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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m184.
Published online 2007 December 12. doi:  10.1107/S1600536807065968
PMCID: PMC2915117

cis-cis-trans-Bis(acetonitrile-κN)dichloridobis(triphenyl­phosphine-κP)ruthenium(II) acetonitrile disolvate

Abstract

The title compound, [RuCl2(C2H3N)2(C18H15P)2]·2C2H3N, was obtained upon stirring an acetonitrile/ethanol solution of [RuCl2(PPh3)3]. In the crystal structure, each RuII ion is coordinated by two Cl [Ru—Cl = 2.4308 (7) and 2.4139 (7) Å], two N [Ru—N = 2.016 (2) and 2.003 (2) Å], and two P [Ru—P = 2.3688 (7) and 2.3887 (7) Å] atoms in a distorted octa­hedral geometry. Packing inter­actions include typical C—H(...)π contacts involving phenyl groups as well as weak hydrogen bonds between CH3CN methyl H atoms and Cl or solvent CH3CN N atoms.

Related literature

For the original synthesis, characterization and reactivity of the title compound and its precursor, see: Gilbert & Wilkinson (1969 [triangle]); Stephenson & Wilkinson (1966 [triangle]); Hallman et al. (1970 [triangle]); Caulton (1974 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m184-scheme1.jpg

Experimental

Crystal data

  • [RuCl2(C2H3N)2(C18H15P)2]·2C2H3N
  • M r = 860.73
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m184-efi3.jpg
  • a = 9.0622 (9) Å
  • b = 18.0167 (18) Å
  • c = 25.628 (2) Å
  • V = 4184.3 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.61 mm−1
  • T = 170 (2) K
  • 0.40 × 0.35 × 0.20 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.791, T max = 0.887
  • 25910 measured reflections
  • 10568 independent reflections
  • 9200 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.072
  • S = 1.02
  • 10568 reflections
  • 482 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.30 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4387 Friedel pairs
  • Flack parameter: −0.02 (2)

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065968/ci2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065968/ci2537Isup2.hkl

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

Acknowledgments

The authors thank Oklahoma State University for financial support and the Oklahoma State Regents for Higher Education for providing funds to purchase the APEXII diffractometer.

supplementary crystallographic information

Comment

[RuCl2(PPh3)3] has been widely used as a convenient synthon for a variety of RuII complexes (Stephenson & Wilkinson, 1966; Hallman et al., 1970). It readily loses one phosphine ligand in solution to give solvent adducts or chlorido-bridged RuII species that are potential catalyst precursors (Caulton, 1974). Gilbert & Wilkinson (1969) previously reported the synthesis of two isomers of [RuCl2(CH3CN)2(PPh3)2] having either cis or trans orientations of the acetonitrile ligands as characterized by infrared spectroscopy. The cis isomer was obtained upon refluxing [RuCl2(PPh3)3] in CH3CN/acetone, whereas the trans isomer was formed upon refluxing in CH3CN/toluene. We found that the cis isomer could also be obtained by stirring [RuCl2(PPh3)3] in CH3CN/ethanol at ambient temperature, confirming the importance of a polar co-solvent in favoring a cis geometry.

The crystal structure of the title compound contains one [RuCl2(CH3CN)2(PPh3)2] complex and two acetonitriles of crystallization in the asymmetric unit. The RuII complex displays a cis orientation of both the chlorido and CH3CN ligands and a trans orientation of the phosphine ligands (Fig. 1). The Ru—Cl [2.4308 (7), 2.4139 (7) Å], Ru—N [2.016 (2), 2.003 (2) Å], and Ru—P [2.3688 (7), 2.3887 (7) Å] distances are in the expected ranges, and the angles between coordinated atoms are in the range 90.02 (6)—93.83 (2)°. In addition to typical C—H···π packing interactions involving phenyl rings, there are several weak hydrogren bonds between C—H bonds of coordinated or solvate acetonitriles and Cl ligands or solvate acetonitrile N atoms (Fig. 2). The H···acceptor distances range from 2.57—2.80 Å, and the C···acceptor distances range from 3.52—3.70 Å (Table 1).

Although it has been little investigated, [RuCl2(CH3CN)2(PPh3)2] is a potentially useful precursor for catalytically active Ru species given the presence of two dissociable ligands in a cis arrangement.

