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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 α-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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059065/sg2202sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059065/sg2202Isup2.hkl
Contains datablock I

CCDC reference: 672715

Key indicators

  • Single-crystal X-ray study
  • T = 100 K, P = 0.0 kPa
  • Mean [sigma](a-O) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.032
  • wR factor = 0.079
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 35.00 Perc.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -C 2ac 2 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.47 Ratio PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 7.60 Deg. C1 -S1 -C1 12.655 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

For related literature, see: El-khateeb et al. (2006).

Experimental top

The compound was prepared by aerobic oxidation of phenylthiol and subsequent treatment with sodium sulfide in THF (yield 10%).

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] 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] Fig. 2. Packing of the title compound in the solid state (without phenyl groups).
Sodium benzenesulfonothioate top
Crystal data top
Na+·C6H5O2S2F(000) = 800
Mr = 196.21Dx = 1.605 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -c 2ac 2Cell parameters from 6649 reflections
a = 9.5579 (10) Åθ = 3.3–56.5°
b = 7.0127 (8) ŵ = 0.65 mm1
c = 24.231 (3) ÅT = 100 K
V = 1624.1 (3) Å3Block, colourless
Z = 80.30 × 0.30 × 0.20 mm
Data collection top
Stoe IPDS 2
diffractometer
1053 independent reflections
Radiation source: fine-focus sealed tube874 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 6.67 pixels mm-1θmax = 28.3°, θmin = 1.7°
rotation scansh = 1212
Absorption correction: numerical
(X-RED32; Stoe & Cie, 2002)
k = 99
Tmin = 0.829, Tmax = 0.881l = 3232
6658 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0377P)2 + 1.7243P]
where P = (Fo2 + 2Fc2)/3
1053 reflections(Δ/σ)max < 0.001
69 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
Na+·C6H5O2S2V = 1624.1 (3) Å3
Mr = 196.21Z = 8
Orthorhombic, CmcaMo Kα radiation
a = 9.5579 (10) ŵ = 0.65 mm1
b = 7.0127 (8) ÅT = 100 K
c = 24.231 (3) Å0.30 × 0.30 × 0.20 mm
Data collection top
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 = 0.881Rint = 0.054
6658 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å3
1053 reflectionsΔρmin = 0.42 e Å3
69 parameters
Special details top

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 > 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)
S10.50000.24418 (9)0.43057 (3)0.01877 (16)
S20.50000.02166 (10)0.40674 (3)0.02647 (18)
Na10.28026 (10)0.00000.50000.0222 (2)
O10.37188 (13)0.2896 (2)0.46085 (5)0.0245 (3)
C10.5122 (3)0.3934 (3)0.37218 (8)0.0208 (6)0.50
C20.4003 (2)0.5052 (4)0.35502 (10)0.0236 (7)0.50
H20.31470.50240.37490.028*0.50
C30.4137 (2)0.6210 (3)0.30877 (11)0.0276 (8)0.50
H30.33720.69750.29700.033*0.50
C40.5390 (3)0.6251 (3)0.27968 (9)0.0297 (10)0.50
H40.54820.70430.24810.036*0.50
C50.6509 (2)0.5133 (4)0.29684 (10)0.0306 (9)0.50
H50.73660.51600.27700.037*0.50
C60.6375 (2)0.3974 (3)0.34309 (10)0.0251 (8)0.50
H60.71400.32100.35480.030*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0143 (3)0.0198 (3)0.0222 (3)0.0000.0000.0004 (2)
S20.0264 (3)0.0217 (3)0.0313 (4)0.0000.0000.0030 (3)
Na10.0168 (5)0.0210 (5)0.0288 (5)0.0000.0000.0000 (4)
O10.0189 (6)0.0270 (7)0.0277 (7)0.0020 (5)0.0052 (5)0.0020 (5)
C10.0183 (16)0.0218 (12)0.0224 (12)0.000 (2)0.001 (2)0.0009 (10)
C20.0222 (16)0.0253 (18)0.0232 (17)0.0019 (15)0.0015 (14)0.0040 (15)
C30.031 (2)0.0244 (18)0.027 (2)0.0005 (17)0.0087 (17)0.0003 (16)
C40.039 (3)0.0242 (17)0.0262 (18)0.0063 (14)0.0034 (15)0.0057 (15)
C50.029 (2)0.033 (2)0.030 (2)0.0069 (18)0.0044 (16)0.0017 (18)
C60.0201 (17)0.029 (2)0.0257 (19)0.0029 (16)0.0008 (15)0.0015 (16)
Geometric parameters (Å, º) top
S1—O11.4627 (13)Na1—Na1iv3.5537 (5)
S1—O1i1.4627 (13)Na1—Na1vi3.5537 (5)
S1—C1i1.7636 (18)Na1—Na1ii4.201 (2)
S1—C11.7636 (18)O1—Na1iv2.2784 (14)
S1—S21.9517 (10)C1—C21.3900
S1—Na13.1896 (8)C1—C61.3900
S1—Na1ii3.1897 (8)C2—C31.3900
S2—Na13.0889 (9)C2—H20.9500
S2—Na1ii3.0889 (9)C3—C41.3900
Na1—O1iii2.2784 (14)C3—H30.9500
Na1—O1iv2.2784 (14)C4—C51.3900
Na1—O12.4065 (14)C4—H40.9500
Na1—O1v2.4066 (14)C5—C61.3900
Na1—S2ii3.0889 (9)C5—H50.9500
Na1—S1ii3.1896 (8)C6—H60.9500
O1—S1—O1i113.68 (11)S2—Na1—S136.176 (19)
O1—S1—C1i102.58 (11)S1ii—Na1—S197.63 (3)
O1i—S1—C1i109.19 (11)O1iii—Na1—Na1iv122.35 (5)
O1—S1—C1109.19 (10)O1iv—Na1—Na1iv42.03 (4)
O1i—S1—C1102.58 (11)O1—Na1—Na1iv39.34 (3)
C1i—S1—C17.60 (18)O1v—Na1—Na1iv153.11 (4)
O1—S1—S2110.89 (6)S2ii—Na1—Na1iv93.56 (2)
O1i—S1—S2110.89 (6)S2—Na1—Na1iv99.16 (2)
C1i—S1—S2109.23 (9)S1ii—Na1—Na1iv129.56 (3)
C1—S1—S2109.23 (9)S1—Na1—Na1iv65.01 (2)
O1—S1—Na145.66 (6)O1iii—Na1—Na1vi42.03 (4)
O1i—S1—Na1113.80 (6)O1iv—Na1—Na1vi122.35 (5)
C1i—S1—Na1134.27 (9)O1—Na1—Na1vi153.11 (4)
C1—S1—Na1141.75 (9)O1v—Na1—Na1vi39.34 (3)
S2—S1—Na169.10 (2)S2ii—Na1—Na1vi99.16 (2)
O1—S1—Na1ii113.80 (6)S2—Na1—Na1vi93.56 (2)
O1i—S1—Na1ii45.66 (6)S1ii—Na1—Na1vi65.01 (2)
C1i—S1—Na1ii141.75 (9)S1—Na1—Na1vi129.56 (3)
C1—S1—Na1ii134.27 (9)Na1iv—Na1—Na1vi161.27 (6)
S2—S1—Na1ii69.10 (2)O1iii—Na1—Na1ii129.66 (4)
Na1—S1—Na1ii82.37 (3)O1iv—Na1—Na1ii129.66 (4)
S1—S2—Na174.72 (2)O1—Na1—Na1ii68.66 (4)
S1—S2—Na1ii74.72 (2)O1v—Na1—Na1ii68.66 (4)
Na1—S2—Na1ii85.68 (3)S2ii—Na1—Na1ii47.160 (17)
O1iii—Na1—O1iv100.68 (8)S2—Na1—Na1ii47.161 (17)
O1iii—Na1—O1127.93 (6)S1ii—Na1—Na1ii48.816 (15)
O1iv—Na1—O181.37 (5)S1—Na1—Na1ii48.817 (15)
O1iii—Na1—O1v81.37 (5)Na1iv—Na1—Na1ii99.37 (3)
O1iv—Na1—O1v127.92 (6)Na1vi—Na1—Na1ii99.37 (3)
O1—Na1—O1v137.32 (8)S1—O1—Na1iv152.16 (9)
O1iii—Na1—S2ii140.39 (4)S1—O1—Na1108.58 (8)
O1iv—Na1—S2ii95.60 (4)Na1iv—O1—Na198.63 (5)
O1—Na1—S2ii89.97 (4)C2—C1—C6120.0
O1v—Na1—S2ii60.38 (4)C2—C1—S1121.58 (15)
O1iii—Na1—S295.60 (4)C6—C1—S1118.42 (15)
O1iv—Na1—S2140.39 (4)C1—C2—C3120.0
O1—Na1—S260.38 (4)C1—C2—H2120.0
O1v—Na1—S289.97 (4)C3—C2—H2120.0
S2ii—Na1—S294.32 (3)C4—C3—C2120.0
O1iii—Na1—S1ii106.99 (4)C4—C3—H3120.0
O1iv—Na1—S1ii123.25 (4)C2—C3—H3120.0
O1—Na1—S1ii114.92 (5)C3—C4—C5120.0
O1v—Na1—S1ii25.76 (3)C3—C4—H4120.0
S2ii—Na1—S1ii36.175 (19)C5—C4—H4120.0
S2—Na1—S1ii84.94 (3)C4—C5—C6120.0
O1iii—Na1—S1123.25 (4)C4—C5—H5120.0
O1iv—Na1—S1106.99 (4)C6—C5—H5120.0
O1—Na1—S125.76 (3)C5—C6—C1120.0
O1v—Na1—S1114.92 (5)C5—C6—H6120.0
S2ii—Na1—S184.94 (3)C1—C6—H6120.0
O1—S1—S2—Na118.83 (6)C1i—S1—Na1—S1ii167.38 (13)
O1i—S1—S2—Na1108.46 (7)C1—S1—Na1—S1ii165.36 (14)
C1i—S1—S2—Na1131.16 (10)S2—S1—Na1—S1ii70.48 (2)
C1—S1—S2—Na1139.21 (9)O1—S1—Na1—Na1iv4.18 (7)
Na1ii—S1—S2—Na189.63 (3)O1i—S1—Na1—Na1iv96.36 (7)
O1—S1—S2—Na1ii108.46 (7)C1i—S1—Na1—Na1iv62.35 (13)
O1i—S1—S2—Na1ii18.82 (6)C1—S1—Na1—Na1iv64.36 (14)
C1i—S1—S2—Na1ii139.21 (9)S2—S1—Na1—Na1iv159.24 (3)
C1—S1—S2—Na1ii131.16 (10)Na1ii—S1—Na1—Na1iv130.28 (2)
Na1—S1—S2—Na1ii89.63 (3)O1—S1—Na1—Na1vi161.79 (9)
S1—S2—Na1—O1iii143.07 (4)O1i—S1—Na1—Na1vi97.67 (7)
Na1ii—S2—Na1—O1iii141.60 (4)C1i—S1—Na1—Na1vi103.62 (13)
S1—S2—Na1—O1iv28.83 (7)C1—S1—Na1—Na1vi101.61 (14)
Na1ii—S2—Na1—O1iv104.16 (7)S2—S1—Na1—Na1vi6.73 (4)
S1—S2—Na1—O112.17 (4)Na1ii—S1—Na1—Na1vi63.75 (4)
Na1ii—S2—Na1—O187.50 (4)O1—S1—Na1—Na1ii134.45 (8)
S1—S2—Na1—O1v135.61 (4)O1i—S1—Na1—Na1ii33.92 (6)
Na1ii—S2—Na1—O1v60.28 (4)C1i—S1—Na1—Na1ii167.38 (13)
S1—S2—Na1—S2ii75.331 (19)C1—S1—Na1—Na1ii165.36 (14)
S1—S2—Na1—S1ii110.31 (2)S2—S1—Na1—Na1ii70.48 (2)
Na1ii—S2—Na1—S1ii34.977 (17)O1i—S1—O1—Na1iv66.5 (2)
Na1ii—S2—Na1—S175.331 (19)C1i—S1—O1—Na1iv51.3 (2)
S1—S2—Na1—Na1iv18.99 (3)C1—S1—O1—Na1iv47.4 (2)
Na1ii—S2—Na1—Na1iv94.32 (3)S2—S1—O1—Na1iv167.80 (15)
S1—S2—Na1—Na1vi174.81 (3)Na1—S1—O1—Na1iv167.3 (2)
Na1ii—S2—Na1—Na1vi99.48 (3)Na1ii—S1—O1—Na1iv116.62 (17)
S1—S2—Na1—Na1ii75.331 (19)O1i—S1—O1—Na1100.80 (10)
