{Bis[2-(diiso­propyl­phosphan­yl)eth­yl]amine}­carbon­yl(tetra­hydro­borato)cobalt(I)

Junge, K.; Cingolani, A.; Spannenberg, A.; Beller, M.

doi:10.1107/S2414314618004716

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 3| March 2018| x180471

https://doi.org/10.1107/S2414314618004716

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{Bis[2-(diisopropylphosphanyl)ethyl]amine}carbonyl(tetrahydroborato)cobalt(I)

Kathrin Junge,^a ^* Andrea Cingolani,^b Anke Spannenberg ^a and Matthias Beller ^a

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany, and ^bUniversity of Bologna, Dipartiento di Chimica Industriale "Toso Montanari", viale Risorgimento 4, 40136 Bologna, Italy
^*Correspondence e-mail: kathrin.junge@catalysis.de

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 2 March 2018; accepted 22 March 2018; online 29 March 2018)

In the structure of title borohydride pincer complex, [Co(BH₄)(C₁₆H₃₇NP₂)(CO)], the cobalt(I) metal exhibits a distorted square-pyramidal coordination geometry with the basal positions occupied by the P and N atoms of the tridentate ligand and by the C atom of the carbon monoxide ligand. In the crystal, molecules interact only by van der Waals forces.

Keywords: crystal structure; colbalt pincer comples; borohydride.

CCDC reference: 1831663

Structure description

The title cobalt(I) borohydride species was formed by the reduction of the complex [CoBr₂(CO){HN((CH₂CH₂)PiPr₂)₂}] with five equivalents of NaBH₄. The title Co^I 18-electron complex consists of a PNP, one CO and a HBH₃ ligand coordinating to the Co^I atom (Fig. 1). The coordination geometry at the Co^I atom is best described as distorted square-pyramidal with the HBH₃ ligand in the apical position (τ = 0.25; Addison et al., 1984 ). The metal atom is displaced by 0.2757 (7) Å from the mean plane through the P, N and C atoms occupying the basal positions (r.m.s. deviation = 0.135 Å). Both five-membered chelate rings involving the PNP ligand display an envelope conformation, with the flap atoms C2 and C3 lying 0.564 (2) and 0.599 (2) Å, respectively, from the Co1/P1/C1/N1 and Co1/P2/C4/N1 plane. The crystal packing is governed only by van der Waals interactions.

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level. Hydrogen atoms except H1A–H1E are omitted for clarity.

Synthesis and crystallization

The synthesis of the starting complex [CoBr₂(CO){HN((CH₂CH₂)PiPr₂)₂}] was described before (Junge et al., 2018 ). [CoBr₂(CO){HN((CH₂CH₂)PiPr₂)₂}] (475.1 g, 0.86 mmol) and five equivalents of NaBH₄ (160.4 mg in 45 ml absolute EtOH) were added in a 100 ml Schlenk tube in an inert atmosphere. The mixture was stirred for 3 h at room temperature giving a dark-brown solution. The solvent was removed under vacuum and the residue was suspended in Et₂O. After filtration, Et₂O was removed in vacuum and the solid was extracted several times with n-heptane (40 ml). Finally, n-heptane was removed leaving a reddish powder. Pure red crystals suitable for single crystal X-ray diffraction analysis were grown from a solution of Et₂O layered with n-heptane. Yield: 158.1 mg (45%). IR ATR ν (CO): 2971, 1914, 1871, ν (NH): 3400, ν (CH): 2959, 2871, 2783, ν (BH): 2368 cm⁻¹.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	[Co(BH₄)(C₁₆H₃₇NP₂)(CO)]
M_r	407.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	8.0249 (2), 27.3200 (8), 10.3546 (3)
β (°)	97.101 (1)
V (Å³)	2252.73 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.91
Crystal size (mm)	0.38 × 0.32 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.72, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections	38885, 5449, 4886
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.08
No. of reflections	5449
No. of parameters	236
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.42
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1831663

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004716/rz4021sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004716/rz4021Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: publCIF (Westrip, 2010).

