Acta Cryst. (2009). E65, o1206 [ doi:10.1107/S1600536809015967 ]
The complete molecule of the title compound, C10H10O4S2, is generated by a crystallographic inversion centre. In the crystal, molecules are linked into a one-dimensional chain by intermolecular O-H
O hydrogen bonds.
The solution of 1,4-benzenebisthiol (7.11 g, 0.05 mol) in water (10 ml) neutralized with NaOH (4.00 g, 0.10 mol) was added to a 1:1 mixture of chloroacetic acid (18.90 g, 0.20 mol) and NaOH (8.00 g, 0.20 mol) with stirring to adjust the pH value of the mixture to ca 11 and refluxed at 363 K for 3 h. Then adjust the pH value to 2–3 with concentrated hydrochloric acid as soon as the reaction finished. The sample was filtrated, washed by water, then dried, the compound (I) was obtained with a yield of 80%.
The H atoms bonded to C atoms were positioned geometrically [aliphatic C—H = 0.97 Å and aromatic C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C)]. The H atoms bonded to O atoms were located in a difference Fourier maps and refined with Uiso(H) = 1.5Ueq(O).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./at2772fig1thm.gif)
| Fig. 1. A view of the molecule of the compound (I), showing the atom-labelling scheme. displacement ellipsoids are shown at the 30% probability level. |
![[Figure 2]](./at2772fig2thm.gif)
| Fig. 2. A view of the one-dimentional chain formed via O—H···O bydrogen bonds. |
| C10H10O4S2 | Z = 1 |
| Mr = 258.30 | F000 = 134 |
| Triclinic, P1 | Dx = 1.603 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 5.5633 (4) Å | Cell parameters from 2874 reflections |
| b = 6.9311 (5) Å | θ = 2.9–27.6º |
| c = 7.6173 (6) Å | µ = 0.49 mm−1 |
| α = 79.809 (5)º | T = 296 K |
| β = 70.738 (4)º | Block, colourless |
| γ = 76.112 (4)º | 0.47 × 0.30 × 0.20 mm |
| V = 267.64 (3) Å3 |
| Bruker APEXII diffractometer | 1209 independent reflections |
| Radiation source: fine-focus sealed tube | 1136 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.016 |
| T = 296 K | θmax = 27.6º |
| ω scans | θmin = 2.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
| Tmin = 0.839, Tmax = 0.908 | k = −8→9 |
| 3837 measured reflections | l = −9→9 |
| 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)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0362P)2 + 0.0845P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max < 0.001 |
| 1209 reflections | Δρmax = 0.19 e Å−3 |
| 77 parameters | Δρmin = −0.26 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C10H10O4S2 | γ = 76.112 (4)º |
| Mr = 258.30 | V = 267.64 (3) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 5.5633 (4) Å | Mo Kα |
| b = 6.9311 (5) Å | µ = 0.49 mm−1 |
| c = 7.6173 (6) Å | T = 296 K |
| α = 79.809 (5)º | 0.47 × 0.30 × 0.20 mm |
| β = 70.738 (4)º |
| Bruker APEXII diffractometer | 1209 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1136 reflections with I > 2σ(I) |
| Tmin = 0.839, Tmax = 0.908 | Rint = 0.016 |
| 3837 measured reflections |
| R[F2 > 2σ(F2)] = 0.027 | 77 parameters |
| wR(F2) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.09 | Δρmax = 0.19 e Å−3 |
| 1209 reflections | Δρmin = −0.26 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 | ||
| S1 | 0.66238 (6) | 0.55947 (5) | 0.67832 (5) | 0.03597 (14) | |
| O2 | 0.6441 (2) | 0.17946 (15) | 0.87948 (16) | 0.0469 (3) | |
| O1 | 0.2166 (2) | 0.19194 (15) | 0.97977 (16) | 0.0425 (3) | |
| H1 | 0.263 (4) | 0.075 (4) | 1.019 (3) | 0.069 (7)* | |
| C1 | 0.5592 (3) | 0.80504 (18) | 0.58268 (18) | 0.0294 (3) | |
| C2 | 0.3044 (3) | 0.9090 (2) | 0.6244 (2) | 0.0396 (3) | |
| H2A | 0.1718 | 0.8488 | 0.7077 | 0.048* | |
| C3 | 0.2472 (3) | 1.1024 (2) | 0.5422 (2) | 0.0390 (3) | |
| H3A | 0.0759 | 1.1712 | 0.5713 | 0.047* | |
| C4 | 0.3615 (3) | 0.47918 (19) | 0.80700 (19) | 0.0327 (3) | |
| H4A | 0.2621 | 0.5652 | 0.9046 | 0.039* | |
| H4B | 0.2589 | 0.4866 | 0.7240 | 0.039* | |
| C5 | 0.4234 (3) | 0.26763 (19) | 0.89175 (19) | 0.0327 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0319 (2) | 0.02282 (19) | 0.0434 (2) | −0.00331 (13) | −0.00692 (15) | 0.01037 (13) |
| O2 | 0.0351 (6) | 0.0282 (5) | 0.0625 (7) | −0.0045 (4) | −0.0070 (5) | 0.0159 (5) |
| O1 | 0.0346 (5) | 0.0263 (5) | 0.0558 (7) | −0.0073 (4) | −0.0062 (5) | 0.0111 (5) |
| C1 | 0.0329 (6) | 0.0197 (6) | 0.0314 (6) | −0.0045 (5) | −0.0078 (5) | 0.0035 (5) |
| C2 | 0.0305 (7) | 0.0276 (7) | 0.0469 (8) | −0.0061 (5) | −0.0006 (6) | 0.0106 (6) |
| C3 | 0.0278 (6) | 0.0274 (7) | 0.0494 (8) | −0.0018 (5) | −0.0038 (6) | 0.0075 (6) |
| C4 | 0.0327 (7) | 0.0227 (6) | 0.0361 (7) | −0.0042 (5) | −0.0071 (5) | 0.0060 (5) |
| C5 | 0.0351 (7) | 0.0241 (6) | 0.0337 (7) | −0.0061 (5) | −0.0065 (5) | 0.0031 (5) |
| S1—C1 | 1.7679 (12) | C2—C3 | 1.3860 (19) |
| S1—C4 | 1.8010 (14) | C2—H2A | 0.9300 |
| O2—C5 | 1.2139 (18) | C3—C1i | 1.3843 (19) |
| O1—C5 | 1.3058 (17) | C3—H3A | 0.9300 |
| O1—H1 | 0.82 (2) | C4—C5 | 1.5015 (17) |
| C1—C3i | 1.3843 (19) | C4—H4A | 0.9700 |
| C1—C2 | 1.3866 (19) | C4—H4B | 0.9700 |
| C1—S1—C4 | 103.14 (6) | C2—C3—H3A | 119.4 |
| C5—O1—H1 | 108.3 (16) | C5—C4—S1 | 108.38 (9) |
| C3i—C1—C2 | 118.87 (12) | C5—C4—H4A | 110.0 |
| C3i—C1—S1 | 115.93 (10) | S1—C4—H4A | 110.0 |
| C2—C1—S1 | 125.20 (10) | C5—C4—H4B | 110.0 |
| C3—C2—C1 | 120.01 (13) | S1—C4—H4B | 110.0 |
| C3—C2—H2A | 120.0 | H4A—C4—H4B | 108.4 |
| C1—C2—H2A | 120.0 | O2—C5—O1 | 124.48 (12) |
| C1i—C3—C2 | 121.12 (13) | O2—C5—C4 | 122.57 (12) |
| C1i—C3—H3A | 119.4 | O1—C5—C4 | 112.95 (12) |
| C4—S1—C1—C3i | −173.10 (11) | C1—C2—C3—C1i | 0.2 (3) |
| C4—S1—C1—C2 | 7.47 (15) | C1—S1—C4—C5 | 178.43 (9) |
| C3i—C1—C2—C3 | −0.2 (3) | S1—C4—C5—O2 | 4.17 (19) |
| S1—C1—C2—C3 | 179.18 (12) | S1—C4—C5—O1 | −176.44 (10) |
| Symmetry codes: (i) −x+1, −y+2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2ii | 0.82 (2) | 1.82 (2) | 2.6440 (14) | 177 (2) |
| Symmetry codes: (ii) −x+1, −y, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.82 (2) | 1.82 (2) | 2.6440 (14) | 177 (2) |
| Symmetry codes: (i) −x+1, −y, −z+2. |
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Researches on the aromatic carboxylic acids mainly focused on the rigid acids (Hu et al., 2006). Compared with the rigid acids, the flexible aromatic carboxylate acids contain more coordination sites and may lead to the versatile and novel metal-organic complexes. We successfully designed and synthesized a new flexible aromatic multicarboxylate acid,1,4-benzenebis(thioacetic acid) (I), on the basis of the 1,4-benzenebisoxyacetate (Li et al., 2006) and phenylthioacetate (Sandhu et al., 1991).
The compound (I) possesses two flexible carboxyl groups (Fig. 1). The centroid of the benzene ring of the molecule is an inversion centre and the asymmetric unit contains an half-molecule. The bond lengths and angles are as expected. In the crystal structure, intermolecular O—H···O hydrogen bonds link the molecules into a one-dimensional chain (Fig. 2).