5-Chloro-2-phenyl-1,3-benzothia-zole.

In the structure of the title compound, C(13)H(8)ClNS, the dihedral angle between the benzothia-zole ring system and the phenyl ring is 7.11 (8)°. In the crystal, mol-ecules are arranged parallel to the c axis.

Related literature

For biological activites of benzothia­zole compounds, see: Venkatesh & Pandeya (2009 ▶); Sreenivasa et al. (2009 ▶); Kok et al. (2008 ▶); Siddiqui et al. (2007 ▶); Maharan et al. (2007 ▶); Pattan et al. (2005 ▶); Hout et al. (2004 ▶); Chohan et al. (2003 ▶); Bénéteau et al. (1999 ▶). For the crystal structure of benzothia­zole derivatives, see: Lakshmanan et al. (2011 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C13H8ClNS

M = 245.71

Monoclinic,

a = 7.4057 (9) Å

b = 5.9100 (7) Å

c = 25.165 (3) Å

β = 93.402 (3)°

V = 1099.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 273 K

0.36 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.840, T max = 0.956

6221 measured reflections

2013 independent reflections

1706 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.04

2013 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 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, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812036057/wn2488sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036057/wn2488Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036057/wn2488Isup3.cml

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

C13H8ClNS	F(000) = 504
Mr = 245.71	Dx = 1.484 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.4057 (9) Å	Cell parameters from 2167 reflections
b = 5.9100 (7) Å	θ = 3.1–28.2°
c = 25.165 (3) Å	µ = 0.50 mm−1
β = 93.402 (3)°	T = 273 K
V = 1099.5 (2) Å3	Plate, colorless
Z = 4	0.36 × 0.13 × 0.09 mm

Bruker SMART APEX CCD area-detector diffractometer	2013 independent reflections
Radiation source: fine-focus sealed tube	1706 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scan	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.840, Tmax = 0.956	k = −7→6
6221 measured reflections	l = −30→30

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.1614P] where P = (Fo2 + 2Fc2)/3
2013 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 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	0.26215 (9)	−0.18042 (11)	0.02881 (2)	0.0660 (2)
S1	0.33963 (7)	0.39652 (8)	0.234075 (19)	0.04489 (18)
N1	0.19011 (19)	−0.0014 (3)	0.22680 (5)	0.0367 (4)
C1	0.2624 (3)	0.3164 (3)	0.35279 (8)	0.0449 (5)
H1B	0.3131	0.4479	0.3399	0.054*
C2	0.2426 (3)	0.2922 (4)	0.40663 (8)	0.0519 (5)
H2A	0.2800	0.4079	0.4298	0.062*
C3	0.1683 (3)	0.0995 (4)	0.42641 (8)	0.0514 (5)
H3A	0.1555	0.0846	0.4628	0.062*
C4	0.1123 (3)	−0.0732 (4)	0.39196 (8)	0.0484 (5)
H4A	0.0617	−0.2040	0.4052	0.058*
C5	0.1315 (2)	−0.0515 (3)	0.33809 (7)	0.0419 (4)
H5A	0.0941	−0.1681	0.3152	0.050*
C6	0.2067 (2)	0.1442 (3)	0.31764 (7)	0.0361 (4)
C7	0.2333 (2)	0.1595 (3)	0.26047 (7)	0.0349 (4)
C9	0.2440 (2)	0.0541 (3)	0.17678 (7)	0.0353 (4)
C10	0.2208 (2)	−0.0858 (3)	0.13211 (7)	0.0395 (4)
H10A	0.1639	−0.2256	0.1340	0.047*
C11	0.2850 (3)	−0.0087 (3)	0.08523 (7)	0.0435 (5)
C12	0.3695 (3)	0.2000 (4)	0.08090 (8)	0.0477 (5)
H12A	0.4101	0.2459	0.0483	0.057*
C13	0.3932 (3)	0.3391 (3)	0.12465 (8)	0.0457 (5)
H13A	0.4498	0.4789	0.1222	0.055*
C14	0.3300 (2)	0.2643 (3)	0.17274 (7)	0.0383 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0921 (5)	0.0674 (4)	0.0395 (3)	−0.0125 (3)	0.0133 (3)	−0.0074 (2)
S1	0.0502 (3)	0.0336 (3)	0.0509 (3)	−0.0091 (2)	0.0039 (2)	−0.0026 (2)
N1	0.0381 (9)	0.0326 (9)	0.0397 (8)	−0.0015 (6)	0.0048 (6)	−0.0006 (6)
C1	0.0482 (12)	0.0366 (11)	0.0496 (11)	−0.0008 (9)	0.0011 (8)	−0.0052 (8)
C2	0.0564 (13)	0.0527 (14)	0.0458 (11)	0.0039 (10)	−0.0028 (9)	−0.0121 (9)
C3	0.0522 (12)	0.0608 (14)	0.0411 (10)	0.0081 (10)	0.0009 (9)	0.0016 (9)
C4	0.0495 (13)	0.0461 (12)	0.0497 (11)	0.0014 (9)	0.0033 (9)	0.0089 (9)
C5	0.0422 (11)	0.0392 (11)	0.0440 (10)	−0.0006 (8)	−0.0007 (8)	−0.0034 (8)
C6	0.0307 (10)	0.0349 (10)	0.0422 (10)	0.0030 (7)	−0.0006 (7)	−0.0025 (7)
C7	0.0282 (9)	0.0308 (10)	0.0453 (10)	0.0003 (7)	−0.0003 (7)	−0.0011 (7)
C9	0.0305 (9)	0.0334 (10)	0.0423 (9)	0.0018 (7)	0.0032 (7)	0.0024 (7)
C10	0.0418 (11)	0.0343 (10)	0.0427 (10)	−0.0029 (8)	0.0041 (8)	0.0000 (8)
C11	0.0456 (12)	0.0464 (12)	0.0388 (10)	0.0020 (9)	0.0045 (8)	0.0000 (8)
C12	0.0472 (12)	0.0511 (13)	0.0457 (11)	0.0002 (9)	0.0102 (8)	0.0110 (9)
C13	0.0435 (11)	0.0398 (11)	0.0545 (11)	−0.0034 (9)	0.0078 (9)	0.0080 (9)
C14	0.0339 (10)	0.0348 (10)	0.0462 (10)	0.0002 (8)	0.0025 (7)	0.0014 (8)

Cl1—C11	1.7453 (19)	C4—H4A	0.9300
S1—C14	1.7279 (18)	C5—C6	1.395 (3)
S1—C7	1.7566 (18)	C5—H5A	0.9300
N1—C7	1.301 (2)	C6—C7	1.466 (2)
N1—C9	1.382 (2)	C9—C10	1.398 (2)
C1—C2	1.379 (3)	C9—C14	1.402 (2)
C1—C6	1.395 (3)	C10—C11	1.376 (2)
C1—H1B	0.9300	C10—H10A	0.9300
C2—C3	1.371 (3)	C11—C12	1.390 (3)
C2—H2A	0.9300	C12—C13	1.377 (3)
C3—C4	1.386 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.395 (3)
C4—C5	1.377 (3)	C13—H13A	0.9300
C14—S1—C7	88.93 (8)	N1—C7—S1	115.77 (13)
C7—N1—C9	110.29 (15)	C6—C7—S1	120.63 (13)
C2—C1—C6	120.18 (19)	N1—C9—C10	124.31 (16)
C2—C1—H1B	119.9	N1—C9—C14	115.66 (15)
C6—C1—H1B	119.9	C10—C9—C14	120.02 (15)
C3—C2—C1	120.75 (19)	C11—C10—C9	117.48 (18)
C3—C2—H2A	119.6	C11—C10—H10A	121.3
C1—C2—H2A	119.6	C9—C10—H10A	121.3
C2—C3—C4	119.73 (18)	C10—C11—C12	122.76 (17)
C2—C3—H3A	120.1	C10—C11—Cl1	118.90 (15)
C4—C3—H3A	120.1	C12—C11—Cl1	118.33 (14)
C5—C4—C3	120.16 (19)	C13—C12—C11	120.25 (17)
C5—C4—H4A	119.9	C13—C12—H12A	119.9
C3—C4—H4A	119.9	C11—C12—H12A	119.9
C4—C5—C6	120.47 (18)	C12—C13—C14	118.07 (18)
C4—C5—H5A	119.8	C12—C13—H13A	121.0
C6—C5—H5A	119.8	C14—C13—H13A	121.0
C1—C6—C5	118.72 (17)	C13—C14—C9	121.40 (17)
C1—C6—C7	121.69 (17)	C13—C14—S1	129.28 (15)
C5—C6—C7	119.52 (15)	C9—C14—S1	109.32 (12)
N1—C7—C6	123.50 (16)
C6—C1—C2—C3	0.1 (3)	C7—N1—C9—C14	−0.3 (2)
C1—C2—C3—C4	0.0 (3)	N1—C9—C10—C11	−178.70 (17)
C2—C3—C4—C5	0.1 (3)	C14—C9—C10—C11	0.1 (3)
C3—C4—C5—C6	−0.2 (3)	C9—C10—C11—C12	−0.4 (3)
C2—C1—C6—C5	−0.1 (3)	C9—C10—C11—Cl1	178.89 (14)
C2—C1—C6—C7	−177.15 (17)	C10—C11—C12—C13	0.5 (3)
C4—C5—C6—C1	0.2 (3)	Cl1—C11—C12—C13	−178.86 (15)
C4—C5—C6—C7	177.29 (16)	C11—C12—C13—C14	−0.2 (3)
C9—N1—C7—C6	−175.21 (15)	C12—C13—C14—C9	−0.2 (3)
C9—N1—C7—S1	1.28 (19)	C12—C13—C14—S1	179.72 (15)
C1—C6—C7—N1	177.03 (17)	N1—C9—C14—C13	179.11 (17)
C5—C6—C7—N1	0.0 (3)	C10—C9—C14—C13	0.2 (3)
C1—C6—C7—S1	0.7 (2)	N1—C9—C14—S1	−0.8 (2)
C5—C6—C7—S1	−176.27 (14)	C10—C9—C14—S1	−179.71 (14)
C14—S1—C7—N1	−1.50 (15)	C7—S1—C14—C13	−178.71 (18)
C14—S1—C7—C6	175.10 (14)	C7—S1—C14—C9	1.20 (14)
C7—N1—C9—C10	178.56 (17)