{2,6-Bis[(di-tert-butyl­phosphino)­methyl]­phenyl}chloridonickel(II)

Boro, B.J.; Dickie, D.A.; Goldberg, K.I.; Kemp, R.A.

doi:10.1107/S1600536808029814

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1304

doi:10.1107/S1600536808029814

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{2,6-Bis[(di-tert-butylphosphino)methyl]phenyl}chloridonickel(II)

Brian J. Boro,^a Diane A. Dickie,^a Karen I. Goldberg ^b and Richard A. Kemp ^a ^*‡

^aDepartment of Chemistry and Chemical Biology, MSC03 2060, 1 University of New Mexico, Albuquerque, NM 87131, USA, and ^bDepartment of Chemistry and Biochemistry, University of Washington, Seattle, WA 98195, USA
^*Correspondence e-mail: rakemp@unm.edu

(Received 3 September 2008; accepted 16 September 2008; online 20 September 2008)

In the title compound, [Ni(C₂₄H₄₃P₂)Cl], the Ni atom adopts a distorted square-planar geometry, with the P atoms of the 2,6-bis[(di-tert-butylphosphino)methyl]phenyl ligand trans to one another. The P—Ni—P plane is twisted out of the plane of the aromatic ring by 21.97 (6)°.

Related literature

For the original synthesis and spectroscopic characterization of the title compound, see: Moulton & Shaw (1976 ). For the crystallographic characterization of the Pd analogue, see: Kimmich et al. (2002 ). For crystallographic characterization of the 2,6-bis[(di-tert-butylphosphino)methyl]benzene ligand, see: Hollink et al. (2003 ). For related literature, see: Denney et al. (2006 ); Keith et al. (2006 ).

Experimental

Crystal data

[Ni(C₂₄H₄₃P₂)Cl]
M_r = 487.68
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.3394 (4) Å
b = 15.0463 (5) Å
c = 15.4184 (5) Å
V = 2630.63 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 225 (2) K
0.50 × 0.50 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.622, T_max = 0.679
84881 measured reflections
10074 independent reflections
8461 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.09
10074 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.50 e Å⁻³
Absolute structure: Flack (1983 ), with 4507 Friedel pairs
Flack parameter: 0.006 (7)

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029814/pv2105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029814/pv2105Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was originally prepared by Moulton & Shaw (1976) but its crystal structure was not determined at that time. We have prepared (I) as part of our studies of PCP 'pincer' complexes of divalent late transition metals, which show promise as catalysts for the epoxidation of olefins (Denney et al., 2006; Keith et al., 2006).

In the molecular stucture of (I) (Fig. 1), the nickel adopts a square planar geometry, with the phosphorus atoms trans to one another. The Ni—P bond lengths 2.1921 (4) and 2.1978 (4) Å, are significantly shorter than the corresponding Pd—P bonds [2.3039 (6) and 2.3969 (6) Å] in the analogous palladium complex (Kimmich et al., 2002). Steric hindrance distorts the P—Ni—P bond angle to 169.651 (18)°, while the less constrained C—Ni—Cl angle is much closer to linearity at 176.13 (5)°.

Significant geometrical changes are observed in the 2,6-bis[(di-tert-butylphosphino)methyl]benzene ligand upon binding to nickel. In the free ligand (Hollink et al., 2003), the average P—C_methylene bond length is 1.870 Å, while in (I), it has decreased to 1.8308 (19) Å (P1—C8) and 1.8341 (18) Å (P2—C7). This bond shortening is accompanied by change in the P—C_methylene—C_phenyl angle, from 114.5° in the free ligand to 106.23 (12)° (P1—C8—C2) and 106.84 (12)° (P2—C7—C6) in (I).

Related literature top

For the original synthesis and spectroscopic characterization of the title compound, see: Moulton & Shaw (1976). For the crystallographic characterization of the Pd analogue, see: Kimmich et al. (2002). For crystallographic characterization of the 2,6-bis[(di-tert-butylphosphino)methyl]benzene ligand, see: Hollink et al. (2003). For related literature, see: Denney et al. (2006); Keith et al. (2006).

