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The mol­ecular structure of the centrosymmetric title compound, [Fe2(C5H5)2(C24H18)], represents a new application of cross-metathesis for the preparation of functionalized olefins containing two organometallic groups. The two benzene and attached cyclopentadienyl (Cp) rings and the double bond are almost coplanar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048197/hg2127sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048197/hg2127Isup2.hkl
Contains datablock I

CCDC reference: 629901

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.061
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2004); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please provide; software used to prepare material for publication: CrystalStructure.

1,2-bis(4-ferrocenylphenyl)ethene top
Crystal data top
[(C5H5)2Fe2(C24H18)]F(000) = 568
Mr = 548.26Dx = 1.477 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 3251 reflections
a = 12.452 (2) Åθ = 1.7–27.9°
b = 8.1688 (14) ŵ = 1.20 mm1
c = 12.5419 (18) ÅT = 113 K
β = 104.880 (9)°Platelet, orange
V = 1233.0 (3) Å30.20 × 0.16 × 0.02 mm
Z = 2
Data collection top
Rigaku Saturn
diffractometer
2424 independent reflections
Radiation source: rotating anode2113 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.066
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.7°
ω scansh = 1515
Absorption correction: multi-scan
(Jacobson, 1998)
k = 910
Tmin = 0.796, Tmax = 0.976l = 1515
12668 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0721P)2 + 1.1009P]
where P = (Fo2 + 2Fc2)/3
2424 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.90 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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*/Ueq
Fe10.32776 (4)0.17867 (7)0.08230 (4)0.0256 (2)
C10.4662 (3)0.3233 (5)0.0886 (3)0.0335 (10)
H10.51410.31700.04080.040*
C20.4778 (3)0.2333 (5)0.1894 (3)0.0321 (9)
H20.53460.15620.21960.038*
C30.3895 (3)0.2797 (5)0.2359 (3)0.0307 (9)
H30.37800.23930.30310.037*
C40.3208 (3)0.3976 (5)0.1651 (3)0.0322 (9)
H40.25600.44810.17680.039*
C50.3678 (4)0.4256 (5)0.0729 (4)0.0386 (10)
H50.33970.49780.01290.046*
C60.2390 (3)0.0939 (5)0.0698 (3)0.0315 (9)
H60.22800.14930.13840.038*
C70.3288 (3)0.0141 (5)0.0232 (3)0.0294 (9)
H70.38800.04270.05460.035*
C80.3134 (3)0.0722 (5)0.0806 (3)0.0280 (9)
H80.36080.14640.12920.034*
C90.2140 (3)0.0013 (4)0.0983 (3)0.0260 (8)
C100.1681 (3)0.1050 (5)0.0037 (3)0.0300 (9)
H100.10250.16910.00760.036*
C110.1672 (3)0.0155 (4)0.1960 (3)0.0238 (8)
C120.0816 (3)0.0891 (5)0.2094 (3)0.0312 (9)
H120.05230.16810.15400.037*
C130.0388 (3)0.0805 (5)0.3013 (3)0.0318 (9)
H130.01880.15330.30750.038*
C140.0799 (3)0.0353 (5)0.3855 (3)0.0244 (8)
C150.1620 (3)0.1440 (5)0.3706 (3)0.0271 (8)
H150.18860.22650.42430.033*
C160.2060 (3)0.1340 (5)0.2783 (3)0.0276 (8)
H160.26260.20810.27130.033*
C170.0384 (3)0.0462 (5)0.4865 (3)0.0266 (8)
H170.07080.12910.53780.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0289 (4)0.0273 (4)0.0215 (4)0.0007 (2)0.0080 (2)0.0006 (2)
C10.033 (2)0.034 (2)0.037 (2)0.0074 (17)0.0147 (18)0.0011 (18)
C20.032 (2)0.032 (2)0.032 (2)0.0018 (18)0.0082 (17)0.0053 (18)
C30.034 (2)0.036 (2)0.023 (2)0.0061 (18)0.0069 (16)0.0078 (17)
C40.035 (2)0.028 (2)0.035 (2)0.0003 (17)0.0115 (18)0.0097 (18)
C50.048 (3)0.028 (2)0.037 (2)0.012 (2)0.006 (2)0.0062 (19)
C60.036 (2)0.038 (2)0.0206 (19)0.0057 (19)0.0083 (16)0.0022 (17)
C70.032 (2)0.034 (2)0.025 (2)0.0050 (17)0.0127 (16)0.0086 (17)
C80.031 (2)0.027 (2)0.027 (2)0.0002 (16)0.0094 (16)0.0017 (16)
C90.0298 (19)0.0236 (19)0.0251 (19)0.0025 (16)0.0082 (15)0.0023 (16)
C100.036 (2)0.032 (2)0.0221 (19)0.0021 (17)0.0064 (16)0.0019 (17)
C110.0246 (18)0.0257 (19)0.0210 (18)0.0050 (15)0.0059 (14)0.0018 (15)
C120.037 (2)0.032 (2)0.028 (2)0.0077 (18)0.0130 (17)0.0075 (17)
C130.033 (2)0.036 (2)0.027 (2)0.0098 (18)0.0097 (17)0.0034 (18)
C140.0277 (19)0.0249 (19)0.0216 (18)0.0055 (15)0.0082 (15)0.0002 (15)
C150.032 (2)0.028 (2)0.0222 (19)0.0003 (16)0.0077 (15)0.0046 (16)
C160.028 (2)0.028 (2)0.028 (2)0.0047 (16)0.0097 (16)0.0007 (17)
C170.034 (2)0.028 (2)0.0187 (18)0.0035 (16)0.0079 (15)0.0002 (15)
Geometric parameters (Å, º) top
Fe1—C12.075 (4)C11—C161.407 (5)
Fe1—C22.051 (4)C12—C131.390 (5)
Fe1—C32.055 (4)C13—C141.412 (5)
Fe1—C42.081 (4)C14—C151.402 (6)
Fe1—C52.088 (4)C14—C171.489 (5)
Fe1—C62.063 (4)C15—C161.405 (5)
Fe1—C72.059 (4)C17—C17i1.329 (6)
Fe1—C82.057 (4)C1—H10.9494
Fe1—C92.072 (4)C2—H20.9501
Fe1—C102.069 (4)C3—H30.9496
C1—C21.437 (5)C4—H40.9506
C1—C51.454 (6)C5—H50.9494
C2—C31.422 (5)C6—H60.9504
C3—C41.434 (6)C7—H70.9498
C4—C51.442 (6)C8—H80.9500
C6—C71.426 (6)C10—H100.9498
C6—C101.434 (5)C12—H120.9498
C7—C81.444 (5)C13—H130.9501
C8—C91.443 (5)C15—H150.9502
C9—C101.450 (5)C16—H160.9501
C9—C111.492 (5)C17—H170.9497
C11—C121.409 (5)
C1—Fe1—C240.78 (15)Fe1—C7—C669.9 (2)
C1—Fe1—C368.19 (15)Fe1—C7—C869.4 (2)
C1—Fe1—C468.42 (15)C6—C7—C8107.5 (3)
C1—Fe1—C540.89 (18)Fe1—C8—C769.5 (2)
C1—Fe1—C6117.96 (15)Fe1—C8—C970.1 (2)
C1—Fe1—C7108.53 (15)C7—C8—C9108.6 (3)
C1—Fe1—C8129.57 (16)Fe1—C9—C869.0 (2)
C1—Fe1—C9167.61 (15)Fe1—C9—C1069.4 (2)
C1—Fe1—C10150.61 (15)Fe1—C9—C11124.4 (2)
C2—Fe1—C340.53 (15)C8—C9—C10106.9 (3)
C2—Fe1—C468.52 (15)C8—C9—C11128.3 (3)
C2—Fe1—C568.67 (18)C10—C9—C11124.8 (3)
C2—Fe1—C6149.35 (15)Fe1—C10—C669.5 (2)
C2—Fe1—C7115.62 (16)Fe1—C10—C969.6 (2)
C2—Fe1—C8106.61 (16)C6—C10—C9108.1 (3)
C2—Fe1—C9128.27 (15)C9—C11—C12120.6 (3)
C2—Fe1—C10167.92 (15)C9—C11—C16122.2 (3)
C3—Fe1—C440.58 (15)C12—C11—C16117.2 (3)
C3—Fe1—C568.15 (17)C11—C12—C13122.1 (4)
C3—Fe1—C6169.79 (16)C12—C13—C14120.8 (4)
C3—Fe1—C7147.89 (16)C13—C14—C15117.5 (3)
C3—Fe1—C8114.87 (15)C13—C14—C17122.6 (3)
C3—Fe1—C9106.89 (15)C15—C14—C17120.0 (3)
C3—Fe1—C10130.24 (15)C14—C15—C16121.7 (4)
C4—Fe1—C540.47 (17)C11—C16—C15120.8 (4)
C4—Fe1—C6131.97 (15)C14—C17—C17i127.8 (4)
C4—Fe1—C7170.36 (15)Fe1—C1—H1126.56
C4—Fe1—C8147.87 (15)C2—C1—H1126.17
C4—Fe1—C9115.82 (15)C5—C1—H1126.14
C4—Fe1—C10109.25 (15)Fe1—C2—H2125.21
C5—Fe1—C6110.54 (18)C1—C2—H2125.88
C5—Fe1—C7131.41 (17)C3—C2—H2126.02
C5—Fe1—C8169.48 (18)Fe1—C3—H3125.95
C5—Fe1—C9149.32 (17)C2—C3—H3125.46
C5—Fe1—C10117.92 (18)C4—C3—H3125.51
C6—Fe1—C740.49 (15)Fe1—C4—H4126.57
C6—Fe1—C868.38 (15)C3—C4—H4126.21
C6—Fe1—C968.75 (15)C5—C4—H4126.18
C6—Fe1—C1040.60 (15)Fe1—C5—H5126.87
C7—Fe1—C841.08 (15)C1—C5—H5126.20
C7—Fe1—C969.19 (15)C4—C5—H5126.25
C7—Fe1—C1068.60 (15)Fe1—C6—H6126.56
C8—Fe1—C940.92 (15)C7—C6—H6125.52
C8—Fe1—C1068.58 (16)C10—C6—H6125.63
C9—Fe1—C1041.01 (15)Fe1—C7—H7126.03
Fe1—C1—C268.7 (2)C6—C7—H7126.33
Fe1—C1—C570.1 (2)C8—C7—H7126.15
C2—C1—C5107.7 (3)Fe1—C8—H8126.23
Fe1—C2—C170.5 (2)C7—C8—H8125.71
Fe1—C2—C369.9 (2)C9—C8—H8125.65
C1—C2—C3108.1 (3)Fe1—C10—H10126.52
Fe1—C3—C269.6 (2)C6—C10—H10125.94
Fe1—C3—C470.7 (2)C9—C10—H10125.96
C2—C3—C4109.0 (3)C11—C12—H12119.00
Fe1—C4—C368.7 (2)C13—C12—H12118.93
Fe1—C4—C570.0 (2)C12—C13—H13119.63
C3—C4—C5107.6 (3)C14—C13—H13119.62
