trans-Chlorido(phenanthren-9-yl)bis-(triphenyl-phosphane)nickel(II).

The title compound, [Ni(C(14)H(9))Cl(C(18)H(15)P)(2)], was synthesized from the reaction between 9-chloro-phenanthrene, NiCl(2)·6H(2)O and triphenyl-phosphane in ethanol. The bond angles around the Ni(II) atom indicate that it exists in a slightly distorted square-planar geometry.

Related literature

For the synthesis, see: Soolinger et al. (1990 ▶). For analogues and related applications, see: Rosen et al. (2011 ▶); Zim et al. (2001 ▶); Chen & Yang (2007a ▶,b ▶); Gao & Yang (2008 ▶); Zhou et al. (2009 ▶); Roma et al. (2011 ▶); Liu et al. (2008 ▶).

Experimental

Crystal data

[Ni(C14H9)Cl(C18H15P)2]

M = 795.91

Orthorhombic,

a = 11.090 (5) Å

b = 15.204 (7) Å

c = 23.679 (10) Å

V = 3993 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 110 K

0.59 × 0.46 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.692, T max = 0.863

53371 measured reflections

6780 independent reflections

6359 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.057

S = 1.02

6780 reflections

488 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 2986 Friedel pairs

Flack parameter: 0.000 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811032326/vm2114sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032326/vm2114Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032326/vm2114Isup3.cdx

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C14H9)Cl(C18H15P)2]	F(000) = 1656
Mr = 795.91	Dx = 1.324 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6845 reflections
a = 11.090 (5) Å	θ = 2.2–26.7°
b = 15.204 (7) Å	µ = 0.67 mm−1
c = 23.679 (10) Å	T = 110 K
V = 3993 (3) Å3	Plate, orange
Z = 4	0.59 × 0.46 × 0.23 mm

Bruker APEXII CCD diffractometer	6780 independent reflections
Radiation source: fine-focus sealed tube	6359 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.692, Tmax = 0.863	k = −18→18
53371 measured reflections	l = −28→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024	H-atom parameters constrained
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
6780 reflections	Δρmax = 0.26 e Å−3
488 parameters	Δρmin = −0.14 e Å−3
0 restraints	Absolute structure: Flack (1983), 2986 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.000 (7)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ni1	0.56721 (2)	0.527489 (15)	−0.047248 (9)	0.02000 (7)
Cl1	0.49242 (4)	0.63193 (3)	0.009025 (18)	0.02449 (11)
P1	0.65475 (5)	0.45655 (3)	0.024960 (19)	0.02055 (11)
P2	0.50725 (4)	0.59607 (3)	−0.125640 (19)	0.02011 (11)
C1	0.65053 (18)	0.44916 (12)	−0.09623 (8)	0.0215 (4)
C2	0.76625 (18)	0.46946 (15)	−0.11185 (8)	0.0264 (4)
H2A	0.8004	0.5235	−0.0997	0.032*
C3	0.83753 (19)	0.41080 (15)	−0.14631 (8)	0.0285 (5)
C4	0.95831 (19)	0.43137 (16)	−0.15978 (10)	0.0373 (6)
H4A	0.9910	0.4862	−0.1482	0.045*
C5	1.0289 (2)	0.37379 (18)	−0.18910 (11)	0.0481 (7)
H5A	1.1103	0.3884	−0.1974	0.058*
C6	0.9811 (3)	0.29272 (18)	−0.20702 (11)	0.0503 (7)
H6A	1.0305	0.2524	−0.2272	0.060*
C7	0.8645 (2)	0.27199 (17)	−0.19557 (9)	0.0409 (6)
H7A	0.8331	0.2174	−0.2083	0.049*
C8	0.7884 (2)	0.33008 (14)	−0.16497 (9)	0.0298 (5)
C9	0.66463 (19)	0.30797 (14)	−0.15135 (8)	0.0272 (5)
C10	0.6079 (2)	0.23092 (15)	−0.16979 (9)	0.0355 (5)
H10A	0.6516	0.1905	−0.1925	0.043*
C11	0.4903 (2)	0.21231 (15)	−0.15580 (9)	0.0387 (6)
H11A	0.4536	0.1598	−0.1691	0.046*
C12	0.4251 (2)	0.26995 (14)	−0.12229 (9)	0.0343 (5)
H12A	0.3441	0.2567	−0.1124	0.041*
C13	0.47822 (19)	0.34736 (14)	−0.10304 (8)	0.0292 (5)
H13A	0.4328	0.3866	−0.0802	0.035*
C14	0.59785 (18)	0.36821 (13)	−0.11689 (8)	0.0242 (4)
C15	0.36705 (18)	0.65927 (14)	−0.12249 (8)	0.0253 (4)
C16	0.2761 (2)	0.63172 (17)	−0.08626 (9)	0.0359 (5)
H16A	0.2892	0.5835	−0.0615	0.043*
C17	0.1658 (2)	0.67511 (19)	−0.08639 (10)	0.0473 (7)
H17A	0.1035	0.6565	−0.0616	0.057*
C18	0.1462 (2)	0.74547 (18)	−0.12253 (10)	0.0451 (6)
H18A	0.0710	0.7753	−0.1221	0.054*
C19	0.2356 (2)	0.77222 (16)	−0.15896 (10)	0.0379 (6)
H19A	0.2215	0.8199	−0.1840	0.046*
C20	0.34575 (19)	0.72989 (14)	−0.15910 (9)	0.0286 (5)
H20A	0.4074	0.7488	−0.1842	0.034*
C21	0.62413 (17)	0.67544 (13)	−0.14485 (8)	0.0230 (4)
