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Acta Cryst. (2007). E63, m1644-m1645    [ doi:10.1107/S1600536807023033 ]

Sodium 4,N-dichlorobenzenesulfonamidate sesquihydrate

B. T. Gowda, K. Jyothi, S. Foro, J. Kozísek and H. Fuess

Abstract top

The structure of the title compound, Na+.C6H4Cl2NO2S-·1.5H2O, resembles the structures of the sodium salts of N-chlorobenzenesulfonamide, N-chloro-4-methylbenzenesulfonamide and N-chloro-2-methyl-4-chlorobenzenesulfonamide. There are two formula units per asymmetric unit. There is no interaction between N and Na, and the Na+ cation is attached to three O atoms from water molecules and three sulfonyl O atoms of three different 4,N-dichlorobenzenesulfonamide anions. There are several hydrogen bonds. The S-N distances of 1.584 (5) and 1.590 (5) Å are consistent with an S=N double bond.

Comment top

The chemistry of arylsulfonamides and their N-halo compounds is of interest as they show distinct physical, chemical and biological properties. Many of these compounds exhibit pharmacological, fungicidal and herbicidal activities due to their oxidizing action in aqueous, partial aqueous and non-aqueous media. Thus N-halo arylsulfonamides are of interest in synthetic, mechanistic, analytical and biological chemistry (Gowda et al., 2002; Gowda, D'Souza & Fuess 2003; Gowda, D'Souza & Kumar, 2003; Gowda, Jyothi et al., 2003; Gowda & Shetty 2004; Gowda & Kumar, 2003; Gowda et al., 2005; Gowda et al., 2007). In the present work, the structure of the sodium salt of N-chloro, 4-chlorobenzenesulfonamde has been determined to explore the effect substituent on the solid state structures of sulfonamides and N-halo arylsulfonamides. The structure (Fig. 1) resembles those of the sodium salts of N-chlorobenzenesulfonamde (George et al., 2000), N-chloro-4-methylbenzenesulfonamde (Olmstead & Power, 1986) and N-chloro-2-methyl-4-chlorobenzenesulfonamde (Gowda et al., 2007). There is no interaction between the nitrogen and sodium atoms in the molecule, and Na+ is attached to one of the sulfonyl O atoms. Na+ coordination sphere involves oxygen from waters of crystallization and neighbouring molecules. Na+ ion coordination in the structure is also similar giving rise to several hydrogen bonding between water hydrogen, oxygen and other atoms in the molecule as shown in Figures 2 and 3. The S—N distances of 1.584 (5)Å and 1.590 (5)Å are in agreement with those of similar compounds, consistent with a S—N double bond.

Related literature top

For related literature, see: George et al. (2000); Gowda & Kumar (2003); Gowda & Shetty (2004); Gowda et al. (2002, 2005, 2007); Gowda, D'Souza & Fuess (2003); Gowda, D'Souza & Kumar (2003); Gowda, Jyothi, Kozisek & Fuess (2003); Olmstead & Power (1986).

Experimental top

The title compound was prepared according to the literature method (Gowda, D'Souza & Fuess 2003; Gowda, D'Souza & Kumar, 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared, NMR and NQR spectra. Single crystals of the title compound were obtained from a slow evaporation of its chloroform solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed down the axis b.
[Figure 3] Fig. 3. Typical Hydrogen bond bridges observed in the title compound.
