Crystal structure of 4-azidomethyl-6-tert-butyl-2H-chromen-2-one

In the title compound, C14H15N3O2, one of the methyl C atoms of the tert-butyl group lies almost in the plane of the chromene ring system [deviation = −0.097 (2) Å], one lies above and one lies below [deviations = 1.460 (3) and 1.006 (3) Å, respectively]. The C—C—N—N torsion angle is 142.33 (17)°. In the crystal, moelcules are linked by weak C—H⋯O hydrogen bonds to generate C(6) chains propagating in the [010] direction.


S1. Comment
Coumarin and its substituents are of well known heterocyclic compounds, which have a variety of biologically activities; such as anti-tumour (Mustafa et al., 2011), anti-bacterial (Basanagouda et al., 2009;Liu et al., 2008) and analgesic (Ronad et al., 2008) agents. In addition, coumarin derivatives have been found to be very useful in many applications; such as nonlinear optical materials and as intermediates for the drug synthesis (Tian et al., 2000). In our previous work (Puttaraju et al., 2013), we have reported the synthesis, in vitro antimicrobial and anticancer activities of new coumarin derivatives substituted dihydrobenzo [4,5]imidazo[1,2-a]pyrimidin-4-ones. In continuation to this, we have synthesized the title compound to study its molecular and crystal structure.
In the molecular structure of the title compound ( Fig. 1), the chromene moiety is almost planar, with the maximum deviation from the mean plane being 0.093 (2) Å for atom C10, respectively. The azidomethyl group is in anti-periplanar conformation with respect to the chromene moiety, as indicated by the torsion angle value of 172.35 (14)° (C3-C4-C14-N1). The bond lengths and angles are within normal ranges and are comparable to related structure (Chandra et al., 2014).
The crystal structure features C-H···O hydrogen bonds, which link the molecules into [010] chains, as shown in Fig. 2.

S2. Experimental
6-tert-Butyl-4-bromomethylcoumarins (0.001 mmol. 0.5 g) were taken in 15 ml acetone in a round bottomed flask and stirred. To this, sodium azide (0.002 mol, 0.13 g) in 5 ml of water was added drop wise with stirring, which was continued for 3 hrs (reaction was monitored by TLC). The reaction mixture was poured in to ice cold water, separated solid was filtered and recrystallized from ethyl alcohol to get pale yelllow blocks of the title compound.

S3. Refinement
The H atoms were positioned geometrically and allowed to ride on their parent atom, with C-H distance in the range of 0  Perspective diagram of the molecule with 50% probability displacement ellipsoids.

Figure 2
Packing diagram of the molecule viewed parallel to the b axis. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.13 e Å −3 Δρ min = −0.17 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1 0.59056 (