4-Amino-3-(4-hy-droxy-benz-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C9H10N4OS, the dihedral angle between the benzene and 1H-1,2,4-triazole-5(4H)-thione rings is 67.51 (16)°. In the crystal, mol-ecules are liked via N-H⋯O hydrogen bonds, forming chains along the c-axis direction. The chains are linked via O-H⋯S hydrogen bonds, forming corrugated layers lying parallel to the bc plane. The layers are linked via N-H⋯N and N-H⋯S hydrogen bonds, forming a three-dimensional network.

Related literature

For biological properties of 1,2,4-triazole derivatives, see: Holla et al. (2001 ▶, 2006 ▶); Mullican et al. (1993 ▶); Jones et al. (1965 ▶); Shams El-Dine et al. (1974 ▶); Misato et al. (1977 ▶); Kane et al. (1988 ▶). For related structures, see: Puviarasan et al. (1999 ▶); Chen et al. (2007 ▶); Karczmarzyk et al. (2012 ▶); Gao et al. (2011 ▶).

Experimental

Crystal data

C9H10N4OS

M = 222.27

Triclinic,

a = 4.2117 (5) Å

b = 6.1891 (7) Å

c = 10.0641 (11) Å

α = 100.590 (9)°

β = 94.916 (9)°

γ = 104.589 (10)°

V = 247.14 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.31 mm−1

T = 173 K

0.34 × 0.30 × 0.24 mm

Data collection

Agilent Gemini EOS diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶). T min = 0.941, T max = 1.000

2555 measured reflections

1897 independent reflections

1826 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.10

1897 reflections

145 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 265 Friedel pairs (15% coverage)

Absolute structure parameter: −0.02 (9)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033370/su2674sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033370/su2674Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033370/su2674Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H10N4OS	Z = 1
Mr = 222.27	F(000) = 116
Triclinic, P1	Dx = 1.493 Mg m−3
a = 4.2117 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.1891 (7) Å	Cell parameters from 1329 reflections
c = 10.0641 (11) Å	θ = 3.5–32.8°
α = 100.590 (9)°	µ = 0.31 mm−1
β = 94.916 (9)°	T = 173 K
γ = 104.589 (10)°	Block, colourless
V = 247.14 (5) Å3	0.34 × 0.30 × 0.24 mm

Agilent Gemini EOS diffractometer	1897 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1826 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.035
ω scans	θmax = 32.9°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012).	h = −6→6
Tmin = 0.941, Tmax = 1.000	k = −8→9
2555 measured reflections	l = −14→12

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.29 e Å−3
1897 reflections	Δρmin = −0.27 e Å−3
145 parameters	Absolute structure: Flack (1983), 265 Friedel pairs (15% coverage)
3 restraints	Absolute structure parameter: −0.02 (9)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
S1	0.98393 (10)	0.49047 (8)	−0.16110 (7)	0.02134 (16)
O1	1.3407 (6)	1.0709 (3)	0.7411 (2)	0.0248 (4)
N1	0.8426 (6)	1.0486 (4)	0.0472 (3)	0.0217 (5)
N2	0.9604 (6)	0.9245 (4)	−0.0560 (2)	0.0205 (5)
H2	1.0738	0.9862	−0.1156	0.025*
N3	0.7176 (5)	0.6844 (3)	0.0529 (2)	0.0164 (4)
N4	0.5720 (6)	0.4828 (4)	0.0952 (3)	0.0227 (5)
H4A	0.3813	0.4158	0.0464	0.027*
C1	0.5336 (7)	0.9471 (5)	0.2357 (3)	0.0211 (5)
H1A	0.3342	0.8192	0.2314	0.025*
H1B	0.4603	1.0871	0.2357	0.025*
C2	0.7593 (7)	0.9795 (4)	0.3678 (3)	0.0187 (5)
C3	0.7404 (8)	0.8033 (5)	0.4367 (3)	0.0238 (6)
H3	0.5876	0.6587	0.3991	0.029*
C4	0.9400 (8)	0.8336 (5)	0.5596 (3)	0.0248 (6)
H4	0.9254	0.7104	0.6049	0.030*
C5	1.1611 (7)	1.0458 (5)	0.6157 (3)	0.0200 (5)
C6	1.1905 (7)	1.2236 (5)	0.5479 (3)	0.0229 (6)
H6	1.3466	1.3672	0.5849	0.027*
C7	0.9885 (8)	1.1898 (5)	0.4243 (3)	0.0219 (5)
H7	1.0071	1.3119	0.3779	0.026*
C8	0.6955 (6)	0.8986 (4)	0.1125 (3)	0.0167 (5)
C9	0.8850 (6)	0.7017 (4)	−0.0565 (3)	0.0168 (5)
H1	1.500 (12)	1.216 (7)	0.758 (5)	0.038 (11)*
H4B	0.713 (8)	0.395 (5)	0.079 (3)	0.009 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0238 (3)	0.0209 (3)	0.0187 (3)	0.0076 (2)	0.0035 (2)	0.0003 (2)
O1	0.0279 (10)	0.0253 (10)	0.0156 (10)	−0.0007 (8)	−0.0003 (8)	0.0027 (8)
N1	0.0283 (12)	0.0185 (10)	0.0187 (11)	0.0085 (9)	0.0033 (9)	0.0020 (8)
N2	0.0267 (12)	0.0182 (10)	0.0158 (11)	0.0041 (9)	0.0051 (9)	0.0039 (8)
N3	0.0182 (10)	0.0157 (9)	0.0148 (10)	0.0033 (8)	0.0018 (8)	0.0041 (8)
N4	0.0253 (11)	0.0180 (10)	0.0247 (13)	0.0021 (9)	0.0074 (10)	0.0079 (9)
C1	0.0215 (11)	0.0252 (12)	0.0185 (13)	0.0102 (10)	0.0038 (10)	0.0038 (10)
C2	0.0221 (11)	0.0212 (11)	0.0132 (12)	0.0070 (9)	0.0053 (9)	0.0017 (9)
C3	0.0278 (13)	0.0204 (11)	0.0203 (13)	0.0018 (10)	0.0023 (11)	0.0043 (10)
C4	0.0322 (14)	0.0202 (12)	0.0194 (13)	0.0012 (10)	0.0023 (11)	0.0061 (10)
C5	0.0215 (12)	0.0234 (12)	0.0145 (11)	0.0059 (10)	0.0058 (10)	0.0016 (9)
C6	0.0253 (13)	0.0194 (11)	0.0199 (13)	0.0007 (10)	0.0050 (11)	0.0008 (10)
C7	0.0289 (13)	0.0193 (11)	0.0187 (13)	0.0067 (10)	0.0067 (11)	0.0051 (9)
C8	0.0185 (11)	0.0173 (11)	0.0138 (11)	0.0059 (9)	−0.0013 (9)	0.0020 (9)
C9	0.0182 (11)	0.0173 (10)	0.0135 (11)	0.0034 (9)	0.0002 (9)	0.0026 (9)

S1—C9	1.683 (3)	C1—H1B	0.9900
O1—C5	1.376 (4)	C1—C2	1.517 (4)
O1—H1	0.95 (4)	C1—C8	1.484 (4)
N1—N2	1.379 (3)	C2—C3	1.385 (4)
N1—C8	1.297 (4)	C2—C7	1.396 (4)
N2—H2	0.8800	C3—H3	0.9500
N2—C9	1.334 (3)	C3—C4	1.389 (4)
N3—N4	1.403 (3)	C4—H4	0.9500
N3—C8	1.380 (3)	C4—C5	1.390 (4)
N3—C9	1.364 (3)	C5—C6	1.384 (4)
N4—H4A	0.8645	C6—H6	0.9500
N4—H4B	0.91 (3)	C6—C7	1.395 (4)
C1—H1A	0.9900	C7—H7	0.9500
C5—O1—H1	106 (3)	C2—C3—C4	121.4 (3)
C8—N1—N2	104.5 (2)	C4—C3—H3	119.3
N1—N2—H2	123.4	C3—C4—H4	120.3
C9—N2—N1	113.2 (2)	C3—C4—C5	119.4 (3)
C9—N2—H2	123.4	C5—C4—H4	120.3
C8—N3—N4	124.5 (2)	O1—C5—C4	117.3 (3)
C9—N3—N4	126.6 (2)	O1—C5—C6	122.3 (2)
C9—N3—C8	108.8 (2)	C6—C5—C4	120.4 (3)
N3—N4—H4A	109.6	C5—C6—H6	120.4
N3—N4—H4B	104 (2)	C5—C6—C7	119.3 (3)
H4A—N4—H4B	109.9	C7—C6—H6	120.4
H1A—C1—H1B	107.8	C2—C7—H7	119.4
C2—C1—H1A	109.0	C6—C7—C2	121.1 (3)
C2—C1—H1B	109.0	C6—C7—H7	119.4
C8—C1—H1A	109.0	N1—C8—N3	110.1 (2)
C8—C1—H1B	109.0	N1—C8—C1	125.8 (2)
C8—C1—C2	113.0 (2)	N3—C8—C1	124.2 (2)
C3—C2—C1	121.1 (2)	N2—C9—S1	129.2 (2)
C3—C2—C7	118.3 (3)	N2—C9—N3	103.4 (2)
C7—C2—C1	120.6 (2)	N3—C9—S1	127.36 (19)
C2—C3—H3	119.3
O1—C5—C6—C7	−176.7 (3)	C3—C2—C7—C6	−0.9 (4)
N1—N2—C9—S1	−178.7 (2)	C3—C4—C5—O1	176.6 (3)
N1—N2—C9—N3	−1.2 (3)	C3—C4—C5—C6	−2.1 (5)
N2—N1—C8—N3	−0.1 (3)	C4—C5—C6—C7	1.9 (4)
N2—N1—C8—C1	178.4 (3)	C5—C6—C7—C2	−0.4 (4)
N4—N3—C8—N1	−177.2 (3)	C7—C2—C3—C4	0.7 (4)
N4—N3—C8—C1	4.3 (4)	C8—N1—N2—C9	0.8 (3)
N4—N3—C9—S1	−4.9 (4)	C8—N3—C9—S1	178.64 (19)
N4—N3—C9—N2	177.5 (3)	C8—N3—C9—N2	1.1 (3)
C1—C2—C3—C4	−178.2 (3)	C8—C1—C2—C3	−98.8 (3)
C1—C2—C7—C6	178.1 (3)	C8—C1—C2—C7	82.2 (3)
C2—C1—C8—N1	−94.8 (3)	C9—N3—C8—N1	−0.7 (3)
C2—C1—C8—N3	83.5 (3)	C9—N3—C8—C1	−179.1 (2)
C2—C3—C4—C5	0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88	1.97	2.840 (3)	170
O1—H1···S1ii	0.95 (5)	2.27 (5)	3.180 (2)	159 (4)
N4—H4A···S1iii	0.86	2.74	3.435 (3)	138
N4—H4B···N1iv	0.91 (3)	2.32 (3)	3.149 (4)	153 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88	1.97	2.840 (3)	170
O1—H1⋯S1ii	0.95 (5)	2.27 (5)	3.180 (2)	159 (4)
N4—H4A⋯S1iii	0.86	2.74	3.435 (3)	138
N4—H4B⋯N1iv	0.91 (3)	2.32 (3)	3.149 (4)	153 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .