5-Chloro-2-(4-meth-oxy-phen-yl)-1,3-benzo-thia-zole.

In the title compound, C14H10ClNOS, the dihedral angle between the benzothia-zole ring system and the meth-oxy-substituted benzene ring is 8.76 (16)°. In the crystal, mol-ecules are stacked in columns along the c axis and no significant inter-molecular inter-actions are observed.

Related literature

For the biological activity of benzothia­zole compounds, see: Chohan et al. (2003 ▶); Khan et al. (2011 ▶); Hutchinson et al. (2002 ▶); Burger & Sawhney (1968 ▶); Palmer et al. (1971 ▶). For related structures, see: Yousuf et al. (2012a ▶,b ▶).

Experimental

Crystal data

C14H10ClNOS

M = 275.74

Orthorhombic,

a = 29.0274 (16) Å

b = 14.5512 (8) Å

c = 5.8686 (3) Å

V = 2478.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.46 mm−1

T = 273 K

0.37 × 0.22 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.848, T max = 0.955

13397 measured reflections

2299 independent reflections

1965 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.208

S = 1.15

2299 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.37 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, 1996 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001955/is5237sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001955/is5237Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001955/is5237Isup3.cml

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

C14H10ClNOS	F(000) = 1136
Mr = 275.74	Dx = 1.478 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3307 reflections
a = 29.0274 (16) Å	θ = 2.5–26.3°
b = 14.5512 (8) Å	µ = 0.46 mm−1
c = 5.8686 (3) Å	T = 273 K
V = 2478.8 (2) Å3	Block, colorles
Z = 8	0.37 × 0.22 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	2299 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scan	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −34→34
Tmin = 0.848, Tmax = 0.955	k = −17→17
13397 measured reflections	l = −6→7

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0983P)2 + 3.3682P] where P = (Fo2 + 2Fc2)/3
2299 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
Cl1	0.04504 (4)	0.17240 (11)	−0.0360 (2)	0.0787 (5)
S1	0.21904 (4)	0.08514 (7)	0.52664 (16)	0.0494 (4)
O1	0.43838 (11)	0.1057 (2)	0.1916 (6)	0.0656 (9)
N1	0.21907 (12)	0.1613 (2)	0.1301 (5)	0.0437 (8)
C1	0.16642 (15)	0.1048 (2)	0.4009 (6)	0.0450 (9)
C2	0.12234 (17)	0.0857 (3)	0.4807 (7)	0.0502 (10)
H2A	0.1179	0.0592	0.6231	0.060*
C3	0.08560 (16)	0.1072 (3)	0.3433 (7)	0.0556 (11)
H3A	0.0558	0.0946	0.3927	0.067*
C4	0.09246 (15)	0.1475 (3)	0.1304 (8)	0.0530 (10)
C5	0.13595 (15)	0.1688 (3)	0.0488 (7)	0.0471 (9)
H5A	0.1400	0.1968	−0.0922	0.057*
C6	0.17346 (14)	0.1466 (2)	0.1872 (6)	0.0420 (9)
C7	0.24620 (14)	0.1318 (2)	0.2888 (6)	0.0409 (9)
C8	0.29667 (14)	0.1305 (2)	0.2692 (6)	0.0420 (9)
C9	0.32493 (16)	0.0941 (3)	0.4380 (7)	0.0511 (10)
H9A	0.3118	0.0730	0.5727	0.061*
C10	0.37175 (16)	0.0885 (3)	0.4104 (7)	0.0535 (11)
H10A	0.3901	0.0646	0.5261	0.064*
C11	0.39169 (15)	0.1187 (3)	0.2077 (7)	0.0487 (10)
C12	0.36468 (15)	0.1576 (3)	0.0376 (7)	0.0479 (9)
H12A	0.3780	0.1795	−0.0959	0.057*
C13	0.31762 (15)	0.1631 (2)	0.0709 (7)	0.0461 (9)
H13A	0.2994	0.1893	−0.0421	0.055*
C14	0.46063 (17)	0.1316 (4)	−0.0114 (9)	0.0717 (14)
H14A	0.4926	0.1149	−0.0032	0.108*
H14B	0.4580	0.1969	−0.0316	0.108*
H14C	0.4465	0.1007	−0.1379	0.108*

	U11	U22	U33	U12	U13	U23
Cl1	0.0538 (7)	0.1036 (11)	0.0787 (9)	0.0116 (7)	0.0019 (6)	0.0106 (7)
S1	0.0692 (7)	0.0454 (6)	0.0336 (5)	−0.0036 (5)	0.0005 (4)	0.0084 (4)
O1	0.0598 (19)	0.072 (2)	0.065 (2)	0.0054 (15)	−0.0097 (16)	0.0031 (16)
N1	0.058 (2)	0.0384 (16)	0.0347 (16)	−0.0028 (14)	0.0022 (15)	0.0019 (13)
C1	0.069 (3)	0.0347 (18)	0.0308 (18)	−0.0014 (17)	0.0019 (18)	0.0005 (14)
C2	0.068 (3)	0.044 (2)	0.039 (2)	−0.0038 (19)	0.0129 (19)	0.0029 (16)
C3	0.066 (3)	0.051 (2)	0.050 (2)	−0.004 (2)	0.020 (2)	−0.0059 (19)
C4	0.061 (3)	0.046 (2)	0.052 (2)	0.0044 (18)	0.007 (2)	−0.0042 (18)
C5	0.061 (2)	0.0386 (19)	0.042 (2)	0.0006 (17)	0.0043 (19)	−0.0007 (16)
C6	0.061 (2)	0.0313 (16)	0.0334 (18)	−0.0018 (16)	0.0071 (17)	−0.0023 (14)
C7	0.064 (2)	0.0315 (17)	0.0269 (17)	−0.0024 (16)	0.0010 (17)	−0.0002 (14)
C8	0.065 (2)	0.0298 (16)	0.0314 (18)	−0.0007 (15)	−0.0052 (17)	−0.0006 (14)
C9	0.072 (3)	0.045 (2)	0.036 (2)	−0.0032 (19)	−0.0038 (19)	0.0056 (16)
C10	0.071 (3)	0.047 (2)	0.043 (2)	0.0017 (19)	−0.016 (2)	0.0052 (17)
C11	0.056 (2)	0.043 (2)	0.047 (2)	0.0021 (17)	−0.0078 (19)	−0.0040 (17)
C12	0.059 (2)	0.042 (2)	0.043 (2)	−0.0012 (18)	−0.0009 (18)	0.0047 (16)
C13	0.061 (2)	0.0376 (19)	0.040 (2)	0.0003 (17)	−0.0088 (18)	0.0040 (15)
C14	0.055 (3)	0.092 (4)	0.068 (3)	−0.007 (3)	0.001 (2)	0.004 (3)