Experimental

[RuCl2(PPh3)3] (20 mg) was dissolved in a mixture of degassed absolute ethanol (2 ml) and freshly distilled CH3CN (3 ml) and stirred for 15 min. During this time, the color of the solution changed from dark brown to yellow. The solvent was removed under vacuum, and the resulting yellow powder was dried for a further 2 h. A 10 mg portion of the solid was dissolved in 0.6 ml of acetonitrile and alllowed to stand for 3 d under nitrogen. Large yellow-orange crystals of the title compound formed over this time. The crystals became opaque due to solvent loss within 20 min of removal from acetonitrile unless placed in a cold stream. The sample used in this study was cut from a larger (>1 mm) block, immersed in Paratone N oil in a 0.5 mm nylon loop, and placed in the nitrogen cold stream of an APEXII diffractometer at 170 (2) K for X-ray diffraction analysis.

Refinement

Phenyl H atoms were fixed at C—H distances of 0.95 Å and refined as riding, with Uiso(H) = 1.2Ueq(C). Methyl H atoms were placed with idealized threefold symmetry and fixed C—H distances of 0.98 Å, and they were refined in a riding model with Uiso(H) = 1.5Ueq(C). In order to assign the absolute structure, 4387 Friedel pairs (71% of all Friedel pairs) were measured, and Friedel opposites were not merged in the reflection list used for structure solution and refinement. The absolute structure parameter (Flack x) refined to -0.02 (2). For the inverted structure, Flack x refined to 1.02 (2), and increases in R[F2>2σ(F2)] and wR(F2) of 0.33% and 1.29%, respectively, were observed.

Figures

Fig. 1.
ORTEP view of the complex portion of the title compound, with displacement ellipsoids at the 50% probability level. Phenyl hydrogen atoms and acetonitriles of crystallization are omitted for clarity.
Fig. 2.
Packing diagram showing a portion of the network of weak hydrogen bonds involving acetonitrile C—H bonds. Symmetry codes: (A) 2 - x, 1/2 + y, 1/2 - z; (B) -1 + x, y, z; (C) 1 + x, y, z; (D) -1/2 + x, 1/2 - y, -z. For solvent symmetry equivalents, ...

Crystal data

[RuCl2(C2H3N)2(C18H15P)2]·2C2H3NF000 = 1768
Mr = 860.73Dx = 1.366 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7584 reflections
a = 9.0622 (9) Åθ = 2.6–29.0º
b = 18.0167 (18) ŵ = 0.61 mm1
c = 25.628 (2) ÅT = 170 (2) K
V = 4184.3 (7) Å3Block, orange
Z = 40.40 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer10568 independent reflections
Radiation source: fine-focus sealed tube9200 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
Detector resolution: 0.75 pixels mm-1θmax = 29.0º
T = 170(2) Kθmin = 2.0º
[var phi] and ω scansh = −12→11
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)k = −23→24
Tmin = 0.791, Tmax = 0.887l = −24→34
25910 measured reflections

Refinement

Refinement on F2  w = 1/[σ2(Fo2) + (0.0197P)2 + 1.2863P] where P = (Fo2 + 2Fc2)/3
Least-squares matrix: full(Δ/σ)max = 0.002
R[F2 > 2σ(F2)] = 0.035Δρmax = 0.38 e Å3
wR(F2) = 0.072Δρmin = −0.30 e Å3
S = 1.02Extinction correction: none
10568 reflectionsAbsolute structure: Flack (1983), 4387 Friedel pairs
482 parametersFlack parameter: −0.02 (2)
H-atom parameters constrained

Special details

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)

