2-Ferrocenyl-6-methyl­pyridin-3-ol

Zhi-Qiang Wang; Chen Xu; Fei-Fei Cen; Ying-Fei Li; Bao-Ming Ji

doi:10.1107/S1600536808039597

. 2008 Nov 29;64(Pt 12):m1633. doi: 10.1107/S1600536808039597

2-Ferrocenyl-6-methylpyridin-3-ol

Zhi-Qiang Wang ^a, Chen Xu ^a, Fei-Fei Cen ^b, Ying-Fei Li ^b, Bao-Ming Ji ^a,^*

PMCID: PMC2960045 PMID: 21581222

Abstract

In the title compound, [Fe(C₅H₅)(C₁₁H₁₀NO)], the dihedral angle between the pyridyl and substituted cyclopentadienyl rings is 20.4 (3)°. The H atoms of the methyl group are disordered over two positions; their site-occupation factors were fixed at 0.5. The crystal structure is stabilized by well defined intermolecular O—H⋯N and C—H⋯O hydrogen bonds, leading to the formation of a two-dimensional network parallel to (101).

Related literature

For ferrocene and its derivatives, see: Beletskaya et al. (2001 ▶); Hayashi & Togni (1995 ▶); Kealy & Pauson (1951 ▶); Sarhan & Izumi (2003 ▶); Staveren & Metzler-Nolte (2004 ▶); Xu et al. (2007 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₁H₁₀NO)]
M _r = 293.14
Monoclinic,
a = 10.4370 (13) Å
b = 12.7196 (15) Å
c = 10.5424 (13) Å
β = 111.0330 (10)°
V = 1306.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 291 (2) K
0.37 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.675, T _max = 0.793
7569 measured reflections
2422 independent reflections
1970 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.099
S = 1.08
2422 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039597/fj2173sup1.cif

e-64-m1633-sup1.cif^{(27.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039597/fj2173Isup2.hkl

e-64-m1633-Isup2.hkl^{(119KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	1.96	2.774 (3)	169
C7—H7⋯O1	0.98	2.39	2.866 (4)	109

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Doctoral Foundation of Luoyang Normal University.

supplementary crystallographic information

Comment

Since the discovery of ferrocene in the 1950's (Kealy & Pauson, 1951), the fascinating structural properties of ferrocene and its derivatives have been the subject of increasing interest in all fields of organometallic chemistry (Hayashi et al., 1995; Staveren et al., 2004; Xu et al., 2007). Among them, ferrocene-heterocycles are one of the most important ones (Sarhan & Izumi, 2003). Herein we report the crystal structure of the title compound.

A view of the molecular structure of the title compound is given in Fig.1. The hydrogen atoms of methyl groups are disordered; site-occupation factors were fixed at 0.5. The pyridyl and Cp ring form a dihedral angle of 20.4 (3)°. In the crystal of the title compound, intermolecular O—H···N and C—H···O hydrogen bonds are present(Table 1), resulting in a two-dimensional supramolecular architecture(Fig.2).

Experimental

The title compound was prepared as described in literature (Beletskaya et al., 2001) and recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as red crystals suitable for single-crystal X-ray diffraction.