr1—C4 | 96.7 (1) | C16—C17—C18 | 119.9 (5) |
Cl1—Zr1—C5 | 75.6 (1) | C13—C18—C17 | 121.6 (5) |
Cl1—Zr1—C6 | 114.1 (1) | N1—C19—C20 | 120.3 (4) |
Cl1—Zr1—C7 | 134.0 (1) | N1—C19—C24 | 118.3 (4) |
Cl1—Zr1—C8 | 110.1 (1) | C20—C19—C24 | 121.3 (4) |
Cl1—Zr1—C9 | 81.5 (1) | C19—C20—C21 | 117.7 (5) |
Cl1—Zr1—C10 | 84.2 (1) | C19—C20—C25 | 123.1 (5) |
N1—Zr1—C1 | 87.3 (2) | C21—C20—C25 | 119.3 (5) |
N1—Zr1—C2 | 84.5 (2) | C20—C21—C22 | 121.3 (5) |
N1—Zr1—C3 | 112.8 (2) | C21—C22—C23 | 120.4 (5) |
N1—Zr1—C4 | 137.1 (2) | C22—C23—C24 | 121.0 (5) |
N1—Zr1—C5 | 117.6 (2) | C19—C24—C23 | 118.2 (5) |
N1—Zr1—C6 | 82.4 (2) | C19—C24—C28 | 122.5 (4) |
N1—Zr1—C7 | 102.3 (2) | C23—C24—C28 | 119.3 (5) |
N1—Zr1—C8 | 133.7 (2) | C20—C25—C26 | 112.0 (5) |
N1—Zr1—C9 | 129.2 (2) | C20—C25—C27 | 111.7 (5) |
N1—Zr1—C10 | 96.6 (2) | C26—C25—C27 | 109.3 (4) |
C1—Zr1—C2 | 32.2 (2) | C24—C28—C29 | 113.8 (5) |
C1—Zr1—C3 | 53.7 (2) | C24—C28—C30 | 111.7 (5) |
C1—Zr1—C4 | 53.1 (2) | C29—C28—C30 | 108.4 (5) |
C1—Zr1—C5 | 31.9 (2) | Zr1—C1—H1 | 117.729 |
C1—Zr1—C6 | 155.4 (2) | C2—C1—H1 | 126.355 |
C1—Zr1—C7 | 131.6 (2) | C5—C1—H1 | 126.235 |
C1—Zr1—C8 | 126.9 (2) | Zr1—C2—H2 | 118.269 |
C1—Zr1—C9 | 143.2 (2) | C1—C2—H2 | 125.627 |
C1—Zr1—C10 | 172.9 (2) | C3—C2—H2 | 125.955 |
C2—Zr1—C3 | 32.5 (2) | Zr1—C3—H3 | 116.567 |
C2—Zr1—C4 | 53.5 (2) | C2—C3—H3 | 126.266 |
C2—Zr1—C5 | 52.9 (2) | C4—C3—H3 | 126.628 |
C2—Zr1—C6 | 124.0 (2) | Zr1—C4—H4 | 117.971 |
C2—Zr1—C7 | 100.8 (2) | C3—C4—H4 | 125.708 |
C2—Zr1—C8 | 108.0 (2) | C5—C4—H4 | 126.017 |
C2—Zr1—C9 | 138.2 (2) | Zr1—C5—H5 | 119.917 |
C2—Zr1—C10 | 153.8 (2) | C1—C5—H5 | 125.645 |
C3—Zr1—C4 | 32.7 (2) | C4—C5—H5 | 125.584 |
C3—Zr1—C5 | 53.2 (2) | Zr1—C6—H6 | 118.884 |
C3—Zr1—C6 | 110.6 (2) | C7—C6—H6 | 125.432 |
C3—Zr1—C7 | 79.5 (2) | C10—C6—H6 | 125.510 |
