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Acta Cryst. (2007). E63, m1415    [ doi:10.1107/S1600536807016832 ]

([eta]5-Cyclopentadienyl)(2-naphthylethynyl)(triphenylphosphine-[kappa]P)nickel(II)

P. Butler, J. F. Gallagher, A. J. Lough and A. R. Manning

Abstract top

The title compound, [Ni(C5H5)(C12H7)(C18H15P)], does not contain strong hydrogen-bond donors or acceptors and the primary interactions are limited to those of the weak C-H...[pi](arene) type and mainly involving the arene rings.

Comment top

The acetylide linkage in Ni(η5-C5H5)(PPh3)-C≡C–X complexes allows facile electronic communication between the electron-rich Ni(η5-C5H5)(PPh3) moiety and the X group (X is alkyl or arene), thus affecting the characteristic chemistry of both X and the acetylide linkage (Gallagher et al., 2002). However, if X is an electron-withdrawing group, the molecule is a donor–π-acceptor (D–π-A) system which may have nonlinear optical (NLO) properties (Whittal et al., 1998a,b), although the phenyl derivative (X = C6H5) does not appear to be particularly effective. We have

demonstrated that polycylic hydrocarbons containing one to five aromatic rings

can act as an electron-donor endgroup in D–π-A systems in the presence of suitable acceptors, and have examined their behaviour attached to the Ni(η5-C5H5)(PPh3) donor moiety (Butler et al., 2005). The spectroscopic and electrochemical evidence suggests limited communication between either end of these Ni(η5-C5H5)(PPh3)-C≡C–X systems, at least in the ground state, and is not sufficient to influence significant changes in the geometric data from diffraction measurements. Here, we present the title 2-naphthyl derivative, (I) (where X = C10H7).

The molecule of (I) has a half-sandwich structure and contains the σ-bonded ethynyl-2-naphthyl ligand, the η5-C5 ring and triphenyl phosphine bonded to the central NiII atom. A view of the molecule with the atomic numbering scheme is presented in Fig. 1 (with selected dimensions in Table 2). The principal Ni–ligand dimensions include Ni1—P1 [2.1484 (9) Å], Ni1—C1 [1.843 (4) Å] and P1—Ni1—C1 [89.04 (9)°], and these are similar to data in related derivatives (Gallagher et al., 1998, 2002; Butler et al., 1998, 2005). The acetylide C≡C and Csp—Car bond lengths are 1.211 (4) and 1.433 (5) Å, respectively. The former is slightly longer than the expected value of 1.18 (1) Å for C≡C (Orpen et al., 1994), while the latter is as expected. The bond angles of the Ni—C≡C—C chain deviate slightly from linearity, with Ni—C≡C = 176.8 (3)° and C≡C—C = 173.0 (3)°.

The η5-C5H5 ring is orthogonal to the P1/Ni1/C1 plane [88.70 (12)°] and to the naphthyl ring [73.83 (10)°]. The naphthyl ring is twisted by 24.23 (9)° from the P1/Ni1/C1 plane.

The closest intramolecular contact to Ni1 involves H42, with H42···Ni1 = 3.11 Å and C42—H42···Ni1 = 113° [C42 is the closest PPh3 ortho-C atom to Ni1, at 3.586 (3) Å]. Although the three Ni1—P—C angles vary, at 111.85 (10), 114.48 (10) and 118.63 (10)°, there is little asymmetry in the PPh3 ligand, with all six P—C—C angles in the range 119.1 (2)–122.6 (3)° and three P—Cipso···Cpara angles of 177.20 (18), 177.42 (16) and 178.25 (18)°.

In the absence of strong hydrogen-bond donors or acceptors, C—H···π(arene) interactions involving the phosphine arene rings arise, with C···Cg in the range 3.549 (4)–3.797 (4) Å and with C—H···Cg angles in the range 138–164° (details in Table 2), where Cg is an aromatic ring centroid (Fig. 2).

Related literature top

For related literature, see: Butler et al. (1998, 2005); Gallagher et al. (1998, 2002); Orpen et al. (1994); Whittal et al. (1998a,b).

Experimental top

Compound (I) was prepared according to literature methods (Butler et al., 2005) and is compound 1 d in the aforementioned paper.

Refinement top

H atoms were treated as riding, with C—H distances of 0.95 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998).

Figures top
[Figure 1] Fig. 1. A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates the intramolecular H42···Ni1 contact.
[Figure 2] Fig. 2. A view of the weak interactions in the crystal structure of (I), with atoms shown as their van der Waals spheres. Three of the C—H···π(arene) interactions have labels.
(η5-Cyclopentadienyl)(2-naphthylethynyl)(triphenylphosphine-κP)nickel(II) top
Crystal data top
[Ni(C5H5)(C12H7)(C18H15P)]F(000) = 1120
Mr = 537.25? #Insert any comments here.
Monoclinic, P21/nDx = 1.338 Mg m−3
Hall symbol: -p 2ynMo Kα radiation, λ = 0.71073 Å
a = 14.4455 (4) ÅCell parameters from 17521 reflections
b = 12.7392 (5) Åθ = 2.6–27.5°
c = 15.2816 (4) ŵ = 0.81 mm−1
β = 108.439 (2)°T = 150 K
V = 2667.80 (15) Å3Block, green
Z = 40.16 × 0.15 × 0.11 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer		5695 independent reflections
Radiation source: fine-focus sealed X-ray tube3173 reflections with I > 2σ(I)
graphiteRint = 0.083
φ and ω scans with κ offsetsθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		h = −18→15
Tmin = 0.813, Tmax = 0.954k = −16→16
8684 measured reflectionsl = −19→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0504P)2]
where P = (Fo2 + 2Fc2)/3
5695 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[Ni(C5H5)(C12H7)(C18H15P)]V = 2667.80 (15) Å3
Mr = 537.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.4455 (4) ŵ = 0.81 mm−1
b = 12.7392 (5) ÅT = 150 K
c = 15.2816 (4) Å0.16 × 0.15 × 0.11 mm
β = 108.439 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		5695 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		3173 reflections with I > 2σ(I)
Tmin = 0.813, Tmax = 0.954Rint = 0.083
8684 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.120Δρmax = 0.54 e Å−3
S = 0.98Δρmin = −0.61 e Å−3
5695 reflectionsAbsolute structure: ?
334 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.07764 (3)0.09838 (3)0.27091 (3)0.02909 (14)
P10.18440 (6)0.08760 (7)0.40539 (5)0.0265 (2)
C10.1713 (2)0.0554 (3)0.2201 (2)0.0309 (8)
C20.2363 (2)0.0278 (2)0.1910 (2)0.0313 (8)
C30.4134 (2)0.0207 (3)0.2268 (2)0.0324 (8)
C40.3212 (2)−0.0016 (2)0.1674 (2)0.0313 (8)
C50.3134 (2)−0.0539 (3)0.0825 (2)0.0339 (8)
C60.3948 (2)−0.0804 (3)0.0611 (2)0.0349 (8)
C70.4892 (2)−0.0577 (3)0.1204 (2)0.0307 (8)
C80.4987 (2)−0.0065 (2)0.2054 (2)0.0292 (8)
C11A0.5747 (2)−0.0834 (3)0.0985 (2)0.0362 (8)
C12A0.6643 (3)−0.0598 (3)0.1573 (2)0.0403 (9)
C13A0.6735 (3)−0.0100 (3)0.2418 (2)0.0421 (9)
C14A0.5928 (2)0.0161 (3)0.2657 (2)0.0371 (9)
C11−0.0315 (2)0.1281 (3)0.1477 (2)0.0460 (10)
C12−0.0613 (2)0.0393 (3)0.1885 (2)0.0430 (9)
C13−0.0665 (2)0.0694 (3)0.2737 (2)0.0415 (9)
C14−0.0426 (2)0.1787 (3)0.2848 (2)0.0412 (9)
C15−0.0263 (2)0.2162 (3)0.2053 (3)0.0478 (10)
C210.1570 (2)0.1480 (2)0.5034 (2)0.0276 (7)
C220.2256 (2)0.2058 (3)0.5702 (2)0.0327 (8)
C230.2028 (2)0.2488 (3)0.6449 (2)0.0359 (8)
C240.1112 (2)0.2351 (3)0.6528 (2)0.0359 (8)
C250.0422 (2)0.1784 (3)0.5873 (2)0.0384 (9)
C260.0648 (2)0.1347 (3)0.5127 (2)0.0363 (8)
C310.2103 (2)−0.0496 (2)0.4429 (2)0.0276 (7)
C320.2333 (2)−0.1217 (3)0.3845 (2)0.0388 (9)
C330.2494 (3)−0.2259 (3)0.4093 (2)0.0428 (9)
C340.2427 (2)−0.2602 (3)0.4926 (2)0.0375 (9)
C350.2215 (2)−0.1900 (3)0.5520 (2)0.0384 (9)
C360.2052 (2)−0.0857 (3)0.5267 (2)0.0346 (8)
C410.3034 (2)0.1433 (2)0.4134 (2)0.0270 (7)
C420.3077 (2)0.2302 (3)0.3603 (2)0.0330 (8)
C430.3962 (2)0.2780 (3)0.3678 (2)0.0406 (9)
C440.4815 (2)0.2370 (3)0.4286 (2)0.0408 (9)
C450.4781 (2)0.1507 (3)0.4819 (2)0.0384 (9)
C460.3893 (2)0.1032 (3)0.4742 (2)0.0319 (8)
H30.41950.05520.28350.039*
H50.2509−0.07010.04070.041*
H60.3878−0.11520.00440.042*
H11A0.5692−0.11760.04190.043*
H12A0.7209−0.07700.14150.048*
H13A0.73660.00580.28270.051*
H14A0.60020.04950.32310.045*
H11−0.01750.12830.09100.055*
H12−0.0751−0.02870.16190.052*
H13−0.08300.02570.31690.050*
H14−0.03850.21920.33810.049*
H15−0.01420.28690.19240.057*
H220.28880.21620.56500.039*
H230.25070.28760.69040.043*
H240.09580.26480.70350.043*
H25−0.02100.16890.59270.046*
H260.01670.09550.46770.044*
H320.2379−0.09890.32690.047*
H330.2653−0.27410.36880.051*
H340.2527−0.33230.50900.045*
H350.2180−0.21310.61010.046*
H360.1902−0.03770.56780.042*
H420.24930.25740.31820.040*
H430.39850.33820.33180.049*
H440.54250.26860.43350.049*
H450.53660.12350.52390.046*
H460.38720.04330.51060.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0241 (3)0.0308 (3)0.0317 (2)0.00182 (19)0.00784 (18)−0.00069 (19)
P10.0234 (5)0.0257 (5)0.0306 (4)0.0002 (4)0.0086 (4)−0.0009 (4)
C10.032 (2)0.0265 (19)0.0322 (17)−0.0016 (15)0.0065 (16)0.0011 (15)
C20.034 (2)0.0252 (19)0.0358 (18)−0.0035 (16)0.0128 (16)−0.0022 (15)
C30.036 (2)0.0290 (19)0.0361 (18)−0.0009 (16)0.0173 (16)−0.0010 (15)
C40.038 (2)0.0245 (19)0.0358 (18)−0.0002 (16)0.0175 (17)0.0039 (15)
C50.033 (2)0.032 (2)0.0362 (18)−0.0044 (16)0.0108 (16)−0.0012 (15)
C60.046 (2)0.027 (2)0.0365 (18)−0.0049 (16)0.0195 (17)−0.0055 (15)
C70.035 (2)0.0245 (18)0.0360 (18)−0.0004 (15)0.0159 (16)0.0037 (15)
C80.033 (2)0.0225 (18)0.0340 (18)0.0025 (15)0.0133 (16)0.0049 (14)
C11A0.037 (2)0.038 (2)0.0390 (18)0.0019 (17)0.0201 (17)0.0023 (17)
C12A0.040 (2)0.040 (2)0.047 (2)0.0039 (17)0.0234 (19)0.0039 (17)
C13A0.032 (2)0.050 (2)0.044 (2)−0.0004 (18)0.0104 (17)0.0050 (18)
C14A0.037 (2)0.039 (2)0.0338 (18)0.0021 (17)0.0099 (17)0.0001 (16)
C110.023 (2)0.077 (3)0.0326 (19)0.0067 (19)0.0015 (16)0.006 (2)
C120.025 (2)0.052 (3)0.048 (2)−0.0013 (18)0.0047 (17)−0.010 (2)
C130.0239 (19)0.053 (3)0.048 (2)0.0009 (17)0.0112 (16)0.0022 (19)
C140.0228 (19)0.048 (2)0.049 (2)0.0098 (17)0.0070 (16)−0.0032 (19)
C150.037 (2)0.044 (2)0.057 (2)0.0111 (19)0.0085 (19)0.012 (2)
C210.0261 (18)0.0245 (18)0.0317 (17)0.0017 (14)0.0084 (14)−0.0014 (14)
C220.0244 (18)0.035 (2)0.0370 (18)0.0006 (15)0.0072 (15)−0.0007 (16)
C230.037 (2)0.033 (2)0.0333 (18)−0.0006 (16)0.0051 (16)−0.0065 (16)
C240.042 (2)0.034 (2)0.0343 (18)0.0070 (17)0.0156 (17)−0.0035 (16)
C250.034 (2)0.041 (2)0.042 (2)−0.0020 (17)0.0154 (17)−0.0062 (17)
C260.033 (2)0.036 (2)0.0381 (19)−0.0050 (16)0.0088 (16)−0.0063 (16)
C310.0206 (17)0.0260 (18)0.0346 (17)0.0001 (14)0.0065 (14)−0.0025 (15)
C320.049 (2)0.033 (2)0.0388 (19)0.0055 (17)0.0202 (17)0.0009 (16)
C330.057 (2)0.032 (2)0.045 (2)0.0059 (18)0.0220 (19)−0.0022 (17)
C340.035 (2)0.027 (2)0.047 (2)−0.0010 (16)0.0076 (17)0.0030 (17)
C350.044 (2)0.036 (2)0.0373 (19)−0.0028 (17)0.0148 (17)0.0013 (17)
C360.037 (2)0.034 (2)0.0335 (18)0.0012 (16)0.0124 (15)−0.0006 (16)
C410.0235 (18)0.0245 (18)0.0334 (17)0.0002 (14)0.0095 (15)−0.0055 (15)
C420.029 (2)0.0294 (19)0.0387 (19)0.0000 (15)0.0083 (15)−0.0019 (16)
C430.040 (2)0.031 (2)0.055 (2)−0.0044 (17)0.0203 (19)0.0004 (17)
C440.028 (2)0.036 (2)0.060 (2)−0.0044 (17)0.0171 (18)−0.0079 (19)
C450.026 (2)0.036 (2)0.050 (2)0.0030 (16)0.0084 (16)−0.0024 (18)
C460.0298 (19)0.0293 (19)0.0360 (17)0.0000 (16)0.0093 (15)0.0015 (15)
Geometric parameters (Å, °) top
Ni1—P12.1484 (9)C33—C341.378 (5)
Ni1—C11.843 (4)C34—C351.376 (5)
Ni1—C112.073 (3)C35—C361.383 (5)
Ni1—C122.141 (3)C41—C421.386 (4)
Ni1—C132.129 (3)C41—C461.391 (4)
Ni1—C142.084 (3)C42—C431.388 (4)
Ni1—C152.136 (3)C43—C441.389 (5)
P1—C211.835 (3)C44—C451.378 (5)
P1—C311.841 (3)C45—C461.390 (4)
P1—C411.828 (3)C3—H30.9500
C1—C21.211 (4)C5—H50.9500
C2—C41.433 (5)C6—H60.9500
C3—C41.384 (4)C11A—H11A0.9500
C3—C81.414 (4)C12A—H12A0.9500
C4—C51.431 (4)C13A—H13A0.9500
C5—C61.359 (4)C14A—H14A0.9500
C6—C71.408 (4)C11—H110.9500
C7—C11A1.416 (4)C12—H120.9500
C7—C81.422 (4)C13—H130.9500
C8—C14A1.410 (4)C14—H140.9500
C11A—C12A1.355 (4)C15—H150.9500
C12A—C13A1.406 (5)C22—H220.9500
C13A—C14A1.369 (5)C23—H230.9500
C11—C151.414 (5)C24—H240.9500
C11—C121.422 (5)C25—H250.9500
C12—C131.382 (5)C26—H260.9500
C13—C141.431 (5)C32—H320.9500
C14—C151.393 (5)C33—H330.9500
C21—C221.387 (4)C34—H340.9500
C21—C261.393 (4)C35—H350.9500
C22—C231.397 (4)C36—H360.9500
C23—C241.378 (4)C42—H420.9500
C24—C251.373 (4)C43—H430.9500
C25—C261.397 (5)C44—H440.9500
C31—C361.385 (4)C45—H450.9500
C31—C321.392 (4)C46—H460.9500
C32—C331.379 (5)
C1—Ni1—C1196.95 (14)C14—C15—C11106.3 (3)
C1—Ni1—C14159.31 (14)C14—C15—Ni168.71 (19)
C11—Ni1—C1465.39 (14)C11—C15—Ni167.98 (19)
C1—Ni1—C13144.11 (14)C22—C21—C26118.3 (3)
C11—Ni1—C1365.26 (14)C22—C21—P1122.3 (2)
C14—Ni1—C1339.69 (13)C26—C21—P1119.5 (2)
C1—Ni1—C15120.81 (14)C21—C22—C23120.7 (3)
C11—Ni1—C1539.21 (14)C24—C23—C22120.2 (3)
C14—Ni1—C1538.54 (13)C25—C24—C23119.9 (3)
C13—Ni1—C1565.41 (14)C24—C25—C26120.1 (3)
C1—Ni1—C12108.92 (14)C21—C26—C25120.8 (3)
C11—Ni1—C1239.42 (14)C36—C31—C32117.8 (3)
C14—Ni1—C1264.91 (14)C36—C31—P1122.6 (2)
C13—Ni1—C1237.78 (13)C32—C31—P1119.6 (2)
C15—Ni1—C1265.28 (15)C33—C32—C31120.9 (3)
C11—Ni1—P1171.96 (12)C34—C33—C32120.2 (3)
C14—Ni1—P1107.64 (10)C35—C34—C33119.9 (3)
C13—Ni1—P1112.38 (10)C34—C35—C36119.6 (3)
C15—Ni1—P1132.79 (11)C35—C36—C31121.6 (3)
C12—Ni1—P1142.77 (11)C42—C41—C46119.3 (3)
C41—P1—C21102.95 (14)C42—C41—P1119.1 (2)
C41—P1—C31104.70 (14)C46—C41—P1121.6 (2)
C21—P1—C31102.64 (14)C41—C42—C43120.9 (3)
Ni1—P1—C21118.63 (10)C42—C43—C44119.3 (3)
Ni1—P1—C31111.85 (10)C45—C44—C43120.4 (3)
Ni1—P1—C41114.48 (10)C44—C45—C46120.1 (3)
P1—Ni1—C189.04 (9)C45—C46—C41120.1 (3)
Ni1—C1—C2176.8 (3)C4—C3—H3119.1
C1—C2—C4173.0 (3)C8—C3—H3119.1
C4—C3—C8121.7 (3)C6—C5—H5119.7
C3—C4—C5118.3 (3)C4—C5—H5119.7
C3—C4—C2120.2 (3)C5—C6—H6119.0
C5—C4—C2121.5 (3)C7—C6—H6119.0
C6—C5—C4120.6 (3)C12A—C11A—H11A119.6
C5—C6—C7122.0 (3)C7—C11A—H11A119.6
C6—C7—C11A122.7 (3)C11A—C12A—H12A119.9
C6—C7—C8118.4 (3)C13A—C12A—H12A119.9
C11A—C7—C8118.9 (3)C14A—C13A—H13A119.6
C14A—C8—C3122.0 (3)C12A—C13A—H13A119.6
C14A—C8—C7119.0 (3)C13A—C14A—H14A119.9
C3—C8—C7119.0 (3)C8—C14A—H14A119.9
C12A—C11A—C7120.9 (3)C15—C11—H11125.6
C11A—C12A—C13A120.2 (3)C12—C11—H11125.6
C14A—C13A—C12A120.8 (3)Ni1—C11—H11120.5
C13A—C14A—C8120.2 (3)C13—C12—H12126.1
C15—C11—C12108.8 (3)C11—C12—H12126.1
C15—C11—Ni172.80 (19)Ni1—C12—H12127.1
C12—C11—Ni172.86 (19)C12—C13—H13126.3
C13—C12—C11107.8 (3)C14—C13—H13126.3
C13—C12—Ni170.64 (19)Ni1—C13—H13125.2
C11—C12—Ni167.72 (19)C15—C14—H14125.3
C12—C13—C14107.4 (3)C13—C14—H14125.3
C12—C13—Ni171.6 (2)Ni1—C14—H14121.7
C14—C13—Ni168.47 (19)C14—C15—H15126.9
C15—C14—C13109.3 (3)C11—C15—H15126.9
C15—C14—Ni172.8 (2)Ni1—C15—H15127.9
C13—C14—Ni171.84 (19)
C1—Ni1—P1—C4144.41 (15)Ni1—C13—C14—C1563.5 (2)
C14—Ni1—P1—C41−123.13 (16)C12—C13—C14—Ni1−61.3 (2)
C13—Ni1—P1—C41−165.20 (15)C1—Ni1—C14—C15−4.2 (5)
C15—Ni1—P1—C41−88.62 (18)C11—Ni1—C14—C15−37.5 (2)
C12—Ni1—P1—C41165.3 (2)C13—Ni1—C14—C15−117.8 (3)
C1—Ni1—P1—C21166.35 (16)C12—Ni1—C14—C15−81.2 (2)
C14—Ni1—P1—C21−1.19 (17)P1—Ni1—C14—C15138.1 (2)
C13—Ni1—P1—C21−43.26 (17)C1—Ni1—C14—C13113.6 (4)
C15—Ni1—P1—C2133.32 (19)C11—Ni1—C14—C1380.3 (2)
C12—Ni1—P1—C21−72.7 (2)C15—Ni1—C14—C13117.8 (3)
C1—Ni1—P1—C31−74.47 (15)C12—Ni1—C14—C1336.6 (2)
C14—Ni1—P1—C31117.99 (15)P1—Ni1—C14—C13−104.03 (19)
C13—Ni1—P1—C3175.91 (16)C13—C14—C15—C11−5.1 (4)
C15—Ni1—P1—C31152.49 (18)Ni1—C14—C15—C1157.8 (2)
C12—Ni1—P1—C3146.5 (2)C13—C14—C15—Ni1−62.9 (2)
C8—C3—C4—C50.2 (5)C12—C11—C15—C146.2 (4)
C8—C3—C4—C2−179.5 (3)Ni1—C11—C15—C14−58.3 (2)
C3—C4—C5—C6−0.2 (5)C12—C11—C15—Ni164.4 (2)
C2—C4—C5—C6179.5 (3)C1—Ni1—C15—C14178.3 (2)
C4—C5—C6—C7−0.2 (5)C11—Ni1—C15—C14118.8 (3)
C5—C6—C7—C11A−179.1 (3)C13—Ni1—C15—C1438.4 (2)
C5—C6—C7—C80.7 (5)C12—Ni1—C15—C1480.1 (2)
C4—C3—C8—C14A179.9 (3)P1—Ni1—C15—C14−60.0 (3)
C4—C3—C8—C70.3 (5)C1—Ni1—C15—C1159.5 (3)
C6—C7—C8—C14A179.7 (3)C14—Ni1—C15—C11−118.8 (3)
C11A—C7—C8—C14A−0.6 (5)C13—Ni1—C15—C11−80.4 (2)
C6—C7—C8—C3−0.7 (5)C12—Ni1—C15—C11−38.6 (2)
C11A—C7—C8—C3179.0 (3)P1—Ni1—C15—C11−178.84 (18)
C6—C7—C11A—C12A179.7 (3)C41—P1—C21—C22−9.5 (3)
C8—C7—C11A—C12A0.0 (5)C31—P1—C21—C2299.1 (3)
C7—C11A—C12A—C13A0.5 (5)Ni1—P1—C21—C22−137.0 (2)
C11A—C12A—C13A—C14A−0.4 (5)C41—P1—C21—C26171.5 (3)
C12A—C13A—C14A—C8−0.2 (5)C31—P1—C21—C26−80.0 (3)
C3—C8—C14A—C13A−178.9 (3)Ni1—P1—C21—C2643.9 (3)
C7—C8—C14A—C13A0.7 (5)C26—C21—C22—C230.4 (5)
C1—Ni1—C11—C15−131.8 (2)P1—C21—C22—C23−178.7 (2)
C14—Ni1—C11—C1536.9 (2)C21—C22—C23—C24−0.6 (5)
C13—Ni1—C11—C1580.8 (2)C22—C23—C24—C250.4 (5)
C12—Ni1—C11—C15116.7 (3)C23—C24—C25—C260.0 (5)
