Vinyl sulfones

Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2-phenyl­ethenylsulfonyl­meth­yl)phosphonate, C₁₅H₂₃O₅PS, (I), diisopropyl {[2-(7-meth­oxy-1,3-benzodi­oxol-5-yl)ethenylsulfon­yl]methyl­sulfonyl­meth­yl}­phos­phon­ate, C₁₈H₂₇O₁₀PS₂, (II), bis­(trans-2-phenyl­ethen­yl) sulfone, C₁₆H₁₄O₂S, (III), and bis­(trans-2-phenyl­ethenylsulfon­yl)­methane, C₁₇H₁₆O₄S₂, (IV). Their structures can be considered as highly functionalized mimics of mono-, di- and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z' > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S-C(vinyl) distance relative to the S-CH₂ distance by ca 0.05 Å. The S-C-S and S-C-P backbones resemble the P-O-P backbone but are not identical because the S-C and P-C distances are longer than the P-O distance and the S-C-S and S-C-P angles are more acute than the P-O-P angle. No prior crystal structures of comparable compounds have been published.

S1. Comment

Recent investigations have focused on the replacement of phosphate backbones with phosphate mimics that possess several desirable characteristics. For example, when the bridging O atom of the phosphate is replaced with a methylene unit, greater stability towards hydrolysis is achieved. Replacement of the P atom with sulfur and oxidation to the sulfone maintains metallophilicity, of potential importance in inhibition that involves metalloenzymes. The non-charged nature of the sulfone improves cellular penetration over ionizable mimics such as L-chicoric acid (Hadd et al., 2001; Meadows et al., 2005; Meadows & Gervay-Hague, 2006a). The vinyl sulfone groups in the compounds reported in this study, (I)–(IV), have been shown to be an important class of antivirals, with the possibility for covalent attachement (Meadows & Gervay-Hague, 2006b; Meadows et al., 2007). As part of these ongoing inhibition studies, we previously reported the structure of saturated phosphonatemono- (Wong, Olmstead & Gervay-Hague, 2007) and disulfone (Wong, Olmstead, Fettinger & Gervay-Hague, 2007) reagents which are the starting materials for the title compounds.

A summary of selected bond distances and angles in (I)–(IV) is presented in Table 5. The bonds between the S and the vinyl C atoms are systematically shorter [average 1.741 (4) Å] than those between the S and a methylene bridging C atoms [average 1.780 (7) Å]. Compound (I) has two molecules in the asymmetric unit, shown in Fig. 1 perpendicular to the vinyl group plane in order to demonstrate the flexibility in the backbone of the molecule. The S1···P1 and S21···P21 distances are 3.0262 (10) and 3.0065 (10) Å, respectively. Compound (II) (Fig. 2) also has Z' = 2. The intermolecular S···P distances are 3.0274 (5) and 3.0304 (5) Å; the S···S distances are slightly longer at 3.0472 (5) and 3.0470 (5) Å. Compound (III) has Z' = 3 (Fig. 3). One of the molecules is disordered in the orientation of the set of atoms C49–C56. The drawing of the three molecules in Fig. 3 shows them in their relative orientations in the structure. Again, there are obvious conformational differences among the three molecules. In Table 5 the metric data for the disordered molecule of (III) has been omitted. Compound (IV) (Fig. 4) has a crystallographic twofold axis passing through atom C9. The S1···S1ⁱ separation is 3.0549 (6) Å.

In order to compare (I)–(IV) with polyphosphates, average values for P—O(bridging) distances, P—O—P angles and P···P distances can be compared with the the P—C, S—C, S—C—S and S—C—P distances and angles, as well as the S···P and S···S distances in di- and triphosphates in the CSD (Allen, 2002; CONQUEST; Cambridge Structural Database, 2007). We selected 21 acyclic structures with R < 0.075. The average P—O distance is 1.603 (18) Å, the P—O—P angle is 133 (2)°, the P···P distance is 2.94 (3) Å and the O···O distance is 2.48 (4) Å. As would be expected, the P—C and S—C distances are longer than the P—O distance, and the S—C—S and S—C—P angles are more acute than P—O—P. Additionally, although the tetrahedral geometry at S and P is similar, the fact that S—C bonds are longer than P—O bonds means that the repeat distance between bridging C atoms is greater than the C···O and O···O distances. Thus, we found that the vinyl sulfone or vinyl sulfone/phosphonate backbone is lengthened relative to the polyphosphate backbone by ca 0.40 Å per repeat. None of the structures (I)–(IV) contains solvent molecules or possesses any strong intermolecular interactions. Since all of the crystals were obtained from non-aqueous solvents, the corresponding structures in hydrophillic environments may significantly differ. However, it is clear that the backbones of these vinyl sulfones and mixed sulfone/phosphonate compounds resemble those of polyphosphates, and replacement of the bridging O atom by a CH₂ group preserves the rotational flexibility of the polyphosphate structure.

Related literature

For related literature, see: Cambridge (2007); Hadd et al. (2001); Meadows & Gervay-Hague (2006a, 2006b); Meadows et al. (2005, 2007); Wong et al. (2007a, 2007b).

S2. Experimental

Compound (I) was prepared as follows. In a flame-dried flask, the monosulfone reagent (Wong, Olmstead & Gervay-Hague, 2007) (600 mg, 1.42 mmol) was dissolved in dry tetrahydrofuran (THF; 1.8 ml) at room temperature under argon. LiBr (180 mg, 2.13 mmol) was added with stirring until all dissolved. At this point, sodium hydride (51 mg, 2.13 mmol) was added until all bubbles disappeared, and then benzaldehyde (75 mg, 0.71 mmol) was added. The reaction mixture was stirred at room temperature for 3 h and then quenched with a 1:1 solution of acetic acid and water (2 ml). The solution was partitioned between ethyl acetate and water, and extracted three times with ethyl acetate. The organic phase was collected and dried over sodium sulfate. The solvent was evaporated to yield a crude oil that was subjected to column chromatography (80% hexane:20% ethyl acetate) and eventually crystallized in a test tube to give compound (I) in 39% yield. ¹H (400 MHz, CDCl₃): δ 7.63 (d, J = 15.2 Hz, 1H), 7.56–7.54 (m, 2H), 7.45–7.41 (m, 3H), 7.28 (d, J = 15.2 Hz, 1H), 4.87–4.82 (m, 2H), 3.67 (d, J = 16.8 Hz, 2H), 1.36 (d, J = 6.4 Hz, 12H). ¹³C (100 MHz, CDCl₃): δ 144.5, 132.3, 131.5, 129.2, 128.9, 126.2, 73.0, 72.9, 54.3 (d, J = 139.7 Hz), 24.3, 24.2, 24.0, 23.9. LRMS (ESI) m/z calculated for C₁₅H₂₃O₅PS (M + Na)⁺ 369.1, found 369.1.

Compound (II) was prepared as follows. In a flame-dried flask, the disulfone reagent (Wong, Olmstead, Fettinger & Gervay-Hague, 2007) (224 mg, 0.44 mmol), 7-methoxybenzo[1,3]dioxole-5-carbaldehyde (169 mg, 0.94 mmol), and LiBr (115 mg, 1.32 mmol) were dissolved in 3–4 ml of dry THF, and then Hunig's base (230 µl, 1.32 mmol) was added to the solution. After stirring overnight, the reaction mixture was quenched by the addition of 5% HCl until the pH was 3–4. The solution was partitioned between ethyl acetate and water, and extracted three times. The organic phase was collected and dried over sodium sulfate. The solvent was evaporated to yield a crude solid material that was subjected to column chromatography (30% ethyl acetate:70% hexanes, Rf = 0.21) to yield crystals of the mono-coupled product as a minor component in a test tube.

Compound (III) was the second product eluted from the column in the preparation of (I). It also crystallized in a test tube in 33% yield.

Compound (IV) was prepared as follows. The disulfone reagent (Wong, Olmstead, Fettinger & Gervay-Hague, 2007) (103 mg, 0.21 mmol), benzaldehyde (0.07 ml, 0.68 mmol) and LiBr (60 mg, 0.069 mmol) were dissolved in 3–4 ml of dry THF, and then Hunig's base (91 µl, 0.069 mmol) was added to the solution. The reaction mixture was stirred overnight before being quenched by the addition of 5% HCl until pH 3–4 was attained. The solution was partitioned between ethyl acetate (80 ml) and water (50 ml), and extracted three times (50 ml). The organic phase was collected and dried over sodium sulfate. After removal of solvent, the crude material was subjected to column chromatography (40% ethyl acetate:60% hexanes, Rf = 0.43) to yield 65 mg (88%) of (IV). ¹H NMR (CDCl₃, 400 MHz): δ 4.68 (s, 2H), 7.21 (d, 2H, J = 15.6 Hz), 7.38–7.54 (m, 10H), 7.67 (d, 2H, J = 15.6 Hz). ¹³C NMR (CDCl₃, 100 MHz): δ 74.11, 124.38, 129.18, 129.31, 131.77, 132.09, 147.02. F T–IR (film): ν 3060, 1612, 1448 (C═C), 1323, 1124 (SO₂ str), 976 (trans C═C str). Analysis calculated for C₁₇H₁₆O₄S₂: C 58.60, H 4.63%; found: C 58.21, H 4.63%.

S3. Refinement

In (I), all H atoms were treated as riding, with C—H distances in the range 0.95–1.00 Å and U_iso(H) values of 1.2U_eq (for primary and secondary) or 1.5U_eq (for tertiary) of the bonded C atom. The structure was refined as a pseudomerohedral twin. The twin law was (100/110/001) and the twin parameter 0.4822 (10). In (II), H atoms were located in a difference Fourier map and their positions were refined. Displacement parameters were treated as for (I) [please check; from data in CIF it looks like the postional parameters were treated as for (I) and the displacement parameters were refined]. In (III), one of the three molecules in the asymmetric unit is disordered in one-half of the molecule. Occupancies for these two components were originally refined and subsequently fixed at values of 0.57 and 0.43 for the major and minor parts, respectively. H atoms were treated as in (I). In (IV), all atoms were fully refined [C—H = 0.92 (2)–0.989 (19) Å].

