(E)-1-Ferrocenyl-3-(2-meth­oxy­phen­yl)prop-2-en-1-one

Myrna R Otaño Vega; Kennett I Rivero; Ingrid Montes González

doi:10.1107/S1600536814003912

. 2014 Feb 26;70(Pt 3):m108–m109. doi: 10.1107/S1600536814003912

(E)-1-Ferrocenyl-3-(2-methoxyphenyl)prop-2-en-1-one

Myrna R Otaño Vega ^a, Kennett I Rivero ^a,^*, Ingrid Montes González ^a

PMCID: PMC3998481 PMID: 24764940

Abstract

The structure of the title compound, [Fe(C₅H₅)(C₁₅H₁₃O₂)], consists of a ferrocenyl moiety and a 2-methoxyphenyl group linked through a prop-2-en-1-one spacer in an E conformation. In the ferrocene unit, the substituted cyclopentadienyl (Cps) ring and the unsubstituted cyclopentadienyl ring (Cp) are almost parallel to one another [dihedral angle = 1.78 (14)°], and the Cp and Cps rings are in a gauche conformation. The benzene ring is twisted by 10.02 (14) and 11.38 (11)° with respect to the Cp and Cps rings, respectively. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds into supramolecular chains running along the b-axis direction.

Related literature

For the synthesis, see: Attar et al. (2011 ▶); Kumar et al. (2012 ▶). For related syntheses and background, see: Liu et al. (2001 ▶); Wu et al. (2002 ▶); Ji et al. (2003 ▶); Maree et al. (2008 ▶); Jiao et al. (2009 ▶); Cardona et al. (2010 ▶). For the biological activity of calcones and chalcone derivatives, see: Wu et al. (2002 ▶); Arezki et al. (2009 ▶); Nabi & Liu (2011 ▶); Zhao & Liu (2012 ▶). For related structures, see: Lindeman et al. (1997 ▶); Wu et al. (2006 ▶); Liu et al. (2008 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₅H₁₃O₂)]
M _r = 346.19
Orthorhombic,
a = 8.8352 (1) Å
b = 11.4047 (1) Å
c = 16.1327 (2) Å
V = 1625.58 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 296 K
0.22 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.821, T _max = 0.896
13238 measured reflections
3659 independent reflections
3242 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.065
S = 1.05
3658 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ▶), 1523 Friedel pairs
Absolute structure parameter: 0.004 (14)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003912/xu5769sup1.cif

e-70-0m108-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003912/xu5769Isup2.hkl

e-70-0m108-Isup2.hkl^{(179.4KB, hkl)}

CCDC reference: 987910

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.48	3.368 (2)	159

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Pfizer Pharmaceuticals Fellowship Program, the UPR–RP RISE Program (No. 2R25GM61151), and the Materials Characterization Center (MCC)-UPR Río Piedras.

supplementary crystallographic information

1. Comment

Chalcones occur in nature as precursors of flavonoids and exhibit various biological activities such as anti-cancer, anti-inflammatory, nitric oxide regulation and anti-hyperglycemic agents (Liu et al., 2001). They are traditionally synthesized in the laboratory, via the Claisen–Schmidt condensation carried out in basic or acidic media under homogeneous conditions (Attar et al., 2011). Structural modifications of the chalcone template are readily achieved. Biological activities of chalcones are equally wide ranging, such as: anti-bacterial and anti-hyperglycemic, anti-malarial, anti-HIV, anti-oxidant, and anti-tumor (Wu et al., 2002).

The crystal structure of the title compound reveals that the configuration about the C12═C13 bond corresponds to the (E)-isomer. The majority of the C and O atoms of the substituted cyclopentadienyl ring (Cps) are sp²-hybridized and the conjugation is lost at the methoxy substituent of C19. In the ferrocenyl moiety, the planes formed by the Cp (unsubstituted cyclopentadienyl ring) and Cps are almost parallel. The C atoms in these two rings have adopted a gauche conformation, and the Fe metal center lies closer to the Cps ring. The Fe—Cg and Fe—Cgs distances are 1.658 (2) and 1.644 (2) Å, respectively, where Cg and Cgs are the centroids of Cp and Cps, respectively. The Cg—Fe—Cgs angle is 178.4 (2)°.

2. Experimental

The title compound was synthesized according to the literature procedure (Cardona et al., 2010). An aqueous solution of sodium hydroxide (5%, 2 ml) was added slowly with stirring to acetylferrocene (0.456 g, 0.002 mol). Then, 2-methoxybenzaldehyde (0.272 g, 0.002 mol) in ethanol (2 ml). The resulting mixture was stirred at room temperature for 2 h. The dark-orange-red precipitated solid was filtered off, washed with cold water and ethanol, dried and recrystallized from a mixture of acetone:water (yield, 84%; M·P. 144–145 °C). Dark violet crystals, suitable for X-ray diffraction, were obtained by the slow evaporation of a 1:1 (v/v) acetone:water solution of the title compound at room temperature over a period of 1 day. NMR analyses were performed on a Bruker AV-500 spectrometer by using CDCl₃ 99.9% pure as a solvent and Me₄Si as external standard.¹H-NMR (δ in p.p.m., CDCl₃): 3.90 (3H, s), 4.20 (5H, s), 4.60 (2H, s), 4.90 (2H, s), 7.05 (1H, d), 6.95, 7.25, 7.35, 8.10 (4H, dd, d,d, dd), 7.65 (1H, d). ¹³C-NMR (δ in p.p.m., CDCl₃): 55.5, 69.7, 70.1, 72.5, 80.9, 111.2, 123.9, 120.7, 124.7, 128.9, 131.2, 136.3, 158.7, 193.5.