2-(Benzothia-zol-2-yl-sulfanyl)-acetic acid.

In the title compound, C(9)H(7)NO(2)S(2), the benzine ring is essentially co-planar with the thia-zole ring, making a dihedral angle of 0.36 (7)°. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯N hydrogen bonds between the carb-oxy group and the thia-zole N atom into chains along [10]. The chains are assembled into a supermolecular layer structure by thia-zole ring S⋯S contacts [3.5679 (7) Å].

Related literature

For the structure of tris­(2-hy­droxy­eth­yl)ammonium 3-benzo­thia­zole-2-thiol­ate, see: Zhu et al. (2009 ▶). For S⋯S contacts in similar compounds, see: Dai et al. (1997 ▶).

Experimental

Crystal data

C9H7NO2S2

M = 225.28

Monoclinic,

a = 6.0374 (5) Å

b = 19.2450 (17) Å

c = 8.1250 (7) Å

β = 90.419 (1)°

V = 944.02 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 296 K

0.23 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.885, T max = 0.914

4800 measured reflections

1695 independent reflections

1439 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.04

1695 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810041796/ds2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041796/ds2058Isup2.hkl

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

C9H7NO2S2	F(000) = 464
Mr = 225.28	Dx = 1.585 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2101 reflections
a = 6.0374 (5) Å	θ = 2.7–27.5°
b = 19.2450 (17) Å	µ = 0.53 mm−1
c = 8.1250 (7) Å	T = 296 K
β = 90.419 (1)°	Block, pink
V = 944.02 (14) Å3	0.23 × 0.21 × 0.17 mm
Z = 4

Bruker APEXII CCD diffractometer	1695 independent reflections
Radiation source: fine-focus sealed tube	1439 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→7
Tmin = 0.885, Tmax = 0.914	k = −22→23
4800 measured reflections	l = −9→9

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.2852P] where P = (Fo2 + 2Fc2)/3
1695 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.16 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
C1	0.5666 (3)	0.77360 (10)	0.5938 (3)	0.0446 (5)
C2	0.4631 (3)	0.70448 (10)	0.5538 (3)	0.0424 (5)
H2A	0.4289	0.6798	0.6546	0.051*
H2B	0.5654	0.6764	0.4906	0.051*
C3	0.1497 (3)	0.63490 (9)	0.3747 (2)	0.0367 (4)
C4	−0.0451 (3)	0.55193 (10)	0.2515 (2)	0.0371 (4)
C5	0.1331 (3)	0.51163 (10)	0.3081 (2)	0.0391 (4)
C6	0.1436 (4)	0.44073 (10)	0.2773 (3)	0.0509 (5)
H6	0.2624	0.4143	0.3154	0.061*
C7	−0.0259 (4)	0.41063 (11)	0.1894 (3)	0.0556 (6)
H7	−0.0223	0.3632	0.1677	0.067*
C8	−0.2024 (4)	0.45021 (12)	0.1327 (3)	0.0531 (6)
H8	−0.3154	0.4287	0.0732	0.064*
C9	−0.2144 (3)	0.52022 (11)	0.1620 (2)	0.0458 (5)
H9	−0.3337	0.5461	0.1228	0.055*
N1	−0.0309 (3)	0.62213 (8)	0.2909 (2)	0.0396 (4)
O1	0.7348 (3)	0.76603 (7)	0.6956 (2)	0.0557 (4)
H1	0.7911	0.8041	0.7140	0.084*
O2	0.5039 (3)	0.82751 (8)	0.5396 (2)	0.0736 (5)
S1	0.21328 (9)	0.71923 (3)	0.43642 (7)	0.04900 (19)
S2	0.31920 (8)	0.56396 (2)	0.41411 (7)	0.04382 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0430 (11)	0.0378 (11)	0.0528 (12)	0.0004 (9)	−0.0105 (10)	−0.0021 (9)
C2	0.0413 (11)	0.0343 (10)	0.0515 (12)	0.0031 (8)	−0.0147 (9)	0.0004 (8)
C3	0.0340 (10)	0.0336 (10)	0.0422 (11)	0.0021 (8)	−0.0077 (8)	0.0014 (8)
C4	0.0402 (10)	0.0332 (10)	0.0378 (10)	−0.0017 (8)	−0.0033 (8)	0.0011 (8)
C5	0.0420 (11)	0.0354 (10)	0.0398 (10)	0.0014 (8)	−0.0068 (9)	0.0023 (8)
C6	0.0621 (14)	0.0344 (11)	0.0560 (13)	0.0066 (9)	−0.0087 (11)	0.0005 (9)
C7	0.0772 (16)	0.0335 (11)	0.0562 (13)	−0.0083 (11)	−0.0032 (12)	−0.0042 (10)
C8	0.0589 (14)	0.0514 (13)	0.0489 (12)	−0.0166 (11)	−0.0080 (10)	−0.0046 (10)
C9	0.0410 (11)	0.0495 (12)	0.0468 (12)	−0.0027 (9)	−0.0099 (9)	0.0009 (9)
N1	0.0387 (9)	0.0344 (8)	0.0455 (9)	0.0022 (7)	−0.0121 (7)	0.0010 (7)
O1	0.0507 (9)	0.0409 (8)	0.0751 (11)	−0.0069 (7)	−0.0270 (8)	0.0023 (7)
O2	0.0777 (12)	0.0336 (9)	0.1090 (14)	−0.0015 (8)	−0.0464 (10)	0.0066 (8)
S1	0.0454 (3)	0.0309 (3)	0.0703 (4)	0.0053 (2)	−0.0231 (3)	−0.0041 (2)
S2	0.0415 (3)	0.0336 (3)	0.0560 (3)	0.00667 (19)	−0.0177 (2)	−0.0010 (2)

C1—O2	1.188 (2)	C4—C5	1.401 (3)
C1—O1	1.313 (2)	C5—C6	1.389 (3)
C1—C2	1.504 (3)	C5—S2	1.7332 (19)
C2—S1	1.8012 (19)	C6—C7	1.372 (3)
C2—H2A	0.9700	C6—H6	0.9300
C2—H2B	0.9700	C7—C8	1.386 (3)
C3—N1	1.304 (2)	C7—H7	0.9300
C3—S2	1.7345 (18)	C8—C9	1.370 (3)
C3—S1	1.7407 (18)	C8—H8	0.9300
C4—N1	1.391 (2)	C9—H9	0.9300
C4—C9	1.391 (3)	O1—H1	0.8200
O2—C1—O1	124.99 (19)	C4—C5—S2	109.55 (14)
O2—C1—C2	124.15 (19)	C7—C6—C5	118.3 (2)
O1—C1—C2	110.86 (17)	C7—C6—H6	120.9
C1—C2—S1	108.66 (14)	C5—C6—H6	120.9
C1—C2—H2A	110.0	C6—C7—C8	120.7 (2)
S1—C2—H2A	110.0	C6—C7—H7	119.7
C1—C2—H2B	110.0	C8—C7—H7	119.7
S1—C2—H2B	110.0	C9—C8—C7	121.6 (2)
H2A—C2—H2B	108.3	C9—C8—H8	119.2
N1—C3—S2	115.97 (14)	C7—C8—H8	119.2
N1—C3—S1	120.51 (14)	C8—C9—C4	118.9 (2)
S2—C3—S1	123.51 (11)	C8—C9—H9	120.6
N1—C4—C9	126.16 (18)	C4—C9—H9	120.6
N1—C4—C5	114.61 (16)	C3—N1—C4	110.65 (15)
C9—C4—C5	119.22 (18)	C1—O1—H1	109.5
C6—C5—C4	121.37 (18)	C3—S1—C2	100.82 (9)
C6—C5—S2	129.08 (16)	C5—S2—C3	89.21 (9)
O2—C1—C2—S1	−7.7 (3)	C5—C4—C9—C8	0.4 (3)
O1—C1—C2—S1	172.54 (15)	S2—C3—N1—C4	0.0 (2)
N1—C4—C5—C6	−179.50 (19)	S1—C3—N1—C4	178.49 (14)
C9—C4—C5—C6	−0.3 (3)	C9—C4—N1—C3	−179.45 (19)
N1—C4—C5—S2	0.5 (2)	C5—C4—N1—C3	−0.3 (2)
C9—C4—C5—S2	179.69 (15)	N1—C3—S1—C2	176.73 (16)
C4—C5—C6—C7	0.0 (3)	S2—C3—S1—C2	−4.87 (16)
S2—C5—C6—C7	−179.96 (17)	C1—C2—S1—C3	170.23 (15)
C5—C6—C7—C8	0.2 (3)	C6—C5—S2—C3	179.6 (2)
C6—C7—C8—C9	−0.1 (4)	C4—C5—S2—C3	−0.40 (15)
C7—C8—C9—C4	−0.2 (3)	N1—C3—S2—C5	0.25 (16)
N1—C4—C9—C8	179.49 (19)	S1—C3—S2—C5	−178.21 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.89	2.686 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.89	2.686 (2)	165

Symmetry code: (i) .