Sodium 4,N-dichlorobenzenesulfonamidate sesquihydrate top
Crystal data top
Na+·C6H4Cl2NO2S−·1.5H2OF(000) = 1112
Mr = 275.09Dx = 1.732 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3193 reflections
a = 6.7041 (4) Åθ = 3.4–25.5°
b = 10.4763 (8) ŵ = 0.84 mm−1
c = 30.037 (2) ÅT = 303 K
V = 2109.6 (2) Å3Laminar, colourless
Z = 80.30 × 0.12 × 0.04 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector		4281 independent reflections
Radiation source: fine-focus sealed tube2959 reflections with I > 2σ(I)
graphiteRint = 0.079
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 4.1°
Absorption correction: analytical
CrysAlis RED (Oxford Diffraction, 2002)		h = −8→5
Tmin = 0.865, Tmax = 0.962k = −12→13
14393 measured reflectionsl = −37→37
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)] = 0.068H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.052P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.039
4281 reflectionsΔρmax = 0.41 e Å−3
280 parametersΔρmin = −0.32 e Å−3
9 restraintsAbsolute structure: Flack (1983), 1777 Friedel pairs'
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.22 (12)
Crystal data top
Na+·C6H4Cl2NO2S−·1.5H2OV = 2109.6 (2) Å3
Mr = 275.09Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 6.7041 (4) ŵ = 0.84 mm−1
b = 10.4763 (8) ÅT = 303 K
c = 30.037 (2) Å0.30 × 0.12 × 0.04 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with Sapphire CCD detector		4281 independent reflections
Absorption correction: analytical
CrysAlis RED (Oxford Diffraction, 2002)		2959 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.962Rint = 0.079
14393 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.068H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140Δρmax = 0.41 e Å−3
S = 1.10Δρmin = −0.32 e Å−3
4281 reflectionsAbsolute structure: Flack (1983), 1777 Friedel pairs'
280 parametersFlack parameter: 0.22 (12)
9 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
C10.2166 (9)0.6230 (6)0.1339 (2)0.0233 (15)
C20.1376 (9)0.5182 (7)0.1569 (2)0.0363 (17)
H20.14200.43660.14480.044*
C30.0543 (10)0.5394 (8)0.1977 (2)0.045 (2)
H3−0.00310.47150.21300.054*
C40.0533 (10)0.6565 (8)0.2162 (2)0.0388 (18)
C50.1311 (11)0.7599 (8)0.1944 (3)0.048 (2)
H50.12800.84020.20760.058*
C60.2147 (10)0.7438 (6)0.1525 (2)0.0376 (18)
H60.26840.81290.13720.045*
C70.2101 (9)0.4255 (6)−0.1317 (2)0.0219 (14)
C80.2049 (11)0.5461 (7)−0.1490 (2)0.0412 (18)
H80.25600.6134−0.13230.049*
C90.1272 (10)0.5704 (7)−0.1899 (3)0.042 (2)
H90.12700.6528−0.20150.050*
C100.0489 (10)0.4707 (8)−0.2138 (2)0.0407 (19)
C110.0500 (11)0.3466 (7)−0.1974 (2)0.0390 (18)
H11−0.00170.2797−0.21410.047*
C120.1303 (9)0.3247 (6)−0.1551 (2)0.0326 (17)
H120.12980.2431−0.14300.039*
N10.4918 (6)0.4958 (5)0.08230 (17)0.0320 (13)
N20.5112 (7)0.4835 (5)−0.07515 (16)0.0275 (12)
O10.1710 (6)0.5457 (4)0.05205 (13)0.0322 (11)
O20.1801 (6)0.4532 (4)−0.04620 (14)0.0345 (11)
O30.3891 (7)0.7264 (4)0.06666 (15)0.0413 (13)
O40.8701 (7)0.7723 (4)0.04198 (15)0.0366 (12)
H41O0.839 (10)0.724 (4)0.0632 (14)0.044*
H42O0.915 (9)0.842 (3)0.0521 (18)0.044*
O5−0.2356 (6)0.5018 (6)0.00285 (14)0.0383 (11)
H51O−0.306 (7)0.487 (7)−0.0200 (10)0.046*
H52O−0.319 (6)0.510 (7)0.0245 (11)0.046*
O60.3547 (7)0.2708 (4)0.03900 (16)0.0398 (12)
H61O0.376 (10)0.204 (3)0.0553 (18)0.048*
H62O0.411 (9)0.332 (4)0.0535 (18)0.048*
O70.3489 (6)0.2636 (4)−0.07503 (14)0.0346 (11)
S10.3222 (2)0.60178 (14)0.08011 (5)0.0255 (4)
S20.3159 (2)0.39894 (14)−0.07852 (5)0.0241 (4)
Cl10.6828 (3)0.54516 (18)0.11769 (6)0.0432 (5)
Cl20.6858 (3)0.43230 (17)−0.11428 (6)0.0436 (5)
Cl3−0.0432 (3)0.6788 (3)0.26962 (6)0.0706 (7)
Cl4−0.0464 (3)0.4965 (2)−0.26702 (6)0.0584 (6)
Na10.5463 (4)0.8486 (2)0.01367 (8)0.0327 (6)
Na20.0289 (4)0.3492 (2)0.01858 (8)0.0336 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.021 (3)0.023 (4)0.026 (3)−0.007 (3)−0.003 (3)−0.003 (3)
C20.041 (4)0.033 (4)0.035 (4)0.004 (3)0.008 (3)−0.002 (3)
C30.038 (4)0.061 (6)0.036 (4)−0.001 (4)0.011 (4)0.012 (4)
C40.025 (4)0.071 (6)0.021 (4)−0.004 (4)0.006 (3)−0.013 (4)
C50.056 (5)0.049 (5)0.039 (5)−0.003 (4)0.001 (4)−0.020 (4)
C60.044 (4)0.028 (4)0.041 (4)0.003 (4)0.014 (4)−0.002 (3)
C70.015 (3)0.027 (4)0.023 (3)0.012 (3)−0.001 (3)0.002 (3)
C80.047 (4)0.037 (4)0.039 (4)−0.004 (4)−0.010 (4)0.003 (3)
C90.040 (4)0.042 (4)0.043 (5)−0.008 (4)−0.015 (4)0.021 (4)
C100.023 (3)0.066 (6)0.033 (4)0.009 (4)−0.002 (3)0.020 (4)
C110.049 (4)0.039 (4)0.030 (4)−0.003 (4)−0.016 (4)−0.009 (3)
C120.038 (4)0.026 (4)0.034 (4)−0.003 (3)−0.001 (3)−0.007 (3)
N10.027 (3)0.038 (3)0.031 (3)−0.001 (3)−0.007 (2)−0.005 (3)
N20.025 (3)0.035 (3)0.022 (3)0.001 (2)0.004 (2)−0.005 (3)
O10.029 (2)0.041 (3)0.027 (2)0.006 (2)−0.008 (2)−0.004 (2)
