(E)-4-(2-Hy-droxy-3-meth-oxy-benzyl-idene-amino)-6-methyl-3-sulfanyl-idene-3,4-dihydro-1,2,4-triazin-5(2H)-one.

In the title mol-ecule, C(12)H(12)N(4)O(3)S, there is an intra-molecular 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 mol-ecules into chains along [010]. In addition, there are weak π-π stacking inter-actions 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 = 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

Δρmax = 0.25 e Å−3

Δρmin = −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 ▶).

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

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N4O3S	F(000) = 608
Mr = 292.32	Dx = 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

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

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(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
2466 reflections	(Δ/σ)max = 0.002
184 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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

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) ; (ii) .