Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059065/sg2202sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059065/sg2202Isup2.hkl |
CCDC reference: 672715
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).
Na+·C6H5O2S2− | F(000) = 800 |
Mr = 196.21 | Dx = 1.605 Mg m−3 |
Orthorhombic, Cmca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -c 2ac 2 | Cell parameters from 6649 reflections |
a = 9.5579 (10) Å | θ = 3.3–56.5° |
b = 7.0127 (8) Å | µ = 0.65 mm−1 |
c = 24.231 (3) Å | T = 100 K |
V = 1624.1 (3) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.30 × 0.20 mm |
Stoe IPDS 2 diffractometer | 1053 independent reflections |
Radiation source: fine-focus sealed tube | 874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
Na+·C6H5O2S2− | V = 1624.1 (3) Å3 |
Mr = 196.21 | Z = 8 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 9.5579 (10) Å | µ = 0.65 mm−1 |
b = 7.0127 (8) Å | T = 100 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 | 0 restraints |
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 |
69 parameters |
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. |
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. |
Experimental details
Crystal data | |
Chemical formula | Na+·C6H5O2S2− |
Mr | 196.21 |
Crystal system, space group | Orthorhombic, Cmca |
Temperature (K) | 100 |
a, b, c (Å) | 9.5579 (10), 7.0127 (8), 24.231 (3) |
V (Å3) | 1624.1 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Numerical (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.829, 0.881 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6658, 1053, 874 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.079, 1.05 |
No. of reflections | 1053 |
No. of parameters | 69 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.42 |
Computer programs: X-AREA (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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.