Computing details

Data collection: SMART (Bruker, 2002) for (I), (III), (IV); APEX2 (Bruker, 2006) for (II). Cell refinement: SAINT (Version 7.23; Bruker, 2005) for (I); SAINT (Version 7.16b; Bruker, 2004) for (II), (III), (IV). Data reduction: SAINT (Version 7.23; Bruker, 2005) for (I); SAINT (Version 7.16b; Bruker, 2004) for (II), (III), (IV). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Version 5.1; Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures

	Fig. 1. A view of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been drawn at an arbitrary size. The two molecules are shown in projection down the vinyl group.
	Fig. 2. A view of the two molecules of (II) in the asymmetric unit, showing displacment ellipsoids at the 50% probability level. H atoms have been drawn at an arbitrary size. The projection of the two molecules is arbitrarily chosen to show the relationship between the two molecules
	Fig. 3. A view of the three molecules of (III), showing displacement ellipsoids at the 50% probability level. The disorder in one of the molecules has been omitted for clarity. H atoms have been drawn at an arbitrary size. The three molecules are shown in the relationship in which they exist in the asymmetric unit.
	Fig. 4. A view of (IV), showing displacement ellipsoids at the 50% probability level. H atoms have been drawn at an arbitrary size. [Symmetry code: (i) -x + 1, y, -z + 1/2.]

(I) (2-phenylethenylsulfonylmethyl)phosphonate

Crystal data

C15H23O5PS	Z = 4
Mr = 346.36	F(000) = 736
Triclinic, P1	Dx = 1.329 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.933 (3) Å	Cell parameters from 8053 reflections
b = 10.014 (3) Å	θ = 2.3–27.5°
c = 22.059 (7) Å	µ = 0.30 mm^−1
α = 79.769 (4)°	T = 90 K
β = 89.938 (4)°	Block, colorless
γ = 63.533 (4)°	0.55 × 0.53 × 0.38 mm
V = 1731.5 (10) Å^3

Data collection

Bruker SMART 1000 diffractometer	7911 independent reflections
Radiation source: fine-focus sealed tube	7462 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.3 pixels mm^-1	θmax = 27.5°, θmin = 0.9°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	k = −13→12
Tmin = 0.853, Tmax = 0.895	l = −28→28
15459 measured reflections

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: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 1.4392P] where P = (Fo^2 + 2Fc^2)/3
7911 reflections	(Δ/σ)max < 0.001
406 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.43 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
P1	0.85678 (8)	0.47936 (7)	0.08729 (3)	0.01641 (13)
S1	0.73714 (7)	0.30153 (7)	0.01997 (3)	0.01515 (12)
C1	0.8855 (3)	0.0767 (3)	−0.17566 (13)	0.0205 (5)
H1	0.9869	0.0084	−0.1509	0.025*
O1	0.5873 (2)	0.3319 (2)	0.05203 (8)	0.0196 (4)
C2	0.8638 (3)	0.0623 (3)	−0.23611 (12)	0.0224 (5)
H2	0.9510	−0.0146	−0.2529	0.027*
O2	0.8852 (2)	0.16304 (19)	0.04341 (9)	0.0205 (4)
C3	0.7167 (4)	0.1592 (3)	−0.27155 (13)	0.0253 (6)
H3	0.7009	0.1485	−0.3127	0.030*
O3	0.7586 (2)	0.4631 (2)	0.13967 (9)	0.0209 (4)
C4	0.5902 (4)	0.2735 (3)	−0.24707 (13)	0.0249 (6)
H4	0.4886	0.3415	−0.2718	0.030*
O4	0.8635 (2)	0.6376 (2)	0.07013 (9)	0.0191 (4)
C5	0.6118 (3)	0.2885 (3)	−0.18692 (13)	0.0212 (5)
H5	0.5248	0.3663	−0.1704	0.025*
O5	1.0471 (2)	0.3645 (2)	0.09252 (8)	0.0206 (4)
C6	0.7588 (3)	0.1912 (3)	−0.15103 (13)	0.0175 (5)
C7	0.7876 (3)	0.2003 (3)	−0.08675 (12)	0.0169 (5)
H7	0.8863	0.1205	−0.0637	0.020*
C8	0.6891 (3)	0.3096 (3)	−0.05745 (13)	0.0169 (5)
H8	0.5910	0.3931	−0.0792	0.020*
C9	0.7853 (3)	0.4584 (3)	0.01471 (12)	0.0156 (5)
H9A	0.6836	0.5533	−0.0031	0.019*
H9B	0.8731	0.4460	−0.0143	0.019*
C10	0.7198 (3)	0.7797 (3)	0.07849 (13)	0.0219 (5)
H10	0.6130	0.7721	0.0729	0.026*
C11	0.7410 (4)	0.8038 (4)	0.14296 (15)	0.0319 (7)
H11A	0.7459	0.7173	0.1733	0.048*
H11B	0.6456	0.8975	0.1493	0.048*
H11C	0.8453	0.8121	0.1481	0.048*
C12	0.7221 (4)	0.9024 (3)	0.02844 (15)	0.0316 (6)
H12A	0.8303	0.9043	0.0323	0.047*
H12B	0.6316	1.0012	0.0326	0.047*
H12C	0.7058	0.8815	−0.0121	0.047*
C13	1.1462 (3)	0.2955 (3)	0.15203 (13)	0.0229 (5)
H13	1.0839	0.2567	0.1820	0.028*
C14	1.3032 (3)	0.1641 (3)	0.13917 (14)	0.0268 (6)
H14A	1.2728	0.0992	0.1188	0.040*
H14B	1.3710	0.1046	0.1782	0.040*
H14C	1.3681	0.2030	0.1122	0.040*
C15	1.1817 (4)	0.4112 (3)	0.17673 (14)	0.0315 (6)
H15A	1.2379	0.4527	0.1463	0.047*
H15B	1.2544	0.3620	0.2154	0.047*
H15C	1.0758	0.4939	0.1844	0.047*
P21	0.83457 (8)	0.48268 (7)	0.41485 (3)	0.01740 (14)
S21	0.56212 (8)	0.68909 (7)	0.48265 (3)	0.01627 (12)
C21	0.4394 (3)	0.9398 (3)	0.67172 (12)	0.0210 (5)
H21	0.4685	1.0103	0.6463	0.025*
O21	0.6023 (2)	0.8142 (2)	0.46114 (9)	0.0223 (4)
C22	0.3910 (4)	0.9609 (3)	0.73062 (13)	0.0262 (6)
H22	0.3866	1.0462	0.7452	0.031*
O22	0.4324 (2)	0.6803 (2)	0.44761 (9)	0.0197 (4)
C23	0.3486 (3)	0.8577 (3)	0.76853 (13)	0.0246 (6)
H23	0.3154	0.8731	0.8087	0.030*
O23	0.7133 (2)	0.5293 (2)	0.36264 (9)	0.0233 (4)
C24	0.3552 (4)	0.7317 (3)	0.74746 (13)	0.0253 (6)
H24	0.3269	0.6612	0.7732	0.030*
O24	0.9595 (2)	0.5557 (2)	0.40632 (9)	0.0216 (4)
C25	0.4035 (3)	0.7101 (3)	0.68854 (13)	0.0226 (5)
H25	0.4084	0.6243	0.6742	0.027*
O25	0.9505 (3)	0.3076 (2)	0.43597 (9)	0.0268 (4)
C26	0.4452 (3)	0.8145 (3)	0.64990 (13)	0.0186 (5)
C27	0.4937 (3)	0.7995 (3)	0.58649 (12)	0.0189 (5)
H27	0.5140	0.8781	0.5631	0.023*
C28	0.5114 (3)	0.6856 (3)	0.55936 (12)	0.0184 (5)
H28	0.4965	0.6025	0.5815	0.022*
C29	0.7466 (3)	0.5160 (3)	0.48798 (12)	0.0180 (5)
H29A	0.7215	0.4312	0.5059	0.022*
H29B	0.8322	0.5150	0.5168	0.022*
C30	0.9264 (4)	0.6907 (3)	0.35856 (13)	0.0256 (6)
H30	0.8029	0.7488	0.3465	0.031*
C31	0.9845 (4)	0.7895 (3)	0.38561 (14)	0.0297 (6)
H31A	0.9339	0.8094	0.4245	0.045*
H31B	0.9504	0.8861	0.3564	0.045*
H31C	1.1071	0.7372	0.3935	0.045*
C32	1.0158 (7)	0.6371 (5)	0.30299 (18)	0.0643 (14)
H32A	1.1359	0.5738	0.3153	0.096*
H32B	0.9998	0.7254	0.2712	0.096*
H32C	0.9697	0.5774	0.2863	0.096*
C33	1.0908 (4)	0.2197 (4)	0.40207 (16)	0.0355 (7)
H33	1.1721	0.2637	0.3990	0.043*
C34	1.0363 (5)	0.2164 (4)	0.33954 (17)	0.0457 (9)
H34A	0.9560	0.1741	0.3425	0.069*
H34B	1.1340	0.1529	0.3197	0.069*
H34C	0.9827	0.3201	0.3149	0.069*
C35	1.1718 (4)	0.0629 (4)	0.44385 (17)	0.0415 (8)
H35A	1.2251	0.0677	0.4817	0.062*
H35B	1.2567	−0.0094	0.4222	0.062*
H35C	1.0857	0.0295	0.4546	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0149 (3)	0.0191 (3)	0.0204 (3)	−0.0098 (3)	0.0046 (2)	−0.0109 (2)
S1	0.0116 (3)	0.0149 (2)	0.0211 (3)	−0.0060 (2)	0.0007 (2)	−0.0087 (2)
C1	0.0165 (12)	0.0173 (11)	0.0299 (14)	−0.0076 (10)	0.0048 (10)	−0.0101 (10)
O1	0.0151 (8)	0.0226 (9)	0.0257 (10)	−0.0107 (7)	0.0056 (7)	−0.0104 (7)
C2	0.0215 (13)	0.0242 (12)	0.0267 (13)	−0.0115 (11)	0.0077 (11)	−0.0142 (10)
O2	0.0172 (9)	0.0153 (8)	0.0259 (10)	−0.0031 (7)	−0.0018 (7)	−0.0082 (7)
C3	0.0289 (15)	0.0315 (14)	0.0240 (14)	−0.0180 (12)	0.0039 (11)	−0.0141 (11)
O3	0.0188 (9)	0.0240 (9)	0.0246 (10)	−0.0113 (8)	0.0082 (8)	−0.0120 (8)
C4	0.0207 (13)	0.0270 (14)	0.0277 (14)	−0.0105 (11)	−0.0020 (11)	−0.0076 (11)
O4	0.0147 (8)	0.0207 (9)	0.0290 (10)	−0.0107 (7)	0.0084 (7)	−0.0147 (8)
C5	0.0155 (12)	0.0204 (12)	0.0293 (14)	−0.0071 (10)	0.0035 (11)	−0.0116 (10)
O5	0.0136 (8)	0.0238 (9)	0.0253 (9)	−0.0065 (7)	0.0003 (7)	−0.0125 (7)
C6	0.0175 (12)	0.0166 (11)	0.0234 (13)	−0.0098 (10)	0.0033 (10)	−0.0101 (10)
C7	0.0119 (11)	0.0178 (11)	0.0238 (13)	−0.0074 (9)	0.0010 (9)	−0.0092 (9)
C8	0.0111 (11)	0.0150 (11)	0.0250 (13)	−0.0047 (9)	−0.0018 (9)	−0.0081 (10)
C9	0.0113 (11)	0.0178 (11)	0.0203 (13)	−0.0072 (9)	0.0018 (9)	−0.0084 (9)
C10	0.0139 (12)	0.0209 (12)	0.0349 (14)	−0.0082 (10)	0.0043 (11)	−0.0141 (10)
C11	0.0311 (16)	0.0330 (16)	0.0375 (17)	−0.0133 (13)	0.0095 (13)	−0.0244 (14)
C12	0.0255 (14)	0.0236 (14)	0.0438 (18)	−0.0090 (12)	−0.0010 (13)	−0.0080 (13)
C13	0.0209 (13)	0.0223 (12)	0.0238 (13)	−0.0074 (11)	−0.0004 (10)	−0.0069 (10)
C14	0.0166 (13)	0.0263 (13)	0.0358 (15)	−0.0076 (11)	0.0028 (11)	−0.0079 (11)
C15	0.0312 (16)	0.0311 (14)	0.0329 (16)	−0.0115 (13)	−0.0047 (13)	−0.0150 (12)
P21	0.0145 (3)	0.0179 (3)	0.0218 (3)	−0.0066 (2)	0.0037 (2)	−0.0110 (2)
S21	0.0152 (3)	0.0149 (2)	0.0218 (3)	−0.0076 (2)	0.0056 (2)	−0.0090 (2)
C21	0.0223 (13)	0.0191 (11)	0.0228 (13)	−0.0091 (10)	0.0055 (11)	−0.0075 (10)
O21	0.0276 (10)	0.0171 (8)	0.0281 (10)	−0.0133 (8)	0.0100 (8)	−0.0102 (7)
C22	0.0268 (14)	0.0222 (12)	0.0282 (14)	−0.0070 (11)	0.0021 (12)	−0.0131 (11)
O22	0.0125 (8)	0.0225 (9)	0.0247 (9)	−0.0065 (7)	0.0009 (7)	−0.0103 (7)
C23	0.0215 (13)	0.0303 (14)	0.0222 (13)	−0.0095 (11)	0.0056 (11)	−0.0112 (11)
O23	0.0191 (9)	0.0280 (10)	0.0269 (10)	−0.0110 (8)	0.0028 (8)	−0.0144 (8)
C24	0.0229 (14)	0.0342 (15)	0.0256 (14)	−0.0183 (12)	0.0054 (11)	−0.0074 (12)
O24	0.0180 (9)	0.0259 (9)	0.0245 (9)	−0.0131 (8)	0.0025 (7)	−0.0049 (7)
C25	0.0205 (13)	0.0274 (13)	0.0278 (14)	−0.0152 (11)	0.0062 (11)	−0.0125 (11)
O25	0.0235 (10)	0.0200 (9)	0.0341 (11)	−0.0050 (8)	0.0070 (9)	−0.0122 (8)
C26	0.0144 (11)	0.0184 (12)	0.0240 (14)	−0.0064 (9)	0.0023 (10)	−0.0092 (10)
C27	0.0157 (12)	0.0174 (11)	0.0255 (13)	−0.0075 (10)	0.0056 (10)	−0.0084 (9)
C28	0.0173 (12)	0.0201 (12)	0.0210 (13)	−0.0098 (10)	0.0050 (10)	−0.0084 (10)
C29	0.0162 (12)	0.0191 (11)	0.0221 (14)	−0.0090 (10)	0.0034 (10)	−0.0093 (10)
C30	0.0313 (15)	0.0242 (13)	0.0270 (14)	−0.0167 (12)	−0.0010 (12)	−0.0076 (11)
C31	0.0331 (16)	0.0335 (15)	0.0329 (15)	−0.0210 (13)	0.0076 (13)	−0.0152 (12)
C32	0.132 (4)	0.073 (3)	0.040 (2)	−0.082 (3)	0.046 (2)	−0.037 (2)
C33	0.0293 (16)	0.0327 (16)	0.0443 (18)	−0.0090 (13)	0.0072 (14)	−0.0212 (14)
C34	0.049 (2)	0.0373 (18)	0.046 (2)	−0.0084 (16)	0.0116 (17)	−0.0275 (16)
C35	0.0340 (17)	0.0271 (15)	0.051 (2)	−0.0006 (14)	0.0002 (15)	−0.0152 (14)

Geometric parameters (Å, º)

P1—O3	1.4794 (19)	P21—O23	1.442 (2)
P1—O5	1.5614 (19)	P21—O25	1.5673 (19)
P1—O4	1.5901 (19)	P21—O24	1.5792 (19)
P1—C9	1.805 (3)	P21—C29	1.813 (3)
S1—O2	1.4324 (18)	S21—O22	1.4368 (19)
S1—O1	1.4480 (19)	S21—O21	1.4539 (19)
S1—C8	1.741 (3)	S21—C28	1.750 (3)
S1—C9	1.790 (2)	S21—C29	1.765 (3)
C1—C2	1.389 (4)	C21—C22	1.391 (4)
C1—C6	1.398 (3)	C21—C26	1.402 (3)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.369 (4)	C22—C23	1.397 (4)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.395 (4)	C23—C24	1.398 (4)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.385 (4)	C24—C25	1.392 (4)
C4—H4	0.9500	C24—H24	0.9500
O4—C10	1.473 (3)	O24—C30	1.471 (3)
C5—C6	1.374 (4)	C25—C26	1.410 (4)
C5—H5	0.9500	C25—H25	0.9500
O5—C13	1.456 (3)	O25—C33	1.468 (3)
C6—C7	1.467 (4)	C26—C27	1.477 (4)
C7—C8	1.335 (3)	C27—C28	1.329 (3)
C7—H7	0.9500	C27—H27	0.9500
C8—H8	0.9500	C28—H28	0.9500
C9—H9A	0.9900	C29—H29A	0.9900
C9—H9B	0.9900	C29—H29B	0.9900
C10—C12	1.507 (4)	C30—C31	1.508 (4)
C10—C11	1.510 (4)	C30—C32	1.509 (4)
C10—H10	1.0000	C30—H30	1.0000
C11—H11A	0.9800	C31—H31A	0.9800
C11—H11B	0.9800	C31—H31B	0.9800
C11—H11C	0.9800	C31—H31C	0.9800
C12—H12A	0.9800	C32—H32A	0.9800
C12—H12B	0.9800	C32—H32B	0.9800
C12—H12C	0.9800	C32—H32C	0.9800
C13—C14	1.506 (4)	C33—C34	1.474 (5)
C13—C15	1.514 (4)	C33—C35	1.521 (5)
C13—H13	1.0000	C33—H33	1.0000
C14—H14A	0.9800	C34—H34A	0.9800
C14—H14B	0.9800	C34—H34B	0.9800
C14—H14C	0.9800	C34—H34C	0.9800
C15—H15A	0.9800	C35—H35A	0.9800
C15—H15B	0.9800	C35—H35B	0.9800
C15—H15C	0.9800	C35—H35C	0.9800
O3—P1—O5	117.92 (11)	O23—P21—O25	116.82 (11)
O3—P1—O4	116.09 (10)	O23—P21—O24	114.32 (12)
O5—P1—O4	101.29 (10)	O25—P21—O24	104.73 (11)
O3—P1—C9	114.89 (11)	O23—P21—C29	115.16 (12)
O5—P1—C9	101.08 (10)	O25—P21—C29	97.14 (11)
O4—P1—C9	103.24 (11)	O24—P21—C29	106.77 (11)
O2—S1—O1	117.76 (12)	O22—S21—O21	118.14 (12)
O2—S1—C8	109.31 (11)	O22—S21—C28	107.76 (12)
O1—S1—C8	108.37 (11)	O21—S21—C28	110.43 (12)
O2—S1—C9	109.06 (11)	O22—S21—C29	107.97 (11)
O1—S1—C9	109.56 (11)	O21—S21—C29	108.66 (12)
C8—S1—C9	101.56 (12)	C28—S21—C29	102.76 (13)
C2—C1—C6	120.3 (3)	C22—C21—C26	119.9 (3)
C2—C1—H1	119.8	C22—C21—H21	120.0
C6—C1—H1	119.8	C26—C21—H21	120.0
C3—C2—C1	120.0 (2)	C21—C22—C23	120.5 (2)
C3—C2—H2	120.0	C21—C22—H22	119.7
C1—C2—H2	120.0	C23—C22—H22	119.7
C2—C3—C4	119.8 (3)	C22—C23—C24	120.0 (3)
C2—C3—H3	120.1	C22—C23—H23	120.0
C4—C3—H3	120.1	C24—C23—H23	120.0
C5—C4—C3	120.3 (3)	C25—C24—C23	119.7 (3)
C5—C4—H4	119.8	C25—C24—H24	120.2
C3—C4—H4	119.8	C23—C24—H24	120.2
C10—O4—P1	120.72 (15)	C30—O24—P21	122.51 (17)
C6—C5—C4	120.1 (2)	C24—C25—C26	120.6 (2)
C6—C5—H5	119.9	C24—C25—H25	119.7
C4—C5—H5	119.9	C26—C25—H25	119.7
C13—O5—P1	121.69 (16)	C33—O25—P21	123.42 (19)
C5—C6—C1	119.4 (3)	C21—C26—C25	119.3 (2)
C5—C6—C7	122.5 (2)	C21—C26—C27	117.7 (2)
C1—C6—C7	118.1 (2)	C25—C26—C27	123.0 (2)
C8—C7—C6	126.5 (2)	C28—C27—C26	125.7 (2)
C8—C7—H7	116.8	C28—C27—H27	117.2
C6—C7—H7	116.8	C26—C27—H27	117.2
C7—C8—S1	121.1 (2)	C27—C28—S21	119.8 (2)
C7—C8—H8	119.5	C27—C28—H28	120.1
S1—C8—H8	119.5	S21—C28—H28	120.1
S1—C9—P1	114.68 (14)	S21—C29—P21	114.35 (15)
S1—C9—H9A	108.6	S21—C29—H29A	108.7
P1—C9—H9A	108.6	P21—C29—H29A	108.7
S1—C9—H9B	108.6	S21—C29—H29B	108.7
P1—C9—H9B	108.6	P21—C29—H29B	108.7
H9A—C9—H9B	107.6	H29A—C29—H29B	107.6
O4—C10—C12	105.5 (2)	O24—C30—C31	108.3 (2)
O4—C10—C11	108.6 (2)	O24—C30—C32	108.0 (3)
C12—C10—C11	113.3 (2)	C31—C30—C32	113.1 (3)
O4—C10—H10	109.8	O24—C30—H30	109.1
C12—C10—H10	109.8	C31—C30—H30	109.1
C11—C10—H10	109.8	C32—C30—H30	109.1
C10—C11—H11A	109.5	C30—C31—H31A	109.5
C10—C11—H11B	109.5	C30—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
C10—C11—H11C	109.5	C30—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C10—C12—H12A	109.5	C30—C32—H32A	109.5
C10—C12—H12B	109.5	C30—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
C10—C12—H12C	109.5	C30—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5
O5—C13—C14	104.7 (2)	O25—C33—C34	112.9 (3)
O5—C13—C15	110.2 (2)	O25—C33—C35	103.0 (3)
C14—C13—C15	112.8 (2)	C34—C33—C35	112.7 (3)
O5—C13—H13	109.7	O25—C33—H33	109.4
C14—C13—H13	109.7	C34—C33—H33	109.4
C15—C13—H13	109.7	C35—C33—H33	109.4
C13—C14—H14A	109.5	C33—C34—H34A	109.5
C13—C14—H14B	109.5	C33—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C13—C14—H14C	109.5	C33—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C13—C15—H15A	109.5	C33—C35—H35A	109.5
C13—C15—H15B	109.5	C33—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C13—C15—H15C	109.5	C33—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C6—C1—C2—C3	−1.0 (4)	C26—C21—C22—C23	0.3 (4)
C1—C2—C3—C4	1.0 (4)	C21—C22—C23—C24	0.2 (4)
C2—C3—C4—C5	−0.7 (4)	C22—C23—C24—C25	−0.2 (4)
O3—P1—O4—C10	−32.6 (2)	O23—P21—O24—C30	16.9 (2)
O5—P1—O4—C10	−161.58 (18)	O25—P21—O24—C30	146.03 (19)
C9—P1—O4—C10	94.05 (19)	C29—P21—O24—C30	−111.6 (2)
C3—C4—C5—C6	0.4 (4)	C23—C24—C25—C26	−0.2 (4)
O3—P1—O5—C13	−29.6 (2)	O23—P21—O25—C33	74.5 (2)
O4—P1—O5—C13	98.3 (2)	O24—P21—O25—C33	−53.1 (2)
C9—P1—O5—C13	−155.65 (19)	C29—P21—O25—C33	−162.6 (2)
C4—C5—C6—C1	−0.3 (4)	C22—C21—C26—C25	−0.8 (4)
C4—C5—C6—C7	−179.1 (2)	C22—C21—C26—C27	178.6 (2)
C2—C1—C6—C5	0.6 (4)	C24—C25—C26—C21	0.7 (4)
C2—C1—C6—C7	179.4 (2)	C24—C25—C26—C27	−178.6 (3)
C5—C6—C7—C8	−8.1 (4)	C21—C26—C27—C28	177.5 (3)
C1—C6—C7—C8	173.1 (3)	C25—C26—C27—C28	−3.2 (4)
C6—C7—C8—S1	178.0 (2)	C26—C27—C28—S21	177.6 (2)
O2—S1—C8—C7	−2.6 (3)	O22—S21—C28—C27	−122.2 (2)
O1—S1—C8—C7	−132.1 (2)	O21—S21—C28—C27	8.2 (3)
C9—S1—C8—C7	112.6 (2)	C29—S21—C28—C27	123.9 (2)
O2—S1—C9—P1	−60.57 (16)	O22—S21—C29—P21	66.18 (16)
O1—S1—C9—P1	69.64 (16)	O21—S21—C29—P21	−63.09 (16)
C8—S1—C9—P1	−175.90 (13)	C28—S21—C29—P21	179.90 (14)
O3—P1—C9—S1	−44.73 (17)	O23—P21—C29—S21	−38.84 (18)
O5—P1—C9—S1	83.36 (15)	O25—P21—C29—S21	−162.98 (14)
O4—P1—C9—S1	−172.11 (12)	O24—P21—C29—S21	89.23 (15)
P1—O4—C10—C12	−148.57 (18)	P21—O24—C30—C31	141.7 (2)
P1—O4—C10—C11	89.7 (2)	P21—O24—C30—C32	−95.5 (3)
P1—O5—C13—C14	164.82 (17)	P21—O25—C33—C34	−63.5 (3)
P1—O5—C13—C15	−73.7 (3)	P21—O25—C33—C35	174.7 (2)

(II) diisopropyl {[2-(7-methoxy-1,3-benzodioxol-5- yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate

Crystal data

C18H27O10PS2	Z = 4
Mr = 498.49	F(000) = 1048
Triclinic, P1	Dx = 1.465 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8656 (3) Å	Cell parameters from 8381 reflections
b = 15.1481 (5) Å	θ = 2.5–30.1°
c = 15.9024 (5) Å	µ = 0.36 mm^−1
α = 86.929 (3)°	T = 90 K
β = 89.893 (3)°	Rod, colorless
γ = 72.267 (3)°	0.49 × 0.08 × 0.07 mm
V = 2260.11 (12) Å^3

Data collection

Bruker SMART ApexII diffractometer	13151 independent reflections
Radiation source: fine-focus sealed tube	11227 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.3 pixels mm^-1	θmax = 30.0°, θmin = 1.9°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	k = −21→21
Tmin = 0.845, Tmax = 0.976	l = −22→22
25647 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	Only H-atom coordinates refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 1.1703P] where P = (Fo^2 + 2Fc^2)/3
13151 reflections	(Δ/σ)max = 0.001
623 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.35 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
P1	0.65255 (4)	0.10258 (2)	0.47019 (2)	0.01360 (7)
S1	0.62912 (3)	0.32474 (2)	0.670000 (19)	0.01231 (6)
S2	0.59986 (3)	0.13154 (2)	0.65576 (2)	0.01348 (7)
C1	0.45611 (15)	0.38667 (9)	1.03805 (8)	0.0152 (2)
C1A	0.56207 (16)	0.40024 (9)	1.08805 (8)	0.0160 (2)
C1B	0.21556 (17)	0.38647 (12)	1.02248 (10)	0.0236 (3)
H1B1	0.2013	0.4328	0.9753	0.031 (5)*
H1B2	0.1280	0.3983	1.0550	0.038 (6)*
H1B3	0.2396	0.3243	1.0008	0.037 (6)*
O1	0.32935 (11)	0.39229 (7)	1.07565 (6)	0.0195 (2)
C2	0.69185 (19)	0.42878 (12)	1.19243 (9)	0.0250 (3)
H2A	0.6815	0.4904	1.2144	0.041 (6)*
H2B	0.7388	0.3805	1.2365	0.029 (5)*
O2	0.55400 (12)	0.42121 (8)	1.17103 (6)	0.0219 (2)
C3	0.72719 (15)	0.38276 (9)	0.97283 (8)	0.0150 (2)
H3	0.8173	0.3824	0.9515	0.024 (5)*
C3A	0.69322 (15)	0.39773 (9)	1.05607 (8)	0.0157 (2)
O3	0.77609 (12)	0.41689 (8)	1.11737 (6)	0.0230 (2)
C4	0.62138 (14)	0.36800 (9)	0.92108 (8)	0.0128 (2)
O4	0.74259 (10)	0.36562 (7)	0.65794 (6)	0.01669 (19)
C5	0.48751 (14)	0.36971 (9)	0.95340 (8)	0.0143 (2)
H5	0.4179	0.3592	0.9174	0.012 (4)*
O5	0.50574 (10)	0.35581 (7)	0.61487 (6)	0.01783 (19)
C6	0.65474 (14)	0.35408 (9)	0.83223 (8)	0.0132 (2)
H6	0.7430	0.3609	0.8141	0.024 (5)*
O6	0.48411 (11)	0.16621 (7)	0.71262 (6)	0.0185 (2)
C7	0.57439 (14)	0.33279 (9)	0.77386 (8)	0.0140 (2)
H7	0.4874	0.3221	0.7892	0.026 (5)*
O7	0.69319 (12)	0.03822 (7)	0.66989 (7)	0.0208 (2)
C8	0.71192 (14)	0.20422 (9)	0.65489 (8)	0.0146 (2)
H8A	0.7612	0.1989	0.6003	0.032 (5)*
H8B	0.7857	0.1795	0.6994	0.022 (5)*
O8	0.54777 (11)	0.13553 (7)	0.39322 (6)	0.0189 (2)
C9	0.52568 (14)	0.14409 (9)	0.55293 (8)	0.0145 (2)
H9A	0.4750	0.2106	0.5399	0.026 (5)*
H9B	0.4542	0.1103	0.5523	0.035 (6)*
O9	0.69009 (10)	−0.00627 (7)	0.47599 (6)	0.01584 (19)
C10	0.60148 (16)	0.13119 (10)	0.30599 (8)	0.0183 (3)
H10	0.6990	0.0855	0.3052	0.029 (5)*
O10	0.77637 (11)	0.13750 (7)	0.47310 (6)	0.0193 (2)
C11	0.6089 (3)	0.22586 (13)	0.27908 (12)	0.0454 (6)
H11A	0.5148	0.2715	0.2843	0.075 (9)*
H11B	0.6389	0.2263	0.2203	0.042 (6)*
H11C	0.6777	0.2417	0.3150	0.086 (11)*
C12	0.5027 (3)	0.0984 (2)	0.25415 (12)	0.0612 (8)
H12A	0.5012	0.0372	0.2767	0.076 (10)*
H12B	0.5351	0.0940	0.1958	0.054 (7)*
H12C	0.4066	0.1425	0.2558	0.085 (11)*
C13	0.83487 (14)	−0.06819 (10)	0.49824 (9)	0.0181 (3)
H13	0.8900	−0.0327	0.5271	0.019 (4)*
C14	0.81785 (17)	−0.14531 (10)	0.55724 (10)	0.0228 (3)
H14A	0.7603	−0.1186	0.6053	0.034 (6)*
H14B	0.9118	−0.1845	0.5775	0.031 (5)*
H14C	0.7704	−0.1828	0.5273	0.032 (5)*
C15	0.90642 (18)	−0.10274 (14)	0.41712 (11)	0.0328 (4)
H15A	0.8478	−0.1328	0.3867	0.034 (6)*
H15B	1.0001	−0.1476	0.4298	0.050 (7)*
H15C	0.9178	−0.0503	0.3822	0.030 (5)*
P21	0.84887 (4)	0.89444 (2)	−0.01877 (2)	0.01329 (7)
S21	0.87260 (3)	0.67349 (2)	0.203910 (19)	0.01180 (6)
S22	0.90315 (3)	0.86631 (2)	0.16972 (2)	0.01342 (7)
O21	1.16970 (11)	0.58996 (8)	0.61561 (6)	0.0213 (2)
O22	0.93511 (12)	0.57667 (7)	0.71458 (6)	0.0207 (2)
O23	0.70836 (11)	0.59387 (8)	0.66088 (6)	0.0210 (2)
O24	0.75916 (10)	0.63298 (7)	0.19439 (6)	0.01615 (19)
O25	0.99720 (10)	0.64304 (7)	0.15231 (6)	0.01645 (19)
O26	1.01940 (11)	0.83121 (7)	0.22947 (6)	0.0188 (2)
O27	0.81100 (12)	0.95983 (7)	0.17469 (7)	0.0210 (2)
O28	0.95287 (11)	0.86026 (7)	−0.09272 (6)	0.0184 (2)
O29	0.81183 (10)	1.00328 (7)	−0.02489 (6)	0.01557 (18)
O30	0.72443 (11)	0.86023 (7)	−0.01101 (6)	0.0185 (2)
C21	1.04116 (15)	0.60162 (9)	0.57723 (8)	0.0153 (2)
C21A	0.93154 (15)	0.59304 (9)	0.62872 (8)	0.0156 (2)
C21B	1.28095 (17)	0.60337 (12)	0.56322 (10)	0.0245 (3)
H21A	1.2528	0.6675	0.5394	0.030 (5)*
H21B	1.2977	0.5606	0.5175	0.029 (5)*
H21C	1.3684	0.5912	0.5970	0.041 (6)*
C22	0.80079 (17)	0.55976 (11)	0.73296 (9)	0.0237 (3)
H22A	0.8159	0.4925	0.7440	0.022 (5)*
H22B	0.7580	0.5924	0.7834	0.037 (6)*
C23	0.76504 (14)	0.61748 (9)	0.51182 (8)	0.0149 (2)
H23	0.6734	0.6216	0.4903	0.016 (4)*
C23A	0.79757 (15)	0.60222 (9)	0.59673 (8)	0.0152 (2)
C24	0.87513 (14)	0.62661 (9)	0.45857 (8)	0.0127 (2)
C25	1.01130 (14)	0.61896 (9)	0.49098 (8)	0.0140 (2)
H25	1.0835	0.6256	0.4538	0.015 (4)*
C26	0.84344 (14)	0.64110 (9)	0.36828 (8)	0.0129 (2)
H26	0.7565	0.6332	0.3499	0.028 (5)*
C27	0.92482 (14)	0.66438 (9)	0.30883 (8)	0.0134 (2)
H27	1.0107	0.6758	0.3241	0.028 (5)*
C28	0.79034 (14)	0.79434 (9)	0.17743 (8)	0.0143 (2)
H28A	0.7396	0.8001	0.1228	0.026 (5)*
H28B	0.7177	0.8191	0.2203	0.029 (5)*
C29	0.97641 (14)	0.85330 (9)	0.06772 (8)	0.0144 (2)
H29A	1.0270	0.7867	0.0615	0.024 (5)*
