3-Diazo-N-[(2S)-1-hydroxypropan-2-yl]-2-oxopropanamide

In the title compound, C6H9N3O3, the 3-diazo-2-oxopropanamide section of the molecule is nearly planar, with a maximum deviation of 0.025 (1) Å from the mean plane of its constituent atoms. The diazo C=N=N angle is 178.0 (3)°. In the crystal, pairs of intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules into infinite double chains along the [100] direction. The double chains are additionally stabilized by weak C—H⋯O contacts with C⋯O distances of 3.039 (3) Å. Neighboring double chains in turn interact with each other through π–π stacking interactions [centroid–centroid distance of the 3-diazo-2-oxopropanamide units = 3.66 (6) Å] to form infinite stacks along the b axis. Molecules from neighboring stacks interdigitate with each other in the c-axis direction, thus leading to an interwoven three-dimensional network held together by O—H⋯O, N—H⋯O and C—H⋯O interactions and π–π stacking.

In the title compound, C 6 H 9 N 3 O 3 , the 3-diazo-2-oxopropanamide section of the molecule is nearly planar, with a maximum deviation of 0.025 (1) Å from the mean plane of its constituent atoms. The diazo C N N angle is 178.0 (3) . In the crystal, pairs of intermolecular O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds link the molecules into infinite double chains along the [100] direction. The double chains are additionally stabilized by weak C-HÁ Á ÁO contacts with CÁ Á ÁO distances of 3.039 (3) Å . Neighboring double chains in turn interact with each other throughstacking interactions [centroid-centroid distance of the 3-diazo-2oxopropanamide units = 3.66 (6) Å ] to form infinite stacks along the b axis. Molecules from neighboring stacks interdigitate with each other in the c-axis direction, thus leading to an interwoven three-dimensional network held together by O-HÁ Á ÁO, N-HÁ Á ÁO and C-HÁ Á ÁO interactions andstacking.
Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. have wide applications in organic synthesis, such as C-H or C-N bonds insertion, 1,3-dipolar cyclization and transition metal complexes catalyzed transformations (Doyle & Forbes, 1998;Zhang & Wang, 2008;Doyle, 1986). To investigate the relationship between structure and reactivity, the title compound was synthesized and its structure was determined by X-ray diffraction. In this article, we present the synthesis and crystal structure of this new diazo compound.

Structure Reports Online
As shown in figure 1, the 3-diazo-2-oxopropanamide section of the molecule is nearly planar with a maximum deviation
This suspension was stirred at room temperature and the reaction was monitored by TLC. When the diazo ethyl pyruvate was consumed, the yellow brown reaction mixture was concentrated to dryness. The crude product was purified by column chromatography on silica gel with petroleum ether/ethyl acetate (1/1) as eluent to give the product in yield of 63% (0.377 g, 2.2 mmol). Single crystals suitable for X-ray diffraction study were obtained by recrystallization of the crude from a diethyl  considerations (AFIX 33 instruction in SHELXL97 (Sheldrick, 2008)). In the absence of significant anomalous scattering effects, 572 Friedel pairs were averaged prior to the final refinement. Fig. 1. The molecular structure of the title compound, with displacement ellipsoids at the 30% probability level.  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.

Figures
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )