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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1043.
Published online 2008 July 19. doi:  10.1107/S1600536808021843
PMCID: PMC2961962

1-[(Z)-2-Cyano-2-(2-pyrid­yl)vin­yl]­ferrocene

Abstract

In the title compound, [Fe(C5H5)(C13H9N2)], the dihedral angle between the substituted cyclo­penta­dienyl plane and the plane of the pyridine ring is 8.43 (14)°. The double bond adopts a Z configuration. In the crystal structure, weak C—H(...)N inter­actions link the molecules into a zigzag chain. A weak intramolecular C—H(...)N hydrogen bond is also present.

Related literature

For the chemistry of ferrocene, see: Chen et al. (2006 [triangle]). For representative ferrocene derivatives, see: Jiao et al. (2003 [triangle]); Mancheno et al. (2004 [triangle]). For similar compounds, see: Boyd & Paauwe (2006 [triangle]); Shao et al. (2005 [triangle]).

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Object name is e-64-m1043-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-m1043-efi1.jpg
  • a = 11.105 (2) Å
  • b = 10.716 (2) Å
  • c = 12.675 (3) Å
  • β = 106.95 (3)°
  • V = 1442.9 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.04 mm−1
  • T = 293 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.725, T max = 0.900
  • 14799 measured reflections
  • 3311 independent reflections
  • 2564 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.094
  • S = 1.07
  • 3311 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.24 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/S1600536808021843/bq2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021843/bq2088Isup2.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 CCD X-ray diffractometer.

supplementary crystallographic information

Comment

The molecular structure of the title compound is shown in Fig. 1. The Fe···Cg1 and Fe···Cg2 distances are 1.6548 (16)Å and 1.6445 (12)Å respectively and the Cg1··· Fe··· Cg2 angle is 179.55 (8)°, where Cg1 and Cg2 are the centroids of the unsubstituted and substituted cyclopentadienyl rings. The double bond (C16═C17) exhibits a cis configuration and the pyridine plane makes an angle of 8.43 (14)Å with the substituted cyclopentadienyl ring. The planar cyclopentadienyl rings of the ferrocenyl unit are nearly parallel to each other [the interplanar angle is 1.33 (17)°]. The crystal structure is stabilized by weak intramolecular C—H···N interactions. Fig 2 shows that the molecules assemble as zigzag chains in the crystal structure along the a axis, formed by weak intermolecular C—H···N hydrogen bonds (Table 1).

Experimental

1 ml pyrrolidine was added to the mixture of formylferrocene (2.15 g, 0.01 mol) and 2-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 as eluant. Brownish red single crystals suitable for X-ray analysis were obtained by slow evaporation of ether at room temperature after several hours.

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.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Hydrojen bond are shown as dashed lines
Fig. 2.
The packing diagram of the title compound, viewed along the a axis.

Crystal data

[Fe(C5H5)(C13H9N2)]F000 = 648
Mr = 314.16Dx = 1.446 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 12734 reflections
a = 11.105 (2) Åθ = 6.7–55.3º
b = 10.716 (2) ŵ = 1.04 mm1
c = 12.675 (3) ÅT = 293 (2) K
β = 106.95 (3)ºPrism, red brown
V = 1442.9 (5) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Rigaku Mercury2 (2x2 bin mode) diffractometer3311 independent reflections
Radiation source: fine-focus sealed tube2564 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
Detector resolution: 13.6612 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.4º
CCD_Profile_fitting scansh = −14→14
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)k = −13→13
Tmin = 0.725, Tmax = 0.900l = −16→16
14799 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)] = 0.041H-atom parameters constrained
wR(F2) = 0.094  w = 1/[σ2(Fo2) + (0.0372P)2 + 0.4341P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3311 reflectionsΔρmax = 0.24 e Å3
190 parametersΔρmin = −0.24 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
Fe10.19959 (3)0.79543 (3)0.08768 (3)0.03864 (12)
C100.1744 (2)0.6098 (2)0.0568 (2)0.0452 (5)
H10A0.17030.54560.11080.054*
C90.2868 (2)0.6523 (2)0.03368 (18)0.0400 (5)
C150.6436 (2)0.5798 (2)0.15481 (19)0.0422 (5)
C170.5244 (2)0.6339 (2)0.08206 (18)0.0404 (5)
C160.4110 (2)0.6083 (2)0.09516 (19)0.0419 (5)
H16A0.41240.55390.15260.050*
N20.63206 (19)0.5064 (2)0.23633 (19)0.0559 (6)
C180.5387 (2)0.7169 (3)−0.0022 (2)0.0523 (6)
C80.2495 (2)0.7467 (2)−0.04956 (19)0.0444 (5)
H8A0.30560.7937−0.08200.053*
C70.1167 (2)0.7601 (3)−0.0764 (2)0.0489 (6)
H7A0.06560.8192−0.13010.059*
N10.5562 (3)0.7837 (3)−0.0659 (2)0.0831 (9)
C140.7600 (2)0.6058 (3)0.1397 (2)0.0545 (6)
H1A0.76580.65680.08200.065*
C50.3262 (2)0.8697 (3)0.2228 (2)0.0551 (7)
H5A0.41380.84270.25320.066*
C110.8554 (3)0.4798 (3)0.2947 (3)0.0659 (8)
H11A0.92600.44430.34410.079*
C130.8671 (2)0.5547 (3)0.2116 (3)0.0658 (8)
H13A0.94600.57140.20320.079*
C40.2841 (3)0.9625 (2)0.1432 (2)0.0570 (7)
H4A0.33621.01230.10860.068*
C60.0708 (2)0.6760 (2)−0.0113 (2)0.0494 (6)
H6A−0.01720.6664−0.01220.059*
C20.1158 (3)0.8840 (4)0.1894 (4)0.0946 (13)
H2A0.02980.87000.19270.114*
C120.7372 (3)0.4577 (3)0.3038 (3)0.0667 (8)
H12A0.72980.40580.36040.080*
C30.2238 (4)0.8212 (3)0.2518 (2)0.0751 (10)
H3A0.22680.75560.30630.090*
C10.1528 (3)0.9719 (3)0.1227 (3)0.0840 (11)
H1B0.09691.02940.07070.101*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.03100 (18)0.0435 (2)0.0417 (2)−0.00034 (14)0.01115 (13)−0.00617 (15)
C100.0451 (13)0.0435 (13)0.0463 (13)−0.0074 (10)0.0122 (10)−0.0034 (11)
C90.0417 (12)0.0401 (12)0.0412 (12)−0.0010 (10)0.0167 (10)−0.0059 (10)
C150.0434 (13)0.0364 (12)0.0505 (14)0.0016 (10)0.0195 (11)−0.0089 (10)
C170.0461 (13)0.0351 (12)0.0445 (13)0.0016 (10)0.0204 (10)−0.0062 (10)
C160.0459 (13)0.0381 (12)0.0454 (13)0.0026 (10)0.0193 (10)−0.0023 (10)
N20.0445 (12)0.0576 (13)0.0678 (14)0.0062 (10)0.0198 (11)0.0123 (11)
C180.0431 (14)0.0598 (17)0.0593 (16)0.0034 (12)0.0233 (12)0.0040 (13)
C80.0453 (13)0.0511 (13)0.0397 (12)0.0000 (11)0.0170 (11)−0.0011 (11)
C70.0461 (14)0.0572 (15)0.0388 (13)0.0002 (11)0.0051 (11)−0.0016 (11)
N10.0676 (17)0.100 (2)0.090 (2)0.0035 (15)0.0367 (15)0.0364 (17)
C140.0470 (14)0.0577 (16)0.0645 (17)0.0010 (12)0.0255 (13)−0.0014 (13)
C50.0505 (14)0.0611 (17)0.0459 (14)0.0000 (13)0.0016 (12)−0.0139 (13)
C110.0457 (15)0.0678 (19)0.081 (2)0.0107 (14)0.0126 (14)0.0006 (16)
C130.0404 (14)0.075 (2)0.085 (2)0.0026 (14)0.0225 (14)−0.0074 (17)
C40.0566 (16)0.0460 (15)0.0618 (17)−0.0087 (12)0.0072 (13)−0.0111 (13)
C60.0359 (12)0.0571 (16)0.0512 (14)−0.0097 (11)0.0066 (11)−0.0082 (12)
C20.058 (2)0.114 (3)0.126 (3)−0.019 (2)0.050 (2)−0.073 (3)
C120.0573 (17)0.068 (2)0.0741 (19)0.0057 (14)0.0184 (15)0.0180 (15)
C30.107 (3)0.079 (2)0.0500 (17)−0.017 (2)0.0393 (18)−0.0222 (15)
C10.064 (2)0.061 (2)0.106 (3)0.0237 (16)−0.0094 (19)−0.0369 (19)

Geometric parameters (Å, °)

Fe1—C102.031 (2)C8—C71.421 (3)
Fe1—C22.032 (3)C8—H8A0.9800
Fe1—C52.034 (2)C7—C61.414 (4)
Fe1—C92.036 (2)C7—H7A0.9800
Fe1—C32.037 (3)C14—C131.383 (4)
Fe1—C82.042 (2)C14—H1A0.9300
Fe1—C42.048 (3)C5—C31.393 (4)
Fe1—C72.050 (2)C5—C41.397 (4)
Fe1—C62.052 (2)C5—H5A0.9800
Fe1—C12.044 (3)C11—C131.361 (4)
C10—C61.411 (3)C11—C121.372 (4)
C10—C91.438 (3)C11—H11A0.9300
C10—H10A0.9800C13—H13A0.9300
C9—C81.432 (3)C4—C11.408 (4)
C9—C161.450 (3)C4—H4A0.9800
C15—N21.334 (3)C6—H6A0.9800
C15—C141.389 (3)C2—C11.404 (5)
C15—C171.492 (3)C2—C31.401 (5)
C17—C161.346 (3)C2—H2A0.9800
C17—C181.433 (3)C12—H12A0.9300
C16—H16A0.9300C3—H3A0.9800
N2—C121.336 (3)C1—H1B0.9800
C18—N11.138 (3)
C10—Fe1—C2121.13 (14)C17—C16—H16A114.9
C10—Fe1—C5124.61 (11)C9—C16—H16A114.9
C2—Fe1—C567.36 (12)C15—N2—C12117.6 (2)
C10—Fe1—C941.40 (9)N1—C18—C17176.5 (3)
C2—Fe1—C9156.35 (17)C7—C8—C9107.8 (2)
C5—Fe1—C9107.32 (10)C7—C8—Fe169.98 (14)
C10—Fe1—C3107.43 (12)C9—C8—Fe169.22 (13)
C2—Fe1—C340.27 (14)C7—C8—H8A126.1
C5—Fe1—C340.03 (12)C9—C8—H8A126.1
C9—Fe1—C3120.76 (13)Fe1—C8—H8A126.1
C10—Fe1—C868.99 (10)C6—C7—C8108.7 (2)
C2—Fe1—C8161.54 (16)C6—C7—Fe169.92 (14)
C5—Fe1—C8121.64 (11)C8—C7—Fe169.38 (14)
C9—Fe1—C841.13 (9)C6—C7—H7A125.6
C3—Fe1—C8156.49 (13)C8—C7—H7A125.6
C10—Fe1—C4161.07 (10)Fe1—C7—H7A125.6
C2—Fe1—C467.80 (14)C13—C14—C15119.1 (3)
C5—Fe1—C440.01 (11)C13—C14—H1A120.5
C9—Fe1—C4123.96 (10)C15—C14—H1A120.5
C3—Fe1—C467.64 (12)C3—C5—C4109.2 (3)
C8—Fe1—C4107.79 (11)C3—C5—Fe170.08 (16)
C10—Fe1—C768.15 (10)C4—C5—Fe170.54 (14)
C2—Fe1—C7125.25 (14)C3—C5—H5A125.4
C5—Fe1—C7157.24 (11)C4—C5—H5A125.4
C9—Fe1—C768.70 (10)Fe1—C5—H5A125.4
C3—Fe1—C7161.43 (13)C13—C11—C12118.5 (3)
C8—Fe1—C740.64 (9)C13—C11—H11A120.8
C4—Fe1—C7122.35 (11)C12—C11—H11A120.8