{Bis[2-(diisopropylphosphanyl)ethyl]amine}carbonyl(tetrahydroborato)cobalt(I) top

Crystal data top

[Co(BH₄)(C₁₆H₃₇NP₂)(CO)]	F(000) = 880
M_r = 407.19	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.0249 (2) Å	Cell parameters from 9366 reflections
b = 27.3200 (8) Å	θ = 2.5–28.8°
c = 10.3546 (3) Å	µ = 0.91 mm⁻¹
β = 97.101 (1)°	T = 150 K
V = 2252.73 (11) Å³	Prism, red
Z = 4	0.38 × 0.32 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	5449 independent reflections
Radiation source: fine-focus sealed tube	4886 reflections with I > 2σ(I)
Curved graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 28.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
T_min = 0.72, T_max = 0.89	k = −36→36
38885 measured reflections	l = −13→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0317P)² + 1.3762P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5449 reflections	Δρ_max = 0.66 e Å⁻³
236 parameters	Δρ_min = −0.42 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Atoms H1A–H1E could be located in a difference Fourier map and were refined freely. All other H atoms were placed in idealized positions with d(C—H) = 1.00 Å (CH), 0.99 Å (CH₂), 0.98 Å (CH₃) and refined using as riding with U_iso(H) fixed at 1.2 U_eq(C) for CH, CH₂ and 1.5 U_eq(C) for CH₃. A rotating model was used for the methyl H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
B1	−0.1303 (2)	0.04214 (7)	0.13590 (18)	0.0227 (3)
C1	0.3578 (2)	0.03751 (6)	0.24641 (16)	0.0265 (3)
H1F	0.4702	0.0332	0.2963	0.032*
H1G	0.2932	0.0069	0.2529	0.032*
C2	0.3747 (2)	0.04845 (6)	0.10518 (16)	0.0256 (3)
H2A	0.4645	0.0730	0.1001	0.031*
H2B	0.4059	0.0182	0.0612	0.031*
C3	0.2323 (2)	0.08158 (6)	−0.09605 (15)	0.0248 (3)
H3A	0.2656	0.0527	−0.1446	0.030*
H3B	0.3208	0.1068	−0.0963	0.030*
C4	0.0664 (2)	0.10156 (6)	−0.16071 (15)	0.0269 (3)
H4A	−0.0158	0.0747	−0.1786	0.032*
H4B	0.0822	0.1175	−0.2443	0.032*
C5	0.1334 (2)	0.05913 (7)	0.43592 (15)	0.0291 (4)
H5	0.0789	0.0297	0.3912	0.035*
C6	0.2471 (3)	0.03910 (8)	0.55335 (18)	0.0403 (5)
H6A	0.3005	0.0664	0.6042	0.060*
H6B	0.3338	0.0182	0.5233	0.060*
H6C	0.1800	0.0199	0.6079	0.060*
C7	−0.0108 (2)	0.09020 (8)	0.47412 (17)	0.0394 (4)
H7A	−0.0722	0.0716	0.5340	0.059*
H7B	−0.0870	0.0987	0.3960	0.059*
H7C	0.0343	0.1202	0.5169	0.059*
C8	0.4209 (2)	0.12393 (7)	0.40695 (18)	0.0325 (4)
H8	0.4845	0.1006	0.4691	0.039*
C9	0.5423 (2)	0.14279 (8)	0.3157 (2)	0.0435 (5)
H9A	0.4805	0.1624	0.2465	0.065*
H9B	0.5955	0.1150	0.2772	0.065*
H9C	0.6288	0.1630	0.3650	0.065*
C10	0.3582 (3)	0.16526 (8)	0.4871 (2)	0.0453 (5)
H10A	0.4544	0.1826	0.5338	0.068*
H10B	0.2889	0.1517	0.5499	0.068*
H10C	0.2911	0.1881	0.4293	0.068*
C11	−0.2425 (2)	0.14304 (8)	−0.07824 (18)	0.0341 (4)
H11	−0.2731	0.1127	−0.0325	0.041*
C12	−0.3163 (3)	0.18517 (9)	−0.0076 (2)	0.0506 (6)
H12A	−0.3013	0.2158	−0.0539	0.076*
H12B	−0.2588	0.1874	0.0813	0.076*
