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

Yao Wang; Rong Wan; Feng Han; Peng Wang

doi:10.1107/S1600536809022594

. 2009 Jun 17;65(Pt 7):o1608. doi: 10.1107/S1600536809022594

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

Yao Wang ^a, Rong Wan ^a,^*, Feng Han ^a, Peng Wang ^a

PMCID: PMC2969462 PMID: 21582881

Abstract

The title compound, C₁₃H₁₇N₃S, was synthesized by the reaction of 4-pentylbenzoic acid and thiosemicarbazide. The dihedral angle between the thiadiazole and phenyl rings is 29.9 (2)°. An intramolecular C—H⋯S interaction is observed. In the crystal, intermolecular N—H⋯N hydrogen bonding links the molecules into centrosymmetric dimers.

Related literature

For general background to the biological activity of 1,3,4-thiadiazole derivatives, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₁₇N₃S
M _r = 247.36
Monoclinic,
a = 14.012 (3) Å
b = 9.1300 (18) Å
c = 10.938 (2) Å
β = 100.64 (3)°
V = 1375.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.958, T _max = 0.989
2596 measured reflections
2492 independent reflections
1405 reflections with I > 2σ(I)
R _int = 0.023
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.179
S = 1.00
2492 reflections
148 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.52 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/S1600536809022594/hg2519sup1.cif

e-65-o1608-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022594/hg2519Isup2.hkl

e-65-o1608-Isup2.hkl^{(122.4KB, 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
C8—H8A⋯S	0.93	2.81	3.177 (4)	104
N3—H3A⋯N2ⁱ	0.86	2.15	3.006 (4)	173

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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 Enraf–Nonius CAD-4 diffractometer for this research project.

supplementary crystallographic information

Comment

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996). These compounds are known to exhibit diverse biological effects, such as insecticidal, fungicidal activities (Wang et al., 1999). The structure of the title compound, (I), is shown in Fig. 1, in which the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. The dihedral angle between the thiadiazole and phenyl ring is 29.90 (19)°. An intramolecular C—H···S interaction is observed (Fig. 1). There is intermolecular N—H···N hydrogen bond (Fig. 2), forming chains along the c axis. The intermolecular N—H···N hydrogen bond creates centrosymmetric dimers.

Experimental

4-Pentylbenzoic acid (5 mmol) and thiosemicarbazide (5 mmol) were mixed in a 25 ml flask, and kept in the oil bath at 90°C for 6 h. After cooling, the crude product (I) precipitated and was filtered. Pure compound (I) was obtained by crystallization from ethanol(20 ml). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.