Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106053480/ln3026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106053480/ln3026Isup2.hkl |
CCDC reference: 267648
Nickel acetate trihydrate (230 mg, 1.0 mmol) dissolved in methanol was added dropwise to a stirred solution of 2,6-bis{[(2-pyridylmethyl)(2-hydroxyethyl)amino]methyl}-4-methylphenol (218.3 mg, 0.5 mmol) in 25 ml of methanol and refluxed for 30 min in air. After the mixture was cooled to room temperature, a white precipitate was formed upon addition of potassium hexafluorophosphate (184.2 mg, 0.5 mmol) in portions. The precipitate was filtered off, and washed with cold methanol and diethyl ether. Green needle-shaped single crystals of (I) suitable for a crystal structure determination were obtained after ca 1 week by slow evaporation of the filtrate at room temperature [m.p. 509.6 (5) K].
The water and hydroxy H atoms were located in a difference Fourier map and their positions were refined with Uiso(H) = 1.2Ueq(O). The methyl H atoms were constrained to an ideal geometry with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent C atom at a distance of 0.93 or 0.97 Å for phenyl or methylene groups, respectively, and with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Ni2(C25H31N4O3)(C2H3O2)2]PF6·0.5H2O | F(000) = 3400 |
Mr = 825.03 | Dx = 1.587 Mg m−3 |
Monoclinic, P21/c | Melting point: 509.6(5) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.7776 (19) Å | Cell parameters from 804 reflections |
b = 17.191 (2) Å | θ = 2.4–15.7° |
c = 25.513 (3) Å | µ = 1.22 mm−1 |
β = 93.914 (3)° | T = 291 K |
V = 6904.0 (14) Å3 | Needle, green |
Z = 8 | 0.28 × 0.24 × 0.22 mm |
Bruker APEX CCD diffractometer | 13513 independent reflections |
Radiation source: sealed tube | 9603 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −19→16 |
Tmin = 0.72, Tmax = 0.76 | k = −20→21 |
36723 measured reflections | l = −30→31 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0298P)2 + 5.0551P] where P = (Fo2 + 2Fc2)/3 |
13513 reflections | (Δ/σ)max = 0.020 |
916 parameters | Δρmax = 0.48 e Å−3 |
3 restraints | Δρmin = −0.42 e Å−3 |
[Ni2(C25H31N4O3)(C2H3O2)2]PF6·0.5H2O | V = 6904.0 (14) Å3 |
Mr = 825.03 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.7776 (19) Å | µ = 1.22 mm−1 |
b = 17.191 (2) Å | T = 291 K |
c = 25.513 (3) Å | 0.28 × 0.24 × 0.22 mm |
β = 93.914 (3)° |
Bruker APEX CCD diffractometer | 13513 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 9603 reflections with I > 2σ(I) |
Tmin = 0.72, Tmax = 0.76 | Rint = 0.044 |
36723 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 3 restraints |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.48 e Å−3 |
13513 reflections | Δρmin = −0.42 e Å−3 |
916 parameters |
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 | ||
Ni1 | 0.54320 (3) | 0.78470 (3) | 0.46951 (2) | 0.03709 (13) | |
Ni2 | 0.33237 (3) | 0.77866 (3) | 0.490289 (19) | 0.03253 (12) | |
N1 | 0.61751 (19) | 0.68250 (16) | 0.47567 (12) | 0.0337 (7) | |
N2 | 0.24926 (19) | 0.7306 (2) | 0.43004 (12) | 0.0409 (8) | |
N3 | 0.56413 (17) | 0.76482 (16) | 0.39065 (12) | 0.0313 (7) | |
N4 | 0.29435 (19) | 0.68072 (17) | 0.52949 (12) | 0.0352 (7) | |
O1 | 0.43301 (15) | 0.72605 (15) | 0.46242 (10) | 0.0375 (6) | |
O2 | 0.66820 (17) | 0.83241 (16) | 0.48823 (12) | 0.0438 (7) | |
H2 | 0.666 (3) | 0.862 (3) | 0.5105 (18) | 0.053* | |
O3 | 0.21475 (17) | 0.83544 (15) | 0.50327 (11) | 0.0401 (6) | |
H3 | 0.199 (3) | 0.812 (2) | 0.5299 (17) | 0.048* | |
O4 | 0.49467 (16) | 0.88996 (14) | 0.45591 (11) | 0.0394 (6) | |
O5 | 0.35525 (16) | 0.88416 (15) | 0.45299 (10) | 0.0415 (7) | |
O6 | 0.53072 (15) | 0.79184 (15) | 0.54994 (10) | 0.0379 (6) | |
O7 | 0.39566 (15) | 0.82015 (15) | 0.55780 (10) | 0.0388 (6) | |
C1 | 0.4303 (2) | 0.6589 (2) | 0.44025 (14) | 0.0340 (8) | |
C2 | 0.3641 (2) | 0.6397 (2) | 0.40119 (16) | 0.0373 (9) | |
C3 | 0.3590 (3) | 0.5685 (3) | 0.37842 (17) | 0.0527 (11) | |
H3A | 0.3129 | 0.5578 | 0.3548 | 0.063* | |
C4 | 0.4178 (3) | 0.5122 (2) | 0.38848 (16) | 0.0452 (10) | |
C5 | 0.4833 (3) | 0.5316 (2) | 0.42539 (15) | 0.0413 (10) | |
H5 | 0.5248 | 0.4942 | 0.4331 | 0.050* | |
C6 | 0.4915 (3) | 0.6006 (2) | 0.45106 (16) | 0.0410 (9) | |
C7 | 0.5603 (2) | 0.6191 (2) | 0.49181 (16) | 0.0385 (9) | |
H7A | 0.5939 | 0.5727 | 0.4994 | 0.046* | |
H7B | 0.5351 | 0.6345 | 0.5238 | 0.046* | |
C8 | 0.4171 (3) | 0.4362 (2) | 0.36068 (16) | 0.0495 (11) | |
H8A | 0.3602 | 0.4162 | 0.3573 | 0.074* | |
H8B | 0.4532 | 0.4001 | 0.3804 | 0.074* | |
H8C | 0.4376 | 0.4432 | 0.3264 | 0.074* | |
C9 | 0.3009 (2) | 0.7031 (2) | 0.38678 (15) | 0.0370 (9) | |
H9A | 0.3314 | 0.7473 | 0.3738 | 0.044* | |
H9B | 0.2624 | 0.6846 | 0.3582 | 0.044* | |
C10 | 0.6551 (2) | 0.6641 (2) | 0.42515 (14) | 0.0455 (10) | |
H10A | 0.7150 | 0.6773 | 0.4281 | 0.055* | |
H10B | 0.6503 | 0.6087 | 0.4186 | 0.055* | |
C11 | 0.6140 (2) | 0.70582 (19) | 0.38106 (13) | 0.0357 (9) | |
C12 | 0.6310 (3) | 0.6866 (3) | 0.33271 (16) | 0.0559 (12) | |
H12 | 0.6689 | 0.6466 | 0.3268 | 0.067* | |
C13 | 0.5916 (3) | 0.7269 (3) | 0.29116 (19) | 0.0657 (14) | |
H13 | 0.6017 | 0.7126 | 0.2570 | 0.079* | |
C14 | 0.5392 (3) | 0.7861 (3) | 0.29914 (19) | 0.0632 (14) | |
H14 | 0.5123 | 0.8139 | 0.2715 | 0.076* | |
C15 | 0.5275 (3) | 0.8035 (2) | 0.35027 (16) | 0.0415 (10) | |
H15 | 0.4918 | 0.8448 | 0.3572 | 0.050* | |
C16 | 0.6876 (3) | 0.7012 (2) | 0.51752 (18) | 0.0520 (12) | |
H16A | 0.6640 | 0.7046 | 0.5516 | 0.062* | |
H16B | 0.7297 | 0.6600 | 0.5190 | 0.062* | |
C17 | 0.7282 (3) | 0.7765 (3) | 0.50487 (18) | 0.0523 (11) | |
H17A | 0.7610 | 0.7954 | 0.5358 | 0.063* | |
H17B | 0.7669 | 0.7681 | 0.4775 | 0.063* | |
C18 | 0.2025 (2) | 0.6660 (2) | 0.45048 (15) | 0.0414 (10) | |
H18A | 0.2030 | 0.6235 | 0.4255 | 0.050* | |
H18B | 0.1438 | 0.6819 | 0.4525 | 0.050* | |
C19 | 0.2345 (2) | 0.6362 (2) | 0.50307 (15) | 0.0320 (8) | |
C20 | 0.2031 (3) | 0.5720 (2) | 0.52414 (18) | 0.0505 (11) | |
H20 | 0.1609 | 0.5435 | 0.5056 | 0.061* | |
C21 | 0.2330 (3) | 0.5485 (3) | 0.5726 (2) | 0.0668 (14) | |
H21 | 0.2124 | 0.5033 | 0.5872 | 0.080* | |
C22 | 0.2934 (3) | 0.5915 (3) | 0.5997 (2) | 0.0673 (15) | |
H22 | 0.3141 | 0.5769 | 0.6333 | 0.081* | |
C23 | 0.3229 (3) | 0.6563 (3) | 0.57677 (18) | 0.0509 (11) | |
H23 | 0.3652 | 0.6851 | 0.5951 | 0.061* | |
C24 | 0.1933 (2) | 0.7948 (3) | 0.41343 (15) | 0.0450 (10) | |
H24A | 0.1487 | 0.7757 | 0.3887 | 0.054* | |