C10—Fe1—C640.43 (9)C11—C13—C14119.1 (3)
C2—Fe1—C6108.25 (12)C11—C13—H13A120.5
C5—Fe1—C6161.08 (11)C14—C13—H13A120.5
C9—Fe1—C668.88 (10)C5—C4—C1107.2 (3)
C3—Fe1—C6124.75 (12)C5—C4—Fe169.45 (15)
C8—Fe1—C668.49 (10)C1—C4—Fe169.68 (16)
C4—Fe1—C6157.37 (11)C5—C4—H4A126.4
C7—Fe1—C640.34 (10)C1—C4—H4A126.4
C10—Fe1—C1156.70 (13)Fe1—C4—H4A126.4
C2—Fe1—C140.31 (16)C10—C6—C7108.0 (2)
C5—Fe1—C167.21 (12)C10—C6—Fe168.98 (13)
C9—Fe1—C1161.07 (15)C7—C6—Fe169.74 (14)
C3—Fe1—C167.60 (15)C10—C6—H6A126.0
C8—Fe1—C1124.84 (15)C7—C6—H6A126.0
C4—Fe1—C140.26 (12)Fe1—C6—H6A126.0
C7—Fe1—C1108.88 (13)C1—C2—C3108.0 (3)
C6—Fe1—C1122.26 (12)C1—C2—Fe170.29 (18)
C6—C10—C9108.5 (2)C3—C2—Fe170.05 (17)
C6—C10—Fe170.59 (14)C1—C2—H2A126.0
C9—C10—Fe169.48 (13)C3—C2—H2A126.0
C6—C10—H10A125.7Fe1—C2—H2A126.0
C9—C10—H10A125.7N2—C12—C11123.9 (3)
Fe1—C10—H10A125.7N2—C12—H12A118.0
C8—C9—C10107.0 (2)C11—C12—H12A118.0
C8—C9—C16130.6 (2)C5—C3—C2107.6 (3)
C10—C9—C16122.2 (2)C5—C3—Fe169.89 (16)
C8—C9—Fe169.65 (13)C2—C3—Fe169.68 (19)
C10—C9—Fe169.11 (13)C5—C3—H3A126.2
C16—C9—Fe1122.35 (16)C2—C3—H3A126.2
N2—C15—C14121.9 (2)Fe1—C3—H3A126.2
N2—C15—C17116.1 (2)C2—C1—C4108.0 (3)
C14—C15—C17122.0 (2)C2—C1—Fe169.40 (18)
C16—C17—C18122.0 (2)C4—C1—Fe170.06 (15)
C16—C17—C15122.5 (2)C2—C1—H1B126.0
C18—C17—C15115.5 (2)C4—C1—H1B126.0
C17—C16—C9130.1 (2)Fe1—C1—H1B126.0
C2—Fe1—C10—C681.7 (2)C3—Fe1—C5—C4−119.9 (3)
C5—Fe1—C10—C6164.22 (16)C8—Fe1—C5—C479.87 (19)
C9—Fe1—C10—C6−119.4 (2)C7—Fe1—C5—C446.5 (4)
C3—Fe1—C10—C6123.55 (18)C6—Fe1—C5—C4−162.1 (3)
C8—Fe1—C10—C6−81.09 (16)C1—Fe1—C5—C4−38.1 (2)
C4—Fe1—C10—C6−164.7 (3)C12—C11—C13—C140.0 (4)
C7—Fe1—C10—C6−37.29 (15)C15—C14—C13—C110.4 (4)
C1—Fe1—C10—C649.9 (4)C3—C5—C4—C10.1 (3)
C2—Fe1—C10—C9−158.91 (18)Fe1—C5—C4—C159.75 (18)
