Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201509X/wn6116sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680201509X/wn6116IIsup2.hkl |
CCDC reference: 197455
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.005 Å
- R factor = 0.030
- wR factor = 0.031
- Data-to-parameter ratio = 10.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
DENSD_01 Alert C The ratio of the submitted crystal density and that calculated from the formula is outside the range 0.99 <> 1.01 Crystal density given = 1.280 Calculated crystal density = 1.335 PLAT_732 Alert C Angle Calc 119.7(4), Rep 119.69(19) .... 2.11 s.u-Ratio C4 -C3 -H31 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 120.3(4), Rep 120.31(19) .... 2.11 s.u-Ratio C3 -C4 -H41 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 120.8(4), Rep 120.77(19) .... 2.11 s.u-Ratio C5 -C4 -H41 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 119.9(4), Rep 119.90(19) .... 2.11 s.u-Ratio C4 -C5 -H51 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.1(3), Rep 109.07(9) .... 3.33 s.u-Ratio P1 -C7 -H71 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.3(3), Rep 109.29(9) .... 3.33 s.u-Ratio P1 -C7 -H72 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.4(3), Rep 109.39(14) .... 2.14 s.u-Ratio C8 -C7 -H72 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 108.7(3), Rep 108.75(9) .... 3.33 s.u-Ratio P2 -C8 -H81 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.1(3), Rep 109.10(9) .... 3.33 s.u-Ratio P2 -C8 -H82 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.5(4), Rep 109.45(18) .... 2.22 s.u-Ratio C12 -C11 -H112 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.9(4), Rep 109.94(17) .... 2.35 s.u-Ratio C11 -C12 -H121 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.8(4), Rep 109.81(18) .... 2.22 s.u-Ratio C13 -C12 -H121 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.5(4), Rep 109.45(18) .... 2.22 s.u-Ratio C14 -C13 -H132 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.4(4), Rep 109.38(16) .... 2.50 s.u-Ratio C9 -C14 -H141 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 106.0(2), Rep 106.04(9) .... 2.22 s.u-Ratio P1 -C15 -H151 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.8(4), Rep 109.80(19) .... 2.11 s.u-Ratio C16 -C17 -H171 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.7(4), Rep 109.76(18) .... 2.22 s.u-Ratio C17 -C18 -H182 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.4(4), Rep 109.28(18) .... 2.22 s.u-Ratio C19 -C18 -H182 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.4(4), Rep 109.41(18) .... 2.22 s.u-Ratio C18 -C19 -H191 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.1(4), Rep 109.14(17) .... 2.35 s.u-Ratio C20 -C19 -H191 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 108.4(4), Rep 108.40(19) .... 2.11 s.u-Ratio C20 -C19 -H192 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 107.2(2), Rep 107.18(8) .... 2.50 s.u-Ratio P2 -C21 -H211 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 108.6(4), Rep 108.65(17) .... 2.35 s.u-Ratio C22 -C23 -H231 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 108.7(4), Rep 108.72(16) .... 2.50 s.u-Ratio C26 -C25 -H251 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.5(4), Rep 109.43(17) .... 2.35 s.u-Ratio C24 -C25 -H252 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.0(4), Rep 109.08(16) .... 2.50 s.u-Ratio C25 -C26 -H262 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 106.5(2), Rep 106.56(9) .... 2.22 s.u-Ratio P2 -C27 -H271 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 108.8(4), Rep 108.84(18) .... 2.22 s.u-Ratio C29 -C28 -H281 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.6(4), Rep 109.70(18) .... 2.22 s.u-Ratio C28 -C29 -H291 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.2(4), Rep 109.26(19) .... 2.11 s.u-Ratio C30 -C29 -H291 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 108.6(4), Rep 108.63(18) .... 2.22 s.u-Ratio C28 -C29 -H292 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.7(4), Rep 109.70(18) .... 2.22 s.u-Ratio C29 -C30 -H302 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 109.7(4), Rep 109.68(18) .... 2.22 s.u-Ratio C30 -C31 -H311 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 110.1(4), Rep 110.04(17) .... 