Bis{μ-cis-1,3-bis-[(di-tert-butyl-phosphan-yl)-oxy]cyclo-hexane-κ(2) P:P'}bis-[carbonylnickel(0)] including an unknown solvent molecule.

The title compound, [Ni2(C22H46P2O2)2(CO)2], is located about a centre of inversion with the Ni(0) atom within a distorted trigonal-planar geometry. The cyclo-hexyl rings are in the usual chair conformation with the 1,3-cis substituents equatorially oriented. No specific inter-molecular inter-actions are noted in the crystal packing. A region of disordered electron density, most probably a disordered deuterobenzene solvent molecule, was treated using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155]. Its formula mass and unit-cell characteristics were not taken into account during refinement.

Related literature

For similar 16-atom macrocyclic dimers with NiII, see: Johnson & Wendt (2011 ▶); Castonguay et al. (2008 ▶); Pandarus et al. (2008 ▶). For 16-atom macrocyclic dimers of PdII and PtII with cis-1,3-bis-(di-alkyl­phosphinito)cyclo­hexane ligands, see: Sjövall et al. (2001 ▶) and Olsson et al. (2007 ▶), respectively. For other examples of Ni0 atoms adopting a close to trigonal–planar geometry, see: Rosenthal et al. (1990 ▶); Maciejewski et al. (2004 ▶); Brun et al. (2013 ▶). For an example of a carbon monoxide-induced reductive elimination from a PNP pincer-supported NiII hydride complex to form a tetra­hedral Ni0 dicarbonyl species (PNP = [N(2-PR 2-C6H3)2]−), see: Liang et al. (2012 ▶).

Experimental

Crystal data

[Ni2(C22H46O2P2)2(CO)2]

M = 982.50

Monoclinic,

a = 31.7851 (9) Å

b = 8.5449 (2) Å

c = 21.3311 (5) Å

β = 90.995 (2)°

V = 5792.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 120 K

0.20 × 0.15 × 0.05 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.883, T max = 1.000

27324 measured reflections

6958 independent reflections

4948 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.125

S = 1.09

6958 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007818/tk5304sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007818/tk5304Isup2.hkl

CCDC reference: 996025

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ni2(C22H46O2P2)2(CO)2]	F(000) = 2128
Mr = 982.50	Dx = 1.127 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6436 reflections
a = 31.7851 (9) Å	θ = 2.5–29.1°
b = 8.5449 (2) Å	µ = 0.80 mm−1
c = 21.3311 (5) Å	T = 120 K
β = 90.995 (2)°	Plates, red
V = 5792.7 (3) Å3	0.2 × 0.15 × 0.05 mm
Z = 4

