4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate

Fun, H.-K.; Quah, C.K.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811010609

Volume 67
Part 4
Pages o977-o978
April 2011

Received 19 March 2011
Accepted 22 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.033
wR = 0.101
Data-to-parameter ratio = 30.5
Details

4-{(Z)-2-[(E)-Benzylidenehydrazinylidene]-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate

Hoong-Kun Fun,^a ^*⁺ Ching Kheng Quah,^a ⁺⁺ Nithinchandra ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

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 [pi] - [pi] interaction.

Related literature

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).

Experimental

Crystal data

C₁₈H₁₄N₆O₂S
M_r = 378.41
Triclinic, $[P \overline 1]$
a = 6.8752 (2) Å
b = 10.1335 (3) Å
c = 12.7374 (4) Å
= 78.578 (1)°
= 88.984 (1)°
= 85.874 (1)°
V = 867.58 (5) Å³
Z = 2
Mo K radiation
= 0.21 mm^-1
T = 100 K
0.58 × 0.27 × 0.08 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.885, T_max = 0.982
29236 measured reflections
7567 independent reflections
6818 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.101
S = 1.03
7567 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.65 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1N3N2ⁱ	0.852 (15)	2.015 (15)	2.8664 (9)	178.3 (11)
C14-H14AO2ⁱⁱ	0.93	2.58	3.2303 (10)	127
C15-H15AO2ⁱⁱⁱ	0.93	2.51	3.2391 (9)	136
C18-H18AS1^iv	0.93	2.84	3.7061 (8)	155
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+2, -z; (iii) x, y-1, z; (iv) x+1, y, z.

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 ).

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Kalluraya, B. & Rahiman, A. M. (1997). Pol. J. Chem. 71, 1049-1052.
Kalluraya, B., Vishwanatha, P., Hedge, J. C., Priya, V. F. & Rai, G. (2003). Indian J. Heterocycl. Chem. 12, 355-356.
Newton, C. G. & Ramsden, C. A. (1982). Tetrahedron, 38, 2965-3011.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wagner, H. & Hill, J. B. (1974). J. Med. Chem. 17, 1337-1338.

organic compounds