Crystal structure of 4-amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Mustafa R Albayati

doi:10.1107/S205698901500938X

. 2015 May 23;71(Pt 6):o417. doi: 10.1107/S205698901500938X

Crystal structure of 4-amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Mustafa R Albayati ^e,^*

PMCID: PMC4459321 PMID: 26090200

Abstract

In the title compound, C₁₂H₁₂N₆S, the dihedral angles between the central pyrazole ring and the pendant triazole and benzene rings are 68.01 (4) and 59.83 (9)°, respectively. In the crystal, molecules are linked by N—H⋯N and N—H⋯S hydrogen bonds, generating (10-1) sheets.

Keywords: crystal structure, aminotriazoles, hydrogen bonding

Related literature

For the bio-activities of aminotriazoles, see: Jin et al. (2007 ▸); Joung et al. (2000 ▸). For aminotriazoles as block-building synthons, see: Curtis (2004 ▸).

Experimental

Crystal data

C₁₂H₁₂N₆S
M _r = 272.34
Monoclinic,
a = 11.3278 (4) Å
b = 8.3970 (3) Å
c = 15.4427 (5) Å
β = 109.053 (1)°
V = 1388.43 (8) Å³
Z = 4
Cu Kα radiation
μ = 2.04 mm⁻¹
T = 150 K
0.24 × 0.18 × 0.10 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.77, T _max = 0.82
10355 measured reflections
2683 independent reflections
2515 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.102
S = 1.09
2683 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500938X/hb7427sup1.cif

e-71-0o417-sup1.cif^{(326.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500938X/hb7427Isup2.hkl

e-71-0o417-Isup2.hkl^{(147.5KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supporting information file. DOI: 10.1107/S205698901500938X/hb7427Isup3.cml

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S205698901500938X/hb7427fig1.tif

The title molecule showing labeling scheme and 50% probability ellipsoids.

Click here for additional data file.^{(1.2MB, tif)}

b . DOI: 10.1107/S205698901500938X/hb7427fig2.tif

Packing viewed down the b axis. N—H⋯N and N—H⋯S hydrogen bonds are shown, respectively, as blue and purple dotted lines.

CCDC reference: 1401505

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N3H3AN1ⁱ	0.91	1.94	2.8429(17)	169
N6H6AS1ⁱⁱ	0.91	2.55	3.4157(13)	159
N6H6BN4ⁱⁱⁱ	0.91	2.43	3.0059(18)	122

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

Amino-1,2,4-triazoles are known to be biologically active compounds (Jin et al., 2007). For example, the 5-amino-1,2,4- triazole itself has been used as the pesticide Amitrole (Joung et al., 2000) and 3,5-diamino-1,2,4-triazole (Guanazole) is an antitumor drug that inhibits ribonucleotide reductase and DNA synthesis. In addition, they play an important role as amidine type synthons in heterocyclic chemistry (Curtis, 2004) particularly fused ring systems, such as imidazo[1,2-b][1,2,4]triazole, imidazo[2,1-c][1,2,4]triazole, 1,2,4-triazolo[1,5-a]pyrimidine and 1,2,4-traizolo[1,5-a][1,3,5]triazine possessing variety of biological effects. In this context, we report in this study the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the dihedral angle between the central 5-membered ring and its attached phenyl ring is 59.83 (5)° while the dihedral angle between the two 5-membered rings is 68.01 (4)°. In the crystal, the molecules form sheets lying parallel to (101) through N—H···N and N—H···S hydrogen bonds (Fig. 2 and Table 1).

S2. Experimental

A mixture of 1 mmol (258 mg) of 5-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1,3,4-oxadiazole-2(3H)-thione and 2 ml of hydrazine in 30 ml ethanol was heated at 351 K for 6 h. On cooling, the solid product was filtered off, dried under vacuum and recrystallized from ethanol to afford colorless blocks of the title compound.