H24B | 0.2255 | 0.8336 | 0.3956 | 0.054* | |
C25 | 0.1535 (3) | 0.8323 (3) | 0.46015 (17) | 0.0483 (11) | |
H25A | 0.1342 | 0.8844 | 0.4509 | 0.058* | |
H25B | 0.1049 | 0.8020 | 0.4695 | 0.058* | |
C26 | 0.4707 (2) | 0.8073 (2) | 0.57660 (15) | 0.0351 (8) | |
C27 | 0.4868 (3) | 0.8130 (3) | 0.63477 (16) | 0.0517 (11) | |
H27A | 0.5041 | 0.7632 | 0.6487 | 0.062* | |
H27C | 0.4358 | 0.8292 | 0.6501 | 0.062* | |
H27B | 0.5310 | 0.8504 | 0.6430 | 0.062* | |
C28 | 0.4236 (2) | 0.9168 (2) | 0.44654 (15) | 0.0378 (9) | |
C29 | 0.4181 (3) | 0.9993 (2) | 0.42881 (18) | 0.0509 (11) | |
H29A | 0.4413 | 1.0326 | 0.4564 | 0.076* | |
H29B | 0.3597 | 1.0128 | 0.4204 | 0.076* | |
H29C | 0.4497 | 1.0058 | 0.3983 | 0.076* | |
Ni3 | 0.18799 (3) | 0.94476 (3) | 0.63169 (2) | 0.03748 (12) | |
Ni4 | −0.02340 (3) | 0.96572 (3) | 0.64428 (2) | 0.04316 (14) | |
O8 | 0.09418 (16) | 0.96703 (14) | 0.67716 (10) | 0.0372 (6) | |
O9 | 0.29492 (18) | 0.94084 (16) | 0.58567 (11) | 0.0426 (7) | |
H9 | 0.317 (3) | 0.899 (3) | 0.5893 (17) | 0.051* | |
O10 | −0.15073 (19) | 0.94549 (18) | 0.61502 (13) | 0.0534 (8) | |
H10 | −0.152 (3) | 0.926 (3) | 0.5861 (19) | 0.064* | |
O11 | 0.14149 (17) | 1.02106 (16) | 0.57337 (11) | 0.0464 (7) | |
O12 | 0.00436 (17) | 1.02009 (16) | 0.57890 (12) | 0.0496 (7) | |
O13 | 0.13024 (18) | 0.85538 (15) | 0.59146 (11) | 0.0468 (7) | |
O14 | −0.00036 (18) | 0.85345 (17) | 0.61917 (13) | 0.0547 (8) | |
N5 | 0.26711 (19) | 1.0279 (2) | 0.67245 (13) | 0.0448 (8) | |
N6 | −0.0742 (2) | 0.9264 (2) | 0.71081 (14) | 0.0509 (9) | |
N7 | 0.2495 (2) | 0.8707 (2) | 0.68456 (13) | 0.0437 (8) | |
N8 | −0.0492 (2) | 1.0699 (2) | 0.67971 (14) | 0.0493 (9) | |
C30 | 0.1054 (3) | 0.9900 (3) | 0.72570 (18) | 0.0546 (12) | |
C31 | 0.1655 (3) | 1.0502 (3) | 0.74111 (19) | 0.0580 (12) | |
C32 | 0.1742 (3) | 1.0723 (3) | 0.7926 (2) | 0.0607 (13) | |
H32 | 0.2121 | 1.1117 | 0.8029 | 0.073* | |
C33 | 0.1264 (4) | 1.0361 (4) | 0.8303 (2) | 0.0767 (16) | |
C34 | 0.0708 (3) | 0.9783 (3) | 0.81221 (19) | 0.0651 (14) | |
H34 | 0.0380 | 0.9547 | 0.8366 | 0.078* | |
C35 | 0.0605 (3) | 0.9544 (3) | 0.7641 (2) | 0.0602 (13) | |
C36 | 0.2133 (3) | 1.0869 (2) | 0.69908 (19) | 0.0527 (12) | |
H36A | 0.2495 | 1.1277 | 0.7143 | 0.063* | |
H36B | 0.1734 | 1.1105 | 0.6731 | 0.063* | |
C37 | 0.1388 (4) | 1.0651 (4) | 0.8866 (2) | 0.0847 (18) | |
H37A | 0.0874 | 1.0574 | 0.9041 | 0.127* | |
H37B | 0.1525 | 1.1195 | 0.8866 | 0.127* | |
H37C | 0.1842 | 1.0368 | 0.9048 | 0.127* | |
C38 | −0.0110 (3) | 0.8959 (3) | 0.74590 (16) | 0.0562 (12) | |
H38A | 0.0147 | 0.8517 | 0.7295 | 0.067* | |
H38B | −0.0374 | 0.8769 | 0.7767 | 0.067* | |
C39 | 0.3264 (3) | 0.9848 (3) | 0.7136 (2) | 0.0659 (14) | |
H39A | 0.3848 | 0.9929 | 0.7052 | 0.079* | |
H39B | 0.3198 | 1.0077 | 0.7478 | 0.079* | |
C40 | 0.3107 (3) | 0.9016 (3) | 0.71669 (15) | 0.0518 (12) | |
C41 | 0.3611 (3) | 0.8561 (3) | 0.75290 (17) | 0.0533 (12) | |
H41 | 0.4048 | 0.8769 | 0.7748 | 0.064* | |
C42 | 0.3403 (4) | 0.7799 (3) | 0.7530 (2) | 0.0659 (14) | |
H42 | 0.3704 | 0.7472 | 0.7767 | 0.079* | |
C43 | 0.2819 (4) | 0.7505 (3) | 0.7224 (2) | 0.0681 (14) | |
H43 | 0.2703 | 0.6975 | 0.7235 | 0.082* | |
C44 | 0.2376 (3) | 0.7963 (3) | 0.68903 (19) | 0.0580 (12) | |
H44 | 0.1949 | 0.7736 | 0.6672 | 0.070* | |
C45 | 0.3141 (3) | 1.0641 (3) | 0.62974 (18) | 0.0521 (11) | |
H45A | 0.2748 | 1.0934 | 0.6064 | 0.063* | |
H45B | 0.3565 | 1.0999 | 0.6449 | 0.063* | |
C46 | 0.3562 (3) | 1.0028 (3) | 0.59936 (17) | 0.0531 (12) | |
H46A | 0.3766 | 1.0251 | 0.5676 | 0.064* | |
H46B | 0.4045 | 0.9817 | 0.6203 | 0.064* | |
C47 | −0.1190 (3) | 0.9880 (3) | 0.7400 (2) | 0.0661 (14) | |
H47A | −0.1793 | 0.9877 | 0.7295 | 0.079* | |
H47B | −0.1118 | 0.9787 | 0.7775 | 0.079* | |
C48 | −0.0822 (3) | 1.0617 (3) | 0.7273 (2) | 0.0648 (14) | |
C49 | −0.0817 (4) | 1.1174 (4) | 0.7612 (2) | 0.0797 (16) | |
H49 | −0.1062 | 1.1092 | 0.7929 | 0.096* | |
C50 | −0.0450 (5) | 1.1900 (4) | 0.7515 (3) | 0.093 (2) | |
H50 | −0.0447 | 1.2297 | 0.7764 | 0.112* | |
C51 | −0.0097 (4) | 1.2008 (3) | 0.7043 (2) | 0.0797 (17) | |
H51 | 0.0154 | 1.2478 | 0.6960 | 0.096* | |
C52 | −0.0129 (3) | 1.1392 (3) | 0.66983 (17) | 0.0534 (11) | |
H52 | 0.0114 | 1.1456 | 0.6379 | 0.064* | |
C53 | −0.1375 (3) | 0.8616 (3) | 0.69253 (18) | 0.0573 (12) | |
H53A | −0.1719 | 0.8468 | 0.7210 | 0.069* | |
H53B | −0.1071 | 0.8161 | 0.6816 | 0.069* | |
C54 | −0.1956 (3) | 0.8950 (3) | 0.64500 (17) | 0.0528 (12) | |
H54A | −0.2176 | 0.8524 | 0.6232 | 0.063* | |
H54B | −0.2436 | 0.9222 | 0.6583 | 0.063* | |
C55 | 0.0606 (3) | 0.8243 (3) | 0.59773 (16) | 0.0467 (11) | |
C56 | 0.0501 (3) | 0.7403 (3) | 0.5808 (2) | 0.0573 (12) | |
H56A | 0.0821 | 0.7310 | 0.5507 | 0.086* | |
H56B | −0.0089 | 0.7297 | 0.5719 | 0.086* | |
H56C | 0.0705 | 0.7068 | 0.6091 | 0.086* | |
C57 | 0.0706 (3) | 1.0425 (3) | 0.55888 (15) | 0.0446 (10) | |
C58 | 0.0618 (3) | 1.1012 (3) | 0.51513 (16) | 0.0495 (11) | |
H58A | 0.0514 | 1.1516 | 0.5295 | 0.074* | |
H58B | 0.0150 | 1.0868 | 0.4910 | 0.074* | |
H58C | 0.1131 | 1.1024 | 0.4970 | 0.074* | |
P1 | 0.38834 (10) | 0.98382 (9) | 0.25655 (6) | 0.0690 (4) | |
F1 | 0.44570 (18) | 1.02820 (16) | 0.21986 (11) | 0.0721 (8) | |
F2 | 0.46706 (18) | 0.97125 (16) | 0.29585 (11) | 0.0716 (8) | |
F3 | 0.3359 (2) | 0.9371 (2) | 0.29229 (12) | 0.0861 (9) | |
F4 | 0.3094 (2) | 0.99697 (18) | 0.21814 (13) | 0.0842 (9) | |
F5 | 0.41148 (18) | 0.90714 (16) | 0.22714 (11) | 0.0710 (8) | |
F6 | 0.3649 (2) | 1.05971 (18) | 0.28480 (12) | 0.0849 (9) | |
P2 | 0.92703 (10) | 0.65001 (9) | 0.42341 (6) | 0.0701 (4) | |
F7 | 0.96839 (18) | 0.70076 (15) | 0.46255 (12) | 0.0700 (8) | |
F8 | 0.97736 (18) | 0.58069 (16) | 0.43800 (11) | 0.0697 (8) | |
F9 | 0.88030 (19) | 0.61357 (17) | 0.37770 (12) | 0.0737 (8) | |
F10 | 0.87439 (19) | 0.72389 (17) | 0.40607 (12) | 0.0762 (8) | |
F11 | 0.99782 (18) | 0.67458 (16) | 0.38628 (12) | 0.0731 (8) | |
F12 | 0.85898 (19) | 0.62638 (18) | 0.46113 (12) | 0.0797 (8) | |
O15 | 0.7575 (2) | 0.9793 (2) | 0.51634 (14) | 0.0543 (8) | |
H15A | 0.758 (3) | 1.008 (3) | 0.544 (2) | 0.065* | |
H15B | 0.733 (3) | 1.003 (3) | 0.492 (2) | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0353 (3) | 0.0351 (3) | 0.0429 (3) | −0.0032 (2) | 0.0183 (2) | 0.0016 (2) |
Ni2 | 0.0251 (2) | 0.0355 (2) | 0.0386 (3) | −0.0017 (2) | 0.01434 (19) | 0.0008 (2) |
N1 | 0.0368 (17) | 0.0276 (15) | 0.0381 (18) | 0.0012 (13) | 0.0116 (14) | 0.0042 (13) |
N2 | 0.0292 (16) | 0.062 (2) | 0.0326 (17) | 0.0009 (15) | 0.0065 (13) | 0.0066 (16) |
N3 | 0.0249 (15) | 0.0283 (16) | 0.0421 (18) | −0.0135 (12) | 0.0118 (13) | −0.0027 (14) |
N4 | 0.0321 (16) | 0.0355 (17) | 0.0401 (19) | −0.0043 (14) | 0.0170 (14) | −0.0010 (15) |
O1 | 0.0292 (13) | 0.0421 (15) | 0.0438 (15) | −0.0043 (11) | 0.0220 (11) | −0.0030 (12) |
O2 | 0.0340 (15) | 0.0445 (17) | 0.0545 (19) | −0.0078 (13) | 0.0154 (14) | −0.0037 (13) |
O3 | 0.0354 (15) | 0.0409 (16) | 0.0452 (17) | 0.0011 (12) | 0.0116 (13) | −0.0066 (13) |
O4 | 0.0296 (14) | 0.0360 (14) | 0.0539 (17) | 0.0064 (11) | 0.0119 (12) | −0.0081 (13) |
O5 | 0.0368 (15) | 0.0518 (16) | 0.0384 (15) | 0.0011 (12) | 0.0205 (12) | 0.0211 (13) |
O6 | 0.0271 (13) | 0.0530 (16) | 0.0334 (14) | 0.0039 (12) | 0.0013 (11) | −0.0103 (12) |
O7 | 0.0280 (14) | 0.0500 (16) | 0.0402 (15) | −0.0091 (12) | 0.0163 (11) | −0.0100 (13) |
C1 | 0.0237 (18) | 0.048 (2) | 0.032 (2) | −0.0084 (16) | 0.0146 (15) | 0.0002 (18) |
C2 | 0.0247 (18) | 0.041 (2) | 0.047 (2) | −0.0001 (16) | 0.0118 (17) | 0.0166 (19) |
C3 | 0.053 (3) | 0.065 (3) | 0.041 (3) | 0.003 (2) | 0.013 (2) | −0.008 (2) |
C4 | 0.055 (3) | 0.050 (2) | 0.033 (2) | −0.006 (2) | 0.023 (2) | 0.0097 (19) |
C5 | 0.045 (2) | 0.046 (2) | 0.036 (2) | 0.0023 (19) | 0.0201 (18) | 0.0200 (19) |
C6 | 0.042 (2) | 0.044 (2) | 0.038 (2) | 0.0002 (18) | 0.0096 (18) | 0.0108 (19) |
C7 | 0.031 (2) | 0.036 (2) | 0.051 (2) | 0.0002 (16) | 0.0152 (17) | 0.0193 (18) |
C8 | 0.063 (3) | 0.047 (2) | 0.038 (2) | −0.016 (2) | 0.006 (2) | 0.002 (2) |
C9 | 0.0192 (17) | 0.056 (2) | 0.035 (2) | 0.0095 (16) | −0.0010 (15) | −0.0012 (18) |
C10 | 0.044 (2) | 0.039 (2) | 0.056 (3) | −0.0038 (18) | 0.024 (2) | 0.002 (2) |
C11 | 0.032 (2) | 0.0297 (19) | 0.047 (2) | −0.0136 (16) | 0.0136 (17) | −0.0078 (17) |
C12 | 0.068 (3) | 0.067 (3) | 0.033 (2) | 0.011 (2) | 0.004 (2) | −0.020 (2) |
C13 | 0.073 (3) | 0.078 (3) | 0.045 (3) | −0.001 (3) | −0.001 (2) | −0.023 (3) |
C14 | 0.060 (3) | 0.079 (3) | 0.047 (3) | 0.014 (3) | −0.023 (2) | −0.014 (3) |
C15 | 0.041 (2) | 0.035 (2) | 0.051 (3) | −0.0039 (17) | 0.0159 (19) | −0.0091 (19) |
C16 | 0.040 (2) | 0.054 (3) | 0.060 (3) | 0.011 (2) | −0.017 (2) | −0.005 (2) |
C17 | 0.034 (2) | 0.066 (3) | 0.057 (3) | −0.001 (2) | −0.0065 (19) | −0.011 (2) |
C18 | 0.0226 (19) | 0.061 (3) | 0.041 (2) | −0.0036 (18) | 0.0027 (16) | −0.002 (2) |
C19 | 0.0224 (17) | 0.0296 (18) | 0.046 (2) | 0.0013 (14) | 0.0163 (16) | −0.0122 (17) |
C20 | 0.058 (3) | 0.044 (2) | 0.051 (3) | −0.015 (2) | 0.016 (2) | −0.003 (2) |
C21 | 0.059 (3) | 0.058 (3) | 0.085 (4) | −0.015 (2) | 0.007 (3) | 0.015 (3) |
C22 | 0.076 (4) | 0.065 (3) | 0.060 (3) | −0.013 (3) | 0.002 (3) | 0.040 (3) |
C23 | 0.047 (3) | 0.055 (3) | 0.050 (3) | −0.014 (2) | −0.001 (2) | 0.012 (2) |
C24 | 0.030 (2) | 0.076 (3) | 0.030 (2) | 0.013 (2) | 0.0094 (16) | −0.005 (2) |
C25 | 0.042 (2) | 0.054 (3) | 0.051 (3) | 0.015 (2) | 0.012 (2) | −0.005 (2) |
C26 | 0.040 (2) | 0.0264 (18) | 0.040 (2) | −0.0004 (16) | 0.0127 (18) | 0.0046 (16) |
C27 | 0.037 (2) | 0.079 (3) | 0.040 (2) | −0.017 (2) | 0.0059 (18) | −0.008 (2) |
C28 | 0.034 (2) | 0.043 (2) | 0.039 (2) | −0.0005 (17) | 0.0243 (17) | −0.0032 (18) |
C29 | 0.050 (3) | 0.046 (2) | 0.059 (3) | 0.016 (2) | 0.015 (2) | −0.003 (2) |
Ni3 | 0.0335 (3) | 0.0340 (3) | 0.0456 (3) | −0.0043 (2) | 0.0069 (2) | 0.0019 (2) |
Ni4 | 0.0294 (3) | 0.0509 (3) | 0.0511 (3) | −0.0032 (2) | 0.0173 (2) | −0.0115 (3) |
O8 | 0.0359 (14) | 0.0377 (14) | 0.0383 (15) | 0.0033 (11) | 0.0052 (11) | −0.0036 (12) |
O9 | 0.0437 (16) | 0.0360 (15) | 0.0503 (17) | 0.0019 (13) | 0.0194 (13) | 0.0021 (14) |
O10 | 0.0497 (18) | 0.0543 (18) | 0.057 (2) | −0.0305 (15) | 0.0082 (16) | −0.0069 (16) |
O11 | 0.0414 (17) | 0.0552 (17) | 0.0451 (17) | 0.0124 (14) | 0.0217 (13) | 0.0100 (14) |
O12 | 0.0415 (16) | 0.0510 (17) | 0.0579 (19) | 0.0091 (13) | 0.0152 (14) | 0.0106 (15) |
O13 | 0.0463 (17) | 0.0450 (16) | 0.0499 (18) | −0.0125 (13) | 0.0076 (14) | −0.0159 (14) |
O14 | 0.0446 (18) | 0.0504 (18) | 0.071 (2) | −0.0164 (14) | 0.0152 (16) | −0.0178 (16) |
N5 | 0.0303 (17) | 0.060 (2) | 0.045 (2) | −0.0073 (16) | 0.0112 (15) | −0.0149 (17) |
N6 | 0.045 (2) | 0.056 (2) | 0.053 (2) | −0.0097 (17) | 0.0205 (18) | 0.0015 (18) |
N7 | 0.0311 (18) | 0.058 (2) | 0.042 (2) | 0.0075 (16) | 0.0018 (15) | 0.0064 (17) |
N8 | 0.042 (2) | 0.053 (2) | 0.053 (2) | 0.0136 (17) | 0.0080 (17) | −0.0054 (18) |
C30 | 0.043 (3) | 0.077 (3) | 0.044 (3) | 0.012 (2) | 0.001 (2) | −0.019 (2) |
C31 | 0.040 (3) | 0.079 (3) | 0.053 (3) | 0.009 (2) | −0.007 (2) | −0.004 (3) |
C32 | 0.049 (3) | 0.058 (3) | 0.073 (4) | −0.005 (2) | −0.005 (2) | −0.020 (3) |
C33 | 0.084 (4) | 0.096 (4) | 0.049 (3) | 0.021 (4) | −0.001 (3) | −0.009 (3) |
C34 | 0.065 (3) | 0.092 (4) | 0.037 (3) | 0.009 (3) | 0.004 (2) | 0.020 (3) |
C35 | 0.041 (3) | 0.082 (4) | 0.055 (3) | 0.014 (2) | −0.010 (2) | 0.001 (3) |
C36 | 0.041 (2) | 0.045 (2) | 0.071 (3) | −0.007 (2) | 0.001 (2) | −0.016 (2) |
C37 | 0.101 (5) | 0.091 (4) | 0.062 (4) | 0.018 (4) | 0.004 (3) | −0.010 (3) |
C38 | 0.072 (3) | 0.072 (3) | 0.025 (2) | −0.014 (3) | 0.004 (2) | 0.013 (2) |
C39 | 0.057 (3) | 0.077 (4) | 0.061 (3) | −0.010 (3) | −0.016 (2) | −0.024 (3) |
C40 | 0.046 (3) | 0.087 (3) | 0.023 (2) | 0.012 (2) | 0.0042 (18) | −0.014 (2) |
C41 | 0.032 (2) | 0.090 (4) | 0.037 (2) | 0.018 (2) | 0.0001 (18) | −0.012 (2) |
C42 | 0.070 (3) | 0.075 (4) | 0.053 (3) | 0.021 (3) | 0.004 (3) | 0.010 (3) |
C43 | 0.087 (4) | 0.051 (3) | 0.066 (3) | 0.025 (3) | 0.006 (3) | 0.014 (3) |
C44 | 0.053 (3) | 0.064 (3) | 0.059 (3) | 0.013 (2) | 0.020 (2) | 0.014 (2) |
C45 | 0.048 (3) | 0.050 (2) | 0.058 (3) | −0.032 (2) | 0.003 (2) | −0.001 (2) |
C46 | 0.040 (2) | 0.080 (3) | 0.041 (2) | −0.026 (2) | 0.0096 (19) | 0.011 (2) |
C47 | 0.062 (3) | 0.088 (4) | 0.050 (3) | −0.007 (3) | 0.015 (2) | −0.017 (3) |
C48 | 0.041 (3) | 0.090 (4) | 0.064 (3) | −0.002 (3) | 0.013 (2) | −0.024 (3) |
C49 | 0.091 (4) | 0.082 (4) | 0.069 (4) | 0.005 (3) | 0.028 (3) | −0.006 (3) |
C50 | 0.134 (6) | 0.068 (4) | 0.081 (4) | 0.032 (4) | 0.032 (4) | −0.001 (3) |
C51 | 0.110 (5) | 0.054 (3) | 0.078 (4) | −0.006 (3) | 0.028 (4) | −0.003 (3) |
C52 | 0.059 (3) | 0.065 (3) | 0.036 (2) | 0.009 (2) | 0.004 (2) | 0.007 (2) |
C53 | 0.064 (3) | 0.063 (3) | 0.047 (3) | −0.018 (2) | 0.022 (2) | −0.009 (2) |
C54 | 0.050 (3) | 0.057 (3) | 0.053 (3) | −0.028 (2) | 0.009 (2) | −0.009 (2) |
C55 | 0.041 (2) | 0.057 (3) | 0.041 (2) | −0.019 (2) | −0.0053 (19) | −0.017 (2) |
C56 | 0.050 (3) | 0.053 (3) | 0.068 (3) | −0.016 (2) | −0.002 (2) | −0.012 (2) |
C57 | 0.046 (3) | 0.063 (3) | 0.026 (2) | 0.001 (2) | 0.0130 (18) | −0.0054 (19) |
C58 | 0.048 (2) | 0.061 (3) | 0.039 (2) | 0.013 (2) | 0.0017 (19) | −0.002 (2) |
P1 | 0.0680 (9) | 0.0725 (9) | 0.0688 (10) | −0.0008 (7) | 0.0213 (8) | 0.0039 (8) |
F1 | 0.075 (2) | 0.0724 (18) | 0.0715 (19) | −0.0003 (15) | 0.0237 (15) | 0.0032 (15) |
F2 | 0.0698 (19) | 0.0741 (19) | 0.0734 (19) | −0.0010 (15) | 0.0223 (15) | 0.0030 (15) |
F3 | 0.080 (2) | 0.102 (2) | 0.079 (2) | −0.0078 (18) | 0.0234 (17) | 0.0141 (18) |
F4 | 0.089 (2) | 0.084 (2) | 0.081 (2) | 0.0103 (18) | 0.0168 (18) | −0.0191 (17) |
F5 | 0.0715 (19) | 0.0727 (18) | 0.0714 (19) | −0.0006 (15) | 0.0235 (15) | 0.0042 (15) |
F6 | 0.093 (2) | 0.082 (2) | 0.081 (2) | 0.0101 (18) | 0.0171 (18) | −0.0185 (18) |
P2 | 0.0721 (9) | 0.0658 (9) | 0.0754 (10) | −0.0031 (7) | 0.0265 (7) | 0.0042 (8) |
F7 | 0.0732 (19) | 0.0573 (16) | 0.081 (2) | −0.0028 (14) | 0.0179 (16) | 0.0122 (15) |
F8 | 0.0707 (18) | 0.0629 (17) | 0.080 (2) | −0.0019 (14) | 0.0353 (15) | 0.0085 (15) |
F9 | 0.076 (2) | 0.0715 (19) | 0.0745 (19) | 0.0003 (15) | 0.0094 (15) | 0.0019 (15) |
F10 | 0.077 (2) | 0.0761 (19) | 0.077 (2) | 0.0134 (16) | 0.0151 (16) | 0.0132 (16) |
F11 | 0.073 (2) | 0.0682 (18) | 0.081 (2) | −0.0015 (15) | 0.0317 (16) | 0.0081 (15) |
F12 | 0.074 (2) | 0.089 (2) | 0.078 (2) | −0.0045 (16) | 0.0223 (14) | 0.0058 (17) |
O15 | 0.0472 (18) | 0.067 (2) | 0.049 (2) | 0.0031 (16) | 0.0061 (15) | 0.0046 (16) |
Ni1—O4 | 1.986 (3) | Ni4—O12 | 1.987 (3) |
Ni1—O1 | 2.007 (2) | Ni4—N6 | 2.041 (3) |
Ni1—O6 | 2.078 (3) | Ni4—N8 | 2.060 (3) |
Ni1—N3 | 2.089 (3) | Ni4—O14 | 2.074 (3) |
Ni1—N1 | 2.112 (3) | Ni4—O10 | 2.124 (3) |
Ni1—O2 | 2.159 (3) | O8—C30 | 1.300 (5) |
Ni2—O1 | 2.000 (2) | O9—C46 | 1.464 (5) |
Ni2—O7 | 2.058 (3) | O9—H9 | 0.80 (4) |
Ni2—N4 | 2.068 (3) | O10—C54 | 1.383 (5) |
Ni2—O5 | 2.091 (2) | O10—H10 | 0.81 (5) |
Ni2—N2 | 2.119 (3) | O11—C57 | 1.210 (5) |
Ni2—O3 | 2.142 (3) | O12—C57 | 1.255 (5) |
N1—C10 | 1.489 (5) | O13—C55 | 1.242 (5) |
N1—C7 | 1.490 (4) | O14—C55 | 1.244 (5) |
N1—C16 | 1.518 (5) | N5—C45 | 1.495 (5) |
N2—C18 | 1.450 (5) | N5—C36 | 1.513 (5) |
N2—C24 | 1.458 (5) | N5—C39 | 1.547 (6) |
N2—C9 | 1.492 (5) | N6—C38 | 1.396 (6) |
N3—C11 | 1.317 (4) | N6—C47 | 1.500 (6) |
N3—C15 | 1.325 (5) | N6—C53 | 1.546 (5) |
N4—C23 | 1.326 (5) | N7—C44 | 1.299 (6) |
N4—C19 | 1.358 (5) | N7—C40 | 1.334 (5) |
O1—C1 | 1.285 (4) | N8—C52 | 1.354 (6) |
O2—C17 | 1.395 (5) | N8—C48 | 1.361 (6) |
O2—H2 | 0.76 (4) | C30—C35 | 1.388 (7) |
O3—C25 | 1.415 (5) | C30—C31 | 1.439 (7) |
O3—H3 | 0.84 (4) | C31—C32 | 1.366 (7) |
O4—C28 | 1.221 (4) | C31—C36 | 1.493 (7) |
O5—C28 | 1.238 (4) | C32—C33 | 1.407 (8) |
O6—C26 | 1.233 (4) | C32—H32 | 0.9300 |
O7—C26 | 1.266 (4) | C33—C34 | 1.382 (8) |
C1—C6 | 1.406 (5) | C33—C37 | 1.521 (7) |
C1—C2 | 1.432 (5) | C34—C35 | 1.295 (7) |
C2—C3 | 1.355 (6) | C34—H34 | 0.9300 |
C2—C9 | 1.506 (5) | C35—C38 | 1.559 (7) |
C3—C4 | 1.353 (6) | C36—H36A | 0.9700 |
C3—H3A | 0.9300 | C36—H36B | 0.9700 |
C4—C5 | 1.390 (6) | C37—H37A | 0.9600 |
C4—C8 | 1.486 (6) | C37—H37B | 0.9600 |
C5—C6 | 1.357 (6) | C37—H37C | 0.9600 |
C5—H5 | 0.9300 | C38—H38A | 0.9700 |
C6—C7 | 1.486 (6) | C38—H38B | 0.9700 |
C7—H7A | 0.9700 | C39—C40 | 1.454 (7) |
C7—H7B | 0.9700 | C39—H39A | 0.9700 |
C8—H8A | 0.9600 | C39—H39B | 0.9700 |
C8—H8B | 0.9600 | C40—C41 | 1.413 (6) |
C8—H8C | 0.9600 | C41—C42 | 1.351 (7) |
C9—H9A | 0.9700 | C41—H41 | 0.9300 |
C9—H9B | 0.9700 | C42—C43 | 1.272 (7) |
C10—C11 | 1.449 (5) | C42—H42 | 0.9300 |
C10—H10A | 0.9700 | C43—C44 | 1.324 (6) |
C10—H10B | 0.9700 | C43—H43 | 0.9300 |
C11—C12 | 1.322 (5) | C44—H44 | 0.9300 |
C12—C13 | 1.378 (7) | C45—C46 | 1.491 (6) |
C12—H12 | 0.9300 | C45—H45A | 0.9700 |
C13—C14 | 1.336 (7) | C45—H45B | 0.9700 |
C13—H13 | 0.9300 | C46—H46A | 0.9700 |
C14—C15 | 1.363 (6) | C46—H46B | 0.9700 |
C14—H14 | 0.9300 | C47—C48 | 1.440 (7) |
C15—H15 | 0.9300 | C47—H47A | 0.9700 |
C16—C17 | 1.489 (6) | C47—H47B | 0.9700 |
C16—H16A | 0.9700 | C48—C49 | 1.290 (7) |
C16—H16B | 0.9700 | C49—C50 | 1.405 (8) |
C17—H17A | 0.9700 | C49—H49 | 0.9300 |
C17—H17B | 0.9700 | C50—C51 | 1.375 (8) |
C18—C19 | 1.492 (5) | C50—H50 | 0.9300 |
C18—H18A | 0.9700 | C51—C52 | 1.375 (7) |
C18—H18B | 0.9700 | C51—H51 | 0.9300 |
C19—C20 | 1.338 (5) | C52—H52 | 0.9300 |
C20—C21 | 1.354 (7) | C53—C54 | 1.578 (6) |
C20—H20 | 0.9300 | C53—H53A | 0.9700 |
C21—C22 | 1.357 (7) | C53—H53B | 0.9700 |
C21—H21 | 0.9300 | C54—H54A | 0.9700 |
C22—C23 | 1.355 (6) | C54—H54B | 0.9700 |
C22—H22 | 0.9300 | C55—C56 | 1.513 (6) |
C23—H23 | 0.9300 | C56—H56A | 0.9600 |
C24—C25 | 1.527 (5) | C56—H56B | 0.9600 |
C24—H24A | 0.9700 | C56—H56C | 0.9600 |
C24—H24B | 0.9700 | C57—C58 | 1.504 (6) |
C25—H25A | 0.9700 | C58—H58A | 0.9600 |
C25—H25B | 0.9700 | C58—H58B | 0.9600 |
C26—C27 | 1.492 (5) | C58—H58C | 0.9600 |
C27—H27A | 0.9600 | P1—F3 | 1.505 (3) |
C27—H27C | 0.9600 | P1—F1 | 1.547 (3) |
C27—H27B | 0.9600 | P1—F6 | 1.547 (3) |
C28—C29 | 1.489 (5) | P1—F4 | 1.547 (4) |
C29—H29A | 0.9600 | P1—F2 | 1.557 (3) |
C29—H29B | 0.9600 | P1—F5 | 1.572 (3) |
C29—H29C | 0.9600 | P2—F7 | 1.447 (3) |
Ni3—O8 | 1.979 (3) | P2—F8 | 1.466 (3) |
Ni3—O13 | 2.029 (3) | P2—F9 | 1.476 (3) |
Ni3—N7 | 2.051 (3) | P2—F12 | 1.544 (3) |
Ni3—O11 | 2.079 (3) | P2—F10 | 1.565 (3) |
Ni3—O9 | 2.121 (3) | P2—F11 | 1.571 (3) |
Ni3—N5 | 2.123 (3) | O15—H15A | 0.85 (5) |
Ni4—O8 | 1.983 (3) | O15—H15B | 0.82 (5) |
O4—Ni1—O1 | 96.93 (11) | O8—Ni4—N6 | 93.50 (13) |
O4—Ni1—O6 | 93.29 (11) | O12—Ni4—N6 | 167.31 (14) |
O1—Ni1—O6 | 88.79 (10) | O8—Ni4—N8 | 90.69 (12) |
O4—Ni1—N3 | 93.73 (11) | O12—Ni4—N8 | 91.20 (14) |
O1—Ni1—N3 | 91.37 (10) | N6—Ni4—N8 | 79.77 (15) |
O6—Ni1—N3 | 172.90 (11) | O8—Ni4—O14 | 87.86 (11) |
O4—Ni1—N1 | 167.49 (11) | O12—Ni4—O14 | 97.18 (12) |
O1—Ni1—N1 | 93.54 (11) | N6—Ni4—O14 | 92.04 (14) |
O6—Ni1—N1 | 93.74 (11) | N8—Ni4—O14 | 171.59 (14) |
N3—Ni1—N1 | 79.17 (12) | O8—Ni4—O10 | 170.31 (11) |
O4—Ni1—O2 | 91.60 (11) | O12—Ni4—O10 | 92.25 (12) |
O1—Ni1—O2 | 169.49 (11) | N6—Ni4—O10 | 79.77 (14) |
O6—Ni1—O2 | 84.60 (11) | N8—Ni4—O10 | 94.92 (14) |
N3—Ni1—O2 | 94.19 (11) | O14—Ni4—O10 | 85.44 (12) |
N1—Ni1—O2 | 78.78 (11) | C30—O8—Ni3 | 123.9 (3) |
O1—Ni2—O7 | 95.89 (10) | C30—O8—Ni4 | 118.0 (2) |
O1—Ni2—N4 | 93.86 (11) | Ni3—O8—Ni4 | 117.73 (13) |
O7—Ni2—N4 | 91.00 (12) | C46—O9—Ni3 | 112.5 (2) |
O1—Ni2—O5 | 93.70 (10) | C46—O9—H9 | 111 (3) |
O7—Ni2—O5 | 89.50 (11) | Ni3—O9—H9 | 108 (3) |
N4—Ni2—O5 | 172.33 (11) | C54—O10—Ni4 | 114.6 (3) |
O1—Ni2—N2 | 91.87 (11) | C54—O10—H10 | 105 (4) |
O7—Ni2—N2 | 169.39 (11) | Ni4—O10—H10 | 111 (4) |
N4—Ni2—N2 | 81.24 (13) | C57—O11—Ni3 | 133.1 (3) |
O5—Ni2—N2 | 97.23 (12) | C57—O12—Ni4 | 136.3 (3) |
O1—Ni2—O3 | 168.01 (11) | C55—O13—Ni3 | 129.1 (3) |
O7—Ni2—O3 | 95.08 (10) | C55—O14—Ni4 | 131.9 (3) |
N4—Ni2—O3 | 90.76 (11) | C45—N5—C36 | 111.7 (3) |
O5—Ni2—O3 | 81.57 (10) | C45—N5—C39 | 112.8 (3) |
N2—Ni2—O3 | 77.90 (11) | C36—N5—C39 | 110.4 (3) |
C10—N1—C7 | 111.6 (3) | C45—N5—Ni3 | 103.1 (2) |
C10—N1—C16 | 109.9 (3) | C36—N5—Ni3 | 110.0 (2) |
C7—N1—C16 | 112.7 (3) | C39—N5—Ni3 | 108.5 (3) |
C10—N1—Ni1 | 111.3 (2) | C38—N6—C47 | 106.7 (4) |
C7—N1—Ni1 | 106.6 (2) | C38—N6—C53 | 110.0 (4) |
C16—N1—Ni1 | 104.5 (2) | C47—N6—C53 | 110.0 (3) |
C18—N2—C24 | 111.8 (3) | C38—N6—Ni4 | 110.7 (3) |
C18—N2—C9 | 109.9 (3) | C47—N6—Ni4 | 113.8 (3) |
C24—N2—C9 | 112.0 (3) | C53—N6—Ni4 | 105.7 (3) |
C18—N2—Ni2 | 110.0 (2) | C44—N7—C40 | 116.2 (4) |
C24—N2—Ni2 | 104.3 (2) | C44—N7—Ni3 | 127.2 (3) |
C9—N2—Ni2 | 108.5 (2) | C40—N7—Ni3 | 116.6 (3) |
C11—N3—C15 | 118.4 (3) | C52—N8—C48 | 116.8 (4) |
C11—N3—Ni1 | 116.2 (2) | C52—N8—Ni4 | 125.8 (3) |
C15—N3—Ni1 | 125.3 (3) | C48—N8—Ni4 | 113.6 (3) |
C23—N4—C19 | 117.0 (3) | O8—C30—C35 | 119.7 (4) |
C23—N4—Ni2 | 127.3 (3) | O8—C30—C31 | 121.5 (4) |
C19—N4—Ni2 | 115.7 (3) | C35—C30—C31 | 118.8 (4) |
C1—O1—Ni2 | 124.0 (2) | C32—C31—C30 | 118.9 (5) |
C1—O1—Ni1 | 119.6 (2) | C32—C31—C36 | 123.4 (5) |
Ni2—O1—Ni1 | 116.40 (12) | C30—C31—C36 | 117.6 (4) |
C17—O2—Ni1 | 113.3 (2) | C31—C32—C33 | 120.7 (5) |
C17—O2—H2 | 107 (4) | C31—C32—H32 | 119.6 |
Ni1—O2—H2 | 109 (4) | C33—C32—H32 | 119.6 |
C25—O3—Ni2 | 114.5 (2) | C34—C33—C32 | 116.5 (5) |
C25—O3—H3 | 113 (3) | C34—C33—C37 | 126.1 (6) |
Ni2—O3—H3 | 102 (3) | C32—C33—C37 | 117.4 (6) |
C28—O4—Ni1 | 135.8 (3) | C35—C34—C33 | 125.5 (5) |
C28—O5—Ni2 | 129.3 (3) | C35—C34—H34 | 117.3 |
C26—O6—Ni1 | 133.3 (3) | C33—C34—H34 | 117.3 |
C26—O7—Ni2 | 130.1 (2) | C34—C35—C30 | 119.5 (5) |
O1—C1—C6 | 123.5 (4) | C34—C35—C38 | 121.9 (5) |
O1—C1—C2 | 120.9 (3) | C30—C35—C38 | 117.9 (4) |
C6—C1—C2 | 115.5 (4) | C31—C36—N5 | 111.4 (4) |
C3—C2—C1 | 121.7 (4) | C31—C36—H36A | 109.3 |
C3—C2—C9 | 122.1 (4) | N5—C36—H36A | 109.3 |
C1—C2—C9 | 116.3 (3) | C31—C36—H36B | 109.3 |
C2—C3—C4 | 123.0 (4) | N5—C36—H36B | 109.3 |
C2—C3—H3A | 118.5 | H36A—C36—H36B | 108.0 |
C4—C3—H3A | 118.5 | C33—C37—H37A | 109.5 |
C3—C4—C5 | 115.2 (4) | C33—C37—H37B | 109.5 |
C3—C4—C8 | 123.8 (4) | H37A—C37—H37B | 109.5 |
C5—C4—C8 | 121.0 (4) | C33—C37—H37C | 109.5 |
C6—C5—C4 | 125.4 (4) | H37A—C37—H37C | 109.5 |
C6—C5—H5 | 117.3 | H37B—C37—H37C | 109.5 |
C4—C5—H5 | 117.3 | N6—C38—C35 | 114.8 (4) |
C5—C6—C1 | 119.1 (4) | N6—C38—H38A | 108.6 |
C5—C6—C7 | 124.5 (4) | C35—C38—H38A | 108.6 |
C1—C6—C7 | 116.3 (4) | N6—C38—H38B | 108.6 |
C6—C7—N1 | 113.0 (3) | C35—C38—H38B | 108.6 |
C6—C7—H7A | 109.0 | H38A—C38—H38B | 107.5 |
N1—C7—H7A | 109.0 | C40—C39—N5 | 114.3 (4) |
C6—C7—H7B | 109.0 | C40—C39—H39A | 108.7 |
N1—C7—H7B | 109.0 | N5—C39—H39A | 108.7 |
H7A—C7—H7B | 107.8 | C40—C39—H39B | 108.7 |
C4—C8—H8A | 109.5 | N5—C39—H39B | 108.7 |
C4—C8—H8B | 109.5 | H39A—C39—H39B | 107.6 |
H8A—C8—H8B | 109.5 | N7—C40—C41 | 122.1 (5) |
C4—C8—H8C | 109.5 | N7—C40—C39 | 118.5 (4) |
H8A—C8—H8C | 109.5 | C41—C40—C39 | 119.3 (4) |
H8B—C8—H8C | 109.5 | C42—C41—C40 | 114.4 (4) |
N2—C9—C2 | 115.7 (3) | C42—C41—H41 | 122.8 |
N2—C9—H9A | 108.3 | C40—C41—H41 | 122.8 |
C2—C9—H9A | 108.3 | C43—C42—C41 | 123.3 (5) |
N2—C9—H9B | 108.4 | C43—C42—H42 | 118.3 |
C2—C9—H9B | 108.4 | C41—C42—H42 | 118.3 |
H9A—C9—H9B | 107.4 | C42—C43—C44 | 119.2 (6) |
C11—C10—N1 | 112.6 (3) | C42—C43—H43 | 120.4 |
C11—C10—H10A | 109.1 | C44—C43—H43 | 120.4 |
N1—C10—H10A | 109.1 | N7—C44—C43 | 124.7 (5) |
C11—C10—H10B | 109.1 | N7—C44—H44 | 117.7 |
N1—C10—H10B | 109.1 | C43—C44—H44 | 117.7 |
H10A—C10—H10B | 107.8 | C46—C45—N5 | 110.2 (3) |
N3—C11—C12 | 121.8 (3) | C46—C45—H45A | 109.6 |
N3—C11—C10 | 118.6 (3) | N5—C45—H45A | 109.6 |
C12—C11—C10 | 119.5 (4) | C46—C45—H45B | 109.6 |
C11—C12—C13 | 118.9 (4) | N5—C45—H45B | 109.6 |
C11—C12—H12 | 120.5 | H45A—C45—H45B | 108.1 |
C13—C12—H12 | 120.5 | O9—C46—C45 | 109.1 (3) |
C14—C13—C12 | 121.1 (5) | O9—C46—H46A | 109.9 |
C14—C13—H13 | 119.4 | C45—C46—H46A | 109.9 |
C12—C13—H13 | 119.4 | O9—C46—H46B | 109.9 |
C13—C14—C15 | 116.0 (4) | C45—C46—H46B | 109.9 |
C13—C14—H14 | 122.0 | H46A—C46—H46B | 108.3 |
C15—C14—H14 | 122.0 | C48—C47—N6 | 107.4 (4) |
N3—C15—C14 | 123.6 (4) | C48—C47—H47A | 110.2 |
N3—C15—H15 | 118.2 | N6—C47—H47A | 110.2 |
C14—C15—H15 | 118.2 | C48—C47—H47B | 110.2 |
C17—C16—N1 | 109.6 (3) | N6—C47—H47B | 110.2 |
C17—C16—H16A | 109.8 | H47A—C47—H47B | 108.5 |
N1—C16—H16A | 109.8 | C49—C48—N8 | 122.4 (5) |
C17—C16—H16B | 109.8 | C49—C48—C47 | 119.1 (5) |
N1—C16—H16B | 109.8 | N8—C48—C47 | 118.5 (4) |
H16A—C16—H16B | 108.2 | C48—C49—C50 | 121.7 (6) |
O2—C17—C16 | 111.9 (3) | C48—C49—H49 | 119.1 |
O2—C17—H17A | 109.2 | C50—C49—H49 | 119.1 |
C16—C17—H17A | 109.2 | C51—C50—C49 | 118.1 (6) |
O2—C17—H17B | 109.2 | C51—C50—H50 | 121.0 |
C16—C17—H17B | 109.2 | C49—C50—H50 | 121.0 |
H17A—C17—H17B | 107.9 | C52—C51—C50 | 117.2 (5) |
N2—C18—C19 | 115.9 (3) | C52—C51—H51 | 121.4 |
N2—C18—H18A | 108.3 | C50—C51—H51 | 121.4 |
C19—C18—H18A | 108.3 | N8—C52—C51 | 123.8 (4) |
N2—C18—H18B | 108.3 | N8—C52—H52 | 118.1 |
C19—C18—H18B | 108.3 | C51—C52—H52 | 118.1 |
H18A—C18—H18B | 107.4 | N6—C53—C54 | 107.4 (3) |
C20—C19—N4 | 122.0 (4) | N6—C53—H53A | 110.2 |
C20—C19—C18 | 122.2 (4) | C54—C53—H53A | 110.2 |
N4—C19—C18 | 115.7 (3) | N6—C53—H53B | 110.2 |
C19—C20—C21 | 119.8 (4) | C54—C53—H53B | 110.2 |
C19—C20—H20 | 120.1 | H53A—C53—H53B | 108.5 |
C21—C20—H20 | 120.1 | O10—C54—C53 | 111.1 (3) |
C20—C21—C22 | 119.4 (4) | O10—C54—H54A | 109.4 |
C20—C21—H21 | 120.3 | C53—C54—H54A | 109.4 |
C22—C21—H21 | 120.3 | O10—C54—H54B | 109.4 |
C23—C22—C21 | 118.5 (5) | C53—C54—H54B | 109.4 |
C23—C22—H22 | 120.7 | H54A—C54—H54B | 108.0 |
C21—C22—H22 | 120.7 | O13—C55—O14 | 126.9 (4) |
N4—C23—C22 | 123.2 (4) | O13—C55—C56 | 117.0 (4) |
N4—C23—H23 | 118.4 | O14—C55—C56 | 115.9 (4) |