C3—Zr1—C8 | 76.8 (2) | Zr1—C7—H7 | 116.381 |
C3—Zr1—C9 | 105.7 (2) | C6—C7—H7 | 126.383 |
C3—Zr1—C10 | 129.0 (2) | C8—C7—H7 | 126.129 |
C4—Zr1—C5 | 31.5 (2) | Zr1—C8—H8 | 119.384 |
C4—Zr1—C6 | 126.0 (2) | C7—C8—H8 | 126.273 |
C4—Zr1—C7 | 94.8 (2) | C9—C8—H8 | 125.958 |
C4—Zr1—C8 | 75.3 (2) | Zr1—C9—H9 | 118.070 |
C4—Zr1—C9 | 92.5 (2) | C8—C9—H9 | 126.119 |
C4—Zr1—C10 | 124.7 (2) | C10—C9—H9 | 126.243 |
C5—Zr1—C6 | 157.1 (2) | Zr1—C10—H10 | 118.161 |
C5—Zr1—C7 | 126.2 (2) | C6—C10—H10 | 126.023 |
C5—Zr1—C8 | 104.4 (2) | C9—C10—H10 | 125.964 |
C5—Zr1—C9 | 111.7 (2) | C11—C12—H11 | 120.110 |
C5—Zr1—C10 | 142.2 (2) | C11—C12—H12 | 120.074 |
C6—Zr1—C7 | 32.3 (2) | H11—C12—H12 | 119.816 |
C6—Zr1—C8 | 53.3 (2) | C13—C14—H13 | 119.884 |
C6—Zr1—C9 | 53.1 (2) | C15—C14—H13 | 119.217 |
C6—Zr1—C10 | 31.6 (2) | C14—C15—H14 | 119.724 |
C7—Zr1—C8 | 32.5 (2) | C16—C15—H14 | 119.268 |
C7—Zr1—C9 | 53.6 (2) | C15—C16—H15 | 120.555 |
C7—Zr1—C10 | 53.3 (2) | C17—C16—H15 | 119.971 |
C8—Zr1—C9 | 32.1 (2) | C16—C17—H16 | 120.310 |
C8—Zr1—C10 | 53.4 (2) | C18—C17—H16 | 119.836 |
C9—Zr1—C10 | 32.6 (2) | C13—C18—H17 | 119.031 |
Zr1—N1—C11 | 121.6 (3) | C17—C18—H17 | 119.328 |
Zr1—N1—C19 | 126.5 (3) | C20—C21—H18 | 119.505 |
C11—N1—C19 | 111.9 (4) | C22—C21—H18 | 119.168 |
Zr1—C1—C2 | 72.9 (3) | C21—C22—H19 | 119.886 |
Zr1—C1—C5 | 74.9 (3) | C23—C22—H19 | 119.715 |
C2)—C1—C5 | 107.4 (5) | C22—C23—H20 | 119.589 |
Zr1—C2—C1 | 74.8 (3) | C24—C23—H20 | 119.390 |
Zr1—C2—C3 | 73.2 (3) | C20—C25—H21 | 108.043 |
C1—C2—C3 | 108.4 (5) | C26—C25—H21 | 107.889 |
Zr1—C3—C2 | 74.3 (3) | C27—C25—H21 | 107.743 |
Zr1—C3—C4 | 74.6 (3) | C25—C26—H22 | 109.522 |
C2—C3—C4 | 107.1 (5) | C25—C26—H23 | 109.406 |
Zr1—C4—C3 | 72.7 (3) | C25—C26—H24 | 109.436 |
Zr1—C4—C5 | 75.6 (3) | H22—C26—H23 | 109.628 |
C3—C4—C5 | 108.3 (5) | H22—C26—H24 | 109.394 |
