6-Iodo-2-methyl-1,3-benzothia­zole

Marijana Đaković; Helena Čičak

doi:10.1107/S1600536811004570

. 2011 Feb 12;67(Pt 3):o620. doi: 10.1107/S1600536811004570

6-Iodo-2-methyl-1,3-benzothiazole

Marijana Đaković ^a,^*, Helena Čičak ^a

PMCID: PMC3051962 PMID: 21522376

Abstract

The title compound, C₈H₆INS, is essentially planar, the largest deviation from the mean plane being for the I atom [0.075 (3) Å]. The crystal structure is mainly stabilized by intermolecular C—I⋯N halogen bonds, forming zigzag supramolecular chains in [10 Inline graphic ]. Relatively short off-set π–π contacts [centroid–centroid distance = 3.758 (2) Å] between the thiazole rings of inversion-related molecules link neighbouring chains and provide the secondary interactions for building the crystal structure.

Related literature

For the application of benzothiazoles as biologically active compounds, see: Leong et al. (2004 ▶); Yildiz-Oren et al. (2004 ▶); Lockhart et al. (2005 ▶); Sheng et al. (2007 ▶). For the synthesis of the title compound, see: Racané et al. (2006 ▶, 2011 ▶). For related 1,3-benzothiazole structures, see: Matković-Čalogović et al. (2003 ▶); Pavlović et al. (2009 ▶); Đaković et al. (2009 ▶); Čičak et al. (2010 ▶). For graph-set theory, see: Etter (1990 ▶); Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C₈H₆INS
M _r = 275.11
Monoclinic,
a = 8.3255 (3) Å
b = 7.6967 (3) Å
c = 13.8083 (5) Å
β = 90.686 (4)°
V = 884.76 (6) Å³
Z = 4
Mo Kα radiation
μ = 3.79 mm⁻¹
T = 296 K
0.47 × 0.38 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Saphire-3 CCD detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.253, T _max = 0.658
13190 measured reflections
1928 independent reflections
1729 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.064
S = 1.06
1928 reflections
101 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004570/fj2389sup1.cif

e-67-0o620-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004570/fj2389Isup2.hkl

e-67-0o620-Isup2.hkl^{(93KB, hkl)}

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

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

	C4—I1	I1⋯N1ⁱ	C4⋯N1ⁱ	C4—I1⋯N1ⁱ
C4—I1⋯N1ⁱ	2.103 (3)	3.158 (2)	5.257 (4)	175.99 (9)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This research was supported by the Ministry of Science, Education and Sports of the Republic of Croatia, Zagreb (grant Nos. 119–1193079–1332 and 119–1191342–1339).

supplementary crystallographic information

Comment

This work was a part of our preparative, structural, mechanistic and computational investigation of a series of substituted benzothiazoles (bta), which attract considerable interest due to their biological activities.

The molecule is almost ideally planar (r.m.s. deviation = 0.009 Å), with the largest deviation from the plane being that of atom I1 [0.075 (3) Å] (Fig.1). The geometry of the benzothiazole rings is consistent with other 1,3-benzothiazoles listed in the CSD base (Allen et al., 2002). The two S—C bonds of the thiazole ring [S1—C1 and S1—C2] differ with respect to each other, but both are within two bortherline cases, single S—C [1.82 Å] and double S=C [1.56 Å], while the endocyclic C—N bond is dominantly double in character. The differences in C—C bonds within benzene ring are common for such fused rings.

In the crystal structure halogen bonds are the principal specific interactions responsible for the crystal packing. There is only one short and directional C—I···N contact [C—I = 2.103 (3) Å] (see Table 1) that link the molecules into antiparallel zigzag C(7) chains (Etter, 1990; Bernstein et al., 1995) in [1 0 - 1] direction (Figs. 2 and 3).

Relatively short off-set π–π contacts [Cg···Cg = 3.758 (2) Å] between the thiazole rings, belonging to the molecules that are related by an inversion centre, link the neighboring supramolecular chains and provide the secondary interactions for building the crystal structure.

The structure of the title compound is one more example showing that halogen bonding is also as effective and reliable tool for assembling molecules into supramolecular architectures.

Experimental

Colourless single crystals of the title compound were obtained by slow evaporation of a dichloromethane solution.