C1—Ni1—C11—C12111.5 (2)C22—C21—C26—C25−0.1 (5)
C14—Ni1—C11—C12−79.8 (2)P1—C21—C26—C25179.0 (3)
C13—Ni1—C11—C12−35.9 (2)C24—C25—C26—C21−0.1 (5)
C15—Ni1—C11—C12−116.7 (3)C41—P1—C31—C36108.2 (3)
C15—C11—C12—C13−4.9 (4)C21—P1—C31—C360.9 (3)
Ni1—C11—C12—C1359.5 (2)Ni1—P1—C31—C36−127.3 (2)
C15—C11—C12—Ni1−64.4 (2)C41—P1—C31—C32−73.7 (3)
C1—Ni1—C12—C13162.9 (2)C21—P1—C31—C32179.1 (3)
C11—Ni1—C12—C13−119.6 (3)Ni1—P1—C31—C3250.8 (3)
C14—Ni1—C12—C13−38.5 (2)C36—C31—C32—C330.7 (5)
C15—Ni1—C12—C13−81.1 (2)P1—C31—C32—C33−177.6 (3)
P1—Ni1—C12—C1347.9 (3)C31—C32—C33—C340.2 (5)
C1—Ni1—C12—C11−77.5 (2)C32—C33—C34—C35−1.2 (5)
C14—Ni1—C12—C1181.1 (2)C33—C34—C35—C361.3 (5)
C13—Ni1—C12—C11119.6 (3)C34—C35—C36—C31−0.4 (5)
C15—Ni1—C12—C1138.4 (2)C32—C31—C36—C35−0.6 (5)
P1—Ni1—C12—C11167.50 (18)P1—C31—C36—C35177.6 (2)
C11—C12—C13—C141.7 (4)C21—P1—C41—C42−96.4 (3)
Ni1—C12—C13—C1459.3 (2)C31—P1—C41—C42156.6 (2)
C11—C12—C13—Ni1−57.7 (2)Ni1—P1—C41—C4233.7 (3)
C1—Ni1—C13—C12−28.4 (4)C21—P1—C41—C4680.9 (3)
C11—Ni1—C13—C1237.4 (2)C31—P1—C41—C46−26.1 (3)
C14—Ni1—C13—C12118.1 (3)Ni1—P1—C41—C46−149.0 (2)
C15—Ni1—C13—C1280.8 (2)C46—C41—C42—C43−0.7 (5)
P1—Ni1—C13—C12−150.9 (2)P1—C41—C42—C43176.7 (3)
C1—Ni1—C13—C14−146.5 (2)C41—C42—C43—C440.9 (5)
C11—Ni1—C13—C14−80.6 (2)C42—C43—C44—C45−1.0 (5)
C15—Ni1—C13—C14−37.3 (2)C43—C44—C45—C460.8 (5)
C12—Ni1—C13—C14−118.1 (3)C44—C45—C46—C41−0.6 (5)
P1—Ni1—C13—C1491.0 (2)C42—C41—C46—C450.5 (5)
C12—C13—C14—C152.2 (4)P1—C41—C46—C45−176.8 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg10.952.843.760 (4)164
C6—H6···Cg2i0.952.743.549 (4)144
C25—H25···Cg3ii0.952.833.722 (3)157
C23—H23···Cg4iii0.953.043.797 (4)138
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x, −y, −z+1; (iii) x+1/2, −y+1/2, z+1/2.
Table 1
Selected geometric parameters (°) top
Ni1—P1—C21118.63 (10)P1—Ni1—C189.04 (9)
Ni1—P1—C31111.85 (10)Ni1—C1—C2176.8 (3)
Ni1—P1—C41114.48 (10)C1—C2—C4173.0 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg10.952.843.760 (4)164
C6—H6···Cg2i0.952.743.549 (4)144
C25—H25···Cg3ii0.952.833.722 (3)157
C23—H23···Cg4iii0.953.043.797 (4)138
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x, −y, −z+1; (iii) x+1/2, −y+1/2, z+1/2.
Acknowledgements top

JFG thanks Dublin City University and the Hospital for Sick Children (HSC), Toronto, for sabbatical leave (2004–2005) at HSC, Toronto, Canada.

references
References top

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