3-Ethyl-4-[(E)-(4-fluoro­benzyl­idene)amino]-1H-1,2,4-triazole-5(4H)-thione

S Jeyaseelan; H C Devarajegowda; R Sathishkumar; Agnes Sylvia D’souza; Alphonsus D’souza

doi:10.1107/S1600536812015346

. 2012 Apr 18;68(Pt 5):o1407. doi: 10.1107/S1600536812015346

3-Ethyl-4-[(E)-(4-fluorobenzylidene)amino]-1H-1,2,4-triazole-5(4H)-thione

S Jeyaseelan ^a, H C Devarajegowda ^a,^*, R Sathishkumar ^b, Agnes Sylvia D’souza ^c, Alphonsus D’souza ^c

PMCID: PMC3344533 PMID: 22590295

Abstract

In the title compound, C₁₁H₁₁FN₄S, the dihedral angle between the 1,2,4-triazole ring and the benzene ring is 25.04 (12)° and an intramoleuclar C—H⋯S interaction leads to an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R ₂ ²(8) loops.

Related literature

For a related structure and background references, see: Devarajegowda et al. (2010 ▶).

Experimental

Crystal data

C₁₁H₁₁FN₄S
M _r = 250.30
Monoclinic,
a = 7.7967 (17) Å
b = 8.4205 (19) Å
c = 19.138 (4) Å
β = 99.780 (4)°
V = 1238.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.770, T _max = 1.000
11403 measured reflections
2182 independent reflections
1586 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.115
S = 1.02
2182 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015346/hb6709sup1.cif

e-68-o1407-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015346/hb6709Isup2.hkl

e-68-o1407-Isup2.hkl^{(105.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015346/hb6709Isup3.cml

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
N4—H4⋯S1ⁱ	0.86	2.48	3.3275 (19)	168
C11—H11⋯S1	0.93	2.55	3.222 (3)	129

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.

supplementary crystallographic information

Comment

Earlier we reported the crystal structure of 1-{1-[2,8- Bis(trifluoromethyl)-4-quinolyl]-5-methyl-1H-1,2,3-triazol- 4-yl}ethanone (Devarajegowda et al.,2010). We report here the crystal structure of the title compound (Fig. 1). The packing of the molecules in the title structure is depicted in Fig. 2. The 1,2,4 triazole ring (N3 N4 N5 C9 C10 is not coplanar with the benzene ring (C12—C17) system; the dihedral angle between the two planes being 25.04 (12)°. The crystal structure is characterized by intermolecular N4—H4···S1 and intramolecular C11—H11···S1 interactions are observed (Table 1).

Experimental

An equimolar mixture of the triazole (0.02 mol) and 4-fluorobenzaldehyde (0.02 mol) in absolute ethanol (30 ml) was refluxed with concentrated H₂S_O4 (0.5 ml) for 1–2 hrs. On cooling the reaction mixture, the solid product separated was crystallized from ethanol as colourless blocks. The synthesized compound was evaluated for antibacterial and antifungal activity by cup-plate diffusion method and used as the standard drugs for antibacterial and antifungal activity respectively.