1-[1-(Hydroxyimino)ethyl]-N-(2-methoxyphenyl)cyclopropanecarboxamide

The title compound, C13H16N2O3, adopts an E configuration with respect to the C=N bond and an intramolecular N—H⋯N hydrogen bond results in the formation of a six-membered ring. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into a chain propagating along the b axis. Very weak π–π stacking interactions [centroid–centroid distance = 4.18 (2) Å] may further consolidate the packing, forming a two-dimensional supramolecular network.


Related literature
as organic synthesis, catalytic reaction and so on (Liu & Montgomery, 2006;Ogoshi et al., 2006). In order to extend our work on structural characterization of cyclopropane compounds, we report the synthesis and the X-ray structure of the title compound, (I), in this paper (Fig. 1).
The title molecule adopts an E configuration with respect to C=N bond. There is an intramolecular O-H···N hydrogen bonds, forming of a six-membered ring (Table 1) and the intermolecular O-H···O hydrogen bonds link the molecules into a one-dimensional chain along the b axis. The crystal structure is further stabilized by π-π interaction involving the benzene rings: Cg1···Cg1 (1 -x, 1 -y, 1 -z) = 4.18 (2) Å, where Cg1 denotes the centroid of the C2-C7 (Fig. 2).

Experimental
To a solution of 1-acetyl-N-(2-methoxyphenyl)cyclopropanecarboxamide (2.33 g, 10 mmol) and NaOAc (1.64 g, 20 mmol) in EtOH (25 ml) and H 2 O (1 ml) was added NH 2 OH.HCl (1.39 g, 20 mmol) in one portion. The reaction mixture was stirred at room temperature for 12 h, and then poured into ice-water (200 ml) under stirring. A white solid was precipitated, which was filtered and the residue was purified by a flash silica gel column chromatography to give colourless blocks of (I) (eluent: ether/ethyl acetate = 1/3 v/v).

Refinement
The N-and O-bound H atoms were located in a difference map and their positions were freely refined. The C-bound H atoms were geometrically placed (C-H = 0.93-0.97Å) and refined as riding. The constraints U iso = 1.2Ueq(C,N) or 1.5Ueq(methyl C,O) were applied. Fig. 1. Molecule structure of (I) with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(F 2 ) is used only for calculating Rfactors(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.