Agilent Xcalibur Sapphire3 diffractometer	6958 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4948 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
Detector resolution: 16.1829 pixels mm-1	θmax = 29.1°, θmin = 2.5°
ω scans	h = −42→35
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.883, Tmax = 1.000	l = −26→26
27324 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
6958 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.882994 (11)	0.29002 (4)	0.082823 (15)	0.01812 (11)
P1	0.83832 (2)	0.33932 (7)	0.15811 (3)	0.01714 (16)
O1	0.78777 (6)	0.29472 (19)	0.16116 (8)	0.0207 (4)
C1	0.78065 (8)	0.2143 (3)	−0.11259 (12)	0.0203 (6)
H1A	0.7814	0.1012	−0.1089	0.024*
H1B	0.7917	0.2423	−0.1532	0.024*
P2	0.88701 (2)	0.22270 (7)	−0.01654 (3)	0.01594 (15)
O2	0.85052 (6)	0.2342 (2)	−0.07197 (8)	0.0218 (4)
C2	0.73525 (8)	0.2701 (3)	−0.10868 (12)	0.0196 (6)
H2	0.7231	0.2309	−0.0698	0.023*
O3	0.96746 (7)	0.3500 (3)	0.13009 (11)	0.0510 (6)
C3	0.73284 (9)	0.4468 (3)	−0.10912 (13)	0.0264 (6)
H3A	0.7038	0.4791	−0.1042	0.032*
H3B	0.7423	0.4857	−0.1492	0.032*
C4	0.75974 (9)	0.5172 (3)	−0.05680 (14)	0.0280 (7)
H4A	0.7487	0.4860	−0.0166	0.034*
H4B	0.7587	0.6304	−0.0594	0.034*
C5	0.80545 (9)	0.4621 (3)	−0.06177 (13)	0.0249 (6)
H5A	0.8172	0.5017	−0.1003	0.030*
H5B	0.8219	0.5041	−0.0269	0.030*
C6	0.80822 (8)	0.2861 (3)	−0.06116 (12)	0.0194 (6)
H6	0.7991	0.2472	−0.0204	0.023*
C7	0.93363 (11)	0.3218 (3)	0.11184 (14)	0.0321 (7)
C11	0.83370 (9)	0.5570 (3)	0.16926 (12)	0.0226 (6)
C12	0.80724 (11)	0.6148 (3)	0.11321 (14)	0.0341 (7)
H12A	0.7798	0.5681	0.1144	0.051*
H12B	0.8207	0.5858	0.0750	0.051*
H12C	0.8046	0.7266	0.1152	0.051*
C13	0.81175 (10)	0.6059 (3)	0.22944 (13)	0.0326 (7)
H13A	0.7845	0.5579	0.2308	0.049*
H13B	0.8087	0.7177	0.2302	0.049*
H13C	0.8283	0.5729	0.2651	0.049*
C14	0.87701 (10)	0.6353 (3)	0.16623 (15)	0.0342 (7)
H14A	0.8942	0.6012	0.2011	0.051*
H14B	0.8737	0.7469	0.1679	0.051*
H14C	0.8903	0.6069	0.1278	0.051*
C15	0.85457 (9)	0.2395 (3)	0.23398 (12)	0.0226 (6)
C16	0.86514 (10)	0.0712 (3)	0.21485 (13)	0.0303 (7)
H16A	0.8870	0.0725	0.1844	0.045*
H16B	0.8405	0.0221	0.1971	0.045*
H16C	0.8745	0.0135	0.2511	0.045*
C17	0.89435 (10)	0.3151 (3)	0.26297 (13)	0.0287 (7)
H17A	0.8883	0.4209	0.2748	0.043*
H17B	0.9164	0.3146	0.2328	0.043*
H17C	0.9032	0.2567	0.2994	0.043*
C18	0.81986 (10)	0.2332 (3)	0.28269 (13)	0.0317 (7)
H18A	0.8128	0.3376	0.2954	0.048*
H18B	0.8296	0.1747	0.3185	0.048*
H18C	0.7954	0.1833	0.2648	0.048*
C21	0.92859 (9)	0.3402 (3)	−0.05827 (13)	0.0227 (6)
C22	0.92236 (10)	0.5106 (3)	−0.03761 (16)	0.0352 (8)
H22A	0.9251	0.5175	0.0072	0.053*
H22B	0.8948	0.5455	−0.0505	0.053*
H22C	0.9433	0.5755	−0.0566	0.053*
C23	0.92422 (10)	0.3335 (3)	−0.12995 (14)	0.0329 (7)
H23A	0.8962	0.3636	−0.1424	0.049*
H23B	0.9296	0.2288	−0.1440	0.049*
H23C	0.9441	0.4039	−0.1483	0.049*
C24	0.97330 (9)	0.2906 (3)	−0.03876 (14)	0.0277 (6)
H24A	0.9762	0.2945	0.0061	0.042*
H24B	0.9933	0.3604	−0.0572	0.042*
H24C	0.9784	0.1858	−0.0530	0.042*
C25	0.89841 (9)	0.0076 (3)	−0.02237 (12)	0.0212 (6)
C26	0.93066 (10)	−0.0421 (3)	0.02756 (13)	0.0306 (7)
H26A	0.9572	0.0072	0.0195	0.046*
H26B	0.9340	−0.1537	0.0265	0.046*
H26C	0.9211	−0.0110	0.0682	0.046*
C27	0.85646 (10)	−0.0734 (3)	−0.00816 (14)	0.0317 (7)
H27A	0.8357	−0.0441	−0.0393	0.047*
H27B	0.8472	−0.0418	0.0325	0.047*
H27C	0.8603	−0.1848	−0.0088	0.047*
C28	0.91206 (10)	−0.0450 (3)	−0.08764 (13)	0.0287 (7)
H28A	0.8912	−0.0139	−0.1182	0.043*
H28B	0.9150	−0.1568	−0.0882	0.043*
H28C	0.9385	0.0028	−0.0973	0.043*

