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The title compound, [Mn(C10H8O5S)(H2O)4]n, a one-dimensional manganese(II) complex comprising helical chains bridged by 4-(carboxylatomethylsulfanyl)phenoxyacetate ligands has been characterized by single-crystal X-ray diffraction analysis. Hydrogen-bonding inter­actions between adjacent chains extend the complex into a three-dimensional supra­molecular architecture.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010601184X/ty1014sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010601184X/ty1014Isup2.hkl
Contains datablock I

CCDC reference: 285221

Comment top

The crystal engineering and synthesis of discrete metallohelicates and infinite metal-containing helical coordination polymers have received much attention from chemists, because helicity is an essential feature of living systems and is important in advanced materials, such as optical devices, enantiomer separation, chiral synthesis, ligand exchange and selective catalysis (Chen & Suslick, 1993; Woods et al., 1996; Piguet et al., 1997; Qi et al., 2003). Most of the recent studies in this area have been involved with the construction of compounds from d10 transition metal ions and functional ligands (Psillakes et al., 1997; Tong et al., 1998; Nomiya et al., 2000). In this context, the fine-tuning of organic ligands and the careful selection of metal ions are especially crucial to the construction of desirable helical frameworks (Nishida et al., 2001; Gao et al., 2003; Barnett & Champness, 2003). We are interested in the solid-state coordination chemistry of p-(carboxylmethoxyl)phenylthioacetic acid (p-CMPTH2), which remains largely unexplored. Although this is a rather simple molecule, it has the potential for coordinative interaction and hydrogen bonding. Firstly, it has two carboxyl groups, one ether O atom and one ether S atom, which induce multiple coordination modes with transition metal ions. Secondly, it can act not only as a hydrogen-bond donor but also as hydrogen-bond acceptor, owing to the existence of deprotonated and/or protonated carboxyl groups. Therefore, it is regarded as an excellent candidate for the construction of different kinds of coordination polymers, including infinite one-dimensional chain compounds, two-dimensional layer compounds and three-dimensional netlike compounds (Gao, Huo et al., 2005; Gao, Su et al., 2005). Here, we report the title novel one-dimensional manganese(II) complex, (I), comprising helical chains bridged by p-(carboxylmethoxyl)phenylthioacetate (p-CMPT2−).

The present X-ray diffraction analysis shows that complex (I) possesses a one-dimensional single-helical structure. The fundamental unit of the crystal structure is illustrated in Fig. 1. Each MnII ion is six-coordinated in a distorted octahedral geometry. Its equatorial plane is defined by atoms O1, O1W, O3W and O4i [symmetry code: (i) −x + 1, y − 1/2, −z + 1], with an r.m.s. deviation of 0.075 (2) Å; the deviation of the MnII atom from this plane is 0.0116 (2) Å. The axial positions are occupied by atoms O2W and O4W, with an angle of 170.53 (6)°. It is interesting to note that each ligand, L, serves as a bridging ligand to link two MnII atoms, forming a single-strand helical coordination polymer. Both carboxylate anions in one L are mono-coordinated to the adjacent metal atom, with Mn—O distances of 2.1599 (15) and 2.1528 (16) Å (Fig. 2). In this way, each L acts as a bidentate group to link two metal atoms and yields a half-turn unit of the helical structure. The distance between neighbouring Mn atoms is 11.377 Å. Extension of the structure in one dimension along the b axis gives a one-dimensional helical Mn–L network (Fig. 2), resulting from the unique coordination feature of the L ligands. Each helical cycle contains three Mn atoms and two bridging L ligands.

The structure of (I) also contains intermolecular hydrogen bonds, which are formed between the free water molecules and uncoordinated carboxylate O atoms [O···O = 2.676 (2) and 2.744 (2) Å], resulting in a two-dimensional layer structure parallel to the bc plane. Adjacent two-dimensional layers form a three-dimensional framework linked by further intermolecular hydrogen bonds formed between the water molecules, coordinated carboxylate O atoms and water molecules of an adjacent layer [O···O = 2.972 (3) and 2.878 (2) Å] (Fig. 3).

In summary, employing the flexibility and unique coordination feature of L, we have successfully prepared a one-dimensional chain coordination polymer consisting of helical chains bridged by L. Knowledge of the chemistry of well defined helical coordination polymers is necessary for the understanding of the detection and amplification of chirality. There is increasing interest in dynamic helical coordination polymers (Yamada et al., 2004; Matsuda et al., 2004), the most important feature of which is high sensitivity to a chiral environment, and therefore such systems might provide the basis to construct a novel chirality-sensing probe. This work has demonstrated that extended structural motifs can be constructed through L ligands bridging neutral one-dimensional helical chains.

