Methyl (E)-2-[(2-nitrophenoxy)methyl]-3-phenylacrylate

The title compound, C17H15NO5, adopts an E conformation with respect to the C=C double bond of the phenylacrylate unit. The phenyl ring and methyl acrylate group of the phenylacrylate unit are disordered over two sets of sites with site-occupancy ratios of 0.705 (5):0.295 (5) and 0.683 (3):0.317 (3), respectively. The mean plane through the benzene ring of the phenyl acrylate makes dihedral angles of 88.4 (8) (major component) and 86.7 (8)° (minor component) with the nitrophenoxy ring; the dihedral angle between the two components is 3.64 (6)°. Intramolecular C—H⋯O interactions stabilise the molecular structure. In the crystal, C—H⋯O interactions result in a chain of molecules running along the b axis.

The title compound, C 17 H 15 NO 5 , adopts an E conformation with respect to the C C double bond of the phenylacrylate unit. The phenyl ring and methyl acrylate group of the phenylacrylate unit are disordered over two sets of sites with site-occupancy ratios of 0.705 (5):0.295 (5) and 0.683 (3): 0.317 (3), respectively. The mean plane through the benzene ring of the phenyl acrylate makes dihedral angles of 88.4 (8) (major component) and 86.7 (8) (minor component) with the nitrophenoxy ring; the dihedral angle between the two components is 3.64 (6) . Intramolecular C-HÁ Á ÁO interactions stabilise the molecular structure. In the crystal, C-HÁ Á ÁO interactions result in a chain of molecules running along the b axis.   Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) x À 1 2 ; Ày þ 3 2 ; z À 1 2 ; (ii) x; y þ 1; z.

Comment
Methyl trans-cinnamate can inhibit both monophenolase activity and diphenolase activity of tyrosinase and thus it can be a potential compound used in antibrowning food additive (Huang et al., 2009). It is a fragrance ingredient used in many fragrances and decorative cosmetics (Bhatia et al., 2007;Sharma, 2011). In view of this industrial importance, we have prepared the title compound which is a nitrophenoxymethyl derivative of methyl trans-cinnamate and determined its crystal structure which is presented in this paper.
The title molecule adopts an E configuration with respect to the C8═C9 double bond ( The crystal structure is stabilized by intramolecular bifurcated C-H···O hydrogen bonds involving two hydrogen atoms (H2/H3) of the benzene ring (C1-C6) and O3 of the acrylate resulting in an R 2 2 (5) ring motif (Bernstein et al., 1995) and C4-H4···O2 interactions resulting in a chain of molecules running along the b-axis (Table 1 and

Experimental
To a stirred solution of 2-nitrophenol (0.14 g, 1 mmol) in acetonitrile (7 ml), potassium carbonate (0.35 g, 2.5 mmol) was added and stirred well for five minutes. To this solution, (Z)-methyl 2-(bromomethyl)-3-phenylacrylate (0.26 g, 1 mmol) in acetonitrile (0.5 ml) was added and allowed to stir well for 6 h. After the completion of the reaction, the reaction mixture was poured into water and extracted using ethyl acetate. The organic layer thus obtained was concentrated under reduced pressure and the residual mass thus obtained was purified by column chromatography on silica gel (Acme 100-200) using EtOAc-hexanes (1:9) to afford the title compound in 90% yield. The crystals suitable for X-ray crystallographic analysis were grown from a solution of ethylacetate by slow evaporation at room temperature.

Refinement
The benzene ring(C10 -C15) and methyl acrylate(C16/C17/O3/O4) group of the phenylacrylate unit are disordered over two orientations with site-occupancy ratio of 0.705 (5):0.295 (5) and 0.683 (3):0.317 (3) representing major and minor components repectively. The command EADP was used in SHELXL-97 (Sheldrick, 2008) to constrain the U eq of the disordered atoms. The hydrogen atoms were placed in calculated positions with C-H = 0.93, 0.96 and 0.97 Å, for acryl, methyl and methylene H-atoms, respectively, and refined in the riding mode; the U iso (H) were allowed at 1.5U eq (C methyl) or 1.2U eq (C non-methyl).   A view of the C--H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o 2 ) + (0.0548P) 2 + 1.2534P]

Methyl (E)-2-[(2-nitrophenoxy)methyl]-3-phenylacrylate
where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.008 Δρ max = 0.18 e Å −3 Δρ min = −0.23 e Å −3 Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ. (