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The crystal and molecular structures of three β-ketosulfones: benzoylmethyl phenyl sulfone (I), benzoylmethyl 4-chlorophenyl sulfone (II) and benzoylphenylmethyl phenyl sulfone (III) have been investigated using X-ray analysis and quantum mechanics ab initio calculations. Compound (I) crystallizes in the monoclinic and orthorhombic crystal systems. The crystal structure of the orthorhombic polymorph has not been reported previously. At room temperature and in the presence of daylight the pale yellow orthorhombic crystals undergo transformation to the stable colourless monoclinic polymorph. Hyperconjugative σ(S—C1) − π*(C2=O3) and σ*(S—C1) − π(C2=O3) stabilization energies in benzoylmethyl phenyl sulfones are highly dependent on the central dihedral angle α: S—C1—C2=O3 and are largest for a gauche arrangement, as found in both crystal forms of (I). The electron density distribution in all compounds (I), (II) and (III) is significantly affected by interactions of oxygen lone pairs with non-bonding orbitals of the adjacent S—C1 and C1—C2 bonds. The latter effect is responsible for back-donation of the electron density from O atoms towards the central part of the molecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101016238/os0077sup1.cif
Contains datablocks Io, Im, II, III, default1

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101016238/os0077Iosup2.fcf
Contains datablock (Io)

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101016238/os0077Imsup3.fcf
Contains datablock (Im)

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101016238/os0077IIsup4.fcf
Contains datablock (II)

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768101016238/os0077IIIsup5.fcf
Contains datablock (III)

CCDC references: 179362; 179363; 179364; 179365

Computing details top

Data collection: KM-4 (Kuma Diffraction, 1991) for (Io), (II); P3 (Siemens, 1989) for (Im), (III). Cell refinement: KM-4 (Kuma Diffraction, 1991) for (Io), (II); P3 (Siemens, 1989) for (Im), (III). Data reduction: DATAPROC 9.0 (Gałdecki et al., 1995) for (Io), (II); XDISK (Siemens, 1991) for (Im), (III). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(Io) benzoylmethyl phenyl sulfone top
Crystal data top
C14H12O3SDx = 1.427 Mg m3
Mr = 260.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 50 reflections
a = 4.8177 (7) Åθ = 5–16°
b = 9.4100 (12) ŵ = 0.26 mm1
c = 26.719 (3) ÅT = 110 K
V = 1211.3 (3) Å3Plate, pale yellow
Z = 40.6 × 0.4 × 0.2 mm
F(000) = 544
Data collection top
Kuma Diffraction KM-4
diffractometer
Rint = 0.049
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 1.5°
Graphite monochromatorh = 16
ω–2θ scansk = 113
2859 measured reflectionsl = 137
2633 independent reflections3 standard reflections every 100 reflections
2498 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032All H-atom parameters refined
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0468P)2 + 0.5406P]
where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max = 0.027
2633 reflectionsΔρmax = 0.38 e Å3
211 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack,(1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Crystal data top
C14H12O3SV = 1211.3 (3) Å3
Mr = 260.30Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.8177 (7) ŵ = 0.26 mm1
b = 9.4100 (12) ÅT = 110 K
c = 26.719 (3) Å0.6 × 0.4 × 0.2 mm
Data collection top
Kuma Diffraction KM-4
diffractometer
Rint = 0.049
2859 measured reflections3 standard reflections every 100 reflections
2633 independent reflections intensity decay: 2%
2498 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.032All H-atom parameters refined
wR(F2) = 0.096Δρmax = 0.38 e Å3
S = 1.23Δρmin = 0.33 e Å3
2633 reflectionsAbsolute structure: Flack,(1983)
211 parametersAbsolute structure parameter: 0.01 (7)
0 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
S0.02113 (9)0.67407 (4)0.081705 (15)0.01274 (10)
O10.1376 (3)0.69740 (15)0.03694 (5)0.0179 (3)
O20.1264 (3)0.66597 (16)0.12864 (5)0.0190 (3)
O30.0356 (5)1.00941 (18)0.09523 (6)0.0360 (5)
C10.2692 (4)0.81462 (19)0.08738 (7)0.0160 (3)
C20.1318 (5)0.93455 (19)0.11625 (7)0.0189 (4)
C30.1963 (4)0.95377 (19)0.17042 (7)0.0162 (3)
C40.0513 (5)1.0583 (2)0.19668 (8)0.0226 (4)
C50.0989 (5)1.0784 (2)0.24725 (8)0.0264 (5)
C60.2903 (5)0.9956 (3)0.27223 (8)0.0242 (4)
