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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m125–m126.
Published online 2010 January 9. doi:  10.1107/S1600536809055512
PMCID: PMC2979835

(4-Amino-3-methyl­benzene­sulfonato)tri-μ-aqua-penta­aqua­disodium 4-amino-3-methyl­benzene­sulfonate

Abstract

In the title compound, [Na2(C7H8NO3S)(H2O)8](C7H8NO3S), one Na+ ion is bonded to six water mol­ecules in a distorted octa­hedral arrangement while the other is bonded to five water mol­ecules and one O atom of a 4-amino-3-methyl­benzene­sulfonate anion, also yielding a distorted NaO6 octa­hedron. Three of the water molecules bridge the metal ions and an intra­molecular O—H(...)O hydrogen bond helps to establish the conformation. In the crystal, the component species inter­act by way of O—H(...)O, O—H(...)N and N—H(...)O hydrogen bonds.

Related literature

For background to coordination networks, see: Tai et al. (2007 [triangle]); Wang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m125-scheme1.jpg

Experimental

Crystal data

  • [Na2(C7H8NO3S)(H2O)8](C7H8NO3S)
  • M r = 562.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m125-efi1.jpg
  • a = 6.2346 (17) Å
  • b = 27.793 (8) Å
  • c = 7.285 (2) Å
  • β = 91.296 (5)°
  • V = 1261.9 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 298 K
  • 0.24 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.929, T max = 0.946
  • 6522 measured reflections
  • 4067 independent reflections
  • 3823 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.097
  • S = 1.05
  • 4067 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.33 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1779 Friedel pairs
  • Flack parameter: 0.03 (7)

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055512/hb5297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055512/hb5297Isup2.hkl

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

Acknowledgments

This project was supported by the National Natural Science Foundation of China (20671073), the Natural Science Foundation of Shandong (Y2007B60) and the Science Foundation of Weifang University.

supplementary crystallographic information

Comment

During the past two decades, the design and synthesis of organic-inorganic hybrid materials have attracted intense attentions owing to their potential practical applications [Wang, et al., 2008; Tai, et al., 2007]. Benzenesulfonic acids can potentially be monodentate, bidentate ligands, they may also be intermolecularly bridging or intramolecularly chelating ligands. As part of our ongoing study in this field, In this paper, we report on the synthesis and crystal structure of the title compound, (I), (Scheme I).

In the crystal of (I), Na1 atom is six coordinate to five water molecules and one ligand, and Na2 atom is six coordinate to water molecules. The bond distances of Na—O are in the range of 2.341 (3)–2.670 (3). Otherwise, the geometrical parameters for (I) are normal. In the crystal packing, the molecules form a thrre-dimensional network by hydrogen bonds.

Experimental

A solution of 1.0 mmol NaOH in 1 ml water was added to a solution of 1.0 mmol 4-amino-3-methyl-benzenesulfonic acid in 5 ml ethanol at room temperature. The mixture was refluxed for 4 h with stirring, then the resulting precipitate was filtered, washed, and dried in vacuo over P4O10 for 48 h. Colourless blocks of (I) were obtained by slowly evaporating from methanol at room temperature.

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids.

Crystal data

[Na2(C7H8NO3S)(H2O)8](C7H8NO3S)F(000) = 592
Mr = 562.52Dx = 1.480 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3297 reflections
a = 6.2346 (17) Åθ = 2.9–26.0°
b = 27.793 (8) ŵ = 0.31 mm1
c = 7.285 (2) ÅT = 298 K
β = 91.296 (5)°Block, colourless
V = 1261.9 (6) Å30.24 × 0.20 × 0.18 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer4067 independent reflections
Radiation source: fine-focus sealed tube3823 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −6→7
Tmin = 0.929, Tmax = 0.946k = −32→33
6522 measured reflectionsl = −8→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.097w = 1/[σ2(Fo2) + (0.0555P)2 + 0.0081P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4067 reflectionsΔρmax = 0.34 e Å3
308 parametersΔρmin = −0.32 e Å3
0 restraintsAbsolute structure: Flack (1983), 1779 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (7)

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
Na10.0286 (2)0.64325 (5)0.33149 (17)0.0375 (3)
Na2−0.2402 (2)0.58785 (5)−0.01371 (18)0.0375 (3)
S10.27757 (12)0.73351 (2)0.04923 (10)0.02893 (18)
S20.40036 (12)0.48468 (3)0.47552 (10)0.02884 (18)
O10.1361 (4)0.71695 (8)0.1890 (3)0.0498 (7)
O20.2497 (4)0.70581 (8)−0.1205 (3)0.0405 (6)
O30.5005 (4)0.73391 (9)0.1084 (4)0.0538 (7)
O40.3033 (4)0.49845 (8)0.2983 (3)0.0407 (6)
O50.6316 (3)0.48784 (9)0.4768 (3)0.0446 (6)
O60.3058 (4)0.51229 (9)0.6233 (3)0.0433 (6)
O7−0.0541 (4)0.69570 (8)0.5914 (3)0.0420 (6)
H15−0.07540.72450.55630.063*
H160.05340.69720.66510.063*
O80.3432 (4)0.61320 (9)0.4858 (4)0.0496 (6)
H170.32310.62990.58170.074*
H180.32690.58370.51350.074*
O9−0.3362 (4)0.64448 (9)0.2270 (3)0.0407 (5)
H19−0.35940.67410.20600.061*
H20−0.43560.63550.29720.061*
O100.1122 (4)0.61615 (8)0.0188 (3)0.0418 (6)
H210.16420.6418−0.02570.063*
H220.19000.5937−0.02260.063*
O11−0.0947 (4)0.55211 (10)0.2810 (4)0.0582 (7)
H230.02490.53740.28120.087*
H24−0.18520.53270.32530.087*
O12−0.3884 (4)0.64884 (9)−0.2325 (3)0.0454 (6)
H25−0.29190.6634−0.29150.068*
H26−0.46640.6701−0.18290.068*
O13−0.1241 (5)0.52949 (13)−0.2223 (5)0.0774 (10)
H270.00020.5263−0.26630.116*
H28−0.20060.5392−0.31300.116*
O14−0.5711 (4)0.54510 (9)−0.0209 (3)0.0397 (5)
H30−0.60700.52810.07040.060*
H29−0.59580.5274−0.11420.060*
N10.0297 (6)0.93420 (11)−0.1088 (5)0.0517 (8)
H1A−0.09570.9406−0.15390.062*
H1B0.11880.9571−0.08540.062*
N20.1911 (5)0.28066 (10)0.6182 (4)0.0353 (6)
H2A0.07010.27310.66480.042*
H2B0.28320.25860.59500.042*
C10.2063 (5)0.79329 (10)−0.0007 (4)0.0281 (7)
C20.3493 (5)0.83016 (11)0.0335 (4)0.0270 (6)
H20.48570.82300.08020.032*
C30.2944 (5)0.87740 (11)−0.0001 (4)0.0294 (7)
C40.0878 (5)0.88746 (11)−0.0741 (4)0.0312 (7)
C5−0.0519 (5)0.84973 (12)−0.1103 (4)0.0336 (7)
H5−0.18660.8564−0.16150.040*
C60.0025 (5)0.80289 (11)−0.0727 (4)0.0309 (7)
H6−0.09480.7781−0.09500.037*
C70.4487 (6)0.91779 (12)0.0394 (5)0.0387 (8)
H7A0.58310.90480.08320.058*
H7B0.39080.93860.13120.058*
H7C0.47090.9358−0.07100.058*
C80.3372 (5)0.42400 (10)0.5119 (4)0.0283 (7)
C90.4831 (5)0.38849 (11)0.4721 (4)0.0254 (6)
H90.61470.39690.42400.031*
C100.4370 (5)0.34040 (11)0.5026 (4)0.0277 (6)
C110.2378 (5)0.32860 (11)0.5801 (4)0.0277 (6)
C120.0921 (5)0.36457 (12)0.6162 (4)0.0314 (7)
H12−0.03970.35650.66480.038*
C130.1375 (5)0.41236 (12)0.5819 (4)0.0314 (6)
H130.03710.43620.60490.038*
C140.5927 (6)0.30165 (12)0.4548 (5)0.0375 (7)
H14A0.70870.31530.38780.056*