Experimental top

A solution of nickel chloride hexahydrate (0.6 g, 2.5 mmol) dissolved in 2 ml of degassed water was added to a solution of 2,6-bis-[(di-tert-butylphosphino)methyl]benzene (1.02 g, 2.6 mmol) in 10 ml ethanol. The solution was heated to reflux. A golden-yellow precipitate began to form only after 0.5 h. The solution was stirred under gentle reflux overnight. After cooling, the product was collected by filtration and washed with cold ethanol. It was recrystallized from a concentrated solution of pentane at 238 K.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. View of the title compound showing numbering scheme. Ellipsoids are shown at 50% probability and hydrogen atoms have been removed for clarity.

{2,6-Bis[(di-tert-butylphosphino)methyl]phenyl}chloridonickel(II) top

Crystal data top

[Ni(C₂₄H₄₃P₂)Cl]	F(000) = 1048
M_r = 487.68	D_x = 1.231 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8656 reflections
a = 11.3394 (4) Å	θ = 2.2–32.5°
b = 15.0463 (5) Å	µ = 0.97 mm⁻¹
c = 15.4184 (5) Å	T = 225 K
V = 2630.63 (15) Å³	Prism, gold-brown
Z = 4	0.50 × 0.50 × 0.40 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	10074 independent reflections
Radiation source: fine-focus sealed tube	8461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 33.2°, θ_min = 1.9°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2004)	h = −17→17
T_min = 0.622, T_max = 0.679	k = −23→23
84881 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0439P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.002
10074 reflections	Δρ_max = 0.32 e Å⁻³
265 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 4507 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (7)

Crystal data top

[Ni(C₂₄H₄₃P₂)Cl]	V = 2630.63 (15) Å³
M_r = 487.68	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.3394 (4) Å	µ = 0.97 mm⁻¹
b = 15.0463 (5) Å	T = 225 K
c = 15.4184 (5) Å	0.50 × 0.50 × 0.40 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	10074 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2004)	8461 reflections with I > 2σ(I)
T_min = 0.622, T_max = 0.679	R_int = 0.048
84881 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.32 e Å⁻³
S = 1.09	Δρ_min = −0.50 e Å⁻³
10074 reflections	Absolute structure: Flack (1983), with 4507 Friedel pairs
265 parameters	Absolute structure parameter: 0.006 (7)
0 restraints

Special details top

Experimental. Yield = 60%. ¹H NMR (250 MHz, C₆D₆) δ 7.00 (t, 1H, ³J_HH = 7.4 Hz, Ar-H_para), 6.84 (d, 2H, ³J_HH = 7.4 Hz, Ar-H_meta), 2.91 (virtual t, 4H, J_HP = 6.8 Hz, CH₂), 1.40 (virtual t, 36H, J_HP = 12.7 Hz, CH₃) p.p.m. ¹³C{¹H} NMR (63 MHz, C₆D₆) δ 155.7 (t, ²J_CP = 16.7 Hz, Ar-C_ipso), 153.0 (virtual t, J_CP = 25.5 Hz, Ar-C_ortho), 125.2 (s, Ar-C_para), 121.8 (virtual t, J_CP = 16.7 Hz, Ar-C_meta), 34.9 (virtual t, J_CP = 13.4 Hz, PCH₂), 34.3 (virtual t, J_CP = 22.7 Hz, PC(CH₃)₃), 29.8 (s, CH₃) p.p.m. ³¹P{¹H} NMR (101 MHz, C₆D₆) δ 66.9 p.p.m.

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	0.536566 (17)	0.968358 (13)	0.925683 (12)	0.02623 (5)
Cl1	0.60025 (5)	1.02689 (4)	0.80121 (3)	0.04914 (12)
P1	0.38227 (4)	0.90497 (3)	0.86644 (3)	0.02696 (8)
P2	0.67658 (4)	1.02487 (3)	1.00738 (3)	0.02786 (8)
C1	0.48595 (14)	0.91031 (10)	1.03045 (10)	0.0278 (3)
C2	0.37594 (16)	0.86671 (11)	1.03569 (11)	0.0326 (3)
C3	0.34528 (18)	0.81652 (13)	1.10805 (13)	0.0405 (4)
H3	0.2723	0.7869	1.1094	0.049*
C4	0.4201 (2)	0.80982 (13)	1.17718 (13)	0.0441 (5)
H4	0.3992	0.7750	1.2254	0.053*
C5	0.52717 (18)	0.85476 (12)	1.17589 (11)	0.0383 (4)
H5	0.5780	0.8516	1.2240	0.046*
C6	0.55930 (16)	0.90460 (11)	1.10322 (11)	0.0327 (3)
C7	0.67683 (17)	0.95101 (13)	1.10201 (12)	0.0391 (4)
H7A	0.7409	0.9076	1.0974	0.047*
H7B	0.6879	0.9854	1.1554	0.047*
C8	0.29202 (16)	0.87651 (14)	0.96090 (12)	0.0382 (4)
H8A	0.2345	0.9236	0.9727	0.046*
H8B	0.2494	0.8208	0.9508	0.046*
C9	0.41665 (16)	0.79598 (10)	0.81364 (12)	0.0339 (3)
C10	0.5097 (2)	0.80785 (14)	0.74313 (14)	0.0488 (5)
H10A	0.5784	0.8371	0.7674	0.073*
H10B	0.4776	0.8439	0.6966	0.073*
H10C	0.5322	0.7501	0.7205	0.073*
C11	0.3068 (2)	0.75117 (14)	0.77561 (15)	0.0497 (5)
H11A	0.2776	0.7861	0.7273	0.075*
H11B	0.2463	0.7471	0.8199	0.075*
H11C	0.3271	0.6920	0.7556	0.075*
C12	0.4694 (2)	0.73571 (12)	0.88360 (14)	0.0471 (5)
H12A	0.4934	0.6798	0.8577	0.071*
H12B	0.4108	0.7245	0.9281	0.071*
H12C	0.5374	0.7646	0.9093	0.071*
C13	0.28236 (17)	0.97553 (14)	0.79810 (13)	0.0422 (4)
C14	0.15386 (19)	0.94355 (18)	0.79892 (18)	0.0618 (6)
H14A	0.1057	0.9840	0.7651	0.093*
H14B	0.1252	0.9420	0.8582	0.093*
H14C	0.1494	0.8844	0.7740	0.093*
C15	0.3241 (2)	0.98364 (15)	0.70379 (13)	0.0539 (5)
H15A	0.3162	0.9266	0.6751	0.081*
H15B	0.4061	1.0020	0.7028	0.081*
H15C	0.2764	1.0275	0.6738	0.081*
C16	0.2868 (3)	1.06881 (15)	0.83988 (18)	0.0642 (7)
H16A	0.2328	1.1081	0.8098	0.096*
H16B	0.3663	1.0923	0.8357	0.096*
H16C	0.2643	1.0646	0.9004	0.096*
C17	0.83287 (16)	1.01907 (13)	0.96814 (12)	0.0369 (4)
C18	0.84152 (19)	0.92899 (15)	0.92080 (17)	0.0524 (5)
H18A	0.9217	0.9200	0.9007	0.079*
H18B	0.7882	0.9288	0.8716	0.079*
H18C	0.8201	0.8815	0.9604	0.079*
C19	0.92396 (18)	1.02033 (17)	1.04173 (15)	0.0514 (5)
H19A	1.0020	1.0103	1.0180	0.077*
H19B	0.9055	0.9739	1.0832	0.077*
H19C	0.9219	1.0776	1.0705	0.077*
C20	0.63680 (18)	1.13804 (12)	1.04915 (13)	0.0403 (4)
C21	0.5238 (2)	1.12685 (15)	1.10274 (17)	0.0593 (6)
H21A	0.5401	1.0901	1.1530	0.089*
H21B	0.4636	1.0987	1.0674	0.089*
H21C	0.4962	1.1847	1.1217	0.089*
C22	0.7314 (2)	1.17943 (16)	1.10738 (16)	0.0585 (6)
H22A	0.8020	1.1907	1.0735	0.088*
H22B	0.7500	1.1389	1.1543	0.088*
H22C	0.7023	1.2349	1.1312	0.088*
C23	0.6101 (3)	1.19968 (14)	0.97333 (16)	0.0571 (6)
H23A	0.5786	1.2553	0.9951	0.086*
H23B	0.5527	1.1719	0.9354	0.086*
H23C	0.6821	1.2111	0.9412	0.086*
C24	0.86278 (18)	1.09373 (16)	0.90427 (14)	0.0491 (5)
H24A	0.8597	1.1505	0.9340	0.074*
H24B	0.8062	1.0936	0.8571	0.074*
H24C	0.9414	1.0844	0.8812	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02964 (9)	0.02516 (9)	0.02389 (9)	−0.00470 (8)	−0.00320 (8)	0.00305 (7)
Cl1	0.0605 (3)	0.0569 (3)	0.02997 (19)	−0.0283 (3)	−0.00855 (19)	0.0151 (2)
P1	0.02591 (18)	0.02588 (17)	0.02911 (19)	−0.00090 (15)	−0.00127 (15)	−0.00323 (15)
P2	0.03048 (18)	0.02878 (18)	0.02431 (17)	−0.00396 (16)	−0.00252 (14)	0.00080 (16)
C1	0.0318 (8)	0.0261 (6)	0.0256 (7)	−0.0007 (6)	0.0043 (6)	0.0008 (6)
C2	0.0343 (8)	0.0312 (8)	0.0321 (8)	−0.0005 (7)	0.0090 (7)	−0.0036 (6)
C3	0.0416 (10)	0.0390 (9)	0.0411 (9)	−0.0050 (8)	0.0187 (8)	−0.0025 (8)
C4	0.0579 (12)	0.0399 (9)	0.0345 (9)	0.0028 (9)	0.0192 (9)	0.0076 (7)
C5	0.0465 (10)	0.0410 (9)	0.0273 (8)	0.0087 (8)	0.0051 (8)	0.0062 (7)
C6	0.0394 (9)	0.0319 (8)	0.0268 (7)	0.0021 (7)	0.0030 (6)	0.0027 (6)
C7	0.0393 (9)	0.0472 (10)	0.0309 (8)	−0.0033 (8)	−0.0079 (7)	0.0094 (7)
C8	0.0301 (8)	0.0469 (10)	0.0377 (9)	−0.0050 (7)	0.0061 (7)	−0.0095 (8)
C9	0.0396 (9)	0.0247 (7)	0.0375 (9)	−0.0030 (6)	0.0075 (7)	−0.0057 (6)
C10	0.0569 (13)	0.0432 (10)	0.0465 (11)	0.0010 (9)	0.0210 (9)	−0.0067 (8)
C11	0.0562 (12)	0.0374 (10)	0.0556 (12)	−0.0123 (9)	0.0036 (10)	−0.0146 (9)
C12	0.0604 (12)	0.0281 (8)	0.0529 (11)	0.0085 (9)	0.0101 (11)	0.0009 (7)
C13	0.0421 (9)	0.0404 (9)	0.0442 (10)	0.0116 (8)	−0.0140 (8)	−0.0054 (9)
C14	0.0352 (10)	0.0807 (17)	0.0696 (15)	0.0119 (10)	−0.0166 (10)	−0.0113 (13)
C15	0.0648 (14)	0.0528 (12)	0.0441 (11)	0.0079 (11)	−0.0195 (10)	0.0053 (9)
C16	0.0812 (18)	0.0433 (11)	0.0682 (16)	0.0299 (12)	−0.0268 (14)	−0.0098 (11)
C17	0.0303 (8)	0.0426 (9)	0.0378 (9)	−0.0044 (7)	−0.0011 (7)	0.0008 (8)
C18	0.0414 (10)	0.0530 (12)	0.0627 (13)	0.0072 (9)	0.0048 (10)	−0.0128 (11)
C19	0.0348 (9)	0.0644 (13)	0.0551 (12)	−0.0068 (9)	−0.0094 (9)	0.0041 (11)
C20	0.0479 (11)	0.0351 (9)	0.0378 (9)	−0.0036 (8)	0.0014 (8)	−0.0089 (7)
C21	0.0600 (14)	0.0528 (12)	0.0650 (14)	0.0047 (11)	0.0205 (12)	−0.0166 (11)
C22	0.0662 (15)	0.0557 (13)	0.0535 (13)	−0.0148 (11)	−0.0036 (12)	−0.0227 (11)
C23	0.0776 (17)	0.0351 (10)	0.0586 (14)	0.0104 (11)	−0.0019 (13)	0.0007 (9)
C24	0.0399 (10)	0.0612 (12)	0.0462 (11)	−0.0106 (9)	0.0041 (8)	0.0102 (10)

