2-(5-Chloro-1,3-benzothia-zol-2-yl)-4-meth-oxy-phenol.

In the mol-ecule of the title compound, C(14)H(10)ClNO(2)S, the dihedral angle between the almost planar benzothia-zole ring system [maximum deviation = 0.005 (2) Å] and the benzene ring is 1.23 (9)°. The conformation of the mol-ecule is stabilized by an intra-molecular O-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, mol-ecules are linked into layers parallel to the ac plane by C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.7365 (12) Å].

Related literature

For the biological activity of benzothia­zole compounds see: Sreenivasa et al. (2009 ▶); Maharan et al. (2007 ▶); Pattan et al. (2005 ▶); Chohan et al. (2003 ▶); Bénéteau et al. (1999 ▶). For the crystal structures of benzothia­zole derivatives, see: Lakshmanan et al. (2011 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C14H10ClNO2S

M = 291.74

Orthorhombic,

a = 7.4877 (4) Å

b = 27.2166 (15) Å

c = 6.1902 (3) Å

V = 1261.50 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 273 K

0.38 × 0.25 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.844, T max = 0.947

7114 measured reflections

2226 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.069

S = 1.07

2226 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 935 Friedel pairs

Flack parameter: 0.07 (6)

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/S1600536812037804/rz5002sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037804/rz5002Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037804/rz5002Isup3.cml

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

C14H10ClNO2S	F(000) = 600
Mr = 291.74	Dx = 1.536 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3878 reflections
a = 7.4877 (4) Å	θ = 3.0–27.6°
b = 27.2166 (15) Å	µ = 0.46 mm−1
c = 6.1902 (3) Å	T = 273 K
V = 1261.50 (11) Å3	Block, colorles
Z = 4	0.38 × 0.25 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	2226 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scan	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.844, Tmax = 0.947	k = −31→32
7114 measured reflections	l = −7→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.1635P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2226 reflections	Δρmax = 0.16 e Å−3
177 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 935 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (6)

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
S1	0.76761 (6)	0.412840 (19)	0.76293 (9)	0.04557 (14)
Cl1	0.10003 (7)	0.45023 (2)	1.33138 (13)	0.06375 (18)
O1	0.9266 (2)	0.31641 (6)	1.3478 (3)	0.0566 (4)
H1A	0.842 (4)	0.3333 (10)	1.319 (5)	0.070 (9)*
O2	1.3785 (2)	0.32630 (6)	0.6457 (3)	0.0618 (4)
N1	0.7107 (2)	0.37543 (6)	1.1415 (3)	0.0409 (4)
C1	0.5714 (2)	0.42859 (7)	0.8955 (3)	0.0414 (5)
C2	0.4317 (2)	0.45863 (7)	0.8272 (4)	0.0474 (5)
H2A	0.4353	0.4742	0.6935	0.057*
C3	0.2873 (3)	0.46464 (8)	0.9648 (4)	0.0494 (5)
H3A	0.1917	0.4843	0.9233	0.059*
C4	0.2850 (3)	0.44153 (7)	1.1632 (4)	0.0454 (5)
C5	0.4197 (2)	0.41145 (7)	1.2349 (4)	0.0433 (5)
H5A	0.4142	0.3960	1.3688	0.052*
C6	0.5656 (3)	0.40510 (7)	1.0969 (3)	0.0384 (4)
C7	0.8262 (3)	0.37562 (7)	0.9832 (3)	0.0373 (4)
C8	0.9925 (2)	0.34762 (6)	0.9893 (3)	0.0374 (4)
C9	1.0346 (3)	0.31950 (7)	1.1723 (3)	0.0422 (5)
C10	1.1925 (3)	0.29284 (8)	1.1754 (4)	0.0485 (5)
H10A	1.2205	0.2740	1.2959	0.058*
C11	1.3085 (3)	0.29387 (8)	1.0030 (4)	0.0477 (5)
H11A	1.4134	0.2756	1.0077	0.057*
C12	1.2696 (2)	0.32199 (7)	0.8226 (4)	0.0437 (5)
C13	1.1118 (3)	0.34856 (7)	0.8157 (4)	0.0425 (5)
H13A	1.0850	0.3672	0.6942	0.051*
C14	1.5246 (3)	0.29354 (9)	0.6280 (5)	0.0654 (7)
H14A	1.5876	0.2998	0.4958	0.098*
H14B	1.4815	0.2603	0.6279	0.098*
H14C	1.6038	0.2982	0.7482	0.098*

	U11	U22	U33	U12	U13	U23
S1	0.0447 (3)	0.0502 (3)	0.0418 (3)	0.0065 (2)	0.0063 (2)	0.0087 (3)
Cl1	0.0472 (3)	0.0645 (3)	0.0795 (4)	0.0118 (2)	0.0193 (3)	−0.0029 (3)
O1	0.0520 (9)	0.0678 (10)	0.0500 (9)	0.0074 (8)	0.0089 (8)	0.0207 (9)
O2	0.0586 (9)	0.0679 (11)	0.0590 (10)	0.0190 (8)	0.0183 (8)	0.0014 (9)
N1	0.0387 (8)	0.0426 (9)	0.0414 (9)	0.0025 (7)	0.0023 (8)	0.0032 (8)
C1	0.0405 (10)	0.0387 (10)	0.0450 (12)	−0.0017 (8)	0.0034 (9)	−0.0009 (9)
C2	0.0443 (10)	0.0467 (11)	0.0513 (12)	0.0031 (9)	−0.0012 (10)	0.0070 (11)
C3	0.0425 (11)	0.0429 (12)	0.0628 (14)	0.0075 (9)	−0.0046 (10)	0.0014 (11)
C4	0.0360 (10)	0.0419 (11)	0.0582 (13)	0.0014 (8)	0.0063 (9)	−0.0064 (10)
C5	0.0417 (10)	0.0422 (11)	0.0460 (12)	0.0003 (8)	0.0064 (10)	−0.0005 (9)
C6	0.0372 (9)	0.0356 (9)	0.0425 (11)	−0.0008 (8)	−0.0009 (8)	−0.0019 (9)
C7	0.0382 (9)	0.0368 (10)	0.0370 (10)	−0.0017 (8)	−0.0007 (8)	0.0016 (8)
C8	0.0377 (9)	0.0341 (9)	0.0405 (10)	−0.0001 (8)	−0.0012 (8)	−0.0028 (8)
C9	0.0397 (10)	0.0424 (11)	0.0445 (11)	−0.0049 (8)	0.0005 (9)	0.0014 (9)
C10	0.0433 (11)	0.0476 (12)	0.0547 (13)	0.0013 (9)	−0.0056 (10)	0.0131 (10)
C11	0.0377 (10)	0.0436 (13)	0.0618 (14)	0.0065 (9)	−0.0022 (10)	−0.0007 (10)
C12	0.0421 (10)	0.0409 (10)	0.0482 (13)	0.0013 (8)	0.0067 (9)	−0.0051 (9)
C13	0.0457 (10)	0.0423 (10)	0.0395 (12)	0.0042 (8)	0.0006 (8)	0.0003 (9)
C14	0.0486 (13)	0.0615 (14)	0.0862 (19)	0.0091 (11)	0.0176 (14)	−0.0097 (14)

S1—C1	1.7364 (19)	C5—C6	1.397 (3)
S1—C7	1.755 (2)	C5—H5A	0.9300
Cl1—C4	1.749 (2)	C7—C8	1.460 (3)
O1—C9	1.357 (3)	C8—C13	1.397 (3)
O1—H1A	0.80 (3)	C8—C9	1.403 (3)
O2—C12	1.370 (3)	C9—C10	1.387 (3)
O2—C14	1.416 (3)	C10—C11	1.376 (3)
N1—C7	1.307 (3)	C10—H10A	0.9300
N1—C6	1.382 (2)	C11—C12	1.385 (3)
C1—C2	1.393 (3)	C11—H11A	0.9300
C1—C6	1.401 (3)	C12—C13	1.386 (3)
C2—C3	1.386 (3)	C13—H13A	0.9300
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.380 (3)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.373 (3)
C1—S1—C7	89.24 (10)	C13—C8—C9	119.16 (17)
C9—O1—H1A	105 (2)	C13—C8—C7	121.04 (18)
C12—O2—C14	117.9 (2)	C9—C8—C7	119.80 (17)
C7—N1—C6	111.61 (17)	O1—C9—C10	117.69 (19)
C2—C1—C6	120.9 (2)	O1—C9—C8	123.10 (18)
C2—C1—S1	129.54 (18)	C10—C9—C8	119.20 (19)
C6—C1—S1	109.53 (15)	C11—C10—C9	121.1 (2)
C3—C2—C1	117.9 (2)	C11—C10—H10A	119.4
C3—C2—H2A	121.0	C9—C10—H10A	119.4
C1—C2—H2A	121.0	C10—C11—C12	120.25 (18)
C4—C3—C2	120.19 (19)	C10—C11—H11A	119.9
C4—C3—H3A	119.9	C12—C11—H11A	119.9
C2—C3—H3A	119.9	O2—C12—C11	124.51 (18)
C5—C4—C3	123.4 (2)	O2—C12—C13	116.0 (2)
C5—C4—Cl1	118.03 (19)	C11—C12—C13	119.5 (2)
C3—C4—Cl1	118.56 (17)	C12—C13—C8	120.8 (2)
C4—C5—C6	116.8 (2)	C12—C13—H13A	119.6
C4—C5—H5A	121.6	C8—C13—H13A	119.6
C6—C5—H5A	121.6	O2—C14—H14A	109.5
N1—C6—C5	124.37 (19)	O2—C14—H14B	109.5
N1—C6—C1	114.83 (18)	H14A—C14—H14B	109.5
C5—C6—C1	120.79 (18)	O2—C14—H14C	109.5
N1—C7—C8	122.89 (18)	H14A—C14—H14C	109.5
N1—C7—S1	114.79 (15)	H14B—C14—H14C	109.5
C8—C7—S1	122.31 (15)
C7—S1—C1—C2	−178.3 (2)	C1—S1—C7—C8	−179.84 (17)
C7—S1—C1—C6	0.67 (15)	N1—C7—C8—C13	179.49 (19)
C6—C1—C2—C3	0.2 (3)	S1—C7—C8—C13	−1.3 (3)
S1—C1—C2—C3	179.04 (17)	N1—C7—C8—C9	−0.9 (3)
C1—C2—C3—C4	0.4 (3)	S1—C7—C8—C9	178.30 (15)
C2—C3—C4—C5	−0.9 (3)	C13—C8—C9—O1	−179.88 (19)
C2—C3—C4—Cl1	179.96 (17)	C7—C8—C9—O1	0.5 (3)
C3—C4—C5—C6	0.7 (3)	C13—C8—C9—C10	−0.8 (3)
Cl1—C4—C5—C6	179.85 (15)	C7—C8—C9—C10	179.61 (19)
C7—N1—C6—C5	178.95 (19)	O1—C9—C10—C11	179.6 (2)
C7—N1—C6—C1	0.3 (2)	C8—C9—C10—C11	0.5 (3)
C4—C5—C6—N1	−178.67 (19)	C9—C10—C11—C12	0.3 (3)
C4—C5—C6—C1	−0.1 (3)	C14—O2—C12—C11	11.7 (3)
C2—C1—C6—N1	178.37 (18)	C14—O2—C12—C13	−169.1 (2)
S1—C1—C6—N1	−0.7 (2)	C10—C11—C12—O2	178.3 (2)
C2—C1—C6—C5	−0.4 (3)	C10—C11—C12—C13	−0.8 (3)
S1—C1—C6—C5	−179.42 (15)	O2—C12—C13—C8	−178.71 (18)
C6—N1—C7—C8	179.54 (18)	C11—C12—C13—C8	0.5 (3)
C6—N1—C7—S1	0.3 (2)	C9—C8—C13—C12	0.3 (3)
C1—S1—C7—N1	−0.57 (17)	C7—C8—C13—C12	179.88 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.80 (3)	1.87 (3)	2.612 (2)	154 (3)
C5—H5A···O2i	0.93	2.57	3.454 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.80 (3)	1.87 (3)	2.612 (2)	154 (3)
C5—H5A⋯O2i	0.93	2.57	3.454 (3)	159

Symmetry code: (i) .