C5—Fe1—C10—C9−76.36 (17)C3—C5—C4—Fe1−59.64 (19)
C3—Fe1—C10—C9−117.04 (17)C10—Fe1—C4—C5−41.3 (4)
C8—Fe1—C10—C938.33 (13)C2—Fe1—C4—C580.8 (2)
C4—Fe1—C10—C9−45.3 (4)C9—Fe1—C4—C5−75.9 (2)
C7—Fe1—C10—C982.13 (15)C3—Fe1—C4—C537.08 (18)
C6—Fe1—C10—C9119.4 (2)C8—Fe1—C4—C5−118.34 (17)
C1—Fe1—C10—C9169.3 (3)C7—Fe1—C4—C5−160.60 (16)
C6—C10—C9—C80.4 (3)C6—Fe1—C4—C5165.0 (3)
Fe1—C10—C9—C8−59.63 (16)C1—Fe1—C4—C5118.3 (3)
C6—C10—C9—C16175.9 (2)C10—Fe1—C4—C1−159.7 (3)
Fe1—C10—C9—C16115.9 (2)C2—Fe1—C4—C1−37.6 (2)
C6—C10—C9—Fe160.04 (17)C5—Fe1—C4—C1−118.3 (3)
C10—Fe1—C9—C8118.34 (19)C9—Fe1—C4—C1165.8 (2)
C2—Fe1—C9—C8168.5 (3)C3—Fe1—C4—C1−81.3 (2)
C5—Fe1—C9—C8−118.57 (15)C8—Fe1—C4—C1123.3 (2)
C3—Fe1—C9—C8−160.17 (16)C7—Fe1—C4—C181.1 (2)
C4—Fe1—C9—C8−77.80 (17)C6—Fe1—C4—C146.7 (4)
C7—Fe1—C9—C837.66 (14)C9—C10—C6—C7−0.4 (3)
C6—Fe1—C9—C881.07 (15)Fe1—C10—C6—C758.99 (17)
C1—Fe1—C9—C8−48.5 (4)C9—C10—C6—Fe1−59.35 (16)
C2—Fe1—C9—C1050.1 (3)C8—C7—C6—C100.2 (3)
C5—Fe1—C9—C10123.08 (15)Fe1—C7—C6—C10−58.51 (17)
C3—Fe1—C9—C1081.49 (18)C8—C7—C6—Fe158.70 (17)
C8—Fe1—C9—C10−118.34 (19)C2—Fe1—C6—C10−116.9 (2)
C4—Fe1—C9—C10163.86 (15)C5—Fe1—C6—C10−43.6 (4)
C7—Fe1—C9—C10−80.68 (15)C9—Fe1—C6—C1038.14 (14)
C6—Fe1—C9—C10−37.27 (14)C3—Fe1—C6—C10−75.4 (2)
C1—Fe1—C9—C10−166.9 (3)C8—Fe1—C6—C1082.44 (15)
C10—Fe1—C9—C16−115.7 (2)C4—Fe1—C6—C10167.2 (3)
C2—Fe1—C9—C16−65.6 (4)C7—Fe1—C6—C10119.7 (2)
C5—Fe1—C9—C167.4 (2)C1—Fe1—C6—C10−159.0 (2)
C3—Fe1—C9—C16−34.2 (2)C10—Fe1—C6—C7−119.7 (2)
C8—Fe1—C9—C16125.9 (3)C2—Fe1—C6—C7123.4 (2)
C4—Fe1—C9—C1648.1 (2)C5—Fe1—C6—C7−163.3 (3)
C7—Fe1—C9—C16163.6 (2)C9—Fe1—C6—C7−81.56 (16)
C6—Fe1—C9—C16−153.0 (2)C3—Fe1—C6—C7164.90 (18)
C1—Fe1—C9—C1677.4 (4)C8—Fe1—C6—C7−37.26 (15)
N2—C15—C17—C16−1.7 (3)C4—Fe1—C6—C747.5 (4)
C14—C15—C17—C16179.2 (2)C1—Fe1—C6—C781.3 (2)
N2—C15—C17—C18177.4 (2)C10—Fe1—C2—C1−161.20 (17)
C14—C15—C17—C18−1.6 (3)C5—Fe1—C2—C181.0 (2)
C18—C17—C16—C90.5 (4)C9—Fe1—C2—C1162.4 (2)
C15—C17—C16—C9179.6 (2)C3—Fe1—C2—C1118.7 (3)
C8—C9—C16—C17−8.6 (4)C8—Fe1—C2—C1−42.1 (5)
C10—C9—C16—C17177.1 (2)C4—Fe1—C2—C137.53 (18)
Fe1—C9—C16—C17−98.6 (3)C7—Fe1—C2—C1−77.3 (2)
C14—C15—N2—C12−0.1 (4)C6—Fe1—C2—C1−118.69 (19)
C17—C15—N2—C12−179.2 (2)C10—Fe1—C2—C380.1 (2)
C10—C9—C8—C7−0.3 (3)C5—Fe1—C2—C3−37.71 (19)
C16—C9—C8—C7−175.3 (2)C9—Fe1—C2—C343.7 (4)
Fe1—C9—C8—C7−59.58 (17)C8—Fe1—C2—C3−160.8 (3)
C10—C9—C8—Fe159.29 (15)C4—Fe1—C2—C3−81.2 (2)
C16—C9—C8—Fe1−115.7 (2)C7—Fe1—C2—C3164.06 (18)
C10—Fe1—C8—C780.51 (16)C6—Fe1—C2—C3122.6 (2)
C2—Fe1—C8—C7−46.3 (4)C1—Fe1—C2—C3−118.7 (3)
C5—Fe1—C8—C7−160.94 (16)C15—N2—C12—C110.6 (5)
C9—Fe1—C8—C7119.1 (2)C13—C11—C12—N2−0.6 (5)
C3—Fe1—C8—C7166.0 (3)C4—C5—C3—C20.2 (3)
C4—Fe1—C8—C7−119.28 (16)Fe1—C5—C3—C2−59.7 (2)
C6—Fe1—C8—C736.99 (15)C4—C5—C3—Fe159.92 (18)
C1—Fe1—C8—C7−78.15 (19)C1—C2—C3—C5−0.4 (3)
C10—Fe1—C8—C9−38.57 (13)Fe1—C2—C3—C559.86 (19)
C2—Fe1—C8—C9−165.4 (3)C1—C2—C3—Fe1−60.3 (2)
C5—Fe1—C8—C979.98 (17)C10—Fe1—C3—C5123.48 (17)
C3—Fe1—C8—C946.9 (3)C2—Fe1—C3—C5−118.6 (3)
C4—Fe1—C8—C9121.64 (15)C9—Fe1—C3—C580.2 (2)
C7—Fe1—C8—C9−119.1 (2)C8—Fe1—C3—C546.2 (4)
C6—Fe1—C8—C9−82.09 (15)C4—Fe1—C3—C5−37.06 (17)
C1—Fe1—C8—C9162.77 (15)C7—Fe1—C3—C5−163.4 (3)
C9—C8—C7—C60.1 (3)C6—Fe1—C3—C5164.61 (16)
Fe1—C8—C7—C6−59.03 (18)C1—Fe1—C3—C5−80.8 (2)
C9—C8—C7—Fe159.10 (16)C10—Fe1—C3—C2−117.9 (2)
C10—Fe1—C7—C637.37 (15)C5—Fe1—C3—C2118.6 (3)
C2—Fe1—C7—C6−76.1 (2)C9—Fe1—C3—C2−161.2 (2)
C5—Fe1—C7—C6166.1 (3)C8—Fe1—C3—C2164.8 (3)
C9—Fe1—C7—C682.05 (16)C4—Fe1—C3—C281.6 (2)
C3—Fe1—C7—C6−42.2 (4)C7—Fe1—C3—C2−44.8 (5)
C8—Fe1—C7—C6120.1 (2)C6—Fe1—C3—C2−76.8 (2)