2.35 s.u-Ratio C32 -C31 -H311 1.555 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(5), Rep 1.00000 .... Missing s.u. C2 -H21 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C3 -H31 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C4 -H41 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C5 -H51 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C6 -H61 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C7 -H71 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C7 -H72 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(4), Rep 1.00000 .... Missing s.u. C8 -H81 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C8 -H82 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(4), Rep 1.00000 .... Missing s.u. C9 -H91 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C10 -H101 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C10 -H102 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C11 -H111 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(4), Rep 1.00000 .... Missing s.u. C11 -H112 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C12 -H121 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C12 -H122 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C13 -H131 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C13 -H132 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C14 -H141 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(6), Rep 1.00000 .... Missing s.u. C14 -H142 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(4), Rep 1.00000 .... Missing s.u. C15 -H151 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C16 -H161 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C16 -H162 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C17 -H171 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C17 -H172 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C18 -H181 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C18 -H182 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(5), Rep 1.00000 .... Missing s.u. C19 -H191 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C19 -H192 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(4), Rep 1.00000 .... Missing s.u. C20 -H201 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(4), Rep 1.00000 .... Missing s.u. C20 -H202 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C21 -H211 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C22 -H221 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C22 -H222 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C23 -H231 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(5), Rep 1.00000 .... Missing s.u. C23 -H232 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C24 -H241 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C24 -H242 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C25 -H251 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C25 -H252 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C26 -H261 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C26 -H262 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(4), Rep 1.00000 .... Missing s.u. C27 -H271 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C28 -H281 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C28 -H282 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C29 -H291 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(6), Rep 1.00000 .... Missing s.u. C29 -H292 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C30 -H301 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C30 -H302 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(5), Rep 1.00000 .... Missing s.u. C31 -H311 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(6), Rep 1.00000 .... Missing s.u. C31 -H312 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(4), Rep 1.00000 .... Missing s.u. C32 -H321 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C32 -H322 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(7), Rep 1.00000 .... Missing s.u. C34 -H341 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(7), Rep 1.00000 .... Missing s.u. C35 -H351 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(6), Rep 1.00000 .... Missing s.u. C36 -H361 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(7), Rep 1.00000 .... Missing s.u. C37 -H371 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(7), Rep 1.00000 .... Missing s.u. C38 -H381 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H71 -C7 -H72 