metal-organic compounds
{Bis[2-(diisopropylphosphanyl)ethyl]amine}carbonyl(tetrahydroborato)cobalt(I)
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
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 CoI 18-electron complex consists of a PNP, one CO and a HBH3 ligand coordinating to the CoI atom (Fig. 1). The coordination geometry at the CoI 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 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.
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 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 .
details are summarized in Table 1Structural data
CCDC reference: 1831663
https://doi.org/10.1107/S2414314618004716/rz4021sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004716/rz4021Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
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).[Co(BH4)(C16H37NP2)(CO)] | F(000) = 880 |
Mr = 407.19 | Dx = 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 |
Bruker APEXII CCD diffractometer | 5449 independent reflections |
Radiation source: fine-focus sealed tube | 4886 reflections with I > 2σ(I) |
Curved graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 28.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −10→10 |
Tmin = 0.72, Tmax = 0.89 | k = −36→36 |
38885 measured reflections | l = −13→13 |
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(Fo2) + (0.0317P)2 + 1.3762P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5449 reflections | Δρmax = 0.66 e Å−3 |
236 parameters | Δρmin = −0.42 e Å−3 |
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 Uiso(H) fixed at 1.2 Ueq(C) for CH, CH2 and 1.5 Ueq(C) for CH3. A rotating model was used for the methyl H atoms. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.