H14B0.52110.27780.38050.056*
H14C0.64810.28700.56530.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Na10.0358 (7)0.0437 (7)0.0328 (7)0.0021 (6)−0.0066 (5)−0.0007 (6)
Na20.0350 (7)0.0406 (7)0.0366 (7)−0.0023 (6)−0.0043 (5)−0.0048 (6)
S10.0361 (4)0.0239 (3)0.0265 (4)0.0027 (3)−0.0054 (3)−0.0012 (3)
S20.0297 (4)0.0278 (4)0.0287 (4)−0.0027 (3)−0.0055 (3)0.0001 (3)
O10.0738 (18)0.0348 (13)0.0415 (14)0.0064 (12)0.0198 (13)0.0056 (11)
O20.0600 (15)0.0307 (12)0.0305 (12)0.0035 (11)−0.0063 (11)−0.0075 (10)
O30.0416 (14)0.0349 (12)0.0834 (19)0.0065 (11)−0.0289 (13)0.0003 (14)
O40.0497 (14)0.0397 (13)0.0322 (12)0.0006 (10)−0.0117 (10)0.0122 (10)
O50.0300 (12)0.0409 (13)0.0627 (16)−0.0061 (11)−0.0063 (10)0.0021 (13)
O60.0531 (14)0.0388 (13)0.0379 (13)−0.0005 (11)−0.0008 (11)−0.0086 (11)
O70.0507 (14)0.0400 (13)0.0349 (13)0.0013 (11)−0.0080 (11)0.0030 (11)
O80.0577 (16)0.0386 (13)0.0517 (16)−0.0001 (12)−0.0126 (12)0.0028 (12)
O90.0391 (12)0.0406 (13)0.0421 (13)0.0112 (10)−0.0043 (10)0.0037 (11)
O100.0422 (13)0.0299 (11)0.0534 (16)−0.0051 (10)0.0052 (11)−0.0034 (11)
O110.0482 (15)0.0604 (17)0.0660 (18)0.0090 (13)0.0051 (13)0.0274 (15)
O120.0454 (14)0.0483 (14)0.0427 (13)0.0031 (12)0.0030 (11)−0.0014 (11)
O130.0479 (16)0.104 (3)0.080 (2)0.0001 (17)0.0021 (15)−0.050 (2)
O140.0467 (14)0.0394 (12)0.0329 (13)−0.0018 (11)0.0004 (10)0.0006 (10)
N10.055 (2)0.0352 (16)0.064 (2)0.0056 (14)−0.0221 (16)0.0098 (15)
N20.0368 (15)0.0323 (14)0.0366 (15)−0.0062 (12)−0.0018 (12)0.0027 (12)
C10.0340 (16)0.0256 (16)0.0246 (14)0.0029 (12)−0.0028 (13)0.0007 (12)
C20.0257 (15)0.0290 (15)0.0259 (15)0.0005 (12)−0.0064 (12)0.0037 (12)
C30.0305 (16)0.0353 (17)0.0222 (15)−0.0003 (13)−0.0036 (12)0.0028 (12)
C40.0368 (17)0.0301 (15)0.0264 (16)0.0069 (13)−0.0052 (13)0.0030 (13)
C50.0268 (16)0.0410 (18)0.0325 (17)0.0060 (13)−0.0105 (13)0.0001 (14)
C60.0301 (16)0.0319 (15)0.0302 (16)−0.0031 (13)−0.0070 (13)−0.0043 (13)
C70.0456 (19)0.0301 (17)0.0401 (19)−0.0033 (15)−0.0080 (15)0.0004 (15)
C80.0314 (16)0.0313 (16)0.0220 (14)−0.0033 (12)−0.0052 (12)0.0027 (12)
C90.0252 (14)0.0327 (15)0.0183 (14)−0.0018 (12)−0.0020 (11)0.0027 (12)
C100.0310 (16)0.0316 (16)0.0202 (15)0.0016 (13)−0.0051 (12)0.0009 (12)
C110.0297 (15)0.0308 (15)0.0223 (14)−0.0063 (13)−0.0085 (12)0.0009 (12)
C120.0259 (15)0.0407 (17)0.0276 (16)−0.0063 (13)0.0002 (12)−0.0002 (14)
C130.0297 (15)0.0329 (15)0.0314 (16)−0.0007 (14)0.0003 (12)−0.0032 (14)
C140.0409 (18)0.0352 (17)0.0364 (18)0.0033 (15)0.0027 (14)0.0041 (14)

Geometric parameters (Å, °)

Na1—O92.382 (3)O14—H300.8500
Na1—O82.390 (3)O14—H290.8500
Na1—O12.399 (3)N1—C41.370 (4)
Na1—O72.453 (3)N1—H1A0.8600
Na1—O102.466 (3)N1—H1B0.8600
Na1—O112.670 (3)N2—C111.393 (4)
Na1—Na23.3634 (18)N2—H2A0.8600
Na2—O102.341 (3)N2—H2B0.8600
Na2—O132.348 (3)C1—C21.377 (4)
Na2—O142.380 (3)C1—C61.390 (4)
Na2—O92.441 (3)C2—C31.377 (4)
Na2—O122.490 (3)C2—H20.9300
Na2—O112.516 (3)C3—C41.413 (4)
S1—O11.438 (3)C3—C71.502 (5)
S1—O31.446 (2)C4—C51.384 (5)
S1—O21.464 (2)C5—C61.371 (5)
S1—C11.756 (3)C5—H50.9300
S2—O51.444 (2)C6—H60.9300
S2—O61.457 (2)C7—H7A0.9600
S2—O41.464 (2)C7—H7B0.9600
S2—C81.753 (3)C7—H7C0.9600
O7—H150.8500C8—C91.377 (4)
O7—H160.8500C8—C131.394 (4)
O8—H170.8499C9—C101.386 (4)
O8—H180.8499C9—H90.9300
O9—H190.8500C10—C111.414 (4)
O9—H200.8500C10—C141.496 (5)
O10—H210.8500C11—C121.380 (5)
O10—H220.8499C12—C131.382 (5)
O11—H230.8500C12—H120.9300
O11—H240.8500C13—H130.9300
O12—H250.8499C14—H14A0.9600
O12—H260.8499C14—H14B0.9600
O13—H270.8500C14—H14C0.9600
O13—H280.8500
O9—Na1—O8157.37 (11)Na1—O11—H24137.9
O9—Na1—O197.10 (10)H23—O11—H24106.5
O8—Na1—O1105.53 (10)Na2—O12—H25113.0
O9—Na1—O791.27 (9)Na2—O12—H26114.1
O8—Na1—O791.68 (10)H25—O12—H26107.6
O1—Na1—O783.80 (9)Na2—O13—H27127.7
O9—Na1—O1085.95 (9)Na2—O13—H2896.2
O8—Na1—O1098.02 (10)H27—O13—H28103.9
O1—Na1—O1078.13 (9)Na2—O14—H30120.3
O7—Na1—O10161.21 (10)Na2—O14—H29116.6
O9—Na1—O1172.53 (9)H30—O14—H29104.9
O8—Na1—O1187.93 (10)C4—N1—H1A120.0
O1—Na1—O11146.41 (10)C4—N1—H1B120.0
O7—Na1—O11127.23 (10)H1A—N1—H1B120.0
O10—Na1—O1169.47 (9)C11—N2—H2A120.0
O10—Na2—O1389.72 (10)C11—N2—H2B120.0
O10—Na2—O14168.83 (10)H2A—N2—H2B120.0
O13—Na2—O1485.43 (10)C2—C1—C6120.5 (3)
O10—Na2—O987.45 (9)C2—C1—S1120.5 (2)
O13—Na2—O9174.00 (13)C6—C1—S1119.0 (2)
O14—Na2—O996.40 (9)C3—C2—C1121.3 (3)
O10—Na2—O1299.78 (9)C3—C2—H2119.3
O13—Na2—O1299.86 (12)C1—C2—H2119.3
O14—Na2—O1290.97 (9)C2—C3—C4118.5 (3)
O9—Na2—O1285.84 (9)C2—C3—C7121.5 (3)
O10—Na2—O1174.15 (10)C4—C3—C7120.0 (3)
O13—Na2—O1199.73 (13)N1—C4—C5121.4 (3)
O14—Na2—O1196.74 (10)N1—C4—C3119.5 (3)
O9—Na2—O1174.40 (9)C5—C4—C3119.1 (3)
O12—Na2—O11159.44 (11)C6—C5—C4122.0 (3)
O1—S1—O3113.08 (18)C6—C5—H5119.0
O1—S1—O2111.53 (15)C4—C5—H5119.0
O3—S1—O2110.55 (16)C5—C6—C1118.5 (3)
O1—S1—C1107.05 (15)C5—C6—H6120.7
O3—S1—C1106.96 (15)C1—C6—H6120.7
O2—S1—C1107.35 (14)C3—C7—H7A109.5
O5—S2—O6112.54 (15)C3—C7—H7B109.5
