(Z)-Methyl 2-[(2-eth­oxy-6-formyl­phen­oxy)meth­yl]-3-(4-ethyl­phen­yl)acrylate

Rajeswari Gangadharan; K Sethusankar; Raman Selvakumar; Manickam Bakthadoss

doi:10.1107/S1600536811046587

. 2011 Nov 9;67(Pt 12):o3245. doi: 10.1107/S1600536811046587

(Z)-Methyl 2-[(2-ethoxy-6-formylphenoxy)methyl]-3-(4-ethylphenyl)acrylate

Rajeswari Gangadharan ^a, K Sethusankar ^b,^*, Raman Selvakumar ^c, Manickam Bakthadoss ^c

PMCID: PMC3238902 PMID: 22199755

Abstract

The title compound, C₂₂H₂₄O₅, consists of two substituted benzene rings linked by an ethyl acrylate group. The dihedral angle between the two benzene rings is 58.39 (7)°. The crystal packing is governed by two C—H⋯O interactions, one of which forms centrosymmetric dimers with a graph-set descriptor of R ₂ ²(18).

Related literature

For applications of acrylate derivatives, see: Xiao et al. (2008 ▶). For a related structure, see: Gong et al. (2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₂H₂₄O₅
M _r = 368.41
Triclinic,
a = 9.6746 (3) Å
b = 9.9435 (3) Å
c = 10.7935 (3) Å
α = 77.595 (1)°
β = 85.433 (2)°
γ = 76.752 (1)°
V = 986.59 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
25506 measured reflections
6646 independent reflections
4400 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.164
S = 1.02
6646 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046587/pv2468sup1.cif

e-67-o3245-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046587/pv2468Isup2.hkl

e-67-o3245-Isup2.hkl^{(318.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811046587/pv2468Isup3.cml

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
C7—H7⋯O5ⁱ	0.93	2.58	3.368 (2)	143
C17—H17⋯O1ⁱⁱ	0.93	2.56	3.454 (2)	161

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

RG and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Department of Physics, for providing facilities in the department to carry out this work.

supplementary crystallographic information

Comment

Phenyl acrylates show considerable antibacterial activities against Staphylococcus aureus (Xiao et al., 2008).

In the title compound (Fig. 1), the methyl acrylate group is planar and forms dihedral angles 33.43 (4)° and 41.71 (4)° with the two phenyl rings (C1–C6) and (C15–C20), respectively. The inter planar angle between the two phenyl rings is 58.39 (7)°. The title compound exhibits structural similarities with the already reported related structure (Gong et al., 2008).

The crystal packing is governed by two C—H···O interactions, one of which forms centrosymmetric dimers with graph set descriptor of R²₂(18) (Bernstein et al.1995) (Fig. 2 and Table 1)

Experimental

A solution of 3-ethoxysalicylaldehyde (3.54 mmol, 0.58 g) and potassium carbonate (3.89 mmol, 0.53 g) in acetonitrile (10 ml) was stirred for 15 minutes at room temperature. To this solution, (Z)-methyl 2-(bromomethyl)-3-(4-ethylphenyl)acrylate (3.54 mmol, 1 g) was added dropwise. After the completion of the reaction as indicated by TLC, acetonitrile was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass and extracted. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product which was purified through pad of silica gel (100–200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colorless solid (1.05 g, 81%). Recrystallization was carried out using ethylacetate as solvent.