(Z)-N-[2-(N′-Hydroxycarbamimidoyl)phenyl]acetamide

The asymmetric unit of the title compound, C9H11N3O2, contains two molecules (A and B), which exist in Z conformations with respect to their C=N double bond. The dihedral angles between the benzene ring and the pendant hydroxycarbamimidoyl and acetamide groups are 28.58 (7) and 1.30 (5)°, respectively, in molecule A and 25.04 (7) and 27.85 (9)°, respectively, in molecule B. An intramolecular N—H⋯N hydrogen bond generates an S(6) ring in both molecules. Molecule A also features an intramolecular C—H⋯O interaction, which closes an S(6) ring. In the crystal, the molecules are linked by N—H⋯O, N—H⋯N, O—H⋯O, O—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π interactions, generating a three-dimensional network.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009  Amidoximes are bi-functional molecules exhibiting a rich and diverse chemistry and provides the shortest way to reach certain heterocycles, such as 1,2,4-oxadiazoles (Clapp, 1976(Clapp, , 1984Jochims, 1996). They are also considered interesting molecules in view of their biological applications (Fylaktakidou et al., 2008). Their ability to release NO or nitrites in vitro and in vivo experiments has recently attracted attention (Mansuy et al., 2004;Kontogiorgis et al., 2002). The discovery that nitric oxide (NO) acts as an important mediator of smooth muscle relaxation has led us to the preparation and testing of a wide variety of compounds with the aim of finding suitable new NO-donors. In the process, the title compound, (Z)-N-(2-(N′-hydroxycarbamimidoyl) phenyl)acetamide (Wang et al., 2002) was prepared.
The title compound consist of two crystallographically independent molecules (A and B) as shown in Fig. 1. The molecules exist in Z configuration with respect to the C7A ═N1A and C7B ═N1B double bonds. The intramolecular N3 -H3···N1 hydrogen bonds (Table 1) form S(6) ring motifs (Bernstein et al., 1995) in both molecules. Molecule A is stabilized by an additional intramolecular C2A-H2AA···O2A hydrogen bond (Table 1) which also generates an S(6) ring motif (Bernstein et al., 1995). The bond lengths (Allen et al., 1987) and angles are within normal ranges.

Experimental
Equimolar amount of N-(2-cyanophenyl)acetamide (10 mmol) and NH 2 OH.HCl (10 mmol) were dissolved in a minimum amount of methanol(10 ml)-water (5 ml) and followed by the addition of Na 2 CO 3 (5 mmol). The solution was refluxed for 2 h. The solid product formed was collected through filtration and then evaporated to dryness. The product was redissolved in MeOH for recrystalliziation as colourless plates. M. P.: 145°C.

Refinement
All N and O bound H atoms were located from the difference map and were refined freely [N-H = 0.857 (19)-0.90 (2) Å and O-H = 0.93 (2) and 0.95 (2) Å]. The remaining H atoms were positioned geometrically and refined using a riding model with U iso (H) = 1.2 or 1.5U eq (C) (C-H = 0.9500 and 0.9800 Å). A rotating group model was applied to the methyl groups.

Figure 1
The molecular structure of the title compound, showing 50% probability displacement ellipsoids. Dashed lines indicate the intramolecular hydrogen bonds.   (Cosier & Glazer, 1986) operating at 100 (1) K. 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.