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The title compound, [Ru2Fe2(C5H5)2(C9H11N2S)2(CO)4]·CH2Cl2 or [FcC(Me)=NNHC(S)NHMe]2Ru2(CO)4·CH2Cl2 (where Fc = ferrocenyl), was isolated from the reaction of FcC(Me)=NNHC(S)NHMe and Ru3(CO)12. In the dimeric mol­ecule, which lies on a crystallographic twofold axis, the two symmetry-related Ru atoms are in distorted octahedral coordination environments with two bridging S atoms in the equatorial plane and Ru—S bond distances of 2.514 (2) and 2.451 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012164/lh6209sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012164/lh6209Isup2.hkl
Contains datablock I

CCDC reference: 242282

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.066
  • wR factor = 0.158
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.167 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.17
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.28 PLAT128_ALERT_4_C Non-standard setting of Space group P2/c .... P2/n PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis[µ-(S)-1-(1-ferrocenylethylidene)-4-methylthiosemicarbazide- κ2C2,N,S:S]bis[dicarbonylruthenium] dichlormethane solvate top
Crystal data top
[Ru2Fe2(C5H5)2(C9H11N2S)2(CO)4]·CH2Cl2F(000) = 1024
Mr = 1027.54Dx = 1.818 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 1101 reflections
a = 7.8664 (12) Åθ = 5.3–43.7°
b = 10.7140 (16) ŵ = 1.85 mm1
c = 22.582 (3) ÅT = 293 K
β = 99.569 (3)°Plate, dark red
V = 1876.7 (5) Å30.40 × 0.19 × 0.05 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer
4307 independent reflections
Radiation source: fine-focus sealed tube2226 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.167
φ and ω scansθmax = 28.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 910
Tmin = 0.629, Tmax = 0.910k = 1514
10883 measured reflectionsl = 2929
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 0.86 w = 1/[σ2(Fo2) + (0.0308P)2]
where P = (Fo2 + 2Fc2)/3
4307 reflections(Δ/σ)max = 0.001
233 parametersΔρmax = 1.60 e Å3
0 restraintsΔρmin = 0.70 e Å3
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)
Ru0.29320 (9)0.10322 (5)0.67187 (3)0.0343 (2)
Fe0.18259 (16)0.25728 (10)0.51621 (5)0.0384 (3)
S0.4606 (3)0.09984 (18)0.77362 (9)0.0392 (5)
O10.2072 (10)0.1644 (6)0.6364 (3)0.080 (2)
O20.6080 (9)0.0827 (6)0.6139 (3)0.0672 (19)
