Acta Cryst. (2007). E63, m3093 [ doi:10.1107/S1600536807059065 ]
The title compound, Na+·C6H5O2S2-, at 100 (2) K has orthorhombic (Cmca) symmetry. The compound has a network structure. It is of interest with respect to inclusion phenomena and structure-activity relationships. The Na atoms are chelated by two different benzenesulfonothioate anions via ![[alpha]](http://journals.iucr.org/logos/entities/alpha_rmgif.gif)
-S and O atoms. Additional coordination by O atoms of two other benzenesulfonothioate anions results in coordination number 6 for each Na atom in the extended two-dimensional polymeric structure. The structure exhibits disorder of the anion in the two-dimensional arrangement. The phenyl group is disordered equally over two positions.
The compound was prepared by aerobic oxidation of phenylthiol and subsequent treatment with sodium sulfide in THF (yield 10%).
All H atoms were positioned in calculated positions and refined using a riding model, with C—H = 0.95 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-AREA (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
![[Figure 1]](./sg2202fig1thm.gif)
| Fig. 1. Structure of the title compound in the solid state (displacement ellipsoids are at the 50% probability level). Connections to neighbouring sodium atoms are indicated by dashed bonds. |
![[Figure 2]](./sg2202fig2thm.gif)
| Fig. 2. Packing of the title compound in the solid state (without phenyl groups). |
| Na+·C6H5O2S2– | Dx = 1.605 Mg m−3 |
| Mr = 196.21 | Mo Kα radiation λ = 0.71073 Å |
| Orthorhombic, Cmca | Cell parameters from 6649 reflections |
| Hall symbol: -c 2ac 2 | θ = 3.3–56.5º |
| a = 9.5579 (10) Å | µ = 0.65 mm−1 |
| b = 7.0127 (8) Å | T = 100 (2) K |
| c = 24.231 (3) Å | Cell measurement pressure: 100 kPa |
| V = 1624.1 (3) Å3 | Block, colourless |
| Z = 8 | 0.30 × 0.30 × 0.20 mm |
| F000 = 800 |
| Stoe IPDS 2 diffractometer | 1053 independent reflections |
| Radiation source: fine-focus sealed tube | 874 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.054 |
| Detector resolution: 6.67 pixels mm-1 | θmax = 28.3º |
| T = 100(2) K | θmin = 1.7º |
| rotation scans | h = −12→12 |
| Absorption correction: numerical (X-RED32; Stoe & Cie, 2002) | k = −9→9 |
| Tmin = 0.829, Tmax = 0.881 | l = −32→32 |
| 6658 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0377P)2 + 1.7243P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 1053 reflections | Δρmax = 0.32 e Å−3 |
| 69 parameters | Δρmin = −0.42 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| Na+·C6H5O2S2– | V = 1624.1 (3) Å3 |
| Mr = 196.21 | Z = 8 |
| Orthorhombic, Cmca | Mo Kα |
| a = 9.5579 (10) Å | µ = 0.65 mm−1 |
| b = 7.0127 (8) Å | T = 100 (2) K |
| c = 24.231 (3) Å | 0.30 × 0.30 × 0.20 mm |
| Stoe IPDS 2 diffractometer | 1053 independent reflections |
| Absorption correction: numerical (X-RED32; Stoe & Cie, 2002) | 874 reflections with I > 2σ(I) |
| Tmin = 0.829, Tmax = 0.881 | Rint = 0.054 |
| 6658 measured reflections |
| R[F2 > 2σ(F2)] = 0.032 | 69 parameters |
| wR(F2) = 0.079 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.32 e Å−3 |
| 1053 reflections | Δρmin = −0.42 e Å−3 |
Experimental. The phenyl groups are disordered over two positions (50:50). This disorder is static and a consequence of the symmetry operations. |
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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| S1 | 0.5000 | 0.24418 (9) | 0.43057 (3) | 0.01877 (16) | |
| S2 | 0.5000 | −0.02166 (10) | 0.40674 (3) | 0.02647 (18) | |
| Na1 | 0.28026 (10) | 0.0000 | 0.5000 | 0.0222 (2) | |
| O1 | 0.37188 (13) | 0.2896 (2) | 0.46085 (5) | 0.0245 (3) | |
| C1 | 0.5122 (3) | 0.3934 (3) | 0.37218 (8) | 0.0208 (6) | 0.50 |
| C2 | 0.4003 (2) | 0.5052 (4) | 0.35502 (10) | 0.0236 (7) | 0.50 |
| H2 | 0.3147 | 0.5024 | 0.3749 | 0.028* | 0.50 |
| C3 | 0.4137 (2) | 0.6210 (3) | 0.30877 (11) | 0.0276 (8) | 0.50 |
| H3 | 0.3372 | 0.6975 | 0.2970 | 0.033* | 0.50 |
| C4 | 0.5390 (3) | 0.6251 (3) | 0.27968 (9) | 0.0297 (10) | 0.50 |
| H4 | 0.5482 | 0.7043 | 0.2481 | 0.036* | 0.50 |
| C5 | 0.6509 (2) | 0.5133 (4) | 0.29684 (10) | 0.0306 (9) | 0.50 |
| H5 | 0.7366 | 0.5160 | 0.2770 | 0.037* | 0.50 |
| C6 | 0.6375 (2) | 0.3974 (3) | 0.34309 (10) | 0.0251 (8) | 0.50 |
| H6 | 0.7140 | 0.3210 | 0.3548 | 0.030* | 0.50 |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0143 (3) | 0.0198 (3) | 0.0222 (3) | 0.000 | 0.000 | −0.0004 (2) |
| S2 | 0.0264 (3) | 0.0217 (3) | 0.0313 (4) | 0.000 | 0.000 | −0.0030 (3) |
| Na1 | 0.0168 (5) | 0.0210 (5) | 0.0288 (5) | 0.000 | 0.000 | 0.0000 (4) |
| O1 | 0.0189 (6) | 0.0270 (7) | 0.0277 (7) | 0.0020 (5) | 0.0052 (5) | −0.0020 (5) |
| C1 | 0.0183 (16) | 0.0218 (12) | 0.0224 (12) | 0.000 (2) | 0.001 (2) | −0.0009 (10) |
| C2 | 0.0222 (16) | 0.0253 (18) | 0.0232 (17) | 0.0019 (15) | −0.0015 (14) | −0.0040 (15) |
| C3 | 0.031 (2) | 0.0244 (18) | 0.027 (2) | −0.0005 (17) | −0.0087 (17) | 0.0003 (16) |
| C4 | 0.039 (3) | 0.0242 (17) | 0.0262 (18) | −0.0063 (14) | −0.0034 (15) | 0.0057 (15) |
| C5 | 0.029 (2) | 0.033 (2) | 0.030 (2) | −0.0069 (18) | 0.0044 (16) | 0.0017 (18) |
| C6 | 0.0201 (17) | 0.029 (2) | 0.0257 (19) | −0.0029 (16) | 0.0008 (15) | 0.0015 (16) |
| S1—O1 | 1.4627 (13) | Na1—Na1iv | 3.5537 (5) |
| S1—O1i | 1.4627 (13) | Na1—Na1vi | 3.5537 (5) |
| S1—C1i | 1.7636 (18) | Na1—Na1ii | 4.201 (2) |
| S1—C1 | 1.7636 (18) | O1—Na1iv | 2.2784 (14) |
| S1—S2 | 1.9517 (10) | C1—C2 | 1.3900 |
| S1—Na1 | 3.1896 (8) | C1—C6 | 1.3900 |
| S1—Na1ii | 3.1897 (8) | C2—C3 | 1.3900 |
| S2—Na1 | 3.0889 (9) | C2—H2 | 0.9500 |
| S2—Na1ii | 3.0889 (9) | C3—C4 | 1.3900 |
| Na1—O1iii | 2.2784 (14) | C3—H3 | 0.9500 |
| Na1—O1iv | 2.2784 (14) | C4—C5 | 1.3900 |
| Na1—O1 | 2.4065 (14) | C4—H4 | 0.9500 |
| Na1—O1v | 2.4066 (14) | C5—C6 | 1.3900 |
| Na1—S2ii | 3.0889 (9) | C5—H5 | 0.9500 |
| Na1—S1ii | 3.1896 (8) | C6—H6 | 0.9500 |
| O1—S1—O1i | 113.68 (11) | S2—Na1—S1 | 36.176 (19) |
| O1—S1—C1i | 102.58 (11) | S1ii—Na1—S1 | 97.63 (3) |
| O1i—S1—C1i | 109.19 (11) | O1iii—Na1—Na1iv | 122.35 (5) |
| O1—S1—C1 | 109.19 (10) | O1iv—Na1—Na1iv | 42.03 (4) |
| O1i—S1—C1 | 102.58 (11) | O1—Na1—Na1iv | 39.34 (3) |
| C1i—S1—C1 | 7.60 (18) | O1v—Na1—Na1iv | 153.11 (4) |
| O1—S1—S2 | 110.89 (6) | S2ii—Na1—Na1iv | 93.56 (2) |
| O1i—S1—S2 | 110.89 (6) | S2—Na1—Na1iv | 99.16 (2) |
| C1i—S1—S2 | 109.23 (9) | S1ii—Na1—Na1iv | 129.56 (3) |
| C1—S1—S2 | 109.23 (9) | S1—Na1—Na1iv | 65.01 (2) |
| O1—S1—Na1 | 45.66 (6) | O1iii—Na1—Na1vi | 42.03 (4) |
| O1i—S1—Na1 | 113.80 (6) | O1iv—Na1—Na1vi | 122.35 (5) |
| C1i—S1—Na1 | 134.27 (9) | O1—Na1—Na1vi | 153.11 (4) |
| C1—S1—Na1 | 141.75 (9) | O1v—Na1—Na1vi | 39.34 (3) |
| S2—S1—Na1 | 69.10 (2) | S2ii—Na1—Na1vi | 99.16 (2) |
| O1—S1—Na1ii | 113.80 (6) | S2—Na1—Na1vi | 93.56 (2) |
| O1i—S1—Na1ii | 45.66 (6) | S1ii—Na1—Na1vi | 65.01 (2) |
| C1i—S1—Na1ii | 141.75 (9) | S1—Na1—Na1vi | 129.56 (3) |
| C1—S1—Na1ii | 134.27 (9) | Na1iv—Na1—Na1vi | 161.27 (6) |
| S2—S1—Na1ii | 69.10 (2) | O1iii—Na1—Na1ii | 129.66 (4) |
| Na1—S1—Na1ii | 82.37 (3) | O1iv—Na1—Na1ii | 129.66 (4) |
| S1—S2—Na1 | 74.72 (2) | O1—Na1—Na1ii | 68.66 (4) |
| S1—S2—Na1ii | 74.72 (2) | O1v—Na1—Na1ii | 68.66 (4) |
| Na1—S2—Na1ii | 85.68 (3) | S2ii—Na1—Na1ii | 47.160 (17) |
| O1iii—Na1—O1iv | 100.68 (8) | S2—Na1—Na1ii | 47.161 (17) |
| O1iii—Na1—O1 | 127.93 (6) | S1ii—Na1—Na1ii | 48.816 (15) |
| O1iv—Na1—O1 | 81.37 (5) | S1—Na1—Na1ii | 48.817 (15) |
| O1iii—Na1—O1v | 81.37 (5) | Na1iv—Na1—Na1ii | 99.37 (3) |
| O1iv—Na1—O1v | 127.92 (6) | Na1vi—Na1—Na1ii | 99.37 (3) |
| O1—Na1—O1v | 137.32 (8) | S1—O1—Na1iv | 152.16 (9) |
| O1iii—Na1—S2ii | 140.39 (4) | S1—O1—Na1 | 108.58 (8) |
| O1iv—Na1—S2ii | 95.60 (4) | Na1iv—O1—Na1 | 98.63 (5) |
| O1—Na1—S2ii | 89.97 (4) | C2—C1—C6 | 120.0 |
| O1v—Na1—S2ii | 60.38 (4) | C2—C1—S1 | 121.58 (15) |
| O1iii—Na1—S2 | 95.60 (4) | C6—C1—S1 | 118.42 (15) |
| O1iv—Na1—S2 | 140.39 (4) | C1—C2—C3 | 120.0 |
| O1—Na1—S2 | 60.38 (4) | C1—C2—H2 | 120.0 |
