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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2912.
Published online 2010 October 23. doi:  10.1107/S1600536810041796
PMCID: PMC3009155

2-(Benzothia­zol-2-yl­sulfanyl)­acetic acid

Abstract

In the title compound, C9H7NO2S2, the benzine ring is essentially co-planar with the thia­zole ring, making a dihedral angle of 0.36 (7)°. In the crystal structure, mol­ecules are linked by inter­molecular O—H(...)N hydrogen bonds between the carb­oxy group and the thia­zole N atom into chains along [10An external file that holds a picture, illustration, etc.
Object name is e-66-o2912-efi2.jpg]. The chains are assembled into a supermolecular layer structure by thia­zole 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 [triangle]). For S(...)S contacts in similar compounds, see: Dai et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2912-scheme1.jpg

Experimental

Crystal data

  • C9H7NO2S2
  • M r = 225.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2912-efi3.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors acknowledge South China Normal University for supporting this work.

supplementary crystallographic information

Experimental

A solution of benzothiazole-2-thiol (167.2 mg, 1.00 mmol) and K2CO3 (207.0 mg, 1.50 mmol) in CH3OH (15 ml) was slowly added to a solution of 2-chloroacetic acid (113.4 mg, 1.20 mmol) in CH3OH (10 ml). The resultant solution was stirred and refluxed for 20 h and then filtered. Colorless crystals suitable for X-ray diffraction were obtained in about a week by slow diffusion of diethyl ether into a dilute solution of the title compound in methanol. yield: ca 82.3% (based on benzothiazole-2-thiol).

Refinement

The structure was solved using direct methods followed by Fourier synthesis. Non-H atoms were refined anisotropically. All of H atoms were placed in idealized positions (C—H = 0.93 or 0.97 Å, O—H = 0.82 Å), forced to ride on the atom to which they are bonded, and were included in the refinement in the riding-model approximation. Uiso values were set equal to 1.5Ueq(parent atom) for carboxylic H atom and to 1.2Ueq(parent atom)for all other H atoms.

Figures

Fig. 1.
The structure of the title compound with 50% probability displacement ellipsoids.
Fig. 2.
Two-dimensional supramolecular layer which is connected by O—H···N [O···N 2.686 (2) Å, H···N 1.89 Å, O—H···N 165.3°, ...

Crystal data

C9H7NO2S2F(000) = 464
Mr = 225.28Dx = 1.585 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2101 reflections
a = 6.0374 (5) Åθ = 2.7–27.5°
b = 19.2450 (17) ŵ = 0.53 mm1
c = 8.1250 (7) ÅT = 296 K
β = 90.419 (1)°Block, pink
V = 944.02 (14) Å30.23 × 0.21 × 0.17 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer1695 independent reflections
Radiation source: fine-focus sealed tube1439 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −4→7
Tmin = 0.885, Tmax = 0.914k = −22→23
4800 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0386P)2 + 0.2852P] where P = (Fo2 + 2Fc2)/3
1695 reflections(Δ/σ)max = 0.001
129 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.5666 (3)0.77360 (10)0.5938 (3)0.0446 (5)
C20.4631 (3)0.70448 (10)0.5538 (3)0.0424 (5)
H2A0.42890.67980.65460.051*
H2B0.56540.67640.49060.051*
C30.1497 (3)0.63490 (9)0.3747 (2)0.0367 (4)
C4−0.0451 (3)0.55193 (10)0.2515 (2)0.0371 (4)
C50.1331 (3)0.51163 (10)0.3081 (2)0.0391 (4)
C60.1436 (4)0.44073 (10)0.2773 (3)0.0509 (5)
H60.26240.41430.31540.061*
C7−0.0259 (4)0.41063 (11)0.1894 (3)0.0556 (6)
H7−0.02230.36320.16770.067*
C8−0.2024 (4)0.45021 (12)0.1327 (3)0.0531 (6)
H8−0.31540.42870.07320.064*
C9−0.2144 (3)0.52022 (11)0.1620 (2)0.0458 (5)
H9−0.33370.54610.12280.055*
N1−0.0309 (3)0.62213 (8)0.2909 (2)0.0396 (4)
O10.7348 (3)0.76603 (7)0.6956 (2)0.0557 (4)
H10.79110.80410.71400.084*
O20.5039 (3)0.82751 (8)0.5396 (2)0.0736 (5)
S10.21328 (9)0.71923 (3)0.43642 (7)0.04900 (19)
S20.31920 (8)0.56396 (2)0.41411 (7)0.04382 (18)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0430 (11)0.0378 (11)0.0528 (12)0.0004 (9)−0.0105 (10)−0.0021 (9)
C20.0413 (11)0.0343 (10)0.0515 (12)0.0031 (8)−0.0147 (9)0.0004 (8)
C30.0340 (10)0.0336 (10)0.0422 (11)0.0021 (8)−0.0077 (8)0.0014 (8)
C40.0402 (10)0.0332 (10)0.0378 (10)−0.0017 (8)−0.0033 (8)0.0011 (8)
C50.0420 (11)0.0354 (10)0.0398 (10)0.0014 (8)−0.0068 (9)0.0023 (8)
C60.0621 (14)0.0344 (11)0.0560 (13)0.0066 (9)−0.0087 (11)0.0005 (9)
C70.0772 (16)0.0335 (11)0.0562 (13)−0.0083 (11)−0.0032 (12)−0.0042 (10)
C80.0589 (14)0.0514 (13)0.0489 (12)−0.0166 (11)−0.0080 (10)−0.0046 (10)
C90.0410 (11)0.0495 (12)0.0468 (12)−0.0027 (9)−0.0099 (9)0.0009 (9)
N10.0387 (9)0.0344 (8)0.0455 (9)0.0022 (7)−0.0121 (7)0.0010 (7)
O10.0507 (9)0.0409 (8)0.0751 (11)−0.0069 (7)−0.0270 (8)0.0023 (7)
O20.0777 (12)0.0336 (9)0.1090 (14)−0.0015 (8)−0.0464 (10)0.0066 (8)
S10.0454 (3)0.0309 (3)0.0703 (4)0.0053 (2)−0.0231 (3)−0.0041 (2)
S20.0415 (3)0.0336 (3)0.0560 (3)0.00667 (19)−0.0177 (2)−0.0010 (2)

Geometric parameters (Å, °)

C1—O21.188 (2)C4—C51.401 (3)
C1—O11.313 (2)C5—C61.389 (3)
C1—C21.504 (3)C5—S21.7332 (19)
C2—S11.8012 (19)C6—C71.372 (3)
C2—H2A0.9700C6—H60.9300
C2—H2B0.9700C7—C81.386 (3)
C3—N11.304 (2)C7—H70.9300
C3—S21.7345 (18)C8—C91.370 (3)
C3—S11.7407 (18)C8—H80.9300
C4—N11.391 (2)C9—H90.9300
C4—C91.391 (3)O1—H10.8200
O2—C1—O1124.99 (19)C4—C5—S2109.55 (14)
O2—C1—C2124.15 (19)C7—C6—C5118.3 (2)
O1—C1—C2110.86 (17)C7—C6—H6120.9
C1—C2—S1108.66 (14)C5—C6—H6120.9
C1—C2—H2A110.0C6—C7—C8120.7 (2)
S1—C2—H2A110.0C6—C7—H7119.7
C1—C2—H2B110.0C8—C7—H7119.7
S1—C2—H2B110.0C9—C8—C7121.6 (2)
H2A—C2—H2B108.3C9—C8—H8119.2
N1—C3—S2115.97 (14)C7—C8—H8119.2
N1—C3—S1120.51 (14)C8—C9—C4118.9 (2)
S2—C3—S1123.51 (11)C8—C9—H9120.6
N1—C4—C9126.16 (18)C4—C9—H9120.6
N1—C4—C5114.61 (16)C3—N1—C4110.65 (15)
C9—C4—C5119.22 (18)C1—O1—H1109.5
C6—C5—C4121.37 (18)C3—S1—C2100.82 (9)
C6—C5—S2129.08 (16)C5—S2—C389.21 (9)
O2—C1—C2—S1−7.7 (3)C5—C4—C9—C80.4 (3)
O1—C1—C2—S1172.54 (15)S2—C3—N1—C40.0 (2)
N1—C4—C5—C6−179.50 (19)S1—C3—N1—C4178.49 (14)
C9—C4—C5—C6−0.3 (3)C9—C4—N1—C3−179.45 (19)
N1—C4—C5—S20.5 (2)C5—C4—N1—C3−0.3 (2)
C9—C4—C5—S2179.69 (15)N1—C3—S1—C2176.73 (16)
C4—C5—C6—C70.0 (3)S2—C3—S1—C2−4.87 (16)
S2—C5—C6—C7−179.96 (17)C1—C2—S1—C3170.23 (15)
C5—C6—C7—C80.2 (3)C6—C5—S2—C3179.6 (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—C50.25 (16)
N1—C4—C9—C8179.49 (19)S1—C3—S2—C5−178.21 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.892.686 (2)165

Symmetry codes: (i) x+1, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2058).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dai, J., Munakata, M., Kuroda-Sowa, T., Suenaga, Y., Wu, L. P. & Yamamoto, M. (1997). Inorg. Chim. Acta, 258, 65–69.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhu, J.-Q., Fang, H.-C., Chen, B.-Y., Feng, M.-S. & Li, J.-N. (2009). Acta Cryst. E65, o1640. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography