2-Amino-4-(4-chlorophenyl)-6-ferrocenylpyridine-3-carbonitrile

In the molecule of the title compound, [Fe(C5H5)(C17H11ClN3)], the dihedral angles between the two five–membered rings and between the two six-membered rings are 3.28 (4) and 51.33 (4)°, respectively. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules into centrosymmetric dimers.

In the molecule of the title compound, [Fe(C 5 H 5 )-(C 17 H 11 ClN 3 )], the dihedral angles between the two fivemembered rings and between the two six-membered rings are 3.28 (4) and 51.33 (4) , respectively. In the crystal structure, intermolecular N-HÁ Á ÁN hydrogen bonds link the molecules into centrosymmetric dimers.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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. supporting information Acta Cryst. (2008). E64, m730 [doi:10.1107/S1600536808008714] 2-Amino-4-(4-chlorophenyl)-6-ferrocenylpyridine-3-carbonitrile Jinpeng Zhang, Shu Yan, Zhen He, Lichun Xu and Shuiping Huang S1. Comment Metallocenes are known to exhibit a wide range of biological activity. Among them, ferrocene has attracted special attention since it is neutral, chemically stable, non-toxic and able to cross cell membranes (Dombrowski et al., 1986). In fact, it is now well established that the incorporation of ferrocene units into organic molecules introduces significant and new properties in these materials. In addition, it has been demonstrated that molecules containing cyanopyridine moiety may be able to work as ligands towards transition-metal ions (Alyoubi, 2000), new drugs (Murata et al., 2004;Desai & Shah, 2003) and significant intermediates for the synthesis of important vitamins such as nicotinic acids and nicotinamides. For these reasons, the synthesis of new compounds containing cyanopyridine derivatives is strongly desired. We report herein the crystal structure of the title compound, (I).
In the molecule of (I), ( In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

S3. Refinement
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH 2 ) and C-H = 0.93 Å for aromatic H,and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C,N).

Figure 1
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.  A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.

2-Amino-4-(4-chlorophenyl)-6-ferrocenylpyridine-3-carbonitrile
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 > 2sigma(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.