Bis­[1,3-bis­(di­phenyl­phosphino)­propane-κ2P,P′]­nickel(0)

Davies, S.C.; Duff, S.E.; Evans, D.J.

doi:10.1107/S1600536805005064

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 3| March 2005| Pages m571-m573

https://doi.org/10.1107/S1600536805005064

Bis[1,3-bis(diphenylphosphino)propane-κ²P,P′]nickel(0)

Sian C. Davies,^a ^* Samantha E. Duff ^a and David J. Evans ^a

^aDepartment of Biological Chemistry, John Innes Centre, Norwich Research Park, Colney, Norwich NR4 7UH, England
^*Correspondence e-mail: sianc.davies@bbsrc.ac.uk

(Received 9 February 2005; accepted 15 February 2005; online 26 February 2005)

The neutral title complex, [Ni(C₂₇H₂₆P₂)₂], contains a distorted tetrahedrally coordinated Ni⁰ atom lying on a twofold rotation axis. The bridging propane groups of the ligands are twisted by approximately 90° with respect to each other.

Comment

As part of our ongoing studies to synthesize nickel compounds relevant to the structure and function of the microbial nickel-containing enzyme acetyl–CoA synthase, a range of new starting materials is required (Duff et al., 2005 ; Evans, 2005 ). The title compound, (I), was obtained as a minor product from the attempted methylation of [NiCl₂(dppp)], where dppp is 1,3-bis(diphenylphosphino)propane. Nickel(0) diphosphine (diphos) compounds of the type [Ni(diphos)₂] were first prepared 45 years ago by Chatt & Hart (1960 ). Compound (I) has since been prepared by various methods (van Hecke & Horrocks, 1966 ; Giannoccaro & Vasapollo, 1983 ; Fisher & Alyea, 1989 ; Bricout et al., 1995 ), but its structure has not been reported until now.

In (I), the Ni atom, which lies on a twofold rotation axis, displays a distorted tetrahedral coordination geometry; bond lengths to the P atoms are as expected, while the P—Ni—P angles range from 99.52 (2)° within one dppp ligand to 120.49 (3)° between the ligands (see Table 1). The ligands are arranged unsymmetrically about the Ni atom, with P—Ni—P angles between the ligands of 106.38 (3) and 115.43 (3)°. The P atoms are also distorted tetrahedral, with angles ranging from 98.58 (9) to 122.21 (6)°; the trend is for angles involving the Ni atom and the ligating phenyl C atoms to be the largest and the angles involving the bridging C atoms and the ligating phenyl C atoms to be the smallest. The P—C—C and C—C—C angles about the bridging C atoms are also distorted, being slightly larger than the ideal tetrahedral value (see Table 1). Dimensions within the phenyl rings are not unusual.

Each molecule is arranged with the bridging propane groups twisted by approximately 90° with respect to each other, the angle between the normals to the NiP₂ planes being 92.44 (2)°. When viewed along the twofold rotation axis, three of the phenyl rings of each dppp ligand lie with their normals at approximately right angles to the crystallographic b axis. The normal to the fourth phenyl ring in each ligand is approximately parallel to the crystallographic b axis. The molecules are arranged in chains parallel to the crystallographic c axis, with four chains enclosing a channel parallel to the c axis with normal van der Waals contacts binding the molecules within and across the rows (see Fig. 2).

The structure of the related compound [Ni(dppe)₂], (II), where dppe is 1,2-bis(diphenylphosphino)ethane, has been reported previously (Hartung et al., 1989 ). The distorted tetrahedral coordination about the Ni atom is similar in both molecules, with bond lengths to the Ni atom in (II) lying in the range 2.152 (3)–2.177 (3) Å. Bond angles are slightly different in the two, due to the steric effects of an ethyl rather than a propyl bridging group; in complex (II), the P—Ni—P angles within ligands are 90.8 (1) and 90.1 (1)°, while interligand P—Ni—P angles lie between 113.8 (1) and 129.3 (1)°.

Figure 1
A view of (I

), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) −x, y, ½ − z.]

