Received 19 March 2011
The title compound, C18H14N6O2S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. The 3,6-dihydro-2H-1,3,4-thiadiazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 53.70 (4) and 60.26 (4)° with the two phenyl rings. In the crystal, molecules are linked via pairs of intermolecular N-HN hydrogen bonds, generating R22(8) ring motifs, and are further linked via intermolecular C-HO and C-HS hydrogen bonds into a three-dimensional network. The short intermolecular distance between the oxadiazol-3-ium rings [3.4154 (4) Å] indicates the existence of a - interaction.
For general background to and the biological activity of sydnone derivatives, see: Newton & Ramsden (1982); Wagner & Hill (1974); Kalluraya & Rahiman (1997). For the preparation, see: Kalluraya et al. (2003). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5123 ).
HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).
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