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In the title compound, [Fe(C5H5)(C13H10Br)], the benzene ring makes a dihedral angle of 14.1 (2)° with the substituted cyclo­penta­dienyl ring. The bond distances imply that there is no conjugation between the cyclo­penta­dienyl and benzene rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001164/xu6103sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001164/xu6103Isup2.hkl
Contains datablock I

CCDC reference: 254716

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.035
  • wR factor = 0.089
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT432_ALERT_2_C Short Inter X...Y Contact Br1 .. C10 .. 3.31 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2601 Count of symmetry unique reflns 1537 Completeness (_total/calc) 169.23% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1064 Fraction of Friedel pairs measured 0.692 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-1-(4-bromobenzylidene)ferrocene top
Crystal data top
[Fe(C5H5)(C13H10Br)]F(000) = 736
Mr = 367.06Dx = 1.647 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2888 reflections
a = 6.0159 (14) Åθ = 2.6–23.8°
b = 11.014 (3) ŵ = 3.70 mm1
c = 22.347 (5) ÅT = 273 K
V = 1480.7 (6) Å3Block, red
Z = 40.47 × 0.45 × 0.44 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2601 independent reflections
Radiation source: fine-focus sealed tube2219 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.185, Tmax = 0.196k = 1313
7751 measured reflectionsl = 1926
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)] = 0.035H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0513P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2601 reflectionsΔρmax = 0.60 e Å3
181 parametersΔρmin = 0.42 e Å3
348 restraintsAbsolute structure: Flack (1983), 1064 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.005 (17)
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*/Ueq
Br10.06334 (11)0.01268 (5)0.47345 (3)0.0627 (2)
Fe10.85911 (11)0.27195 (6)0.82307 (3)0.03664 (19)
C10.8607 (9)0.3284 (4)0.7359 (2)0.0438 (12)
C21.0815 (9)0.3122 (5)0.7572 (2)0.0478 (12)
H21.18640.25940.74120.057*
C31.1147 (9)0.3894 (5)0.8066 (2)0.0480 (13)
H31.24560.39650.82850.058*
C40.9158 (9)0.4542 (4)0.8174 (2)0.0464 (12)
H40.89240.51070.84770.056*
C50.7572 (9)0.4172 (4)0.7734 (2)0.0448 (12)
H50.61240.44590.76970.054*
C60.5979 (11)0.1680 (6)0.8457 (3)0.0786 (18)
H60.45710.17470.82880.094*
C70.7674 (13)0.0950 (5)0.8269 (3)0.0703 (17)
H70.76230.04220.79440.084*
C80.9451 (14)0.1125 (6)0.8635 (3)0.0808 (18)
H81.08150.07320.86040.097*
C90.8917 (16)0.1954 (7)0.9047 (3)0.090 (2)
H90.98530.22390.93470.108*
C100.6792 (16)0.2310 (5)0.8957 (3)0.0843 (19)
H100.60090.28710.91860.101*
C110.7625 (9)0.2594 (5)0.6864 (2)0.0459 (12)
H110.83590.18920.67430.055*
C120.5789 (9)0.2886 (4)0.6578 (2)0.0467 (12)
H120.51310.36210.66810.056*
C130.4684 (9)0.2180 (4)0.6117 (2)0.0420 (12)
C140.2576 (8)0.2544 (4)0.5910 (2)0.0420 (12)
H140.19580.32560.60600.050*
C150.1412 (10)0.1890 (4)0.5501 (2)0.0465 (12)
H150.00180.21500.53750.056*
C160.2318 (9)0.0838 (4)0.5274 (2)0.0421 (12)
C170.4413 (9)0.0461 (4)0.5436 (2)0.0457 (13)
H170.50440.02280.52660.055*
C180.5554 (9)0.1132 (4)0.5858 (2)0.0441 (12)
H180.69610.08740.59740.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0671 (4)0.0628 (4)0.0583 (4)0.0039 (3)0.0180 (3)0.0108 (3)
Fe10.0411 (4)0.0325 (3)0.0362 (4)0.0066 (3)0.0010 (3)0.0012 (3)
C10.055 (3)0.040 (2)0.036 (2)0.006 (2)0.002 (2)0.000 (2)
C20.046 (3)0.051 (3)0.047 (3)0.005 (2)0.007 (3)0.006 (2)
C30.043 (3)0.054 (3)0.047 (3)0.016 (2)0.000 (2)0.003 (2)
C40.059 (3)0.033 (2)0.047 (3)0.011 (2)0.005 (3)0.003 (2)
C50.048 (3)0.038 (2)0.048 (3)0.005 (2)0.003 (2)0.012 (2)
C60.047 (3)0.087 (4)0.101 (4)0.021 (3)0.003 (3)0.057 (3)
C70.103 (4)0.043 (3)0.066 (4)0.019 (3)0.013 (4)0.003 (3)
C80.071 (4)0.069 (3)0.103 (4)0.011 (3)0.011 (4)0.046 (3)
C90.123 (5)0.088 (4)0.059 (3)0.042 (4)0.023 (4)0.029 (3)
C100.122 (5)0.050 (3)0.081 (4)0.001 (4)0.060 (4)0.010 (3)
C110.048 (3)0.046 (3)0.044 (3)0.002 (2)0.003 (3)0.007 (2)
C120.051 (3)0.045 (3)0.044 (3)0.000 (3)0.004 (3)0.004 (2)
C130.048 (3)0.045 (3)0.034 (3)0.009 (3)0.002 (2)0.006 (2)
C140.042 (3)0.041 (3)0.044 (3)0.002 (2)0.001 (2)0.000 (2)
C150.042 (3)0.052 (3)0.046 (3)0.002 (3)0.000 (3)0.004 (2)
C160.048 (3)0.042 (3)0.037 (3)0.008 (2)0.006 (3)0.009 (2)
C170.049 (3)0.039 (2)0.049 (3)0.000 (2)0.001 (3)0.003 (2)
C180.035 (3)0.051 (3)0.047 (3)0.004 (2)0.004 (2)0.006 (2)
Geometric parameters (Å, º) top
Br1—C161.901 (5)C6—H60.9300
Fe1—C102.003 (6)C7—C81.360 (9)
Fe1—C62.009 (6)C7—H70.9300
Fe1—C92.020 (6)C8—C91.336 (10)
Fe1—C72.027 (6)C8—H80.9300
Fe1—C22.037 (5)C9—C101.352 (11)
Fe1—C42.040 (4)C9—H90.9300
Fe1—C82.042 (6)C10—H100.9300
Fe1—C52.042 (5)C11—C121.317 (7)
Fe1—C32.043 (5)C11—H110.9300
Fe1—C12.044 (5)C12—C131.452 (7)
C1—C21.422 (8)C12—H120.9300
C1—C51.430 (7)C13—C181.393 (7)
C1—C111.466 (7)C13—C141.408 (7)
C2—C31.407 (7)C14—C151.359 (6)
C2—H20.9300C14—H140.9300
