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The title compound, C10H12O6S, has been obtained as dark-yellow chunk-shaped crystals, together with the expected thin white needles. The structures of the two phases are identical. Two independent mol­ecules compose the asymmetric unit: one mol­ecule is totally planar, whereas a methyl group of the second mol­ecule points out of the plane. Each mol­ecule participates in several intra- and intermolecular hydrogen bonds and short contacts. The overall structure can be regarded as parallel sheets of mol­ecules. Within a sheet, mol­ecules are connected to one another in an infinite network via numerous short intermolecular contacts. Sheets are connected via hydrogen bonds and short contacts, in particular involving the methyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104006754/sk1705sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104006754/sk1705IIsup2.hkl
Contains datablock II

CCDC reference: 241231

Comment top

Electrically conducting polymers are a widely and intensively researched class of materials in both industry and academia (Skotheim et al., 1998). One particular family of conducting polymers, poly(ethylenedioxythiophenes) (PEDOTs), have shown extraordinary promise in a variety of applications due to their low oxidation state, high conductivity, oxidation-state stability and thin-film transparency (Groenendaal et al., 2003). Several commercially available products use a PEDOT-based material (Groenendaal et al., 2000). Utilizing the electronic properties of PEDOT, which are superior to those of other conducting polymer systems, we set out to design and synthesize substituted PEDOT-based polymers.

According to previously reported procedures, PEDOTs can be readily derivatized at the ethylenedioxy bridge (Sankaran & Reynolds, 1997; Lima et al., 1998). During purification of the substituted EDOT precursor diethyl-3,4-dihydroxy-2,5-thiophenedicarboxylate, (II), which was prepared from the diethyl thiodiglycolate, (I), in two steps, unexpected dark-yellow chunk-like crystals formed alongside, to a lesser extent, the expected and previously reported white needles. The 1H NMR data for the two samples were the same and agreed with those previously reported (Sankaran & Reynolds, 1997). The stark contrast in crystal morphology and color, yet similar NMR properties, piqued our interest in determining the crystal structure of the unexpected product.

The asymmetric unit of the title compound contains two independent C10H12O6S molecules, named hereafter as A and B (Fig. 1), which lie almost in the same plane, close to (101). The planes of molecules A and B form an angle of ca 1.52 (4)°. Comparison of intramolecular bond lengths and angles does not show any discrepencies between units A and B. For each type of bond, distances are very homogeneous, except for one methyl group (see below). The only structural difference between these two units lies in the conformation of one of the terminal methyl groups. In molecule A, the methyl group that involves atom C7 points out of the plane of the molecule [C7 lies 1.128 (3) Å from the molecular plane], whereas molecule B is almost planar [the largest deviation is 0.164 (1) Å for atom O15].

The result of this non-planarity in molecule A is the existence of one short intermolecular contact, which can be regarded as a potential hydrogen-bond between A and B via atoms C7, H71 and O12(1 − x,1 − y,2 − z) (see Table 2). As a result of these short contacts, the C—H bond lengths around atom C7 [mean distance 1.02 (4) Å] are slightly larger than those of the other methyl groups [mean distance 0.96 (4) Å]. Atom C17 is also involved in a short intermolecular contact with atoms O5(2 − x,1 − y,1 − z) and H173 [C—H = 0.95 (2) Å, H—O = 2.57 (3) Å and C—O = 3.384 (3) Å], but this contact cannot be regarded as a potential hydrogen bond because the C17—H173—O5 angle [144 (2)°] is relatively bent. There is also another short contact, of 3.458 (2) Å, between atoms C17 and S1(1 + x,y,-1 + z). In contrast, the other methyl groups (C10 and C20) are not involved in any intermolecular contacts shorter than the sum of the van der Waals radii.

Contrary to what is observed in C7H8O4S (Hada et al., 1993), the hydroxy groups of C10H12O6S lie in the plane of the molecules. This planarity leads to a larger number of potential intra- and intermolecular hydrogen bonds between units than are present in C7H8O4S (see Table 2); in C10H12O6S, each hydroxy group is involved in one intra- and one intermolecular contact, whereas in C7H8O4S, only half of the OH groups generate such contacts. In addition, there also exist some short intermolecular contacts between non-H atoms. These numerous short intermolecular contacts involve only nearly coplanar molecules, which creates a relatively dense network of interactions, within and between C10H12O6S molecules. Therefore, the overall structure of the title compound can be regarded as sheets of C10H12O6S molecules (Fig. 2), which spread out parallel to the b axis almost in the (101) plane. However, the sheets are not independent of each other, since there exist intersheet contacts (Table 2). These contacts involve? not only the out-of-plane methyl group (C7) and one of the hydroxy groups (O12) but also other hetero atoms in the molecule (see Table 2). As a result of these intersheet contacts, the intersheet distance is relatively short (ca 3.55 Å). The observed hydrogen-bonding and other intermolecular interactions are likely to be the main contributors to the low solubility in lower-polarity solvents. The compound was recrystallized in small portions from large amounts of boiling ethyl acetate. The compound is observed to be more soluble in higher-polarity solvents, such as methanol and, to a lesser extent, ethanol.

The structure of the needle phase has also been determined, but its low quality (due to the very thin morphology and the poor diffracting power of the sample), prevents its presentation in this article. Nevertheless, the needle phase exhibits the same structural arrangement as the block phase, with the same features.

Experimental top

Compound (II) was synthesized from (I) and purified in 72% yield using previously reported procedures (Sankaran & Reynolds, 1997; Lima et al., 1998). During purification/recrystallization in ethyl acetate, white needles were obtained, along with a lesser amount of dark-yellow chunk-like crystals. The 1H NMR data were in agreement with those reported previously (Sankaran & Reynolds, 1997) for (II).

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1996); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: Sir97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of C10H12O6S, with 50% probability displacement ellipsoids (top: onto the plane of the molecules; bottom: side- view of the molecules). Hydrogen bonds are represented by dashed lines.
[Figure 2] Fig. 2. A projection of the structure of C10H12O6S along the b axis (S and O atoms are represented by shaded ellipsoids).
diethyl 3,4-dihydroxythiophene-2,5-dicarboxylate top
Crystal data top
C10H12O6SF(000) = 1088
Mr = 260.27Dx = 1.484 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7998 reflections
a = 8.7337 (9) Åθ = 2.4–25.9°
b = 19.8208 (14) ŵ = 0.29 mm1
c = 13.6271 (15) ÅT = 160 K
β = 99.059 (13)°Block, yellow
V = 2329.5 (4) Å30.48 × 0.23 × 0.1 mm
Z = 8
Data collection top
STOE imaging-plate
diffractometer
4535 independent reflections
Radiation source: fine-focus sealed tube3225 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ scanθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1010
Tmin = 0.928, Tmax = 0.971k = 2424
20063 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.072All H-atom parameters refined
S = 0.94 w = 1/[σ2(Fo2) + (0.0369P)2]
where P = (Fo2 + 2Fc2)/3
4535 reflections(Δ/σ)max = 0.001
403 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C10H12O6SV = 2329.5 (4) Å3
Mr = 260.27Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.7337 (9) ŵ = 0.29 mm1
b = 19.8208 (14) ÅT = 160 K
c = 13.6271 (15) Å0.48 × 0.23 × 0.1 mm
β = 99.059 (13)°
Data collection top
STOE imaging-plate
diffractometer
4535 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
3225 reflections with I > 2σ(I)
Tmin = 0.928, Tmax = 0.971Rint = 0.069
20063 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.072All H-atom parameters refined
S = 0.94Δρmax = 0.28 e Å3
4535 reflectionsΔρmin = 0.21 e Å3
403 parameters
Special details top

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS) equipped with an Oxford Cryosystems cooler device. The crystal-to-detector distance was 70 mm. 147 exposures (2.75 min per exposure) were obtained with 0 < ϕ < 220° and with the crystals rotated through 1.5° in ϕ. Crystal decay was monitored by measuring a maximum 200 reflections per image. Crystal orientation was checked with a maximum of 50 reflections per image.

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) top
xyzUiso*/Ueq
S110.85873 (6)0.48644 (2)0.38516 (3)0.02004 (11)
O110.7740 (2)0.66417 (7)0.48496 (11)0.0322 (4)
O120.64258 (17)0.56371 (7)0.58835 (10)0.0260 (3)
O130.95794 (18)0.67624 (7)0.33965 (11)0.0328 (4)
O141.01487 (16)0.58045 (6)0.26416 (9)0.0231 (3)
O150.63195 (17)0.42017 (6)0.59256 (9)0.0270 (3)
O160.72980 (17)0.36798 (6)0.46918 (10)0.0255 (3)
C110.8650 (2)0.57350 (9)0.39067 (13)0.0203 (4)
C120.7873 (2)0.59905 (9)0.46229 (14)0.0212 (4)
C130.7206 (2)0.54751 (9)0.51480 (13)0.0195 (4)
C140.7495 (2)0.48445 (9)0.48036 (13)0.0195 (4)
C150.9491 (2)0.61536 (9)0.33009 (14)0.0211 (4)
C161.1066 (2)0.61952 (10)0.20410 (15)0.0236 (4)
C171.1600 (3)0.57140 (11)0.13206 (16)0.0271 (4)
C180.6973 (2)0.42213 (9)0.52046 (13)0.0203 (4)
C190.6771 (3)0.30384 (10)0.50360 (18)0.0334 (5)
C200.7282 (4)0.25021 (11)0.4399 (2)0.0387 (6)
S10.28102 (6)0.46940 (2)0.95314 (3)0.02113 (12)
O10.31948 (19)0.28012 (6)0.88187 (11)0.0289 (3)
O20.46599 (18)0.36389 (7)0.76029 (10)0.0263 (3)
O30.12833 (19)0.29392 (7)1.02739 (11)0.0350 (4)
O40.10577 (17)0.39817 (7)1.08905 (10)0.0304 (3)
O50.51859 (16)0.49875 (6)0.73610 (10)0.0262 (3)
O60.41913 (16)0.57246 (6)0.83475 (9)0.0233 (3)
C10.2525 (2)0.38380 (9)0.96184 (13)0.0207 (4)
C20.3199 (2)0.34747 (9)0.89392 (14)0.0208 (4)
C30.3956 (2)0.38997 (9)0.83227 (13)0.0204 (4)
C40.3833 (2)0.45679 (9)0.85669 (13)0.0192 (4)
C50.1583 (2)0.35385 (9)1.02943 (14)0.0238 (4)
C60.0067 (3)0.37400 (13)1.15042 (18)0.0375 (5)
C70.0719 (4)0.34598 (15)1.24700 (19)0.0458 (6)
C80.4464 (2)0.51090 (9)0.80323 (13)0.0191 (4)
C90.4858 (3)0.62695 (9)0.78255 (16)0.0276 (5)
C100.4508 (3)0.69182 (11)0.83122 (19)0.0356 (5)
H110.824 (3)0.6842 (14)0.453 (2)0.051 (9)*
H120.619 (3)0.5292 (13)0.6178 (19)0.044 (7)*
H10.266 (3)0.2656 (13)0.9214 (19)0.047 (8)*
H20.496 (3)0.3940 (11)0.7330 (16)0.026 (6)*
H1611.191 (3)0.6391 (11)0.2472 (17)0.034 (6)*
H1721.071 (3)0.5519 (10)0.0887 (16)0.029 (6)*
H1621.042 (2)0.6550 (10)0.1718 (15)0.024 (5)*
H1020.493 (3)0.6915 (11)0.900 (2)0.040 (7)*
H1731.217 (3)0.5349 (12)0.1656 (17)0.034 (6)*
H910.600 (3)0.6196 (11)0.7886 (16)0.035 (6)*
H1711.225 (3)0.5938 (12)0.0927 (18)0.041 (7)*
H610.074 (3)0.3404 (13)1.114 (2)0.053 (8)*
H620.069 (3)0.4163 (13)1.1661 (19)0.058 (8)*
H1910.568 (3)0.3077 (12)0.4997 (19)0.051 (8)*
H1030.338 (3)0.6996 (12)0.8245 (18)0.044 (7)*
H2030.696 (3)0.2069 (13)0.4614 (18)0.047 (7)*
H920.435 (3)0.6269 (10)0.7154 (17)0.029 (6)*
H1010.499 (3)0.7267 (12)0.7987 (18)0.043 (7)*
H1920.729 (3)0.2981 (12)0.5712 (19)0.041 (7)*
H2010.682 (4)0.2569 (14)0.372 (2)0.068 (9)*
H2020.840 (4)0.2488 (15)0.443 (2)0.064 (9)*
H710.144 (3)0.3805 (14)1.283 (2)0.063 (8)*
H720.136 (4)0.3059 (15)1.233 (2)0.066 (9)*
H730.011 (4)0.3362 (16)1.293 (3)0.086 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0222 (3)0.0191 (2)0.0194 (2)0.00026 (18)0.00496 (19)0.00035 (17)
O110.0504 (10)0.0184 (7)0.0332 (8)0.0011 (7)0.0228 (8)0.0000 (6)
O120.0356 (9)0.0234 (7)0.0222 (7)0.0018 (6)0.0140 (6)0.0002 (6)
O130.0471 (10)0.0207 (7)0.0350 (8)0.0026 (6)0.0203 (7)0.0003 (6)
O140.0266 (8)0.0231 (6)0.0221 (7)0.0019 (5)0.0117 (6)0.0000 (5)
O150.0363 (9)0.0249 (7)0.0219 (7)0.0037 (6)0.0107 (6)0.0002 (5)
O160.0342 (8)0.0181 (6)0.0259 (7)0.0012 (6)0.0101 (6)0.0009 (5)
C110.0217 (10)0.0191 (9)0.0195 (9)0.0009 (7)0.0018 (8)0.0005 (7)
C120.0267 (11)0.0176 (8)0.0196 (9)0.0001 (8)0.0043 (8)0.0005 (7)
C130.0205 (10)0.0216 (9)0.0165 (9)0.0006 (7)0.0030 (8)0.0003 (7)
C140.0189 (10)0.0217 (9)0.0176 (9)0.0001 (7)0.0018 (7)0.0006 (7)
C150.0222 (10)0.0228 (9)0.0186 (9)0.0010 (8)0.0039 (8)0.0010 (7)
C160.0237 (11)0.0256 (10)0.0231 (10)0.0028 (9)0.0088 (9)0.0035 (8)
C170.0262 (12)0.0304 (11)0.0263 (11)0.0009 (10)0.0091 (10)0.0009 (9)
C180.0204 (10)0.0200 (9)0.0193 (9)0.0003 (7)0.0010 (8)0.0008 (7)
C190.0460 (16)0.0191 (10)0.0366 (14)0.0063 (9)0.0111 (11)0.0003 (9)
C200.0509 (17)0.0231 (11)0.0413 (15)0.0028 (10)0.0049 (12)0.0019 (9)
S10.0255 (3)0.0192 (2)0.0203 (2)0.00019 (19)0.00830 (19)0.00020 (18)
O10.0372 (9)0.0174 (7)0.0349 (8)0.0001 (6)0.0142 (7)0.0005 (6)
O20.0342 (9)0.0229 (7)0.0249 (8)0.0030 (6)0.0138 (7)0.0002 (6)
O30.0450 (10)0.0225 (7)0.0402 (9)0.0044 (6)0.0147 (7)0.0046 (6)
O40.0384 (9)0.0290 (7)0.0278 (8)0.0007 (6)0.0172 (7)0.0019 (6)
O50.0298 (8)0.0276 (7)0.0235 (7)0.0031 (6)0.0117 (6)0.0026 (6)
O60.0292 (8)0.0192 (6)0.0233 (7)0.0013 (5)0.0093 (6)0.0008 (5)
C10.0215 (10)0.0210 (9)0.0189 (9)0.0008 (7)0.0010 (8)0.0026 (7)
C20.0197 (10)0.0193 (9)0.0228 (10)0.0024 (7)0.0015 (8)0.0011 (7)
C30.0196 (10)0.0229 (9)0.0184 (9)0.0027 (8)0.0020 (8)0.0014 (7)
C40.0189 (10)0.0224 (9)0.0161 (9)0.0012 (7)0.0026 (8)0.0006 (7)
C50.0248 (11)0.0244 (10)0.0226 (10)0.0016 (8)0.0048 (8)0.0049 (8)
C60.0347 (14)0.0470 (14)0.0340 (12)0.0006 (11)0.0154 (11)0.0064 (10)
C70.0524 (17)0.0560 (16)0.0305 (13)0.0036 (14)0.0114 (12)0.0035 (11)
C80.0174 (10)0.0223 (9)0.0170 (9)0.0024 (7)0.0013 (8)0.0014 (7)
C90.0365 (13)0.0229 (10)0.0245 (11)0.0047 (9)0.0076 (10)0.0054 (8)
C100.0479 (17)0.0234 (11)0.0347 (13)0.0027 (10)0.0039 (12)0.0009 (9)
Geometric parameters (Å, º) top
S11—C141.7275 (19)S1—C41.7196 (19)
S11—C111.7277 (18)S1—C11.7217 (18)
O11—C121.337 (2)O1—C21.345 (2)
O11—H110.77 (3)O1—H10.82 (3)
O12—C131.337 (2)O2—C31.340 (2)
O12—H120.83 (3)O2—H20.77 (2)
O13—C151.215 (2)O3—C51.216 (2)
O14—C151.333 (2)O4—C51.326 (2)
O14—C161.455 (2)O4—C61.467 (3)
O15—C181.212 (2)O5—C81.214 (2)
O16—C181.335 (2)O6—C81.327 (2)
O16—C191.455 (2)O6—C91.464 (2)
C11—C121.371 (3)C1—C21.376 (3)
C11—C151.449 (3)C1—C51.455 (3)
C12—C131.423 (3)C2—C31.424 (3)
C13—C141.372 (3)C3—C41.374 (3)
C14—C181.453 (3)C4—C81.453 (3)
C16—C171.495 (3)C6—C71.492 (3)
C16—H1610.95 (2)C6—H610.97 (3)
C16—H1620.96 (2)C6—H621.04 (3)
C17—H1720.98 (2)C7—H711.01 (3)
C17—H1730.95 (2)C7—H721.01 (3)
C17—H1710.95 (3)C7—H731.05 (4)
C19—C201.485 (3)C9—C101.500 (3)
C19—H1910.95 (3)C9—H911.00 (2)
C19—H1920.97 (3)C9—H920.95 (2)
C20—H2030.96 (3)C10—H1020.95 (3)
C20—H2010.96 (3)C10—H1030.98 (3)
C20—H2020.97 (3)C10—H1010.96 (3)
C14—S11—C1190.45 (9)C4—S1—C190.43 (9)
C12—O11—H11107 (2)C2—O1—H1105.0 (18)
C13—O12—H12110.9 (18)C3—O2—H2106.5 (17)
C15—O14—C16115.88 (14)C5—O4—C6117.38 (16)
