metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[1,1′-Bis(di­phenyl­phosphan­yl)ferrocene-κ2P,P′](η5-cyclo­penta­dien­yl)(dicyanamido-κN)ruthenium(II) di­chloro­methane monosolvate

aInstitute of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, People's Republic of China
*Correspondence e-mail: lbgao@126.com

(Received 27 January 2012; accepted 2 April 2012; online 13 April 2012)

The title compound, [FeRu(C5H5)(C2N3)(C17H14P)2], was obtained by reaction of Cp(dppf)RuCl [dppf = 1,1′-bis­(diphenyl­phosphan­yl)ferrocene] with sodium dicyanamide in dichloro­methane. The RuII atom is capped by an η5-cyclo­penta­dienyl (Cp) ring, a chelating dppf and a terminal C2N3 unit, giving three-legged piano-stool geometry. The C—N—C angle of the N(CN)2 ligand [120.8 (6)°] is significantly smaller than that in the corresponding diruthenium complex [127.2 (9)°; Zhang et al. (2003[Zhang, L. Y., Shi, L. X. & Chen, Z. N. (2003). Inorg. Chem. 42, 633-640.]). Inorg. Chem. 42, 633–640] due to steric hindrance between the two {Cp(PPh3)2Ru} building blocks. Disorder was found in the dichloro­methane solvent mol­ecule, which was refined as disordered over two positions, with a site-occupancy ratio of 0.53:0.47 (2).

Related literature

For background to the use of CpRu(dppf), see: Gao et al. (2005[Gao, L. B., Zhang, L. Y., Shi, L. X. & Chen, Z. N. (2005). Organometallics, 24, 1678-1684.]). For the structure of [CpRu(dppf)(NCS)], which has a related geometry, see: Lu et al. (2004[Lu, X. L., Vittal, J. J., Tiekink, E. R. T., Tan, G. K., Kuan, S. L., Goh, L. Y. & Hor, T. S. N. (2004). J. Organomet. Chem. 689, 1978-1990]). For the corresponding diruthenium complex bridged with an N(CN)2 ligand, see: Zhang et al. (2003[Zhang, L. Y., Shi, L. X. & Chen, Z. N. (2003). Inorg. Chem. 42, 633-640.]).

[Scheme 1]

Experimental

Crystal data
  • [FeRu(C5H5)(C2N3)(C17H14P)2]

  • Mr = 871.49

  • Monoclinic, P 21 /c

  • a = 10.7858 (2) Å

  • b = 23.2456 (4) Å

  • c = 15.1530 (3) Å

  • β = 91.916 (1)°

  • V = 3797.07 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.04 mm−1

  • T = 293 K

  • 1.00 × 0.48 × 0.40 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.721, Tmax = 1.000

  • 11634 measured reflections

  • 6675 independent reflections

  • 5179 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.111

  • S = 1.12

  • 6675 reflections

  • 488 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.84 e Å−3

Table 1
Selected geometric parameters (Å, °)

Ru1—N1 2.071 (4)
Ru1—P2 2.3050 (13)
Ru1—P2 2.3050 (13)
Ru1—P1 2.3164 (13)
Ru1—Cg(C21–C25) 1.863 (2)

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

CpRu(dppf) (Gao et al.,2005) unit is a good building block for preparing heteronuclear molecular wires with excellent electrochemistry and photophysical properties. The overall geometry of the title compound (Fig. 1) is similar to that of [CpRu(dppf)(NCS)] (Lu et al., 2004), which shows a mononuclear RuII capped by an η5-Cp ring, a chelating η2-dppf and a terminal N(CN)2 ligand, thus completing a three-legged piano-stool configuration. The molecule of the title compound is shown in Fig.1 and the selected geometric parameters are given in Table 1. The distances of Ru—N (2.072 (5) Å) is slightly shorter than that found in compound [{Cp(PPh3)2Ru}2 N(CN)2](SbF6) (Zhang et al., 2003). The angle of the N(CN)2 ligand (120.8 (6)°) is significantly smaller than that in compound [{Cp(PPh3)2Ru}2 N(CN)2] (SbF6) (127.2 (9)°) due to the steric hindrance between the two {Cp(PPh3)2Ru} building blocks. The P1—Ru1—P2 chelate angle (96.60 (5)°) in the title compound is similar to that in the dppf analogue [CpRu (dppf)(NCS)](96.77 (3)°) (Lu et al., 2004) The overall coordination environment of RuII ion is a distorted octahedral geometry.

Related literature top

For a background to the use of CpRu(dppf), see: Gao et al. (2005). For the structure of [CpRu(dppf)(NCS)], which has a related geometry, see: Lu et al. (2004). For the corresponding diruthenium complex bridged with an N(CN)2 ligand, see: Zhang et al. (2003).

Experimental top

To a dichloromethane (20 ml) solution of Cp(dppf)2RuCl (0.20 mmol, 151.6 mg) was added a methanol (5 ml) solution of NaN(CN)2 (0.50 mmol, 44.5 mg) with the color change from orange into pale yellow. After the solution was stirred at room temperature for 4 h, the solvents were evaporated in vacuo to leave a residue which was dissolved in 3 ml of dichloromethane. After taken by filtration, the filtrate was layered with petroleum ether to give pale yellow crystals of the product. Yield: 83%. Crystals suitable for data collection were obtained by slow evaporation from a dichloromethane and hexane solution at room temperature

Refinement top

H atoms were positioned geometrically, with C—H distances of 0.96 or 0.93 Å, and allowed to ride on their respective parent C atoms, with Uiso(H) = 1.2Ueq(C). Disorder was found in the solvent dichloromethane, which was refined as disordered over two positions, with site occupancy ratio 0.53:0.47 (2)

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title compound with 20% displacment ellipsoids. H atoms and solvent CH2Cl2 are not shown clarity.
[1,1'-Bis(diphenylphosphanyl)ferrocene-κ2P,P'](η5- cyclopentadienyl)(dicyanamido-κN)ruthenium(II) dichloromethane monosolvate top
Crystal data top
[FeRu(C5H5)(C2N3)(C17H14P)2]F(000) = 1768
Mr = 871.49Dx = 1.524 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.7858 (2) ÅCell parameters from 5840 reflections
b = 23.2456 (4) Åθ = 1.6–25.0°
c = 15.1530 (3) ŵ = 1.04 mm1
β = 91.916 (1)°T = 293 K
V = 3797.07 (12) Å3Prism, yellow
Z = 41.00 × 0.48 × 0.40 mm
Data collection top
Bruker SMART CCD
diffractometer
6675 independent reflections
Radiation source: fine-focus sealed tube5179 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
phi and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.721, Tmax = 1.000k = 2723
11634 measured reflectionsl = 1813
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0223P)2 + 9.9372P]
where P = (Fo2 + 2Fc2)/3
6675 reflections(Δ/σ)max = 0.002
488 parametersΔρmax = 0.55 e Å3
3 restraintsΔρmin = 0.84 e Å3
Crystal data top
[FeRu(C5H5)(C2N3)(C17H14P)2]V = 3797.07 (12) Å3
Mr = 871.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.7858 (2) ŵ = 1.04 mm1
b = 23.2456 (4) ÅT = 293 K
c = 15.1530 (3) Å1.00 × 0.48 × 0.40 mm
β = 91.916 (1)°
Data collection top
Bruker SMART CCD
diffractometer
6675 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5179 reflections with I > 2σ(I)
Tmin = 0.721, Tmax = 1.000Rint = 0.029
11634 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0503 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.12Δρmax = 0.55 e Å3
6675 reflectionsΔρmin = 0.84 e Å3
488 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ru10.45845 (4)0.634892 (17)0.57549 (2)0.03596 (12)
Fe0.35171 (7)0.60717 (3)0.84919 (4)0.0468 (2)
P10.58633 (12)0.61849 (6)0.69878 (8)0.0396 (3)
P20.29837 (12)0.67701 (5)0.64910 (8)0.0369 (3)
N10.3711 (4)0.55699 (18)0.5966 (3)0.0429 (10)
N20.2399 (5)0.4731 (2)0.6204 (4)0.0723 (15)
N30.2171 (11)0.4231 (3)0.7574 (5)0.167 (4)
C030.1926 (5)0.5967 (2)0.7760 (3)0.0495 (13)
H03A0.17550.56540.73390.059*
C040.2479 (4)0.6511 (2)0.7555 (3)0.0404 (11)
C050.2557 (5)0.6825 (2)0.8375 (3)0.0550 (14)
H05A0.29060.72110.84560.066*
C020.1668 (5)0.5957 (3)0.8671 (4)0.0602 (15)
H02A0.12940.56370.89870.072*
C010.2059 (6)0.6479 (3)0.9045 (4)0.0641 (17)
H01A0.20070.65860.96690.077*
C60.2320 (7)0.4478 (3)0.6950 (5)0.078 (2)
C70.3122 (5)0.5173 (2)0.6117 (3)0.0449 (12)
C110.4735 (6)0.5853 (3)0.9495 (4)0.077 (2)
H11E0.46250.59271.01240.093*
C120.4347 (6)0.5359 (3)0.9036 (4)0.0730 (19)
H12C0.39200.50280.92870.088*
C130.4661 (5)0.5423 (2)0.8142 (4)0.0558 (14)
H13A0.44930.51430.76690.067*
C140.5258 (5)0.5963 (2)0.8042 (3)0.0483 (13)
C150.5314 (5)0.6229 (3)0.8893 (3)0.0633 (16)
H15A0.56720.66060.90340.076*
C210.5799 (5)0.6942 (3)0.5066 (3)0.0556 (15)
H21E0.63630.72230.53470.067*
C220.4560 (6)0.7048 (3)0.4777 (3)0.0553 (14)
H22B0.41180.74150.48260.066*
C230.5079 (5)0.6137 (3)0.4372 (3)0.0554 (15)
H23A0.50390.57540.41030.066*
C240.4105 (5)0.6550 (3)0.4349 (3)0.0564 (15)
H24A0.32880.65060.40540.068*
C250.6121 (5)0.6378 (3)0.4802 (3)0.0551 (14)
H25A0.69370.61970.48820.066*
C1110.7006 (5)0.5605 (2)0.6884 (3)0.0443 (12)
C1120.7948 (5)0.5537 (3)0.7530 (4)0.0618 (16)
H11D0.79750.57780.80190.074*
C1130.8841 (6)0.5114 (3)0.7452 (4)0.0689 (17)
H11C0.94590.50710.78900.083*
C1140.8815 (5)0.4757 (3)0.6727 (4)0.0603 (15)
H11F0.94280.44800.66660.072*
C1150.7879 (5)0.4812 (2)0.6093 (4)0.0569 (15)
H11B0.78520.45640.56110.068*
C1160.6977 (5)0.5232 (2)0.6164 (3)0.0476 (13)
H11A0.63510.52660.57290.057*
C1210.6855 (5)0.6805 (2)0.7238 (3)0.0442 (12)
C1220.6462 (5)0.7273 (2)0.7714 (3)0.0502 (13)
H12D0.57030.72580.79860.060*
C1230.7179 (6)0.7763 (3)0.7793 (4)0.0652 (16)
H12B0.69090.80700.81310.078*
C1240.8274 (7)0.7802 (3)0.7380 (4)0.078 (2)
H12F0.87490.81340.74320.094*
C1250.8679 (6)0.7347 (3)0.6885 (5)0.085 (2)
H12E0.94200.73740.65910.102*
C1260.7980 (5)0.6849 (3)0.6826 (4)0.0633 (16)
H12A0.82690.65390.65040.076*
C2110.1572 (4)0.6711 (2)0.5762 (3)0.0407 (11)
C2120.1320 (5)0.7133 (2)0.5137 (4)0.0554 (14)
H21C0.18010.74650.51410.066*
C2130.0370 (5)0.7073 (3)0.4506 (4)0.0646 (16)