Fe1—C5—C169.0 (2)C14—C15—H15119.21
Fe1—C5—C469.5 (2)C16—C15—H15119.12
C1—C5—C4107.6 (4)C11—C16—H16119.58
Fe1—C6—C769.6 (2)C15—C16—H16119.65
Fe1—C6—C1069.9 (2)C14—C17—H17116.06
C7—C6—C10108.8 (3)C17i—C17—H17116.15
C2—Fe1—C1—C5119.2 (3)C2—Fe1—C8—C9130.0 (2)
C3—Fe1—C1—C237.9 (2)C3—Fe1—C8—C7152.8 (2)
C3—Fe1—C1—C581.4 (3)C3—Fe1—C8—C987.4 (2)
C4—Fe1—C1—C281.7 (2)C4—Fe1—C8—C7174.0 (3)
C4—Fe1—C1—C537.5 (2)C4—Fe1—C8—C954.1 (4)
C5—Fe1—C1—C2119.2 (3)C6—Fe1—C8—C737.8 (2)
C6—Fe1—C1—C2151.1 (2)C6—Fe1—C8—C982.1 (2)
C6—Fe1—C1—C589.6 (3)C7—Fe1—C8—C9119.9 (3)
C7—Fe1—C1—C2108.0 (2)C9—Fe1—C8—C7119.9 (3)
C7—Fe1—C1—C5132.7 (3)C10—Fe1—C8—C781.6 (2)
C8—Fe1—C1—C267.0 (3)C10—Fe1—C8—C938.3 (2)
C8—Fe1—C1—C5173.8 (2)C2—Fe1—C9—C869.2 (3)
C10—Fe1—C1—C2172.9 (3)C2—Fe1—C9—C10172.3 (2)
C10—Fe1—C1—C553.6 (4)C2—Fe1—C9—C1153.5 (4)
C1—Fe1—C2—C3118.7 (3)C3—Fe1—C9—C8108.7 (2)
C3—Fe1—C2—C1118.7 (3)C3—Fe1—C9—C10132.8 (2)
C4—Fe1—C2—C181.4 (2)C3—Fe1—C9—C1114.0 (3)
C4—Fe1—C2—C337.3 (2)C4—Fe1—C9—C8151.4 (2)
C5—Fe1—C2—C137.8 (2)C4—Fe1—C9—C1090.1 (2)
C5—Fe1—C2—C380.9 (3)C4—Fe1—C9—C1128.7 (3)
C6—Fe1—C2—C156.8 (4)C5—Fe1—C9—C8175.8 (3)
C6—Fe1—C2—C3175.5 (3)C5—Fe1—C9—C1057.3 (4)
C7—Fe1—C2—C189.1 (3)C5—Fe1—C9—C1161.4 (5)
C7—Fe1—C2—C3152.2 (2)C6—Fe1—C9—C881.1 (2)
C8—Fe1—C2—C1132.2 (2)C6—Fe1—C9—C1037.4 (2)
C8—Fe1—C2—C3109.1 (2)C6—Fe1—C9—C11156.2 (3)
C9—Fe1—C2—C1172.0 (2)C7—Fe1—C9—C837.6 (2)
C9—Fe1—C2—C369.3 (3)C7—Fe1—C9—C1080.9 (2)
C1—Fe1—C3—C238.1 (2)C7—Fe1—C9—C11160.3 (3)
C1—Fe1—C3—C481.9 (2)C8—Fe1—C9—C10118.5 (3)
C2—Fe1—C3—C4120.0 (3)C8—Fe1—C9—C11122.7 (4)
C4—Fe1—C3—C2120.0 (3)C10—Fe1—C9—C8118.5 (3)
C5—Fe1—C3—C282.3 (3)C10—Fe1—C9—C11118.8 (4)
C5—Fe1—C3—C437.7 (2)C1—Fe1—C10—C652.9 (4)
C7—Fe1—C3—C252.3 (4)C1—Fe1—C10—C9172.5 (3)
C7—Fe1—C3—C4172.2 (3)C3—Fe1—C10—C6173.6 (2)
C8—Fe1—C3—C286.7 (3)C3—Fe1—C10—C966.9 (3)
C8—Fe1—C3—C4153.3 (2)C4—Fe1—C10—C6132.9 (2)
C9—Fe1—C3—C2129.9 (2)C4—Fe1—C10—C9107.5 (2)
C9—Fe1—C3—C4110.2 (2)C5—Fe1—C10—C689.5 (3)
C10—Fe1—C3—C2169.0 (2)C5—Fe1—C10—C9150.9 (2)
C10—Fe1—C3—C471.1 (3)C6—Fe1—C10—C9119.5 (3)
C1—Fe1—C4—C381.2 (2)C7—Fe1—C10—C637.1 (2)
C1—Fe1—C4—C537.9 (3)C7—Fe1—C10—C982.5 (2)
C2—Fe1—C4—C337.2 (2)C8—Fe1—C10—C681.3 (2)
C2—Fe1—C4—C581.9 (3)C8—Fe1—C10—C938.2 (2)
C3—Fe1—C4—C5119.1 (3)C9—Fe1—C10—C6119.5 (3)
C5—Fe1—C4—C3119.1 (3)C5—C1—C2—C30.6 (5)
C6—Fe1—C4—C3170.0 (2)Fe1—C1—C5—C459.0 (3)