C3—C41.414 (7)C15—C161.377 (7)
C3—H30.9300C15—H150.9300
C4—C51.430 (7)C16—C171.375 (7)
C4—H40.9300C17—C181.381 (7)
C5—H50.9300C17—H170.9300
C6—C71.365 (9)C18—H180.9300
C6—C101.404 (10)
C10—Fe1—C641.0 (3)C5—C4—Fe169.6 (3)
C10—Fe1—C939.3 (3)C3—C4—H4126.2
C6—Fe1—C967.1 (3)C5—C4—H4126.2
C10—Fe1—C766.6 (3)Fe1—C4—H4126.0
C6—Fe1—C739.5 (3)C4—C5—C1107.9 (5)
C9—Fe1—C765.6 (3)C4—C5—Fe169.4 (3)
C10—Fe1—C2171.6 (3)C1—C5—Fe169.6 (3)
C6—Fe1—C2145.0 (3)C4—C5—H5126.1
C9—Fe1—C2132.8 (3)C1—C5—H5126.1
C7—Fe1—C2114.7 (2)Fe1—C5—H5126.5
C10—Fe1—C4111.2 (2)C7—C6—C10106.0 (6)
C6—Fe1—C4135.0 (3)C7—C6—Fe170.9 (3)
C9—Fe1—C4116.8 (3)C10—C6—Fe169.3 (4)
C7—Fe1—C4173.7 (3)C7—C6—H6127.0
C2—Fe1—C468.4 (2)C10—C6—H6127.0
C10—Fe1—C865.4 (3)Fe1—C6—H6124.4
C6—Fe1—C866.2 (3)C8—C7—C6108.6 (6)
C9—Fe1—C838.4 (3)C8—C7—Fe171.1 (4)
C7—Fe1—C839.1 (3)C6—C7—Fe169.5 (3)
C2—Fe1—C8109.9 (3)C8—C7—H7125.7
C4—Fe1—C8146.2 (3)C6—C7—H7125.7
C10—Fe1—C5117.1 (3)Fe1—C7—H7125.3
C6—Fe1—C5110.4 (2)C9—C8—C7108.8 (7)
C9—Fe1—C5148.0 (3)C9—C8—Fe169.9 (4)
C7—Fe1—C5134.0 (3)C7—C8—Fe169.9 (4)
C2—Fe1—C568.5 (2)C9—C8—H8125.6
C4—Fe1—C541.02 (19)C7—C8—H8125.6
C8—Fe1—C5172.2 (3)Fe1—C8—H8126.2
C10—Fe1—C3134.0 (3)C8—C9—C10108.9 (7)
C6—Fe1—C3174.3 (3)C8—C9—Fe171.7 (4)
C9—Fe1—C3110.7 (3)C10—C9—Fe169.7 (4)
C7—Fe1—C3145.2 (3)C8—C9—H9125.6
C2—Fe1—C340.4 (2)C10—C9—H9125.6
C4—Fe1—C340.5 (2)Fe1—C9—H9124.6
C8—Fe1—C3115.7 (3)C9—C10—C6107.7 (6)
C5—Fe1—C368.4 (2)C9—C10—Fe171.0 (4)
C10—Fe1—C1147.5 (3)C6—C10—Fe169.7 (4)
C6—Fe1—C1114.6 (3)C9—C10—H10126.1
C9—Fe1—C1170.8 (3)C6—C10—H10126.1
C7—Fe1—C1109.5 (2)Fe1—C10—H10124.7
C2—Fe1—C140.8 (2)C12—C11—C1125.3 (5)
C4—Fe1—C168.96 (19)C12—C11—H11117.3
C8—Fe1—C1133.0 (3)C1—C11—H11117.3
C5—Fe1—C140.98 (19)C11—C12—C13126.7 (5)
C3—Fe1—C168.4 (2)C11—C12—H12116.6
C2—C1—C5107.2 (4)C13—C12—H12116.6
C2—C1—C11124.3 (5)C18—C13—C14116.0 (4)
C5—C1—C11128.4 (5)C18—C13—C12124.5 (5)
C2—C1—Fe169.3 (3)C14—C13—C12119.5 (5)
C5—C1—Fe169.4 (3)C15—C14—C13122.3 (5)
C11—C1—Fe1124.0 (3)C15—C14—H14118.9
C3—C2—C1108.7 (5)C13—C14—H14118.9
C3—C2—Fe170.0 (3)C14—C15—C16119.3 (5)
C1—C2—Fe169.9 (3)C14—C15—H15120.4
C3—C2—H2125.7C16—C15—H15120.4
C1—C2—H2125.7C17—C16—C15121.4 (5)
Fe1—C2—H2126.0C17—C16—Br1119.1 (4)
C2—C3—C4108.5 (5)C15—C16—Br1119.5 (4)
C2—C3—Fe169.6 (3)C16—C17—C18118.2 (5)
C4—C3—Fe169.6 (3)C16—C17—H17120.9
C2—C3—H3125.7C18—C17—H17120.9
C4—C3—H3125.7C17—C18—C13122.7 (5)
Fe1—C3—H3126.6C17—C18—H18118.7
C3—C4—C5107.7 (4)C13—C18—H18118.7
C3—C4—Fe169.8 (3)
 

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