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.47 .... Missing s.u. H81 -C8 -H82 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H101 -C10 -H102 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H111 -C11 -H112 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(5), Rep 109.47 .... Missing s.u. H121 -C12 -H122 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H131 -C13 -H132 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(5), Rep 109.47 .... Missing s.u. H141 -C14 -H142 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H161 -C16 -H162 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H171 -C17 -H172 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(5), Rep 109.47 .... Missing s.u. H181 -C18 -H182 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(5), Rep 109.47 .... Missing s.u. H191 -C19 -H192 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H201 -C20 -H202 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H221 -C22 -H222 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H231 -C23 -H232 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(4), Rep 109.47 .... Missing s.u. H241 -C24 -H242 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H251 -C25 -H252 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H261 -C26 -H262 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H281 -C28 -H282 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H291 -C29 -H292 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(5), Rep 109.47 .... Missing s.u. H301 -C30 -H302 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(5), Rep 109.47 .... Missing s.u. H311 -C31 -H312 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(4), Rep 109.47 .... Missing s.u. H321 -C32 -H322 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
115 Alert Level C = Please check
A solution of the boronic ester complex (I) (50 mg) was prepared with chlorobenzene (3 ml) and pentane was diffused into it at room temperature. Crystallization was very slow, but after 72 h, orange crystals of the title compound formed. Attempted recrystallizations of the title compound from CH2Cl2/hexane or THF/hexane had similar outcomes. The NMR data are analogous to those of the iodo analogue [NiI(Ph)(dcpe)] (Bennett et al., 1985). 1H NMR (300 MHz, CD2Cl2, p.p.m.): δ 1.15–1.95 (m, 42H, dcpe), 2.04–2.18 (m, 4H, dcpe), 2.34–2.46 (m, 2H, dcpe), 6.77 (t, 1H, J = 7.2 Hz, p-Ph), 6.95 (t, 2H, J = 7.2 Hz, m-Ph), 7.45 (br t, 2H, J = 6.0 Hz, o-Ph); 13C NMR (75.4 MHz, CD2Cl2, p.p.m.): δ 19.24 (dd, J = 19.9, 11.7 Hz, PCH2), 24.90 (t, J = 23.1 Hz, PCH2), 26.17–30.68 (m, CH2), 34.50 (d, J = 18.7 Hz, PCH), 34.75 (br d, J = 25.3 Hz, PCH), 121.88 (s, p-CH), 126.04 (d, J = 6.0 Hz, o-CH), 137.68 (s, m-CH), 159.10 (dd, J = 85.7, 37.5, Ni—C); 31P{1H} NMR (80.96 MHz, CD2Cl2, p.p.m.): δ 63.3 (d), 67.6 (d, JPP = 19.5 Hz)
H atoms were included at calculated positions riding on the attached C atom and individual isotropic displacement parameters were refined.
Data collection: COLLECT (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001) and maXus (Mackay et al., 1999); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS and maXus.
Fig. 1. The molecular structure of the title compound, with the atom-labelling scheme. Dispacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. |
[NiBr(C6H5)(C26H48P2)]·C6H5Cl | F(000) = 1584 |
Mr = 750.89 | Dx = 1.280 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8308 (1) Å | Cell parameters from 89742 reflections |
b = 22.7790 (3) Å | θ = 2.9–27.5° |
c = 14.5238 (2) Å | µ = 1.77 mm−1 |
β = 107.4072 (5)° | T = 200 K |
V = 3734.82 (8) Å3 | Prism, yellow |
Z = 4 | 0.20 × 0.16 × 0.15 mm |
Nonius KappaCCD diffractometer | 4771 reflections with I > 3σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: integration (Coppens, 1970) | h = −15→15 |
Tmin = 0.662, Tmax = 0.808 | k = −29→29 |
94198 measured reflections | l = −18→18 |
8553 independent reflections |
Refinement on F | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | Only H-atom displacement parameters refined |
wR(F2) = 0.031 | Chebychev polynomial with 4 parameters 0.522, -.637, 0.215, -.339 (Carruthers & Watkin , 1979) |
S = 1.05 | (Δ/σ)max = 0.001 |
4771 reflections | Δρmax = 0.56 e Å−3 |
446 parameters | Δρmin = −0.51 e Å−3 |
Primary atom site location: structure-invariant direct methods |
[NiBr(C6H5)(C26H48P2)]·C6H5Cl | V = 3734.82 (8) Å3 |
Mr = 750.89 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.8308 (1) Å | µ = 1.77 mm−1 |
b = 22.7790 (3) Å | T = 200 K |
c = 14.5238 (2) Å | 0.20 × 0.16 × 0.15 mm |
β = 107.4072 (5)° |
Nonius KappaCCD diffractometer | 8553 independent reflections |
Absorption correction: integration (Coppens, 1970) | 4771 reflections with I > 3σ(I) |
Tmin = 0.662, Tmax = 0.808 | Rint = 0.044 |
94198 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 446 parameters |
wR(F2) = 0.031 | Only H-atom displacement parameters refined |
S = 1.05 | Δρmax = 0.56 e Å−3 |
4771 reflections | Δρmin = −0.51 e Å−3 |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.46259 (3) | 0.280369 (14) | 0.76672 (2) | 0.0320 | |
Br1 | 0.50019 (3) | 0.237201 (14) | 0.91905 (2) | 0.0479 | |
Cl1 | 0.12559 (17) | 0.45200 (6) | 0.91951 (11) | 0.1250 | |
P1 | 0.43070 (6) | 0.19424 (3) | 0.69151 (5) | 0.0341 | |
P2 | 0.41007 (6) | 0.32327 (3) | 0.62946 (5) | 0.0331 | |
C1 | 0.5164 (2) | 0.35707 (11) | 0.82877 (19) | 0.0346 | |
C2 | 0.6396 (3) | 0.36330 (13) | 0.8622 (2) | 0.0464 | |
C3 | 0.6881 (3) | 0.41487 (14) | 0.9088 (2) | 0.0522 | |
C4 | 0.6166 (3) | 0.45927 (14) | 0.9227 (2) | 0.0579 | |
C5 | 0.4953 (3) | 0.45158 (14) | 0.8913 (2) | 0.0543 | |
C6 | 0.4465 (3) | 0.39970 (13) | 0.8444 (2) | 0.0462 | |
C7 | 0.4077 (3) | 0.20758 (12) | 0.5624 (2) | 0.0415 | |
C8 | 0.3512 (2) | 0.26822 (12) | 0.5332 (2) | 0.0384 | |
C9 | 0.5612 (2) | 0.14528 (11) | 0.7269 (2) | 0.0387 | |
C10 | 0.6748 (2) | 0.17813 (13) | 0.7289 (2) | 0.0450 | |
C11 | 0.7839 (2) | 0.13823 (14) | 0.7623 (3) | 0.0507 | |
C12 | 0.7689 (3) | 0.08257 (15) | 0.7015 (3) | 0.0601 | |
C13 | 0.6565 (3) | 0.05017 (14) | 0.7002 (3) | 0.0615 | |
C14 | 0.5472 (3) | 0.08941 (13) | 0.6649 (3) | 0.0517 | |
C15 | 0.3056 (2) | 0.14549 (12) | 0.6914 (2) | 0.0391 | |
C16 | 0.3216 (3) | 0.11250 (14) | 0.7864 (2) | 0.0502 | |
C17 | 0.2187 (3) | 0.06967 (15) | 0.7773 (3) | 0.0592 | |
C18 | 0.1001 (3) | 0.10106 (16) | 0.7466 (3) | 0.0616 | |
C19 | 0.0837 (3) | 0.13651 (16) | 0.6551 (3) | 0.0578 | |
C20 | 0.1872 (2) | 0.17861 (13) | 0.6627 (2) | 0.0455 | |
C21 | 0.2859 (2) | 0.37508 (12) | 0.6137 (2) | 0.0369 | |
C22 | 0.1879 (2) | 0.34906 (13) | 0.6516 (2) | 0.0427 | |
C23 | 0.0915 (3) | 0.39504 (14) | 0.6456 (2) | 0.0512 | |
C24 | 0.0406 (3) | 0.41700 (14) | 0.5431 (2) | 0.0511 | |
C25 | 0.1357 (3) | 0.44119 (13) | 0.5029 (2) | 0.0461 | |
C26 | 0.2343 (3) | 0.39626 (12) | 0.5102 (2) | 0.0414 | |
C27 | 0.5197 (2) | 0.36377 (12) | 0.5862 (2) | 0.0385 | |
C28 | 0.5440 (3) | 0.42697 (12) | 0.6240 (2) | 0.0445 | |
C29 | 0.6324 (3) | 0.45680 (14) | 0.5813 (3) | 0.0547 | |
C30 | 0.7479 (3) | 0.42215 (15) | 0.6046 (3) | 0.0642 | |
C31 | 0.7253 (3) | 0.35961 (15) | 0.5663 (3) | 0.0619 | |
C32 | 0.6350 (2) | 0.32872 (13) | 0.6060 (2) | 0.0453 | |
C33 | 0.0998 (4) | 0.37829 (18) | 0.8979 (3) | 0.0677 | |
C34 | 0.1933 (4) | 0.3385 (2) | 0.9245 (3) | 0.0744 | |
C35 | 0.1682 (4) | 0.2797 (2) | 0.9050 (3) | 0.0761 | |
C36 | 0.0554 (5) | 0.2615 (2) | 0.8595 (3) | 0.0834 | |
C37 | −0.0367 (4) | 0.2994 (2) | 0.8329 (3) | 0.0834 | |
C38 | −0.0136 (4) | 0.3598 (2) | 0.8543 (3) | 0.0730 | |
H21 | 0.6920 (3) | 0.33094 (13) | 0.8523 (2) | 0.049 (9)* | |
H31 | 0.7761 (3) | 0.41972 (14) | 0.9318 (2) | 0.067 (11)* | |
H41 | 0.6521 (3) | 0.49642 (14) | 0.9555 (2) | 0.06 (1)* | |
H51 | 0.4420 (3) | 0.48313 (14) | 0.9023 (2) | 0.067 (11)* | |
H61 | 0.3586 (3) | 0.39431 (13) | 0.8217 (2) | 0.068 (11)* | |
H71 | 0.4859 (3) | 0.20609 (12) | 0.5492 (2) | 0.035 (7)* | |
H72 | 0.3544 (3) | 0.17652 (12) | 0.5239 (2) | 0.044 (8)* | |
H81 | 0.3687 (2) | 0.28158 (12) | 0.4734 (2) | 0.034 (7)* | |
H82 | 0.2635 (2) | 0.26493 (12) | 0.5203 (2) | 0.043 (8)* | |
H91 | 0.5694 (2) | 0.13146 (11) | 0.7940 (2) | 0.045 (8)* | |
H101 | 0.6848 (2) | 0.21262 (13) | 0.7732 (2) | 0.053 (9)* | |
H102 | 0.6669 (2) | 0.19213 (13) | 0.6620 (2) | 0.051 (9)* | |
H111 | 0.7950 (2) | 0.12656 (14) | 0.8308 (3) | 0.06 (1)* | |
H112 | 0.8553 (2) | 0.16017 (14) | 0.7580 (3) | 0.075 (12)* | |
H121 | 0.8390 (3) | 0.05629 (15) | 0.7273 (3) | 0.074 (11)* | |
H122 | 0.7628 (3) | 0.09403 (15) | 0.6337 (3) | 0.072 (12)* | |
H131 | 0.6639 (3) | 0.03752 (14) | 0.7677 (3) | 0.06 (1)* | |
H132 | 0.6467 (3) | 0.01483 (14) | 0.6577 (3) | 0.079 (12)* | |
H141 | 0.4750 (3) | 0.06755 (13) | 0.6677 (3) | 0.069 (11)* | |