C6—Fe1—C4—C570.9 (3)C5—C1—C2—Fe159.4 (3)
C8—Fe1—C4—C349.9 (4)C2—C1—C5—C40.4 (5)
C8—Fe1—C4—C5169.1 (3)C2—C1—C5—Fe158.6 (3)
C9—Fe1—C4—C386.1 (2)Fe1—C1—C2—C360.0 (3)
C9—Fe1—C4—C5154.8 (3)Fe1—C2—C3—C459.9 (3)
C10—Fe1—C4—C3130.1 (2)C1—C2—C3—C40.5 (5)
C10—Fe1—C4—C5110.8 (3)C1—C2—C3—Fe160.4 (3)
C1—Fe1—C5—C4119.2 (3)Fe1—C3—C4—C559.5 (3)
C2—Fe1—C5—C137.7 (2)C2—C3—C4—Fe159.2 (3)
C2—Fe1—C5—C481.5 (3)C2—C3—C4—C50.3 (5)
C3—Fe1—C5—C181.5 (2)Fe1—C4—C5—C158.7 (3)
C3—Fe1—C5—C437.8 (2)C3—C4—C5—Fe158.7 (3)
C4—Fe1—C5—C1119.2 (3)C3—C4—C5—C10.1 (5)
C6—Fe1—C5—C1109.4 (2)C10—C6—C7—C80.4 (4)
C6—Fe1—C5—C4131.4 (2)Fe1—C6—C10—C959.1 (3)
C7—Fe1—C5—C168.2 (3)C10—C6—C7—Fe159.0 (3)
C7—Fe1—C5—C4172.6 (2)C7—C6—C10—C90.2 (4)
C9—Fe1—C5—C1167.9 (3)C7—C6—C10—Fe158.9 (3)
C9—Fe1—C5—C448.7 (4)Fe1—C6—C7—C859.4 (3)
C10—Fe1—C5—C1153.4 (2)Fe1—C7—C8—C959.4 (3)
C10—Fe1—C5—C487.4 (3)C6—C7—C8—Fe159.8 (3)
C1—Fe1—C6—C786.1 (3)C6—C7—C8—C90.4 (4)
C1—Fe1—C6—C10153.7 (2)Fe1—C8—C9—C1059.3 (2)
C2—Fe1—C6—C747.9 (4)Fe1—C8—C9—C11117.9 (4)
C2—Fe1—C6—C10168.1 (3)C7—C8—C9—Fe159.0 (3)
C4—Fe1—C6—C7171.4 (2)C7—C8—C9—C100.2 (4)
C4—Fe1—C6—C1068.4 (3)C7—C8—C9—C11176.9 (3)
C5—Fe1—C6—C7130.5 (2)C8—C9—C10—C60.0 (4)
C5—Fe1—C6—C10109.3 (3)C11—C9—C10—Fe1118.3 (3)
C7—Fe1—C6—C10120.2 (3)C11—C9—C10—C6177.3 (3)
C8—Fe1—C6—C738.3 (2)Fe1—C9—C11—C1278.4 (4)
C8—Fe1—C6—C1081.9 (2)Fe1—C9—C11—C16101.3 (4)
C9—Fe1—C6—C782.4 (2)C8—C9—C11—C12167.6 (4)
C9—Fe1—C6—C1037.8 (2)C8—C9—C11—C1612.1 (6)
C10—Fe1—C6—C7120.2 (3)Fe1—C9—C10—C659.0 (3)
C1—Fe1—C7—C6111.7 (2)C8—C9—C10—Fe159.0 (3)
C1—Fe1—C7—C8129.6 (2)C10—C9—C11—C16171.2 (4)
C2—Fe1—C7—C6155.2 (2)C10—C9—C11—C129.1 (6)
C2—Fe1—C7—C886.1 (2)C9—C11—C12—C13177.7 (4)
C3—Fe1—C7—C6170.1 (3)C16—C11—C12—C132.0 (6)
C3—Fe1—C7—C851.4 (4)C12—C11—C16—C151.2 (5)
C5—Fe1—C7—C671.8 (3)C9—C11—C16—C15178.4 (3)
C5—Fe1—C7—C8169.5 (3)C11—C12—C13—C140.2 (6)
C6—Fe1—C7—C8118.7 (3)C12—C13—C14—C17178.5 (4)
C8—Fe1—C7—C6118.7 (3)C12—C13—C14—C152.3 (6)
C9—Fe1—C7—C681.3 (2)C17—C14—C15—C16177.8 (4)
C9—Fe1—C7—C837.4 (2)C13—C14—C17—C17i0.8 (7)
C10—Fe1—C7—C637.2 (2)C13—C14—C15—C163.0 (6)
C10—Fe1—C7—C881.5 (2)C15—C14—C17—C17i180.0 (4)
C1—Fe1—C8—C771.3 (3)C14—C15—C16—C111.3 (6)
C1—Fe1—C8—C9168.9 (2)C14—C17—C17i—C14i180.0 (4)
C2—Fe1—C8—C7110.2 (2)
Symmetry code: (i) x, y, z+1.
 

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