N10.4601 (8)0.3399 (6)0.7333 (3)0.0357 (15)
H1A0.49090.41700.73540.043*
N20.6433 (9)0.2952 (6)0.8200 (3)0.0443 (17)
H2A0.69160.23850.84400.053*
N30.3404 (8)0.2951 (6)0.6862 (3)0.0380 (16)
C10.2389 (12)0.0652 (8)0.6508 (4)0.052 (2)
C20.4841 (13)0.0931 (7)0.6342 (4)0.044 (2)
C30.4363 (13)0.2873 (10)0.5060 (5)0.067 (3)
H3A0.53350.30710.53770.081*
C40.3240 (13)0.3736 (9)0.4710 (4)0.057 (3)
H4A0.32980.46480.47460.068*
C50.2055 (13)0.3063 (8)0.4302 (4)0.054 (2)
H5A0.11370.34310.40070.065*
C60.2370 (15)0.1763 (9)0.4384 (4)0.067 (3)
H6A0.17430.10790.41560.081*
C70.3800 (15)0.1661 (9)0.4851 (4)0.069 (3)
H7A0.43180.08740.50120.082*
C80.0153 (11)0.3634 (7)0.5534 (3)0.042 (2)
H8A0.01010.45200.54530.050*
C90.0709 (12)0.2625 (8)0.5231 (4)0.050 (2)
H9A0.16670.26820.48940.060*
C100.0003 (11)0.1503 (8)0.5499 (3)0.043 (2)
H10A0.03560.06600.53650.051*
C110.1361 (10)0.1792 (7)0.5981 (3)0.0345 (18)
C120.1435 (10)0.3143 (7)0.5993 (3)0.0371 (19)
C130.2657 (10)0.3744 (7)0.6458 (3)0.0353 (19)
C140.2953 (11)0.5119 (7)0.6497 (3)0.045 (2)
H14A0.41660.52820.65970.068*
H14B0.23720.54630.68010.068*
H14C0.25100.54950.61160.068*
C150.5233 (11)0.2603 (7)0.7741 (3)0.0382 (19)
C160.6965 (12)0.4238 (7)0.8314 (4)0.053 (2)
H16A0.78670.42740.86560.079*
H16B0.59990.47230.83910.079*
H16C0.73790.45680.79690.079*
Cl0.5650 (6)0.7525 (3)0.7498 (3)0.163 (2)
C170.75000.825 (2)0.75000.244 (18)
H17A0.76630.87930.78490.292*0.50
H17B0.73370.87930.71510.292*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.0389 (4)0.0225 (3)0.0402 (4)0.0012 (3)0.0028 (3)0.0031 (3)
Fe0.0413 (8)0.0327 (6)0.0426 (7)0.0048 (5)0.0106 (6)0.0001 (5)
S0.0412 (13)0.0292 (10)0.0449 (11)0.0041 (9)0.0010 (9)0.0023 (9)
O10.094 (6)0.031 (4)0.112 (5)0.018 (4)0.010 (5)0.029 (4)
O20.045 (4)0.084 (5)0.075 (4)0.015 (4)0.015 (4)0.018 (4)
N10.035 (4)0.022 (3)0.050 (4)0.003 (3)0.006 (3)0.007 (3)
N20.031 (4)0.054 (5)0.045 (4)0.001 (3)0.002 (3)0.008 (3)
N30.037 (4)0.034 (4)0.043 (4)0.006 (3)0.006 (3)0.007 (3)
C10.045 (6)0.039 (5)0.066 (6)0.007 (4)0.005 (5)0.009 (4)
C20.060 (6)0.025 (4)0.046 (5)0.001 (4)0.002 (4)0.004 (4)
C30.044 (6)0.082 (8)0.082 (7)0.012 (6)0.026 (6)0.007 (6)
C40.056 (7)0.050 (6)0.072 (6)0.000 (5)0.031 (5)0.008 (5)
C50.062 (7)0.044 (5)0.060 (6)0.000 (5)0.024 (5)0.011 (5)
C60.108 (10)0.054 (6)0.043 (6)0.022 (6)0.022 (6)0.004 (5)