H142 | 0.5380 (3) | 0.10126 (13) | 0.5967 (3) | 0.063 (11)* | |
H151 | 0.3030 (2) | 0.11455 (12) | 0.6419 (2) | 0.055 (9)* | |
H161 | 0.3214 (3) | 0.14192 (14) | 0.8375 (2) | 0.06 (1)* | |
H162 | 0.3988 (3) | 0.09101 (14) | 0.8049 (2) | 0.054 (9)* | |
H171 | 0.2293 (3) | 0.04915 (15) | 0.8402 (3) | 0.074 (12)* | |
H172 | 0.2194 (3) | 0.04017 (15) | 0.7265 (3) | 0.06 (1)* | |
H181 | 0.0974 (3) | 0.12853 (16) | 0.7996 (3) | 0.071 (12)* | |
H182 | 0.0345 (3) | 0.07179 (16) | 0.7361 (3) | 0.075 (12)* | |
H191 | 0.0086 (3) | 0.15959 (16) | 0.6410 (3) | 0.074 (11)* | |
H192 | 0.0786 (3) | 0.10850 (16) | 0.6010 (3) | 0.082 (13)* | |
H201 | 0.1893 (2) | 0.20875 (13) | 0.7133 (2) | 0.044 (8)* | |
H202 | 0.1761 (2) | 0.19851 (13) | 0.5993 (2) | 0.044 (8)* | |
H211 | 0.3181 (2) | 0.41070 (12) | 0.6531 (2) | 0.034 (7)* | |
H221 | 0.2232 (2) | 0.33592 (13) | 0.7199 (2) | 0.055 (9)* | |
H222 | 0.1517 (2) | 0.31463 (13) | 0.6106 (2) | 0.039 (8)* | |
H231 | 0.1277 (3) | 0.42907 (14) | 0.6876 (2) | 0.06 (1)* | |
H232 | 0.0270 (3) | 0.37772 (14) | 0.6684 (2) | 0.06 (1)* | |
H241 | −0.0198 (3) | 0.44815 (14) | 0.5406 (2) | 0.054 (9)* | |
H242 | 0.0019 (3) | 0.38304 (14) | 0.5020 (2) | 0.046 (8)* | |
H251 | 0.1709 (3) | 0.47673 (13) | 0.5412 (2) | 0.040 (8)* | |
H252 | 0.0993 (3) | 0.45245 (13) | 0.4338 (2) | 0.051 (9)* | |
H261 | 0.2986 (3) | 0.41464 (12) | 0.4883 (2) | 0.034 (7)* | |
H262 | 0.2007 (3) | 0.36189 (12) | 0.4681 (2) | 0.048 (9)* | |
H271 | 0.4840 (2) | 0.36861 (12) | 0.5150 (2) | 0.043 (8)* | |
H281 | 0.5783 (3) | 0.42575 (12) | 0.6958 (2) | 0.051 (9)* | |
H282 | 0.4682 (3) | 0.44964 (12) | 0.6064 (2) | 0.051 (9)* | |
H291 | 0.6494 (3) | 0.49741 (14) | 0.6081 (3) | 0.051 (9)* | |
H292 | 0.5970 (3) | 0.45887 (14) | 0.5097 (3) | 0.072 (12)* | |
H301 | 0.7834 (3) | 0.42029 (15) | 0.6763 (3) | 0.073 (12)* | |
H302 | 0.8043 (3) | 0.44215 (15) | 0.5755 (3) | 0.086 (13)* | |
H311 | 0.8014 (3) | 0.33716 (15) | 0.5842 (3) | 0.07 (1)* | |
H312 | 0.6922 (3) | 0.36139 (15) | 0.4944 (3) | 0.063 (11)* | |
H321 | 0.6704 (2) | 0.32440 (13) | 0.6773 (2) | 0.049 (9)* | |
H322 | 0.6168 (2) | 0.28901 (13) | 0.5758 (2) | 0.033 (7)* | |
H341 | 0.2755 (4) | 0.3525 (2) | 0.9579 (3) | 0.068 (11)* | |
H351 | 0.2329 (4) | 0.2498 (2) | 0.9240 (3) | 0.100 (15)* | |
H361 | 0.0404 (5) | 0.2188 (2) | 0.8444 (3) | 0.19 (3)* | |
H371 | −0.1188 (4) | 0.2854 (2) | 0.7991 (3) | 0.070 (11)* | |
H381 | −0.0792 (4) | 0.3893 (2) | 0.8380 (3) | 0.127 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02780 (15) | 0.02679 (16) | 0.03603 (19) | 0.00113 (13) | 0.00120 (13) | −0.00099 (13) |
Br1 | 0.05188 (17) | 0.03917 (15) | 0.04293 (16) | −0.00306 (13) | −0.00057 (13) | 0.00557 (13) |
Cl1 | 0.1838 (16) | 0.0630 (7) | 0.104 (1) | −0.0126 (8) | 0.006 (1) | 0.0053 (7) |
P1 | 0.0284 (3) | 0.0271 (3) | 0.0415 (4) | 0.0008 (3) | 0.0026 (3) | −0.0011 (3) |
P2 | 0.0282 (3) | 0.0278 (3) | 0.0384 (4) | 0.0001 (2) | 0.0025 (3) | −0.0001 (3) |
C1 | 0.0351 (13) | 0.0326 (14) | 0.0308 (13) | −0.006 (1) | 0.0015 (11) | 0.008 (1) |
C2 | 0.0410 (15) | 0.0433 (16) | 0.0490 (18) | −0.0022 (13) | 0.0042 (13) | −0.0030 (13) |
C3 | 0.0519 (19) | 0.0463 (18) | 0.0521 (19) | −0.0141 (15) | 0.0059 (15) | −0.0012 (14) |
C4 | 0.075 (2) | 0.0376 (17) | 0.055 (2) | −0.0140 (16) | 0.0095 (17) | −0.0064 (14) |
C5 | 0.068 (2) | 0.0407 (17) | 0.0506 (19) | 0.0060 (15) | 0.0117 (16) | −0.0066 (14) |
C6 | 0.0467 (17) | 0.0475 (17) | 0.0392 (17) | −0.0064 (13) | 0.0049 (13) | −0.0043 (13) |
C7 | 0.0368 (14) | 0.0338 (15) | 0.0482 (17) | −0.0002 (11) | 0.0042 (12) | −0.0055 (12) |
C8 | 0.0345 (13) | 0.0385 (15) | 0.0366 (14) | 0.0004 (11) | 0.0024 (11) | −0.0004 (12) |
C9 | 0.0292 (13) | 0.0312 (13) | 0.0510 (18) | 0.002 (1) | 0.0048 (12) | 0.0016 (12) |
C10 | 0.0332 (14) | 0.0386 (15) | 0.060 (2) | −0.0007 (11) | 0.0089 (13) | −0.0000 (14) |
C11 | 0.0286 (14) | 0.0568 (19) | 0.065 (2) | 0.0037 (13) | 0.0110 (14) | 0.0009 (16) |
C12 | 0.0402 (17) | 0.0534 (19) | 0.089 (3) | 0.0105 (14) | 0.0226 (17) | −0.0006 (18) |
C13 | 0.0468 (18) | 0.0384 (17) | 0.098 (3) | 0.0089 (14) | 0.0205 (18) | −0.0063 (17) |
C14 | 0.0379 (16) | 0.0334 (15) | 0.079 (3) | 0.0036 (12) | 0.0106 (15) | −0.0091 (15) |
C15 | 0.0285 (13) | 0.0322 (14) | 0.0527 (18) | −0.001 (1) | 0.0064 (12) | −0.0030 (12) |
C16 | 0.0347 (15) | 0.0439 (17) | 0.067 (2) | −0.0034 (12) | 0.0070 (14) | 0.0118 (15) |
