(S)-1-Ferrocenyl-3-hy­droxy-3-phenyl­propan-1-one

Ping-An Wang

doi:10.1107/S1600536811000766

. 2011 Jan 15;67(Pt 2):m183. doi: 10.1107/S1600536811000766

(S)-1-Ferrocenyl-3-hydroxy-3-phenylpropan-1-one

Ping-An Wang ^a,^*

PMCID: PMC3051583 PMID: 21522855

Abstract

In the title compound, [Fe(C₅H₅)(C₁₄H₁₃O₂)], the dihedral angle between the phenyl ring and the unsubstituted cyclopetadienyl ring is 85.0 (2)°while that between the phenyl ring and the substituted cyclopetadienyl ring is 83.6 (2)°. The dihedral angle between the two cyclopenta-1,3-diene rings of the ferrocene unit is 2.2 (2)°. The molecules are stabilized by intermolecular O—H⋯O hydrogen-bonding interaction within the crystal lattice.

Related literature

For the preparation, see: Patti & Pedotti (2006a ▶); Hashiguchi et al. (1995 ▶). For use of the title compound in the preparation of chiral diols, see: Patti & Pedotti (2006b ▶) and of phosphine ligands, see: Zhang et al. (2007 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₄H₁₃O₂)]
M _r = 334.18
Orthorhombic,
a = 10.0609 (14) Å
b = 10.6054 (15) Å
c = 14.335 (2) Å
V = 1529.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 296 K
0.34 × 0.28 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.728, T _max = 0.840
7586 measured reflections
2721 independent reflections
2424 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.066
S = 1.06
2721 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ▶), 1146 Friedel pairs
Flack parameter: −0.004 (19)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: Mercury (Macrae et al., 2006 ▶) and ORTEP-3 (Farrugia, 1997 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000766/pb2052sup1.cif

e-67-0m183-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000766/pb2052Isup2.hkl

e-67-0m183-Isup2.hkl^{(133.6KB, 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⋯O2ⁱ	0.82	2.04	2.841 (3)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks the Natural Science Foundation of China (grant No. 20802092) for financial support.

supplementary crystallographic information

Comment

The title compound, (S)-1-ferrocenyl-3-phenyl-3-hydroxypropane- 1-one, was obtained from the catalytic asymmetric transfer hydrogenation of 1-ferrocenyl-3-phenyl-1,3-dione with the mixed solution of Et₃N and HCOOH by using Noyori's catalyst (Hashiguchi et al. 1995) and it was used for the preparation of chiral diols (Patti et al. 2006b) and phosphine ligands (Zhang et al. 2007).

In the title compound, C₁₉H₁₈FeO₂, the dihedral angle between the phenyl ring and the plane defined by the cyclopetadienyl ring ( C15, C16, C17,C18 and C19) is 85.0°. However, the dihedral angle between the phenyl ring and the plane defined by the second Cp ring (C10, C11, C12, C13 and C14) is 83.6°. The dihedral angle between the two cyclopenta-1,3-diene rings of the ferrocene moiety is 2.21°. The packing of molecules is stabilized by intermolecular O—H···O hydrogen bonds.

Experimental

A mixture of [RuCl₂(</>p-cymene)]₂ (20.0 mg, 0.030 mmol) and (1</>S,2</>S)-[</>N-(tosyl)- 1,2-diphenylethylendiamine](22.5 mg, 0.061 mmol) in 2-propanol (1.0 cm³) was heated at 80°C for 30 min under argon, then the solvent was removed under vacuum. the mixed solution of Et₃N and HCOOH (1.5 cm³) and 1-ferrocenyl-3-phenyl- 1,3-dione (0.34 g, 1.2 mmol) were added to the Ru-complex and the mixture stirred at 50°C while monitoring the reaction progress by thin layer chromatography. After 1.0 h, the solution was diluted with water (3.0 cm³) and extracted with ethyl acetate (2×, 20.0 cm³). The organic layer was washed with brine (2×, 10.0 cm³), dried over Na₂SO₄ and taken to dryness under vacuum. The residue was purified on silica gel column to give the title compound (0.31 g, 92% yield), and also produced (1</>S,3</>S)-1-ferrocenyl-3-phenyl- 1,3-dihydroxypropane (11.6 mg, 3.5% yield). The melting point and the spectroscopic data of the title compound were consisted with the reported literature (Patti & Pedotti, 2006a).