6-Iodo-2-methyl-1,3-benzothia-zole.

The title compound, C(8)H(6)INS, 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 inter-molecular C-I⋯N halogen bonds, forming zigzag supra-molecular chains in [10]. Relatively short off-set π-π contacts [centroid-centroid distance = 3.758 (2) Å] between the thia-zole rings of inversion-related mol-ecules link neighbouring chains and provide the secondary inter-actions 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 = 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

Δρmax = 0.84 e Å−3

Δρmin = −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 ▶).

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

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

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

C8H6INS	F(000) = 520
Mr = 275.11	Dx = 2.065 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10010 reflections
a = 8.3255 (3) Å	θ = 4.4–32.6°
b = 7.6967 (3) Å	µ = 3.79 mm−1
c = 13.8083 (5) Å	T = 296 K
β = 90.686 (4)°	Plate, colourless
V = 884.76 (6) Å3	0.47 × 0.38 × 0.14 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Saphire-3 CCD detector	1928 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1729 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 16.3426 pixels mm-1	θmax = 27.0°, θmin = 4.6°
CCD scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.253, Tmax = 0.658	l = −17→17
13190 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.4162P] where P = (Fo2 + 2Fc2)/3
1928 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Experimental. Solvent used: CH2Cl2 Crystal mount: glued on a glass fibre Mosaicity (°): 1.1 (1) Frames collected: 892 Seconds exposure per frame: 5 Degree rotation per frame: 1.0 Crystal-Detector distance (mm): 50.0.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
I1	0.96733 (2)	0.14994 (3)	0.30624 (1)	0.0485 (1)
S1	0.66879 (11)	0.75187 (9)	0.49021 (6)	0.0518 (3)
N1	0.6453 (3)	0.5615 (3)	0.64355 (18)	0.0447 (8)
C1	0.6117 (4)	0.7135 (4)	0.6097 (2)	0.0457 (9)
C2	0.7440 (3)	0.5425 (3)	0.4842 (2)	0.0392 (8)
C3	0.8155 (3)	0.4585 (4)	0.40718 (19)	0.0430 (8)
C4	0.8633 (3)	0.2887 (4)	0.42068 (19)	0.0399 (8)
C5	0.8427 (4)	0.2058 (4)	0.5097 (2)	0.0452 (9)
C6	0.7728 (4)	0.2900 (4)	0.5857 (2)	0.0467 (9)
C7	0.7211 (3)	0.4614 (3)	0.5734 (2)	0.0386 (7)
C8	0.5343 (5)	0.8546 (4)	0.6669 (3)	0.0600 (11)
H3	0.83070	0.51470	0.34840	0.0520*
H5	0.87710	0.09160	0.51740	0.0540*
H6	0.75980	0.23380	0.64480	0.0560*
H8A	0.46780	0.80420	0.71580	0.0900*
H8B	0.46950	0.92540	0.62460	0.0900*
H8C	0.61580	0.92510	0.69710	0.0900*

	U11	U22	U33	U12	U13	U23
I1	0.0488 (1)	0.0567 (2)	0.0402 (1)	0.0012 (1)	0.0048 (1)	−0.0055 (1)
S1	0.0658 (5)	0.0376 (4)	0.0518 (4)	0.0063 (3)	−0.0035 (3)	0.0058 (3)
N1	0.0487 (13)	0.0419 (13)	0.0437 (13)	−0.0022 (10)	0.0082 (10)	−0.0014 (10)
C1	0.0416 (14)	0.0411 (14)	0.0543 (17)	−0.0019 (12)	−0.0027 (12)	−0.0054 (12)
C2	0.0424 (14)	0.0345 (12)	0.0407 (13)	−0.0029 (11)	−0.0035 (11)	0.0049 (11)
C3	0.0482 (15)	0.0457 (14)	0.0351 (13)	−0.0040 (12)	−0.0001 (11)	0.0075 (12)
C4	0.0393 (14)	0.0457 (14)	0.0347 (13)	−0.0025 (11)	0.0025 (11)	−0.0027 (11)
C5	0.0536 (16)	0.0347 (13)	0.0474 (16)	0.0044 (12)	0.0043 (13)	0.0030 (11)
C6	0.0593 (18)	0.0394 (13)	0.0415 (15)	−0.0005 (13)	0.0114 (13)	0.0073 (12)
C7	0.0396 (13)	0.0364 (12)	0.0399 (13)	−0.0035 (11)	0.0037 (10)	0.0013 (10)
C8	0.062 (2)	0.0511 (19)	0.067 (2)	0.0089 (15)	−0.0004 (17)	−0.0108 (15)

I1—C4	2.103 (3)	C4—C5	1.397 (4)
S1—C1	1.748 (3)	C5—C6	1.369 (4)
S1—C2	1.731 (2)	C6—C7	1.397 (4)
N1—C1	1.289 (4)	C3—H3	0.9300
N1—C7	1.395 (4)	C5—H5	0.9300
C1—C8	1.494 (5)	C6—H6	0.9300
C2—C3	1.385 (4)	C8—H8A	0.9600
C2—C7	1.396 (4)	C8—H8B	0.9600
C3—C4	1.378 (4)	C8—H8C	0.9600
I1···C1i	3.826 (3)	H3···H8Avii	2.5800
I1···N1ii	3.158 (2)	H5···S1viii	3.1600
I1···H5iii	3.3100	H5···I1iii	3.3100
S1···H5iv	3.1600	H5···H5iii	2.5400
S1···H8Bv	3.1600	H8A···H3ix	2.5800
N1···I1vi	3.158 (2)	H8B···S1v	3.1600
C1···I1i	3.826 (3)
C1—S1—C2	89.46 (14)	N1—C7—C6	125.3 (2)
C1—N1—C7	110.3 (2)	C2—C7—C6	119.0 (2)
S1—C1—N1	115.8 (2)	C2—C3—H3	121.00
S1—C1—C8	120.0 (2)	C4—C3—H3	121.00
N1—C1—C8	124.1 (3)	C4—C5—H5	119.00
S1—C2—C3	129.1 (2)	C6—C5—H5	120.00
S1—C2—C7	108.70 (19)	C5—C6—H6	120.00
C3—C2—C7	122.2 (2)	C7—C6—H6	120.00
C2—C3—C4	117.7 (2)	C1—C8—H8A	110.00
I1—C4—C3	120.06 (19)	C1—C8—H8B	110.00
I1—C4—C5	119.0 (2)	C1—C8—H8C	109.00
C3—C4—C5	120.9 (3)	H8A—C8—H8B	109.00
C4—C5—C6	121.1 (3)	H8A—C8—H8C	109.00
C5—C6—C7	119.1 (3)	H8B—C8—H8C	109.00
N1—C7—C2	115.7 (2)
C2—S1—C1—N1	0.5 (3)	S1—C2—C7—C6	180.0 (2)
C2—S1—C1—C8	178.5 (3)	C3—C2—C7—N1	−179.1 (2)
C1—S1—C2—C3	179.0 (3)	C3—C2—C7—C6	0.4 (4)
C1—S1—C2—C7	−0.6 (2)	C2—C3—C4—I1	178.41 (19)
C7—N1—C1—S1	−0.3 (3)	C2—C3—C4—C5	−1.1 (4)
C7—N1—C1—C8	−178.2 (3)	I1—C4—C5—C6	−178.8 (2)
C1—N1—C7—C2	−0.2 (3)	C3—C4—C5—C6	0.8 (5)
C1—N1—C7—C6	−179.6 (3)	C4—C5—C6—C7	0.2 (5)
S1—C2—C3—C4	−179.0 (2)	C5—C6—C7—N1	178.6 (3)
C7—C2—C3—C4	0.6 (4)	C5—C6—C7—C2	−0.8 (4)
S1—C2—C7—N1	0.5 (3)

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

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)

Symmetry code: (i) .