C70.4365 (5)0.8924 (2)0.24636 (8)0.0253 (4)
C80.3900 (5)0.8710 (2)0.19574 (8)0.0214 (4)
C90.2231 (4)0.51963 (19)0.07534 (7)0.0138 (3)
C100.2590 (5)0.4315 (2)0.11653 (7)0.0201 (4)
C110.4265 (5)0.3123 (2)0.11141 (8)0.0248 (4)
C120.5559 (5)0.2843 (2)0.06634 (8)0.0230 (4)
C130.5162 (5)0.3733 (2)0.02559 (7)0.0203 (4)
C140.3480 (4)0.4920 (2)0.02953 (7)0.0168 (3)
H10.438 (5)0.776 (2)0.1036 (8)0.011 (5)*
H20.317 (6)0.838 (3)0.0510 (10)0.024 (7)*
H40.069 (7)1.114 (3)0.1798 (11)0.038 (9)*
H50.010 (8)1.157 (4)0.2660 (12)0.051 (10)*
H60.326 (7)1.013 (3)0.3070 (11)0.031 (8)*
H70.566 (7)0.845 (3)0.2611 (10)0.033 (8)*
H80.499 (6)0.798 (3)0.1787 (9)0.020 (6)*
H100.173 (6)0.452 (3)0.1467 (10)0.024 (7)*
H110.452 (6)0.246 (3)0.1393 (9)0.018 (6)*
H120.684 (7)0.208 (3)0.0639 (11)0.035 (8)*
H130.610 (7)0.355 (3)0.0055 (11)0.035 (8)*
H140.325 (6)0.559 (2)0.0023 (9)0.013 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.01141 (17)0.01502 (17)0.01179 (17)0.00158 (16)0.00080 (15)0.00152 (13)
O10.0153 (6)0.0219 (6)0.0166 (6)0.0018 (6)0.0043 (5)0.0025 (5)
O20.0176 (6)0.0231 (6)0.0163 (6)0.0029 (7)0.0065 (5)0.0029 (5)
O30.0540 (12)0.0285 (7)0.0253 (7)0.0223 (9)0.0123 (8)0.0030 (6)
C10.0166 (8)0.0162 (7)0.0153 (7)0.0008 (7)0.0012 (7)0.0016 (6)
C20.0232 (9)0.0152 (7)0.0181 (8)0.0030 (8)0.0011 (8)0.0017 (6)
C30.0178 (8)0.0150 (7)0.0159 (8)0.0004 (7)0.0016 (7)0.0017 (6)
C40.0255 (10)0.0206 (8)0.0217 (9)0.0057 (9)0.0003 (8)0.0056 (7)
C50.0294 (11)0.0287 (10)0.0211 (9)0.0046 (10)0.0044 (8)0.0105 (8)
C60.0267 (10)0.0305 (10)0.0154 (8)0.0023 (10)0.0018 (8)0.0070 (8)
C70.0283 (11)0.0310 (10)0.0167 (8)0.0066 (10)0.0041 (8)0.0034 (7)
C80.0236 (10)0.0223 (8)0.0181 (8)0.0068 (8)0.0001 (8)0.0037 (7)
C90.0129 (7)0.0142 (7)0.0145 (8)0.0004 (6)0.0013 (6)0.0007 (6)
C100.0242 (10)0.0215 (8)0.0145 (8)0.0035 (9)0.0000 (7)0.0033 (7)
C110.0318 (11)0.0204 (8)0.0221 (9)0.0058 (9)0.0036 (8)0.0051 (7)
C120.0254 (10)0.0154 (7)0.0282 (9)0.0054 (8)0.0036 (8)0.0027 (7)
C130.0221 (9)0.0189 (7)0.0200 (8)0.0034 (8)0.0012 (8)0.0033 (6)
C140.0193 (9)0.0164 (7)0.0145 (8)0.0006 (8)0.0014 (7)0.0008 (6)
Geometric parameters (Å, º) top
S—O11.4366 (13)C11—C121.381 (3)
S—O21.4434 (13)C12—C131.387 (3)
S—C91.7572 (18)C13—C141.384 (3)
S—C11.7890 (19)C1—H10.99 (3)
O3—C21.209 (3)C1—H21.02 (3)
C1—C21.519 (3)C4—H40.90 (3)
C2—C31.491 (3)C5—H50.99 (3)
C3—C81.391 (3)C6—H60.96 (3)
C3—C41.396 (3)C7—H70.86 (3)
C4—C51.383 (3)C8—H80.97 (3)
C5—C61.380 (3)C10—H100.93 (3)
C6—C71.384 (3)C11—H110.98 (2)
C7—C81.386 (3)C12—H120.95 (3)
C9—C141.389 (2)C13—H130.96 (3)
C9—C101.389 (3)C14—H140.97 (2)
C10—C111.388 (3)
O1—S—O2117.99 (8)C2—C1—H1114.0 (13)
O1—S—C9109.91 (8)S—C1—H1108.4 (14)
O2—S—C9108.24 (9)C2—C1—H2114.8 (15)
O1—S—C1108.25 (9)S—C1—H2103.3 (16)
O2—S—C1107.12 (9)H1—C1—H2108 (2)
C9—S—C1104.46 (9)C5—C4—H4121 (2)
C2—C1—S107.53 (13)C3—C4—H4118.6 (19)
O3—C2—C3121.27 (18)C6—C5—H5118 (2)
O3—C2—C1119.18 (18)C4—C5—H5122 (2)
C3—C2—C1119.50 (17)C5—C6—H6119.6 (19)
C8—C3—C4119.08 (18)C7—C6—H6120.7 (19)
C8—C3—C2122.94 (18)C6—C7—H7120.2 (19)
C4—C3—C2117.97 (18)C8—C7—H7119.2 (19)
C5—C4—C3120.3 (2)C7—C8—H8118.1 (15)
C6—C5—C4120.4 (2)C3—C8—H8121.8 (15)
C5—C6—C7119.7 (2)C11—C10—H10120.8 (17)
C6—C7—C8120.5 (2)C9—C10—H10120.7 (17)
C7—C8—C3120.1 (2)C12—C11—H11118.9 (15)
C14—C9—C10122.18 (17)C10—C11—H11120.9 (15)
C14—C9—S118.69 (13)C11—C12—H12119.9 (18)
C10—C9—S119.10 (14)C13—C12—H12119.5 (18)
C11—C10—C9118.48 (18)C14—C13—H13119.2 (18)
C12—C11—C10120.15 (18)C12—C13—H13120.3 (18)
C11—C12—C13120.48 (19)C13—C14—H14122.3 (15)
C14—C13—C12120.55 (18)C9—C14—H14119.4 (15)
C13—C14—C9118.16 (16)
O1—S—C1—C288.93 (14)C2—C3—C8—C7178.8 (2)
O2—S—C1—C239.29 (15)O1—S—C9—C1439.29 (18)
C9—S—C1—C2153.98 (13)O2—S—C9—C14169.46 (15)
S—C1—C2—O376.0 (2)C1—S—C9—C1476.65 (17)
S—C1—C2—C3101.30 (18)O1—S—C9—C10142.48 (16)
O3—C2—C3—C8179.2 (2)O2—S—C9—C1012.31 (19)
C1—C2—C3—C83.6 (3)C1—S—C9—C10101.58 (17)
O3—C2—C3—C41.9 (3)C14—C9—C10—C110.2 (3)
C1—C2—C3—C4175.39 (19)S—C9—C10—C11177.93 (16)
C8—C3—C4—C50.4 (3)C9—C10—C11—C120.8 (3)
C2—C3—C4—C5178.6 (2)C10—C11—C12—C131.1 (3)
C3—C4—C5—C60.1 (4)C11—C12—C13—C140.4 (3)
C4—C5—C6—C70.4 (4)C12—C13—C14—C90.5 (3)
C5—C6—C7—C80.6 (4)C10—C9—C14—C130.9 (3)
C6—C7—C8—C30.3 (4)S—C9—C14—C13177.28 (15)
C4—C3—C8—C70.2 (3)
(Im) benzoylmethyl phenyl sulfone top
Crystal data top
C14H12O3SF(000) = 544
Mr = 260.30Dx = 1.379 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.2145 (9) ÅCell parameters from 43 reflections