H12C	−0.4363	0.1793	−0.0049	0.076*
C13	−0.3250 (3)	0.13749 (11)	−0.2184 (2)	0.0572 (6)
H13A	−0.4430	0.1282	−0.2187	0.086*
H13B	−0.2664	0.1121	−0.2622	0.086*
H13C	−0.3186	0.1686	−0.2645	0.086*
C14	0.0493 (2)	0.20699 (6)	−0.10655 (18)	0.0313 (4)
H14	0.0024	0.2317	−0.0497	0.038*
C15	0.2386 (3)	0.21286 (8)	−0.0862 (2)	0.0471 (5)
H15A	0.2890	0.1915	−0.1469	0.071*
H15B	0.2814	0.2038	0.0034	0.071*
H15C	0.2678	0.2470	−0.1019	0.071*
C16	−0.0198 (3)	0.21952 (8)	−0.2475 (2)	0.0476 (5)
H16A	0.0344	0.2494	−0.2742	0.071*
H16B	−0.1413	0.2248	−0.2536	0.071*
H16C	0.0034	0.1924	−0.3047	0.071*
C17	0.0784 (2)	0.17611 (6)	0.20485 (17)	0.0305 (4)
Co1	0.09870 (2)	0.11960 (2)	0.14107 (2)	0.01695 (6)
H1A	−0.065 (3)	0.0841 (8)	0.157 (2)	0.037 (5)*
H1B	−0.034 (3)	0.0148 (8)	0.172 (2)	0.037 (6)*
H1C	−0.241 (3)	0.0384 (8)	0.188 (2)	0.037 (6)*
H1D	−0.161 (3)	0.0376 (8)	0.027 (2)	0.049 (6)*
N1	0.21356 (16)	0.06750 (5)	0.03935 (12)	0.0187 (2)
O1	0.0642 (2)	0.21577 (5)	0.24275 (16)	0.0561 (4)
P1	0.24794 (5)	0.08916 (2)	0.31343 (4)	0.02044 (9)
P2	−0.01034 (5)	0.14623 (2)	−0.04995 (4)	0.02156 (9)
H1E	0.147 (2)	0.0444 (7)	0.0339 (18)	0.022 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0229 (8)	0.0229 (8)	0.0225 (8)	−0.0002 (7)	0.0032 (7)	0.0005 (7)
C1	0.0223 (7)	0.0280 (8)	0.0284 (8)	0.0071 (6)	0.0001 (6)	0.0051 (6)
C2	0.0198 (7)	0.0296 (8)	0.0280 (8)	0.0084 (6)	0.0050 (6)	0.0004 (6)
C3	0.0305 (8)	0.0261 (8)	0.0197 (7)	0.0018 (6)	0.0106 (6)	−0.0003 (6)
C4	0.0381 (9)	0.0268 (8)	0.0155 (7)	0.0014 (7)	0.0024 (6)	0.0008 (6)
C5	0.0304 (8)	0.0383 (9)	0.0180 (7)	−0.0017 (7)	0.0014 (6)	0.0042 (7)
C6	0.0432 (11)	0.0521 (12)	0.0246 (9)	0.0009 (9)	0.0006 (8)	0.0161 (8)
C7	0.0363 (10)	0.0616 (13)	0.0212 (8)	0.0040 (9)	0.0069 (7)	−0.0010 (8)
C8	0.0304 (9)	0.0334 (9)	0.0298 (9)	−0.0032 (7)	−0.0115 (7)	0.0038 (7)
C9	0.0310 (10)	0.0447 (11)	0.0520 (12)	−0.0119 (8)	−0.0061 (9)	0.0058 (9)
C10	0.0531 (12)	0.0415 (11)	0.0365 (11)	−0.0053 (9)	−0.0136 (9)	−0.0112 (9)
C11	0.0230 (8)	0.0481 (11)	0.0297 (9)	0.0017 (7)	−0.0023 (7)	0.0102 (8)
C12	0.0283 (10)	0.0668 (15)	0.0578 (14)	0.0146 (10)	0.0095 (9)	0.0066 (11)
C13	0.0343 (11)	0.096 (2)	0.0382 (12)	−0.0045 (12)	−0.0089 (9)	0.0083 (12)
C14	0.0337 (9)	0.0252 (8)	0.0351 (9)	0.0038 (7)	0.0054 (7)	0.0069 (7)
C15	0.0371 (11)	0.0400 (11)	0.0643 (14)	−0.0026 (9)	0.0064 (10)	0.0167 (10)
C16	0.0615 (14)	0.0382 (11)	0.0422 (11)	0.0023 (10)	0.0028 (10)	0.0180 (9)
C17	0.0318 (9)	0.0290 (9)	0.0284 (9)	0.0075 (7)	−0.0059 (7)	−0.0058 (7)
Co1	0.01843 (10)	0.01766 (10)	0.01438 (10)	0.00293 (7)	0.00046 (7)	−0.00097 (7)
N1	0.0181 (6)	0.0198 (6)	0.0186 (6)	0.0015 (5)	0.0043 (5)	−0.0003 (5)
O1	0.0681 (11)	0.0346 (8)	0.0595 (10)	0.0175 (7)	−0.0161 (8)	−0.0228 (7)
P1	0.02065 (18)	0.0236 (2)	0.01616 (18)	0.00142 (15)	−0.00147 (14)	0.00128 (14)
P2	0.0239 (2)	0.0226 (2)	0.01789 (19)	0.00427 (15)	0.00123 (14)	0.00319 (14)

