X-ray investigations of sulfur-containing fungicides. III. Intramolecular forces governing the conformation of a novel orthorhombic polymorph of benzoylmethyl phenyl sulfone, benzoylmethyl 4-chlorophenyl sulfone and benzoylphenylmethyl phenyl sulfone

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.

Computing details

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

(Io) benzoylmethyl phenyl sulfone

Crystal data

C14H12O3S	Dx = 1.427 Mg m^−3
Mr = 260.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 50 reflections
a = 4.8177 (7) Å	θ = 5–16°
b = 9.4100 (12) Å	µ = 0.26 mm^−1
c = 26.719 (3) Å	T = 110 K
V = 1211.3 (3) Å^3	Plate, pale yellow
Z = 4	0.6 × 0.4 × 0.2 mm
F(000) = 544

Data collection

Kuma Diffraction KM-4 diffractometer	Rint = 0.049
Radiation source: fine-focus sealed tube	θmax = 30.1°, θmin = 1.5°
Graphite monochromator	h = −1→6
ω–2θ scans	k = −1→13
2859 measured reflections	l = −1→37
2633 independent reflections	3 standard reflections every 100 reflections
2498 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	All H-atom parameters refined
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 0.5406P] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max = 0.027
2633 reflections	Δρmax = 0.38 e Å^−3
211 parameters	Δρmin = −0.33 e Å^−3
0 restraints	Absolute structure: Flack,(1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.02113 (9)	0.67407 (4)	0.081705 (15)	0.01274 (10)
O1	−0.1376 (3)	0.69740 (15)	0.03694 (5)	0.0179 (3)
O2	−0.1264 (3)	0.66597 (16)	0.12864 (5)	0.0190 (3)
O3	−0.0356 (5)	1.00941 (18)	0.09523 (6)	0.0360 (5)
C1	0.2692 (4)	0.81462 (19)	0.08738 (7)	0.0160 (3)
C2	0.1318 (5)	0.93455 (19)	0.11625 (7)	0.0189 (4)
C3	0.1963 (4)	0.95377 (19)	0.17042 (7)	0.0162 (3)
C4	0.0513 (5)	1.0583 (2)	0.19668 (8)	0.0226 (4)
C5	0.0989 (5)	1.0784 (2)	0.24725 (8)	0.0264 (5)
C6	0.2903 (5)	0.9956 (3)	0.27223 (8)	0.0242 (4)
C7	0.4365 (5)	0.8924 (2)	0.24636 (8)	0.0253 (4)
C8	0.3900 (5)	0.8710 (2)	0.19574 (8)	0.0214 (4)
C9	0.2231 (4)	0.51963 (19)	0.07534 (7)	0.0138 (3)
C10	0.2590 (5)	0.4315 (2)	0.11653 (7)	0.0201 (4)
C11	0.4265 (5)	0.3123 (2)	0.11141 (8)	0.0248 (4)
C12	0.5559 (5)	0.2843 (2)	0.06634 (8)	0.0230 (4)
C13	0.5162 (5)	0.3733 (2)	0.02559 (7)	0.0203 (4)
C14	0.3480 (4)	0.4920 (2)	0.02953 (7)	0.0168 (3)
H1	0.438 (5)	0.776 (2)	0.1036 (8)	0.011 (5)*
H2	0.317 (6)	0.838 (3)	0.0510 (10)	0.024 (7)*
H4	−0.069 (7)	1.114 (3)	0.1798 (11)	0.038 (9)*
H5	0.010 (8)	1.157 (4)	0.2660 (12)	0.051 (10)*
H6	0.326 (7)	1.013 (3)	0.3070 (11)	0.031 (8)*
H7	0.566 (7)	0.845 (3)	0.2611 (10)	0.033 (8)*
H8	0.499 (6)	0.798 (3)	0.1787 (9)	0.020 (6)*
H10	0.173 (6)	0.452 (3)	0.1467 (10)	0.024 (7)*
H11	0.452 (6)	0.246 (3)	0.1393 (9)	0.018 (6)*
H12	0.684 (7)	0.208 (3)	0.0639 (11)	0.035 (8)*
H13	0.610 (7)	0.355 (3)	−0.0055 (11)	0.035 (8)*
H14	0.325 (6)	0.559 (2)	0.0023 (9)	0.013 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01141 (17)	0.01502 (17)	0.01179 (17)	0.00158 (16)	0.00080 (15)	0.00152 (13)
O1	0.0153 (6)	0.0219 (6)	0.0166 (6)	0.0018 (6)	−0.0043 (5)	0.0025 (5)
O2	0.0176 (6)	0.0231 (6)	0.0163 (6)	0.0029 (7)	0.0065 (5)	0.0029 (5)
O3	0.0540 (12)	0.0285 (7)	0.0253 (7)	0.0223 (9)	−0.0123 (8)	−0.0030 (6)
C1	0.0166 (8)	0.0162 (7)	0.0153 (7)	0.0008 (7)	0.0012 (7)	−0.0016 (6)
C2	0.0232 (9)	0.0152 (7)	0.0181 (8)	0.0030 (8)	0.0011 (8)	−0.0017 (6)
C3	0.0178 (8)	0.0150 (7)	0.0159 (8)	−0.0004 (7)	0.0016 (7)	−0.0017 (6)
C4	0.0255 (10)	0.0206 (8)	0.0217 (9)	0.0057 (9)	0.0003 (8)	−0.0056 (7)
C5	0.0294 (11)	0.0287 (10)	0.0211 (9)	0.0046 (10)	0.0044 (8)	−0.0105 (8)
C6	0.0267 (10)	0.0305 (10)	0.0154 (8)	−0.0023 (10)	0.0018 (8)	−0.0070 (8)
C7	0.0283 (11)	0.0310 (10)	0.0167 (8)	0.0066 (10)	−0.0041 (8)	−0.0034 (7)
C8	0.0236 (10)	0.0223 (8)	0.0181 (8)	0.0068 (8)	0.0001 (8)	−0.0037 (7)
C9	0.0129 (7)	0.0142 (7)	0.0145 (8)	0.0004 (6)	−0.0013 (6)	0.0007 (6)
C10	0.0242 (10)	0.0215 (8)	0.0145 (8)	0.0035 (9)	0.0000 (7)	0.0033 (7)
C11	0.0318 (11)	0.0204 (8)	0.0221 (9)	0.0058 (9)	−0.0036 (8)	0.0051 (7)
C12	0.0254 (10)	0.0154 (7)	0.0282 (9)	0.0054 (8)	−0.0036 (8)	−0.0027 (7)
C13	0.0221 (9)	0.0189 (7)	0.0200 (8)	0.0034 (8)	0.0012 (8)	−0.0033 (6)
C14	0.0193 (9)	0.0164 (7)	0.0145 (8)	0.0006 (8)	0.0014 (7)	0.0008 (6)

Geometric parameters (Å, º)

S—O1	1.4366 (13)	C11—C12	1.381 (3)
S—O2	1.4434 (13)	C12—C13	1.387 (3)
S—C9	1.7572 (18)	C13—C14	1.384 (3)
S—C1	1.7890 (19)	C1—H1	0.99 (3)
O3—C2	1.209 (3)	C1—H2	1.02 (3)
C1—C2	1.519 (3)	C4—H4	0.90 (3)
C2—C3	1.491 (3)	C5—H5	0.99 (3)
C3—C8	1.391 (3)	C6—H6	0.96 (3)
C3—C4	1.396 (3)	C7—H7	0.86 (3)
C4—C5	1.383 (3)	C8—H8	0.97 (3)
C5—C6	1.380 (3)	C10—H10	0.93 (3)
C6—C7	1.384 (3)	C11—H11	0.98 (2)
C7—C8	1.386 (3)	C12—H12	0.95 (3)
C9—C14	1.389 (2)	C13—H13	0.96 (3)
C9—C10	1.389 (3)	C14—H14	0.97 (2)
C10—C11	1.388 (3)
O1—S—O2	117.99 (8)	C2—C1—H1	114.0 (13)
O1—S—C9	109.91 (8)	S—C1—H1	108.4 (14)
O2—S—C9	108.24 (9)	C2—C1—H2	114.8 (15)
O1—S—C1	108.25 (9)	S—C1—H2	103.3 (16)
O2—S—C1	107.12 (9)	H1—C1—H2	108 (2)
C9—S—C1	104.46 (9)	C5—C4—H4	121 (2)
C2—C1—S	107.53 (13)	C3—C4—H4	118.6 (19)
O3—C2—C3	121.27 (18)	C6—C5—H5	118 (2)
O3—C2—C1	119.18 (18)	C4—C5—H5	122 (2)
C3—C2—C1	119.50 (17)	C5—C6—H6	119.6 (19)
C8—C3—C4	119.08 (18)	C7—C6—H6	120.7 (19)
C8—C3—C2	122.94 (18)	C6—C7—H7	120.2 (19)
C4—C3—C2	117.97 (18)	C8—C7—H7	119.2 (19)
C5—C4—C3	120.3 (2)	C7—C8—H8	118.1 (15)
C6—C5—C4	120.4 (2)	C3—C8—H8	121.8 (15)
C5—C6—C7	119.7 (2)	C11—C10—H10	120.8 (17)
C6—C7—C8	120.5 (2)	C9—C10—H10	120.7 (17)
C7—C8—C3	120.1 (2)	C12—C11—H11	118.9 (15)
C14—C9—C10	122.18 (17)	C10—C11—H11	120.9 (15)
C14—C9—S	118.69 (13)	C11—C12—H12	119.9 (18)
C10—C9—S	119.10 (14)	C13—C12—H12	119.5 (18)
C11—C10—C9	118.48 (18)	C14—C13—H13	119.2 (18)
C12—C11—C10	120.15 (18)	C12—C13—H13	120.3 (18)
C11—C12—C13	120.48 (19)	C13—C14—H14	122.3 (15)
C14—C13—C12	120.55 (18)	C9—C14—H14	119.4 (15)
C13—C14—C9	118.16 (16)
O1—S—C1—C2	88.93 (14)	C2—C3—C8—C7	−178.8 (2)
O2—S—C1—C2	−39.29 (15)	O1—S—C9—C14	39.29 (18)
C9—S—C1—C2	−153.98 (13)	O2—S—C9—C14	169.46 (15)
S—C1—C2—O3	−76.0 (2)	C1—S—C9—C14	−76.65 (17)
S—C1—C2—C3	101.30 (18)	O1—S—C9—C10	−142.48 (16)
O3—C2—C3—C8	−179.2 (2)	O2—S—C9—C10	−12.31 (19)
C1—C2—C3—C8	3.6 (3)	C1—S—C9—C10	101.58 (17)
O3—C2—C3—C4	1.9 (3)	C14—C9—C10—C11	0.2 (3)
C1—C2—C3—C4	−175.39 (19)	S—C9—C10—C11	−177.93 (16)
C8—C3—C4—C5	−0.4 (3)	C9—C10—C11—C12	0.8 (3)
C2—C3—C4—C5	178.6 (2)	C10—C11—C12—C13	−1.1 (3)
C3—C4—C5—C6	0.1 (4)	C11—C12—C13—C14	0.4 (3)
C4—C5—C6—C7	0.4 (4)	C12—C13—C14—C9	0.5 (3)
C5—C6—C7—C8	−0.6 (4)	C10—C9—C14—C13	−0.9 (3)
C6—C7—C8—C3	0.3 (4)	S—C9—C14—C13	177.28 (15)
C4—C3—C8—C7	0.2 (3)

(Im) benzoylmethyl phenyl sulfone

Crystal data

C14H12O3S	F(000) = 544
Mr = 260.30	Dx = 1.379 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.2145 (9) Å	Cell parameters from 43 reflections
b = 5.3594 (6) Å	θ = 4.6–14.0°
c = 25.665 (3) Å	µ = 0.26 mm^−1
β = 98.448 (9)°	T = 290 K
V = 1253.7 (2) Å^3	Plate, colourless
Z = 4	0.6 × 0.4 × 0.2 mm

Data collection

Siemens P3 diffractometer	Rint = 0.046
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.2°
Graphite monochromator	h = −12→12
ω–2θ scans	k = −1→7
4892 measured reflections	l = −1→36
3636 independent reflections	3 standard reflections every 97 reflections
2755 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.120	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 0.0258P] where P = (Fo^2 + 2Fc^2)/3
3636 reflections	(Δ/σ)max = 0.004
211 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.09491 (4)	0.19700 (7)	0.077586 (14)	0.03667 (12)
O1	0.20112 (13)	0.3263 (2)	0.05208 (4)	0.0507 (3)
O2	0.06363 (14)	−0.0592 (2)	0.06416 (5)	0.0508 (3)
O3	−0.16839 (14)	0.4582 (3)	0.14195 (5)	0.0623 (4)
C1	−0.07059 (17)	0.3738 (3)	0.06458 (6)	0.0394 (3)
C2	−0.17871 (16)	0.3281 (3)	0.10309 (6)	0.0404 (3)
C3	−0.29138 (15)	0.1303 (3)	0.09240 (6)	0.0382 (3)
C4	−0.39483 (19)	0.1077 (4)	0.12681 (8)	0.0536 (4)
C5	−0.5018 (2)	−0.0736 (4)	0.11815 (10)	0.0667 (6)
C6	−0.5066 (2)	−0.2361 (4)	0.07634 (9)	0.0634 (5)
C7	−0.4049 (2)	−0.2140 (4)	0.04214 (9)	0.0568 (4)
C8	−0.29814 (17)	−0.0306 (3)	0.05010 (6)	0.0455 (4)
C9	0.14917 (16)	0.2122 (3)	0.14626 (6)	0.0385 (3)
C10	0.2426 (2)	0.4002 (4)	0.16687 (7)	0.0579 (5)
C11	0.2885 (3)	0.4059 (5)	0.22083 (9)	0.0747 (7)
C12	0.2386 (3)	0.2310 (5)	0.25292 (8)	0.0683 (6)
C13	0.1451 (2)	0.0462 (4)	0.23220 (8)	0.0659 (5)
C14	0.0992 (2)	0.0344 (4)	0.17828 (7)	0.0508 (4)
H11	0.343 (3)	0.550 (5)	0.2359 (10)	0.093 (8)*
H12	0.261 (3)	0.243 (4)	0.2885 (11)	0.081 (7)*
H4	−0.392 (2)	0.230 (4)	0.1531 (9)	0.060 (6)*
H5	−0.561 (3)	−0.080 (4)	0.1462 (9)	0.075 (7)*
H6	−0.588 (3)	−0.365 (5)	0.0705 (11)	0.096 (8)*
H7	−0.406 (2)	−0.328 (4)	0.0155 (10)	0.075 (7)*
H8	−0.228 (2)	−0.012 (4)	0.0230 (7)	0.052 (5)*
H10	0.281 (2)	0.516 (5)	0.1430 (9)	0.072 (6)*
H1	−0.1072 (18)	0.336 (3)	0.0299 (7)	0.042 (4)*
H2	−0.043 (2)	0.537 (4)	0.0665 (7)	0.047 (5)*
H13	0.100 (2)	−0.076 (4)	0.2576 (9)	0.077 (7)*
H14	0.038 (2)	−0.093 (4)	0.1644 (9)	0.066 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.04197 (19)	0.03412 (19)	0.03544 (18)	−0.00811 (14)	0.01074 (13)	−0.00182 (14)
O1	0.0523 (6)	0.0601 (7)	0.0436 (6)	−0.0142 (6)	0.0202 (5)	0.0010 (5)
O2	0.0610 (7)	0.0355 (6)	0.0562 (7)	−0.0063 (5)	0.0098 (5)	−0.0095 (5)
O3	0.0640 (7)	0.0734 (9)	0.0508 (7)	−0.0066 (7)	0.0129 (6)	−0.0252 (7)
C1	0.0463 (7)	0.0350 (7)	0.0368 (7)	−0.0070 (6)	0.0058 (6)	0.0034 (6)
C2	0.0428 (7)	0.0424 (8)	0.0359 (7)	0.0015 (6)	0.0055 (5)	−0.0011 (6)
C3	0.0357 (6)	0.0409 (7)	0.0388 (7)	0.0018 (6)	0.0073 (5)	0.0052 (6)
C4	0.0523 (9)	0.0591 (11)	0.0540 (10)	0.0042 (8)	0.0225 (7)	0.0032 (9)
C5	0.0501 (9)	0.0741 (14)	0.0823 (14)	−0.0026 (9)	0.0311 (9)	0.0130 (11)
C6	0.0460 (9)	0.0623 (12)	0.0826 (14)	−0.0144 (9)	0.0123 (9)	0.0074 (10)
C7	0.0479 (9)	0.0576 (11)	0.0648 (11)	−0.0129 (8)	0.0076 (8)	−0.0078 (9)
C8	0.0414 (7)	0.0503 (9)	0.0456 (8)	−0.0066 (7)	0.0093 (6)	−0.0030 (7)
C9	0.0405 (7)	0.0386 (7)	0.0369 (7)	−0.0043 (6)	0.0078 (5)	0.0028 (6)
C10	0.0698 (11)	0.0566 (11)	0.0472 (9)	−0.0259 (9)	0.0084 (8)	−0.0023 (8)
C11	0.0890 (15)	0.0786 (15)	0.0521 (11)	−0.0305 (13)	−0.0041 (10)	−0.0099 (11)
C12	0.0821 (14)	0.0811 (15)	0.0385 (9)	−0.0043 (12)	−0.0017 (9)	0.0036 (9)
C13	0.0805 (13)	0.0710 (13)	0.0455 (9)	−0.0073 (11)	0.0075 (9)	0.0193 (9)
C14	0.0576 (9)	0.0481 (9)	0.0464 (9)	−0.0101 (8)	0.0069 (7)	0.0096 (7)

Geometric parameters (Å, º)

S—O1	1.4332 (11)	C11—C12	1.371 (3)
S—O2	1.4343 (12)	C12—C13	1.368 (3)
S—C9	1.7618 (15)	C13—C14	1.388 (3)
S—C1	1.7848 (17)	C1—H1	0.928 (18)
O3—C2	1.2091 (18)	C1—H2	0.91 (2)
C1—C2	1.523 (2)	C4—H4	0.94 (2)
C2—C3	1.481 (2)	C5—H5	0.96 (2)
C3—C8	1.381 (2)	C6—H6	1.01 (3)
C3—C4	1.397 (2)	C7—H7	0.92 (2)
C4—C5	1.379 (3)	C8—H8	1.021 (18)
C5—C6	1.378 (3)	C10—H10	0.98 (2)
C6—C7	1.380 (3)	C11—H11	0.97 (3)
C7—C8	1.384 (2)	C12—H12	0.91 (3)
C9—C10	1.379 (2)	C13—H13	1.05 (2)
C9—C14	1.381 (2)	C14—H14	0.92 (2)
C10—C11	1.388 (3)
O1—S—O2	118.66 (7)	C2—C1—H1	114.0 (10)
O1—S—C9	108.79 (7)	S—C1—H1	104.0 (10)
O2—S—C9	107.57 (7)	C2—C1—H2	108.9 (11)
O1—S—C1	106.25 (7)	S—C1—H2	106.0 (12)
O2—S—C1	109.10 (7)	H1—C1—H2	108.8 (15)
C9—S—C1	105.77 (7)	C5—C4—H4	123.7 (13)
C2—C1—S	114.57 (10)	C3—C4—H4	116.2 (13)
O3—C2—C3	122.26 (14)	C6—C5—H5	127.1 (14)
O3—C2—C1	117.58 (14)	C4—C5—H5	111.8 (14)
C3—C2—C1	120.16 (13)	C5—C6—H6	118.9 (15)
C8—C3—C4	119.13 (15)	C7—C6—H6	121.4 (15)
C8—C3—C2	122.84 (13)	C6—C7—H7	119.0 (14)
C4—C3—C2	118.03 (15)	C8—C7—H7	120.8 (14)
C5—C4—C3	119.82 (19)	C3—C8—H8	121.0 (11)
C6—C5—C4	120.78 (18)	C7—C8—H8	118.4 (11)
C5—C6—C7	119.60 (18)	C9—C10—H10	119.4 (13)
C3—C8—C7	120.57 (16)	C11—C10—H10	121.7 (13)
C6—C7—C8	120.08 (19)	C12—C11—H11	120.3 (15)
C10—C9—C14	121.32 (15)	C10—C11—H11	118.6 (15)
C10—C9—S	119.13 (12)	C13—C12—H12	118.6 (15)
C14—C9—S	119.55 (12)	C11—C12—H12	120.6 (15)
C9—C10—C11	118.71 (18)	C12—C13—H13	119.5 (13)
C12—C11—C10	120.3 (2)	C14—C13—H13	120.1 (13)
C13—C12—C11	120.61 (18)	C9—C14—H14	121.3 (14)
C12—C13—C14	120.19 (18)	C13—C14—H14	119.9 (14)
C9—C14—C13	118.86 (17)
O1—S—C1—C2	−158.70 (11)	C6—C7—C8—C3	0.6 (3)
O2—S—C1—C2	72.28 (13)	O1—S—C9—C10	22.43 (16)
C9—S—C1—C2	−43.17 (13)	O2—S—C9—C10	152.16 (15)
S—C1—C2—O3	89.85 (17)	C1—S—C9—C10	−91.35 (15)
S—C1—C2—C3	−90.16 (15)	O1—S—C9—C14	−156.69 (14)
O3—C2—C3—C8	−175.47 (17)	O2—S—C9—C14	−26.96 (15)
C1—C2—C3—C8	4.5 (2)	C1—S—C9—C14	89.53 (14)
O3—C2—C3—C4	4.6 (2)	C14—C9—C10—C11	1.2 (3)
C1—C2—C3—C4	−175.35 (14)	S—C9—C10—C11	−177.94 (18)
C8—C3—C4—C5	−0.1 (3)	C9—C10—C11—C12	−1.6 (4)
C2—C3—C4—C5	179.83 (16)	C10—C11—C12—C13	1.1 (4)
C3—C4—C5—C6	1.1 (3)	C11—C12—C13—C14	−0.3 (4)
C4—C5—C6—C7	−1.3 (3)	C10—C9—C14—C13	−0.3 (3)
C5—C6—C7—C8	0.4 (3)	S—C9—C14—C13	178.81 (15)
C4—C3—C8—C7	−0.8 (3)	C12—C13—C14—C9	−0.2 (3)
C2—C3—C8—C7	179.36 (16)

(II) benzoylmethyl 4-chlorophenyl sulfone

Crystal data

C14H11ClO3S	Dx = 1.462 Mg m^−3
Mr = 294.74	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 60 reflections
a = 13.469 (1) Å	θ = 6–18°
b = 7.4580 (1) Å	µ = 4.00 mm^−1
c = 26.656 (2) Å	T = 290 K
V = 2677.6 (5) Å^3	Needle, colourless
Z = 8	0.50 × 0.20 × 0.15 mm
F(000) = 1216

Data collection

Kuma Diffraction KM-4 diffractometer	1761 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 75.0°, θmin = 3.3°
ω–2θ scans	h = −1→16
Absorption correction: ψ scan XEMP (Siemens, 1991)	k = −9→1
Tmin = 0.514, Tmax = 0.987	l = −1→33
3067 measured reflections	3 standard reflections every 100 reflections
2274 independent reflections	intensity decay: 20%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	All H-atom parameters refined
wR(F^2) = 0.198	w = 1/[σ^2(Fo^2) + (0.1429P)^2 + 0.272P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.011
2274 reflections	Δρmax = 0.33 e Å^−3
217 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 97a), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.89767 (6)	0.16997 (13)	0.27403 (3)	0.0610 (3)
Cl	0.70572 (10)	−0.0456 (2)	0.07047 (4)	0.1005 (5)
O1	1.00088 (18)	0.1996 (4)	0.26575 (10)	0.0736 (7)
O2	0.83895 (19)	0.3126 (4)	0.29542 (11)	0.0768 (8)
O3	0.9554 (2)	0.1320 (4)	0.37933 (10)	0.0780 (8)
C1	0.8831 (3)	−0.0268 (6)	0.31064 (13)	0.0627 (8)
C2	0.9166 (2)	−0.0061 (6)	0.36464 (13)	0.0631 (8)
H1	0.813 (2)	−0.067 (4)	0.3102 (12)	0.047 (8)*
H2	0.925 (3)	−0.120 (7)	0.2946 (17)	0.083 (13)*
C3	0.9010 (2)	−0.1633 (5)	0.39785 (13)	0.0647 (9)
C4	0.8667 (3)	−0.3268 (6)	0.38052 (15)	0.0708 (10)
H4	0.856 (3)	−0.338 (6)	0.3457 (17)	0.080 (12)*
C5	0.8553 (4)	−0.4697 (7)	0.4130 (2)	0.0840 (12)
H5	0.843 (3)	−0.577 (7)	0.4000 (18)	0.082 (13)*
C6	0.8777 (5)	−0.4475 (9)	0.4633 (2)	0.1022 (17)
H6	0.861 (4)	−0.541 (8)	0.484 (2)	0.109 (18)*
C7	0.9118 (5)	−0.2864 (9)	0.48067 (18)	0.1105 (18)
H7	0.920 (4)	−0.264 (9)	0.520 (2)	0.127 (19)*
C8	0.9231 (4)	−0.1451 (8)	0.44844 (16)	0.0891 (13)
H8	0.943 (4)	−0.033 (8)	0.4573 (19)	0.093 (15)*
C9	0.8433 (2)	0.1068 (5)	0.21634 (12)	0.0607 (8)
C10	0.7416 (3)	0.1196 (6)	0.21055 (13)	0.0637 (8)
H10	0.701 (3)	0.164 (6)	0.2366 (16)	0.076 (12)*
C11	0.6992 (3)	0.0740 (6)	0.16534 (15)	0.0710 (10)
H11	0.626 (3)	0.082 (5)	0.1612 (14)	0.062 (9)*
C12	0.7602 (3)	0.0134 (6)	0.12689 (13)	0.0719 (10)
C13	0.8615 (3)	0.0000 (7)	0.13253 (15)	0.0774 (11)
H13	0.900 (3)	−0.038 (6)	0.1028 (19)	0.085 (13)*
C14	0.9036 (3)	0.0469 (6)	0.17766 (14)	0.0684 (10)
H14	0.969 (3)	0.051 (5)	0.1824 (12)	0.051 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0554 (5)	0.0605 (6)	0.0670 (5)	0.0008 (3)	0.0009 (3)	0.0025 (4)
Cl	0.1150 (9)	0.1147 (11)	0.0716 (6)	0.0048 (7)	−0.0179 (5)	−0.0043 (6)
O1	0.0583 (13)	0.0815 (19)	0.0812 (14)	−0.0090 (13)	−0.0012 (11)	0.0062 (14)
O2	0.0779 (16)	0.0662 (17)	0.0864 (16)	0.0181 (13)	−0.0036 (13)	−0.0083 (14)
O3	0.0906 (18)	0.0668 (17)	0.0768 (15)	−0.0136 (14)	−0.0092 (13)	−0.0071 (14)
C1	0.0600 (17)	0.066 (2)	0.0625 (16)	−0.0039 (16)	0.0022 (14)	0.0007 (17)
C2	0.0560 (15)	0.068 (2)	0.0654 (16)	0.0014 (16)	0.0021 (13)	−0.0014 (18)
C3	0.0604 (17)	0.069 (2)	0.0642 (17)	0.0068 (15)	0.0029 (13)	0.0008 (17)
C4	0.0698 (19)	0.071 (3)	0.0714 (19)	−0.0016 (18)	0.0018 (16)	−0.002 (2)
C5	0.091 (3)	0.065 (3)	0.096 (3)	0.002 (2)	0.013 (2)	0.005 (3)
C6	0.129 (4)	0.090 (4)	0.087 (3)	0.010 (3)	0.021 (3)	0.029 (3)
C7	0.172 (6)	0.095 (4)	0.065 (2)	0.003 (4)	0.000 (3)	0.007 (3)
C8	0.120 (4)	0.083 (3)	0.064 (2)	−0.002 (3)	−0.003 (2)	−0.004 (2)
C9	0.0546 (15)	0.065 (2)	0.0625 (16)	−0.0003 (16)	0.0015 (12)	0.0077 (16)
C10	0.0597 (17)	0.064 (2)	0.0673 (17)	0.0033 (16)	0.0032 (14)	0.0008 (18)
C11	0.0587 (18)	0.077 (3)	0.077 (2)	0.0011 (17)	−0.0038 (15)	0.006 (2)
C12	0.077 (2)	0.076 (3)	0.0627 (17)	0.0014 (19)	−0.0044 (16)	0.0084 (18)
C13	0.079 (2)	0.089 (3)	0.0644 (18)	0.007 (2)	0.0099 (16)	0.005 (2)
C14	0.0560 (18)	0.079 (3)	0.0700 (18)	0.0055 (16)	0.0053 (14)	0.0094 (19)

Geometric parameters (Å, º)

S—O1	1.425 (2)	C11—C12	1.389 (6)
S—O2	1.443 (3)	C12—C13	1.376 (6)
S—C9	1.767 (3)	C13—C14	1.375 (6)
S—C1	1.773 (4)	Cl—C12	1.730 (4)
O3—C2	1.219 (5)	C1—H1	0.99 (3)
C1—C2	1.517 (5)	C1—H2	1.00 (5)
C2—C3	1.484 (5)	C4—H4	0.94 (4)
C3—C4	1.384 (6)	C5—H5	0.89 (5)
C3—C8	1.387 (5)	C6—H6	0.92 (6)
C4—C5	1.381 (6)	C7—H7	1.06 (6)
C5—C6	1.385 (8)	C8—H8	0.91 (6)
C6—C7	1.367 (9)	C10—H10	0.94 (4)
C7—C8	1.368 (8)	C11—H11	0.99 (4)
C9—C10	1.382 (5)	C13—H13	0.99 (5)
C9—C14	1.386 (5)	C14—H14	0.89 (3)
C10—C11	1.376 (5)
O1—S—O2	118.79 (18)	C14—C13—C12	119.1 (4)
O1—S—C9	108.12 (16)	C13—C14—C9	119.4 (3)
O2—S—C9	108.27 (17)	C2—C1—H1	109.1 (18)
O1—S—C1	108.77 (17)	S—C1—H1	110.3 (19)
O2—S—C1	109.37 (18)	C2—C1—H2	108 (3)
C9—S—C1	102.25 (18)	S—C1—H2	106 (3)
C2—C1—S	113.9 (3)	H1—C1—H2	109 (3)
O3—C2—C3	122.4 (3)	C5—C4—H4	122 (3)
O3—C2—C1	121.2 (3)	C3—C4—H4	117 (3)
C3—C2—C1	116.3 (3)	C4—C5—H5	118 (3)
C4—C3—C8	118.8 (4)	C6—C5—H5	122 (3)
C4—C3—C2	123.0 (3)	C7—C6—H6	123 (4)
C8—C3—C2	118.2 (4)	C5—C6—H6	116 (4)
C5—C4—C3	120.5 (4)	C6—C7—H7	120 (4)
C4—C5—C6	119.4 (5)	C8—C7—H7	119 (4)
C7—C6—C5	120.4 (5)	C7—C8—H8	125 (3)
C6—C7—C8	120.1 (5)	C3—C8—H8	114 (3)
C7—C8—C3	120.7 (5)	C11—C10—H10	119 (2)
C10—C9—C14	121.3 (3)	C9—C10—H10	121 (2)
C10—C9—S	119.3 (3)	C10—C11—H11	120 (2)
C14—C9—S	119.4 (3)	C12—C11—H11	122 (2)
C11—C10—C9	119.5 (3)	C14—C13—H13	124 (3)
C10—C11—C12	118.7 (3)	C12—C13—H13	117 (3)
C13—C12—C11	122.0 (4)	C13—C14—H14	123 (2)
C13—C12—Cl	119.8 (3)	C9—C14—H14	118 (2)
C11—C12—Cl	118.2 (3)
O1—S—C1—C2	70.4 (3)	O1—S—C9—C10	−161.7 (3)
O2—S—C1—C2	−60.8 (3)	O2—S—C9—C10	−31.8 (4)
C9—S—C1—C2	−175.4 (3)	C1—S—C9—C10	83.6 (3)
S—C1—C2—O3	−4.1 (5)	O1—S—C9—C14	17.7 (4)
S—C1—C2—C3	176.7 (2)	O2—S—C9—C14	147.6 (3)
O3—C2—C3—C4	−173.1 (4)	C1—S—C9—C14	−97.0 (3)
C1—C2—C3—C4	6.0 (5)	C14—C9—C10—C11	−0.7 (6)
O3—C2—C3—C8	6.1 (5)	S—C9—C10—C11	178.7 (3)
C1—C2—C3—C8	−174.8 (4)	C9—C10—C11—C12	1.0 (6)
C8—C3—C4—C5	−0.5 (6)	C10—C11—C12—C13	−0.9 (7)
C2—C3—C4—C5	178.7 (4)	C10—C11—C12—Cl	179.4 (3)
C3—C4—C5—C6	0.7 (7)	C11—C12—C13—C14	0.4 (7)
C4—C5—C6—C7	−0.7 (8)	Cl—C12—C13—C14	−179.8 (4)
C5—C6—C7—C8	0.7 (9)	C12—C13—C14—C9	−0.1 (7)
C6—C7—C8—C3	−0.5 (9)	C10—C9—C14—C13	0.3 (6)
C4—C3—C8—C7	0.4 (7)	S—C9—C14—C13	−179.1 (3)
C2—C3—C8—C7	−178.8 (5)

(III) benzoylphenylmethyl phenyl sulfone

Crystal data

C20H16O3S	F(000) = 704
Mr = 336.39	Dx = 1.357 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1282 (8) Å	Cell parameters from 48 reflections
b = 17.2532 (19) Å	θ = 4.1–17.0°
c = 10.8670 (11) Å	µ = 0.21 mm^−1
β = 105.794 (7)°	T = 290 K
V = 1646.8 (3) Å^3	Prism, colourless
Z = 4	0.5 × 0.4 × 0.3 mm

