Chloro­bis­(tri­phenyl­phosphine)­nickel(I)

Crystals of the title compound, [NiCl(C₁₈H₁₅P)₂], contain one mol­ecule per asymmetric unit with no short intermolecular interactions. This is noteworthy since previous studies have reported that the formally 15-electron species oligomerizes in the solid state. The nickel(I) centre has a distorted trigonal-planar coordination geometry, the origin of which is suggested to be electronic in nature.

S1. Comment

Although little evidence has been presented to confirm the existence of a nickel(II)–boryl compound, nickel(0) (Suginome et al., 1998) and nickel(II) (Gridnev et al., 1993) complexes have been shown to catalyse certain alkyne boration reactions by mechanisms which are proposed to involve such species. As part of our continuing studies into the syntheses of transition metal–boryl complexes, we therefore attempted a direct stoichiometric preparation. The reaction between B-chlorocatecholborane and bis(triphenylphosphine)ethenenickel(0) failed to afford the desired oxidative–addition product, instead yielding bis(triphenylphosphine)nickel(I) chloride, (I), and tris(triphenylphosphine)nickel(I) chloride as part of a product mixture (Whittell, 2000).

Complexes of nickel(I) are far less numerous than those of either nickel(0) or nickel(II), with most of those isolated as solids containing phosphine or arsine ligands (Sacconi et al., 1987). Of those containing halide ions and monodentate phosphines, only [NiX(PPh₃)₃] (X = Cl, Br) had been characterized by X-ray crystallography prior to this study (Cassidy & Whitmire, 1991; Mealli et al., 1983). Both of these compounds dissociate in benzene solution to afford the title compound (Heimbach, 1964) and its bromide analogue (Porri et al., 1967), respectively, in addition to free triphenylphosphine. While this manuscript was in preparation, a new polymorph of [NiCl(PPh₃)₃] was reported, along with the crystal structure of a tetrahydrofuran (THF) solvate of (I) (Ellis & Spek, 2000). The latter contains no short intermolecular interactions. Although not characterized crystallographically, other compounds of the formulation [NiX(PR₃)₂] have been studied by different analytical techniques, but these are reported to be either oligomeric (X = Cl, Br; R = Ph; Lappert & Speier, 1974; Cundy & Nöth, 1971) or dimeric with a square-planar configuration (X = Cl, Br; R = Cy; Aresta et al., 1975) in the solid state.

Consistent with the findings of Ellis & Spek (2000), complex (I) is monomeric in the crystal, with the nickel(I) coordination geometry being best described as distorted trigonal–planar (Fig. 1). This is particularly noteworthy as the formally 15-electron species might well be expected to oligomerize, as previously suggested (Lappert & Speier, 1974). The Ni—Cl bond length [2.1669 (6) Å] is comparable to that observed in [NiCl(PPh₃)₂]·THF [2.1481 (6) Å], but significantly shorter than in both polymorphs of [NiCl(PPh₃)₃] [2.2785 (9) and 2.2933 (17) Å; Cassidy & Whitmire, 1991; Ellis & Spek, 2000]. The Ni—P distances [2.2532 (6) and 2.2393 (6) Å] and Cl—Ni—P angles [123.55 (2) and 121.13 (2)°] in (I) differ significantly from one another, and are also different to the corresponding parameters in [NiCl(PPh₃)₂]·THF [2.2091 (6) and 2.2012 (6) Å, and 126.98 (2) and 121.33 (2)°, respectively], which also has crystallographically independent triphenylphosphine ligands. This distortion of the trigonal plane is consistent with the chemical inequivalence of the phosphorus nuclei as suggested by electron spin resonance studies on a single-crystal of [CuBr(PPh₃)₂] doped with (I) (Nilges et al., 1977). A distorted trigonal–planar geometry is also apparent in [Ni{N(SiMe₃)₂}(PPh₃)₂] (Bradley et al., 1972), although the Ni—P bond lengths [2.220 (4) and 2.213 (4) Å] are equivalent. These, however, are both significantly shorter than those in (I) and longer than in [NiCl(PPh₃)₂]·THF. Nonetheless, common to all three complexes is a contraction of the P—Ni—P angle relative to the ideal value (120°); 114.95 (2), 111.52 (2) and 107.0 (2)° for (I), [NiCl(PPh₃)₂]·THF and [Ni{N(SiMe₃)₂}(PPh₃)₂], respectively. A review article by Eller et al. (1977) inferred this to mean, in the case of the Ni^I–amide complex, that the amide was of larger steric bulk than the triphenylphosphine ligands, an assertion which is not consistent with the presence of this same structural feature in both (I) and [NiCl(PPh₃)₂]·THF. Consideration of steric factors alone would predict a P—Ni—P angle for all three complexes greater than 120°, as observed for the P—Cu—P angle [126.0 (1)°] in the copper(I) bromide analogue, [CuBr(PPh₃)₂] (Davis et al., 1973), the molecular structure of which would be expected to be determined solely by steric effects on account of the d¹⁰ electron configuration at copper. The angular distortion most probably arises from a first-order Jahn–Teller effect which, for a d⁹ metal complex, is expected to destabilize an ML₃ structure from D_{3 h} to C_2v symmetry (Albright et al., 1985).

