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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1072.
Published online 2008 July 26. doi:  10.1107/S1600536808023106
PMCID: PMC2961982

(Z)-3-Ferrocenyl-2-(4-pyridyl)­propene­nitrile

Abstract

In the title compound, [Fe(C5H5)(C13H9N2)], the pyridine ring makes a dihedral angle of 9.91 (17)° with the substituted cyclo­penta­dienyl ring and the double bond adopts a Z configuration. In the crystal structure, inter­molecular C—H(...)N hydrogen bonds link the molecules into a one-dimensional chain in the a+c direction.

Related literature

For related literature, see: Dupont et al. (2005 [triangle]); Shao et al. (2005 [triangle]).

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Object name is e-64-m1072-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C13H9N2)]
  • M r = 314.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1072-efi1.jpg
  • a = 11.520 (2) Å
  • b = 6.0650 (15) Å
  • c = 20.421 (5) Å
  • β = 91.194 (18)°
  • V = 1426.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.05 mm−1
  • T = 293 (2) K
  • 0.40 × 0.35 × 0.10 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.779, T max = 1.000 (expected range = 0.701–0.900)
  • 13960 measured reflections
  • 3229 independent reflections
  • 2543 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.122
  • S = 1.05
  • 3229 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023106/kj2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023106/kj2092Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the Starter Fund of Southeast University for financial support to buy the Rigaku SCXmini CCD X-ray diffractometer.

supplementary crystallographic information

Comment

The chemistry of ferrocene has received much attention not only because of its exquisite structure but also its potential applications in many fields such as non-linear optical materials, catalyst and magnetoelectric materials (Dupont et al., 2005). The molecular structure of the title compound is shown in Fig. 1. The C11═C17 bond exhibits a Z configuration and the dihedral angle between the pyridine ring and the substituted cyclopentadienyl ring is 9.91 (17)°. The two cyclopentadienyl rings are nearly parallel with the dihedral angle of 3.3 (2)°. The Fe···Cg1 and Fe···Cg2 distances are 1.6611 (19) Å and 1.6563 (15) Å respectively and the Cg1···Fe···Cg2 angle is 176.18 (8), where Cg1 and Cg2 are the centroids of the unsubstituted and substituted Cp rings. Weak intermolecular C—H···N interactions are also found in the crystal structure, which link the compound into one-dimensional chain running in the a+c direction. Similar C—H···N hydrogen bonds in a ferrocene derivative were communicated by Shao et al. (2005).

Experimental

1 ml pyrrolidine was added to the mixture of formylferrocene (2.15 g, 0.01 mol) and 4-pyridineacetonitrile (1.18 g, 0.01 mol) in dichloromethane (100 ml). The mixture was stirred at room temperature for 5 h. After removing the solvent under reduced pressure, the residue was collected and dried in a vacuum desiccator. This crude product was purified by chromatography on silica gel, with petroleum ether and ethyl acetate (10:1 v/v) as eluent. Brownish red single crystals suitable for X-ray analysis were obtained by slow evaporation of ethanol at room temperature after 24 h.

Refinement

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and all H atoms have been omitted for clarity.
Fig. 2.
Packing of the title compound, viewed along the b axis. Dashed lines indicate C—H···N hydrogen-bond interactions.

Crystal data

[Fe(C5H5)(C13H9N2)]F000 = 648
Mr = 314.16Dx = 1.463 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3207 reflections
a = 11.520 (2) Åθ = 2.6–27.5º
b = 6.0650 (15) ŵ = 1.05 mm1
c = 20.421 (5) ÅT = 293 (2) K
β = 91.194 (18)ºPrism, red brown
V = 1426.5 (6) Å30.40 × 0.35 × 0.10 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer3229 independent reflections
Radiation source: fine-focus sealed tube2543 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.5º
ω scansh = −14→14
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −7→7
Tmin = 0.779, Tmax = 1.000l = −26→26
13960 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0583P)2 + 0.4315P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3229 reflectionsΔρmax = 0.36 e Å3
190 parametersΔρmin = −0.46 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 2σ(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)

