[1,2-Bis(diisopropyl­phosphan­yl)ethane-κ2P,P′](carbonato-κ2O,O′)nickel(II)

Morales-Becerril, I.; Flores-Alamo, M.; Garcia, J.J.

doi:10.1107/S1600536813006521

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages m200-m201

doi:10.1107/S1600536813006521

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[1,2-Bis(diisopropylphosphanyl)ethane-κ²P,P′](carbonato-κ²O,O′)nickel(II)

Illan Morales-Becerril,^a Marcos Flores-Alamo ^a and Juventino J. Garcia ^a ^*

^aFacultad de Química, Universidad Nacional Autónoma de México, México DF, 04510, Mexico
^*Correspondence e-mail: juvent@unam.mx

(Received 22 February 2013; accepted 6 March 2013; online 13 March 2013)

In the crystal of the title compound, [Ni(CO₃)(C₁₄H₃₂P₂)], the metal center in each of three independent molecules shows slight tetrahedral distortion from ideal square-planar coordination geometry, with angles between the normals to the planes defined by the cis-P—Ni—P and cis-O—Ni—O fragments of 3.92 (17), 0.70 (16) and 2.17 (14)° in the three molecules. In the crystal, there are intermolecular C—H⋯O hydrogen bonds that show a laminar growth in the ab plane.

Related literature

For the synthesis and related structures, see: González-Sebastián et al. (2012 ); Cañavera-Buelvas et al. (2011 ); Castellanos-Blanco et al. (2011 ); Angulo et al. (2003 ); Dahlenburg & Kurth (2001 ). For applications of nickel complexes to catalytic systems, see: Vicic & Jones (1997 ); Arévalo & García (2010 ). For nickel compounds in CO₂ activation, see: Anderson et al. (2010 ); Aresta et al. (1975 ).

Experimental

Crystal data

[Ni(CO₃)(C₁₄H₃₂P₂)]
M_r = 381.06
Monoclinic, P 2₁ /n
a = 8.4974 (4) Å
b = 46.582 (2) Å
c = 14.7342 (7) Å
β = 103.618 (4)°
V = 5668.2 (5) Å³
Z = 12
Mo Kα radiation
μ = 1.20 mm⁻¹
T = 130 K
0.33 × 0.06 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.813, T_max = 0.965
42978 measured reflections
10329 independent reflections
7642 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.096
S = 1.09
10329 reflections
592 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1A—O1A	1.879 (2)
Ni1A—O2A	1.885 (3)
Ni1A—P1A	2.1390 (12)
Ni1A—P2A	2.1460 (11)
Ni1B—O2B	1.887 (2)
Ni1B—O1B	1.890 (3)
Ni1B—P2B	2.1399 (12)
Ni1B—P1B	2.1415 (11)
Ni1C—O2C	1.877 (3)
Ni1C—O1C	1.889 (2)
Ni1C—P2C	2.1433 (10)
Ni1C—P1C	2.1481 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5A—H5A1⋯O3Aⁱ	0.98	2.70	3.670 (5)	169
C4A—H4A3⋯O1Aⁱ	0.98	2.69	3.448 (5)	134
C8C—H8C1⋯O3Cⁱⁱ	0.98	2.71	3.595 (5)	150
C10B—H10F⋯O3Bⁱⁱ	0.98	2.52	3.335 (5)	141
C1A—H1A2⋯O3Bⁱⁱ	0.99	2.23	3.204 (5)	168
C1C—H1C2⋯O3Aⁱⁱⁱ	0.99	2.50	3.443 (5)	159
C9C—H9C⋯O2Aⁱⁱⁱ	1.00	2.48	3.455 (5)	165
C1B—H1B1⋯O3C^iv	0.99	2.50	3.452 (5)	161
C6B—H6B⋯O3C^iv	1.00	2.60	3.516 (5)	153
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813006521/ru2049sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006521/ru2049Isup2.hkl

checkCIF report

Comment top

Nickel compounds are highly active in CO₂ activation (Aresta et al., 1975, Anderson et al., 2010), to produce carbonyl and carbonato derivatives. We recently published the complex [(dippe)Ni(CO₃)] with a methanol solvate (González-Sebastián et al., 2012).

The asymmetric unit consists of three [(dippe)Ni(CO₃)] discrete molecules of the neutral complex (Figure 1). The Ni(II) atom is coordinated by two P atoms of dippe ligand and two oxygen atoms of the carbonato anion. The metal center in 3 independent molecules A, B and C of [(dippe)Ni(CO₃)] shows slight tetrahedral distortion from ideal square planar coordination geometry, with the angle between the normals to the planes defined by the two cis-P–Ni–P and cis- O–Ni–O fragments of 3.92 (17), 0.70 (16) and 2.17 (14)° respectively, these being larger than the limiting value of 0° for square-planar coordination in [(dippe)Ni(CO)₂]CH₃OH (González-Sebastián et al. 2012). Additionally the Ni(II) atom is situated 0.040 (1), 0.0057 (9), 0.0095 (9) Å above the P1/P2/O1/O2 plane in A, B and C molecules respectively. These deviations from planarity, which can be attributed to some steric efect of the dippe ligand and intermolecular interactions of the carbonato ligand, are somewhat shorter than the distortion from ideal square-planar coordination geometry observed on [(dippe)Ni(carbazole)₂ (Cañavera-Buelvas et al., 2011) and [(dippe)NiCl₂] (Castellanos-Blanco et al., 2011,) complexes where the NiCl2/NiP2 dihedral angles of 15.32 and 10.01 ° respectively, and similar to the distortion from ideal square-planar coordination geometry observed for related [(dcpe)NiCl₂] (Angulo et al., 2003) and [(1S,2S)- C₅H₈{P(C₆H₁1)₂}₂NiCl₂] (Dahlenburg & Kurth, 2001) complexes, where the NiCl2/NiP2 dihedral angles of 3.96 and 5.37°, respectively.

In the crystal packing, there are intermolecular contacts of the type hydrogen bond (Table 2) mainly between the carbon donor atom of the dippe to O oxygen atom acceptor of the metallic complex mainly. The C5A-H5A1···O3A (2.7 Å) and C4A-H4A3···O1A (2.69 Å) intermolecular interactions in molecule A forming a motif graph R₂²(8) along the a axes, while the C10B—H10F···O3B (2.52 Å) and C8C-H8C1···O3C (2.71 Å) intermolecular interactions in molecules B and C forming a C(8) motif along to c axis. All these interactions show a laminar growing in the a, b plane (Figure 2).

Related literature top

For the synthesis and related structures, see: González-Sebastián et al. (2012); Cañavera-Buelvas et al. (2011); Castellanos-Blanco et al. (2011); Angulo et al. (2003); Dahlenburg & Kurth (2001). For applications of nickel complexes to catalytic systems, see: Vicic & Jones (1997); Arévalo & García (2010). For nickel compounds in CO₂ activation, see: Anderson et al. (2010); Aresta et al. (1975).

Experimental top

The compound [(dippe)NiCl₂] (98.0 mg, 0.25 mmol) was slowly added into a solution of commercially available KOH (28.0 mg, 0. 50 mmol) in H₂O (5 ml) under constant stirring at room temperature. After 15 min of reaction, a red solution was observed. At this point the reaction mixture was evaporated to dryness under vacuum and the obtained red-wine residue was re-dissolved in THF (5 mL) and filtrated via cannula using a Schlenk flask. After a couple of days of cooling in the dry-box fridge at -30 °C, yellow crystals suitable for X ray diffraction studies were obtained.

The yellow crystals for complex [(dippe)Ni(CO₃)] displayed a singlet in ³¹P{¹H} NMR (THF-d₈): 87.8 p.p.m., clearly this product raised from the carbonate present in the commercial KOH.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as circles of arbitrary size.
	Fig. 2. Crystal structure of the title compound viewed along the c axis, showing the short contacts between the symmetry equivalent for molecule A (blue), molecule B (green) and molecule C (red) extending along the a-b plane.

