Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109002492/gd3267sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109002492/gd3267Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109002492/gd3267IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109002492/gd32672sup4.hkl |
CCDC references: 690163; 690164; 690165
The synthetic procedure used by Zeller et al. (2003) for the preparation of compound (1) was followed. Orange monoclinic crystals of (1) (form I), contaminated by bluish–green 1:1 cocrystals of (1) and (2), were grown from toluene double-layered with n-hexane at 253 K.
Orange orthorhombic crystals of (1) (form II) were isolated in the workup procedure of an equimolar reaction of the iminopyrrolyl salt Na[NC4H3C(H)═N-2,6-iPr2C6H3] with complex (1), prepared by the procedure of Zeller et al. (2003), in similar conditions to those reported by Bellabarba et al. (2003). The toluene reaction mixture was concentrated by partial evaporation of the solvent, and n-hexane was added, with stirring, to precipitate the desired compound, [Ni{κ2N,N'-NC4H3C(H)═ N-2,6-iPr2C6H3}2(Ph)(PPh3)], at room temperature; it was isolated by filtration. The remaining mother liquor was cooled to 253 K, from which crystals of unreacted complex (1) (form II) were grown.
All H atoms were placed in idealized positions and allowed to refine riding on their parent C atoms, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C).
For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999).
[Ni(C6H5)Cl(C18H15P)2] | F(000) = 1448 |
Mr = 695.80 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6083 reflections |
a = 15.601 (1) Å | θ = 2.7–25.8° |
b = 11.8690 (9) Å | µ = 0.77 mm−1 |
c = 19.857 (2) Å | T = 150 K |
β = 112.139 (4)° | Needle, yellow-orange |
V = 3405.8 (5) Å3 | 0.17 × 0.10 × 0.06 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 6506 independent reflections |
Radiation source: fine-focus sealed tube | 5091 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ and ω scans | θmax = 25.8°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −19→19 |
Tmin = 0.880, Tmax = 0.955 | k = −14→14 |
77866 measured reflections | l = −24→24 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0306P)2 + 1.391P] where P = (Fo2 + 2Fc2)/3 |
6506 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
[Ni(C6H5)Cl(C18H15P)2] | V = 3405.8 (5) Å3 |
Mr = 695.80 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.601 (1) Å | µ = 0.77 mm−1 |
b = 11.8690 (9) Å | T = 150 K |
c = 19.857 (2) Å | 0.17 × 0.10 × 0.06 mm |
β = 112.139 (4)° |
Bruker SMART CCD area-detector diffractometer | 6506 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 5091 reflections with I > 2σ(I) |
Tmin = 0.880, Tmax = 0.955 | Rint = 0.069 |
77866 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
6506 reflections | Δρmin = −0.30 e Å−3 |
415 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 | ||
Ni | 0.270802 (17) | 0.41758 (2) | 0.077518 (13) | 0.01862 (8) | |
Cl | 0.36107 (4) | 0.38722 (4) | 0.19284 (3) | 0.02837 (13) | |
P1 | 0.26377 (4) | 0.23528 (4) | 0.05103 (3) | 0.01915 (12) | |
P2 | 0.29885 (4) | 0.59967 (4) | 0.09728 (3) | 0.02008 (12) | |
C11 | 0.37710 (14) | 0.16781 (17) | 0.08610 (11) | 0.0233 (5) | |
C12 | 0.38877 (16) | 0.05381 (19) | 0.10179 (12) | 0.0339 (5) | |
H12 | 0.3378 | 0.0095 | 0.0974 | 0.041* | |
C13 | 0.47575 (19) | 0.0053 (2) | 0.12394 (15) | 0.0482 (7) | |
H13 | 0.4835 | −0.0710 | 0.1354 | 0.058* | |
C14 | 0.55060 (18) | 0.0708 (3) | 0.12881 (14) | 0.0493 (7) | |
H14 | 0.6090 | 0.0383 | 0.1430 | 0.059* | |
C15 | 0.53997 (16) | 0.1837 (2) | 0.11299 (13) | 0.0424 (6) | |
H15 | 0.5909 | 0.2271 | 0.1159 | 0.051* | |
C16 | 0.45399 (15) | 0.2330 (2) | 0.09275 (12) | 0.0326 (5) | |
H16 | 0.4473 | 0.3099 | 0.0835 | 0.039* | |
C21 | 0.19287 (13) | 0.15443 (16) | 0.08896 (11) | 0.0202 (4) | |
C22 | 0.15294 (15) | 0.05157 (17) | 0.05957 (12) | 0.0278 (5) | |
H22 | 0.1597 | 0.0243 | 0.0179 | 0.033* | |
C23 | 0.10349 (16) | −0.01028 (18) | 0.09161 (12) | 0.0314 (5) | |
H23 | 0.0770 | −0.0786 | 0.0714 | 0.038* | |
C24 | 0.09348 (15) | 0.02917 (18) | 0.15325 (12) | 0.0292 (5) | |
H24 | 0.0606 | −0.0128 | 0.1750 | 0.035* | |
C25 | 0.13202 (15) | 0.13089 (18) | 0.18287 (12) | 0.0292 (5) | |
H25 | 0.1249 | 0.1575 | 0.2245 | 0.035* | |
C26 | 0.18124 (14) | 0.19343 (17) | 0.15095 (11) | 0.0238 (5) | |
H26 | 0.2068 | 0.2622 | 0.1711 | 0.029* | |
C31 | 0.22009 (14) | 0.19332 (16) | −0.04478 (11) | 0.0217 (4) | |
C36 | 0.28093 (16) | 0.16878 (17) | −0.07955 (12) | 0.0275 (5) | |
H36 | 0.3444 | 0.1677 | −0.0529 | 0.033* | |
C35 | 0.24730 (18) | 0.14597 (18) | −0.15366 (12) | 0.0350 (6) | |
H35 | 0.2883 | 0.1299 | −0.1763 | 0.042* | |
C34 | 0.15395 (19) | 0.14701 (18) | −0.19344 (12) | 0.0365 (6) | |
H34 | 0.1317 | 0.1311 | −0.2429 | 0.044* | |
C33 | 0.09294 (17) | 0.17170 (18) | −0.16003 (12) | 0.0340 (6) | |
H33 | 0.0297 | 0.1733 | −0.1872 | 0.041* | |
C32 | 0.12580 (15) | 0.19407 (17) | −0.08615 (12) | 0.0280 (5) | |
H32 | 0.0842 | 0.2098 | −0.0640 | 0.034* | |
C41 | 0.42249 (14) | 0.61628 (16) | 0.11985 (11) | 0.0216 (4) | |
C42 | 0.48365 (15) | 0.63308 (18) | 0.19039 (12) | 0.0282 (5) | |
H42 | 0.4615 | 0.6435 | 0.2274 | 0.034* | |
C43 | 0.57830 (16) | 0.6344 (2) | 0.20606 (13) | 0.0336 (5) | |
H43 | 0.6193 | 0.6453 | 0.2537 | 0.040* | |
C44 | 0.61182 (16) | 0.61977 (19) | 0.15184 (13) | 0.0331 (5) | |
H44 | 0.6752 | 0.6211 | 0.1626 | 0.040* | |
C45 | 0.55096 (16) | 0.60313 (19) | 0.08142 (13) | 0.0333 (5) | |
H45 | 0.5734 | 0.5936 | 0.0445 | 0.040* | |
C46 | 0.45689 (15) | 0.60055 (18) | 0.06537 (12) | 0.0286 (5) | |
H46 | 0.4162 | 0.5882 | 0.0178 | 0.034* | |
C51 | 0.27388 (14) | 0.66309 (17) | 0.17147 (11) | 0.0225 (5) | |
C52 | 0.29719 (17) | 0.77480 (18) | 0.19139 (12) | 0.0329 (5) | |
H52 | 0.3305 | 0.8159 | 0.1695 | 0.039* | |
C53 | 0.27097 (19) | 0.8250 (2) | 0.24371 (13) | 0.0408 (6) | |
H53 | 0.2871 | 0.8995 | 0.2571 | 0.049* | |
C54 | 0.22138 (17) | 0.7653 (2) | 0.27576 (12) | 0.0376 (6) | |
H54 | 0.2035 | 0.7995 | 0.3106 | 0.045* | |
C55 | 0.19793 (16) | 0.6548 (2) | 0.25650 (12) | 0.0340 (6) | |
H55 | 0.1642 | 0.6143 | 0.2783 | 0.041* | |
C56 | 0.22454 (14) | 0.60390 (18) | 0.20481 (11) | 0.0266 (5) | |
H56 | 0.2090 | 0.5290 | 0.1923 | 0.032* | |
C61 | 0.24311 (15) | 0.70392 (16) | 0.02609 (11) | 0.0231 (5) | |
C66 | 0.29020 (16) | 0.78075 (18) | 0.00011 (12) | 0.0296 (5) | |
H66 | 0.3545 | 0.7807 | 0.0183 | 0.036* | |
C65 | 0.24083 (19) | 0.85791 (19) | −0.05325 (13) | 0.0376 (6) | |
H65 | 0.2724 | 0.9091 | −0.0709 | 0.045* | |
C64 | 0.14618 (19) | 0.8589 (2) | −0.07987 (13) | 0.0397 (6) | |
H64 | 0.1138 | 0.9105 | −0.1157 | 0.048* | |
C63 | 0.09874 (17) | 0.7844 (2) | −0.05402 (12) | 0.0365 (6) | |
H63 | 0.0344 | 0.7858 | −0.0719 | 0.044* | |
C62 | 0.14690 (16) | 0.70724 (18) | −0.00125 (12) | 0.0308 (5) | |
H62 | 0.1146 | 0.6568 | 0.0162 | 0.037* | |
C71 | 0.18264 (14) | 0.44409 (16) | −0.01655 (10) | 0.0197 (4) | |
C76 | 0.20491 (15) | 0.47127 (17) | −0.07631 (11) | 0.0241 (5) | |
H76 | 0.2668 | 0.4785 | −0.0701 | 0.029* | |
C75 | 0.13721 (17) | 0.48768 (18) | −0.14451 (12) | 0.0329 (6) | |
H75 | 0.1540 | 0.5050 | −0.1836 | 0.040* | |
C74 | 0.04551 (18) | 0.4786 (2) | −0.15490 (13) | 0.0402 (6) | |
H74 | 0.0000 | 0.4896 | −0.2008 | 0.048* | |
C73 | 0.02134 (16) | 0.4530 (2) | −0.09683 (13) | 0.0390 (6) | |
H73 | −0.0408 | 0.4475 | −0.1035 | 0.047* | |
C72 | 0.08879 (15) | 0.43532 (18) | −0.02846 (12) | 0.0285 (5) | |
H72 | 0.0713 | 0.4173 | 0.0101 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.02119 (14) | 0.01574 (14) | 0.01592 (14) | −0.00161 (11) | 0.00356 (11) | 0.00028 (10) |
Cl | 0.0351 (3) | 0.0218 (3) | 0.0191 (3) | −0.0030 (2) | −0.0002 (2) | 0.0017 (2) |
P1 | 0.0209 (3) | 0.0163 (3) | 0.0181 (3) | −0.0015 (2) | 0.0049 (2) | 0.0003 (2) |
P2 | 0.0243 (3) | 0.0165 (3) | 0.0178 (3) | −0.0008 (2) | 0.0061 (2) | 0.0006 (2) |
C11 | 0.0234 (11) | 0.0272 (12) | 0.0170 (11) | 0.0022 (9) | 0.0051 (9) | 0.0011 (9) |
C12 | 0.0325 (13) | 0.0315 (13) | 0.0357 (13) | 0.0050 (10) | 0.0105 (11) | 0.0032 (10) |
C13 | 0.0450 (17) | 0.0422 (16) | 0.0499 (17) | 0.0193 (13) | 0.0095 (14) | 0.0087 (13) |
C14 | 0.0303 (14) | 0.069 (2) | 0.0415 (16) | 0.0202 (14) | 0.0050 (12) | −0.0004 (14) |
C15 | 0.0255 (13) | 0.0625 (19) | 0.0387 (15) | −0.0027 (12) | 0.0116 (12) | −0.0071 (13) |
C16 | 0.0267 (12) | 0.0408 (14) | 0.0284 (12) | −0.0012 (10) | 0.0082 (10) | 0.0008 (10) |
C21 | 0.0185 (10) | 0.0189 (10) | 0.0203 (11) | 0.0010 (8) | 0.0040 (9) | 0.0036 (8) |
C22 | 0.0366 (13) | 0.0220 (11) | 0.0267 (12) | −0.0046 (10) | 0.0140 (10) | −0.0037 (9) |
C23 | 0.0369 (14) | 0.0205 (12) | 0.0346 (13) | −0.0087 (10) | 0.0108 (11) | −0.0014 (10) |
C24 | 0.0290 (13) | 0.0280 (12) | 0.0312 (13) | −0.0029 (10) | 0.0121 (10) | 0.0061 (10) |
C25 | 0.0352 (13) | 0.0304 (12) | 0.0249 (12) | −0.0011 (10) | 0.0146 (10) | 0.0005 (10) |
C26 | 0.0252 (11) | 0.0212 (11) | 0.0222 (11) | −0.0017 (9) | 0.0057 (9) | −0.0012 (9) |
C31 | 0.0296 (12) | 0.0116 (10) | 0.0204 (11) | −0.0033 (8) | 0.0056 (9) | 0.0013 (8) |
C36 | 0.0358 (13) | 0.0203 (11) | 0.0267 (12) | 0.0005 (9) | 0.0121 (10) | 0.0011 (9) |
C35 | 0.0598 (17) | 0.0219 (12) | 0.0290 (13) | −0.0016 (11) | 0.0232 (13) | −0.0006 (10) |
C34 | 0.0610 (17) | 0.0194 (12) | 0.0220 (12) | −0.0114 (11) | 0.0075 (12) | −0.0003 (9) |
C33 | 0.0396 (14) | 0.0232 (12) | 0.0275 (13) | −0.0133 (10) | −0.0008 (11) | 0.0042 (10) |
C32 | 0.0324 (13) | 0.0205 (11) | 0.0272 (12) | −0.0075 (9) | 0.0071 (10) | 0.0017 (9) |
C41 | 0.0261 (11) | 0.0161 (10) | 0.0221 (11) | −0.0020 (8) | 0.0086 (9) | 0.0001 (8) |
C42 | 0.0311 (13) | 0.0308 (12) | 0.0234 (12) | −0.0042 (10) | 0.0112 (10) | −0.0045 (9) |
C43 | 0.0287 (13) | 0.0372 (14) | 0.0286 (13) | −0.0071 (10) | 0.0039 (11) | −0.0074 (10) |
C44 | 0.0270 (12) | 0.0333 (13) | 0.0384 (14) | −0.0054 (10) | 0.0118 (11) | −0.0024 (11) |
C45 | 0.0338 (13) | 0.0392 (14) | 0.0320 (13) | −0.0005 (11) | 0.0182 (11) | −0.0012 (10) |
C46 | 0.0314 (13) | 0.0305 (13) | 0.0222 (11) | −0.0017 (10) | 0.0080 (10) | −0.0047 (9) |
C51 | 0.0252 (11) | 0.0216 (11) | 0.0182 (11) | 0.0039 (9) | 0.0052 (9) | 0.0013 (8) |
C52 | 0.0494 (15) | 0.0220 (12) | 0.0291 (13) | −0.0009 (10) | 0.0169 (12) | −0.0006 (9) |
C53 | 0.0663 (18) | 0.0218 (12) | 0.0320 (14) | 0.0103 (12) | 0.0159 (13) | −0.0024 (10) |
C54 | 0.0474 (15) | 0.0413 (15) | 0.0246 (13) | 0.0155 (12) | 0.0143 (12) | −0.0009 (11) |
C55 | 0.0337 (13) | 0.0430 (15) | 0.0286 (13) | 0.0046 (11) | 0.0153 (11) | 0.0007 (11) |
C56 | 0.0245 (11) | 0.0287 (12) | 0.0249 (12) | 0.0005 (9) | 0.0075 (10) | −0.0006 (9) |
C61 | 0.0346 (12) | 0.0160 (10) | 0.0180 (11) | 0.0021 (9) | 0.0090 (10) | −0.0006 (8) |