b = 5.3594 (6) Åθ = 4.6–14.0°
c = 25.665 (3) ŵ = 0.26 mm1
β = 98.448 (9)°T = 290 K
V = 1253.7 (2) Å3Plate, colourless
Z = 40.6 × 0.4 × 0.2 mm
Data collection top
Siemens P3
diffractometer
Rint = 0.046
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 2.2°
Graphite monochromatorh = 1212
ω–2θ scansk = 17
4892 measured reflectionsl = 136
3636 independent reflections3 standard reflections every 97 reflections
2755 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.120All H-atom parameters refined
S = 1.09 w = 1/[σ2(Fo2) + (0.0684P)2 + 0.0258P]
where P = (Fo2 + 2Fc2)/3
3636 reflections(Δ/σ)max = 0.004
211 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H12O3SV = 1253.7 (2) Å3
Mr = 260.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.2145 (9) ŵ = 0.26 mm1
b = 5.3594 (6) ÅT = 290 K
c = 25.665 (3) Å0.6 × 0.4 × 0.2 mm
β = 98.448 (9)°
Data collection top
Siemens P3
diffractometer
Rint = 0.046
4892 measured reflections3 standard reflections every 97 reflections
3636 independent reflections intensity decay: 2%
2755 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.120All H-atom parameters refined
S = 1.09Δρmax = 0.31 e Å3
3636 reflectionsΔρmin = 0.29 e Å3
211 parameters
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
S0.09491 (4)0.19700 (7)0.077586 (14)0.03667 (12)
O10.20112 (13)0.3263 (2)0.05208 (4)0.0507 (3)
O20.06363 (14)0.0592 (2)0.06416 (5)0.0508 (3)
O30.16839 (14)0.4582 (3)0.14195 (5)0.0623 (4)
C10.07059 (17)0.3738 (3)0.06458 (6)0.0394 (3)
C20.17871 (16)0.3281 (3)0.10309 (6)0.0404 (3)
C30.29138 (15)0.1303 (3)0.09240 (6)0.0382 (3)
C40.39483 (19)0.1077 (4)0.12681 (8)0.0536 (4)
C50.5018 (2)0.0736 (4)0.11815 (10)0.0667 (6)
C60.5066 (2)0.2361 (4)0.07634 (9)0.0634 (5)
C70.4049 (2)0.2140 (4)0.04214 (9)0.0568 (4)
C80.29814 (17)0.0306 (3)0.05010 (6)0.0455 (4)
C90.14917 (16)0.2122 (3)0.14626 (6)0.0385 (3)
C100.2426 (2)0.4002 (4)0.16687 (7)0.0579 (5)
C110.2885 (3)0.4059 (5)0.22083 (9)0.0747 (7)
C120.2386 (3)0.2310 (5)0.25292 (8)0.0683 (6)
C130.1451 (2)0.0462 (4)0.23220 (8)0.0659 (5)
C140.0992 (2)0.0344 (4)0.17828 (7)0.0508 (4)
H110.343 (3)0.550 (5)0.2359 (10)0.093 (8)*
H120.261 (3)0.243 (4)0.2885 (11)0.081 (7)*
H40.392 (2)0.230 (4)0.1531 (9)0.060 (6)*
H50.561 (3)0.080 (4)0.1462 (9)0.075 (7)*
H60.588 (3)0.365 (5)0.0705 (11)0.096 (8)*
H70.406 (2)0.328 (4)0.0155 (10)0.075 (7)*
H80.228 (2)0.012 (4)0.0230 (7)0.052 (5)*
H100.281 (2)0.516 (5)0.1430 (9)0.072 (6)*
H10.1072 (18)0.336 (3)0.0299 (7)0.042 (4)*
H20.043 (2)0.537 (4)0.0665 (7)0.047 (5)*
H130.100 (2)0.076 (4)0.2576 (9)0.077 (7)*
H140.038 (2)0.093 (4)0.1644 (9)0.066 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.04197 (19)0.03412 (19)0.03544 (18)0.00811 (14)0.01074 (13)0.00182 (14)
O10.0523 (6)0.0601 (7)0.0436 (6)0.0142 (6)0.0202 (5)0.0010 (5)
O20.0610 (7)0.0355 (6)0.0562 (7)0.0063 (5)0.0098 (5)0.0095 (5)
O30.0640 (7)0.0734 (9)0.0508 (7)0.0066 (7)0.0129 (6)0.0252 (7)
C10.0463 (7)0.0350 (7)0.0368 (7)0.0070 (6)0.0058 (6)0.0034 (6)
C20.0428 (7)0.0424 (8)0.0359 (7)0.0015 (6)0.0055 (5)0.0011 (6)
C30.0357 (6)0.0409 (7)0.0388 (7)0.0018 (6)0.0073 (5)0.0052 (6)
C40.0523 (9)0.0591 (11)0.0540 (10)0.0042 (8)0.0225 (7)0.0032 (9)
C50.0501 (9)0.0741 (14)0.0823 (14)0.0026 (9)0.0311 (9)0.0130 (11)
C60.0460 (9)0.0623 (12)0.0826 (14)0.0144 (9)0.0123 (9)0.0074 (10)
C70.0479 (9)0.0576 (11)0.0648 (11)0.0129 (8)0.0076 (8)0.0078 (9)
C80.0414 (7)0.0503 (9)0.0456 (8)0.0066 (7)0.0093 (6)0.0030 (7)
C90.0405 (7)0.0386 (7)0.0369 (7)0.0043 (6)0.0078 (5)0.0028 (6)
C100.0698 (11)0.0566 (11)0.0472 (9)0.0259 (9)0.0084 (8)0.0023 (8)
C110.0890 (15)0.0786 (15)0.0521 (11)0.0305 (13)0.0041 (10)0.0099 (11)
C120.0821 (14)0.0811 (15)0.0385 (9)0.0043 (12)0.0017 (9)0.0036 (9)
C130.0805 (13)0.0710 (13)0.0455 (9)0.0073 (11)0.0075 (9)0.0193 (9)
C140.0576 (9)0.0481 (9)0.0464 (9)0.0101 (8)0.0069 (7)0.0096 (7)
Geometric parameters (Å, º) top
S—O11.4332 (11)C11—C121.371 (3)
S—O21.4343 (12)C12—C131.368 (3)
S—C91.7618 (15)C13—C141.388 (3)
S—C11.7848 (17)C1—H10.928 (18)
O3—C21.2091 (18)C1—H20.91 (2)
C1—C21.523 (2)C4—H40.94 (2)
C2—C31.481 (2)C5—H50.96 (2)
C3—C81.381 (2)C6—H61.01 (3)
C3—C41.397 (2)C7—H70.92 (2)
C4—C51.379 (3)C8—H81.021 (18)
C5—C61.378 (3)C10—H100.98 (2)
C6—C71.380 (3)C11—H110.97 (3)
C7—C81.384 (2)C12—H120.91 (3)
C9—C101.379 (2)C13—H131.05 (2)
C9—C141.381 (2)C14—H140.92 (2)
C10—C111.388 (3)
O1—S—O2118.66 (7)C2—C1—H1114.0 (10)
O1—S—C9108.79 (7)S—C1—H1104.0 (10)
O2—S—C9107.57 (7)C2—C1—H2108.9 (11)
O1—S—C1106.25 (7)S—C1—H2106.0 (12)
O2—S—C1109.10 (7)H1—C1—H2108.8 (15)
C9—S—C1105.77 (7)C5—C4—H4123.7 (13)
C2—C1—S114.57 (10)C3—C4—H4116.2 (13)
O3—C2—C3122.26 (14)C6—C5—H5127.1 (14)
O3—C2—C1117.58 (14)C4—C5—H5111.8 (14)
C3—C2—C1120.16 (13)C5—C6—H6118.9 (15)
C8—C3—C4119.13 (15)C7—C6—H6121.4 (15)
C8—C3—C2122.84 (13)C6—C7—H7119.0 (14)
C4—C3—C2118.03 (15)C8—C7—H7120.8 (14)
C5—C4—C3119.82 (19)C3—C8—H8121.0 (11)
C6—C5—C4120.78 (18)C7—C8—H8118.4 (11)
C5—C6—C7119.60 (18)C9—C10—H10119.4 (13)
C3—C8—C7120.57 (16)C11—C10—H10121.7 (13)
C6—C7—C8120.08 (19)C12—C11—H11120.3 (15)
C10—C9—C14121.32 (15)C10—C11—H11118.6 (15)
C10—C9—S119.13 (12)C13—C12—H12118.6 (15)
C14—C9—S119.55 (12)C11—C12—H12120.6 (15)
C9—C10—C11118.71 (18)C12—C13—H13119.5 (13)
C12—C11—C10120.3 (2)C14—C13—H13120.1 (13)
C13—C12—C11120.61 (18)C9—C14—H14121.3 (14)
C12—C13—C14120.19 (18)C13—C14—H14119.9 (14)
C9—C14—C13118.86 (17)
O1—S—C1—C2158.70 (11)C6—C7—C8—C30.6 (3)
O2—S—C1—C272.28 (13)O1—S—C9—C1022.43 (16)
C9—S—C1—C243.17 (13)O2—S—C9—C10152.16 (15)
S—C1—C2—O389.85 (17)C1—S—C9—C1091.35 (15)
S—C1—C2—C390.16 (15)O1—S—C9—C14156.69 (14)
O3—C2—C3—C8175.47 (17)O2—S—C9—C1426.96 (15)
C1—C2—C3—C84.5 (2)C1—S—C9—C1489.53 (14)
O3—C2—C3—C44.6 (2)C14—C9—C10—C111.2 (3)
C1—C2—C3—C4175.35 (14)S—C9—C10—C11177.94 (18)
C8—C3—C4—C50.1 (3)C9—C10—C11—C121.6 (4)
C2—C3—C4—C5179.83 (16)C10—C11—C12—C131.1 (4)
C3—C4—C5—C61.1 (3)C11—C12—C13—C140.3 (4)
C4—C5—C6—C71.3 (3)C10—C9—C14—C130.3 (3)
C5—C6—C7—C80.4 (3)S—C9—C14—C13178.81 (15)
C4—C3—C8—C70.8 (3)C12—C13—C14—C90.2 (3)
C2—C3—C8—C7179.36 (16)
(II) benzoylmethyl 4-chlorophenyl sulfone top
Crystal data top
C14H11ClO3SDx = 1.462 Mg m3
Mr = 294.74Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcaCell parameters from 60 reflections
a = 13.469 (1) Åθ = 6–18°
b = 7.4580 (1) ŵ = 4.00 mm1
c = 26.656 (2) ÅT = 290 K
V = 2677.6 (5) Å3Needle, colourless
Z = 80.50 × 0.20 × 0.15 mm
F(000) = 1216
Data collection top
Kuma Diffraction KM-4
diffractometer
1761 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 75.0°, θmin = 3.3°
ω–2θ scansh = 116
Absorption correction: ψ scan
XEMP (Siemens, 1991)
k = 91
Tmin = 0.514, Tmax = 0.987l = 133
3067 measured reflections3 standard reflections every 100 reflections
2274 independent reflections intensity decay: 20%
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)] = 0.064All H-atom parameters refined
wR(F2) = 0.198 w = 1/[σ2(Fo2) + (0.1429P)2 + 0.272P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.011
2274 reflectionsΔρmax = 0.33 e Å3
217 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 97a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0031 (6)
Crystal data top
C14H11ClO3SV = 2677.6 (5) Å3
Mr = 294.74Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 13.469 (1) ŵ = 4.00 mm1
b = 7.4580 (1) ÅT = 290 K
c = 26.656 (2) Å0.50 × 0.20 × 0.15 mm
Data collection top
Kuma Diffraction KM-4
diffractometer
1761 reflections with I > 2σ(I)
Absorption correction: ψ scan
XEMP (Siemens, 1991)
Rint = 0.055
Tmin = 0.514, Tmax = 0.9873 standard reflections every 100 reflections
3067 measured reflections intensity decay: 20%
2274 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.198All H-atom parameters refined
S = 1.05Δρmax = 0.33 e Å3
2274 reflectionsΔρmin = 0.34 e Å3
217 parameters
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
S0.89767 (6)0.16997 (13)0.27403 (3)0.0610 (3)
Cl0.70572 (10)0.0456 (2)0.07047 (4)0.1005 (5)
O11.00088 (18)0.1996 (4)0.26575 (10)0.0736 (7)
O20.83895 (19)0.3126 (4)0.29542 (11)0.0768 (8)
O30.9554 (2)0.1320 (4)0.37933 (10)0.0780 (8)
C10.8831 (3)0.0268 (6)0.31064 (13)0.0627 (8)
C20.9166 (2)0.0061 (6)0.36464 (13)0.0631 (8)
H10.813 (2)0.067 (4)0.3102 (12)0.047 (8)*
H20.925 (3)0.120 (7)0.2946 (17)0.083 (13)*
C30.9010 (2)0.1633 (5)0.39785 (13)0.0647 (9)
C40.8667 (3)0.3268 (6)0.38052 (15)0.0708 (10)
H40.856 (3)0.338 (6)0.3457 (17)0.080 (12)*
C50.8553 (4)0.4697 (7)0.4130 (2)0.0840 (12)
H50.843 (3)0.577 (7)0.4000 (18)0.082 (13)*
C60.8777 (5)0.4475 (9)0.4633 (2)0.1022 (17)
H60.861 (4)0.541 (8)0.484 (2)0.109 (18)*
C70.9118 (5)0.2864 (9)0.48067 (18)0.1105 (18)
H70.920 (4)0.264 (9)0.520 (2)0.127 (19)*
C80.9231 (4)0.1451 (8)0.44844 (16)0.0891 (13)
H80.943 (4)0.033 (8)0.4573 (19)0.093 (15)*
C90.8433 (2)0.1068 (5)0.21634 (12)0.0607 (8)
C100.7416 (3)0.1196 (6)0.21055 (13)0.0637 (8)