xyzUiso*/Ueq
Ru10.98665 (2)0.525404 (10)0.202447 (8)0.01835 (5)
N11.1935 (2)0.56649 (11)0.20310 (9)0.0221 (4)
C11.3072 (3)0.59216 (14)0.20769 (11)0.0260 (6)
C21.4541 (3)0.62345 (18)0.21633 (14)0.0424 (9)
H2A1.45720.64780.25050.064*
H2B1.47590.65990.18900.064*
H2C1.52780.58360.21520.064*
N20.9070 (2)0.62612 (12)0.21976 (8)0.0220 (5)
C30.8554 (3)0.68174 (16)0.22992 (11)0.0268 (6)
C40.7865 (4)0.75235 (16)0.24243 (12)0.0371 (7)
H4A0.74770.77490.21050.056*
H4B0.85980.78550.25810.056*
H4C0.70550.74420.26710.056*
Cl11.07873 (8)0.40246 (4)0.18086 (3)0.02873 (15)
Cl20.73218 (6)0.48601 (4)0.20527 (3)0.02807 (14)
P10.95830 (7)0.55102 (4)0.11234 (3)0.02106 (14)
P21.00686 (7)0.49955 (3)0.29358 (2)0.02023 (12)
C110.8461 (3)0.63406 (16)0.10137 (10)0.0234 (6)
C120.9038 (4)0.70435 (16)0.11118 (11)0.0311 (7)
H121.00540.70950.11950.037*
C130.8153 (4)0.76658 (17)0.10896 (13)0.0392 (8)
H130.85690.81410.11550.047*
C140.6677 (4)0.76067 (19)0.09743 (13)0.0409 (8)
H140.60730.80370.09570.049*
C150.6078 (4)0.69085 (19)0.08828 (14)0.0426 (8)
H150.50580.68610.08050.051*
C160.6965 (3)0.62787 (17)0.09043 (12)0.0321 (7)
H160.65450.58030.08440.039*
C210.8672 (3)0.48398 (16)0.06914 (10)0.0235 (6)
C220.8493 (3)0.50217 (17)0.01617 (11)0.0304 (7)
H220.88620.54800.00330.036*
C230.7778 (4)0.45353 (19)−0.01746 (12)0.0376 (7)
H230.76520.4664−0.05310.045*
C240.7249 (4)0.3863 (2)0.00102 (13)0.0407 (8)
H240.67640.3529−0.02190.049*
C250.7430 (3)0.36848 (18)0.05247 (12)0.0367 (7)
H250.70590.32250.06500.044*
C260.8147 (3)0.41607 (16)0.08707 (12)0.0302 (7)
H260.82760.40230.12250.036*
C311.1296 (3)0.56553 (17)0.07510 (11)0.0274 (6)
C321.2373 (3)0.51060 (18)0.07986 (12)0.0356 (7)
H321.22350.47130.10410.043*
C331.3649 (4)0.5126 (2)0.04960 (13)0.0429 (8)
H331.43690.47450.05290.052*
C341.3864 (4)0.5699 (2)0.01487 (13)0.0474 (9)
H341.47260.5711−0.00620.057*
C351.2835 (4)0.6250 (2)0.01071 (13)0.0498 (10)
H351.30050.6652−0.01250.060*
C361.1541 (4)0.6232 (2)0.03999 (12)0.0408 (8)
H361.08250.66130.03600.049*
C410.9408 (3)0.57923 (16)0.33105 (10)0.0287 (7)
C420.7897 (4)0.5863 (2)0.34125 (12)0.0411 (8)
H420.72380.54700.33310.049*
C430.7367 (5)0.6519 (2)0.36353 (14)0.0612 (13)
H430.63460.65670.37140.073*
C440.8310 (7)0.7095 (2)0.37417 (15)0.0737 (16)
H440.79390.75400.38920.088*
C450.9794 (7)0.7031 (2)0.36316 (14)0.0654 (13)
H451.04410.74320.37050.078*
C461.0343 (4)0.63864 (18)0.34158 (12)0.0433 (9)
H461.13650.63480.33390.052*
C510.9060 (3)0.42064 (16)0.32141 (12)0.0267 (6)
