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

Shirinkam, B.; Tabatabaee, M.; Gassemzadeh, M.; Neumuller, B.

doi:10.1107/S1600536812036756

organic compounds

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Volume 68| Part 9| September 2012| Page o2815

doi:10.1107/S1600536812036756

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(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 and Bernhard Neumuller ^c

^aDepartment of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran, ^bChemistry and Chemical Engineering Research Center of Iran, Tehran, Iran, and ^cDepartment of Chemistry, Marburg University, Marburg, Germany
^*Correspondence e-mail: tabatabaee45@gmail.com

(Received 7 August 2012; accepted 24 August 2012; online 31 August 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.063
wR(F²) = 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

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
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036756/lh5515sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812036756/lh5515Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); 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).

Figures top

Fig. 1 The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Fig 2. Part of the crystal structure with hydrogen bonds drawn as dashed lines.

Fig. 3 A view of a π–π stacking interaction.

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

Crystal data top

C₁₂H₁₂N₄O₃S	F(000) = 608
M_r = 292.32	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2500 reflections
a = 13.679 (3) Å	θ = 1.5–25.9°
b = 6.799 (1) Å	µ = 0.27 mm⁻¹
c = 13.797 (3) Å	T = 100 K
β = 97.37 (2)°	Plate, yellow
V = 1272.6 (4) Å³	0.17 × 0.16 × 0.05 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	2466 independent reflections
Radiation source: fine-focus sealed tube	781 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.168
ω scans	θ_max = 25.9°, θ_min = 1.5°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −16→16
T_min = 0.19, T_max = 1.0	k = −8→7
6252 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 0.69	w = 1/[σ²(F_o²) + (0.0454P)²] where P = (F_o² + 2F_c²)/3
2466 reflections	(Δ/σ)_max = 0.002
184 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₂H₁₂N₄O₃S	V = 1272.6 (4) Å³
M_r = 292.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.679 (3) Å	µ = 0.27 mm⁻¹
b = 6.799 (1) Å	T = 100 K
c = 13.797 (3) Å	0.17 × 0.16 × 0.05 mm
β = 97.37 (2)°

Data collection top

Stoe IPDS II diffractometer	2466 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	781 reflections with I > 2σ(I)
T_min = 0.19, T_max = 1.0	R_int = 0.168
6252 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 0.69	Δρ_max = 0.25 e Å⁻³
2466 reflections	Δρ_min = −0.25 e Å⁻³
184 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.63854 (13)	0.3469 (2)	0.97729 (12)	0.0493 (5)
O1	0.4940 (3)	−0.2444 (6)	0.8000 (3)	0.0543 (12)
O2	0.8173 (3)	−0.1839 (6)	1.0066 (3)	0.0502 (11)
H2	0.7563	−0.1360	0.9959	0.062 (6)*
O3	1.0050 (3)	−0.2641 (5)	1.0104 (3)	0.0533 (11)
N1	0.5557 (4)	0.0250 (6)	0.8869 (3)	0.0424 (12)
N2	0.6523 (4)	−0.0561 (6)	0.9024 (4)	0.0448 (13)
N3	0.3669 (4)	0.1720 (7)	0.8798 (3)	0.0466 (13)
N4	0.4513 (4)	0.2673 (6)	0.9210 (3)	0.0425 (13)
H1	0.4422	0.3832	0.9467	0.062 (6)*
C1	0.5420 (5)	0.2093 (8)	0.9268 (4)	0.0450 (16)
C2	0.4779 (5)	−0.0841 (8)	0.8374 (4)	0.0417 (15)
C3	0.3819 (4)	0.0048 (8)	0.8378 (4)	0.0451 (16)
C4	0.2920 (5)	−0.1023 (8)	0.7908 (4)	0.0570 (19)
H41	0.2328	−0.0300	0.8028	0.062 (6)*
H42	0.2905	−0.2346	0.8188	0.062 (6)*
H43	0.2943	−0.1121	0.7203	0.062 (6)*
C5	0.6952 (5)	−0.0721 (8)	0.8260 (5)	0.0473 (17)
H51	0.6594	−0.0394	0.7645	0.062 (6)*
C6	0.7947 (5)	−0.1371 (9)	0.8290 (5)	0.0478 (16)
C7	0.8550 (5)	−0.1852 (9)	0.9182 (5)	0.0504 (17)
C8	0.9545 (5)	−0.2297 (8)	0.9195 (5)	0.0491 (17)
C9	0.9954 (5)	−0.2408 (8)	0.8333 (5)	0.0551 (17)
H91	1.0629	−0.2745	0.8340	0.062 (6)*
C10	0.9358 (5)	−0.2017 (8)	0.7439 (5)	0.0462 (16)
H101	0.9634	−0.2126	0.6844	0.062 (6)*
C11	0.8401 (5)	−0.1490 (9)	0.7416 (4)	0.0485 (16)
H111	0.8024	−0.1194	0.6807	0.062 (6)*
C12	1.1069 (4)	−0.3021 (9)	1.0169 (5)	0.0521 (17)
H121	1.1341	−0.3196	1.0856	0.062 (6)*
H122	1.1398	−0.1911	0.9893	0.062 (6)*
H123	1.1178	−0.4220	0.9803	0.062 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0519 (10)	0.0425 (8)	0.0543 (10)	−0.0001 (8)	0.0096 (8)	−0.0035 (8)
O1	0.066 (3)	0.044 (2)	0.052 (3)	0.000 (2)	0.008 (2)	−0.003 (2)
O2	0.042 (3)	0.055 (3)	0.055 (3)	0.011 (2)	0.011 (2)	0.005 (2)
O3	0.047 (3)	0.055 (2)	0.057 (3)	0.007 (2)	0.003 (2)	0.000 (2)
N1	0.045 (3)	0.037 (3)	0.045 (3)	0.002 (2)	0.007 (3)	0.002 (2)
N2	0.042 (3)	0.040 (3)	0.054 (3)	0.007 (2)	0.014 (3)	0.003 (3)
N3	0.056 (3)	0.039 (3)	0.045 (3)	0.002 (3)	0.008 (3)	0.000 (2)
N4	0.040 (3)	0.036 (3)	0.052 (3)	−0.004 (3)	0.008 (3)	−0.004 (2)
C1	0.042 (4)	0.039 (3)	0.054 (4)	−0.001 (3)	0.008 (3)	0.009 (3)
C2	0.053 (4)	0.035 (3)	0.040 (4)	0.002 (3)	0.019 (3)	−0.001 (3)
C3	0.050 (4)	0.040 (3)	0.046 (4)	0.002 (3)	0.010 (3)	0.004 (3)
C4	0.084 (5)	0.035 (4)	0.051 (4)	0.006 (3)	0.004 (4)	−0.006 (3)
C5	0.047 (4)	0.034 (3)	0.061 (5)	0.002 (3)	0.003 (4)	0.002 (3)
C6	0.045 (4)	0.038 (3)	0.061 (4)	−0.007 (3)	0.007 (4)	0.004 (3)
C7	0.057 (5)	0.043 (4)	0.053 (4)	−0.004 (3)	0.013 (4)	−0.002 (3)
C8	0.044 (4)	0.036 (3)	0.067 (5)	0.002 (3)	0.006 (4)	0.000 (3)
C9	0.059 (5)	0.045 (3)	0.064 (5)	−0.004 (3)	0.018 (4)	0.002 (3)
C10	0.047 (4)	0.043 (4)	0.054 (4)	−0.007 (3)	0.025 (4)	0.004 (3)
C11	0.051 (4)	0.047 (3)	0.047 (4)	−0.004 (3)	0.009 (3)	−0.005 (3)
C12	0.033 (4)	0.055 (4)	0.070 (4)	0.004 (3)	0.015 (3)	0.008 (3)

