(E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylonitrile

Suresh Govindan; Sabari Vijayakumar; Srinivasan Jayakumar; Bakthadoss Mannickam; Aravindhan Sanmargam

doi:10.1107/S1600536812003923

. 2012 Feb 4;68(Pt 3):o596. doi: 10.1107/S1600536812003923

(E)-2-({2-[(E)-(Hydroxyimino)methyl]phenoxy}methyl)-3-phenylacrylonitrile

Suresh Govindan ^a, Sabari Vijayakumar ^a, Srinivasan Jayakumar ^b, Bakthadoss Mannickam ^b, Aravindhan Sanmargam ^a,^*

PMCID: PMC3297320 PMID: 22412510

Abstract

In the title compound, C₁₇H₁₄N₂O₂, the hydroxyethanimine group adopts an antiperiplanar conformation. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming zigzag chains running along the c axis.

Related literature

For the structures of other acrylate derivatives, see: Zhang et al. (2009 ▶); Wang et al. (2011 ▶); SakthiMurugesan et al. (2011 ▶); Govindan et al. (2011 ▶). For the use of oxime ligands in coordination chemistry, see: Chaudhuri (2003 ▶). For the biological activity of caffeic acids, see: Hwang et al. (2001 ▶); Altug et al. (2008 ▶); Ates et al. (2006 ▶); Atik et al. (2006 ▶); Padinchare et al. (2001 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O₂
M _r = 278.30
Monoclinic,
a = 15.8867 (5) Å
b = 6.2381 (2) Å
c = 15.1874 (4) Å
β = 107.199 (2)°
V = 1437.81 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.980, T _max = 0.990
19516 measured reflections
4490 independent reflections
2774 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.131
S = 0.99
4490 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003923/bt5765sup1.cif

e-68-0o596-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003923/bt5765Isup2.hkl

e-68-0o596-Isup2.hkl^{(215.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812003923/bt5765Isup3.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
O1—H1A⋯N2ⁱ	0.82	2.10	2.9187 (17)	178

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Symmetry code: (i) Inline graphic .

Acknowledgments

AS thanks the UGC, India, for financial support.

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). Some naturally occurring caffeic acids and their esters attract much attention in biology and medicine (Hwang et al., 2001; Altug et al., 2008). These compounds show antiviral, antibacterial, vasoactive, antiatherogenic, antiproliferative, antioxidant and antiinflammatory properties (Atik et al., 2006; Padinchare et al., 2001; Ates et al., 2006). 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 and the results are presented here. X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The oxime group has the C=N bond in an E configuration. The hydroxy ethanimine group is essentially coplanar with the ring to which it is attached. The crystal packing is stabilized by an O—H···N hydrogen bond(Fig. 2).

Experimental

To a stirred solution of (E)-2-((2-formylphenoxy)methyl)-3-phenylacrylonitrile (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 τimes 15 ml). The combined organic layer was washed with brine (2 τimes 10 ml) and dried over anhydrous Na2SO4 and then evaporated under reduced pressure to obtain (E)-2-((2-((E)-(Hydroxyimino)methyl)phenoxy)methyl)-3-phenylacrylonitrile as a colourless solid.