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

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ISSN: 2056-9890

(15-Crown-5-κ5O)[S-(E)-1,2-di­chloro­vinyl thio­sulfato-κO]sodium

aCollege of Chemistry and Chemical Engineering, Graduate University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China
*Correspondence e-mail: dqsun19820901@163.com

(Received 23 May 2011; accepted 8 June 2011; online 18 June 2011)

In the title complex, [Na(C2HCl2O3S2)(C10H20O5)], there are two independent complex units in the asymmetric unit, one of which has a 55:45% disorder in the 15-crown-5 component. The coordination sphere about the Na atom in each complex unit comprises five bonds to O atoms of the crown ether [Na—O = 2.390 (7)–2.466 (6) Å] and one to a thio­sulfate O atom [Na—O = 2.305 (4) and 2.447 (3) Å].

Related literature

For the usage of sodium alkyl thio­sulfate in synthesis, see: Crich et al. (2007[Crich, D., Krishnamurthy, V., Brebion, F., Karatholuvhu, M., Subramanian, V. & Hutton, T. K. (2007). J. Am. Chem. Soc. 129, 10282-10294.]); Cruz et al. (2001[Cruz, A., Vasquez-Badillo, A., Ramos-Garcia, I. & Contreras, R. (2001). Tetrahedron Asymmetry, 12, 711-717.]); Guth et al. (1979[Guth, J. J., Sokol, P. E. & Lindemann, M. K. O. (1979). J. Org. Chem. 44, 1550-1551.]); Huang et al. (1997[Huang, Y., Zhang, Y. M. & Wang, Y. L. (1997). Synth. Commun. 27, 1043-1047.]); Wille et al. (1977[Wille, F., Schwab, W., Schmitzer, J. & Jochum, C. (1977). Chem. Ber. 110, 264-268.]). For the crystal structure of similiar 15-crown-5 complexes, see: Blais et al. (2001[Blais, P., Brask, J. K., Chivers, T. & Schatte, G. (2001). Inorg. Chem. 40, 384-388.]); McIntosh et al. (2001[McIntosh, N. N., Kahwa, I. A. & Mague, J. T. (2001). Acta Cryst. E57, m21-m22.]).

[Scheme 1]

Experimental

Crystal data
  • [Na(C2HCl2O3S2)(C10H20O5)]

  • Mr = 451.30

  • Triclinic, [P \overline 1]

  • a = 8.4455 (18) Å

  • b = 15.787 (4) Å

  • c = 16.778 (4) Å

  • α = 110.854 (19)°

  • β = 99.53 (2)°

  • γ = 100.76 (2)°

  • V = 1987.0 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.59 mm−1

  • T = 295 K

  • 0.50 × 0.40 × 0.30 mm

Data collection
  • Bruker P4 four-circle diffractometer

  • Absorption correction: empirical (using intensity measurements) (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.465, Tmax = 0.506

  • 8439 measured reflections

  • 6904 independent reflections

  • 5027 reflections with I > 2σ(I)

  • Rint = 0.027

  • 3 standard reflections every 97 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.120

  • S = 1.07

  • 6904 reflections

  • 587 parameters

  • 52 restraints

  • H-atom parameters constrained

  • Δρmax = 0.62 e Å−3

  • Δρmin = −0.46 e Å−3

Data collection: XSCANS (Bruker, 1997[Bruker (1997). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; 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


Comment top

Sodium alkyl thiosulfates are a class of useful synthetic intermediates, and are widely used in the construction of C—S, S—S, C—N, C—O and S—N bonds (Crich et al., 2007; Cruz et al., 2001; Guth et al., 1979; Huang et al., 1997; Wille et al., 1977). However, most of these reactions are carried out under vigorous chemical conditions. When the alkyl chain is short, the reaction can be only carried out in highly polar solvents such as water and methanol, due to the restricted solubility of the products. These factors restrict the applications of sodium alkyl thiosulfates, especially thermolabile compounds. In addition, most groups associated with the sulfur atoms are saturated whereas research on sodium olefinic thiosulfate has rarely been reported. We synthesized the title compound C12H21Cl2NaO8S2 (I) by reaction of sodium thiosulfate with trichloroethylene and 15-crown-5 in acetonitrile at room temperature. Compound (I) showed significantly improved solubility in some moderately polar solvents such as ethyl acetate, dichloromethane, acetone and toluene.

In the structure of (I) there are two independent complex units in the asymmetric unit (Fig. 1), one of which (involving Na2) has a 55/45% disorder in the 15-crown-5 component. The coordination sphere about the Na centre in each complex unit comprises five bonds to O atoms of the crown ether [Na—O range 2.390 (7)–2.466 (6) Å] and one to a thiosulfato O donor [Na1—O13, 2.447 (3) and Na2—O15, 2.305 (4) Å]. There is a longer Na1···O12 (thiosulfate) contact in one of the complex units. The vinyl chain conformation of the two (E)-dichlorovinylsulfato ligands is similar [torsion angles S2—S1—C21—C22, -88.8 (5)°; S4—S3—C23—C24, -96.8 (6)°].

Related literature top

For the usage of sodium alkyl thiosulfate in synthesis, see: Crich et al. (2007); Cruz et al. (2001); Guth et al. (1979); Huang et al. (1997); Wille et al. (1977). For the crystal structure of similiar 15-crown-5 complexes, see: Blais et al. (2001); McIntosh et al. (2001).