H29B	1.0479	0.8871	0.0630	0.037 (6)*
C30	0.89854 (16)	0.86548 (10)	−0.18037 (8)	0.0183 (3)
H30	0.8022	0.9126	−0.1859	0.020 (4)*
C31	0.8875 (3)	0.77142 (13)	−0.19814 (12)	0.0435 (5)
H31A	0.8160	0.7572	−0.1615	0.084 (10)*
H31B	0.9799	0.7244	−0.1874	0.054 (7)*
H31C	0.8592	0.7713	−0.2572	0.056 (7)*
C32	1.0005 (3)	0.8958 (2)	−0.23556 (11)	0.0503 (6)
H32A	1.0030	0.9571	−0.2202	0.059 (8)*
H32B	0.9697	0.8992	−0.2945	0.046 (7)*
H32C	1.0957	0.8510	−0.2282	0.078 (10)*
C33	0.66698 (14)	1.06512 (10)	−0.00853 (9)	0.0173 (3)
H33	0.6120	1.0294	0.0238	0.022 (5)*
C34	0.68405 (17)	1.14179 (10)	0.04343 (10)	0.0215 (3)
H34A	0.7421	1.1146	0.0937	0.030 (5)*
H34B	0.5902	1.1806	0.0604	0.027 (5)*
H34C	0.7310	1.1799	0.0099	0.033 (5)*
C35	0.59535 (18)	1.10003 (13)	−0.09271 (11)	0.0293 (3)
H35A	0.5849	1.0476	−0.1228	0.032 (5)*
H35B	0.6533	1.1309	−0.1259	0.038 (6)*
H35C	0.5012	1.1443	−0.0841	0.037 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01522 (16)	0.01506 (15)	0.01169 (15)	−0.00611 (12)	0.00153 (11)	−0.00241 (12)
S1	0.01125 (14)	0.01576 (14)	0.01087 (13)	−0.00527 (11)	0.00094 (10)	−0.00223 (11)
S2	0.01464 (14)	0.01453 (14)	0.01182 (14)	−0.00497 (11)	0.00171 (11)	−0.00260 (11)
C1	0.0196 (6)	0.0113 (5)	0.0139 (6)	−0.0036 (5)	0.0038 (5)	0.0007 (4)
C1A	0.0258 (7)	0.0111 (6)	0.0099 (5)	−0.0037 (5)	0.0011 (5)	−0.0003 (4)
C1B	0.0236 (7)	0.0292 (8)	0.0205 (7)	−0.0118 (6)	0.0042 (6)	−0.0016 (6)
O1	0.0220 (5)	0.0248 (5)	0.0132 (4)	−0.0093 (4)	0.0063 (4)	−0.0024 (4)
C2	0.0382 (9)	0.0268 (8)	0.0148 (6)	−0.0167 (7)	−0.0012 (6)	−0.0024 (6)
O2	0.0325 (6)	0.0230 (5)	0.0102 (4)	−0.0079 (4)	0.0015 (4)	−0.0028 (4)
C3	0.0172 (6)	0.0133 (6)	0.0137 (6)	−0.0035 (5)	−0.0002 (5)	−0.0016 (4)
C3A	0.0218 (6)	0.0116 (6)	0.0132 (6)	−0.0041 (5)	−0.0031 (5)	−0.0013 (4)
O3	0.0255 (5)	0.0310 (6)	0.0141 (5)	−0.0101 (5)	−0.0031 (4)	−0.0054 (4)
C4	0.0168 (6)	0.0096 (5)	0.0115 (5)	−0.0031 (4)	0.0014 (4)	−0.0016 (4)
O4	0.0160 (5)	0.0229 (5)	0.0147 (4)	−0.0111 (4)	0.0016 (3)	−0.0018 (4)
C5	0.0175 (6)	0.0130 (6)	0.0123 (6)	−0.0047 (5)	0.0020 (5)	−0.0017 (4)
O5	0.0147 (5)	0.0222 (5)	0.0160 (5)	−0.0050 (4)	−0.0035 (4)	0.0002 (4)
C6	0.0136 (6)	0.0124 (5)	0.0134 (6)	−0.0033 (4)	0.0028 (4)	−0.0020 (4)
O6	0.0184 (5)	0.0237 (5)	0.0158 (5)	−0.0094 (4)	0.0066 (4)	−0.0052 (4)
C7	0.0157 (6)	0.0152 (6)	0.0116 (5)	−0.0051 (5)	0.0037 (4)	−0.0037 (4)
O7	0.0253 (5)	0.0152 (5)	0.0190 (5)	−0.0020 (4)	−0.0010 (4)	−0.0006 (4)
C8	0.0112 (6)	0.0179 (6)	0.0156 (6)	−0.0049 (5)	0.0016 (4)	−0.0050 (5)
O8	0.0199 (5)	0.0240 (5)	0.0117 (4)	−0.0050 (4)	0.0011 (4)	−0.0006 (4)
C9	0.0153 (6)	0.0164 (6)	0.0130 (6)	−0.0061 (5)	0.0005 (4)	−0.0037 (5)
O9	0.0141 (4)	0.0146 (4)	0.0189 (5)	−0.0039 (4)	−0.0002 (4)	−0.0038 (4)
C10	0.0247 (7)	0.0204 (7)	0.0116 (6)	−0.0094 (5)	0.0031 (5)	−0.0005 (5)
O10	0.0196 (5)	0.0227 (5)	0.0190 (5)	−0.0113 (4)	0.0045 (4)	−0.0041 (4)
C11	0.0868 (17)	0.0212 (8)	0.0284 (9)	−0.0170 (10)	0.0228 (10)	−0.0004 (7)
C12	0.0697 (17)	0.127 (2)	0.0188 (9)	−0.0754 (18)	0.0069 (9)	−0.0132 (11)
C13	0.0124 (6)	0.0201 (6)	0.0198 (6)	−0.0014 (5)	−0.0008 (5)	−0.0044 (5)
C14	0.0262 (7)	0.0157 (6)	0.0233 (7)	−0.0013 (6)	−0.0024 (6)	−0.0030 (5)
C15	0.0231 (8)	0.0405 (10)	0.0279 (8)	0.0011 (7)	0.0089 (6)	−0.0059 (7)
P21	0.01503 (15)	0.01381 (15)	0.01130 (14)	−0.00494 (12)	−0.00077 (11)	0.00029 (11)
S21	0.01100 (13)	0.01500 (14)	0.00989 (13)	−0.00484 (11)	0.00037 (10)	0.00008 (10)
S22	0.01514 (14)	0.01413 (14)	0.01127 (14)	−0.00507 (11)	−0.00118 (11)	0.00037 (11)
O21	0.0218 (5)	0.0299 (6)	0.0142 (5)	−0.0116 (4)	−0.0052 (4)	0.0017 (4)
O22	0.0309 (6)	0.0222 (5)	0.0098 (4)	−0.0093 (4)	0.0004 (4)	−0.0004 (4)
O23	0.0226 (5)	0.0253 (5)	0.0130 (5)	−0.0047 (4)	0.0054 (4)	0.0024 (4)
O24	0.0155 (4)	0.0215 (5)	0.0146 (4)	−0.0103 (4)	0.0004 (3)	−0.0015 (4)
O25	0.0137 (4)	0.0206 (5)	0.0146 (4)	−0.0044 (4)	0.0039 (3)	−0.0016 (4)
O26	0.0190 (5)	0.0241 (5)	0.0153 (5)	−0.0099 (4)	−0.0053 (4)	0.0022 (4)
O27	0.0264 (5)	0.0151 (5)	0.0191 (5)	−0.0027 (4)	0.0014 (4)	−0.0017 (4)
O28	0.0194 (5)	0.0222 (5)	0.0117 (4)	−0.0031 (4)	−0.0005 (4)	−0.0026 (4)
O29	0.0135 (4)	0.0135 (4)	0.0186 (5)	−0.0030 (3)	0.0011 (3)	0.0017 (4)
O30	0.0198 (5)	0.0198 (5)	0.0184 (5)	−0.0097 (4)	−0.0036 (4)	0.0013 (4)
C21	0.0186 (6)	0.0138 (6)	0.0137 (6)	−0.0051 (5)	−0.0020 (5)	−0.0008 (5)
C21A	0.0246 (7)	0.0122 (6)	0.0093 (5)	−0.0045 (5)	0.0001 (5)	−0.0004 (4)
C21B	0.0229 (7)	0.0327 (8)	0.0213 (7)	−0.0137 (6)	−0.0035 (6)	0.0008 (6)
C22	0.0299 (8)	0.0262 (7)	0.0146 (6)	−0.0086 (6)	0.0020 (6)	0.0019 (5)
C23	0.0163 (6)	0.0137 (6)	0.0136 (6)	−0.0034 (5)	0.0016 (5)	0.0001 (4)
C23A	0.0192 (6)	0.0117 (6)	0.0135 (6)	−0.0031 (5)	0.0046 (5)	−0.0007 (4)
C24	0.0155 (6)	0.0113 (5)	0.0107 (5)	−0.0032 (4)	0.0005 (4)	0.0000 (4)
C25	0.0168 (6)	0.0129 (6)	0.0124 (6)	−0.0045 (5)	−0.0005 (4)	−0.0006 (4)
C26	0.0133 (6)	0.0125 (6)	0.0123 (6)	−0.0033 (4)	−0.0004 (4)	−0.0003 (4)
C27	0.0142 (6)	0.0152 (6)	0.0111 (5)	−0.0051 (5)	−0.0013 (4)	0.0005 (4)
C28	0.0116 (6)	0.0169 (6)	0.0136 (6)	−0.0039 (5)	−0.0006 (4)	0.0027 (5)
C29	0.0147 (6)	0.0159 (6)	0.0126 (6)	−0.0049 (5)	0.0005 (4)	0.0011 (5)
C30	0.0244 (7)	0.0197 (6)	0.0116 (6)	−0.0078 (5)	−0.0020 (5)	−0.0004 (5)
C31	0.0826 (16)	0.0248 (9)	0.0264 (9)	−0.0207 (10)	−0.0144 (10)	−0.0027 (7)
C32	0.0581 (14)	0.0979 (19)	0.0167 (8)	−0.0569 (14)	−0.0002 (8)	0.0016 (9)
C33	0.0136 (6)	0.0176 (6)	0.0184 (6)	−0.0019 (5)	0.0020 (5)	0.0015 (5)
C34	0.0250 (7)	0.0153 (6)	0.0210 (7)	−0.0015 (5)	0.0018 (5)	0.0003 (5)
C35	0.0230 (8)	0.0327 (9)	0.0264 (8)	−0.0002 (7)	−0.0081 (6)	0.0007 (7)