C18—O16—C19115.43 (16)C8—O6—C9114.56 (15)
C12—C11—C15123.13 (17)C2—C1—C5123.84 (17)
C12—C11—S11112.57 (14)C2—C1—S1112.80 (14)
C15—C11—S11124.24 (14)C5—C1—S1123.23 (14)
O11—C12—C11126.31 (18)O1—C2—C1127.47 (18)
O11—C12—C13121.31 (17)O1—C2—C3120.51 (17)
C11—C12—C13112.37 (16)C1—C2—C3112.02 (16)
O12—C13—C14128.17 (17)O2—C3—C4127.69 (17)
O12—C13—C12120.11 (16)O2—C3—C2120.84 (17)
C14—C13—C12111.73 (17)C4—C3—C2111.46 (16)
C13—C14—C18124.08 (17)C3—C4—C8122.67 (17)
C13—C14—S11112.88 (14)C3—C4—S1113.28 (14)
C18—C14—S11123.03 (13)C8—C4—S1124.02 (14)
O13—C15—O14124.11 (17)O3—C5—O4124.56 (18)
O13—C15—C11122.47 (18)O3—C5—C1121.68 (18)
O14—C15—C11113.42 (15)O4—C5—C1113.71 (16)
O14—C16—C17106.62 (15)O4—C6—C7111.6 (2)
O14—C16—H161108.2 (13)O4—C6—H61109.5 (16)
C17—C16—H161112.0 (14)C7—C6—H61110.9 (16)
O14—C16—H162108.2 (13)O4—C6—H62105.7 (15)
C17—C16—H162112.7 (12)C7—C6—H62107.5 (15)
H161—C16—H162108.9 (17)H61—C6—H62112 (2)
C16—C17—H172110.4 (13)C6—C7—H71110.1 (16)
C16—C17—H173111.2 (13)C6—C7—H72108.2 (17)
H172—C17—H173107.1 (18)H71—C7—H72108 (2)
C16—C17—H171110.4 (14)C6—C7—H73109.3 (19)
H172—C17—H171109.4 (19)H71—C7—H73106 (2)
H173—C17—H171108 (2)H72—C7—H73115 (2)
O15—C18—O16124.37 (17)O5—C8—O6124.53 (16)
O15—C18—C14123.22 (16)O5—C8—C4120.95 (16)
O16—C18—C14112.41 (16)O6—C8—C4114.52 (16)
O16—C19—C20107.32 (19)O6—C9—C10107.05 (18)
O16—C19—H191106.1 (15)O6—C9—H91108.8 (13)
C20—C19—H191114.7 (16)C10—C9—H91111.0 (13)
O16—C19—H192106.7 (14)O6—C9—H92107.9 (13)
C20—C19—H192109.6 (14)C10—C9—H92109.3 (13)
H191—C19—H192112 (2)H91—C9—H92112.6 (19)
C19—C20—H203109.3 (15)C9—C10—H102110.9 (14)
C19—C20—H201110.3 (18)C9—C10—H103111.3 (14)
H203—C20—H201109 (2)H102—C10—H103108 (2)
C19—C20—H202113.1 (18)C9—C10—H101106.3 (15)
H203—C20—H202108 (2)H102—C10—H101109 (2)
H201—C20—H202108 (2)H103—C10—H101111 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.82 (3)2.10 (3)2.799 (2)144 (2)
O1—H1···O11i0.82 (3)2.44 (3)3.116 (2)141 (2)
O2—H2···O50.77 (2)2.09 (2)2.7409 (19)143 (2)
O2—H2···O150.77 (2)2.46 (2)3.101 (2)141 (2)
O11—H11···O130.77 (3)2.09 (3)2.750 (2)144 (3)
O11—H11···O3ii0.77 (3)2.22 (3)2.723 (2)123 (2)
O12—H12···O50.84 (3)2.04 (3)2.752 (2)142 (2)
O12—H12···O150.84 (3)2.19 (3)2.8475 (19)135 (2)
C7—H71···O12iii1.00 (3)2.60 (3)3.563 (3)162 (2)
C17—H173···O5iv0.95 (2)2.57 (3)3.384 (3)144 (2)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1/2, z+3/2; (iii) x+1, y+1, z+2; (iv) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC10H12O6S
Mr260.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)160
a, b, c (Å)8.7337 (9), 19.8208 (14), 13.6271 (15)
β (°) 99.059 (13)
V3)2329.5 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.29
Crystal size (mm)0.48 × 0.23 × 0.1
Data collection
DiffractometerSTOE imaging-plate
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.928, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
20063, 4535, 3225
Rint0.069
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.072, 0.94
No. of reflections4535
No. of parameters403
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.28, 0.21

Computer programs: IPDS Software (Stoe & Cie, 1996), IPDS Software, Sir97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
S11—C141.7275 (19)S1—C41.7196 (19)
S11—C111.7277 (18)S1—C11.7217 (18)
O11—C121.337 (2)O1—C21.345 (2)
O12—C131.337 (2)O2—C31.340 (2)
O13—C151.215 (2)O3—C51.216 (2)
O14—C151.333 (2)O4—C51.326 (2)
O14—C161.455 (2)O4—C61.467 (3)
O15—C181.212 (2)O5—C81.214 (2)
O16—C181.335 (2)O6—C81.327 (2)
O16—C191.455 (2)O6—C91.464 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.82 (3)2.10 (3)2.799 (2)144 (2)
O1—H1···O11i0.82 (3)2.44 (3)3.116 (2)141 (2)
O2—H2···O50.77 (2)2.09 (2)2.7409 (19)143 (2)
O2—H2···O150.77 (2)2.46 (2)3.101 (2)141 (2)
O11—H11···O130.77 (3)2.09 (3)2.750 (2)144 (3)
O11—H11···O3ii0.77 (3)2.22 (3)2.723 (2)123 (2)
O12—H12···O50.84 (3)2.04 (3)2.752 (2)142 (2)
O12—H12···O150.84 (3)2.19 (3)2.8475 (19)135 (2)
C7—H71···O12iii1.00 (3)2.60 (3)3.563 (3)162 (2)
C17—H173···O5iv0.95 (2)2.57 (3)3.384 (3)144 (2)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1/2, z+3/2; (iii) x+1, y+1, z+2; (iv) x+2, y+1, z+1.
 

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