5-Chloro-2-phenyl-1,3-benzothia­zole

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

doi:10.1107/S1600536812036057

. 2012 Aug 31;68(Pt 9):o2799. doi: 10.1107/S1600536812036057

5-Chloro-2-phenyl-1,3-benzothiazole

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

PMCID: PMC3435826 PMID: 22969672

Abstract

In the structure of the title compound, C₁₃H₈ClNS, the dihedral angle between the benzothiazole ring system and the phenyl ring is 7.11 (8)°. In the crystal, molecules are arranged parallel to the c axis.

Related literature

For biological activites of benzothiazole compounds, see: Venkatesh & Pandeya (2009 ▶); Sreenivasa et al. (2009 ▶); Kok et al. (2008 ▶); Siddiqui et al. (2007 ▶); Maharan et al. (2007 ▶); Pattan et al. (2005 ▶); Hout et al. (2004 ▶); Chohan et al. (2003 ▶); Bénéteau et al. (1999 ▶). For the crystal structure of benzothiazole derivatives, see: Lakshmanan et al. (2011 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C₁₃H₈ClNS
M _r = 245.71
Monoclinic,
a = 7.4057 (9) Å
b = 5.9100 (7) Å
c = 25.165 (3) Å
β = 93.402 (3)°
V = 1099.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 273 K
0.36 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.840, T _max = 0.956
6221 measured reflections
2013 independent reflections
1706 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.093
S = 1.04
2013 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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/S1600536812036057/wn2488sup1.cif

e-68-o2799-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036057/wn2488Isup2.hkl

e-68-o2799-Isup2.hkl^{(99KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036057/wn2488Isup3.cml

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

Acknowledgments

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

supplementary crystallographic information

Comment

Benzothiazoles represent an important class of heterocyclic compounds and are known to have numerous biological activities, including antimicrobial, antimalarial, anticancer, anti-inflamatory, antidiabetic, anticonvulsant, antitumor and anthelmintic properties (Venkatesh & Pandeya, 2009; Sreenivasa et al., 2009; Kok et al., 2008; Siddiqui et al., 2007; Maharan et al., 2007; Pattan et al., 2005; Hout et al., 2004; Chohan et al., 2003; Bénéteau et al., 1999). The title compound was prepared as part of an ongoing research effort to synthesize libraries of hetereocyclic compounds and evaluate thei different biological activities.

In the structure (Fig. 1) of the title compound, C₁₃H₈ClNS, the dihedral angle between the benzothiazole ring system and the phenyl ring is 7.11 (8)°. The bond lengths and angles are similar to those in structurally related benzothiazole compounds (Lakshmanan et al., 2011; Zhang et al., 2008). In the crystal structure the molecules are arranged parallel to the c-axis (Fig. 2).

Experimental

In a 50 ml round-bottomed flask 2-amino-4-chlorobenzenethiol (0.159 g, 1 mmol), benzaldehyde (0.106 g, 1 mmol), N,N-dimethylformamide (10 ml), and sodium metabisulfite (0.2 g) were added with continuous stirring and allowed to reflux for 2 h. Progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was allowed to cool at room temperature and addition of cold water produced a solid precipitate. Crystallization from ethanol afforded pure crystals of the title compound (0.245 g, 91.8% yield); these were found to be suitable for single-crystal X-ray diffraction studies.