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The reaction of NiCl2 with 1,3-bis­[(di­phenyl­phosphan­yl)meth­yl]hexa­hydro­pyrimidine in the presence of 2,6-di­methyl­phenyl isocyanide and KPF6 afforded a new penta­coordinated PCP pincer NiII complex, namely {1,3-bis­[(di­phenyl­phosphan­yl)meth­yl]hexa­hydro­pyrimidin-2-yl-κN2}(2,6-di­methyl­phenyl isocyanide-κC)nickel(II) hexa­fluorido­phosphate 0.70-hydrate, [Ni(C9H9N)(C30H30ClN2P2)]PF6·0.7H2O or [NiCl{C(NCH2PPh2)2(CH2)33P,C,P′}(Xylyl-NC)]PF6·0.7H2O, in very good yield. Its X-ray structure showed a distorted square-pyramidal geometry and the compound does not undergo dissociation in solution, as shown by variable-temperature NMR and UV–Vis studies. Density functional theory (DFT) calculations provided an insight into the bonding; the nickel dsp2-hybridized orbitals form the basal plane and the nearly pure p orbital forms the axial bond. This is consistent with the NBO (natural bond orbital) analysis of analogous nickel(II) complexes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619006211/ky3175sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619006211/ky3175Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619006211/ky3175sup3.pdf
NMR, IR and absorption spectra, fractional coordinates and computational details

CCDC reference: 1911358

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{1,3-Bis[(diphenylphosphanyl)methyl]hexahydropyrimidin-2-yl-κN2}(2,6-dimethylphenyl isocyanide-κC)nickel(II) hexafluoridophosphate 0.70-hydrate top
Crystal data top
[Ni(C9H9N)(C30H30ClN2P2)]PF6·0.7H2OZ = 2
Mr = 863.42F(000) = 890
Triclinic, P1Dx = 1.477 Mg m3
a = 9.7632 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.8846 (5) ÅCell parameters from 24485 reflections
c = 18.5771 (9) Åθ = 1.9–26.0°
α = 99.687 (1)°µ = 0.76 mm1
β = 91.504 (1)°T = 100 K
γ = 93.472 (1)°Prism, brown
V = 1941.11 (16) Å30.38 × 0.3 × 0.25 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
6603 reflections with I > 2σ(I)
Radiation source: Fine focused sealed tubeRint = 0.027
hemisphere scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 912
Tmin = 0.761, Tmax = 0.827k = 1313
24485 measured reflectionsl = 2222
7473 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0324P)2 + 1.1895P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
7473 reflectionsΔρmax = 0.46 e Å3
548 parametersΔρmin = 0.30 e Å3
6 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.55256 (2)0.31871 (2)0.26588 (2)0.01216 (7)
Cl10.69379 (5)0.48010 (4)0.34566 (2)0.02068 (11)
P10.36300 (5)0.41089 (4)0.25893 (2)0.01180 (10)
P20.69958 (5)0.18756 (4)0.22150 (3)0.01532 (11)
P30.08955 (5)0.27772 (4)0.12213 (3)0.02086 (12)
F60.036 (2)0.3978 (15)0.0644 (9)0.025 (2)0.55 (5)
F50.109 (3)0.188 (3)0.0628 (15)0.032 (3)0.55 (5)
F30.088 (2)0.3692 (17)0.1820 (9)0.0241 (19)0.55 (5)
F20.2452 (11)0.3114 (18)0.1056 (10)0.032 (2)0.55 (5)
F40.0652 (11)0.2419 (18)0.1362 (12)0.044 (3)0.55 (5)
N30.44606 (16)0.15472 (14)0.36875 (9)0.0159 (3)
N10.53457 (16)0.50139 (13)0.17225 (8)0.0150 (3)
F10.1476 (19)0.1573 (11)0.1788 (8)0.040 (2)0.55 (5)
N20.71308 (16)0.37449 (14)0.14738 (8)0.0162 (3)
C320.38943 (18)0.06971 (16)0.41075 (10)0.0155 (4)
C10.26903 (19)0.47385 (15)0.33755 (10)0.0140 (4)
C380.35888 (19)0.11449 (17)0.48307 (11)0.0181 (4)
C120.20483 (19)0.36069 (17)0.12668 (10)0.0165 (4)
H120.2352750.4395810.1184410.020*
C330.3661 (2)0.05508 (17)0.37706 (11)0.0190 (4)
C20.3351 (2)0.49687 (17)0.40612 (10)0.0181 (4)
H20.4260930.4780100.4112430.022*
C70.24123 (18)0.32191 (16)0.19222 (10)0.0136 (4)
C180.80227 (19)0.28382 (18)0.16859 (11)0.0188 (4)
H18A0.8804630.3258150.1979290.023*
H18B0.8357270.2325000.1256480.023*
C310.48922 (18)0.22008 (16)0.33020 (10)0.0149 (4)
C60.1329 (2)0.50450 (18)0.32994 (11)0.0205 (4)
H60.0885620.4903720.2840870.025*
C130.42924 (19)0.54658 (16)0.22191 (10)0.0150 (4)
H13A0.3567440.5804390.1960480.018*
H13B0.4679560.6112370.2607340.018*
C90.11236 (19)0.12481 (17)0.15070 (11)0.0209 (4)
H90.0809470.0459930.1586560.025*
C170.60348 (18)0.40447 (16)0.18644 (10)0.0137 (4)
C80.19203 (19)0.20390 (17)0.20411 (11)0.0173 (4)
H80.2129330.1782890.2481960.021*
C350.3081 (2)0.13671 (18)0.41933 (12)0.0233 (4)
H350.2899790.2203680.3989390.028*
C110.12359 (19)0.28188 (18)0.07404 (10)0.0201 (4)
H110.0983970.3085060.0308490.024*
C100.07972 (19)0.16365 (18)0.08544 (11)0.0222 (4)
H100.0280660.1099940.0491020.027*
C370.3021 (2)0.02781 (19)0.52254 (11)0.0229 (4)
H370.2808530.0535740.5710220.028*
C250.6284 (2)0.05732 (17)0.15465 (10)0.0179 (4)
C260.4871 (2)0.04360 (17)0.14133 (11)0.0193 (4)
H260.4310480.0987970.1683290.023*
