metal-organic compounds
The crystal and molecular structures of the title compound, 3-bromo-3-(dibenzylphenylphosphonio)-2,2-diphenyl-5-trifluoromethyl-1H-benzo[e][1,2]phosphanickelepine, [NiBr(C22H17F3P)(C20H19P)], which was obtained as the major regioisomer from insertion of HCCCF3 into the Ni—C bond of the five-membered phosphanickelacycle [NiBr(o-C6H4CH2PPh2-κ2C,P){PPh(CH2Ph)2}], have been determined. Principal geometric data include the Ni—X bond lengths Ni—Br 2.3343 (4) Å, Ni—P 2.1867 (7) and 2.2094 (7) Å, and Ni—C 1.882 (3) Å, and the two trans angles P—Ni—P 171.55 (3)° and Br—Ni—C 176.88 (9)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102002883/gg1096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102002883/gg1096Isup2.hkl |
CCDC reference: 184466
Computing details top
Data collection: COLLECT (Nonius BV, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS and maXus (Mackay et al., 1999).
(I) top
Crystal data top
C42H36BrF3NiP2 | F(000) = 1632 |
Mr = 798.28 | Dx = 1.463 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 58628 reflections |
a = 18.3307 (2) Å | θ = 2.9–27.5° |
b = 10.9887 (1) Å | µ = 1.77 mm−1 |
c = 18.7279 (2) Å | T = 200 K |
β = 106.1717 (7)° | Prism, orange |
V = 3623.10 (6) Å3 | 0.24 × 0.21 × 0.12 mm |
Z = 4 |
Data collection top
KappaCCD diffractometer | 5217 reflections with I > 3σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.075 |
CCD scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: integration Gaussian integration (Coppens, 1970) | h = −23→23 |
Tmin = 0.668, Tmax = 0.831 | k = −13→14 |
71633 measured reflections | l = −24→24 |
8294 independent reflections |
Refinement top
Refinement on F | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.031 | Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979): 0.650, 0.286 and0.339 |
wR(F2) = 0.036 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.73 e Å−3 |
5217 reflections | Δρmin = −0.54 e Å−3 |
447 parameters | Extinction correction: Larson (1970) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 191 (18) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.191505 (17) | 0.31524 (3) | 0.951709 (17) | 0.0298 | |
Br1 | 0.104524 (15) | 0.44827 (3) | 0.875488 (17) | 0.0453 | |
P1 | 0.10451 (4) | 0.21906 (6) | 0.98931 (4) | 0.0313 | |
P2 | 0.29158 (4) | 0.39606 (6) | 0.92591 (4) | 0.0358 | |
C1 | 0.22934 (16) | 0.0181 (2) | 0.94918 (15) | 0.0379 | |
C2 | 0.25705 (19) | −0.0377 (3) | 0.89492 (19) | 0.0518 | |
C3 | 0.2108 (2) | −0.1141 (3) | 0.84242 (19) | 0.0591 | |
C4 | 0.1375 (2) | −0.1364 (3) | 0.84341 (18) | 0.0575 | |
C5 | 0.10914 (17) | −0.0814 (3) | 0.89652 (17) | 0.0449 | |
C6 | 0.15411 (16) | −0.0040 (2) | 0.94971 (15) | 0.0369 | |
C7 | 0.27757 (15) | 0.0967 (3) | 1.00880 (16) | 0.0397 | |
C8 | 0.26259 (15) | 0.2145 (2) | 1.01725 (16) | 0.0372 | |
C9 | 0.12346 (15) | 0.0556 (2) | 1.00807 (15) | 0.0372 | |
C10 | 0.33860 (19) | 0.0315 (3) | 1.0648 (2) | 0.0568 | |
C11 | 0.00591 (15) | 0.2138 (2) | 0.93185 (14) | 0.0362 | |
C12 | −0.00863 (17) | 0.1673 (3) | 0.85992 (16) | 0.0440 | |
C13 | −0.08304 (19) | 0.1470 (3) | 0.81729 (18) | 0.0517 | |
C14 | −0.14286 (17) | 0.1744 (3) | 0.84580 (19) | 0.0528 | |
C15 | −0.12876 (17) | 0.2229 (3) | 0.91642 (18) | 0.0492 | |
C16 | −0.05486 (15) | 0.2430 (3) | 0.95957 (16) | 0.0395 | |
C17 | 0.09796 (14) | 0.2834 (2) | 1.07643 (14) | 0.0344 | |
C18 | 0.09180 (15) | 0.2123 (3) | 1.13653 (15) | 0.0393 | |
C19 | 0.08415 (18) | 0.2670 (3) | 1.20051 (16) | 0.0476 | |
C20 | 0.08389 (19) | 0.3924 (3) | 1.20606 (17) | 0.0513 | |
C21 | 0.08972 (18) | 0.4641 (3) | 1.14733 (17) | 0.0486 | |
C22 | 0.09649 (16) | 0.4103 (3) | 1.08282 (16) | 0.0409 | |
C23 | 0.32788 (16) | 0.2882 (3) | 0.86904 (16) | 0.0414 | |
C24 | 0.28064 (19) | 0.2598 (3) | 0.79976 (18) | 0.0527 | |
C25 | 0.3028 (2) | 0.1771 (3) | 0.7543 (2) | 0.0624 | |
C26 | 0.3726 (2) | 0.1200 (4) | 0.7772 (2) | 0.0629 | |
C27 | 0.4198 (2) | 0.1470 (3) | 0.8470 (2) | 0.0630 | |
C28 | 0.39705 (17) | 0.2316 (3) | 0.89262 (18) | 0.0487 | |
C29 | 0.37385 (15) | 0.4279 (3) | 1.00427 (15) | 0.0395 | |
C30 | 0.35979 (16) | 0.5166 (2) | 1.06102 (15) | 0.0398 | |
C31 | 0.29280 (17) | 0.5175 (3) | 1.08283 (16) | 0.0440 | |
C32 | 0.28553 (17) | 0.5938 (3) | 1.13987 (17) | 0.0459 | |
C33 | 0.34436 (19) | 0.6694 (3) | 1.17485 (18) | 0.0518 | |
C34 | 0.4095 (2) | 0.6707 (3) | 1.1528 (2) | 0.0588 | |
C35 | 0.41738 (18) | 0.5954 (3) | 1.09725 (18) | 0.0509 | |
C36 | 0.27737 (15) | 0.5392 (3) | 0.87159 (16) | 0.0412 | |
C37 | 0.34838 (15) | 0.5937 (3) | 0.85925 (16) | 0.0406 | |
C38 | 0.37976 (17) | 0.5463 (3) | 0.80507 (17) | 0.0474 | |
C39 | 0.44533 (18) | 0.5957 (3) | 0.7943 (2) | 0.0575 | |
C40 | 0.48025 (18) | 0.6930 (4) | 0.8362 (2) | 0.0608 | |
C41 | 0.4494 (2) | 0.7419 (3) | 0.8891 (2) | 0.0608 | |
C42 | 0.38394 (18) | 0.6920 (3) | 0.90139 (18) | 0.0508 | |
F1 | 0.31173 (14) | −0.0608 (2) | 1.09672 (15) | 0.0967 | |
F2 | 0.39044 (15) | −0.0183 (3) | 1.03628 (17) | 0.1126 | |
F3 | 0.37703 (13) | 0.0996 (2) | 1.12142 (14) | 0.0883 | |
H21 | 0.31063 | −0.0222 | 0.89432 | 0.0630* | |
H31 | 0.2312 | −0.1526 | 0.80361 | 0.0711* | |
H41 | 0.1046 | −0.1924 | 0.80586 | 0.0675* | |
H51 | 0.05560 | −0.0974 | 0.89710 | 0.0513* | |
H91 | 0.16158 | 0.0463 | 1.05767 | 0.0448* | |
H92 | 0.07508 | 0.0143 | 1.00881 | 0.0448* | |
H121 | 0.03475 | 0.1490 | 0.83899 | 0.0504* | |
H131 | −0.09299 | 0.1124 | 0.76609 | 0.0578* | |
H141 | −0.19622 | 0.1590 | 0.81535 | 0.0586* | |
H151 | −0.17227 | 0.2437 | 0.93663 | 0.0566* | |
H161 | −0.04494 | 0.2785 | 1.01053 | 0.0463* | |
H181 | 0.09299 | 0.1216 | 1.13303 | 0.0458* | |
H191 | 0.07889 | 0.2158 | 1.24292 | 0.0569* | |
H201 | 0.07976 | 0.4316 | 1.25299 | 0.0617* | |
H211 | 0.08841 | 0.5548 | 1.15114 | 0.0599* | |
H221 | 0.10048 | 0.4622 | 1.04018 | 0.0501* | |
H241 | 0.22973 | 0.2998 | 0.78285 | 0.0608* | |
H251 | 0.2679 | 0.1588 | 0.7041 | 0.0750* | |
H261 | 0.3888 | 0.0609 | 0.7440 | 0.0770* | |
H271 | 0.4700 | 0.1050 | 0.8650 | 0.0777* | |
H281 | 0.43167 | 0.2514 | 0.94277 | 0.0593* | |
H291 | 0.39125 | 0.3493 | 1.03040 | 0.0459* | |
H292 | 0.41497 | 0.4619 | 0.98450 | 0.0459* | |
H311 | 0.24975 | 0.4633 | 1.05700 | 0.0508* | |
H321 | 0.23753 | 0.5930 | 1.15534 | 0.0536* | |
H331 | 0.33948 | 0.7230 | 1.21642 | 0.0602* | |
H341 | 0.4517 | 0.7273 | 1.1773 | 0.0701* | |
H351 | 0.46567 | 0.5965 | 1.08231 | 0.0604* | |
H361 | 0.25446 | 0.6006 | 0.89838 | 0.0501* | |
H362 | 0.24128 | 0.5222 | 0.82175 | 0.0501* | |
H381 | 0.35442 | 0.4758 | 0.77418 | 0.0569* | |
H391 | 0.46700 | 0.5610 | 0.7552 | 0.0694* | |
H401 | 0.52819 | 0.7271 | 0.8288 | 0.0715* | |
H411 | 0.4739 | 0.8144 | 0.9184 | 0.0674* | |
H421 | 0.36232 | 0.7264 | 0.94056 | 0.0591* | |
H81 | 0.2924 (17) | 0.251 (3) | 1.0582 (17) | 0.037 (7)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02967 (16) | 0.03002 (16) | 0.03116 (16) | −0.00106 (13) | 0.01104 (12) | 0.00390 (12) |
Br1 | 0.03471 (14) | 0.04891 (18) | 0.05261 (17) | 0.00381 (12) | 0.01280 (12) | 0.01897 (13) |
P1 | 0.0327 (3) | 0.0317 (3) | 0.0323 (3) | −0.0020 (3) | 0.0136 (3) | 0.0027 (2) |
P2 | 0.0312 (3) | 0.0377 (4) | 0.0391 (4) | −0.0021 (3) | 0.0107 (3) | 0.0072 (3) |
C1 | 0.0422 (14) | 0.0305 (13) | 0.0436 (14) | 0.0026 (11) | 0.0162 (12) | 0.0051 (11) |
C2 | 0.0579 (18) | 0.0420 (16) | 0.065 (2) | 0.0111 (14) | 0.0323 (16) | 0.0080 (15) |