Zr1—C5—C1 | 73.2 (3) | H23—C26—H24 | 109.441 |
Zr1—C5—C4 | 72.9 (3) | C25—C27—H25 | 109.505 |
C1—C5—C4 | 108.8 (5) | C25—C27—H26 | 109.540 |
Zr1—C6—C7 | 73.2 (3) | C25—C27—H27 | 109.555 |
Zr1—C6—C10 | 74.3 (3) | H25—C27—H26 | 109.384 |
C7—C6—C10 | 109.1 (5) | H25—C27—H27 | 109.315 |
Zr1—C7—C6 | 74.5 (3) | H26—C27—H27 | 109.528 |
Zr1—C7—C8 | 74.7 (3) | C24—C28—H28 | 107.761 |
C6—C7—C8 | 107.5 (5) | C29—C28—H28 | 107.412 |
Zr1—C8—C7 | 72.8 (3) | C30—C28—H28 | 107.466 |
Zr1—C8—C9 | 73.8 (3) | C28—C29—H29 | 109.374 |
C7—C8—C9 | 107.8 (5) | C28—C29—H30 | 109.583 |
Zr1—C9—C8 | 74.2 (3) | C28—C29—H31 | 109.335 |
Zr1—C9—C10 | 73.7 (3) | H29—C29—H30 | 109.676 |
C8—C9—C10 | 107.6 (5) | H29—C29—H31 | 109.366 |
Zr1—C10—C6 | 74.1 (3) | H30—C29—H31 | 109.492 |
Zr1—C10—C9 | 73.7 (3) | C28—C30—H32 | 109.564 |
C6—C10—C9 | 108.0 (5) | C28—C30—H33 | 109.678 |
N1—C11—C12 | 120.2 (5) | C28—C30—H34 | 109.498 |
N1—C11—C13 | 122.8 (5) | H32—C30—H33 | 109.376 |
C12—C11—C13 | 117.0 (5) | H32—C30—H34 | 109.292 |
C11—C13—C14 | 123.8 (5) | H33—C30—H34 | 109.418 |
C11—C13—C18 | 118.8 (5) | | |
| | | |
Zr1—N1—C11—C12 | 38.4 (6) | C3—Zr1—C6—C10 | 132.3 (4) |
Zr1—N1—C11—C13 | −139.9 (4) | C3—Zr1—C7—C6 | −164.5 (4) |
Zr1—N1—C19—C20 | 87.5 (5) | C3—Zr1—C7—C8 | 82.0 (4) |
Zr1—N1—C19—C24 | −94.9 (5) | C3—Zr1—C8—C7 | −91.0 (4) |
Zr1—C1—C2—C3 | −66.1 (4) | C3—Zr1—C8—C9 | 153.9 (4) |
Zr1—C1—C5—C4 | 64.8 (4) | C3—Zr1—C9—C8 | −26.4 (4) |
Zr1—C2—C1—C5 | 67.5 (4) | C3—Zr1—C9—C10 | −140.7 (3) |
Zr1—C2—C3—C4 | −68.0 (4) | C3—Zr1—C10—C6 | −63.0 (4) |
Zr1—C3—C2—C1 | 67.1 (4) | C3—Zr1—C10—C9 | 51.7 (4) |
Zr1—C3—C4—C5 | −67.8 (4) | C3—C2—Zr1—C4 | 38.2 (3) |
Zr1—C4—C3—C2 | 67.8 (4) | C3—C2—Zr1—C5 | 77.8 (4) |
Zr1—C4—C5—C1 | −64.9 (4) | C3—C2—Zr1—C6 | −74.3 (4) |
Zr1—C5—C1—C2 | −66.2 (4) | C3—C2—Zr1—C7 | −49.8 (4) |
Zr1—C5—C4—C3 | 65.9 (4) | C3—C2—Zr1—C8 | −17.0 (4) |
Zr1—C6—C7—C8 | 68.0 (4) | C3—C2—Zr1—C9 | −3.6 (5) |
Zr1—C6—C10—C9 | −66.5 (4) | C3—C2—Zr1—C10 | −57.4 (6) |
Zr1—C7—C6—C10 | −66.3 (4) | C3—C2—C1—C5 | 1.4 (6) |
Zr1—C7—C8—C9 | 66.0 (4) | C3—C4—Zr1—C5 | −114.8 (5) |
Zr1—C8—C7—C6 | −67.9 (4) | C3—C4—Zr1—C6 | 70.9 (4) |
Zr1—C8—C9—C10 | 66.7 (4) | C3—C4—Zr1—C7 | 62.0 (3) |
Zr1—C9—C8—C7 | −65.3 (4) | C3—C4—Zr1—C8 | 88.3 (3) |
Zr1—C9—C10—C6 | 66.7 (4) | C3—C4—Zr1—C9 | 115.7 (3) |
Zr1—C10—C6—C7 | 65.5 (4) | C3—C4—Zr1—C10 | 109.8 (3) |
Zr1—C10—C9—C8 | −67.0 (4) | C4—Zr1—N1—C11 | −173.4 (3) |
Cl1—Zr1—N1—C11 | −63.3 (4) | C4—Zr1—N1—C19 | 7.9 (5) |
Cl1—Zr1—N1—C19 | 117.9 (4) | C4—Zr1—C1—C5 | −35.8 (3) |
Cl1—Zr1—C1—C2 | 177.1 (3) | C4—Zr1—C6—C7 | −16.8 (4) |
Cl1—Zr1—C1—C5 | 63.1 (3) | C4—Zr1—C6—C10 | 99.2 (4) |
Cl1—Zr1—C2—C1 | −3.4 (4) | C4—Zr1—C7—C6 | 166.4 (3) |
Cl1—Zr1—C2—C3 | 111.7 (3) | C4—Zr1—C7—C8 | 52.9 (4) |
Cl1—Zr1—C3—C2 | −91.2 (4) | C4—Zr1—C8—C7 | −124.7 (4) |
Cl1—Zr1—C3—C4 | 22.0 (4) | C4—Zr1—C8—C9 | 120.2 (3) |
Cl1—Zr1—C4—C3 | −162.6 (3) | C4—Zr1—C9—C8 | −56.8 (3) |
Cl1—Zr1—C4—C5 | −47.8 (3) | C4—Zr1—C9—C10 | −171.1 (4) |
Cl1—Zr1—C5—C1 | −113.0 (4) | C4—Zr1—C10—C6 | −103.9 (4) |
Cl1—Zr1—C5—C4 | 130.6 (3) | C4—Zr1—C10—C9 | 10.9 (4) |
Cl1—Zr1—C6—C7 | −135.8 (3) | C4—C3—Zr1—C5 | 36.3 (3) |
Cl1—Zr1—C6—C10 | −19.7 (4) | C4—C3—Zr1—C6 | −125.2 (3) |
Cl1—Zr1—C7—C6 | 62.3 (4) | C4—C3—Zr1—C7 | −116.5 (3) |
Cl1—Zr1—C7—C8 | −51.2 (4) | C4—C3—Zr1—C8 | −83.3 (3) |
Cl1—Zr1—C8—C7 | 143.3 (3) | C4—C3—Zr1—C9 | −69.3 (3) |
Cl1—Zr1—C8—C9 | 28.3 (3) | C4—C3—Zr1—C10 | −95.4 (4) |
Cl1—Zr1—C9—C8 | −153.2 (3) | C4—C5—Zr1—C6 | 12.0 (7) |
Cl1—Zr1—C9—C10 | 92.5 (3) | C4—C5—Zr1—C7 | −3.9 (4) |
Cl1—Zr1—C10—C6 | 162.0 (4) | C4—C5—Zr1—C8 | 23.1 (4) |
Cl1—Zr1—C10—C9 | −83.3 (3) | C4—C5—Zr1—C9 | 56.0 (4) |
