N-Ferrocenymethyl-N-phenylpropionamide

In the title compound, [Fe(C5H5)(C15H16NO)], the two cyclopentadienyl (Cp) rings are nearly parallel to each other, forming a dihedral angle of 3.7 (1)°, and adopt a staggered conformation. The amide group is almost perpendicular to the plane of the substituted Cp ring, with a C—N—C—C torsion angle of 101.3 (2)°, and the N and O atoms in the ethanoyl group are coplanar, with a C—N—C—O torsion angle of −0.7 (3)°. Weak C—H⋯O hydrogen bonds link adjacent molecules.

In the title compound, [Fe(C 5 H 5 )(C 15 H 16 NO)], the two cyclopentadienyl (Cp) rings are nearly parallel to each other, forming a dihedral angle of 3.7 (1) , and adopt a staggered conformation. The amide group is almost perpendicular to the plane of the substituted Cp ring, with a C-N-C-C torsion angle of 101.3 (2) , and the N and O atoms in the ethanoyl group are coplanar, with a C-N-C-O torsion angle of À0.7 (3) . Weak C-HÁ Á ÁO hydrogen bonds link adjacent molecules.

Experimental
N-ferrocenylmethylaniline was obtained according to literature procedures (Osgerby & Pauson, 1961). To a round bottom flask equipped with a reflux condenser and a magnetic stirrer was added under a nitrogen atmosphere a portion of Nferrocenylmethylaniline (6 g, 20 mmol) in 50 ml of anhydride toluene. The resulting suspension was heated at 65°C until total dissolution. 10 ml of propenoique acid was then added and the resulting mixture was vigorously stirred under reflux for 25 min. The reaction mixture was then allowed to cool to room temperature and washed twice with water. The organic layer was then dried and evaporated. The residue was recrystallized from a mixture of ethanol-water to yield Nferrocenymethyl-N-phenylpropionamide as yellow-orange needles (yield: 5.85 g, 84%). m.p. 121-122°C. The compounds gave clean 1 H and 13 C NMR spectra in CDCl 3 .

Figure 1
The molecular structure of the title compound, showing the 50% probability displacement ellipsoids.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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