Bis­[methyl­enebis­(di­phenyl­phosphine)-P,P']­nickel(II) diperchlorate

The title compound, [Ni(Ph₂PCH₂PPh₂)₂](ClO₄)₂, was synthesized and its structure determined crystallographically. The Ni atom lies on an inversion centre and is at the center of a square formed by four P atoms which are necessarily coplanar. The Ni-P distances are 2.2188 (5) and 2.2322 (5) Å, and the P-Ni-P angle is 73.12 (3)°. The unique perchlorate anion is not coordinated to the Ni atom.

S1. Comment

Much interest has been given to metal–phosphine complexes because they not only have special geometrical and electronical structures, but also serve as catalysts in industry. In order to understand the microstructures of these complexes and research their catalytical mechanisms to provide more information for the development of catalysts, we now report the crystal structure of the title compound, (I). The four P atoms and the Ni^II atom are coplanar. At the same time, the two diphenylphosphine groups are linked by a methylene group. The Ni^II ion lies in the center of the square formed by atoms of P1, P2, P1' and P2'. The dihedral angles between the plane which these four P atoms are sited in and each of the eight benzene rings fall in the range 63–93°. It can be inferred that a negtively charged area is formed around the Ni^II ion, while the center of the positively charged Ni^II ion is completely exposed and easily coordinated by some gas or solid molecules along the axis vertical to the plane formed by four P atoms. Perhaps that is the reason that the title complex has high catalytical activities. The Ni—P bond lengths are 2.2322 (5), 2.2322 (5), 2.2188 (5) and 2.2188 (5) Å; the average length is 2.2255 (5) Å, which is in the normal range of Ni—P bond lengths. The Ni atom lies on an inversion centre.

S2. Experimental

A methanol solution of tris(N-methyl-1-benzimidazol-z-yl)amine (TMBMA; 100 mg, 0.222 mmol) and a methylene chloride solution of methylenebis(diphenylphosphine) (44 mg, 0.111 mmol) were mixed at room temperature. With stirring, the methanol solution of Ni(ClO₄)·6H₂O (81 mg, 0.222 mmol) was added to the mixture. After stirred for 12 h, the precipate was filtered, washed with methanol and ethanol in turn, then dried in vacuo to obtain a, green–yellow powder. Green–yellow monocrystals suitable for X-ray determination were formed by slowly evaporating the acetonitrile solution for a period of one month at room temperature.

S3. Refinement

All H atoms were located in difference Fourier maps and refined with isotropic displacement paramenters; the C—H range is 0.86 (3)–1.03 (4) Å.

Computing details

Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD-4 Operations Manual; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1987); program(s) used to solve structure: MITHRIL (Gilmore, 1983); program(s) used to refine structure: LS in TEXSAN); software used to prepare material for publication: GCIF (local program).

Bis[methylenebis(diphenylphosphine)-P,P']nickel(II) diperchlorate

Crystal data

[Ni(C25H22P2)2](ClO4)2	F(000) = 1060
Mr = 1026.32	Dx = 1.413 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 11.226 (2) Å	Cell parameters from 25 reflections
b = 17.836 (2) Å	θ = 14.2–14.8°
c = 12.932 (2) Å	µ = 0.70 mm^−1
β = 111.32 (1)°	T = 296 K
V = 2412.0 (6) Å^3	Block, green yellow
Z = 2	0.38 × 0.30 × 0.17 mm

Data collection

Enraf Nonius CAD-4 diffractometer	Rint = 0.033
ω/2θ scans	θmax = 25°
Absorption correction: ψ scans (North et al., 1968)	h = 0→13
Tmin = 0.773, Tmax = 0.889	k = 0→21
4624 measured reflections	l = −15→15
4431 independent reflections	3 standard reflections every 300 reflections
4340 reflections with I > 3σ(I)	intensity decay: 1.0%

Refinement

Refinement on F	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(F)]
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max = 0.05
wR(F^2) = 0.044	Δρmax = 0.29 e Å^−3
S = 1.22	Δρmin = −0.25 e Å^−3
3262 reflections	Extinction correction: ω/2θ
323 parameters	Extinction coefficient: 0

Special details

Geometry. ——-Plane number 1——- 0 Atoms Defining Plane Distance e.s.d. P1 0.0000 0.0006 P2 0.0000 0.0006 P1 (3) 0.0000 0.0006 P2 (3) 0.0000 0.0006 Ni 0.0000 0.0010 0 Additional Atoms Distance C1 0.6647 C1 (3) −0.6647 0 Mean deviation from plane is 0.0000 angstroms Chi-squared: 1.9 0 —— Plane number 2 ——- 0 Atoms Defining Plane Distance e.s.d. C11 0.0031 0.0023 C12 − 0.0035 0.0035 C13 − 0.0065 0.0041 C14 0.0096 0.0037 C15 − 0.0040 0.0033 C16 − 0.0027 0.0030 0 Additional Atoms Distance P1 0.1016 C1 − 0.9283 0 Mean deviation from plane is 0.0049 angstroms Chi-squared: 15.1 0 Dihedral angles between least-squares planes plane plane angle 2 1 86.01 0 —— Plane number 3 —— 0 Atoms Defining Plane Distance e.s.d. C21 − 0.0039 0.0023 C22 0.0016 0.0029 C23 0.0048 0.0036 C24 − 0.0072 0.0041 C25 − 0.0030 0.0044 C26 0.0080 0.0034 0 Additional Atoms Distance P1 − 0.0030 C1 − 1.2643 0 Mean deviation from plane is 0.0047 angstroms Chi-squared: 14.1 0 Dihedral angles between least-squares planes plane plane angle 3 1 77.80 3 2 82.99 0 —— Plane number 4 ——- 0 Atoms Defining Plane Distance e.s.d. C31 0.0052 0.0022 C32 − 0.0041 0.0028 C33 − 0.0006 0.0035 C34 0.0010 0.0036 C35 0.0056 0.0036 C36 − 0.0085 0.0029 0 Additional Atoms Distance P2 0.1107 C1 − 0.1682 0 Mean deviation from plane is 0.0042 angstroms Chi-squared: 17.5 0 Dihedral angles between least-squares planes plane plane angle 4 1 63.49 4 2 27.72 4 3 63.94 0 ——– Plane number 5 ——- 0 Atoms Defining Plane Distance e.s.d. C41 0.0039 0.0023 C42 − 0.0026 0.0027 C43 − 0.0038 0.0033 C44 0.0087 0.0038 C45 − 0.0025 0.0041 C46 − 0.0046 0.0031 0 Additional Atoms Distance P2 0.1321 C1 1.6443 0 Mean deviation from plane is 0.0044 angstroms Chi-squared: 12.4 0 Dihedral angles between least-squares planes plane plane angle 5 1 92.85 5 2 104.04 5 3 25.10 5 4 88.58 0 ——- Plane number 6 ——— 0 Atoms Defining Plane Distance e.s.d. C11 (3) −0.0031 0.0023 C12 (3) 0.0035 0.0035 C13 (3) 0.0065 0.0041 C14 (3) −0.0096 0.0037 C15 (3) 0.0040 0.0033 C16 (3) 0.0027 0.0030 0 Additional Atoms Distance P1 (3) −0.1016 C1 (3) 0.9283 0 Mean deviation from plane is 0.0049 angstroms Chi-squared: 15.1 0 Dihedral angles between least-squares planes plane plane angle 6 1 86.01 6 2 0.00 6 3 82.99 6 4 27.72 6 5 104.04 0 ——- Plane number 7 ——– 0 Atoms Defining Plane Distance e.s.d. C21 (3) 0.0039 0.0023 C22 (3) −0.0016 0.0029 C23 (3) −0.0048 0.0036 C24 (3) 0.0072 0.0041 C25 (3) 0.0030 0.0044 C26 (3) −0.0080 0.0034 0 Additional Atoms Distance P1 (3) 0.0030 C1 (3) 1.2643 0 Mean deviation from plane is 0.0047 angstroms Chi-squared: 14.1 0 Dihedral angles between least-squares planes plane plane angle 7 1 77.80 7 2 82.99 7 3 0.00 7 4 63.94 7 5 25.10 7 6 82.99 0 ——– Plane number 8 ——– 0 Atoms Defining Plane Distance e.s.d. C31 (3) −0.0052 0.0022 C32 (3) 0.0041 0.0028 C33 (3) 0.0006 0.0035 C34 (3) −0.0010 0.0036 C35 (3) −0.0056 0.0036 C36 (3) 0.0085 0.0029 0 Additional Atoms Distance P2 (3) −0.1107 C1 (3) 0.1682 0 Mean deviation from plane is 0.0042 angstroms Chi-squared: 17.5 0 Dihedral angles between least-squares planes plane plane angle 8 1 63.49 8 2 27.72 8 3 63.94 8 4 0.00 8 5 88.58 8 6 27.72 8 7 63.94 0 ——- Plane number 9 ——– 0 Atoms Defining Plane Distance e.s.d. C41 (3) −0.0039 0.0023 C42 (3) 0.0026 0.0027 C43 (3) 0.0038 0.0033 C44 (3) −0.0087 0.0038 C45 (3) 0.0025 0.0041 C46 (3) 0.0046 0.0031 0 Additional Atoms Distance P2 (3) −0.1321 C1 (3) −1.6443 0 Mean deviation from plane is 0.0044 angstroms Chi-squared: 12.4 0 Dihedral angles between least-squares planes plane plane angle 9 1 92.85 9 2 104.04 9 3 25.10 9 4 88.58 9 5 0.00 9 6 104.04 9 7 25.10 9 8 88.58