Geometric parameters (Å, º)

P1—O10	1.4734 (10)	P21—O30	1.4736 (10)
P1—O8	1.5623 (10)	P21—O28	1.5623 (10)
P1—O9	1.5736 (10)	P21—O29	1.5739 (10)
P1—C9	1.8156 (14)	P21—C29	1.8167 (14)
S1—O4	1.4430 (10)	S21—O24	1.4424 (10)
S1—O5	1.4431 (10)	S21—O25	1.4452 (10)
S1—C7	1.7356 (13)	S21—C27	1.7330 (13)
S1—C8	1.7877 (14)	S21—C28	1.7891 (14)
S2—O7	1.4389 (11)	S22—O27	1.4376 (11)
S2—O6	1.4420 (10)	S22—O26	1.4420 (10)
S2—C9	1.7698 (13)	S22—C29	1.7707 (13)
S2—C8	1.7816 (14)	S22—C28	1.7795 (14)
C1—O1	1.3662 (16)	O21—C21	1.3663 (16)
C1—C1A	1.385 (2)	O21—C21B	1.4333 (19)
C1—C5	1.4004 (18)	O22—C21A	1.3730 (16)
C1A—O2	1.3702 (16)	O22—C22	1.4506 (19)
C1A—C3A	1.380 (2)	O23—C23A	1.3718 (16)
C1B—O1	1.4333 (18)	O23—C22	1.4374 (18)
C1B—H1B1	0.9800	O28—C30	1.4836 (16)
C1B—H1B2	0.9800	O29—C33	1.4821 (16)
C1B—H1B3	0.9800	C21—C21A	1.3885 (19)
C2—O3	1.4409 (19)	C21—C25	1.3974 (18)
C2—O2	1.442 (2)	C21A—C23A	1.381 (2)
C2—H2A	0.9900	C21B—H21A	0.9800
C2—H2B	0.9900	C21B—H21B	0.9800
C3—C3A	1.3785 (18)	C21B—H21C	0.9800
C3—C4	1.4078 (18)	C22—H22A	0.9900
C3—H3	0.9500	C22—H22B	0.9900
C3A—O3	1.3714 (16)	C23—C23A	1.3793 (18)
C4—C5	1.4097 (18)	C23—C24	1.4111 (18)
C4—C6	1.4619 (17)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.4090 (18)
C6—C7	1.3359 (18)	C24—C26	1.4607 (17)
C6—H6	0.9500	C25—H25	0.9500
C7—H7	0.9500	C26—C27	1.3405 (18)
C8—H8A	0.9900	C26—H26	0.9500
C8—H8B	0.9900	C27—H27	0.9500
O8—C10	1.4816 (16)	C28—H28A	0.9900
C9—H9A	0.9900	C28—H28B	0.9900
C9—H9B	0.9900	C29—H29A	0.9900
O9—C13	1.4817 (16)	C29—H29B	0.9900
C10—C12	1.490 (2)	C30—C32	1.492 (2)
C10—C11	1.497 (2)	C30—C31	1.503 (2)
C10—H10	1.0000	C30—H30	1.0000
C11—H11A	0.9800	C31—H31A	0.9800
C11—H11B	0.9800	C31—H31B	0.9800
C11—H11C	0.9800	C31—H31C	0.9800
C12—H12A	0.9800	C32—H32A	0.9800
C12—H12B	0.9800	C32—H32B	0.9800
C12—H12C	0.9800	C32—H32C	0.9800
C13—C14	1.508 (2)	C33—C35	1.507 (2)
C13—C15	1.510 (2)	C33—C34	1.511 (2)
C13—H13	1.0000	C33—H33	1.0000
C14—H14A	0.9800	C34—H34A	0.9800
C14—H14B	0.9800	C34—H34B	0.9800
C14—H14C	0.9800	C34—H34C	0.9800
C15—H15A	0.9800	C35—H35A	0.9800
C15—H15B	0.9800	C35—H35B	0.9800
C15—H15C	0.9800	C35—H35C	0.9800
O10—P1—O8	117.77 (6)	O30—P21—O28	117.77 (6)
O10—P1—O9	114.75 (6)	O30—P21—O29	114.53 (6)
O8—P1—O9	104.94 (6)	O28—P21—O29	105.13 (6)
O10—P1—C9	113.38 (6)	O30—P21—C29	113.39 (6)
O8—P1—C9	98.04 (6)	O28—P21—C29	98.02 (6)
O9—P1—C9	106.09 (6)	O29—P21—C29	106.17 (6)
O4—S1—O5	118.93 (6)	O24—S21—O25	118.95 (6)
O4—S1—C7	109.81 (6)	O24—S21—C27	109.91 (6)
O5—S1—C7	109.18 (6)	O25—S21—C27	109.31 (6)
O4—S1—C8	104.10 (6)	O24—S21—C28	103.98 (6)
O5—S1—C8	107.37 (6)	O25—S21—C28	107.25 (6)
C7—S1—C8	106.68 (6)	C27—S21—C28	106.64 (6)
O7—S2—O6	119.22 (6)	O27—S22—O26	119.17 (6)
O7—S2—C9	108.75 (6)	O27—S22—C29	108.77 (6)
O6—S2—C9	107.35 (6)	O26—S22—C29	107.31 (6)
O7—S2—C8	105.71 (6)	O27—S22—C28	105.81 (7)
O6—S2—C8	109.27 (6)	O26—S22—C28	109.14 (6)
C9—S2—C8	105.80 (6)	C29—S22—C28	105.93 (6)
O1—C1—C1A	116.90 (12)	C21—O21—C21B	116.72 (11)
O1—C1—C5	125.79 (13)	C21A—O22—C22	104.17 (11)
C1A—C1—C5	117.30 (12)	C23A—O23—C22	104.67 (11)
O2—C1A—C3A	110.70 (12)	C30—O28—P21	120.88 (9)
O2—C1A—C1	127.59 (13)	C33—O29—P21	122.05 (9)
C3A—C1A—C1	121.65 (12)	O21—C21—C21A	116.68 (12)
O1—C1B—H1B1	109.5	O21—C21—C25	125.99 (13)
O1—C1B—H1B2	109.5	C21A—C21—C25	117.31 (12)
H1B1—C1B—H1B2	109.5	O22—C21A—C23A	110.39 (12)
O1—C1B—H1B3	109.5	O22—C21A—C21	127.84 (13)
H1B1—C1B—H1B3	109.5	C23A—C21A—C21	121.77 (12)
H1B2—C1B—H1B3	109.5	O21—C21B—H21A	109.5
C1—O1—C1B	117.02 (11)	O21—C21B—H21B	109.5
O3—C2—O2	108.07 (11)	H21A—C21B—H21B	109.5
O3—C2—H2A	110.1	O21—C21B—H21C	109.5
O2—C2—H2A	110.1	H21A—C21B—H21C	109.5
O3—C2—H2B	110.1	H21B—C21B—H21C	109.5
O2—C2—H2B	110.1	O23—C22—O22	107.57 (11)
H2A—C2—H2B	108.4	O23—C22—H22A	110.2
C1A—O2—C2	105.36 (11)	O22—C22—H22A	110.2
C3A—C3—C4	116.55 (13)	O23—C22—H22B	110.2
C3A—C3—H3	121.7	O22—C22—H22B	110.2
C4—C3—H3	121.7	H22A—C22—H22B	108.5
O3—C3A—C3	127.20 (13)	C23A—C23—C24	116.45 (12)
O3—C3A—C1A	110.01 (12)	C23A—C23—H23	121.8
C3—C3A—C1A	122.70 (13)	C24—C23—H23	121.8
C3A—O3—C2	105.74 (11)	O23—C23A—C23	127.45 (13)
C3—C4—C5	121.11 (12)	O23—C23A—C21A	110.05 (12)
C3—C4—C6	117.16 (12)	C23—C23A—C21A	122.51 (13)
C5—C4—C6	121.70 (12)	C25—C24—C23	121.30 (12)
C1—C5—C4	120.67 (12)	C25—C24—C26	121.44 (12)
C1—C5—H5	119.7	C23—C24—C26	117.23 (12)
C4—C5—H5	119.7	C21—C25—C24	120.63 (12)
C7—C6—C4	126.94 (12)	C21—C25—H25	119.7
C7—C6—H6	116.5	C24—C25—H25	119.7
C4—C6—H6	116.5	C27—C26—C24	126.48 (12)
C6—C7—S1	119.94 (10)	C27—C26—H26	116.8
C6—C7—H7	120.0	C24—C26—H26	116.8
S1—C7—H7	120.0	C26—C27—S21	119.69 (10)
S2—C8—S1	117.24 (7)	C26—C27—H27	120.2
S2—C8—H8A	108.0	S21—C27—H27	120.2
S1—C8—H8A	108.0	S22—C28—S21	117.26 (7)
S2—C8—H8B	108.0	S22—C28—H28A	108.0
S1—C8—H8B	108.0	S21—C28—H28A	108.0
H8A—C8—H8B	107.2	S22—C28—H28B	108.0
C10—O8—P1	120.86 (9)	S21—C28—H28B	108.0
S2—C9—P1	115.21 (7)	H28A—C28—H28B	107.2
S2—C9—H9A	108.5	S22—C29—P21	115.28 (7)
P1—C9—H9A	108.5	S22—C29—H29A	108.5
S2—C9—H9B	108.5	P21—C29—H29A	108.5
P1—C9—H9B	108.5	S22—C29—H29B	108.5
H9A—C9—H9B	107.5	P21—C29—H29B	108.5
C13—O9—P1	122.41 (9)	H29A—C29—H29B	107.5
O8—C10—C12	106.87 (13)	O28—C30—C32	106.53 (12)
O8—C10—C11	107.37 (12)	O28—C30—C31	107.63 (12)
C12—C10—C11	114.31 (18)	C32—C30—C31	113.87 (17)
O8—C10—H10	109.4	O28—C30—H30	109.6
C12—C10—H10	109.4	C32—C30—H30	109.6
C11—C10—H10	109.4	C31—C30—H30	109.6
C10—C11—H11A	109.5	C30—C31—H31A	109.5
C10—C11—H11B	109.5	C30—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
C10—C11—H11C	109.5	C30—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C10—C12—H12A	109.5	C30—C32—H32A	109.5
C10—C12—H12B	109.5	C30—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
C10—C12—H12C	109.5	C30—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5
O9—C13—C14	107.19 (11)	O29—C33—C35	107.41 (12)
O9—C13—C15	107.30 (12)	O29—C33—C34	107.16 (11)
C14—C13—C15	112.90 (13)	C35—C33—C34	113.15 (13)
O9—C13—H13	109.8	O29—C33—H33	109.7
C14—C13—H13	109.8	C35—C33—H33	109.7
C15—C13—H13	109.8	C34—C33—H33	109.7
C13—C14—H14A	109.5	C33—C34—H34A	109.5
C13—C14—H14B	109.5	C33—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C13—C14—H14C	109.5	C33—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C13—C15—H15A	109.5	C33—C35—H35A	109.5
C13—C15—H15B	109.5	C33—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C13—C15—H15C	109.5	C33—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
O1—C1—C1A—O2	−1.9 (2)	O30—P21—O28—C30	50.10 (12)
C5—C1—C1A—O2	177.30 (13)	O29—P21—O28—C30	−78.84 (11)
O1—C1—C1A—C3A	−178.82 (12)	C29—P21—O28—C30	171.92 (10)
C5—C1—C1A—C3A	0.3 (2)	O30—P21—O29—C33	10.58 (12)
C1A—C1—O1—C1B	174.64 (12)	O28—P21—O29—C33	141.42 (10)
C5—C1—O1—C1B	−4.4 (2)	C29—P21—O29—C33	−115.35 (10)
C3A—C1A—O2—C2	−2.20 (15)	C21B—O21—C21—C21A	−176.98 (13)
C1—C1A—O2—C2	−179.44 (14)	C21B—O21—C21—C25	4.8 (2)
O3—C2—O2—C1A	3.39 (15)	C22—O22—C21A—C23A	9.79 (15)
C4—C3—C3A—O3	−177.47 (13)	C22—O22—C21A—C21	−171.22 (14)
C4—C3—C3A—C1A	−1.2 (2)	O21—C21—C21A—O22	2.0 (2)
O2—C1A—C3A—O3	0.12 (16)	C25—C21—C21A—O22	−179.61 (13)
C1—C1A—C3A—O3	177.56 (12)	O21—C21—C21A—C23A	−179.14 (12)
O2—C1A—C3A—C3	−176.68 (12)	C25—C21—C21A—C23A	−0.7 (2)
C1—C1A—C3A—C3	0.8 (2)	C23A—O23—C22—O22	17.55 (15)
C3—C3A—O3—C2	178.64 (14)	C21A—O22—C22—O23	−16.83 (15)
C1A—C3A—O3—C2	2.02 (15)	C22—O23—C23A—C23	168.34 (14)
O2—C2—O3—C3A	−3.34 (15)	C22—O23—C23A—C21A	−11.66 (15)
C3A—C3—C4—C5	0.70 (19)	C24—C23—C23A—O23	177.88 (13)
C3A—C3—C4—C6	178.68 (12)	C24—C23—C23A—C21A	−2.1 (2)
O1—C1—C5—C4	178.22 (12)	O22—C21A—C23A—O23	1.14 (16)
C1A—C1—C5—C4	−0.85 (19)	C21—C21A—C23A—O23	−177.92 (12)
C3—C4—C5—C1	0.33 (19)	O22—C21A—C23A—C23	−178.86 (12)
C6—C4—C5—C1	−177.56 (12)	C21—C21A—C23A—C23	2.1 (2)
C3—C4—C6—C7	175.05 (13)	C23A—C23—C24—C25	0.96 (19)
C5—C4—C6—C7	−7.0 (2)	C23A—C23—C24—C26	178.91 (12)
C4—C6—C7—S1	176.81 (10)	O21—C21—C25—C24	177.84 (13)
O4—S1—C7—C6	−14.21 (13)	C21A—C21—C25—C24	−0.41 (19)
O5—S1—C7—C6	−146.25 (11)	C23—C24—C25—C21	0.3 (2)
C8—S1—C7—C6	98.02 (12)	C26—C24—C25—C21	−177.58 (12)
O7—S2—C8—S1	−161.90 (8)	C25—C24—C26—C27	−12.2 (2)
O6—S2—C8—S1	−32.44 (10)	C23—C24—C26—C27	169.83 (13)
C9—S2—C8—S1	82.85 (9)	C24—C26—C27—S21	177.14 (10)
O4—S1—C8—S2	−174.59 (7)	O24—S21—C27—C26	−13.10 (13)
O5—S1—C8—S2	−47.64 (9)	O25—S21—C27—C26	−145.35 (11)
C7—S1—C8—S2	69.30 (9)	C28—S21—C27—C26	99.01 (12)
O10—P1—O8—C10	48.97 (12)	O27—S22—C28—S21	−162.34 (7)
O9—P1—O8—C10	−80.09 (11)	O26—S22—C28—S21	−32.96 (10)
C9—P1—O8—C10	170.79 (10)	C29—S22—C28—S21	82.28 (9)
O7—S2—C9—P1	−48.66 (9)	O24—S21—C28—S22	−172.71 (7)
O6—S2—C9—P1	−178.91 (7)	O25—S21—C28—S22	−45.87 (9)
C8—S2—C9—P1	64.49 (9)	C27—S21—C28—S22	71.14 (9)
O10—P1—C9—S2	−49.50 (10)	O27—S22—C29—P21	−49.17 (9)
O8—P1—C9—S2	−174.50 (7)	O26—S22—C29—P21	−179.34 (7)
O9—P1—C9—S2	77.33 (8)	C28—S22—C29—P21	64.17 (9)
O10—P1—O9—C13	10.69 (12)	O30—P21—C29—S22	−49.00 (10)
O8—P1—O9—C13	141.53 (10)	O28—P21—C29—S22	−174.00 (8)
C9—P1—O9—C13	−115.31 (10)	O29—P21—C29—S22	77.62 (8)
P1—O8—C10—C12	139.11 (17)	P21—O28—C30—C32	139.65 (15)
P1—O8—C10—C11	−97.83 (16)	P21—O28—C30—C31	−97.84 (15)
P1—O9—C13—C14	138.74 (10)	P21—O29—C33—C35	−100.52 (13)
P1—O9—C13—C15	−99.73 (13)	P21—O29—C33—C34	137.61 (10)

(III) bis(trans-2-phenylethenyl) sulfone

Crystal data

C16H14O2S	F(000) = 3408
Mr = 270.33	Dx = 1.304 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5361 reflections
a = 10.1632 (7) Å	θ = 2.3–25.5°
b = 23.6753 (16) Å	µ = 0.23 mm^−1
c = 34.339 (2) Å	T = 90 K
V = 8262.5 (9) Å^3	Rod, colorless
Z = 24	0.51 × 0.09 × 0.06 mm