S2. Experimental

All manipulations were conducted under an atmosphere of dry dinitrogen or in vacuo, using standard glove-box techniques. The solvents were dried over sodium and distilled under dinitrogen immediately prior to use. ClB(cat) (cat is 1,2-O₂C₆H₄) was purchased from commercial sources and used without further purification. [Ni(η-C₂H₄)(PPh₃)₂] was prepared in accordance with the literature (Schramm & Ibers, 1980). A solution of ClB(cat) (0.013 g, 0.084 mmol) in toluene (ca 1 ml) was prepared in a small sample vial and then transferred to a similar vessel containing [Ni(η-C₂H₄)(PPh₃)₂] (0.046 g, 0.076 mmol). After ca 5 min at room temperature, a cloudy dark-green solution resulted. Hexane (ca 4 ml) was then added to the reaction mixture, leading to the formation of a dark-green precipitate. This was allowed to settle prior to removal and filtration of the orange mother liquors. These were concentrated in vacuo to afford an orange oil, which was further diluted with toluene (ca 1 ml) and transferred to a small Schlenk tube. A hexane overlayer was added which, upon slow solvent diffusion at 251 K, afforded yellow crystals of (I) and orange crystals of [NiCl(PPh₃)₃]. The latter were shown by X-ray crystallography to be isomorphous with the polymorph reported by Ellis & Spek (2000).

S3. Refinement

H atoms were constrained to idealized geometries at a distance of 0.95 Å from their parent C atoms and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of the title compound with ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.

Chlorobis(triphenylphosphine)nickel(I)

Crystal data

[NiCl(C18H15P)2]	F(000) = 1284
Mr = 618.70	Dx = 1.388 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.0778 (11) Å	Cell parameters from 8192 reflections
b = 17.535 (2) Å	θ = 2–25°
c = 15.4159 (18) Å	µ = 0.88 mm^−1
β = 98.722 (8)°	T = 173 K
V = 2960.0 (6) Å^3	Plate, yellow
Z = 4	0.40 × 0.25 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer	6788 independent reflections
Radiation source: fine-focus sealed tube	4961 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→14
Tmin = 0.720, Tmax = 0.924	k = −22→22
18753 measured reflections	l = −20→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.034P)^2] where P = (Fo^2 + 2Fc^2)/3
6788 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. Unit-cell dimensions were determined from reflections taken from three sets of 30 frames (at 0.3° steps in ω) at 10 s per frame. A full hemisphere of reciprocal space was scanned by 0.3° ω steps at ϕ = 0, 90 and 180° and 20 s per frame, with the area detector held at 2θ = -27°. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed.

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.