Geometric parameters (Å, º) top

S1—C1	1.694 (6)	C4—H42	0.9800
O1—C2	1.238 (6)	C4—H43	0.9800
O2—C7	1.383 (7)	C5—C6	1.427 (8)
O2—H2	0.8900	C5—H51	0.9500
O3—C8	1.372 (7)	C6—C11	1.427 (8)
O3—C12	1.409 (7)	C6—C7	1.428 (8)
N1—C1	1.391 (7)	C7—C8	1.393 (8)
N1—C2	1.401 (7)	C8—C9	1.380 (9)
N1—N2	1.422 (6)	C9—C10	1.413 (8)
N2—C5	1.275 (7)	C9—H91	0.9500
N3—C3	1.303 (7)	C10—C11	1.354 (8)
N3—N4	1.381 (6)	C10—H101	0.9500
N4—C1	1.295 (7)	C11—H111	0.9500
N4—H1	0.8800	C12—H121	0.9800
C2—C3	1.447 (8)	C12—H122	0.9800
C3—C4	1.503 (8)	C12—H123	0.9800
C4—H41	0.9800

C7—O2—H2	107.6	N2—C5—H51	118.6
C8—O3—C12	117.9 (5)	C6—C5—H51	118.6
C1—N1—C2	122.5 (5)	C11—C6—C7	116.7 (6)
C1—N1—N2	117.3 (5)	C11—C6—C5	120.6 (6)
C2—N1—N2	120.1 (4)	C7—C6—C5	122.6 (6)
C5—N2—N1	115.2 (5)	O2—C7—C8	117.6 (6)
C3—N3—N4	114.9 (5)	O2—C7—C6	121.3 (6)
C1—N4—N3	128.8 (5)	C8—C7—C6	121.1 (6)
C1—N4—H1	115.6	O3—C8—C9	124.5 (6)
N3—N4—H1	115.6	O3—C8—C7	115.2 (6)
N4—C1—N1	115.2 (5)	C9—C8—C7	120.3 (6)
N4—C1—S1	123.2 (5)	C8—C9—C10	119.4 (6)
N1—C1—S1	121.6 (5)	C8—C9—H91	120.3
O1—C2—N1	120.3 (5)	C10—C9—H91	120.3
O1—C2—C3	125.5 (6)	C11—C10—C9	121.2 (6)
N1—C2—C3	114.2 (5)	C11—C10—H101	119.4
N3—C3—C2	124.1 (5)	C9—C10—H101	119.4
N3—C3—C4	116.6 (5)	C10—C11—C6	121.3 (6)
C2—C3—C4	119.2 (5)	C10—C11—H111	119.4
C3—C4—H41	109.5	C6—C11—H111	119.4
C3—C4—H42	109.5	O3—C12—H121	109.5
H41—C4—H42	109.5	O3—C12—H122	109.5
C3—C4—H43	109.5	H121—C12—H122	109.5
H41—C4—H43	109.5	O3—C12—H123	109.5
H42—C4—H43	109.5	H121—C12—H123	109.5
N2—C5—C6	122.8 (6)	H122—C12—H123	109.5

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₄O₃S
M_r	292.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.679 (3), 6.799 (1), 13.797 (3)
β (°)	97.37 (2)
V (Å³)	1272.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.17 × 0.16 × 0.05

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)
T_min, T_max	0.19, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	6252, 2466, 781
R_int	0.168
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.148, 0.69
No. of reflections	2466
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

Computer programs: X-AREA (Stoe & Cie, 2008), X-RED32 (Stoe & Cie, 2008), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2.

Acknowledgements

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

References

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Volume 68| Part 9| September 2012| Page o2815

doi:10.1107/S1600536812036756

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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