Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110027678/eg3053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110027678/eg3053Isup2.hkl |
CCDC reference: 796079
All reactions were carried out under an atmosphere of purified nitrogen. Solvents were dried and distilled prior to use. Equimolar quantities of 4-nitrobenzenesulfenyl chloride (0.01 mol) and secondary amines [please specify exact compounds] (0.01 mol) in dichloromethane solution were reacted in the presence of an excess of triethylamine. Crystals suitable for X-ray analysis were grown by slow evaporation from dichloromethane at room temperature. The spectroscopic properties of (I) were not determined because of the small amount of sample available.
All H atoms could be located by difference Fourier synthesis but were ultimately placed in calculated positions and treated using a riding model with C—H distances of 0.95 Å and fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C)]. The absolute structure was determined on the basis of 950 measured Bijvoet pairs (coverage 99%). Since the molecules is achiral, the directions of the polar axes had been determined. Two reflections were not included in the data set as they were either partially obscured by the beam stop or were eliminated during data reduction.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Release 4.1; Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C12H8N2O6S2 | F(000) = 696 |
Mr = 340.32 | Dx = 1.687 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4988 reflections |
a = 5.2585 (7) Å | θ = 2.0–25.7° |
b = 6.0483 (5) Å | µ = 0.43 mm−1 |
c = 42.133 (4) Å | T = 173 K |
V = 1340.0 (2) Å3 | Needle, colourless |
Z = 4 | 0.32 × 0.12 × 0.12 mm |
Stoe IPDS II two-circle diffractometer | 2453 independent reflections |
Radiation source: fine-focus sealed tube | 1791 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.096 |
ω scans | θmax = 25.3°, θmin = 1.9° |
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) | h = −5→6 |
Tmin = 0.875, Tmax = 0.950 | k = −6→7 |
5902 measured reflections | l = −50→50 |
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.157 | w = 1/[σ2(Fo2) + (0.0908P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
2453 reflections | Δρmax = 0.67 e Å−3 |
199 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (18) |
C12H8N2O6S2 | V = 1340.0 (2) Å3 |
Mr = 340.32 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.2585 (7) Å | µ = 0.43 mm−1 |
b = 6.0483 (5) Å | T = 173 K |
c = 42.133 (4) Å | 0.32 × 0.12 × 0.12 mm |
Stoe IPDS II two-circle diffractometer | 2453 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) | 1791 reflections with I > 2σ(I) |
Tmin = 0.875, Tmax = 0.950 | Rint = 0.096 |
5902 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.157 | Δρmax = 0.67 e Å−3 |
S = 0.97 | Δρmin = −0.37 e Å−3 |
2453 reflections | Absolute structure: Flack (1983) |
199 parameters | Absolute structure parameter: 0.06 (18) |
0 restraints |
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 | ||
S1 | 0.7532 (3) | 0.1284 (2) | 0.13848 (3) | 0.0430 (4) | |
O1S | 0.5146 (9) | 0.0560 (6) | 0.12587 (9) | 0.0512 (10) | |
O2S | 0.9251 (9) | −0.0251 (7) | 0.15338 (9) | 0.0549 (11) | |
S2 | 0.9680 (3) | 0.2585 (3) | 0.10100 (3) | 0.0449 (4) | |
C1 | 0.7159 (10) | 0.3891 (10) | 0.07893 (11) | 0.0376 (12) | |
C2 | 0.6414 (12) | 0.5995 (10) | 0.08645 (12) | 0.0431 (13) | |
H2 | 0.7272 | 0.6796 | 0.1026 | 0.052* | |
C3 | 0.4394 (12) | 0.6950 (9) | 0.07026 (12) | 0.0425 (13) | |
H3 | 0.3774 | 0.8368 | 0.0761 | 0.051* | |
C4 | 0.3307 (10) | 0.5800 (9) | 0.04553 (11) | 0.0382 (12) | |
C5 | 0.4087 (10) | 0.3732 (10) | 0.03674 (11) | 0.0392 (12) | |
H5 | 0.3296 | 0.2989 | 0.0195 | 0.047* | |
C6 | 0.6064 (11) | 0.2733 (10) | 0.05350 (11) | 0.0411 (13) | |
H6 | 0.6656 | 0.1302 | 0.0478 | 0.049* | |
N1 | 0.1166 (10) | 0.6836 (8) | 0.02834 (10) | 0.0431 (12) | |
O1 | 0.0541 (9) | 0.8705 (8) | 0.03555 (9) | 0.0526 (10) | |
O2 | 0.0128 (9) | 0.5764 (7) | 0.00718 (9) | 0.0527 (10) | |
C11 | 0.6907 (11) | 0.3493 (10) | 0.16476 (12) | 0.0408 (13) | |
C12 | 0.8576 (11) | 0.3951 (11) | 0.18970 (12) | 0.0450 (14) | |
H12 | 1.0010 | 0.3029 | 0.1933 | 0.054* | |
C13 | 0.8134 (11) | 0.5734 (12) | 0.20894 (12) | 0.0482 (16) | |
H13 | 0.9252 | 0.6056 | 0.2260 | 0.058* | |
C14 | 0.6055 (11) | 0.7053 (9) | 0.20322 (12) | 0.0408 (13) | |
C15 | 0.4340 (11) | 0.6621 (10) | 0.17876 (12) | 0.0417 (13) | |
H15 | 0.2900 | 0.7542 | 0.1755 | 0.050* | |
C16 | 0.4780 (12) | 0.4828 (10) | 0.15942 (12) | 0.0434 (13) | |
H16 | 0.3645 | 0.4500 | 0.1425 | 0.052* | |
N11 | 0.5632 (11) | 0.9037 (9) | 0.22251 (11) | 0.0519 (13) | |
O11 | 0.7262 (10) | 0.9562 (8) | 0.24196 (10) | 0.0657 (13) | |
O12 | 0.3680 (11) | 1.0082 (9) | 0.21853 (11) | 0.0722 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0489 (8) | 0.0347 (7) | 0.0454 (6) | −0.0011 (7) | −0.0022 (7) | 0.0023 (6) |
O1S | 0.048 (2) | 0.043 (2) | 0.062 (2) | −0.006 (2) | −0.003 (2) | 0.0001 (18) |
O2S | 0.059 (3) | 0.046 (2) | 0.060 (2) | 0.007 (2) | 0.000 (2) | 0.009 (2) |
S2 | 0.0474 (8) | 0.0457 (8) | 0.0417 (6) | 0.0006 (8) | −0.0031 (6) | 0.0029 (6) |
C1 | 0.036 (3) | 0.037 (3) | 0.039 (2) | 0.001 (3) | −0.002 (2) | 0.003 (2) |
C2 | 0.059 (4) | 0.031 (3) | 0.039 (2) | −0.006 (3) | −0.003 (2) | 0.004 (2) |
C3 | 0.057 (4) | 0.028 (3) | 0.042 (2) | 0.004 (3) | 0.005 (2) | 0.000 (2) |
C4 | 0.043 (3) | 0.032 (3) | 0.039 (2) | −0.002 (2) | 0.000 (2) | 0.003 (2) |
C5 | 0.044 (3) | 0.036 (3) | 0.038 (2) | −0.005 (3) | −0.003 (2) | 0.001 (2) |
C6 | 0.053 (4) | 0.031 (3) | 0.039 (2) | −0.003 (3) | 0.002 (2) | −0.002 (2) |
N1 | 0.046 (3) | 0.039 (3) | 0.044 (2) | −0.001 (2) | 0.003 (2) | 0.003 (2) |
O1 | 0.052 (3) | 0.046 (2) | 0.059 (2) | 0.009 (2) | 0.001 (2) | −0.002 (2) |
O2 | 0.049 (3) | 0.053 (3) | 0.056 (2) | −0.001 (2) | −0.007 (2) | 0.0013 (19) |
C11 | 0.045 (3) | 0.035 (3) | 0.043 (3) | −0.002 (2) | −0.001 (2) | 0.009 (2) |
