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

Xue-Qun Fu; Wei Wang

doi:10.1107/S1600536808023106

. 2008 Jul 26;64(Pt 8):m1072. doi: 10.1107/S1600536808023106

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

Xue-Qun Fu ^a, Wei Wang ^a,^*

PMCID: PMC2961982 PMID: 21203052

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 ▶); Shao et al. (2005 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₃H₉N₂)]
M _r = 314.16
Monoclinic,
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 ▶) 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
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

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

e-64-m1072-sup1.cif^{(26.9KB, cif)}

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

e-64-m1072-Isup2.hkl^{(158.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯N2ⁱ	0.98	2.57	3.476 (4)	153

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Symmetry code: (i) Inline graphic .

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.