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

	x	y	z	Uiso*/Ueq
Ni1	0.81960 (2)	0.196069 (12)	0.557896 (14)	0.01875 (7)
Cl1	0.82054 (4)	0.07281 (3)	0.56762 (3)	0.03381 (12)
P1	0.98846 (4)	0.26492 (3)	0.60546 (3)	0.01882 (11)
P2	0.65054 (4)	0.26491 (3)	0.51600 (3)	0.02017 (11)
C1	1.04768 (16)	0.32941 (10)	0.52857 (11)	0.0208 (4)
C2	0.96831 (18)	0.35570 (12)	0.45650 (13)	0.0347 (5)
H2	0.8853	0.3399	0.4483	0.042*
C3	1.0080 (2)	0.40445 (13)	0.39642 (15)	0.0484 (6)
H3	0.9523	0.4217	0.3473	0.058*
C4	1.1272 (2)	0.42818 (12)	0.40711 (14)	0.0398 (5)
H4	1.1545	0.4615	0.3655	0.048*
C5	1.20709 (19)	0.40317 (11)	0.47903 (14)	0.0354 (5)
H5	1.2895	0.4200	0.4873	0.042*
C6	1.16834 (17)	0.35405 (11)	0.53879 (13)	0.0307 (5)
H6	1.2246	0.3368	0.5875	0.037*
C11	1.11895 (16)	0.20166 (10)	0.64110 (11)	0.0205 (4)
C12	1.21097 (17)	0.22057 (11)	0.71007 (12)	0.0260 (4)
H12	1.2050	0.2662	0.7424	0.031*
C13	1.31122 (17)	0.17281 (11)	0.73151 (13)	0.0303 (5)
H13	1.3737	0.1859	0.7784	0.036*
C14	1.32003 (17)	0.10645 (11)	0.68483 (13)	0.0306 (5)
H14	1.3892	0.0743	0.6992	0.037*
C15	1.22874 (17)	0.08652 (11)	0.61731 (13)	0.0293 (4)
H15	1.2345	0.0404	0.5858	0.035*
C16	1.12844 (16)	0.13414 (10)	0.59558 (12)	0.0256 (4)
H16	1.0658	0.1204	0.5491	0.031*
C21	0.98375 (15)	0.32423 (10)	0.70235 (11)	0.0207 (4)
C22	0.94466 (17)	0.29060 (11)	0.77540 (12)	0.0291 (4)
H22	0.9234	0.2381	0.7739	0.035*
C23	0.93656 (18)	0.33313 (12)	0.85008 (12)	0.0328 (5)
H23	0.9105	0.3094	0.8995	0.039*
C24	0.96602 (17)	0.40968 (11)	0.85319 (12)	0.0296 (5)
H24	0.9593	0.4388	0.9042	0.036*
C25	1.00539 (17)	0.44373 (11)	0.78157 (12)	0.0289 (4)
H25	1.0264	0.4963	0.7836	0.035*
C26	1.01428 (16)	0.40136 (10)	0.70662 (12)	0.0250 (4)
H26	1.0415	0.4253	0.6578	0.030*
C31	0.64480 (16)	0.33238 (11)	0.42463 (11)	0.0232 (4)
C32	0.6162 (2)	0.40922 (11)	0.42925 (13)	0.0366 (5)
H32	0.5934	0.4294	0.4816	0.044*
C33	0.6208 (2)	0.45700 (13)	0.35750 (15)	0.0480 (6)
H33	0.6015	0.5096	0.3614	0.058*
C34	0.6530 (2)	0.42846 (14)	0.28090 (14)	0.0446 (6)
H34	0.6577	0.4615	0.2327	0.053*
C35	0.67834 (19)	0.35204 (13)	0.27457 (13)	0.0387 (5)
H35	0.6985	0.3320	0.2213	0.046*
C36	0.67456 (17)	0.30394 (12)	0.34581 (12)	0.0294 (4)
H36	0.6924	0.2513	0.3409	0.035*
C41	0.51249 (16)	0.20842 (10)	0.47999 (11)	0.0227 (4)
C42	0.51788 (17)	0.12966 (11)	0.47687 (12)	0.0279 (4)
H42	0.5929	0.1042	0.4961	0.033*
C43	0.41386 (18)	0.08744 (12)	0.44566 (13)	0.0327 (5)
H43	0.4185	0.0334	0.4424	0.039*
C44	0.30396 (18)	0.12399 (12)	0.41940 (12)	0.0334 (5)
H44	0.2330	0.0950	0.3986	0.040*
C45	0.29703 (17)	0.20234 (12)	0.42333 (12)	0.0322 (5)
H45	0.2211	0.2273	0.4059	0.039*
C46	0.40103 (17)	0.24491 (11)	0.45270 (12)	0.0289 (4)
H46	0.3963	0.2990	0.4542	0.035*
C51	0.61319 (16)	0.32193 (10)	0.60753 (11)	0.0210 (4)
C52	0.51643 (17)	0.30485 (10)	0.65235 (12)	0.0262 (4)
H52	0.4611	0.2651	0.6318	0.031*
C53	0.50072 (19)	0.34566 (11)	0.72674 (13)	0.0320 (5)
H53	0.4347	0.3335	0.7571	0.038*
C54	0.57992 (18)	0.40366 (11)	0.75712 (13)	0.0312 (5)
H54	0.5684	0.4314	0.8082	0.037*
C55	0.67622 (17)	0.42144 (11)	0.71310 (12)	0.0290 (4)
H55	0.7305	0.4617	0.7336	0.035*
C56	0.69326 (16)	0.38068 (10)	0.63953 (12)	0.0249 (4)
H56	0.7603	0.3926	0.6101	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01897 (13)	0.01748 (12)	0.01960 (12)	−0.00112 (10)	0.00228 (8)	0.00032 (9)
Cl1	0.0304 (3)	0.0192 (2)	0.0501 (3)	−0.0012 (2)	0.0008 (2)	0.0045 (2)
P1	0.0190 (2)	0.0192 (2)	0.0181 (2)	−0.00103 (19)	0.00204 (17)	−0.00008 (18)
P2	0.0181 (2)	0.0203 (2)	0.0218 (2)	−0.00096 (19)	0.00228 (18)	−0.00031 (19)
C1	0.0225 (10)	0.0192 (9)	0.0211 (9)	−0.0015 (8)	0.0051 (7)	−0.0011 (7)
C2	0.0269 (11)	0.0399 (12)	0.0350 (11)	−0.0106 (9)	−0.0030 (8)	0.0113 (10)
C3	0.0452 (15)	0.0539 (15)	0.0422 (13)	−0.0127 (12)	−0.0060 (11)	0.0246 (12)
C4	0.0451 (14)	0.0350 (12)	0.0411 (13)	−0.0067 (10)	0.0125 (10)	0.0127 (10)
C5	0.0267 (11)	0.0331 (12)	0.0487 (13)	−0.0045 (9)	0.0132 (9)	0.0052 (10)
C6	0.0240 (11)	0.0333 (11)	0.0342 (11)	−0.0010 (9)	0.0027 (8)	0.0066 (9)
C11	0.0194 (9)	0.0215 (9)	0.0207 (9)	−0.0026 (7)	0.0034 (7)	0.0033 (7)
C12	0.0266 (10)	0.0256 (10)	0.0249 (10)	−0.0013 (8)	0.0010 (8)	−0.0017 (8)
