5-(4-Meth­ylphenyl)-1,3,4-thia­diazol-2-amine

Jian-Ning Guan; Rong Wan; Yao Wang; Feng Han; Cheng-Zhen Xu

doi:10.1107/S1600536809012434

. 2009 Apr 8;65(Pt 5):o976. doi: 10.1107/S1600536809012434

5-(4-Methylphenyl)-1,3,4-thiadiazol-2-amine

Jian-Ning Guan ^a, Rong Wan ^a,^*, Yao Wang ^a, Feng Han ^a, Cheng-Zhen Xu ^a

PMCID: PMC2977673 PMID: 21584016

Abstract

The title compound, C₉H₉N₃S, was synthesized by the reaction of 4-methyl-benzoic acid and thiosemicarbazide. The thiadiazol ring adopts a planar conformation and makes a dihedral angle of 31.19 (18)° with the phenyl ring. In the crystal, molecules are linked by N—H⋯N hydrogen bonds.

Related literature

For applications of thiadiazole ligands, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶); Han et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₉H₉N₃S
M _r = 191.25
Monoclinic,
a = 12.284 (3) Å
b = 7.3730 (15) Å
c = 11.263 (2) Å
β = 109.09 (3)°
V = 964.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Nonius CAD4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.918, T _max = 0.972
1963 measured reflections
1875 independent reflections
1351 reflections with I > 2σ(I)
R _int = 0.067
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.181
S = 1.01
1875 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); 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/S1600536809012434/at2758sup1.cif

e-65-0o976-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012434/at2758Isup2.hkl

e-65-0o976-Isup2.hkl^{(92.3KB, 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
N3—H3A⋯N2ⁱ	0.86	2.13	2.970 (5)	166
N3—H3B⋯N1ⁱⁱ	0.86	2.18	3.025 (4)	166

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

Acknowledgments

The authors thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for collecting the crystallographic data.

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing 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). We are focusing our synthetic and structural studies on thiadiazole derivatives and we have recently published the structure of 5-m-tolyl-[1,3,4]thiadiazol-2-ylamine (Han et al., 2007). We report here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The thiadiazole and the phenyl ring make a dihedral angle of 31.19 (18)°. The molecules link by N—H···N hydrogen bonds to stabilize the crystal structure (Fig. 2).

Experimental

4-Methyl-benzoic acid (5 mmol) and thiosemicarbazide (5 mmol) were added in toluene (50 ml), which is heated under reflux for 4 h. The reaction mixture was left to cool to room temperature, poured into ice water, filtered, and the filter cake was crystallized from acetone to give pure compound (I). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.