2-(6-Phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-3-yl)-1,3-benzothia­zole

Hatem A Abdel-Aziz; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536811036452

. 2011 Sep 14;67(Pt 10):o2610. doi: 10.1107/S1600536811036452

2-(6-Phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1,3-benzothiazole

Hatem A Abdel-Aziz ^a,^‡, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3201480 PMID: 22058756

Abstract

In the title compound, C₁₇H₁₁N₅S₂, the dihedral angles formed between the triazole ring and the benzene ring and the 1,3-benzothiazole ring system are 8.67 (8) and 13.90 (9)°, respectively. The conformation of the triazolo-thiadiazin-3-yl fused ring system is a twisted half-chair. Overall, the molecule adopts a flattened shape. Supramolecular helical chains along the a axis sustained by C—H⋯N interactions are found in the crystal structure. These are linked via C—H⋯π contacts as well as π–π [centroid–centroid distance = 3.5911 (12) Å] interactions between the triazole and thiazole rings.

Related literature

For background to the synthesis and biological activity of benzothiazoles and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, see: Abdel-Aziz et al. (2007 ▶, 2010 ▶); Dawood et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₁N₅S₂
M _r = 349.43
Orthorhombic,
a = 12.1437 (3) Å
b = 21.2950 (5) Å
c = 5.7946 (1) Å
V = 1498.48 (6) Å³
Z = 4
Cu Kα radiation
μ = 3.29 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.715, T _max = 1.000
5754 measured reflections
2902 independent reflections
2751 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.083
S = 1.06
2902 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ▶), 1150 Friedel pairs
Flack parameter: −0.006 (16)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036452/hg5092sup1.cif

e-67-o2610-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036452/hg5092Isup2.hkl

e-67-o2610-Isup2.hkl^{(142.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036452/hg5092Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10a⋯N3ⁱ	0.99	2.45	3.333 (3)	148
C3—H3⋯Cg1ⁱⁱ	0.95	2.65	3.377 (2)	134

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank King Saud University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The title compound, (I), was investigated in relation to the established biological activities exhibited by benzothiazoles and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (Abdel-Aziz et al. 2007; Abdel-Aziz et al. 2010; Dawood et al. 2005).

In (I), Fig. 1, the 1,3-benzothiazole ring is planar with r.m.s. deviations of 0.034 Å. By contrast, the triazolo-thiadiazin-3-yl fused ring system has a twisted half-chair form owing to the presence of the methylene-C10 group with the C10 atom lying 0.702 (3) Å out of the least-squares plane defined by the S2,N4,N5,C9,C11 atoms (r.m.s. deviation = 0.109 Å). The 1,3-benzothiazole ring forms dihedral angles of 13.90 (9) and 8.67 (8) °, respectively, with the triazole and benzene rings so that the entire molecule has a flattened shape.

In the crystal packing, C—H···N interactions, Table 1, lead to the formation of supramolecular chains along the a axis with an helical topology, Fig. 2. These assemble into zigzag layers in the ac plane with connections between them of the type C—H···π involving a methylene-H and the benzene ring, and π···π. The shortest interaction of the latter type of 3.5911 (12) Å occurs between the S1,N1,C1,C6,C7 and N2–N4,C8,C9 five-membered rings, Fig. 3.

Experimental

The title compound was prepared according to the reported method (Abdel-Aziz et al., 2007). Colourless crystals were obtained from an EtOH/DMF (v/v = 2/1) solution by slow evaporation at room temperature.