3-(3-Methoxy­benz­yl)-4-(2-methoxy­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Hanif, M.; Qadeer, G.; Rama, N.H.; Ruzicka, A.

doi:10.1107/S1600536808037215

Volume 64
Part 12
Pages o2345-o2346
December 2008

Received 1 November 2008
Accepted 10 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.073
wR = 0.159
Data-to-parameter ratio = 17.8
Details

3-(3-Methoxybenzyl)-4-(2-methoxyphenyl)-1H-1,2,4-triazole-5(4H)-thione

Muhammad Hanif,^a Ghulam Qadeer,^a ^* Nasim Hasan Rama ^a and Ales Ruzicka ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nam. Cs. Legii' 565, 53210 Pardubice, Czech Republic
Correspondence e-mail: qadeerqau@yahoo.com

In the title compound, C₁₇H₁₇N₃O₂S, the five-membered ring forms dihedral angles of 53.02 (3) and 78.57 (3)° with the 3-methoxy-substituted and 2-methoxy-substituted benzene rings, respectively. In the crystal structure, molecules are linked into centrosymmetric dimers via intermolecular N-HS hydrogen bonds.

Related literature

For background information on the biological activity of substituted triazole derivatives, see: Demirbas et al. (2002); Holla et al. (1998); Omar et al. (1986); Paulvannan et al. (2000); Turan-Zitouni et al. (1999); Kritsanida et al. (2002). For related structures, see: Öztürk et al. (2004a,b); Zhang et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₇N₃O₂S
M_r = 327.40
Triclinic, $[P \overline 1]$
a = 7.3941 (3) Å
b = 10.6459 (5) Å
c = 12.1940 (8) Å
= 68.841 (5)°
= 74.317 (5)°
= 75.187 (5)°
V = 848.37 (8) Å³
Z = 2
Mo K radiation
= 0.20 mm^-1
T = 293 (2) K
0.40 × 0.24 × 0.15 mm

Data collection

Bruker-Nonius KappaCCD area-detector diffractometer
Absorption correction: integration (Gaussian; Coppens, 1970) T_min = 0.946, T_max = 0.983
10764 measured reflections
3708 independent reflections
2064 reflections with I > 2(I)
R_int = 0.079

Refinement

R[F² > 2(F²)] = 0.073
wR(F²) = 0.159
S = 1.10
3708 reflections
208 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2S1ⁱ	0.86	2.42	3.277 (3)	172
Symmetry code: (i) -x-1, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2729 ).

Acknowledgements

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

References

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organic compounds