Experimental top

Ground Na2S2O3 . 5H2O (0.496 g, 2 mmol) and 15-crown-5 (0.441 g, 2 mmol) were suspended in 40 ml of acetonitrile. Trichloroethylene (0.526 g, 4 mmol) and NaOH (0.08 g, 2 mmol) were added with stirring which was continued for 72 h at room temperature. The reaction product was filtered and washed with acetonitrile and after removal of solvent, the products were separated using silica gel column chromatography to give the title compound in 51% yield. Crystals were obtained by diffusing n-pentane into a concentrated solution of the compound in acetone at room temperature.

Refinement top

One of the 15-crown-5 components, coordinated to Na2, was disordered and occupancies were assigned to be 0.55 and 0.45 in the final refinement. All non-hydrogen atoms were subjected to anisotropic refinement. All hydrogen atoms were generated geometically and were included in the refinement with C—H bond distances of 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C), using a riding model.

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS (Bruker, 1997); data reduction: XSCANS (Bruker, 1997); 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. Molecular structure and atom labeling scheme for the two independent molecules of the title compound in the asymmetric unit. Atoms of the minor component of the 55/45% disordered 15-crown-5 ligand associated with Na2 have been omitted. The displacement ellipsoids are drawn at the 35% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound.
[S-(E)-1,2-dichlorovinyl thiosulfato- κO](1,4,7,10,13-pentaoxacyclopentadecane)sodium top
Crystal data top
[Na(C2HCl2O3S2)(C10H20O5)]Z = 4
Mr = 451.30F(000) = 936
Triclinic, P1Dx = 1.509 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4455 (18) ÅCell parameters from 38 reflections
b = 15.787 (4) Åθ = 7.2–12.5°
c = 16.778 (4) ŵ = 0.59 mm1
α = 110.854 (19)°T = 295 K
β = 99.53 (2)°Prism, colorless
γ = 100.76 (2)°0.50 × 0.40 × 0.30 mm
V = 1987.0 (9) Å3
Data collection top
Bruker P4 four-circle
diffractometer
5027 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.1°, θmin = 2.3°
ω scansh = 101
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 1717
Tmin = 0.465, Tmax = 0.506l = 1919
8439 measured reflections3 standard reflections every 97 reflections
6904 independent reflections intensity decay: none
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.001P)2 + 2.5P]
where P = (Fo2 + 2Fc2)/3
6904 reflections(Δ/σ)max < 0.001
587 parametersΔρmax = 0.62 e Å3
52 restraintsΔρmin = 0.46 e Å3
Crystal data top
[Na(C2HCl2O3S2)(C10H20O5)]γ = 100.76 (2)°
Mr = 451.30V = 1987.0 (9) Å3
Triclinic, P1Z = 4
a = 8.4455 (18) ÅMo Kα radiation
b = 15.787 (4) ŵ = 0.59 mm1
c = 16.778 (4) ÅT = 295 K
α = 110.854 (19)°0.50 × 0.40 × 0.30 mm
β = 99.53 (2)°
Data collection top
Bruker P4 four-circle
diffractometer
5027 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
Rint = 0.027
Tmin = 0.465, Tmax = 0.5063 standard reflections every 97 reflections
8439 measured reflections intensity decay: none
6904 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05952 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.07Δρmax = 0.62 e Å3
6904 reflectionsΔρmin = 0.46 e Å3
587 parameters
