5-[(4-Meth­oxy­benz­yl)sulfan­yl]-2-methyl-1,3,4-thia­diazole

Hoong-Kun Fun; Suchada Chantrapromma; B Chandrakantha; Arun M Isloor; Prakash Shetty

doi:10.1107/S1600536810051858

. 2010 Dec 18;67(Pt 1):o163. doi: 10.1107/S1600536810051858

5-[(4-Methoxybenzyl)sulfanyl]-2-methyl-1,3,4-thiadiazole

Hoong-Kun Fun ^a,^*,^‡, Suchada Chantrapromma ^b,^§, B Chandrakantha ^c, Arun M Isloor ^d, Prakash Shetty ^e

PMCID: PMC3050388 PMID: 21522670

Abstract

The title molecule, C₁₁H₁₂N₂OS₂, is twisted with a dihedral angle of 83.63 (12)° between the 1,3,4-thiadiazole and benzene rings. The methoxy group deviates slightly from the attached benzene ring, with a C—C—O—C torsion angle of 4.2 (4)°. In the crystal, molecules are linked by weak C—H⋯N interactions and stacked along the c axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Wang et al. (2010 ▶). For background to and applications of thiadiazole derivatives, see: Bernard et al. (1985 ▶); Chandrakantha et al. (2010 ▶); El-Sabbagh et al. (2009) ▶; Isloor et al. (2010 ▶); Kalluraya et al. (2004 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₁H₁₂N₂OS₂
M _r = 252.35
Monoclinic,
a = 14.7765 (4) Å
b = 8.6916 (3) Å
c = 9.7339 (3) Å
β = 96.477 (1)°
V = 1242.16 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 296 K
0.25 × 0.19 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.907, T _max = 0.987
11429 measured reflections
2828 independent reflections
1660 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.118
S = 1.02
2828 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 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/S1600536810051858/is2640sup1.cif

e-67-0o163-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051858/is2640Isup2.hkl

e-67-0o163-Isup2.hkl^{(138.9KB, 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
C1—H1B⋯N1ⁱ	0.96	2.59	3.532 (4)	164

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award. SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Thiadiazole are a class of heterocyclic compounds having a five membered ring. They occur in nature and are predominant among all types of pharmaceuticals, agrochemicals and veterinary products (El-Sabbagh et al., 2009). The amino and mercapto groups in thiadiazole are readily-accessible nucleophilic centers. 1,3,4-Thiadiazole exhibit a wide spectrum of biological activities (Bernard et al., 1985). Due to the presence of the –N—C—S moiety (Kalluraya et al., 2004), they are found to be used as antibacterial, antimicrobial and anti-inflammatory agents (Chandrakantha et al., 2010). Antibacterial and antifungal (Isloor et al., 2010) activities of the azoles are most widely studied and azoles are also used as antimicrobial agents. Herein we report the crystal structure of the title 1,3,4-thiadiazole derivative, (I).

The molecule of (I) (Fig. 1) is twisted with a dihedral angle between the 1,3,4-thiadiazole and benzene rings being 83.63 (12)°. Atoms C3, S2, C4 and C5 lie nearly on the same plane with r.m.s. 0.0517 (5) Å and the torsion angle C3–S2–C4–C5 = 172.25 (18)°. The mean plane through C3/S2/C4/C5 makes the dihedral angles of 9.02 (15) and 75.92 (16)° with the 1,3,4-thiadiazole and benzene rings, respectively. The methoxy group is slightly deviated with respect to the attached benzene ring with the torsion angle C11–O1–C8–C9 = 4.2 (4)°. The bond distances are of normal values (Allen et al., 1987) and are comparable with the related structure (Wang et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked by C1—H1B···N1 weak interactions (Table 1) and stacked along the c axis. S···N [3.340 (2) Å] short contacts (symmetry codes: x, 1/2 - y, 1/2 + z and x, 1/2 - y, -1/2 + z) are presented in the crystal.

Experimental

The title compound was synthesized by adding 4-methoxybenzylbromide (3.02 g, 0.0151 mol) dropwise to a stirred solution of 5-methyl-1,3,4-thiadiazole-2-thiol (2.00 g, 0.0151 mol) and anhydrous potassiumcarbonate (4.16 g, 0.03 mol) in dry acetonitrile (50 ml) at room temperature and the reaction mixture was stirred at room temperature for 5 h. After the completion of reaction, the reaction mixture was filtered and the filtrate was concentrated. The crude product was recrystallized with hot ethanol to afford the title compound as yellow solid (2.00 g, yield 57%). Yellow plate-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days (m.p. 413–415 K).