C70.095 (9)0.056 (6)0.062 (6)0.042 (6)0.036 (6)0.016 (5)
C80.041 (5)0.039 (5)0.046 (5)0.015 (4)0.014 (4)0.003 (4)
C90.043 (6)0.064 (6)0.041 (5)0.001 (5)0.003 (4)0.002 (4)
C100.037 (5)0.047 (5)0.046 (5)0.003 (4)0.008 (4)0.002 (4)
C110.029 (5)0.028 (4)0.046 (5)0.002 (3)0.006 (4)0.005 (4)
C120.037 (5)0.035 (4)0.041 (5)0.005 (4)0.009 (4)0.004 (4)
C130.039 (5)0.030 (4)0.039 (4)0.002 (4)0.013 (4)0.005 (4)
C140.050 (6)0.028 (4)0.056 (5)0.000 (4)0.005 (4)0.006 (4)
C150.030 (5)0.041 (5)0.044 (5)0.005 (4)0.009 (4)0.007 (4)
C160.054 (6)0.051 (6)0.056 (5)0.026 (5)0.015 (5)0.013 (5)
Cl0.119 (4)0.088 (3)0.267 (5)0.017 (2)0.016 (4)0.006 (3)
C170.16 (3)0.068 (15)0.54 (5)0.0000.18 (3)0.000
Geometric parameters (Å, º) top
Ru—C21.847 (10)C3—C71.426 (13)
Ru—C11.897 (9)C3—H3A0.9800
Ru—C112.069 (7)C4—C51.398 (12)
Ru—N32.105 (6)C4—H4A0.9800
Ru—S2.451 (2)C5—C61.421 (12)
Ru—Si2.514 (2)C5—H5A0.9800
Ru—Rui3.7027 (13)C6—C71.413 (14)
Fe—C82.024 (8)C6—H6A0.9800
Fe—C92.027 (9)C7—H7A0.9800
Fe—C122.044 (7)C8—C91.393 (11)
Fe—C52.049 (8)C8—C121.422 (10)
Fe—C42.052 (9)C8—H8A0.9800
Fe—C72.054 (9)C9—C101.419 (11)
Fe—C62.067 (8)C9—H9A0.9800
Fe—C32.072 (10)C10—C111.425 (10)
Fe—C102.076 (8)C10—H10A0.9800
Fe—C112.117 (7)C11—C121.449 (10)
S—C151.788 (8)C12—C131.452 (10)
S—Rui2.514 (2)C13—C141.491 (10)
O1—C11.126 (9)C14—H14A0.9600
O2—C21.150 (10)C14—H14B0.9600
N1—C151.292 (9)C14—H14C0.9600
N1—N31.385 (8)C16—H16A0.9600
N1—H1A0.8600C16—H16B0.9600
N2—C151.334 (9)C16—H16C0.9600
N2—C161.451 (9)Cl—C171.650 (10)
N2—H2A0.8600C17—Clii1.650 (10)
N3—C131.312 (9)C17—H17A0.9700
C3—C41.424 (12)C17—H17B0.9700
C2—Ru—C189.7 (4)C7—C3—Fe69.1 (6)
C2—Ru—C1194.3 (3)C4—C3—H3A126.9
C1—Ru—C1195.3 (3)C7—C3—H3A126.9
C2—Ru—N389.5 (3)Fe—C3—H3A126.9
C1—Ru—N3174.0 (3)C5—C4—C3108.3 (9)
C11—Ru—N378.8 (3)C5—C4—Fe69.9 (5)
C2—Ru—S94.5 (3)C3—C4—Fe70.6 (5)
C1—Ru—S106.5 (3)C5—C4—H4A125.8
C11—Ru—S156.4 (2)C3—C4—H4A125.8
N3—Ru—S79.45 (18)Fe—C4—H4A125.8
C2—Ru—Si175.4 (2)C4—C5—C6109.7 (9)
C1—Ru—Si86.9 (3)C4—C5—Fe70.2 (5)
C11—Ru—Si89.0 (2)C6—C5—Fe70.5 (5)
N3—Ru—Si94.18 (18)C4—C5—H5A125.2
S—Ru—Si83.53 (8)C6—C5—H5A125.2
C2—Ru—Rui136.9 (3)Fe—C5—H5A125.2
C1—Ru—Rui99.8 (3)C7—C6—C5105.9 (9)
C11—Ru—Rui126.0 (2)C7—C6—Fe69.5 (5)
N3—Ru—Rui84.79 (16)C5—C6—Fe69.1 (5)
S—Ru—Rui42.43 (5)C7—C6—H6A127.1
Si—Ru—Rui41.13 (5)C5—C6—H6A127.1
C8—Fe—C940.2 (3)Fe—C6—H6A127.1
