supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, m138    [ doi:10.1107/S1600536808043493 ]

Dichlorido{[2-(diphenylphosphino)phenyliminomethyl]ferrocene-[kappa]2N,P}platinum(II) dichloromethane hemisolvate

Y. Xie, Y. Wei, J.-G. Hu, J.-S. Zhao and F.-X. Jiang

Abstract top

In the title compound, [FePt(C5H5)(C24H19NP)Cl2]·0.5CH2Cl2, the PtII atom adopts a distorted square-planar geometry defined by one P atom and one N atom from the bidentate [2-(diphenylphosphino)phenyliminomethyl]ferrocene ligand and two Cl atoms. Two disordered dichloromethane solvent molecules are each 0.25-occupied on a twofold rotation axis.

Comment top

Ferrocene derivatives containing heteroatoms with good donor abilities have attracted great interest during the last few years in organometallic chemistry, since the coordination of a metal to these heteroatoms produces polymetallic molecules (Cullen & Woolins, 1981). Some examples showing the utility of these polymetallic compounds in homogeneous catalysis (Farrell et al., 2002; Wu et al., 2001) or for the design of new materials with outstanding properties (Gul et al., 2002) have been described. Here we report a new bimetallic platinum(II) complex with a ferrocenyliminophosphine ligand.

In the title compound, the PtII atom adopts a distorted square planar geometry, defined by one P atom and one N atom from the bidentate ferrocenyliminophosphine ligand (L) and two Cl atoms (Fig. 1), with N—Pt—Cl1 = 176.29 (9)° and P—Pt—Cl2 = 170.19 (4)°. The difference between the Pt—Cl bond lengths [2.2996 (13) and 2.3673 (11) Å] (Table 1) reflects the stronger trans influence of the tertiary phosphine compared with the imino group. The ligand L adopts a five-membered chelating ring. The benzene ring and the cyclopentadienyl ring are trans, with respect to the C11—N double bond.

Related literature top

For general background, see: Cullen & Woolins (1981); Farrell et al. (2002); Gul et al. (2002); Wu et al. (2001). For the ligand synthesis, see: Gong et al. (2006); Zhang et al. (2006).

Experimental top

The ligand L was prepared by literature method (Gong et al., 2006; Zhang et al., 2006). The title compound was prepared by reacting equal molar K2PtCl4 and L in CH2Cl2 (yield 83%). Brown needle crystals suitable for X-ray analysis were obtained by vapor diffusion of diethyl ether into a solution of the title compound in CH2Cl2. Analysis calculated for C29.5H25Cl3FeNPPt: C 45.32, H 3.22, N 1.79%; found: C 45.61, H 3.33, N 1.70%.