Experimental top

p-(Carboxylmethoxyl)phenylthioacetic acid was prepared following the method described for the synthesis of benzene-1,2-dioxyacetic acid by Mirci (1990). MnCl2·6H2O (0.099 g, 0.5 mmol) and p-(carboxylmethoxyl)phenylthioacetic acid (0.224 g, 1 mmol) were dissolved separately in water (25 ml) and the two solutions mixed slowly with stirring for about 15 min at room temperature. The pH value was adjusted to 6 with 0.1 M sodium hydroxide. Colourless crystals of (I) separated from the filtered solution after several days (yield ca 56%). Elementary analysis, calculated for C10H16O9SMn (367.23): C 32.70, H 4.39%; found: C 33.02, H 4.41%.

Refinement top

C-bound H atoms were placed in calculated positions, with C—H = 0.93 Å (aromatic) or 0.97 Å (aliphatic) and Uiso(H) = 1.2Ueq(C), and treated using the riding-model approximation. The H atoms of the water molecules were located in a difference Fourier map and refined with O—H distance restraints of 0.85 (1) Å and with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the title compound, showing the atom-numbering scheme. Non-water H atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1 − x, y − 1/2, 1 − z.] [Please check added symmetry code]
[Figure 2] Fig. 2. Ball-and-stick and space-filling plots of (I), showing the one-dimensional helical Mn–L network along the b axis. H atoms have been omitted. [H atoms are shown in the key - please revise]
[Figure 3] Fig. 3. A packing diagram for (I). Hydrogen bonds are depicted as dashed lines.
catena-Poly[[tetraaquamanganese(II)]-µ-4- (carboxylatomethylsulfanyl)phenoxyacetato] top
Crystal data top
[Mn(C10H8O5S)(H2O)4]F(000) = 378
Mr = 367.24Dx = 1.724 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6619 reflections
a = 5.0977 (10) Åθ = 3.4–27.5°
b = 11.444 (2) ŵ = 1.12 mm1
c = 12.183 (2) ÅT = 295 K
β = 95.58 (3)°Prism, colourless
V = 707.4 (2) Å30.37 × 0.25 × 0.16 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3164 independent reflections
Radiation source: fine-focus sealed tube2967 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.4°
ω scansh = 65
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1414
Tmin = 0.709, Tmax = 0.840l = 1515
6919 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054 w = 1/[σ2(Fo2) + (0.0264P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3164 reflectionsΔρmax = 0.29 e Å3
214 parametersΔρmin = 0.18 e Å3
13 restraintsAbsolute structure: Flack (1983), with 1457 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (11)
Crystal data top
[Mn(C10H8O5S)(H2O)4]V = 707.4 (2) Å3
Mr = 367.24Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.0977 (10) ŵ = 1.12 mm1
b = 11.444 (2) ÅT = 295 K
c = 12.183 (2) Å0.37 × 0.25 × 0.16 mm
β = 95.58 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3164 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2967 reflections with I > 2σ(I)
Tmin = 0.709, Tmax = 0.840Rint = 0.024
6919 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054Δρmax = 0.29 e Å3
S = 1.04Δρmin = 0.18 e Å3
3164 reflectionsAbsolute structure: Flack (1983), with 1457 Friedel pairs
214 parametersAbsolute structure parameter: 0.004 (11)
13 restraints
Special details top

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
Mn10.57346 (5)0.22290 (2)0.90542 (2)0.02444 (8)
S10.07105 (9)0.44281 (5)0.63645 (4)0.03256 (12)
O1W0.8489 (3)0.36610 (14)0.96036 (14)0.0344 (4)
H100.985 (3)0.348 (2)0.9282 (19)0.052*
H110.778 (4)0.4260 (16)0.9273 (19)0.052*
O2W0.8179 (3)0.19439 (13)0.76427 (13)0.0363 (4)
H120.959 (3)0.1549 (18)0.773 (2)0.054*
H130.848 (5)0.2597 (14)0.736 (2)0.054*
O3W0.8603 (3)0.11184 (13)1.00137 (13)0.0326 (3)
H140.850 (4)0.0485 (14)0.966 (2)0.049*
H151.008 (3)0.1433 (18)1.000 (2)0.049*
O4W0.3616 (2)0.22385 (16)1.05590 (10)0.0286 (3)
H160.361 (5)0.2882 (11)1.0907 (17)0.043*
H170.407 (5)0.1686 (13)1.1003 (16)0.043*
O10.3120 (3)0.35505 (13)0.83019 (14)0.0315 (3)
O20.5573 (2)0.51541 (13)0.83481 (12)0.0332 (3)
O30.6315 (3)0.31153 (13)0.29508 (12)0.0331 (3)
O40.6867 (3)0.58507 (14)0.15736 (13)0.0312 (3)
O50.3842 (3)0.44466 (14)0.12859 (12)0.0334 (3)
C10.3536 (3)0.45932 (18)0.80449 (16)0.0245 (4)
C20.1383 (4)0.52629 (18)0.73539 (16)0.0290 (4)
H2A0.22140.58750.69600.035*
H2B0.02730.56400.78520.035*
C30.1481 (4)0.40705 (18)0.53770 (16)0.0300 (4)
C40.1804 (4)0.29063 (18)0.50549 (19)0.0373 (5)
H40.09430.23130.53990.045*
C50.3374 (4)0.2630 (2)0.42371 (19)0.0381 (5)
H50.35220.18570.40150.046*
C60.4739 (4)0.35008 (18)0.37413 (16)0.0302 (4)
C70.4455 (4)0.46576 (18)0.40495 (16)0.0307 (4)
H70.53660.52460.37210.037*
C80.2800 (4)0.49277 (18)0.48513 (16)0.0317 (4)
H80.25720.57060.50400.038*
C90.7775 (4)0.40147 (19)0.24398 (18)0.0313 (4)
H9A0.90360.36490.20010.038*
H9B0.87540.44730.30110.038*
C100.6010 (4)0.48206 (18)0.17092 (16)0.0254 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.01891 (12)0.02570 (13)0.02851 (14)0.00052 (12)0.00124 (10)0.00161 (13)
S10.0263 (2)0.0406 (3)0.0303 (2)0.0005 (2)0.0003 (2)0.0039 (2)
O1W0.0235 (7)0.0335 (9)0.0454 (9)0.0016 (6)0.0004 (7)0.0016 (7)
O2W0.0345 (7)0.0369 (11)0.0383 (8)0.0017 (6)0.0085 (7)0.0026 (6)
O3W0.0253 (7)0.0342 (9)0.0382 (8)0.0007 (6)0.0020 (7)0.0061 (7)
O4W0.0284 (6)0.0266 (6)0.0305 (6)0.0026 (8)0.0019 (5)0.0002 (7)
O10.0252 (7)0.0283 (8)0.0398 (8)0.0016 (6)0.0023 (7)0.0076 (6)
O20.0254 (7)0.0284 (8)0.0451 (9)0.0024 (6)0.0004 (7)0.0006 (7)
O30.0377 (7)0.0303 (7)0.0322 (7)0.0061 (6)0.0076 (7)0.0019 (6)
O40.0267 (7)0.0277 (8)0.0391 (8)0.0021 (6)0.0027 (7)0.0032 (7)
O50.0300 (7)0.0314 (8)0.0372 (8)0.0007 (6)0.0054 (6)0.0009 (7)
C10.0237 (8)0.0282 (11)0.0226 (9)0.0003 (8)0.0074 (7)0.0030 (8)
C20.0312 (10)0.0283 (10)0.0277 (10)0.0020 (8)0.0037 (9)0.0016 (8)
C30.0263 (9)0.0326 (11)0.0302 (10)0.0008 (8)0.0021 (9)0.0039 (8)
C40.0401 (12)0.0272 (11)0.0451 (12)0.0065 (9)0.0063 (11)0.0076 (9)
C50.0425 (11)0.0231 (9)0.0482 (13)0.0006 (8)0.0011 (11)0.0010 (9)
C60.0290 (9)0.0310 (11)0.0293 (10)0.0039 (8)0.0045 (9)0.0031 (8)
C70.0356 (10)0.0286 (11)0.0279 (10)0.0042 (8)0.0028 (9)0.0033 (8)
C80.0380 (10)0.0252 (10)0.0306 (10)0.0006 (8)0.0024 (9)0.0002 (8)
C90.0267 (9)0.0332 (11)0.0343 (11)0.0036 (8)0.0053 (9)0.0035 (9)
C100.0252 (9)0.0265 (10)0.0253 (9)0.0037 (7)0.0063 (8)0.0023 (8)
Geometric parameters (Å, º) top
Mn1—O4i2.1528 (16)O4—C101.274 (3)
Mn1—O12.1599 (15)O4—Mn1ii2.1528 (15)
Mn1—O3W2.1881 (15)O5—C101.249 (2)
Mn1—O4W2.2164 (14)C1—C21.524 (3)
Mn1—O1W2.2185 (15)C2—H2A0.9700
Mn1—O2W2.2435 (17)C2—H2B0.9700
S1—C31.768 (2)C3—C81.381 (3)
S1—C21.804 (2)C3—C41.403 (3)
O1W—H100.85 (3)C4—C51.374 (3)
O1W—H110.86 (2)C4—H40.9300
O2W—H120.85 (2)C5—C61.387 (3)
O2W—H130.85 (2)C5—H50.9300
O3W—H140.85 (2)C6—C71.388 (3)
O3W—H150.84 (2)C7—C81.386 (3)
O4W—H160.85 (2)C7—H70.9300
O4W—H170.85 (2)C8—H80.9300
O1—C11.257 (3)C9—C101.516 (3)
O2—C11.246 (2)C9—H9A0.9700
O3—C61.385 (3)C9—H9B0.9700
O3—C91.446 (3)
O4i—Mn1—O191.66 (5)C1—C2—S1116.77 (14)
O4i—Mn1—O3W96.94 (6)C1—C2—H2A108.1
O1—Mn1—O3W170.43 (6)S1—C2—H2A108.1
O4i—Mn1—O4W87.97 (6)C1—C2—H2B108.1
O1—Mn1—O4W91.00 (6)S1—C2—H2B108.1
O3W—Mn1—O4W85.13 (6)H2A—C2—H2B107.3
O4i—Mn1—O1W176.68 (7)C8—C3—C4118.0 (2)
O1—Mn1—O1W87.54 (6)C8—C3—S1121.29 (16)
O3W—Mn1—O1W84.11 (6)C4—C3—S1120.60 (16)
O4W—Mn1—O1W95.27 (6)C5—C4—C3120.9 (2)
O4i—Mn1—O2W89.43 (6)C5—C4—H4119.6
O1—Mn1—O2W98.19 (6)C3—C4—H4119.6
O3W—Mn1—O2W86.15 (6)C4—C5—C6120.2 (2)
O4W—Mn1—O2W170.53 (6)C4—C5—H5119.9
O1W—Mn1—O2W87.49 (6)C6—C5—H5119.9
C3—S1—C2101.86 (9)O3—C6—C7125.09 (19)
Mn1—O1W—H10101.8 (19)O3—C6—C5115.06 (18)
Mn1—O1W—H11102.9 (18)C7—C6—C5119.8 (2)
H10—O1W—H11107.5 (14)C8—C7—C6119.35 (19)
Mn1—O2W—H12120.3 (18)C8—C7—H7120.3
Mn1—O2W—H13108.9 (19)C6—C7—H7120.3
H12—O2W—H13109.9 (15)C3—C8—C7121.69 (19)
Mn1—O3W—H14102.5 (18)C3—C8—H8119.2
Mn1—O3W—H15107.0 (18)C7—C8—H8119.2
H14—O3W—H15111.6 (16)O3—C9—C10112.64 (16)
Mn1—O4W—H16116.2 (17)O3—C9—H9A109.1
Mn1—O4W—H17113.6 (17)C10—C9—H9A109.1
H16—O4W—H17109.9 (14)O3—C9—H9B109.1
C1—O1—Mn1131.18 (13)C10—C9—H9B109.1
C6—O3—C9115.49 (16)H9A—C9—H9B107.8
C10—O4—Mn1ii121.13 (12)O5—C10—O4124.39 (18)
O2—C1—O1124.83 (18)O5—C10—C9119.01 (18)
O2—C1—C2116.08 (18)O4—C10—C9116.60 (17)
O1—C1—C2119.04 (17)
O4i—Mn1—O1—C1158.7 (2)C9—O3—C6—C71.0 (3)
O4W—Mn1—O1—C1113.28 (19)C9—O3—C6—C5179.18 (17)
O1W—Mn1—O1—C118.05 (19)C4—C5—C6—O3178.25 (17)
O2W—Mn1—O1—C169.06 (19)C4—C5—C6—C71.9 (3)
Mn1—O1—C1—O212.5 (3)O3—C6—C7—C8179.73 (17)
Mn1—O1—C1—C2170.33 (13)C5—C6—C7—C80.1 (3)
O2—C1—C2—S1150.04 (15)C4—C3—C8—C71.7 (3)
O1—C1—C2—S132.5 (2)S1—C3—C8—C7177.82 (14)
C3—S1—C2—C169.78 (16)C6—C7—C8—C31.9 (3)
C2—S1—C3—C856.96 (17)C6—O3—C9—C1068.7 (2)
C2—S1—C3—C4127.05 (17)Mn1ii—O4—C10—O516.5 (3)
C8—C3—C4—C50.3 (3)Mn1ii—O4—C10—C9163.30 (13)
S1—C3—C4—C5175.80 (15)O3—C9—C10—O526.1 (3)
C3—C4—C5—C62.1 (3)O3—C9—C10—O4153.70 (18)
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H10···O1iii0.85 (3)2.15 (3)2.972 (3)163 (2)
O1W—H11···O20.86 (2)1.83 (3)2.651 (2)161 (3)
O2W—H12···O4iv0.85 (2)2.08 (3)2.896 (2)162 (3)
O2W—H13···S1iii0.85 (2)2.47 (3)3.316 (2)175 (3)
O3W—H14···O5i0.85 (2)1.97 (3)2.709 (2)145 (2)
O3W—H15···O4Wiii0.84 (2)2.08 (3)2.878 (2)159 (2)
O4W—H16···O5v0.85 (2)1.85 (2)2.676 (2)164 (2)
O4W—H17···O2vi0.85 (2)1.93 (3)2.744 (2)162 (2)
Symmetry codes: (i) x+1, y1/2, z+1; (iii) x+1, y, z; (iv) x+2, y1/2, z+1; (v) x, y, z+1; (vi) x+1, y1/2, z+2.

Experimental details

Crystal data
Chemical formula[Mn(C10H8O5S)(H2O)4]
Mr367.24
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)5.0977 (10), 11.444 (2), 12.183 (2)
β (°) 95.58 (3)
V3)707.4 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.12
Crystal size (mm)0.37 × 0.25 × 0.16
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.709, 0.840
No. of measured, independent and
observed [I > 2σ(I)] reflections
6919, 3164, 2967
Rint0.024
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.054, 1.04
No. of reflections3164
No. of parameters214
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.18
Absolute structureFlack (1983), with 1457 Friedel pairs
Absolute structure parameter0.004 (11)

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXL97.

Selected geometric parameters (Å, º) top
Mn1—O4i2.1528 (16)Mn1—O4W2.2164 (14)
Mn1—O12.1599 (15)Mn1—O1W2.2185 (15)
Mn1—O3W2.1881 (15)Mn1—O2W2.2435 (17)
O4i—Mn1—O191.66 (5)O1—Mn1—O1W87.54 (6)
O4i—Mn1—O3W96.94 (6)O3W—Mn1—O1W84.11 (6)
O1—Mn1—O3W170.43 (6)O4W—Mn1—O1W95.27 (6)
O4i—Mn1—O4W87.97 (6)O4i—Mn1—O2W89.43 (6)
O1—Mn1—O4W91.00 (6)O1—Mn1—O2W98.19 (6)
O3W—Mn1—O4W85.13 (6)O3W—Mn1—O2W86.15 (6)
O4i—Mn1—O1W176.68 (7)O4W—Mn1—O2W170.53 (6)
Symmetry code: (i) x+1, y1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H10···O1ii0.85 (3)2.15 (3)2.972 (3)163 (2)
O1W—H11···O20.86 (2)1.83 (3)2.651 (2)161 (3)
O2W—H12···O4iii0.85 (2)2.08 (3)2.896 (2)162 (3)
O2W—H13···S1ii0.85 (2)2.47 (3)3.316 (2)175 (3)
O3W—H14···O5i0.85 (2)1.97 (3)2.709 (2)145 (2)
O3W—H15···O4Wii0.84 (2)2.08 (3)2.878 (2)159 (2)
O4W—H16···O5iv0.85 (2)1.85 (2)2.676 (2)164 (2)
O4W—H17···O2v0.85 (2)1.93 (3)2.744 (2)162 (2)
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y, z; (iii) x+2, y1/2, z+1; (iv) x, y, z+1; (v) x+1, y1/2, z+2.
 

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