C22	0.69398 (18)	0.71257 (14)	−0.10193 (9)	0.0259 (5)
H22A	0.6773	0.6984	−0.0637	0.031*
C23	0.7876 (2)	0.77001 (15)	−0.11455 (9)	0.0315 (5)
H23A	0.8341	0.7953	−0.0850	0.038*
C24	0.81292 (19)	0.79046 (15)	−0.17089 (9)	0.0318 (5)
H24A	0.8782	0.8285	−0.1797	0.038*
C25	0.74276 (19)	0.75518 (14)	−0.21397 (10)	0.0331 (5)
H25A	0.7591	0.7699	−0.2522	0.040*
C26	0.64865 (19)	0.69838 (14)	−0.20099 (8)	0.0265 (5)
H26A	0.6004	0.6748	−0.2305	0.032*
C27	0.48354 (17)	0.53297 (13)	−0.19152 (7)	0.0222 (4)
C28	0.36738 (19)	0.51242 (14)	−0.20905 (8)	0.0278 (5)
H28A	0.3002	0.5325	−0.1878	0.033*
C29	0.3486 (2)	0.46246 (15)	−0.25774 (9)	0.0349 (5)
H29A	0.2687	0.4483	−0.2690	0.042*
C30	0.4445 (2)	0.43348 (15)	−0.28973 (9)	0.0353 (5)
H30A	0.4310	0.4001	−0.3231	0.042*
C31	0.5605 (2)	0.45350 (14)	−0.27274 (8)	0.0312 (5)
H31A	0.6272	0.4337	−0.2945	0.037*
C32	0.58031 (19)	0.50237 (13)	−0.22399 (8)	0.0258 (4)
H32A	0.6605	0.5152	−0.2126	0.031*
C33	0.76549 (19)	0.30173 (14)	−0.01596 (8)	0.0267 (5)
H33A	0.8154	0.3402	−0.0372	0.032*
C34	0.7797 (2)	0.21147 (14)	−0.02159 (9)	0.0294 (5)
H34A	0.8389	0.1888	−0.0467	0.035*
C35	0.7080 (2)	0.15427 (15)	0.00917 (9)	0.0336 (5)
H35A	0.7178	0.0925	0.0052	0.040*
C36	0.6218 (2)	0.18761 (14)	0.04567 (11)	0.0357 (5)
H36A	0.5718	0.1486	0.0666	0.043*
C37	0.60811 (18)	0.27826 (13)	0.05175 (9)	0.0296 (5)
H37A	0.5499	0.3006	0.0775	0.036*
C38	0.67883 (17)	0.33683 (13)	0.02052 (8)	0.0222 (4)
C39	0.80445 (17)	0.50331 (13)	0.03660 (7)	0.0223 (4)
C40	0.90278 (18)	0.45309 (13)	0.05382 (8)	0.0275 (5)
H40A	0.8941	0.3915	0.0591	0.033*
C41	1.0134 (2)	0.49305 (15)	0.06328 (9)	0.0315 (5)
H41A	1.0800	0.4588	0.0756	0.038*
C42	1.02723 (19)	0.58275 (15)	0.05485 (9)	0.0325 (5)
H42A	1.1038	0.6094	0.0604	0.039*
C43	0.9301 (2)	0.63360 (13)	0.03836 (8)	0.0320 (5)
H43A	0.9395	0.6951	0.0329	0.038*
C44	0.81898 (18)	0.59436 (14)	0.02980 (8)	0.0265 (4)
H44A	0.7518	0.6295	0.0192	0.032*
C45	0.58119 (18)	0.46590 (13)	0.09426 (7)	0.0235 (4)
C46	0.6465 (2)	0.46476 (15)	0.14471 (8)	0.0316 (5)
H46A	0.7321	0.4650	0.1435	0.038*
C47	0.5875 (2)	0.46324 (17)	0.19689 (8)	0.0380 (5)
H47A	0.6328	0.4635	0.2310	0.046*
C48	0.4638 (2)	0.46144 (15)	0.19862 (8)	0.0345 (5)
H48A	0.4233	0.4591	0.2339	0.041*
C49	0.3976 (2)	0.46299 (15)	0.14867 (9)	0.0311 (5)
H49A	0.3120	0.4622	0.1500	0.037*
C50	0.45626 (18)	0.46568 (14)	0.09676 (8)	0.0264 (4)
H50A	0.4105	0.4674	0.0629	0.032*

