2-(2H-1,3-Benzodioxol-5-yl)-1,3-benzo-thia-zole.

In the title compound, C(14)H(9)O(2)S, the benzothia-zole unit is oriented at a dihedral angle of 7.1 (1)° with respect to the benzodioxole unit. The dioxole ring adopts flattened envelope conformation with the methyl-ene C atom at the flap. The crystal packing is stabilized by π-π inter-actions [centroid-centroid distances = 3.705 (1) and 3.752 (1) Å], C-H⋯π inter-actions and a short S⋯S contact of 3.485 (1) Å.

Related literature

For background to the applications of benzothia­zoles in the chemical industry, see: Bradshaw et al. (2002 ▶); Delmas et al. (2002 ▶); Hutchinson et al. (2002 ▶). For the pharmacological activity of benzothia­zole derivatives, see: Repiĉ et al. (2001 ▶); Schwartz et al. (1992 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For related structures, see: Baryala et al. (2010 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C14H9NO2S

M = 255.28

Orthorhombic,

a = 6.3356 (2) Å

b = 16.3222 (5) Å

c = 22.0471 (7) Å

V = 2279.91 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.952

15338 measured reflections

3135 independent reflections

2243 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.02

3135 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008914/gk2459sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008914/gk2459Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008914/gk2459Isup3.cml

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

C14H9NO2S	F(000) = 1056
Mr = 255.28	Dx = 1.487 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3185 reflections
a = 6.3356 (2) Å	θ = 2.7–29.5°
b = 16.3222 (5) Å	µ = 0.28 mm−1
c = 22.0471 (7) Å	T = 293 K
V = 2279.91 (12) Å3	Block, colourless
Z = 8	0.25 × 0.23 × 0.18 mm

Bruker APEXII CCD diffractometer	3135 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 29.5°, θmin = 2.7°
ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −22→19
Tmin = 0.934, Tmax = 0.952	l = −30→30
15338 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.5885P] where P = (Fo2 + 2Fc2)/3
3135 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 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
C2	0.3453 (2)	0.55583 (8)	0.34631 (6)	0.0361 (3)
C3	0.5016 (3)	0.53503 (10)	0.30472 (7)	0.0467 (4)
H3	0.5044	0.5591	0.2665	0.056*
C4	0.6519 (3)	0.47847 (11)	0.32101 (8)	0.0536 (4)
H4	0.7554	0.4637	0.2932	0.064*
C5	0.6523 (3)	0.44284 (10)	0.37826 (9)	0.0540 (4)
H5	0.7562	0.4049	0.3882	0.065*
C6	0.5011 (3)	0.46295 (10)	0.42024 (8)	0.0497 (4)
H6	0.5013	0.4393	0.4586	0.060*
C7	0.3482 (2)	0.51935 (9)	0.40395 (7)	0.0389 (3)
C1	0.0600 (2)	0.61568 (8)	0.38384 (6)	0.0352 (3)
C8	−0.1316 (2)	0.66515 (9)	0.38831 (6)	0.0361 (3)
C9	−0.2413 (3)	0.67047 (10)	0.44268 (6)	0.0426 (4)
H9	−0.1896	0.6427	0.4764	0.051*
C10	−0.4255 (3)	0.71583 (10)	0.44857 (7)	0.0482 (4)
H10	−0.4971	0.7194	0.4853	0.058*
C11	−0.4962 (2)	0.75501 (9)	0.39779 (7)	0.0423 (3)
C14	−0.6822 (3)	0.82343 (13)	0.32904 (9)	0.0610 (5)
H14A	−0.8035	0.7967	0.3110	0.073*
H14B	−0.6977	0.8821	0.3238	0.073*
C12	−0.3898 (2)	0.74996 (9)	0.34317 (7)	0.0399 (3)
C13	−0.2079 (2)	0.70649 (9)	0.33649 (7)	0.0395 (3)
H13	−0.1373	0.7041	0.2996	0.047*
N1	0.17928 (19)	0.61002 (7)	0.33610 (5)	0.0374 (3)
O1	−0.6701 (2)	0.80397 (8)	0.39209 (6)	0.0589 (3)
O2	−0.49343 (19)	0.79602 (7)	0.30038 (5)	0.0559 (3)
S1	0.13899 (7)	0.55612 (3)	0.445920 (18)	0.05001 (14)

