2-Azido-1-(4-fluorophenyl)ethanone

The crystal structure of the title compound, C8H6FN3O, is stabilized by C—H⋯O hydrogen bonds, which link the molecules into chains running parallel to the a axis.


Experimental
In the molecule of the title compound ( Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges.
The crystal structure ( Fig. 2) is stabilized by intermolecular hydrogen bonds (Table 1) linking the m olecules to form chains parallel to the a axis.
Experimental 1-(4-Fluorophenyl)ethanone (7.239 mmol, 1.0 equiv.) was dissolved in acetonitrile (18 ml) in a round bottom flask. To the stirred mixture, p-toluenesulphonic acid (10.858 mmol, 1.5 equiv.) and N-bromosuccinimide (10.134 mmol, 1.4 equiv.) were added, and the solution was heated to reflux for 1 to 1.5 h until completion of the reaction as monitored by TLC analysis. The reaction mixture was cooled to room temperature and sodium azide (21.717 mmol, 3.0 equiv.) was added. After additional stirring for 2 to 3 h, ice cooled water was added to quench the reaction. The reaction mixture was extracted with diethyl ether (2 × 25 ml) and the combined organic layer was dried over anhydrous Na 2 SO 4 , filtered and concentrated in vacuum to get the crude product. The crude product was purified by flash silica gel chromatography (EtOAc/hexane, 1:9-3:7 v/v) to afford the title compound in 65% yield. Recrystallization by slow evaporation of an ethanol solution afforded crystals suitable for single-crystal X-ray studies. All chemicals were purchased from Sigma-Aldrich.

Refinement
H atoms were positioned geometrically with C-H = 0.93-0.97 Å, and constrained to ride on their parent atoms with

Computing details
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009   The molecular structure of the title compound with displacement ellipsoids drawn at 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 > 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.