4,4′-[(1,3,4-Thia­diazole-2,5-di­yl)bis­(thio­methyl­ene)]dibenzonitrile

Wenxiang Wang; Hong Zhao

doi:10.1107/S1600536808022848

. 2008 Jul 26;64(Pt 8):o1599. doi: 10.1107/S1600536808022848

4,4′-[(1,3,4-Thiadiazole-2,5-diyl)bis(thiomethylene)]dibenzonitrile

Wenxiang Wang ^a, Hong Zhao ^a,^*

PMCID: PMC2962212 PMID: 21203293

Abstract

The title molecule, C₁₈H₁₂N₄S₃, consists of three essentially planar fragments, viz. two methyl-substituted benzonitrile rings and a substituted thiadiazole ring. The dihedral angles between the substituted benzonitrile rings and the central thiadiazole ring are 28.29 (10) and 78.83 (6)°, and the dihedral angle between the two benzonitrile rings is 72.89 (7)°.

Related literature

For related literature, see: Tarafder et al., (2000 ▶); El-Shekeil et al. (1988 ▶); Jinxia et al. (2003 ▶).

Experimental

Crystal data

C₁₈H₁₂N₄S₃
M _r = 380.50
Monoclinic,
a = 7.6974 (15) Å
b = 8.4375 (17) Å
c = 27.272 (6) Å
β = 92.53 (3)°
V = 1769.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 (2) K
0.45 × 0.40 × 0.30 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.814, T _max = 0.903
15327 measured reflections
4028 independent reflections
2754 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.115
S = 1.05
4028 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022848/fl2207sup1.cif

e-64-o1599-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022848/fl2207Isup2.hkl

e-64-o1599-Isup2.hkl^{(197.4KB, hkl)}

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to HZ.

supplementary crystallographic information

Comment

1,3,4-thiadiazole-2,5-dithiol and its derivatives are interesting compounds that have attracted the attention of researchers because of their wide range of applications in many fields, such as the determination of trace elements, the synthesis of novel heterocyclic compounds with antimicrobial activity(El-Shekeil et al. 1988), advanced materials, and battery cathodes (Jinxia et al.2003, Tarafder et al., (2000)). In this paper, we report the structure of one such derviative, the title compound (I).

In (I, Fig. 1) all bond lengths and angles are normal. There are three planar fragments in the molecule, viz. the central S1—S2—S3—C1—C2—N1—N2 plane with C1 farthest out at (0.0077 (19) Å) and the two benzonitrile systems C11—C18 and N4 with C11 farthest out at 0.0280 (19) Å) and C3—C19 and N3 with N3 farthest out at 0.0738 (21) Å. The dihedral angles between the central substituted ring and benzonitrile systems are 28.29 (10)° and 78.83 (6)° and 72.89 (7)° between the two benzonitrile moieties. There is no evidence of typical hydrogenn bonding or intermolecular π–π interactions. Only van-der-waals interactions are observed in the crystal is packing (Fig.2).

Experimental

A dry 50 ml flask was charged with 1,3,4-thiadiazole-2,5-dithiol (10 mmol), 4-(bromomethyl)benzonitrile (20 mmol), K₂CO₃(10 mmol), and methanol (30 mL). The mixture was stirred with refluxing for 4 h and then was poured into water (40 ml), the precipitate was washed with water for 2–3 times and purified by recrystallization from methanol to give the crystals of the target material.