3-{2-[(1,3-Benzothia­zol-2-yl)sulfanyl­meth­yl]phen­yl}-4-meth­oxy-5,5-dimethyl­furan-2(5H)-one

Anna Duan; Haikui Yang; Peiliang Zhao; Wenwei You

doi:10.1107/S1600536812022404

. 2012 May 23;68(Pt 6):o1854. doi: 10.1107/S1600536812022404

3-{2-[(1,3-Benzothiazol-2-yl)sulfanylmethyl]phenyl}-4-methoxy-5,5-dimethylfuran-2(5H)-one

Anna Duan ^a, Haikui Yang ^a, Peiliang Zhao ^a, Wenwei You ^a,^*

PMCID: PMC3379421 PMID: 22719619

Abstract

In the title compound, C₂₁H₁₉NO₃S₂, the dihedral angles formed between the thiazole ring and the adjacent benzene ring and the other benzene ring are 1.58 (3) and 76.48 (6)°, respectively. The crystal structure features a weak C—H⋯O interaction.

Related literature

For the anti-tumor activity of benzothiazole derivatives, see: Brantley et al. (2004 ▶) and for their anti-tuberculous properties, see: Palmer et al. (1971 ▶). For fungicidal properties of benzothiazolines and the preparation of the title compound, see: Zhao et al. (2010 ▶). For general background to furan-2(5H)-ones and their derivatives, see: Iannazzo et al. (2008 ▶).

Experimental

Crystal data

C₂₁H₁₉NO₃S₂
M _r = 397.49
Triclinic,
a = 10.4702 (9) Å
b = 10.4851 (9) Å
c = 10.5169 (9) Å
α = 117.567 (1)°
β = 100.398 (1)°
γ = 95.257 (1)°
V = 986.15 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 292 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ▶) T _min = 0.944, T _max = 0.972
7206 measured reflections
3804 independent reflections
2713 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.109
S = 0.90
3804 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022404/im2376sup1.cif

e-68-o1854-sup1.cif^{(27.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022404/im2376Isup2.hkl

e-68-o1854-Isup2.hkl^{(186.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022404/im2376Isup3.cml

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
C2—H2⋯O1ⁱ	0.93	2.56	3.302 (3)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the Science Foundation of the Medical Scientific Research Foundation of Guangdong Province (B2010185), and the Natural Science Foundation of Guangdong Province (No. 10451051501004725)

supplementary crystallographic information

Comment

Benzothiazole derivatives are well known to exhibit a wide spectrum of biological activities, including fungicidal, anticancer and anti-tuberculous properties. (Brantley et al., 2004; Zhao et al., 2010; Palmer et al., 1971). In addition, furan-2(5H)-one derivatives also have good biological activities (Iannazzo et al., 2008). These findings prompted us to synthesize a new series of benzothiazole derivatives by incorporating furan-2(5H)-one at the 2-position, in the hope of finding molecules showing an improved bioactivity. We present here the X-ray crystallographic analysis of the title compound, (I), which was designed and synthesized in our laboratory.

A view of the molecular structure of the title compound is given in Fig.1. The bond lengths and angles are unremarkable.The dihedral angles formed between the triazole ring and the adjacent benzene ring and the other benzene ring system are 1.58 (3)° and 76.48 (6)°, respectively. One intermolecular C—H···O hydrogen bond exists in the crystal structure (Table 1). Atom C2 in the molecule acts as donor, via the H atom H2, towards O1 of an adjacent molecule (Fig.2). No π-π-stacking interactions are observed in the crystal structure.

Experimental

The title compound was synthesized according to a published procedure (Zhao et al., 2010). Crystals appropriate for X-ray data collection were obtained by slow evaporation of a methanolic solution at 292 K.