4-Amino-3-(4-hy­droxy­benz­yl)-1H-1,2,4-triazole-5(4H)-thione

Sarojini, B.K.; Manjula, P.S.; Kaur, M.; Anderson, B.J.; Jasinski, J.P.

doi:10.1107/S1600536813033370

organic compounds

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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o48-o49

https://doi.org/10.1107/S1600536813033370

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4-Amino-3-(4-hydroxybenzyl)-1H-1,2,4-triazole-5(4H)-thione

B. K. Sarojini,^a,^b P. S. Manjula,^a Manpreet Kaur,^c Brian J. Anderson ^d and Jerry P. Jasinski ^d ^*

^aDepartment of Chemistry, P.A. College of Engineering, Nadupadavu 574 153, D.K., Mangalore, India, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 8 December 2013; accepted 9 December 2013; online 14 December 2013)

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, molecules 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.

CCDC reference: 976026

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_r = 222.27
Triclinic, P 1
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.102
S = 1.10
1897 reflections
145 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 265 Friedel pairs (15% coverage)
Absolute structure parameter: −0.02 (9)

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⋯N1^iv	0.91 (3)	2.32 (3)	3.149 (4)	153 (3)
Symmetry codes: (i) x, y, z-1; (ii) x+1, y+1, z+1; (iii) x-1, y, z; (iv) x, y-1, z.

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.

Supporting information

CCDC reference: 976026

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813033370/su2674sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033370/su2674Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813033370/su2674Isup3.cml

checkCIF report

Comment top

The chemistry of triazoles has received considerable attention in recent years because of their versatility in the synthesis of many other heterocyclic compounds. 1,2,4-Triazole derivatives are well known for their different biological activities, therefore various 1,2,4-triazole derivatives and their N-bridged heterocyclic analogs have been extensively studied (Holla et al., 2001,2006). The derivatives of 1,2,4-triazole are known to exhibit anti-inflammatory (Mullican et al., 1993), antiviral (Jones et al., 1965), antimicrobial (Shams El-Dine et al., 1974; Misato et al., 1977) and antidepressant activity (Kane et al., 1988). Hence synthesis of the corresponding heterocyclic compounds could be of interest from the viewpoint of chemical reactivity and biological activity.

The crystal structures of some related triazoles have been reported: 5-(2-Chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4-triazole-3-thione (Puviarasan et al., 1999); 4-Amino-5-(2-ethoxyphenyl)-2,4-dihydro- 2H-1,2,4-triazole-3-thione-triphenylphosphine oxide (Chen et al., 2007); Ethyl2-(3-methyl-5-sulfanylidene-4,5-dihydro- 1H-1,2,4-triazol-4-yl)acetate (Karczmarzyk et al., 2012); 3-(4-Amino-3-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1- yl)-3-(2-chlorophenyl)-1-phenylpropan-1-one (Gao et al., 2011). The present work describes the synthesis and crystal structure of the title compound.

In the title compound, Fig. 1, the dihedral angle between the benzene ring (C2-C7) and the 1H-1,2,4-triazole-5(4H)-thione ring (N1/N2/C9/N3/C8) is 67.51 (16) °.

In the crystal, a single N2—H2···O1 hydrogen bond and additional weak O1—H1···S1, N4—H4A···S1 and N4—H4B···N1 hydrogen bonds are observed (Table 1 and Fig. 2). These interactions link the molecules into one-dimensional chains extending along each of the three axes forming a three-dimensional supramolecular framework.

Related literature top

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 top

The synthesis of the title compound is described in Fig. 3. A well triturated mixture of 4-hydroxyphenylacetic acid (0.755 g, 0.005 mol) and thiocarbohydrazide (0.53 g, 0.005 mol) was fused in a round bottom flask for one hour on an oil bath at 413 K. It was cooled to room temperature and washed with sodium bicarbonate (5%) solution to remove unreacted acid and again washed with water. The dried compound was recrystallized from methanol yielding colourless block-like crystals (M.p. 475-477 K).

Structure description top

In the title compound, Fig. 1, the dihedral angle between the benzene ring (C2-C7) and the 1H-1,2,4-triazole-5(4H)-thione ring (N1/N2/C9/N3/C8) is 67.51 (16) °.

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); 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 (Dolomanov et al., 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines; see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. Synthesis of the title compound.

4-Amino-3-(4-hydroxybenzyl)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₉H₁₀N₄OS	Z = 1
M_r = 222.27	F(000) = 116
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.035
ω scans	θ_max = 32.9°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012).	h = −6→6
T_min = 0.941, T_max = 1.000	k = −8→9
2555 measured reflections	l = −14→12

Refinement top

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(F_o²) + (0.0512P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.102	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.29 e Å⁻³
1897 reflections	Δρ_min = −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

Crystal data top

C₉H₁₀N₄OS	γ = 104.589 (10)°
M_r = 222.27	V = 247.14 (5) Å³
Triclinic, P1	Z = 1
a = 4.2117 (5) Å	Mo Kα radiation
b = 6.1891 (7) Å	µ = 0.31 mm⁻¹
c = 10.0641 (11) Å	T = 173 K
α = 100.590 (9)°	0.34 × 0.30 × 0.24 mm
β = 94.916 (9)°

Data collection top

Agilent Gemini EOS diffractometer	1897 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012).	1826 reflections with I > 2σ(I)
T_min = 0.941, T_max = 1.000	R_int = 0.035
2555 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	Δρ_max = 0.29 e Å⁻³
S = 1.10	Δρ_min = −0.27 e Å⁻³
1897 reflections	Absolute structure: Flack (1983), 265 Friedel pairs (15% coverage)
145 parameters	Absolute structure parameter: −0.02 (9)
3 restraints

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···N1^iv	0.91 (3)	2.32 (3)	3.149 (4)	153 (3)

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

Hydrogen-bond geometry (Å, º) top

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···N1^iv	0.91 (3)	2.32 (3)	3.149 (4)	153 (3)

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

Acknowledgements

BKS and PSM gratefully acknowledge the Department of Chemistry, P. A. College of Engineering, for providing research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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