C22—C23—H23 | 118.4 | C55—C56—H56A | 109.5 |
N2—C24—C25 | 111.4 (3) | C55—C56—H56B | 109.5 |
N2—C24—H24A | 109.3 | H56A—C56—H56B | 109.5 |
C25—C24—H24A | 109.3 | C55—C56—H56C | 109.5 |
N2—C24—H24B | 109.3 | H56A—C56—H56C | 109.5 |
C25—C24—H24B | 109.3 | H56B—C56—H56C | 109.5 |
H24A—C24—H24B | 108.0 | O11—C57—O12 | 124.1 (4) |
O3—C25—C24 | 109.1 (3) | O11—C57—C58 | 117.9 (4) |
O3—C25—H25A | 109.9 | O12—C57—C58 | 118.0 (4) |
C24—C25—H25A | 109.9 | C57—C58—H58A | 109.5 |
O3—C25—H25B | 109.9 | C57—C58—H58B | 109.5 |
C24—C25—H25B | 109.9 | H58A—C58—H58B | 109.5 |
H25A—C25—H25B | 108.3 | C57—C58—H58C | 109.5 |
O6—C26—O7 | 124.2 (4) | H58A—C58—H58C | 109.5 |
O6—C26—C27 | 118.5 (4) | H58B—C58—H58C | 109.5 |
O7—C26—C27 | 117.2 (3) | F3—P1—F1 | 176.9 (2) |
C26—C27—H27A | 109.5 | F3—P1—F6 | 90.5 (2) |
C26—C27—H27C | 109.5 | F1—P1—F6 | 91.95 (18) |
H27A—C27—H27C | 109.5 | F3—P1—F4 | 90.5 (2) |
C26—C27—H27B | 109.5 | F1—P1—F4 | 91.35 (19) |
H27A—C27—H27B | 109.5 | F6—P1—F4 | 87.96 (18) |
H27C—C27—H27B | 109.5 | F3—P1—F2 | 89.04 (18) |
O4—C28—O5 | 126.8 (4) | F1—P1—F2 | 89.10 (17) |
O4—C28—C29 | 117.0 (3) | F6—P1—F2 | 91.28 (18) |
O5—C28—C29 | 116.0 (4) | F4—P1—F2 | 179.1 (2) |
C28—C29—H29A | 109.5 | F3—P1—F5 | 89.84 (18) |
C28—C29—H29B | 109.5 | F1—P1—F5 | 87.73 (16) |
H29A—C29—H29B | 109.5 | F6—P1—F5 | 179.2 (2) |
C28—C29—H29C | 109.5 | F4—P1—F5 | 91.34 (17) |
H29A—C29—H29C | 109.5 | F2—P1—F5 | 89.43 (17) |
H29B—C29—H29C | 109.5 | F7—P2—F8 | 95.96 (19) |
O8—Ni3—O13 | 96.61 (11) | F7—P2—F9 | 168.0 (2) |
O8—Ni3—N7 | 94.24 (12) | F8—P2—F9 | 95.06 (19) |
O13—Ni3—N7 | 92.22 (13) | F7—P2—F12 | 91.63 (19) |
O8—Ni3—O11 | 93.21 (10) | F8—P2—F12 | 90.89 (18) |
O13—Ni3—O11 | 89.51 (12) | F9—P2—F12 | 92.84 (19) |
N7—Ni3—O11 | 172.11 (12) | F7—P2—F10 | 84.92 (18) |
O8—Ni3—O9 | 170.19 (11) | F8—P2—F10 | 178.2 (2) |
O13—Ni3—O9 | 92.44 (11) | F9—P2—F10 | 83.93 (18) |
N7—Ni3—O9 | 89.18 (12) | F12—P2—F10 | 90.66 (18) |
O11—Ni3—O9 | 83.06 (11) | F7—P2—F11 | 87.04 (18) |
O8—Ni3—N5 | 91.19 (11) | F8—P2—F11 | 88.65 (17) |
O13—Ni3—N5 | 170.59 (12) | F9—P2—F11 | 88.58 (18) |
N7—Ni3—N5 | 81.93 (14) | F12—P2—F11 | 178.5 (2) |
O11—Ni3—N5 | 95.32 (13) | F10—P2—F11 | 89.82 (17) |
O9—Ni3—N5 | 80.17 (12) | H15A—O15—H15B | 108 (5) |
O8—Ni4—O12 | 95.53 (11) | ||
O4—Ni1—N1—C10 | −45.4 (7) | Ni2—O7—C26—C27 | −152.0 (3) |
O1—Ni1—N1—C10 | 101.6 (2) | Ni1—O4—C28—O5 | 15.7 (6) |
O6—Ni1—N1—C10 | −169.4 (2) | Ni1—O4—C28—C29 | −168.7 (3) |
N3—Ni1—N1—C10 | 10.9 (2) | Ni2—O5—C28—O4 | 8.6 (6) |
O2—Ni1—N1—C10 | −85.7 (2) | Ni2—O5—C28—C29 | −167.1 (3) |
O4—Ni1—N1—C7 | −167.3 (5) | O13—Ni3—O8—C30 | 144.9 (3) |
O1—Ni1—N1—C7 | −20.4 (2) | N7—Ni3—O8—C30 | 52.2 (4) |
O6—Ni1—N1—C7 | 68.7 (2) | O11—Ni3—O8—C30 | −125.2 (3) |
N3—Ni1—N1—C7 | −111.1 (2) | N5—Ni3—O8—C30 | −29.8 (3) |
O2—Ni1—N1—C7 | 152.4 (2) | O13—Ni3—O8—Ni4 | −42.25 (15) |
O4—Ni1—N1—C16 | 73.2 (6) | N7—Ni3—O8—Ni4 | −134.98 (15) |
O1—Ni1—N1—C16 | −139.9 (2) | O11—Ni3—O8—Ni4 | 47.62 (15) |
O6—Ni1—N1—C16 | −50.9 (3) | N5—Ni3—O8—Ni4 | 143.02 (15) |
N3—Ni1—N1—C16 | 129.4 (3) | O12—Ni4—O8—C30 | 132.0 (3) |
O2—Ni1—N1—C16 | 32.9 (2) | N6—Ni4—O8—C30 | −39.1 (3) |
O1—Ni2—N2—C18 | 102.7 (2) | N8—Ni4—O8—C30 | 40.7 (3) |
O7—Ni2—N2—C18 | −34.3 (8) | O14—Ni4—O8—C30 | −131.0 (3) |
N4—Ni2—N2—C18 | 9.1 (2) | O12—Ni4—O8—Ni3 | −41.25 (15) |
O5—Ni2—N2—C18 | −163.3 (2) | N6—Ni4—O8—Ni3 | 147.68 (16) |
O3—Ni2—N2—C18 | −83.6 (2) | N8—Ni4—O8—Ni3 | −132.53 (16) |
O1—Ni2—N2—C24 | −137.2 (2) | O14—Ni4—O8—Ni3 | 55.76 (15) |
O7—Ni2—N2—C24 | 85.8 (7) | O13—Ni3—O9—C46 | 176.3 (3) |
N4—Ni2—N2—C24 | 129.2 (2) | N7—Ni3—O9—C46 | −91.5 (3) |
O5—Ni2—N2—C24 | −43.2 (2) | O11—Ni3—O9—C46 | 87.1 (3) |
O3—Ni2—N2—C24 | 36.5 (2) | N5—Ni3—O9—C46 | −9.6 (3) |
O1—Ni2—N2—C9 | −17.6 (2) | O12—Ni4—O10—C54 | 169.5 (3) |
O7—Ni2—N2—C9 | −154.7 (6) | N6—Ni4—O10—C54 | −20.4 (3) |
N4—Ni2—N2—C9 | −111.3 (2) | N8—Ni4—O10—C54 | −99.1 (3) |
O5—Ni2—N2—C9 | 76.3 (2) | O14—Ni4—O10—C54 | 72.5 (3) |
O3—Ni2—N2—C9 | 156.1 (3) | O8—Ni3—O11—C57 | −30.1 (4) |
O4—Ni1—N3—C11 | 165.9 (2) | O13—Ni3—O11—C57 | 66.4 (4) |
O1—Ni1—N3—C11 | −97.1 (2) | O9—Ni3—O11—C57 | 159.0 (4) |
N1—Ni1—N3—C11 | −3.7 (2) | N5—Ni3—O11—C57 | −121.6 (4) |
O2—Ni1—N3—C11 | 74.0 (2) | O8—Ni4—O12—C57 | 6.9 (4) |
O4—Ni1—N3—C15 | −18.4 (3) | N6—Ni4—O12—C57 | 142.0 (6) |
O1—Ni1—N3—C15 | 78.6 (3) | N8—Ni4—O12—C57 | 97.7 (4) |
N1—Ni1—N3—C15 | 172.0 (3) | O14—Ni4—O12—C57 | −81.7 (4) |
O2—Ni1—N3—C15 | −110.3 (3) | O10—Ni4—O12—C57 | −167.4 (4) |
O1—Ni2—N4—C23 | 83.6 (3) | O8—Ni3—O13—C55 | −4.0 (4) |
O7—Ni2—N4—C23 | −12.4 (3) | N7—Ni3—O13—C55 | 90.5 (4) |
N2—Ni2—N4—C23 | 174.9 (4) | O11—Ni3—O13—C55 | −97.2 (4) |
O3—Ni2—N4—C23 | −107.5 (3) | O9—Ni3—O13—C55 | 179.8 (4) |
O1—Ni2—N4—C19 | −95.2 (2) | O8—Ni4—O14—C55 | −46.3 (4) |
O7—Ni2—N4—C19 | 168.8 (2) | O12—Ni4—O14—C55 | 49.0 (4) |
N2—Ni2—N4—C19 | −3.9 (2) | N6—Ni4—O14—C55 | −139.7 (4) |
O3—Ni2—N4—C19 | 73.7 (2) | O10—Ni4—O14—C55 | 140.7 (4) |
O7—Ni2—O1—C1 | 138.9 (3) | O8—Ni3—N5—C45 | −142.3 (3) |
N4—Ni2—O1—C1 | 47.5 (3) | N7—Ni3—N5—C45 | 123.6 (3) |
O5—Ni2—O1—C1 | −131.2 (3) | O11—Ni3—N5—C45 | −48.9 (3) |
N2—Ni2—O1—C1 | −33.8 (3) | O9—Ni3—N5—C45 | 33.1 (3) |
O3—Ni2—O1—C1 | −64.9 (6) | O8—Ni3—N5—C36 | −23.0 (3) |
O7—Ni2—O1—Ni1 | −41.94 (15) | N7—Ni3—N5—C36 | −117.1 (3) |
N4—Ni2—O1—Ni1 | −133.35 (15) | O11—Ni3—N5—C36 | 70.4 (3) |
O5—Ni2—O1—Ni1 | 47.94 (15) | O9—Ni3—N5—C36 | 152.3 (3) |
N2—Ni2—O1—Ni1 | 145.31 (15) | O8—Ni3—N5—C39 | 97.9 (3) |
O3—Ni2—O1—Ni1 | 114.2 (5) | N7—Ni3—N5—C39 | 3.8 (3) |
O4—Ni1—O1—C1 | 142.1 (3) | O11—Ni3—N5—C39 | −168.8 (3) |
O6—Ni1—O1—C1 | −124.7 (3) | O9—Ni3—N5—C39 | −86.8 (3) |
N3—Ni1—O1—C1 | 48.2 (3) | O8—Ni4—N6—C38 | −16.5 (3) |
N1—Ni1—O1—C1 | −31.1 (3) | O12—Ni4—N6—C38 | −151.8 (6) |
O2—Ni1—O1—C1 | −73.8 (7) | N8—Ni4—N6—C38 | −106.5 (3) |
O4—Ni1—O1—Ni2 | −37.06 (15) | O14—Ni4—N6—C38 | 71.5 (3) |
O6—Ni1—O1—Ni2 | 56.11 (14) | O10—Ni4—N6—C38 | 156.5 (3) |
N3—Ni1—O1—Ni2 | −130.99 (15) | O8—Ni4—N6—C47 | 103.7 (3) |
N1—Ni1—O1—Ni2 | 149.78 (14) | O12—Ni4—N6—C47 | −31.6 (8) |
O2—Ni1—O1—Ni2 | 107.1 (6) | N8—Ni4—N6—C47 | 13.6 (3) |
O4—Ni1—O2—C17 | 176.0 (3) | O14—Ni4—N6—C47 | −168.3 (3) |
O1—Ni1—O2—C17 | 31.6 (7) | O10—Ni4—N6—C47 | −83.3 (3) |
O6—Ni1—O2—C17 | 82.8 (3) | O8—Ni4—N6—C53 | −135.5 (3) |
N3—Ni1—O2—C17 | −90.2 (3) | O12—Ni4—N6—C53 | 89.2 (7) |
N1—Ni1—O2—C17 | −12.1 (3) | N8—Ni4—N6—C53 | 134.4 (3) |
O1—Ni2—O3—C25 | 14.3 (6) | O14—Ni4—N6—C53 | −47.5 (3) |
O7—Ni2—O3—C25 | 170.5 (3) | O10—Ni4—N6—C53 | 37.5 (3) |
