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Acta Cryst. (2008). E64, m1072    [ doi:10.1107/S1600536808023106 ]

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

X.-Q. Fu and W. Wang

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. Packing of the title compound, viewed along the b axis. Dashed lines indicate C—H···N hydrogen-bond interactions.
(Z)-3-Ferrocenyl-2-(4-pyridyl)propenenitrile top
Crystal data top
[Fe(C5H5)(C13H9N2)]F000 = 648
Mr = 314.16Dx = 1.463 Mg m−3
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 mm−1
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 top
Rigaku SCXmini
diffractometer		3229 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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-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 Å−3
190 parametersΔρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Fe(C5H5)(C13H9N2)]V = 1426.5 (6) Å3
Mr = 314.16Z = 4
Monoclinic, P21/nMo Kα
a = 11.520 (2) ŵ = 1.05 mm−1
b = 6.0650 (15) ÅT = 293 (2) K
c = 20.421 (5) Å0.40 × 0.35 × 0.10 mm
β = 91.194 (18)º
Data collection top
Rigaku SCXmini
diffractometer		3229 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2543 reflections with I > 2σ(I)
Tmin = 0.779, Tmax = 1.000Rint = 0.051
13960 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049190 parameters
wR(F2) = 0.123H-atom parameters constrained
S = 1.05Δρmax = 0.36 e Å−3
3229 reflectionsΔρmin = −0.46 e Å−3
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 > 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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

Dupont, J., Consorti, C. S. & Spencer, J. (2005). Chem. Rev. 105, 2527–2571.

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.