(E)-Methyl 3-(4-ethyl­phen­yl)-2-{2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy­meth­yl}acrylate

E Govindan; K SakthiMurugesan; J Srinivasan; M Bakthadoss; A SubbiahPandi

doi:10.1107/S1600536811038359

. 2011 Sep 30;67(Pt 10):o2753. doi: 10.1107/S1600536811038359

(E)-Methyl 3-(4-ethylphenyl)-2-{2-[(E)-(hydroxyimino)methyl]phenoxymethyl}acrylate

E Govindan ^a, K SakthiMurugesan ^a, J Srinivasan ^b, M Bakthadoss ^b, A SubbiahPandi ^a,^*

PMCID: PMC3201344 PMID: 22058811

Abstract

In the title compound, C₂₀H₂₁NO₄, the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hydroxyethanimine [C=N—OH] group being 0.011 (1) Å for the O atom. An intramolecular C—H⋯O hydrogen bond occurs. The molecules are linked into cyclic centrosymmetric R ₂ ²(6) dimers via O—H⋯N hydrogen bonds. Intermolecular C—H⋯O hydrogen bonds link the molecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C—H⋯π interactions.

Related literature

For structures of other acrylate derivatives, see: Zhang et al. (2009 ▶); Wang et al. (2011 ▶); SakthiMurugesan et al. (2011 ▶). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003 ▶).

Experimental

Crystal data

C₂₀H₂₁NO₄
M _r = 339.38
Triclinic,
a = 9.0053 (2) Å
b = 9.3655 (3) Å
c = 12.1793 (3) Å
α = 75.299 (1)°
β = 74.756 (1)°
γ = 64.891 (1)°
V = 885.43 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.978, T _max = 0.983
24628 measured reflections
6955 independent reflections
4453 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.189
S = 1.02
6955 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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: 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/S1600536811038359/nk2110sup1.cif

e-67-o2753-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038359/nk2110Isup2.hkl

e-67-o2753-Isup2.hkl^{(333.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038359/nk2110Isup3.cml

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

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

Cg2 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	2.15	2.8568 (15)	145
C14—H14⋯O2	0.93	2.51	3.3002 (16)	143
C15—H15⋯O4ⁱⁱ	0.93	2.50	3.3524 (16)	152
C5—H5⋯Cg2ⁱⁱⁱ	0.93	2.94	3.7756 (14)	150

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

Acknowledgments

EG and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Recently, 2-cyanoacrylates have been extensively used as agrochemicals because of their unique mechanism of action and good environmental profiles (Zhang et al., 2009). Oximes are a classical type of chelating ligands which are widely used in coordination and analytical chemistry (Chaudhuri, 2003). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other acrylate derivatives (Wang et al., 2011). The whole molecule is not planar as the dihedral angle between the two aryl rings is 86.1 (7)°, it shows that both the rings are almost perpendicular to each other. The oxime group having the C═N forming an E configuration. The hydroxyethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hydroxyethanimine [C═N—OH] group is 0.011 (1)Å for the O1 atom.

The enoate group assumes an extended conformation as can be seen from torsion angles C9—C10—O3—C11 [178.1 (1) °] and C12—C9—C10—O3 [171.6 (1) °]. The atom C15 in the molecule (x,y,z) donate one proton to atom O4 of the molecule at (-1 + x,y,z) forming a C(8) chain along a axis. The hydroxyethanimine group in the molecules are linked into cyclic centrosymmetric dimers via O—H···N hydrogen bonds with the motif R₂²(6) (Figure 2). In addition to van der Waals interaction, the crystal packing is stabilized by C–H..O, O–H···N and C–H···π interactions.

Experimental

To a stirred solution of (E)-methyl 2-((2-formylphenoxy)methyl) -3-(4-ethylphenyl)acrylate (4 mmol) in 10 ml of EtOH/H₂O mixture (1:1) was added NH₂OH.HCl (6 mmol) in the presence of 50% NaOH at room temperature. Then the reaction mixture was allowed to stir at room temperature for 1.5 h. After completion of the reaction, solvent was removed and the crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 x 15 ml). The combined organic layer was washed with brine (2 x 10 ml) and dried over anhydrous Na₂SO₄ and then evaporated under reduced pressure to obtain (E)-methyl3- (4-ethylphenyl)-2-((2-((E)-(hydroxyimino)methyl)phenoxy)methyl)acrylate as a colourless solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.