C300.7118 (2)0.02539 (18)0.11313 (12)0.0255 (5)
H300.8066210.0168100.1210140.031*
C190.8240 (2)0.13232 (19)0.28081 (11)0.0224 (4)
C40.1308 (2)0.57660 (17)0.45901 (11)0.0232 (4)
H40.0841520.6102340.4999690.028*
C30.2654 (2)0.54791 (17)0.46685 (11)0.0217 (4)
H30.3092880.5627880.5128070.026*
C360.2767 (2)0.09613 (19)0.49107 (12)0.0257 (5)
H360.2381980.1526030.5184310.031*
C140.5814 (2)0.58512 (18)0.12208 (11)0.0238 (4)
H14A0.6413210.6532200.1483860.029*
H14B0.5031140.6203240.1018770.029*
C390.3842 (2)0.25003 (18)0.51604 (12)0.0283 (5)
H39A0.4768800.2775720.5078430.042*
H39B0.3702290.2606700.5676230.042*
H39C0.3216710.2984620.4937340.042*
C280.5118 (2)0.13257 (18)0.04791 (12)0.0276 (5)
H280.4731170.1962200.0121270.033*
C50.0643 (2)0.55601 (19)0.39104 (12)0.0258 (5)
H50.0261990.5766350.3863030.031*
C270.4288 (2)0.05118 (18)0.08840 (11)0.0241 (4)
H270.3341210.0599790.0801420.029*
C200.9067 (2)0.2225 (2)0.32790 (11)0.0289 (5)
H200.8953680.3067700.3280830.035*
C160.7709 (2)0.4468 (2)0.09361 (12)0.0258 (5)
H16A0.8128150.3913530.0552200.031*
H16B0.8412480.5081510.1172980.031*
C150.6580 (2)0.5119 (2)0.06104 (12)0.0278 (5)
H15A0.5951320.4507100.0309080.033*
H15B0.6971950.5679560.0304640.033*
C340.4018 (3)0.0976 (2)0.29920 (12)0.0329 (5)
H34A0.3600080.0464660.2686010.049*
H34B0.3686210.1831240.2839520.049*
H34C0.4997160.0904700.2952070.049*
C290.6531 (2)0.11956 (19)0.06054 (13)0.0309 (5)
H290.7085600.1749200.0332520.037*
C230.9387 (2)0.0265 (2)0.32980 (15)0.0406 (6)
H230.9495790.1104100.3310060.049*
C211.0052 (2)0.1878 (3)0.37425 (12)0.0362 (6)
H211.0606090.2483250.4048520.043*
C240.8388 (2)0.0065 (2)0.28204 (13)0.0310 (5)
H240.7835580.0547140.2517980.037*
C221.0204 (2)0.0630 (3)0.37465 (13)0.0399 (6)
H221.0865400.0393240.4055780.048*
F3A0.058 (2)0.359 (2)0.1853 (11)0.026 (2)0.45 (5)
F6A0.060 (3)0.3932 (17)0.0566 (11)0.021 (2)0.45 (5)
F5A0.099 (4)0.197 (3)0.0574 (18)0.036 (5)0.45 (5)
F2A0.2487 (12)0.305 (2)0.1246 (13)0.036 (3)0.45 (5)
F4A0.0717 (12)0.258 (2)0.1210 (13)0.034 (3)0.45 (5)
F1A0.115 (3)0.1645 (14)0.1886 (10)0.047 (4)0.45 (5)
O10.7722 (3)0.7080 (2)0.26718 (16)0.0506 (10)0.702 (6)
H1A0.8452470.6908520.2447370.076*0.702 (6)
H1B0.7561700.6473240.2898120.076*0.702 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01062 (12)0.01432 (12)0.01261 (13)0.00193 (9)0.00260 (9)0.00463 (9)