C66 | 0.0403 (14) | 0.0228 (11) | 0.0279 (12) | 0.0020 (10) | 0.0153 (11) | 0.0004 (9) |
C65 | 0.0643 (18) | 0.0233 (12) | 0.0339 (14) | 0.0051 (12) | 0.0285 (13) | 0.0062 (10) |
C64 | 0.0661 (19) | 0.0280 (13) | 0.0258 (13) | 0.0212 (12) | 0.0183 (13) | 0.0085 (10) |
C63 | 0.0413 (14) | 0.0312 (13) | 0.0315 (13) | 0.0135 (11) | 0.0076 (11) | 0.0006 (11) |
C62 | 0.0372 (14) | 0.0236 (12) | 0.0294 (13) | 0.0049 (10) | 0.0099 (11) | 0.0029 (9) |
C71 | 0.0212 (11) | 0.0157 (10) | 0.0194 (10) | 0.0012 (8) | 0.0044 (9) | −0.0025 (8) |
C76 | 0.0281 (12) | 0.0211 (11) | 0.0214 (11) | −0.0027 (9) | 0.0072 (10) | −0.0026 (9) |
C75 | 0.0495 (16) | 0.0265 (12) | 0.0187 (12) | −0.0010 (11) | 0.0082 (11) | 0.0014 (9) |
C74 | 0.0415 (16) | 0.0375 (14) | 0.0237 (13) | 0.0087 (12) | −0.0082 (11) | 0.0002 (11) |
C73 | 0.0221 (12) | 0.0465 (15) | 0.0395 (15) | 0.0056 (11) | 0.0013 (11) | −0.0080 (12) |
C72 | 0.0267 (12) | 0.0329 (13) | 0.0253 (12) | 0.0014 (10) | 0.0090 (10) | −0.0046 (10) |
Ni—C71 | 1.8825 (19) | C41—C46 | 1.390 (3) |
Ni—P2 | 2.2107 (6) | C42—C43 | 1.390 (3) |
Ni—Cl | 2.2195 (6) | C42—H42 | 0.9300 |
Ni—P1 | 2.2197 (6) | C43—C44 | 1.374 (3) |
P1—C11 | 1.823 (2) | C43—H43 | 0.9300 |
P1—C21 | 1.827 (2) | C44—C45 | 1.377 (3) |
P1—C31 | 1.832 (2) | C44—H44 | 0.9300 |
P2—C41 | 1.819 (2) | C45—C46 | 1.380 (3) |
P2—C51 | 1.822 (2) | C45—H45 | 0.9300 |
P2—C61 | 1.833 (2) | C46—H46 | 0.9300 |
C11—C12 | 1.385 (3) | C51—C56 | 1.381 (3) |
C11—C16 | 1.391 (3) | C51—C52 | 1.392 (3) |
C12—C13 | 1.384 (3) | C52—C53 | 1.387 (3) |
C12—H12 | 0.9300 | C52—H52 | 0.9300 |
C13—C14 | 1.376 (4) | C53—C54 | 1.370 (3) |
C13—H13 | 0.9300 | C53—H53 | 0.9300 |
C14—C15 | 1.372 (4) | C54—C55 | 1.377 (3) |
C14—H14 | 0.9300 | C54—H54 | 0.9300 |
C15—C16 | 1.377 (3) | C55—C56 | 1.382 (3) |
C15—H15 | 0.9300 | C55—H55 | 0.9300 |
C16—H16 | 0.9300 | C56—H56 | 0.9300 |
C21—C26 | 1.390 (3) | C61—C66 | 1.387 (3) |
C21—C22 | 1.395 (3) | C61—C62 | 1.391 (3) |
C22—C23 | 1.382 (3) | C66—C65 | 1.393 (3) |
C22—H22 | 0.9300 | C66—H66 | 0.9300 |
C23—C24 | 1.373 (3) | C65—C64 | 1.368 (4) |
C23—H23 | 0.9300 | C65—H65 | 0.9300 |
C24—C25 | 1.378 (3) | C64—C63 | 1.371 (3) |
C24—H24 | 0.9300 | C64—H64 | 0.9300 |
C25—C26 | 1.382 (3) | C63—C62 | 1.381 (3) |
C25—H25 | 0.9300 | C63—H63 | 0.9300 |
C26—H26 | 0.9300 | C62—H62 | 0.9300 |
C31—C32 | 1.389 (3) | C71—C76 | 1.394 (3) |
C31—C36 | 1.399 (3) | C71—C72 | 1.396 (3) |
C36—C35 | 1.390 (3) | C76—C75 | 1.382 (3) |
C36—H36 | 0.9300 | C76—H76 | 0.9300 |
C35—C34 | 1.370 (3) | C75—C74 | 1.370 (3) |
C35—H35 | 0.9300 | C75—H75 | 0.9300 |
C34—C33 | 1.381 (3) | C74—C73 | 1.376 (3) |
C34—H34 | 0.9300 | C74—H74 | 0.9300 |
C33—C32 | 1.385 (3) | C73—C72 | 1.385 (3) |
C33—H33 | 0.9300 | C73—H73 | 0.9300 |
C32—H32 | 0.9300 | C72—H72 | 0.9300 |
C41—C42 | 1.380 (3) | ||
C71—Ni—P2 | 91.98 (6) | C42—C41—C46 | 119.17 (19) |
C71—Ni—Cl | 173.29 (6) | C42—C41—P2 | 121.94 (16) |
P2—Ni—Cl | 88.24 (2) | C46—C41—P2 | 118.59 (16) |
C71—Ni—P1 | 88.59 (6) | C41—C42—C43 | 119.9 (2) |
P2—Ni—P1 | 169.69 (2) | C41—C42—H42 | 120.0 |
Cl—Ni—P1 | 92.39 (2) | C43—C42—H42 | 120.0 |
C11—P1—C21 | 105.21 (9) | C44—C43—C42 | 120.6 (2) |
C11—P1—C31 | 101.83 (9) | C44—C43—H43 | 119.7 |
C21—P1—C31 | 103.85 (9) | C42—C43—H43 | 119.7 |
C11—P1—Ni | 112.54 (7) | C43—C44—C45 | 119.6 (2) |
C21—P1—Ni | 113.43 (7) | C43—C44—H44 | 120.2 |
C31—P1—Ni | 118.49 (6) | C45—C44—H44 | 120.2 |
C41—P2—C51 | 106.62 (9) | C44—C45—C46 | 120.3 (2) |
C41—P2—C61 | 105.53 (9) | C44—C45—H45 | 119.9 |
C51—P2—C61 | 99.25 (9) | C46—C45—H45 | 119.9 |
C41—P2—Ni | 105.68 (7) | C45—C46—C41 | 120.4 (2) |
C51—P2—Ni | 117.32 (7) | C45—C46—H46 | 119.8 |
C61—P2—Ni | 121.23 (7) | C41—C46—H46 | 119.8 |
C12—C11—C16 | 119.1 (2) | C56—C51—C52 | 118.77 (19) |
C12—C11—P1 | 122.77 (17) | C56—C51—P2 | 120.31 (16) |
C16—C11—P1 | 118.00 (16) | C52—C51—P2 | 120.69 (16) |
C13—C12—C11 | 120.5 (2) | C53—C52—C51 | 120.2 (2) |
C13—C12—H12 | 119.7 | C53—C52—H52 | 119.9 |
C11—C12—H12 | 119.7 | C51—C52—H52 | 119.9 |
C14—C13—C12 | 119.4 (2) | C54—C53—C52 | 120.2 (2) |
C14—C13—H13 | 120.3 | C54—C53—H53 | 119.9 |
C12—C13—H13 | 120.3 | C52—C53—H53 | 119.9 |
C15—C14—C13 | 120.7 (2) | C53—C54—C55 | 120.1 (2) |
C15—C14—H14 | 119.7 | C53—C54—H54 | 119.9 |
C13—C14—H14 | 119.7 | C55—C54—H54 | 119.9 |
C14—C15—C16 | 120.1 (2) | C54—C55—C56 | 120.0 (2) |
C14—C15—H15 | 119.9 | C54—C55—H55 | 120.0 |
C16—C15—H15 | 119.9 | C56—C55—H55 | 120.0 |
C15—C16—C11 | 120.1 (2) | C51—C56—C55 | 120.7 (2) |
C15—C16—H16 | 119.9 | C51—C56—H56 | 119.6 |
C11—C16—H16 | 119.9 | C55—C56—H56 | 119.6 |
C26—C21—C22 | 118.39 (18) | C66—C61—C62 | 118.8 (2) |
C26—C21—P1 | 119.45 (15) | C66—C61—P2 | 124.54 (17) |
C22—C21—P1 | 122.10 (16) | C62—C61—P2 | 116.66 (16) |
C23—C22—C21 | 120.8 (2) | C61—C66—C65 | 119.8 (2) |
C23—C22—H22 | 119.6 | C61—C66—H66 | 120.1 |
C21—C22—H22 | 119.6 | C65—C66—H66 | 120.1 |
C24—C23—C22 | 120.0 (2) | C64—C65—C66 | 120.4 (2) |
C24—C23—H23 | 120.0 | C64—C65—H65 | 119.8 |
C22—C23—H23 | 120.0 | C66—C65—H65 | 119.8 |
C23—C24—C25 | 120.1 (2) | C65—C64—C63 | 120.4 (2) |
C23—C24—H24 | 120.0 | C65—C64—H64 | 119.8 |
C25—C24—H24 | 120.0 | C63—C64—H64 | 119.8 |
C24—C25—C26 | 120.2 (2) | C64—C63—C62 | 119.7 (2) |
C24—C25—H25 | 119.9 | C64—C63—H63 | 120.1 |
C26—C25—H25 | 119.9 | C62—C63—H63 | 120.1 |
C25—C26—C21 | 120.54 (19) | C63—C62—C61 | 120.9 (2) |
C25—C26—H26 | 119.7 | C63—C62—H62 | 119.6 |
C21—C26—H26 | 119.7 | C61—C62—H62 | 119.6 |
C32—C31—C36 | 118.30 (19) | C76—C71—C72 | 117.06 (19) |
C32—C31—P1 | 120.62 (16) | C76—C71—Ni | 124.05 (15) |
C36—C31—P1 | 120.88 (16) | C72—C71—Ni | 118.88 (15) |
C35—C36—C31 | 120.5 (2) | C75—C76—C71 | 121.5 (2) |
C35—C36—H36 | 119.8 | C75—C76—H76 | 119.2 |
C31—C36—H36 | 119.8 | C71—C76—H76 | 119.2 |
C34—C35—C36 | 120.2 (2) | C74—C75—C76 | 120.4 (2) |
C34—C35—H35 | 119.9 | C74—C75—H75 | 119.8 |
C36—C35—H35 | 119.9 | C76—C75—H75 | 119.8 |
C35—C34—C33 | 120.0 (2) | C75—C74—C73 | 119.4 (2) |
C35—C34—H34 | 120.0 | C75—C74—H74 | 120.3 |
C33—C34—H34 | 120.0 | C73—C74—H74 | 120.3 |
C34—C33—C32 | 120.2 (2) | C74—C73—C72 | 120.5 (2) |
C34—C33—H33 | 119.9 | C74—C73—H73 | 119.7 |
C32—C33—H33 | 119.9 | C72—C73—H73 | 119.7 |
C33—C32—C31 | 120.8 (2) | C73—C72—C71 | 121.0 (2) |
C33—C32—H32 | 119.6 | C73—C72—H72 | 119.5 |
C31—C32—H32 | 119.6 | C71—C72—H72 | 119.5 |
C71—Ni—P1—C11 | 139.55 (9) | C34—C33—C32—C31 | 0.7 (3) |
P2—Ni—P1—C11 | 46.25 (15) | C36—C31—C32—C33 | −0.4 (3) |
Cl—Ni—P1—C11 | −47.09 (7) | P1—C31—C32—C33 | 174.47 (16) |
C71—Ni—P1—C21 | −101.14 (9) | C51—P2—C41—C42 | 21.9 (2) |
P2—Ni—P1—C21 | 165.56 (13) | C61—P2—C41—C42 | 126.75 (18) |
Cl—Ni—P1—C21 | 72.22 (7) | Ni—P2—C41—C42 | −103.69 (17) |
C71—Ni—P1—C31 | 21.00 (10) | C51—P2—C41—C46 | −164.53 (16) |
P2—Ni—P1—C31 | −72.30 (16) | C61—P2—C41—C46 | −59.64 (18) |
Cl—Ni—P1—C31 | −165.64 (8) | Ni—P2—C41—C46 | 69.92 (17) |
C71—Ni—P2—C41 | −123.24 (9) | C46—C41—C42—C43 | 0.2 (3) |
Cl—Ni—P2—C41 | 63.47 (7) | P2—C41—C42—C43 | 173.77 (17) |
P1—Ni—P2—C41 | −30.24 (15) | C41—C42—C43—C44 | 0.4 (3) |
C71—Ni—P2—C51 | 118.12 (10) | C42—C43—C44—C45 | −0.3 (4) |
Cl—Ni—P2—C51 | −55.18 (8) | C43—C44—C45—C46 | −0.3 (4) |
P1—Ni—P2—C51 | −148.88 (14) | C44—C45—C46—C41 | 0.9 (3) |
C71—Ni—P2—C61 | −3.55 (10) | C42—C41—C46—C45 | −0.8 (3) |
Cl—Ni—P2—C61 | −176.84 (8) | P2—C41—C46—C45 | −174.61 (17) |
P1—Ni—P2—C61 | 89.46 (15) | C41—P2—C51—C56 | −129.25 (17) |
C21—P1—C11—C12 | 30.5 (2) | C61—P2—C51—C56 | 121.37 (18) |
C31—P1—C11—C12 | −77.57 (19) | Ni—P2—C51—C56 | −11.1 (2) |
Ni—P1—C11—C12 | 154.50 (16) | C41—P2—C51—C52 | 56.2 (2) |
C21—P1—C11—C16 | −153.71 (17) | C61—P2—C51—C52 | −53.2 (2) |
C31—P1—C11—C16 | 98.21 (17) | Ni—P2—C51—C52 | 174.34 (15) |
Ni—P1—C11—C16 | −29.71 (18) | C56—C51—C52—C53 | −0.1 (3) |
C16—C11—C12—C13 | 0.1 (3) | P2—C51—C52—C53 | 174.56 (18) |
P1—C11—C12—C13 | 175.88 (19) | C51—C52—C53—C54 | −0.5 (4) |
C11—C12—C13—C14 | −1.4 (4) | C52—C53—C54—C55 | 0.5 (4) |
C12—C13—C14—C15 | 1.0 (4) | C53—C54—C55—C56 | 0.1 (4) |
C13—C14—C15—C16 | 0.7 (4) | C52—C51—C56—C55 | 0.6 (3) |
C14—C15—C16—C11 | −2.0 (4) | P2—C51—C56—C55 | −174.04 (16) |
C12—C11—C16—C15 | 1.5 (3) | C54—C55—C56—C51 | −0.6 (3) |
P1—C11—C16—C15 | −174.41 (17) | C41—P2—C61—C66 | −2.9 (2) |
C11—P1—C21—C26 | 97.56 (17) | C51—P2—C61—C66 | 107.36 (19) |
C31—P1—C21—C26 | −155.83 (16) | Ni—P2—C61—C66 | −122.65 (16) |
Ni—P1—C21—C26 | −25.87 (18) | C41—P2—C61—C62 | 179.39 (16) |
C11—P1—C21—C22 | −79.56 (18) | C51—P2—C61—C62 | −70.37 (17) |
C31—P1—C21—C22 | 27.05 (19) | Ni—P2—C61—C62 | 59.62 (18) |
Ni—P1—C21—C22 | 157.01 (15) | C62—C61—C66—C65 | −1.1 (3) |
C26—C21—C22—C23 | −0.4 (3) | P2—C61—C66—C65 | −178.75 (16) |
P1—C21—C22—C23 | 176.78 (17) | C61—C66—C65—C64 | 0.4 (3) |
C21—C22—C23—C24 | −0.2 (3) | C66—C65—C64—C63 | 0.4 (4) |
C22—C23—C24—C25 | 0.6 (3) | C65—C64—C63—C62 | −0.6 (3) |
C23—C24—C25—C26 | −0.3 (3) | C64—C63—C62—C61 | −0.1 (3) |
C24—C25—C26—C21 | −0.3 (3) | C66—C61—C62—C63 | 0.9 (3) |
C22—C21—C26—C25 | 0.6 (3) | P2—C61—C62—C63 | 178.75 (17) |
P1—C21—C26—C25 | −176.58 (16) | P2—Ni—C71—C76 | 76.70 (17) |
C11—P1—C31—C32 | 158.37 (16) | P1—Ni—C71—C76 | −93.01 (17) |
C21—P1—C31—C32 | 49.24 (18) | P2—Ni—C71—C72 | −103.96 (16) |
Ni—P1—C31—C32 | −77.61 (17) | P1—Ni—C71—C72 | 86.33 (16) |
C11—P1—C31—C36 | −26.93 (18) | C72—C71—C76—C75 | −0.7 (3) |
C21—P1—C31—C36 | −136.06 (16) | Ni—C71—C76—C75 | 178.70 (16) |
Ni—P1—C31—C36 | 97.09 (16) | C71—C76—C75—C74 | 0.7 (3) |
C32—C31—C36—C35 | 0.1 (3) | C76—C75—C74—C73 | 0.0 (4) |
P1—C31—C36—C35 | −174.73 (16) | C75—C74—C73—C72 | −0.7 (4) |
C31—C36—C35—C34 | −0.2 (3) | C74—C73—C72—C71 | 0.7 (4) |
C36—C35—C34—C33 | 0.5 (3) | C76—C71—C72—C73 | 0.0 (3) |
C35—C34—C33—C32 | −0.8 (3) | Ni—C71—C72—C73 | −179.39 (17) |
[Ni(C6H5)Cl(C18H15P)2] | F(000) = 2896 |
Mr = 695.80 | Dx = 1.334 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3061 reflections |
a = 11.7990 (5) Å | θ = 2.5–22.7° |
b = 23.368 (2) Å | µ = 0.76 mm−1 |
c = 25.1300 (11) Å | T = 150 K |
V = 6928.8 (7) Å3 | Prism, brown |
Z = 8 | 0.22 × 0.14 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 6075 independent reflections |
Radiation source: fine-focus sealed tube | 3874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −12→14 |
Tmin = 0.851, Tmax = 0.942 | k = −27→27 |
35219 measured reflections | l = −27→29 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0359P)2] where P = (Fo2 + 2Fc2)/3 |
6075 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
[Ni(C6H5)Cl(C18H15P)2] | V = 6928.8 (7) Å3 |
Mr = 695.80 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.7990 (5) Å | µ = 0.76 mm−1 |
b = 23.368 (2) Å | T = 150 K |
c = 25.1300 (11) Å | 0.22 × 0.14 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 6075 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 3874 reflections with I > 2σ(I) |
Tmin = 0.851, Tmax = 0.942 | Rint = 0.094 |
35219 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.39 e Å−3 |
6075 reflections | Δρmin = −0.28 e Å−3 |
415 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 | ||
Ni | 0.40369 (3) | 0.166985 (16) | 0.640882 (15) | 0.01697 (11) | |
Cl | 0.41156 (6) | 0.16620 (3) | 0.55195 (3) | 0.02381 (18) | |
P1 | 0.37135 (6) | 0.07364 (3) | 0.63898 (3) | 0.01788 (19) | |
P2 | 0.43082 (6) | 0.26055 (3) | 0.64000 (3) | 0.01815 (19) | |
C11 | 0.2355 (2) | 0.05352 (13) | 0.60836 (12) | 0.0218 (7) | |
C12 | 0.1900 (3) | −0.00083 (15) | 0.61566 (13) | 0.0332 (9) | |
H12 | 0.2290 | −0.0279 | 0.6357 | 0.040* | |
C13 | 0.0870 (3) | −0.01466 (17) | 0.59322 (15) | 0.0446 (10) | |
H13 | 0.0574 | −0.0512 | 0.5979 | 0.054* | |
C14 | 0.0275 (3) | 0.02485 (19) | 0.56401 (14) | 0.0461 (11) | |
H14 | −0.0422 | 0.0152 | 0.5492 | 0.055* | |
C15 | 0.0713 (3) | 0.07874 (18) | 0.55667 (14) | 0.0438 (10) | |
H15 | 0.0312 | 0.1056 | 0.5369 | 0.053* | |
C16 | 0.1752 (3) | 0.09325 (15) | 0.57871 (13) | 0.0309 (8) | |
H16 | 0.2045 | 0.1298 | 0.5736 | 0.037* | |
C21 | 0.4841 (2) | 0.03754 (13) | 0.60203 (11) | 0.0198 (7) | |
C22 | 0.4702 (3) | −0.01416 (13) | 0.57540 (12) | 0.0273 (8) | |
H22 | 0.3999 | −0.0322 | 0.5754 | 0.033* | |
C23 | 0.5609 (3) | −0.03902 (14) | 0.54874 (13) | 0.0364 (9) | |
H23 | 0.5509 | −0.0735 | 0.5308 | 0.044* | |
C24 | 0.6656 (3) | −0.01288 (14) | 0.54868 (13) | 0.0334 (9) | |
H24 | 0.7259 | −0.0294 | 0.5304 | 0.040* | |
C25 | 0.6805 (3) | 0.03778 (14) | 0.57582 (12) | 0.0300 (8) | |
H25 | 0.7516 | 0.0550 | 0.5768 | 0.036* | |
C26 | 0.5901 (2) | 0.06305 (13) | 0.60164 (12) | 0.0239 (7) | |
H26 | 0.6005 | 0.0978 | 0.6190 | 0.029* | |
C31 | 0.3677 (2) | 0.03480 (12) | 0.70189 (12) | 0.0196 (7) | |
C32 | 0.4559 (3) | 0.00099 (13) | 0.71931 (13) | 0.0261 (8) | |
H32 | 0.5155 | −0.0072 | 0.6963 | 0.031* | |
C33 | 0.4572 (3) | −0.02091 (14) | 0.77053 (13) | 0.0318 (8) | |
H33 | 0.5173 | −0.0436 | 0.7818 | 0.038* | |
C34 | 0.3691 (3) | −0.00889 (14) | 0.80480 (13) | 0.0307 (8) | |
H34 | 0.3707 | −0.0226 | 0.8395 | 0.037* | |
C35 | 0.2782 (3) | 0.02354 (14) | 0.78753 (13) | 0.0290 (8) | |
H35 | 0.2178 | 0.0309 | 0.8103 | 0.035* | |
C36 | 0.2772 (3) | 0.04510 (13) | 0.73608 (12) | 0.0258 (8) | |
H36 | 0.2157 | 0.0666 | 0.7244 | 0.031* | |
C41 | 0.3246 (3) | 0.29258 (13) | 0.59646 (13) | 0.0260 (8) | |
C42 | 0.3509 (3) | 0.33619 (14) | 0.56072 (14) | 0.0436 (10) | |
H42 | 0.4253 | 0.3491 | 0.5578 | 0.052* | |
C43 | 0.2675 (4) | 0.36028 (17) | 0.52980 (17) | 0.0633 (14) | |
H43 | 0.2859 | 0.3896 | 0.5064 | 0.076* | |
C44 | 0.1589 (4) | 0.34199 (19) | 0.53291 (18) | 0.0689 (16) | |
H44 | 0.1035 | 0.3587 | 0.5117 | 0.083* | |
C45 | 0.1303 (3) | 0.2986 (2) | 0.56746 (18) | 0.0600 (14) | |
H45 | 0.0557 | 0.2860 | 0.5696 | 0.072* | |
C46 | 0.2141 (3) | 0.27361 (16) | 0.59940 (15) | 0.0430 (10) | |
H46 | 0.1951 | 0.2442 | 0.6226 | 0.052* | |
C51 | 0.5666 (2) | 0.28617 (13) | 0.61389 (12) | 0.0193 (7) | |
C52 | 0.6037 (3) | 0.34139 (13) | 0.62500 (12) | 0.0256 (8) | |
H52 | 0.5618 | 0.3644 | 0.6479 | 0.031* | |
C53 | 0.7015 (3) | 0.36239 (14) | 0.60250 (13) | 0.0346 (9) | |
H53 | 0.7247 | 0.3996 | 0.6099 | 0.042* | |
C54 | 0.7653 (3) | 0.32844 (15) | 0.56908 (13) | 0.0409 (10) | |
H54 | 0.8311 | 0.3427 | 0.5537 | 0.049* | |
C55 | 0.7308 (3) | 0.27343 (15) | 0.55872 (14) | 0.0406 (10) | |
H55 | 0.7741 | 0.2504 | 0.5364 | 0.049* | |
C56 | 0.6328 (3) | 0.25187 (14) | 0.58095 (12) | 0.0293 (8) | |
H56 | 0.6109 | 0.2144 | 0.5739 | 0.035* | |
C61 | 0.4179 (2) | 0.30207 (12) | 0.70136 (12) | 0.0214 (7) | |
C62 | 0.5011 (3) | 0.29551 (13) | 0.74016 (12) | 0.0290 (8) | |
H62 | 0.5619 | 0.2711 | 0.7339 | 0.035* | |
C63 | 0.4947 (3) | 0.32475 (14) | 0.78776 (13) | 0.0367 (9) | |
H63 | 0.5513 | 0.3203 | 0.8132 | 0.044* | |
C64 | 0.4042 (3) | 0.36050 (16) | 0.79752 (15) | 0.0448 (10) | |
H64 | 0.3995 | 0.3801 | 0.8296 | 0.054* | |
C65 | 0.3210 (3) | 0.36721 (15) | 0.76000 (16) | 0.0425 (10) | |
H65 | 0.2597 | 0.3911 | 0.7669 | 0.051* | |
C66 | 0.3277 (3) | 0.33849 (13) | 0.71150 (13) | 0.0305 (8) | |
H66 | 0.2716 | 0.3437 | 0.6859 | 0.037* | |
C71 | 0.3970 (2) | 0.16783 (12) | 0.71614 (11) | 0.0189 (7) | |
C72 | 0.4881 (3) | 0.14855 (13) | 0.74677 (12) | 0.0250 (8) | |
H72 | 0.5525 | 0.1347 | 0.7298 | 0.030* | |
C73 | 0.4846 (3) | 0.14966 (14) | 0.80205 (14) | 0.0363 (9) | |
H73 | 0.5465 | 0.1367 | 0.8215 | 0.044* | |
C74 | 0.3896 (3) | 0.16999 (15) | 0.82824 (14) | 0.0406 (9) | |
H74 | 0.3873 | 0.1708 | 0.8652 | 0.049* | |
C75 | 0.2984 (3) | 0.18909 (14) | 0.79879 (13) | 0.0347 (9) | |
H75 | 0.2341 | 0.2028 | 0.8160 | 0.042* | |
C76 | 0.3023 (3) | 0.18798 (13) | 0.74365 (13) | 0.0265 (8) | |
H76 | 0.2400 | 0.2010 | 0.7245 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0190 (2) | 0.0162 (2) | 0.0157 (2) | 0.00067 (15) | 0.00048 (18) | −0.00147 (18) |
Cl | 0.0319 (4) | 0.0230 (4) | 0.0165 (4) | 0.0006 (4) | 0.0001 (3) | −0.0016 (4) |
P1 | 0.0187 (4) | 0.0179 (4) | 0.0170 (5) | 0.0008 (3) | 0.0009 (4) | −0.0009 (4) |
P2 | 0.0189 (4) | 0.0177 (4) | 0.0179 (5) | 0.0022 (3) | −0.0003 (4) | −0.0010 (4) |
C11 | 0.0172 (16) | 0.029 (2) | 0.0187 (19) | −0.0018 (14) | 0.0018 (14) | −0.0075 (14) |
C12 | 0.029 (2) | 0.035 (2) | 0.035 (2) | −0.0058 (16) | 0.0058 (17) | −0.0082 (17) |
C13 | 0.033 (2) | 0.055 (3) | 0.046 (3) | −0.017 (2) | 0.0118 (19) | −0.023 (2) |
C14 | 0.024 (2) | 0.082 (3) | 0.033 (2) | −0.010 (2) | 0.0004 (17) | −0.023 (2) |
C15 | 0.024 (2) | 0.077 (3) | 0.031 (2) | 0.004 (2) | −0.0043 (16) | −0.005 (2) |
C16 | 0.0218 (18) | 0.041 (2) | 0.029 (2) | 0.0006 (16) | 0.0017 (15) | −0.0037 (17) |
C21 | 0.0212 (17) | 0.0225 (18) | 0.0157 (18) | 0.0048 (13) | 0.0022 (13) | 0.0017 (14) |
C22 | 0.0263 (19) | 0.0237 (19) | 0.032 (2) | 0.0044 (15) | 0.0021 (15) | −0.0031 (16) |
C23 | 0.046 (2) | 0.028 (2) | 0.035 (2) | 0.0166 (18) | −0.0014 (18) | −0.0063 (17) |
C24 | 0.035 (2) | 0.044 (2) | 0.022 (2) | 0.0229 (18) | 0.0072 (16) | 0.0062 (17) |
C25 | 0.0251 (19) | 0.039 (2) | 0.026 (2) | 0.0081 (16) | 0.0039 (15) | 0.0130 (17) |
C26 | 0.0238 (17) | 0.0238 (18) | 0.024 (2) | 0.0018 (15) | 0.0005 (15) | 0.0070 (14) |
C31 | 0.0207 (16) | 0.0194 (17) | 0.0188 (18) | −0.0037 (13) | 0.0013 (14) | −0.0024 (14) |
C32 | 0.0271 (18) | 0.0245 (19) | 0.027 (2) | 0.0008 (15) | 0.0029 (15) | 0.0022 (15) |
C33 | 0.040 (2) | 0.028 (2) | 0.028 (2) | 0.0020 (16) | −0.0030 (17) | 0.0080 (16) |
C34 | 0.043 (2) | 0.031 (2) | 0.018 (2) | −0.0051 (17) | −0.0033 (16) | 0.0050 (16) |
C35 | 0.0297 (19) | 0.034 (2) | 0.023 (2) | −0.0070 (16) | 0.0067 (16) | −0.0034 (16) |
C36 | 0.0256 (18) | 0.0266 (19) | 0.025 (2) | −0.0011 (15) | 0.0002 (15) | 0.0016 (15) |
C41 | 0.0280 (19) | 0.0251 (19) | 0.025 (2) | 0.0111 (15) | −0.0085 (15) | −0.0116 (16) |
C42 | 0.060 (3) | 0.029 (2) | 0.041 (2) | 0.0074 (19) | −0.025 (2) | 0.0000 (19) |
C43 | 0.098 (4) | 0.038 (3) | 0.055 (3) | 0.018 (3) | −0.050 (3) | −0.007 (2) |
C44 | 0.085 (4) | 0.053 (3) | 0.069 (4) | 0.047 (3) | −0.054 (3) | −0.033 (3) |
C45 | 0.036 (2) | 0.072 (3) | 0.072 (4) | 0.023 (2) | −0.025 (2) | −0.044 (3) |
C46 | 0.031 (2) | 0.052 (3) | 0.046 (3) | 0.0108 (18) | −0.0078 (19) | −0.018 (2) |
C51 | 0.0226 (17) | 0.0219 (18) | 0.0135 (17) | −0.0012 (14) | −0.0009 (13) | 0.0026 (14) |
C52 | 0.0308 (19) | 0.0245 (19) | 0.0214 (19) | 0.0000 (15) | 0.0011 (15) | −0.0036 (15) |
C53 | 0.046 (2) | 0.029 (2) | 0.029 (2) | −0.0173 (17) | 0.0042 (18) | −0.0068 (16) |
C54 | 0.042 (2) | 0.054 (3) | 0.027 (2) | −0.021 (2) | 0.0140 (17) | −0.0083 (19) |
C55 | 0.036 (2) | 0.050 (3) | 0.036 (2) | −0.0116 (19) | 0.0175 (18) | −0.0206 (19) |
C56 | 0.0284 (19) | 0.033 (2) | 0.027 (2) | −0.0057 (15) | 0.0050 (15) | −0.0062 (16) |
C61 | 0.0236 (17) | 0.0170 (17) | 0.0235 (19) | −0.0031 (14) | 0.0029 (15) | −0.0034 (14) |
C62 | 0.033 (2) | 0.028 (2) | 0.025 (2) | −0.0019 (15) | 0.0041 (16) | −0.0029 (16) |
C63 | 0.045 (2) | 0.041 (2) | 0.024 (2) | −0.0140 (19) | −0.0001 (17) | −0.0070 (17) |
C64 | 0.058 (3) | 0.044 (2) | 0.032 (2) | −0.015 (2) | 0.022 (2) | −0.0180 (19) |
C65 | 0.039 (2) | 0.036 (2) | 0.053 (3) | 0.0021 (18) | 0.015 (2) | −0.017 (2) |
C66 | 0.0277 (19) | 0.025 (2) | 0.038 (2) | −0.0007 (16) | 0.0068 (16) | −0.0073 (17) |
C71 | 0.0233 (16) | 0.0157 (16) | 0.0178 (17) | −0.0018 (13) | 0.0010 (14) | −0.0043 (14) |
C72 | 0.0286 (19) | 0.0240 (19) | 0.022 (2) | 0.0035 (15) | −0.0006 (15) | −0.0006 (14) |
C73 | 0.043 (2) | 0.040 (2) | 0.026 (2) | 0.0020 (18) | −0.0121 (18) | 0.0036 (17) |
C74 | 0.065 (3) | 0.043 (2) | 0.0138 (19) | −0.002 (2) | 0.0012 (19) | −0.0022 (18) |
C75 | 0.045 (2) | 0.033 (2) | 0.026 (2) | 0.0031 (18) | 0.0163 (18) | −0.0055 (17) |
C76 | 0.0296 (19) | 0.0221 (18) | 0.028 (2) | −0.0013 (15) | 0.0011 (16) | −0.0008 (15) |
Ni—C71 | 1.893 (3) | C41—C42 | 1.393 (5) |
Ni—P2 | 2.2099 (9) | C42—C43 | 1.375 (5) |
Ni—P1 | 2.2149 (8) | C42—H42 | 0.9300 |
Ni—Cl | 2.2368 (8) | C43—C44 | 1.352 (6) |
P1—C31 | 1.823 (3) | C43—H43 | 0.9300 |
P1—C21 | 1.829 (3) | C44—C45 | 1.376 (6) |
P1—C11 | 1.839 (3) | C44—H44 | 0.9300 |
P2—C41 | 1.824 (3) | C45—C46 | 1.401 (5) |
P2—C61 | 1.828 (3) | C45—H45 | 0.9300 |
P2—C51 | 1.832 (3) | C46—H46 | 0.9300 |
C11—C16 | 1.387 (4) | C51—C52 | 1.391 (4) |
C11—C12 | 1.391 (4) | C51—C56 | 1.392 (4) |
C12—C13 | 1.378 (4) | C52—C53 | 1.376 (4) |
C12—H12 | 0.9300 | C52—H52 | 0.9300 |
C13—C14 | 1.372 (5) | C53—C54 | 1.379 (4) |
C13—H13 | 0.9300 | C53—H53 | 0.9300 |
C14—C15 | 1.374 (5) | C54—C55 | 1.373 (4) |
C14—H14 | 0.9300 | C54—H54 | 0.9300 |
C15—C16 | 1.387 (4) | C55—C56 | 1.380 (4) |
C15—H15 | 0.9300 | C55—H55 | 0.9300 |
C16—H16 | 0.9300 | C56—H56 | 0.9300 |
C21—C26 | 1.385 (4) | C61—C66 | 1.387 (4) |
C21—C22 | 1.391 (4) | C61—C62 | 1.392 (4) |
C22—C23 | 1.389 (4) | C62—C63 | 1.380 (4) |
C22—H22 | 0.9300 | C62—H62 | 0.9300 |
C23—C24 | 1.378 (5) | C63—C64 | 1.378 (5) |
C23—H23 | 0.9300 | C63—H63 | 0.9300 |
C24—C25 | 1.377 (4) | C64—C65 | 1.370 (5) |
C24—H24 | 0.9300 | C64—H64 | 0.9300 |
C25—C26 | 1.382 (4) | C65—C66 | 1.394 (4) |
C25—H25 | 0.9300 | C65—H65 | 0.9300 |
C26—H26 | 0.9300 | C66—H66 | 0.9300 |
C31—C32 | 1.378 (4) | C71—C76 | 1.396 (4) |
C31—C36 | 1.392 (4) | C71—C72 | 1.396 (4) |
C32—C33 | 1.385 (4) | C72—C73 | 1.390 (4) |
C32—H32 | 0.9300 | C72—H72 | 0.9300 |
C33—C34 | 1.379 (4) | C73—C74 | 1.384 (5) |
C33—H33 | 0.9300 | C73—H73 | 0.9300 |
C34—C35 | 1.383 (4) | C74—C75 | 1.380 (5) |
C34—H34 | 0.9300 | C74—H74 | 0.9300 |
C35—C36 | 1.388 (4) | C75—C76 | 1.387 (4) |
C35—H35 | 0.9300 | C75—H75 | 0.9300 |
C36—H36 | 0.9300 | C76—H76 | 0.9300 |
