2-(2-Nitro­phen­yl)-1,3-benzothia­zole

S Vijayakumar; S Murugavel; R Selvakumar; M Bakthadoss

doi:10.1107/S1600536812029844

. 2012 Jul 7;68(Pt 8):o2362. doi: 10.1107/S1600536812029844

2-(2-Nitrophenyl)-1,3-benzothiazole

S Vijayakumar ^a, S Murugavel ^b,^*, R Selvakumar ^c, M Bakthadoss ^c,^‡

PMCID: PMC3414295 PMID: 22904828

Abstract

In the title compound, C₁₃H₈N₂O₂S, the essentially planar benzothiazole system [maximum deviation = −0.012 (1) Å for the S atom] is oriented at a dihedral angle of 48.3 (1)° with respect to the benzene ring. The nitro group is substantially twisted from the plane of its attached benzene ring [dihedral angle = 52.0 (1)°]. The crystal packing features C—H⋯O hydrogen bonds, which generate C(6) helical chains propagating along [010]. Weak C—H⋯π interactions also occur in the crystal.

Related literature

For the pharmacological activity of benzothiazole derivatives, see: Repiĉ et al. (2001 ▶); Schwartz et al. (1992 ▶). For related structures, see: Lakshmanan et al. (2011 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C₁₃H₈N₂O₂S
M _r = 256.27
Monoclinic,
a = 7.6092 (2) Å
b = 12.7854 (3) Å
c = 11.9938 (3) Å
β = 90.556 (2)°
V = 1166.78 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.937, T _max = 0.958
14037 measured reflections
3258 independent reflections
2559 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.113
S = 1.05
3258 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029844/hb6879sup1.cif

e-68-o2362-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029844/hb6879Isup2.hkl

e-68-o2362-Isup2.hkl^{(156.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029844/hb6879Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg3 are the centroids of the S1/N1/C1/C2/C7 thiazole ring, the C2–C7 benzene ring and the C8–C13 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.51	3.236 (2)	135
C9—H9⋯Cg1ⁱⁱ	0.93	2.92	3.468 (2)	119
C10—H10⋯Cg2ⁱⁱ	0.93	2.90	3.536 (2)	127
C3—H3⋯Cg3ⁱⁱⁱ	0.93	2.99	3.673 (2)	132

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

SM thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

supplementary crystallographic information

Comment

The benzothiazole nucleus is associated with several pharmacological activities such as anti-tumor (Repiĉ et al., 2001) and antimicrobial (Schwartz et al., 1992). As part of our studies in this area, the crystal structure of the title compound has been determined and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The benzothiazole moiety (S1/N1/C1—C7) is essentially planar [maximum deviation = -0.012 (1) Å for the S atom] and lies at an angle 48.3 (1)° with respect to the benzene ring. The nitro group (N2/O1/O2) is twisted from the attached benzene ring, forming a dihedral angle of 52.0 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Lakshmanan et al., 2011, Zhang et al., 2008).

The crystal packing features C—H···O hydrogen bonds. Atom C11 at x, y, z donates one proton to atom O1 at 1 - x, -1/2 + y, 3/2 - z, forming C(6) zigzag chains along the b axis (Fig. 2). The crystal packing also features three weak C—H···π interactions, the first one between a benzene H9 atom and the thiazole ring (S1/N1/C1/C2/C7) of an adjacent molecule, with a C9—H9···Cg1ⁱⁱ seperation of 2.92 Å, the second one between a benzene H10 atom and the benzene ring (C2–C7) of a neighbouring molecule, with a C10—H10···Cg2ⁱⁱ seperation of 2.90 Å and the third one between a benzene H3 atom and the benzene ring (C8–C13) of a neighbouring molecule, with a C3—H3···Cg3ⁱⁱⁱ seperation of 2.99 Å (Table 1 and Fig. 3; Cg1, Cg2 and Cg3 are the centroids of the (S1/N1/C1/C2/C7) thiazole ring, (C2–C7) benzene ring and (C8–C13) benzene ring, respectively. symmetry code as in Fig. 3).

Experimental

A mixture of 2-nitrobenzaldehyde (1 g, 6.6 mmol), 2-aminobenzenethiol (0.827 g, 6.6 mmol) and bakers' yeast (2.05 g) were stirred at room temperature for 24 h in dichloro methane(DCM). After completion of the reaction, the bakers' yeast was filtered through a bed of Celite, and the filtrate was concentrated under reduced pressure. On cooling, the solid product (1.60 g, 94%) obtained was separated and crystallized from ethylacetate to afford the title compound as yellow blocks.