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*/UeqOcc. (<1)
Na10.14966 (18)0.28710 (10)0.45817 (10)0.0609 (4)
Na20.5805 (2)0.29126 (11)0.97277 (11)0.0736 (4)
S10.10492 (14)0.25340 (8)0.18327 (7)0.0712 (3)
S20.09233 (13)0.34225 (7)0.29733 (7)0.0640 (3)
S30.33363 (13)0.23429 (8)0.67908 (7)0.0670 (3)
S40.23814 (13)0.21257 (8)0.78255 (7)0.0672 (3)
Cl10.0369 (2)0.06689 (10)0.14297 (12)0.1146 (5)
Cl20.33675 (17)0.16304 (11)0.26409 (9)0.1013 (4)
Cl30.69742 (18)0.36967 (9)0.78535 (11)0.1159 (5)
Cl40.5072 (2)0.07699 (10)0.63686 (15)0.1431 (7)
O10.0689 (4)0.1173 (2)0.4015 (2)0.0860 (9)
O20.0849 (4)0.2292 (2)0.5087 (2)0.0854 (9)
O30.1483 (3)0.3996 (2)0.6056 (2)0.0766 (8)
O40.4074 (3)0.41335 (19)0.53040 (18)0.0685 (7)
O50.3958 (4)0.2259 (2)0.4629 (2)0.0786 (8)
O110.1432 (4)0.4189 (2)0.2724 (2)0.0852 (9)
O120.2101 (4)0.2893 (2)0.3038 (2)0.0847 (9)
O130.0179 (4)0.3630 (2)0.37160 (19)0.0840 (9)
O140.2177 (6)0.1163 (3)0.7663 (3)0.1230 (14)
O150.3597 (4)0.2733 (3)0.8616 (2)0.0997 (11)
O160.0893 (4)0.2409 (3)0.7701 (2)0.1097 (13)
C10.0696 (8)0.0775 (4)0.4247 (4)0.123 (2)
H1A0.05160.02200.43320.147*
H1B0.16630.05690.37560.147*
C20.1070 (8)0.1365 (4)0.5015 (5)0.126 (2)
H2A0.22160.11120.50030.151*
H2B0.03600.13630.55310.151*
C30.0934 (6)0.2894 (4)0.5921 (3)0.0826 (14)
H3A0.03040.27590.63790.099*
H3B0.20820.28030.59600.099*
C40.0214 (5)0.3892 (3)0.6038 (3)0.0817 (13)
H4A0.07800.40130.55540.098*
H4B0.03410.43310.65850.098*
C50.2332 (6)0.4879 (3)0.6108 (3)0.0809 (13)
H5A0.22890.53780.66410.097*
H5B0.18390.49910.56030.097*
C60.4105 (5)0.4838 (3)0.6120 (3)0.0757 (12)
H6A0.47870.54410.61940.091*
H6B0.45670.46830.66030.091*
C70.5549 (5)0.3840 (3)0.5322 (3)0.0743 (12)
H7A0.58940.37570.58640.089*
H7B0.64340.43100.52940.089*
C80.5207 (5)0.2915 (3)0.4533 (3)0.0769 (12)
H8A0.48370.29920.39900.092*
H8B0.62110.27010.45150.092*
C90.3475 (7)0.1367 (3)0.3907 (4)0.0943 (16)
H9A0.43950.10800.38840.113*
H9B0.31490.14380.33570.113*
C100.2015 (7)0.0758 (3)0.4046 (4)0.0973 (16)
H10A0.16940.01270.35880.117*
H10B0.23210.07180.46120.117*
O60.4038 (7)0.3119 (5)1.0723 (4)0.0780 (16)0.55
O70.4955 (9)0.1478 (4)0.9969 (5)0.085 (2)0.55
O80.7302 (8)0.1748 (6)0.9068 (6)0.094 (3)0.55
O90.8806 (8)0.3433 (5)1.0235 (5)0.100 (2)0.55
O100.6642 (9)0.4528 (5)1.0732 (5)0.111 (2)0.55
C110.3517 (17)0.2311 (6)1.0891 (9)0.092 (3)0.55
H11A0.24510.23011.10380.110*0.55
H11B0.43150.23491.13980.110*0.55
C120.3349 (14)0.1412 (9)1.0124 (9)0.083 (4)0.55
H12A0.29980.08731.02650.099*0.55
H12B0.25420.13510.96090.099*0.55
C130.5037 (15)0.0754 (7)0.9207 (8)0.102 (4)0.55
H13A0.43240.07650.86960.123*0.55
H13B0.46230.01530.92370.123*0.55
C140.6777 (19)0.0846 (9)0.9097 (12)0.096 (6)0.55
H14A0.75020.08070.95880.116*0.55
H14B0.67980.03510.85560.116*0.55
C150.9060 (10)0.1998 (9)0.9349 (11)0.090 (4)0.55
H15A0.95220.16520.88820.107*0.55
H15B0.94130.18600.98590.107*0.55
C160.9630 (12)0.3044 (8)0.9581 (8)0.085 (4)0.55
H16A1.08290.32780.98090.102*0.55
H16B0.93000.31870.90710.102*0.55
C170.933 (2)0.4411 (7)1.0672 (11)0.108 (5)0.55
H17A0.93930.46711.02300.129*0.55
H17B1.04490.45771.10360.129*0.55
C180.8304 (10)0.4900 (9)1.1248 (8)0.099 (7)0.55
H18A0.84160.47751.17780.118*0.55
H18B0.86580.55751.14180.118*0.55
C190.5348 (15)0.4655 (10)1.1164 (10)0.125 (5)0.55
H19A0.44170.46801.07570.150*0.55
H19B0.57370.52651.16550.150*0.55
C200.470 (2)0.3941 (8)1.1513 (8)0.099 (6)0.55
H20A0.55850.38691.19110.118*0.55
H20B0.38420.41061.18120.118*0.55
O6'0.3803 (12)0.2310 (8)1.0416 (6)0.112 (4)0.45
O7'0.5950 (12)0.1367 (6)0.9737 (7)0.108 (3)0.45
O8'0.8220 (11)0.2517 (6)0.9298 (6)0.098 (2)0.45
O9'0.8282 (9)0.4264 (6)1.0408 (6)0.096 (3)0.45
O10'0.5751 (15)0.4058 (6)1.1183 (6)0.130 (4)0.45
C11'0.382 (3)0.1423 (11)1.0431 (11)0.106 (8)0.45
H11C0.27350.10971.04410.127*0.45
H11D0.46390.14911.09450.127*0.45
C12'0.4276 (15)0.0896 (13)0.9594 (11)0.107 (6)0.45
H12C0.41600.02420.95010.128*0.45
H12D0.35800.09240.90880.128*0.45
C13'0.643 (2)0.0950 (14)0.8934 (13)0.127 (11)0.45
H13C0.57060.09790.84360.153*0.45
H13D0.64380.03020.88080.153*0.45
C14'0.819 (2)0.1582 (8)0.9158 (15)0.111 (8)0.45
H14C0.88490.15730.96850.134*0.45
H14D0.87040.13300.86810.134*0.45
C15'0.964 (2)0.3298 (13)0.9621 (12)0.182 (14)0.45
H15C0.96040.36030.92110.218*0.45
H15D1.06240.30670.96310.218*0.45
C16'0.9809 (15)0.4026 (12)1.0529 (12)0.099 (6)0.45
H16C0.99210.37641.09710.118*0.45
H16D1.07510.45651.06930.118*0.45
C17'0.812 (3)0.4761 (18)1.1276 (9)0.175 (16)0.45
H17C0.90050.53441.15530.210*0.45
H17D0.82990.43871.16170.210*0.45
C18'0.648 (2)0.4992 (8)1.1327 (12)0.125 (6)0.45
H18C0.64940.54471.18990.150*0.45
H18D0.60260.51711.08600.150*0.45
C19'0.4106 (17)0.3922 (12)1.1280 (14)0.095 (6)0.45
H19C0.33720.39961.08140.114*0.45
H19D0.40620.43671.18450.114*0.45
C20'0.362 (2)0.2922 (10)1.1220 (9)0.105 (5)0.45
H20C0.43220.28661.17080.126*0.45
H20D0.24700.27591.12520.126*0.45
C210.1712 (5)0.1594 (3)0.2119 (3)0.0723 (11)
C220.1165 (6)0.0862 (3)0.1972 (3)0.0857 (14)
H22A0.16230.04140.21690.103*
C230.5175 (6)0.2014 (4)0.6936 (3)0.0930 (15)
C240.6631 (7)0.2484 (4)0.7327 (3)0.1042 (18)
H24A0.75020.22010.73390.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0573 (9)0.0594 (9)0.0700 (10)0.0169 (7)0.0187 (7)0.0285 (8)
Na20.0671 (10)0.0654 (10)0.0815 (11)0.0129 (8)0.0205 (9)0.0231 (9)
S10.0762 (7)0.0715 (7)0.0614 (6)0.0100 (6)0.0057 (5)0.0314 (5)
S20.0701 (6)0.0523 (6)0.0648 (6)0.0154 (5)0.0086 (5)0.0220 (5)
S30.0574 (6)0.0833 (7)0.0655 (6)0.0198 (5)0.0175 (5)0.0343 (6)
S40.0627 (6)0.0799 (7)0.0688 (7)0.0219 (6)0.0221 (5)0.0372 (6)
Cl10.1166 (11)0.0807 (9)0.1507 (14)0.0348 (8)0.0682 (10)0.0316 (9)
Cl20.0950 (9)0.1228 (11)0.0983 (10)0.0292 (8)0.0479 (8)0.0474 (9)
Cl30.0907 (9)0.0727 (8)0.1356 (13)0.0064 (7)0.0031 (9)0.0048 (8)
Cl40.1041 (11)0.0637 (8)0.223 (2)0.0245 (8)0.0387 (12)0.0141 (10)
O10.093 (2)0.0693 (19)0.108 (3)0.0224 (18)0.038 (2)0.0427 (18)
O20.082 (2)0.083 (2)0.105 (3)0.0229 (17)0.0408 (19)0.046 (2)
O30.0617 (18)0.087 (2)0.087 (2)0.0267 (16)0.0211 (15)0.0370 (17)
O40.0539 (16)0.0707 (18)0.0757 (19)0.0153 (14)0.0110 (14)0.0261 (15)
O50.078 (2)0.079 (2)0.085 (2)0.0280 (17)0.0244 (17)0.0351 (18)
O110.106 (2)0.0587 (17)0.085 (2)0.0095 (16)0.0151 (18)0.0311 (16)
O120.0725 (19)0.078 (2)0.095 (2)0.0273 (16)0.0029 (17)0.0288 (17)
O130.101 (2)0.088 (2)0.0633 (19)0.0288 (18)0.0237 (17)0.0277 (16)
O140.179 (4)0.087 (3)0.129 (3)0.031 (3)0.066 (3)0.063 (2)
O150.093 (2)0.133 (3)0.062 (2)0.020 (2)0.0162 (18)0.033 (2)
O160.078 (2)0.191 (4)0.107 (3)0.066 (2)0.047 (2)0.087 (3)