Geometric parameters (Å, º) top

B1—H1A	1.27 (2)	C9—H9B	0.9800
B1—H1B	1.10 (2)	C9—H9C	0.9800
B1—H1C	1.10 (2)	C10—H10A	0.9800
B1—H1D	1.13 (2)	C10—H10B	0.9800
C1—C2	1.515 (2)	C10—H10C	0.9800
C1—P1	1.8440 (17)	C11—C12	1.522 (3)
C1—H1F	0.9900	C11—C13	1.527 (3)
C1—H1G	0.9900	C11—P2	1.8520 (18)
C2—N1	1.4796 (19)	C11—H11	1.0000
C2—H2A	0.9900	C12—H12A	0.9800
C2—H2B	0.9900	C12—H12B	0.9800
C3—N1	1.4792 (19)	C12—H12C	0.9800
C3—C4	1.516 (2)	C13—H13A	0.9800
C3—H3A	0.9900	C13—H13B	0.9800
C3—H3B	0.9900	C13—H13C	0.9800
C4—P2	1.8327 (17)	C14—C15	1.516 (3)
C4—H4A	0.9900	C14—C16	1.535 (3)
C4—H4B	0.9900	C14—P2	1.8431 (18)
C5—C7	1.526 (3)	C14—H14	1.0000
C5—C6	1.528 (2)	C15—H15A	0.9800
C5—P1	1.8480 (17)	C15—H15B	0.9800
C5—H5	1.0000	C15—H15C	0.9800
C6—H6A	0.9800	C16—H16A	0.9800
C6—H6B	0.9800	C16—H16B	0.9800
C6—H6C	0.9800	C16—H16C	0.9800
C7—H7A	0.9800	C17—O1	1.163 (2)
C7—H7B	0.9800	C17—Co1	1.6949 (17)
C7—H7C	0.9800	Co1—N1	2.0555 (12)
C8—C10	1.523 (3)	Co1—P2	2.1863 (4)
C8—C9	1.528 (3)	Co1—P1	2.1869 (4)
C8—P1	1.8531 (18)	Co1—H1A	1.66 (2)
C8—H8	1.0000	N1—H1E	0.823 (19)
C9—H9A	0.9800

H1A—B1—H1B	107.3 (14)	C12—C11—C13	112.53 (18)
H1A—B1—H1C	109.8 (14)	C12—C11—P2	109.38 (14)
H1B—B1—H1C	110.3 (15)	C13—C11—P2	117.68 (14)
H1A—B1—H1D	108.0 (15)	C12—C11—H11	105.4
H1B—B1—H1D	108.5 (16)	C13—C11—H11	105.4
H1C—B1—H1D	112.8 (16)	P2—C11—H11	105.4
C2—C1—P1	108.44 (11)	C11—C12—H12A	109.5
C2—C1—H1F	110.0	C11—C12—H12B	109.5
P1—C1—H1F	110.0	H12A—C12—H12B	109.5
C2—C1—H1G	110.0	C11—C12—H12C	109.5
P1—C1—H1G	110.0	H12A—C12—H12C	109.5
H1F—C1—H1G	108.4	H12B—C12—H12C	109.5
N1—C2—C1	109.67 (12)	C11—C13—H13A	109.5
N1—C2—H2A	109.7	C11—C13—H13B	109.5
C1—C2—H2A	109.7	H13A—C13—H13B	109.5
N1—C2—H2B	109.7	C11—C13—H13C	109.5
C1—C2—H2B	109.7	H13A—C13—H13C	109.5
H2A—C2—H2B	108.2	H13B—C13—H13C	109.5
N1—C3—C4	109.02 (12)	C15—C14—C16	110.30 (17)
N1—C3—H3A	109.9	C15—C14—P2	110.25 (13)
C4—C3—H3A	109.9	C16—C14—P2	115.20 (14)
N1—C3—H3B	109.9	C15—C14—H14	106.9
C4—C3—H3B	109.9	C16—C14—H14	106.9
H3A—C3—H3B	108.3	P2—C14—H14	106.9
C3—C4—P2	107.94 (11)	C14—C15—H15A	109.5
C3—C4—H4A	110.1	C14—C15—H15B	109.5
P2—C4—H4A	110.1	H15A—C15—H15B	109.5
C3—C4—H4B	110.1	C14—C15—H15C	109.5
P2—C4—H4B	110.1	H15A—C15—H15C	109.5
H4A—C4—H4B	108.4	H15B—C15—H15C	109.5
C7—C5—C6	112.97 (15)	C14—C16—H16A	109.5
C7—C5—P1	112.85 (13)	C14—C16—H16B	109.5
C6—C5—P1	113.96 (13)	H16A—C16—H16B	109.5
C7—C5—H5	105.3	C14—C16—H16C	109.5
C6—C5—H5	105.3	H16A—C16—H16C	109.5
P1—C5—H5	105.3	H16B—C16—H16C	109.5
C5—C6—H6A	109.5	O1—C17—Co1	176.79 (18)
C5—C6—H6B	109.5	C17—Co1—N1	154.31 (8)
H6A—C6—H6B	109.5	C17—Co1—P2	90.14 (6)
C5—C6—H6C	109.5	N1—Co1—P2	85.50 (4)
H6A—C6—H6C	109.5	C17—Co1—P1	95.61 (6)
H6B—C6—H6C	109.5	N1—Co1—P1	85.40 (4)
C5—C7—H7A	109.5	P2—Co1—P1	169.253 (18)
C5—C7—H7B	109.5	C17—Co1—H1A	112.2 (7)
H7A—C7—H7B	109.5	N1—Co1—H1A	93.4 (7)
C5—C7—H7C	109.5	P2—Co1—H1A	93.1 (7)
H7A—C7—H7C	109.5	P1—Co1—H1A	93.2 (7)
H7B—C7—H7C	109.5	C3—N1—C2	110.05 (12)
C10—C8—C9	111.44 (17)	C3—N1—Co1	114.21 (9)
C10—C8—P1	112.85 (13)	C2—N1—Co1	115.41 (10)
C9—C8—P1	110.08 (13)	C3—N1—H1E	106.0 (13)
C10—C8—H8	107.4	C2—N1—H1E	106.4 (13)
C9—C8—H8	107.4	Co1—N1—H1E	103.8 (13)
P1—C8—H8	107.4	C1—P1—C5	102.71 (8)
C8—C9—H9A	109.5	C1—P1—C8	103.12 (8)
C8—C9—H9B	109.5	C5—P1—C8	105.84 (8)
H9A—C9—H9B	109.5	C1—P1—Co1	102.88 (5)
C8—C9—H9C	109.5	C5—P1—Co1	117.40 (6)
H9A—C9—H9C	109.5	C8—P1—Co1	122.06 (6)
H9B—C9—H9C	109.5	C4—P2—C14	106.27 (8)
C8—C10—H10A	109.5	C4—P2—C11	106.20 (9)
C8—C10—H10B	109.5	C14—P2—C11	106.73 (8)
H10A—C10—H10B	109.5	C4—P2—Co1	102.51 (5)
C8—C10—H10C	109.5	C14—P2—Co1	119.79 (6)
H10A—C10—H10C	109.5	C11—P2—Co1	114.19 (6)
H10B—C10—H10C	109.5