C17 | 0.0438 (17) | 0.0456 (18) | 0.084 (3) | −0.0072 (14) | 0.0133 (17) | 0.0086 (18) |
C18 | 0.0432 (18) | 0.058 (2) | 0.086 (3) | −0.0068 (15) | 0.0234 (18) | 0.0021 (19) |
C19 | 0.0299 (15) | 0.062 (2) | 0.076 (2) | −0.0014 (14) | 0.0079 (15) | −0.0051 (18) |
C20 | 0.0321 (14) | 0.0435 (16) | 0.0566 (19) | 0.0038 (12) | 0.0069 (13) | 0.0039 (14) |
C21 | 0.0314 (13) | 0.0306 (13) | 0.0438 (16) | 0.001 (1) | 0.0038 (11) | −0.0015 (11) |
C22 | 0.0367 (15) | 0.0392 (15) | 0.0505 (18) | 0.0016 (12) | 0.0103 (13) | 0.0038 (13) |
C23 | 0.0433 (17) | 0.0494 (18) | 0.063 (2) | 0.0057 (14) | 0.0195 (15) | −0.0009 (15) |
C24 | 0.0405 (16) | 0.0426 (17) | 0.068 (2) | 0.0104 (13) | 0.0134 (15) | 0.0021 (15) |
C25 | 0.0435 (15) | 0.0350 (15) | 0.0543 (19) | 0.0066 (12) | 0.0063 (14) | 0.0028 (13) |
C26 | 0.0380 (14) | 0.0365 (14) | 0.0459 (17) | 0.0033 (11) | 0.0066 (12) | 0.0024 (12) |
C27 | 0.0331 (13) | 0.0367 (14) | 0.0412 (16) | −0.0002 (11) | 0.0045 (11) | 0.0037 (12) |
C28 | 0.0387 (15) | 0.0331 (15) | 0.057 (2) | −0.0027 (12) | 0.0073 (13) | 0.0068 (13) |
C29 | 0.0458 (17) | 0.0408 (17) | 0.073 (2) | −0.0056 (13) | 0.0107 (16) | 0.0098 (15) |
C30 | 0.0400 (18) | 0.053 (2) | 0.097 (3) | −0.0058 (15) | 0.0172 (19) | 0.0113 (19) |
C31 | 0.0429 (18) | 0.056 (2) | 0.090 (3) | 0.0035 (15) | 0.0248 (18) | 0.0093 (19) |
C32 | 0.0365 (15) | 0.0381 (15) | 0.061 (2) | −0.0002 (12) | 0.0137 (14) | 0.0064 (14) |
C33 | 0.085 (3) | 0.064 (2) | 0.052 (2) | 0.003 (2) | 0.0155 (19) | 0.0069 (17) |
C34 | 0.066 (3) | 0.091 (3) | 0.070 (3) | 0.001 (2) | 0.025 (2) | 0.015 (2) |
C35 | 0.078 (3) | 0.075 (3) | 0.085 (3) | 0.014 (2) | 0.038 (2) | 0.005 (2) |
C36 | 0.093 (3) | 0.079 (3) | 0.088 (3) | −0.004 (3) | 0.042 (3) | −0.008 (2) |
C37 | 0.077 (3) | 0.107 (4) | 0.075 (3) | 0.002 (3) | 0.035 (2) | 0.012 (3) |
C38 | 0.073 (3) | 0.085 (3) | 0.063 (3) | 0.014 (2) | 0.023 (2) | 0.011 (2) |
Ni1—Br1 | 2.3390 (5) | C18—C19 | 1.518 (5) |
Ni1—P1 | 2.2223 (7) | C18—H181 | 1.000 |
Ni1—P2 | 2.1387 (8) | C18—H182 | 1.000 |
Ni1—C1 | 1.981 (3) | C19—C20 | 1.533 (4) |
Cl1—C33 | 1.719 (4) | C19—H191 | 1.000 |
P1—C7 | 1.838 (3) | C19—H192 | 1.000 |
P1—C9 | 1.848 (3) | C20—H201 | 1.000 |
P1—C15 | 1.850 (3) | C20—H202 | 1.000 |
P2—C8 | 1.851 (3) | C21—C22 | 1.543 (4) |
P2—C21 | 1.844 (3) | C21—C26 | 1.522 (4) |
P2—C27 | 1.848 (3) | C21—H211 | 1.000 |
C1—C2 | 1.400 (4) | C22—C23 | 1.532 (4) |
C1—C6 | 1.338 (4) | C22—H221 | 1.000 |
C2—C3 | 1.391 (4) | C22—H222 | 1.000 |
C2—H21 | 1.000 | C23—C24 | 1.514 (5) |
C3—C4 | 1.372 (5) | C23—H231 | 1.000 |
C3—H31 | 1.000 | C23—H232 | 1.000 |
C4—C5 | 1.381 (5) | C24—C25 | 1.518 (4) |
C4—H41 | 1.000 | C24—H241 | 1.000 |
C5—C6 | 1.399 (4) | C24—H242 | 1.000 |
C5—H51 | 1.000 | C25—C26 | 1.531 (4) |
C6—H61 | 1.000 | C25—H251 | 1.000 |
C7—C8 | 1.538 (4) | C25—H252 | 1.000 |
C7—H71 | 1.000 | C26—H261 | 1.000 |
C7—H72 | 1.000 | C26—H262 | 1.000 |
C8—H81 | 1.000 | C27—C28 | 1.537 (4) |
C8—H82 | 1.000 | C27—C32 | 1.532 (4) |
C9—C10 | 1.531 (4) | C27—H271 | 1.000 |
C9—C14 | 1.539 (4) | C28—C29 | 1.526 (4) |
C9—H91 | 1.000 | C28—H281 | 1.000 |
C10—C11 | 1.534 (4) | C28—H282 | 1.000 |
C10—H101 | 1.000 | C29—C30 | 1.526 (4) |
C10—H102 | 1.000 | C29—H291 | 1.000 |
C11—C12 | 1.525 (5) | C29—H292 | 1.000 |
C11—H111 | 1.000 | C30—C31 | 1.524 (5) |
C11—H112 | 1.000 | C30—H301 | 1.000 |
C12—C13 | 1.516 (5) | C30—H302 | 1.000 |
C12—H121 | 1.000 | C31—C32 | 1.528 (4) |
C12—H122 | 1.000 | C31—H311 | 1.000 |
C13—C14 | 1.529 (4) | C31—H312 | 1.000 |
C13—H131 | 1.000 | C32—H321 | 1.000 |
C13—H132 | 1.000 | C32—H322 | 1.000 |
C14—H141 | 1.000 | C33—C34 | 1.393 (6) |
C14—H142 | 1.000 | C33—C38 | 1.367 (6) |
C15—C16 | 1.533 (4) | C34—C35 | 1.382 (6) |
C15—C20 | 1.535 (4) | C34—H341 | 1.000 |
C15—H151 | 1.000 | C35—C36 | 1.365 (6) |
C16—C17 | 1.535 (4) | C35—H351 | 1.000 |
C16—H161 | 1.000 | C36—C37 | 1.353 (6) |
C16—H162 | 1.000 | C36—H361 | 1.000 |
C17—C18 | 1.517 (5) | C37—C38 | 1.420 (6) |
C17—H171 | 1.000 | C37—H371 | 1.000 |
C17—H172 | 1.000 | C38—H381 | 1.000 |
Br1—Ni1—P1 | 92.87 (2) | C17—C18—H182 | 109.76 (18) |
Br1—Ni1—P2 | 173.61 (3) | C19—C18—H182 | 109.28 (18) |
P1—Ni1—P2 | 89.19 (3) | H181—C18—H182 | 109.467 |
Br1—Ni1—C1 | 89.78 (7) | C18—C19—C20 | 112.3 (3) |
P1—Ni1—C1 | 170.47 (8) | C18—C19—H191 | 109.41 (18) |
P2—Ni1—C1 | 89.16 (7) | C20—C19—H191 | 109.14 (17) |
Ni1—P1—C7 | 107.89 (9) | C18—C19—H192 | 108.1 (2) |
Ni1—P1—C9 | 113.02 (9) | C20—C19—H192 | 108.40 (19) |
C7—P1—C9 | 103.90 (13) | H191—C19—H192 | 109.467 |
Ni1—P1—C15 | 123.3 (1) | C15—C20—C19 | 110.9 (2) |
C7—P1—C15 | 102.94 (13) | C15—C20—H201 | 108.56 (16) |
C9—P1—C15 | 103.85 (12) | C19—C20—H201 | 109.07 (19) |
Ni1—P2—C8 | 109.45 (9) | C15—C20—H202 | 109.29 (17) |
Ni1—P2—C21 | 113.97 (9) | C19—C20—H202 | 109.55 (18) |
C8—P2—C21 | 103.53 (12) | H201—C20—H202 | 109.467 |
Ni1—P2—C27 | 120.48 (9) | P2—C21—C22 | 111.44 (18) |
C8—P2—C27 | 103.03 (13) | P2—C21—C26 | 113.26 (19) |
C21—P2—C27 | 104.61 (12) | C22—C21—C26 | 110.6 (2) |
Ni1—C1—C2 | 114.0 (2) | P2—C21—H211 | 107.18 (8) |
Ni1—C1—C6 | 125.9 (2) | C22—C21—H211 | 107.86 (15) |
C2—C1—C6 | 120.0 (3) | C26—C21—H211 | 106.20 (15) |
C1—C2—C3 | 119.3 (3) | C21—C22—C23 | 110.1 (2) |
C1—C2—H21 | 120.07 (17) | C21—C22—H221 | 109.47 (15) |
C3—C2—H21 | 120.6 (2) | C23—C22—H221 | 110.13 (17) |
C2—C3—C4 | 120.8 (3) | C21—C22—H222 | 108.84 (15) |
C2—C3—H31 | 119.5 (2) | C23—C22—H222 | 108.85 (17) |
C4—C3—H31 | 119.69 (19) | H221—C22—H222 | 109.467 |
C3—C4—C5 | 118.9 (3) | C22—C23—C24 | 110.7 (3) |
C3—C4—H41 | 120.31 (19) | C22—C23—H231 | 108.65 (17) |
C5—C4—H41 | 120.77 (19) | C24—C23—H231 | 108.41 (18) |
C4—C5—C6 | 120.3 (3) | C22—C23—H232 | 109.91 (17) |
C4—C5—H51 | 119.90 (19) | C24—C23—H232 | 109.72 (17) |
C6—C5—H51 | 119.8 (2) | H231—C23—H232 | 109.467 |
C1—C6—C5 | 120.7 (3) | C23—C24—C25 | 112.0 (3) |
C1—C6—H61 | 119.28 (16) | C23—C24—H241 | 109.84 (16) |
C5—C6—H61 | 120.0 (2) | C25—C24—H241 | 109.44 (15) |
P1—C7—C8 | 110.43 (19) | C23—C24—H242 | 107.88 (18) |
P1—C7—H71 | 109.07 (9) | C25—C24—H242 | 108.15 (18) |
C8—C7—H71 | 109.17 (16) | H241—C24—H242 | 109.467 |
P1—C7—H72 | 109.29 (9) | C24—C25—C26 | 111.6 (2) |
C8—C7—H72 | 109.39 (14) | C24—C25—H251 | 108.26 (18) |
H71—C7—H72 | 109.467 | C26—C25—H251 | 108.72 (16) |
P2—C8—C7 | 111.46 (18) | C24—C25—H252 | 109.43 (17) |
P2—C8—H81 | 108.75 (9) | C26—C25—H252 | 109.36 (16) |
C7—C8—H81 | 109.06 (16) | H251—C25—H252 | 109.467 |
P2—C8—H82 | 109.10 (9) | C21—C26—C25 | 110.7 (2) |
C7—C8—H82 | 108.98 (15) | C21—C26—H261 | 109.12 (15) |
H81—C8—H82 | 109.467 | C25—C26—H261 | 109.53 (16) |
P1—C9—C10 | 111.44 (18) | C21—C26—H262 | 108.96 (15) |
P1—C9—C14 | 113.66 (19) | C25—C26—H262 | 109.08 (16) |
C10—C9—C14 | 110.8 (2) | H261—C26—H262 | 109.466 |
P1—C9—H91 | 106.9 (1) | P2—C27—C28 | 115.0 (2) |
C10—C9—H91 | 107.86 (17) | P2—C27—C32 | 110.65 (19) |
C14—C9—H91 | 105.77 (18) | C28—C27—C32 | 111.1 (2) |
C9—C10—C11 | 111.5 (2) | P2—C27—H271 | 106.56 (9) |
C9—C10—H101 | 109.29 (16) | C28—C27—H271 | 104.02 (16) |
C11—C10—H101 | 109.58 (17) | C32—C27—H271 | 109.11 (17) |
C9—C10—H102 | 108.18 (17) | C27—C28—C29 | 110.5 (3) |
C11—C10—H102 | 108.76 (18) | C27—C28—H281 | 108.71 (16) |
H101—C10—H102 | 109.467 | C29—C28—H281 | 108.84 (18) |
C10—C11—C12 | 111.6 (3) | C27—C28—H282 | 109.55 (15) |
C10—C11—H111 | 108.69 (18) | C29—C28—H282 | 109.75 (16) |
C12—C11—H111 | 108.2 (2) | H281—C28—H282 | 109.467 |
C10—C11—H112 | 109.34 (17) | C28—C29—C30 | 110.9 (3) |
C12—C11—H112 | 109.45 (18) | C28—C29—H291 | 109.70 (18) |
H111—C11—H112 | 109.467 | C30—C29—H291 | 109.26 (19) |
C11—C12—C13 | 111.2 (3) | C28—C29—H292 | 108.63 (18) |
C11—C12—H121 | 109.94 (17) | C30—C29—H292 | 108.8 (2) |
C13—C12—H121 | 109.81 (18) | H291—C29—H292 | 109.467 |
C11—C12—H122 | 108.3 (2) | C29—C30—C31 | 110.8 (3) |
C13—C12—H122 | 108.1 (2) | C29—C30—H301 | 108.8 (2) |
H121—C12—H122 | 109.467 | C31—C30—H301 | 108.3 (2) |
C12—C13—C14 | 111.7 (3) | C29—C30—H302 | 109.70 (18) |
C12—C13—H131 | 108.0 (2) | C31—C30—H302 | 109.7 (2) |
C14—C13—H131 | 108.4 (2) | H301—C30—H302 | 109.467 |
C12—C13—H132 | 109.8 (2) | C30—C31—C32 | 111.0 (3) |
C14—C13—H132 | 109.45 (18) | C30—C31—H311 | 109.68 (18) |
H131—C13—H132 | 109.467 | C32—C31—H311 | 110.04 (17) |
C9—C14—C13 | 110.8 (3) | C30—C31—H312 | 108.3 (2) |
C9—C14—H141 | 109.38 (16) | C32—C31—H312 | 108.3 (2) |
C13—C14—H141 | 110.01 (18) | H311—C31—H312 | 109.467 |
C9—C14—H142 | 108.48 (18) | C27—C32—C31 | 111.9 (2) |
C13—C14—H142 | 108.7 (2) | C27—C32—H321 | 108.54 (17) |
H141—C14—H142 | 109.467 | C31—C32—H321 | 108.3 (2) |
P1—C15—C16 | 114.22 (19) | C27—C32—H322 | 109.02 (15) |
P1—C15—C20 | 111.73 (19) | C31—C32—H322 | 109.58 (19) |
C16—C15—C20 | 110.0 (2) | H321—C32—H322 | 109.467 |