[1,2-Bis(diisopropylphosphanyl)ethane-κ²P,P'](carbonato-κ²O,O')nickel(II) top

Crystal data top

[Ni(CO₃)(C₁₄H₃₂P₂)]	F(000) = 2448
M_r = 381.06	D_x = 1.34 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4974 (4) Å	Cell parameters from 6343 reflections
b = 46.582 (2) Å	θ = 3.4–29.5°
c = 14.7342 (7) Å	µ = 1.20 mm⁻¹
β = 103.618 (4)°	T = 130 K
V = 5668.2 (5) Å³	Needle, pale yellow
Z = 12	0.33 × 0.06 × 0.03 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	10329 independent reflections
Graphite monochromator	7642 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.088
ω scans	θ_max = 25.4°, θ_min = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	h = −10→10
T_min = 0.813, T_max = 0.965	k = −56→55
42978 measured reflections	l = −13→17

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0167P)² + 0.6693P] where P = (F_o² + 2F_c²)/3
10329 reflections	(Δ/σ)_max = 0.001
592 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ni(CO₃)(C₁₄H₃₂P₂)]	V = 5668.2 (5) Å³
M_r = 381.06	Z = 12
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4974 (4) Å	µ = 1.20 mm⁻¹
b = 46.582 (2) Å	T = 130 K
c = 14.7342 (7) Å	0.33 × 0.06 × 0.03 mm
β = 103.618 (4)°

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	10329 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	7642 reflections with I > 2σ(I)
T_min = 0.813, T_max = 0.965	R_int = 0.088
42978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.09	Δρ_max = 0.57 e Å⁻³
10329 reflections	Δρ_min = −0.59 e Å⁻³
592 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1A	0.0622 (4)	0.19012 (9)	0.3969 (3)	0.0260 (11)
H1A1	0.0615	0.1964	0.4611	0.031*
H1A2	0.0722	0.169	0.3969	0.031*
C2A	0.2069 (5)	0.20374 (10)	0.3671 (3)	0.0317 (12)
H2A1	0.2366	0.1919	0.3179	0.038*
H2A2	0.3014	0.2046	0.4212	0.038*
C3A	0.2999 (5)	0.24984 (10)	0.2547 (3)	0.0295 (11)
H3A	0.4108	0.2472	0.2957	0.035*
C4A	0.2828 (5)	0.22929 (11)	0.1706 (3)	0.0365 (12)
H4A1	0.176	0.2318	0.1283	0.055*
H4A2	0.2944	0.2094	0.1929	0.055*
H4A3	0.3672	0.2336	0.1373	0.055*
C5A	0.2843 (5)	0.28071 (11)	0.2228 (4)	0.0429 (14)
H5A1	0.3655	0.2849	0.1872	0.064*
H5A2	0.3015	0.2934	0.2774	0.064*
H5A3	0.1757	0.2839	0.1833	0.064*
C6A	0.1872 (5)	0.26167 (10)	0.4291 (3)	0.0334 (12)
H6A	0.1319	0.2511	0.4719	0.04*
C7A	0.3645 (5)	0.26406 (12)	0.4821 (3)	0.0446 (14)
H7A1	0.4255	0.2745	0.444	0.067*
H7A2	0.4104	0.2448	0.4955	0.067*
H7A3	0.3714	0.2744	0.5409	0.067*
C8A	0.1082 (6)	0.29068 (12)	0.4154 (4)	0.0540 (16)
H8A1	0.0955	0.298	0.4756	0.081*
H8A2	0.0016	0.2891	0.3721	0.081*
H8A3	0.176	0.3039	0.3895	0.081*
C9A	−0.1868 (5)	0.17146 (9)	0.2339 (3)	0.0281 (11)
H9A	−0.1931	0.1536	0.2704	0.034*
C10A	−0.0589 (5)	0.16688 (11)	0.1779 (3)	0.0404 (13)
H10A	−0.0914	0.1509	0.1343	0.061*
H10B	0.0453	0.1624	0.2206	0.061*
H10C	−0.0484	0.1844	0.1428	0.061*
C11A	−0.3540 (5)	0.17688 (10)	0.1700 (3)	0.0396 (13)
H11A	−0.3556	0.1958	0.1409	0.059*
H11B	−0.4361	0.1762	0.2069	0.059*
H11C	−0.3775	0.1621	0.1214	0.059*
C12A	−0.2795 (5)	0.20298 (10)	0.3847 (3)	0.0304 (11)
H12A	−0.3867	0.2059	0.34	0.036*
C13A	−0.2494 (6)	0.22872 (12)	0.4501 (3)	0.0444 (14)
H13A	−0.3357	0.23	0.4838	0.067*
H13B	−0.2484	0.2463	0.4136	0.067*
H13C	−0.1448	0.2265	0.4948	0.067*
C14A	−0.2903 (6)	0.17527 (12)	0.4394 (4)	0.0522 (15)
H14A	−0.188	0.1722	0.4855	0.078*
H14B	−0.3113	0.159	0.3962	0.078*
H14C	−0.3787	0.177	0.4715	0.078*
C15A	−0.2766 (5)	0.27222 (9)	0.1602 (3)	0.0198 (10)
Ni1A	−0.09895 (6)	0.241123 (11)	0.25206 (4)	0.01761 (14)
O1A	−0.3167 (3)	0.24726 (6)	0.1911 (2)	0.0264 (7)
O2A	−0.1191 (3)	0.27667 (6)	0.18928 (19)	0.0223 (7)
O3A	−0.3730 (3)	0.28892 (6)	0.11296 (19)	0.0271 (7)
P1A	−0.12663 (12)	0.20091 (2)	0.31662 (8)	0.0214 (3)
P2A	0.15252 (12)	0.24007 (3)	0.32275 (8)	0.0228 (3)
C1B	0.4161 (4)	0.03946 (9)	0.1585 (3)	0.0208 (10)
H1B1	0.4405	0.0188	0.1704	0.025*
H1B2	0.297	0.0419	0.144	0.025*
C2B	0.4810 (4)	0.04938 (9)	0.0755 (3)	0.0201 (10)
H2B1	0.4232	0.0669	0.0478	0.024*
H2B2	0.4638	0.0342	0.0271	0.024*
C3B	0.7525 (5)	0.07725 (9)	0.0237 (3)	0.0240 (10)
H3B	0.7128	0.0666	−0.0362	0.029*
C4B	0.6691 (6)	0.10641 (10)	0.0144 (3)	0.0397 (13)
H4B1	0.6932	0.116	0.0753	0.06*
H4B2	0.5519	0.1038	−0.0073	0.06*
H4B3	0.7087	0.1182	−0.0307	0.06*
C5B	0.9357 (5)	0.08070 (11)	0.0401 (3)	0.0389 (13)
H5B1	0.9608	0.0925	−0.0097	0.058*
H5B2	0.986	0.0618	0.0401	0.058*
H5B3	0.9781	0.09	0.1006	0.058*
C6B	0.7921 (4)	0.02135 (9)	0.1257 (3)	0.0187 (10)
H6B	0.7227	0.0085	0.1542	0.022*
C7B	0.7946 (5)	0.00803 (10)	0.0308 (3)	0.0270 (11)
H7B1	0.8736	0.0182	0.0037	0.04*
H7B2	0.6868	0.0096	−0.0112	0.04*
H7B3	0.825	−0.0123	0.0393	0.04*
C8B	0.9599 (4)	0.02111 (10)	0.1927 (3)	0.0289 (11)
H8B1	0.9987	0.0013	0.2028	0.043*
H8B2	0.9531	0.0296	0.2526	0.043*
H8B3	1.0354	0.0323	0.1658	0.043*
C9B	0.3595 (4)	0.08739 (10)	0.2764 (3)	0.0267 (11)
H9B	0.2538	0.0774	0.2725	0.032*
C10B	0.4088 (5)	0.10235 (11)	0.3715 (4)	0.0437 (14)
H10D	0.515	0.1114	0.378	0.065*
H10E	0.4146	0.0882	0.4213	0.065*
H10F	0.3283	0.117	0.3759	0.065*
C11B	0.3360 (5)	0.10932 (11)	0.1977 (4)	0.0439 (14)
H11D	0.2513	0.123	0.2037	0.066*
H11E	0.3038	0.0994	0.1374	0.066*
H11F	0.4377	0.1197	0.2012	0.066*
C12B	0.5298 (4)	0.03565 (10)	0.3619 (3)	0.0239 (10)
H12B	0.5646	0.0473	0.4202	0.029*
C13B	0.6622 (5)	0.01380 (10)	0.3618 (3)	0.0307 (11)
H13D	0.6762	0.0016	0.4173	0.046*
H13E	0.7639	0.0238	0.3625	0.046*
H13F	0.632	0.0019	0.3055	0.046*
C14B	0.3705 (5)	0.02115 (11)	0.3657 (3)	0.0383 (13)
H14D	0.3359	0.0086	0.3113	0.057*
H14E	0.2876	0.0358	0.3651	0.057*
H14F	0.3857	0.0098	0.423	0.057*
C15B	0.9336 (4)	0.10590 (9)	0.3390 (3)	0.0195 (10)
Ni1B	0.73598 (5)	0.077729 (11)	0.24982 (4)	0.01499 (13)
O1B	0.7989 (3)	0.09799 (6)	0.36375 (18)	0.0198 (7)
O2B	0.9390 (3)	0.09517 (6)	0.25715 (19)	0.0204 (7)
O3B	1.0375 (3)	0.12153 (6)	0.38621 (19)	0.0250 (7)
P1B	0.50899 (11)	0.06037 (2)	0.26289 (7)	0.0180 (3)
P2B	0.69677 (11)	0.05682 (2)	0.11706 (7)	0.0153 (2)
C1C	0.0137 (4)	0.14384 (9)	0.6708 (3)	0.0212 (10)
H1C1	−0.0619	0.1474	0.7115	0.025*
H1C2	0.0272	0.162	0.6385	0.025*
C2C	−0.0556 (4)	0.12052 (9)	0.5987 (3)	0.0229 (10)
H2C1	−0.0037	0.1217	0.5453	0.027*
H2C2	−0.1735	0.1234	0.5749	0.027*
C3C	−0.0352 (4)	0.05938 (9)	0.5589 (3)	0.0188 (9)
H3C	−0.1338	0.0641	0.5091	0.023*
C4C	0.1129 (5)	0.06146 (10)	0.5169 (3)	0.0300 (11)
H4C1	0.2098	0.0556	0.5636	0.045*
H4C2	0.1257	0.0813	0.4978	0.045*
H4C3	0.098	0.0488	0.4624	0.045*
C5C	−0.0524 (5)	0.02856 (9)	0.5923 (3)	0.0237 (10)
H5C1	−0.0582	0.0152	0.5402	0.036*
H5C2	−0.1514	0.027	0.6152	0.036*
H5C3	0.0415	0.0238	0.6428	0.036*
C6C	−0.1881 (4)	0.08059 (10)	0.7094 (3)	0.0225 (10)
H6C	−0.2004	0.0993	0.7402	0.027*
C7C	−0.3499 (4)	0.07530 (10)	0.6393 (3)	0.0290 (11)
H7C1	−0.3472	0.0566	0.6094	0.044*
H7C2	−0.3682	0.0904	0.5916	0.044*
H7C3	−0.4379	0.0756	0.672	0.044*
C8C	−0.1566 (5)	0.05835 (10)	0.7871 (3)	0.0281 (11)
H8C1	−0.2466	0.0583	0.8181	0.042*
H8C2	−0.0558	0.063	0.8325	0.042*
