2-Ferrocenyl-3-methoxy-6-methylpyridine

In the title compound, [Fe(C5H5)(C12H12NO)], the dihedral angle between the pyridyl and substituted cyclopentadienyl rings is 23.58 (3)°. The crystal structure is characterized by weak intermolecular C—H⋯N hydrogen-bonding contacts, leading to the formation of chains running parallel to the n-glide planes. A weak intermolecular C—H⋯π contact is also present.

In the title compound, [Fe(C 5 H 5 )(C 12 H 12 NO)], the dihedral angle between the pyridyl and substituted cyclopentadienyl rings is 23.58 (3) . The crystal structure is characterized by weak intermolecular C-HÁ Á ÁN hydrogen-bonding contacts, leading to the formation of chains running parallel to the nglide planes. A weak intermolecular C-HÁ Á Á contact is also present.

Comment
Since the discovery of ferrocene in the 1950s, the fascinating structural properties of ferrocene and its derivatives have been the subject of increasing interest in all fields of organometallic chemistry (Hao et al., 2008;Xu et al., 2009;Wang et al., 2008 with relevant literature cited therein). Among them, ferrocene-heterocycles are one of the most important ones (Sarhan & Izumi, 2003).
In the title compound ( Fig. 1), the dihedral angle between the pyridyl and substituted cyclopentadienyl rings is 23.58 (3)°.
The crystal structure is characterised by weak intermolecular C-H···N hydrogen bonding contacts (Table 1), leading to the formation of one-dimensional chains running parallel to the n-glide planes (Fig. 2). Furthermore, a weak intermolecular C-H···π contact may also be considered in the structure (Table 1). Cg1 is the centroid of the Cp ring C8 -C12. The perpendicular distance of H4 to the Cp ring is 2.812 Å. C-H···π contacts were also observed in a triazol-ferrocene derivative (Hao et al., 2008). The n-glide plane symmetry operation is also observed in the structure of 2-Ferrocenyl-6-methylpyridin-3-ol (Wang et al., 2008), in which the nitrogen atoms form classic intermolecular O-H···N hydrogen bonds with the adjacent -OH groups. Both compounds crystallize in the space group P2 1 /n .

Experimental
The title compound was prepared as described in the literature (Beletskaya et al., 2001;Xu et al., 2009) and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as red crystals.

Refinement
H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C-H distances constrained to 0.93-0.96 Å, and with U iso (H)=1.2U eq (C) (1.5U eq for methyl H). Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.