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.00000 (2)	0.00000 (2)	0.00000 (2)	2.89 (2)
P1	0.00278 (6)	0.06311 (4)	−0.14818 (5)	2.92 (3)
P2	−0.18977 (6)	0.05440 (4)	−0.07613 (6)	2.90 (3)
C1	−0.1284 (3)	0.12426 (16)	−0.1482 (2)	3.1 (1)
C11	0.1363 (2)	0.11841 (17)	−0.1532 (2)	3.4 (1)
C12	0.1711 (4)	0.1833 (2)	−0.0934 (3)	5.9 (2)
C13	0.2779 (4)	0.2231 (3)	−0.0931 (4)	7.3 (2)
C14	0.3479 (4)	0.1967 (3)	−0.1519 (3)	6.6 (2)
C15	0.3130 (3)	0.1337 (3)	−0.2120 (3)	5.6 (2)
C16	0.2075 (3)	0.0941 (2)	−0.2128 (3)	4.5 (1)
C21	−0.0539 (3)	0.01166 (15)	−0.2768 (2)	3.2 (1)
C22	−0.1176 (3)	0.0485 (2)	−0.3760 (3)	4.5 (1)
C23	−0.1603 (4)	0.0087 (3)	−0.4739 (3)	6.0 (2)
C24	−0.1407 (5)	−0.0666 (3)	−0.4730 (4)	6.6 (2)
C25	−0.0780 (5)	−0.1030 (3)	−0.3770 (4)	7.2 (2)
C26	−0.0332 (4)	−0.0642 (2)	−0.2782 (3)	5.2 (2)
C31	−0.2759 (2)	0.09965 (16)	0.0001 (2)	3.2 (1)
C32	−0.2709 (3)	0.1760 (2)	0.0182 (3)	4.3 (1)
C33	−0.3327 (4)	0.2065 (2)	0.0834 (3)	5.7 (2)
C34	−0.3987 (4)	0.1626 (3)	0.1288 (3)	6.1 (2)
C35	−0.4050 (4)	0.0863 (3)	0.1112 (3)	5.7 (2)
C36	−0.3448 (3)	0.0550 (2)	0.0457 (3)	4.4 (1)
C41	−0.3027 (2)	−0.00250 (15)	−0.1822 (2)	3.1 (1)
C42	−0.4039 (3)	0.0321 (2)	−0.2644 (3)	4.1 (1)
C43	−0.4859 (3)	−0.0090 (3)	−0.3504 (3)	5.5 (2)
C44	−0.4674 (4)	−0.0847 (3)	−0.3554 (3)	6.4 (2)
C45	−0.3695 (4)	−0.1196 (3)	−0.2746 (4)	6.6 (2)
C46	−0.2858 (3)	−0.0784 (2)	−0.1867 (3)	4.7 (1)
Cl	0.06093 (7)	0.26883 (4)	0.13398 (6)	4.1 (3)
O1	0.0351 (2)	0.19307 (12)	0.09475 (6)	4.8 (1)
O2	0.0946 (3)	0.27031 (16)	0.2509 (2)	7.1 (1)
O3	−0.0507 (3)	0.31392 (14)	0.0838 (3)	7.5 (1)
O4	0.1636 (2)	0.29876 (16)	0.1077 (2)	6.9 (1)
H1	−0.187 (3)	0.1438 (14)	−0.217 (2)	3.3 (6)*
