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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages m125-m126
https://doi.org/10.1107/S1600536809055512

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

Xi-Shi Taia* and Fu-Gong Zhangb

aCollege of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and bDepartment of Physics, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 27 December 2009; accepted 28 December 2009; online 9 January 2010)

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[Tai, X. S., Yin, J., Feng, Y. M. & Kong, F. Y. (2007). Chin. J. Inorg. Chem. 24, 1812-1814.]); Wang et al. (2008[Wang, J. G., Shen, R., Wu, W. N., Wu, J. C. & Tang, N. (2008). Anal. Sci. 24, x61-x62.]).

[Scheme 1]

Experimental

Crystal data

  • [Na2(C7H8NO3S)(H2O)8](C7H8NO3S)

  • Mr = 562.52

  • Monoclinic, P 21

  • 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 0.946

  • 6522 measured reflections

  • 4067 independent reflections

  • 3823 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1779 Friedel pairs

  • Flack parameter: 0.03 (7)

Table 1
Selected bond lengths (Å)

Na1—O9 2.382 (3)
Na1—O8 2.390 (3)
Na1—O1 2.399 (3)
Na1—O7 2.453 (3)
Na1—O10 2.466 (3)
Na1—O11 2.670 (3)
Na2—O10 2.341 (3)
Na2—O13 2.348 (3)
Na2—O14 2.380 (3)
Na2—O9 2.441 (3)
Na2—O12 2.490 (3)
Na2—O11 2.516 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯O4i 0.86 2.30 3.046 (4) 145
N2—H2A⋯O1ii 0.86 2.30 3.066 (4) 149
O7—H15⋯N2iii 0.85 2.13 2.929 (4) 157
O7—H16⋯O2iv 0.85 1.98 2.809 (3) 166
O8—H17⋯O12v 0.85 2.29 2.800 (4) 119
O8—H18⋯O6 0.85 2.14 2.989 (4) 171
O9—H19⋯O3vi 0.85 2.00 2.814 (4) 160
O9—H20⋯O8vi 0.85 2.06 2.911 (4) 175
O10—H21⋯O2 0.85 1.99 2.831 (3) 172
O10—H22⋯O14vii 0.85 2.01 2.812 (4) 157
O11—H23⋯O4 0.85 2.05 2.895 (4) 175
O11—H24⋯O5vi 0.85 2.03 2.872 (4) 169
O12—H25⋯O7viii 0.85 1.95 2.794 (3) 175
O12—H26⋯O2vi 0.85 2.09 2.889 (4) 157
O13—H27⋯O6viii 0.85 2.12 2.969 (4) 175
O13—H28⋯O5ix 0.85 2.32 2.883 (4) 124
O14—H29⋯O6ix 0.85 2.04 2.837 (3) 156
O14—H30⋯O4vi 0.85 1.95 2.790 (3) 171
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z]; (ii) [-x, y-{\script{1\over 2}}, -z+1]; (iii) [-x, y+{\script{1\over 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.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055512/hb5297Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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.

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

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.
(4-Amino-3-methylbenzenesulfonato)tri-µ-aqua-pentaaquadisodium 4-amino-3-methylbenzenesulfonate top
Crystal data top
[Na2(C7H8NO3S)(H2O)8](C7H8NO3S)F(000) = 592
Mr = 562.52Dx = 1.480 Mg m−3
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 mm−1
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 top
Bruker SMART CCD
diffractometer		4067 independent reflections
Radiation source: fine-focus sealed tube3823 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.097 w = 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 Å−3
308 parametersΔρmin = −0.33 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1779 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (7)
Crystal data top
[Na2(C7H8NO3S)(H2O)8](C7H8NO3S)V = 1261.9 (6) Å3
Mr = 562.52Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.2346 (17) ŵ = 0.31 mm−1
b = 27.793 (8) ÅT = 298 K
c = 7.285 (2) Å0.24 × 0.20 × 0.18 mm
β = 91.296 (5)°
Data collection top
Bruker SMART CCD
diffractometer		4067 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3823 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.946Rint = 0.034
6522 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.097Δρmax = 0.34 e Å−3
S = 1.05Δρmin = −0.33 e Å−3
4067 reflectionsAbsolute structure: Flack (1983), 1779 Friedel pairs
308 parametersAbsolute structure parameter: 0.03 (7)
0 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
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formula[Na2(C7H8NO3S)(H2O)8](C7H8NO3S)
Mr562.52
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)6.2346 (17), 27.793 (8), 7.285 (2)
β (°) 91.296 (5)
V (Å3)1261.9 (6)
Z2
Radiation typeMo Kα
µ (mm−1)0.31
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.929, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections		6522, 4067, 3823
Rint0.034
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.097, 1.05
No. of reflections4067
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.34, −0.33
Absolute structureFlack (1983), 1779 Friedel pairs
Absolute structure parameter0.03 (7)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Na1—O92.382 (3)Na2—O102.341 (3)
Na1—O82.390 (3)Na2—O132.348 (3)
Na1—O12.399 (3)Na2—O142.380 (3)
Na1—O72.453 (3)Na2—O92.441 (3)
Na1—O102.466 (3)Na2—O122.490 (3)
Na1—O112.670 (3)Na2—O112.516 (3)
Hydrogen-bond geometry (Å, º) top
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.
 

Acknowledgements

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.

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTai, X. S., Yin, J., Feng, Y. M. & Kong, F. Y. (2007). Chin. J. Inorg. Chem. 24, 1812–1814.  Google Scholar
 First citationWang, J. G., Shen, R., Wu, W. N., Wu, J. C. & Tang, N. (2008). Anal. Sci. 24, x61–x62.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages m125-m126
https://doi.org/10.1107/S1600536809055512
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