H8C3	−0.147	0.0393	0.7605	0.042*
C9C	0.3637 (4)	0.14924 (9)	0.6907 (3)	0.0233 (10)
H9C	0.3468	0.1705	0.6917	0.028*
C10C	0.3441 (5)	0.14000 (11)	0.5898 (3)	0.0353 (12)
H10G	0.4288	0.1489	0.5643	0.053*
H10H	0.2376	0.146	0.5531	0.053*
H10I	0.3533	0.1191	0.5869	0.053*
C11C	0.5336 (4)	0.14270 (10)	0.7485 (3)	0.0286 (11)
H11G	0.5498	0.1219	0.7526	0.043*
H11H	0.5465	0.1507	0.8114	0.043*
H11I	0.6137	0.1514	0.7187	0.043*
C12C	0.2326 (5)	0.14893 (9)	0.8573 (3)	0.0241 (10)
H12C	0.3496	0.1475	0.8901	0.029*
C13C	0.1385 (6)	0.13196 (11)	0.9153 (3)	0.0457 (14)
H13G	0.159	0.1401	0.9784	0.069*
H13H	0.1734	0.1119	0.9188	0.069*
H13I	0.0225	0.133	0.886	0.069*
C14C	0.1893 (5)	0.18064 (10)	0.8518 (3)	0.0333 (12)
H14G	0.073	0.1829	0.8248	0.05*
H14H	0.2504	0.1905	0.8125	0.05*
H14I	0.2166	0.1889	0.9147	0.05*
C15C	0.3927 (4)	0.05090 (9)	0.8190 (3)	0.0196 (10)
Ni1C	0.21570 (5)	0.085830 (11)	0.74854 (4)	0.01691 (13)
O1C	0.4212 (3)	0.07890 (6)	0.82835 (19)	0.0234 (7)
O2C	0.2466 (3)	0.04613 (6)	0.76615 (19)	0.0220 (7)
O3C	0.4888 (3)	0.03226 (6)	0.85383 (19)	0.0231 (7)
P1C	0.21058 (12)	0.13190 (2)	0.74185 (8)	0.0189 (3)
P2C	−0.01785 (11)	0.08543 (2)	0.65341 (7)	0.0171 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.030 (2)	0.016 (3)	0.028 (3)	0.0080 (19)	−0.0017 (19)	0.005 (2)
C2A	0.026 (2)	0.030 (3)	0.035 (3)	0.009 (2)	−0.001 (2)	0.006 (2)
C3A	0.018 (2)	0.035 (3)	0.034 (3)	−0.001 (2)	0.0039 (19)	−0.001 (2)
C4A	0.034 (3)	0.041 (3)	0.037 (3)	−0.001 (2)	0.015 (2)	−0.003 (3)
C5A	0.038 (3)	0.047 (4)	0.047 (4)	−0.008 (2)	0.016 (2)	0.012 (3)
C6A	0.027 (2)	0.035 (3)	0.034 (3)	−0.004 (2)	0.000 (2)	−0.010 (2)
C7A	0.032 (3)	0.054 (4)	0.042 (3)	−0.004 (2)	−0.005 (2)	−0.014 (3)
C8A	0.061 (3)	0.046 (4)	0.046 (4)	0.009 (3)	−0.006 (3)	−0.017 (3)
C9A	0.035 (2)	0.011 (2)	0.033 (3)	−0.0028 (19)	−0.004 (2)	0.002 (2)
C10A	0.050 (3)	0.029 (3)	0.039 (3)	0.003 (2)	0.004 (2)	−0.014 (2)
C11A	0.041 (3)	0.022 (3)	0.045 (3)	0.001 (2)	−0.011 (2)	−0.003 (2)
C12A	0.034 (2)	0.026 (3)	0.033 (3)	−0.003 (2)	0.011 (2)	0.007 (2)
C13A	0.048 (3)	0.052 (4)	0.039 (3)	0.019 (3)	0.021 (2)	0.005 (3)
C14A	0.054 (3)	0.049 (4)	0.060 (4)	0.001 (3)	0.027 (3)	0.025 (3)
C15A	0.031 (2)	0.014 (2)	0.013 (2)	0.0052 (19)	0.0028 (18)	−0.0026 (19)
Ni1A	0.0189 (3)	0.0126 (3)	0.0195 (3)	0.0011 (2)	0.0009 (2)	0.0015 (2)
O1A	0.0207 (15)	0.0216 (18)	0.0339 (19)	−0.0012 (13)	0.0005 (12)	0.0099 (15)
O2A	0.0219 (15)	0.0147 (17)	0.0279 (18)	0.0003 (12)	0.0011 (12)	0.0043 (13)
O3A	0.0320 (16)	0.0214 (18)	0.0234 (18)	0.0081 (14)	−0.0024 (13)	0.0046 (14)
P1A	0.0227 (6)	0.0149 (6)	0.0240 (7)	0.0013 (5)	0.0001 (5)	0.0031 (5)
P2A	0.0190 (5)	0.0212 (7)	0.0257 (7)	−0.0001 (5)	0.0004 (5)	0.0001 (5)
C1B	0.0146 (19)	0.024 (3)	0.021 (3)	−0.0017 (18)	0.0000 (17)	−0.003 (2)
C2B	0.0146 (19)	0.027 (3)	0.018 (2)	0.0008 (18)	0.0021 (16)	−0.004 (2)
C3B	0.036 (2)	0.023 (3)	0.014 (2)	−0.010 (2)	0.0070 (18)	0.000 (2)
C4B	0.064 (3)	0.022 (3)	0.031 (3)	−0.012 (2)	0.007 (2)	0.006 (2)
C5B	0.045 (3)	0.049 (4)	0.027 (3)	−0.024 (3)	0.018 (2)	0.002 (2)
C6B	0.018 (2)	0.014 (2)	0.023 (3)	−0.0004 (17)	0.0038 (17)	0.0015 (19)
C7B	0.024 (2)	0.025 (3)	0.031 (3)	0.0029 (19)	0.0052 (19)	−0.011 (2)
C8B	0.023 (2)	0.029 (3)	0.032 (3)	0.002 (2)	0.0027 (19)	−0.001 (2)
C9B	0.019 (2)	0.032 (3)	0.031 (3)	0.000 (2)	0.0095 (18)	−0.011 (2)
C10B	0.027 (2)	0.049 (4)	0.056 (4)	0.003 (2)	0.012 (2)	−0.027 (3)
C11B	0.036 (3)	0.034 (3)	0.062 (4)	0.013 (2)	0.012 (2)	−0.002 (3)
C12B	0.023 (2)	0.032 (3)	0.018 (3)	−0.010 (2)	0.0069 (18)	−0.005 (2)
C13B	0.037 (3)	0.034 (3)	0.022 (3)	−0.003 (2)	0.008 (2)	0.007 (2)
C14B	0.034 (3)	0.053 (4)	0.030 (3)	−0.011 (2)	0.012 (2)	0.008 (3)
C15B	0.023 (2)	0.013 (2)	0.018 (3)	−0.0016 (18)	−0.0032 (18)	0.0047 (19)
Ni1B	0.0141 (2)	0.0162 (3)	0.0144 (3)	−0.0024 (2)	0.0028 (2)	−0.0025 (2)
O1B	0.0186 (14)	0.0237 (17)	0.0173 (17)	−0.0043 (12)	0.0044 (12)	−0.0058 (13)
O2B	0.0173 (14)	0.0265 (18)	0.0169 (17)	−0.0090 (12)	0.0031 (11)	−0.0040 (14)
O3B	0.0250 (15)	0.0214 (18)	0.0246 (18)	−0.0047 (13)	−0.0021 (12)	−0.0014 (14)
P1B	0.0153 (5)	0.0207 (6)	0.0184 (7)	−0.0013 (5)	0.0047 (4)	−0.0047 (5)
P2B	0.0162 (5)	0.0151 (6)	0.0145 (6)	−0.0025 (4)	0.0036 (4)	−0.0006 (5)
C1C	0.025 (2)	0.013 (2)	0.028 (3)	0.0046 (18)	0.0096 (18)	0.009 (2)
C2C	0.020 (2)	0.022 (3)	0.025 (3)	0.0040 (19)	0.0026 (18)	0.001 (2)
C3C	0.020 (2)	0.021 (3)	0.015 (2)	0.0029 (18)	0.0052 (17)	−0.0022 (19)
C4C	0.041 (3)	0.029 (3)	0.023 (3)	0.006 (2)	0.014 (2)	0.002 (2)
C5C	0.026 (2)	0.022 (3)	0.024 (3)	0.0001 (19)	0.0064 (18)	−0.007 (2)
C6C	0.020 (2)	0.027 (3)	0.022 (3)	0.0052 (19)	0.0075 (17)	−0.005 (2)
C7C	0.023 (2)	0.030 (3)	0.035 (3)	−0.002 (2)	0.0091 (19)	−0.004 (2)
C8C	0.033 (2)	0.031 (3)	0.023 (3)	−0.004 (2)	0.013 (2)	0.001 (2)
C9C	0.027 (2)	0.013 (2)	0.032 (3)	−0.0003 (18)	0.0121 (19)	0.004 (2)
C10C	0.034 (3)	0.044 (3)	0.032 (3)	0.001 (2)	0.015 (2)	0.012 (2)
C11C	0.021 (2)	0.028 (3)	0.037 (3)	−0.004 (2)	0.0090 (19)	−0.004 (2)
C12C	0.032 (2)	0.019 (3)	0.023 (3)	−0.0006 (19)	0.0099 (19)	0.000 (2)
C13C	0.074 (4)	0.034 (3)	0.040 (4)	−0.012 (3)	0.034 (3)	−0.006 (3)
C14C	0.044 (3)	0.023 (3)	0.034 (3)	−0.001 (2)	0.010 (2)	−0.008 (2)
C15C	0.019 (2)	0.024 (3)	0.017 (3)	−0.002 (2)	0.0054 (18)	−0.004 (2)
Ni1C	0.0175 (3)	0.0123 (3)	0.0202 (3)	0.0011 (2)	0.0029 (2)	0.0022 (2)
O1C	0.0202 (14)	0.0162 (17)	0.0295 (19)	−0.0020 (12)	−0.0030 (12)	−0.0007 (14)
O2C	0.0171 (14)	0.0165 (16)	0.0277 (18)	0.0028 (12)	−0.0039 (12)	0.0004 (13)
O3C	0.0216 (14)	0.0179 (17)	0.0268 (18)	0.0047 (13)	−0.0004 (12)	0.0065 (14)
P1C	0.0198 (5)	0.0145 (6)	0.0228 (7)	0.0012 (5)	0.0061 (4)	0.0027 (5)
P2C	0.0183 (5)	0.0142 (6)	0.0185 (6)	0.0021 (5)	0.0039 (4)	0.0007 (5)

Geometric parameters (Å, º) top

C1A—C2A	1.537 (6)	C9B—C10B	1.532 (6)
C1A—P1A	1.825 (4)	C9B—P1B	1.832 (4)
C1A—H1A1	0.99	C9B—H9B	1
C1A—H1A2	0.99	C10B—H10D	0.98
C2A—P2A	1.833 (4)	C10B—H10E	0.98
C2A—H2A1	0.99	C10B—H10F	0.98
C2A—H2A2	0.99	C11B—H11D	0.98
C3A—C5A	1.509 (6)	C11B—H11E	0.98
C3A—C4A	1.545 (6)	C11B—H11F	0.98
C3A—P2A	1.837 (4)	C12B—C13B	1.517 (6)
C3A—H3A	1	C12B—C14B	1.525 (5)
C4A—H4A1	0.98	C12B—P1B	1.834 (4)
C4A—H4A2	0.98	C12B—H12B	1
C4A—H4A3	0.98	C13B—H13D	0.98
C5A—H5A1	0.98	C13B—H13E	0.98
C5A—H5A2	0.98	C13B—H13F	0.98
C5A—H5A3	0.98	C14B—H14D	0.98
C6A—C8A	1.501 (6)	C14B—H14E	0.98
C6A—C7A	1.530 (5)	C14B—H14F	0.98
C6A—P2A	1.827 (5)	C15B—O3B	1.227 (4)
C6A—H6A	1	C15B—O2B	1.316 (5)
C7A—H7A1	0.98	C15B—O1B	1.332 (4)
C7A—H7A2	0.98	C15B—Ni1B	2.287 (4)
C7A—H7A3	0.98	Ni1B—O2B	1.887 (2)
C8A—H8A1	0.98	Ni1B—O1B	1.890 (3)
C8A—H8A2	0.98	Ni1B—P2B	2.1399 (12)
C8A—H8A3	0.98	Ni1B—P1B	2.1415 (11)
C9A—C10A	1.526 (6)	C1C—C2C	1.536 (6)
C9A—C11A	1.529 (5)	C1C—P1C	1.838 (4)
C9A—P1A	1.826 (4)	C1C—H1C1	0.99
C9A—H9A	1	C1C—H1C2	0.99
C10A—H10A	0.98	C2C—P2C	1.817 (4)
C10A—H10B	0.98	C2C—H2C1	0.99
C10A—H10C	0.98	C2C—H2C2	0.99
C11A—H11A	0.98	C3C—C4C	1.531 (5)
C11A—H11B	0.98	C3C—C5C	1.536 (6)
C11A—H11C	0.98	C3C—P2C	1.827 (4)
C12A—C13A	1.521 (7)	C3C—H3C	1
C12A—C14A	1.536 (6)	C4C—H4C1	0.98
C12A—P1A	1.821 (4)	C4C—H4C2	0.98
C12A—H12A	1	C4C—H4C3	0.98
C13A—H13A	0.98	C5C—H5C1	0.98
C13A—H13B	0.98	C5C—H5C2	0.98
C13A—H13C	0.98	C5C—H5C3	0.98
C14A—H14A	0.98	C6C—C8C	1.520 (6)
C14A—H14B	0.98	C6C—C7C	1.533 (5)
C14A—H14C	0.98	C6C—P2C	1.841 (4)
C15A—O3A	1.221 (4)	C6C—H6C	1
C15A—O2A	1.322 (4)	C7C—H7C1	0.98
C15A—O1A	1.322 (5)	C7C—H7C2	0.98
C15A—Ni1A	2.291 (4)	C7C—H7C3	0.98
Ni1A—O1A	1.879 (2)	C8C—H8C1	0.98
Ni1A—O2A	1.885 (3)	C8C—H8C2	0.98
Ni1A—P1A	2.1390 (12)	C8C—H8C3	0.98
Ni1A—P2A	2.1460 (11)	C9C—C10C	1.520 (6)
C1B—C2B	1.526 (5)	C9C—C11C	1.524 (5)
C1B—P1B	1.835 (4)	C9C—P1C	1.837 (4)
C1B—H1B1	0.99	C9C—H9C	1
C1B—H1B2	0.99	C10C—H10G	0.98
C2B—P2B	1.825 (3)	C10C—H10H	0.98
C2B—H2B1	0.99	C10C—H10I	0.98
C2B—H2B2	0.99	C11C—H11G	0.98
C3B—C4B	1.523 (6)	C11C—H11H	0.98
C3B—C5B	1.527 (5)	C11C—H11I	0.98
C3B—P2B	1.825 (4)	C12C—C14C	1.520 (6)
C3B—H3B	1	C12C—C13C	1.522 (6)
C4B—H4B1	0.98	C12C—P1C	1.847 (4)
C4B—H4B2	0.98	C12C—H12C	1
C4B—H4B3	0.98	C13C—H13G	0.98
C5B—H5B1	0.98	C13C—H13H	0.98
C5B—H5B2	0.98	C13C—H13I	0.98
C5B—H5B3	0.98	C14C—H14G	0.98
C6B—C8B	1.532 (5)	C14C—H14H	0.98
C6B—C7B	1.535 (5)	C14C—H14I	0.98
C6B—P2B	1.831 (4)	C15C—O3C	1.220 (4)
C6B—H6B	1	C15C—O2C	1.320 (4)
C7B—H7B1	0.98	C15C—O1C	1.328 (5)
C7B—H7B2	0.98	C15C—Ni1C	2.291 (4)
C7B—H7B3	0.98	Ni1C—O2C	1.877 (3)
C8B—H8B1	0.98	Ni1C—O1C	1.889 (2)
C8B—H8B2	0.98	Ni1C—P2C	2.1433 (10)
C8B—H8B3	0.98	Ni1C—P1C	2.1481 (12)
C9B—C11B	1.523 (6)