H21F0.02110.73640.40970.078*
C2140.0336 (5)0.6581 (3)0.4490 (4)0.0613 (16)
H21A0.09710.65370.40650.074*
C2150.0105 (5)0.6157 (3)0.5099 (4)0.0552 (14)
H21D0.05890.58260.50920.066*
C2160.0848 (5)0.6220 (2)0.5728 (3)0.0479 (13)
H21B0.10050.59260.61340.057*
C2210.3073 (5)0.7550 (2)0.6697 (3)0.0447 (12)
C2220.2047 (6)0.7856 (3)0.6977 (4)0.0643 (16)
H22E0.13080.76610.70680.077*
C2230.2104 (7)0.8439 (3)0.7123 (5)0.079 (2)
H22F0.14000.86380.72880.094*
C2240.3204 (7)0.8729 (3)0.7023 (4)0.0733 (19)
H22D0.32470.91230.71240.088*
C2250.4237 (6)0.8433 (3)0.6775 (4)0.0621 (16)
H22C0.49860.86260.67220.075*
C2260.4169 (5)0.7846 (2)0.6603 (3)0.0485 (13)
H22A0.48700.76510.64230.058*
Cl10.950 (3)0.5700 (14)1.048 (2)0.318 (16)0.47 (2)
Cl20.8391 (7)0.6687 (4)0.9689 (7)0.109 (3)0.47 (2)
C990.872 (5)0.6209 (15)1.0479 (18)0.29 (4)0.47 (2)
H99A0.90430.64381.09710.351*0.47 (2)
H99B0.79190.60701.06560.351*0.47 (2)
Cl1'0.8624 (17)0.5479 (4)0.9963 (7)0.175 (5)0.53 (2)
Cl2'0.8505 (18)0.6653 (7)0.9971 (15)0.282 (9)0.53 (2)
C99'0.821 (2)0.6008 (10)1.0370 (18)0.160 (17)0.53 (2)
H99C0.85450.60041.09730.192*0.53 (2)
H99D0.73190.59791.04050.192*0.53 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0352 (2)0.0436 (2)0.02893 (19)0.00103 (19)0.00017 (14)0.00060 (17)
Fe0.0538 (5)0.0545 (5)0.0325 (4)0.0030 (4)0.0056 (3)0.0018 (3)
P10.0368 (7)0.0498 (8)0.0321 (6)0.0009 (6)0.0022 (5)0.0040 (5)
P20.0369 (7)0.0363 (7)0.0375 (7)0.0016 (5)0.0003 (5)0.0013 (5)
N10.045 (2)0.045 (2)0.039 (2)0.001 (2)0.0005 (19)0.0042 (19)
N20.090 (4)0.060 (3)0.068 (3)0.030 (3)0.016 (3)0.008 (3)
N30.317 (13)0.086 (5)0.101 (6)0.056 (7)0.052 (7)0.024 (5)
C030.051 (3)0.051 (3)0.047 (3)0.003 (3)0.005 (2)0.001 (2)
C040.039 (3)0.042 (3)0.041 (3)0.003 (2)0.005 (2)0.003 (2)
C050.067 (4)0.050 (3)0.048 (3)0.001 (3)0.005 (3)0.014 (3)
C020.058 (4)0.068 (4)0.057 (3)0.006 (3)0.022 (3)0.006 (3)
C010.083 (4)0.065 (4)0.046 (3)0.004 (3)0.027 (3)0.002 (3)
C60.117 (6)0.042 (4)0.078 (5)0.014 (4)0.026 (4)0.005 (3)
C70.047 (3)0.046 (3)0.042 (3)0.005 (3)0.005 (2)0.009 (2)
C110.073 (4)0.119 (6)0.040 (3)0.002 (4)0.003 (3)0.017 (4)
C120.072 (4)0.084 (5)0.063 (4)0.008 (4)0.008 (3)0.031 (4)
C130.062 (4)0.056 (4)0.049 (3)0.011 (3)0.002 (3)0.013 (3)
C140.042 (3)0.064 (4)0.038 (3)0.006 (3)0.005 (2)0.006 (2)
C150.059 (4)0.092 (5)0.037 (3)0.013 (3)0.009 (3)0.001 (3)
C210.057 (4)0.073 (4)0.038 (3)0.016 (3)0.006 (3)0.011 (3)
C220.069 (4)0.061 (4)0.036 (3)0.001 (3)0.003 (3)0.014 (3)
C230.071 (4)0.066 (4)0.030 (3)0.011 (3)0.010 (3)0.009 (2)
C240.061 (4)0.081 (4)0.027 (3)0.003 (3)0.003 (2)0.006 (3)
C250.049 (3)0.073 (4)0.044 (3)0.004 (3)0.019 (2)0.008 (3)
C1110.039 (3)0.051 (3)0.043 (3)0.006 (2)0.002 (2)0.003 (2)
C1120.061 (4)0.069 (4)0.054 (3)0.011 (3)0.015 (3)0.015 (3)
C1130.065 (4)0.067 (4)0.072 (4)0.015 (3)0.021 (3)0.001 (3)
C1140.053 (4)0.054 (4)0.074 (4)0.013 (3)0.006 (3)0.006 (3)
C1150.066 (4)0.051 (3)0.054 (3)0.005 (3)0.004 (3)0.005 (3)
C1160.050 (3)0.049 (3)0.044 (3)0.002 (3)0.003 (2)0.004 (2)
C1210.042 (3)0.055 (3)0.035 (3)0.002 (2)0.003 (2)0.010 (2)
C1220.050 (3)0.061 (4)0.040 (3)0.001 (3)0.001 (2)0.009 (2)
C1230.077 (4)0.061 (4)0.057 (4)0.001 (3)0.003 (3)0.020 (3)
C1240.078 (5)0.078 (5)0.078 (5)0.027 (4)0.003 (4)0.026 (4)
C1250.058 (4)0.097 (5)0.101 (5)0.031 (4)0.017 (4)0.031 (5)
C1260.052 (4)0.068 (4)0.070 (4)0.006 (3)0.012 (3)0.022 (3)
C2110.035 (3)0.043 (3)0.043 (3)0.003 (2)0.002 (2)0.005 (2)
C2120.049 (3)0.057 (3)0.060 (3)0.005 (3)0.007 (3)0.011 (3)
C2130.058 (4)0.074 (4)0.061 (4)0.007 (3)0.017 (3)0.014 (3)
C2140.044 (3)0.087 (5)0.052 (3)0.001 (3)0.011 (3)0.000 (3)
C2150.036 (3)0.065 (4)0.063 (4)0.004 (3)0.006 (3)0.014 (3)
C2160.043 (3)0.050 (3)0.050 (3)0.000 (2)0.003 (2)0.002 (2)
C2210.050 (3)0.039 (3)0.045 (3)0.000 (2)0.006 (2)0.003 (2)
C2220.053 (4)0.055 (4)0.085 (4)0.001 (3)0.000 (3)0.015 (3)
C2230.086 (5)0.051 (4)0.098 (5)0.017 (4)0.004 (4)0.018 (4)
C2240.114 (6)0.042 (3)0.064 (4)0.005 (4)0.009 (4)0.004 (3)
C2250.077 (4)0.052 (4)0.056 (4)0.014 (3)0.002 (3)0.001 (3)
C2260.058 (3)0.044 (3)0.043 (3)0.002 (3)0.001 (2)0.000 (2)
Cl10.28 (2)0.41 (2)0.27 (2)0.215 (19)0.182 (17)0.23 (2)
Cl20.114 (6)0.104 (5)0.106 (5)0.040 (4)0.026 (3)0.037 (3)
C990.72 (13)0.067 (17)0.11 (2)0.10 (4)0.19 (5)0.051 (15)
Cl1'0.265 (13)0.124 (6)0.140 (7)0.037 (6)0.077 (7)0.049 (5)
Cl2'0.43 (2)0.211 (13)0.200 (14)0.049 (13)0.006 (12)0.005 (10)
C99'0.14 (2)0.16 (4)0.18 (3)0.03 (2)0.013 (19)0.11 (3)
Geometric parameters (Å, º) top
Ru1—N12.071 (4)C24—H24A0.9800
Ru1—C212.191 (5)C25—H25A0.9794
Ru1—C222.200 (5)C111—C1161.392 (7)
Ru1—C242.225 (5)C111—C1121.396 (7)
Ru1—C232.234 (5)C112—C1131.383 (8)
Ru1—C252.234 (5)C112—H11D0.9300
Ru1—P22.3050 (13)C113—C1141.376 (8)
Ru1—P12.3164 (13)C113—H11C0.9300
Fe—C032.027 (5)C114—C1151.376 (8)
Fe—C132.029 (6)C114—H11F0.9300
Fe—C142.035 (5)C115—C1161.385 (7)
Fe—C052.038 (6)C115—H11B0.9300
Fe—C012.039 (6)C116—H11A0.9300
Fe—C022.039 (6)C121—C1221.379 (7)
Fe—C112.040 (6)C121—C1261.388 (7)
Fe—C122.043 (6)C122—C1231.380 (8)
Fe—C152.044 (6)C122—H12D0.9300
Fe—C042.050 (5)C123—C1241.358 (9)
P1—C141.821 (5)C123—H12B0.9300
P1—C1211.827 (5)C124—C1251.377 (9)
P1—C1111.837 (5)C124—H12F0.9300
P2—C041.822 (5)C125—C1261.382 (8)
P2—C2211.842 (5)C125—H12E0.9300
P2—C2111.856 (5)C126—H12A0.9300
N1—C71.148 (6)C211—C2121.383 (7)
N2—C61.280 (8)C211—C2161.384 (7)
N2—C71.297 (7)C212—C2131.385 (7)
N3—C61.123 (9)C212—H21C0.9300
C03—C021.417 (7)C213—C2141.374 (8)
C03—C041.436 (7)C213—H21F0.9300
C03—H03A0.9811C214—C2151.368 (8)
C04—C051.441 (7)C214—H21A0.9300
C05—C011.414 (8)C215—C2161.386 (7)
C05—H05A0.9791C215—H21D0.9300
C02—C011.398 (8)C216—H21B0.9300
C02—H02A0.9789C221—C2261.380 (7)
C01—H01A0.9811C221—C2221.393 (7)
C11—C121.398 (9)C222—C2231.375 (8)
C11—C151.424 (8)C222—H22E0.9300
C11—H11E0.9796C223—C2241.377 (9)
C12—C131.414 (8)C223—H22F0.9300
C12—H12C0.9800C224—C2251.373 (9)
C13—C141.421 (8)C224—H22D0.9300
C13—H13A0.9806C225—C2261.390 (7)
C14—C151.429 (7)C225—H22C0.9300
C15—H15A0.9784C226—H22A0.9300
C21—C221.414 (8)Cl1—C991.45 (2)
C21—C251.418 (8)Cl2—C991.663 (19)
C21—H21E0.9802C99—H99A0.9700
C22—C241.407 (8)C99—H99B0.9700
C22—H22B0.9813Cl1'—C99'1.45 (2)
C23—C251.397 (8)Cl2'—C99'1.651 (18)
C23—C241.423 (8)C99'—H99C0.9700
C23—H23A0.9795C99'—H99D0.9700
N1—Ru1—C21155.02 (19)C12—C13—Fe70.2 (4)
N1—Ru1—C22139.02 (19)C14—C13—Fe69.7 (3)
C21—Ru1—C2237.6 (2)C12—C13—H13A125.9
N1—Ru1—C24103.84 (19)C14—C13—H13A125.5
C21—Ru1—C2462.3 (2)Fe—C13—H13A125.8
C22—Ru1—C2437.1 (2)C13—C14—C15106.9 (5)
N1—Ru1—C2394.37 (18)C13—C14—P1121.4 (4)
C21—Ru1—C2361.7 (2)C15—C14—P1131.6 (4)
C22—Ru1—C2361.9 (2)C13—C14—Fe69.3 (3)
C24—Ru1—C2337.2 (2)C15—C14—Fe69.9 (3)
N1—Ru1—C25118.49 (19)P1—C14—Fe128.4 (3)
C21—Ru1—C2537.4 (2)C11—C15—C14107.8 (6)
C22—Ru1—C2562.3 (2)C11—C15—Fe69.4 (4)
C24—Ru1—C2561.9 (2)C14—C15—Fe69.1 (3)
C23—Ru1—C2536.4 (2)C11—C15—H15A126.1
N1—Ru1—P286.83 (12)C14—C15—H15A126.1
C21—Ru1—P2115.62 (17)Fe—C15—H15A126.0
C22—Ru1—P291.14 (16)C22—C21—C25108.1 (5)
C24—Ru1—P2102.70 (16)C22—C21—Ru171.6 (3)
C23—Ru1—P2138.90 (16)C25—C21—Ru173.0 (3)
C25—Ru1—P2152.06 (16)C22—C21—H21E125.8
N1—Ru1—P189.63 (11)C25—C21—H21E125.8
C21—Ru1—P197.96 (15)Ru1—C21—H21E125.8
C22—Ru1—P1131.18 (16)C24—C22—C21108.1 (5)
C24—Ru1—P1156.91 (16)C24—C22—Ru172.4 (3)
C23—Ru1—P1124.46 (16)C21—C22—Ru170.9 (3)
C25—Ru1—P195.25 (15)C24—C22—H22B125.9
P2—Ru1—P196.61 (5)C21—C22—H22B125.8
C03—Fe—C13106.2 (2)Ru1—C22—H22B125.9
C03—Fe—C14125.2 (2)C25—C23—C24108.8 (5)
C13—Fe—C1440.9 (2)C25—C23—Ru171.8 (3)
C03—Fe—C0568.7 (2)C24—C23—Ru171.0 (3)
C13—Fe—C05157.9 (2)C25—C23—H23A125.6
C14—Fe—C05123.3 (2)C24—C23—H23A125.5
C03—Fe—C0168.3 (2)Ru1—C23—H23A125.6
C13—Fe—C01159.3 (2)C22—C24—C23107.3 (5)
C14—Fe—C01158.2 (2)C22—C24—Ru170.5 (3)
C05—Fe—C0140.6 (2)C23—C24—Ru171.7 (3)
C03—Fe—C0240.8 (2)C22—C24—H24A126.2
C13—Fe—C02122.9 (2)C23—C24—H24A126.3
C14—Fe—C02161.1 (2)Ru1—C24—H24A126.3
C05—Fe—C0268.1 (2)C23—C25—C21107.5 (5)
C01—Fe—C0240.1 (2)C23—C25—Ru171.8 (3)
C03—Fe—C11152.9 (3)C21—C25—Ru169.6 (3)
C13—Fe—C1168.1 (3)C23—C25—H25A126.2
C14—Fe—C1168.9 (2)C21—C25—H25A126.2
C05—Fe—C11126.3 (3)Ru1—C25—H25A126.1
C01—Fe—C11107.2 (3)C116—C111—C112118.4 (5)
C02—Fe—C11118.5 (2)C116—C111—P1121.8 (4)
C03—Fe—C12118.4 (3)C112—C111—P1119.8 (4)
C13—Fe—C1240.6 (2)C113—C112—C111120.9 (5)
C14—Fe—C1268.8 (2)C113—C112—H11D119.6
C05—Fe—C12161.0 (2)C111—C112—H11D119.6
C01—Fe—C12122.9 (2)C114—C113—C112120.0 (5)
C02—Fe—C12104.9 (3)C114—C113—H11C120.0
C11—Fe—C1240.0 (3)C112—C113—H11C120.0
C03—Fe—C15163.9 (2)C113—C114—C115119.8 (5)
C13—Fe—C1568.4 (3)C113—C114—H11F120.1
C14—Fe—C1541.0 (2)C115—C114—H11F120.1
C05—Fe—C15110.2 (3)C114—C115—C116120.8 (5)
C01—Fe—C15122.1 (3)C114—C115—H11B119.6
C02—Fe—C15154.9 (2)C116—C115—H11B119.6
C11—Fe—C1540.8 (2)C115—C116—C111120.1 (5)
C12—Fe—C1568.1 (3)C115—C116—H11A119.9
C03—Fe—C0441.25 (19)C111—C116—H11A119.9
C13—Fe—C04120.8 (2)C122—C121—C126117.8 (5)
C14—Fe—C04108.57 (19)C122—C121—P1122.9 (4)
C05—Fe—C0441.27 (19)C126—C121—P1118.6 (4)
C01—Fe—C0469.1 (2)C121—C122—C123121.1 (5)
C02—Fe—C0469.1 (2)C121—C122—H12D119.5
C11—Fe—C04164.4 (3)C123—C122—H12D119.5
C12—Fe—C04154.8 (3)C124—C123—C122120.5 (6)
C15—Fe—C04127.4 (2)C124—C123—H12B119.8
C14—P1—C121105.4 (2)C122—C123—H12B119.8
C14—P1—C11197.4 (2)C123—C124—C125119.8 (6)
C121—P1—C111102.0 (2)C123—C124—H12F120.1
C14—P1—Ru1122.21 (17)C125—C124—H12F120.1
C121—P1—Ru1111.49 (17)C124—C125—C126119.8 (6)
C111—P1—Ru1115.75 (16)C124—C125—H12E120.1
C04—P2—C221101.0 (2)C126—C125—H12E120.1
C04—P2—C211103.9 (2)C125—C126—C121121.0 (6)
C221—P2—C211102.1 (2)C125—C126—H12A119.5
C04—P2—Ru1122.59 (16)C121—C126—H12A119.5
C221—P2—Ru1117.67 (18)C212—C211—C216117.5 (5)
C211—P2—Ru1107.06 (16)C212—C211—P2119.6 (4)
C7—N1—Ru1172.6 (4)C216—C211—P2122.2 (4)
C6—N2—C7120.8 (6)C211—C212—C213121.7 (5)
C02—C03—C04108.8 (5)C211—C212—H21C119.2
C02—C03—Fe70.1 (3)C213—C212—H21C119.2
C04—C03—Fe70.3 (3)C214—C213—C212119.5 (5)
C02—C03—H03A125.6C214—C213—H21F120.2
C04—C03—H03A125.7C212—C213—H21F120.2
Fe—C03—H03A125.6C215—C214—C213119.9 (5)
C03—C04—C05105.8 (4)C215—C214—H21A120.0
C03—C04—P2128.4 (4)C213—C214—H21A120.0
C05—C04—P2125.8 (4)C214—C215—C216120.2 (5)
C03—C04—Fe68.5 (3)C214—C215—H21D119.9
C05—C04—Fe68.9 (3)C216—C215—H21D119.9
P2—C04—Fe127.3 (3)C211—C216—C215121.1 (5)
C01—C05—C04108.5 (5)C211—C216—H21B119.4
C01—C05—Fe69.7 (3)C215—C216—H21B119.4
C04—C05—Fe69.8 (3)C226—C221—C222118.0 (5)
C01—C05—H05A125.8C226—C221—P2120.9 (4)
C04—C05—H05A125.7C222—C221—P2121.1 (4)
Fe—C05—H05A125.7C223—C222—C221121.3 (6)
C01—C02—C03108.3 (5)C223—C222—H22E119.3
C01—C02—Fe69.9 (3)C221—C222—H22E119.3
C03—C02—Fe69.1 (3)C222—C223—C224120.0 (6)
C01—C02—H02A125.8C222—C223—H22F120.0
C03—C02—H02A125.9C224—C223—H22F120.0
Fe—C02—H02A125.8C225—C224—C223119.6 (6)
C02—C01—C05108.6 (5)C225—C224—H22D120.2
C02—C01—Fe70.0 (3)C223—C224—H22D120.2
C05—C01—Fe69.7 (3)C224—C225—C226120.4 (6)
C02—C01—H01A125.8C224—C225—H22C119.8
C05—C01—H01A125.6C226—C225—H22C119.8
Fe—C01—H01A125.7C221—C226—C225120.7 (5)
N3—C6—N2174.3 (10)C221—C226—H22A119.7
N1—C7—N2173.8 (6)C225—C226—H22A119.7
C12—C11—C15108.4 (6)Cl1—C99—Cl2131.1 (15)
C12—C11—Fe70.1 (4)Cl1—C99—H99A104.5
C15—C11—Fe69.8 (3)Cl2—C99—H99A104.5
C12—C11—H11E125.8Cl1—C99—H99B104.5
C15—C11—H11E125.9Cl2—C99—H99B104.5
Fe—C11—H11E125.8H99A—C99—H99B105.6
C11—C12—C13108.2 (6)Cl1'—C99'—Cl2'123.3 (17)
C11—C12—Fe69.9 (4)Cl1'—C99'—H99C106.5
C13—C12—Fe69.2 (3)Cl2'—C99'—H99C106.5
C11—C12—H12C126.0Cl1'—C99'—H99D106.5
C13—C12—H12C125.8Cl2'—C99'—H99D106.5
Fe—C12—H12C126.0H99C—C99'—H99D106.5
C12—C13—C14108.6 (6)
N1—Ru1—P1—C1448.8 (2)C05—Fe—C13—C12171.9 (6)
C21—Ru1—P1—C14155.1 (3)C01—Fe—C13—C1243.7 (9)
C22—Ru1—P1—C14135.4 (3)C02—Fe—C13—C1273.6 (5)
C24—Ru1—P1—C14175.2 (5)C11—Fe—C13—C1237.0 (4)
C23—Ru1—P1—C14143.8 (3)C15—Fe—C13—C1281.1 (4)
C25—Ru1—P1—C14167.3 (3)C04—Fe—C13—C12157.3 (4)
P2—Ru1—P1—C1438.0 (2)C03—Fe—C13—C14125.5 (3)
N1—Ru1—P1—C121174.6 (2)C05—Fe—C13—C1452.2 (7)
C21—Ru1—P1—C12129.3 (2)C01—Fe—C13—C14163.3 (6)
C22—Ru1—P1—C1219.5 (3)C02—Fe—C13—C14166.8 (3)
C24—Ru1—P1—C12158.9 (5)C11—Fe—C13—C1482.6 (4)
C23—Ru1—P1—C12190.4 (3)C12—Fe—C13—C14119.6 (5)
C25—Ru1—P1—C12166.8 (2)C15—Fe—C13—C1438.5 (3)
P2—Ru1—P1—C12187.82 (18)C04—Fe—C13—C1483.0 (3)
N1—Ru1—P1—C11169.5 (2)C12—C13—C14—C150.4 (6)
C21—Ru1—P1—C11186.6 (3)Fe—C13—C14—C1560.0 (4)
C22—Ru1—P1—C111106.4 (3)C12—C13—C14—P1177.2 (4)
C24—Ru1—P1—C11157.0 (5)Fe—C13—C14—P1123.2 (4)
C23—Ru1—P1—C11125.6 (3)C12—C13—C14—Fe59.6 (4)
C25—Ru1—P1—C11149.1 (2)C121—P1—C14—C13166.6 (4)
P2—Ru1—P1—C111156.26 (19)C111—P1—C14—C1361.9 (5)
N1—Ru1—P2—C0449.5 (2)Ru1—P1—C14—C1364.9 (5)
C21—Ru1—P2—C04141.9 (2)C121—P1—C14—C159.3 (6)
C22—Ru1—P2—C04171.5 (2)C111—P1—C14—C15114.0 (5)
C24—Ru1—P2—C04152.9 (2)Ru1—P1—C14—C15119.2 (5)
C23—Ru1—P2—C04142.5 (3)C121—P1—C14—Fe106.0 (4)
C25—Ru1—P2—C04154.3 (4)C111—P1—C14—Fe149.4 (4)
P1—Ru1—P2—C0439.8 (2)Ru1—P1—C14—Fe22.6 (5)
N1—Ru1—P2—C221175.7 (2)C03—Fe—C14—C1373.1 (4)
C21—Ru1—P2—C22115.6 (2)C05—Fe—C14—C13159.2 (3)
C22—Ru1—P2—C22145.2 (2)C01—Fe—C14—C13164.2 (6)
C24—Ru1—P2—C22180.8 (2)C02—Fe—C14—C1336.3 (8)
C23—Ru1—P2—C22191.2 (3)C11—Fe—C14—C1380.5 (4)
C25—Ru1—P2—C22128.0 (4)C12—Fe—C14—C1337.4 (4)
P1—Ru1—P2—C22186.49 (18)C15—Fe—C14—C13118.0 (5)
N1—Ru1—P2—C21170.1 (2)C04—Fe—C14—C13115.9 (3)
C21—Ru1—P2—C21198.5 (2)C03—Fe—C14—C15168.9 (3)
C22—Ru1—P2—C21168.9 (2)C13—Fe—C14—C15118.0 (5)
C24—Ru1—P2—C21133.4 (2)C05—Fe—C14—C1582.8 (4)
C23—Ru1—P2—C21122.9 (3)C01—Fe—C14—C1546.2 (7)
C25—Ru1—P2—C21186.1 (4)C02—Fe—C14—C15154.3 (7)
P1—Ru1—P2—C211159.37 (17)C11—Fe—C14—C1537.5 (4)
C21—Ru1—N1—C7148 (3)C12—Fe—C14—C1580.6 (4)
C22—Ru1—N1—C781 (3)C04—Fe—C14—C15126.1 (3)
C24—Ru1—N1—C795 (3)C03—Fe—C14—P141.2 (5)
C23—Ru1—N1—C7131 (3)C13—Fe—C14—P1114.3 (5)
C25—Ru1—N1—C7160 (3)C05—Fe—C14—P144.9 (5)
P2—Ru1—N1—C78 (3)C01—Fe—C14—P181.5 (7)
P1—Ru1—N1—C7104 (3)C02—Fe—C14—P178.0 (8)
C13—Fe—C03—C02121.9 (4)C11—Fe—C14—P1165.2 (5)
C14—Fe—C03—C02162.7 (3)C12—Fe—C14—P1151.7 (5)
C05—Fe—C03—C0280.8 (4)C15—Fe—C14—P1127.7 (6)
C01—Fe—C03—C0237.0 (3)C04—Fe—C14—P11.6 (4)
C11—Fe—C03—C0248.5 (7)C12—C11—C15—C141.0 (7)
C12—Fe—C03—C0279.8 (4)Fe—C11—C15—C1458.6 (4)
C15—Fe—C03—C02170.2 (8)C12—C11—C15—Fe59.7 (5)
C04—Fe—C03—C02119.6 (5)C13—C14—C15—C110.9 (6)
C13—Fe—C03—C04118.5 (3)P1—C14—C15—C11177.2 (4)
C14—Fe—C03—C0477.7 (4)Fe—C14—C15—C1158.8 (4)
C05—Fe—C03—C0438.8 (3)C13—C14—C15—Fe59.7 (4)
C01—Fe—C03—C0482.6 (3)P1—C14—C15—Fe124.0 (5)
C02—Fe—C03—C04119.6 (5)C03—Fe—C15—C11154.2 (8)
C11—Fe—C03—C04168.0 (5)C13—Fe—C15—C1181.1 (4)
C12—Fe—C03—C04160.7 (3)C14—Fe—C15—C11119.5 (6)
C15—Fe—C03—C0450.6 (10)C05—Fe—C15—C11122.5 (4)
C02—C03—C04—C050.6 (6)C01—Fe—C15—C1178.9 (5)
Fe—C03—C04—C0559.1 (4)C02—Fe—C15—C1141.1 (8)
C02—C03—C04—P2179.1 (4)C12—Fe—C15—C1137.2 (4)
Fe—C03—C04—P2121.2 (4)C04—Fe—C15—C11166.0 (4)
C02—C03—C04—Fe59.7 (4)C03—Fe—C15—C1434.7 (11)
C221—P2—C04—C03161.8 (5)C13—Fe—C15—C1438.5 (3)
C211—P2—C04—C0356.2 (5)C05—Fe—C15—C14117.9 (3)
Ru1—P2—C04—C0364.9 (5)C01—Fe—C15—C14161.5 (3)
C221—P2—C04—C0517.8 (5)C02—Fe—C15—C14160.6 (5)
C211—P2—C04—C05123.4 (5)C11—Fe—C15—C14119.5 (6)
Ru1—P2—C04—C05115.5 (4)C12—Fe—C15—C1482.4 (4)
C221—P2—C04—Fe107.4 (3)C04—Fe—C15—C1474.5 (4)
C211—P2—C04—Fe147.1 (3)N1—Ru1—C21—C2298.1 (5)
Ru1—P2—C04—Fe26.0 (4)C24—Ru1—C21—C2237.3 (3)
C13—Fe—C04—C0379.2 (3)C23—Ru1—C21—C2279.7 (4)
C14—Fe—C04—C03122.6 (3)C25—Ru1—C21—C22116.4 (5)
C05—Fe—C04—C03117.7 (4)P2—Ru1—C21—C2254.0 (4)
C01—Fe—C04—C0380.5 (3)P1—Ru1—C21—C22155.3 (3)
C02—Fe—C04—C0337.5 (3)N1—Ru1—C21—C2518.3 (6)
C11—Fe—C04—C03159.5 (8)C22—Ru1—C21—C25116.4 (5)
C12—Fe—C04—C0343.1 (6)C24—Ru1—C21—C2579.1 (4)
C15—Fe—C04—C03164.4 (3)C23—Ru1—C21—C2536.8 (3)
C03—Fe—C04—C05117.7 (4)P2—Ru1—C21—C25170.5 (3)
C13—Fe—C04—C05163.0 (3)P1—Ru1—C21—C2588.2 (3)
C14—Fe—C04—C05119.7 (3)C25—C21—C22—C241.0 (6)
C01—Fe—C04—C0537.2 (3)Ru1—C21—C22—C2463.3 (4)
C02—Fe—C04—C0580.3 (3)C25—C21—C22—Ru164.3 (3)
C11—Fe—C04—C0541.7 (9)N1—Ru1—C22—C2423.3 (5)
C12—Fe—C04—C05160.9 (5)C21—Ru1—C22—C24117.1 (5)
C15—Fe—C04—C0577.9 (4)C23—Ru1—C22—C2437.8 (3)
C03—Fe—C04—P2122.6 (4)C25—Ru1—C22—C2479.2 (4)
C13—Fe—C04—P243.4 (4)P2—Ru1—C22—C24109.8 (3)
C14—Fe—C04—P20.0 (4)P1—Ru1—C22—C24150.4 (3)
C05—Fe—C04—P2119.7 (5)N1—Ru1—C22—C21140.4 (3)
C01—Fe—C04—P2156.9 (4)C24—Ru1—C22—C21117.1 (5)
C02—Fe—C04—P2160.1 (4)C23—Ru1—C22—C2179.3 (4)
C11—Fe—C04—P277.9 (9)C25—Ru1—C22—C2137.9 (3)
C12—Fe—C04—P279.4 (6)P2—Ru1—C22—C21133.1 (3)
C15—Fe—C04—P241.8 (4)P1—Ru1—C22—C2133.3 (4)
C03—C04—C05—C010.3 (6)N1—Ru1—C23—C25134.6 (4)
P2—C04—C05—C01179.4 (4)C21—Ru1—C23—C2537.7 (3)
Fe—C04—C05—C0159.1 (4)C22—Ru1—C23—C2580.6 (4)
C03—C04—C05—Fe58.9 (3)C24—Ru1—C23—C25118.2 (5)
P2—C04—C05—Fe121.5 (4)P2—Ru1—C23—C25135.2 (3)
C03—Fe—C05—C0181.0 (4)P1—Ru1—C23—C2542.0 (4)
C13—Fe—C05—C01161.6 (6)N1—Ru1—C23—C24107.2 (3)
C14—Fe—C05—C01160.1 (3)C21—Ru1—C23—C2480.5 (4)
C02—Fe—C05—C0137.0 (4)C22—Ru1—C23—C2437.6 (3)
C11—Fe—C05—C0173.0 (5)C25—Ru1—C23—C24118.2 (5)
C12—Fe—C05—C0134.8 (10)P2—Ru1—C23—C2417.0 (4)
C15—Fe—C05—C01116.1 (4)P1—Ru1—C23—C24160.2 (3)
C04—Fe—C05—C01119.8 (5)C21—C22—C24—C230.4 (6)
C03—Fe—C05—C0438.8 (3)Ru1—C22—C24—C2362.7 (4)
C13—Fe—C05—C0441.8 (8)C21—C22—C24—Ru162.3 (3)
C14—Fe—C05—C0480.1 (4)C25—C23—C24—C220.3 (6)
C01—Fe—C05—C04119.8 (5)Ru1—C23—C24—C2261.9 (3)
C02—Fe—C05—C0482.8 (3)C25—C23—C24—Ru162.2 (4)
C11—Fe—C05—C04167.2 (3)N1—Ru1—C24—C22164.5 (3)
C12—Fe—C05—C04154.6 (8)C21—Ru1—C24—C2237.8 (3)
C15—Fe—C05—C04124.1 (3)C23—Ru1—C24—C22116.7 (5)
C04—C03—C02—C010.7 (7)C25—Ru1—C24—C2280.3 (4)
Fe—C03—C02—C0159.1 (4)P2—Ru1—C24—C2274.7 (3)
C04—C03—C02—Fe59.8 (4)P1—Ru1—C24—C2271.4 (6)
C03—Fe—C02—C01119.8 (5)N1—Ru1—C24—C2378.8 (3)
C13—Fe—C02—C01164.2 (3)C21—Ru1—C24—C2378.9 (4)
C14—Fe—C02—C01168.4 (6)C22—Ru1—C24—C23116.7 (5)
C05—Fe—C02—C0137.5 (3)C25—Ru1—C24—C2336.4 (3)
C11—Fe—C02—C0183.0 (4)P2—Ru1—C24—C23168.6 (3)
C12—Fe—C02—C01123.9 (4)P1—Ru1—C24—C2345.3 (6)
C15—Fe—C02—C0153.8 (7)C24—C23—C25—C211.0 (6)
C04—Fe—C02—C0181.9 (4)Ru1—C23—C25—C2160.8 (3)
C13—Fe—C02—C0376.1 (4)C24—C23—C25—Ru161.7 (4)
C14—Fe—C02—C0348.6 (8)C22—C21—C25—C231.2 (6)
C05—Fe—C02—C0382.3 (3)Ru1—C21—C25—C2362.1 (3)
C01—Fe—C02—C03119.8 (5)C22—C21—C25—Ru163.4 (3)
C11—Fe—C02—C03157.2 (4)N1—Ru1—C25—C2353.9 (4)
C12—Fe—C02—C03116.3 (4)C21—Ru1—C25—C23117.4 (5)
C15—Fe—C02—C03173.6 (5)C22—Ru1—C25—C2379.4 (4)
C04—Fe—C02—C0337.9 (3)C24—Ru1—C25—C2337.2 (3)
C03—C02—C01—C050.5 (7)P2—Ru1—C25—C2398.8 (4)
Fe—C02—C01—C0559.1 (4)P1—Ru1—C25—C23146.3 (3)
C03—C02—C01—Fe58.6 (4)N1—Ru1—C25—C21171.3 (3)
C04—C05—C01—C020.1 (7)C22—Ru1—C25—C2138.1 (3)
Fe—C05—C01—C0259.3 (4)C24—Ru1—C25—C2180.2 (4)
C04—C05—C01—Fe59.2 (4)C23—Ru1—C25—C21117.4 (5)
C03—Fe—C01—C0237.6 (3)P2—Ru1—C25—C2118.6 (5)
C13—Fe—C01—C0240.5 (8)P1—Ru1—C25—C2196.2 (3)
C14—Fe—C01—C02169.9 (5)C14—P1—C111—C116121.8 (5)
C05—Fe—C01—C02119.8 (5)C121—P1—C111—C116130.7 (4)
C11—Fe—C01—C02114.0 (4)Ru1—P1—C111—C1169.5 (5)
C12—Fe—C01—C0273.0 (5)C14—P1—C111—C11259.4 (5)
C15—Fe—C01—C02156.2 (3)C121—P1—C111—C11248.2 (5)
C04—Fe—C01—C0282.0 (4)Ru1—P1—C111—C112169.4 (4)
C03—Fe—C01—C0582.2 (4)C116—C111—C112—C1130.9 (9)
C13—Fe—C01—C05160.4 (6)P1—C111—C112—C113178.0 (5)
C14—Fe—C01—C0550.0 (7)C111—C112—C113—C1140.5 (10)
C02—Fe—C01—C05119.8 (5)C112—C113—C114—C1151.8 (10)
C11—Fe—C01—C05126.2 (4)C113—C114—C115—C1161.6 (9)
C12—Fe—C01—C05167.2 (4)C114—C115—C116—C1110.2 (8)
C15—Fe—C01—C0584.0 (4)C112—C111—C116—C1151.0 (8)
C04—Fe—C01—C0537.8 (3)P1—C111—C116—C115177.8 (4)
C7—N2—C6—N3171 (9)C14—P1—C121—C12251.4 (5)
Ru1—N1—C7—N286 (6)C111—P1—C121—C122152.7 (4)
C6—N2—C7—N1170 (5)Ru1—P1—C121—C12283.2 (4)
C03—Fe—C11—C1245.3 (7)C14—P1—C121—C126138.5 (5)
C13—Fe—C11—C1237.5 (4)C111—P1—C121—C12637.3 (5)
C14—Fe—C11—C1281.7 (4)Ru1—P1—C121—C12686.8 (5)
C05—Fe—C11—C12161.8 (4)C126—C121—C122—C1231.4 (8)
C01—Fe—C11—C12121.1 (4)P1—C121—C122—C123171.6 (4)
C02—Fe—C11—C1279.1 (4)C121—C122—C123—C1241.9 (9)
C15—Fe—C11—C12119.4 (6)C122—C123—C124—C1250.5 (11)
C04—Fe—C11—C12165.2 (7)C123—C124—C125—C1261.3 (11)
C03—Fe—C11—C15164.7 (5)C124—C125—C126—C1211.8 (11)
C13—Fe—C11—C1581.9 (4)C122—C121—C126—C1250.4 (9)
C14—Fe—C11—C1537.7 (4)P1—C121—C126—C125170.2 (5)
C05—Fe—C11—C1578.8 (5)C04—P2—C211—C212141.9 (4)
C01—Fe—C11—C15119.5 (4)C221—P2—C211—C21237.1 (5)
C02—Fe—C11—C15161.5 (4)Ru1—P2—C211—C21287.1 (4)
C12—Fe—C11—C15119.4 (6)C04—P2—C211—C21647.7 (5)
C04—Fe—C11—C1545.8 (10)C221—P2—C211—C216152.5 (4)
C15—C11—C12—C130.8 (8)Ru1—P2—C211—C21683.3 (4)
Fe—C11—C12—C1358.7 (4)C216—C211—C212—C2130.9 (8)
C15—C11—C12—Fe59.5 (5)P2—C211—C212—C213171.7 (5)
C03—Fe—C12—C11158.4 (4)C211—C212—C213—C2140.7 (9)
C13—Fe—C12—C11119.8 (6)C212—C213—C214—C2150.6 (9)
C14—Fe—C12—C1182.1 (4)C213—C214—C215—C2160.7 (9)
C05—Fe—C12—C1150.8 (10)C212—C211—C216—C2151.0 (8)
C01—Fe—C12—C1177.1 (5)P2—C211—C216—C215171.6 (4)
C02—Fe—C12—C11116.7 (4)C214—C215—C216—C2110.9 (8)
C15—Fe—C12—C1137.8 (4)C04—P2—C221—C226121.5 (4)
C04—Fe—C12—C11170.8 (5)C211—P2—C221—C226131.6 (4)
C03—Fe—C12—C1381.8 (4)Ru1—P2—C221—C22614.7 (5)
C14—Fe—C12—C1337.7 (4)C04—P2—C221—C22256.5 (5)
C05—Fe—C12—C13170.6 (7)C211—P2—C221—C22250.4 (5)
C01—Fe—C12—C13163.1 (4)Ru1—P2—C221—C222167.3 (4)
C02—Fe—C12—C13123.5 (4)C226—C221—C222—C2232.6 (9)
C11—Fe—C12—C13119.8 (6)P2—C221—C222—C223179.3 (5)
C15—Fe—C12—C1381.9 (4)C221—C222—C223—C2242.5 (10)
C04—Fe—C12—C1351.0 (7)C222—C223—C224—C2250.3 (10)
C11—C12—C13—C140.3 (7)C223—C224—C225—C2261.6 (9)
Fe—C12—C13—C1459.4 (4)C222—C221—C226—C2250.7 (8)
C11—C12—C13—Fe59.1 (5)P2—C221—C226—C225178.8 (4)
C03—Fe—C13—C12114.9 (4)C224—C225—C226—C2211.4 (8)
C14—Fe—C13—C12119.6 (5)

Experimental details

Crystal data
Chemical formula[FeRu(C5H5)(C2N3)(C17H14P)2]
Mr871.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.7858 (2), 23.2456 (4), 15.1530 (3)
β (°) 91.916 (1)
V3)3797.07 (12)
Z4
Radiation typeMo Kα
µ (mm1)1.04
Crystal size (mm)1.00 × 0.48 × 0.40
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.721, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
11634, 6675, 5179
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.111, 1.12
No. of reflections6675
No. of parameters488
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.84

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Ru1—N12.071 (4)N2—C71.297 (7)
Ru1—P22.3050 (13)N3—C61.123 (9)
Ru1—P12.3164 (13)Cl1—C991.45 (2)
N1—C71.148 (6)Cl2—C991.663 (19)
N2—C61.280 (8)
N1—Ru1—C21155.02 (19)C14—P1—Ru1122.21 (17)
N1—Ru1—C22139.02 (19)C04—P2—Ru1122.59 (16)
N1—Ru1—C24103.84 (19)P2—C04—Fe127.3 (3)
N1—Ru1—C2394.37 (18)N3—C6—N2174.3 (10)
N1—Ru1—P286.83 (12)N1—C7—N2173.8 (6)
N1—Ru1—P189.63 (11)P1—C14—Fe128.4 (3)
P2—Ru1—P196.61 (5)Cl1—C99—Cl2131.1 (15)
 

Acknowledgements

X-ray data were collected at the Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences.

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGao, L. B., Zhang, L. Y., Shi, L. X. & Chen, Z. N. (2005). Organometallics, 24, 1678–1684.  Web of Science CSD CrossRef CAS Google Scholar
First citationLu, X. L., Vittal, J. J., Tiekink, E. R. T., Tan, G. K., Kuan, S. L., Goh, L. Y. & Hor, T. S. N. (2004). J. Organomet. Chem. 689, 1978–1990  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, L. Y., Shi, L. X. & Chen, Z. N. (2003). Inorg. Chem. 42, 633–640.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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