N-[(E)-(5-Methyl­thio­phen-2-yl)methyl­idene]-1H-1,2,4-triazol-3-amine

Zahid H Chohan; Muhammad Hanif; M Nawaz Tahir

doi:10.1107/S1600536808041494

. 2008 Dec 13;65(Pt 1):o117. doi: 10.1107/S1600536808041494

N-[(E)-(5-Methylthiophen-2-yl)methylidene]-1H-1,2,4-triazol-3-amine

Zahid H Chohan ^a, Muhammad Hanif ^a, M Nawaz Tahir ^b,^*

PMCID: PMC2968039 PMID: 21581579

Abstract

In the title Schiff base, C₈H₈N₄S, a condensation product of 5-methylthiophene-2-carboxaldehyde and 3-amino-1,2,4-triazole, the dihedral angle between the triazolyl and thienyl rings is 6.44 (14)°. The compound exists as a polymeric chain arising from intermolecular N—H⋯N bonding.

Related literature

For a related comound, see: Chohan et al. (2009 ▶). For the biological properties of such compounds, see: Foroumadi et al. (2003 ▶); Manfredini et al. (2000 ▶).

Experimental

Crystal data

C₈H₈N₄S
M _r = 192.24
Orthorhombic,
a = 7.2570 (7) Å
b = 8.9522 (8) Å
c = 14.2930 (15) Å
V = 928.56 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 (2) K
0.24 × 0.16 × 0.14 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.928, T _max = 0.956
5793 measured reflections
2206 independent reflections
1859 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.097
S = 1.05
2206 reflections
134 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 854 Friedel pairs
Flack parameter: −0.02 (10)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536808041494/ng2524sup1.cif

e-65-0o117-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041494/ng2524Isup2.hkl

e-65-0o117-Isup2.hkl^{(106.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯N1ⁱ	0.85 (3)	2.12 (3)	2.963 (2)	172 (2)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

supplementary crystallographic information

Comment

Compounds derived from triazole possess antimicrobial, analgesic, anti-inflammatory, local anesthetic, antineoplastic and antimalarial properties (Foroumadi et al., 2003). Some triazole Schiff bases also exhibited antiproliferative and anticancer activity (Manfredini et al., 2000). Due to their significant biological applications they have gained much attention in bioinorganic and metal-based drug discovery. In view of its structural and biological importance, we have synthesized (Chohan et al., 2009), series of triazole derived Schiff bases along with the title compound (I). We report herein, its preperation and crystal structure.

In the molecule of title compound, (Fig 1), the bond lengths and angles are within normal ranges. In this molecule 5-methylthiophen ring is attached to 5-membered ring of triazole moiety through the Schiff bond C=N. The dihedral angle between ring A(S1/C1—C4) and B(C7/N2/N3/C8/N4) is 6.44 (14)°. There exist intramolecular as well as an intermolecular H-bonds as given in Table 1. The molecules are connected to each other through intermolecular H-bonds of N–H···N type in a helical way (Fig 2).

Experimental

A mixture of 5-methylthiophene-2-carboxaldehyde (1.09 ml, 0.01 M) and 3-amino-1,2,4-triazole (0.84 g, 0.01 M) in 1:1 molar proportions in methanol (40 ml) was boiled under reflux for 5 h by monitoring through TLC. The reaction mixture was cooled at room temperature and filtered; within an hour a light brown solid product separated from the clear solution. It was filtered, washed with methanol, dried and recrystallized from a mixture of ethanol:methanol (1:1).