N1—Zr1—C1—C2 | −84.0 (3) | C4—C5—Zr1—C10 | 70.7 (4) |
N1—Zr1—C1—C5 | 162.0 (4) | C5—Zr1—N1—C11 | −141.7 (3) |
N1—Zr1—C2—C1 | 93.7 (4) | C5—Zr1—N1—C19 | 39.5 (4) |
N1—Zr1—C2—C3 | −151.2 (4) | C5—Zr1—C6—C7 | −24.5 (7) |
N1—Zr1—C3—C2 | 31.3 (4) | C5—Zr1—C6—C10 | 91.6 (6) |
N1—Zr1—C3—C4 | 144.5 (3) | C5—Zr1—C7—C6 | 168.5 (3) |
N1—Zr1—C4—C3 | −51.8 (4) | C5—Zr1—C7—C8 | 55.0 (4) |
N1—Zr1—C4—C5 | 63.0 (4) | C5—Zr1—C8—C7 | −137.0 (3) |
N1—Zr1—C5—C1 | −20.4 (4) | C5—Zr1—C8—C9 | 108.0 (3) |
N1—Zr1—C5—C4 | −136.8 (3) | C5—Zr1—C9—C8 | −82.5 (3) |
N1—Zr1—C6—C7 | 127.9 (4) | C5—Zr1—C9—C10 | 163.3 (3) |
N1—Zr1—C6—C10 | −116.1 (4) | C5—Zr1—C10—C6 | −140.7 (3) |
N1—Zr1—C7—C6 | −53.2 (4) | C5—Zr1—C10—C9 | −25.9 (5) |
N1—Zr1—C7—C8 | −166.7 (3) | C5—C1—Zr1—C6 | −132.9 (4) |
N1—Zr1—C8—C7 | 18.1 (5) | C5—C1—Zr1—C7 | −93.9 (4) |
N1—Zr1—C8—C9 | −97.0 (4) | C5—C1—Zr1—C8 | −51.9 (4) |
N1—Zr1—C9—C8 | 112.2 (3) | C5—C1—Zr1—C9 | −11.8 (6) |
N1—Zr1—C9—C10 | −2.1 (4) | C5—C4—Zr1—C6 | −174.3 (3) |
N1—Zr1—C10—C6 | 63.6 (4) | C5—C4—Zr1—C7 | 176.8 (3) |
N1—Zr1—C10—C9 | 178.4 (3) | C5—C4—Zr1—C8 | −156.9 (4) |
N1—C11—C13—C14 | −64.8 (7) | C5—C4—Zr1—C9 | −129.5 (3) |
N1—C11—C13—C18 | 120.9 (5) | C5—C4—Zr1—C10 | −135.4 (3) |
N1—C19—C20—C21 | 179.0 (4) | C6—Zr1—N1—C11 | 50.0 (4) |
N1—C19—C20—C25 | −0.8 (7) | C6—Zr1—N1—C19 | −128.7 (4) |
N1—C19—C24—C23 | −177.1 (5) | C6—Zr1—C7—C8 | −113.5 (5) |
N1—C19—C24—C28 | 0.3 (7) | C6—Zr1—C8—C7 | 37.7 (3) |
C1—Zr1—N1—C11 | −152.3 (4) | C6—Zr1—C8—C9 | −77.3 (4) |
C1—Zr1—N1—C19 | 28.9 (4) | C6—Zr1—C9—C8 | 77.8 (3) |
C1—Zr1—C2—C3 | 115.1 (5) | C6—Zr1—C9—C10 | −36.5 (3) |
C1—Zr1—C3—C2 | −36.8 (3) | C6—Zr1—C10—C9 | 114.7 (5) |
C1—Zr1—C3—C4 | 76.4 (3) | C6—C7—Zr1—C8 | 113.5 (5) |
C1—Zr1—C4—C3 | −78.4 (3) | C6—C7—Zr1—C9 | 76.8 (4) |
C1—Zr1—C4—C5 | 36.4 (3) | C6—C7—Zr1—C10 | 35.9 (3) |
C1—Zr1—C5—C4 | −116.4 (5) | C6—C7—C8—C9 | −1.9 (6) |