Figure 2
Packing diagram of (I

), viewed along the crystallographic c axis. Atoms are represented by arbitrary spheres. H atoms have been omitted.

Experimental

To a stirred slurry of [NiCl₂(dppp)] (0.20 g, 0.37 mmol) in tetrahydrofuran (13 ml) was added a solution of methyl magnesium iodide in diethyl ether (3 M solution, 1.6 ml, 4.8 mmol) and additional tetrahydrofuran (20 ml). After 2 d, the mixture was filtered, and the filtrate was allowed to stand for two weeks; the solvent was then removed in vacuo. The solid residue was washed with diethyl ether to give a mixture of a brown solid and orange crystals of (I).

Crystal data

[Ni(C₂₇H₂₆P₂)₂]
M_r = 883.55
Monoclinic, C2/c
a = 18.303 (6) Å
b = 13.212 (2) Å
c = 20.023 (4) Å
β = 109.67 (2)°
V = 4559 (2) Å³
Z = 4
D_x = 1.287 Mg m⁻³
Mo Kα radiation
Cell parameters from 25 reflections
θ = 10–11°
μ = 0.60 mm⁻¹
T = 293 (2) K
Rhomb, orange
0.67 × 0.52 × 0.24 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
ω/θ scans
Absorption correction: ψ scan (EMPABS; Sheldrick et al., 1977 ) T_min = 0.823, T_max = 0.865
7286 measured reflections
6631 independent reflections
4569 reflections with I > 2σ(I)
R_int = 0.008
θ_max = 30°
h = −1 → 25
k = −1 → 18
l = −28 → 28
3 standard reflections frequency: 167 min intensity decay: none

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.092
S = 1.07
6631 reflections
371 parameters
All H-atom parameters refined
w = 1/[σ²(F_o²) + (0.033P)² + 0.7751P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.003
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—P1	2.1752 (6)
Ni1—P1ⁱ	2.1753 (6)
Ni1—P2	2.1790 (6)
Ni1—P2ⁱ	2.1790 (6)
P1—C121	1.8413 (18)
P1—C111	1.8449 (18)
P1—C12	1.8484 (19)
P2—C21	1.8473 (19)
P2—C211	1.8486 (19)
P2—C221	1.8552 (19)

P1—Ni1—P1ⁱ	106.38 (3)
P1—Ni1—P2	99.52 (2)
P1ⁱ—Ni1—P2	115.43 (3)
P1—Ni1—P2ⁱ	115.43 (3)
P1ⁱ—Ni1—P2ⁱ	99.51 (2)
P2—Ni1—P2ⁱ	120.49 (3)
C121—P1—C111	100.36 (8)
C121—P1—C12	100.74 (9)
C111—P1—C12	98.71 (9)
C121—P1—Ni1	118.59 (6)
C111—P1—Ni1	119.59 (6)
C12—P1—Ni1	115.31 (7)
C21—P2—C211	98.92 (9)
C21—P2—C221	98.58 (9)
C211—P2—C221	99.78 (9)
C21—P2—Ni1	112.49 (7)
C211—P2—Ni1	122.21 (6)
C221—P2—Ni1	120.47 (7)
C1—C12—P1	113.75 (14)
C12—C1—C21	113.54 (17)
C1—C21—P2	113.02 (13)

Ni1—P1—C12—C1	−46.88 (17)
P1—C12—C1—C21	73.0 (2)
C12—C1—C21—P2	−78.6 (2)
C1—C21—P2—Ni1	55.34 (16)
Symmetry code: (i) $[-x,y,{\script{1\over 2}}-z]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992 ); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 Processing Program (Hursthouse, 1976 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536805005064/sj6048sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805005064/sj6048Isup2.hkl