O1—S1—Na1—O1iii109.42 (8)C1i—S1—O1—Na1141.44 (10)
O1i—S1—Na1—O1iii150.05 (10)C1—S1—O1—Na1145.33 (11)
C1i—S1—Na1—O1iii51.25 (14)S2—S1—O1—Na124.93 (8)
C1—S1—Na1—O1iii49.23 (15)Na1ii—S1—O1—Na150.65 (8)
S2—S1—Na1—O1iii45.65 (5)O1iii—Na1—O1—S189.13 (7)
Na1ii—S1—Na1—O1iii116.13 (5)O1iv—Na1—O1—S1174.02 (11)
O1—S1—Na1—O1iv6.18 (11)O1v—Na1—O1—S135.23 (6)
O1i—S1—Na1—O1iv94.36 (6)S2ii—Na1—O1—S178.36 (7)
C1i—S1—Na1—O1iv64.35 (13)S2—Na1—O1—S116.63 (5)
C1—S1—Na1—O1iv66.37 (15)S1ii—Na1—O1—S151.27 (8)
S2—S1—Na1—O1iv161.25 (4)Na1iv—Na1—O1—S1174.02 (11)
Na1ii—S1—Na1—O1iv128.27 (4)Na1vi—Na1—O1—S132.18 (16)
O1i—S1—Na1—O1100.54 (13)Na1ii—Na1—O1—S135.23 (6)
C1i—S1—Na1—O158.17 (14)O1iii—Na1—O1—Na1iv96.85 (9)
C1—S1—Na1—O160.19 (16)O1v—Na1—O1—Na1iv138.80 (5)
S2—S1—Na1—O1155.07 (8)S2ii—Na1—O1—Na1iv95.67 (4)
Na1ii—S1—Na1—O1134.45 (8)S2—Na1—O1—Na1iv169.34 (6)
O1—S1—Na1—O1v154.46 (6)S1ii—Na1—O1—Na1iv122.75 (4)
O1i—S1—Na1—O1v53.92 (9)S1—Na1—O1—Na1iv174.02 (11)
C1i—S1—Na1—O1v147.37 (13)Na1vi—Na1—O1—Na1iv153.79 (12)
C1—S1—Na1—O1v145.35 (14)Na1ii—Na1—O1—Na1iv138.80 (5)
S2—S1—Na1—O1v50.48 (4)O1—S1—C1—C211.20 (17)
Na1ii—S1—Na1—O1v20.01 (4)O1i—S1—C1—C2132.10 (14)
O1—S1—Na1—S2ii100.50 (8)C1i—S1—C1—C218.88 (14)
O1i—S1—Na1—S2ii0.04 (7)S2—S1—C1—C2110.21 (13)
C1i—S1—Na1—S2ii158.67 (13)Na1—S1—C1—C229.9 (2)
C1—S1—Na1—S2ii160.69 (14)Na1ii—S1—C1—C2170.60 (10)
S2—S1—Na1—S2ii104.44 (3)O1—S1—C1—C6168.83 (12)
Na1ii—S1—Na1—S2ii33.953 (17)O1i—S1—C1—C647.94 (15)
O1—S1—Na1—S2155.07 (8)C1i—S1—C1—C6161.08 (13)
O1i—S1—Na1—S2104.40 (7)S2—S1—C1—C669.76 (14)
C1i—S1—Na1—S296.90 (13)Na1—S1—C1—C6150.09 (11)
C1—S1—Na1—S294.88 (14)Na1ii—S1—C1—C69.4 (2)
Na1ii—S1—Na1—S270.48 (2)S1—C1—C2—C3180.0 (2)
O1—S1—Na1—S1ii134.45 (8)S1—C1—C6—C5179.97 (19)
O1i—S1—Na1—S1ii33.92 (6)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1; (iii) x+1/2, y1/2, z; (iv) x+1/2, y+1/2, z+1; (v) x, y, z+1; (vi) x+1/2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaNa+·C6H5O2S2
Mr196.21
Crystal system, space groupOrthorhombic, Cmca
Temperature (K)100
a, b, c (Å)9.5579 (10), 7.0127 (8), 24.231 (3)
V3)1624.1 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.65
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerStoe IPDS 2
diffractometer
Absorption correctionNumerical
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.829, 0.881
No. of measured, independent and
observed [I > 2σ(I)] reflections
6658, 1053, 874
Rint0.054
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.079, 1.05
No. of reflections1053
No. of parameters69
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.42

Computer programs: X-AREA (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

 

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