2-(3-Oxo-2,3-dihydro-1,2-benzothia-zol-2-yl)acetic acid.

In the title compound, C(9)H(7)NO(3)S, the benzoisothia-zolone ring system is essentially planar, with a maximum deviation of 0.013 (2) Å. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds, forming chains along [010]. In addition, weak inter-molecular C-H⋯O hydrogen bonds are present.

Related literature

For background to the sythesis of benzisothia­zolone derivatives, see: Davis (1972 ▶); Maggiali et al. (1982 ▶, 1983 ▶), Elgazwy & Abdel-Sattar (2003 ▶). For details of their biological activity, see: Taubert et al. (2002 ▶); Mor et al. (1996 ▶). For related structures, see: Xu et al. (2006 ▶), Wang et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C9H7NO3S

M = 209.22

Orthorhombic,

a = 4.7774 (11) Å

b = 11.367 (3) Å

c = 16.159 (4) Å

V = 877.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 153 K

0.29 × 0.22 × 0.20 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.907, T max = 0.934

7675 measured reflections

2340 independent reflections

2141 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.068

S = 1.00

2340 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 945 Friedel pairs

Flack parameter: 0.08 (7)

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047490/lh5367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047490/lh5367Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047490/lh5367Isup3.cml

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

C9H7NO3S	F(000) = 432
Mr = 209.22	Dx = 1.584 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3259 reflections
a = 4.7774 (11) Å	θ = 3.1–29.1°
b = 11.367 (3) Å	µ = 0.35 mm−1
c = 16.159 (4) Å	T = 153 K
V = 877.6 (4) Å3	Block, colorless
Z = 4	0.29 × 0.22 × 0.20 mm

Rigaku AFC10/Saturn724+ diffractometer	2340 independent reflections
Radiation source: Rotating Anode	2141 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 3.1°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.907, Tmax = 0.934	l = −22→16
7675 measured reflections

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0304P)2 + 0.136P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2340 reflections	Δρmax = 0.27 e Å−3
131 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 945 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (7)

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	0.79701 (8)	0.63585 (3)	0.49404 (2)	0.01821 (10)
O1	0.4484 (3)	0.48499 (11)	0.67636 (7)	0.0275 (3)
O2	0.4545 (3)	0.79003 (11)	0.67052 (8)	0.0253 (3)
O3	0.7852 (3)	0.79542 (12)	0.76921 (7)	0.0266 (3)
N1	0.7188 (3)	0.60058 (12)	0.59414 (8)	0.0196 (3)
C1	0.5586 (3)	0.53095 (14)	0.45995 (10)	0.0170 (3)
C2	0.4940 (4)	0.50367 (15)	0.37799 (10)	0.0208 (4)
H2	0.5850	0.5422	0.3333	0.025*
C3	0.2934 (4)	0.41885 (16)	0.36417 (11)	0.0251 (4)
H3	0.2443	0.3992	0.3089	0.030*
C4	0.1598 (4)	0.36082 (17)	0.42984 (11)	0.0251 (4)
H4	0.0224	0.3027	0.4184	0.030*
C5	0.2255 (3)	0.38708 (13)	0.51040 (11)	0.0216 (3)
H5	0.1357	0.3475	0.5548	0.026*
C6	0.4278 (4)	0.47343 (14)	0.52566 (10)	0.0176 (3)
C7	0.5239 (4)	0.51590 (14)	0.60561 (10)	0.0191 (4)
C8	0.8509 (4)	0.65927 (15)	0.66335 (10)	0.0212 (4)
H8A	1.0303	0.6939	0.6447	0.025*
H8B	0.8936	0.6005	0.7067	0.025*
C9	0.6707 (4)	0.75520 (14)	0.70016 (10)	0.0193 (3)
H3O	0.695 (5)	0.855 (3)	0.7888 (16)	0.070 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.01808 (17)	0.01776 (17)	0.01879 (19)	−0.00127 (16)	0.00143 (16)	−0.00022 (16)
O1	0.0388 (8)	0.0262 (7)	0.0175 (6)	−0.0044 (6)	0.0032 (5)	0.0031 (5)
O2	0.0208 (6)	0.0279 (7)	0.0271 (7)	0.0030 (6)	−0.0043 (5)	−0.0024 (6)
O3	0.0313 (7)	0.0287 (7)	0.0198 (6)	0.0057 (6)	−0.0071 (6)	−0.0065 (5)
N1	0.0228 (7)	0.0204 (7)	0.0157 (6)	−0.0026 (6)	0.0014 (6)	−0.0006 (5)
C1	0.0147 (8)	0.0162 (8)	0.0202 (8)	0.0017 (7)	−0.0005 (6)	−0.0009 (6)
C2	0.0217 (10)	0.0227 (9)	0.0179 (8)	0.0021 (7)	0.0002 (7)	0.0004 (7)
C3	0.0262 (9)	0.0293 (9)	0.0199 (8)	0.0010 (8)	−0.0050 (8)	−0.0042 (7)
C4	0.0220 (9)	0.0220 (8)	0.0311 (10)	−0.0046 (8)	−0.0031 (7)	−0.0033 (7)
C5	0.0208 (8)	0.0186 (8)	0.0253 (9)	−0.0002 (6)	0.0011 (7)	0.0026 (6)
C6	0.0184 (8)	0.0153 (7)	0.0191 (8)	0.0034 (7)	0.0006 (6)	0.0002 (6)
C7	0.0217 (9)	0.0159 (8)	0.0195 (9)	−0.0003 (7)	−0.0002 (7)	0.0017 (6)
C8	0.0229 (9)	0.0216 (8)	0.0190 (8)	0.0008 (7)	−0.0037 (7)	−0.0034 (6)
C9	0.0206 (9)	0.0201 (8)	0.0173 (8)	−0.0038 (7)	−0.0001 (7)	0.0029 (6)

S1—N1	1.7079 (15)	C2—H2	0.9500
S1—C1	1.7385 (17)	C3—C4	1.403 (3)
O1—C7	1.249 (2)	C3—H3	0.9500
O2—C9	1.206 (2)	C4—C5	1.372 (2)
O3—C9	1.324 (2)	C4—H4	0.9500
O3—H3O	0.87 (3)	C5—C6	1.399 (2)
N1—C7	1.352 (2)	C5—H5	0.9500
N1—C8	1.447 (2)	C6—C7	1.454 (2)
C1—C6	1.395 (2)	C8—C9	1.511 (2)
C1—C2	1.395 (2)	C8—H8A	0.9900
C2—C3	1.378 (2)	C8—H8B	0.9900
N1—S1—C1	89.76 (8)	C4—C5—H5	120.7
C9—O3—H3O	112.0 (17)	C6—C5—H5	120.7
C7—N1—C8	121.51 (14)	C1—C6—C5	120.26 (15)
C7—N1—S1	116.59 (11)	C1—C6—C7	112.31 (15)
C8—N1—S1	121.90 (11)	C5—C6—C7	127.43 (15)
C6—C1—C2	121.30 (15)	O1—C7—N1	121.64 (15)
C6—C1—S1	111.95 (12)	O1—C7—C6	128.96 (17)
C2—C1—S1	126.75 (13)	N1—C7—C6	109.40 (14)
C3—C2—C1	117.61 (15)	N1—C8—C9	112.86 (14)
C3—C2—H2	121.2	N1—C8—H8A	109.0
C1—C2—H2	121.2	C9—C8—H8A	109.0
C2—C3—C4	121.52 (16)	N1—C8—H8B	109.0
C2—C3—H3	119.2	C9—C8—H8B	109.0
C4—C3—H3	119.2	H8A—C8—H8B	107.8
C5—C4—C3	120.75 (17)	O2—C9—O3	125.12 (17)
C5—C4—H4	119.6	O2—C9—C8	124.66 (16)
C3—C4—H4	119.6	O3—C9—C8	110.22 (15)
C4—C5—C6	118.55 (15)
C1—S1—N1—C7	−0.51 (14)	C4—C5—C6—C7	178.74 (17)
C1—S1—N1—C8	−179.65 (14)	C8—N1—C7—O1	0.3 (3)
N1—S1—C1—C6	0.23 (13)	S1—N1—C7—O1	−178.81 (14)
N1—S1—C1—C2	179.76 (16)	C8—N1—C7—C6	179.77 (14)
C6—C1—C2—C3	0.8 (2)	S1—N1—C7—C6	0.63 (18)
S1—C1—C2—C3	−178.65 (14)	C1—C6—C7—O1	178.96 (17)
C1—C2—C3—C4	−0.6 (3)	C5—C6—C7—O1	0.1 (3)
C2—C3—C4—C5	0.0 (3)	C1—C6—C7—N1	−0.4 (2)
C3—C4—C5—C6	0.3 (3)	C5—C6—C7—N1	−179.27 (15)
C2—C1—C6—C5	−0.5 (2)	C7—N1—C8—C9	−80.1 (2)
S1—C1—C6—C5	179.01 (12)	S1—N1—C8—C9	99.03 (15)
C2—C1—C6—C7	−179.49 (15)	N1—C8—C9—O2	−8.2 (2)
S1—C1—C6—C7	0.06 (18)	N1—C8—C9—O3	172.04 (14)
C4—C5—C6—C1	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1i	0.86 (3)	1.72 (3)	2.581 (2)	173 (3)
C2—H2···O2ii	0.95	2.60	3.310 (2)	132
C8—H8A···O2iii	0.99	2.34	3.246 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O1i	0.86 (3)	1.72 (3)	2.581 (2)	173 (3)
C2—H2⋯O2ii	0.95	2.60	3.310 (2)	132
C8—H8A⋯O2iii	0.99	2.34	3.246 (2)	152

Symmetry codes: (i) ; (ii) ; (iii) .