	U11	U22	U33	U12	U13	U23
Ni1	0.02228 (12)	0.01963 (13)	0.01808 (11)	0.00345 (10)	0.00132 (10)	−0.00025 (10)
Cl1	0.0339 (3)	0.0210 (2)	0.0185 (2)	0.0106 (2)	0.00216 (19)	−0.00120 (17)
P1	0.0232 (2)	0.0196 (3)	0.0189 (2)	0.0014 (2)	0.00066 (19)	0.00014 (19)
P2	0.0200 (2)	0.0211 (3)	0.0192 (2)	0.0012 (2)	−0.0001 (2)	0.00030 (19)
C1	0.0253 (10)	0.0201 (11)	0.0192 (9)	0.0044 (8)	−0.0008 (8)	0.0023 (8)
C2	0.0291 (11)	0.0271 (11)	0.0230 (10)	0.0051 (10)	0.0002 (8)	0.0050 (9)
C3	0.0296 (11)	0.0336 (12)	0.0224 (10)	0.0084 (10)	0.0051 (9)	0.0095 (9)
C4	0.0291 (12)	0.0431 (14)	0.0397 (12)	0.0084 (10)	0.0064 (10)	0.0168 (11)
C5	0.0366 (14)	0.0590 (18)	0.0486 (14)	0.0147 (12)	0.0174 (11)	0.0199 (13)
C6	0.0603 (17)	0.0449 (16)	0.0458 (14)	0.0219 (14)	0.0245 (13)	0.0119 (12)
C7	0.0564 (17)	0.0369 (14)	0.0294 (12)	0.0162 (12)	0.0137 (11)	0.0041 (10)
C8	0.0387 (12)	0.0292 (12)	0.0214 (10)	0.0093 (10)	0.0030 (9)	0.0065 (9)
C9	0.0369 (12)	0.0262 (11)	0.0186 (10)	0.0055 (10)	0.0016 (9)	0.0051 (8)
C10	0.0581 (16)	0.0252 (12)	0.0231 (11)	0.0030 (11)	0.0017 (10)	−0.0013 (9)
C11	0.0580 (16)	0.0295 (12)	0.0286 (11)	−0.0104 (12)	−0.0067 (11)	0.0028 (9)
C12	0.0386 (13)	0.0324 (12)	0.0317 (11)	−0.0112 (11)	−0.0052 (10)	0.0069 (10)
C13	0.0368 (12)	0.0267 (11)	0.0242 (10)	0.0001 (9)	0.0009 (9)	0.0027 (8)
C14	0.0317 (11)	0.0206 (10)	0.0204 (9)	0.0016 (9)	−0.0016 (8)	0.0041 (8)
C15	0.0226 (10)	0.0305 (12)	0.0229 (10)	0.0022 (9)	−0.0035 (8)	−0.0069 (9)
C16	0.0275 (12)	0.0529 (15)	0.0273 (11)	0.0050 (11)	0.0031 (9)	0.0064 (10)
C17	0.0261 (12)	0.081 (2)	0.0345 (12)	0.0106 (13)	0.0081 (10)	0.0030 (13)
C18	0.0279 (13)	0.0627 (18)	0.0446 (14)	0.0183 (12)	−0.0054 (11)	−0.0085 (13)
C19	0.0352 (13)	0.0349 (13)	0.0437 (14)	0.0099 (11)	−0.0099 (11)	−0.0031 (11)
C20	0.0248 (11)	0.0279 (12)	0.0330 (11)	0.0030 (9)	−0.0052 (9)	−0.0019 (9)
C21	0.0202 (10)	0.0205 (11)	0.0285 (10)	0.0029 (8)	−0.0024 (8)	0.0030 (8)
C22	0.0271 (11)	0.0264 (11)	0.0241 (10)	0.0014 (9)	−0.0014 (9)	0.0011 (8)
C23	0.0269 (11)	0.0310 (12)	0.0365 (12)	−0.0009 (10)	−0.0075 (9)	−0.0010 (10)
C24	0.0244 (11)	0.0301 (12)	0.0410 (13)	−0.0030 (9)	0.0033 (10)	0.0042 (10)
C25	0.0323 (13)	0.0340 (13)	0.0329 (12)	−0.0025 (10)	0.0030 (10)	0.0056 (10)
C26	0.0264 (11)	0.0278 (11)	0.0254 (10)	−0.0023 (9)	−0.0023 (9)	0.0032 (9)
C27	0.0260 (10)	0.0198 (10)	0.0208 (8)	0.0011 (9)	−0.0009 (8)	0.0023 (8)
C28	0.0267 (11)	0.0272 (12)	0.0295 (10)	0.0003 (9)	−0.0012 (9)	−0.0008 (9)
C29	0.0354 (12)	0.0337 (12)	0.0357 (11)	−0.0023 (11)	−0.0091 (10)	−0.0031 (10)
C30	0.0488 (14)	0.0311 (12)	0.0260 (10)	−0.0010 (11)	−0.0045 (11)	−0.0048 (9)
C31	0.0388 (12)	0.0300 (12)	0.0248 (10)	0.0017 (11)	0.0091 (9)	−0.0002 (9)
C32	0.0264 (11)	0.0277 (11)	0.0233 (9)	−0.0010 (9)	0.0018 (8)	0.0022 (8)
C33	0.0302 (11)	0.0260 (11)	0.0238 (10)	0.0026 (9)	−0.0011 (9)	0.0026 (9)
C34	0.0304 (12)	0.0271 (12)	0.0307 (11)	0.0062 (9)	−0.0043 (9)	−0.0030 (9)
C35	0.0373 (12)	0.0212 (11)	0.0422 (13)	0.0002 (10)	−0.0084 (10)	0.0001 (10)
C36	0.0327 (12)	0.0256 (12)	0.0488 (13)	−0.0056 (9)	−0.0014 (11)	0.0050 (11)
C37	0.0251 (11)	0.0295 (12)	0.0342 (11)	0.0005 (9)	0.0020 (9)	0.0031 (10)
C38	0.0234 (10)	0.0217 (10)	0.0216 (9)	0.0006 (8)	−0.0041 (8)	−0.0004 (8)
C39	0.0251 (10)	0.0239 (10)	0.0180 (9)	−0.0004 (8)	0.0021 (8)	0.0001 (8)
C40	0.0306 (11)	0.0215 (11)	0.0305 (10)	−0.0008 (8)	−0.0020 (9)	−0.0001 (9)
C41	0.0260 (11)	0.0343 (12)	0.0344 (11)	0.0020 (10)	−0.0017 (9)	−0.0033 (9)
C42	0.0324 (12)	0.0362 (13)	0.0288 (11)	−0.0099 (10)	0.0028 (9)	−0.0061 (9)
C43	0.0435 (12)	0.0238 (11)	0.0285 (11)	−0.0071 (10)	0.0022 (10)	0.0001 (9)
C44	0.0312 (11)	0.0231 (10)	0.0252 (10)	−0.0010 (9)	0.0005 (8)	0.0024 (8)
C45	0.0299 (11)	0.0189 (10)	0.0217 (9)	−0.0011 (9)	0.0025 (8)	−0.0011 (8)
C46	0.0294 (11)	0.0398 (13)	0.0257 (10)	0.0010 (11)	−0.0010 (8)	−0.0010 (10)
C47	0.0425 (14)	0.0489 (15)	0.0225 (10)	−0.0009 (12)	−0.0034 (9)	−0.0010 (10)
C48	0.0449 (14)	0.0355 (13)	0.0232 (10)	−0.0007 (11)	0.0102 (9)	−0.0028 (9)
C49	0.0320 (11)	0.0284 (12)	0.0331 (11)	−0.0021 (10)	0.0054 (9)	−0.0012 (10)
C50	0.0288 (11)	0.0249 (10)	0.0255 (9)	−0.0017 (9)	−0.0015 (8)	−0.0001 (9)

