Download citation
Download citation
link to html
The structure of 1,1′-di­bromo­ferrocene, [Fe(C5H4Br)2], has been determined by single-crystal X-ray diffraction at 100 K. The two Br substituents are eclipsed in the solid state, with a Br...Br distance of 3.6172 (6) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028429/sj6016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028429/sj6016Isup2.hkl
Contains datablock I

CCDC reference: 258656

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.037
  • wR factor = 0.094
  • Data-to-parameter ratio = 24.3

checkCIF/PLATON results

No syntax errors found



Alert level A ABSTM02_ALERT_3_A Crystal and compound unsuitable for non-numerical corrections. Product of mu and tmid > 3.0 Value of mu given = 9.746 tmid = 0.360 PLAT065_ALERT_3_A Crystal Requires Numerical Correction mu*tmid .. 3.51
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br2 .. 3.59 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 30.50 From the CIF: _reflns_number_total 2890 Count of symmetry unique reflns 1554 Completeness (_total/calc) 185.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1336 Fraction of Friedel pairs measured 0.860 Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997–2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,1'-Dibromoferrocene top
Crystal data top
[Fe(C5H4Br)2]F(000) = 328
Mr = 343.83Dx = 2.357 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.2289 (6) ÅCell parameters from 5466 reflections
b = 10.024 (1) Åθ = 2.6–31.9°
c = 7.8351 (8) ŵ = 9.75 mm1
β = 97.987 (2)°T = 100 K
V = 484.49 (8) Å3Irregular, brown
Z = 20.50 × 0.36 × 0.31 mm
Data collection top
Bruker AXS SMART APEX CCD
diffractometer
2890 independent reflections
Radiation source: fine-focus sealed tube2850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ and ω scansθmax = 30.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 88
Tmin = 0.021, Tmax = 0.05k = 1414
5736 measured reflectionsl = 1110
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0733P)2 + 0.3107P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2890 reflectionsΔρmax = 1.12 e Å3
119 parametersΔρmin = 0.66 e Å3
1 restraintAbsolute structure: Flack (1983), 1339 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.116 (13)
Special details top

Experimental. The product of the linear absorption coefficient and the median crystal dimension for the crystal investigated here is 3.51, and an analytical absorption correction was thus advisable. However, the crystals under investigation had been of irregular shape and had to be cut to size, making face indexing impossible. The absorption correction used here was multi-scan, based on the program SADABS as implemented in the SAINT-Plus (Bruker, 2003). The experimental values for Tmin and Tmax after scaling are 0.021 and 0.050, respectively, and do not differ significantly from the expected values (0.021 and 0.049).

