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

Muhammad Hanif; Ghulam Qadeer; Nasim Hasan Rama; Ales Ruzicka

doi:10.1107/S1600536808037215

. 2008 Nov 13;64(Pt 12):o2345–o2346. doi: 10.1107/S1600536808037215

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

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

PMCID: PMC2959946 PMID: 21581320

Abstract

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—H⋯S 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,
a = 7.3941 (3) Å
b = 10.6459 (5) Å
c = 12.1940 (8) Å
α = 68.841 (5)°
β = 74.317 (5)°
γ = 75.187 (5)°
V = 848.37 (8) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.079

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.159
S = 1.10
3708 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037215/lh2729sup1.cif

e-64-o2345-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037215/lh2729Isup2.hkl

e-64-o2345-Isup2.hkl^{(181.8KB, 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
N2—H2⋯S1ⁱ	0.86	2.42	3.277 (3)	172

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Substituted triazole derivatives display significant biological activity including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). The biological activity is closely related to structure, possibly being due to the presence of the —N—C=S unit (Omar et al., 1986). We are interested in the synthesis and biological activity of substituted triazole derivatives and report here the synthesis and crystal structure of the title compound, (I) (Fig. 1).

In the molecluar structure of (I), the bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those observed in related structures (Öztürk et al., 2004a,b). The C7-S1 bond length [1.679 (3) A °] compares with 1.6773 (19) A ° in 4-(4-chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione (Ozturk et al., 2004a) and 1.668 (5) A ° in 4-amino-3-(1,2,3,4,5- pentahydroxypentyl)-1H-1,2,4-triazole-5(4H)-thione (Zhang et al., 2004). In the triazole ring, the N3-C8 bond [1.294 (4)] bond shows the expected double bond character.

The rings A (N1—N3/C7/C8), B (C1—C6) and C (C10—C15) are eesentially planar and dihedral angles between them are A/B = 78.57 (3)°, A/C = 53.02 (3)° and B/C = 16.23 (3)°. In the crystal structure, molecules are linked into centrosymmetric dimers via intermolecular N–H···S hydrogen bonds.

Experimental

The synthesis of the title compound was carried out by refluxing a solution of 4-(2-methoxyphenyl)-1-(2-(3-methoxyphenyl)acetyl)thiosemicarbazide (3.45 g, 10 mmol) in 2 M NaOH for 5 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield: 75%; m.p. 469–470 K).