C520.8560 (3)0.36297 (16)0.28975 (13)0.0337 (7)
H520.87110.36530.25310.040*
C530.7839 (3)0.30185 (18)0.31140 (17)0.0461 (10)
H530.74930.26300.28950.055*
C540.7629 (4)0.2979 (2)0.36451 (18)0.0509 (11)
H540.71470.25600.37920.061*
C550.8113 (4)0.3542 (2)0.39642 (15)0.0464 (9)
H550.79620.35090.43300.056*
C560.8823 (3)0.41577 (18)0.37543 (12)0.0338 (7)
H560.91480.45460.39770.041*
C611.1917 (3)0.48226 (16)0.32086 (11)0.0266 (6)
C621.2245 (3)0.49623 (18)0.37348 (12)0.0370 (7)
H621.15170.51740.39560.044*
C631.3620 (3)0.4794 (2)0.39327 (14)0.0445 (8)
H631.38250.48800.42910.053*
C641.4698 (4)0.45017 (19)0.36158 (16)0.0490 (9)
H641.56500.43980.37530.059*
C651.4394 (3)0.43590 (18)0.30962 (15)0.0429 (9)
H651.51350.41560.28760.051*
C661.3001 (3)0.45142 (16)0.28976 (13)0.0314 (7)
H661.27910.44060.25420.038*
N1000.6221 (4)0.2438 (2)0.17890 (18)0.0832 (13)
C1000.5542 (4)0.2940 (3)0.16867 (16)0.0563 (11)
C1010.4699 (4)0.3596 (2)0.15297 (16)0.0562 (10)
H1030.45610.35930.11500.084*
H1020.52370.40450.16320.084*
H1010.37340.35910.17020.084*
N2000.3740 (5)0.3076 (2)0.01978 (17)0.0726 (11)
C2000.2643 (5)0.3231 (2)0.00348 (18)0.0559 (11)
C2010.1228 (6)0.3429 (3)−0.0176 (3)0.113 (2)
H2030.12570.3389−0.05580.169*
H2020.09880.3940−0.00770.169*
H2010.04730.3092−0.00380.169*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ru10.01907 (9)0.01683 (8)0.01915 (9)0.00050 (8)−0.00009 (8)0.00030 (9)
N10.0268 (11)0.0175 (10)0.0219 (11)0.0018 (8)0.0020 (11)0.0027 (11)
C10.0260 (13)0.0215 (13)0.0304 (15)0.0033 (10)0.0048 (12)0.0006 (14)
C20.0214 (15)0.0347 (16)0.071 (2)−0.0042 (12)0.0039 (14)−0.0045 (17)
N20.0266 (12)0.0218 (11)0.0176 (11)0.0005 (9)−0.0019 (9)0.0036 (10)
C30.0361 (16)0.0250 (15)0.0192 (14)0.0006 (12)−0.0029 (12)0.0004 (13)
C40.058 (2)0.0217 (15)0.0312 (16)0.0095 (14)−0.0018 (14)−0.0020 (13)
Cl10.0313 (4)0.0206 (3)0.0342 (4)0.0044 (3)0.0042 (3)−0.0014 (3)
Cl20.0233 (3)0.0293 (3)0.0316 (3)−0.0013 (2)−0.0012 (3)−0.0008 (3)
P10.0222 (3)0.0215 (3)0.0195 (3)−0.0017 (3)−0.0008 (3)−0.0003 (3)
P20.0188 (3)0.0210 (3)0.0209 (3)0.0012 (2)0.0001 (3)0.0029 (3)
C110.0292 (15)0.0234 (14)0.0176 (13)−0.0022 (11)−0.0036 (11)0.0013 (12)
C120.0438 (18)0.0250 (15)0.0245 (15)−0.0099 (13)−0.0056 (13)0.0047 (13)
C130.067 (2)0.0201 (14)0.0305 (16)−0.0038 (16)−0.0063 (15)0.0059 (14)
C140.057 (2)0.0299 (17)0.0356 (18)0.0124 (16)−0.0032 (15)0.0021 (16)
C150.0358 (19)0.0411 (19)0.051 (2)0.0057 (15)−0.0049 (15)−0.0085 (18)
C160.0297 (16)0.0246 (15)0.0421 (18)0.0022 (12)−0.0026 (13)−0.0073 (14)