N4—Ni2—O3—C25 | −98.5 (3) | O8—Ni3—N7—C44 | 88.3 (4) |
O5—Ni2—O3—C25 | 81.7 (3) | O13—Ni3—N7—C44 | −8.5 (4) |
N2—Ni2—O3—C25 | −17.6 (3) | O9—Ni3—N7—C44 | −100.9 (4) |
O1—Ni1—O4—C28 | 0.6 (4) | N5—Ni3—N7—C44 | 178.9 (4) |
O6—Ni1—O4—C28 | −88.5 (4) | O8—Ni3—N7—C40 | −94.4 (3) |
N3—Ni1—O4—C28 | 92.5 (4) | O13—Ni3—N7—C40 | 168.8 (3) |
N1—Ni1—O4—C28 | 147.4 (5) | O9—Ni3—N7—C40 | 76.4 (3) |
O2—Ni1—O4—C28 | −173.2 (4) | N5—Ni3—N7—C40 | −3.8 (3) |
O1—Ni2—O5—C28 | −38.6 (3) | O8—Ni4—N8—C52 | 65.7 (4) |
O7—Ni2—O5—C28 | 57.3 (3) | O12—Ni4—N8—C52 | −29.9 (4) |
N2—Ni2—O5—C28 | −130.9 (3) | N6—Ni4—N8—C52 | 159.1 (4) |
O3—Ni2—O5—C28 | 152.5 (3) | O10—Ni4—N8—C52 | −122.3 (4) |
O4—Ni1—O6—C26 | 52.6 (3) | O8—Ni4—N8—C48 | −91.4 (3) |
O1—Ni1—O6—C26 | −44.2 (3) | O12—Ni4—N8—C48 | 173.0 (3) |
N1—Ni1—O6—C26 | −137.7 (3) | N6—Ni4—N8—C48 | 2.0 (3) |
O2—Ni1—O6—C26 | 143.9 (3) | O10—Ni4—N8—C48 | 80.7 (3) |
O1—Ni2—O7—C26 | −7.2 (3) | Ni3—O8—C30—C35 | −132.8 (4) |
N4—Ni2—O7—C26 | 86.8 (3) | Ni4—O8—C30—C35 | 54.4 (5) |
O5—Ni2—O7—C26 | −100.8 (3) | Ni3—O8—C30—C31 | 45.4 (6) |
N2—Ni2—O7—C26 | 129.6 (6) | Ni4—O8—C30—C31 | −127.4 (4) |
O3—Ni2—O7—C26 | 177.7 (3) | O8—C30—C31—C32 | 179.5 (4) |
Ni2—O1—C1—C6 | −135.8 (3) | C35—C30—C31—C32 | −2.3 (7) |
Ni1—O1—C1—C6 | 45.1 (4) | O8—C30—C31—C36 | 1.4 (6) |
Ni2—O1—C1—C2 | 45.9 (4) | C35—C30—C31—C36 | 179.6 (4) |
Ni1—O1—C1—C2 | −133.2 (3) | C30—C31—C32—C33 | 1.0 (7) |
O1—C1—C2—C3 | −178.3 (4) | C36—C31—C32—C33 | 179.1 (5) |
C6—C1—C2—C3 | 3.3 (5) | C31—C32—C33—C34 | −0.5 (8) |
O1—C1—C2—C9 | 2.0 (5) | C31—C32—C33—C37 | −179.0 (5) |
C6—C1—C2—C9 | −176.5 (3) | C32—C33—C34—C35 | 1.3 (8) |
C1—C2—C3—C4 | −3.8 (6) | C37—C33—C34—C35 | 179.6 (5) |
C9—C2—C3—C4 | 176.0 (4) | C33—C34—C35—C30 | −2.6 (8) |
C2—C3—C4—C5 | 1.9 (6) | C33—C34—C35—C38 | −172.7 (5) |
C2—C3—C4—C8 | −174.7 (4) | O8—C30—C35—C34 | −178.8 (4) |
C3—C4—C5—C6 | 0.2 (6) | C31—C30—C35—C34 | 3.0 (7) |
C8—C4—C5—C6 | 176.9 (4) | O8—C30—C35—C38 | −8.3 (7) |
C4—C5—C6—C1 | −0.4 (6) | C31—C30—C35—C38 | 173.5 (4) |
C4—C5—C6—C7 | 177.7 (4) | C32—C31—C36—N5 | 120.5 (5) |
O1—C1—C6—C5 | −179.7 (3) | C30—C31—C36—N5 | −61.4 (5) |
C2—C1—C6—C5 | −1.3 (5) | C45—N5—C36—C31 | 179.1 (3) |
O1—C1—C6—C7 | 2.1 (5) | C39—N5—C36—C31 | −54.6 (4) |
C2—C1—C6—C7 | −179.5 (3) | Ni3—N5—C36—C31 | 65.2 (4) |
C5—C6—C7—N1 | 115.3 (4) | C47—N6—C38—C35 | −65.0 (5) |
C1—C6—C7—N1 | −66.6 (4) | C53—N6—C38—C35 | 175.8 (4) |
C10—N1—C7—C6 | −55.9 (4) | Ni4—N6—C38—C35 | 59.4 (5) |
C16—N1—C7—C6 | 179.9 (3) | C34—C35—C38—N6 | 113.3 (5) |
Ni1—N1—C7—C6 | 65.9 (3) | C30—C35—C38—N6 | −57.0 (6) |
C18—N2—C9—C2 | −58.2 (4) | C45—N5—C39—C40 | −117.2 (4) |
C24—N2—C9—C2 | 176.8 (3) | C36—N5—C39—C40 | 117.1 (4) |
Ni2—N2—C9—C2 | 62.2 (4) | Ni3—N5—C39—C40 | −3.6 (5) |
C3—C2—C9—N2 | 117.5 (4) | C44—N7—C40—C41 | 1.2 (6) |
C1—C2—C9—N2 | −62.7 (4) | Ni3—N7—C40—C41 | −176.4 (3) |
C7—N1—C10—C11 | 102.6 (4) | C44—N7—C40—C39 | −179.6 (4) |
C16—N1—C10—C11 | −131.6 (3) | Ni3—N7—C40—C39 | 2.8 (5) |
Ni1—N1—C10—C11 | −16.3 (4) | N5—C39—C40—N7 | 0.7 (6) |
C15—N3—C11—C12 | 2.9 (5) | N5—C39—C40—C41 | 179.9 (4) |
Ni1—N3—C11—C12 | 178.9 (3) | N7—C40—C41—C42 | −1.7 (6) |
C15—N3—C11—C10 | 179.1 (3) | C39—C40—C41—C42 | 179.1 (5) |
Ni1—N3—C11—C10 | −4.8 (4) | C40—C41—C42—C43 | 1.6 (8) |
N1—C10—C11—N3 | 14.3 (5) | C41—C42—C43—C44 | −1.0 (9) |
N1—C10—C11—C12 | −169.4 (4) | C40—N7—C44—C43 | −0.5 (7) |
N3—C11—C12—C13 | −3.6 (7) | Ni3—N7—C44—C43 | 176.8 (4) |
C10—C11—C12—C13 | −179.9 (4) | C42—C43—C44—N7 | 0.4 (8) |
C11—C12—C13—C14 | 2.2 (8) | C36—N5—C45—C46 | −171.8 (3) |
C12—C13—C14—C15 | −0.1 (8) | C39—N5—C45—C46 | 63.2 (4) |
C11—N3—C15—C14 | −0.7 (6) | Ni3—N5—C45—C46 | −53.7 (4) |
Ni1—N3—C15—C14 | −176.3 (3) | Ni3—O9—C46—C45 | −17.1 (4) |
C13—C14—C15—N3 | −0.6 (7) | N5—C45—C46—O9 | 47.9 (5) |
C10—N1—C16—C17 | 68.8 (4) | C38—N6—C47—C48 | 96.8 (5) |
C7—N1—C16—C17 | −166.0 (3) | C53—N6—C47—C48 | −144.0 (4) |
Ni1—N1—C16—C17 | −50.7 (4) | Ni4—N6—C47—C48 | −25.7 (5) |
Ni1—O2—C17—C16 | −13.3 (4) | C52—N8—C48—C49 | 2.0 (7) |
N1—C16—C17—O2 | 43.1 (5) | Ni4—N8—C48—C49 | 161.3 (5) |
C24—N2—C18—C19 | −128.5 (3) | C52—N8—C48—C47 | −178.0 (4) |
C9—N2—C18—C19 | 106.4 (4) | Ni4—N8—C48—C47 | −18.7 (6) |
Ni2—N2—C18—C19 | −13.1 (4) | N6—C47—C48—C49 | −151.1 (5) |
C23—N4—C19—C20 | 2.3 (5) | N6—C47—C48—N8 | 28.9 (6) |
Ni2—N4—C19—C20 | −178.8 (3) | N8—C48—C49—C50 | −1.4 (9) |
C23—N4—C19—C18 | 178.9 (3) | C47—C48—C49—C50 | 178.6 (6) |
Ni2—N4—C19—C18 | −2.2 (4) | C48—C49—C50—C51 | 0.4 (10) |
N2—C18—C19—C20 | −172.8 (4) | C49—C50—C51—C52 | 0.0 (9) |
N2—C18—C19—N4 | 10.6 (5) | C48—N8—C52—C51 | −1.6 (7) |
N4—C19—C20—C21 | −2.0 (6) | Ni4—N8—C52—C51 | −158.1 (4) |
C18—C19—C20—C21 | −178.4 (4) | C50—C51—C52—N8 | 0.7 (9) |
C19—C20—C21—C22 | 1.4 (8) | C38—N6—C53—C54 | −168.8 (4) |
C20—C21—C22—C23 | −1.1 (8) | C47—N6—C53—C54 | 74.0 (4) |
C19—N4—C23—C22 | −2.0 (6) | Ni4—N6—C53—C54 | −49.2 (4) |
Ni2—N4—C23—C22 | 179.2 (4) | Ni4—O10—C54—C53 | −3.1 (4) |
C21—C22—C23—N4 | 1.5 (8) | N6—C53—C54—O10 | 34.1 (5) |
C18—N2—C24—C25 | 66.8 (4) | Ni3—O13—C55—O14 | 22.5 (7) |
C9—N2—C24—C25 | −169.3 (3) | Ni3—O13—C55—C56 | −153.2 (3) |
Ni2—N2—C24—C25 | −52.1 (4) | Ni4—O14—C55—O13 | 9.5 (7) |
Ni2—O3—C25—C24 | −5.6 (4) | Ni4—O14—C55—C56 | −174.7 (3) |
N2—C24—C25—O3 | 38.9 (5) | Ni3—O11—C57—O12 | 0.3 (7) |
Ni1—O6—C26—O7 | 3.4 (6) | Ni3—O11—C57—C58 | 178.6 (3) |
Ni1—O6—C26—C27 | −175.3 (3) | Ni4—O12—C57—O11 | 14.9 (7) |
Ni2—O7—C26—O6 | 29.3 (5) | Ni4—O12—C57—C58 | −163.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O15 | 0.76 (4) | 2.48 (5) | 2.956 (4) | 122 (4) |
O3—H3···O13 | 0.84 (4) | 2.11 (4) | 2.714 (4) | 129 (4) |
O9—H9···O7 | 0.80 (4) | 2.04 (4) | 2.737 (4) | 145 (4) |
O10—H10···O15i | 0.81 (5) | 2.39 (5) | 2.876 (5) | 120 (4) |
O15—H15A···O10ii | 0.85 (5) | 2.48 (5) | 2.876 (5) | 109 (4) |
O15—H15A···O5iii | 0.85 (5) | 2.58 (5) | 3.079 (4) | 118 (4) |
O15—H15B···O9iii | 0.82 (5) | 2.22 (5) | 3.009 (4) | 162 (5) |
C8—H8C···F1iv | 0.96 | 2.69 | 3.466 (5) | 139 |
C10—H10A···F12 | 0.97 | 2.52 | 3.348 (5) | 143 |
C14—H14···F5 | 0.93 | 2.48 | 3.355 (6) | 158 |
C22—H22···F4v | 0.93 | 2.52 | 3.377 (5) | 154 |
C29—H29B···O15iii | 0.96 | 2.54 | 3.209 (5) | 127 |
C34—H34···F11vi | 0.93 | 2.66 | 3.479 (6) | 148 |
C39—H39A···F2iii | 0.97 | 2.42 | 3.370 (6) | 166 |
C46—H46A···O4iii | 0.97 | 2.61 | 3.373 (5) | 136 |
C47—H47A···F4vii | 0.97 | 2.54 | 3.267 (6) | 132 |
C54—H54B···F6vii | 0.97 | 2.50 | 3.406 (6) | 155 |
C58—H58A···F7iii | 0.96 | 2.57 | 3.491 (5) | 162 |
C58—H58B···O12vii | 0.96 | 2.56 | 3.293 (5) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x−1, −y+3/2, z+1/2; (vii) −x, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ni2(C25H31N4O3)(C2H3O2)2]PF6·0.5H2O |
Mr | 825.03 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 15.7776 (19), 17.191 (2), 25.513 (3) |
β (°) | 93.914 (3) |
V (Å3) | 6904.0 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.22 |
Crystal size (mm) | 0.28 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.72, 0.76 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36723, 13513, 9603 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.102, 1.10 |
No. of reflections | 13513 |
No. of parameters | 916 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.48, −0.42 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O15 | 0.76 (4) | 2.48 (5) | 2.956 (4) | 122 (4) |
O3—H3···O13 | 0.84 (4) | 2.11 (4) | 2.714 (4) | 129 (4) |
O9—H9···O7 | 0.80 (4) | 2.04 (4) | 2.737 (4) | 145 (4) |
O10—H10···O15i | 0.81 (5) | 2.39 (5) | 2.876 (5) | 120 (4) |
O15—H15A···O10ii | 0.85 (5) | 2.48 (5) | 2.876 (5) | 109 (4) |
O15—H15A···O5iii | 0.85 (5) | 2.58 (5) | 3.079 (4) | 118 (4) |
O15—H15B···O9iii | 0.82 (5) | 2.22 (5) | 3.009 (4) | 162 (5) |
C8—H8C···F1iv | 0.96 | 2.69 | 3.466 (5) | 139 |
C10—H10A···F12 | 0.97 | 2.52 | 3.348 (5) | 143 |
C14—H14···F5 | 0.93 | 2.48 | 3.355 (6) | 158 |
C22—H22···F4v | 0.93 | 2.52 | 3.377 (5) | 154 |
C29—H29B···O15iii | 0.96 | 2.54 | 3.209 (5) | 127 |
C34—H34···F11vi | 0.93 | 2.66 | 3.479 (6) | 148 |
C39—H39A···F2iii | 0.97 | 2.42 | 3.370 (6) | 166 |
C46—H46A···O4iii | 0.97 | 2.61 | 3.373 (5) | 136 |
C47—H47A···F4vii | 0.97 | 2.54 | 3.267 (6) | 132 |
C54—H54B···F6vii | 0.97 | 2.50 | 3.406 (6) | 155 |
C58—H58A···F7iii | 0.96 | 2.57 | 3.491 (5) | 162 |
C58—H58B···O12vii | 0.96 | 2.56 | 3.293 (5) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x−1, −y+3/2, z+1/2; (vii) −x, −y+2, −z+1. |
The hydrolysis of biomolecules by dinuclear metallohydrolases has been a hot subject for bioinorganic chemists for many years (Wilcox, 1996). Dinuclear nickel complexes have long been of great interest because the Ni atom was found to act as the active center of urease (Lippard, 1995), which is an enzyme isolated from various bacteria and plants that can hydrolyze urea to form carbamate and ammonia. To gain an insight into the relationship of the structure and catalytic activity of urease, as well as its hydrolytic mechanism, a number of synthetic functional models containing dinuclear nickel of relevance of the active site of urease has been reported (Barrios & Lippard, 2000; Carlsson et al., 2004; Beddie et al., 2005). We have synthesized previously a symmetrical ligand, 2,6-bis{[(2-pyridylmethyl)(2-hydroxyethyl)amino] methyl}-4-methylphenol, (L), and showed that it can form a dinuclear zinc complex with a phenolate and an acetate bridge (Chen et al., 2005). We report here the crystal structure of the title compound, (I), whose structure is different from that of the previously reported dinuclear zinc complex (discussed later).
The asymmetric unit of (I) (Fig. 1), contains two dinuclear nickel cations, two hexafluorophosphate anions and one water molecule of crystallization. The two symmetry-independent dinuclear cations are linked into a dimeric unit through cooperative O—H···O hydrogen bonds (O9—H9···O7 and O3—-H3···O13; Table 2). The second hydroxy O atom in each cation forms a hydrogen bond with the O atom of a neighbouring water molecule. The water H atoms, in turn, interact with hydroxy O atoms and an acetate O atom in two different but symmetry-related cations. Together, these interactions link the cations into extended chains which run parallel to the [100] direction. Additional weak intermolecular C—H···F and C—H···O interactions (Table 1), link all of the units in the structure into a three-dimensional framework.
Within each cation, the two Ni atoms are bridged by two exogenous acetate groups and an endogenous cresolic O atom of L in a syn–syn mode, providing a (µ-phenolato)bis(µ-acetato)dinickel(II) core. Both nickel centers have an N2O4 coordination environment and the geometry around each Ni atom can be regarded as that of a slightly distorted octahedron. The two octahedra in each dinuclear nickel cation are corner-shared via the bridging phenol O atom. The planes defined by each Ni atom and its coordinated N atoms from the imine pendant arm (represented by atoms N1, N2, N5 and N6) and the pyridine ring include the two coordinated O atoms of the acetate bridges and are almost coplanar with the associated pyridine ring. The structure of (I) is different from that of the analogous dinuclear zinc complex (Chen et al., 2005). In the latter complex, the independent Zn atoms have different coordination numbers and geometry. One Zn atom is six-coordinate with an N2O4 donor set having a slightly distorted octahedral geometry, whereas the other Zn atom is five-coordinate with an N2O3 donor set having a roughly trigonal–bipyramidal geometry. Moreover, the two zinc-bound terminal alcohol hydroxy groups are also different; one is deprotonated but the other is protonated.
The average separation between the two Ni atoms in (I) is 3.399 (1) Å, which is comparable with that in urease (3.5 Å) (Jabri et al., 1995) and also similar to the Ni···Ni distances in most of the `end-off' compartmental ligand-derived dinuclear nickel complexes with additional bridges (Koga et al., 1998; Uozumi et al., 1998; Adams et al., 2003; Carlsson et al., 2004). The average Ni—Oethanol bond length is 2.136 (3) Å, which is longer than those for Ni—Ocresol [1.992 (3) Å] and Ni—Oacetate [2.048 (2) Å]. The Ni—O distances for the acetate O atom not accepting a hydrogen bond and longer than those where a hydrogen bond is involved. As a result of the two exogenous acetate bridges, the Ni···Ni distance and the Ni—Ocresol—Ni angle [116.37 (14)°] are somewhat smaller than those observed in similar binuclear nickel complexes without additional bridges, e.g. [Ni2L4(OAc)(µ-OAc)(CH3OH)(OH2)]+ [Ni···Ni = 3.5419 (12) Å and Ni—Ocresol—Ni = 121.40 (19)°; Adams et al., 2003] and [Ni2(BPPMP)(H2O)4]+ [Ni···Ni = 3.775 (1) Å and Ni—Ocresol—Ni = 131.8 (1)°; de Brito et al., 2000]. The average Ni—N distance in (I) [2.083 (3) Å] agrees with the values expected for octahedral NiII complexes (Buchanan et al., 1989).