Geometric parameters (Å, º) top

Ni1—C1	1.9239 (15)	C13—C15	1.534 (3)
Ni1—P1	2.1921 (4)	C13—C14	1.535 (3)
Ni1—P2	2.1978 (4)	C13—C16	1.545 (3)
Ni1—Cl1	2.2317 (5)	C14—H14A	0.9700
P1—C8	1.8308 (19)	C14—H14B	0.9700
P1—C9	1.8720 (16)	C14—H14C	0.9700
P1—C13	1.8763 (18)	C15—H15A	0.9700
P2—C7	1.8341 (18)	C15—H15B	0.9700
P2—C17	1.8746 (19)	C15—H15C	0.9700
P2—C20	1.8756 (19)	C16—H16A	0.9700
C1—C6	1.399 (2)	C16—H16B	0.9700
C1—C2	1.412 (2)	C16—H16C	0.9700
C2—C3	1.391 (2)	C17—C24	1.532 (3)
C2—C8	1.502 (3)	C17—C19	1.534 (3)
C3—C4	1.366 (3)	C17—C18	1.543 (3)
C3—H3	0.9400	C18—H18A	0.9700
C4—C5	1.390 (3)	C18—H18B	0.9700
C4—H4	0.9400	C18—H18C	0.9700
C5—C6	1.397 (2)	C19—H19A	0.9700
C5—H5	0.9400	C19—H19B	0.9700
C6—C7	1.505 (3)	C19—H19C	0.9700
C7—H7A	0.9800	C20—C23	1.523 (3)
C7—H7B	0.9800	C20—C22	1.532 (3)
C8—H8A	0.9800	C20—C21	1.534 (3)
C8—H8B	0.9800	C21—H21A	0.9700
C9—C10	1.525 (3)	C21—H21B	0.9700
C9—C12	1.531 (3)	C21—H21C	0.9700
C9—C11	1.533 (3)	C22—H22A	0.9700
C10—H10A	0.9700	C22—H22B	0.9700
C10—H10B	0.9700	C22—H22C	0.9700
C10—H10C	0.9700	C23—H23A	0.9700
C11—H11A	0.9700	C23—H23B	0.9700
C11—H11B	0.9700	C23—H23C	0.9700
C11—H11C	0.9700	C24—H24A	0.9700
C12—H12A	0.9700	C24—H24B	0.9700
C12—H12B	0.9700	C24—H24C	0.9700
C12—H12C	0.9700