| O1v—Na1—S2 | 89.97 (4) | C3—C2—H2 | 120.0 |
| S2ii—Na1—S2 | 94.32 (3) | C4—C3—C2 | 120.0 |
| O1iii—Na1—S1ii | 106.99 (4) | C4—C3—H3 | 120.0 |
| O1iv—Na1—S1ii | 123.25 (4) | C2—C3—H3 | 120.0 |
| O1—Na1—S1ii | 114.92 (5) | C3—C4—C5 | 120.0 |
| O1v—Na1—S1ii | 25.76 (3) | C3—C4—H4 | 120.0 |
| S2ii—Na1—S1ii | 36.175 (19) | C5—C4—H4 | 120.0 |
| S2—Na1—S1ii | 84.94 (3) | C4—C5—C6 | 120.0 |
| O1iii—Na1—S1 | 123.25 (4) | C4—C5—H5 | 120.0 |
| O1iv—Na1—S1 | 106.99 (4) | C6—C5—H5 | 120.0 |
| O1—Na1—S1 | 25.76 (3) | C5—C6—C1 | 120.0 |
| O1v—Na1—S1 | 114.92 (5) | C5—C6—H6 | 120.0 |
| S2ii—Na1—S1 | 84.94 (3) | C1—C6—H6 | 120.0 |
| O1—S1—S2—Na1 | −18.83 (6) | C1i—S1—Na1—S1ii | 167.38 (13) |
| O1i—S1—S2—Na1 | 108.46 (7) | C1—S1—Na1—S1ii | 165.36 (14) |
| C1i—S1—S2—Na1 | −131.16 (10) | S2—S1—Na1—S1ii | 70.48 (2) |
| C1—S1—S2—Na1 | −139.21 (9) | O1—S1—Na1—Na1iv | −4.18 (7) |
| Na1ii—S1—S2—Na1 | 89.63 (3) | O1i—S1—Na1—Na1iv | 96.36 (7) |
| O1—S1—S2—Na1ii | −108.46 (7) | C1i—S1—Na1—Na1iv | −62.35 (13) |
| O1i—S1—S2—Na1ii | 18.82 (6) | C1—S1—Na1—Na1iv | −64.36 (14) |
| C1i—S1—S2—Na1ii | 139.21 (9) | S2—S1—Na1—Na1iv | −159.24 (3) |
| C1—S1—S2—Na1ii | 131.16 (10) | Na1ii—S1—Na1—Na1iv | 130.28 (2) |
| Na1—S1—S2—Na1ii | −89.63 (3) | O1—S1—Na1—Na1vi | 161.79 (9) |
| S1—S2—Na1—O1iii | 143.07 (4) | O1i—S1—Na1—Na1vi | −97.67 (7) |
| Na1ii—S2—Na1—O1iii | −141.60 (4) | C1i—S1—Na1—Na1vi | 103.62 (13) |
| S1—S2—Na1—O1iv | 28.83 (7) | C1—S1—Na1—Na1vi | 101.61 (14) |
| Na1ii—S2—Na1—O1iv | 104.16 (7) | S2—S1—Na1—Na1vi | 6.73 (4) |
| S1—S2—Na1—O1 | 12.17 (4) | Na1ii—S1—Na1—Na1vi | −63.75 (4) |
| Na1ii—S2—Na1—O1 | 87.50 (4) | O1—S1—Na1—Na1ii | −134.45 (8) |
| S1—S2—Na1—O1v | −135.61 (4) | O1i—S1—Na1—Na1ii | −33.92 (6) |
| Na1ii—S2—Na1—O1v | −60.28 (4) | C1i—S1—Na1—Na1ii | 167.38 (13) |
| S1—S2—Na1—S2ii | −75.331 (19) | C1—S1—Na1—Na1ii | 165.36 (14) |
| S1—S2—Na1—S1ii | −110.31 (2) | S2—S1—Na1—Na1ii | 70.48 (2) |
| Na1ii—S2—Na1—S1ii | −34.977 (17) | O1i—S1—O1—Na1iv | 66.5 (2) |
| Na1ii—S2—Na1—S1 | 75.331 (19) | C1i—S1—O1—Na1iv | −51.3 (2) |
| S1—S2—Na1—Na1iv | 18.99 (3) | C1—S1—O1—Na1iv | −47.4 (2) |
| Na1ii—S2—Na1—Na1iv | 94.32 (3) | S2—S1—O1—Na1iv | −167.80 (15) |
| S1—S2—Na1—Na1vi | −174.81 (3) | Na1—S1—O1—Na1iv | 167.3 (2) |
| Na1ii—S2—Na1—Na1vi | −99.48 (3) | Na1ii—S1—O1—Na1iv | 116.62 (17) |
| S1—S2—Na1—Na1ii | −75.331 (19) | O1i—S1—O1—Na1 | −100.80 (10) |
| O1—S1—Na1—O1iii | 109.42 (8) | C1i—S1—O1—Na1 | 141.44 (10) |
| O1i—S1—Na1—O1iii | −150.05 (10) | C1—S1—O1—Na1 | 145.33 (11) |
| C1i—S1—Na1—O1iii | 51.25 (14) | S2—S1—O1—Na1 | 24.93 (8) |
| C1—S1—Na1—O1iii | 49.23 (15) | Na1ii—S1—O1—Na1 | −50.65 (8) |
| S2—S1—Na1—O1iii | −45.65 (5) | O1iii—Na1—O1—S1 | −89.13 (7) |
| Na1ii—S1—Na1—O1iii | −116.13 (5) | O1iv—Na1—O1—S1 | 174.02 (11) |
| O1—S1—Na1—O1iv | −6.18 (11) | O1v—Na1—O1—S1 | 35.23 (6) |
| O1i—S1—Na1—O1iv | 94.36 (6) | S2ii—Na1—O1—S1 | 78.36 (7) |
| C1i—S1—Na1—O1iv | −64.35 (13) | S2—Na1—O1—S1 | −16.63 (5) |
| C1—S1—Na1—O1iv | −66.37 (15) | S1ii—Na1—O1—S1 | 51.27 (8) |
| S2—S1—Na1—O1iv | −161.25 (4) | Na1iv—Na1—O1—S1 | 174.02 (11) |
| Na1ii—S1—Na1—O1iv | 128.27 (4) | Na1vi—Na1—O1—S1 | −32.18 (16) |
| O1i—S1—Na1—O1 | 100.54 (13) | Na1ii—Na1—O1—S1 | 35.23 (6) |
| C1i—S1—Na1—O1 | −58.17 (14) | O1iii—Na1—O1—Na1iv | 96.85 (9) |
| C1—S1—Na1—O1 | −60.19 (16) | O1v—Na1—O1—Na1iv | −138.80 (5) |
| S2—S1—Na1—O1 | −155.07 (8) | S2ii—Na1—O1—Na1iv | −95.67 (4) |
| Na1ii—S1—Na1—O1 | 134.45 (8) | S2—Na1—O1—Na1iv | 169.34 (6) |
| O1—S1—Na1—O1v | −154.46 (6) | S1ii—Na1—O1—Na1iv | −122.75 (4) |
| O1i—S1—Na1—O1v | −53.92 (9) | S1—Na1—O1—Na1iv | −174.02 (11) |
| C1i—S1—Na1—O1v | 147.37 (13) | Na1vi—Na1—O1—Na1iv | 153.79 (12) |
| C1—S1—Na1—O1v | 145.35 (14) | Na1ii—Na1—O1—Na1iv | −138.80 (5) |
| S2—S1—Na1—O1v | 50.48 (4) | O1—S1—C1—C2 | −11.20 (17) |
| Na1ii—S1—Na1—O1v | −20.01 (4) | O1i—S1—C1—C2 | −132.10 (14) |
| O1—S1—Na1—S2ii | −100.50 (8) | C1i—S1—C1—C2 | 18.88 (14) |
| O1i—S1—Na1—S2ii | 0.04 (7) | S2—S1—C1—C2 | 110.21 (13) |
| C1i—S1—Na1—S2ii | −158.67 (13) | Na1—S1—C1—C2 | 29.9 (2) |
| C1—S1—Na1—S2ii | −160.69 (14) | Na1ii—S1—C1—C2 | −170.60 (10) |
| S2—S1—Na1—S2ii | 104.44 (3) | O1—S1—C1—C6 | 168.83 (12) |
| Na1ii—S1—Na1—S2ii | 33.953 (17) | O1i—S1—C1—C6 | 47.94 (15) |
| O1—S1—Na1—S2 | 155.07 (8) | C1i—S1—C1—C6 | −161.08 (13) |
| O1i—S1—Na1—S2 | −104.40 (7) | S2—S1—C1—C6 | −69.76 (14) |
| C1i—S1—Na1—S2 | 96.90 (13) | Na1—S1—C1—C6 | −150.09 (11) |
| C1—S1—Na1—S2 | 94.88 (14) | Na1ii—S1—C1—C6 | 9.4 (2) |
| Na1ii—S1—Na1—S2 | −70.48 (2) | S1—C1—C2—C3 | −180.0 (2) |
| O1—S1—Na1—S1ii | −134.45 (8) | S1—C1—C6—C5 | 179.97 (19) |
| O1i—S1—Na1—S1ii | −33.92 (6) |
| Symmetry codes: (i) −x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, z; (iv) −x+1/2, −y+1/2, −z+1; (v) x, −y, −z+1; (vi) −x+1/2, −y−1/2, −z+1. |
The authors thank the Forschungszentrum Karlsruhe and Professor Dieter Fenske for support.
El-khateeb, M., Görls, H. & Weigend, W. (2006). J. Organomet. Chem. 691, 5804–5808.
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany.
The stucture of the title compound, (I), is shown below (Fig. 1). Dimensions are available in the archived CIF. I forms a two-dimensional polymeric arrangement in the solid state and may serve in future as a polydentate ligand with hard and soft donor centres.
For related literature, see El-khateeb et al., 2006.