C41—C46 | 1.379 (4) | ||
C71—Ni—P2 | 90.33 (9) | C46—C41—C42 | 118.7 (3) |
C71—Ni—P1 | 91.41 (9) | C46—C41—P2 | 119.0 (3) |
P2—Ni—P1 | 177.59 (4) | C42—C41—P2 | 122.3 (3) |
C71—Ni—Cl | 179.87 (10) | C43—C42—C41 | 120.3 (4) |
P2—Ni—Cl | 89.55 (3) | C43—C42—H42 | 119.9 |
P1—Ni—Cl | 88.71 (3) | C41—C42—H42 | 119.9 |
C31—P1—C21 | 103.17 (13) | C44—C43—C42 | 121.1 (4) |
C31—P1—C11 | 102.40 (14) | C44—C43—H43 | 119.5 |
C21—P1—C11 | 107.68 (13) | C42—C43—H43 | 119.5 |
C31—P1—Ni | 118.40 (10) | C43—C44—C45 | 120.1 (4) |
C21—P1—Ni | 109.87 (10) | C43—C44—H44 | 120.0 |
C11—P1—Ni | 114.27 (10) | C45—C44—H44 | 120.0 |
C41—P2—C61 | 103.35 (14) | C44—C45—C46 | 119.7 (4) |
C41—P2—C51 | 104.58 (14) | C44—C45—H45 | 120.1 |
C61—P2—C51 | 101.63 (14) | C46—C45—H45 | 120.1 |
C41—P2—Ni | 108.21 (10) | C41—C46—C45 | 120.1 (4) |
C61—P2—Ni | 120.31 (10) | C41—C46—H46 | 119.9 |
C51—P2—Ni | 116.97 (10) | C45—C46—H46 | 119.9 |
C16—C11—C12 | 118.9 (3) | C52—C51—C56 | 118.5 (3) |
C16—C11—P1 | 120.1 (2) | C52—C51—P2 | 120.4 (2) |
C12—C11—P1 | 121.0 (2) | C56—C51—P2 | 121.0 (2) |
C13—C12—C11 | 120.1 (3) | C53—C52—C51 | 120.8 (3) |
C13—C12—H12 | 120.0 | C53—C52—H52 | 119.6 |
C11—C12—H12 | 120.0 | C51—C52—H52 | 119.6 |
C14—C13—C12 | 120.8 (4) | C52—C53—C54 | 120.2 (3) |
C14—C13—H13 | 119.6 | C52—C53—H53 | 119.9 |
C12—C13—H13 | 119.6 | C54—C53—H53 | 119.9 |
C13—C14—C15 | 119.8 (3) | C55—C54—C53 | 119.5 (3) |
C13—C14—H14 | 120.1 | C55—C54—H54 | 120.2 |
C15—C14—H14 | 120.1 | C53—C54—H54 | 120.2 |
C14—C15—C16 | 120.2 (4) | C54—C55—C56 | 120.9 (3) |
C14—C15—H15 | 119.9 | C54—C55—H55 | 119.6 |
C16—C15—H15 | 119.9 | C56—C55—H55 | 119.6 |
C15—C16—C11 | 120.3 (3) | C55—C56—C51 | 120.1 (3) |
C15—C16—H16 | 119.8 | C55—C56—H56 | 120.0 |
C11—C16—H16 | 119.8 | C51—C56—H56 | 120.0 |
C26—C21—C22 | 118.5 (3) | C66—C61—C62 | 118.7 (3) |
C26—C21—P1 | 117.5 (2) | C66—C61—P2 | 123.0 (2) |
C22—C21—P1 | 124.0 (2) | C62—C61—P2 | 118.3 (2) |
C23—C22—C21 | 120.3 (3) | C63—C62—C61 | 120.9 (3) |
C23—C22—H22 | 119.9 | C63—C62—H62 | 119.5 |
C21—C22—H22 | 119.9 | C61—C62—H62 | 119.5 |
C24—C23—C22 | 120.4 (3) | C64—C63—C62 | 119.8 (3) |
C24—C23—H23 | 119.8 | C64—C63—H63 | 120.1 |
C22—C23—H23 | 119.8 | C62—C63—H63 | 120.1 |
C25—C24—C23 | 119.7 (3) | C65—C64—C63 | 120.1 (3) |
C25—C24—H24 | 120.2 | C65—C64—H64 | 119.9 |
C23—C24—H24 | 120.2 | C63—C64—H64 | 119.9 |
C24—C25—C26 | 120.1 (3) | C64—C65—C66 | 120.4 (3) |
C24—C25—H25 | 120.0 | C64—C65—H65 | 119.8 |
C26—C25—H25 | 120.0 | C66—C65—H65 | 119.8 |
C25—C26—C21 | 121.1 (3) | C61—C66—C65 | 120.0 (3) |
C25—C26—H26 | 119.4 | C61—C66—H66 | 120.0 |
C21—C26—H26 | 119.4 | C65—C66—H66 | 120.0 |
C32—C31—C36 | 118.9 (3) | C76—C71—C72 | 116.9 (3) |
C32—C31—P1 | 122.9 (2) | C76—C71—Ni | 122.1 (2) |
C36—C31—P1 | 117.9 (2) | C72—C71—Ni | 121.0 (2) |
C31—C32—C33 | 121.0 (3) | C73—C72—C71 | 121.5 (3) |
C31—C32—H32 | 119.5 | C73—C72—H72 | 119.3 |
C33—C32—H32 | 119.5 | C71—C72—H72 | 119.3 |
C34—C33—C32 | 119.8 (3) | C74—C73—C72 | 120.3 (3) |
C34—C33—H33 | 120.1 | C74—C73—H73 | 119.8 |
C32—C33—H33 | 120.1 | C72—C73—H73 | 119.8 |
C33—C34—C35 | 120.0 (3) | C75—C74—C73 | 119.2 (3) |
C33—C34—H34 | 120.0 | C75—C74—H74 | 120.4 |
C35—C34—H34 | 120.0 | C73—C74—H74 | 120.4 |
C34—C35—C36 | 119.9 (3) | C74—C75—C76 | 120.3 (3) |
C34—C35—H35 | 120.1 | C74—C75—H75 | 119.8 |
C36—C35—H35 | 120.1 | C76—C75—H75 | 119.8 |
C35—C36—C31 | 120.4 (3) | C75—C76—C71 | 121.8 (3) |
C35—C36—H36 | 119.8 | C75—C76—H76 | 119.1 |
C31—C36—H36 | 119.8 | C71—C76—H76 | 119.1 |
C71—Ni—P1—C31 | −6.53 (14) | C61—P2—C41—C46 | −85.6 (3) |
Cl—Ni—P1—C31 | 173.51 (11) | C51—P2—C41—C46 | 168.4 (3) |
C71—Ni—P1—C21 | −124.61 (13) | Ni—P2—C41—C46 | 43.0 (3) |
Cl—Ni—P1—C21 | 55.42 (10) | C61—P2—C41—C42 | 93.5 (3) |
C71—Ni—P1—C11 | 114.24 (14) | C51—P2—C41—C42 | −12.5 (3) |
Cl—Ni—P1—C11 | −65.72 (11) | Ni—P2—C41—C42 | −137.9 (3) |
C71—Ni—P2—C41 | −126.47 (14) | C46—C41—C42—C43 | 1.1 (5) |
Cl—Ni—P2—C41 | 53.50 (11) | P2—C41—C42—C43 | −178.0 (3) |
C71—Ni—P2—C61 | −8.19 (15) | C41—C42—C43—C44 | −0.7 (6) |
Cl—Ni—P2—C61 | 171.78 (12) | C42—C43—C44—C45 | 0.1 (7) |
C71—Ni—P2—C51 | 115.84 (14) | C43—C44—C45—C46 | 0.1 (6) |
Cl—Ni—P2—C51 | −64.19 (11) | C42—C41—C46—C45 | −0.9 (5) |
C31—P1—C11—C16 | 143.5 (3) | P2—C41—C46—C45 | 178.2 (3) |
C21—P1—C11—C16 | −108.2 (3) | C44—C45—C46—C41 | 0.4 (6) |
Ni—P1—C11—C16 | 14.2 (3) | C41—P2—C51—C52 | 78.1 (3) |
C31—P1—C11—C12 | −34.7 (3) | C61—P2—C51—C52 | −29.2 (3) |
C21—P1—C11—C12 | 73.7 (3) | Ni—P2—C51—C52 | −162.2 (2) |
Ni—P1—C11—C12 | −164.0 (2) | C41—P2—C51—C56 | −99.4 (3) |
C16—C11—C12—C13 | 0.6 (5) | C61—P2—C51—C56 | 153.3 (3) |
P1—C11—C12—C13 | 178.7 (2) | Ni—P2—C51—C56 | 20.3 (3) |
C11—C12—C13—C14 | −0.7 (5) | C56—C51—C52—C53 | 2.2 (5) |
C12—C13—C14—C15 | 0.5 (5) | P2—C51—C52—C53 | −175.3 (2) |
C13—C14—C15—C16 | −0.1 (5) | C51—C52—C53—C54 | −1.0 (5) |
C14—C15—C16—C11 | −0.1 (5) | C52—C53—C54—C55 | −0.4 (5) |
C12—C11—C16—C15 | −0.2 (5) | C53—C54—C55—C56 | 0.6 (6) |
P1—C11—C16—C15 | −178.3 (2) | C54—C55—C56—C51 | 0.7 (5) |
C31—P1—C21—C26 | −99.1 (2) | C52—C51—C56—C55 | −2.1 (5) |
C11—P1—C21—C26 | 153.1 (2) | P2—C51—C56—C55 | 175.5 (3) |
Ni—P1—C21—C26 | 28.0 (3) | C41—P2—C61—C66 | 13.1 (3) |
C31—P1—C21—C22 | 79.6 (3) | C51—P2—C61—C66 | 121.3 (3) |
C11—P1—C21—C22 | −28.2 (3) | Ni—P2—C61—C66 | −107.6 (3) |
Ni—P1—C21—C22 | −153.2 (2) | C41—P2—C61—C62 | −168.7 (2) |
C26—C21—C22—C23 | −0.5 (5) | C51—P2—C61—C62 | −60.5 (3) |
P1—C21—C22—C23 | −179.3 (2) | Ni—P2—C61—C62 | 70.6 (3) |
C21—C22—C23—C24 | 0.4 (5) | C66—C61—C62—C63 | −0.3 (5) |
C22—C23—C24—C25 | 0.9 (5) | P2—C61—C62—C63 | −178.6 (2) |
C23—C24—C25—C26 | −1.9 (5) | C61—C62—C63—C64 | 0.8 (5) |
C24—C25—C26—C21 | 1.7 (5) | C62—C63—C64—C65 | −0.3 (5) |
C22—C21—C26—C25 | −0.5 (5) | C63—C64—C65—C66 | −0.7 (5) |
P1—C21—C26—C25 | 178.3 (2) | C62—C61—C66—C65 | −0.6 (5) |
C21—P1—C31—C32 | 18.3 (3) | P2—C61—C66—C65 | 177.6 (2) |
C11—P1—C31—C32 | 130.1 (3) | C64—C65—C66—C61 | 1.1 (5) |
Ni—P1—C31—C32 | −103.2 (3) | P2—Ni—C71—C76 | 75.2 (2) |
C21—P1—C31—C36 | −169.1 (2) | P1—Ni—C71—C76 | −103.1 (2) |
C11—P1—C31—C36 | −57.3 (3) | P2—Ni—C71—C72 | −104.2 (2) |
Ni—P1—C31—C36 | 69.4 (3) | P1—Ni—C71—C72 | 77.5 (2) |
C36—C31—C32—C33 | −2.2 (5) | C76—C71—C72—C73 | −0.3 (4) |
P1—C31—C32—C33 | 170.3 (2) | Ni—C71—C72—C73 | 179.2 (2) |
C31—C32—C33—C34 | 0.0 (5) | C71—C72—C73—C74 | 0.2 (5) |
C32—C33—C34—C35 | 1.9 (5) | C72—C73—C74—C75 | 0.0 (5) |
C33—C34—C35—C36 | −1.6 (5) | C73—C74—C75—C76 | −0.1 (5) |
C34—C35—C36—C31 | −0.7 (5) | C74—C75—C76—C71 | 0.0 (5) |
C32—C31—C36—C35 | 2.5 (5) | C72—C71—C76—C75 | 0.2 (5) |
P1—C31—C36—C35 | −170.4 (2) | Ni—C71—C76—C75 | −179.2 (2) |
[Ni(C6H5)Cl(C18H15P)2]·[NiCl(C18H15P)2] | F(000) = 2732 |
Mr = 1314.50 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6984 reflections |
a = 24.183 (6) Å | θ = 2.4–25.7° |
b = 12.257 (3) Å | µ = 0.81 mm−1 |
c = 23.712 (5) Å | T = 150 K |
β = 113.781 (8)° | Prism, green |
V = 6432 (3) Å3 | 0.23 × 0.17 × 0.07 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 13903 independent reflections |
Radiation source: fine-focus sealed tube | 10162 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
ϕ and ω scans | θmax = 26.9°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −30→30 |
Tmin = 0.835, Tmax = 0.945 | k = −15→15 |
109681 measured reflections | l = −30→30 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0427P)2 + 1.0369P] where P = (Fo2 + 2Fc2)/3 |
13903 reflections | (Δ/σ)max = 0.002 |
775 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
[Ni(C6H5)Cl(C18H15P)2]·[NiCl(C18H15P)2] | V = 6432 (3) Å3 |
Mr = 1314.50 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 24.183 (6) Å | µ = 0.81 mm−1 |
b = 12.257 (3) Å | T = 150 K |
c = 23.712 (5) Å | 0.23 × 0.17 × 0.07 mm |
β = 113.781 (8)° |
Bruker SMART CCD area-detector diffractometer | 13903 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 10162 reflections with I > 2σ(I) |
Tmin = 0.835, Tmax = 0.945 | Rint = 0.078 |
109681 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.43 e Å−3 |
13903 reflections | Δρmin = −0.50 e Å−3 |
775 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 | ||
Ni | 0.117497 (13) | 0.26358 (2) | 0.326312 (13) | 0.01769 (7) | |
Ni1 | 0.362867 (13) | −0.18707 (2) | 0.637873 (13) | 0.01907 (8) | |
P1 | 0.09365 (3) | 0.25357 (4) | 0.40700 (3) | 0.01779 (12) | |
P2 | 0.14279 (3) | 0.28251 (4) | 0.24711 (3) | 0.01821 (13) | |
P11 | 0.40688 (3) | −0.04026 (5) | 0.69177 (3) | 0.02100 (13) | |
P21 | 0.39781 (3) | −0.23344 (5) | 0.56815 (3) | 0.02028 (13) | |
Cl | 0.21572 (3) | 0.25632 (4) | 0.38879 (3) | 0.02513 (13) | |
Cl1 | 0.28231 (3) | −0.25962 (4) | 0.63957 (3) | 0.02797 (13) | |
C11 | 0.11791 (10) | 0.12969 (17) | 0.45316 (10) | 0.0209 (5) | |
C12 | 0.09906 (11) | 0.10726 (19) | 0.50079 (10) | 0.0270 (5) | |
H12 | 0.0737 | 0.1558 | 0.5091 | 0.032* | |
C13 | 0.11805 (11) | 0.0134 (2) | 0.53524 (11) | 0.0322 (6) | |
H13 | 0.1057 | −0.0006 | 0.5670 | 0.039* | |
C14 | 0.15500 (12) | −0.0596 (2) | 0.52323 (12) | 0.0340 (6) | |
H14 | 0.1680 | −0.1223 | 0.5471 | 0.041* | |
C15 | 0.17276 (11) | −0.04003 (19) | 0.47597 (12) | 0.0328 (6) | |
H15 | 0.1973 | −0.0901 | 0.4676 | 0.039* | |
C16 | 0.15431 (10) | 0.05394 (17) | 0.44061 (11) | 0.0245 (5) | |
H16 | 0.1663 | 0.0663 | 0.4085 | 0.029* | |
C21 | 0.12747 (10) | 0.37008 (18) | 0.45698 (10) | 0.0216 (5) | |
C22 | 0.15000 (11) | 0.3688 (2) | 0.52082 (11) | 0.0293 (6) | |
H22 | 0.1503 | 0.3042 | 0.5415 | 0.035* | |
C23 | 0.17202 (11) | 0.4643 (2) | 0.55364 (12) | 0.0356 (6) | |
H23 | 0.1879 | 0.4627 | 0.5965 | 0.043* | |
C24 | 0.17082 (12) | 0.5607 (2) | 0.52412 (13) | 0.0395 (7) | |
H24 | 0.1853 | 0.6242 | 0.5467 | 0.047* | |
C25 | 0.14800 (13) | 0.5633 (2) | 0.46051 (13) | 0.0416 (7) | |
H25 | 0.1466 | 0.6286 | 0.4401 | 0.050* | |
C26 | 0.12731 (12) | 0.46819 (19) | 0.42755 (12) | 0.0332 (6) | |
H26 | 0.1130 | 0.4698 | 0.3848 | 0.040* | |
C31 | 0.01467 (10) | 0.26363 (17) | 0.39578 (10) | 0.0208 (5) | |
C32 | −0.00979 (11) | 0.35609 (19) | 0.41053 (11) | 0.0276 (5) | |
H32 | 0.0148 | 0.4158 | 0.4284 | 0.033* | |
C33 | −0.07066 (12) | 0.3599 (2) | 0.39877 (12) | 0.0350 (6) | |
H33 | −0.0867 | 0.4222 | 0.4088 | 0.042* | |
C34 | −0.10758 (11) | 0.2723 (2) | 0.37232 (12) | 0.0352 (6) | |
H34 | −0.1483 | 0.2750 | 0.3650 | 0.042* | |
C35 | −0.08396 (11) | 0.1804 (2) | 0.35674 (12) | 0.0363 (6) | |
H35 | −0.1090 | 0.1217 | 0.3380 | 0.044* | |
C36 | −0.02297 (11) | 0.17577 (19) | 0.36906 (11) | 0.0289 (5) | |
H36 | −0.0070 | 0.1130 | 0.3593 | 0.035* | |
C41 | 0.18937 (10) | 0.16818 (17) | 0.24425 (10) | 0.0210 (5) | |
C42 | 0.24121 (11) | 0.17443 (19) | 0.23298 (11) | 0.0270 (5) | |
H42 | 0.2576 | 0.2420 | 0.2306 | 0.032* | |
C43 | 0.26848 (11) | 0.0792 (2) | 0.22527 (11) | 0.0331 (6) | |