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 Processing Program (Hursthouse, 1976); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

bis[1,3-bis(diphenylphosphino)propane]nickel(0) top

Crystal data top

[Ni(C₂₇H₂₆P₂)₂]	F(000) = 1856
M_r = 883.55	D_x = 1.287 Mg m⁻³
Monoclinic, C2/c	Mo_ Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 18.303 (6) Å	θ = 10–11°
b = 13.212 (2) Å	µ = 0.60 mm⁻¹
c = 20.023 (4) Å	T = 293 K
β = 109.67 (2)°	Rhomb, orange
V = 4559 (2) Å³	0.67 × 0.52 × 0.24 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	4569 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.008
Graphite monochromator	θ_max = 30°, θ_min = 1.5°
ω/θ scans	h = −1→25
Absorption correction: ψ scan (EMPABS; Sheldrick et al., 1977)	k = −1→18
T_min = 0.823, T_max = 0.865	l = −28→28
7286 measured reflections	3 standard reflections every 167 min
6631 independent reflections	intensity decay: none

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	All H-atom parameters refined
S = 1.07	w = 1/[σ²(F_o²) + (0.033P)² + 0.7751P] where P = (F_o² + 2F_c²)/3
6631 reflections	(Δ/σ)_max = 0.003
371 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

Experimental. Data were corrected for Lorentz polarization effects (Hursthouse, 1976), absorption by semiempirical ψ-scan methods (Sheldrick et al., 1977) and negative intensities by Bayesian statistics (French & Wilson, 1978).

French, S. & Wilson, K. (1978). Acta Cryst. A34, 517–525.

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.0000	−0.00211 (2)	0.2500	0.02603 (8)
P1	0.04468 (2)	−0.10075 (3)	0.34176 (2)	0.02942 (10)
P2	−0.08743 (2)	0.07975 (3)	0.28021 (2)	0.03126 (10)
C111	0.12759 (10)	−0.05877 (14)	0.41856 (9)	0.0344 (4)
C112	0.13913 (11)	0.04289 (16)	0.43062 (10)	0.0406 (4)
H112	0.1056 (13)	0.0891 (17)	0.3983 (12)	0.057 (7)*
C113	0.19995 (13)	0.07926 (18)	0.48799 (11)	0.0502 (5)
H113	0.2042 (14)	0.155 (2)	0.4927 (13)	0.074 (8)*
C114	0.25006 (13)	0.0130 (2)	0.53318 (11)	0.0570 (6)
H114	0.2924 (13)	0.0361 (17)	0.5729 (12)	0.057 (6)*
C115	0.23919 (15)	−0.0889 (2)	0.52262 (13)	0.0682 (7)
H115	0.2733 (16)	−0.141 (2)	0.5581 (14)	0.085 (8)*
C116	0.17854 (14)	−0.12530 (18)	0.46590 (12)	0.0567 (6)
H116	0.1697 (14)	−0.1929 (19)	0.4588 (12)	0.063 (7)*
C121	0.07722 (10)	−0.22882 (13)	0.32874 (8)	0.0333 (4)
C122	0.04587 (12)	−0.31772 (16)	0.34380 (11)	0.0457 (5)
H122	0.0055 (13)	−0.3146 (17)	0.3628 (12)	0.059 (7)*
C123	0.07029 (14)	−0.41097 (17)	0.32785 (13)	0.0565 (6)
H123	0.0494 (13)	−0.4704 (19)	0.3373 (12)	0.059 (7)*
C124	0.12711 (15)	−0.41724 (18)	0.29788 (12)	0.0570 (6)
H124	0.1449 (15)	−0.481 (2)	0.2875 (13)	0.075 (8)*
C125	0.16018 (14)	−0.33040 (18)	0.28383 (11)	0.0533 (5)
H125	0.1982 (14)	−0.3318 (19)	0.2608 (13)	0.073 (8)*
C126	0.13487 (12)	−0.23706 (16)	0.29849 (11)	0.0441 (4)
H126	0.1576 (12)	−0.1790 (16)	0.2872 (10)	0.049 (6)*
C12	−0.02427 (11)	−0.13028 (16)	0.38852 (10)	0.0387 (4)
H12A	−0.0594 (11)	−0.1765 (15)	0.3599 (10)	0.039 (5)*
H12B	0.0039 (12)	−0.1644 (16)	0.4323 (11)	0.051 (6)*
C1	−0.06657 (12)	−0.03820 (17)	0.40259 (10)	0.0419 (4)
H1A	−0.0319 (11)	0.0144 (14)	0.4246 (10)	0.033 (5)*
H1B	−0.0900 (12)	−0.0558 (15)	0.4353 (10)	0.045 (6)*
C21	−0.12839 (10)	0.00308 (16)	0.33623 (10)	0.0383 (4)
H21A	−0.1655 (12)	0.0442 (16)	0.3475 (10)	0.042 (5)*
H21B	−0.1575 (12)	−0.0511 (16)	0.3064 (11)	0.045 (6)*
C211	−0.17899 (10)	0.12446 (15)	0.21406 (9)	0.0381 (4)
C212	−0.19222 (13)	0.22572 (17)	0.19513 (12)	0.0478 (5)
H212	−0.1570 (11)	0.2741 (15)	0.2186 (10)	0.041 (6)*
C213	−0.26050 (16)	0.2561 (2)	0.14274 (13)	0.0605 (6)
H213	−0.2650 (15)	0.328 (2)	0.1318 (13)	0.074 (8)*
C214	−0.31584 (15)	0.1867 (2)	0.10910 (13)	0.0659 (7)
H214	−0.3636 (17)	0.204 (2)	0.0721 (15)	0.095 (9)*
C215	−0.30412 (14)	0.0864 (2)	0.12650 (13)	0.0610 (6)
H215	−0.3406 (16)	0.034 (2)	0.1062 (15)	0.084 (9)*
C216	−0.23574 (12)	0.05534 (18)	0.17845 (11)	0.0469 (5)
H216	−0.2283 (13)	−0.0155 (17)	0.1895 (11)	0.054 (7)*
C221	−0.06057 (11)	0.19386 (14)	0.33727 (10)	0.0407 (4)
C222	0.00923 (14)	0.24073 (16)	0.34617 (13)	0.0509 (5)
H222	0.0392 (14)	0.2186 (19)	0.3225 (13)	0.069 (8)*
C223	0.03409 (19)	0.3226 (2)	0.39189 (17)	0.0753 (8)
H223	0.0810 (16)	0.349 (2)	0.3959 (14)	0.078 (9)*
C224	−0.0111 (2)	0.3577 (2)	0.42868 (17)	0.0862 (10)
H224	0.0044 (18)	0.409 (2)	0.4578 (16)	0.094 (10)*
C225	−0.0812 (2)	0.3138 (2)	0.41992 (17)	0.0876 (10)
H225	−0.1124 (18)	0.341 (2)	0.4459 (16)	0.103 (10)*
C226	−0.10644 (17)	0.2326 (2)	0.37443 (15)	0.0663 (7)
H226	−0.1560 (15)	0.199 (2)	0.3690 (13)	0.082 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02445 (14)	0.02904 (15)	0.02616 (14)	0.000	0.01059 (11)	0.000
P1	0.0278 (2)	0.0329 (2)	0.0280 (2)	0.00107 (17)	0.00993 (16)	0.00261 (17)
P2	0.0289 (2)	0.0340 (2)	0.0336 (2)	0.00280 (17)	0.01413 (17)	−0.00095 (18)
C111	0.0335 (9)	0.0417 (10)	0.0273 (8)	0.0000 (7)	0.0093 (7)	0.0011 (7)
C112	0.0436 (10)	0.0457 (11)	0.0313 (9)	−0.0015 (9)	0.0110 (8)	0.0024 (8)
C113	0.0575 (13)	0.0526 (13)	0.0406 (10)	−0.0115 (11)	0.0167 (10)	−0.0071 (10)
C114	0.0456 (12)	0.0739 (17)	0.0404 (11)	−0.0060 (11)	0.0000 (9)	−0.0150 (11)
C115	0.0611 (15)	0.0683 (17)	0.0513 (13)	0.0150 (13)	−0.0124 (11)	−0.0063 (12)
C116	0.0598 (14)	0.0455 (12)	0.0473 (12)	0.0082 (11)	−0.0051 (10)	−0.0029 (10)
C121	0.0341 (9)	0.0337 (9)	0.0281 (8)	0.0029 (7)	0.0051 (7)	0.0021 (7)
C122	0.0453 (11)	0.0382 (10)	0.0521 (11)	0.0005 (9)	0.0144 (9)	0.0064 (9)
C123	0.0609 (14)	0.0353 (11)	0.0638 (14)	−0.0009 (10)	0.0085 (12)	0.0059 (10)
C124	0.0652 (15)	0.0409 (12)	0.0541 (13)	0.0170 (11)	0.0058 (11)	−0.0035 (10)
C125	0.0560 (13)	0.0559 (14)	0.0495 (12)	0.0181 (11)	0.0196 (10)	−0.0004 (10)
C126	0.0451 (11)	0.0450 (11)	0.0440 (10)	0.0027 (9)	0.0173 (9)	0.0016 (9)
C12	0.0372 (10)	0.0452 (11)	0.0372 (9)	−0.0001 (8)	0.0172 (8)	0.0089 (8)
C1	0.0436 (11)	0.0547 (12)	0.0346 (9)	0.0010 (9)	0.0227 (8)	0.0032 (9)
C21	0.0343 (9)	0.0457 (11)	0.0414 (9)	0.0031 (9)	0.0214 (8)	0.0014 (9)
C211	0.0342 (9)	0.0468 (11)	0.0377 (9)	0.0108 (8)	0.0180 (8)	0.0013 (8)
C212	0.0477 (12)	0.0490 (12)	0.0515 (12)	0.0092 (10)	0.0231 (10)	0.0072 (10)
C213	0.0672 (16)	0.0634 (16)	0.0570 (13)	0.0298 (13)	0.0291 (12)	0.0210 (12)
C214	0.0538 (14)	0.093 (2)	0.0480 (13)	0.0289 (14)	0.0132 (11)	0.0053 (13)
C215	0.0432 (12)	0.0832 (19)	0.0508 (12)	0.0117 (13)	0.0080 (10)	−0.0121 (13)
C216	0.0392 (10)	0.0542 (13)	0.0456 (11)	0.0085 (9)	0.0121 (9)	−0.0055 (10)
C221	0.0448 (10)	0.0371 (10)	0.0412 (10)	0.0045 (8)	0.0158 (8)	−0.0046 (8)
C222	0.0527 (13)	0.0392 (11)	0.0606 (13)	−0.0006 (10)	0.0186 (11)	−0.0066 (10)
C223	0.0733 (18)	0.0480 (14)	0.095 (2)	−0.0121 (14)	0.0153 (16)	−0.0154 (14)
C224	0.117 (3)	0.0536 (17)	0.083 (2)	−0.0052 (18)	0.0271 (19)	−0.0309 (15)
C225	0.128 (3)	0.0631 (18)	0.090 (2)	0.0032 (19)	0.060 (2)	−0.0292 (16)
C226	0.0747 (17)	0.0596 (15)	0.0774 (17)	−0.0023 (13)	0.0426 (14)	−0.0234 (13)