P1—C15—H151 | 106.04 (9) | Cl1—C33—C34 | 120.2 (3) |
C16—C15—H151 | 105.67 (17) | Cl1—C33—C38 | 118.7 (3) |
C20—C15—H151 | 108.82 (16) | C34—C33—C38 | 121.1 (4) |
C15—C16—C17 | 110.7 (3) | C33—C34—C35 | 118.0 (4) |
C15—C16—H161 | 108.18 (17) | C33—C34—H341 | 120.2 (3) |
C17—C16—H161 | 108.2 (2) | C35—C34—H341 | 121.8 (3) |
C15—C16—H162 | 109.79 (15) | C34—C35—C36 | 120.9 (4) |
C17—C16—H162 | 110.47 (17) | C34—C35—H351 | 120.2 (3) |
H161—C16—H162 | 109.467 | C36—C35—H351 | 118.9 (3) |
C16—C17—C18 | 111.4 (3) | C35—C36—C37 | 122.1 (5) |
C16—C17—H171 | 109.80 (19) | C35—C36—H361 | 119.1 (3) |
C18—C17—H171 | 110.0 (2) | C37—C36—H361 | 118.9 (3) |
C16—C17—H172 | 108.0 (2) | C36—C37—C38 | 118.1 (5) |
C18—C17—H172 | 108.2 (2) | C36—C37—H371 | 121.1 (3) |
H171—C17—H172 | 109.467 | C38—C37—H371 | 120.8 (3) |
C17—C18—C19 | 111.9 (3) | C33—C38—C37 | 119.8 (4) |
C17—C18—H181 | 108.0 (2) | C33—C38—H381 | 119.2 (3) |
C19—C18—H181 | 108.4 (2) | C37—C38—H381 | 120.9 (3) |
Experimental details
Crystal data | |
Chemical formula | [NiBr(C6H5)(C26H48P2)]·C6H5Cl |
Mr | 750.89 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 200 |
a, b, c (Å) | 11.8308 (1), 22.7790 (3), 14.5238 (2) |
β (°) | 107.4072 (5) |
V (Å3) | 3734.82 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.77 |
Crystal size (mm) | 0.20 × 0.16 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Integration (Coppens, 1970) |
Tmin, Tmax | 0.662, 0.808 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 94198, 8553, 4771 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.031, 1.05 |
No. of reflections | 4771 |
No. of parameters | 446 |
No. of restraints | ? |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.56, −0.51 |
Computer programs: COLLECT (Nonius, 1997), HKL SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Watkin et al., 2001) and maXus (Mackay et al., 1999), CAMERON (Watkin et al., 1996), CRYSTALS and maXus.
Ni1—Br1 | 2.3390 (5) | P2—C27 | 1.848 (3) |
Ni1—P1 | 2.2223 (7) | C1—C2 | 1.400 (4) |
Ni1—P2 | 2.1387 (8) | C1—C6 | 1.338 (4) |
Ni1—C1 | 1.981 (3) | C2—C3 | 1.391 (4) |
P1—C7 | 1.838 (3) | C3—C4 | 1.372 (5) |
P1—C9 | 1.848 (3) | C4—C5 | 1.381 (5) |
P1—C15 | 1.850 (3) | C5—C6 | 1.399 (4) |
P2—C8 | 1.851 (3) | C7—C8 | 1.538 (4) |
P2—C21 | 1.844 (3) | ||
Br1—Ni1—P1 | 92.87 (2) | Ni1—P1—C15 | 123.3 (1) |
Br1—Ni1—P2 | 173.61 (3) | Ni1—P2—C8 | 109.45 (9) |
P1—Ni1—P2 | 89.19 (3) | Ni1—P2—C21 | 113.97 (9) |
Br1—Ni1—C1 | 89.78 (7) | Ni1—P2—C27 | 120.48 (9) |
P1—Ni1—C1 | 170.47 (8) | Ni1—C1—C2 | 114.0 (2) |
P2—Ni1—C1 | 89.16 (7) | Ni1—C1—C6 | 125.9 (2) |
Ni1—P1—C7 | 107.89 (9) | P1—C7—C8 | 110.43 (19) |
Ni1—P1—C9 | 113.02 (9) | P2—C8—C7 | 111.46 (18) |
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Arylnickel(II) complexes are usually prepared by oxidative addition of aryl halides to a nickel(0) centre. Compound (II) and related species have been obtained by reaction of bromobenzene with [Ni(η2-C2H4)(dcpe)] (Bennett et al., 1985) or with [NiBr2(PPh3)2] in the presence of activated zinc, followed by ligand exchange with dcpe (Bennett & Wenger, 1995). The present sample, however, was isolated after hydrolysis of the arylnickel(II) complex (I) bearing a boronic ester group in the ortho position. The latter complex, which has been studied as a precursor to the benzynenickel(0) complex [Ni(η2-C6H4)(dcpe)] (Bennett et al., 2002), is highly reactive towards moisture, due to the large steric interaction between the boronic ester substituent and the cyclohexyl groups on the diphosphine ligand. Cleavage of the C—B bond in (I) occurs readily and compound (II) was obtained from attempted crystallizations of (I).
Complex (II) crystallized as a chlorobenzene solvate, and the solvent molecule was clearly defined. The nickel centre of (II) is in a square-planar environment, with C1—Ni—P1 and Br1—Ni—P2 angles of 170.47 (8) and 173.61 (3)°, respectively. The Ni—P distances are not equivalent, the bond trans to atom C1 being longer than the bond trans to Br, as expected from the larger trans influence of the phenyl group. Similarly, the Ni—C1 distance [1.981 (3) Å] is longer than that in complexes having trans phosphines and a halide trans to Ni—C; see for example [NiCl(o-C6H4Me)(PPh3)2] (1.900 Å; Spek et al., 2000) and [NiCl(o-C6H4CF3)(PPh3)2] (1.890%A; Lutz et al., 1998). The other geometric data of complex (II) are unexceptional.