Refinement top

H atoms were positioned geomertrically and treated as riding, with C—H = 0.98 (cyclopentadienyl), 0.93 (phenyl) and 0.96 (CH2) Å and with Uiso(H) = 1.2Ueq(C). The highest residual electron density was found 0.67 Å from atom Cl4 and the deepest hole 0.79 Å from atom Pt. The disordered dichloromethane solvent molecules are each 0.25-occupied on a twofold rotation axis.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms and disordered dichloromethane solvent molecules have been omitted for clarity.
Dichlorido{[2-(diphenylphosphino)phenyliminomethyl]ferrocene- κ2N,P}platinum(II) dichloromethane hemisolvate top
Crystal data top
[FePt(C5H5)(C24H19NP)Cl2]·0.5CH2Cl2F(000) = 1516
Mr = 781.75Dx = 1.707 Mg m−3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 892 reflections
a = 19.5045 (11) Åθ = 3.2–25.8°
b = 12.0182 (7) ŵ = 5.40 mm−1
c = 12.9800 (8) ÅT = 293 K
V = 3042.6 (3) Å3Needle, brown–yellow
Z = 40.3 × 0.1 × 0.1 mm
Data collection top
Siemens SMART CCD
diffractometer		5902 independent reflections
Radiation source: fine-focus sealed tube4954 reflections with I > 2σ(I)
graphiteRint = 0.058
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −23→24
Tmin = 0.532, Tmax = 0.588k = −14→14
19964 measured reflectionsl = −16→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.024
5902 reflectionsΔρmax = 1.18 e Å−3
345 parametersΔρmin = −0.93 e Å−3
24 restraintsAbsolute structure: Flack (1983), 856 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.002 (11)
Crystal data top
[FePt(C5H5)(C24H19NP)Cl2]·0.5CH2Cl2V = 3042.6 (3) Å3
Mr = 781.75Z = 4
Orthorhombic, P21212Mo Kα radiation
a = 19.5045 (11) ŵ = 5.40 mm−1
b = 12.0182 (7) ÅT = 293 K
c = 12.9800 (8) Å0.3 × 0.1 × 0.1 mm
Data collection top
Siemens SMART CCD
diffractometer		5902 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4954 reflections with I > 2σ(I)
Tmin = 0.532, Tmax = 0.588Rint = 0.058
19964 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.116Δρmax = 1.18 e Å−3
S = 1.04Δρmin = −0.93 e Å−3
5902 reflectionsAbsolute structure: Flack (1983), 856 Friedel pairs
345 parametersFlack parameter: 0.002 (11)
24 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pt0.270357 (7)0.911967 (14)0.143789 (12)0.03558 (4)
Fe0.34183 (3)0.52770 (6)0.19921 (5)0.04447 (19)
Cl10.32009 (6)1.06905 (11)0.21198 (10)0.0568 (4)
Cl20.35362 (5)0.90898 (12)0.01112 (9)0.0538 (3)
Cl30.4874 (2)0.8826 (5)0.3249 (4)0.167 (2)0.50
Cl40.06774 (11)0.54821 (19)0.23620 (19)0.0506 (7)0.50
P0.17978 (5)0.91268 (11)0.24594 (8)0.0378 (3)
N0.22282 (15)0.7723 (3)0.0921 (2)0.0337 (9)
C10.3477 (4)0.3728 (6)0.2664 (5)0.097 (3)
H1A0.37710.31100.24470.117*
C20.3629 (4)0.4509 (6)0.3371 (4)0.096 (3)
H2A0.40660.45630.37420.115*
C30.3087 (4)0.5257 (7)0.3468 (5)0.102 (2)
H3A0.30670.58960.39360.123*
C40.2585 (4)0.4921 (8)0.2825 (6)0.112 (2)
H4A0.21370.52820.27490.135*
C50.2797 (4)0.3974 (6)0.2289 (6)0.110 (3)
H5A0.25300.35430.17890.132*
C60.3711 (2)0.6848 (4)0.1581 (3)0.0451 (13)
H6A0.36660.75170.20070.054*
C70.3221 (2)0.6444 (4)0.0886 (3)0.0402 (12)
C80.3478 (2)0.5451 (4)0.0462 (3)0.0442 (13)
H8A0.32460.4984−0.00500.053*
C90.4145 (2)0.5275 (4)0.0860 (4)0.0482 (13)
H9A0.44520.46580.06860.058*
C100.4278 (2)0.6129 (4)0.1561 (4)0.0539 (15)
H10A0.46960.62100.19730.065*
C110.25027 (18)0.6757 (4)0.0722 (3)0.0360 (11)
H11A0.22150.62150.04490.043*
C120.1890 (2)0.8272 (4)0.3601 (4)0.0516 (13)
C130.1388 (3)0.7539 (5)0.3915 (4)0.0752 (19)
H13A0.09850.74620.35390.090*
C140.1495 (4)0.6915 (6)0.4806 (4)0.090 (2)
H14A0.11740.63920.50220.108*
C150.2068 (3)0.7088 (6)0.5338 (5)0.092 (2)
H15A0.21390.66600.59250.111*
C160.2540 (3)0.7823 (6)0.5090 (5)0.0902 (19)
H16A0.29230.79460.55020.108*
C170.2437 (3)0.8398 (6)0.4191 (4)0.086 (2)
H17A0.27700.89040.39850.104*
C180.1426 (2)1.0435 (4)0.2854 (3)0.0443 (13)
C190.1014 (3)1.0460 (5)0.3785 (4)0.0586 (16)
H19A0.09660.98310.41950.070*
C200.0699 (3)1.1442 (5)0.4040 (5)0.0793 (19)
H20A0.04161.14620.46170.095*
C210.0784 (3)1.2379 (4)0.3481 (5)0.0659 (17)
H21A0.05791.30390.36930.079*
C220.1165 (3)1.2358 (5)0.2618 (5)0.0641 (17)
H22A0.11981.29990.22190.077*
C230.1507 (2)1.1413 (4)0.2307 (4)0.0505 (14)
H23A0.17921.14340.17320.061*
C240.1200 (2)0.8442 (4)0.1607 (3)0.0378 (11)
C250.0481 (2)0.8598 (4)0.1615 (3)0.0404 (12)
H25A0.02730.90380.21150.049*
C260.0092 (2)0.8074 (4)0.0854 (4)0.0536 (15)
H26A−0.03810.81640.08410.064*
C270.0420 (2)0.7399 (4)0.0095 (3)0.0506 (14)
H27A0.01590.7044−0.04060.061*
C280.1120 (2)0.7269 (4)0.0100 (3)0.0410 (12)
H28A0.13360.6825−0.03890.049*
C290.14973 (19)0.7811 (3)0.0845 (3)0.0372 (11)
C300.50001.00000.2754 (18)0.104 (8)0.50
H30A0.53860.98850.23080.125*0.50
C310.00000.50000.1697 (9)0.051 (4)0.50
H31A−0.01590.55900.12600.061*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt0.03605 (6)0.03424 (7)0.03646 (7)0.00216 (7)−0.00032 (7)0.00005 (8)
Fe0.0432 (3)0.0405 (4)0.0497 (4)0.0021 (3)0.0018 (3)−0.0005 (3)
Cl10.0584 (6)0.0514 (7)0.0608 (7)−0.0109 (6)0.0017 (5)−0.0103 (6)
Cl20.0508 (5)0.0506 (6)0.0598 (6)0.0014 (6)0.0200 (5)0.0055 (6)
Cl30.131 (3)0.146 (5)0.223 (5)−0.030 (3)−0.087 (3)0.041 (4)
Cl40.0373 (10)0.0439 (13)0.0706 (14)−0.0113 (9)−0.0071 (10)−0.0009 (11)
P0.0425 (5)0.0380 (6)0.0329 (5)0.0046 (6)0.0017 (4)0.0009 (5)
N0.0341 (15)0.0340 (17)0.0331 (15)0.0043 (15)0.0016 (14)−0.0008 (14)
C10.132 (5)0.060 (4)0.100 (5)−0.006 (4)0.029 (4)0.016 (3)
C20.119 (5)0.115 (6)0.054 (3)−0.001 (4)0.009 (3)0.029 (3)
C30.124 (4)0.104 (4)0.078 (3)0.008 (3)0.032 (3)−0.005 (3)
C40.097 (4)0.117 (4)0.123 (4)0.006 (3)0.030 (3)0.021 (4)
C50.123 (5)0.113 (5)0.095 (5)−0.060 (5)−0.009 (4)0.023 (4)
C60.046 (2)0.038 (2)0.051 (3)−0.004 (2)−0.010 (2)−0.004 (2)
C70.051 (2)0.031 (2)0.039 (2)0.009 (2)0.001 (2)−0.0032 (19)
C80.038 (2)0.045 (3)0.049 (2)0.004 (2)−0.0016 (19)−0.003 (2)
C90.036 (2)0.042 (3)0.066 (3)0.005 (2)0.002 (2)−0.006 (2)
C100.0300 (18)0.065 (3)0.067 (3)0.004 (2)−0.006 (2)−0.011 (3)
C110.0337 (19)0.044 (2)0.0302 (19)0.0036 (17)−0.0006 (16)0.0032 (19)
C120.063 (2)0.047 (3)0.044 (2)0.020 (2)0.016 (2)−0.005 (2)
C130.095 (4)0.068 (4)0.063 (3)0.015 (3)0.018 (3)0.018 (3)
C140.129 (5)0.075 (4)0.067 (3)0.004 (4)0.045 (3)0.023 (3)
C150.121 (4)0.087 (4)0.069 (3)0.035 (3)0.006 (3)0.011 (3)
C160.093 (3)0.095 (4)0.083 (3)0.028 (3)−0.014 (3)0.018 (3)
C170.108 (4)0.114 (5)0.037 (2)0.045 (4)−0.034 (3)−0.007 (3)
C180.040 (2)0.049 (3)0.044 (2)0.013 (2)−0.0078 (19)−0.007 (2)
C190.065 (3)0.058 (3)0.053 (3)−0.002 (3)0.011 (2)−0.011 (2)
C200.070 (3)0.093 (4)0.075 (3)0.038 (3)0.015 (3)−0.029 (3)
C210.071 (3)0.037 (3)0.090 (4)0.016 (2)−0.010 (3)−0.006 (3)
C220.064 (3)0.042 (3)0.085 (4)0.010 (3)−0.007 (3)−0.017 (3)
C230.052 (2)0.048 (3)0.051 (3)−0.003 (2)−0.007 (2)0.002 (2)
C240.048 (2)0.039 (2)0.026 (2)0.0119 (19)0.0011 (18)0.0000 (18)
C250.0375 (19)0.042 (2)0.042 (2)−0.0011 (19)0.0028 (18)0.003 (2)
C260.039 (2)0.056 (3)0.065 (3)0.005 (2)−0.004 (2)0.017 (3)
C270.047 (2)0.051 (3)0.054 (3)0.003 (2)−0.018 (2)0.001 (2)
C280.040 (2)0.028 (2)0.055 (3)0.0042 (19)0.003 (2)−0.0047 (19)
C290.0346 (18)0.029 (2)0.048 (2)0.0037 (18)0.0009 (18)0.0088 (19)
C300.017 (6)0.121 (17)0.174 (19)0.001 (8)0.0000.000
C310.093 (9)0.020 (6)0.040 (7)−0.019 (7)0.0000.000
Geometric parameters (Å, °) top
Pt—N2.031 (3)C9—H9A0.9800
Pt—P2.2089 (10)C10—H10A0.9800
Pt—Cl12.2996 (13)C11—H11A0.9300
Pt—Cl22.3673 (11)C12—C171.323 (7)
Fe—C12.059 (7)C12—C131.379 (8)
Fe—C22.055 (6)C13—C141.394 (8)
Fe—C32.022 (7)C13—H13A0.9300
Fe—C41.998 (8)C14—C151.330 (9)
Fe—C52.017 (7)C14—H14A0.9300
Fe—C62.043 (5)C15—C161.317 (10)
Fe—C72.044 (4)C15—H15A0.9300
Fe—C82.000 (5)C16—C171.371 (9)
Fe—C92.041 (5)C16—H16A0.9300
Fe—C102.042 (5)C17—H17A0.9300
Cl3—C301.570 (11)C18—C231.382 (7)
Cl4—C311.681 (6)C18—C191.451 (6)
P—C181.806 (5)C19—C201.371 (8)
P—C241.806 (4)C19—H19A0.9300
P—C121.812 (5)C20—C211.350 (8)
N—C111.304 (5)C20—H20A0.9300
N—C291.433 (5)C21—C221.345 (8)
C1—C21.346 (10)C21—H21A0.9300
C1—C51.443 (10)C22—C231.378 (7)
C1—H1A0.9800C22—H22A0.9300
C2—C31.393 (10)C23—H23A0.9300
C2—H2A0.9800C24—C291.375 (6)
C3—C41.348 (11)C24—C251.413 (6)
C3—H3A0.9800C25—C261.397 (6)
C4—C51.396 (11)C25—H25A0.9300
C4—H4A0.9800C26—C271.427 (7)
C5—H5A0.9800C26—H26A0.9300
C6—C71.401 (6)C27—C281.375 (6)
C6—C101.404 (6)C27—H27A0.9300
C6—H6A0.9800C28—C291.378 (6)
C7—C81.407 (6)C28—H28A0.9300
C7—C111.466 (6)C30—Cl3i1.570 (11)
C8—C91.415 (6)C30—H30A0.9600
C8—H8A0.9800C31—Cl4ii1.681 (6)
C9—C101.396 (7)C31—H31A0.9600
N—Pt—P80.59 (9)C10—C6—Fe69.9 (3)
N—Pt—Cl1176.29 (9)C7—C6—H6A125.9
P—Pt—Cl195.92 (4)C10—C6—H6A125.9
N—Pt—Cl293.46 (9)Fe—C6—H6A125.9
P—Pt—Cl2170.19 (4)C6—C7—C8107.6 (4)
Cl1—Pt—Cl290.17 (4)C6—C7—C11131.0 (4)
C4—Fe—C8127.4 (3)C8—C7—C11120.1 (4)
C4—Fe—C540.7 (3)C6—C7—Fe69.9 (3)
C8—Fe—C5107.8 (3)C8—C7—Fe68.0 (3)
C4—Fe—C339.2 (3)C11—C7—Fe117.3 (3)
C8—Fe—C3163.9 (2)C7—C8—C9108.2 (4)
C5—Fe—C367.5 (3)C7—C8—Fe71.3 (3)
C4—Fe—C9162.5 (3)C9—C8—Fe71.1 (3)
C8—Fe—C940.96 (18)C7—C8—H8A125.9
C5—Fe—C9123.6 (3)C9—C8—H8A125.9
C3—Fe—C9154.7 (2)Fe—C8—H8A125.9
C4—Fe—C10157.4 (3)C10—C9—C8107.4 (4)
C8—Fe—C1068.14 (19)C10—C9—Fe70.1 (3)
C5—Fe—C10159.2 (3)C8—C9—Fe68.0 (3)
C3—Fe—C10121.9 (3)C10—C9—H9A126.3
C9—Fe—C1039.98 (19)C8—C9—H9A126.3
C4—Fe—C6124.5 (3)Fe—C9—H9A126.3
C8—Fe—C668.16 (18)C9—C10—C6108.6 (4)
C5—Fe—C6159.2 (2)C9—C10—Fe70.0 (3)
C3—Fe—C6110.3 (3)C6—C10—Fe69.9 (3)
C9—Fe—C667.63 (19)C9—C10—H10A125.7
C10—Fe—C640.19 (18)C6—C10—H10A125.7
C4—Fe—C7111.9 (3)Fe—C10—H10A125.7
C8—Fe—C740.71 (18)N—C11—C7126.3 (4)
C5—Fe—C7123.6 (2)N—C11—H11A116.9
C3—Fe—C7127.8 (3)C7—C11—H11A116.9
C9—Fe—C768.04 (18)C17—C12—C13118.3 (5)
C10—Fe—C767.55 (18)C17—C12—P119.3 (4)
C6—Fe—C740.09 (17)C13—C12—P122.3 (4)
C4—Fe—C266.2 (3)C12—C13—C14118.9 (6)
C8—Fe—C2154.1 (2)C12—C13—H13A120.6
C5—Fe—C266.8 (3)C14—C13—H13A120.6
C3—Fe—C240.0 (3)C15—C14—C13118.2 (6)
C9—Fe—C2119.2 (2)C15—C14—H14A120.9
C10—Fe—C2107.4 (3)C13—C14—H14A120.9
C6—Fe—C2125.9 (2)C16—C15—C14124.5 (7)
C7—Fe—C2163.2 (2)C16—C15—H15A117.8
C4—Fe—C167.8 (3)C14—C15—H15A117.8
C8—Fe—C1120.8 (2)C15—C16—C17116.3 (6)
C5—Fe—C141.5 (3)C15—C16—H16A121.8