C3 | 0.084 (2) | 0.0480 (18) | 0.0523 (19) | 0.0085 (17) | 0.0313 (18) | −0.0043 (15) |
C4 | 0.081 (2) | 0.0417 (16) | 0.0474 (18) | −0.0023 (16) | 0.0141 (17) | −0.0077 (14) |
C5 | 0.0498 (16) | 0.0354 (14) | 0.0489 (16) | −0.0055 (12) | 0.0129 (13) | −0.0007 (12) |
C6 | 0.0439 (14) | 0.0289 (13) | 0.0395 (14) | 0.0004 (11) | 0.0143 (11) | 0.005 (1) |
C7 | 0.0349 (13) | 0.0364 (14) | 0.0478 (16) | −0.0001 (11) | 0.0116 (12) | 0.0093 (12) |
C8 | 0.0362 (13) | 0.0394 (14) | 0.0366 (14) | −0.0081 (11) | 0.0110 (11) | 0.0015 (11) |
C9 | 0.0383 (13) | 0.0341 (13) | 0.0420 (14) | −0.0024 (11) | 0.0159 (11) | 0.0041 (11) |
C10 | 0.0452 (16) | 0.0483 (18) | 0.070 (2) | 0.0014 (14) | 0.0052 (15) | 0.0147 (16) |
C11 | 0.0381 (13) | 0.0353 (14) | 0.0361 (13) | −0.0032 (11) | 0.0119 (11) | 0.006 (1) |
C12 | 0.0501 (16) | 0.0436 (16) | 0.0393 (15) | −0.0009 (13) | 0.0139 (13) | 0.0022 (12) |
C13 | 0.0588 (19) | 0.0441 (17) | 0.0430 (16) | −0.0047 (14) | −0.0010 (14) | 0.0051 (13) |
C14 | 0.0407 (15) | 0.0488 (17) | 0.061 (2) | −0.0072 (13) | 0.0006 (14) | 0.0164 (15) |
C15 | 0.0380 (14) | 0.0518 (17) | 0.0589 (19) | 0.0021 (13) | 0.0155 (14) | 0.0189 (15) |
C16 | 0.0368 (13) | 0.0411 (15) | 0.0424 (15) | −0.0000 (11) | 0.0142 (11) | 0.0098 (12) |
C17 | 0.0323 (12) | 0.0393 (14) | 0.0335 (13) | −0.003 (1) | 0.012 (1) | 0.001 (1) |
C18 | 0.0426 (14) | 0.0409 (15) | 0.0364 (14) | −0.0039 (12) | 0.0145 (11) | 0.0037 (11) |
C19 | 0.0543 (17) | 0.0559 (18) | 0.0364 (15) | −0.0031 (14) | 0.0187 (13) | 0.0050 (13) |
C20 | 0.0603 (19) | 0.0560 (19) | 0.0447 (16) | −0.0068 (15) | 0.0265 (15) | −0.0080 (14) |
C21 | 0.0582 (18) | 0.0428 (16) | 0.0526 (17) | −0.0044 (14) | 0.0282 (15) | −0.0060 (13) |
C22 | 0.0465 (15) | 0.0382 (14) | 0.0433 (15) | −0.0011 (12) | 0.0215 (12) | 0.0034 (12) |
C23 | 0.0419 (14) | 0.0400 (15) | 0.0459 (15) | −0.0073 (12) | 0.0181 (12) | 0.0007 (12) |
C24 | 0.0541 (18) | 0.0556 (19) | 0.0512 (18) | −0.0059 (15) | 0.0194 (15) | −0.0113 (15) |
C25 | 0.062 (2) | 0.072 (2) | 0.058 (2) | −0.0136 (18) | 0.0238 (17) | −0.0256 (18) |
C26 | 0.058 (2) | 0.070 (2) | 0.070 (2) | −0.0151 (18) | 0.0338 (18) | −0.0271 (19) |
C27 | 0.0478 (17) | 0.062 (2) | 0.086 (3) | −0.0021 (16) | 0.0305 (18) | −0.0085 (19) |
C28 | 0.0479 (16) | 0.0515 (17) | 0.0504 (17) | −0.0102 (14) | 0.0198 (14) | −0.0086 (14) |
C29 | 0.0355 (13) | 0.0402 (15) | 0.0434 (14) | −0.0019 (11) | 0.0120 (11) | 0.0007 (12) |
C30 | 0.0475 (16) | 0.0344 (14) | 0.0388 (14) | 0.0005 (12) | 0.0140 (12) | 0.0007 (11) |
C31 | 0.0462 (15) | 0.0416 (15) | 0.0449 (15) | −0.0043 (13) | 0.0136 (13) | −0.0035 (12) |
C32 | 0.0470 (16) | 0.0420 (15) | 0.0510 (17) | 0.0033 (13) | 0.0173 (13) | −0.0017 (13) |
C33 | 0.0611 (19) | 0.0424 (16) | 0.0508 (17) | −0.0025 (14) | 0.0136 (15) | −0.0082 (13) |
C34 | 0.060 (2) | 0.0525 (19) | 0.063 (2) | −0.0144 (16) | 0.0158 (17) | −0.0120 (16) |
C35 | 0.0456 (16) | 0.0512 (18) | 0.0572 (18) | −0.0069 (14) | 0.0163 (14) | −0.0023 (15) |
C36 | 0.0373 (13) | 0.0419 (15) | 0.0464 (15) | −0.0002 (12) | 0.0150 (12) | 0.0103 (12) |
C37 | 0.0359 (13) | 0.0397 (14) | 0.0449 (15) | −0.0012 (12) | 0.0091 (12) | 0.0149 (12) |
C38 | 0.0479 (16) | 0.0482 (16) | 0.0496 (16) | −0.0038 (13) | 0.0196 (13) | 0.0127 (14) |
C39 | 0.0490 (17) | 0.066 (2) | 0.063 (2) | 0.0022 (16) | 0.0252 (16) | 0.0259 (17) |
C40 | 0.0403 (16) | 0.077 (2) | 0.064 (2) | −0.0061 (16) | 0.0125 (15) | 0.0314 (19) |
C41 | 0.0551 (19) | 0.056 (2) | 0.061 (2) | −0.0176 (16) | −0.0007 (16) | 0.0195 (17) |
C42 | 0.0524 (17) | 0.0467 (17) | 0.0513 (17) | −0.0073 (14) | 0.0110 (14) | 0.0122 (14) |
F1 | 0.0836 (16) | 0.0679 (15) | 0.113 (2) | −0.0135 (12) | −0.0149 (14) | 0.0544 (14) |
F2 | 0.0706 (16) | 0.139 (3) | 0.121 (2) | 0.0623 (17) | 0.0143 (15) | 0.0209 (19) |
F3 | 0.0766 (14) | 0.0647 (13) | 0.0889 (16) | −0.0049 (12) | −0.0343 (13) | 0.0180 (12) |
Geometric parameters (Å, º) top
Ni1—Br1 | 2.3343 (4) | C19—H191 | 1.00 |
Ni1—P1 | 2.1867 (7) | C20—C21 | 1.381 (4) |
Ni1—P2 | 2.2094 (7) | C20—H201 | 1.00 |
Ni1—C8 | 1.882 (3) | C21—C22 | 1.381 (4) |
P1—C9 | 1.844 (3) | C21—H211 | 1.00 |
P1—C11 | 1.829 (3) | C22—H221 | 1.00 |
P1—C17 | 1.813 (3) | C23—C24 | 1.380 (4) |
P2—C23 | 1.838 (3) | C23—C28 | 1.370 (4) |
P2—C29 | 1.821 (3) | C24—C25 | 1.380 (4) |
P2—C36 | 1.852 (3) | C24—H241 | 1.00 |
C1—C2 | 1.398 (4) | C25—C26 | 1.382 (5) |
C1—C6 | 1.403 (4) | C25—H251 | 1.00 |
C1—C7 | 1.491 (4) | C26—C27 | 1.384 (5) |
C2—C3 | 1.388 (5) | C26—H261 | 1.00 |
C2—H21 | 1.00 | C27—C28 | 1.403 (5) |
C3—C4 | 1.371 (5) | C27—H271 | 1.00 |
C3—H31 | 1.00 | C28—H281 | 1.00 |
C4—C5 | 1.383 (4) | C29—C30 | 1.516 (4) |
C4—H41 | 1.00 | C29—H291 | 1.00 |
C5—C6 | 1.392 (4) | C29—H292 | 1.00 |
C5—H51 | 1.00 | C30—C31 | 1.398 (4) |
C6—C9 | 1.511 (4) | C30—C35 | 1.387 (4) |
C7—C8 | 1.342 (4) | C31—C32 | 1.393 (4) |
C7—C10 | 1.487 (4) | C31—H311 | 1.00 |
C8—H81 | 0.90 (3) | C32—C33 | 1.374 (4) |
C9—H91 | 1.00 | C32—H321 | 1.00 |
C9—H92 | 1.00 | C33—C34 | 1.368 (5) |
C10—F1 | 1.339 (4) | C33—H331 | 1.00 |
C10—F2 | 1.331 (4) | C34—C35 | 1.367 (5) |
C10—F3 | 1.328 (4) | C34—H341 | 1.00 |
C11—C12 | 1.395 (4) | C35—H351 | 1.00 |
C11—C16 | 1.391 (4) | C36—C37 | 1.508 (4) |
C12—C13 | 1.393 (4) | C36—H361 | 1.00 |
C12—H121 | 1.00 | C36—H362 | 1.00 |
C13—C14 | 1.380 (5) | C37—C38 | 1.399 (4) |
C13—H131 | 1.00 | C37—C42 | 1.388 (4) |
C14—C15 | 1.382 (5) | C38—C39 | 1.384 (4) |
C14—H141 | 1.00 | C38—H381 | 1.00 |
C15—C16 | 1.388 (4) | C39—C40 | 1.375 (5) |
C15—H151 | 1.00 | C39—H391 | 1.00 |
C16—H161 | 1.00 | C40—C41 | 1.380 (5) |
C17—C18 | 1.400 (4) | C40—H401 | 1.00 |
C17—C22 | 1.401 (4) | C41—C42 | 1.394 (5) |
C18—C19 | 1.382 (4) | C41—H411 | 1.00 |
C18—H181 | 1.00 | C42—H421 | 1.00 |
C19—C20 | 1.382 (5) | ||
Br1—Ni1—P1 | 93.69 (2) | C18—C19—C20 | 120.1 (3) |
Br1—Ni1—P2 | 94.70 (2) | C18—C19—H191 | 119.97 (17) |
P1—Ni1—P2 | 171.55 (3) | C20—C19—H191 | 119.90 (17) |
Br1—Ni1—C8 | 176.88 (9) | C19—C20—C21 | 120.4 (3) |
P1—Ni1—C8 | 86.57 (8) | C19—C20—H201 | 119.83 (18) |
P2—Ni1—C8 | 85.00 (8) | C21—C20—H201 | 119.77 (18) |
Ni1—P1—C9 | 114.61 (9) | C20—C21—C22 | 119.9 (3) |
Ni1—P1—C11 | 121.05 (8) | C20—C21—H211 | 120.18 (18) |
C9—P1—C11 | 100.60 (12) | C22—C21—H211 | 119.89 (18) |
Ni1—P1—C17 | 109.77 (8) | C17—C22—C21 | 120.6 (3) |
C9—P1—C17 | 105.35 (12) | C17—C22—H221 | 119.43 (15) |
C11—P1—C17 | 103.87 (12) | C21—C22—H221 | 119.97 (18) |
Ni1—P2—C23 | 108.91 (9) | P2—C23—C24 | 117.2 (2) |
Ni1—P2—C29 | 116.91 (9) | P2—C23—C28 | 123.9 (2) |
C23—P2—C29 | 103.81 (13) | C24—C23—C28 | 118.9 (3) |
Ni1—P2—C36 | 117.59 (9) | C23—C24—C25 | 120.9 (3) |
C23—P2—C36 | 104.36 (13) | C23—C24—H241 | 118.95 (19) |
C29—P2—C36 | 103.74 (13) | C25—C24—H241 | 120.2 (2) |
C2—C1—C6 | 119.1 (3) | C24—C25—C26 | 120.9 (3) |
C2—C1—C7 | 122.6 (3) | C24—C25—H251 | 119.5 (2) |
C6—C1—C7 | 118.3 (2) | C26—C25—H251 | 119.6 (2) |
C1—C2—C3 | 120.4 (3) | C25—C26—C27 | 118.5 (3) |
C1—C2—H21 | 119.35 (19) | C25—C26—H261 | 120.8 (2) |
C3—C2—H21 | 120.23 (19) | C27—C26—H261 | 120.7 (2) |
C2—C3—C4 | 120.4 (3) | C26—C27—C28 | 120.2 (3) |
C2—C3—H31 | 119.49 (19) | C26—C27—H271 | 119.6 (2) |
C4—C3—H31 | 120.08 (19) | C28—C27—H271 | 120.2 (2) |
C3—C4—C5 | 119.8 (3) | C23—C28—C27 | 120.7 (3) |
C3—C4—H41 | 120.13 (19) | C23—C28—H281 | 119.51 (18) |
C5—C4—H41 | 120.1 (2) | C27—C28—H281 | 119.8 (2) |
C4—C5—C6 | 121.0 (3) | P2—C29—C30 | 115.09 (19) |
C4—C5—H51 | 119.8 (2) | P2—C29—H291 | 107.94 (9) |