xyzUiso*/Ueq
Fe10.51801 (3)0.90867 (6)0.199529 (18)0.03900 (15)
C120.4765 (2)0.8530 (5)0.29581 (12)0.0390 (6)
C110.5556 (2)0.8741 (5)0.35128 (13)0.0414 (6)
H11A0.61060.76240.35530.050*
C170.5622 (2)1.0306 (5)0.39804 (12)0.0383 (6)
C180.4829 (3)1.2149 (5)0.39637 (13)0.0468 (7)
C160.3975 (2)1.0073 (6)0.26614 (14)0.0473 (7)
H16A0.38401.15900.28070.057*
C150.3415 (3)0.9013 (6)0.21203 (16)0.0567 (8)
H15A0.28320.96840.18260.068*
C10.6478 (2)1.0312 (5)0.45305 (12)0.0397 (6)
C100.5885 (3)0.8562 (7)0.10971 (17)0.0654 (10)
H10A0.56450.74040.07880.079*
C50.6533 (3)1.2051 (5)0.49758 (14)0.0540 (8)
H5A0.60071.32110.49410.065*
C20.7280 (3)0.8635 (5)0.46294 (15)0.0526 (8)
H2A0.72740.74110.43550.063*
C130.4691 (3)0.6536 (5)0.25760 (14)0.0496 (7)
H13A0.51380.51850.26580.060*
C70.5411 (3)1.0641 (8)0.1125 (2)0.0766 (13)
H7A0.48001.12360.08350.092*
N20.8151 (3)1.0472 (6)0.55546 (14)0.0719 (9)
C90.6729 (3)0.8351 (7)0.15696 (17)0.0628 (9)
H9A0.71890.70190.16540.075*
N10.4213 (3)1.3642 (5)0.39676 (15)0.0733 (9)
C80.6822 (3)1.0285 (8)0.19148 (19)0.0735 (11)
H8A0.73711.05870.22770.088*
C40.7369 (3)1.2044 (6)0.54673 (17)0.0683 (10)
H4A0.73841.32260.57580.082*
C140.3852 (3)0.6842 (6)0.20690 (15)0.0584 (9)
H14A0.36210.57500.17370.070*
C60.5998 (4)1.1787 (6)0.1642 (3)0.0914 (16)
H6A0.58771.33220.17740.110*
C30.8088 (3)0.8783 (7)0.51349 (18)0.0696 (10)
H3A0.86210.76410.51870.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0337 (2)0.0464 (3)0.0369 (2)−0.00351 (17)0.00162 (15)−0.00326 (17)
C120.0347 (13)0.0474 (15)0.0352 (13)−0.0041 (11)0.0052 (11)−0.0042 (11)
C110.0385 (14)0.0476 (16)0.0381 (14)0.0034 (12)0.0023 (11)−0.0023 (12)
C170.0381 (13)0.0438 (15)0.0331 (13)0.0010 (11)0.0043 (11)−0.0007 (11)
C180.0560 (17)0.0494 (17)0.0350 (14)0.0059 (14)−0.0010 (13)−0.0052 (12)
C160.0337 (13)0.0643 (18)0.0439 (16)0.0046 (14)0.0025 (12)−0.0034 (14)
C150.0327 (14)0.090 (3)0.0468 (17)−0.0094 (16)−0.0024 (13)−0.0015 (16)
C10.0403 (14)0.0479 (15)0.0311 (13)−0.0009 (12)0.0054 (11)−0.0001 (11)
C100.067 (2)0.085 (3)0.0450 (18)−0.007 (2)0.0142 (17)−0.0103 (17)
C50.0583 (18)0.0573 (19)0.0461 (16)0.0090 (15)−0.0074 (14)−0.0147 (14)
C20.0554 (18)0.0564 (18)0.0457 (16)0.0118 (14)−0.0065 (14)−0.0081 (14)
C130.0584 (18)0.0493 (16)0.0412 (15)−0.0135 (14)0.0041 (14)−0.0039 (13)
C70.051 (2)0.108 (4)0.071 (2)0.008 (2)0.0099 (18)0.045 (2)
N20.076 (2)0.089 (2)0.0502 (16)0.0058 (18)−0.0193 (15)−0.0102 (16)
C90.0493 (18)0.079 (2)0.061 (2)0.0138 (17)0.0159 (16)0.0095 (18)
N10.091 (2)0.0681 (19)0.0603 (18)0.0309 (18)−0.0086 (17)−0.0103 (15)
C80.0479 (19)0.114 (3)0.058 (2)−0.036 (2)0.0079 (17)−0.008 (2)
C40.073 (2)0.074 (2)0.057 (2)0.006 (2)−0.0164 (18)−0.0215 (19)
C140.0529 (18)0.077 (2)0.0453 (17)−0.0288 (17)0.0042 (14)−0.0083 (16)
C60.113 (4)0.0426 (19)0.121 (4)−0.017 (2)0.073 (3)−0.004 (2)
C30.066 (2)0.082 (2)0.060 (2)0.0230 (19)−0.0200 (18)−0.0055 (19)

Geometric parameters (Å, °)

Fe1—C62.030 (4)C1—C51.393 (4)
Fe1—C72.034 (3)C10—C91.361 (5)
Fe1—C132.036 (3)C10—C71.376 (5)
Fe1—C82.037 (3)C10—H10A0.9800
Fe1—C102.046 (3)C5—C41.376 (4)
Fe1—C92.050 (3)C5—H5A0.9300
Fe1—C162.053 (3)C2—C31.378 (5)
Fe1—C152.055 (3)C2—H2A0.9300
Fe1—C142.056 (3)C13—C141.414 (4)
Fe1—C122.061 (3)C13—H13A0.9800
C12—C161.431 (4)C7—C61.423 (6)
C12—C131.441 (4)C7—H7A0.9800
C12—C111.445 (4)N2—C41.321 (5)
C11—C171.347 (4)N2—C31.336 (5)
C11—H11A0.9300C9—C81.371 (6)
C17—C181.443 (4)C9—H9A0.9800
C17—C11.480 (4)C8—C61.421 (6)
C18—N11.150 (4)C8—H8A0.9800
C16—C151.422 (4)C4—H4A0.9300
C16—H16A0.9800C14—H14A0.9800
C15—C141.414 (5)C6—H6A0.9800
C15—H15A0.9800C3—H3A0.9300
C1—C21.386 (4)
C6—Fe1—C740.99 (18)C14—C15—C16108.8 (3)
C6—Fe1—C13163.0 (2)C14—C15—Fe169.91 (17)
C7—Fe1—C13154.67 (17)C16—C15—Fe169.67 (16)
C6—Fe1—C840.91 (19)C14—C15—H15A125.6
C7—Fe1—C868.01 (16)C16—C15—H15A125.6
C13—Fe1—C8125.95 (17)Fe1—C15—H15A125.6
C6—Fe1—C1067.09 (16)C2—C1—C5116.1 (3)
C7—Fe1—C1039.40 (16)C2—C1—C17122.7 (3)
C13—Fe1—C10121.59 (14)C5—C1—C17121.2 (3)
C8—Fe1—C1066.19 (15)C9—C10—C7109.6 (4)
C6—Fe1—C967.04 (16)C9—C10—Fe170.72 (19)
C7—Fe1—C966.39 (15)C7—C10—Fe169.8 (2)
C13—Fe1—C9109.61 (14)C9—C10—H10A125.2
C8—Fe1—C939.21 (16)C7—C10—H10A125.2
C10—Fe1—C938.82 (14)Fe1—C10—H10A125.2
C6—Fe1—C16109.02 (14)C4—C5—C1119.7 (3)
C7—Fe1—C16123.12 (15)C4—C5—H5A120.2
C13—Fe1—C1668.68 (14)C1—C5—H5A120.2
C8—Fe1—C16126.27 (15)C3—C2—C1119.9 (3)
C10—Fe1—C16157.78 (14)C3—C2—H2A120.0
C9—Fe1—C16161.98 (14)C1—C2—H2A120.0
C6—Fe1—C15122.00 (18)C14—C13—C12108.5 (3)
C7—Fe1—C15105.45 (14)C14—C13—Fe170.54 (18)
C13—Fe1—C1567.94 (14)C12—C13—Fe170.35 (16)
C8—Fe1—C15160.24 (18)C14—C13—H13A125.7
C10—Fe1—C15121.34 (14)C12—C13—H13A125.7
C9—Fe1—C15156.93 (15)Fe1—C13—H13A125.7