C3—Fe—C166.8 (3)C17—C16—H16A121.8
C9—Fe—C1105.4 (2)C12—C17—C16123.7 (6)
C10—Fe—C1121.6 (3)C12—C17—H17A118.2
C6—Fe—C1158.5 (2)C16—C17—H17A118.2
C7—Fe—C1158.2 (2)C23—C18—C19118.3 (4)
C2—Fe—C138.2 (3)C23—C18—P123.3 (3)
C18—P—C24108.1 (2)C19—C18—P118.4 (4)
C18—P—C12107.6 (2)C20—C19—C18117.9 (5)
C24—P—C12107.9 (2)C20—C19—H19A121.1
C18—P—Pt119.65 (15)C18—C19—H19A121.1
C24—P—Pt98.46 (13)C21—C20—C19122.2 (5)
C12—P—Pt114.18 (15)C21—C20—H20A118.9
C11—N—C29117.4 (3)C19—C20—H20A118.9
C11—N—Pt127.8 (3)C22—C21—C20120.0 (5)
C29—N—Pt114.6 (2)C22—C21—H21A120.0
C2—C1—C5106.8 (7)C20—C21—H21A120.0
C2—C1—Fe70.7 (4)C21—C22—C23121.8 (5)
C5—C1—Fe67.7 (4)C21—C22—H22A119.1
C2—C1—H1A126.6C23—C22—H22A119.1
C5—C1—H1A126.6C22—C23—C18119.6 (5)
Fe—C1—H1A126.6C22—C23—H23A120.2
C1—C2—C3110.1 (7)C18—C23—H23A120.2
C1—C2—Fe71.1 (4)C29—C24—C25119.8 (4)
C3—C2—Fe68.7 (4)C29—C24—P114.8 (3)
C1—C2—H2A124.9C25—C24—P125.1 (3)
C3—C2—H2A124.9C26—C25—C24118.3 (4)
Fe—C2—H2A124.9C26—C25—H25A120.9
C4—C3—C2107.6 (7)C24—C25—H25A120.9
C4—C3—Fe69.5 (4)C25—C26—C27120.1 (4)
C2—C3—Fe71.3 (4)C25—C26—H26A120.0
C4—C3—H3A126.2C27—C26—H26A120.0
C2—C3—H3A126.2C28—C27—C26120.4 (4)
Fe—C3—H3A126.2C28—C27—H27A119.8
C3—C4—C5109.7 (7)C26—C27—H27A119.8
C3—C4—Fe71.3 (5)C27—C28—C29118.7 (4)
C5—C4—Fe70.4 (4)C27—C28—H28A120.7
C3—C4—H4A125.1C29—C28—H28A120.7
C5—C4—H4A125.1C24—C29—C28122.7 (4)
Fe—C4—H4A125.1C24—C29—N114.3 (4)
C4—C5—C1105.7 (7)C28—C29—N123.0 (4)
C4—C5—Fe68.9 (5)Cl3i—C30—Cl3131.7 (16)
C1—C5—Fe70.8 (4)Cl3i—C30—H30A104.6
C4—C5—H5A127.1Cl3—C30—H30A104.0
C1—C5—H5A127.1Cl4—C31—Cl4ii118.2 (7)
Fe—C5—H5A127.1Cl4—C31—H31A107.6
C7—C6—C10108.2 (4)Cl4ii—C31—H31A107.7
C7—C6—Fe70.0 (3)
Symmetry codes: (i) −x+1, −y+2, z; (ii) −x, −y+1, z.
Table 1
Selected geometric parameters (Å) top
Pt—N2.031 (3)Pt—Cl12.2996 (13)
Pt—P2.2089 (10)Pt—Cl22.3673 (11)
references
References top

Cullen, W. R. & Woolins, J. D. (1981). Coord. Chem. Rev. 39, 1–47.

Farrell, A., Goddard, R. & Guiry, P. J. (2002). J. Org. Chem. 67, 4209–4217.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Gong, J. F., Wang, D. W., Zhang, Y. H., Zhu, Y. & Wu, Y. J. (2006). Inorg. Chim. Acta, 359, 2115–2119.

Gul, N., Nelson, J. H., Willis, A. C. & Ross, A. D. (2002). Organometallics, 21, 2041–2045.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Wu, Y., Hou, J., Cui, X. & Yuan, R. (2001). J. Organomet. Chem. 637–639, 793–798.

Zhang, X.-L., Kuang, R.-Y., Cao, Q.-Y., Li, Y.-X. & Luo, L.-T. (2006). Acta Cryst. E62, m2491–m2492.