	U11	U22	U33	U12	U13	U23
Ni1	0.0181 (2)	0.01832 (18)	0.01790 (19)	0.00151 (13)	−0.00099 (14)	−0.00328 (12)
P1	0.0194 (4)	0.0159 (3)	0.0160 (3)	0.0014 (3)	−0.0019 (3)	−0.0026 (2)
O1	0.0177 (10)	0.0275 (10)	0.0168 (9)	−0.0013 (8)	−0.0016 (8)	−0.0021 (7)
C1	0.0189 (15)	0.0226 (13)	0.0195 (13)	0.0009 (11)	0.0016 (11)	0.0035 (10)
P2	0.0155 (4)	0.0157 (3)	0.0166 (3)	0.0024 (3)	−0.0002 (3)	0.0007 (2)
O2	0.0164 (10)	0.0310 (10)	0.0179 (9)	0.0043 (8)	−0.0004 (8)	0.0011 (7)
C2	0.0185 (15)	0.0272 (14)	0.0130 (12)	−0.0007 (11)	−0.0015 (11)	0.0003 (10)
O3	0.0249 (14)	0.0843 (18)	0.0434 (15)	−0.0081 (13)	−0.0078 (11)	−0.0117 (12)
C3	0.0228 (16)	0.0263 (14)	0.0299 (16)	0.0042 (12)	−0.0022 (13)	−0.0033 (11)
C4	0.0252 (17)	0.0259 (14)	0.0328 (16)	0.0066 (12)	−0.0059 (13)	−0.0069 (11)
C5	0.0227 (16)	0.0273 (14)	0.0246 (14)	0.0012 (12)	−0.0034 (12)	−0.0039 (11)
C6	0.0168 (15)	0.0271 (14)	0.0141 (12)	0.0027 (11)	−0.0002 (11)	0.0019 (10)
C7	0.0313 (19)	0.0401 (17)	0.0249 (16)	−0.0002 (14)	−0.0007 (14)	−0.0080 (12)
C11	0.0256 (16)	0.0165 (12)	0.0257 (14)	0.0024 (11)	0.0002 (12)	−0.0032 (10)
C12	0.047 (2)	0.0236 (15)	0.0315 (17)	0.0094 (14)	−0.0019 (15)	0.0035 (12)
C13	0.042 (2)	0.0256 (15)	0.0302 (16)	0.0111 (14)	0.0045 (14)	−0.0059 (12)
C14	0.0341 (19)	0.0184 (13)	0.050 (2)	−0.0020 (13)	0.0053 (15)	−0.0072 (12)
C15	0.0227 (16)	0.0261 (14)	0.0188 (13)	0.0022 (12)	−0.0047 (11)	0.0017 (10)
C16	0.0355 (19)	0.0226 (14)	0.0325 (16)	0.0049 (13)	−0.0088 (14)	0.0020 (11)
C17	0.0278 (18)	0.0333 (16)	0.0247 (15)	0.0007 (13)	−0.0099 (13)	−0.0024 (11)
C18	0.0328 (19)	0.0401 (17)	0.0221 (15)	0.0033 (14)	−0.0012 (13)	0.0046 (12)
C21	0.0180 (15)	0.0223 (13)	0.0278 (15)	0.0008 (11)	0.0010 (12)	0.0032 (11)
C22	0.0286 (18)	0.0213 (14)	0.056 (2)	−0.0025 (13)	0.0063 (15)	0.0081 (13)
C23	0.0265 (18)	0.0400 (17)	0.0326 (17)	0.0019 (14)	0.0078 (14)	0.0152 (13)
C24	0.0205 (16)	0.0283 (15)	0.0343 (16)	0.0002 (12)	0.0023 (13)	0.0002 (11)
C25	0.0267 (16)	0.0163 (12)	0.0204 (13)	0.0015 (11)	−0.0003 (12)	−0.0013 (10)
C26	0.042 (2)	0.0225 (14)	0.0273 (15)	0.0094 (13)	−0.0057 (14)	0.0014 (11)
C27	0.039 (2)	0.0168 (13)	0.0390 (18)	−0.0041 (13)	0.0057 (15)	−0.0002 (12)
C28	0.042 (2)	0.0203 (13)	0.0242 (15)	0.0059 (13)	−0.0012 (13)	−0.0048 (11)

