2-Ferrocenyl-6-(3-nitrophenyl)quinoline

In the title compound, [Fe(C5H5)(C20H13N2O2)], the substituted cyclopentadienyl ring and quinoline system are approximately coplanar, making a dihedral angle of 5.18 (6)°, while the dihedral angle between the quinoline system and the benzene ring is 28.45 (8)°. There is high thermal motion in the free cyclopentadienyl ring compared with the substituted cyclopentadienyl ring. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.

In the title compound, [Fe(C 5 H 5 )(C 20 H 13 N 2 O 2 )], the substituted cyclopentadienyl ring and quinoline system are approximately coplanar, making a dihedral angle of 5.18 (6) , while the dihedral angle between the quinoline system and the benzene ring is 28.45 (8) . There is high thermal motion in the free cyclopentadienyl ring compared with the substituted cyclopentadienyl ring. The conformation of the two cyclopentadienyl rings in the ferrocenyl moiety is eclipsed.

Comment
In recent years, there has been an increasing interest in the design of new ferrocenyl derivatives, owing to their utility in diverse fields of chemistry, such as organic synthesis, catalysis and materials science (Staveren & Metzler-Nolte 2004;Stepnicka 2008;Xu et al., 2010). In addition, quinolines and their derivatives are important natural products (Carey et al., 2006;Michael 2007). Here we report the crystal structure of the title compound, derived from the via A-alkylation and Suzuki reaction of acetylferrocene, (2-amino-5-bromophenyl)methanol and 3-nitrylphenylboronic acid.
A view on the molecular structure of the title compound is given in Fig. 1. The two cyclopentadienyl rings are almost parallel (dihedral angle of 0.94 (3)°). The substituted cyclopentadienyl and quinolinyl ring are approximately coplanar, making dihedral angle of 5.18 (6)°, and the dihedral angle between the quinolinyl and phenyl ring is 28.45 (8)°.

Experimental
The title compound was prepared as described in literature (Xu et al. 2013) and recrystallized from dichloromethane/petroleum ether solution at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

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 Uĩso~(H)=1.2Ueq(C).

Figure 1
The molecular structure of the title compound with displacement ellipsoids at the 30% probability level. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.018 Δρ max = 0.25 e Å −3 Δρ min = −0.33 e Å −3 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 > 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 )
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