C6—C5—H51 | 119.15 (17) | C30—C29—H291 | 107.79 (15) |
C1—C6—C5 | 119.2 (3) | P2—C29—H292 | 108.28 (9) |
C1—C6—C9 | 119.6 (2) | C30—C29—H292 | 108.18 (15) |
C5—C6—C9 | 121.2 (2) | H291—C29—H292 | 109.467 |
C1—C7—C8 | 123.3 (3) | C29—C30—C31 | 123.0 (2) |
C1—C7—C10 | 115.0 (2) | C29—C30—C35 | 119.3 (3) |
C8—C7—C10 | 121.3 (3) | C31—C30—C35 | 117.6 (3) |
Ni1—C8—C7 | 128.2 (2) | C30—C31—C32 | 120.5 (3) |
Ni1—C8—H81 | 115.7 (19) | C30—C31—H311 | 119.57 (16) |
C7—C8—H81 | 116.0 (19) | C32—C31—H311 | 119.91 (18) |
P1—C9—C6 | 111.90 (18) | C31—C32—C33 | 119.9 (3) |
P1—C9—H91 | 108.85 (9) | C31—C32—H321 | 119.77 (18) |
C6—C9—H91 | 108.85 (15) | C33—C32—H321 | 120.28 (19) |
P1—C9—H92 | 108.93 (8) | C32—C33—C34 | 119.8 (3) |
C6—C9—H92 | 108.82 (14) | C32—C33—H331 | 119.92 (19) |
H91—C9—H92 | 109.467 | C34—C33—H331 | 120.28 (19) |
C7—C10—F1 | 112.4 (3) | C33—C34—C35 | 120.6 (3) |
C7—C10—F2 | 113.4 (3) | C33—C34—H341 | 119.74 (19) |
F1—C10—F2 | 105.1 (3) | C35—C34—H341 | 119.61 (19) |
C7—C10—F3 | 114.8 (3) | C30—C35—C34 | 121.5 (3) |
F1—C10—F3 | 104.4 (3) | C30—C35—H351 | 118.89 (18) |
F2—C10—F3 | 105.8 (3) | C34—C35—H351 | 119.6 (2) |
P1—C11—C12 | 118.1 (2) | P2—C36—C37 | 115.23 (19) |
P1—C11—C16 | 122.4 (2) | P2—C36—H361 | 108.15 (9) |
C12—C11—C16 | 119.2 (3) | C37—C36—H361 | 108.07 (16) |
C11—C12—C13 | 120.3 (3) | P2—C36—H362 | 108.0 (1) |
C11—C12—H121 | 119.56 (17) | C37—C36—H362 | 107.82 (16) |
C13—C12—H121 | 120.09 (19) | H361—C36—H362 | 109.467 |
C12—C13—C14 | 120.0 (3) | C36—C37—C38 | 120.6 (3) |
C12—C13—H131 | 119.90 (19) | C36—C37—C42 | 120.7 (3) |
C14—C13—H131 | 120.12 (19) | C38—C37—C42 | 118.7 (3) |
C13—C14—C15 | 119.8 (3) | C37—C38—C39 | 120.6 (3) |
C13—C14—H141 | 119.92 (19) | C37—C38—H381 | 119.32 (17) |
C15—C14—H141 | 120.23 (18) | C39—C38—H381 | 120.1 (2) |
C14—C15—C16 | 120.7 (3) | C38—C39—C40 | 120.4 (3) |
C14—C15—H151 | 119.62 (18) | C38—C39—H391 | 119.7 (2) |
C16—C15—H151 | 119.69 (18) | C40—C39—H391 | 119.8 (2) |
C11—C16—C15 | 119.9 (3) | C39—C40—C41 | 119.6 (3) |
C11—C16—H161 | 119.64 (16) | C39—C40—H401 | 119.9 (2) |
C15—C16—H161 | 120.42 (18) | C41—C40—H401 | 120.5 (2) |
P1—C17—C18 | 123.1 (2) | C40—C41—C42 | 120.6 (3) |
P1—C17—C22 | 118.2 (2) | C40—C41—H411 | 119.4 (2) |
C18—C17—C22 | 118.6 (2) | C42—C41—H411 | 120.0 (2) |
C17—C18—C19 | 120.3 (3) | C37—C42—C41 | 120.1 (3) |
C17—C18—H181 | 119.72 (16) | C37—C42—H421 | 119.46 (18) |
C19—C18—H181 | 119.97 (17) | C41—C42—H421 | 120.4 (2) |