H43 | 0.3037 | 0.0834 | 0.2185 | 0.040* | |
C44 | 0.24415 (11) | −0.02119 (19) | 0.22745 (10) | 0.0299 (6) | |
H44 | 0.2618 | −0.0842 | 0.2204 | 0.036* | |
C45 | 0.19351 (11) | −0.02834 (18) | 0.24012 (11) | 0.0284 (5) | |
H45 | 0.1775 | −0.0962 | 0.2427 | 0.034* | |
C46 | 0.16652 (11) | 0.06549 (18) | 0.24900 (11) | 0.0265 (5) | |
H46 | 0.1327 | 0.0603 | 0.2583 | 0.032* | |
C51 | 0.18329 (10) | 0.40862 (17) | 0.24939 (10) | 0.0206 (5) | |
C52 | 0.19796 (11) | 0.43998 (18) | 0.20055 (11) | 0.0249 (5) | |
H52 | 0.1883 | 0.3946 | 0.1665 | 0.030* | |
C53 | 0.22673 (11) | 0.53807 (19) | 0.20250 (12) | 0.0288 (6) | |
H53 | 0.2369 | 0.5578 | 0.1700 | 0.035* | |
C54 | 0.24047 (11) | 0.6069 (2) | 0.25211 (12) | 0.0347 (6) | |
H54 | 0.2597 | 0.6730 | 0.2530 | 0.042* | |
C55 | 0.22578 (12) | 0.57785 (19) | 0.30061 (12) | 0.0352 (6) | |
H55 | 0.2349 | 0.6247 | 0.3340 | 0.042* | |
C56 | 0.19748 (11) | 0.47912 (18) | 0.29965 (11) | 0.0291 (6) | |
H56 | 0.1879 | 0.4597 | 0.3326 | 0.035* | |
C61 | 0.08400 (10) | 0.28269 (17) | 0.16862 (10) | 0.0208 (5) | |
C62 | 0.04638 (11) | 0.37295 (18) | 0.14884 (11) | 0.0280 (5) | |
H62 | 0.0542 | 0.4343 | 0.1739 | 0.034* | |
C63 | −0.00254 (12) | 0.3731 (2) | 0.09238 (11) | 0.0351 (6) | |
H63 | −0.0272 | 0.4343 | 0.0799 | 0.042* | |
C64 | −0.01488 (12) | 0.2827 (2) | 0.05458 (11) | 0.0320 (6) | |
H64 | −0.0479 | 0.2825 | 0.0168 | 0.038* | |
C65 | 0.02186 (12) | 0.1935 (2) | 0.07319 (11) | 0.0319 (6) | |
H65 | 0.0137 | 0.1325 | 0.0478 | 0.038* | |
C66 | 0.07101 (12) | 0.19296 (19) | 0.12936 (11) | 0.0289 (6) | |
H66 | 0.0958 | 0.1317 | 0.1411 | 0.035* | |
C71 | 0.03453 (10) | 0.26810 (18) | 0.27256 (10) | 0.0229 (5) | |
C72 | 0.00099 (12) | 0.3635 (2) | 0.26125 (12) | 0.0351 (6) | |
H72 | 0.0194 | 0.4276 | 0.2810 | 0.042* | |
C73 | −0.05955 (13) | 0.3653 (3) | 0.22103 (13) | 0.0496 (8) | |
H73 | −0.0807 | 0.4308 | 0.2131 | 0.060* | |
C74 | −0.08807 (14) | 0.2726 (3) | 0.19324 (15) | 0.0594 (9) | |
H74 | −0.1289 | 0.2738 | 0.1671 | 0.071* | |
C75 | −0.05638 (14) | 0.1778 (3) | 0.20398 (15) | 0.0605 (9) | |
H75 | −0.0756 | 0.1139 | 0.1850 | 0.073* | |
C76 | 0.00459 (12) | 0.1756 (2) | 0.24302 (13) | 0.0412 (7) | |
H76 | 0.0256 | 0.1101 | 0.2493 | 0.049* | |
C111 | 0.40649 (12) | −0.05068 (19) | 0.76847 (11) | 0.0316 (6) | |
C112 | 0.37942 (13) | 0.0259 (2) | 0.79205 (12) | 0.0421 (7) | |
H112 | 0.3600 | 0.0859 | 0.7683 | 0.051* | |
C113 | 0.38117 (17) | 0.0135 (3) | 0.85107 (15) | 0.0645 (11) | |
H113 | 0.3632 | 0.0655 | 0.8668 | 0.077* | |
C114 | 0.4091 (2) | −0.0743 (3) | 0.88568 (15) | 0.0816 (15) | |
H114 | 0.4106 | −0.0818 | 0.9253 | 0.098* | |
C115 | 0.4349 (2) | −0.1516 (3) | 0.86277 (14) | 0.0820 (14) | |
H115 | 0.4537 | −0.2118 | 0.8867 | 0.098* | |
C116 | 0.43339 (16) | −0.1409 (2) | 0.80401 (12) | 0.0541 (9) | |
H116 | 0.4505 | −0.1946 | 0.7884 | 0.065* | |
C221 | 0.36532 (10) | 0.08452 (17) | 0.65897 (10) | 0.0213 (5) | |
C222 | 0.30600 (11) | 0.07743 (19) | 0.61591 (11) | 0.0267 (5) | |
H222 | 0.2875 | 0.0095 | 0.6054 | 0.032* | |
C223 | 0.27415 (12) | 0.1701 (2) | 0.58849 (12) | 0.0339 (6) | |
H223 | 0.2343 | 0.1645 | 0.5601 | 0.041* | |
C224 | 0.30123 (12) | 0.2707 (2) | 0.60308 (13) | 0.0365 (6) | |
H224 | 0.2798 | 0.3330 | 0.5842 | 0.044* | |
C225 | 0.36016 (12) | 0.2794 (2) | 0.64569 (13) | 0.0385 (7) | |
H225 | 0.3783 | 0.3477 | 0.6557 | 0.046* | |
C226 | 0.39229 (11) | 0.18719 (18) | 0.67360 (11) | 0.0294 (6) | |
H226 | 0.4320 | 0.1935 | 0.7022 | 0.035* | |
C331 | 0.48362 (10) | 0.00358 (17) | 0.70755 (11) | 0.0257 (5) | |
C332 | 0.52756 (12) | 0.02189 (19) | 0.76641 (13) | 0.0377 (7) | |
H332 | 0.5191 | 0.0068 | 0.8005 | 0.045* | |
C333 | 0.58376 (13) | 0.0624 (2) | 0.77480 (17) | 0.0536 (9) | |
H333 | 0.6128 | 0.0748 | 0.8144 | 0.064* | |
C334 | 0.59658 (13) | 0.0841 (2) | 0.72459 (19) | 0.0586 (10) | |
H334 | 0.6342 | 0.1123 | 0.7304 | 0.070* | |
C335 | 0.55403 (14) | 0.0644 (2) | 0.66519 (17) | 0.0496 (8) | |
H335 | 0.5634 | 0.0779 | 0.6314 | 0.060* | |
C336 | 0.49760 (12) | 0.02473 (19) | 0.65661 (13) | 0.0357 (6) | |
H336 | 0.4689 | 0.0120 | 0.6169 | 0.043* | |
C441 | 0.38296 (11) | −0.37529 (17) | 0.54246 (10) | 0.0233 (5) | |
C442 | 0.42815 (12) | −0.44863 (18) | 0.54818 (11) | 0.0298 (6) | |
H442 | 0.4684 | −0.4270 | 0.5661 | 0.036* | |
C443 | 0.41346 (14) | −0.5548 (2) | 0.52710 (13) | 0.0404 (7) | |
H443 | 0.4441 | −0.6043 | 0.5314 | 0.048* | |
C444 | 0.35407 (14) | −0.5877 (2) | 0.49995 (13) | 0.0399 (7) | |
H444 | 0.3446 | −0.6584 | 0.4849 | 0.048* | |
C445 | 0.30892 (13) | −0.5161 (2) | 0.49509 (12) | 0.0380 (6) | |
H445 | 0.2688 | −0.5383 | 0.4771 | 0.046* | |
C446 | 0.32313 (12) | −0.4105 (2) | 0.51701 (12) | 0.0324 (6) | |
H446 | 0.2924 | −0.3627 | 0.5147 | 0.039* | |
C551 | 0.35740 (10) | −0.15455 (18) | 0.49785 (10) | 0.0217 (5) | |
C552 | 0.33789 (12) | −0.1961 (2) | 0.43820 (11) | 0.0338 (6) | |
H552 | 0.3458 | −0.2684 | 0.4321 | 0.041* | |
C553 | 0.30681 (14) | −0.1303 (2) | 0.38805 (12) | 0.0417 (7) | |
H553 | 0.2944 | −0.1585 | 0.3484 | 0.050* | |
C554 | 0.29394 (12) | −0.0234 (2) | 0.39605 (12) | 0.0343 (6) | |
H554 | 0.2726 | 0.0201 | 0.3621 | 0.041* | |
C555 | 0.31295 (11) | 0.01847 (19) | 0.45484 (11) | 0.0288 (6) | |
H555 | 0.3045 | 0.0906 | 0.4606 | 0.035* | |
C556 | 0.34455 (10) | −0.04684 (18) | 0.50520 (11) | 0.0237 (5) | |
H556 | 0.3574 | −0.0178 | 0.5447 | 0.028* | |
C661 | 0.47717 (11) | −0.21517 (18) | 0.58341 (11) | 0.0252 (5) | |
C662 | 0.51970 (11) | −0.23035 (19) | 0.64320 (12) | 0.0311 (6) | |
H662 | 0.5072 | −0.2511 | 0.6739 | 0.037* | |
C663 | 0.58058 (12) | −0.2148 (2) | 0.65742 (14) | 0.0426 (7) | |
H663 | 0.6087 | −0.2242 | 0.6977 | 0.051* | |
C664 | 0.59966 (13) | −0.1853 (2) | 0.61207 (15) | 0.0482 (8) | |
H664 | 0.6406 | −0.1756 | 0.6215 | 0.058* | |
C665 | 0.55763 (14) | −0.1704 (2) | 0.55280 (15) | 0.0502 (8) | |
H665 | 0.5704 | −0.1504 | 0.5222 | 0.060* | |
C666 | 0.49686 (13) | −0.1846 (2) | 0.53803 (13) | 0.0372 (6) | |
H666 | 0.4690 | −0.1738 | 0.4977 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.01759 (15) | 0.01849 (14) | 0.01589 (15) | 0.00033 (11) | 0.00562 (12) | −0.00031 (11) |
Ni1 | 0.02074 (16) | 0.01845 (14) | 0.01757 (16) | −0.00343 (12) | 0.00726 (13) | −0.00114 (11) |
P1 | 0.0166 (3) | 0.0202 (3) | 0.0155 (3) | 0.0007 (2) | 0.0055 (2) | 0.0007 (2) |
P2 | 0.0187 (3) | 0.0183 (3) | 0.0170 (3) | 0.0010 (2) | 0.0066 (3) | 0.0002 (2) |
P11 | 0.0220 (3) | 0.0205 (3) | 0.0184 (3) | −0.0040 (2) | 0.0059 (3) | −0.0020 (2) |
P21 | 0.0221 (3) | 0.0201 (3) | 0.0182 (3) | 0.0003 (2) | 0.0077 (3) | 0.0005 (2) |
Cl | 0.0198 (3) | 0.0291 (3) | 0.0227 (3) | 0.0009 (2) | 0.0047 (2) | 0.0021 (2) |
Cl1 | 0.0241 (3) | 0.0275 (3) | 0.0353 (4) | −0.0042 (2) | 0.0150 (3) | −0.0019 (2) |
C11 | 0.0192 (12) | 0.0210 (11) | 0.0181 (12) | −0.0024 (9) | 0.0029 (10) | 0.0027 (9) |
C12 | 0.0252 (14) | 0.0324 (13) | 0.0223 (13) | 0.0000 (11) | 0.0085 (11) | 0.0010 (10) |
C13 | 0.0317 (15) | 0.0410 (14) | 0.0190 (13) | −0.0095 (12) | 0.0052 (11) | 0.0066 (11) |
C14 | 0.0323 (15) | 0.0291 (13) | 0.0282 (15) | −0.0035 (11) | −0.0005 (12) | 0.0118 (11) |
C15 | 0.0289 (14) | 0.0223 (12) | 0.0426 (17) | 0.0024 (11) | 0.0098 (13) | 0.0032 (11) |
C16 | 0.0248 (13) | 0.0215 (11) | 0.0271 (14) | −0.0005 (10) | 0.0105 (11) | 0.0019 (10) |
C21 | 0.0179 (12) | 0.0261 (12) | 0.0198 (13) | 0.0013 (9) | 0.0067 (10) | −0.0055 (9) |
C22 | 0.0293 (14) | 0.0322 (13) | 0.0230 (14) | 0.0085 (11) | 0.0071 (11) | −0.0025 (11) |
C23 | 0.0288 (15) | 0.0474 (16) | 0.0233 (14) | 0.0063 (12) | 0.0029 (12) | −0.0142 (12) |
C24 | 0.0286 (15) | 0.0392 (15) | 0.0499 (19) | −0.0065 (12) | 0.0150 (14) | −0.0246 (13) |
C25 | 0.0543 (19) | 0.0311 (14) | 0.0441 (18) | −0.0094 (13) | 0.0247 (15) | −0.0082 (12) |
C26 | 0.0453 (17) | 0.0292 (13) | 0.0274 (14) | −0.0077 (12) | 0.0171 (13) | −0.0069 (11) |
C31 | 0.0187 (12) | 0.0269 (12) | 0.0165 (12) | 0.0035 (9) | 0.0069 (10) | 0.0063 (9) |
C32 | 0.0277 (14) | 0.0305 (12) | 0.0249 (14) | 0.0039 (11) | 0.0111 (11) | 0.0040 (10) |
C33 | 0.0307 (15) | 0.0431 (15) | 0.0331 (15) | 0.0135 (12) | 0.0149 (13) | 0.0078 (12) |
C34 | 0.0197 (13) | 0.0524 (16) | 0.0327 (15) | 0.0088 (12) | 0.0097 (12) | 0.0197 (13) |
C35 | 0.0233 (14) | 0.0401 (15) | 0.0405 (16) | −0.0050 (12) | 0.0075 (12) | 0.0106 (12) |
C36 | 0.0247 (13) | 0.0269 (12) | 0.0336 (15) | 0.0009 (10) | 0.0102 (12) | 0.0047 (11) |
C41 | 0.0225 (12) | 0.0220 (11) | 0.0159 (12) | 0.0045 (9) | 0.0051 (10) | 0.0006 (9) |
C42 | 0.0246 (13) | 0.0292 (12) | 0.0260 (14) | 0.0025 (10) | 0.0091 (11) | 0.0026 (10) |
C43 | 0.0255 (14) | 0.0446 (15) | 0.0303 (15) | 0.0102 (12) | 0.0123 (12) | 0.0011 (12) |
C44 | 0.0350 (15) | 0.0296 (13) | 0.0183 (13) | 0.0133 (11) | 0.0038 (11) | −0.0034 (10) |
C45 | 0.0294 (14) | 0.0223 (12) | 0.0246 (14) | 0.0025 (10) | 0.0017 (11) | −0.0011 (10) |
C46 | 0.0255 (13) | 0.0248 (12) | 0.0292 (14) | 0.0027 (10) | 0.0110 (11) | 0.0017 (10) |
C51 | 0.0194 (12) | 0.0197 (11) | 0.0216 (13) | 0.0013 (9) | 0.0072 (10) | 0.0015 (9) |
C52 | 0.0265 (13) | 0.0279 (12) | 0.0212 (13) | 0.0023 (10) | 0.0105 (11) | 0.0013 (10) |
C53 | 0.0245 (13) | 0.0313 (13) | 0.0334 (15) | 0.0016 (11) | 0.0147 (12) | 0.0079 (11) |
C54 | 0.0302 (15) | 0.0270 (13) | 0.0466 (17) | −0.0054 (11) | 0.0154 (13) | 0.0045 (12) |
C55 | 0.0430 (17) | 0.0264 (13) | 0.0361 (16) | −0.0075 (12) | 0.0156 (14) | −0.0075 (11) |
C56 | 0.0348 (15) | 0.0277 (12) | 0.0284 (14) | −0.0021 (11) | 0.0165 (12) | 0.0000 (11) |
C61 | 0.0229 (12) | 0.0230 (11) | 0.0169 (12) | −0.0017 (9) | 0.0086 (10) | 0.0014 (9) |
C62 | 0.0306 (14) | 0.0231 (12) | 0.0239 (14) | 0.0024 (10) | 0.0045 (11) | −0.0015 (10) |
C63 | 0.0332 (16) | 0.0351 (14) | 0.0277 (15) | 0.0098 (12) | 0.0026 (12) | 0.0006 (11) |
C64 | 0.0279 (14) | 0.0399 (14) | 0.0207 (14) | −0.0022 (12) | 0.0019 (11) | −0.0016 (11) |
C65 | 0.0393 (16) | 0.0314 (13) | 0.0193 (13) | −0.0010 (12) | 0.0060 (12) | −0.0056 (11) |
C66 | 0.0386 (15) | 0.0245 (12) | 0.0201 (13) | 0.0053 (11) | 0.0084 (12) | 0.0022 (10) |
C71 | 0.0205 (12) | 0.0321 (12) | 0.0161 (12) | 0.0034 (10) | 0.0076 (10) | 0.0006 (10) |
C72 | 0.0308 (15) | 0.0390 (14) | 0.0299 (15) | 0.0089 (12) | 0.0063 (12) | −0.0071 (12) |
C73 | 0.0347 (17) | 0.067 (2) | 0.0395 (18) | 0.0243 (16) | 0.0067 (14) | −0.0065 (16) |
C74 | 0.0218 (16) | 0.097 (3) | 0.046 (2) | 0.0094 (17) | −0.0009 (14) | −0.0236 (19) |
C75 | 0.0322 (18) | 0.064 (2) | 0.067 (2) | −0.0133 (16) | 0.0013 (16) | −0.0313 (18) |
C76 | 0.0283 (15) | 0.0380 (15) | 0.0477 (18) | −0.0033 (12) | 0.0052 (13) | −0.0167 (13) |
C111 | 0.0419 (16) | 0.0285 (13) | 0.0191 (13) | −0.0194 (12) | 0.0066 (12) | −0.0059 (10) |
