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

Wang, Y.; Wan, R.; Han, F.; Wang, P.

doi:10.1107/S1600536809022594

Volume 65
Part 7
Page o1608
July 2009

Received 26 May 2009
Accepted 12 June 2009
Online 17 June 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.066
wR = 0.179
Data-to-parameter ratio = 16.8
Details

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

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

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: rwan@njut.edu.cn

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-HS interaction is observed. In the crystal, intermolecular N-HN 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, P 2₁ /c
a = 14.012 (3) Å
b = 9.1300 (18) Å
c = 10.938 (2) Å
= 100.64 (3)°
V = 1375.2 (5) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 293 K
0.20 × 0.10 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.958, T_max = 0.989
2596 measured reflections
2492 independent reflections
1405 reflections with I > 2(I)
R_int = 0.023
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.179
S = 1.00
2492 reflections
148 parameters
1 restraint
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8AS	0.93	2.81	3.177 (4)	104
N3-H3AN2ⁱ	0.86	2.15	3.006 (4)	173
Symmetry code: (i) -x, -y+1, -z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: HG2519 ).

Acknowledgements

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.

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.
Enraf-Nonius (1989). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Nakagawa, Y., Nishimura, K., Izumi, K., Kinoshita, K., Kimura, T. & Kurihara, N. (1996). J. Pestic. Sci. 21, 195-201.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y. G., Cao, L., Yan, J., Ye, W. F., Zhou, Q. C. & Lu, B. X. (1999). Chem. J. Chin. Univ. 20, 1903-1905.

organic compounds