	U11	U22	U33	U12	U13	U23
C2	0.0354 (8)	0.0350 (7)	0.0380 (7)	−0.0045 (6)	−0.0022 (6)	−0.0013 (5)
C3	0.0491 (10)	0.0484 (9)	0.0426 (8)	−0.0004 (8)	0.0053 (7)	−0.0030 (6)
C4	0.0486 (10)	0.0508 (9)	0.0613 (11)	0.0041 (8)	0.0078 (8)	−0.0119 (8)
C5	0.0499 (10)	0.0412 (9)	0.0710 (12)	0.0092 (8)	−0.0066 (9)	−0.0042 (8)
C6	0.0515 (10)	0.0455 (8)	0.0523 (9)	0.0040 (8)	−0.0069 (8)	0.0062 (7)
C7	0.0387 (8)	0.0389 (7)	0.0391 (7)	−0.0033 (6)	−0.0013 (6)	0.0022 (6)
C1	0.0336 (7)	0.0396 (7)	0.0323 (6)	−0.0061 (6)	−0.0033 (6)	0.0018 (5)
C8	0.0326 (7)	0.0390 (7)	0.0367 (7)	−0.0043 (6)	−0.0021 (6)	−0.0033 (5)
C9	0.0443 (9)	0.0464 (8)	0.0372 (7)	−0.0018 (7)	0.0001 (7)	−0.0014 (6)
C10	0.0477 (9)	0.0531 (9)	0.0439 (8)	0.0007 (8)	0.0093 (7)	−0.0072 (7)
C11	0.0368 (8)	0.0372 (7)	0.0528 (8)	0.0005 (7)	0.0023 (7)	−0.0094 (6)
C14	0.0496 (11)	0.0653 (12)	0.0680 (12)	0.0174 (9)	−0.0045 (9)	−0.0032 (9)
C12	0.0391 (8)	0.0368 (7)	0.0439 (8)	−0.0016 (7)	−0.0050 (6)	−0.0027 (6)
C13	0.0381 (8)	0.0429 (8)	0.0375 (7)	−0.0013 (7)	0.0011 (6)	−0.0020 (6)
N1	0.0378 (7)	0.0409 (6)	0.0334 (6)	0.0007 (5)	−0.0006 (5)	0.0012 (5)
O1	0.0511 (8)	0.0612 (7)	0.0644 (8)	0.0187 (6)	0.0052 (6)	−0.0041 (6)
O2	0.0511 (7)	0.0618 (7)	0.0549 (7)	0.0179 (6)	−0.0032 (6)	0.0060 (5)
S1	0.0452 (3)	0.0662 (3)	0.0386 (2)	0.0075 (2)	0.00557 (17)	0.01540 (17)

C2—C3	1.392 (2)	C8—C9	1.388 (2)
C2—N1	1.3926 (18)	C8—C13	1.412 (2)
C2—C7	1.403 (2)	C9—C10	1.388 (2)
C3—C4	1.374 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.365 (2)
C4—C5	1.390 (3)	C10—H10	0.9300
C4—H4	0.9300	C11—O1	1.3668 (19)
C5—C6	1.372 (3)	C11—C12	1.383 (2)
C5—H5	0.9300	C14—O2	1.424 (2)
C6—C7	1.384 (2)	C14—O1	1.428 (2)
C6—H6	0.9300	C14—H14A	0.9700
C7—S1	1.7243 (16)	C14—H14B	0.9700
C1—N1	1.2991 (18)	C12—C13	1.361 (2)
C1—C8	1.461 (2)	C12—O2	1.3731 (18)
C1—S1	1.7517 (14)	C13—H13	0.9300
C3—C2—N1	125.86 (13)	C10—C9—H9	118.8
C3—C2—C7	118.93 (14)	C8—C9—H9	118.8
N1—C2—C7	115.20 (13)	C11—C10—C9	116.70 (14)
C4—C3—C2	118.99 (15)	C11—C10—H10	121.7
C4—C3—H3	120.5	C9—C10—H10	121.7
C2—C3—H3	120.5	C10—C11—O1	127.88 (15)
C3—C4—C5	121.33 (16)	C10—C11—C12	121.77 (15)
C3—C4—H4	119.3	O1—C11—C12	110.34 (14)
C5—C4—H4	119.3	O2—C14—O1	108.49 (14)
C6—C5—C4	120.75 (16)	O2—C14—H14A	110.0
C6—C5—H5	119.6	O1—C14—H14A	110.0
C4—C5—H5	119.6	O2—C14—H14B	110.0
C5—C6—C7	118.21 (15)	O1—C14—H14B	110.0
C5—C6—H6	120.9	H14A—C14—H14B	108.4
C7—C6—H6	120.9	C13—C12—O2	128.00 (14)
C6—C7—C2	121.78 (15)	C13—C12—C11	122.54 (14)
C6—C7—S1	129.07 (12)	O2—C12—C11	109.44 (13)
C2—C7—S1	109.16 (11)	C12—C13—C8	116.84 (14)
N1—C1—C8	125.25 (13)	C12—C13—H13	121.6
N1—C1—S1	115.30 (11)	C8—C13—H13	121.6
C8—C1—S1	119.43 (10)	C1—N1—C2	110.70 (12)
C9—C8—C13	119.81 (14)	C11—O1—C14	105.23 (13)
C9—C8—C1	120.58 (13)	C12—O2—C14	105.57 (13)
C13—C8—C1	119.60 (13)	C7—S1—C1	89.62 (7)
C10—C9—C8	122.34 (14)
N1—C2—C3—C4	−178.02 (14)	O1—C11—C12—C13	178.48 (13)
C7—C2—C3—C4	1.1 (2)	C10—C11—C12—O2	−179.03 (14)
C2—C3—C4—C5	−1.0 (3)	O1—C11—C12—O2	0.01 (18)
C3—C4—C5—C6	0.4 (3)	O2—C12—C13—C8	178.89 (14)
C4—C5—C6—C7	0.2 (3)	C11—C12—C13—C8	0.7 (2)
C5—C6—C7—C2	−0.1 (2)	C9—C8—C13—C12	−0.3 (2)
C5—C6—C7—S1	179.51 (13)	C1—C8—C13—C12	178.46 (13)
C3—C2—C7—C6	−0.5 (2)	C8—C1—N1—C2	−178.07 (12)
N1—C2—C7—C6	178.66 (14)	S1—C1—N1—C2	0.36 (15)
C3—C2—C7—S1	179.79 (12)	C3—C2—N1—C1	179.57 (14)
N1—C2—C7—S1	−1.03 (16)	C7—C2—N1—C1	0.45 (17)
N1—C1—C8—C9	−176.37 (14)	C10—C11—O1—C14	−175.20 (17)
S1—C1—C8—C9	5.26 (19)	C12—C11—O1—C14	5.84 (18)
N1—C1—C8—C13	4.9 (2)	O2—C14—O1—C11	−9.44 (19)
S1—C1—C8—C13	−173.44 (11)	C13—C12—O2—C14	175.75 (16)
C13—C8—C9—C10	−0.4 (2)	C11—C12—O2—C14	−5.88 (18)
C1—C8—C9—C10	−179.06 (14)	O1—C14—O2—C12	9.48 (19)
C8—C9—C10—C11	0.5 (2)	C6—C7—S1—C1	−178.68 (15)
C9—C10—C11—O1	−178.94 (14)	C2—C7—S1—C1	0.98 (11)
C9—C10—C11—C12	−0.1 (2)	N1—C1—S1—C7	−0.81 (12)
C10—C11—C12—C13	−0.6 (2)	C8—C1—S1—C7	177.71 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.93	2.79	3.624 (2)	150
C14—H14B···Cg2ii	0.97	2.84	3.580 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the dioxole ring and Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.93	2.79	3.624 (2)	150
C14—H14B⋯Cg2ii	0.97	2.84	3.580 (2)	134

Symmetry codes: (i) ; (ii) .