C13	0.0250 (11)	0.0335 (11)	0.0297 (11)	−0.0015 (9)	−0.0048 (8)	0.0033 (9)
C14	0.0248 (11)	0.0278 (11)	0.0389 (12)	0.0035 (9)	0.0043 (8)	0.0096 (9)
C15	0.0301 (11)	0.0250 (10)	0.0339 (11)	0.0024 (9)	0.0081 (8)	−0.0018 (9)
C16	0.0248 (10)	0.0275 (10)	0.0242 (10)	−0.0011 (8)	0.0023 (7)	−0.0007 (8)
C21	0.0184 (9)	0.0238 (10)	0.0192 (9)	−0.0010 (7)	0.0010 (7)	−0.0017 (7)
C22	0.0345 (12)	0.0275 (11)	0.0259 (10)	−0.0048 (9)	0.0068 (8)	−0.0001 (8)
C23	0.0381 (12)	0.0391 (12)	0.0221 (10)	−0.0021 (10)	0.0076 (8)	0.0009 (9)
C24	0.0302 (11)	0.0363 (12)	0.0212 (10)	0.0054 (9)	−0.0001 (8)	−0.0066 (8)
C25	0.0332 (11)	0.0235 (10)	0.0277 (10)	0.0000 (9)	−0.0021 (8)	−0.0038 (8)
C26	0.0269 (10)	0.0247 (10)	0.0230 (10)	−0.0005 (8)	0.0030 (7)	−0.0012 (8)
C31	0.0172 (9)	0.0275 (10)	0.0239 (10)	−0.0037 (8)	0.0002 (7)	0.0015 (8)
C32	0.0498 (14)	0.0302 (11)	0.0293 (11)	0.0051 (10)	0.0047 (9)	0.0032 (9)
C33	0.0683 (17)	0.0314 (12)	0.0408 (14)	0.0028 (12)	−0.0033 (12)	0.0104 (10)
C34	0.0460 (14)	0.0536 (15)	0.0306 (12)	−0.0127 (12)	−0.0054 (10)	0.0171 (11)
C35	0.0341 (12)	0.0561 (15)	0.0251 (11)	−0.0082 (11)	0.0016 (9)	0.0037 (10)
C36	0.0244 (10)	0.0373 (12)	0.0255 (10)	−0.0030 (9)	0.0008 (8)	−0.0017 (9)
C41	0.0204 (10)	0.0270 (10)	0.0207 (9)	−0.0024 (8)	0.0029 (7)	0.0006 (8)
C42	0.0223 (10)	0.0293 (11)	0.0316 (11)	−0.0010 (8)	0.0021 (8)	0.0013 (9)
C43	0.0324 (12)	0.0287 (11)	0.0365 (12)	−0.0087 (9)	0.0033 (9)	−0.0012 (9)
C44	0.0243 (11)	0.0466 (13)	0.0283 (11)	−0.0139 (10)	0.0014 (8)	−0.0002 (9)
C45	0.0202 (10)	0.0472 (13)	0.0285 (11)	−0.0012 (9)	0.0011 (8)	0.0048 (9)
C46	0.0263 (11)	0.0307 (11)	0.0288 (10)	0.0004 (9)	0.0016 (8)	0.0013 (8)
C51	0.0189 (9)	0.0216 (9)	0.0219 (9)	0.0036 (7)	0.0011 (7)	0.0024 (7)
C52	0.0268 (10)	0.0243 (10)	0.0279 (10)	−0.0021 (8)	0.0052 (8)	0.0014 (8)
C53	0.0358 (12)	0.0323 (11)	0.0310 (11)	−0.0008 (9)	0.0151 (9)	0.0038 (9)
C54	0.0405 (12)	0.0296 (11)	0.0246 (10)	0.0038 (10)	0.0089 (8)	−0.0026 (8)
C55	0.0294 (11)	0.0267 (11)	0.0299 (11)	0.0010 (9)	0.0014 (8)	−0.0043 (8)
C56	0.0198 (10)	0.0269 (10)	0.0283 (10)	0.0006 (8)	0.0050 (7)	−0.0012 (8)