Cl1—C4	1.726 (5)	C5—H5A	0.9300
S1—C1	1.720 (4)	C7—C8	1.470 (6)
S1—C7	1.741 (4)	C8—C9	1.391 (5)
O1—C11	1.372 (5)	C8—C13	1.396 (5)
O1—C14	1.407 (5)	C9—C10	1.371 (7)
N1—C7	1.293 (5)	C9—H9A	0.9300
N1—C6	1.382 (5)	C10—C11	1.394 (6)
C1—C2	1.391 (6)	C10—H10A	0.9300
C1—C6	1.409 (5)	C11—C12	1.390 (5)
C2—C3	1.373 (7)	C12—C13	1.382 (6)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.394 (6)	C13—H13A	0.9300
C3—H3A	0.9300	C14—H14A	0.9600
C4—C5	1.386 (6)	C14—H14B	0.9600
C5—C6	1.396 (6)	C14—H14C	0.9600
C1—S1—C7	89.62 (18)	C9—C8—C13	117.8 (4)
C11—O1—C14	118.4 (4)	C9—C8—C7	122.5 (4)
C7—N1—C6	110.9 (3)	C13—C8—C7	119.7 (3)
C2—C1—C6	121.3 (4)	C10—C9—C8	121.5 (4)
C2—C1—S1	129.8 (3)	C10—C9—H9A	119.2
C6—C1—S1	109.0 (3)	C8—C9—H9A	119.2
C3—C2—C1	118.2 (4)	C9—C10—C11	119.6 (4)
C3—C2—H2A	120.9	C9—C10—H10A	120.2
C1—C2—H2A	120.9	C11—C10—H10A	120.2
C2—C3—C4	120.7 (4)	O1—C11—C12	124.4 (4)
C2—C3—H3A	119.6	O1—C11—C10	115.2 (4)
C4—C3—H3A	119.6	C12—C11—C10	120.5 (4)
C5—C4—C3	122.3 (4)	C13—C12—C11	118.7 (4)
C5—C4—Cl1	118.9 (3)	C13—C12—H12A	120.7
C3—C4—Cl1	118.8 (3)	C11—C12—H12A	120.7
C4—C5—C6	117.2 (4)	C12—C13—C8	121.9 (4)
C4—C5—H5A	121.4	C12—C13—H13A	119.0
C6—C5—H5A	121.4	C8—C13—H13A	119.0
N1—C6—C5	124.7 (3)	O1—C14—H14A	109.5
N1—C6—C1	114.9 (4)	O1—C14—H14B	109.5
C5—C6—C1	120.3 (4)	H14A—C14—H14B	109.5
N1—C7—C8	123.7 (3)	O1—C14—H14C	109.5
N1—C7—S1	115.5 (3)	H14A—C14—H14C	109.5
C8—C7—S1	120.6 (3)	H14B—C14—H14C	109.5
C7—S1—C1—C2	179.4 (4)	C1—S1—C7—N1	1.1 (3)
C7—S1—C1—C6	−0.7 (3)	C1—S1—C7—C8	−174.8 (3)
C6—C1—C2—C3	1.2 (6)	N1—C7—C8—C9	−176.7 (3)
S1—C1—C2—C3	−178.9 (3)	S1—C7—C8—C9	−1.1 (5)
C1—C2—C3—C4	−0.4 (6)	N1—C7—C8—C13	0.5 (5)
C2—C3—C4—C5	−0.9 (6)	S1—C7—C8—C13	176.0 (3)
C2—C3—C4—Cl1	179.6 (3)	C13—C8—C9—C10	−1.2 (6)
C3—C4—C5—C6	1.3 (6)	C7—C8—C9—C10	176.0 (4)
Cl1—C4—C5—C6	−179.2 (3)	C8—C9—C10—C11	−0.9 (6)
C7—N1—C6—C5	−178.4 (3)	C14—O1—C11—C12	−1.3 (6)
C7—N1—C6—C1	0.7 (4)	C14—O1—C11—C10	177.8 (4)
C4—C5—C6—N1	178.6 (3)	C9—C10—C11—O1	−176.6 (4)
C4—C5—C6—C1	−0.4 (5)	C9—C10—C11—C12	2.5 (6)
C2—C1—C6—N1	−179.9 (3)	O1—C11—C12—C13	177.1 (4)
S1—C1—C6—N1	0.2 (4)	C10—C11—C12—C13	−1.9 (6)
C2—C1—C6—C5	−0.8 (5)	C11—C12—C13—C8	−0.2 (6)
S1—C1—C6—C5	179.3 (3)	C9—C8—C13—C12	1.8 (5)
C6—N1—C7—C8	174.5 (3)	C7—C8—C13—C12	−175.5 (3)
C6—N1—C7—S1	−1.2 (4)