7-(4-Chloro­benzyl­idene)-3-[(4-chloro­phen­oxy)meth­yl]-6-(4-nitro­thio­phen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

Fun, H.-K.; Asik, S.I.J.; Razak, I.A.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811015637

Volume 67
Part 5
Pages o1266-o1267
May 2011

Received 21 April 2011
Accepted 26 April 2011
Online 29 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.133
Data-to-parameter ratio = 21.3
Details

7-(4-Chlorobenzylidene)-3-[(4-chlorophenoxy)methyl]-6-(4-nitrothiophen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

Hoong-Kun Fun,^a ^*⁺ Safra Izuani Jama Asik,^a Ibrahim Abdul Razak,^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

In the title compound, C₂₂H₁₃Cl₂N₅O₃S₂, the thiadiazine ring adopts a half-chair conformation. The benzene rings of the chlorophenoxy and chlorobenzyl groups and the thiophene ring form dihedral angles of 35.6 (1), 80.7 (1) and 14.2 (1)°, respectively, with the triazole ring. In the crystal, molecules are connected into sheets parallel to ( $[\overline{1}]$ 11) by intermolecular C-HN and C-HCl hydrogen bonds. In addition, [pi] - [pi] stacking interactions are observed between thiophene and triazole rings, and between inversion-related triazole rings [centroid-centroid distances = 3.5975 (11) and 3.4324 (11) Å].

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Shujuan et al. (2004); Clemons et al. (2004); Johnston (2002); Wei et al. (2007). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987); Jin et al. (2004). For related structures, see: Goh et al. (2010a,b,c,d).

Experimental

Crystal data

C₂₂H₁₃Cl₂N₅O₃S₂
M_r = 530.39
Triclinic, $[P \overline 1]$
a = 8.5021 (2) Å
b = 10.0379 (2) Å
c = 14.3623 (3) Å
= 94.434 (1)°
= 97.981 (1)°
= 109.242 (1)°
V = 1136.07 (4) Å³
Z = 2
Mo K radiation
= 0.51 mm^-1
T = 296 K
0.39 × 0.32 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.827, T_max = 0.946
19590 measured reflections
6548 independent reflections
5142 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.133
S = 1.04
6548 reflections
307 parameters
H-atom parameters constrained
_max = 0.59 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15AN2ⁱ	0.93	2.60	3.495 (3)	162
C21-H21ACl1ⁱⁱ	0.93	2.81	3.691 (2)	159
Symmetry codes: (i) x+1, y+1, z; (ii) x, y-1, z+1.

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: CI5185 ).

Acknowledgements

HKF, SIJA and IAR thank Universiti Sains Malaysia for the Research University Grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/811151).

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.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Clemons, M., Coleman, R. E. & Verma, S. (2004). Cancer Treat. Rev. 30, 325-332.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010a). Acta Cryst. E66, o1303.
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010b). Acta Cryst. E66, o1394-o1395.
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010c). Acta Cryst. E66, o2162-o2163.
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010d). Acta Cryst. E66, o2178-o2179.
Jin, Z.-M., Li, L., Li, M.-C., Hu, M.-L. & Shen, L. (2004). Acta Cryst. C60, o642-o643.
Johnston, G. A. R. (2002). Curr. Top. Med. Chem. 2, 903-913.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shujuan, S., Hongxiang, L., Gao, Y., Fan, P., Ma, B., Ge, W. & Wang, X. (2004). J. Pharm. Biomed. Anal. 34, 1117-1124.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wei, T.-B., Tang, J., Liu, H. & Zhang, Y.-M. (2007). Phosphorus Sulfur Silicon, 182, 1581-1587.

organic compounds