3-Phenyl-4-{3-[(p-tolyloxy)methyl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl}sydnone

In the title compound (systematic name: 3-phenyl-4-{3-[(p-tolyloxy)methyl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl}-1,2,3-oxadiazol-3-ium-5-olate), C20H16N6O3S, an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thiadiazine ring adopts a twist-boat conformation. The 1,2,3-oxadiazole and 1,2,4-triazole rings are inclined to each other at an interplanar angle of 44.13 (13)°. The phenyl ring makes an interplanar angle of 67.40 (13)° with the attached 1,2,3-oxadiazole ring. In the crystal structure, adjacent molecules are interconnected into two-molecule-thick arrays parallel to (100) via C—H⋯O and C—H⋯N hydrogen bonds. A short S⋯O contact [2.9512 (18) Å] is observed.


Experimental
A solution of triazole (0.01 mol) and 4-bromoacetyl-3-phenylsydnone (0.01 mol) in absolute ethanol (20 ml) was heated under reflux for 10-12 h. The solution was concentrated, cooled to room temperature and neutrallized with 10 % sodium bicarbonate solution. The separated solid was filtered, washed with water, dried and recrystallized from ethanol. Colourless blocks of (I) were obtained from a 1:2 mixture of DMF and ethanol by slow evaporation.

Refinement
All hydrogen atoms were placed in their calculated positions, with C-H = 0.93-0.97 Å, and refined using a riding model, with U iso = 1.2 or 1.5 U eq (C). The rotating group model was used for the methyl group.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms. An intramolecular hydrogen bond is shown as dashed line. Fig. 2. The crystal structure of (I), viewed along the b axis, showing two-molecule-thick arrays parallel to the (100) plane. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
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 > 2sigma(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.