O5—S2—O4112.49 (15)H7A—C7—H7B109.5
O6—S2—O4110.33 (15)C3—C7—H7C109.5
O5—S2—C8106.57 (15)H7A—C7—H7C109.5
O6—S2—C8107.40 (15)H7B—C7—H7C109.5
O4—S2—C8107.16 (14)C9—C8—C13120.7 (3)
S1—O1—Na1139.61 (15)C9—C8—S2120.4 (2)
Na1—O7—H15111.2C13—C8—S2119.0 (2)
Na1—O7—H16109.9C8—C9—C10121.1 (3)
H15—O7—H16105.1C8—C9—H9119.4
Na1—O8—H1793.5C10—C9—H9119.4
Na1—O8—H18110.3C9—C10—C11118.3 (3)
H17—O8—H18108.1C9—C10—C14121.3 (3)
Na1—O9—Na288.42 (8)C11—C10—C14120.4 (3)
Na1—O9—H19103.2C12—C11—N2120.9 (3)
Na2—O9—H19122.6C12—C11—C10119.7 (3)
Na1—O9—H20120.5N2—C11—C10119.4 (3)
Na2—O9—H20115.9C11—C12—C13121.6 (3)
H19—O9—H20105.6C11—C12—H12119.2
Na2—O10—Na188.77 (9)C13—C12—H12119.2
Na2—O10—H21127.5C12—C13—C8118.5 (3)
Na1—O10—H21100.8C12—C13—H13120.7
Na2—O10—H22105.1C8—C13—H13120.7
Na1—O10—H22133.3C10—C14—H14A109.5
H21—O10—H22104.7C10—C14—H14B109.5
Na2—O11—Na180.80 (8)H14A—C14—H14B109.5
Na2—O11—H23119.3C10—C14—H14C109.5
Na1—O11—H23101.9H14A—C14—H14C109.5
Na2—O11—H24110.2H14B—C14—H14C109.5
O9—Na1—Na2—O10147.11 (13)O12—Na2—O10—Na1107.97 (9)
O8—Na1—Na2—O10−60.55 (13)O11—Na2—O10—Na1−51.87 (9)
O1—Na1—Na2—O1058.64 (11)O9—Na1—O10—Na2−23.26 (9)
O7—Na1—Na2—O10152.54 (15)O8—Na1—O10—Na2134.33 (10)
O11—Na1—Na2—O10−105.07 (12)O1—Na1—O10—Na2−121.39 (10)
O9—Na1—Na2—O13−175.12 (17)O7—Na1—O10—Na2−105.3 (3)
O8—Na1—Na2—O13−22.78 (18)O11—Na1—O10—Na249.60 (9)
O1—Na1—Na2—O1396.41 (16)O10—Na2—O11—Na147.38 (8)
O7—Na1—Na2—O13−169.69 (17)O13—Na2—O11—Na1134.30 (10)
O10—Na1—Na2—O1337.77 (16)O14—Na2—O11—Na1−139.21 (9)
O11—Na1—Na2—O13−67.30 (17)O9—Na2—O11—Na1−44.41 (8)
O9—Na1—Na2—O14−47.85 (12)O12—Na2—O11—Na1−27.9 (3)
O8—Na1—Na2—O14104.49 (14)O9—Na1—O11—Na246.39 (8)
O1—Na1—Na2—O14−136.33 (12)O8—Na1—O11—Na2−145.20 (10)
O7—Na1—Na2—O14−42.43 (17)O1—Na1—O11—Na2−29.7 (2)
O10—Na1—Na2—O14165.03 (14)O7—Na1—O11—Na2124.26 (11)
O11—Na1—Na2—O1459.97 (13)O10—Na1—O11—Na2−45.84 (8)
O8—Na1—Na2—O9152.34 (13)O1—S1—C1—C2116.4 (3)
O1—Na1—Na2—O9−88.48 (11)O3—S1—C1—C2−5.1 (3)
O7—Na1—Na2—O95.42 (14)O2—S1—C1—C2−123.7 (3)
O10—Na1—Na2—O9−147.11 (13)O1—S1—C1—C6−62.7 (3)
O11—Na1—Na2—O9107.82 (12)O3—S1—C1—C6175.8 (3)
O9—Na1—Na2—O1262.13 (11)O2—S1—C1—C657.2 (3)
O8—Na1—Na2—O12−145.53 (11)C6—C1—C2—C30.9 (5)
O1—Na1—Na2—O12−26.35 (10)S1—C1—C2—C3−178.2 (2)
O7—Na1—Na2—O1267.56 (14)C1—C2—C3—C4−1.1 (5)
O10—Na1—Na2—O12−84.98 (11)C1—C2—C3—C7179.2 (3)
O11—Na1—Na2—O12169.95 (11)C2—C3—C4—N1−180.0 (3)
O9—Na1—Na2—O11−107.82 (12)C7—C3—C4—N1−0.2 (5)
O8—Na1—Na2—O1144.52 (13)C2—C3—C4—C50.0 (5)
O1—Na1—Na2—O11163.70 (12)C7—C3—C4—C5179.7 (3)
O7—Na1—Na2—O11−102.39 (15)N1—C4—C5—C6−178.6 (3)
O10—Na1—Na2—O11105.07 (12)C3—C4—C5—C61.4 (5)
O3—S1—O1—Na1−75.9 (3)C4—C5—C6—C1−1.7 (5)
O2—S1—O1—Na149.4 (3)C2—C1—C6—C50.5 (5)
C1—S1—O1—Na1166.6 (2)S1—C1—C6—C5179.6 (2)
O9—Na1—O1—S1−115.0 (3)O5—S2—C8—C9−22.7 (3)
O8—Na1—O1—S164.5 (3)O6—S2—C8—C9−143.5 (3)
O7—Na1—O1—S1154.5 (3)O4—S2—C8—C998.0 (3)
O10—Na1—O1—S1−30.6 (3)O5—S2—C8—C13157.2 (2)
O11—Na1—O1—S1−46.0 (4)O6—S2—C8—C1336.4 (3)
Na2—Na1—O1—S1−68.0 (3)O4—S2—C8—C13−82.1 (3)
O8—Na1—O9—Na2−78.9 (3)C13—C8—C9—C10−0.9 (5)
O1—Na1—O9—Na299.74 (9)S2—C8—C9—C10179.0 (2)
O7—Na1—O9—Na2−176.35 (9)C8—C9—C10—C11−1.5 (5)
O10—Na1—O9—Na222.25 (8)C8—C9—C10—C14178.3 (3)
O11—Na1—O9—Na2−47.48 (9)C9—C10—C11—C122.6 (4)
O10—Na2—O9—Na1−23.48 (9)C14—C10—C11—C12−177.2 (3)
O13—Na2—O9—Na138.5 (12)C9—C10—C11—N2−177.7 (3)
O14—Na2—O9—Na1146.00 (9)C14—C10—C11—N22.5 (4)
O12—Na2—O9—Na1−123.48 (9)N2—C11—C12—C13179.0 (3)
O11—Na2—O9—Na150.77 (9)C10—C11—C12—C13−1.3 (5)
O13—Na2—O10—Na1−152.07 (12)C11—C12—C13—C8−1.1 (5)
O14—Na2—O10—Na1−87.9 (5)C9—C8—C13—C122.2 (4)
O9—Na2—O10—Na122.63 (8)S2—C8—C13—C12−177.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.862.303.046 (4)145
N2—H2A···O1ii0.862.303.066 (4)149
O7—H15···N2iii0.852.132.929 (4)157
O7—H16···O2iv0.851.982.809 (3)166
O8—H17···O12v0.852.292.800 (4)119
O8—H18···O60.852.142.989 (4)171
O9—H19···O3vi0.852.002.814 (4)160
O9—H20···O8vi0.852.062.911 (4)175
O10—H21···O20.851.992.831 (3)172
O10—H22···O14vii0.852.012.812 (4)157
O11—H23···O40.852.052.895 (4)175
O11—H24···O5vi0.852.032.872 (4)169
O12—H25···O7viii0.851.952.794 (3)175
O12—H26···O2vi0.852.092.889 (4)157
O13—H27···O6viii0.852.122.969 (4)175
O13—H28···O5ix0.852.322.883 (4)124
O14—H29···O6ix0.852.042.837 (3)156
O14—H30···O4vi0.851.952.790 (3)171

Symmetry codes: (i) −x, y+1/2, −z; (ii) −x, y−1/2, −z+1; (iii) −x, y+1/2, −z+1; (iv) x, y, z+1; (v) x+1, y, z+1; (vi) x−1, y, z; (vii) x+1, y, z; (viii) x, y, z−1; (ix) x−1, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5297).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tai, X. S., Yin, J., Feng, Y. M. & Kong, F. Y. (2007). Chin. J. Inorg. Chem.24, 1812–1814.
  • Wang, J. G., Shen, R., Wu, W. N., Wu, J. C. & Tang, N. (2008). Anal. Sci.24, x61–x62.

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