C1—Ni1—P1	85.08 (5)	C15—C13—C14	109.01 (18)
C1—Ni1—P2	84.83 (5)	C15—C13—C16	108.2 (2)
P1—Ni1—P2	169.651 (18)	C14—C13—C16	108.22 (19)
C1—Ni1—Cl1	176.13 (5)	C15—C13—P1	113.01 (14)
P1—Ni1—Cl1	94.109 (18)	C14—C13—P1	113.03 (17)
P2—Ni1—Cl1	96.109 (17)	C16—C13—P1	105.07 (13)
C8—P1—C9	104.92 (9)	C13—C14—H14A	109.5
C8—P1—C13	103.98 (9)	C13—C14—H14B	109.5
C9—P1—C13	112.16 (9)	H14A—C14—H14B	109.5
C8—P1—Ni1	102.50 (6)	C13—C14—H14C	109.5
C9—P1—Ni1	113.34 (6)	H14A—C14—H14C	109.5
C13—P1—Ni1	118.02 (7)	H14B—C14—H14C	109.5
C7—P2—C17	103.12 (9)	C13—C15—H15A	109.5
C7—P2—C20	106.10 (9)	C13—C15—H15B	109.5
C17—P2—C20	112.36 (9)	H15A—C15—H15B	109.5
C7—P2—Ni1	102.87 (6)	C13—C15—H15C	109.5
C17—P2—Ni1	118.68 (6)	H15A—C15—H15C	109.5
C20—P2—Ni1	111.98 (7)	H15B—C15—H15C	109.5
C6—C1—C2	116.79 (15)	C13—C16—H16A	109.5
C6—C1—Ni1	121.59 (12)	C13—C16—H16B	109.5
C2—C1—Ni1	121.51 (12)	H16A—C16—H16B	109.5
C3—C2—C1	121.26 (17)	C13—C16—H16C	109.5
C3—C2—C8	120.69 (17)	H16A—C16—H16C	109.5
C1—C2—C8	118.05 (15)	H16B—C16—H16C	109.5
C4—C3—C2	120.70 (18)	C24—C17—C19	108.50 (16)
C4—C3—H3	119.6	C24—C17—C18	109.02 (17)
C2—C3—H3	119.6	C19—C17—C18	108.54 (18)
C3—C4—C5	119.69 (17)	C24—C17—P2	112.50 (14)
C3—C4—H4	120.2	C19—C17—P2	113.40 (13)
C5—C4—H4	120.2	C18—C17—P2	104.70 (13)
C4—C5—C6	120.04 (18)	C17—C18—H18A	109.5
C4—C5—H5	120.0	C17—C18—H18B	109.5
C6—C5—H5	120.0	H18A—C18—H18B	109.5
C5—C6—C1	121.42 (16)	C17—C18—H18C	109.5
C5—C6—C7	119.36 (17)	H18A—C18—H18C	109.5
C1—C6—C7	119.21 (14)	H18B—C18—H18C	109.5
C6—C7—P2	106.84 (12)	C17—C19—H19A	109.5
C6—C7—H7A	110.4	C17—C19—H19B	109.5
P2—C7—H7A	110.4	H19A—C19—H19B	109.5
C6—C7—H7B	110.4	C17—C19—H19C	109.5
P2—C7—H7B	110.4	H19A—C19—H19C	109.5
H7A—C7—H7B	108.6	H19B—C19—H19C	109.5
C2—C8—P1	106.23 (12)	C23—C20—C22	109.96 (19)
C2—C8—H8A	110.5	C23—C20—C21	108.3 (2)
P1—C8—H8A	110.5	C22—C20—C21	108.32 (18)
C2—C8—H8B	110.5	C23—C20—P2	109.70 (13)
P1—C8—H8B	110.5	C22—C20—P2	113.70 (16)
H8A—C8—H8B	108.7	C21—C20—P2	106.63 (13)
C10—C9—C12	107.52 (16)	C20—C21—H21A	109.5
C10—C9—C11	109.93 (16)	C20—C21—H21B	109.5
C12—C9—C11	109.06 (16)	H21A—C21—H21B	109.5
C10—C9—P1	110.57 (12)	C20—C21—H21C	109.5
C12—C9—P1	107.09 (12)	H21A—C21—H21C	109.5
C11—C9—P1	112.49 (13)	H21B—C21—H21C	109.5
C9—C10—H10A	109.5	C20—C22—H22A	109.5
C9—C10—H10B	109.5	C20—C22—H22B	109.5
H10A—C10—H10B	109.5	H22A—C22—H22B	109.5
C9—C10—H10C	109.5	C20—C22—H22C	109.5
H10A—C10—H10C	109.5	H22A—C22—H22C	109.5
H10B—C10—H10C	109.5	H22B—C22—H22C	109.5
C9—C11—H11A	109.5	C20—C23—H23A	109.5
C9—C11—H11B	109.5	C20—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C9—C11—H11C	109.5	C20—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
C9—C12—H12A	109.5	C17—C24—H24A	109.5
C9—C12—H12B	109.5	C17—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
C9—C12—H12C	109.5	C17—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5

Experimental details

Crystal data
Chemical formula	[Ni(C₂₄H₄₃P₂)Cl]
M_r	487.68
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	225
a, b, c (Å)	11.3394 (4), 15.0463 (5), 15.4184 (5)
V (Å³)	2630.63 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.50 × 0.50 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Bruker, 2004)
T_min, T_max	0.622, 0.679
No. of measured, independent and observed [I > 2σ(I)] reflections	84881, 10074, 8461
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.771

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.09
No. of reflections	10074
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.50
Absolute structure	Flack (1983), with 4507 Friedel pairs
Absolute structure parameter	0.006 (7)

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2008).

Footnotes

‡Concurrent address: Advanced Materials Laboratory, Sandia National Laboratories, 1001 University Boulevard SE, Albuquerque, NM 87106, USA.

Acknowledgements

The authors thank Eileen Duesler and Ana Felix (UNM) for the X-ray data collection. Funding was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC PDF to DAD), and the Department of Energy (DE-FG02-06ER15765). The Bruker X-ray diffractometer was purchased via a National Science Foundation CRIF:MU award to the University of New Mexico (CHE-0443580). Sandia is a multiprogram laboratory operated by Sandia Corporation, a Lockheed Martin Company, for the US Department of Energy under contract No. DE-AC04-94AL85000.

References

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