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1,12-Diferrocenyldo­decane, [Fe2(C5H5)2(C22H32)], was synthesized from ferrocene and 1,12-do­decane­dioyl chloride, followed by Clemmensen reduction. The single-crystal structure was determined at 100 K by X-ray diffraction and the spectroscopic and cyclic voltammetric data of 1,12-diferrocenyldo­decane and its precursor are reported.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501367X/fl6164sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501367X/fl61641sup2.hkl
Contains datablock 1

CCDC reference: 274395

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.075
  • Data-to-parameter ratio = 25.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 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.

1,12-Diferrocenyldodecane top
Crystal data top
[Fe2(C5H5)2(C22H32)]F(000) = 572
Mr = 538.36Dx = 1.363 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.0203 (9) ÅCell parameters from 6072 reflections
b = 7.5367 (4) Åθ = 2.7–30.5°
c = 11.1773 (6) ŵ = 1.12 mm1
β = 103.597 (1)°T = 100 K
V = 1311.73 (12) Å3Block, red
Z = 20.47 × 0.29 × 0.25 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
3988 independent reflections
Radiation source: fine-focus sealed tube3769 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 30.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 2222
Tmin = 0.644, Tmax = 0.75k = 1010
15135 measured reflectionsl = 1515
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0461P)2 + 0.3363P]
where P = (Fo2 + 2Fc2)/3
3988 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.37 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*/Ueq
Fe10.150648 (8)0.456529 (18)0.201472 (12)0.01482 (6)
C150.47083 (7)0.47571 (14)0.82064 (9)0.01875 (18)
H15A0.48670.34920.81700.022*
H15B0.51880.54790.80510.022*
C100.27129 (6)0.56166 (13)0.25528 (9)0.01603 (17)
C130.40387 (7)0.47918 (15)0.59021 (9)0.01925 (19)
H13A0.41640.35170.58190.023*
H13B0.45460.54740.58000.023*
C110.34316 (6)0.50312 (15)0.35980 (9)0.01843 (17)
H11A0.39580.56880.35510.022*
H11B0.35420.37550.34930.022*
C120.32668 (7)0.53082 (14)0.48777 (9)0.01899 (19)
H12A0.31260.65710.49750.023*
H12B0.27650.45890.49530.023*
C140.39067 (7)0.51228 (15)0.71907 (9)0.01973 (18)
H14A0.34340.43570.73210.024*
H14B0.37310.63730.72510.024*
C90.20809 (7)0.69370 (13)0.25968 (9)0.01905 (18)
H90.20250.76040.33470.023*
C160.45963 (7)0.51663 (15)0.94941 (9)0.01907 (18)
H16A0.41240.44260.96560.023*
H16B0.44260.64250.95260.023*
C60.25518 (7)0.49900 (15)0.13089 (9)0.01910 (18)
H60.28880.40550.09940.023*
C70.18182 (7)0.59061 (15)0.06002 (9)0.02098 (19)
H70.15550.57280.02960.025*
C80.15281 (7)0.71108 (14)0.13960 (10)0.02141 (19)
H80.10230.79250.11590.026*
C40.05170 (7)0.28888 (15)0.12628 (10)0.0237 (2)
H40.02240.28000.03700.028*
C20.14696 (9)0.24562 (18)0.31325 (12)0.0354 (3)
H20.19600.20000.37860.043*
C30.12559 (8)0.19140 (15)0.18762 (13)0.0290 (2)
H30.15700.10130.14930.035*
C50.02764 (7)0.40330 (18)0.21393 (11)0.0273 (2)
H50.02150.48880.19690.033*
C10.08646 (9)0.3764 (2)0.32950 (11)0.0347 (3)
H10.08570.43910.40810.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.01573 (9)0.01515 (9)0.01276 (8)0.00131 (4)0.00170 (5)0.00044 (4)
C150.0205 (4)0.0223 (5)0.0124 (4)0.0036 (3)0.0016 (3)0.0006 (3)
C100.0169 (4)0.0178 (4)0.0126 (4)0.0021 (3)0.0017 (3)0.0005 (3)
C130.0195 (4)0.0241 (5)0.0123 (4)0.0046 (3)0.0000 (3)0.0010 (3)
C110.0170 (4)0.0232 (4)0.0138 (4)0.0021 (4)0.0011 (3)0.0016 (4)
C120.0168 (4)0.0262 (5)0.0126 (4)0.0017 (3)0.0005 (3)0.0009 (3)
C140.0193 (4)0.0262 (5)0.0126 (4)0.0026 (4)0.0017 (3)0.0002 (3)
C90.0219 (4)0.0158 (4)0.0173 (4)0.0007 (3)0.0003 (3)0.0020 (3)
C160.0209 (5)0.0236 (5)0.0118 (4)0.0036 (4)0.0019 (3)0.0002 (3)
C60.0200 (4)0.0247 (4)0.0129 (4)0.0025 (4)0.0044 (3)0.0011 (4)
C70.0242 (5)0.0235 (5)0.0137 (4)0.0043 (4)0.0014 (3)0.0032 (4)
C80.0239 (5)0.0161 (4)0.0205 (4)0.0003 (3)0.0023 (4)0.0025 (3)
C40.0191 (4)0.0255 (5)0.0249 (5)0.0063 (4)0.0020 (4)0.0025 (4)
C20.0329 (6)0.0331 (6)0.0335 (6)0.0139 (5)0.0059 (5)0.0180 (5)
C30.0244 (5)0.0169 (5)0.0437 (7)0.0049 (4)0.0039 (4)0.0014 (4)
C50.0199 (5)0.0331 (6)0.0308 (6)0.0048 (4)0.0097 (4)0.0032 (5)
C10.0375 (6)0.0475 (8)0.0212 (5)0.0200 (6)0.0111 (5)0.0010 (5)
Geometric parameters (Å, º) top
Fe1—C22.0312 (11)C12—H12A0.9900
Fe1—C72.0351 (10)C12—H12B0.9900
Fe1—C32.0368 (11)C14—H14A0.9900
Fe1—C62.0373 (10)C14—H14B0.9900
Fe1—C12.0401 (12)C9—C81.4297 (14)
Fe1—C82.0424 (10)C9—H91.0000
Fe1—C102.0441 (10)C16—C16i1.525 (2)
Fe1—C92.0454 (10)C16—H16A0.9900
Fe1—C42.0468 (10)C16—H16B0.9900
Fe1—C52.0476 (11)C6—C71.4310 (15)
C15—C161.5232 (14)C6—H61.0000
C15—C141.5260 (14)C7—C81.4234 (16)
C15—H15A0.9900C7—H71.0000
C15—H15B0.9900C8—H81.0000
C10—C91.4287 (14)C4—C31.4246 (17)
C10—C61.4331 (13)C4—C51.4247 (16)
C10—C111.5009 (14)C4—H41.0000
C13—C141.5248 (14)C2—C11.424 (2)
C13—C121.5252 (14)C2—C31.4248 (19)
C13—H13A0.9900C2—H21.0000
C13—H13B0.9900C3—H31.0000
C11—C121.5287 (14)C5—C11.4232 (18)
C11—H11A0.9900C5—H51.0000
C11—H11B0.9900C1—H11.0000
C2—Fe1—C7156.12 (6)C11—C12—H12A109.1
C2—Fe1—C341.00 (6)C13—C12—H12B109.1