Cl10.0178 (2)0.0266 (2)0.0157 (2)0.00350 (18)0.00200 (18)0.00054 (18)
P10.0113 (2)0.0128 (2)0.0116 (2)0.00111 (17)0.00153 (18)0.00263 (17)
P20.0119 (2)0.0184 (2)0.0172 (2)0.00412 (18)0.00352 (19)0.00604 (19)
P30.0233 (3)0.0153 (2)0.0239 (3)0.0010 (2)0.0062 (2)0.0043 (2)
F60.027 (5)0.026 (2)0.020 (3)0.015 (2)0.012 (3)0.002 (2)
F50.033 (4)0.023 (3)0.039 (5)0.011 (4)0.019 (4)0.013 (3)
F30.028 (5)0.025 (3)0.023 (2)0.011 (3)0.006 (3)0.011 (2)
F20.020 (2)0.042 (2)0.038 (5)0.003 (2)0.003 (2)0.022 (4)
F40.033 (3)0.045 (4)0.051 (8)0.021 (2)0.002 (3)0.004 (4)
N30.0152 (8)0.0156 (7)0.0184 (8)0.0025 (6)0.0022 (7)0.0060 (7)
N10.0163 (8)0.0154 (7)0.0147 (8)0.0009 (6)0.0040 (6)0.0060 (6)
F10.062 (5)0.026 (3)0.030 (3)0.009 (2)0.018 (3)0.005 (2)
N20.0135 (8)0.0202 (8)0.0166 (8)0.0017 (6)0.0063 (6)0.0072 (6)
C320.0128 (9)0.0166 (9)0.0188 (10)0.0008 (7)0.0010 (7)0.0084 (7)
C10.0158 (9)0.0114 (8)0.0146 (9)0.0005 (7)0.0034 (7)0.0015 (7)
C380.0148 (10)0.0207 (9)0.0200 (10)0.0028 (7)0.0003 (8)0.0065 (8)
C120.0138 (9)0.0185 (9)0.0175 (10)0.0018 (7)0.0037 (8)0.0030 (7)
C330.0171 (10)0.0193 (9)0.0215 (10)0.0022 (7)0.0023 (8)0.0060 (8)
C20.0199 (10)0.0176 (9)0.0173 (10)0.0030 (7)0.0006 (8)0.0037 (7)
C70.0093 (9)0.0168 (8)0.0140 (9)0.0041 (7)0.0023 (7)0.0004 (7)
C180.0125 (9)0.0228 (9)0.0224 (10)0.0033 (7)0.0058 (8)0.0064 (8)
C310.0134 (9)0.0159 (9)0.0150 (9)0.0045 (7)0.0004 (7)0.0006 (7)
C60.0162 (10)0.0229 (10)0.0209 (10)0.0008 (8)0.0006 (8)0.0005 (8)
C130.0149 (9)0.0136 (8)0.0169 (9)0.0005 (7)0.0021 (8)0.0035 (7)
C90.0122 (9)0.0152 (9)0.0341 (12)0.0012 (7)0.0037 (8)0.0002 (8)
C170.0126 (9)0.0156 (8)0.0125 (9)0.0019 (7)0.0002 (7)0.0022 (7)
C80.0134 (9)0.0180 (9)0.0215 (10)0.0034 (7)0.0019 (8)0.0055 (8)
C350.0232 (11)0.0167 (9)0.0313 (12)0.0015 (8)0.0025 (9)0.0091 (8)
C110.0141 (10)0.0309 (11)0.0138 (9)0.0041 (8)0.0002 (8)0.0008 (8)
C100.0124 (10)0.0267 (10)0.0231 (11)0.0022 (8)0.0009 (8)0.0086 (8)
C370.0228 (11)0.0299 (11)0.0188 (10)0.0042 (8)0.0051 (8)0.0104 (8)
C250.0201 (10)0.0167 (9)0.0186 (10)0.0035 (7)0.0062 (8)0.0061 (7)
C260.0203 (10)0.0198 (9)0.0187 (10)0.0033 (8)0.0050 (8)0.0047 (8)
C300.0219 (11)0.0209 (10)0.0347 (12)0.0045 (8)0.0124 (9)0.0051 (9)
C190.0143 (10)0.0355 (11)0.0215 (10)0.0107 (8)0.0084 (8)0.0124 (9)
C40.0271 (11)0.0169 (9)0.0233 (11)0.0051 (8)0.0142 (9)0.0030 (8)
C30.0309 (12)0.0190 (9)0.0154 (10)0.0005 (8)0.0037 (8)0.0038 (8)
C360.0219 (11)0.0277 (11)0.0324 (12)0.0007 (8)0.0039 (9)0.0201 (9)
C140.0272 (11)0.0230 (10)0.0256 (11)0.0034 (8)0.0093 (9)0.0149 (9)
C390.0397 (13)0.0222 (10)0.0233 (11)0.0040 (9)0.0028 (10)0.0038 (9)
C280.0413 (13)0.0168 (9)0.0234 (11)0.0044 (9)0.0053 (10)0.0014 (8)
C50.0152 (10)0.0252 (10)0.0337 (12)0.0009 (8)0.0070 (9)0.0048 (9)
C270.0249 (11)0.0240 (10)0.0248 (11)0.0005 (8)0.0017 (9)0.0086 (8)
C200.0204 (11)0.0455 (13)0.0216 (11)0.0131 (10)0.0019 (9)0.0036 (10)
C160.0229 (11)0.0324 (11)0.0261 (11)0.0040 (9)0.0136 (9)0.0137 (9)
C150.0320 (12)0.0342 (11)0.0231 (11)0.0079 (9)0.0120 (9)0.0177 (9)
C340.0499 (15)0.0228 (11)0.0248 (12)0.0007 (10)0.0058 (11)0.0009 (9)
C290.0376 (13)0.0198 (10)0.0347 (13)0.0038 (9)0.0191 (11)0.0002 (9)
C230.0297 (13)0.0500 (15)0.0540 (16)0.0168 (11)0.0141 (12)0.0360 (13)
C210.0213 (12)0.0648 (17)0.0238 (12)0.0162 (11)0.0034 (9)0.0064 (11)
C240.0205 (11)0.0388 (12)0.0407 (14)0.0079 (9)0.0068 (10)0.0234 (11)
C220.0202 (12)0.0762 (19)0.0308 (13)0.0149 (12)0.0050 (10)0.0262 (13)
F3A0.029 (7)0.025 (3)0.027 (3)0.014 (4)0.006 (4)0.007 (2)
F6A0.024 (6)0.018 (3)0.018 (3)0.010 (3)0.013 (3)0.001 (2)
F5A0.042 (8)0.030 (7)0.036 (5)0.016 (4)0.023 (4)0.023 (7)
F2A0.019 (3)0.048 (4)0.047 (8)0.008 (2)0.017 (3)0.032 (6)
F4A0.031 (3)0.039 (5)0.034 (6)0.014 (2)0.006 (3)0.006 (5)
F1A0.088 (10)0.016 (3)0.033 (4)0.013 (4)0.012 (5)0.002 (3)
O10.061 (2)0.0390 (16)0.054 (2)0.0134 (13)0.0005 (14)0.0197 (13)
Geometric parameters (Å, º) top
Ni1—Cl12.4305 (5)C9—C101.385 (3)
Ni1—P12.1690 (5)C8—H80.9300
Ni1—P22.1660 (5)C35—H350.9300
Ni1—C311.8311 (19)C35—C361.380 (3)
Ni1—C171.9344 (18)C11—H110.9300
P1—C11.8039 (19)C11—C101.383 (3)
P1—C71.8074 (18)C10—H100.9300
P1—C131.8226 (18)C37—H370.9300
P2—C181.8276 (19)C37—C361.382 (3)
P2—C251.811 (2)C25—C261.389 (3)
P2—C191.814 (2)C25—C301.399 (3)
P3—F61.596 (9)C26—H260.9300
P3—F51.600 (9)C26—C271.383 (3)
P3—F31.613 (8)C30—H300.9300
P3—F21.610 (8)C30—C291.377 (3)
P3—F41.600 (9)C19—C201.400 (3)
P3—F11.601 (8)C19—C241.390 (3)
P3—F3A1.606 (11)C4—H40.9300
P3—F6A1.601 (11)C4—C31.378 (3)
P3—F5A1.609 (11)C4—C51.382 (3)
P3—F2A1.600 (11)C3—H30.9300
P3—F4A1.602 (11)C36—H360.9300
P3—F1A1.593 (10)C14—H14A0.9700
N3—C321.405 (2)C14—H14B0.9700
N1—C131.452 (2)C14—C151.514 (3)
N1—C171.344 (2)C39—H39A0.9600
N1—C141.472 (2)C39—H39B0.9600
N2—C171.335 (2)C39—H39C0.9600
N2—C181.451 (2)C28—H280.9300
N2—C161.475 (2)C28—C271.379 (3)
N3—C311.161 (2)C28—C291.387 (3)
C32—C381.396 (3)C5—H50.9300
C32—C331.399 (3)C27—H270.9300
C1—C21.390 (3)C20—H200.9300
C1—C61.399 (3)C20—C211.385 (3)
C38—C371.388 (3)C16—H16A0.9700
C38—C391.502 (3)C16—H16B0.9700
C12—H120.9300C16—C151.513 (3)
C12—C71.398 (3)C15—H15A0.9700
C12—C111.384 (3)C15—H15B0.9700
C33—C351.387 (3)C34—H34A0.9600
C33—C341.500 (3)C34—H34B0.9600
C2—H20.9300C34—H34C0.9600
C2—C31.386 (3)C29—H290.9300
C7—C81.399 (3)C23—H230.9300
C18—H18A0.9700C23—C241.404 (3)
C18—H18B0.9700C23—C221.370 (4)
C6—H60.9300C21—H210.9300
C6—C51.387 (3)C21—C221.376 (4)
C13—H13A0.9700C24—H240.9300
C13—H13B0.9700C22—H220.9300
C9—H90.9300O1—H1A0.8504
C9—C81.386 (3)O1—H1B0.8497
P1—Ni1—Cl1100.968 (19)C10—C9—C8119.72 (18)
P2—Ni1—Cl1103.29 (2)N1—C17—Ni1120.68 (13)
P2—Ni1—P1152.21 (2)N2—C17—Ni1121.04 (13)
C31—Ni1—Cl1101.89 (6)N2—C17—N1118.13 (16)
C31—Ni1—P194.89 (6)C7—C8—H8119.7
C31—Ni1—P293.19 (6)C9—C8—C7120.51 (18)
C31—Ni1—C17171.10 (8)C9—C8—H8119.7
C17—Ni1—Cl187.02 (5)C33—C35—H35119.4
C17—Ni1—P183.42 (5)C36—C35—C33121.26 (18)
C17—Ni1—P284.51 (5)C36—C35—H35119.4
C1—P1—Ni1123.61 (6)C12—C11—H11119.9
C1—P1—C7107.69 (8)C10—C11—C12120.25 (18)
C1—P1—C13105.08 (8)C10—C11—H11119.9
C7—P1—Ni1112.12 (6)C9—C10—H10119.8
C7—P1—C13107.81 (8)C11—C10—C9120.33 (18)
C13—P1—Ni198.98 (6)C11—C10—H10119.8
C18—P2—Ni1100.44 (6)C38—C37—H37119.4
C25—P2—Ni1114.87 (6)C36—C37—C38121.15 (19)
C25—P2—C18104.57 (9)C36—C37—H37119.4
C25—P2—C19109.27 (9)C26—C25—P2118.84 (14)
C19—P2—Ni1120.87 (7)C26—C25—C30119.10 (18)
C19—P2—C18104.45 (9)C30—C25—P2121.95 (16)
F6—P3—F595.0 (17)C25—C26—H26119.6
F6—P3—F386.3 (11)C27—C26—C25120.79 (18)
F6—P3—F289.4 (9)C27—C26—H26119.6
F6—P3—F490.5 (9)C25—C30—H30120.1
F6—P3—F1178.2 (8)C29—C30—C25119.8 (2)
F5—P3—F3173.9 (14)C29—C30—H30120.1
F5—P3—F285.4 (12)C20—C19—P2117.36 (15)
F5—P3—F184.2 (16)C24—C19—P2123.23 (17)
F2—P3—F388.7 (7)C24—C19—C20119.40 (19)
F4—P3—F592.7 (12)C3—C4—H4119.6
F4—P3—F393.2 (8)C3—C4—C5120.83 (19)
F4—P3—F2178.1 (8)C5—C4—H4119.6
F4—P3—F191.2 (9)C2—C3—H3120.1
F1—P3—F394.3 (10)C4—C3—C2119.87 (19)
F1—P3—F289.0 (8)C4—C3—H3120.1
F3A—P3—F5A172.4 (18)C35—C36—C37120.48 (18)
F6A—P3—F3A94.6 (13)C35—C36—H36119.8
F6A—P3—F5A84 (2)C37—C36—H36119.8
F6A—P3—F4A88.4 (11)N1—C14—H14A109.8
F2A—P3—F3A91.5 (9)N1—C14—H14B109.8
F2A—P3—F6A90.3 (11)N1—C14—C15109.24 (15)
F2A—P3—F5A96.0 (17)H14A—C14—H14B108.3
F2A—P3—F4A176.9 (11)C15—C14—H14A109.8
F4A—P3—F3A85.8 (10)C15—C14—H14B109.8
F4A—P3—F5A86.7 (16)C38—C39—H39A109.5
F1A—P3—F3A84.0 (13)C38—C39—H39B109.5
F1A—P3—F6A178.3 (10)C38—C39—H39C109.5
F1A—P3—F5A97.3 (19)H39A—C39—H39B109.5
F1A—P3—F2A90.7 (10)H39A—C39—H39C109.5
F1A—P3—F4A90.5 (11)H39B—C39—H39C109.5
C31—N3—C32175.71 (18)C27—C28—H28120.0
C13—N1—C14116.07 (14)C27—C28—C29120.0 (2)
C17—N1—C13118.15 (15)C29—C28—H28120.0
C17—N1—C14123.79 (16)C6—C5—H5120.1
C18—N2—C16114.51 (15)C4—C5—C6119.78 (19)
C17—N2—C18119.58 (15)C4—C5—H5120.1
C17—N2—C16124.39 (15)C26—C27—H27120.1
C38—C32—N3118.38 (16)C28—C27—C26119.7 (2)
C38—C32—C33123.96 (17)C28—C27—H27120.1
C33—C32—N3117.66 (17)C19—C20—H20119.6
C2—C1—P1119.25 (14)C21—C20—C19120.8 (2)
C2—C1—C6119.76 (17)C21—C20—H20119.6
C6—C1—P1120.93 (14)N2—C16—H16A109.8
C32—C38—C39121.63 (17)N2—C16—H16B109.8
C37—C38—C32116.62 (17)N2—C16—C15109.58 (16)
C37—C38—C39121.75 (18)H16A—C16—H16B108.2
C7—C12—H12119.9C15—C16—H16A109.8
C11—C12—H12119.9C15—C16—H16B109.8
C11—C12—C7120.13 (17)C14—C15—H15A109.8
C32—C33—C34121.45 (17)C14—C15—H15B109.8
C35—C33—C32116.53 (18)C16—C15—C14109.25 (17)
C35—C33—C34122.02 (18)C16—C15—H15A109.8
C1—C2—H2120.0C16—C15—H15B109.8
C3—C2—C1120.01 (18)H15A—C15—H15B108.3
C3—C2—H2120.0C33—C34—H34A109.5
C12—C7—P1122.88 (14)C33—C34—H34B109.5
C12—C7—C8119.00 (17)C33—C34—H34C109.5
C8—C7—P1117.83 (14)H34A—C34—H34B109.5
P2—C18—H18A110.4H34A—C34—H34C109.5
P2—C18—H18B110.4H34B—C34—H34C109.5
N2—C18—P2106.75 (12)C30—C29—C28120.59 (19)
N2—C18—H18A110.4C30—C29—H29119.7
N2—C18—H18B110.4C28—C29—H29119.7
H18A—C18—H18B108.6C24—C23—H23119.5
N3—C31—Ni1177.33 (17)C22—C23—H23119.5
C1—C6—H6120.1C22—C23—C24121.0 (2)
C5—C6—C1119.74 (18)C20—C21—H21120.3
C5—C6—H6120.1C22—C21—C20119.5 (2)
P1—C13—H13A110.6C22—C21—H21120.3
P1—C13—H13B110.6C19—C24—C23118.8 (2)
N1—C13—P1105.48 (11)C19—C24—H24120.6
N1—C13—H13A110.6C23—C24—H24120.6
N1—C13—H13B110.6C23—C22—C21120.5 (2)
H13A—C13—H13B108.8C23—C22—H22119.8
C8—C9—H9120.1C21—C22—H22119.8
C10—C9—H9120.1H1A—O1—H1B104.4
Ni1—P1—C1—C218.36 (17)C18—N2—C17—Ni15.4 (2)
Ni1—P1—C1—C6164.32 (12)C18—N2—C17—N1170.37 (16)
Ni1—P1—C7—C12110.89 (14)C18—N2—C16—C15165.17 (17)
