3-[1-(4-Isobutyl­phen­yl)eth­yl]-6-(4-methyl­phen­yl)-1,2,4-triazolo[3,4-b][1,3,4]thia­diazole

Hoong-Kun Fun; Samuel Robinson Jebas; Ibrahim Abdul Razak; K V Sujith; P S Patil; B Kalluraya; S M Dharmaprakash

doi:10.1107/S1600536808013883

. 2008 May 14;64(Pt 6):o1076–o1077. doi: 10.1107/S1600536808013883

3-[1-(4-Isobutylphenyl)ethyl]-6-(4-methylphenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

Hoong-Kun Fun ^a,^*, Samuel Robinson Jebas ^a,^‡, Ibrahim Abdul Razak ^a, K V Sujith ^b, P S Patil ^c, B Kalluraya ^b, S M Dharmaprakash ^c

PMCID: PMC2961563 PMID: 21202594

Abstract

In the title compound, C₂₂H₂₄N₄S, the methylphenyl and isobutylphenyl rings are inclined at an angle of 79.98 (1)° and they form dihedral angles of 4.59 (1) and 75.47 (1)°, respectively, with the triazolothiadiazole unit. An intramolecular C—H⋯S hydrogen bond generates an S(5) ring motif. The crystal structure is stabilized by intermolecular C—H⋯N hydrogen bonds and weak C—H⋯π and π–π interactions [centroid–centroid distances between the thiadiazole ring and a symmetry-related phenyl ring and between the triazole ring and the phenyl ring range from 3.5680 (8) to 3.7313 (8) Å].

Related literature

For information on the biological activity of triazole derivatives, thiadiazoles and triazolothiadiazole compounds, see: Holla et al. (2003 ▶); Bekircan & Bektas (2006 ▶); Zhou et al. (2007 ▶); Bhat et al. (2004 ▶); Mathew et al. (2007 ▶); Karthikeyan et al. (2007 ▶); Chaturvedi et al. (1988 ▶); Shawali & Sayed (2006 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related literature, see: Tayseer et al. (2002 ▶).

Experimental

Crystal data

C₂₂H₂₄N₄S
M _r = 376.51
Triclinic,
a = 7.2545 (1) Å
b = 8.1764 (1) Å
c = 17.6556 (3) Å
α = 97.390 (1)°
β = 96.120 (1)°
γ = 106.240 (1)°
V = 984.90 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100.0 (1) K
0.46 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.922, T _max = 0.969
15868 measured reflections
5687 independent reflections
4391 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.141
S = 1.08
5687 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013883/sj2495sup1.cif

e-64-o1076-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013883/sj2495Isup2.hkl

e-64-o1076-Isup2.hkl^{(272.8KB, 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
C5—H5A⋯S1	0.93	2.70	3.1194 (16)	108
C15—H15A⋯N3ⁱ	0.93	2.48	3.343 (2)	155
C4—H4A⋯Cg1ⁱⁱ	0.93	2.62	3.5063	160

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C11–C16 ring.

Acknowledgments

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. FHK and IAR also thank the Malaysian Government and Universiti Sains Malaysia for the FRGS grant No. 203/PFIZIK/671064. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Triazoles and their heterocyclic derivatives represent an interesting class of compounds possessing a wide spectrum of biological activity, such as anticancer, anticonvulsant, analgesic, antibacterial, anthelmintic, antitubercular and anti-inflammatory activities (Holla et al., 2003; Bekircan & Bektas, 2006; Zhou et al., 2007). Similarly 1, 3,4-thiadiazoles were also found to possess antitumor, anti-inflammatory, antibacterial, antifungal, anticonvulsant and antitubercular properties (Bhat et al., 2004; Mathew et al., 2007). Thus triazolothiadiazole systems may be viewed as cyclic analogues of two very important components, which often display diverse pharmacological properties. Triazolothiadiazoles obtained by fusing the biolabile 1,2,4-triazole and 1,3,4-thiadiazole rings together have been reported to possess similar biological properties (Karthikeyan et al., 2007; Chaturvedi et al., 1988; Shawali & Sayed 2006) and the crystal structure of the title triazolothiadiazole compound is reported here.

Bond lengths and angles in the title compound (Fig 1) have normal values (Allen et al., 1987). The triazolothiadiazole ring is planar with the maximum deviation of 0.016 (2)Å for atom C7. The planes through the C1—C6 and C11—C16 rings form dihedral angles of 4.59 (1)° and 75.47 (1)° respectively, with the triazolothiadiazole unit. This is also planar with a dihedral angle of 1.34 (2) ° between the two five membered rings. A weak intramolecular C—H···S hydrogen bond generates an S(5) ring motif (Bernstein et al., (1995) and contributes to the planarity of the 4-methylphenyl-triazolothiadiazole portion of the molecule.

The crystal packing is stabilized by intermolecular C—H···N hydrogen bonds and a weak C—H···π interaction involving the C11—C16 ring (centroid Cg1, Table 1). π–π interactions are observed between the thiadiazole ring (S1/C7/N1—N2/C8) and the symmetry related phenyl rings (C1—C6) and between the triazole ring and the phenyl ring (C1—C6) with centroid to centroid distances ranging from 3.5680 (8)–3.7313 (8)Å [symmetry codes:1-X,-Y,1-Z;2-X, -Y,1-Z].

Experimental

A mixture of 4-amino-3-mercapto-5-[1-(4-isobutylphenyl)ethyl]-1, 2,4-triazole (0.01 mol), p-toluic acid (0.01 mol) and 10 ml POCl₃ was refluxed on a water bath for about 9 h. Excess of POCl₃ was removed under reduced pressure. The reaction mixture was cooled, poured into crushed ice, and neutralized with aqueous ammonia. The resulting solid product was filtered off, washed with water, dried, and recrystallized from a mixture of ethanol and dimethylformamide, 1/1, v/v. (Yield 61%; m.p. 134–1360 C). Analysis (%) for C₂₂H₂₄N₄S found (calculated): C 70.16 (70.21), H 6.31 (6.38), N 14.78 (14.89).