H100.701 (3)0.164 (6)0.2366 (16)0.076 (12)*
C110.6992 (3)0.0740 (6)0.16534 (15)0.0710 (10)
H110.626 (3)0.082 (5)0.1612 (14)0.062 (9)*
C120.7602 (3)0.0134 (6)0.12689 (13)0.0719 (10)
C130.8615 (3)0.0000 (7)0.13253 (15)0.0774 (11)
H130.900 (3)0.038 (6)0.1028 (19)0.085 (13)*
C140.9036 (3)0.0469 (6)0.17766 (14)0.0684 (10)
H140.969 (3)0.051 (5)0.1824 (12)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0554 (5)0.0605 (6)0.0670 (5)0.0008 (3)0.0009 (3)0.0025 (4)
Cl0.1150 (9)0.1147 (11)0.0716 (6)0.0048 (7)0.0179 (5)0.0043 (6)
O10.0583 (13)0.0815 (19)0.0812 (14)0.0090 (13)0.0012 (11)0.0062 (14)
O20.0779 (16)0.0662 (17)0.0864 (16)0.0181 (13)0.0036 (13)0.0083 (14)
O30.0906 (18)0.0668 (17)0.0768 (15)0.0136 (14)0.0092 (13)0.0071 (14)
C10.0600 (17)0.066 (2)0.0625 (16)0.0039 (16)0.0022 (14)0.0007 (17)
C20.0560 (15)0.068 (2)0.0654 (16)0.0014 (16)0.0021 (13)0.0014 (18)
C30.0604 (17)0.069 (2)0.0642 (17)0.0068 (15)0.0029 (13)0.0008 (17)
C40.0698 (19)0.071 (3)0.0714 (19)0.0016 (18)0.0018 (16)0.002 (2)
C50.091 (3)0.065 (3)0.096 (3)0.002 (2)0.013 (2)0.005 (3)
C60.129 (4)0.090 (4)0.087 (3)0.010 (3)0.021 (3)0.029 (3)
C70.172 (6)0.095 (4)0.065 (2)0.003 (4)0.000 (3)0.007 (3)
C80.120 (4)0.083 (3)0.064 (2)0.002 (3)0.003 (2)0.004 (2)
C90.0546 (15)0.065 (2)0.0625 (16)0.0003 (16)0.0015 (12)0.0077 (16)
C100.0597 (17)0.064 (2)0.0673 (17)0.0033 (16)0.0032 (14)0.0008 (18)
C110.0587 (18)0.077 (3)0.077 (2)0.0011 (17)0.0038 (15)0.006 (2)
C120.077 (2)0.076 (3)0.0627 (17)0.0014 (19)0.0044 (16)0.0084 (18)
C130.079 (2)0.089 (3)0.0644 (18)0.007 (2)0.0099 (16)0.005 (2)
C140.0560 (18)0.079 (3)0.0700 (18)0.0055 (16)0.0053 (14)0.0094 (19)
Geometric parameters (Å, º) top
S—O11.425 (2)C11—C121.389 (6)
S—O21.443 (3)C12—C131.376 (6)
S—C91.767 (3)C13—C141.375 (6)
S—C11.773 (4)Cl—C121.730 (4)
O3—C21.219 (5)C1—H10.99 (3)
C1—C21.517 (5)C1—H21.00 (5)
C2—C31.484 (5)C4—H40.94 (4)
C3—C41.384 (6)C5—H50.89 (5)
C3—C81.387 (5)C6—H60.92 (6)
C4—C51.381 (6)C7—H71.06 (6)
C5—C61.385 (8)C8—H80.91 (6)
C6—C71.367 (9)C10—H100.94 (4)
C7—C81.368 (8)C11—H110.99 (4)
C9—C101.382 (5)C13—H130.99 (5)
C9—C141.386 (5)C14—H140.89 (3)
C10—C111.376 (5)
O1—S—O2118.79 (18)C14—C13—C12119.1 (4)
O1—S—C9108.12 (16)C13—C14—C9119.4 (3)
O2—S—C9108.27 (17)C2—C1—H1109.1 (18)
O1—S—C1108.77 (17)S—C1—H1110.3 (19)
O2—S—C1109.37 (18)C2—C1—H2108 (3)
C9—S—C1102.25 (18)S—C1—H2106 (3)
C2—C1—S113.9 (3)H1—C1—H2109 (3)
O3—C2—C3122.4 (3)C5—C4—H4122 (3)
O3—C2—C1121.2 (3)C3—C4—H4117 (3)
C3—C2—C1116.3 (3)C4—C5—H5118 (3)
C4—C3—C8118.8 (4)C6—C5—H5122 (3)
C4—C3—C2123.0 (3)C7—C6—H6123 (4)
C8—C3—C2118.2 (4)C5—C6—H6116 (4)
C5—C4—C3120.5 (4)C6—C7—H7120 (4)
C4—C5—C6119.4 (5)C8—C7—H7119 (4)
C7—C6—C5120.4 (5)C7—C8—H8125 (3)
C6—C7—C8120.1 (5)C3—C8—H8114 (3)
C7—C8—C3120.7 (5)C11—C10—H10119 (2)
C10—C9—C14121.3 (3)C9—C10—H10121 (2)
C10—C9—S119.3 (3)C10—C11—H11120 (2)
C14—C9—S119.4 (3)C12—C11—H11122 (2)
C11—C10—C9119.5 (3)C14—C13—H13124 (3)
C10—C11—C12118.7 (3)C12—C13—H13117 (3)
C13—C12—C11122.0 (4)C13—C14—H14123 (2)
C13—C12—Cl119.8 (3)C9—C14—H14118 (2)
C11—C12—Cl118.2 (3)
O1—S—C1—C270.4 (3)O1—S—C9—C10161.7 (3)
O2—S—C1—C260.8 (3)O2—S—C9—C1031.8 (4)
C9—S—C1—C2175.4 (3)C1—S—C9—C1083.6 (3)
S—C1—C2—O34.1 (5)O1—S—C9—C1417.7 (4)
S—C1—C2—C3176.7 (2)O2—S—C9—C14147.6 (3)
O3—C2—C3—C4173.1 (4)C1—S—C9—C1497.0 (3)
C1—C2—C3—C46.0 (5)C14—C9—C10—C110.7 (6)
O3—C2—C3—C86.1 (5)S—C9—C10—C11178.7 (3)
C1—C2—C3—C8174.8 (4)C9—C10—C11—C121.0 (6)
C8—C3—C4—C50.5 (6)C10—C11—C12—C130.9 (7)
C2—C3—C4—C5178.7 (4)C10—C11—C12—Cl179.4 (3)
C3—C4—C5—C60.7 (7)C11—C12—C13—C140.4 (7)
C4—C5—C6—C70.7 (8)Cl—C12—C13—C14179.8 (4)
C5—C6—C7—C80.7 (9)C12—C13—C14—C90.1 (7)
C6—C7—C8—C30.5 (9)C10—C9—C14—C130.3 (6)
C4—C3—C8—C70.4 (7)S—C9—C14—C13179.1 (3)
C2—C3—C8—C7178.8 (5)
(III) benzoylphenylmethyl phenyl sulfone top
Crystal data top
C20H16O3SF(000) = 704
Mr = 336.39Dx = 1.357 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.1282 (8) ÅCell parameters from 48 reflections
b = 17.2532 (19) Åθ = 4.1–17.0°
c = 10.8670 (11) ŵ = 0.21 mm1
β = 105.794 (7)°T = 290 K
V = 1646.8 (3) Å3Prism, colourless
Z = 40.5 × 0.4 × 0.3 mm
Data collection top
Siemens P3
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.3°
Graphite monochromatorh = 1111
ω–2θ scansk = 221
5033 measured reflectionsl = 141
3780 independent reflections3 standard reflections every 97 reflections
3072 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.101All H-atom parameters refined
S = 0.99 w = 1/[σ2(Fo2) + (0.0577P)2 + 0.3264P]
where P = (Fo2 + 2Fc2)/3
3780 reflections(Δ/σ)max = 0.001
281 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C20H16O3SV = 1646.8 (3) Å3
Mr = 336.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.1282 (8) ŵ = 0.21 mm1
b = 17.2532 (19) ÅT = 290 K
c = 10.8670 (11) Å0.5 × 0.4 × 0.3 mm
β = 105.794 (7)°
Data collection top
Siemens P3
diffractometer
Rint = 0.017
5033 measured reflections3 standard reflections every 97 reflections
3780 independent reflections intensity decay: 2%
3072 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.101All H-atom parameters refined
S = 0.99Δρmax = 0.22 e Å3
3780 reflectionsΔρmin = 0.37 e Å3
281 parameters
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
S0.87350 (4)0.23768 (2)0.74558 (3)0.03462 (11)
O11.02984 (12)0.23730 (7)0.82103 (12)0.0487 (3)
O20.83938 (14)0.23792 (6)0.60839 (11)0.0478 (3)
O30.93818 (14)0.39862 (7)0.70675 (11)0.0536 (3)
C10.78060 (15)0.31923 (8)0.79952 (13)0.0320 (3)
C20.85870 (16)0.39546 (8)0.77974 (13)0.0358 (3)
C30.82897 (15)0.46533 (8)0.84917 (14)0.0353 (3)
C40.8577 (2)0.53787 (9)0.80453 (19)0.0496 (4)
C50.8389 (2)0.60462 (10)0.8680 (2)0.0576 (5)
C60.7941 (2)0.60012 (10)0.9788 (2)0.0559 (5)
C70.7656 (2)0.52905 (10)1.02495 (19)0.0576 (5)
C80.7814 (2)0.46181 (9)0.95982 (15)0.0456 (4)
C90.78308 (15)0.15557 (8)0.78915 (14)0.0344 (3)
C100.64040 (18)0.13351 (9)0.71388 (18)0.0484 (4)
C110.5735 (2)0.06792 (11)0.7466 (2)0.0624 (5)
C120.6481 (2)0.02416 (11)0.8496 (2)0.0630 (5)
C130.7893 (3)0.04586 (11)0.9233 (2)0.0613 (5)
C140.8577 (2)0.11261 (10)0.89460 (16)0.0476 (4)
C150.61130 (15)0.32069 (7)0.73352 (14)0.0337 (3)
C160.55831 (19)0.33573 (9)0.60337 (16)0.0433 (3)
C170.4032 (2)0.33113 (10)0.5431 (2)0.0571 (5)
C180.3020 (2)0.31293 (11)0.6127 (2)0.0639 (6)
C190.3533 (2)0.29999 (12)0.7413 (2)0.0606 (5)
C200.50769 (19)0.30348 (10)0.80254 (18)0.0458 (4)
H10.8004 (18)0.3096 (9)0.8889 (16)0.040 (4)*
H40.894 (3)0.5389 (13)0.732 (2)0.078 (7)*
H50.853 (3)0.6543 (13)0.834 (2)0.080 (7)*
H60.780 (3)0.6478 (13)1.024 (2)0.080 (7)*
H70.734 (3)0.5259 (13)1.098 (2)0.078 (7)*
H80.762 (2)0.4114 (12)0.9918 (18)0.062 (5)*
H100.593 (2)0.1622 (11)0.6410 (19)0.058 (5)*
H110.481 (3)0.0524 (15)0.701 (2)0.093 (8)*
H120.601 (3)0.0215 (13)0.872 (2)0.078 (7)*
H130.850 (3)0.0130 (15)0.994 (2)0.089 (7)*
H140.951 (3)0.1290 (12)0.9409 (19)0.066 (6)*
H160.626 (2)0.3468 (10)0.5537 (17)0.050 (5)*
H170.373 (2)0.3416 (12)0.455 (2)0.071 (6)*
H180.200 (3)0.3117 (14)0.576 (2)0.082 (7)*
H190.288 (3)0.2894 (14)0.789 (2)0.083 (7)*
H200.544 (2)0.2926 (12)0.890 (2)0.058 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.03161 (18)0.03479 (19)0.0391 (2)0.00018 (13)0.01246 (14)0.00386 (14)
O10.0299 (5)0.0519 (6)0.0640 (8)0.0016 (4)0.0121 (5)0.0053 (5)
O20.0611 (7)0.0473 (6)0.0400 (6)0.0023 (5)0.0223 (5)0.0038 (5)
O30.0606 (7)0.0513 (7)0.0591 (7)0.0151 (5)0.0335 (6)0.0061 (5)
C10.0345 (7)0.0301 (6)0.0327 (7)0.0024 (5)0.0112 (5)0.0029 (5)
C20.0340 (7)0.0367 (7)0.0356 (7)0.0057 (5)0.0075 (6)0.0002 (6)
C30.0310 (6)0.0322 (7)0.0402 (8)0.0042 (5)0.0056 (6)0.0003 (6)
C40.0502 (9)0.0381 (8)0.0661 (11)0.0070 (7)0.0254 (8)0.0040 (8)
C50.0524 (10)0.0320 (8)0.0908 (14)0.0070 (7)0.0238 (10)0.0002 (9)
C60.0569 (10)0.0355 (8)0.0723 (12)0.0030 (7)0.0123 (9)0.0135 (8)
C70.0803 (13)0.0449 (9)0.0496 (10)0.0014 (8)0.0207 (9)0.0086 (8)
C80.0632 (10)0.0325 (7)0.0409 (8)0.0031 (7)0.0140 (7)0.0002 (6)
C90.0343 (7)0.0297 (6)0.0397 (7)0.0011 (5)0.0112 (6)0.0056 (6)
C100.0398 (8)0.0371 (8)0.0606 (10)0.0010 (6)0.0004 (7)0.0017 (7)
C110.0435 (9)0.0422 (9)0.0954 (16)0.0084 (7)0.0088 (10)0.0041 (10)
C120.0699 (12)0.0363 (9)0.0883 (15)0.0075 (8)0.0308 (11)0.0002 (9)
C130.0837 (14)0.0417 (9)0.0567 (11)0.0027 (9)0.0163 (10)0.0081 (8)
C140.0494 (9)0.0427 (9)0.0455 (9)0.0001 (7)0.0044 (7)0.0002 (7)
C150.0327 (7)0.0256 (6)0.0432 (8)0.0026 (5)0.0111 (6)0.0055 (5)
C160.0440 (8)0.0366 (8)0.0472 (9)0.0035 (6)0.0087 (7)0.0011 (7)
C170.0548 (10)0.0441 (9)0.0595 (11)0.0081 (8)0.0066 (9)0.0057 (8)
C180.0337 (8)0.0464 (10)0.1010 (17)0.0015 (7)0.0005 (10)0.0139 (10)
C190.0399 (9)0.0544 (11)0.0928 (16)0.0100 (8)0.0273 (10)0.0145 (10)
C200.0413 (8)0.0436 (8)0.0570 (10)0.0081 (6)0.0208 (7)0.0097 (7)
Geometric parameters (Å, º) top
S—O21.4377 (12)C15—C201.390 (2)
S—O11.4394 (11)C16—C171.391 (2)
S—C91.7678 (14)C17—C181.380 (3)
S—C11.8202 (13)C18—C191.366 (3)
