1-Benzoyl-3,3-dinitroazetidine

In the title gem-dinitroazetidine derivative, C10H9N3O5, the azetidine ring is almost planar, the maximum value of the endocyclic torsion angle being 0.92 (14)°. The gem-dinitro groups are mutually perpendicular and the dihedral angle between the azetidine and benzene rings is 46.70 (10)°

In the title gem-dinitroazetidine derivative, C 10 H 9 N 3 O 5 , the azetidine ring is almost planar, the maximum value of the endocyclic torsion angle being 0.92 (14) . The gem-dinitro groups are mutually perpendicular and the dihedral angle between the azetidine and benzene rings is 46.70 (10)

Experimental
A solution of DNAZ (0.40 g, 2.72 mmol), benzoyl chloride (0.35 ml, 2.99 mmol) and NaHCO 3 (0.23 g, 2.72 mmol) in dichloromethane (20.0 ml) was stirred under reflux for 16 h. The reaction mixture was concentrated in vacuo, acetone (30.0 ml) was added, and the mixture was stirred for 30 min, standing, filtered. The solid product was washed with ethanol and purified by recrystallization from dichloromethane to give the pure colorless compound in 81.7% yield. The title compound (52 mg,0.2 mmol) was dissolved in chloroform (10 ml

Refinement
All H atoms were placed at calculated idealized positions and refined using a riding model, with C-H distances in the range 0.93-0.97 Å. Fig. 1. The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are drawn as spheres of arbitrary radius.

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