C10.148 (6)0.080 (4)0.141 (6)0.001 (4)0.071 (5)0.046 (4)
C20.142 (6)0.076 (4)0.171 (7)0.006 (4)0.070 (5)0.061 (4)
C30.066 (3)0.121 (4)0.088 (3)0.039 (3)0.033 (3)0.060 (3)
C40.065 (3)0.096 (4)0.089 (3)0.035 (3)0.027 (2)0.032 (3)
C50.081 (3)0.069 (3)0.082 (3)0.023 (2)0.014 (3)0.020 (2)
C60.070 (3)0.069 (3)0.072 (3)0.013 (2)0.011 (2)0.016 (2)
C70.054 (2)0.088 (3)0.079 (3)0.021 (2)0.012 (2)0.031 (3)
C80.056 (3)0.099 (4)0.079 (3)0.030 (2)0.018 (2)0.035 (3)
C90.107 (4)0.065 (3)0.116 (4)0.038 (3)0.044 (3)0.027 (3)
C100.108 (4)0.073 (3)0.111 (4)0.039 (3)0.028 (3)0.029 (3)
O60.089 (4)0.074 (4)0.064 (4)0.023 (4)0.023 (3)0.018 (4)
O70.051 (4)0.080 (5)0.119 (6)0.005 (4)0.026 (4)0.041 (4)
O80.079 (5)0.094 (7)0.121 (6)0.044 (5)0.042 (4)0.039 (5)
O90.089 (5)0.098 (5)0.101 (5)0.013 (5)0.021 (4)0.031 (5)
O100.123 (7)0.082 (5)0.108 (6)0.018 (5)0.024 (5)0.023 (5)
C110.091 (8)0.094 (10)0.099 (11)0.019 (8)0.038 (8)0.045 (8)
C120.076 (8)0.079 (8)0.085 (9)0.002 (6)0.020 (7)0.035 (7)
C130.093 (9)0.056 (6)0.135 (11)0.007 (6)0.035 (8)0.016 (7)
C140.096 (10)0.092 (12)0.104 (10)0.053 (9)0.033 (7)0.024 (8)
C150.086 (8)0.123 (13)0.091 (8)0.058 (8)0.042 (7)0.055 (11)
C160.031 (5)0.102 (8)0.105 (10)0.021 (6)0.034 (6)0.015 (7)
C170.112 (14)0.066 (9)0.127 (12)0.015 (8)0.003 (12)0.049 (8)
C180.068 (7)0.080 (9)0.092 (12)0.031 (7)0.031 (7)0.010 (7)
C190.106 (10)0.085 (10)0.145 (12)0.012 (8)0.054 (10)0.003 (9)
C200.083 (10)0.119 (12)0.065 (8)0.033 (8)0.020 (8)0.000 (7)
O6'0.139 (8)0.128 (11)0.073 (6)0.018 (7)0.053 (6)0.041 (7)
O7'0.088 (7)0.107 (8)0.107 (7)0.005 (6)0.021 (6)0.036 (6)
O8'0.106 (7)0.076 (5)0.114 (7)0.026 (6)0.038 (5)0.035 (5)
O9'0.068 (6)0.102 (8)0.110 (8)0.004 (5)0.009 (5)0.052 (6)
O10'0.160 (11)0.073 (6)0.141 (9)0.032 (7)0.060 (8)0.014 (6)
C11'0.107 (15)0.108 (14)0.096 (14)0.006 (10)0.003 (10)0.060 (12)
C12'0.095 (13)0.099 (12)0.104 (13)0.018 (11)0.005 (10)0.046 (10)
C13'0.16 (3)0.054 (10)0.17 (2)0.015 (12)0.046 (17)0.043 (13)
C14'0.20 (2)0.062 (10)0.114 (16)0.063 (15)0.09 (2)0.040 (11)
C15'0.18 (2)0.20 (2)0.083 (14)0.104 (17)0.033 (13)0.067 (15)
C16'0.067 (8)0.104 (14)0.114 (14)0.022 (9)0.021 (8)0.071 (12)
C17'0.29 (4)0.19 (2)0.061 (14)0.16 (3)0.011 (18)0.036 (15)
C18'0.20 (2)0.060 (9)0.096 (11)0.043 (12)0.046 (13)0.001 (8)
C19'0.073 (11)0.118 (14)0.075 (11)0.031 (9)0.010 (8)0.020 (10)
C20'0.102 (10)0.120 (14)0.083 (10)0.004 (12)0.033 (9)0.039 (11)
C210.072 (3)0.074 (3)0.063 (3)0.011 (2)0.013 (2)0.025 (2)
C220.088 (3)0.075 (3)0.087 (3)0.009 (3)0.020 (3)0.031 (3)
C230.072 (3)0.130 (5)0.091 (4)0.025 (3)0.028 (3)0.058 (3)
C240.086 (4)0.151 (5)0.094 (4)0.029 (4)0.034 (3)0.067 (4)
Geometric parameters (Å, º) top
Na1—O12.417 (3)O7—C121.414 (9)
Na1—O22.432 (3)O8—C151.414 (9)
Na1—O42.442 (3)O8—C141.431 (10)
Na1—O132.447 (3)O9—C171.396 (9)
Na1—O52.452 (3)O9—C161.413 (8)
Na1—O32.482 (3)O10—C181.412 (8)
Na1—O122.732 (4)O10—C191.415 (9)
Na1—S23.110 (2)C11—C121.503 (9)
Na2—O152.305 (4)C11—H11A0.9700
Na2—O8'2.389 (7)C11—H11B0.9700
Na2—O102.390 (7)C12—H12A0.9700
Na2—O62.396 (6)C12—H12B0.9700
Na2—O92.415 (7)C13—C141.498 (10)
Na2—O6'2.434 (8)C13—H13A0.9700
Na2—O72.439 (6)C13—H13B0.9700
Na2—O9'2.457 (7)C14—H14A0.9700
Na2—O82.466 (6)C14—H14B0.9700
Na2—O7'2.471 (8)C15—C161.515 (9)