Data collection

Siemens P3 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.3°
Graphite monochromator	h = −11→11
ω–2θ scans	k = −22→1
5033 measured reflections	l = −14→1
3780 independent reflections	3 standard reflections every 97 reflections
3072 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: difference Fourier map
wR(F^2) = 0.101	All H-atom parameters refined
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.3264P] where P = (Fo^2 + 2Fc^2)/3
3780 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S	0.87350 (4)	0.23768 (2)	0.74558 (3)	0.03462 (11)
O1	1.02984 (12)	0.23730 (7)	0.82103 (12)	0.0487 (3)
O2	0.83938 (14)	0.23792 (6)	0.60839 (11)	0.0478 (3)
O3	0.93818 (14)	0.39862 (7)	0.70675 (11)	0.0536 (3)
C1	0.78060 (15)	0.31923 (8)	0.79952 (13)	0.0320 (3)
C2	0.85870 (16)	0.39546 (8)	0.77974 (13)	0.0358 (3)
C3	0.82897 (15)	0.46533 (8)	0.84917 (14)	0.0353 (3)
C4	0.8577 (2)	0.53787 (9)	0.80453 (19)	0.0496 (4)
C5	0.8389 (2)	0.60462 (10)	0.8680 (2)	0.0576 (5)
C6	0.7941 (2)	0.60012 (10)	0.9788 (2)	0.0559 (5)
C7	0.7656 (2)	0.52905 (10)	1.02495 (19)	0.0576 (5)
C8	0.7814 (2)	0.46181 (9)	0.95982 (15)	0.0456 (4)
C9	0.78308 (15)	0.15557 (8)	0.78915 (14)	0.0344 (3)
C10	0.64040 (18)	0.13351 (9)	0.71388 (18)	0.0484 (4)
C11	0.5735 (2)	0.06792 (11)	0.7466 (2)	0.0624 (5)
C12	0.6481 (2)	0.02416 (11)	0.8496 (2)	0.0630 (5)
C13	0.7893 (3)	0.04586 (11)	0.9233 (2)	0.0613 (5)
C14	0.8577 (2)	0.11261 (10)	0.89460 (16)	0.0476 (4)
C15	0.61130 (15)	0.32069 (7)	0.73352 (14)	0.0337 (3)
C16	0.55831 (19)	0.33573 (9)	0.60337 (16)	0.0433 (3)
C17	0.4032 (2)	0.33113 (10)	0.5431 (2)	0.0571 (5)
C18	0.3020 (2)	0.31293 (11)	0.6127 (2)	0.0639 (6)
C19	0.3533 (2)	0.29999 (12)	0.7413 (2)	0.0606 (5)
C20	0.50769 (19)	0.30348 (10)	0.80254 (18)	0.0458 (4)
H1	0.8004 (18)	0.3096 (9)	0.8889 (16)	0.040 (4)*
H4	0.894 (3)	0.5389 (13)	0.732 (2)	0.078 (7)*
H5	0.853 (3)	0.6543 (13)	0.834 (2)	0.080 (7)*
H6	0.780 (3)	0.6478 (13)	1.024 (2)	0.080 (7)*
H7	0.734 (3)	0.5259 (13)	1.098 (2)	0.078 (7)*
H8	0.762 (2)	0.4114 (12)	0.9918 (18)	0.062 (5)*
H10	0.593 (2)	0.1622 (11)	0.6410 (19)	0.058 (5)*
H11	0.481 (3)	0.0524 (15)	0.701 (2)	0.093 (8)*
H12	0.601 (3)	−0.0215 (13)	0.872 (2)	0.078 (7)*
H13	0.850 (3)	0.0130 (15)	0.994 (2)	0.089 (7)*
H14	0.951 (3)	0.1290 (12)	0.9409 (19)	0.066 (6)*
H16	0.626 (2)	0.3468 (10)	0.5537 (17)	0.050 (5)*
H17	0.373 (2)	0.3416 (12)	0.455 (2)	0.071 (6)*
H18	0.200 (3)	0.3117 (14)	0.576 (2)	0.082 (7)*
H19	0.288 (3)	0.2894 (14)	0.789 (2)	0.083 (7)*
H20	0.544 (2)	0.2926 (12)	0.890 (2)	0.058 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.03161 (18)	0.03479 (19)	0.0391 (2)	−0.00018 (13)	0.01246 (14)	−0.00386 (14)
O1	0.0299 (5)	0.0519 (6)	0.0640 (8)	−0.0016 (4)	0.0121 (5)	−0.0053 (5)
O2	0.0611 (7)	0.0473 (6)	0.0400 (6)	0.0023 (5)	0.0223 (5)	−0.0038 (5)
O3	0.0606 (7)	0.0513 (7)	0.0591 (7)	−0.0151 (5)	0.0335 (6)	−0.0061 (5)
C1	0.0345 (7)	0.0301 (6)	0.0327 (7)	−0.0024 (5)	0.0112 (5)	−0.0029 (5)
C2	0.0340 (7)	0.0367 (7)	0.0356 (7)	−0.0057 (5)	0.0075 (6)	−0.0002 (6)
C3	0.0310 (6)	0.0322 (7)	0.0402 (8)	−0.0042 (5)	0.0056 (6)	0.0003 (6)
C4	0.0502 (9)	0.0381 (8)	0.0661 (11)	−0.0070 (7)	0.0254 (8)	0.0040 (8)
C5	0.0524 (10)	0.0320 (8)	0.0908 (14)	−0.0070 (7)	0.0238 (10)	0.0002 (9)
C6	0.0569 (10)	0.0355 (8)	0.0723 (12)	−0.0030 (7)	0.0123 (9)	−0.0135 (8)
C7	0.0803 (13)	0.0449 (9)	0.0496 (10)	−0.0014 (8)	0.0207 (9)	−0.0086 (8)
C8	0.0632 (10)	0.0325 (7)	0.0409 (8)	−0.0031 (7)	0.0140 (7)	0.0002 (6)
C9	0.0343 (7)	0.0297 (6)	0.0397 (7)	0.0011 (5)	0.0112 (6)	−0.0056 (6)
C10	0.0398 (8)	0.0371 (8)	0.0606 (10)	−0.0010 (6)	0.0004 (7)	−0.0017 (7)
C11	0.0435 (9)	0.0422 (9)	0.0954 (16)	−0.0084 (7)	0.0088 (10)	−0.0041 (10)
C12	0.0699 (12)	0.0363 (9)	0.0883 (15)	−0.0075 (8)	0.0308 (11)	0.0002 (9)
C13	0.0837 (14)	0.0417 (9)	0.0567 (11)	0.0027 (9)	0.0163 (10)	0.0081 (8)
C14	0.0494 (9)	0.0427 (9)	0.0455 (9)	0.0001 (7)	0.0044 (7)	0.0002 (7)
C15	0.0327 (7)	0.0256 (6)	0.0432 (8)	−0.0026 (5)	0.0111 (6)	−0.0055 (5)
C16	0.0440 (8)	0.0366 (8)	0.0472 (9)	0.0035 (6)	0.0087 (7)	−0.0011 (7)
C17	0.0548 (10)	0.0441 (9)	0.0595 (11)	0.0081 (8)	−0.0066 (9)	−0.0057 (8)
C18	0.0337 (8)	0.0464 (10)	0.1010 (17)	0.0015 (7)	0.0005 (10)	−0.0139 (10)
C19	0.0399 (9)	0.0544 (11)	0.0928 (16)	−0.0100 (8)	0.0273 (10)	−0.0145 (10)
C20	0.0413 (8)	0.0436 (8)	0.0570 (10)	−0.0081 (6)	0.0208 (7)	−0.0097 (7)

Geometric parameters (Å, º)

S—O2	1.4377 (12)	C15—C20	1.390 (2)
S—O1	1.4394 (11)	C16—C17	1.391 (2)
S—C9	1.7678 (14)	C17—C18	1.380 (3)
S—C1	1.8202 (13)	C18—C19	1.366 (3)
O3—C2	1.2131 (17)	C19—C20	1.387 (3)
C1—C15	1.5165 (18)	C1—H1	0.953 (16)
C1—C2	1.5388 (18)	C4—H4	0.93 (2)
C2—C3	1.486 (2)	C5—H5	0.96 (2)
C3—C8	1.386 (2)	C6—H6	0.99 (2)
C3—C4	1.393 (2)	C7—H7	0.92 (2)
C4—C5	1.377 (2)	C8—H8	0.97 (2)
C5—C6	1.375 (3)	C10—H10	0.93 (2)
C6—C7	1.376 (3)	C11—H11	0.90 (3)
C7—C8	1.387 (2)	C12—H12	0.96 (2)
C9—C14	1.379 (2)	C13—H13	0.99 (2)
C9—C10	1.389 (2)	C14—H14	0.91 (2)
C10—C11	1.378 (2)	C16—H16	0.945 (18)
C11—C12	1.369 (3)	C17—H17	0.94 (2)
C12—C13	1.371 (3)	C18—H18	0.91 (2)
C13—C14	1.385 (3)	C19—H19	0.91 (2)
C15—C16	1.389 (2)	C20—H20	0.94 (2)
O2—S—O1	119.48 (7)	C19—C20—C15	120.17 (18)
O2—S—C9	107.15 (7)	C5—C4—H4	121.8 (14)
O1—S—C9	107.86 (7)	C3—C4—H4	117.0 (14)
O2—S—C1	110.07 (7)	C15—C1—H1	111.8 (10)
O1—S—C1	107.25 (7)	C2—C1—H1	109.0 (10)
C9—S—C1	103.93 (6)	S—C1—H1	102.6 (10)
C15—C1—C2	111.77 (11)	C6—C5—H5	119.3 (14)
C15—C1—S	111.39 (9)	C4—C5—H5	120.7 (14)
C2—C1—S	109.97 (9)	C5—C6—H6	120.1 (13)
O3—C2—C3	121.33 (13)	C7—C6—H6	119.8 (13)
O3—C2—C1	120.80 (13)	C6—C7—H7	120.2 (14)
C3—C2—C1	117.83 (11)	C8—C7—H7	119.6 (14)
C8—C3—C4	118.32 (14)	C3—C8—H8	118.8 (11)
C8—C3—C2	123.27 (13)	C7—C8—H8	120.7 (11)
C4—C3—C2	118.33 (14)	C11—C10—H10	121.3 (12)
C5—C4—C3	121.10 (17)	C9—C10—H10	119.7 (12)
C6—C5—C4	119.91 (16)	C12—C11—H11	118.2 (16)
C5—C6—C7	120.02 (17)	C10—C11—H11	121.3 (16)
C6—C7—C8	120.19 (18)	C11—C12—H12	120.4 (13)
C3—C8—C7	120.45 (15)	C13—C12—H12	119.2 (13)
C14—C9—C10	120.91 (15)	C12—C13—H13	122.4 (14)
C14—C9—S	119.50 (11)	C14—C13—H13	117.1 (14)
C10—C9—S	119.54 (12)	C9—C14—H14	118.0 (13)
C11—C10—C9	118.93 (17)	C13—C14—H14	123.1 (13)
C12—C11—C10	120.48 (18)	C15—C16—H16	121.2 (11)
C11—C12—C13	120.43 (18)	C17—C16—H16	118.9 (11)
C12—C13—C14	120.35 (18)	C18—C17—H17	123.1 (13)
C9—C14—C13	118.87 (17)	C16—C17—H17	116.7 (14)
C16—C15—C20	119.33 (14)	C19—C18—H18	118.3 (15)
C16—C15—C1	120.82 (12)	C17—C18—H18	121.4 (15)
C20—C15—C1	119.78 (14)	C18—C19—H19	121.4 (16)
C15—C16—C17	119.77 (16)	C20—C19—H19	118.3 (16)
C18—C17—C16	120.15 (19)	C19—C20—H20	120.7 (12)
C19—C18—C17	120.24 (17)	C15—C20—H20	119.1 (12)
C18—C19—C20	120.30 (18)
O1—S—C1—C2	60.42 (11)	C1—S—C9—C14	−103.51 (13)
O2—S—C1—C2	−71.04 (11)	O2—S—C9—C10	−37.57 (14)
C9—S—C1—C2	174.49 (9)	O1—S—C9—C10	−167.40 (12)
S—C1—C2—O3	18.71 (17)	C1—S—C9—C10	78.96 (13)
S—C1—C2—C3	−163.46 (10)	C14—C9—C10—C11	0.4 (3)
O3—C2—C3—C8	−159.26 (15)	S—C9—C10—C11	177.86 (14)
O2—S—C1—C15	53.44 (11)	C9—C10—C11—C12	−1.7 (3)
O1—S—C1—C15	−175.11 (9)	C10—C11—C12—C13	1.3 (3)
C9—S—C1—C15	−61.03 (11)	C11—C12—C13—C14	0.3 (3)
C15—C1—C2—O3	−105.55 (15)	C10—C9—C14—C13	1.2 (2)
C15—C1—C2—C3	72.28 (15)	S—C9—C14—C13	−176.26 (13)
C1—C2—C3—C8	22.9 (2)	C12—C13—C14—C9	−1.6 (3)
O3—C2—C3—C4	17.4 (2)	C2—C1—C15—C16	56.02 (16)
C1—C2—C3—C4	−160.44 (14)	S—C1—C15—C16	−67.44 (15)
C8—C3—C4—C5	−0.3 (3)	C2—C1—C15—C20	−126.82 (14)
C2—C3—C4—C5	−177.08 (16)	S—C1—C15—C20	109.72 (13)
C3—C4—C5—C6	1.4 (3)	C20—C15—C16—C17	−1.9 (2)
C4—C5—C6—C7	−1.1 (3)	C1—C15—C16—C17	175.26 (13)
C5—C6—C7—C8	−0.2 (3)	C15—C16—C17—C18	1.0 (2)
C4—C3—C8—C7	−1.0 (3)	C16—C17—C18—C19	0.6 (3)
C2—C3—C8—C7	175.60 (15)	C17—C18—C19—C20	−1.3 (3)
C6—C7—C8—C3	1.3 (3)	C18—C19—C20—C15	0.4 (3)
O2—S—C9—C14	139.96 (13)	C16—C15—C20—C19	1.2 (2)
O1—S—C9—C14	10.13 (14)	C1—C15—C20—C19	−176.01 (14)