4-(2,3-Dihydroxybenzyl-ideneamino)-3-methyl-1H-1,2,4-triazol-5(4H)-one.

All the non-H atoms of the title compound, C(10)H(10)N(4)O(3), are almost coplanar, the maximum deviation from planarity being 0.065 (3) Å. The dihedral angle between the aromatic rings is 1.66 (6)°. The mol-ecule adopts the enol-imine tautomeric form with an intra-molecular hydrogen-bonding inter-action between the Schiff base N atom and the hydr-oxy group. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For the synthesis of the title compound, see Ünver et al. (2008 ▶). For related compounds, see: Köysal et al. (2007 ▶); Tanak et al., (2009 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H10N4O3

M = 234.22

Monoclinic,

a = 13.944 (3) Å

b = 6.2551 (7) Å

c = 11.882 (2) Å

β = 93.857 (17)°

V = 1034.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.60 × 0.42 × 0.20 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.944, T max = 0.974

3000 measured reflections

1118 independent reflections

1058 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.116

S = 1.09

1118 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045772/bt5118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045772/bt5118Isup2.hkl

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

C10H10N4O3	F(000) = 488
Mr = 234.22	Dx = 1.505 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 4561 reflections
a = 13.944 (3) Å	θ = 1.7–28.0°
b = 6.2551 (7) Å	µ = 0.12 mm−1
c = 11.882 (2) Å	T = 296 K
β = 93.857 (17)°	Prism., yellow
V = 1034.0 (3) Å3	0.60 × 0.42 × 0.20 mm
Z = 4

Stoe IPDS II diffractometer	1118 independent reflections
Radiation source: fine-focus sealed tube	1058 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.7°
rotation method scans	h = −17→17
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
Tmin = 0.944, Tmax = 0.974	l = −14→12
3000 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0817P)2 + 0.2531P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1118 reflections	Δρmax = 0.31 e Å−3
159 parameters	Δρmin = −0.27 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
C1	0.42468 (17)	0.3934 (5)	0.2738 (2)	0.0359 (6)
C2	0.4051 (2)	0.2125 (6)	0.3388 (2)	0.0437 (7)
H8	0.4384	0.1927	0.4084	0.052*
C3	0.3379 (2)	0.0655 (5)	0.3012 (3)	0.0468 (7)
H9	0.3259	−0.0535	0.3451	0.056*
C4	0.28754 (19)	0.0937 (5)	0.1977 (3)	0.0423 (7)
H44	0.2419	−0.0067	0.1722	0.051*
C5	0.30481 (17)	0.2698 (5)	0.1325 (2)	0.0367 (6)
C6	0.37377 (17)	0.4209 (5)	0.1696 (2)	0.0339 (6)
C7	0.49894 (18)	0.5409 (5)	0.3167 (2)	0.0375 (6)
H13	0.5301	0.5190	0.3874	0.045*
C8	0.64752 (17)	0.8427 (5)	0.3996 (2)	0.0369 (6)
C9	0.61215 (17)	1.0237 (5)	0.2381 (2)	0.0367 (6)
C10	0.5679 (2)	1.0718 (6)	0.1242 (2)	0.0463 (7)
H15A	0.5240	0.9595	0.1009	0.069*
H15B	0.6172	1.0821	0.0718	0.069*
H15C	0.5338	1.2049	0.1259	0.069*
N1	0.52117 (14)	0.7007 (4)	0.25680 (18)	0.0346 (5)
N2	0.58991 (14)	0.8440 (4)	0.29821 (17)	0.0347 (5)
N3	0.69709 (17)	1.0251 (5)	0.3919 (2)	0.0441 (6)
H3	0.7380	1.0693	0.4442	0.053*
N4	0.67653 (16)	1.1360 (5)	0.2924 (2)	0.0436 (6)
O1	0.38826 (15)	0.5879 (4)	0.09998 (18)	0.0464 (6)
O2	0.25821 (14)	0.3108 (4)	0.03004 (16)	0.0478 (6)
H2	0.2197	0.2146	0.0141	0.072*
O3	0.64859 (14)	0.7078 (4)	0.47417 (16)	0.0471 (5)
H1	0.438 (3)	0.656 (9)	0.131 (4)	0.074 (13)*

	U11	U22	U33	U12	U13	U23
C1	0.0356 (12)	0.0356 (15)	0.0357 (12)	−0.0006 (11)	−0.0031 (10)	−0.0023 (12)
C2	0.0501 (15)	0.0436 (17)	0.0362 (13)	−0.0019 (14)	−0.0062 (11)	0.0060 (14)
C3	0.0557 (16)	0.0408 (17)	0.0446 (15)	−0.0055 (14)	0.0084 (12)	0.0037 (13)
C4	0.0385 (13)	0.0375 (15)	0.0507 (16)	−0.0066 (12)	0.0007 (11)	−0.0069 (13)
C5	0.0301 (11)	0.0395 (16)	0.0396 (13)	0.0018 (11)	−0.0040 (10)	−0.0078 (11)
C6	0.0325 (11)	0.0311 (13)	0.0371 (12)	0.0012 (11)	−0.0041 (9)	−0.0008 (11)
C7	0.0393 (12)	0.0398 (16)	0.0322 (11)	0.0013 (12)	−0.0072 (9)	−0.0004 (12)
C8	0.0327 (11)	0.0408 (14)	0.0354 (12)	0.0039 (11)	−0.0101 (9)	−0.0046 (12)
C9	0.0360 (12)	0.0369 (14)	0.0365 (12)	0.0004 (11)	−0.0031 (9)	0.0007 (12)
C10	0.0431 (14)	0.0524 (19)	0.0420 (14)	−0.0001 (13)	−0.0081 (11)	0.0084 (14)
N1	0.0334 (10)	0.0329 (12)	0.0360 (10)	−0.0011 (9)	−0.0096 (8)	−0.0030 (10)
N2	0.0326 (10)	0.0359 (12)	0.0339 (10)	−0.0007 (9)	−0.0107 (8)	−0.0002 (10)
N3	0.0433 (11)	0.0432 (14)	0.0431 (12)	−0.0087 (11)	−0.0172 (9)	−0.0034 (12)
N4	0.0402 (11)	0.0448 (14)	0.0445 (12)	−0.0061 (11)	−0.0077 (9)	0.0013 (12)
O1	0.0493 (11)	0.0393 (12)	0.0472 (11)	−0.0091 (10)	−0.0206 (9)	0.0101 (9)
O2	0.0463 (10)	0.0471 (13)	0.0470 (12)	−0.0054 (10)	−0.0183 (9)	−0.0041 (10)
O3	0.0477 (10)	0.0514 (13)	0.0392 (10)	−0.0007 (10)	−0.0178 (8)	0.0063 (10)

C1—C6	1.396 (4)	C8—O3	1.223 (4)
C1—C2	1.407 (4)	C8—N3	1.340 (4)
C1—C7	1.453 (4)	C8—N2	1.402 (3)
C2—C3	1.367 (4)	C9—N4	1.280 (4)
C2—H8	0.9300	C9—N2	1.378 (4)
C3—C4	1.386 (4)	C9—C10	1.480 (4)
C3—H9	0.9300	C10—H15A	0.9600
C4—C5	1.377 (4)	C10—H15B	0.9600
C4—H44	0.9300	C10—H15C	0.9600
C5—O2	1.365 (3)	N1—N2	1.379 (3)
C5—C6	1.398 (4)	N3—N4	1.384 (4)
C6—O1	1.356 (3)	N3—H3	0.8600
C7—N1	1.277 (4)	O1—H1	0.87 (5)
C7—H13	0.9300	O2—H2	0.8200
C6—C1—C2	118.7 (2)	O3—C8—N2	127.2 (3)
C6—C1—C7	122.7 (2)	N3—C8—N2	101.8 (2)
C2—C1—C7	118.6 (2)	N4—C9—N2	111.1 (2)
C3—C2—C1	121.1 (3)	N4—C9—C10	125.8 (3)
C3—C2—H8	119.5	N2—C9—C10	123.0 (3)
C1—C2—H8	119.5	C9—C10—H15A	109.5
C2—C3—C4	120.0 (3)	C9—C10—H15B	109.5
C2—C3—H9	120.0	H15A—C10—H15B	109.5
C4—C3—H9	120.0	C9—C10—H15C	109.5
C5—C4—C3	120.3 (3)	H15A—C10—H15C	109.5
C5—C4—H44	119.9	H15B—C10—H15C	109.5
C3—C4—H44	119.9	C7—N1—N2	119.9 (2)
O2—C5—C4	124.1 (2)	N1—N2—C9	121.4 (2)
O2—C5—C6	115.5 (3)	N1—N2—C8	130.3 (2)
C4—C5—C6	120.4 (2)	C9—N2—C8	108.3 (2)
O1—C6—C1	123.3 (2)	C8—N3—N4	114.0 (2)
O1—C6—C5	117.1 (2)	C8—N3—H3	123.0
C1—C6—C5	119.6 (3)	N4—N3—H3	123.0
N1—C7—C1	119.7 (2)	C9—N4—N3	104.7 (2)
N1—C7—H13	120.2	C6—O1—H1	105 (3)
C1—C7—H13	120.2	C5—O2—H2	109.5
O3—C8—N3	131.0 (2)
C6—C1—C2—C3	0.2 (4)	C1—C7—N1—N2	178.4 (2)
C7—C1—C2—C3	−178.2 (3)	C7—N1—N2—C9	−176.8 (2)
C1—C2—C3—C4	−0.2 (5)	C7—N1—N2—C8	3.3 (4)
C2—C3—C4—C5	−0.1 (4)	N4—C9—N2—N1	179.0 (2)
C3—C4—C5—O2	−179.6 (3)	C10—C9—N2—N1	−2.6 (4)
C3—C4—C5—C6	0.5 (4)	N4—C9—N2—C8	−1.1 (3)
C2—C1—C6—O1	−179.0 (2)	C10—C9—N2—C8	177.3 (3)
C7—C1—C6—O1	−0.7 (4)	O3—C8—N2—N1	0.5 (5)
C2—C1—C6—C5	0.2 (4)	N3—C8—N2—N1	−178.5 (3)
C7—C1—C6—C5	178.5 (2)	O3—C8—N2—C9	−179.4 (3)
O2—C5—C6—O1	−1.2 (4)	N3—C8—N2—C9	1.6 (3)
C4—C5—C6—O1	178.7 (2)	O3—C8—N3—N4	179.4 (3)
O2—C5—C6—C1	179.5 (2)	N2—C8—N3—N4	−1.7 (3)
C4—C5—C6—C1	−0.5 (4)	N2—C9—N4—N3	0.0 (3)
C6—C1—C7—N1	−1.6 (4)	C10—C9—N4—N3	−178.3 (3)
C2—C1—C7—N1	176.7 (3)	C8—N3—N4—C9	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.11	2.842 (3)	148
N3—H3···O3ii	0.86	2.00	2.830 (3)	163
O1—H1···N1	0.87 (5)	1.85 (5)	2.634 (3)	148 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.11	2.842 (3)	148
N3—H3⋯O3ii	0.86	2.00	2.830 (3)	163
O1—H1⋯N1	0.87 (5)	1.85 (5)	2.634 (3)	148 (4)

Symmetry codes: (i) ; (ii) .