P1—C1—C2—N1	−44.85 (16)	C9—C8—P1—C5	169.94 (13)
N1—C3—C4—P2	48.02 (15)	C10—C8—P1—Co1	73.05 (15)
C4—C3—N1—C2	−179.27 (13)	C9—C8—P1—Co1	−52.15 (16)
C4—C3—N1—Co1	−47.59 (15)	C3—C4—P2—C14	98.19 (12)
C1—C2—N1—C3	176.00 (13)	C3—C4—P2—C11	−148.41 (12)
C1—C2—N1—Co1	44.96 (16)	C3—C4—P2—Co1	−28.31 (12)
C2—C1—P1—C5	148.85 (12)	C15—C14—P2—C4	−67.28 (16)
C2—C1—P1—C8	−101.28 (12)	C16—C14—P2—C4	58.33 (16)
C2—C1—P1—Co1	26.47 (12)	C15—C14—P2—C11	179.69 (15)
C7—C5—P1—C1	−161.14 (13)	C16—C14—P2—C11	−54.70 (17)
C6—C5—P1—C1	68.27 (15)	C15—C14—P2—Co1	48.01 (16)
C7—C5—P1—C8	91.05 (14)	C16—C14—P2—Co1	173.62 (12)
C6—C5—P1—C8	−39.53 (16)	C12—C11—P2—C4	−170.08 (14)
C7—C5—P1—Co1	−49.16 (14)	C13—C11—P2—C4	−40.04 (19)
C6—C5—P1—Co1	−179.75 (12)	C12—C11—P2—C14	−57.00 (16)
C10—C8—P1—C1	−172.37 (14)	C13—C11—P2—C14	73.03 (19)
C9—C8—P1—C1	62.42 (15)	C12—C11—P2—Co1	77.72 (14)
C10—C8—P1—C5	−64.86 (15)	C13—C11—P2—Co1	−152.24 (16)

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Junge, K., Wendt, B., Cingolani, A., Spannenberg, A., Wei, Z., Jiao, H. & Beller, M. (2018). Chem. Eur. J. 24, 1046–1052. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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