C7—Fe1—C3120.54 (5)C11—C12—H12B109.1
C2—Fe1—C6120.43 (5)H12A—C12—H12B107.9
C7—Fe1—C641.15 (4)C13—C14—C15113.19 (9)
C3—Fe1—C6106.86 (5)C13—C14—H14A108.9
C2—Fe1—C140.94 (6)C15—C14—H14A108.9
C7—Fe1—C1161.47 (6)C13—C14—H14B108.9
C3—Fe1—C168.91 (6)C15—C14—H14B108.9
C6—Fe1—C1156.06 (5)H14A—C14—H14B107.8
C2—Fe1—C8161.55 (6)C10—C9—C8108.61 (9)
C7—Fe1—C840.86 (4)C10—C9—Fe169.50 (6)
C3—Fe1—C8156.14 (5)C8—C9—Fe169.41 (6)
C6—Fe1—C868.92 (5)C10—C9—H9125.7
C1—Fe1—C8124.54 (6)C8—C9—H9125.7
C2—Fe1—C10106.53 (4)Fe1—C9—H9125.7
C7—Fe1—C1069.41 (4)C15—C16—C16i113.55 (11)
C3—Fe1—C10123.95 (5)C15—C16—H16A108.9
C6—Fe1—C1041.11 (4)C16i—C16—H16A108.9
C1—Fe1—C10120.40 (5)C15—C16—H16B108.9
C8—Fe1—C1069.23 (4)C16i—C16—H16B108.9
C2—Fe1—C9124.35 (5)H16A—C16—H16B107.7
C7—Fe1—C968.83 (4)C7—C6—C10108.37 (9)
C3—Fe1—C9161.33 (5)C7—C6—Fe169.35 (6)
C6—Fe1—C968.69 (4)C10—C6—Fe169.70 (6)
C1—Fe1—C9107.39 (5)C7—C6—H6125.8
C8—Fe1—C940.94 (4)C10—C6—H6125.8
C10—Fe1—C940.90 (4)Fe1—C6—H6125.8
C2—Fe1—C468.76 (5)C8—C7—C6107.95 (9)
C7—Fe1—C4107.18 (4)C8—C7—Fe169.84 (6)
C3—Fe1—C440.83 (5)C6—C7—Fe169.51 (6)
C6—Fe1—C4124.46 (4)C8—C7—H7126.0
C1—Fe1—C468.65 (5)C6—C7—H7126.0
C8—Fe1—C4120.93 (4)Fe1—C7—H7126.0
C10—Fe1—C4161.36 (4)C7—C8—C9107.88 (9)
C9—Fe1—C4156.52 (4)C7—C8—Fe169.30 (6)
C2—Fe1—C568.73 (5)C9—C8—Fe169.64 (6)
C7—Fe1—C5124.47 (5)C7—C8—H8126.1
C3—Fe1—C568.74 (5)C9—C8—H8126.1
C6—Fe1—C5161.62 (5)Fe1—C8—H8126.1
C1—Fe1—C540.75 (5)C3—C4—C5108.04 (10)
C8—Fe1—C5107.47 (5)C3—C4—Fe169.21 (6)
C10—Fe1—C5156.13 (4)C5—C4—Fe169.67 (6)
C9—Fe1—C5121.19 (5)C3—C4—H4126.0
C4—Fe1—C540.72 (5)C5—C4—H4126.0
C16—C15—C14113.63 (9)Fe1—C4—H4126.0
C16—C15—H15A108.8C1—C2—C3108.13 (11)
C14—C15—H15A108.8C1—C2—Fe169.86 (7)
C16—C15—H15B108.8C3—C2—Fe169.71 (7)
C14—C15—H15B108.8C1—C2—H2125.9
H15A—C15—H15B107.7C3—C2—H2125.9
C9—C10—C6107.19 (9)Fe1—C2—H2125.9
C9—C10—C11126.73 (9)C4—C3—C2107.85 (11)
C6—C10—C11126.05 (9)C4—C3—Fe169.96 (6)
C9—C10—Fe169.60 (6)C2—C3—Fe169.29 (7)
C6—C10—Fe169.19 (6)C4—C3—H3126.1
C11—C10—Fe1127.90 (7)C2—C3—H3126.1
C14—C13—C12113.53 (9)Fe1—C3—H3126.1
C14—C13—H13A108.9C1—C5—C4108.03 (11)
C12—C13—H13A108.9C1—C5—Fe169.34 (7)
C14—C13—H13B108.9C4—C5—Fe169.61 (6)
C12—C13—H13B108.9C1—C5—H5126.0
H13A—C13—H13B107.7C4—C5—H5126.0
C10—C11—C12114.74 (8)Fe1—C5—H5126.0
C10—C11—H11A108.6C5—C1—C2107.95 (11)
C12—C11—H11A108.6C5—C1—Fe169.91 (6)
C10—C11—H11B108.6C2—C1—Fe169.20 (7)
C12—C11—H11B108.6C5—C1—H1126.0
H11A—C11—H11B107.6C2—C1—H1126.0
C13—C12—C11112.31 (8)Fe1—C1—H1126.0
C13—C12—H12A109.1
Symmetry code: (i) x+1, y+1, z+2.
 

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