Ni1—P1—C7—C862.89 (15)C6—C1—C2—C31.2 (3)
Ni1—P1—C13—N136.09 (12)C13—P1—C1—C293.55 (15)
Ni1—P2—C18—N227.67 (13)C13—P1—C1—C683.77 (16)
Ni1—P2—C25—C265.68 (17)C13—P1—C7—C122.98 (18)
Ni1—P2—C25—C30170.53 (14)C13—P1—C7—C8170.80 (14)
Ni1—P2—C19—C2053.86 (18)C13—N1—C17—Ni15.3 (2)
Ni1—P2—C19—C24125.23 (16)C13—N1—C17—N2170.45 (16)
P1—C1—C2—C3178.51 (14)C13—N1—C14—C15163.90 (17)
P1—C1—C6—C5178.20 (15)C17—N1—C13—P129.47 (19)
P1—C7—C8—C9171.79 (14)C17—N1—C14—C1532.5 (3)
P2—C25—C26—C27177.05 (14)C17—N2—C18—P223.4 (2)
P2—C25—C30—C29176.95 (16)C17—N2—C16—C1529.0 (3)
P2—C19—C20—C21179.24 (17)C8—C9—C10—C111.5 (3)
P2—C19—C24—C23179.73 (17)C11—C12—C7—P1172.42 (14)
N3—C32—C38—C37179.53 (16)C11—C12—C7—C81.3 (3)
N3—C32—C38—C390.4 (3)C10—C9—C8—C70.9 (3)
N3—C32—C33—C35178.99 (16)C25—P2—C18—N291.66 (14)
N3—C32—C33—C340.8 (3)C25—P2—C19—C20169.40 (15)
N1—C14—C15—C1653.8 (2)C25—P2—C19—C2411.5 (2)
N2—C16—C15—C1452.2 (2)C25—C26—C27—C280.5 (3)
C32—C38—C37—C360.5 (3)C25—C30—C29—C280.5 (3)
C32—C33—C35—C360.6 (3)C26—C25—C30—C290.7 (3)
C1—P1—C7—C12109.92 (16)C30—C25—C26—C270.7 (3)
C1—P1—C7—C876.30 (15)C19—P2—C18—N2153.56 (13)
C1—P1—C13—N1164.62 (12)C19—P2—C25—C26133.90 (15)
C1—C2—C3—C40.5 (3)C19—P2—C25—C3049.89 (19)
C1—C6—C5—C40.1 (3)C19—C20—C21—C220.9 (3)
C38—C32—C33—C350.5 (3)C3—C4—C5—C60.8 (3)
C38—C32—C33—C34179.68 (19)C14—N1—C13—P1165.93 (13)
C38—C37—C36—C350.3 (3)C14—N1—C17—Ni1168.61 (14)
C12—C7—C8—C92.2 (3)C14—N1—C17—N27.1 (3)
C12—C11—C10—C92.4 (3)C39—C38—C37—C36178.63 (19)
C33—C32—C38—C370.0 (3)C5—C4—C3—C20.5 (3)
C33—C32—C38—C39179.05 (18)C27—C28—C29—C300.3 (3)
C33—C35—C36—C370.3 (3)C20—C19—C24—C231.2 (3)
C2—C1—C6—C50.9 (3)C20—C21—C22—C230.2 (4)
C7—P1—C1—C2151.72 (14)C16—N2—C18—P2170.03 (14)
C7—P1—C1—C630.96 (17)C16—N2—C17—Ni1170.47 (14)
C7—P1—C13—N180.73 (13)C16—N2—C17—N15.2 (3)
C7—C12—C11—C101.0 (3)C34—C33—C35—C36179.6 (2)
C18—P2—C25—C26114.76 (15)C29—C28—C27—C260.3 (3)
C18—P2—C25—C3061.46 (18)C24—C19—C20—C211.6 (3)
C18—P2—C19—C2057.98 (18)C24—C23—C22—C210.6 (4)
C18—P2—C19—C24122.93 (18)C22—C23—C24—C190.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···F10.932.433.237 (15)145
C9—H9···F1A0.932.493.342 (19)153
C14—H14A···O10.972.483.278 (4)139
C20—H20···Cl10.932.803.567 (2)141
O1—H1B···Cl10.852.303.148 (3)175
 

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