C12 | 0.041 (3) | 0.053 (4) | 0.041 (3) | −0.006 (3) | −0.006 (2) | 0.012 (3) |
C13 | 0.042 (3) | 0.066 (4) | 0.036 (2) | −0.010 (3) | −0.002 (2) | −0.003 (3) |
C14 | 0.049 (3) | 0.036 (3) | 0.038 (2) | −0.009 (3) | 0.004 (2) | 0.001 (2) |
C15 | 0.036 (3) | 0.041 (3) | 0.048 (3) | 0.001 (3) | 0.001 (2) | 0.004 (2) |
C16 | 0.041 (3) | 0.046 (3) | 0.044 (2) | −0.005 (3) | −0.004 (2) | −0.002 (2) |
N11 | 0.058 (3) | 0.052 (3) | 0.047 (2) | −0.009 (3) | 0.005 (2) | −0.002 (2) |
O11 | 0.068 (3) | 0.070 (3) | 0.059 (2) | −0.008 (3) | −0.004 (2) | −0.017 (2) |
O12 | 0.083 (4) | 0.070 (4) | 0.063 (3) | 0.026 (3) | −0.003 (3) | −0.019 (3) |
S1—O1S | 1.431 (5) | N1—O1 | 1.216 (6) |
S1—O2S | 1.440 (4) | N1—O2 | 1.230 (6) |
S1—C11 | 1.767 (6) | C11—C12 | 1.397 (7) |
S1—S2 | 2.095 (2) | C11—C16 | 1.398 (8) |
S2—C1 | 1.801 (5) | C12—C13 | 1.369 (9) |
C1—C2 | 1.369 (8) | C12—H12 | 0.9500 |
C1—C6 | 1.404 (7) | C13—C14 | 1.375 (8) |
C2—C3 | 1.388 (8) | C13—H13 | 0.9500 |
C2—H2 | 0.9500 | C14—C15 | 1.394 (7) |
C3—C4 | 1.377 (7) | C14—N11 | 1.466 (8) |
C3—H3 | 0.9500 | C15—C16 | 1.376 (8) |
C4—C5 | 1.367 (8) | C15—H15 | 0.9500 |
C4—N1 | 1.478 (7) | C16—H16 | 0.9500 |
C5—C6 | 1.395 (7) | N11—O11 | 1.228 (7) |
C5—H5 | 0.9500 | N11—O12 | 1.217 (7) |
C6—H6 | 0.9500 | ||
O1S—S1—O2S | 121.0 (3) | O1—N1—O2 | 123.4 (5) |
O1S—S1—C11 | 107.5 (3) | O1—N1—C4 | 118.5 (5) |
O2S—S1—C11 | 109.4 (2) | O2—N1—C4 | 118.0 (5) |
O1S—S1—S2 | 107.92 (17) | C12—C11—C16 | 120.6 (6) |
O2S—S1—S2 | 103.46 (19) | C12—C11—S1 | 120.3 (5) |
C11—S1—S2 | 106.77 (19) | C16—C11—S1 | 119.0 (4) |
C1—S2—S1 | 99.05 (18) | C13—C12—C11 | 119.7 (6) |
C2—C1—C6 | 121.5 (5) | C13—C12—H12 | 120.2 |
C2—C1—S2 | 119.9 (4) | C11—C12—H12 | 120.2 |
C6—C1—S2 | 118.5 (4) | C12—C13—C14 | 119.2 (5) |
C1—C2—C3 | 119.5 (5) | C12—C13—H13 | 120.4 |
C1—C2—H2 | 120.3 | C14—C13—H13 | 120.4 |
C3—C2—H2 | 120.3 | C13—C14—C15 | 122.4 (5) |
C4—C3—C2 | 118.6 (5) | C13—C14—N11 | 119.9 (5) |
C4—C3—H3 | 120.7 | C15—C14—N11 | 117.7 (5) |
C2—C3—H3 | 120.7 | C16—C15—C14 | 118.5 (6) |
C5—C4—C3 | 122.9 (5) | C16—C15—H15 | 120.8 |
C5—C4—N1 | 118.9 (5) | C14—C15—H15 | 120.8 |
C3—C4—N1 | 118.2 (5) | C15—C16—C11 | 119.6 (5) |
C4—C5—C6 | 118.9 (5) | C15—C16—H16 | 120.2 |
C4—C5—H5 | 120.6 | C11—C16—H16 | 120.2 |
C6—C5—H5 | 120.6 | O12—N11—O11 | 123.1 (6) |
C5—C6—C1 | 118.4 (5) | O12—N11—C14 | 118.5 (5) |
C5—C6—H6 | 120.8 | O11—N11—C14 | 118.4 (6) |
C1—C6—H6 | 120.8 | ||
O1S—S1—S2—C1 | 36.9 (3) | O2S—S1—C11—C12 | 20.7 (5) |
O2S—S1—S2—C1 | 166.3 (3) | S2—S1—C11—C12 | −90.6 (4) |
C11—S1—S2—C1 | −78.4 (3) | O1S—S1—C11—C16 | −28.8 (5) |
S1—S2—C1—C2 | 86.1 (5) | O2S—S1—C11—C16 | −161.9 (4) |
S1—S2—C1—C6 | −96.1 (4) | S2—S1—C11—C16 | 86.8 (4) |
C6—C1—C2—C3 | 5.2 (8) | C16—C11—C12—C13 | −0.5 (8) |
S2—C1—C2—C3 | −177.1 (4) | S1—C11—C12—C13 | 176.8 (4) |
C1—C2—C3—C4 | −4.4 (8) | C11—C12—C13—C14 | −0.3 (8) |
C2—C3—C4—C5 | 1.7 (8) | C12—C13—C14—C15 | 1.2 (8) |
C2—C3—C4—N1 | −179.7 (5) | C12—C13—C14—N11 | −176.7 (5) |
C3—C4—C5—C6 | 0.2 (8) | C13—C14—C15—C16 | −1.2 (8) |
N1—C4—C5—C6 | −178.4 (5) | N11—C14—C15—C16 | 176.8 (5) |
C4—C5—C6—C1 | 0.5 (8) | C14—C15—C16—C11 | 0.3 (8) |
C2—C1—C6—C5 | −3.2 (8) | C12—C11—C16—C15 | 0.5 (8) |
S2—C1—C6—C5 | 179.0 (4) | S1—C11—C16—C15 | −176.8 (4) |
C5—C4—N1—O1 | −177.4 (5) | C13—C14—N11—O12 | −174.6 (6) |
C3—C4—N1—O1 | 3.9 (7) | C15—C14—N11—O12 | 7.5 (8) |
C5—C4—N1—O2 | 1.7 (7) | C13—C14—N11—O11 | 5.3 (8) |
C3—C4—N1—O2 | −176.9 (5) | C15—C14—N11—O11 | −172.7 (5) |
O1S—S1—C11—C12 | 153.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O11i | 0.95 | 2.45 | 3.262 (7) | 144 |
C15—H15···O(2S)ii | 0.95 | 2.52 | 3.447 (7) | 166 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C12H8N2O6S2 |
Mr | 340.32 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 5.2585 (7), 6.0483 (5), 42.133 (4) |
V (Å3) | 1340.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.32 × 0.12 × 0.12 |
Data collection | |
Diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2009; Blessing, 1995) |
Tmin, Tmax | 0.875, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5902, 2453, 1791 |
Rint | 0.096 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.157, 0.97 |
No. of reflections | 2453 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.37 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.06 (18) |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Release 4.1; Sheldrick, 2008).
S1—O1S | 1.431 (5) | N1—O1 | 1.216 (6) |
S1—O2S | 1.440 (4) | N1—O2 | 1.230 (6) |
S1—C11 | 1.767 (6) | C14—N11 | 1.466 (8) |
S1—S2 | 2.095 (2) | N11—O11 | 1.228 (7) |
S2—C1 | 1.801 (5) | N11—O12 | 1.217 (7) |
C4—N1 | 1.478 (7) | ||
O1S—S1—O2S | 121.0 (3) | O1—N1—O2 | 123.4 (5) |
O1S—S1—C11 | 107.5 (3) | O1—N1—C4 | 118.5 (5) |
O2S—S1—C11 | 109.4 (2) | O2—N1—C4 | 118.0 (5) |
O1S—S1—S2 | 107.92 (17) | O12—N11—O11 | 123.1 (6) |
O2S—S1—S2 | 103.46 (19) | O12—N11—C14 | 118.5 (5) |
C11—S1—S2 | 106.77 (19) | O11—N11—C14 | 118.4 (6) |
C1—S2—S1 | 99.05 (18) | ||
S1—S2—C1—C2 | 86.1 (5) | S2—S1—C11—C12 | −90.6 (4) |
S1—S2—C1—C6 | −96.1 (4) | S2—S1—C11—C16 | 86.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O11i | 0.95 | 2.45 | 3.262 (7) | 144 |
C15—H15···O(2S)ii | 0.95 | 2.52 | 3.447 (7) | 166 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1, y+1, z. |
This paper forms part of our continuing study of the synthesis and structural characterization of divalent sulfur compounds (Brito et al., 2008, and references therein). The title compound, (I), was isolated during attempts to synthesize sulfenamides by a condensation reaction between 4-nitrobenzenesulfenyl chloride, (III), and secondary amines. Compound (III) was purchased from Aldrich (purity 95%, CAS No. 937–32-6). Impurities were not identified in the technical information accompanying the compound, but we believe that (I) was probably an impurity in the commercial sample of (III). To our knowledge, compound (I) is not commercially available. We report here the structure of (I), 4-O2NC6H4SSO2C6H4O2N-4.
The molecular structure of (I) is shown in Fig. 1 and selected geometric parameters are given in Table 1. Compound (I) is a positional isomer of S-(2-nitrophenyl) 2-nitrobenzenethiosulfonate, (II), which crystallizes with Z = 3 and S—S bond distances in the range 2.070 (2)–2.076 (2) Å (Glidewell et al., 2000). The two isomers exhibit important differences with respect to bonding geometries and conformation. The S—S bond distance in (I) is somewhat longer than that in (II). The S—S distances vary upon oxidation of the S centers in the order S—S < SO2—S (Aucott et al., 2005). A survey of C—S—S—C fragments (Allen et al., 1987) found that S—S bond distances are bimodally distributed: for torsion angles in the ranges 75–105 and 0–20°, the mean S—S bond distances are 2.031 (15) and 2.070 (22) Å, respectively.
The nitro groups are rotated by 6.7 (7)° and 2.4 (6)° in (I), while in (II) the nitro groups are rotated by between 37 and 52°, in every case associated with S—S—C—C torsion angles close to 90°, and at the same time the SO2C6H4O2N group is also displaced from the C6S plane. In general this conformation is observed where there are intermolecular C—H···O hydrogen bonds in the crystal structure, although this is not a sufficient condition for the occurrence of the twisted conformer (Aupers et al., 1999; Kucsman et al., 1984; Low, Storey et al., 2000). Other important differences between the isomers are the C—S—S(O2)—C torsion angle [78.39 (2)° for (I) and 69.8 (3)° for (II) (mean)] and the torsion angles between the aromatic rings [12.3 (3)° for (I) and 28.6 (3)° for (II) (mean)].
The molecules in (I) are linked into a continuous two-dimensional framework by means of C—H···O hydrogen bonds. The C—H···O(S) hydrogen bonds connect the molecules to form chains running along the diagonal between the a and b axes. Pairs of these chains, which are perpendicular to each other, are further connected by C—H···O hydrogen bonds (Table 2 and Fig. 2).
The aromatic C—H bonds betweeen the nitro and sulfone groups (C13—H13 and C15—H15) are expected to be the most acidic bonds in the molecule and thus to show the highest propensity for C—H···O hydrogen bond formation. Each molecule in (I) acts as a twofold donor at (x, y, z) and as a twofold acceptor; sulfone atom O15 acts as a single acceptor and nitro group atom O11 as an acceptor of hydrogen bond at (-x + 2, y - 1/2, -z + 1/2) and (x - 1, y + 1, z), respectively, while in (II) both of the sulfone O atoms acts as hydrogen-bond acceptors. The nitro group O atoms of the S-(4-nitrophenyl) fragment are not involved. The hydrogen-bond acceptor properties differ between the isomers.
The molecular conformation of (I) can be described by four independent torsion angles. The S—S—C—C angles are all close to 90° (Fig. 1 and Table 1), so that the projection of the S—S bond is approximately normal to the aryl ring. The conformation about the central S—S bond in (I) has one of the S—O bonds antiperiplanar to the remote aryl ring C1–C6. This same conformation is observed in (II) and is that usually observed in S-aryl arenethiosulfonates, ArSSO2Ar' (Caputo et al., 1984; Ferguson et al., 2000; Low, Glidewell & Wardell, 2000) in preference to the alternative conformation having the two aryl groups antiperiplanar rather than synclinal. The S—SO2 distance is somewhat larger than that in (II) [2.095 (2) Å for (I) and 2.073 (2) Å (mean) for (II)] and is characteristic in esters of this type.
A search in the Cambridge Structural Database (CSD; Version 5.31; Allen 2002) for phenylthiolates fragment C6H5-ySX (X = SO2C6H5-y; y = 0, 1) yielded seven structures: benzenethiosulfonic acid phenyl ester (CSD refcode BILCII10; Caputo et al., 1984), S-(p-tolyl) p-toluenethiosulfonate (refcode BILCOO01; Ferguson et al., 2000), p-tolylthiosulfonic acid p-tolyl ester (refcode BILCOO10; Caputo et al., 1984), di(p-bromophenyl)thiosulfonate (refcode BPTSLF; Noordik & Vos, 1967), S-(2-nitrophenyl) 2-nitrobenzene thiosulfonate (refcode FUQMIN; Glidewell et al., 2000), S-(2-nitrophenyl) p-toluenethiosulfonate (refcode LIYQOZ; Low, Glidewell &Wardell, 2000) and bis[2-(N,N-dipropylcarbamoyl)phenyl]thiosulfinate (refcode NAJBIJ; Kim et al., 1996), with an average S—SO2 distance of 2.087 (4) Å (restraint used in the search: only three-dimensional coordinates available; no private communication; only one sulfone group and no cyclic disulfide). The O—S—O angle is much larger than the ideal tetrahedral values, doubtless as a consequence of the substantial negative charge on the paired O atoms (Table 2), which is observed also in (II) as well as in the seven compound found in the search of the CSD described above.