C2A—C1A—P1A	110.0 (3)	C9B—C10B—H10F	109.5
C2A—C1A—H1A1	109.7	H10D—C10B—H10F	109.5
P1A—C1A—H1A1	109.7	H10E—C10B—H10F	109.5
C2A—C1A—H1A2	109.7	C9B—C11B—H11D	109.5
P1A—C1A—H1A2	109.7	C9B—C11B—H11E	109.5
H1A1—C1A—H1A2	108.2	H11D—C11B—H11E	109.5
C1A—C2A—P2A	109.4 (3)	C9B—C11B—H11F	109.5
C1A—C2A—H2A1	109.8	H11D—C11B—H11F	109.5
P2A—C2A—H2A1	109.8	H11E—C11B—H11F	109.5
C1A—C2A—H2A2	109.8	C13B—C12B—C14B	111.6 (4)
P2A—C2A—H2A2	109.8	C13B—C12B—P1B	110.7 (3)
H2A1—C2A—H2A2	108.2	C14B—C12B—P1B	112.8 (3)
C5A—C3A—C4A	110.9 (4)	C13B—C12B—H12B	107.2
C5A—C3A—P2A	112.6 (3)	C14B—C12B—H12B	107.2
C4A—C3A—P2A	109.7 (3)	P1B—C12B—H12B	107.2
C5A—C3A—H3A	107.8	C12B—C13B—H13D	109.5
C4A—C3A—H3A	107.8	C12B—C13B—H13E	109.5
P2A—C3A—H3A	107.8	H13D—C13B—H13E	109.5
C3A—C4A—H4A1	109.5	C12B—C13B—H13F	109.5
C3A—C4A—H4A2	109.5	H13D—C13B—H13F	109.5
H4A1—C4A—H4A2	109.5	H13E—C13B—H13F	109.5
C3A—C4A—H4A3	109.5	C12B—C14B—H14D	109.5
H4A1—C4A—H4A3	109.5	C12B—C14B—H14E	109.5
H4A2—C4A—H4A3	109.5	H14D—C14B—H14E	109.5
C3A—C5A—H5A1	109.5	C12B—C14B—H14F	109.5
C3A—C5A—H5A2	109.5	H14D—C14B—H14F	109.5
H5A1—C5A—H5A2	109.5	H14E—C14B—H14F	109.5
C3A—C5A—H5A3	109.5	O3B—C15B—O2B	124.7 (4)
H5A1—C5A—H5A3	109.5	O3B—C15B—O1B	124.0 (4)
H5A2—C5A—H5A3	109.5	O2B—C15B—O1B	111.3 (3)
C8A—C6A—C7A	111.0 (4)	O3B—C15B—Ni1B	178.6 (3)
C8A—C6A—P2A	113.8 (3)	O2B—C15B—Ni1B	55.59 (18)
C7A—C6A—P2A	114.8 (3)	O1B—C15B—Ni1B	55.71 (18)
C8A—C6A—H6A	105.4	O2B—Ni1B—O1B	70.75 (11)
C7A—C6A—H6A	105.4	O2B—Ni1B—P2B	101.06 (9)
P2A—C6A—H6A	105.4	O1B—Ni1B—P2B	171.81 (8)
C6A—C7A—H7A1	109.5	O2B—Ni1B—P1B	171.17 (9)
C6A—C7A—H7A2	109.5	O1B—Ni1B—P1B	100.44 (8)
H7A1—C7A—H7A2	109.5	P2B—Ni1B—P1B	87.75 (4)
C6A—C7A—H7A3	109.5	O2B—Ni1B—C15B	35.14 (13)
H7A1—C7A—H7A3	109.5	O1B—Ni1B—C15B	35.62 (13)
H7A2—C7A—H7A3	109.5	P2B—Ni1B—C15B	136.19 (11)
C6A—C8A—H8A1	109.5	P1B—Ni1B—C15B	136.06 (12)
C6A—C8A—H8A2	109.5	C15B—O1B—Ni1B	88.7 (2)
H8A1—C8A—H8A2	109.5	C15B—O2B—Ni1B	89.3 (2)
C6A—C8A—H8A3	109.5	C9B—P1B—C12B	106.5 (2)
H8A1—C8A—H8A3	109.5	C9B—P1B—C1B	106.47 (18)
H8A2—C8A—H8A3	109.5	C12B—P1B—C1B	106.0 (2)
C10A—C9A—C11A	111.6 (4)	C9B—P1B—Ni1B	114.38 (15)
C10A—C9A—P1A	110.0 (3)	C12B—P1B—Ni1B	112.86 (12)
C11A—C9A—P1A	111.1 (3)	C1B—P1B—Ni1B	110.11 (13)
C10A—C9A—H9A	108	C2B—P2B—C3B	105.38 (18)
C11A—C9A—H9A	108	C2B—P2B—C6B	104.17 (18)
P1A—C9A—H9A	108	C3B—P2B—C6B	109.5 (2)
C9A—C10A—H10A	109.5	C2B—P2B—Ni1B	108.71 (14)
C9A—C10A—H10B	109.5	C3B—P2B—Ni1B	116.09 (15)
H10A—C10A—H10B	109.5	C6B—P2B—Ni1B	112.08 (13)
C9A—C10A—H10C	109.5	C2C—C1C—P1C	109.2 (3)
H10A—C10A—H10C	109.5	C2C—C1C—H1C1	109.8
H10B—C10A—H10C	109.5	P1C—C1C—H1C1	109.8
C9A—C11A—H11A	109.5	C2C—C1C—H1C2	109.8
C9A—C11A—H11B	109.5	P1C—C1C—H1C2	109.8
H11A—C11A—H11B	109.5	H1C1—C1C—H1C2	108.3
C9A—C11A—H11C	109.5	C1C—C2C—P2C	109.3 (3)
H11A—C11A—H11C	109.5	C1C—C2C—H2C1	109.8
H11B—C11A—H11C	109.5	P2C—C2C—H2C1	109.8
C13A—C12A—C14A	110.6 (4)	C1C—C2C—H2C2	109.8
C13A—C12A—P1A	110.8 (3)	P2C—C2C—H2C2	109.8
C14A—C12A—P1A	112.5 (3)	H2C1—C2C—H2C2	108.3
C13A—C12A—H12A	107.5	C4C—C3C—C5C	109.7 (3)
C14A—C12A—H12A	107.5	C4C—C3C—P2C	109.8 (3)
P1A—C12A—H12A	107.5	C5C—C3C—P2C	111.9 (3)
C12A—C13A—H13A	109.5	C4C—C3C—H3C	108.4
C12A—C13A—H13B	109.5	C5C—C3C—H3C	108.4
H13A—C13A—H13B	109.5	P2C—C3C—H3C	108.4
C12A—C13A—H13C	109.5	C3C—C4C—H4C1	109.5
H13A—C13A—H13C	109.5	C3C—C4C—H4C2	109.5
H13B—C13A—H13C	109.5	H4C1—C4C—H4C2	109.5
C12A—C14A—H14A	109.5	C3C—C4C—H4C3	109.5
C12A—C14A—H14B	109.5	H4C1—C4C—H4C3	109.5
H14A—C14A—H14B	109.5	H4C2—C4C—H4C3	109.5
C12A—C14A—H14C	109.5	C3C—C5C—H5C1	109.5
H14A—C14A—H14C	109.5	C3C—C5C—H5C2	109.5
H14B—C14A—H14C	109.5	H5C1—C5C—H5C2	109.5
O3A—C15A—O2A	125.2 (4)	C3C—C5C—H5C3	109.5
O3A—C15A—O1A	124.3 (4)	H5C1—C5C—H5C3	109.5
O2A—C15A—O1A	110.5 (3)	H5C2—C5C—H5C3	109.5
O3A—C15A—Ni1A	178.5 (3)	C8C—C6C—C7C	111.7 (4)
O2A—C15A—Ni1A	55.36 (18)	C8C—C6C—P2C	113.8 (3)
O1A—C15A—Ni1A	55.10 (18)	C7C—C6C—P2C	113.1 (3)
O1A—Ni1A—O2A	70.50 (11)	C8C—C6C—H6C	105.8
O1A—Ni1A—P1A	98.44 (9)	C7C—C6C—H6C	105.8
O2A—Ni1A—P1A	168.79 (8)	P2C—C6C—H6C	105.8
O1A—Ni1A—P2A	172.56 (10)	C6C—C7C—H7C1	109.5
O2A—Ni1A—P2A	102.91 (8)	C6C—C7C—H7C2	109.5
P1A—Ni1A—P2A	88.01 (4)	H7C1—C7C—H7C2	109.5
O1A—Ni1A—C15A	35.25 (13)	C6C—C7C—H7C3	109.5
O2A—Ni1A—C15A	35.25 (12)	H7C1—C7C—H7C3	109.5
P1A—Ni1A—C15A	133.66 (11)	H7C2—C7C—H7C3	109.5
P2A—Ni1A—C15A	138.05 (11)	C6C—C8C—H8C1	109.5
C15A—O1A—Ni1A	89.7 (2)	C6C—C8C—H8C2	109.5
C15A—O2A—Ni1A	89.4 (2)	H8C1—C8C—H8C2	109.5
C12A—P1A—C1A	106.8 (2)	C6C—C8C—H8C3	109.5
C12A—P1A—C9A	106.5 (2)	H8C1—C8C—H8C3	109.5
C1A—P1A—C9A	106.93 (19)	H8C2—C8C—H8C3	109.5
C12A—P1A—Ni1A	111.46 (15)	C10C—C9C—C11C	111.2 (3)
C1A—P1A—Ni1A	110.94 (14)	C10C—C9C—P1C	110.6 (3)
C9A—P1A—Ni1A	113.81 (16)	C11C—C9C—P1C	110.6 (3)
C6A—P2A—C2A	103.1 (2)	C10C—C9C—H9C	108.1
C6A—P2A—C3A	109.8 (2)	C11C—C9C—H9C	108.1
C2A—P2A—C3A	106.0 (2)	P1C—C9C—H9C	108.1
C6A—P2A—Ni1A	110.17 (14)	C9C—C10C—H10G	109.5
C2A—P2A—Ni1A	109.42 (14)	C9C—C10C—H10H	109.5
C3A—P2A—Ni1A	117.29 (15)	H10G—C10C—H10H	109.5
C2B—C1B—P1B	110.2 (3)	C9C—C10C—H10I	109.5
C2B—C1B—H1B1	109.6	H10G—C10C—H10I	109.5
P1B—C1B—H1B1	109.6	H10H—C10C—H10I	109.5
C2B—C1B—H1B2	109.6	C9C—C11C—H11G	109.5
P1B—C1B—H1B2	109.6	C9C—C11C—H11H	109.5
H1B1—C1B—H1B2	108.1	H11G—C11C—H11H	109.5
C1B—C2B—P2B	108.3 (3)	C9C—C11C—H11I	109.5
C1B—C2B—H2B1	110	H11G—C11C—H11I	109.5
P2B—C2B—H2B1	110	H11H—C11C—H11I	109.5
C1B—C2B—H2B2	110	C14C—C12C—C13C	112.5 (4)
P2B—C2B—H2B2	110	C14C—C12C—P1C	113.4 (3)
H2B1—C2B—H2B2	108.4	C13C—C12C—P1C	110.0 (3)
C4B—C3B—C5B	110.8 (4)	C14C—C12C—H12C	106.8
C4B—C3B—P2B	109.6 (3)	C13C—C12C—H12C	106.8
C5B—C3B—P2B	111.8 (3)	P1C—C12C—H12C	106.8
C4B—C3B—H3B	108.2	C12C—C13C—H13G	109.5
C5B—C3B—H3B	108.2	C12C—C13C—H13H	109.5
P2B—C3B—H3B	108.2	H13G—C13C—H13H	109.5
C3B—C4B—H4B1	109.5	C12C—C13C—H13I	109.5
C3B—C4B—H4B2	109.5	H13G—C13C—H13I	109.5
H4B1—C4B—H4B2	109.5	H13H—C13C—H13I	109.5
C3B—C4B—H4B3	109.5	C12C—C14C—H14G	109.5
H4B1—C4B—H4B3	109.5	C12C—C14C—H14H	109.5
H4B2—C4B—H4B3	109.5	H14G—C14C—H14H	109.5
C3B—C5B—H5B1	109.5	C12C—C14C—H14I	109.5
C3B—C5B—H5B2	109.5	H14G—C14C—H14I	109.5
H5B1—C5B—H5B2	109.5	H14H—C14C—H14I	109.5
C3B—C5B—H5B3	109.5	O3C—C15C—O2C	124.9 (4)
H5B1—C5B—H5B3	109.5	O3C—C15C—O1C	124.6 (3)
H5B2—C5B—H5B3	109.5	O2C—C15C—O1C	110.5 (3)
C8B—C6B—C7B	112.0 (3)	O3C—C15C—Ni1C	177.9 (3)
C8B—C6B—P2B	112.4 (3)	O2C—C15C—Ni1C	55.01 (19)
C7B—C6B—P2B	113.7 (3)	O1C—C15C—Ni1C	55.54 (19)
C8B—C6B—H6B	106	O2C—Ni1C—O1C	70.55 (11)
C7B—C6B—H6B	106	O2C—Ni1C—P2C	99.18 (8)
P2B—C6B—H6B	106	O1C—Ni1C—P2C	169.54 (9)
C6B—C7B—H7B1	109.5	O2C—Ni1C—P1C	172.35 (8)
C6B—C7B—H7B2	109.5	O1C—Ni1C—P1C	101.83 (9)
H7B1—C7B—H7B2	109.5	P2C—Ni1C—P1C	88.46 (4)
C6B—C7B—H7B3	109.5	O2C—Ni1C—C15C	35.16 (12)
H7B1—C7B—H7B3	109.5	O1C—Ni1C—C15C	35.40 (12)
H7B2—C7B—H7B3	109.5	P2C—Ni1C—C15C	134.25 (11)
C6B—C8B—H8B1	109.5	P1C—Ni1C—C15C	137.23 (11)
C6B—C8B—H8B2	109.5	C15C—O1C—Ni1C	89.1 (2)
H8B1—C8B—H8B2	109.5	C15C—O2C—Ni1C	89.8 (2)
C6B—C8B—H8B3	109.5	C9C—P1C—C1C	105.72 (19)
H8B1—C8B—H8B3	109.5	C9C—P1C—C12C	105.13 (19)
H8B2—C8B—H8B3	109.5	C1C—P1C—C12C	106.01 (19)
C11B—C9B—C10B	110.5 (4)	C9C—P1C—Ni1C	116.71 (14)
C11B—C9B—P1B	110.3 (3)	C1C—P1C—Ni1C	109.53 (14)
C10B—C9B—P1B	111.4 (3)	C12C—P1C—Ni1C	112.98 (14)
C11B—C9B—H9B	108.2	C2C—P2C—C3C	106.6 (2)
C10B—C9B—H9B	108.2	C2C—P2C—C6C	103.51 (19)
P1B—C9B—H9B	108.2	C3C—P2C—C6C	109.25 (18)
C9B—C10B—H10D	109.5	C2C—P2C—Ni1C	108.77 (13)
C9B—C10B—H10E	109.5	C3C—P2C—Ni1C	113.61 (13)
H10D—C10B—H10E	109.5	C6C—P2C—Ni1C	114.35 (13)

P1A—C1A—C2A—P2A	37.1 (4)	P2B—Ni1B—P1B—C9B	−120.77 (16)
O3A—C15A—Ni1A—O1A	68 (13)	C15B—Ni1B—P1B—C9B	59.6 (2)
O2A—C15A—Ni1A—O1A	−179.5 (4)	O2B—Ni1B—P1B—C12B	−58.2 (6)
O3A—C15A—Ni1A—O2A	−112 (13)	O1B—Ni1B—P1B—C12B	−62.57 (18)
O1A—C15A—Ni1A—O2A	179.5 (4)	P2B—Ni1B—P1B—C12B	117.26 (16)
O3A—C15A—Ni1A—P1A	65 (13)	C15B—Ni1B—P1B—C12B	−62.4 (2)
O2A—C15A—Ni1A—P1A	177.52 (17)	O2B—Ni1B—P1B—C1B	−176.4 (6)
O1A—C15A—Ni1A—P1A	−2.9 (3)	O1B—Ni1B—P1B—C1B	179.23 (17)
O3A—C15A—Ni1A—P2A	−106 (13)	P2B—Ni1B—P1B—C1B	−0.95 (15)
O2A—C15A—Ni1A—P2A	5.7 (3)	C15B—Ni1B—P1B—C1B	179.4 (2)
O1A—C15A—Ni1A—P2A	−174.78 (18)	C1B—C2B—P2B—C3B	−165.3 (3)
O3A—C15A—O1A—Ni1A	−178.3 (4)	C1B—C2B—P2B—C6B	79.5 (3)
O2A—C15A—O1A—Ni1A	0.4 (3)	C1B—C2B—P2B—Ni1B	−40.2 (3)
O2A—Ni1A—O1A—C15A	−0.3 (2)	C4B—C3B—P2B—C2B	66.7 (3)
P1A—Ni1A—O1A—C15A	177.8 (2)	C5B—C3B—P2B—C2B	−170.0 (3)
P2A—Ni1A—O1A—C15A	28.0 (9)	C4B—C3B—P2B—C6B	178.3 (3)
O3A—C15A—O2A—Ni1A	178.3 (4)	C5B—C3B—P2B—C6B	−58.5 (4)
O1A—C15A—O2A—Ni1A	−0.4 (3)	C4B—C3B—P2B—Ni1B	−53.6 (3)
O1A—Ni1A—O2A—C15A	0.3 (2)	C5B—C3B—P2B—Ni1B	69.7 (3)
P1A—Ni1A—O2A—C15A	−9.3 (6)	C8B—C6B—P2B—C2B	−158.0 (3)
P2A—Ni1A—O2A—C15A	−176.1 (2)	C7B—C6B—P2B—C2B	73.5 (3)
C13A—C12A—P1A—C1A	71.3 (4)	C8B—C6B—P2B—C3B	89.7 (3)
C14A—C12A—P1A—C1A	−53.2 (4)	C7B—C6B—P2B—C3B	−38.8 (3)
C13A—C12A—P1A—C9A	−174.7 (3)	C8B—C6B—P2B—Ni1B	−40.6 (3)
C14A—C12A—P1A—C9A	60.8 (4)	C7B—C6B—P2B—Ni1B	−169.2 (2)
C13A—C12A—P1A—Ni1A	−50.1 (4)	O2B—Ni1B—P2B—C2B	−159.86 (17)
C14A—C12A—P1A—Ni1A	−174.5 (3)	O1B—Ni1B—P2B—C2B	−160.4 (6)
C2A—C1A—P1A—C12A	−147.5 (3)	P1B—Ni1B—P2B—C2B	20.84 (15)
C2A—C1A—P1A—C9A	98.8 (3)	C15B—Ni1B—P2B—C2B	−159.5 (2)
C2A—C1A—P1A—Ni1A	−25.9 (3)	O2B—Ni1B—P2B—C3B	−41.33 (17)
C10A—C9A—P1A—C12A	−176.3 (3)	O1B—Ni1B—P2B—C3B	−41.8 (7)
C11A—C9A—P1A—C12A	59.6 (4)	P1B—Ni1B—P2B—C3B	139.38 (15)
C10A—C9A—P1A—C1A	−62.3 (4)	C15B—Ni1B—P2B—C3B	−41.0 (2)
C11A—C9A—P1A—C1A	173.6 (3)	O2B—Ni1B—P2B—C6B	85.53 (16)
C10A—C9A—P1A—Ni1A	60.5 (3)	O1B—Ni1B—P2B—C6B	85.0 (7)
C11A—C9A—P1A—Ni1A	−63.6 (3)	P1B—Ni1B—P2B—C6B	−93.76 (14)
O1A—Ni1A—P1A—C12A	−53.44 (19)	C15B—Ni1B—P2B—C6B	85.9 (2)
O2A—Ni1A—P1A—C12A	−44.3 (5)	P1C—C1C—C2C—P2C	40.7 (3)
P2A—Ni1A—P1A—C12A	122.83 (16)	O3C—C15C—Ni1C—O2C	89 (9)
C15A—Ni1A—P1A—C12A	−51.7 (2)	O1C—C15C—Ni1C—O2C	−177.6 (4)
O1A—Ni1A—P1A—C1A	−172.34 (19)	O3C—C15C—Ni1C—O1C	−94 (9)
O2A—Ni1A—P1A—C1A	−163.2 (5)	O2C—C15C—Ni1C—O1C	177.6 (4)
P2A—Ni1A—P1A—C1A	3.92 (17)	O3C—C15C—Ni1C—P2C	84 (9)
C15A—Ni1A—P1A—C1A	−170.6 (2)	O2C—C15C—Ni1C—P2C	−4.9 (3)
O1A—Ni1A—P1A—C9A	67.01 (17)	O1C—C15C—Ni1C—P2C	177.53 (16)
O2A—Ni1A—P1A—C9A	76.1 (5)	O3C—C15C—Ni1C—P1C	−93 (9)
P2A—Ni1A—P1A—C9A	−116.72 (15)	O2C—C15C—Ni1C—P1C	178.66 (16)
C15A—Ni1A—P1A—C9A	68.7 (2)	O1C—C15C—Ni1C—P1C	1.1 (3)
C8A—C6A—P2A—C2A	−163.5 (4)	O3C—C15C—O1C—Ni1C	177.4 (4)
C7A—C6A—P2A—C2A	67.0 (4)	O2C—C15C—O1C—Ni1C	−2.1 (3)
C8A—C6A—P2A—C3A	83.8 (4)	O2C—Ni1C—O1C—C15C	1.5 (2)
C7A—C6A—P2A—C3A	−45.6 (4)	P2C—Ni1C—O1C—C15C	−9.8 (6)
C8A—C6A—P2A—Ni1A	−46.8 (4)	P1C—Ni1C—O1C—C15C	−179.3 (2)
C7A—C6A—P2A—Ni1A	−176.3 (3)	O3C—C15C—O2C—Ni1C	−177.4 (4)
C1A—C2A—P2A—C6A	82.8 (3)	O1C—C15C—O2C—Ni1C	2.1 (3)
C1A—C2A—P2A—C3A	−161.8 (3)	O1C—Ni1C—O2C—C15C	−1.5 (2)
C1A—C2A—P2A—Ni1A	−34.4 (3)	P2C—Ni1C—O2C—C15C	176.5 (2)
C5A—C3A—P2A—C6A	−62.3 (4)	P1C—Ni1C—O2C—C15C	−6.9 (8)
C4A—C3A—P2A—C6A	173.7 (3)	C10C—C9C—P1C—C1C	−60.6 (3)
C5A—C3A—P2A—C2A	−173.0 (3)	C11C—C9C—P1C—C1C	175.8 (3)
C4A—C3A—P2A—C2A	63.0 (3)	C10C—C9C—P1C—C12C	−172.5 (3)
C5A—C3A—P2A—Ni1A	64.4 (4)	C11C—C9C—P1C—C12C	63.9 (3)
C4A—C3A—P2A—Ni1A	−59.5 (3)	C10C—C9C—P1C—Ni1C	61.4 (3)
O1A—Ni1A—P2A—C6A	52.5 (8)	C11C—C9C—P1C—Ni1C	−62.2 (3)
O2A—Ni1A—P2A—C6A	79.8 (2)	C2C—C1C—P1C—C9C	98.3 (3)
P1A—Ni1A—P2A—C6A	−97.68 (18)	C2C—C1C—P1C—C12C	−150.4 (3)
C15A—Ni1A—P2A—C6A	76.4 (2)	C2C—C1C—P1C—Ni1C	−28.2 (3)
O1A—Ni1A—P2A—C2A	165.2 (8)	C14C—C12C—P1C—C9C	65.5 (3)
O2A—Ni1A—P2A—C2A	−167.56 (19)	C13C—C12C—P1C—C9C	−167.6 (3)
P1A—Ni1A—P2A—C2A	14.98 (17)	C14C—C12C—P1C—C1C	−46.2 (3)
C15A—Ni1A—P2A—C2A	−170.9 (2)	C13C—C12C—P1C—C1C	80.7 (3)
O1A—Ni1A—P2A—C3A	−74.1 (8)	C14C—C12C—P1C—Ni1C	−166.1 (3)
O2A—Ni1A—P2A—C3A	−46.8 (2)	C13C—C12C—P1C—Ni1C	−39.2 (3)
P1A—Ni1A—P2A—C3A	135.75 (18)	O2C—Ni1C—P1C—C9C	67.8 (7)
C15A—Ni1A—P2A—C3A	−50.1 (2)	O1C—Ni1C—P1C—C9C	62.63 (18)
P1B—C1B—C2B—P2B	39.2 (3)	P2C—Ni1C—P1C—C9C	−115.47 (16)
O3B—C15B—Ni1B—O2B	102 (14)	C15C—Ni1C—P1C—C9C	62.0 (2)
O1B—C15B—Ni1B—O2B	−179.2 (4)	O2C—Ni1C—P1C—C1C	−172.2 (7)
O3B—C15B—Ni1B—O1B	−79 (14)	O1C—Ni1C—P1C—C1C	−177.35 (17)
O2B—C15B—Ni1B—O1B	179.2 (4)	P2C—Ni1C—P1C—C1C	4.55 (15)
O3B—C15B—Ni1B—P2B	101 (14)	C15C—Ni1C—P1C—C1C	−178.0 (2)
O2B—C15B—Ni1B—P2B	−0.6 (3)	O2C—Ni1C—P1C—C12C	−54.2 (7)
O1B—C15B—Ni1B—P2B	−179.80 (16)	O1C—Ni1C—P1C—C12C	−59.43 (17)
O3B—C15B—Ni1B—P1B	−79 (14)	P2C—Ni1C—P1C—C12C	122.47 (15)
O2B—C15B—Ni1B—P1B	178.89 (16)	C15C—Ni1C—P1C—C12C	−60.1 (2)
O1B—C15B—Ni1B—P1B	−0.4 (3)	C1C—C2C—P2C—C3C	−160.3 (3)
O3B—C15B—O1B—Ni1B	178.3 (4)	C1C—C2C—P2C—C6C	84.6 (3)
O2B—C15B—O1B—Ni1B	−0.7 (3)	C1C—C2C—P2C—Ni1C	−37.4 (3)
O2B—Ni1B—O1B—C15B	0.5 (2)	C4C—C3C—P2C—C2C	73.4 (3)
P2B—Ni1B—O1B—C15B	1.0 (8)	C5C—C3C—P2C—C2C	−164.4 (3)
P1B—Ni1B—O1B—C15B	179.7 (2)	C4C—C3C—P2C—C6C	−175.3 (3)
O3B—C15B—O2B—Ni1B	−178.3 (4)	C5C—C3C—P2C—C6C	−53.2 (3)
O1B—C15B—O2B—Ni1B	0.7 (3)	C4C—C3C—P2C—Ni1C	−46.3 (3)
O1B—Ni1B—O2B—C15B	−0.5 (2)	C5C—C3C—P2C—Ni1C	75.8 (3)
P2B—Ni1B—O2B—C15B	179.6 (2)	C8C—C6C—P2C—C2C	−159.7 (3)
P1B—Ni1B—O2B—C15B	−5.0 (7)	C7C—C6C—P2C—C2C	71.6 (3)
C11B—C9B—P1B—C12B	179.1 (3)	C8C—C6C—P2C—C3C	87.1 (3)
C10B—C9B—P1B—C12B	56.0 (4)	C7C—C6C—P2C—C3C	−41.7 (4)
C11B—C9B—P1B—C1B	−68.2 (3)	C8C—C6C—P2C—Ni1C	−41.5 (4)
C10B—C9B—P1B—C1B	168.7 (3)	C7C—C6C—P2C—Ni1C	−170.3 (3)
C11B—C9B—P1B—Ni1B	53.7 (3)	O2C—Ni1C—P2C—C2C	−164.43 (17)
C10B—C9B—P1B—Ni1B	−69.4 (4)	O1C—Ni1C—P2C—C2C	−153.7 (5)
C13B—C12B—P1B—C9B	−175.1 (3)	P1C—Ni1C—P2C—C2C	16.01 (15)
C14B—C12B—P1B—C9B	59.1 (4)	C15C—Ni1C—P2C—C2C	−161.6 (2)
C13B—C12B—P1B—C1B	71.8 (3)	O2C—Ni1C—P2C—C3C	−45.93 (17)
C14B—C12B—P1B—C1B	−54.0 (4)	O1C—Ni1C—P2C—C3C	−35.2 (6)
C13B—C12B—P1B—Ni1B	−48.8 (3)	P1C—Ni1C—P2C—C3C	134.52 (15)
C14B—C12B—P1B—Ni1B	−174.6 (3)	C15C—Ni1C—P2C—C3C	−43.1 (2)
C2B—C1B—P1B—C9B	101.0 (3)	O2C—Ni1C—P2C—C6C	80.43 (18)
C2B—C1B—P1B—C12B	−145.9 (3)	O1C—Ni1C—P2C—C6C	91.2 (5)
C2B—C1B—P1B—Ni1B	−23.5 (3)	P1C—Ni1C—P2C—C6C	−99.12 (16)
O2B—Ni1B—P1B—C9B	63.8 (6)	C15C—Ni1C—P2C—C6C	83.3 (2)
O1B—Ni1B—P1B—C9B	59.40 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A1···O3Aⁱ	0.98	2.7	3.670 (5)	169
C4A—H4A3···O1Aⁱ	0.98	2.69	3.448 (5)	134
C8C—H8C1···O3Cⁱⁱ	0.98	2.71	3.595 (5)	150
C10B—H10F···O3Bⁱⁱ	0.98	2.52	3.335 (5)	141
C1A—H1A2···O3Bⁱⁱ	0.99	2.23	3.204 (5)	168
C1C—H1C2···O3Aⁱⁱⁱ	0.99	2.5	3.443 (5)	159
C9C—H9C···O2Aⁱⁱⁱ	1	2.48	3.455 (5)	165
C1B—H1B1···O3C^iv	0.99	2.5	3.452 (5)	161
C6B—H6B···O3C^iv	1	2.6	3.516 (5)	153

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

Experimental details

Crystal data
Chemical formula	[Ni(CO₃)(C₁₄H₃₂P₂)]
M_r	381.06
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	130
a, b, c (Å)	8.4974 (4), 46.582 (2), 14.7342 (7)
β (°)	103.618 (4)
V (Å³)	5668.2 (5)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	1.20
Crystal size (mm)	0.33 × 0.06 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.813, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	42978, 10329, 7642
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.096, 1.09
No. of reflections	10329
No. of parameters	592
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.59

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Selected bond lengths (Å) top

Ni1A—O1A	1.879 (2)	Ni1B—P2B	2.1399 (12)
Ni1A—O2A	1.885 (3)	Ni1B—P1B	2.1415 (11)
Ni1A—P1A	2.1390 (12)	Ni1C—O2C	1.877 (3)
Ni1A—P2A	2.1460 (11)	Ni1C—O1C	1.889 (2)
Ni1B—O2B	1.887 (2)	Ni1C—P2C	2.1433 (10)
Ni1B—O1B	1.890 (3)	Ni1C—P1C	2.1481 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5A1···O3Aⁱ	0.98	2.7	3.670 (5)	168.5
C4A—H4A3···O1Aⁱ	0.98	2.69	3.448 (5)	134.2
C8C—H8C1···O3Cⁱⁱ	0.98	2.71	3.595 (5)	149.8
C10B—H10F···O3Bⁱⁱ	0.98	2.52	3.335 (5)	140.5
C1A—H1A2···O3Bⁱⁱ	0.99	2.23	3.204 (5)	167.8
C1C—H1C2···O3Aⁱⁱⁱ	0.99	2.5	3.443 (5)	159.3
C9C—H9C···O2Aⁱⁱⁱ	1	2.48	3.455 (5)	164.5
C1B—H1B1···O3C^iv	0.99	2.5	3.452 (5)	161.1
C6B—H6B···O3C^iv	1	2.6	3.516 (5)	152.8

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

Acknowledgements

The authors thank PAPIIT-DGAPA-UNAM (IN-210613) and CONACYT (178265) for their financial support of this work.

References

Anderson, J. S., Iluc, V. M. & Hillhouse, G. L. (2010). Inorg. Chem. 49, 10203–10207. Web of Science CSD CrossRef CAS PubMed Google Scholar
Angulo, I. M., Bouwman, E., van Gorkum, R., Lok, S. M., Lutz, M. & Spek, A. L. (2003). J. Mol. Catal. A Chem. 202, 97–106. Web of Science CSD CrossRef CAS Google Scholar
Aresta, M. N., Nobile, C. F., Albano, V. G., Forni, E. & Manasero, M. (1975). J. Chem. Soc. Chem. Commun. pp. 636–637. Google Scholar
Arévalo, A. & García, J. J. (2010). Eur. J. Inorg. Chem. pp. 4063–4074. Google Scholar
Cañavera-Buelvas, F., Flores-Alamo, M. & García, J. J. (2011). Acta Cryst. E67, m501. Web of Science CSD CrossRef IUCr Journals Google Scholar
Castellanos-Blanco, N. Y., García, J. J. & Flores-Alamo, M. (2011). Acta Cryst. E67, m871. Web of Science CrossRef IUCr Journals Google Scholar
Dahlenburg, L. & Kurth, V. (2001). Inorg. Chim. Acta, 319, 176–182. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
González-Sebastián, L., Flores-Alamo, M. & García, J. J. (2012). Organometallics, 31, 8200–8207. Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vicic, D. A. & Jones, W. D. (1997). J. Am. Chem. Soc. 119, 10855–10856. CSD CrossRef CAS Web of Science Google Scholar