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
Br10.00953 (7)0.61869 (4)1.02185 (5)0.01565 (10)
Br20.12003 (6)0.38079 (4)0.69804 (6)0.01804 (11)
C10.1934 (7)0.7361 (4)0.9230 (5)0.0136 (7)
C20.1292 (7)0.8295 (4)0.7888 (6)0.0146 (7)
H20.01280.84150.72880.018*
C30.3196 (8)0.9018 (4)0.7615 (6)0.0187 (8)
H30.32620.97100.67960.022*
C40.4979 (7)0.8521 (4)0.8785 (6)0.0183 (8)
H40.64340.88270.88750.022*
C50.4210 (7)0.7484 (4)0.9798 (5)0.0151 (7)
H50.50460.69781.06760.018*
C60.3011 (6)0.5130 (4)0.6298 (5)0.0128 (7)
C70.5271 (6)0.5286 (4)0.6923 (5)0.0140 (7)
H70.60900.47870.78180.017*
C80.6049 (7)0.6328 (4)0.5947 (5)0.0182 (8)
H80.75020.66400.60670.022*
C90.4290 (8)0.6830 (5)0.4755 (5)0.0198 (8)
H90.43680.75410.39640.024*
C100.2400 (7)0.6080 (4)0.4960 (5)0.0156 (7)
H100.09970.61900.43260.019*
Fe10.36191 (8)0.70162 (5)0.72275 (6)0.00994 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01640 (17)0.01861 (18)0.01314 (18)0.00105 (13)0.00630 (12)0.00039 (14)
Br20.01915 (18)0.01436 (18)0.0212 (2)0.00441 (14)0.00490 (14)0.00214 (14)
C10.0163 (16)0.0139 (16)0.0115 (15)0.0000 (13)0.0055 (13)0.0015 (12)
C20.0171 (17)0.0126 (16)0.0153 (17)0.0036 (13)0.0066 (14)0.0003 (13)
C30.027 (2)0.0119 (18)0.0189 (18)0.0037 (14)0.0095 (16)0.0026 (13)
C40.0203 (17)0.0182 (19)0.0178 (18)0.0067 (14)0.0078 (15)0.0077 (14)
C50.0168 (17)0.0181 (17)0.0105 (15)0.0019 (13)0.0016 (13)0.0054 (13)
C60.0153 (16)0.0110 (16)0.0117 (16)0.0021 (13)0.0007 (13)0.0028 (12)
C70.0131 (16)0.0148 (16)0.0142 (16)0.0007 (13)0.0029 (13)0.0051 (13)
C80.0193 (17)0.019 (2)0.0182 (17)0.0029 (15)0.0112 (14)0.0056 (15)
C90.031 (2)0.0178 (19)0.0129 (17)0.0001 (17)0.0108 (16)0.0002 (14)
C100.0221 (17)0.0144 (16)0.0101 (14)0.0016 (15)0.0010 (13)0.0028 (13)
Fe10.0129 (2)0.0091 (2)0.0084 (2)0.00081 (17)0.00358 (17)0.00135 (17)
Geometric parameters (Å, º) top
Br1—C11.882 (4)C5—H50.9500
Br2—C61.866 (4)C6—C101.428 (5)
C1—C21.423 (6)C6—C71.433 (5)
C1—C51.431 (6)C6—Fe12.042 (4)
C1—Fe12.035 (4)C7—C81.419 (6)
C2—C31.431 (6)C7—Fe12.048 (4)
C2—Fe12.054 (4)C7—H70.9500
C2—H20.9500C8—C91.429 (7)
C3—C41.428 (7)C8—Fe12.048 (4)
C3—Fe12.052 (4)C8—H80.9500
C3—H30.9500C9—C101.425 (6)
C4—C51.430 (6)C9—Fe12.046 (4)
C4—Fe12.048 (4)C9—H90.9500
C4—H40.9500C10—Fe12.059 (4)
C5—Fe12.051 (4)C10—H100.9500
C2—C1—C5109.7 (4)Fe1—C9—H9125.8
C2—C1—Br1126.2 (3)C9—C10—C6107.1 (4)
C5—C1—Br1124.0 (3)C9—C10—Fe169.2 (2)
C2—C1—Fe170.4 (2)C6—C10—Fe169.0 (2)
C5—C1—Fe170.1 (2)C9—C10—H10126.4
Br1—C1—Fe1128.3 (2)C6—C10—H10126.4
C1—C2—C3106.9 (4)Fe1—C10—H10126.9
C1—C2—Fe168.9 (2)C1—Fe1—C6110.01 (17)
C3—C2—Fe169.5 (2)C1—Fe1—C9160.16 (18)
C1—C2—H2126.6C6—Fe1—C968.31 (17)
C3—C2—H2126.6C1—Fe1—C7123.71 (16)
Fe1—C2—H2126.6C6—Fe1—C741.03 (15)
C4—C3—C2108.3 (4)C9—Fe1—C768.93 (17)
C4—C3—Fe169.5 (2)C1—Fe1—C468.31 (17)
C2—C3—Fe169.7 (2)C6—Fe1—C4159.23 (18)
C4—C3—H3125.8C9—Fe1—C4120.60 (18)
C2—C3—H3125.8C7—Fe1—C4121.35 (17)
Fe1—C3—H3126.6C1—Fe1—C8158.47 (18)
C3—C4—C5108.6 (4)C6—Fe1—C868.07 (16)
C3—C4—Fe169.8 (2)C9—Fe1—C840.85 (18)
C5—C4—Fe169.7 (2)C7—Fe1—C840.53 (16)
C3—C4—H4125.7C4—Fe1—C8105.51 (18)
C5—C4—H4125.7C1—Fe1—C541.00 (16)
Fe1—C4—H4126.4C6—Fe1—C5124.14 (16)
C4—C5—C1106.5 (4)C9—Fe1—C5156.65 (19)
C4—C5—Fe169.5 (2)C7—Fe1—C5106.49 (17)
C1—C5—Fe168.9 (2)C4—Fe1—C540.83 (17)
C4—C5—H5126.7C8—Fe1—C5120.94 (18)
C1—C5—H5126.7C1—Fe1—C368.24 (17)
Fe1—C5—H5126.4C6—Fe1—C3159.50 (18)
C10—C6—C7109.1 (4)C9—Fe1—C3106.05 (18)
C10—C6—Br2125.0 (3)C7—Fe1—C3157.31 (18)
C7—C6—Br2125.7 (3)C4—Fe1—C340.77 (19)
C10—C6—Fe170.3 (2)C8—Fe1—C3121.39 (17)
C7—C6—Fe169.7 (2)C5—Fe1—C368.90 (18)
Br2—C6—Fe1130.2 (2)C1—Fe1—C240.74 (16)
C8—C7—C6106.8 (4)C6—Fe1—C2124.40 (16)
C8—C7—Fe169.8 (2)C9—Fe1—C2122.64 (18)
C6—C7—Fe169.3 (2)C7—Fe1—C2160.31 (17)
C8—C7—H7126.6C4—Fe1—C268.80 (17)
C6—C7—H7126.6C8—Fe1—C2158.26 (17)
Fe1—C7—H7125.9C5—Fe1—C269.30 (17)
C7—C8—C9108.9 (4)C3—Fe1—C240.79 (17)
C7—C8—Fe169.7 (2)C1—Fe1—C10125.10 (17)
C9—C8—Fe169.5 (2)C6—Fe1—C1040.74 (16)
C7—C8—H8125.6C9—Fe1—C1040.63 (18)
C9—C8—H8125.6C7—Fe1—C1069.16 (16)
Fe1—C8—H8126.8C4—Fe1—C10157.27 (18)
C10—C9—C8108.1 (4)C8—Fe1—C1068.45 (17)
C10—C9—Fe170.2 (2)C5—Fe1—C10161.10 (17)
C8—C9—Fe169.6 (2)C3—Fe1—C10122.28 (18)
C10—C9—H9126.0C2—Fe1—C10108.26 (17)
C8—C9—H9126.0
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds