(E)-4-(2-Hy­droxy-3-meth­oxy­benzyl­idene­amino)-6-methyl-3-sulfanyl­idene-3,4-dihydro-1,2,4-triazin-5(2H)-one

Bahareh Shirinkam; Masoumeh Tabatabaee; Mitra Gassemzadeh; Bernhard Neumuller

doi:10.1107/S1600536812036756

. 2012 Aug 31;68(Pt 9):o2815. doi: 10.1107/S1600536812036756

(E)-4-(2-Hydroxy-3-methoxybenzylideneamino)-6-methyl-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-one

Bahareh Shirinkam ^a, Masoumeh Tabatabaee ^a,^*, Mitra Gassemzadeh ^b, Bernhard Neumuller ^c

PMCID: PMC3435839 PMID: 22969685

Abstract

In the title molecule, C₁₂H₁₂N₄O₃S, there is an intramolecular O—H⋯N hydrogen bond. The dihedral angle between the benzene and triazine rings is 65.9 (3)°. In the crystal, N—H⋯S and O—H⋯N hydrogen bonds link the molecules into chains along [010]. In addition, there are weak π–π stacking interactions between symmetry-related triazine rings with a centroid–centroid distance of 3.560 (3)°.

Related literature

For the biological activity of azomethine compounds, see: Todeschini et al. (1998 ▶); Demirbas (2004 ▶); Rando et al. (2002 ▶). For general applications of Schiff base compounds, see: Galic et al. (2001 ▶); Wyrzykiewicz & Prukah (1998 ▶); Dubey et al. (1991 ▶). For the crystal structures of related Schiff base compounds, see: Tabatabaee et al. (2006 ▶, 2007 ▶, 2008 ▶, 2009 ▶). For the synthesis of the starting material, see: Dornow et al. (1964 ▶).

Experimental

Crystal data

C₁₂H₁₂N₄O₃S
M _r = 292.32
Monoclinic,
a = 13.679 (3) Å
b = 6.799 (1) Å
c = 13.797 (3) Å
β = 97.37 (2)°
V = 1272.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.17 × 0.16 × 0.05 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ▶) T _min = 0.19, T _max = 1.0
6252 measured reflections
2466 independent reflections
781 reflections with I > 2σ(I)
R _int = 0.168

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.148
S = 0.69
2466 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036756/lh5515sup1.cif

e-68-o2815-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036756/lh5515Isup2.hkl

e-68-o2815-Isup2.hkl^{(118.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036756/lh5515Isup3.cml

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
N4—H1⋯S1ⁱ	0.88	2.45	3.287 (5)	160
O2—H2⋯N2	0.89	1.87	2.662 (7)	146
O2—H2⋯N3ⁱⁱ	0.89	2.57	3.135 (7)	122

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

Acknowledgments

This research was supported by the Islamic Azad University, Yazd Branch.

supplementary crystallographic information

Comment

Azomethine compounds have been extensively studied for various reasons, one of which is their biological activity (Todeschini et al., 1998; Demirbas, 2004; Rando et al., 2002). Schiff bases, containing different donor atoms, also find use in analytical applications and metal coordination (Galic et al., 2001; Wyrzykiewicz & Prukah, 1998; Dubey et al., 1991). In a sequence of studies, we have investigated the synthesis and crystal structure of several Schiff bases derived 4-amino-5-methyl-2H-1,2,4-triazole-3(4H)-thione (AMTT) and 4-amino-6-methyl-3-thio-3,4-dihydro-1,2,4-triazin-5(2H)-one (AMTTO) compounds (Tabatabaee et al. 2006;2007;2008;2009) with various aldehydes. Herein, we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond distances and angles agree with related compounds (Tabatabaee et al., 2006; 2007; 2008; 2009). In the crystal, N—H···S and O—H···N hydrogen bonds link molecules into chains along [010] (Fig. 2). In addition, there are weak π–π stacking interactions between triazine rings Cg···Cg(1-x,-y,2-z) = 3.560 (3)Å, where Cg is the centroid defined by N1/C1/N4/N3/C3/C2.

Experimental

4-Amino-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (AMTTO) was prepared according to the literature procedure (Dornow et al., 1964). A solution of (AMTTO) (0.632 g, 4 mmol) in ethanol (10 ml) was treated with 2-hydroxy-3-methoxybenzaldehyde (0.608 g, 4 mmol) and the resulting mixture was acidified with 3 drops of hydrochloric acid (37.5%). The reaction mixture was refluxed. The progress of the reaction was monitored by TLC. After completion of the reaction (8 hrs), the pale yellow precipitate was filtered off and the clear solution was kept at 277K to give yellow plates crystals of the title compound (yield 79%).