C210.0220 (13)0.0255 (15)0.0229 (13)0.0007 (11)0.0003 (10)−0.0039 (12)
C220.0348 (16)0.0285 (15)0.0278 (15)0.0031 (12)−0.0038 (12)−0.0016 (13)
C230.0430 (18)0.0436 (19)0.0262 (15)0.0044 (15)−0.0070 (13)−0.0106 (15)
C240.0390 (19)0.047 (2)0.0360 (18)−0.0087 (16)−0.0020 (15)−0.0214 (17)
C250.0400 (18)0.0325 (17)0.0377 (18)−0.0120 (14)0.0066 (14)−0.0113 (15)
C260.0353 (17)0.0288 (16)0.0265 (15)−0.0020 (13)0.0026 (12)−0.0057 (13)
C310.0253 (15)0.0366 (17)0.0204 (13)−0.0082 (12)0.0006 (11)0.0014 (13)
C320.0330 (16)0.0366 (18)0.0371 (17)−0.0018 (13)0.0112 (13)−0.0009 (15)
C330.0334 (17)0.052 (2)0.0434 (19)0.0000 (15)0.0108 (14)−0.0045 (18)
C340.0332 (19)0.079 (3)0.0303 (17)−0.0140 (19)0.0083 (14)−0.0010 (19)
C350.043 (2)0.079 (3)0.0277 (17)−0.015 (2)0.0050 (15)0.0214 (19)
C360.0340 (17)0.060 (2)0.0289 (16)−0.0080 (16)−0.0044 (13)0.0162 (17)
C410.0408 (17)0.0272 (15)0.0182 (13)0.0104 (12)−0.0003 (11)0.0039 (12)
C420.050 (2)0.045 (2)0.0290 (16)0.0171 (16)0.0111 (15)0.0141 (16)
C430.085 (3)0.066 (3)0.0331 (19)0.047 (2)0.029 (2)0.023 (2)
C440.153 (5)0.043 (2)0.026 (2)0.044 (3)0.003 (3)−0.0040 (18)
C450.124 (4)0.0335 (18)0.0388 (19)0.017 (3)−0.025 (3)−0.0080 (16)
C460.063 (2)0.0347 (17)0.0319 (16)0.0037 (16)−0.0126 (16)−0.0022 (14)
C510.0171 (13)0.0287 (15)0.0345 (16)0.0022 (11)−0.0015 (11)0.0107 (13)
C520.0248 (14)0.0306 (15)0.0458 (19)0.0031 (11)−0.0007 (14)0.0083 (16)
C530.0288 (17)0.0316 (17)0.078 (3)−0.0054 (13)−0.0054 (17)0.0155 (19)
C540.0262 (17)0.043 (2)0.083 (3)0.0007 (15)0.0091 (18)0.039 (2)
C550.0317 (18)0.056 (2)0.052 (2)0.0063 (16)0.0099 (16)0.028 (2)
C560.0280 (16)0.0389 (18)0.0346 (17)0.0086 (13)0.0062 (13)0.0143 (15)
C610.0203 (13)0.0268 (14)0.0327 (15)−0.0007 (12)−0.0045 (10)0.0073 (14)
C620.0336 (17)0.0422 (18)0.0351 (17)−0.0014 (13)−0.0066 (13)0.0064 (15)
C630.0435 (19)0.0426 (19)0.0474 (19)−0.0066 (17)−0.0238 (15)0.0127 (19)
C640.0262 (17)0.0414 (18)0.079 (3)−0.0039 (14)−0.0204 (17)0.0235 (19)
C650.0259 (15)0.0375 (18)0.065 (2)0.0039 (12)0.0045 (15)0.0139 (18)
C660.0255 (14)0.0282 (14)0.0405 (18)0.0014 (11)0.0018 (12)0.0080 (14)
N1000.064 (2)0.071 (3)0.115 (4)0.008 (2)−0.011 (2)0.041 (3)
C1000.041 (2)0.072 (3)0.056 (2)−0.021 (2)0.0030 (17)0.004 (2)
C1010.039 (2)0.062 (2)0.067 (2)−0.0101 (18)0.0026 (18)−0.014 (2)
N2000.061 (3)0.065 (2)0.092 (3)−0.011 (2)0.001 (2)−0.012 (2)
C2000.047 (3)0.040 (2)0.081 (3)−0.0072 (18)0.009 (2)−0.007 (2)
C2010.079 (4)0.077 (4)0.183 (7)0.013 (3)−0.035 (4)−0.006 (4)

