4-[(E)-4-Bromo­benzyl­ideneamino]-3-[1-(4-isobutyl­phen­yl)eth­yl]-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun; Samuel Robinson Jebas; K V Sujith; Balakrishna Kalluraya

doi:10.1107/S1600536809018030

. 2009 May 20;65(Pt 6):o1340–o1341. doi: 10.1107/S1600536809018030

4-[(E)-4-Bromobenzylideneamino]-3-[1-(4-isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun ^a,^*,^‡, Samuel Robinson Jebas ^a,^§, K V Sujith ^b, Balakrishna Kalluraya ^b

PMCID: PMC2969682 PMID: 21583193

Abstract

In the title compound, C₂₁H₂₃BrN₄S, the 4-bromobenzylidene group is disordered over two orientations with occupancies of 0.504 (5) and 0.496 (5). One of the methyl groups of the isobutyl unit is disordered over two sites with occupancies of 0.751 (19) and 0.249 (19). The benzene rings of the isobutylphenyl and bromophenyl (major disorder component) groups form dihedral angles of 71.63 (11) and 21.8 (3)°, respectively, with the triazole ring. In the crystal, centrosymmetrically related molecules exist as centrosymmetric N—H⋯S hydrogen-bonded dimers.

Related literature

For the pharmaceutical applications of triazole derivatives, see: Al-Soud et al. (2003 ▶); Almasirad et al. (2004 ▶); Amir & Shikha (2004 ▶); Demirbas et al. (2004 ▶); Holla et al. (2003 ▶); Kawashima et al. (1987 ▶); Zitouni et al. (2005 ▶); Walczak et al. (2004 ▶); For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₁H₂₃BrN₄S
M _r = 443.40
Triclinic,
a = 5.5791 (2) Å
b = 11.3052 (3) Å
c = 17.3688 (4) Å
α = 75.421 (1)°
β = 86.614 (1)°
γ = 79.616 (1)°
V = 1042.75 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.08 mm⁻¹
T = 100 K
0.27 × 0.17 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.602, T _max = 0.908
26698 measured reflections
8529 independent reflections
5907 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.141
S = 1.05
8529 reflections
331 parameters
44 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018030/ci2795sup1.cif

e-65-o1340-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018030/ci2795Isup2.hkl

e-65-o1340-Isup2.hkl^{(408.8KB, 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
N1—H1N1⋯S1ⁱ	0.91 (4)	2.35 (4)	3.2582 (18)	175 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Some degree of respectability has been bestowed on 1,2,4-triazole derivatives due to their antibacterial, antifungal (Zitouni et al., 2005), antitubercular (Walczak et al., 2004), anticancer (Holla et al., 2003), antitumor (Al-Soud et al., 2003), anticonvulsant (Almasirad et al., 2004), anti-inflammatory, and analgesic properties (Amir & Shikha, 2004). Certain 1,2,4-triazoles also find applications in the preparation of photographic plates, polymers, and as analytical agents (Kawashima et al., 1987). Similarly Schiff base derivatives of 1,2,4-triazol-5-ones have been found to possess antitumor activity (Demirbas et al., 2004). In our earlier studies, we have reported the crystal structure of heterocyclic compounds containing both the ibuprofen and 1,2,4- triazole fragments (Fun et al., 2008a,b). Prompted by these observations and in continuation of our interest in the synthesis of chemically and biologically important heterocycles, we synthesized the title compound and report here its crystal structure.

Bond lengths (Allen et al., 1987) and angles are normal. The (4-bromophenyl)methylidene group is disordered over two orientations. The C11-C16 benzene ring forms a dihedral angle of 71.63 (11)° with the triazole ring (N1-N3/C8/C9). The dihedral angle between the C1A-C6A and N1-N3/C8/C9 rings is 21.8 (3)°.

The crystal packing (Fig 2) is consolidated by intermolecular N—H···S hygrogen bonds. These hydrogen bonds link centrosymmetrically related molecules into dimers.

Experimental

The title Schiff base compound was obtained by refluxing 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,2,4-triazole-3-thiol (0.01 mol) and 4-bromobenzaldehyde (0.01 mol) in ethanol (50 ml) with 3 drops of concentrated sulfuric acid for 3 h. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.