Geometric parameters (Å, º)

Ni1—Cl1	2.1666 (6)	C24—H24	0.9500
Ni1—P2	2.2393 (5)	C25—C26	1.390 (2)
Ni1—P1	2.2536 (5)	C25—H25	0.9500
P1—C21	1.8274 (18)	C26—H26	0.9500
P1—C1	1.8302 (18)	C31—C32	1.388 (3)
P1—C11	1.8388 (18)	C31—C36	1.398 (3)
P2—C51	1.8273 (19)	C32—C33	1.395 (3)
P2—C31	1.8333 (19)	C32—H32	0.9500
P2—C41	1.8359 (18)	C33—C34	1.379 (3)
C1—C2	1.387 (2)	C33—H33	0.9500
C1—C6	1.391 (2)	C34—C35	1.376 (3)
C2—C3	1.380 (3)	C34—H34	0.9500
C2—H2	0.9500	C35—C36	1.390 (3)
C3—C4	1.371 (3)	C35—H35	0.9500
C3—H3	0.9500	C36—H36	0.9500
C4—C5	1.381 (3)	C41—C42	1.384 (2)
C4—H4	0.9500	C41—C46	1.398 (2)
C5—C6	1.376 (3)	C42—C43	1.393 (2)
C5—H5	0.9500	C42—H42	0.9500
C6—H6	0.9500	C43—C44	1.381 (3)
C11—C16	1.388 (2)	C43—H43	0.9500
C11—C12	1.397 (2)	C44—C45	1.378 (3)
C12—C13	1.390 (3)	C44—H44	0.9500
C12—H12	0.9500	C45—C46	1.390 (3)
C13—C14	1.379 (3)	C45—H45	0.9500
C13—H13	0.9500	C46—H46	0.9500
C14—C15	1.382 (3)	C51—C52	1.393 (3)
C14—H14	0.9500	C51—C56	1.400 (2)
C15—C16	1.390 (2)	C52—C53	1.385 (3)
C15—H15	0.9500	C52—H52	0.9500
C16—H16	0.9500	C53—C54	1.378 (3)
C21—C26	1.393 (2)	C53—H53	0.9500
C21—C22	1.397 (3)	C54—C55	1.384 (3)
C22—C23	1.386 (3)	C54—H54	0.9500
C22—H22	0.9500	C55—C56	1.378 (3)
C23—C24	1.381 (3)	C55—H55	0.9500
C23—H23	0.9500	C56—H56	0.9500
C24—C25	1.383 (3)
Cl1—Ni1—P1	121.12 (2)	C25—C24—H24	120.2
Cl1—Ni1—P2	123.56 (2)	C24—C25—C26	120.25 (18)
P1—Ni1—P2	114.94 (2)	C24—C25—H25	119.9
C21—P1—C1	103.60 (8)	C26—C25—H25	119.9
C21—P1—C11	102.58 (8)	C25—C26—C21	120.73 (18)
C1—P1—C11	102.91 (8)	C25—C26—H26	119.6
C21—P1—Ni1	116.47 (6)	C21—C26—H26	119.6
C1—P1—Ni1	118.79 (6)	C32—C31—C36	118.45 (18)
C11—P1—Ni1	110.50 (6)	C32—C31—P2	124.64 (15)
C51—P2—C31	104.75 (8)	C36—C31—P2	116.89 (15)
C51—P2—C41	104.65 (8)	C31—C32—C33	120.4 (2)
C31—P2—C41	100.70 (8)	C31—C32—H32	119.8
C51—P2—Ni1	110.47 (6)	C33—C32—H32	119.8
C31—P2—Ni1	119.97 (6)	C34—C33—C32	120.4 (2)
C41—P2—Ni1	114.72 (6)	C34—C33—H33	119.8
C2—C1—C6	117.97 (17)	C32—C33—H33	119.8
C2—C1—P1	118.57 (14)	C35—C34—C33	119.8 (2)
C6—C1—P1	123.46 (13)	C35—C34—H34	120.1
C3—C2—C1	121.05 (18)	C33—C34—H34	120.1
C3—C2—H2	119.5	C34—C35—C36	120.3 (2)
C1—C2—H2	119.5	C34—C35—H35	119.9
C4—C3—C2	120.42 (19)	C36—C35—H35	119.9
C4—C3—H3	119.8	C35—C36—C31	120.6 (2)
C2—C3—H3	119.8	C35—C36—H36	119.7
C3—C4—C5	119.2 (2)	C31—C36—H36	119.7
C3—C4—H4	120.4	C42—C41—C46	119.16 (16)
C5—C4—H4	120.4	C42—C41—P2	120.72 (13)
C6—C5—C4	120.60 (19)	C46—C41—P2	120.09 (14)
C6—C5—H5	119.7	C41—C42—C43	120.33 (17)
C4—C5—H5	119.7	C41—C42—H42	119.8
C5—C6—C1	120.70 (18)	C43—C42—H42	119.8
C5—C6—H6	119.6	C44—C43—C42	120.07 (19)
C1—C6—H6	119.6	C44—C43—H43	120.0
C16—C11—C12	119.00 (16)	C42—C43—H43	120.0
C16—C11—P1	118.67 (13)	C45—C44—C43	120.16 (18)
C12—C11—P1	122.28 (14)	C45—C44—H44	119.9
C13—C12—C11	120.16 (17)	C43—C44—H44	119.9
C13—C12—H12	119.9	C44—C45—C46	120.06 (18)
C11—C12—H12	119.9	C44—C45—H45	120.0
C14—C13—C12	120.09 (17)	C46—C45—H45	120.0
C14—C13—H13	120.0	C45—C46—C41	120.20 (19)
C12—C13—H13	120.0	C45—C46—H46	119.9
C13—C14—C15	120.32 (18)	C41—C46—H46	119.9
C13—C14—H14	119.8	C52—C51—C56	118.53 (17)
C15—C14—H14	119.8	C52—C51—P2	123.14 (14)
C14—C15—C16	119.78 (18)	C56—C51—P2	117.99 (14)
C14—C15—H15	120.1	C53—C52—C51	120.16 (18)
C16—C15—H15	120.1	C53—C52—H52	119.9
C11—C16—C15	120.64 (16)	C51—C52—H52	119.9
C11—C16—H16	119.7	C54—C53—C52	120.62 (19)
C15—C16—H16	119.7	C54—C53—H53	119.7
C26—C21—C22	118.32 (17)	C52—C53—H53	119.7
C26—C21—P1	123.67 (14)	C53—C54—C55	119.86 (19)
C22—C21—P1	117.99 (14)	C53—C54—H54	120.1
C23—C22—C21	120.63 (18)	C55—C54—H54	120.1
C23—C22—H22	119.7	C56—C55—C54	119.93 (18)
C21—C22—H22	119.7	C56—C55—H55	120.0
C24—C23—C22	120.48 (19)	C54—C55—H55	120.0
C24—C23—H23	119.8	C55—C56—C51	120.89 (18)
C22—C23—H23	119.8	C55—C56—H56	119.6
C23—C24—C25	119.59 (18)	C51—C56—H56	119.6
C23—C24—H24	120.2
Cl1—Ni1—P1—C21	−111.54 (7)	C21—C22—C23—C24	0.6 (3)
P2—Ni1—P1—C21	61.66 (7)	C22—C23—C24—C25	−0.9 (3)
Cl1—Ni1—P1—C1	123.48 (7)	C23—C24—C25—C26	0.6 (3)
P2—Ni1—P1—C1	−63.33 (7)	C24—C25—C26—C21	0.0 (3)
Cl1—Ni1—P1—C11	4.94 (7)	C22—C21—C26—C25	−0.3 (3)
P2—Ni1—P1—C11	178.14 (6)	P1—C21—C26—C25	178.16 (14)
Cl1—Ni1—P2—C51	112.48 (7)	C51—P2—C31—C32	−0.58 (18)