C112 | 0.0519 (19) | 0.0479 (16) | 0.0323 (16) | −0.0213 (14) | 0.0229 (14) | −0.0134 (13) |
C113 | 0.103 (3) | 0.065 (2) | 0.046 (2) | −0.048 (2) | 0.052 (2) | −0.0275 (18) |
C114 | 0.157 (4) | 0.064 (2) | 0.0326 (19) | −0.072 (3) | 0.047 (2) | −0.0210 (17) |
C115 | 0.161 (4) | 0.0430 (19) | 0.0261 (18) | −0.035 (2) | 0.021 (2) | 0.0039 (15) |
C116 | 0.096 (3) | 0.0285 (14) | 0.0281 (16) | −0.0134 (16) | 0.0147 (17) | 0.0008 (12) |
C221 | 0.0239 (13) | 0.0228 (11) | 0.0195 (12) | −0.0020 (9) | 0.0112 (10) | −0.0041 (9) |
C222 | 0.0272 (14) | 0.0275 (12) | 0.0265 (14) | −0.0039 (10) | 0.0122 (11) | −0.0058 (10) |
C223 | 0.0233 (14) | 0.0413 (15) | 0.0327 (15) | 0.0046 (11) | 0.0066 (12) | −0.0012 (12) |
C224 | 0.0330 (16) | 0.0302 (13) | 0.0449 (17) | 0.0104 (12) | 0.0141 (14) | 0.0067 (12) |
C225 | 0.0358 (16) | 0.0211 (12) | 0.0582 (19) | −0.0014 (11) | 0.0186 (15) | −0.0026 (12) |
C226 | 0.0256 (14) | 0.0250 (12) | 0.0336 (15) | −0.0045 (10) | 0.0078 (12) | −0.0063 (11) |
C331 | 0.0198 (13) | 0.0170 (11) | 0.0363 (15) | −0.0010 (9) | 0.0071 (11) | −0.0006 (10) |
C332 | 0.0292 (15) | 0.0242 (13) | 0.0440 (17) | 0.0001 (11) | −0.0017 (13) | 0.0024 (12) |
C333 | 0.0239 (16) | 0.0266 (14) | 0.083 (3) | 0.0002 (12) | −0.0066 (16) | 0.0053 (15) |
C334 | 0.0195 (16) | 0.0267 (15) | 0.120 (3) | 0.0004 (12) | 0.018 (2) | 0.0056 (18) |
C335 | 0.0429 (19) | 0.0283 (14) | 0.092 (3) | −0.0005 (13) | 0.042 (2) | 0.0051 (15) |
C336 | 0.0310 (15) | 0.0243 (13) | 0.0538 (18) | −0.0021 (11) | 0.0193 (14) | −0.0036 (12) |
C441 | 0.0342 (14) | 0.0201 (11) | 0.0174 (12) | −0.0008 (10) | 0.0122 (11) | 0.0021 (9) |
C442 | 0.0320 (15) | 0.0267 (12) | 0.0290 (14) | 0.0008 (11) | 0.0106 (12) | 0.0017 (10) |
C443 | 0.0522 (19) | 0.0246 (13) | 0.0501 (18) | 0.0096 (13) | 0.0266 (16) | 0.0022 (12) |
C444 | 0.061 (2) | 0.0217 (12) | 0.0436 (17) | −0.0074 (13) | 0.0282 (16) | −0.0063 (12) |
C445 | 0.0422 (17) | 0.0314 (14) | 0.0404 (17) | −0.0115 (12) | 0.0166 (14) | −0.0072 (12) |
C446 | 0.0336 (15) | 0.0288 (13) | 0.0353 (16) | −0.0018 (11) | 0.0143 (13) | −0.0051 (11) |
C551 | 0.0211 (12) | 0.0264 (11) | 0.0182 (12) | 0.0013 (10) | 0.0084 (10) | 0.0024 (9) |
C552 | 0.0477 (17) | 0.0260 (12) | 0.0247 (14) | 0.0032 (12) | 0.0117 (13) | −0.0031 (11) |
C553 | 0.059 (2) | 0.0416 (16) | 0.0152 (14) | 0.0001 (14) | 0.0048 (13) | 0.0004 (12) |
C554 | 0.0359 (16) | 0.0332 (14) | 0.0250 (14) | 0.0003 (12) | 0.0032 (12) | 0.0103 (11) |
C555 | 0.0308 (14) | 0.0259 (12) | 0.0289 (14) | 0.0026 (10) | 0.0112 (12) | 0.0032 (10) |
C556 | 0.0259 (13) | 0.0261 (12) | 0.0190 (13) | 0.0008 (10) | 0.0087 (11) | 0.0007 (10) |
C661 | 0.0251 (13) | 0.0201 (11) | 0.0302 (14) | 0.0006 (10) | 0.0111 (11) | −0.0004 (10) |
C662 | 0.0285 (14) | 0.0308 (13) | 0.0309 (15) | 0.0033 (11) | 0.0089 (12) | 0.0079 (11) |
C663 | 0.0271 (15) | 0.0369 (15) | 0.0520 (19) | 0.0031 (12) | 0.0037 (14) | 0.0099 (13) |
C664 | 0.0303 (16) | 0.0429 (17) | 0.070 (2) | −0.0019 (13) | 0.0191 (17) | 0.0056 (15) |
C665 | 0.0407 (18) | 0.0594 (19) | 0.062 (2) | −0.0075 (15) | 0.0330 (17) | 0.0062 (16) |
C666 | 0.0365 (16) | 0.0462 (16) | 0.0325 (15) | −0.0037 (13) | 0.0177 (13) | 0.0011 (13) |
Ni—C71 | 1.895 (2) | C64—H64 | 0.9300 |
Ni—P2 | 2.2094 (7) | C65—C66 | 1.382 (3) |
Ni—P1 | 2.2131 (7) | C65—H65 | 0.9300 |
Ni—Cl | 2.2377 (8) | C66—H66 | 0.9300 |
Ni1—Cl1 | 2.1566 (8) | C71—C76 | 1.375 (3) |
Ni1—P21 | 2.2128 (7) | C71—C72 | 1.387 (3) |
Ni1—P11 | 2.2152 (7) | C72—C73 | 1.388 (4) |
P1—C31 | 1.823 (2) | C72—H72 | 0.9300 |
P1—C11 | 1.825 (2) | C73—C74 | 1.355 (4) |
P1—C21 | 1.825 (2) | C73—H73 | 0.9300 |
P2—C41 | 1.816 (2) | C74—C75 | 1.358 (4) |
P2—C51 | 1.819 (2) | C74—H74 | 0.9300 |
P2—C61 | 1.831 (2) | C75—C76 | 1.390 (4) |
P11—C331 | 1.820 (2) | C75—H75 | 0.9300 |
P11—C221 | 1.823 (2) | C76—H76 | 0.9300 |
P11—C111 | 1.827 (2) | C111—C116 | 1.384 (4) |
P21—C661 | 1.818 (2) | C111—C112 | 1.385 (4) |
P21—C441 | 1.829 (2) | C112—C113 | 1.391 (4) |
P21—C551 | 1.832 (2) | C112—H112 | 0.9300 |
C11—C16 | 1.392 (3) | C113—C114 | 1.357 (5) |
C11—C12 | 1.405 (3) | C113—H113 | 0.9300 |
C12—C13 | 1.378 (3) | C114—C115 | 1.363 (5) |
C12—H12 | 0.9300 | C114—H114 | 0.9300 |
C13—C14 | 1.373 (4) | C115—C116 | 1.385 (4) |
C13—H13 | 0.9300 | C115—H115 | 0.9300 |
C14—C15 | 1.373 (4) | C116—H116 | 0.9300 |
C14—H14 | 0.9300 | C221—C222 | 1.388 (3) |
C15—C16 | 1.388 (3) | C221—C226 | 1.395 (3) |
C15—H15 | 0.9300 | C222—C223 | 1.380 (3) |
C16—H16 | 0.9300 | C222—H222 | 0.9300 |
C21—C22 | 1.387 (3) | C223—C224 | 1.372 (4) |
C21—C26 | 1.390 (3) | C223—H223 | 0.9300 |
C22—C23 | 1.388 (3) | C224—C225 | 1.379 (4) |
C22—H22 | 0.9300 | C224—H224 | 0.9300 |
C23—C24 | 1.368 (4) | C225—C226 | 1.380 (3) |
C23—H23 | 0.9300 | C225—H225 | 0.9300 |
C24—C25 | 1.382 (4) | C226—H226 | 0.9300 |
C24—H24 | 0.9300 | C331—C332 | 1.390 (4) |
C25—C26 | 1.380 (3) | C331—C336 | 1.404 (3) |
C25—H25 | 0.9300 | C332—C333 | 1.384 (4) |
C26—H26 | 0.9300 | C332—H332 | 0.9300 |
C31—C32 | 1.387 (3) | C333—C334 | 1.372 (5) |
C31—C36 | 1.387 (3) | C333—H333 | 0.9300 |
C32—C33 | 1.384 (3) | C334—C335 | 1.390 (5) |
C32—H32 | 0.9300 | C334—H334 | 0.9300 |
C33—C34 | 1.376 (4) | C335—C336 | 1.384 (4) |
C33—H33 | 0.9300 | C335—H335 | 0.9300 |
C34—C35 | 1.379 (4) | C336—H336 | 0.9300 |
C34—H34 | 0.9300 | C441—C442 | 1.379 (3) |
C35—C36 | 1.384 (3) | C441—C446 | 1.393 (3) |
C35—H35 | 0.9300 | C442—C443 | 1.388 (3) |
C36—H36 | 0.9300 | C442—H442 | 0.9300 |
C41—C42 | 1.385 (3) | C443—C444 | 1.376 (4) |
C41—C46 | 1.397 (3) | C443—H443 | 0.9300 |
C42—C43 | 1.388 (3) | C444—C445 | 1.369 (4) |
C42—H42 | 0.9300 | C444—H444 | 0.9300 |
C43—C44 | 1.374 (3) | C445—C446 | 1.385 (3) |
C43—H43 | 0.9300 | C445—H445 | 0.9300 |
C44—C45 | 1.376 (3) | C446—H446 | 0.9300 |
C44—H44 | 0.9300 | C551—C556 | 1.383 (3) |
C45—C46 | 1.380 (3) | C551—C552 | 1.394 (3) |
C45—H45 | 0.9300 | C552—C553 | 1.382 (3) |
C46—H46 | 0.9300 | C552—H552 | 0.9300 |
C51—C52 | 1.395 (3) | C553—C554 | 1.377 (4) |
C51—C56 | 1.398 (3) | C553—H553 | 0.9300 |
C52—C53 | 1.380 (3) | C554—C555 | 1.379 (3) |
C52—H52 | 0.9300 | C554—H554 | 0.9300 |
C53—C54 | 1.375 (3) | C555—C556 | 1.384 (3) |
C53—H53 | 0.9300 | C555—H555 | 0.9300 |
C54—C55 | 1.380 (3) | C556—H556 | 0.9300 |
C54—H54 | 0.9300 | C661—C662 | 1.388 (3) |
C55—C56 | 1.386 (3) | C661—C666 | 1.392 (3) |
C55—H55 | 0.9300 | C662—C663 | 1.385 (4) |
C56—H56 | 0.9300 | C662—H662 | 0.9300 |
C61—C62 | 1.388 (3) | C663—C664 | 1.378 (4) |
C61—C66 | 1.393 (3) | C663—H663 | 0.9300 |
C62—C63 | 1.384 (3) | C664—C665 | 1.375 (4) |
C62—H62 | 0.9300 | C664—H664 | 0.9300 |
C63—C64 | 1.380 (3) | C665—C666 | 1.378 (4) |
C63—H63 | 0.9300 | C665—H665 | 0.9300 |
C64—C65 | 1.365 (3) | C666—H666 | 0.9300 |
C71—Ni—P2 | 90.35 (7) | C63—C64—H64 | 120.3 |
C71—Ni—P1 | 90.50 (7) | C64—C65—C66 | 120.7 (2) |
P2—Ni—P1 | 177.00 (2) | C64—C65—H65 | 119.7 |
C71—Ni—Cl | 179.09 (7) | C66—C65—H65 | 119.7 |
P2—Ni—Cl | 89.03 (3) | C65—C66—C61 | 121.0 (2) |
P1—Ni—Cl | 90.14 (3) | C65—C66—H66 | 119.5 |
Cl1—Ni1—P21 | 121.87 (3) | C61—C66—H66 | 119.5 |
Cl1—Ni1—P11 | 123.48 (3) | C76—C71—C72 | 116.8 (2) |
P21—Ni1—P11 | 113.60 (3) | C76—C71—Ni | 121.05 (18) |
C31—P1—C11 | 102.02 (10) | C72—C71—Ni | 122.19 (18) |
C31—P1—C21 | 102.15 (10) | C71—C72—C73 | 121.2 (3) |
C11—P1—C21 | 108.06 (10) | C71—C72—H72 | 119.4 |
C31—P1—Ni | 119.54 (7) | C73—C72—H72 | 119.4 |
C11—P1—Ni | 115.59 (7) | C74—C73—C72 | 120.7 (3) |
C21—P1—Ni | 108.26 (7) | C74—C73—H73 | 119.7 |
C41—P2—C51 | 108.79 (10) | C72—C73—H73 | 119.7 |
C41—P2—C61 | 101.66 (10) | C73—C74—C75 | 119.2 (3) |
C51—P2—C61 | 102.54 (10) | C73—C74—H74 | 120.4 |
C41—P2—Ni | 109.83 (7) | C75—C74—H74 | 120.4 |
C51—P2—Ni | 113.22 (7) | C74—C75—C76 | 120.6 (3) |
C61—P2—Ni | 119.78 (7) | C74—C75—H75 | 119.7 |
C331—P11—C221 | 100.42 (10) | C76—C75—H75 | 119.7 |
C331—P11—C111 | 103.30 (11) | C71—C76—C75 | 121.5 (3) |
C221—P11—C111 | 105.07 (11) | C71—C76—H76 | 119.2 |
C331—P11—Ni1 | 124.84 (8) | C75—C76—H76 | 119.2 |
C221—P11—Ni1 | 112.42 (8) | C116—C111—C112 | 118.6 (2) |
C111—P11—Ni1 | 108.87 (7) | C116—C111—P11 | 118.2 (2) |
C661—P21—C441 | 103.48 (11) | C112—C111—P11 | 123.2 (2) |
C661—P21—C551 | 104.42 (11) | C111—C112—C113 | 120.3 (3) |
C441—P21—C551 | 103.74 (10) | C111—C112—H112 | 119.8 |
C661—P21—Ni1 | 120.68 (8) | C113—C112—H112 | 119.8 |
C441—P21—Ni1 | 114.21 (7) | C114—C113—C112 | 120.0 (3) |
C551—P21—Ni1 | 108.67 (7) | C114—C113—H113 | 120.0 |
C16—C11—C12 | 118.7 (2) | C112—C113—H113 | 120.0 |
C16—C11—P1 | 120.33 (16) | C113—C114—C115 | 120.4 (3) |
C12—C11—P1 | 120.99 (17) | C113—C114—H114 | 119.8 |
C13—C12—C11 | 120.1 (2) | C115—C114—H114 | 119.8 |
C13—C12—H12 | 120.0 | C114—C115—C116 | 120.3 (3) |
C11—C12—H12 | 120.0 | C114—C115—H115 | 119.8 |
C14—C13—C12 | 120.7 (2) | C116—C115—H115 | 119.8 |
C14—C13—H13 | 119.7 | C111—C116—C115 | 120.2 (3) |
C12—C13—H13 | 119.7 | C111—C116—H116 | 119.9 |
C15—C14—C13 | 119.9 (2) | C115—C116—H116 | 119.9 |
C15—C14—H14 | 120.0 | C222—C221—C226 | 118.7 (2) |
C13—C14—H14 | 120.0 | C222—C221—P11 | 119.32 (17) |
C14—C15—C16 | 120.5 (2) | C226—C221—P11 | 121.91 (18) |
C14—C15—H15 | 119.7 | C223—C222—C221 | 120.7 (2) |
C16—C15—H15 | 119.7 | C223—C222—H222 | 119.7 |
C15—C16—C11 | 120.1 (2) | C221—C222—H222 | 119.7 |
C15—C16—H16 | 120.0 | C224—C223—C222 | 120.1 (2) |
C11—C16—H16 | 120.0 | C224—C223—H223 | 119.9 |
C22—C21—C26 | 118.6 (2) | C222—C223—H223 | 119.9 |
C22—C21—P1 | 125.17 (18) | C223—C224—C225 | 120.1 (2) |
C26—C21—P1 | 116.18 (17) | C223—C224—H224 | 120.0 |
C21—C22—C23 | 119.7 (2) | C225—C224—H224 | 120.0 |
C21—C22—H22 | 120.1 | C224—C225—C226 | 120.2 (2) |
C23—C22—H22 | 120.1 | C224—C225—H225 | 119.9 |
C24—C23—C22 | 121.2 (2) | C226—C225—H225 | 119.9 |
C24—C23—H23 | 119.4 | C225—C226—C221 | 120.2 (2) |
C22—C23—H23 | 119.4 | C225—C226—H226 | 119.9 |
C23—C24—C25 | 119.7 (2) | C221—C226—H226 | 119.9 |
C23—C24—H24 | 120.2 | C332—C331—C336 | 118.8 (2) |
C25—C24—H24 | 120.2 | C332—C331—P11 | 123.9 (2) |
C26—C25—C24 | 119.6 (2) | C336—C331—P11 | 117.20 (19) |
C26—C25—H25 | 120.2 | C333—C332—C331 | 120.8 (3) |
C24—C25—H25 | 120.2 | C333—C332—H332 | 119.6 |
C25—C26—C21 | 121.3 (2) | C331—C332—H332 | 119.6 |
C25—C26—H26 | 119.4 | C334—C333—C332 | 119.8 (3) |
C21—C26—H26 | 119.4 | C334—C333—H333 | 120.1 |
C32—C31—C36 | 118.8 (2) | C332—C333—H333 | 120.1 |
C32—C31—P1 | 123.14 (18) | C333—C334—C335 | 120.8 (3) |
C36—C31—P1 | 118.03 (17) | C333—C334—H334 | 119.6 |
C33—C32—C31 | 120.3 (2) | C335—C334—H334 | 119.6 |
C33—C32—H32 | 119.9 | C336—C335—C334 | 119.5 (3) |
C31—C32—H32 | 119.9 | C336—C335—H335 | 120.2 |
C34—C33—C32 | 120.5 (2) | C334—C335—H335 | 120.2 |
C34—C33—H33 | 119.8 | C335—C336—C331 | 120.2 (3) |
C32—C33—H33 | 119.8 | C335—C336—H336 | 119.9 |
C33—C34—C35 | 119.8 (2) | C331—C336—H336 | 119.9 |
C33—C34—H34 | 120.1 | C442—C441—C446 | 119.0 (2) |
C35—C34—H34 | 120.1 | C442—C441—P21 | 123.06 (19) |
C34—C35—C36 | 119.9 (2) | C446—C441—P21 | 117.97 (18) |
C34—C35—H35 | 120.1 | C441—C442—C443 | 119.9 (2) |
C36—C35—H35 | 120.1 | C441—C442—H442 | 120.1 |
C35—C36—C31 | 120.8 (2) | C443—C442—H442 | 120.1 |
C35—C36—H36 | 119.6 | C444—C443—C442 | 120.7 (2) |
C31—C36—H36 | 119.6 | C444—C443—H443 | 119.7 |
C42—C41—C46 | 118.9 (2) | C442—C443—H443 | 119.7 |
C42—C41—P2 | 125.99 (17) | C445—C444—C443 | 119.9 (2) |
C46—C41—P2 | 114.87 (17) | C445—C444—H444 | 120.1 |
C41—C42—C43 | 119.6 (2) | C443—C444—H444 | 120.1 |
C41—C42—H42 | 120.2 | C444—C445—C446 | 119.9 (3) |
C43—C42—H42 | 120.2 | C444—C445—H445 | 120.0 |
C44—C43—C42 | 121.0 (2) | C446—C445—H445 | 120.0 |
C44—C43—H43 | 119.5 | C445—C446—C441 | 120.6 (2) |
C42—C43—H43 | 119.5 | C445—C446—H446 | 119.7 |
C43—C44—C45 | 119.8 (2) | C441—C446—H446 | 119.7 |
C43—C44—H44 | 120.1 | C556—C551—C552 | 118.4 (2) |
C45—C44—H44 | 120.1 | C556—C551—P21 | 116.97 (17) |
C44—C45—C46 | 119.8 (2) | C552—C551—P21 | 124.65 (18) |
C44—C45—H45 | 120.1 | C553—C552—C551 | 120.3 (2) |
C46—C45—H45 | 120.1 | C553—C552—H552 | 119.9 |
C45—C46—C41 | 120.8 (2) | C551—C552—H552 | 119.9 |
C45—C46—H46 | 119.6 | C554—C553—C552 | 120.8 (2) |
C41—C46—H46 | 119.6 | C554—C553—H553 | 119.6 |
C52—C51—C56 | 118.7 (2) | C552—C553—H553 | 119.6 |
C52—C51—P2 | 121.58 (17) | C553—C554—C555 | 119.5 (2) |
C56—C51—P2 | 119.64 (17) | C553—C554—H554 | 120.3 |
C53—C52—C51 | 120.4 (2) | C555—C554—H554 | 120.3 |
C53—C52—H52 | 119.8 | C554—C555—C556 | 120.0 (2) |
C51—C52—H52 | 119.8 | C554—C555—H555 | 120.0 |
C54—C53—C52 | 120.5 (2) | C556—C555—H555 | 120.0 |
C54—C53—H53 | 119.7 | C551—C556—C555 | 121.1 (2) |
C52—C53—H53 | 119.7 | C551—C556—H556 | 119.4 |
C53—C54—C55 | 120.0 (2) | C555—C556—H556 | 119.4 |
C53—C54—H54 | 120.0 | C662—C661—C666 | 118.8 (2) |
C55—C54—H54 | 120.0 | C662—C661—P21 | 118.34 (18) |
C54—C55—C56 | 120.2 (2) | C666—C661—P21 | 122.8 (2) |
C54—C55—H55 | 119.9 | C663—C662—C661 | 120.5 (2) |
C56—C55—H55 | 119.9 | C663—C662—H662 | 119.8 |
C55—C56—C51 | 120.2 (2) | C661—C662—H662 | 119.8 |
C55—C56—H56 | 119.9 | C664—C663—C662 | 120.2 (3) |
C51—C56—H56 | 119.9 | C664—C663—H663 | 119.9 |
C62—C61—C66 | 117.6 (2) | C662—C663—H663 | 119.9 |
C62—C61—P2 | 118.62 (17) | C665—C664—C663 | 119.4 (3) |
C66—C61—P2 | 123.51 (17) | C665—C664—H664 | 120.3 |
C63—C62—C61 | 121.1 (2) | C663—C664—H664 | 120.3 |
C63—C62—H62 | 119.5 | C664—C665—C666 | 121.1 (3) |
C61—C62—H62 | 119.5 | C664—C665—H665 | 119.5 |
C64—C63—C62 | 120.3 (2) | C666—C665—H665 | 119.5 |
C64—C63—H63 | 119.9 | C665—C666—C661 | 120.0 (3) |
C62—C63—H63 | 119.9 | C665—C666—H666 | 120.0 |
C65—C64—C63 | 119.4 (2) | C661—C666—H666 | 120.0 |
C65—C64—H64 | 120.3 | ||
C71—Ni—P1—C31 | −4.63 (11) | C61—C62—C63—C64 | 0.1 (4) |
Cl—Ni—P1—C31 | 176.01 (8) | C62—C63—C64—C65 | −0.5 (4) |
C71—Ni—P1—C11 | 117.83 (11) | C63—C64—C65—C66 | 0.1 (4) |
Cl—Ni—P1—C11 | −61.53 (8) | C64—C65—C66—C61 | 0.6 (4) |
C71—Ni—P1—C21 | −120.84 (10) | C62—C61—C66—C65 | −0.9 (3) |
Cl—Ni—P1—C21 | 59.80 (8) | P2—C61—C66—C65 | 172.75 (19) |
C71—Ni—P2—C41 | −122.09 (11) | P2—Ni—C71—C76 | 84.6 (2) |
Cl—Ni—P2—C41 | 57.24 (8) | P1—Ni—C71—C76 | −98.3 (2) |
C71—Ni—P2—C51 | 116.09 (10) | P2—Ni—C71—C72 | −95.7 (2) |
Cl—Ni—P2—C51 | −64.59 (8) | P1—Ni—C71—C72 | 81.4 (2) |
C71—Ni—P2—C61 | −5.10 (11) | C76—C71—C72—C73 | −1.2 (4) |
Cl—Ni—P2—C61 | 174.23 (8) | Ni—C71—C72—C73 | 179.1 (2) |
Cl1—Ni1—P11—C331 | 163.57 (10) | C71—C72—C73—C74 | 2.2 (4) |
P21—Ni1—P11—C331 | −28.00 (10) | C72—C73—C74—C75 | −1.6 (5) |
Cl1—Ni1—P11—C221 | −74.72 (8) | C73—C74—C75—C76 | 0.0 (5) |
P21—Ni1—P11—C221 | 93.72 (8) | C72—C71—C76—C75 | −0.3 (4) |
Cl1—Ni1—P11—C111 | 41.28 (10) | Ni—C71—C76—C75 | 179.4 (2) |
P21—Ni1—P11—C111 | −150.29 (10) | C74—C75—C76—C71 | 0.9 (5) |
Cl1—Ni1—P21—C661 | −155.93 (9) | C331—P11—C111—C116 | −77.3 (2) |
P11—Ni1—P21—C661 | 35.43 (9) | C221—P11—C111—C116 | 177.8 (2) |
Cl1—Ni1—P21—C441 | −31.60 (9) | Ni1—P11—C111—C116 | 57.2 (2) |
P11—Ni1—P21—C441 | 159.75 (9) | C331—P11—C111—C112 | 104.2 (2) |
Cl1—Ni1—P21—C551 | 83.66 (8) | C221—P11—C111—C112 | −0.7 (2) |
P11—Ni1—P21—C551 | −84.98 (8) | Ni1—P11—C111—C112 | −121.3 (2) |
C31—P1—C11—C16 | 137.71 (19) | C116—C111—C112—C113 | 2.1 (4) |
C21—P1—C11—C16 | −115.08 (19) | P11—C111—C112—C113 | −179.5 (2) |
Ni—P1—C11—C16 | 6.4 (2) | C111—C112—C113—C114 | −0.5 (5) |
C31—P1—C11—C12 | −40.5 (2) | C112—C113—C114—C115 | −0.8 (5) |
C21—P1—C11—C12 | 66.7 (2) | C113—C114—C115—C116 | 0.5 (6) |
Ni—P1—C11—C12 | −171.90 (16) | C112—C111—C116—C115 | −2.4 (4) |
C16—C11—C12—C13 | 1.9 (3) | P11—C111—C116—C115 | 179.1 (3) |
P1—C11—C12—C13 | −179.79 (18) | C114—C115—C116—C111 | 1.1 (5) |
C11—C12—C13—C14 | −0.6 (4) | C331—P11—C221—C222 | 150.55 (18) |
C12—C13—C14—C15 | −0.8 (4) | C111—P11—C221—C222 | −102.48 (19) |
C13—C14—C15—C16 | 0.9 (4) | Ni1—P11—C221—C222 | 15.8 (2) |
C14—C15—C16—C11 | 0.5 (4) | C331—P11—C221—C226 | −26.3 (2) |
C12—C11—C16—C15 | −1.9 (3) | C111—P11—C221—C226 | 80.7 (2) |
P1—C11—C16—C15 | 179.84 (18) | Ni1—P11—C221—C226 | −161.03 (17) |
C31—P1—C21—C22 | 87.6 (2) | C226—C221—C222—C223 | −0.6 (3) |
C11—P1—C21—C22 | −19.5 (2) | P11—C221—C222—C223 | −177.47 (18) |
Ni—P1—C21—C22 | −145.42 (18) | C221—C222—C223—C224 | 0.8 (4) |
C31—P1—C21—C26 | −89.00 (19) | C222—C223—C224—C225 | −0.7 (4) |
C11—P1—C21—C26 | 163.89 (18) | C223—C224—C225—C226 | 0.4 (4) |
Ni—P1—C21—C26 | 38.0 (2) | C224—C225—C226—C221 | −0.1 (4) |
C26—C21—C22—C23 | −0.4 (3) | C222—C221—C226—C225 | 0.2 (3) |
P1—C21—C22—C23 | −176.90 (18) | P11—C221—C226—C225 | 177.05 (19) |
C21—C22—C23—C24 | 1.4 (4) | C221—P11—C331—C332 | 108.5 (2) |
C22—C23—C24—C25 | −0.8 (4) | C111—P11—C331—C332 | 0.1 (2) |
C23—C24—C25—C26 | −0.7 (4) | Ni1—P11—C331—C332 | −124.61 (18) |
C24—C25—C26—C21 | 1.7 (4) | C221—P11—C331—C336 | −68.39 (19) |
C22—C21—C26—C25 | −1.1 (4) | C111—P11—C331—C336 | −176.77 (18) |
P1—C21—C26—C25 | 175.7 (2) | Ni1—P11—C331—C336 | 58.5 (2) |
C11—P1—C31—C32 | 126.00 (19) | C336—C331—C332—C333 | 1.3 (4) |
C21—P1—C31—C32 | 14.3 (2) | P11—C331—C332—C333 | −175.52 (19) |
Ni—P1—C31—C32 | −105.08 (18) | C331—C332—C333—C334 | −0.4 (4) |
C11—P1—C31—C36 | −56.5 (2) | C332—C333—C334—C335 | −0.9 (4) |
C21—P1—C31—C36 | −168.20 (18) | C333—C334—C335—C336 | 1.4 (4) |
Ni—P1—C31—C36 | 72.44 (19) | C334—C335—C336—C331 | −0.5 (4) |
C36—C31—C32—C33 | 0.1 (3) | C332—C331—C336—C335 | −0.8 (3) |
P1—C31—C32—C33 | 177.62 (18) | P11—C331—C336—C335 | 176.23 (19) |
C31—C32—C33—C34 | 0.0 (4) | C661—P21—C441—C442 | 11.8 (2) |
C32—C33—C34—C35 | −0.8 (4) | C551—P21—C441—C442 | 120.6 (2) |
C33—C34—C35—C36 | 1.5 (4) | Ni1—P21—C441—C442 | −121.24 (18) |
C34—C35—C36—C31 | −1.4 (4) | C661—P21—C441—C446 | −169.34 (18) |
C32—C31—C36—C35 | 0.6 (3) | C551—P21—C441—C446 | −60.5 (2) |
P1—C31—C36—C35 | −177.01 (19) | Ni1—P21—C441—C446 | 57.6 (2) |
C51—P2—C41—C42 | −12.1 (2) | C446—C441—C442—C443 | 1.8 (4) |
C61—P2—C41—C42 | 95.6 (2) | P21—C441—C442—C443 | −179.38 (19) |
Ni—P2—C41—C42 | −136.57 (19) | C441—C442—C443—C444 | 0.6 (4) |
C51—P2—C41—C46 | 173.44 (17) | C442—C443—C444—C445 | −1.8 (4) |
C61—P2—C41—C46 | −78.83 (19) | C443—C444—C445—C446 | 0.6 (4) |
Ni—P2—C41—C46 | 49.01 (19) | C444—C445—C446—C441 | 1.8 (4) |
C46—C41—C42—C43 | 1.5 (4) | C442—C441—C446—C445 | −3.0 (4) |
P2—C41—C42—C43 | −172.77 (18) | P21—C441—C446—C445 | 178.11 (19) |
C41—C42—C43—C44 | 1.3 (4) | C661—P21—C551—C556 | −91.14 (19) |
C42—C43—C44—C45 | −2.9 (4) | C441—P21—C551—C556 | 160.77 (18) |
C43—C44—C45—C46 | 1.7 (4) | Ni1—P21—C551—C556 | 38.88 (19) |
C44—C45—C46—C41 | 1.1 (4) | C661—P21—C551—C552 | 90.2 (2) |
C42—C41—C46—C45 | −2.7 (4) | C441—P21—C551—C552 | −17.8 (2) |
P2—C41—C46—C45 | 172.19 (19) | Ni1—P21—C551—C552 | −139.73 (19) |
C41—P2—C51—C52 | 63.8 (2) | C556—C551—C552—C553 | 0.3 (4) |
C61—P2—C51—C52 | −43.3 (2) | P21—C551—C552—C553 | 178.9 (2) |
Ni—P2—C51—C52 | −173.81 (16) | C551—C552—C553—C554 | −0.8 (4) |
C41—P2—C51—C56 | −119.61 (19) | C552—C553—C554—C555 | 0.7 (4) |
C61—P2—C51—C56 | 133.27 (19) | C553—C554—C555—C556 | −0.2 (4) |
Ni—P2—C51—C56 | 2.8 (2) | C552—C551—C556—C555 | 0.2 (3) |
C56—C51—C52—C53 | 1.0 (3) | P21—C551—C556—C555 | −178.48 (18) |
P2—C51—C52—C53 | 177.58 (18) | C554—C555—C556—C551 | −0.3 (4) |
C51—C52—C53—C54 | −1.0 (4) | C441—P21—C661—C662 | −94.50 (19) |
C52—C53—C54—C55 | 0.3 (4) | C551—P21—C661—C662 | 157.21 (18) |
C53—C54—C55—C56 | 0.4 (4) | Ni1—P21—C661—C662 | 34.7 (2) |
C54—C55—C56—C51 | −0.4 (4) | C441—P21—C661—C666 | 86.8 (2) |
C52—C51—C56—C55 | −0.3 (4) | C551—P21—C661—C666 | −21.5 (2) |
P2—C51—C56—C55 | −176.9 (2) | Ni1—P21—C661—C666 | −143.97 (18) |
C41—P2—C61—C62 | −166.85 (18) | C666—C661—C662—C663 | 0.3 (4) |
C51—P2—C61—C62 | −54.3 (2) | P21—C661—C662—C663 | −178.43 (19) |
Ni—P2—C61—C62 | 72.01 (19) | C661—C662—C663—C664 | −0.8 (4) |
C41—P2—C61—C66 | 19.5 (2) | C662—C663—C664—C665 | 0.7 (4) |
C51—P2—C61—C66 | 132.0 (2) | C663—C664—C665—C666 | −0.1 (5) |
Ni—P2—C61—C66 | −101.63 (19) | C664—C665—C666—C661 | −0.4 (4) |
C66—C61—C62—C63 | 0.6 (4) | C662—C661—C666—C665 | 0.3 (4) |
P2—C61—C62—C63 | −173.43 (19) | P21—C661—C666—C665 | 179.0 (2) |
Experimental details
(I) | (II) | (2) | |
Crystal data | |||
Chemical formula | [Ni(C6H5)Cl(C18H15P)2] | [Ni(C6H5)Cl(C18H15P)2] | [Ni(C6H5)Cl(C18H15P)2]·[NiCl(C18H15P)2] |
Mr | 695.80 | 695.80 | 1314.50 |
Crystal system, space group | Monoclinic, P21/c | Orthorhombic, Pbca | Monoclinic, P21/c |
Temperature (K) | 150 | 150 | 150 |
a, b, c (Å) | 15.601 (1), 11.8690 (9), 19.857 (2) | 11.7990 (5), 23.368 (2), 25.1300 (11) | 24.183 (6), 12.257 (3), 23.712 (5) |
α, β, γ (°) | 90, 112.139 (4), 90 | 90, 90, 90 | 90, 113.781 (8), 90 |
V (Å3) | 3405.8 (5) | 6928.8 (7) | 6432 (3) |
Z | 4 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.77 | 0.76 | 0.81 |
Crystal size (mm) | 0.17 × 0.10 × 0.06 | 0.22 × 0.14 × 0.08 | 0.23 × 0.17 × 0.07 |
Data collection | |||
Diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) | Multi-scan (SADABS; Sheldrick, 2003) | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.880, 0.955 | 0.851, 0.942 | 0.835, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 77866, 6506, 5091 | 35219, 6075, 3874 | 109681, 13903, 10162 |
Rint | 0.069 | 0.094 | 0.078 |
(sin θ/λ)max (Å−1) | 0.613 | 0.595 | 0.637 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.073, 1.04 | 0.042, 0.088, 0.97 | 0.038, 0.093, 1.04 |
No. of reflections | 6506 | 6075 | 13903 |
No. of parameters | 415 | 415 | 775 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.30 | 0.39, −0.28 | 0.43, −0.50 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999).
Form I | Form II | |
Ni—Cl | 2.2195 (6) | 2.2369 (9) |
Ni—C71 | 1.8824 (19) | 1.893 (3) |
Ni—P1 | 2.2197 (6) | 2.2149 (8) |
Ni—P2 | 2.2106 (6) | 2.2099 (8) |
Cl—Ni—P1 | 92.39 (2) | 88.71 (3) |
Cl—Ni—P2 | 88.25 (2) | 89.55 (3) |
C71—Ni—P1 | 88.59 (6) | 91.41 (9) |
C71—Ni—P2 | 91.98 (6) | 90.33 (9) |
Cl—Ni—P1—C11 | -47.09 (8) | -65.73 (11) |
Cl—Ni—P1—C21 | 72.23 (8) | 55.42 (10) |
Cl—Ni—P1—C31 | -165.63 (9) | 173.50 (9) |
Cl—Ni—P2—C41 | 63.46 (7) | 53.51 (12) |
Cl—Ni—P2—C51 | -55.18 (9) | -64.20 (11) |
Cl—Ni—P2—C61 | -176.84 (10) | 171.78 (10) |
C71—Ni—P1—C11 | 139.55 (10) | 114.24 (13) |
C71—Ni—P1—C21 | -101.13 (10) | -124.62 (12) |
C71—Ni—P1—C31 | 21.01 (11) | -6.53 (12) |
C71—Ni—P2—C41 | -123.24 (10) | -126.46 (14) |
C71—Ni—P2—C51 | 118.12 (11) | 115.83 (13) |
C71—Ni—P2—C61 | -3.55 (12) | -8.19 (12) |
P2—Ni—P1—C11 | 46.26 (17) | -21.89 (80) |
P2—Ni—P1—C21 | 165.58 (14) | 99.25 (78) |
P2—Ni—P1—C31 | -72.28 (16) | -142.67 (72) |
P1—Ni—P2—C41 | -30.26 (17) | 9.69 (80) |
P1—Ni—P2—C51 | -148.90 (15) | -108.01 (78) |
P1—Ni—P2—C61 | 89.44 (16) | 127.97 (77) |
D—H···A | H···A | D···A | D—H···A | |
Form I of (1) | C63—H63···Cg2i | 2.94 | 3.788 (3) | 151 |
Form II of (1) | C54—H54···Clii | 2.83 | 3.499 (3) | 130 |
Cocrystal (2) | C35—H35···Cg4iii | 2.89 | 3.763 (3) | 158 |
C63—H63···Cg1iv | 2.76 | 3.607 (3) | 152 | |
C114—H114···Cg5v | 2.96 | 3.794 (4) | 150 | |
C223—H223···Cg1 | 2.80 | 3.629 (3) | 149 | |
C554—H554···Cg3 | 2.80 | 3.673 (3) | 156 |
Symmetry codes: (i) -x, 1-y, -z; (ii) 1/2-x, 1/2-y, 1-z; (iii) -x, -1/2+y, 1/2-z; (iv) x, -1/2-y, 1/2+z; (v) -x, 1/2+y, 1/2-z. Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the rings C11–C16, C21–C26, C41–C46, C51–C56 and C441–C446, respectively. |
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In the last decade, a new class of neutral nickel catalysts based on salicylaldimine or anilinotropone ligands, which are highly active in alkene polymerization and which do not need to be activated by the expensive methylaluminoxane (MAO) cocatalyst, has attracted increasing interest in academia and industry (Wang et al., 1998; Younkin et al., 2000; Hicks & Brookhart, 2001). Due to their reduced oxophilicity and better tolerance to functional groups, these catalysts are able to copolymerize alkenes with polar comonomers showing good activities. Such polymerizations can be run in polar media, even in aqueous solutions or emulsions (Bauers & Mecking, 2001; Mecking et al., 2002; Held et al., 2000; Gottker-Schenetmann et al., 2006; Soula et al., 2001; Tomov et al., 2000). In addition, they are capable of forming polymers with controllable topologies by virtue of the `chain walking' mechanism (Johnson et al., 1995).
A key intermediate and organometallic precursor for the synthesis of this type of catalyst is the title compound, trans-[NiCl(Ph)(PPh3)2], (1). Compound (1) and its analogues trans-[NiX(R)(PR'3)2] (X = Cl or Br; R = C6H5, 2-ClC6H4, C6F5, CF═ CF2, etc.; R' = Ph, Me or Et) have been prepared mainly by two methods, namely the reaction of compounds of the type [NiX2(PR3)2] with aryl Grignard reagents or alkali metal compounds (Chatt & Shaw, 1960; Rausch & Tibbetts, 1970; Miller et al., 1968), and the oxidative addition of aryl halides to nickel(0) complexes (Dahey, 1970; Hidai et al., 1971). Recently, Zeller et al. (2003) reported a one-pot synthesis of complex (1) from readily available and inexpensive reagents, with an apparently improved overall yield, and they reported its structure at 293 K [Cambridge Structural Database (Allen, 2002) refcode VALCIV].
In this context, we have prepared compound (1) employing Zeller's method but we have found that, besides the orange monoclinic crystals of (1) (form I) already described (Zeller et al., 2003), bluish–green crystals of its 1:1 cocrystal with the NiI complex [NiCl(PPh3)2], (2), were also formed. This by-product very likely originated from the elimination of a phenyl radical from complex (1). In fact, while repeating Zeller's procedure several times, we have consistently observed the presence of significant amounts of the paramagnetic NiI complex (2). This observation agrees with the characterization data presented in the original paper, namely the microanalysis of (1), which reported an experimental value of the carbon content 0.66% lower than that expected [corresponding to a fraction of (2) > 10 mol%], and with the corresponding 1H NMR spectrum, the resonances of which were described as broad, not presenting the expected multiplicities (Zeller et al., 2003). We have reacted complex (1), which was synthesized by the latter method, with iminopyrrolyl sodium salts (Bellabarba et al., 2003; Carabineiro et al., 2007, 2008) in order to obtain nickel iminopyrrolyl complexes of the type [Ni{κ2N,N'-NC4H3C(R)═N-2,6- iPr2C6H3}2(Ph)(PPh3)] (R = H, Me) (Bellabarba et al., 2003). After isolating the desired compound, we recovered from the mother liquor a new orthorhombic polymorph of unreacted (1) (form II). Here, we report the structures of complex (1) in the two polymorphic forms I and II, and in a 1:1 cocrystal of complex (1) with complex (2).
The molecular and crystal structure of (1) in form I is the same as in VALCIV (the only difference being the data collection temperature: VALCIV at 293 K and form I at 150 K), whereas the molecular and crystal structures of (1) in form II are noticeably different from those in form I. Complex (1) crystallizes in the monoclinic space group P21/c (form I) and in the orthorhombic space group Pbca (form II). Table 1 summarizes the most relevant bond distances, bond angles and torsion angles of the two polymorphic forms. The molecules of (1) in both forms I and II are structurally similar. The NiII atom is coordinated by two PPh3 groups in a trans fashion, by a Cl- atom and by a phenyl group, in total showing a square-planar geometry, as displayed in Fig. 1. A more pronounced distortion around the metal centre, as given by the dihedral angle between the planes formed by atoms P1/Ni/Cl and P2/Ni/C71, can be observed in form I [12.09 (4)°], whereas in form II the molecules show a virtually undistorted square-planar geometry [1.67 (3)°] which deviates very slightly from an optimum value of 0°. The corresponding dihedral angle observed for complex (1) in the cocrystal is 2.96 (6)°. Fig. 2 compares schematically the differences in the molecules of (1) in forms I and II. It can be seen that forms I and II lead to different conformers. In molecule (1), the phenyl groups are subjected to rotations about the single bonds Pn—Cm1 (n = 1 or 2, m = 1–6) and Ni—C71, ultimately leading to diverse molecular conformations (see Table 1).
Molecular conformations can differ by rotations about single bonds (intramolecular torsions), which commonly involve energies around 1–3 kcal mol-1 (1 kcal mol-1 = 4.184 kJ mol-1) (Nangia, 2008). The packing of molecules in crystals depends upon diverse intermolecular interactions, including hydrogen-bonding and van der Waals interactions. Generally, the energy of intramolecular torsions and intermolecular interactions lies in the same range of magnitude, meaning that they can compensate each other. In the molecular packing of complex (1), due to the absence of strong intermolecular interactions (e.g. hydrogen bonds), the torsional geometries produced in forms I and II are mainly compensated by diverse weak intermolecular interactions. Form I only has weak C—H···π interactions, while polymorph II presents stronger C—H···Cl interactions which are responsible for the different conformation. Table 2 summarizes these weak intermolecular interactions as well as those present in the cocrystal.
Complexes of nickel(I) are far less known than those of nickel(0) and nickel(II). Compounds of the type [NiX(PR3)2] have been reported to be either dimeric or oligomeric, since these 15-electron species could possibly associate due to their unsaturated nature (Cundy & Nöth, 1971; Lappert & Speier, 1974; Aresta et al., 1975). Recently, the monomeric complex (2) and its tetrahydrofuran (THF) solvate have been prepared as side-products from the decomposition of (1) or [NiCl(PPh3)3] and crystallographically characterized (Ellis & Spek, 2000; Norman et al., 2002). Consistent with the findings of those workers, complex (2) is monomeric in the present 1:1 cocrystal with complex (1) (Fig. 3). The Ni centre is coordinated by two PPh3 groups, with Ni—P distances of 2.2152 (9) and 2.2129 (10) Å, and by a Cl- atom, with an Ni—Cl distance of 2.1566 (10) Å, and it lies 0.1302 (4) Å out of the P···P···Cl plane, thus showing a distorted trigonal–planar geometry. The P—Ni—P angle of 113.59 (3)° is significantly smaller than the corresponding Cl—Ni—P angles of 121.87 (3) and 123.48 (3)°, their sum [358.94 (3)°] being slightly lower than the expected 360°. These angular differences are thought to be caused by a first-order Jahn–Teller effect (Norman et al., 2002). All the Ni—P and Ni—Cl bonds in the present cocrystal are slightly shorter than those reported for the pure crystal (Ellis & Spek, 2000) [2.2152 (9) in the cocrystal versus 2.2536 (5) Å in the pure crystal, 2.2129 (10) versus 2.2393 (5) Å and 2.1566 (10) versus 2.1666 (6) Å] [NB Cocrystal values in the CIF are 2.2152</span>(7), 2.2128 (7) and 2.1566 (8) - please clarify], while the P—Ni—P and Cl—Ni—P angles are very close [113.59 (3) [113.60 (3) in CIF]versus 114.94 (2)°, 121.87 (3) versus 121.12 (2)° and 123.48 (3) versus 123.56 (2)°]. Comparisons of compound (2) in the cocrystal with that of the THF solvate (Norman et al., 2002) also show some differences. All the Ni—P and Ni—Cl bond distances of (2) in the cocrystal are slightly longer than those in the THF solvate [2.2152 (9) versus 2.2091 (6) Å, 2.2129 (10) versus 2.2012 (6) Å and 2.1566 (10) versus 2.1481 (6) Å] [NB Cocrystal values in the CIF are 2.2152 (7), 2.2128 (7) and 2.1566<span style=" font-weight:600;">(8) - please clarify]. One of the Cl—Ni—P angles [121.87 (3) versus 121.33 (2)°] is similar, while the other is slightly more different [123.48 (3) versus 126.98 (2)°]. Additionally, the P—Ni—P angle of (2) in the cocrystal [113.59 (3)°] [113.60 (3) in CIF] is larger than that in the THF solvate [111.52 (2)°].
In the cocrystal concomitantly crystallized with form I, the main intermolecular interactions are of the C—H···π type and are present between molecules of complex (1) (C35—H35···Cg5 and C63—H63···Cg1), between molecules of complex (2) (C114—H114···Cg11) and between molecules of (1) and (2) (C223—H223···Cg1 and C554—H554···Cg4) (Table 2). Fig. 4 shows the overall crystal packing viewed along the c axis, where alternating layers of complex (1) can be seen packed in an almost completely eclipsed fashion, and complex (2) packed in a staggered manner. As described above, both the molecular and crystal structures of forms I and II of complex (1) and of the cocrystal of molecules (1) and (2) are determined by an energetic interplay between intramolecular torsions and weak intermolecular interactions (e.g. C—H···π and C—H···Cl).