Ni1—C1	1.9020 (19)	C23—H23A	0.9500
Ni1—P2	2.2305 (9)	C24—C25	1.391 (3)
Ni1—Cl1	2.2327 (8)	C24—H24A	0.9500
Ni1—P1	2.2426 (8)	C25—C26	1.389 (3)
P1—C39	1.827 (2)	C25—H25A	0.9500
P1—C45	1.8381 (19)	C26—H26A	0.9500
P1—C38	1.843 (2)	C27—C28	1.389 (3)
P2—C21	1.829 (2)	C27—C32	1.400 (3)
P2—C15	1.829 (2)	C28—C29	1.396 (3)
P2—C27	1.850 (2)	C28—H28A	0.9500
C1—C2	1.371 (3)	C29—C30	1.378 (3)
C1—C14	1.448 (3)	C29—H29A	0.9500
C2—C3	1.444 (3)	C30—C31	1.383 (3)
C2—H2A	0.9500	C30—H30A	0.9500
C3—C4	1.412 (3)	C31—C32	1.390 (3)
C3—C8	1.414 (3)	C31—H31A	0.9500
C4—C5	1.364 (3)	C32—H32A	0.9500
C4—H4A	0.9500	C33—C34	1.388 (3)
C5—C6	1.407 (4)	C33—C38	1.398 (3)
C5—H5A	0.9500	C33—H33A	0.9500
C6—C7	1.358 (4)	C34—C35	1.386 (3)
C6—H6A	0.9500	C34—H34A	0.9500
C7—C8	1.420 (3)	C35—C36	1.385 (3)
C7—H7A	0.9500	C35—H35A	0.9500
C8—C9	1.450 (3)	C36—C37	1.394 (3)
C9—C10	1.400 (3)	C36—H36A	0.9500
C9—C14	1.433 (3)	C37—C38	1.398 (3)
C10—C11	1.375 (3)	C37—H37A	0.9500
C10—H10A	0.9500	C39—C40	1.392 (3)
C11—C12	1.386 (3)	C39—C44	1.403 (3)
C11—H11A	0.9500	C40—C41	1.387 (3)
C12—C13	1.393 (3)	C40—H40A	0.9500
C12—H12A	0.9500	C41—C42	1.387 (3)
C13—C14	1.403 (3)	C41—H41A	0.9500
C13—H13A	0.9500	C42—C43	1.382 (3)
C15—C16	1.389 (3)	C42—H42A	0.9500
C15—C20	1.400 (3)	C43—C44	1.384 (3)
C16—C17	1.390 (3)	C43—H43A	0.9500
C16—H16A	0.9500	C44—H44A	0.9500
C17—C18	1.387 (4)	C45—C50	1.387 (3)
C17—H17A	0.9500	C45—C46	1.397 (3)
C18—C19	1.375 (4)	C46—C47	1.398 (3)
C18—H18A	0.9500	C46—H46A	0.9500
C19—C20	1.381 (3)	C47—C48	1.373 (3)
C19—H19A	0.9500	C47—H47A	0.9500
C20—H20A	0.9500	C48—C49	1.392 (3)
C21—C22	1.397 (3)	C48—H48A	0.9500
C21—C26	1.401 (3)	C49—C50	1.391 (3)
C22—C23	1.389 (3)	C49—H49A	0.9500
C22—H22A	0.9500	C50—H50A	0.9500
C23—C24	1.398 (3)
C1—Ni1—P2	85.99 (6)	C22—C23—C24	119.7 (2)
C1—Ni1—Cl1	171.79 (6)	C22—C23—H23A	120.2
P2—Ni1—Cl1	93.06 (4)	C24—C23—H23A	120.2
C1—Ni1—P1	87.33 (6)	C25—C24—C23	120.1 (2)
P2—Ni1—P1	171.26 (2)	C25—C24—H24A	120.0
Cl1—Ni1—P1	92.74 (3)	C23—C24—H24A	120.0
C39—P1—C45	103.80 (9)	C26—C25—C24	119.9 (2)
C39—P1—C38	105.14 (9)	C26—C25—H25A	120.1
C45—P1—C38	101.05 (9)	C24—C25—H25A	120.1
C39—P1—Ni1	108.74 (6)	C25—C26—C21	120.70 (19)
C45—P1—Ni1	116.83 (7)	C25—C26—H26A	119.7
C38—P1—Ni1	119.63 (6)	C21—C26—H26A	119.7
C21—P2—C15	105.43 (10)	C28—C27—C32	118.18 (18)
C21—P2—C27	103.49 (9)	C28—C27—P2	120.03 (15)
C15—P2—C27	100.72 (9)	C32—C27—P2	121.77 (15)
C21—P2—Ni1	107.71 (7)	C27—C28—C29	120.5 (2)
C15—P2—Ni1	117.71 (7)	C27—C28—H28A	119.8
C27—P2—Ni1	120.11 (7)	C29—C28—H28A	119.8
C2—C1—C14	118.56 (18)	C30—C29—C28	120.9 (2)
C2—C1—Ni1	118.58 (15)	C30—C29—H29A	119.6
C14—C1—Ni1	122.85 (15)	C28—C29—H29A	119.6
C1—C2—C3	121.7 (2)	C29—C30—C31	119.21 (19)
C1—C2—H2A	119.1	C29—C30—H30A	120.4
C3—C2—H2A	119.1	C31—C30—H30A	120.4
C4—C3—C8	119.2 (2)	C30—C31—C32	120.4 (2)
C4—C3—C2	120.7 (2)	C30—C31—H31A	119.8
C8—C3—C2	120.11 (19)	C32—C31—H31A	119.8
C5—C4—C3	121.2 (2)	C31—C32—C27	120.8 (2)
C5—C4—H4A	119.4	C31—C32—H32A	119.6
C3—C4—H4A	119.4	C27—C32—H32A	119.6
C4—C5—C6	120.0 (2)	C34—C33—C38	121.0 (2)
C4—C5—H5A	120.0	C34—C33—H33A	119.5
C6—C5—H5A	120.0	C38—C33—H33A	119.5
C7—C6—C5	120.1 (2)	C35—C34—C33	120.3 (2)
C7—C6—H6A	119.9	C35—C34—H34A	119.8
C5—C6—H6A	119.9	C33—C34—H34A	119.8
C6—C7—C8	121.6 (3)	C36—C35—C34	119.7 (2)
C6—C7—H7A	119.2	C36—C35—H35A	120.2
C8—C7—H7A	119.2	C34—C35—H35A	120.2
C3—C8—C7	118.1 (2)	C35—C36—C37	120.1 (2)
C3—C8—C9	119.78 (19)	C35—C36—H36A	120.0
C7—C8—C9	122.1 (2)	C37—C36—H36A	120.0
C10—C9—C14	118.7 (2)	C36—C37—C38	120.9 (2)
C10—C9—C8	123.4 (2)	C36—C37—H37A	119.5
C14—C9—C8	117.90 (19)	C38—C37—H37A	119.5
C11—C10—C9	121.6 (2)	C33—C38—C37	117.99 (19)
C11—C10—H10A	119.2	C33—C38—P1	120.79 (15)
C9—C10—H10A	119.2	C37—C38—P1	121.17 (15)
C10—C11—C12	120.2 (2)	C40—C39—C44	119.01 (18)
C10—C11—H11A	119.9	C40—C39—P1	122.85 (15)
C12—C11—H11A	119.9	C44—C39—P1	118.10 (15)
C11—C12—C13	120.1 (2)	C41—C40—C39	119.98 (19)
C11—C12—H12A	120.0	C41—C40—H40A	120.0
C13—C12—H12A	120.0	C39—C40—H40A	120.0
C12—C13—C14	121.0 (2)	C42—C41—C40	120.4 (2)
C12—C13—H13A	119.5	C42—C41—H41A	119.8
C14—C13—H13A	119.5	C40—C41—H41A	119.8
C13—C14—C9	118.52 (19)	C43—C42—C41	120.3 (2)
C13—C14—C1	119.65 (18)	C43—C42—H42A	119.9
C9—C14—C1	121.82 (18)	C41—C42—H42A	119.9
C16—C15—C20	119.42 (19)	C42—C43—C44	119.61 (19)
C16—C15—P2	118.96 (16)	C42—C43—H43A	120.2
C20—C15—P2	121.39 (16)	C44—C43—H43A	120.2
C15—C16—C17	119.7 (2)	C43—C44—C39	120.7 (2)
C15—C16—H16A	120.2	C43—C44—H44A	119.6
C17—C16—H16A	120.2	C39—C44—H44A	119.6
C18—C17—C16	120.3 (2)	C50—C45—C46	118.78 (17)
C18—C17—H17A	119.8	C50—C45—P1	118.76 (15)
C16—C17—H17A	119.8	C46—C45—P1	122.17 (15)
C19—C18—C17	120.2 (2)	C45—C46—C47	120.9 (2)
C19—C18—H18A	119.9	C45—C46—H46A	119.6
C17—C18—H18A	119.9	C47—C46—H46A	119.6
C18—C19—C20	120.1 (2)	C48—C47—C46	119.60 (19)
C18—C19—H19A	120.0	C48—C47—H47A	120.2
C20—C19—H19A	120.0	C46—C47—H47A	120.2
C19—C20—C15	120.3 (2)	C47—C48—C49	120.08 (18)
C19—C20—H20A	119.8	C47—C48—H48A	120.0
C15—C20—H20A	119.8	C49—C48—H48A	120.0
C22—C21—C26	118.82 (19)	C50—C49—C48	120.31 (19)
C22—C21—P2	118.61 (15)	C50—C49—H49A	119.8
C26—C21—P2	122.54 (15)	C48—C49—H49A	119.8
C23—C22—C21	120.79 (19)	C45—C50—C49	120.32 (19)
C23—C22—H22A	119.6	C45—C50—H50A	119.8
C21—C22—H22A	119.6	C49—C50—H50A	119.8
C1—Ni1—P1—C39	84.48 (9)	P2—C15—C20—C19	174.90 (16)
P2—Ni1—P1—C39	44.27 (16)	C15—P2—C21—C22	96.93 (17)
Cl1—Ni1—P1—C39	−87.30 (7)	C27—P2—C21—C22	−157.73 (16)
C1—Ni1—P1—C45	−158.52 (9)	Ni1—P2—C21—C22	−29.55 (17)
P2—Ni1—P1—C45	161.27 (15)	C15—P2—C21—C26	−85.05 (18)
Cl1—Ni1—P1—C45	29.69 (8)	C27—P2—C21—C26	20.30 (19)
C1—Ni1—P1—C38	−36.20 (10)	Ni1—P2—C21—C26	148.47 (16)
P2—Ni1—P1—C38	−76.41 (16)	C26—C21—C22—C23	−1.1 (3)
Cl1—Ni1—P1—C38	152.02 (8)	P2—C21—C22—C23	176.97 (16)
C1—Ni1—P2—C21	−86.28 (9)	C21—C22—C23—C24	−0.5 (3)
Cl1—Ni1—P2—C21	85.55 (7)	C22—C23—C24—C25	1.7 (3)
P1—Ni1—P2—C21	−46.01 (17)	C23—C24—C25—C26	−1.1 (3)
C1—Ni1—P2—C15	154.82 (10)	C24—C25—C26—C21	−0.6 (3)
Cl1—Ni1—P2—C15	−33.35 (8)	C22—C21—C26—C25	1.7 (3)
P1—Ni1—P2—C15	−164.90 (15)	P2—C21—C26—C25	−176.32 (16)
C1—Ni1—P2—C27	31.63 (10)	C21—P2—C27—C28	−136.92 (17)
Cl1—Ni1—P2—C27	−156.53 (8)	C15—P2—C27—C28	−28.02 (19)
P1—Ni1—P2—C27	71.91 (17)	Ni1—P2—C27—C28	103.04 (16)
P2—Ni1—C1—C2	88.87 (15)	C21—P2—C27—C32	45.10 (18)
Cl1—Ni1—C1—C2	5.2 (5)	C15—P2—C27—C32	154.00 (17)
P1—Ni1—C1—C2	−85.49 (15)	Ni1—P2—C27—C32	−74.95 (17)
P2—Ni1—C1—C14	−92.31 (15)	C32—C27—C28—C29	0.1 (3)
Cl1—Ni1—C1—C14	−176.0 (3)	P2—C27—C28—C29	−177.97 (16)
P1—Ni1—C1—C14	93.33 (15)	C27—C28—C29—C30	−0.8 (3)
C14—C1—C2—C3	−2.4 (3)	C28—C29—C30—C31	0.8 (3)
Ni1—C1—C2—C3	176.45 (14)	C29—C30—C31—C32	−0.1 (3)
C1—C2—C3—C4	−177.19 (18)	C30—C31—C32—C27	−0.6 (3)
C1—C2—C3—C8	0.1 (3)	C28—C27—C32—C31	0.6 (3)
C8—C3—C4—C5	−1.7 (3)	P2—C27—C32—C31	178.65 (15)
C2—C3—C4—C5	175.6 (2)	C38—C33—C34—C35	−0.2 (3)
C3—C4—C5—C6	0.7 (4)	C33—C34—C35—C36	0.0 (3)
C4—C5—C6—C7	0.5 (4)	C34—C35—C36—C37	−0.6 (3)
C5—C6—C7—C8	−0.8 (4)	C35—C36—C37—C38	1.3 (3)
C4—C3—C8—C7	1.4 (3)	C34—C33—C38—C37	0.9 (3)
C2—C3—C8—C7	−175.90 (19)	C34—C33—C38—P1	−176.66 (16)
C4—C3—C8—C9	179.86 (18)	C36—C37—C38—C33	−1.5 (3)
C2—C3—C8—C9	2.5 (3)	C36—C37—C38—P1	176.07 (17)
C6—C7—C8—C3	−0.2 (3)	C39—P1—C38—C33	−51.45 (17)
C6—C7—C8—C9	−178.6 (2)	C45—P1—C38—C33	−159.19 (16)
C3—C8—C9—C10	177.74 (19)	Ni1—P1—C38—C33	71.01 (17)
C7—C8—C9—C10	−3.9 (3)	C39—P1—C38—C37	131.07 (17)
C3—C8—C9—C14	−2.7 (3)	C45—P1—C38—C37	23.33 (18)
C7—C8—C9—C14	175.66 (19)	Ni1—P1—C38—C37	−106.46 (16)
C14—C9—C10—C11	0.3 (3)	C45—P1—C39—C40	89.94 (17)
C8—C9—C10—C11	179.84 (19)	C38—P1—C39—C40	−15.78 (18)
C9—C10—C11—C12	−0.6 (3)	Ni1—P1—C39—C40	−145.03 (15)
C10—C11—C12—C13	0.5 (3)	C45—P1—C39—C44	−87.64 (16)
C11—C12—C13—C14	−0.2 (3)	C38—P1—C39—C44	166.64 (15)
C12—C13—C14—C9	−0.1 (3)	Ni1—P1—C39—C44	37.40 (16)
C12—C13—C14—C1	−179.99 (18)	C44—C39—C40—C41	−0.8 (3)
C10—C9—C14—C13	0.0 (3)	P1—C39—C40—C41	−178.37 (15)
C8—C9—C14—C13	−179.55 (17)	C39—C40—C41—C42	−1.0 (3)
C10—C9—C14—C1	179.97 (18)	C40—C41—C42—C43	1.7 (3)
C8—C9—C14—C1	0.4 (3)	C41—C42—C43—C44	−0.6 (3)
C2—C1—C14—C13	−177.90 (18)	C42—C43—C44—C39	−1.3 (3)
Ni1—C1—C14—C13	3.3 (2)	C40—C39—C44—C43	2.0 (3)
C2—C1—C14—C9	2.2 (3)	P1—C39—C44—C43	179.63 (15)
Ni1—C1—C14—C9	−176.64 (14)	C39—P1—C45—C50	157.71 (17)
C21—P2—C15—C16	−151.15 (17)	C38—P1—C45—C50	−93.51 (18)
C27—P2—C15—C16	101.48 (18)	Ni1—P1—C45—C50	38.04 (19)
Ni1—P2—C15—C16	−31.05 (19)	C39—P1—C45—C46	−28.5 (2)
C21—P2—C15—C20	34.37 (18)	C38—P1—C45—C46	80.25 (19)
C27—P2—C15—C20	−73.00 (18)	Ni1—P1—C45—C46	−148.20 (16)
Ni1—P2—C15—C20	154.47 (14)	C50—C45—C46—C47	0.1 (3)
C20—C15—C16—C17	−0.7 (3)	P1—C45—C46—C47	−173.63 (19)
P2—C15—C16—C17	−175.27 (19)	C45—C46—C47—C48	1.0 (4)
C15—C16—C17—C18	0.1 (4)	C46—C47—C48—C49	−1.4 (4)
C16—C17—C18—C19	0.7 (4)	C47—C48—C49—C50	0.5 (4)
C17—C18—C19—C20	−0.9 (4)	C46—C45—C50—C49	−1.0 (3)
C18—C19—C20—C15	0.4 (3)	P1—C45—C50—C49	173.00 (16)
C16—C15—C20—C19	0.4 (3)	C48—C49—C50—C45	0.7 (3)