P1—Ni1—P2—C51	−60.53 (7)	C41—P2—C31—C32	107.84 (17)
Cl1—Ni1—P2—C31	−125.59 (7)	Ni1—P2—C31—C32	−125.28 (15)
P1—Ni1—P2—C31	61.40 (7)	C51—P2—C31—C36	177.73 (14)
Cl1—Ni1—P2—C41	−5.50 (7)	C41—P2—C31—C36	−73.85 (15)
P1—Ni1—P2—C41	−178.51 (6)	Ni1—P2—C31—C36	53.04 (15)
C21—P1—C1—C2	−107.73 (16)	C36—C31—C32—C33	−1.8 (3)
C11—P1—C1—C2	145.69 (16)	P2—C31—C32—C33	176.46 (16)
Ni1—P1—C1—C2	23.28 (18)	C31—C32—C33—C34	0.4 (3)
C21—P1—C1—C6	71.82 (17)	C32—C33—C34—C35	1.4 (3)
C11—P1—C1—C6	−34.76 (17)	C33—C34—C35—C36	−1.6 (3)
Ni1—P1—C1—C6	−157.17 (14)	C34—C35—C36—C31	0.1 (3)
C6—C1—C2—C3	0.4 (3)	C32—C31—C36—C35	1.6 (3)
P1—C1—C2—C3	179.97 (18)	P2—C31—C36—C35	−176.84 (14)
C1—C2—C3—C4	−0.2 (4)	C51—P2—C41—C42	−123.57 (16)
C2—C3—C4—C5	−0.4 (4)	C31—P2—C41—C42	127.93 (16)
C3—C4—C5—C6	1.0 (3)	Ni1—P2—C41—C42	−2.35 (17)
C4—C5—C6—C1	−0.8 (3)	C51—P2—C41—C46	58.45 (16)
C2—C1—C6—C5	0.1 (3)	C31—P2—C41—C46	−50.05 (17)
P1—C1—C6—C5	−179.42 (16)	Ni1—P2—C41—C46	179.67 (13)
C21—P1—C11—C16	160.61 (15)	C46—C41—C42—C43	1.0 (3)
C1—P1—C11—C16	−92.03 (16)	P2—C41—C42—C43	−177.04 (15)
Ni1—P1—C11—C16	35.79 (16)	C41—C42—C43—C44	−1.4 (3)
C21—P1—C11—C12	−21.88 (17)	C42—C43—C44—C45	0.5 (3)
C1—P1—C11—C12	85.48 (17)	C43—C44—C45—C46	0.8 (3)
Ni1—P1—C11—C12	−146.70 (14)	C44—C45—C46—C41	−1.3 (3)
C16—C11—C12—C13	1.0 (3)	C42—C41—C46—C45	0.4 (3)
P1—C11—C12—C13	−176.49 (14)	P2—C41—C46—C45	178.38 (15)
C11—C12—C13—C14	−0.1 (3)	C31—P2—C51—C52	123.00 (15)
C12—C13—C14—C15	−0.8 (3)	C41—P2—C51—C52	17.50 (17)
C13—C14—C15—C16	0.9 (3)	Ni1—P2—C51—C52	−106.49 (14)
C12—C11—C16—C15	−0.9 (3)	C31—P2—C51—C56	−63.77 (15)
P1—C11—C16—C15	176.66 (14)	C41—P2—C51—C56	−169.27 (13)
C14—C15—C16—C11	0.0 (3)	Ni1—P2—C51—C56	66.74 (14)
C1—P1—C21—C26	3.07 (17)	C56—C51—C52—C53	0.1 (3)
C11—P1—C21—C26	109.91 (15)	P2—C51—C52—C53	173.33 (14)
Ni1—P1—C21—C26	−129.30 (14)	C51—C52—C53—C54	0.3 (3)
C1—P1—C21—C22	−178.44 (14)	C52—C53—C54—C55	0.0 (3)
C11—P1—C21—C22	−71.60 (15)	C53—C54—C55—C56	−0.6 (3)
Ni1—P1—C21—C22	49.19 (15)	C54—C55—C56—C51	1.0 (3)
C26—C21—C22—C23	0.0 (3)	C52—C51—C56—C55	−0.8 (3)
P1—C21—C22—C23	−178.55 (15)	P2—C51—C56—C55	−174.31 (14)