5-Chloro-2-(3,4,5-trimeth­oxy­phen­yl)-1,3-benzothia­zole

Sammer Yousuf; Shazia Shah; Nida Ambreen; Khalid M Khan; Shakil Ahmad

doi:10.1107/S1600536812039372

. 2012 Sep 29;68(Pt 10):o3057. doi: 10.1107/S1600536812039372

5-Chloro-2-(3,4,5-trimethoxyphenyl)-1,3-benzothiazole

Sammer Yousuf ^a,^*, Shazia Shah ^a, Nida Ambreen ^a, Khalid M Khan ^a, Shakil Ahmad ^a

PMCID: PMC3470404 PMID: 23125817

Abstract

In the title compound, C₁₆H₁₄ClNO₃S, the dihedral angle between the almost-planar benzothiazole ring system [maximum deviation = 0.012 (3) Å] and the aromatic ring of the trimethoxyphenyl group is 15.56 (6)°. In the crystal, the molecules are arranged into layers parallel to the bc plane, held together only by weak van der Waals forces.

Related literature

For the biological activites of benzothiazole compounds, see: Chohan et al. (2003 ▶); Hutchinson et al. (2002 ▶); Chua et al. (1999 ▶); Burger & Sawhney (1968 ▶); Palmer et al. (1971 ▶). For the crystal structures of related benzothiazole derivatives, see: Yousuf et al. (2012a ▶,b ▶).

Experimental

Crystal data

C₁₆H₁₄ClNO₃S
M _r = 335.79
Triclinic,
a = 4.0656 (6) Å
b = 7.7855 (11) Å
c = 12.2420 (17) Å
α = 96.263 (3)°
β = 91.380 (3)°
γ = 97.228 (3)°
V = 381.84 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 273 K
0.52 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.820, T _max = 0.965
4277 measured reflections
2816 independent reflections
2621 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.080
S = 1.07
2816 reflections
202 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1402 Friedel pairs
Flack parameter: 0.12 (6)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039372/rz5005sup1.cif

e-68-o3057-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039372/rz5005Isup2.hkl

e-68-o3057-Isup2.hkl^{(138.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039372/rz5005Isup3.cml

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

Acknowledgments

The authors are grateful to OPCW, The Netherlands, and the Higher Education Commission (HEC), Pakistan (project No. 1910), for their financial support.

supplementary crystallographic information

Comment

Benzothiazole is a well known class of sulfur- and nitrogen-containing heterocyclic aromatic molecules with a broad range of biological activities, such as antimicrobial, antitumoral, antimalarial and antitubercular (Chohan et al., 2003; Hutchinson et al., 2002; Chua et al., 1999; Burger & Sawhney, 1968; Palmer et al., 1971). The title compound is a benzothiazole derivative synthesized as a part of our ongoing project on bioactive hetereocyclic compounds.

The molecular structure of the title compound (Fig. 1) is similar to that reported for the recently published compounds 5-chloro-2-phenyl-1,3-benzothiazole (Yousuf et al., 2012a) and 2-(5-chloro-1,3-benzothiazol-2-yl)-4-methoxyphenol (Yousuf et al., 2012b) with the difference that the phenyl or p-methoxyphenol group is replaced by a trimethoxyphenyl group. The dihedral angle between the almost planar benzothiazole ring system (S1/N1/C1–C7) and the benzene ring of the trimethoxyphenyl group (C8–C13) is 15.56 (6)°. Bond lengths and angles are unexceptional. In the crystal structure the molecules are arranged into layers parallel to the bc plane (Fig. 2) held together only by weak van der Waals forces.

Experimental

A mixture of 2-amino-4-cholorobenzenethiol (0.159 g, 1 mmol), 3,4,5-trimethoxybenz-aldehyde (0.196 g, 1 mmol), sodium metabisulfite (0.2 g) and N,N-dimethylformamide (10 ml) was refluxed for 2 h in a round-bottomed flask. The completion of reaction was monitored by TLC. After cooling the mixture to room temperature, cold water was added to obtain a white precipitate. Crystallization from ethanol afforded crystals of the title compound (0.298 g, 88.9% yield) found suitable for X-ray diffraction studies.