C16—Fe1—C1540.50 (12)C10—C7—C6107.2 (4)
C6—Fe1—C14155.8 (2)C10—C7—Fe170.8 (2)
C7—Fe1—C14118.82 (16)C6—C7—Fe169.3 (2)
C13—Fe1—C1440.42 (13)C10—C7—H7A126.4
C8—Fe1—C14159.43 (18)C6—C7—H7A126.4
C10—Fe1—C14105.82 (14)Fe1—C7—H7A126.4
C9—Fe1—C14122.86 (16)C4—N2—C3116.0 (3)
C16—Fe1—C1468.28 (14)C10—C9—C8109.4 (4)
C15—Fe1—C1440.23 (14)C10—C9—Fe170.5 (2)
C6—Fe1—C12126.17 (16)C8—C9—Fe169.9 (2)
C7—Fe1—C12161.19 (16)C10—C9—H9A125.3
C13—Fe1—C1241.18 (11)C8—C9—H9A125.3
C8—Fe1—C12111.72 (13)Fe1—C9—H9A125.3
C10—Fe1—C12159.07 (14)C9—C8—C6107.6 (4)
C9—Fe1—C12126.18 (13)C9—C8—Fe170.9 (2)
C16—Fe1—C1240.71 (11)C6—C8—Fe169.3 (2)
C15—Fe1—C1268.16 (12)C9—C8—H8A126.2
C14—Fe1—C1268.51 (11)C6—C8—H8A126.2
C16—C12—C13106.9 (3)Fe1—C8—H8A126.2
C16—C12—C11131.2 (3)N2—C4—C5124.4 (3)
C13—C12—C11121.9 (3)N2—C4—H4A117.8
C16—C12—Fe169.33 (16)C5—C4—H4A117.8
C13—C12—Fe168.48 (15)C13—C14—C15107.9 (3)
C11—C12—Fe1125.30 (18)C13—C14—Fe169.05 (17)
C17—C11—C12130.0 (3)C15—C14—Fe169.85 (18)
C17—C11—H11A115.0C13—C14—H14A126.1
C12—C11—H11A115.0C15—C14—H14A126.1
C11—C17—C18120.2 (3)Fe1—C14—H14A126.1
C11—C17—C1124.5 (3)C8—C6—C7106.3 (3)
C18—C17—C1115.3 (2)C8—C6—Fe169.8 (2)
N1—C18—C17177.9 (3)C7—C6—Fe169.7 (2)
C15—C16—C12107.9 (3)C8—C6—H6A126.8
C15—C16—Fe169.83 (17)C7—C6—H6A126.8
C12—C16—Fe169.96 (15)Fe1—C6—H6A126.8
C15—C16—H16A126.1N2—C3—C2123.9 (3)
C12—C16—H16A126.1N2—C3—H3A118.1
Fe1—C16—H16A126.1C2—C3—H3A118.1
C6—Fe1—C12—C1676.7 (3)C10—Fe1—C13—C12164.24 (18)
C7—Fe1—C12—C1635.5 (5)C9—Fe1—C13—C12123.00 (19)
C13—Fe1—C12—C16−118.8 (3)C16—Fe1—C13—C12−37.84 (16)
C8—Fe1—C12—C16120.9 (2)C15—Fe1—C13—C12−81.58 (19)
C10—Fe1—C12—C16−159.2 (3)C14—Fe1—C13—C12−119.0 (3)
C9—Fe1—C12—C16163.0 (2)C9—C10—C7—C60.3 (4)
C15—Fe1—C12—C16−37.80 (19)Fe1—C10—C7—C660.1 (2)