C4—Fe1—C7—C6−160.39 (15)C1—Fe1—C3—C237.9 (2)
C1—Fe1—C7—C6−117.96 (19)C3—C2—C1—C40.5 (3)
C10—Fe1—C7—C8−82.78 (16)Fe1—C2—C1—C4−59.6 (2)
C2—Fe1—C7—C8163.7 (2)C3—C2—C1—Fe160.1 (2)
C5—Fe1—C7—C846.0 (3)C5—C4—C1—C2−0.4 (3)
C9—Fe1—C7—C8−38.10 (15)Fe1—C4—C1—C259.2 (2)
C3—Fe1—C7—C8−162.4 (4)C5—C4—C1—Fe1−59.61 (19)
C4—Fe1—C7—C879.47 (18)C10—Fe1—C1—C244.2 (4)
C6—Fe1—C7—C8−120.1 (2)C5—Fe1—C1—C2−81.4 (2)
C1—Fe1—C7—C8121.90 (19)C9—Fe1—C1—C2−158.1 (3)
N2—C15—C14—C13−0.4 (4)C3—Fe1—C1—C2−37.8 (2)
C17—C15—C14—C13178.6 (2)C8—Fe1—C1—C2165.02 (19)
C10—Fe1—C5—C3−75.2 (2)C4—Fe1—C1—C2−119.2 (3)
C2—Fe1—C5—C337.9 (2)C7—Fe1—C1—C2122.7 (2)
C9—Fe1—C5—C3−117.5 (2)C6—Fe1—C1—C280.1 (2)
C8—Fe1—C5—C3−160.23 (19)C10—Fe1—C1—C4163.4 (3)
C4—Fe1—C5—C3119.9 (3)C2—Fe1—C1—C4119.2 (3)
C7—Fe1—C5—C3166.4 (3)C5—Fe1—C1—C437.87 (18)
C6—Fe1—C5—C3−42.2 (4)C9—Fe1—C1—C4−38.8 (5)
C1—Fe1—C5—C381.8 (2)C3—Fe1—C1—C481.4 (2)
C10—Fe1—C5—C4164.91 (16)C8—Fe1—C1—C4−75.8 (2)
C2—Fe1—C5—C4−82.0 (2)C7—Fe1—C1—C4−118.11 (19)
C9—Fe1—C5—C4122.60 (17)C6—Fe1—C1—C4−160.66 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···N20.932.412.804 (3)105
C4—H4A···N1i0.982.623.538 (4)156

Symmetry codes: (i) −x+1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2088).

References

  • Boyd, P. D. W. & Paauwe, J. D. (2006). Acta Cryst. E62, m2153–m2155.
  • Chen, W., Mbafor, W., Roberts, S. M. & Whittall, J. (2006). J. Am. Chem. Soc.128, 3922–3923. [PubMed]
  • Jiao, J., Long, G. J., Grandjean, F., Beatty, A. M. & Fehlner, T. P. (2003). J. Am. Chem. Soc.125, 7522–7523. [PubMed]
  • Mancheno, O. G., Arrayas, R. G. & Carretero, J. C. (2004). J. Am. Chem. Soc.126, 456–457. [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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