O20.035 (2)0.045 (3)0.023 (2)0.004 (2)0.011 (2)0.001 (2)
O30.059 (3)0.031 (3)0.034 (3)−0.010 (2)0.006 (2)0.004 (2)
O40.039 (3)0.027 (3)0.044 (3)−0.002 (2)0.003 (2)−0.005 (2)
O50.029 (2)0.054 (3)0.031 (3)0.004 (3)−0.002 (2)−0.002 (2)
O60.040 (3)0.031 (3)0.049 (3)0.006 (3)−0.002 (2)0.000 (2)
O70.049 (3)0.028 (2)0.027 (2)0.003 (2)−0.005 (2)−0.003 (2)
S10.0274 (9)0.0283 (9)0.0206 (8)0.0012 (8)−0.0010 (8)0.0019 (7)
S20.0274 (9)0.0252 (9)0.0198 (8)−0.0001 (8)−0.0027 (8)0.0005 (7)
Cl10.0306 (9)0.0603 (12)0.0386 (10)−0.0009 (9)−0.0082 (9)0.0034 (10)
Cl20.0330 (10)0.0552 (11)0.0426 (11)0.0059 (9)0.0097 (9)0.0101 (9)
Cl30.0490 (11)0.128 (2)0.0349 (11)−0.0072 (13)0.0123 (11)−0.0199 (13)
Cl40.0469 (10)0.0969 (17)0.0313 (10)0.0015 (12)−0.0133 (10)0.0145 (11)
Na10.0331 (14)0.0343 (15)0.0307 (14)−0.0085 (13)0.0027 (13)0.0041 (12)
Na20.0316 (14)0.0309 (15)0.0384 (15)−0.0046 (13)0.0013 (13)0.0051 (12)
Geometric parameters (Å, °) top
C1—C61.382 (9)O2—S21.447 (4)
C1—C21.401 (9)O2—Na22.450 (5)
C1—S11.779 (6)O2—Na1i2.464 (5)
C2—C31.363 (9)O3—S11.438 (5)
C2—H20.9300O3—Na12.298 (5)
C3—C41.348 (10)O4—Na1ii2.407 (5)
C3—H30.9300O4—Na12.465 (5)
C4—C51.369 (10)O4—H41O0.842 (19)
C4—Cl31.745 (7)O4—H42O0.841 (19)
C5—C61.389 (10)O5—Na22.433 (5)
C5—H50.9300O5—Na1i2.505 (5)
C6—H60.9300O5—H51O0.848 (19)
C7—C81.366 (9)O5—H52O0.861 (19)
C7—C121.377 (8)O6—Na22.413 (5)
C7—S21.770 (6)O6—Na2iii2.437 (6)
C8—C91.360 (9)O6—H61O0.87 (2)
C8—H80.9300O6—H62O0.86 (2)
C9—C101.372 (10)O7—S21.439 (4)
C9—H90.9300O7—Na2iii2.393 (5)
C10—C111.391 (9)Na1—O4i2.407 (5)
C10—Cl41.742 (7)Na1—O1ii2.413 (5)
C11—C121.397 (9)Na1—O2ii2.464 (5)
C11—H110.9300Na1—O5ii2.505 (5)
C12—H120.9300Na1—Na2ii3.313 (3)
N1—S11.590 (5)Na1—Na1i4.022 (3)
N1—Cl11.743 (5)Na1—Na1ii4.022 (3)
N2—S21.584 (5)Na2—O7iv2.393 (5)
N2—Cl21.743 (5)Na2—O6iv2.437 (6)
O1—S11.443 (4)Na2—Na1i3.313 (3)
O1—Na1i2.413 (5)Na2—Na2iv4.100 (3)
O1—Na22.481 (5)Na2—Na2iii4.100 (3)
C6—C1—C2121.0 (6)O2—S2—C7107.0 (3)
C6—C1—S1119.0 (5)N2—S2—C7107.5 (3)
C2—C1—S1120.0 (5)O3—Na1—O4i87.87 (18)
C3—C2—C1118.1 (7)O3—Na1—O1ii168.82 (19)
C3—C2—H2121.0O4i—Na1—O1ii80.99 (17)
C1—C2—H2121.0O3—Na1—O2ii111.21 (17)
C4—C3—C2121.4 (7)O4i—Na1—O2ii153.84 (19)
C4—C3—H3119.3O1ii—Na1—O2ii79.13 (16)
C2—C3—H3119.3O3—Na1—O489.11 (18)
C3—C4—C5121.4 (6)O4i—Na1—O4120.08 (15)
C3—C4—Cl3120.2 (6)O1ii—Na1—O497.22 (17)
C5—C4—Cl3118.4 (6)O2ii—Na1—O479.37 (16)
C4—C5—C6119.5 (7)O3—Na1—O5ii98.04 (18)
C4—C5—H5120.3O4i—Na1—O5ii79.73 (17)
C6—C5—H5120.3O1ii—Na1—O5ii79.17 (16)
C1—C6—C5118.7 (7)O2ii—Na1—O5ii79.97 (17)
C1—C6—H6120.6O4—Na1—O5ii159.34 (19)
C5—C6—H6120.6O3—Na1—Na2ii135.94 (16)
C8—C7—C12120.3 (6)O4i—Na1—Na2ii106.41 (15)
C8—C7—S2119.9 (5)O1ii—Na1—Na2ii48.27 (12)
C12—C7—S2119.7 (5)O2ii—Na1—Na2ii47.43 (11)
C9—C8—C7121.8 (7)O4—Na1—Na2ii116.21 (14)
C9—C8—H8119.1O5ii—Na1—Na2ii46.95 (13)
C7—C8—H8119.1O3—Na1—Na1i58.21 (13)
C8—C9—C10118.5 (7)O4i—Na1—Na1i34.82 (13)
C8—C9—H9120.8O1ii—Na1—Na1i110.94 (14)
C10—C9—H9120.8O2ii—Na1—Na1i144.81 (14)
C9—C10—C11121.6 (6)O4—Na1—Na1i129.66 (16)
C9—C10—Cl4120.1 (6)O5ii—Na1—Na1i69.65 (13)
C11—C10—Cl4118.2 (6)Na2ii—Na1—Na1i113.68 (9)
C10—C11—C12118.6 (7)O3—Na1—Na1ii103.73 (16)
C10—C11—H11120.7O4i—Na1—Na1ii89.82 (15)
C12—C11—H11120.7O1ii—Na1—Na1ii77.28 (12)
C7—C12—C11119.2 (6)O2ii—Na1—Na1ii102.14 (12)
C7—C12—H12120.4O4—Na1—Na1ii33.89 (11)
C11—C12—H12120.4O5ii—Na1—Na1ii155.46 (15)
S1—N1—Cl1110.1 (3)Na2ii—Na1—Na1ii117.42 (9)
S2—N2—Cl2109.9 (3)Na1i—Na1—Na1ii112.90 (12)
S1—O1—Na1i122.3 (3)O7iv—Na2—O696.20 (18)
S1—O1—Na2147.6 (3)O7iv—Na2—O595.44 (17)
Na1i—O1—Na285.19 (15)O6—Na2—O5158.84 (19)
S2—O2—Na2128.2 (3)O7iv—Na2—O6iv90.36 (17)
S2—O2—Na1i145.7 (3)O6—Na2—O6iv116.01 (15)
Na2—O2—Na1i84.77 (15)O5—Na2—O6iv81.49 (18)
S1—O3—Na1147.5 (3)O7iv—Na2—O2172.32 (18)
Na1ii—O4—Na1111.29 (19)O6—Na2—O288.76 (17)
Na1ii—O4—H41O109 (4)O5—Na2—O281.69 (16)
Na1—O4—H41O104 (5)O6iv—Na2—O282.19 (17)
Na1ii—O4—H42O122 (4)O7iv—Na2—O1108.44 (17)
Na1—O4—H42O99 (5)O6—Na2—O180.31 (16)
H41O—O4—H42O110 (3)O5—Na2—O179.27 (17)
Na2—O5—Na1i84.24 (14)O6iv—Na2—O1154.16 (19)
Na2—O5—H51O116 (5)O2—Na2—O178.11 (16)
Na1i—O5—H51O112 (4)O7iv—Na2—Na1i134.19 (15)
Na2—O5—H52O113 (4)O6—Na2—Na1i111.57 (14)
Na1i—O5—H52O125 (4)O5—Na2—Na1i48.80 (13)
H51O—O5—H52O106 (3)O6iv—Na2—Na1i107.62 (15)
Na2—O6—Na2iii115.42 (19)O2—Na2—Na1i47.80 (12)
Na2—O6—H61O125 (4)O1—Na2—Na1i46.54 (11)
Na2iii—O6—H61O84 (5)O7iv—Na2—Na2iv61.98 (12)
Na2—O6—H62O106 (4)O6—Na2—Na2iv129.55 (16)
Na2iii—O6—H62O122 (5)O5—Na2—Na2iv71.60 (13)
H61O—O6—H62O104 (3)O6iv—Na2—Na2iv32.11 (12)
S2—O7—Na2iii128.0 (3)O2—Na2—Na2iv110.35 (15)
O3—S1—O1115.1 (3)O1—Na2—Na2iv147.69 (13)
O3—S1—N1115.0 (3)Na1i—Na2—Na2iv115.72 (10)
O1—S1—N1104.0 (3)O7iv—Na2—Na2iii110.76 (15)
O3—S1—C1105.4 (3)O6—Na2—Na2iii32.47 (11)
O1—S1—C1107.6 (3)O5—Na2—Na2iii151.17 (16)
N1—S1—C1109.5 (3)O6iv—Na2—Na2iii86.37 (15)
O7—S2—O2115.8 (3)O2—Na2—Na2iii70.77 (12)
O7—S2—N2114.8 (3)O1—Na2—Na2iii102.54 (11)
O2—S2—N2104.9 (3)Na1i—Na2—Na2iii112.10 (9)
O7—S2—C7106.4 (3)Na2iv—Na2—Na2iii109.70 (12)
C6—C1—C2—C31.7 (10)S1—O3—Na1—O2ii−157.2 (5)
S1—C1—C2—C3−178.6 (5)S1—O3—Na1—O4−78.9 (6)
C1—C2—C3—C4−2.3 (10)S1—O3—Na1—O5ii120.5 (5)
C2—C3—C4—C51.8 (11)S1—O3—Na1—Na2ii152.8 (5)
C2—C3—C4—Cl3−176.7 (5)S1—O3—Na1—Na1i60.6 (5)
C3—C4—C5—C6−0.7 (11)S1—O3—Na1—Na1ii−48.1 (6)
Cl3—C4—C5—C6177.9 (5)Na1ii—O4—Na1—O3116.7 (2)
C2—C1—C6—C5−0.6 (10)Na1ii—O4—Na1—O4i29.7 (2)
S1—C1—C6—C5179.7 (5)Na1ii—O4—Na1—O1ii−54.1 (2)
C4—C5—C6—C10.1 (11)Na1ii—O4—Na1—O2ii−131.5 (2)
C12—C7—C8—C9−1.9 (11)Na1ii—O4—Na1—O5ii−132.5 (5)
S2—C7—C8—C9179.2 (6)Na1ii—O4—Na1—Na2ii−100.81 (19)
C7—C8—C9—C101.2 (11)Na1ii—O4—Na1—Na1i70.9 (3)
C8—C9—C10—C11−0.8 (11)Na2iii—O6—Na2—O7iv119.6 (2)
C8—C9—C10—Cl4−178.3 (6)Na2iii—O6—Na2—O5−117.4 (5)
C9—C10—C11—C121.0 (11)Na2iii—O6—Na2—O6iv26.1 (2)
Cl4—C10—C11—C12178.6 (5)Na2iii—O6—Na2—O2−54.6 (2)
C8—C7—C12—C112.1 (10)Na2iii—O6—Na2—O1−132.7 (2)
S2—C7—C12—C11−179.0 (5)Na2iii—O6—Na2—Na1i−97.6 (2)
C10—C11—C12—C7−1.7 (10)Na2iii—O6—Na2—Na2iv61.1 (3)
Na1—O3—S1—O1−64.0 (6)Na1i—O5—Na2—O7iv147.92 (16)
Na1—O3—S1—N156.9 (6)Na1i—O5—Na2—O624.8 (6)
Na1—O3—S1—C1177.6 (5)Na1i—O5—Na2—O6iv−122.54 (16)
Na1i—O1—S1—O31.5 (4)Na1i—O5—Na2—O2−39.25 (15)
Na2—O1—S1—O3145.6 (5)Na1i—O5—Na2—O140.13 (15)
Na1i—O1—S1—N1−125.2 (3)Na1i—O5—Na2—Na2iv−154.02 (14)
Na2—O1—S1—N118.9 (5)Na1i—O5—Na2—Na2iii−56.4 (3)
Na1i—O1—S1—C1118.7 (3)S2—O2—Na2—O7iv−81.8 (15)
Na2—O1—S1—C1−97.2 (5)Na1i—O2—Na2—O7iv108.5 (14)
Cl1—N1—S1—O356.3 (4)S2—O2—Na2—O648.6 (3)
Cl1—N1—S1—O1−176.9 (3)Na1i—O2—Na2—O6−121.07 (17)
Cl1—N1—S1—C1−62.1 (4)S2—O2—Na2—O5−150.3 (3)
C6—C1—S1—O30.2 (6)Na1i—O2—Na2—O539.99 (16)
C2—C1—S1—O3−179.5 (5)S2—O2—Na2—O6iv−67.8 (3)
C6—C1—S1—O1−123.1 (5)Na1i—O2—Na2—O6iv122.47 (17)
C2—C1—S1—O157.2 (6)S2—O2—Na2—O1129.0 (3)
C6—C1—S1—N1124.5 (5)Na1i—O2—Na2—O1−40.71 (14)
C2—C1—S1—N1−55.3 (6)S2—O2—Na2—Na1i169.7 (4)
Na2iii—O7—S2—O2−70.9 (4)S2—O2—Na2—Na2iv−83.5 (3)
Na2iii—O7—S2—N251.7 (4)Na1i—O2—Na2—Na2iv106.77 (14)
Na2iii—O7—S2—C7170.4 (3)S2—O2—Na2—Na2iii21.0 (3)
Na2—O2—S2—O77.5 (4)Na1i—O2—Na2—Na2iii−148.67 (15)
Na1i—O2—S2—O7169.1 (4)S1—O1—Na2—O7iv75.7 (5)
Na2—O2—S2—N2−120.1 (3)Na1i—O1—Na2—O7iv−134.14 (17)
Na1i—O2—S2—N241.4 (5)S1—O1—Na2—O6−17.7 (5)
Na2—O2—S2—C7125.9 (3)Na1i—O1—Na2—O6132.51 (17)
Na1i—O2—S2—C7−72.5 (5)S1—O1—Na2—O5167.9 (5)
Cl2—N2—S2—O754.2 (4)Na1i—O1—Na2—O5−41.93 (15)
Cl2—N2—S2—O2−177.6 (3)S1—O1—Na2—O6iv−149.6 (4)
Cl2—N2—S2—C7−64.0 (4)Na1i—O1—Na2—O6iv0.6 (5)
C8—C7—S2—O7−164.6 (6)S1—O1—Na2—O2−108.4 (5)
C12—C7—S2—O716.5 (6)Na1i—O1—Na2—O241.73 (15)
C8—C7—S2—O271.0 (6)S1—O1—Na2—Na1i−150.2 (6)
C12—C7—S2—O2−107.9 (5)S1—O1—Na2—Na2iv142.2 (4)
C8—C7—S2—N2−41.2 (6)Na1i—O1—Na2—Na2iv−67.7 (3)
C12—C7—S2—N2139.9 (5)S1—O1—Na2—Na2iii−41.5 (5)
S1—O3—Na1—O4i41.2 (6)Na1i—O1—Na2—Na2iii108.68 (13)
S1—O3—Na1—O1ii45.8 (14)
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z; (iii) x+1/2, −y+1/2, −z; (iv) x−1/2, −y+1/2, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H41O···Cl10.84 (2)2.70 (2)3.523 (5)167 (5)
O4—H42O···N2ii0.84 (2)2.06 (2)2.903 (7)177 (7)
O4—H42O···S2ii0.84 (2)2.91 (4)3.633 (5)145 (6)
O5—H51O···N2v0.85 (2)2.06 (2)2.899 (6)170 (7)
O5—H51O···Cl2v0.85 (2)2.89 (3)3.631 (5)147 (4)
O5—H52O···N1v0.86 (2)2.16 (2)3.006 (6)169 (7)
O5—H52O···Cl1v0.86 (2)2.82 (3)3.522 (5)139 (4)
O6—H61O···Cl2iv0.87 (2)2.61 (5)3.305 (5)138 (6)
O6—H61O···O2iii0.87 (2)2.63 (6)3.212 (6)125 (6)
O6—H62O···N10.86 (2)2.00 (2)2.845 (7)167 (6)
O6—H62O···S10.86 (2)3.00 (4)3.687 (5)138 (5)
Symmetry codes: (ii) x+1/2, −y+3/2, −z; (v) x−1, y, z; (iv) x−1/2, −y+1/2, −z; (iii) x+1/2, −y+1/2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H41O···Cl10.84 (2)2.70 (2)3.523 (5)167 (5)
O4—H42O···N2i0.84 (2)2.06 (2)2.903 (7)177 (7)
O4—H42O···S2i0.84 (2)2.91 (4)3.633 (5)145 (6)
O5—H51O···N2ii0.85 (2)2.06 (2)2.899 (6)170 (7)
O5—H51O···Cl2ii0.85 (2)2.89 (3)3.631 (5)147 (4)
O5—H52O···N1ii0.86 (2)2.16 (2)3.006 (6)169 (7)
O5—H52O···Cl1ii0.86 (2)2.82 (3)3.522 (5)139 (4)
O6—H61O···Cl2iii0.87 (2)2.61 (5)3.305 (5)138 (6)
O6—H61O···O2iv0.87 (2)2.63 (6)3.212 (6)125 (6)
O6—H62O···N10.86 (2)2.00 (2)2.845 (7)167 (6)
O6—H62O···S10.86 (2)3.00 (4)3.687 (5)138 (5)
Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x−1, y, z; (iii) x−1/2, −y+1/2, −z; (iv) x+1/2, −y+1/2, −z.
Acknowledgements top

BTG gratefully thanks the Alexander von Humboldt Foundation, Bonn, Germany for the extension of his research fellowship. JK thanks the Grant Agency of the Slovak Republic (grant No. 1/2449/05).

references
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