(Z)-3-Ferrocenyl-2-phenylacrylonitrile

In the structure of the title compound, [Fe(C5H5)(C14H10N)], the unsubstituted cyclopentadiene (Cp) ring is disordered over two positions, with site-occupancy factors 0.76 (2) and 0.24 (2). The dihedral angles between the substituted Cp ring and the major and the minor components of the disordered ring are 0.9 (5) and 6(2)°, repectively. The plane of the acrylonitrile unit makes dihedral angles of 6.1 (18) and 6.5 (4)° with the substituted Cp ring and the phenyl ring planes, respectively.


Experimental
Crystal data [Fe(C 5  supporting information . E64, m822 [doi:10.1107/S1600536808014517] (Z)-3-Ferrocenyl-2-phenylacrylonitrile Lu-Yang Cao and Heng-Yun Ye S1. Comment The chemistry of ferrocene has received much attention because of its applications in many fields, such as in catalysis, organic or organometallic synthesis and materials (Togni, et al.(1995)). The use of ferrocene and its derivatives as nonlinear optical(NLO) materials has also been reported (Long, 1995;Roberto et al., 2000). As part of our on going studies of the chemistry of ferrocene, we present here the structure of the title compound, (Z)-2-Phenyl-3-(ferrocenyl)acrylonitrile (I).

S2. Experimental
To a mixture of ferrocenecarboxaldehyde and 2-phenyletonitrile in CH 2 Cl 2 was added pyrrolidine and the mixture was heated to reflux temperature for 3 h. The reaction was cooled to room temperature and solvent removed. The crude product was purified by column chromatography on silica gel using ethyl acetate-petroleum ether (v:v, 1:3) as eluent to collect the main yellow band. Red crystals suitable for X-ray analysis were obtained by slow evaporation of a saturated solution of ethyl acetate-petroleum ether (v:v,1:3). BAND YELLOW, CRYSTALS RED. IS THIS CORRECT??

S3. Refinement
All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.93Å, U iso =1.2U eq (C). The unsubstituted Cp ring is disordered over two positions with site occupancy factors 0.76 (2) and 0.24 (2) respectively; corresponding C atoms were restrained to have the same anisotropic displacement parameters.  The structure of I showing the atom numbering scheme with displacement ellipsoids drawn at the 30% probability level.
For clarity only atoms of the major disorder component of the unsubstituted cyclopentadiene ring are included. Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ. (