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

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.

In the title compound, [Fe(C 5 H 5 )(C 13 H 9 N 2 )], 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-HÁ Á ÁN hydrogen bonds link the molecules into a onedimensional chain in the a+c direction. 190 parameters H-atom parameters constrained Á max = 0.36 e Å À3 Á min = À0.46 e Å À3 Table 1 Hydrogen-bond geometry (Å , ).
supporting information . E64, m1072 [doi:10.1107/S1600536808023106] (Z)-3-Ferrocenyl-2-(4-pyridyl)propenenitrile Xue-Qun Fu and Wei Wang S1. 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)

S2. 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.

S3. 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 U iso (H) = 1.2U eq (C).

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 F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.