Ni1—C7	1.736 (3)	C14—H14B	0.9600
Ni1—P2	2.2021 (7)	C14—H14C	0.9600
Ni1—P1	2.2028 (7)	C15—C18	1.530 (4)
P1—O1	1.654 (2)	C15—C16	1.534 (4)
P1—C11	1.882 (2)	C15—C17	1.540 (4)
P1—C15	1.893 (3)	C16—H16A	0.9600
O1—C2i	1.438 (3)	C16—H16B	0.9600
C1—C6	1.521 (4)	C16—H16C	0.9600
C1—C2	1.523 (4)	C17—H17A	0.9600
C1—H1A	0.9700	C17—H17B	0.9600
C1—H1B	0.9700	C17—H17C	0.9600
P2—O2	1.6448 (19)	C18—H18A	0.9600
P2—C25	1.878 (2)	C18—H18B	0.9600
P2—C21	1.894 (3)	C18—H18C	0.9600
O2—C6	1.438 (3)	C21—C24	1.534 (4)
C2—O1i	1.438 (3)	C21—C23	1.534 (4)
C2—C3	1.512 (3)	C21—C22	1.536 (4)
C2—H2	0.9800	C22—H22A	0.9600
O3—C7	1.162 (4)	C22—H22B	0.9600
C3—C4	1.518 (4)	C22—H22C	0.9600
C3—H3A	0.9700	C23—H23A	0.9600
C3—H3B	0.9700	C23—H23B	0.9600
C4—C5	1.533 (4)	C23—H23C	0.9600
C4—H4A	0.9700	C24—H24A	0.9600
C4—H4B	0.9700	C24—H24B	0.9600
C5—C6	1.507 (3)	C24—H24C	0.9600
C5—H5A	0.9700	C25—C26	1.526 (4)
C5—H5B	0.9700	C25—C28	1.533 (4)
C6—H6	0.9800	C25—C27	1.537 (4)
C11—C13	1.530 (4)	C26—H26A	0.9600
C11—C12	1.532 (4)	C26—H26B	0.9600
C11—C14	1.533 (4)	C26—H26C	0.9600
C12—H12A	0.9600	C27—H27A	0.9600
C12—H12B	0.9600	C27—H27B	0.9600
C12—H12C	0.9600	C27—H27C	0.9600
C13—H13A	0.9600	C28—H28A	0.9600
C13—H13B	0.9600	C28—H28B	0.9600
C13—H13C	0.9600	C28—H28C	0.9600
C14—H14A	0.9600
C7—Ni1—P2	108.38 (10)	C11—C14—H14C	109.5
C7—Ni1—P1	108.39 (10)	H14A—C14—H14C	109.5
P2—Ni1—P1	143.19 (3)	H14B—C14—H14C	109.5
O1—P1—C11	98.33 (11)	C18—C15—C16	108.2 (2)
O1—P1—C15	96.52 (11)	C18—C15—C17	109.8 (2)
C11—P1—C15	110.98 (12)	C16—C15—C17	108.5 (2)
O1—P1—Ni1	128.58 (7)	C18—C15—P1	114.0 (2)
C11—P1—Ni1	109.51 (9)	C16—C15—P1	104.64 (18)
C15—P1—Ni1	111.55 (9)	C17—C15—P1	111.38 (18)
C2i—O1—P1	122.67 (16)	C15—C16—H16A	109.5
C6—C1—C2	111.6 (2)	C15—C16—H16B	109.5
C6—C1—H1A	109.3	H16A—C16—H16B	109.5
C2—C1—H1A	109.3	C15—C16—H16C	109.5
C6—C1—H1B	109.3	H16A—C16—H16C	109.5
C2—C1—H1B	109.3	H16B—C16—H16C	109.5
H1A—C1—H1B	108.0	C15—C17—H17A	109.5
O2—P2—C25	98.35 (11)	C15—C17—H17B	109.5
O2—P2—C21	96.88 (11)	H17A—C17—H17B	109.5
C25—P2—C21	110.52 (12)	C15—C17—H17C	109.5
O2—P2—Ni1	128.64 (7)	H17A—C17—H17C	109.5
C25—P2—Ni1	109.50 (8)	H17B—C17—H17C	109.5
C21—P2—Ni1	111.50 (9)	C15—C18—H18A	109.5
C6—O2—P2	123.55 (15)	C15—C18—H18B	109.5
O1i—C2—C3	110.8 (2)	H18A—C18—H18B	109.5
O1i—C2—C1	107.85 (19)	C15—C18—H18C	109.5
C3—C2—C1	111.1 (2)	H18A—C18—H18C	109.5
O1i—C2—H2	109.0	H18B—C18—H18C	109.5
C3—C2—H2	109.0	C24—C21—C23	109.1 (2)
C1—C2—H2	109.0	C24—C21—C22	107.9 (2)
C2—C3—C4	111.3 (2)	C23—C21—C22	108.1 (2)
C2—C3—H3A	109.4	C24—C21—P2	112.14 (18)
C4—C3—H3A	109.4	C23—C21—P2	113.38 (19)
C2—C3—H3B	109.4	C22—C21—P2	105.86 (19)
C4—C3—H3B	109.4	C21—C22—H22A	109.5
H3A—C3—H3B	108.0	C21—C22—H22B	109.5
C3—C4—C5	110.5 (2)	H22A—C22—H22B	109.5
C3—C4—H4A	109.6	C21—C22—H22C	109.5
C5—C4—H4A	109.6	H22A—C22—H22C	109.5
C3—C4—H4B	109.6	H22B—C22—H22C	109.5
C5—C4—H4B	109.6	C21—C23—H23A	109.5
H4A—C4—H4B	108.1	C21—C23—H23B	109.5
C6—C5—C4	111.2 (2)	H23A—C23—H23B	109.5
C6—C5—H5A	109.4	C21—C23—H23C	109.5
C4—C5—H5A	109.4	H23A—C23—H23C	109.5
C6—C5—H5B	109.4	H23B—C23—H23C	109.5
C4—C5—H5B	109.4	C21—C24—H24A	109.5
H5A—C5—H5B	108.0	C21—C24—H24B	109.5
O2—C6—C5	111.2 (2)	H24A—C24—H24B	109.5
O2—C6—C1	106.77 (19)	C21—C24—H24C	109.5
C5—C6—C1	111.3 (2)	H24A—C24—H24C	109.5
O2—C6—H6	109.2	H24B—C24—H24C	109.5
C5—C6—H6	109.2	C26—C25—C28	110.8 (2)
C1—C6—H6	109.2	C26—C25—C27	108.1 (2)
O3—C7—Ni1	176.8 (3)	C28—C25—C27	107.9 (2)
C13—C11—C12	108.3 (2)	C26—C25—P2	110.76 (18)
C13—C11—C14	109.8 (2)	C28—C25—P2	113.90 (17)
C12—C11—C14	107.9 (2)	C27—C25—P2	104.98 (18)
C13—C11—P1	114.45 (18)	C25—C26—H26A	109.5
C12—C11—P1	105.24 (18)	C25—C26—H26B	109.5
C14—C11—P1	110.74 (18)	H26A—C26—H26B	109.5
C11—C12—H12A	109.5	C25—C26—H26C	109.5
C11—C12—H12B	109.5	H26A—C26—H26C	109.5
H12A—C12—H12B	109.5	H26B—C26—H26C	109.5
C11—C12—H12C	109.5	C25—C27—H27A	109.5
H12A—C12—H12C	109.5	C25—C27—H27B	109.5
H12B—C12—H12C	109.5	H27A—C27—H27B	109.5
C11—C13—H13A	109.5	C25—C27—H27C	109.5
C11—C13—H13B	109.5	H27A—C27—H27C	109.5
H13A—C13—H13B	109.5	H27B—C27—H27C	109.5
C11—C13—H13C	109.5	C25—C28—H28A	109.5
H13A—C13—H13C	109.5	C25—C28—H28B	109.5
H13B—C13—H13C	109.5	H28A—C28—H28B	109.5
C11—C14—H14A	109.5	C25—C28—H28C	109.5
C11—C14—H14B	109.5	H28A—C28—H28C	109.5
H14A—C14—H14B	109.5	H28B—C28—H28C	109.5