C1—Zr1—C6—C7 | 61.8 (6) | C6—C10—Zr1—C7 | −36.8 (3) |
C1—Zr1—C6—C10 | 177.8 (5) | C6—C10—Zr1—C8 | −77.6 (4) |
C1—Zr1—C7—C6 | −150.7 (3) | C6—C10—Zr1—C9 | −114.7 (5) |
C1—Zr1—C7—C8 | 95.8 (4) | C6—C10—C9—C8 | −0.2 (7) |
C1—Zr1—C8—C7 | −111.5 (4) | C7—Zr1—N1—C11 | 75.6 (4) |
C1—Zr1—C8—C9 | 133.5 (3) | C7—Zr1—N1—C19 | −103.2 (4) |
C1—Zr1—C9—C8 | −75.8 (4) | C7—Zr1—C6—C10 | 116.0 (5) |
C1—Zr1—C9—C10 | 170.0 (4) | C7—Zr1—C8—C9 | −115.0 (5) |
C1—C2—Zr1—C3 | −115.1 (5) | C7—Zr1—C9—C8 | 37.3 (3) |
C1—C2—Zr1—C4 | −76.9 (4) | C7—Zr1—C9—C10 | −77.0 (4) |
C1—C2—Zr1—C5 | −37.3 (3) | C7—Zr1—C10—C9 | 78.0 (4) |
C1—C2—Zr1—C6 | 170.6 (3) | C7—C6—Zr1—C8 | −38.0 (3) |
C1—C2—Zr1—C7 | −164.8 (4) | C7—C6—Zr1—C9 | −78.3 (4) |
C1—C2—Zr1—C8 | −132.0 (4) | C7—C6—Zr1—C10 | −116.0 (5) |
C1—C2—Zr1—C9 | −118.7 (4) | C7—C6—C10—C9 | −0.9 (7) |
C1—C2—Zr1—C10 | −172.4 (5) | C7—C8—Zr1—C9 | 115.0 (5) |
C1—C2—C3—C4 | −0.9 (6) | C7—C8—Zr1—C10 | 77.3 (4) |
C1—C5—Zr1—C2 | 37.6 (3) | C7—C8—C9—C10 | 1.3 (6) |
C1—C5—Zr1—C3 | 78.6 (4) | C8—Zr1—N1—C11 | 65.8 (4) |
C1—C5—Zr1—C4 | 116.4 (5) | C8—Zr1—N1—C19 | −113.0 (4) |
C1—C5—Zr1—C6 | 128.4 (5) | C8—Zr1—C6—C10 | 78.1 (4) |
C1—C5—Zr1—C7 | 112.4 (4) | C8—Zr1—C9—C10 | −114.3 (5) |
C1—C5—Zr1—C8 | 139.5 (4) | C8—Zr1—C10—C9 | 37.1 (3) |
C1—C5—Zr1—C9 | 172.4 (4) | C8—C7—Zr1—C9 | −36.7 (3) |
C1—C5—Zr1—C10 | −172.9 (4) | C8—C7—Zr1—C10 | −77.6 (4) |
C1—C5—C4—C3 | 0.9 (6) | C8—C7—C6—C10 | 1.8 (7) |
C2—Zr1—N1—C11 | 175.5 (4) | C8—C9—Zr1—C10 | 114.3 (5) |
C2—Zr1—N1—C19 | −3.3 (4) | C9—Zr1—N1—C11 | 22.9 (4) |
C2—Zr1—C1—C5 | −114.0 (5) | C9—Zr1—N1—C19 | −155.8 (4) |
C2—Zr1—C3—C4 | 113.2 (5) | C9—Zr1—C6—C10 | 37.7 (4) |
C2—Zr1—C4—C3 | −37.9 (3) | C9—C8—Zr1—C10 | −37.7 (3) |
C2—Zr1—C4—C5 | 76.9 (4) | C10—Zr1—N1—C11 | 21.8 (4) |
C2—Zr1—C5—C4 | −78.8 (4) | C10—Zr1—N1—C19 | −157.0 (4) |