C8—Fe—C1240.9 (3)C6—C7—C3110.0 (8)
C9—Fe—C1267.7 (3)C6—C7—Fe70.4 (5)
C8—Fe—C5114.5 (3)C3—C7—Fe70.5 (5)
C9—Fe—C5108.0 (4)C6—C7—H7A125.0
C12—Fe—C5147.5 (3)C3—C7—H7A125.0
C8—Fe—C4108.0 (4)Fe—C7—H7A125.0
C9—Fe—C4130.0 (4)C9—C8—C12107.3 (7)
C12—Fe—C4116.9 (3)C9—C8—Fe70.0 (5)
C5—Fe—C439.9 (3)C12—C8—Fe70.3 (4)
C8—Fe—C7171.6 (4)C9—C8—H8A126.3
C9—Fe—C7148.1 (4)C12—C8—H8A126.3
C12—Fe—C7133.9 (4)Fe—C8—H8A126.3
C5—Fe—C766.9 (4)C8—C9—C10108.8 (7)
C4—Fe—C767.4 (4)C8—C9—Fe69.8 (5)
C8—Fe—C6146.0 (4)C10—C9—Fe71.7 (5)
C9—Fe—C6115.0 (4)C8—C9—H9A125.6
C12—Fe—C6171.7 (3)C10—C9—H9A125.6
C5—Fe—C640.4 (3)Fe—C9—H9A125.6
C4—Fe—C668.0 (4)C9—C10—C11109.5 (7)
C7—Fe—C640.1 (4)C9—C10—Fe67.9 (5)
C8—Fe—C3131.6 (4)C11—C10—Fe71.6 (5)
C9—Fe—C3169.3 (4)C9—C10—H10A125.2
C12—Fe—C3110.5 (4)C11—C10—H10A125.2
C5—Fe—C367.4 (4)Fe—C10—H10A125.2
C4—Fe—C340.4 (4)C10—C11—C12104.7 (7)
C7—Fe—C340.4 (4)C10—C11—Ru143.2 (6)
C6—Fe—C368.3 (4)C12—C11—Ru111.2 (5)
C8—Fe—C1067.8 (3)C10—C11—Fe68.6 (4)
C9—Fe—C1040.4 (3)C12—C11—Fe67.0 (4)
C12—Fe—C1067.0 (3)Ru—C11—Fe133.8 (4)
C5—Fe—C10131.6 (4)C8—C12—C11109.6 (7)
C4—Fe—C10169.2 (4)C8—C12—C13131.9 (7)
C7—Fe—C10118.0 (4)C11—C12—C13118.5 (7)
C6—Fe—C10109.5 (4)C8—C12—Fe68.8 (4)
C3—Fe—C10149.7 (4)C11—C12—Fe72.3 (4)
C8—Fe—C1169.0 (3)C13—C12—Fe127.9 (6)
C9—Fe—C1168.2 (3)N3—C13—C12112.4 (7)
C12—Fe—C1140.7 (3)N3—C13—C14123.5 (7)
C5—Fe—C11170.1 (3)C12—C13—C14123.9 (7)
C4—Fe—C11149.5 (3)C13—C14—H14A109.5
C7—Fe—C11111.1 (3)C13—C14—H14B109.5
C6—Fe—C11131.8 (3)H14A—C14—H14B109.5
C3—Fe—C11117.9 (4)C13—C14—H14C109.5
C10—Fe—C1139.7 (3)H14A—C14—H14C109.5
C15—S—Ru95.5 (3)H14B—C14—H14C109.5
C15—S—Rui103.0 (3)N1—C15—N2120.5 (7)
Ru—S—Rui96.44 (7)N1—C15—S123.9 (6)
C15—N1—N3116.8 (6)N2—C15—S115.7 (6)
C15—N1—H1A121.6N2—C16—H16A109.5
N3—N1—H1A121.6N2—C16—H16B109.5
C15—N2—C16123.4 (7)H16A—C16—H16B109.5
C15—N2—H2A118.3N2—C16—H16C109.5
C16—N2—H2A118.3H16A—C16—H16C109.5
C13—N3—N1118.6 (6)H16B—C16—H16C109.5
C13—N3—Ru118.6 (5)Cl—C17—Clii123.7 (14)
N1—N3—Ru122.5 (5)Cl—C17—H17A106.4
O1—C1—Ru177.7 (9)Clii—C17—H17A106.4
O2—C2—Ru175.7 (7)Cl—C17—H17B106.4
C4—C3—C7106.2 (9)Clii—C17—H17B106.4
C4—C3—Fe69.0 (5)H17A—C17—H17B106.5
Symmetry codes: (i) x+1/2, y, z+3/2; (ii) x+3/2, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2ii0.862.383.205 (9)160
Symmetry code: (ii) x+3/2, y, z+3/2.
 

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