O3—C21.2131 (17)C19—C201.387 (3)
C1—C151.5165 (18)C1—H10.953 (16)
C1—C21.5388 (18)C4—H40.93 (2)
C2—C31.486 (2)C5—H50.96 (2)
C3—C81.386 (2)C6—H60.99 (2)
C3—C41.393 (2)C7—H70.92 (2)
C4—C51.377 (2)C8—H80.97 (2)
C5—C61.375 (3)C10—H100.93 (2)
C6—C71.376 (3)C11—H110.90 (3)
C7—C81.387 (2)C12—H120.96 (2)
C9—C141.379 (2)C13—H130.99 (2)
C9—C101.389 (2)C14—H140.91 (2)
C10—C111.378 (2)C16—H160.945 (18)
C11—C121.369 (3)C17—H170.94 (2)
C12—C131.371 (3)C18—H180.91 (2)
C13—C141.385 (3)C19—H190.91 (2)
C15—C161.389 (2)C20—H200.94 (2)
O2—S—O1119.48 (7)C19—C20—C15120.17 (18)
O2—S—C9107.15 (7)C5—C4—H4121.8 (14)
O1—S—C9107.86 (7)C3—C4—H4117.0 (14)
O2—S—C1110.07 (7)C15—C1—H1111.8 (10)
O1—S—C1107.25 (7)C2—C1—H1109.0 (10)
C9—S—C1103.93 (6)S—C1—H1102.6 (10)
C15—C1—C2111.77 (11)C6—C5—H5119.3 (14)
C15—C1—S111.39 (9)C4—C5—H5120.7 (14)
C2—C1—S109.97 (9)C5—C6—H6120.1 (13)
O3—C2—C3121.33 (13)C7—C6—H6119.8 (13)
O3—C2—C1120.80 (13)C6—C7—H7120.2 (14)
C3—C2—C1117.83 (11)C8—C7—H7119.6 (14)
C8—C3—C4118.32 (14)C3—C8—H8118.8 (11)
C8—C3—C2123.27 (13)C7—C8—H8120.7 (11)
C4—C3—C2118.33 (14)C11—C10—H10121.3 (12)
C5—C4—C3121.10 (17)C9—C10—H10119.7 (12)
C6—C5—C4119.91 (16)C12—C11—H11118.2 (16)
C5—C6—C7120.02 (17)C10—C11—H11121.3 (16)
C6—C7—C8120.19 (18)C11—C12—H12120.4 (13)
C3—C8—C7120.45 (15)C13—C12—H12119.2 (13)
C14—C9—C10120.91 (15)C12—C13—H13122.4 (14)
C14—C9—S119.50 (11)C14—C13—H13117.1 (14)
C10—C9—S119.54 (12)C9—C14—H14118.0 (13)
C11—C10—C9118.93 (17)C13—C14—H14123.1 (13)
C12—C11—C10120.48 (18)C15—C16—H16121.2 (11)
C11—C12—C13120.43 (18)C17—C16—H16118.9 (11)
C12—C13—C14120.35 (18)C18—C17—H17123.1 (13)
C9—C14—C13118.87 (17)C16—C17—H17116.7 (14)
C16—C15—C20119.33 (14)C19—C18—H18118.3 (15)
C16—C15—C1120.82 (12)C17—C18—H18121.4 (15)
C20—C15—C1119.78 (14)C18—C19—H19121.4 (16)
C15—C16—C17119.77 (16)C20—C19—H19118.3 (16)
C18—C17—C16120.15 (19)C19—C20—H20120.7 (12)
C19—C18—C17120.24 (17)C15—C20—H20119.1 (12)
C18—C19—C20120.30 (18)
O1—S—C1—C260.42 (11)C1—S—C9—C14103.51 (13)
O2—S—C1—C271.04 (11)O2—S—C9—C1037.57 (14)
C9—S—C1—C2174.49 (9)O1—S—C9—C10167.40 (12)
S—C1—C2—O318.71 (17)C1—S—C9—C1078.96 (13)
S—C1—C2—C3163.46 (10)C14—C9—C10—C110.4 (3)
O3—C2—C3—C8159.26 (15)S—C9—C10—C11177.86 (14)
O2—S—C1—C1553.44 (11)C9—C10—C11—C121.7 (3)
O1—S—C1—C15175.11 (9)C10—C11—C12—C131.3 (3)
C9—S—C1—C1561.03 (11)C11—C12—C13—C140.3 (3)
C15—C1—C2—O3105.55 (15)C10—C9—C14—C131.2 (2)
C15—C1—C2—C372.28 (15)S—C9—C14—C13176.26 (13)
C1—C2—C3—C822.9 (2)C12—C13—C14—C91.6 (3)
O3—C2—C3—C417.4 (2)C2—C1—C15—C1656.02 (16)
C1—C2—C3—C4160.44 (14)S—C1—C15—C1667.44 (15)
C8—C3—C4—C50.3 (3)C2—C1—C15—C20126.82 (14)
C2—C3—C4—C5177.08 (16)S—C1—C15—C20109.72 (13)
C3—C4—C5—C61.4 (3)C20—C15—C16—C171.9 (2)
C4—C5—C6—C71.1 (3)C1—C15—C16—C17175.26 (13)
C5—C6—C7—C80.2 (3)C15—C16—C17—C181.0 (2)
C4—C3—C8—C71.0 (3)C16—C17—C18—C190.6 (3)
C2—C3—C8—C7175.60 (15)C17—C18—C19—C201.3 (3)
C6—C7—C8—C31.3 (3)C18—C19—C20—C150.4 (3)
O2—S—C9—C14139.96 (13)C16—C15—C20—C191.2 (2)
O1—S—C9—C1410.13 (14)C1—C15—C20—C19176.01 (14)

Experimental details

(Io)(Im)(II)(III)
Crystal data
Chemical formulaC14H12O3SC14H12O3SC14H11ClO3SC20H16O3S
Mr260.30260.30294.74336.39
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21/cOrthorhombic, PbcaMonoclinic, P21/c
Temperature (K)110290290290
a, b, c (Å)4.8177 (7), 9.4100 (12), 26.719 (3)9.2145 (9), 5.3594 (6), 25.665 (3)13.469 (1), 7.4580 (1), 26.656 (2)9.1282 (8), 17.2532 (19), 10.8670 (11)
α, β, γ (°)90, 90, 9090, 98.448 (9), 9090, 90, 9090, 105.794 (7), 90
V3)1211.3 (3)1253.7 (2)2677.6 (5)1646.8 (3)
Z4484
Radiation typeMo KαMo KαCu KαMo Kα
µ (mm1)0.260.264.000.21
Crystal size (mm)0.6 × 0.4 × 0.20.6 × 0.4 × 0.20.50 × 0.20 × 0.150.5 × 0.4 × 0.3
Data collection
DiffractometerKuma Diffraction KM-4
diffractometer
Siemens P3
diffractometer
Kuma Diffraction KM-4
diffractometer
Siemens P3
diffractometer
Absorption correctionψ scan
XEMP (Siemens, 1991)
Tmin, Tmax0.514, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
2859, 2633, 2498 4892, 3636, 2755 3067, 2274, 1761 5033, 3780, 3072
Rint0.0490.0460.0550.017
(sin θ/λ)max1)0.7050.7030.6260.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.096, 1.23 0.041, 0.120, 1.09 0.064, 0.198, 1.05 0.036, 0.101, 0.99
No. of reflections2633363622743780
No. of parameters211211217281
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.38, 0.330.31, 0.290.33, 0.340.22, 0.37
Absolute structureFlack,(1983)???