C14—Fe1—C12—C16−81.2 (2)C9—C10—C7—Fe1−59.7 (2)
C6—Fe1—C12—C13−164.5 (2)C6—Fe1—C7—C10117.8 (3)
C7—Fe1—C12—C13154.3 (4)C13—Fe1—C7—C10−50.0 (4)
C8—Fe1—C12—C13−120.3 (2)C8—Fe1—C7—C1078.8 (3)
C10—Fe1—C12—C13−40.4 (4)C9—Fe1—C7—C1036.1 (2)
C9—Fe1—C12—C13−78.2 (2)C16—Fe1—C7—C10−161.3 (2)
C16—Fe1—C12—C13118.8 (3)C15—Fe1—C7—C10−120.9 (2)
C15—Fe1—C12—C1381.0 (2)C14—Fe1—C7—C10−79.7 (3)
C14—Fe1—C12—C1337.6 (2)C12—Fe1—C7—C10171.8 (3)
C6—Fe1—C12—C11−49.9 (3)C13—Fe1—C7—C6−167.7 (3)
C7—Fe1—C12—C11−91.0 (5)C8—Fe1—C7—C6−38.9 (2)
C13—Fe1—C12—C11114.6 (3)C10—Fe1—C7—C6−117.8 (3)
C8—Fe1—C12—C11−5.7 (3)C9—Fe1—C7—C6−81.6 (3)
C10—Fe1—C12—C1174.3 (5)C16—Fe1—C7—C680.9 (3)
C9—Fe1—C12—C1136.4 (3)C15—Fe1—C7—C6121.3 (3)
C16—Fe1—C12—C11−126.6 (3)C14—Fe1—C7—C6162.6 (2)
C15—Fe1—C12—C11−164.4 (3)C12—Fe1—C7—C654.0 (5)
C14—Fe1—C12—C11152.2 (3)C7—C10—C9—C80.0 (4)
C16—C12—C11—C1714.0 (5)Fe1—C10—C9—C8−59.2 (2)
C13—C12—C11—C17−168.5 (3)C7—C10—C9—Fe159.2 (2)
Fe1—C12—C11—C17106.6 (3)C6—Fe1—C9—C10−81.5 (3)
C12—C11—C17—C18−1.2 (5)C7—Fe1—C9—C10−36.7 (3)
C12—C11—C17—C1179.4 (3)C13—Fe1—C9—C10116.4 (2)
C13—C12—C16—C151.4 (3)C8—Fe1—C9—C10−120.3 (4)
C11—C12—C16—C15179.2 (3)C16—Fe1—C9—C10−162.4 (4)
Fe1—C12—C16—C1559.8 (2)C15—Fe1—C9—C1036.8 (5)
C13—C12—C16—Fe1−58.40 (19)C14—Fe1—C9—C1073.4 (3)
C11—C12—C16—Fe1119.4 (3)C12—Fe1—C9—C10159.5 (2)
C6—Fe1—C16—C15117.3 (3)C6—Fe1—C9—C838.8 (3)
C7—Fe1—C16—C1574.1 (3)C7—Fe1—C9—C883.6 (3)
C13—Fe1—C16—C15−80.6 (2)C13—Fe1—C9—C8−123.3 (2)
C8—Fe1—C16—C15159.7 (2)C10—Fe1—C9—C8120.3 (4)
C10—Fe1—C16—C1541.5 (5)C16—Fe1—C9—C8−42.1 (6)
C9—Fe1—C16—C15−168.5 (4)C15—Fe1—C9—C8157.1 (4)
C14—Fe1—C16—C15−37.0 (2)C14—Fe1—C9—C8−166.2 (2)
C12—Fe1—C16—C15−118.8 (3)C12—Fe1—C9—C8−80.1 (3)
C6—Fe1—C16—C12−123.8 (2)C10—C9—C8—C6−0.3 (4)
C7—Fe1—C16—C12−167.1 (2)Fe1—C9—C8—C6−59.9 (2)
C13—Fe1—C16—C1238.27 (17)C10—C9—C8—Fe159.6 (3)
C8—Fe1—C16—C12−81.4 (3)C6—Fe1—C8—C9−118.2 (3)
C10—Fe1—C16—C12160.4 (4)C7—Fe1—C8—C9−79.1 (3)
C9—Fe1—C16—C12−49.7 (5)C13—Fe1—C8—C976.5 (3)
C15—Fe1—C16—C12118.8 (3)C10—Fe1—C8—C9−36.3 (2)
C14—Fe1—C16—C1281.86 (19)C16—Fe1—C8—C9165.1 (2)
C12—C16—C15—C14−0.7 (3)C15—Fe1—C8—C9−153.2 (4)
Fe1—C16—C15—C1459.1 (2)C14—Fe1—C8—C934.6 (5)
C12—C16—C15—Fe1−59.86 (19)C12—Fe1—C8—C9121.1 (2)
C6—Fe1—C15—C14157.9 (2)C7—Fe1—C8—C639.0 (3)
C7—Fe1—C15—C14116.6 (2)C13—Fe1—C8—C6−165.3 (2)
C13—Fe1—C15—C14−37.55 (18)C10—Fe1—C8—C681.9 (3)
C8—Fe1—C15—C14−175.7 (4)C9—Fe1—C8—C6118.2 (3)
C10—Fe1—C15—C1477.0 (2)C16—Fe1—C8—C6−76.7 (3)
C9—Fe1—C15—C1450.9 (4)C15—Fe1—C8—C6−35.1 (5)
C16—Fe1—C15—C14−120.1 (3)C14—Fe1—C8—C6152.8 (4)
C12—Fe1—C15—C14−82.1 (2)C12—Fe1—C8—C6−120.7 (3)
C6—Fe1—C15—C16−82.0 (3)C3—N2—C4—C5−1.1 (6)
C7—Fe1—C15—C16−123.3 (2)C1—C5—C4—N20.0 (6)
C13—Fe1—C15—C1682.6 (2)C12—C13—C14—C151.1 (3)
C8—Fe1—C15—C16−55.6 (5)Fe1—C13—C14—C15−59.3 (2)
C10—Fe1—C15—C16−162.9 (2)C12—C13—C14—Fe160.35 (19)
C9—Fe1—C15—C16171.0 (3)C16—C15—C14—C13−0.2 (3)
C14—Fe1—C15—C16120.1 (3)Fe1—C15—C14—C1358.8 (2)
C12—Fe1—C15—C1637.99 (19)C16—C15—C14—Fe1−59.0 (2)
C11—C17—C1—C2−2.4 (4)C6—Fe1—C14—C13−170.4 (3)
C18—C17—C1—C2178.2 (3)C7—Fe1—C14—C13160.9 (2)
C11—C17—C1—C5176.5 (3)C8—Fe1—C14—C1356.5 (4)
C18—C17—C1—C5−3.0 (4)C10—Fe1—C14—C13120.5 (2)
C6—Fe1—C10—C981.4 (3)C9—Fe1—C14—C1381.8 (2)
C7—Fe1—C10—C9120.4 (4)C16—Fe1—C14—C13−82.2 (2)
C13—Fe1—C10—C9−82.2 (3)C15—Fe1—C14—C13−119.4 (3)
C8—Fe1—C10—C936.6 (3)C12—Fe1—C14—C13−38.25 (18)
C16—Fe1—C10—C9165.7 (3)C6—Fe1—C14—C15−51.0 (4)
C15—Fe1—C10—C9−164.0 (2)C7—Fe1—C14—C15−79.7 (2)
C14—Fe1—C10—C9−123.2 (2)C13—Fe1—C14—C15119.4 (3)
C12—Fe1—C10—C9−52.2 (5)C8—Fe1—C14—C15175.9 (4)