Geometric parameters (Å, °)

Ru1—N22.003 (2)C33—H330.95
Ru1—N12.016 (2)C34—C351.366 (5)
Ru1—P12.3688 (7)C34—H340.95
Ru1—P22.3887 (7)C35—C361.393 (5)
Ru1—Cl22.4139 (7)C35—H350.95
Ru1—Cl12.4308 (7)C36—H360.95
N1—C11.135 (3)C41—C461.391 (4)
C1—C21.463 (4)C41—C421.401 (4)
C2—H2A0.98C42—C431.398 (5)
C2—H2B0.98C42—H420.95
C2—H2C0.98C43—C441.371 (7)
N2—C31.136 (3)C43—H430.95
C3—C41.453 (4)C44—C451.380 (7)
C4—H4A0.98C44—H440.95
C4—H4B0.98C45—C461.378 (5)
C4—H4C0.98C45—H450.95
P1—C111.831 (3)C46—H460.95
P1—C211.835 (3)C51—C521.394 (4)
P1—C311.841 (3)C51—C561.404 (4)
P2—C411.828 (3)C52—C531.396 (4)
P2—C511.834 (3)C52—H520.95
P2—C611.841 (3)C53—C541.376 (6)
C11—C161.389 (4)C53—H530.95
C11—C121.393 (4)C54—C551.374 (6)
C12—C131.380 (4)C54—H540.95
C12—H120.95C55—C561.391 (4)
C13—C141.374 (5)C55—H550.95
C13—H130.95C56—H560.95
C14—C151.390 (5)C61—C661.382 (4)
C14—H140.95C61—C621.404 (4)
C15—C161.392 (4)C62—C631.379 (4)
C15—H150.95C62—H620.95
C16—H160.95C63—C641.375 (5)
C21—C261.391 (4)C63—H630.95
C21—C221.406 (4)C64—C651.384 (5)
C22—C231.389 (4)C64—H640.95
C22—H220.95C65—C661.390 (4)
C23—C241.386 (5)C65—H650.95
C23—H230.95C66—H660.95
C24—C251.367 (4)N100—C1001.125 (5)
C24—H240.95C100—C1011.464 (6)
C25—C261.394 (4)C101—H1030.98
C25—H250.95C101—H1020.98
C26—H260.95C101—H1010.98
C31—C361.392 (4)N200—C2001.114 (5)
C31—C321.396 (4)C200—C2011.437 (7)
C32—C331.393 (4)C201—H2030.98
C32—H320.95C201—H2020.98
C33—C341.377 (5)C201—H2010.98
N2—Ru1—N190.03 (9)C33—C32—H32119.5
N2—Ru1—P190.02 (6)C31—C32—H32119.5
N1—Ru1—P192.15 (7)C34—C33—C32119.7 (3)
N2—Ru1—P289.29 (6)C34—C33—H33120.1
N1—Ru1—P289.55 (7)C32—C33—H33120.1
P1—Ru1—P2178.17 (2)C35—C34—C33120.0 (3)
N2—Ru1—Cl285.16 (7)C35—C34—H34120.0
N1—Ru1—Cl2175.05 (6)C33—C34—H34120.0
P1—Ru1—Cl289.02 (2)C34—C35—C36121.0 (3)
P2—Ru1—Cl289.23 (2)C34—C35—H35119.5
N2—Ru1—Cl1178.93 (7)C36—C35—H35119.5
N1—Ru1—Cl190.99 (6)C31—C36—C35120.1 (3)
P1—Ru1—Cl189.59 (3)C31—C36—H36120.0
P2—Ru1—Cl191.06 (2)C35—C36—H36120.0
Cl2—Ru1—Cl193.83 (2)C46—C41—C42119.3 (3)
C1—N1—Ru1173.9 (2)C46—C41—P2120.5 (2)
N1—C1—C2177.0 (3)C42—C41—P2119.3 (3)
C1—C2—H2A109.5C43—C42—C41119.3 (4)
C1—C2—H2B109.5C43—C42—H42120.3
H2A—C2—H2B109.5C41—C42—H42120.3
C1—C2—H2C109.5C44—C43—C42120.5 (4)
H2A—C2—H2C109.5C44—C43—H43119.8
H2B—C2—H2C109.5C42—C43—H43119.8
C3—N2—Ru1176.7 (2)C43—C44—C45120.2 (4)
N2—C3—C4178.8 (3)C43—C44—H44119.9
C3—C4—H4A109.5C45—C44—H44119.9
C3—C4—H4B109.5C46—C45—C44120.3 (4)
H4A—C4—H4B109.5C46—C45—H45119.8
C3—C4—H4C109.5C44—C45—H45119.8
H4A—C4—H4C109.5C45—C46—C41120.4 (4)
H4B—C4—H4C109.5C45—C46—H46119.8
C11—P1—C21101.26 (12)C41—C46—H46119.8
C11—P1—C31105.82 (14)C52—C51—C56118.5 (3)
C21—P1—C3199.21 (12)C52—C51—P2120.9 (2)
C11—P1—Ru1111.67 (9)C56—C51—P2120.6 (2)
C21—P1—Ru1120.58 (9)C51—C52—C53120.6 (3)
C31—P1—Ru1116.22 (9)C51—C52—H52119.7
C41—P2—C51103.96 (13)C53—C52—H52119.7
C41—P2—C61103.37 (13)C54—C53—C52119.9 (4)
C51—P2—C61100.04 (12)C54—C53—H53120.1
C41—P2—Ru1109.60 (9)C52—C53—H53120.1
C51—P2—Ru1119.54 (10)C55—C54—C53120.5 (3)
C61—P2—Ru1118.29 (9)C55—C54—H54119.8
C16—C11—C12118.4 (3)C53—C54—H54119.8
C16—C11—P1120.5 (2)C54—C55—C56120.4 (3)
C12—C11—P1120.5 (2)C54—C55—H55119.8
C13—C12—C11120.9 (3)C56—C55—H55119.8
C13—C12—H12119.6C55—C56—C51120.1 (3)
C11—C12—H12119.6C55—C56—H56119.9
C14—C13—C12120.8 (3)C51—C56—H56119.9
C14—C13—H13119.6C66—C61—C62118.4 (3)
C12—C13—H13119.6C66—C61—P2119.7 (2)
C13—C14—C15119.1 (3)C62—C61—P2121.8 (2)
C13—C14—H14120.5C63—C62—C61120.4 (3)
C15—C14—H14120.5C63—C62—H62119.8
C14—C15—C16120.4 (3)C61—C62—H62119.8
C14—C15—H15119.8C64—C63—C62120.6 (3)
C16—C15—H15119.8C64—C63—H63119.7
C11—C16—C15120.4 (3)C62—C63—H63119.7
C11—C16—H16119.8C63—C64—C65119.9 (3)
C15—C16—H16119.8C63—C64—H64120.1
C26—C21—C22119.0 (3)C65—C64—H64120.1
C26—C21—P1122.3 (2)C64—C65—C66119.7 (3)
C22—C21—P1118.8 (2)C64—C65—H65120.1
C23—C22—C21120.4 (3)C66—C65—H65120.1
C23—C22—H22119.8C61—C66—C65121.0 (3)
C21—C22—H22119.8C61—C66—H66119.5
C24—C23—C22120.0 (3)C65—C66—H66119.5
C24—C23—H23120.0N100—C100—C101177.2 (5)
C22—C23—H23120.0C100—C101—H103109.5
C25—C24—C23119.6 (3)C100—C101—H102109.5
C25—C24—H24120.2H103—C101—H102109.5
C23—C24—H24120.2C100—C101—H101109.5
C24—C25—C26121.7 (3)H103—C101—H101109.5
C24—C25—H25119.2H102—C101—H101109.5
C26—C25—H25119.2N200—C200—C201179.8 (6)
C21—C26—C25119.4 (3)C200—C201—H203109.5
C21—C26—H26120.3C200—C201—H202109.5
C25—C26—H26120.3H203—C201—H202109.5
C36—C31—C32118.3 (3)C200—C201—H201109.5
C36—C31—P1125.2 (2)H203—C201—H201109.5
C32—C31—P1116.4 (2)H202—C201—H201109.5
C33—C32—C31120.9 (3)
N2—Ru1—P1—C11−12.66 (12)Ru1—P1—C31—C36−133.4 (2)
N1—Ru1—P1—C11−102.69 (11)C11—P1—C31—C32176.5 (2)
Cl2—Ru1—P1—C1172.50 (10)C21—P1—C31—C32−78.9 (2)
Cl1—Ru1—P1—C11166.34 (10)Ru1—P1—C31—C3252.0 (3)
N2—Ru1—P1—C21−131.27 (12)C36—C31—C32—C33−1.2 (5)
N1—Ru1—P1—C21138.70 (11)P1—C31—C32—C33173.9 (2)
Cl2—Ru1—P1—C21−46.11 (10)C31—C32—C33—C340.8 (5)
Cl1—Ru1—P1—C2147.73 (10)C32—C33—C34—C350.8 (5)
N2—Ru1—P1—C31108.85 (13)C33—C34—C35—C36−2.0 (6)
N1—Ru1—P1—C3118.82 (13)C32—C31—C36—C350.0 (5)
Cl2—Ru1—P1—C31−165.99 (11)P1—C31—C36—C35−174.6 (3)
Cl1—Ru1—P1—C31−72.16 (11)C34—C35—C36—C311.6 (5)
N2—Ru1—P2—C410.84 (12)C51—P2—C41—C46147.0 (2)
N1—Ru1—P2—C4190.87 (12)C61—P2—C41—C4642.9 (3)
Cl2—Ru1—P2—C41−84.33 (11)Ru1—P2—C41—C46−84.1 (2)
Cl1—Ru1—P2—C41−178.15 (11)C51—P2—C41—C42−44.1 (3)
N2—Ru1—P2—C51120.59 (12)C61—P2—C41—C42−148.2 (2)
N1—Ru1—P2—C51−149.38 (12)Ru1—P2—C41—C4284.8 (2)
Cl2—Ru1—P2—C5135.42 (10)C46—C41—C42—C43−2.3 (4)