Geometric parameters (Å, º) top

Ni1—P1	2.1752 (6)	C126—H126	0.94 (2)
Ni1—P1ⁱ	2.1753 (6)	C12—C1	1.519 (3)
Ni1—P2	2.1790 (6)	C12—H12A	0.93 (2)
Ni1—P2ⁱ	2.1790 (6)	C12—H12B	0.97 (2)
P1—C121	1.8413 (18)	C1—C21	1.527 (3)
P1—C111	1.8449 (18)	C1—H1A	0.944 (19)
P1—C12	1.8484 (19)	C1—H1B	0.93 (2)
P2—C21	1.8473 (19)	C21—H21A	0.95 (2)
P2—C211	1.8486 (19)	C21—H21B	0.97 (2)
P2—C221	1.8552 (19)	C211—C216	1.387 (3)
C111—C112	1.369 (3)	C211—C212	1.389 (3)
C111—C116	1.395 (3)	C212—C213	1.393 (3)
C112—C113	1.389 (3)	C212—H212	0.92 (2)
C112—H112	0.95 (2)	C213—C214	1.364 (4)
C113—C114	1.366 (3)	C213—H213	0.97 (3)
C113—H113	1.00 (3)	C214—C215	1.369 (4)
C114—C115	1.368 (3)	C214—H214	0.96 (3)
C114—H114	0.95 (2)	C215—C216	1.393 (3)
C115—C116	1.380 (3)	C215—H215	0.95 (3)
C115—H115	1.03 (3)	C216—H216	0.96 (2)
C116—H116	0.91 (2)	C221—C222	1.376 (3)
C121—C122	1.384 (3)	C221—C226	1.393 (3)
C121—C126	1.386 (3)	C222—C223	1.390 (3)
C122—C123	1.384 (3)	C222—H222	0.89 (2)
C122—H122	0.94 (2)	C223—C224	1.361 (4)
C123—C124	1.367 (4)	C223—H223	0.91 (3)
C123—H123	0.92 (2)	C224—C225	1.365 (5)
C124—C125	1.370 (3)	C224—H224	0.87 (3)
C124—H124	0.95 (3)	C225—C226	1.381 (4)
C125—C126	1.383 (3)	C225—H225	0.96 (3)
C125—H125	0.95 (3)	C226—H226	0.98 (3)

P1—Ni1—P1ⁱ	106.38 (3)	C1—C12—P1	113.75 (14)
P1—Ni1—P2	99.52 (2)	C1—C12—H12A	110.4 (12)
P1ⁱ—Ni1—P2	115.43 (3)	P1—C12—H12A	106.0 (12)
P1—Ni1—P2ⁱ	115.43 (3)	C1—C12—H12B	110.8 (12)
P1ⁱ—Ni1—P2ⁱ	99.51 (2)	P1—C12—H12B	108.1 (12)
P2—Ni1—P2ⁱ	120.49 (3)	H12A—C12—H12B	107.5 (17)
C121—P1—C111	100.36 (8)	C12—C1—C21	113.54 (17)
C121—P1—C12	100.74 (9)	C12—C1—H1A	111.8 (11)
C111—P1—C12	98.71 (9)	C21—C1—H1A	109.2 (11)
C121—P1—Ni1	118.59 (6)	C12—C1—H1B	108.5 (13)
C111—P1—Ni1	119.59 (6)	C21—C1—H1B	108.8 (13)
C12—P1—Ni1	115.31 (7)	H1A—C1—H1B	104.7 (17)
C21—P2—C211	98.92 (9)	C1—C21—P2	113.02 (13)
C21—P2—C221	98.58 (9)	C1—C21—H21A	112.1 (12)
C211—P2—C221	99.78 (9)	P2—C21—H21A	107.3 (12)
C21—P2—Ni1	112.49 (7)	C1—C21—H21B	111.4 (12)
C211—P2—Ni1	122.21 (6)	P2—C21—H21B	106.4 (12)
C221—P2—Ni1	120.47 (7)	H21A—C21—H21B	106.2 (17)
C112—C111—C116	118.06 (18)	C216—C211—C212	117.54 (19)
C112—C111—P1	118.49 (14)	C216—C211—P2	119.96 (15)
C116—C111—P1	123.44 (16)	C212—C211—P2	122.40 (16)
C111—C112—C113	121.25 (19)	C211—C212—C213	120.8 (2)
C111—C112—H112	119.0 (13)	C211—C212—H212	120.2 (13)
C113—C112—H112	119.7 (13)	C213—C212—H212	118.9 (13)
C114—C113—C112	119.9 (2)	C214—C213—C212	120.5 (2)
C114—C113—H113	124.1 (14)	C214—C213—H213	123.5 (15)
C112—C113—H113	116.0 (14)	C212—C213—H213	116.0 (16)
C113—C114—C115	119.9 (2)	C213—C214—C215	119.9 (2)
C113—C114—H114	121.5 (14)	C213—C214—H214	123.7 (18)
C115—C114—H114	118.6 (14)	C215—C214—H214	116.4 (18)
C114—C115—C116	120.3 (2)	C214—C215—C216	120.0 (3)
C114—C115—H115	121.5 (15)	C214—C215—H215	124.4 (17)
C116—C115—H115	118.0 (15)	C216—C215—H215	115.6 (17)
C115—C116—C111	120.6 (2)	C211—C216—C215	121.3 (2)
C115—C116—H116	121.4 (15)	C211—C216—H216	120.0 (13)
C111—C116—H116	118.0 (15)	C215—C216—H216	118.8 (13)
C122—C121—C126	117.44 (18)	C222—C221—C226	117.7 (2)
C122—C121—P1	124.83 (15)	C222—C221—P2	119.18 (15)
C126—C121—P1	117.65 (14)	C226—C221—P2	123.04 (17)
C123—C122—C121	121.0 (2)	C221—C222—C223	121.3 (2)
C123—C122—H122	119.4 (14)	C221—C222—H222	119.8 (16)
C121—C122—H122	119.5 (14)	C223—C222—H222	119.0 (17)
C124—C123—C122	120.5 (2)	C224—C223—C222	119.9 (3)
C124—C123—H123	117.9 (15)	C224—C223—H223	123.1 (18)
C122—C123—H123	121.5 (15)	C222—C223—H223	117.0 (18)
C123—C124—C125	119.6 (2)	C223—C224—C225	120.1 (3)
C123—C124—H124	121.2 (16)	C223—C224—H224	120 (2)
C125—C124—H124	119.3 (16)	C225—C224—H224	120 (2)
C124—C125—C126	120.0 (2)	C224—C225—C226	120.4 (3)
C124—C125—H125	121.8 (16)	C224—C225—H225	118.4 (19)
C126—C125—H125	118.0 (16)	C226—C225—H225	121.2 (19)
C125—C126—C121	121.4 (2)	C225—C226—C221	120.6 (3)
C125—C126—H126	118.1 (13)	C225—C226—H226	121.0 (16)
C121—C126—H126	120.5 (13)	C221—C226—H226	118.3 (16)

Ni1—P1—C12—C1	−46.88 (17)	C12—C1—C21—P2	−78.6 (2)
P1—C12—C1—C21	73.0 (2)	C1—C21—P2—Ni1	55.34 (16)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

The BBSRC (UK) and the John Innes Foundation (SED) are thanked for financial support.

References

Bricout, H., Carpentier, J.-F. & Mortreux, A. (1995). J. Chem. Soc. Chem Commun. pp. 1863–1864. CrossRef Web of Science Google Scholar
Chatt, J. & Hart, F. A. (1960). J. Chem. Soc. pp. 1378–1389. CrossRef Web of Science Google Scholar
Duff, S. E., Barclay, J. E., Davies, S. C. & Evans, D. J. (2005). Inorg. Chem. Commun. 8, 170–173. Web of Science CSD CrossRef CAS Google Scholar
Enraf–Nonius (1992). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Evans, D. J. (2005). Coord. Chem. Rev. In the press. (Available online at www.sciencedirect.com; doi:10.1016/j.ccr.2004.09.012.) Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fisher, K. J. & Alyea, E. C. (1989). Polyhedron, 8, 13–15. CrossRef CAS Web of Science Google Scholar
Giannoccaro, P. & Vasapollo, G. (1983). Inorg. Chim. Acta, 72, 51–55. CrossRef CAS Web of Science Google Scholar
Hartung, H., Baumeister, U., Walther, B. & Maschmeier, M. (1989). Z. Anorg. Allg. Chem. 578, 177–184. CSD CrossRef CAS Web of Science Google Scholar
Hecke, G. R. van & Horrocks, W. D. Jr (1966). Inorg. Chem. pp. 1968–1974. Google Scholar
Hursthouse, M. B. (1976). CAD-4 Processing Program. Queen Mary College, London. Google Scholar
Sheldrick, G. M., Orpen, A. G., Reichert, B. E. & Raithby, P. R. (1977). EMPABS. 4th European Crystallographic Meeting, Oxford. Abstracts, p. 147. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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Volume 61| Part 3| March 2005| Pages m571-m573

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