C6—Fe1—C10—C7−39.1 (3)C10—Fe1—C14—C15−120.1 (2)
C13—Fe1—C10—C7157.4 (2)C9—Fe1—C14—C15−158.78 (19)
C8—Fe1—C10—C7−83.8 (3)C16—Fe1—C14—C1537.22 (19)
C9—Fe1—C10—C7−120.4 (4)C12—Fe1—C14—C1581.2 (2)
C16—Fe1—C10—C745.3 (5)C9—C8—C6—C70.5 (4)
C15—Fe1—C10—C775.5 (3)Fe1—C8—C6—C7−60.4 (2)
C14—Fe1—C10—C7116.4 (3)C9—C8—C6—Fe160.9 (2)
C12—Fe1—C10—C7−172.6 (3)C10—C7—C6—C8−0.5 (4)
C2—C1—C5—C41.4 (5)Fe1—C7—C6—C860.5 (3)
C17—C1—C5—C4−177.6 (3)C10—C7—C6—Fe1−61.0 (2)
C5—C1—C2—C3−1.7 (5)C7—Fe1—C6—C8−117.1 (3)
C17—C1—C2—C3177.2 (3)C13—Fe1—C6—C844.7 (6)
C16—C12—C13—C14−1.5 (3)C10—Fe1—C6—C8−79.6 (3)
C11—C12—C13—C14−179.6 (2)C9—Fe1—C6—C8−37.2 (2)
Fe1—C12—C13—C14−60.5 (2)C16—Fe1—C6—C8123.9 (2)
C16—C12—C13—Fe158.94 (19)C15—Fe1—C6—C8166.8 (2)
C11—C12—C13—Fe1−119.1 (2)C14—Fe1—C6—C8−156.9 (3)
C6—Fe1—C13—C14166.5 (5)C12—Fe1—C6—C881.7 (3)
C7—Fe1—C13—C14−42.0 (4)C13—Fe1—C6—C7161.9 (4)
C8—Fe1—C13—C14−158.8 (2)C8—Fe1—C6—C7117.1 (3)
C10—Fe1—C13—C14−76.8 (2)C10—Fe1—C6—C737.6 (2)
C9—Fe1—C13—C14−118.0 (2)C9—Fe1—C6—C779.9 (2)
C16—Fe1—C13—C1481.1 (2)C16—Fe1—C6—C7−119.0 (2)
C15—Fe1—C13—C1437.38 (19)C15—Fe1—C6—C7−76.1 (3)
C12—Fe1—C13—C14119.0 (3)C14—Fe1—C6—C7−39.8 (5)
C6—Fe1—C13—C1247.5 (6)C12—Fe1—C6—C7−161.1 (2)
C7—Fe1—C13—C12−161.0 (3)C4—N2—C3—C20.8 (6)
C8—Fe1—C13—C1282.3 (2)C1—C2—C3—N20.7 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14A···N2i0.982.573.476 (4)153

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2092).

References

  • Dupont, J., Consorti, C. S. & Spencer, J. (2005). Chem. Rev.105, 2527–2571. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Shao, L., Hu, Y., Tao, W.-F., Jin, Z. & Fang, J.-X. (2005). Acta Cryst. E61, m1837–m1839.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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