Cl1—Ru1—P2—C51−58.40 (10)P2—C41—C42—C43−171.3 (2)
N2—Ru1—P2—C61−117.22 (13)C41—C42—C43—C441.6 (5)
N1—Ru1—P2—C61−27.19 (12)C42—C43—C44—C45−0.3 (6)
Cl2—Ru1—P2—C61157.61 (11)C43—C44—C45—C46−0.3 (6)
Cl1—Ru1—P2—C6163.79 (11)C44—C45—C46—C41−0.5 (5)
C21—P1—C11—C1632.4 (3)C42—C41—C46—C451.8 (4)
C31—P1—C11—C16135.5 (2)P2—C41—C46—C45170.7 (2)
Ru1—P1—C11—C16−97.1 (2)C41—P2—C51—C52142.5 (2)
C21—P1—C11—C12−156.8 (2)C61—P2—C51—C52−110.9 (2)
C31—P1—C11—C12−53.8 (3)Ru1—P2—C51—C5219.9 (3)
Ru1—P1—C11—C1273.6 (2)C41—P2—C51—C56−39.8 (3)
C16—C11—C12—C13−1.4 (4)C61—P2—C51—C5666.8 (3)
P1—C11—C12—C13−172.3 (2)Ru1—P2—C51—C56−162.40 (19)
C11—C12—C13—C140.5 (5)C56—C51—C52—C530.0 (4)
C12—C13—C14—C150.4 (5)P2—C51—C52—C53177.7 (2)
C13—C14—C15—C16−0.4 (5)C51—C52—C53—C54−0.6 (5)
C12—C11—C16—C151.4 (5)C52—C53—C54—C550.6 (5)
P1—C11—C16—C15172.3 (3)C53—C54—C55—C56−0.1 (5)
C14—C15—C16—C11−0.5 (5)C54—C55—C56—C51−0.5 (5)
C11—P1—C21—C26−125.0 (2)C52—C51—C56—C550.5 (4)
C31—P1—C21—C26126.7 (2)P2—C51—C56—C55−177.2 (2)
Ru1—P1—C21—C26−1.3 (3)C41—P2—C61—C66−150.7 (2)
C11—P1—C21—C2254.7 (2)C51—P2—C61—C66102.2 (2)
C31—P1—C21—C22−53.6 (2)Ru1—P2—C61—C66−29.4 (3)
Ru1—P1—C21—C22178.40 (18)C41—P2—C61—C6232.4 (3)
C26—C21—C22—C231.2 (4)C51—P2—C61—C62−74.7 (3)
P1—C21—C22—C23−178.5 (2)Ru1—P2—C61—C62153.7 (2)
C21—C22—C23—C24−0.6 (5)C66—C61—C62—C630.0 (5)
C22—C23—C24—C250.3 (5)P2—C61—C62—C63176.9 (2)
C23—C24—C25—C26−0.5 (5)C61—C62—C63—C641.4 (5)
C22—C21—C26—C25−1.3 (4)C62—C63—C64—C65−1.5 (5)
P1—C21—C26—C25178.3 (2)C63—C64—C65—C660.2 (5)
C24—C25—C26—C211.0 (5)C62—C61—C66—C65−1.3 (4)
C11—P1—C31—C36−8.8 (3)P2—C61—C66—C65−178.3 (2)
C21—P1—C31—C3695.7 (3)C64—C65—C66—C611.2 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4B···Cl1i0.982.683.560 (3)149
C101—H101···Cl1ii0.982.803.698 (4)153
C2—H2C···Cl2iii0.982.573.544 (3)175
C101—H102···Cl20.982.623.554 (4)158
C2—H2A···N100i0.982.603.519 (5)155
C101—H103···N2000.982.723.645 (6)158
C201—H201···N200iv0.982.663.526 (7)148
C64—H64···Cg1iii0.952.963.715 (4)138

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) x−1/2, −y+1/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2537).

References

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  • Caulton, K. G. (1974). J. Am. Chem. Soc.96, 3005–3006.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gilbert, J. D. & Wilkinson, G. (1969). J. Chem. Soc. A, pp. 1749–1753.
  • Hallman, P. S., Stephenson, T. A. & Wilkinson, G. (1970). Inorg. Synth.12, 237–240.
  • Sheldrick, G. M. (2000). SADABS (Version 2.10) and SHELXTL (Version 6.14). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Stephenson, T. A. & Wilkinson, G. (1966). J. Inorg. Nucl. Chem.28, 945–956.

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