Na2—O10'2.482 (8)C15—H15A0.9700
Na2—C193.084 (13)C15—H15B0.9700
S1—C211.742 (5)C16—H16A0.9700
S1—S22.1367 (17)C16—H16B0.9700
S2—O121.428 (3)C17—C181.507 (10)
S2—O111.432 (3)C17—H17A0.9700
S2—O131.449 (3)C17—H17B0.9700
S3—C231.734 (5)C18—H18A0.9700
S3—S42.1368 (16)C18—H18B0.9700
S4—O141.416 (4)C19—C201.501 (10)
S4—O151.417 (3)C19—H19A0.9700
S4—O161.419 (3)C19—H19B0.9700
Cl1—C221.715 (5)C20—H20A0.9700
Cl2—C211.768 (5)C20—H20B0.9700
Cl3—C241.742 (6)O6'—C20'1.407 (9)
Cl4—C231.830 (6)O6'—C11'1.413 (10)
O1—C101.401 (5)O7'—C12'1.406 (9)
O1—C11.402 (6)O7'—C13'1.437 (10)
O2—C21.398 (6)O8'—C14'1.405 (9)
O2—C31.407 (5)O8'—C15'1.415 (10)
O3—C41.406 (5)O9'—C16'1.413 (10)
O3—C51.409 (5)O9'—C17'1.430 (10)
O4—C71.408 (5)O10'—C18'1.403 (9)
O4—C61.416 (5)O10'—C19'1.410 (10)
O5—C81.407 (5)C11'—C12'1.510 (10)
O5—C91.422 (5)C11'—H11C0.9700
C1—C21.420 (6)C11'—H11D0.9700
C1—H1A0.9700C12'—H12C0.9700
C1—H1B0.9700C12'—H12D0.9700
C2—H2A0.9700C13'—C14'1.529 (10)
C2—H2B0.9700C13'—H13C0.9700
C3—C41.509 (6)C13'—H13D0.9700
C3—H3A0.9700C14'—H14C0.9700
C3—H3B0.9700C14'—H14D0.9700
C4—H4A0.9700C15'—C16'1.510 (10)
C4—H4B0.9700C15'—H15C0.9700
C5—C61.509 (6)C15'—H15D0.9700
C5—H5A0.9700C16'—H16C0.9700
C5—H5B0.9700C16'—H16D0.9700
C6—H6A0.9700C17'—C18'1.508 (10)
C6—H6B0.9700C17'—H17C0.9700
C7—C81.520 (6)C17'—H17D0.9700
C7—H7A0.9700C18'—H18C0.9700
C7—H7B0.9700C18'—H18D0.9700
C8—H8A0.9700C19'—C20'1.518 (10)
C8—H8B0.9700C19'—H19C0.9700
C9—C101.520 (7)C19'—H19D0.9700
C9—H9A0.9700C20'—H20C0.9700
C9—H9B0.9700C20'—H20D0.9700
C10—H10A0.9700C21—C221.282 (6)
C10—H10B0.9700C22—H22A0.9300
O6—C111.411 (8)C23—C241.241 (6)
O6—C201.419 (9)C24—H24A0.9300
O7—C131.402 (8)
O1—Na1—O268.31 (12)O1—C10—C9107.7 (4)
O1—Na1—O4137.10 (12)O1—C10—H10A110.2
O2—Na1—O4133.84 (13)C9—C10—H10A110.2
O1—Na1—O13118.23 (13)O1—C10—H10B110.2
O2—Na1—O1399.92 (12)C9—C10—H10B110.2
O4—Na1—O1395.82 (11)H10A—C10—H10B108.5
O1—Na1—O569.23 (12)C11—O6—C20111.8 (10)
O2—Na1—O5121.52 (12)C11—O6—Na2112.6 (7)
O4—Na1—O568.16 (11)C20—O6—Na2114.0 (8)
O13—Na1—O5135.41 (12)C13—O7—C12114.7 (10)
O1—Na1—O3127.39 (12)C13—O7—Na2104.8 (7)
O2—Na1—O368.27 (12)C12—O7—Na2108.1 (7)
O4—Na1—O366.85 (11)C15—O8—C14104.7 (10)
O13—Na1—O397.24 (11)C15—O8—Na2118.9 (7)
O5—Na1—O3112.06 (11)C14—O8—Na2116.4 (7)
O1—Na1—O1293.38 (11)C17—O9—C16115.2 (9)
O2—Na1—O12137.70 (12)C17—O9—Na2110.1 (8)
O4—Na1—O1285.79 (10)C16—O9—Na2113.8 (6)
O13—Na1—O1254.35 (10)C18—O10—C19118.2 (10)
O5—Na1—O1282.33 (10)C18—O10—Na2117.8 (7)
O3—Na1—O12139.14 (11)C19—O10—Na2105.4 (7)
O1—Na1—S2107.27 (10)O6—C11—C12113.0 (12)
O2—Na1—S2120.56 (10)O6—C11—H11A109.0
O4—Na1—S291.16 (8)C12—C11—H11A109.0
O13—Na1—S227.02 (7)O6—C11—H11B109.0
O5—Na1—S2109.18 (9)C12—C11—H11B109.0
O3—Na1—S2119.74 (9)H11A—C11—H11B107.8
O12—Na1—S227.34 (6)O7—C12—C11105.2 (10)
O15—Na2—O8'116.7 (2)O7—C12—H12A110.7
O15—Na2—O10107.5 (2)C11—C12—H12A110.7
O8'—Na2—O10107.4 (3)O7—C12—H12B110.7
O15—Na2—O689.46 (18)C11—C12—H12B110.7
O8'—Na2—O6151.6 (3)H12A—C12—H12B108.8
O10—Na2—O672.0 (2)O7—C13—C14112.1 (11)
O15—Na2—O9143.1 (2)O7—C13—Na249.4 (5)
O8'—Na2—O939.7 (3)C14—C13—Na286.1 (8)
O10—Na2—O970.4 (2)O7—C13—H13A109.2
O6—Na2—O9122.4 (2)C14—C13—H13A109.2
O15—Na2—O6'88.3 (3)Na2—C13—H13A80.2
O8'—Na2—O6'134.8 (4)O7—C13—H13B109.2
O10—Na2—O6'98.8 (3)C14—C13—H13B109.2
O6—Na2—O6'27.7 (3)Na2—C13—H13B158.2
O9—Na2—O6'128.6 (3)H13A—C13—H13B107.9
O15—Na2—O7101.9 (2)O8—C14—C13105.8 (11)
O8'—Na2—O792.7 (3)O8—C14—H14A110.6
O10—Na2—O7130.9 (3)C13—C14—H14A110.6
O6—Na2—O769.8 (2)O8—C14—H14B110.6
O9—Na2—O7106.3 (3)C13—C14—H14B110.6
O6'—Na2—O743.4 (3)H14A—C14—H14B108.7
O15—Na2—O9'125.0 (2)O8—C15—C16106.0 (9)
O8'—Na2—O9'67.9 (3)O8—C15—H15A110.5
O10—Na2—O9'39.5 (3)C16—C15—H15A110.5
O6—Na2—O9'107.3 (3)O8—C15—H15B110.5
O9—Na2—O9'33.6 (3)C16—C15—H15B110.5
O6'—Na2—O9'129.1 (3)H15A—C15—H15B108.7
O7—Na2—O9'133.1 (3)O9—C16—C15103.3 (10)
O15—Na2—O8106.7 (2)O9—C16—H16A111.1
O8'—Na2—O828.6 (3)C15—C16—H16A111.1
O10—Na2—O8134.5 (3)O9—C16—H16B111.1
O6—Na2—O8137.0 (3)C15—C16—H16B111.1
O9—Na2—O864.2 (2)H16A—C16—H16B109.1
O6'—Na2—O8111.4 (4)O9—C17—C18118.6 (11)
O7—Na2—O868.0 (3)O9—C17—H17A107.7
O9'—Na2—O895.6 (3)C18—C17—H17A107.7
O15—Na2—O7'110.4 (2)O9—C17—H17B107.7
O8'—Na2—O7'69.3 (3)C18—C17—H17B107.7
O10—Na2—O7'138.6 (3)H17A—C17—H17B107.1
O6—Na2—O7'92.2 (3)O10—C18—C17105.5 (10)
O9—Na2—O7'88.4 (3)O10—C18—H18A110.6
O6'—Na2—O7'66.8 (4)C17—C18—H18A110.6
O7—Na2—O7'23.5 (3)O10—C18—H18B110.6
O9'—Na2—O7'120.5 (3)C17—C18—H18B110.6
O8—Na2—O7'45.0 (4)H18A—C18—H18B108.8
O15—Na2—O10'112.3 (3)O10—C19—C20118.4 (14)
O8'—Na2—O10'126.2 (4)O10—C19—Na248.4 (6)
O10—Na2—O10'34.3 (3)C20—C19—Na282.3 (8)
O6—Na2—O10'40.8 (3)O10—C19—H19A107.7
O9—Na2—O10'87.0 (3)C20—C19—H19A107.7
O6'—Na2—O10'65.4 (4)Na2—C19—H19A91.5
O7—Na2—O10'98.1 (3)O10—C19—H19B107.7
O9'—Na2—O10'66.5 (4)C20—C19—H19B107.7
O8—Na2—O10'140.7 (4)Na2—C19—H19B154.3
O7'—Na2—O10'112.8 (4)H19A—C19—H19B107.1
O15—Na2—C1997.5 (3)O6—C20—C19101.2 (10)
O8'—Na2—C19132.2 (3)O6—C20—H20A111.5
O10—Na2—C1926.3 (2)C19—C20—H20A111.5
O6—Na2—C1946.6 (3)O6—C20—H20B111.5
O9—Na2—C1993.1 (3)C19—C20—H20B111.5
O6'—Na2—C1974.1 (3)H20A—C20—H20B109.3
O7—Na2—C19112.8 (3)C20'—O6'—C11'110.7 (12)
O9'—Na2—C1965.2 (3)C20'—O6'—Na2118.8 (9)
O8—Na2—C19155.2 (4)C11'—O6'—Na2115.6 (10)
O7'—Na2—C19130.3 (4)C12'—O7'—C13'107.0 (13)
O10'—Na2—C1918.3 (4)C12'—O7'—Na2103.6 (10)
C21—S1—S2100.39 (15)C13'—O7'—Na2101.2 (11)
O12—S2—O11116.0 (2)C14'—O8'—C15'127.3 (16)
O12—S2—O13111.5 (2)C14'—O8'—Na2111.8 (9)
O11—S2—O13115.70 (19)C15'—O8'—Na2113.5 (11)
O12—S2—S1106.39 (14)C16'—O9'—C17'105.4 (11)
O11—S2—S199.14 (14)C16'—O9'—Na2114.6 (8)
O13—S2—S1106.32 (14)C17'—O9'—Na2104.8 (12)
O12—S2—Na161.45 (14)C18'—O10'—C19'112.4 (13)
O11—S2—Na1141.11 (14)C18'—O10'—Na2112.7 (9)
O13—S2—Na150.06 (13)C19'—O10'—Na2109.8 (11)
S1—S2—Na1119.20 (6)O6'—C11'—C12'104.8 (14)
C23—S3—S4100.79 (17)O6'—C11'—H11C110.8
O14—S4—O15112.8 (3)C12'—C11'—H11C110.8
O14—S4—O16116.0 (3)O6'—C11'—H11D110.8
O15—S4—O16114.3 (2)C12'—C11'—H11D110.8
O14—S4—S3106.64 (17)H11C—C11'—H11D108.9
O15—S4—S3105.45 (15)O7'—C12'—C11'103.9 (17)
O16—S4—S399.79 (15)O7'—C12'—Na250.4 (8)
C10—O1—C1115.6 (4)C11'—C12'—Na283.3 (11)
C10—O1—Na1115.0 (3)O7'—C12'—H12C111.0
C1—O1—Na1115.6 (3)C11'—C12'—H12C111.0
C2—O2—C3111.5 (4)Na2—C12'—H12C160.1
C2—O2—Na1114.7 (3)O7'—C12'—H12D111.0
C3—O2—Na1114.8 (3)C11'—C12'—H12D111.0
C4—O3—C5114.4 (3)Na2—C12'—H12D76.7
C4—O3—Na1104.6 (3)H12C—C12'—H12D109.0
C5—O3—Na1104.4 (3)O7'—C13'—C14'101.0 (14)
C7—O4—C6112.6 (3)O7'—C13'—Na251.6 (8)
C7—O4—Na1115.3 (2)C14'—C13'—Na279.5 (10)
C6—O4—Na1116.1 (2)O7'—C13'—H13C111.6
C8—O5—C9112.7 (4)C14'—C13'—H13C111.6
C8—O5—Na1105.6 (2)Na2—C13'—H13C77.1
C9—O5—Na1105.5 (3)O7'—C13'—H13D111.6
S2—O12—Na191.22 (16)C14'—C13'—H13D111.6
S2—O13—Na1102.92 (17)Na2—C13'—H13D162.5
S4—O15—Na2148.2 (2)H13C—C13'—H13D109.4
O1—C1—C2116.3 (5)O8'—C14'—C13'113.1 (16)
O1—C1—H1A108.2O8'—C14'—H14C109.0
C2—C1—H1A108.2C13'—C14'—H14C109.0
O1—C1—H1B108.2O8'—C14'—H14D109.0
C2—C1—H1B108.2C13'—C14'—H14D109.0
H1A—C1—H1B107.4H14C—C14'—H14D107.8
O2—C2—C1112.8 (5)O8'—C15'—C16'115.5 (14)
O2—C2—H2A109.0O8'—C15'—H15C108.4
C1—C2—H2A109.0C16'—C15'—H15C108.4
O2—C2—H2B109.0O8'—C15'—H15D108.4
C1—C2—H2B109.0C16'—C15'—H15D108.4
H2A—C2—H2B107.8H15C—C15'—H15D107.5
O2—C3—C4107.9 (4)O9'—C16'—C15'101.1 (15)
O2—C3—H3A110.1O9'—C16'—H16C111.5
C4—C3—H3A110.1C15'—C16'—H16C111.5
O2—C3—H3B110.1O9'—C16'—H16D111.5
C4—C3—H3B110.1C15'—C16'—H16D111.5
H3A—C3—H3B108.4H16C—C16'—H16D109.4
O3—C4—C3106.9 (4)O9'—C17'—C18'115.5 (14)
O3—C4—H4A110.3O9'—C17'—H17C108.4
C3—C4—H4A110.3C18'—C17'—H17C108.4
O3—C4—H4B110.3O9'—C17'—H17D108.4
C3—C4—H4B110.3C18'—C17'—H17D108.4
H4A—C4—H4B108.6H17C—C17'—H17D107.5
O3—C5—C6105.6 (4)O10'—C18'—C17'89.7 (15)
O3—C5—H5A110.6O10'—C18'—H18C113.7
C6—C5—H5A110.6C17'—C18'—H18C113.7
O3—C5—H5B110.6O10'—C18'—H18D113.7
C6—C5—H5B110.6C17'—C18'—H18D113.7
H5A—C5—H5B108.8H18C—C18'—H18D110.9
O4—C6—C5107.2 (3)O10'—C19'—C20'104.7 (13)
O4—C6—H6A110.3O10'—C19'—H19C110.8
C5—C6—H6A110.3C20'—C19'—H19C110.8
O4—C6—H6B110.3O10'—C19'—H19D110.8
C5—C6—H6B110.3C20'—C19'—H19D110.8
H6A—C6—H6B108.5H19C—C19'—H19D108.9
O4—C7—C8108.1 (3)O6'—C20'—C19'108.7 (15)
O4—C7—H7A110.1O6'—C20'—H20C110.0
C8—C7—H7A110.1C19'—C20'—H20C110.0
O4—C7—H7B110.1O6'—C20'—H20D110.0
C8—C7—H7B110.1C19'—C20'—H20D110.0
H7A—C7—H7B108.4H20C—C20'—H20D108.3
O5—C8—C7107.2 (4)C22—C21—S1127.3 (4)
O5—C8—H8A110.3C22—C21—Cl2116.0 (4)
C7—C8—H8A110.3S1—C21—Cl2116.6 (3)
O5—C8—H8B110.3C21—C22—Cl1123.1 (4)
C7—C8—H8B110.3C21—C22—H22A118.4
H8A—C8—H8B108.5Cl1—C22—H22A118.4
O5—C9—C10107.5 (4)C24—C23—S3131.6 (5)
O5—C9—H9A110.2C24—C23—Cl4110.9 (5)
C10—C9—H9A110.2S3—C23—Cl4117.3 (3)
O5—C9—H9B110.2C23—C24—Cl3117.1 (5)
C10—C9—H9B110.2C23—C24—H24A121.5
H9A—C9—H9B108.5Cl3—C24—H24A121.5

Experimental details

Crystal data
Chemical formula[Na(C2HCl2O3S2)(C10H20O5)]
Mr451.30
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.4455 (18), 15.787 (4), 16.778 (4)
α, β, γ (°)110.854 (19), 99.53 (2), 100.76 (2)
V3)1987.0 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.50 × 0.40 × 0.30
Data collection
DiffractometerBruker P4 four-circle
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(North et al., 1968)
Tmin, Tmax0.465, 0.506
No. of measured, independent and
observed [I > 2σ(I)] reflections
8439, 6904, 5027
Rint0.027
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.120, 1.07
No. of reflections6904
No. of parameters587
No. of restraints52
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.62, 0.46

Computer programs: XSCANS (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We thank the National Natural Science Foundation of China and the Laboratory of Mol­ecular Nanostructure and Nanotechnology, Institute of Chemistry, Chinese Academy of Sciences for financial support.

References

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