Absolute structure parameter0.01 (7)???

Computer programs: KM-4 (Kuma Diffraction, 1991), P3 (Siemens, 1989), DATAPROC 9.0 (Gałdecki et al., 1995), XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1997b), SHELXL97 (Sheldrick, 1997a), XP (Siemens, 1990).

Selected geometric parameters (Å, º) for (Io) top
S—O11.4366 (13)C6—C71.384 (3)
S—O21.4434 (13)C7—C81.386 (3)
S—C91.7572 (18)C9—C141.389 (2)
S—C11.7890 (19)C9—C101.389 (3)
O3—C21.209 (3)C10—C111.388 (3)
C1—C21.519 (3)C11—C121.381 (3)
C2—C31.491 (3)C12—C131.387 (3)
C3—C81.391 (3)C13—C141.384 (3)
C3—C41.396 (3)C12—H120.95 (3)
C4—C51.383 (3)C13—H130.96 (3)
C5—C61.380 (3)C14—H140.97 (2)
O1—S—O2117.99 (8)C9—S—C1104.46 (9)
O1—S—C9109.91 (8)C2—C1—S107.53 (13)
O2—S—C9108.24 (9)O3—C2—C3121.27 (18)
O1—S—C1108.25 (9)O3—C2—C1119.18 (18)
O2—S—C1107.12 (9)C3—C2—C1119.50 (17)
O1—S—C1—C288.93 (14)S—C1—C2—O376.0 (2)
O2—S—C1—C239.29 (15)S—C1—C2—C3101.30 (18)
C9—S—C1—C2153.98 (13)O3—C2—C3—C8179.2 (2)
Selected geometric parameters (Å, º) for (Im) top
S—O11.4332 (11)C5—C61.378 (3)
S—O21.4343 (12)C6—C71.380 (3)
S—C91.7618 (15)C7—C81.384 (2)
S—C11.7848 (17)C9—C101.379 (2)
O3—C21.2091 (18)C9—C141.381 (2)
C1—C21.523 (2)C10—C111.388 (3)
C2—C31.481 (2)C11—C121.371 (3)
C3—C81.381 (2)C12—C131.368 (3)
C3—C41.397 (2)C13—C141.388 (3)
C4—C51.379 (3)
O1—S—O2118.66 (7)C9—S—C1105.77 (7)
O1—S—C9108.79 (7)C2—C1—S114.57 (10)
O2—S—C9107.57 (7)O3—C2—C3122.26 (14)
O1—S—C1106.25 (7)O3—C2—C1117.58 (14)
O2—S—C1109.10 (7)C3—C2—C1120.16 (13)
O1—S—C1—C2158.70 (11)S—C1—C2—O389.85 (17)
O2—S—C1—C272.28 (13)S—C1—C2—C390.16 (15)
C9—S—C1—C243.17 (13)O3—C2—C3—C8175.47 (17)
Selected geometric parameters (Å, º) for (II) top
S—O11.425 (2)C5—C61.385 (8)
S—O21.443 (3)C6—C71.367 (9)
S—C91.767 (3)C7—C81.368 (8)
S—C11.773 (4)C9—C101.382 (5)
O3—C21.219 (5)C9—C141.386 (5)
C1—C21.517 (5)C10—C111.376 (5)
C2—C31.484 (5)C11—C121.389 (6)
C3—C41.384 (6)C12—C131.376 (6)
C3—C81.387 (5)C13—C141.375 (6)
C4—C51.381 (6)Cl—C121.730 (4)
O1—S—O2118.79 (18)C9—S—C1102.25 (18)
O1—S—C9108.12 (16)C2—C1—S113.9 (3)
O2—S—C9108.27 (17)O3—C2—C3122.4 (3)
O1—S—C1108.77 (17)O3—C2—C1121.2 (3)
O2—S—C1109.37 (18)C3—C2—C1116.3 (3)
O1—S—C1—C270.4 (3)S—C1—C2—O34.1 (5)
O2—S—C1—C260.8 (3)S—C1—C2—C3176.7 (2)
C9—S—C1—C2175.4 (3)O3—C2—C3—C4173.1 (4)
Selected geometric parameters (Å, º) for (III) top
S—O21.4377 (12)C7—C81.387 (2)
S—O11.4394 (11)C9—C141.379 (2)
S—C91.7678 (14)C9—C101.389 (2)
S—C11.8202 (13)C10—C111.378 (2)
O3—C21.2131 (17)C11—C121.369 (3)
C1—C151.5165 (18)C12—C131.371 (3)
C1—C21.5388 (18)C13—C141.385 (3)
C2—C31.486 (2)C15—C161.389 (2)
C3—C81.386 (2)C15—C201.390 (2)
C3—C41.393 (2)C16—C171.391 (2)
C4—C51.377 (2)C17—C181.380 (3)
C5—C61.375 (3)C18—C191.366 (3)
C6—C71.376 (3)C19—C201.387 (3)
O2—S—O1119.48 (7)C15—C1—C2111.77 (11)
O2—S—C9107.15 (7)C15—C1—S111.39 (9)
O1—S—C9107.86 (7)C2—C1—S109.97 (9)
O2—S—C1110.07 (7)O3—C2—C3121.33 (13)
O1—S—C1107.25 (7)O3—C2—C1120.80 (13)
C9—S—C1103.93 (6)C3—C2—C1117.83 (11)
O1—S—C1—C260.42 (11)O3—C2—C3—C8159.26 (15)
O2—S—C1—C271.04 (11)O2—S—C1—C1553.44 (11)
C9—S—C1—C2174.49 (9)O1—S—C1—C15175.11 (9)
S—C1—C2—O318.71 (17)C9—S—C1—C1561.03 (11)
S—C1—C2—C3163.46 (10)
 

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