(E)-5-(3,5-Dimethyl­phen­yl)-N-[4-(methyl­sulfan­yl)benzyl­idene]-1,3,4-thia­diazol-2-amine

Jun Hu; Jin-xiu Ji; Ying Zhou; Ji-kui Wang; Yan-hua Xu

doi:10.1107/S1600536810001558

. 2010 Jan 20;66(Pt 2):o410. doi: 10.1107/S1600536810001558

(E)-5-(3,5-Dimethylphenyl)-N-[4-(methylsulfanyl)benzylidene]-1,3,4-thiadiazol-2-amine

Jun Hu ^a, Jin-xiu Ji ^b, Ying Zhou ^c, Ji-kui Wang ^d, Yan-hua Xu ^a,^*

PMCID: PMC2979762 PMID: 21579829

Abstract

The title compound, C₁₈H₁₇N₃S₂, was synthesized by the reaction of 5-(3,5-dimethylphenyl)-1,3,4-thiadiazol-2-amine and 4-(methylsulfanyl)benzaldehyde. An intramolecular C—H⋯S hydrogen bond results in the formation of a planar (r.m.s. deviation = 0.003 Å) five-membered ring. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules to form layers parallel to (011).

Related literature

For the broad spectrum biological activity of 1,3,4-thiadiazole derivatives, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶).

Experimental

Crystal data

C₁₈H₁₇N₃S₂
M _r = 339.47
Triclinic,
a = 8.5640 (17) Å
b = 9.3370 (19) Å
c = 11.570 (2) Å
α = 90.98 (3)°
β = 110.03 (3)°
γ = 99.66 (3)°
V = 854.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.912, T _max = 0.969
3324 measured reflections
3098 independent reflections
2286 reflections with I > 2σ(I)
R _int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.208
S = 1.00
3098 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001558/bt5165sup1.cif

e-66-0o410-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001558/bt5165Isup2.hkl

e-66-0o410-Isup2.hkl^{(152KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N2ⁱ	0.93	2.58	3.223 (6)	126
C8—H8A⋯S2	0.93	2.59	3.041 (5)	110

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge Professor Hua-Qin Wang of the Analysis Center, Nanjing University, for providing the diffractometer for this research project. This work was supported by the National High Technology Research and Development (863 Program) of China (No. 2007AA06A402) and the Key Projects in the National Water Pollution Control and Management Pillar Program (No. 2008ZX07101-003).

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing a broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal, fungicidal activities (Wang et al., 1999). The molecule (Fig. 1) is almost planar (r.m.s. deviation for all non-H atoms 0.149Å). An intramolecular C—H···N hydrogen bond (Table 1) results in the formation of a planar five-membered ring. In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules to form layers parallel to the (0 1 1) plane (Fig. 2).

Experimental

5-(3,5-dimethylphenyl)-1,3,4-thiadiazol-2-amine(5 mmol) and 4-methylthio benzaldehyde(5 mmol) were added in toluene (50 ml). The water was removed by distillation for 5 h. The reaction mixture was left to cool to room temperature, filtered, and the filter cake was crystallized from acetone to give pure compound (I) (m.p. 408 K).Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.