C2—Zr1—C6—C7 | 49.8 (4) | C11—N1—C19—C20 | −91.3 (5) |
C2—Zr1—C6—C10 | 165.8 (4) | C11—N1—C19—C24 | 86.3 (5) |
C2—Zr1—C7—C6 | −139.9 (3) | C11—C13—C14—C15 | −174.3 (5) |
C2—Zr1—C7—C8 | 106.6 (4) | C11—C13—C18—C17 | 175.3 (5) |
C2—Zr1—C8—C7 | −81.8 (4) | C12—C11—N1—C19 | −142.7 (5) |
C2—Zr1—C8—C9 | 163.2 (3) | C12—C11—C13—C14 | 116.8 (6) |
C2—Zr1—C9—C8 | −24.4 (5) | C12—C11—C13—C18 | −57.4 (7) |
C2—Zr1—C9—C10 | −138.6 (4) | C13—C11—N1—C19 | 39.0 (6) |
C2—Zr1—C10—C6 | −27.4 (7) | C13—C14—C15—C16 | −0.1 (8) |
C2—Zr1—C10—C9 | 87.3 (5) | C13—C18—C17—C16 | −1.3 (8) |
C2—C1—Zr1—C3 | 37.1 (3) | C14—C13—C18—C17 | 0.7 (8) |
C2—C1—Zr1—C4 | 78.2 (4) | C14—C15—C16—C17 | −0.5 (9) |
C2—C1—Zr1—C5 | 114.0 (5) | C15—C14—C13—C18 | 0.1 (7) |
C2—C1—Zr1—C6 | −18.9 (6) | C15—C16—C17—C18 | 1.2 (8) |
C2—C1—Zr1—C7 | 20.1 (5) | C19—C20—C21—C22 | −2.3 (8) |
C2—C1—Zr1—C8 | 62.1 (4) | C19—C20—C25—C26 | −112.9 (6) |
C2—C1—Zr1—C9 | 102.2 (4) | C19—C20—C25—C27 | 124.1 (5) |
C2—C1—C5—C4 | −1.5 (6) | C19—C24—C23—C22 | −1.7 (9) |
C2—C3—Zr1—C4 | −113.2 (5) | C19—C24—C28—C29 | 141.3 (6) |
C2—C3—Zr1—C5 | −76.9 (4) | C19—C24—C28—C30 | −95.5 (6) |
C2—C3—Zr1—C6 | 121.5 (3) | C20—C19—C24—C23 | 0.5 (8) |
C2—C3—Zr1—C7 | 130.3 (4) | C20—C19—C24—C28 | 177.9 (5) |
C2—C3—Zr1—C8 | 163.4 (4) | C20—C21—C22—C23 | 1.2 (9) |
C2—C3—Zr1—C9 | 177.5 (3) | C21—C20—C19—C24 | 1.4 (8) |
C2—C3—Zr1—C10 | 151.4 (3) | C21—C20—C25—C26 | 67.3 (7) |
C2—C3—C4—C5 | −0.0 (6) | C21—C20—C25—C27 | −55.7 (6) |
C3—Zr1—N1—C11 | 159.2 (4) | C21—C22—C23—C24 | 0.9 (10) |
C3—Zr1—N1—C19 | −19.6 (4) | C22—C21—C20—C25 | 177.5 (5) |
C3—Zr1—C1—C5 | −76.9 (4) | C22—C23—C24—C28 | −179.2 (5) |
C3—Zr1—C4—C5 | 114.8 (5) | C23—C24—C28—C29 | −41.3 (7) |
C3—Zr1—C5—C4 | −37.8 (3) | C23—C24—C28—C30 | 81.8 (7) |
C3—Zr1—C6—C7 | 16.3 (4) | C24—C19—C20—C25 | −178.4 (5) |