H2	−0.095 (3)	0.1627 (16)	−0.098 (2)	3.5 (6)*
H3	0.125 (4)	0.205 (2)	−0.052 (3)	7 (1)*
H4	0.292 (4)	0.272 (2)	−0.051 (4)	8 (1)*
H5	0.412 (4)	0.226 (2)	−0.155 (3)	7 (1)*
H6	0.365 (4)	0.115 (2)	−0.257 (3)	7 (1)*
H7	0.189 (3)	0.0529 (18)	−0.249 (3)	4.7 (8)*
H8	−0.134 (3)	0.1013 (19)	−0.375 (3)	4.8 (8)*
H9	−0.197 (4)	0.036 (2)	−0.536 (3)	6.0 (9)*
H10	−0.174 (4)	−0.091 (2)	−0.541 (4)	8 (1)*
H11	−0.063 (5)	−0.155 (3)	−0.370 (4)	11 (2)*
H12	0.004 (3)	−0.0904 (18)	−0.212 (3)	5.0 (8)*
H13	−0.229 (3)	0.2060 (16)	−0.014 (2)	3.8 (7)*
H14	−0.325 (4)	0.258 (2)	0.099 (3)	6 (1)*
H15	−0.442 (4)	0.181 (2)	0.179 (3)	8 (1)*
H16	−0.445 (3)	0.053 (2)	0.139 (3)	5.5 (8)*
H17	−0.348 (3)	0.0021 (18)	0.033 (3)	4.7 (8)*
H18	−0.418 (3)	0.082 (2)	−0.260 (3)	4.7 (8)*
H19	−0.561 (4)	0.0172 (18)	−0.410 (3)	5.8 (8)*
H20	−0.522 (4)	−0.112 (2)	−0.415 (3)	7 (1)*
H21	−0.350 (4)	−0.168 (3)	−0.276 (3)	8 (1)*
H22	−0.221 (3)	−0.102 (2)	−0.134 (3)	5.7 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0250 (2)	0.0554 (3)	0.0304 (2)	0.0019 (2)	0.01144 (19)	0.0068 (2)
P1	0.0301 (3)	0.0510 (4)	0.0312 (4)	−0.0005 (3)	0.0128 (3)	0.0040 (3)
P2	0.0261 (3)	0.0496 (4)	0.0346 (4)	0.0004 (3)	0.0114 (3)	0.0036 (3)
C1	0.0328 (14)	0.0471 (17)	0.0367 (15)	−0.0003 (12)	0.0133 (12)	0.0017 (13)
C11	0.0337 (14)	0.0621 (18)	0.0333 (14)	−0.0059 (13)	0.0127 (12)	0.0069 (13)
C12	0.069 (2)	0.095 (3)	0.078 (2)	−0.030 (2)	0.047 (2)	−0.026 (2)
C13	0.085 (3)	0.110 (3)	0.098 (3)	−0.056 (3)	0.052 (3)	−0.039 (3)
C14	0.054 (2)	0.129 (4)	0.072 (3)	−0.039 (2)	0.028 (2)	−0.002 (3)
C15	0.048 (2)	0.107 (3)	0.068 (2)	−0.009 (2)	0.0347 (18)	0.004 (2)
C16	0.0448 (18)	0.076 (2)	0.057 (2)	−0.0041 (17)	0.0284 (15)	−0.0007 (19)
C21	0.0382 (14)	0.0506 (18)	0.0366 (14)	−0.0036 (12)	0.0172 (12)	0.0017 (12)
C22	0.059 (2)	0.066 (2)	0.0395 (17)	0.0040 (17)	0.0107 (15)	0.0013 (15)
C23	0.076 (3)	0.103 (4)	0.0365 (19)	−0.003 (2)	0.0058 (18)	0.000 (2)
C24	0.104 (3)	0.092 (3)	0.058 (2)	−0.024 (3)	0.032 (2)	−0.028 (2)
C25	0.146 (4)	0.060 (3)	0.076 (3)	−0.004 (3)	0.049 (3)	−0.013 (2)
C26	0.093 (3)	0.057 (2)	0.053 (2)	0.006 (2)	0.032 (2)	0.0028 (17)
C31	0.0294 (13)	0.0566 (18)	0.0336 (14)	0.0009 (12)	0.0106 (11)	−0.0029 (12)
C32	0.0434 (17)	0.063 (2)	0.061 (2)	−0.0082 (15)	0.0258 (15)	−0.0101 (16)
C33	0.075 (2)	0.073 (3)	0.079 (3)	−0.007 (2)	0.042 (2)	−0.023 (2)
C34	0.076 (3)	0.102 (3)	0.073 (2)	−0.004 (2)	0.048 (2)	−0.019 (2)
C35	0.072 (2)	0.090 (3)	0.076 (2)	−0.011 (2)	0.051 (2)	−0.001 (2)
C36	0.0546 (19)	0.065 (2)	0.057 (2)	−0.0033 (16)	0.0318 (16)	−0.0001 (16)
C41	0.0302 (13)	0.0495 (16)	0.0407 (14)	−0.0011 (12)	0.0166 (11)	0.0021 (12)
C42	0.0370 (16)	0.062 (2)	0.0494 (18)	−0.0061 (15)	0.0086 (14)	0.0070 (16)
C43	0.050 (2)	0.103 (3)	0.048 (2)	−0.017 (2)	0.0088 (17)	0.000 (2)
C44	0.063 (3)	0.116 (4)	0.066 (3)	−0.030 (3)	0.027 (2)	−0.040 (3)
C45	0.075 (3)	0.063 (3)	0.118 (4)	−0.010 (2)	0.042 (3)	−0.037 (3)
C46	0.0473 (19)	0.054 (2)	0.073 (2)	0.0042 (16)	0.0173 (17)	−0.0056 (18)
Cl	0.0511 (4)	0.0580 (5)	0.0479 (4)	−0.0087 (3)	0.0185 (3)	−0.0067 (3)
O1	0.0602 (13)	0.0585 (14)	0.0643 (14)	−0.0058 (11)	0.0221 (11)	−0.0099 (11)
O2	0.121 (2)	0.102 (2)	0.0509 (15)	−0.0165 (17)	0.0357 (15)	−0.0113 (14)
O3	0.0703 (16)	0.0653 (16)	0.125 (2)	0.0097 (14)	0.0051 (16)	0.0106 (16)
O4	0.0798 (18)	0.106 (2)	0.095 (2)	−0.0428 (16)	0.0544 (16)	−0.0359 (16)

Geometric parameters (Å, º)

Ni—P2	2.2188 (5)	C42—C43	1.370 (5)
Ni—P2^i	2.2188 (5)	C43—C44	1.371 (6)
Ni—P1	2.2322 (5)	C44—C45	1.360 (6)
Ni—P1^i	2.2322 (5)	C45—C46	1.392 (5)
P1—C21	1.802 (3)	Cl—O4	1.419 (2)
P1—C11	1.815 (3)	Cl—O2	1.420 (3)
P1—C1	1.832 (3)	Cl—O3	1.430 (3)
P2—C31	1.803 (3)	Cl—O1	1.435 (2)
P2—C41	1.805 (3)	C1—H2	0.92 (3)
P2—C1	1.834 (3)	C1—H1	0.96 (3)
C11—C12	1.367 (5)	C12—H3	0.95 (4)
C11—C16	1.368 (4)	C13—H4	1.01 (4)
C12—C13	1.393 (5)	C14—H5	0.90 (4)
C13—C14	1.362 (6)	C15—H6	1.02 (4)
C14—C15	1.341 (6)	C16—H7	0.86 (3)
C15—C16	1.377 (5)	C22—H8	0.96 (3)
C21—C26	1.374 (4)	C23—H9	0.90 (4)
C21—C22	1.385 (4)	C24—H10	0.93 (4)
C22—C23	1.377 (5)	C25—H11	0.94 (5)
C23—C24	1.361 (6)	C26—H12	0.93 (3)
C24—C25	1.350 (6)	C32—H13	0.91 (3)
C25—C26	1.378 (5)	C33—H14	0.94 (4)
C31—C32	1.380 (4)	C34—H15	1.00 (4)
C31—C36	1.382 (4)	C35—H16	0.89 (3)
C32—C33	1.383 (5)	C36—H17	0.96 (3)
C33—C34	1.352 (5)	C42—H18	0.91 (3)
C34—C35	1.376 (6)	C43—H19	1.02 (4)
C35—C36	1.379 (5)	C44—H20	0.93 (4)
C41—C46	1.371 (4)	C45—H21	0.89 (4)
C41—C42	1.386 (4)	C46—H22	0.90 (3)
C1···O1	3.248 (4)	C32···O1	3.224 (4)
C1···O4^ii	3.456 (4)	C32···O2^ii	3.369 (4)
C1···O2^ii	3.459 (4)	C32···O3	3.370 (4)
C12···O1	3.314 (4)	C42···O3^ii	3.429 (4)
C12···O4	3.343 (5)	C42···O2^ii	3.531 (5)
C13···O4	3.554 (5)	C43···O3^ii	3.594 (5)
C14···O2^iii	3.481 (5)	C44···O3^iv	3.532 (5)
C25···O2^i	3.438 (6)	C46···O1^i	3.329 (4)
C26···O1^i	3.308 (4)
P2—Ni—P2	180.00 (3)	O4—Cl—O2	108.9 (2)
P2—Ni—P1	73.12 (3)	O4—Cl—O3	109.5 (2)
P2—Ni—P1	106.88 (3)	O4—Cl—O1	110.3 (1)
P2^i—Ni—P1	106.88 (3)	O2—Cl—O3	108.8 (2)
P2^i—Ni—P1	73.12 (3)	O2—Cl—O1	109.6 (2)
P1—Ni—P1	180.00 (2)	O3—Cl—O1	109.7 (1)
C21—P1—C11	105.3 (1)	H2—C1—H1	110.0 (2)
C21—P1—C1	106.8 (1)	H2—C1—P1	109.0 (2)
C21—P1—Ni	115.2 (1)	H2—C1—P2	106.0 (2)
C11—P1—C1	110.5 (1)	H1—C1—P1	120.0 (2)
C11—P1—Ni	125.03 (9)	H1—C1—P2	117.0 (2)
C1—P1—Ni	92.2 (1)	H3—C12—C11	124.0 (2)
C31—P2—C41	107.4 (1)	H3—C12—C13	115.0 (2)
C31—P2—C1	110.4 (1)	H4—C13—C14	127.0 (2)
C31—P2—Ni	124.91 (9)	H4—C13—C12	114.0 (3)
C41—P2—C1	106.6 (1)	H5—C14—C15	122.0 (3)
C41—P2—Ni	112.8 (1)	H5—C14—C13	117.0 (3)
C1—P2—Ni	92.57 (9)	H6—C15—C14	120.0 (2)
P1—C1—P2	92.6 (1)	H6—C15—C16	120.0 (2)
C12—C11—C16	118.8 (3)	H7—C16—C11	120.0 (2)
C12—C11—P1	120.62 (7)	H7—C16—C15	119.0 (2)
C16—C11—P1	120.5 (2)	H8—C22—C23	121.0 (2)
C11—C12—C13	120.1 (4)	H8—C22—C21	119.0 (2)
C14—C13—C12	119.6 (4)	H9—C23—C24	124.0 (2)
C15—C14—C13	120.5 (4)	H9—C23—C22	116.0 (2)
C14—C15—C16	120.3 (4)	H10—C24—C25	123.0 (3)
C11—C16—C15	120.7 (4)	H10—C24—C23	116.0 (3)
C26—C21—C22	119.2 (3)	H11—C25—C24	126.0 (3)
C26—C21—P1	120.6 (2)	H11—C25—C26	114.0 (3)
C22—C21—P1	120.2 (2)	H12—C26—C21	120.0 (5)
C23—C22—C21	119.8 (4)	H12—C26—C25	119.0 (5)
C24—C23—C22	120.0 (4)	H13—C32—C31	120.0 (5)
C25—C24—C23	120.8 (4)	H13—C32—C33	120.4 (5)
C24—C25—C26	120.3 (4)	H14—C33—C34	120.0 (5)
C21—C26—C25	120.0 (4)	H14—C33—C32	119.0 (5)
C32—C31—C36	119.3 (3)	H15—C34—C33	125.0 (5)
C32—C31—P2	122.6 (2)	H15—C34—C35	115.0 (5)
C36—C31—P2	118.0 (2)	H16—C35—C34	126.0 (5)
C31—C32—C33	119.6 (3)	H16—C35—C36	114.0 (5)
C34—C33—C32	120.8 (4)	H17—C36—C35	121.0 (5)
C33—C34—C35	120.3 (4)	H17—C36—C31	119.0 (5)
C34—C35—C36	119.6 (4)	H18—C42—C43	120.0 (5)
C35—C36—C31	120.3 (4)	H18—C42—C41	120.0 (5)
C46—C41—C42	119.6 (3)	H19—C43—C42	119.5 (5)
C46—C41—P2	121.2 (2)	H19—C43—C44	120.7 (5)
C42—C41—P2	119.1 (2)	H20—C44—C45	120.0 (5)
C43—C42—C41	120.4 (4)	H20—C44—C43	119.0 (5)
C42—C43—C44	119.8 (4)	H21—C45—C44	124.0 (5)
C45—C44—C43	120.5 (4)	H21—C45—C46	115.0 (5)
C44—C45—C46	120.2 (4)	H22—C46—C41	121.0 (5)
C41—C46—C45	119.5 (4)	H22—C46—C45	119.0 (5)
Ni—P2—C41—C46	20.5 (3)	C1—P1—C21—C26	−134.6 (3)
Ni—P2—C41—C42	−155.5 (2)	C1—P1—C21—C22	46.3 (3)
Ni—P2—C1—P1	25.1 (1)	C11—C12—C13—C14	−0.6 (7)
Ni—P2—C31—C32	96.3 (3)	C11—C16—C15—C14	0.5 (6)
Ni—P2—C31—C36	−80.9 (2)	C11—P1—C21—C26	107.9 (3)
Ni—P2—C41—C46	20.5 (3)	C11—P1—C21—C22	−71.2 (3)
Ni—P2—C41—C42	−155.5 (2)	C12—C11—C16—C15	0.5 (6)
Ni—P2—C1—P1	25.03 (9)	C12—C11—P1—C21	154.9 (3)
Ni—P1—C21—C26	−33.9 (3)	C12—C13—C14—C15	1.6 (8)
Ni—P1—C21—C22	147.0 (2)	C13—C14—C15—C16	−1.5 (7)
Ni—P1—C11—C12	−68.2 (3)	C13—C12—C11—C16	−0.5 (6)
Ni—P1—C11—C16	108.7 (2)	C16—C11—P1—C21	−28.2 (3)
Ni—P1—C1—P2	−24.9 (1)	C21—C26—C25—C24	0.9 (7)
Ni—P1—C21—C26	−33.9 (4)	C21—C22—C23—C24	0.5 (7)
Ni—P1—C21—C22	147.0 (3)	C22—C23—C24—C25	−1.0 (7)
Ni—P1—C11—C12	−68.3 (3)	C22—C21—C26—C25	−1.4 (6)
Ni—P1—C11—C16	108.7 (2)	C23—C24—C25—C26	0.3 (9)
Ni—P1—C1—P2	−24.86 (9)	C23—C22—C21—C26	0.7 (5)
P1—C21—C26—C25	179.5 (4)	C31—C32—C33—C34	−0.5 (6)
P1—C21—C22—C23	179.8 (8)	C31—C36—C35—C34	1.6 (6)
P1—C11—C16—C15	−176.5 (3)	C31—P2—C41—C46	−121.0 (3)
P1—C1—P2—C31	154.0 (1)	C31—P2—C41—C42	63.0 (3)
P1—C1—P2—C41	−89.68 (13)	C32—C31—C36—C35	−1.8 (5)
P1—Ni—P2—C31	−138.48 (12)	C32—C31—P2—C41	−128.2 (2)
P1—Ni—P2—C41	88.0 (1)	C32—C33—C34—C35	0.3 (7)
P1—Ni—P2—C1	−21.3 (1)	C33—C34—C35—C36	−0.8 (7)
P1—Ni—P2—C31	−138.48 (12)	C33—C32—C31—C36	1.3 (5)
P1—Ni—P2—C41	87.97 (9)	C36—C31—P2—C41	54.6 (3)
P1—Ni—P2—C1	−21.26 (9)	C1—P1—C11—C12	39.9 (3)
P2—C31—C32—C33	−175.9 (3)	C1—P1—C11—C16	−143.1 (2)
P2—C31—C36—C35	175.5 (3)	C1—P2—C31—C32	−12.3 (3)
P2—C41—C46—C45	−175.2 (3)	C1—P2—C31—C36	170.5 (2)
P2—C41—C42—C43	175.4 (3)	C1—P2—C41—C46	120.6 (3)
P2—C1—P1—C21	92.3 (1)	C1—P2—C41—C42	−55.3 (3)
P2—C1—P1—C11	−153.7 (1)	C41—C46—C45—C44	0.0 (3)
P2—Ni—P1—C21	−88.5 (1)	C41—C42—C43—C44	−0.4 (6)
P2—Ni—P1—C11	138.3 (1)	C42—C43—C44—C45	1.2 (6)
P2—Ni—P1—C1	21.3 (1)	C42—C41—C46—C45	0.8 (5)
P2—Ni—P1—C21	−88.46 (13)	C43—C42—C41—C46	−0.7 (5)
P2—Ni—P1—C11	138.35 (12)	C43—C44—C45—C46	−1.1 (6)
P2—Ni—P1—C1	21.27 (9)

Symmetry codes: (i) −x, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x−1/2, y−1/2, −z−1/2.