Data collection

Bruker SMART 1000 diffractometer	9492 independent reflections
Radiation source: fine-focus sealed tube	5497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
Detector resolution: 8.3 pixels mm^-1	θmax = 27.5°, θmin = 1.7°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	k = −27→30
Tmin = 0.892, Tmax = 0.987	l = −44→44
60803 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0624P)^2] where P = (Fo^2 + 2Fc^2)/3
9492 reflections	(Δ/σ)max < 0.001
562 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −1.02 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	Occ. (<1)
S1	0.73682 (6)	0.00321 (3)	0.232714 (17)	0.02295 (15)
C1	0.4491 (2)	0.16964 (11)	0.27948 (7)	0.0265 (6)
H1	0.4955	0.1655	0.3033	0.032*
O1	0.76152 (17)	−0.00309 (7)	0.27387 (5)	0.0286 (4)
C2	0.3564 (2)	0.21182 (11)	0.27595 (7)	0.0274 (6)
H2	0.3407	0.2369	0.2970	0.033*
O2	0.84810 (16)	0.00625 (7)	0.20674 (5)	0.0291 (4)
C3	0.2858 (3)	0.21764 (11)	0.24148 (7)	0.0297 (6)
H3	0.2214	0.2465	0.2389	0.036*
C4	0.3107 (2)	0.18070 (11)	0.21066 (7)	0.0282 (6)
H4	0.2625	0.1843	0.1871	0.034*
C5	0.4044 (2)	0.13909 (10)	0.21418 (7)	0.0246 (6)
H5	0.4204	0.1143	0.1929	0.029*
C6	0.4765 (2)	0.13276 (10)	0.24868 (6)	0.0213 (5)
C7	0.5756 (2)	0.08836 (10)	0.25336 (6)	0.0230 (5)
H7	0.6005	0.0787	0.2792	0.028*
C8	0.6335 (2)	0.06054 (10)	0.22464 (7)	0.0230 (5)
H8	0.6180	0.0724	0.1986	0.028*
C9	0.6357 (2)	−0.05240 (10)	0.21741 (6)	0.0219 (5)
H9	0.5549	−0.0588	0.2306	0.026*
C10	0.6681 (2)	−0.08582 (10)	0.18800 (7)	0.0230 (5)
H10	0.7507	−0.0788	0.1759	0.028*
C11	0.5896 (2)	−0.13257 (10)	0.17211 (6)	0.0210 (5)
C12	0.4599 (2)	−0.14266 (10)	0.18350 (6)	0.0231 (5)
H12	0.4194	−0.1189	0.2023	0.028*
C13	0.3896 (3)	−0.18732 (10)	0.16748 (7)	0.0276 (6)
H13	0.3018	−0.1944	0.1756	0.033*
C14	0.4474 (3)	−0.22156 (10)	0.13964 (7)	0.0313 (6)
H14	0.3990	−0.2520	0.1287	0.038*
C15	0.5750 (3)	−0.21166 (11)	0.12773 (7)	0.0310 (6)
H15	0.6139	−0.2350	0.1084	0.037*
C16	0.6464 (3)	−0.16771 (10)	0.14400 (7)	0.0280 (6)
H16	0.7346	−0.1614	0.1360	0.034*
S21	0.63705 (6)	0.13450 (2)	0.111526 (15)	0.01896 (14)
C21	1.0923 (2)	0.05528 (10)	0.14105 (6)	0.0240 (6)
H21	1.0444	0.0323	0.1587	0.029*
O21	0.57348 (16)	0.13957 (7)	0.07412 (4)	0.0216 (4)
C22	1.2262 (2)	0.04665 (11)	0.13596 (7)	0.0264 (6)
H22	1.2700	0.0179	0.1502	0.032*
O22	0.60780 (16)	0.08544 (7)	0.13483 (4)	0.0226 (4)
C23	1.2962 (2)	0.08001 (11)	0.11002 (7)	0.0270 (6)
H23	1.3873	0.0733	0.1060	0.032*
C24	1.2333 (2)	0.12320 (11)	0.08992 (7)	0.0272 (6)
H24	1.2819	0.1467	0.0727	0.033*
C25	1.1003 (2)	0.13195 (10)	0.09502 (7)	0.0233 (5)
H25	1.0577	0.1615	0.0812	0.028*
C26	1.0275 (2)	0.09796 (10)	0.12016 (6)	0.0205 (5)
C27	0.8854 (2)	0.10328 (10)	0.12458 (6)	0.0207 (5)
H27	0.8452	0.0803	0.1439	0.025*
C28	0.8063 (2)	0.13697 (10)	0.10438 (6)	0.0192 (5)
H28	0.8424	0.1625	0.0859	0.023*
C29	0.6010 (2)	0.19422 (10)	0.13919 (6)	0.0211 (5)
H29	0.6301	0.1962	0.1655	0.025*
C30	0.5334 (2)	0.23709 (10)	0.12411 (6)	0.0204 (5)
H30	0.5072	0.2338	0.0977	0.024*
C31	0.4955 (2)	0.28898 (10)	0.14453 (6)	0.0212 (5)
C32	0.4441 (2)	0.33379 (10)	0.12321 (7)	0.0241 (6)
H32	0.4320	0.3298	0.0959	0.029*
C33	0.4102 (3)	0.38435 (11)	0.14113 (7)	0.0294 (6)
H33	0.3763	0.4147	0.1261	0.035*
C34	0.4259 (3)	0.39030 (11)	0.18078 (7)	0.0327 (6)
H34	0.4029	0.4248	0.1931	0.039*
C35	0.4754 (3)	0.34574 (11)	0.20264 (7)	0.0313 (6)
H35	0.4857	0.3499	0.2300	0.038*
C36	0.5100 (2)	0.29535 (11)	0.18501 (7)	0.0252 (6)
H36	0.5434	0.2651	0.2002	0.030*
S41	0.78425 (8)	0.24464 (3)	−0.00204 (2)	0.0411 (2)
C41	0.5670 (3)	0.08760 (14)	−0.08228 (8)	0.0438 (8)
H41	0.6199	0.1021	−0.1028	0.053*
O41	0.8547 (2)	0.25138 (8)	−0.03837 (5)	0.0456 (6)
C42	0.4912 (3)	0.03983 (14)	−0.08854 (8)	0.0488 (9)
H42	0.4925	0.0217	−0.1132	0.059*
O42	0.8609 (2)	0.23348 (8)	0.03280 (5)	0.0429 (5)
C43	0.4144 (3)	0.01861 (14)	−0.05919 (9)	0.0497 (8)
H43	0.3631	−0.0144	−0.0634	0.060*
C44	0.4120 (3)	0.04571 (15)	−0.02327 (8)	0.0491 (8)
H44	0.3575	0.0314	−0.0031	0.059*
C45	0.4874 (3)	0.09283 (14)	−0.01668 (8)	0.0412 (8)
H45	0.4857	0.1106	0.0081	0.049*
C46	0.5664 (3)	0.11460 (13)	−0.04612 (7)	0.0370 (7)
C47	0.6524 (3)	0.16347 (13)	−0.03997 (7)	0.0397 (8)
H47	0.7012	0.1763	−0.0618	0.048*
C48	0.6689 (3)	0.19161 (13)	−0.00679 (7)	0.0373 (7)
H48	0.6155	0.1822	0.0150	0.045*
C49	0.6698 (6)	0.29921 (19)	0.00007 (13)	0.0197 (9)	0.57
H49	0.6046	0.3033	−0.0195	0.024*	0.57
C50	0.6761 (6)	0.3361 (2)	0.03064 (13)	0.0227 (11)	0.57
H50	0.7417	0.3288	0.0497	0.027*	0.57
C51	0.5944 (5)	0.3845 (2)	0.03700 (13)	0.0266 (15)	0.57
C52	0.4818 (5)	0.3946 (3)	0.01514 (16)	0.0306 (19)	0.57
H52	0.4565	0.3689	−0.0047	0.037*	0.57
C53	0.4061 (7)	0.4424 (3)	0.0224 (2)	0.0354 (18)	0.57
H53	0.3291	0.4493	0.0074	0.043*	0.57
C54	0.4430 (9)	0.4800 (3)	0.0515 (3)	0.040 (2)	0.57
H54	0.3913	0.5126	0.0564	0.048*	0.57
C55	0.5557 (9)	0.4698 (3)	0.0733 (2)	0.042 (2)	0.57
H55	0.5810	0.4956	0.0932	0.050*	0.57
C56	0.6314 (6)	0.4221 (3)	0.06609 (15)	0.0358 (16)	0.57
H56	0.7084	0.4151	0.0810	0.043*	0.57
C49B	0.7286 (8)	0.3135 (4)	0.0187 (3)	0.0390 (18)	0.43
H49B	0.7838	0.3361	0.0347	0.047*	0.43
C50B	0.6152 (7)	0.3278 (4)	0.0102 (2)	0.0335 (16)	0.43
H50B	0.5645	0.3026	−0.0051	0.040*	0.43
C51B	0.5513 (7)	0.3827 (3)	0.02257 (19)	0.028 (2)	0.43
C52B	0.4340 (8)	0.3963 (4)	0.0040 (2)	0.030 (2)	0.43
H52B	0.3999	0.3721	−0.0157	0.037*	0.43
C53B	0.3665 (9)	0.4452 (5)	0.0141 (3)	0.036 (2)	0.43
H53B	0.2864	0.4544	0.0014	0.043*	0.43
C54B	0.4164 (12)	0.4805 (5)	0.0429 (4)	0.046 (3)	0.43
H54B	0.3702	0.5139	0.0498	0.055*	0.43
C55B	0.5337 (12)	0.4670 (4)	0.0615 (3)	0.047 (3)	0.43
H55B	0.5677	0.4911	0.0811	0.056*	0.43
C56B	0.6011 (8)	0.4181 (4)	0.0513 (2)	0.042 (3)	0.43
H56B	0.6813	0.4088	0.0640	0.051*	0.43

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0245 (3)	0.0217 (3)	0.0226 (3)	−0.0035 (3)	−0.0005 (3)	−0.0001 (2)
C1	0.0271 (14)	0.0299 (15)	0.0226 (12)	−0.0053 (12)	0.0026 (11)	−0.0007 (11)
O1	0.0347 (10)	0.0255 (9)	0.0255 (9)	−0.0022 (9)	−0.0075 (8)	0.0022 (7)
C2	0.0261 (15)	0.0280 (14)	0.0282 (13)	−0.0022 (12)	0.0066 (11)	−0.0033 (11)
O2	0.0253 (10)	0.0296 (10)	0.0323 (9)	−0.0033 (8)	0.0047 (8)	−0.0011 (8)
C3	0.0267 (15)	0.0294 (15)	0.0331 (14)	−0.0013 (12)	0.0057 (11)	0.0058 (11)
C4	0.0253 (14)	0.0333 (16)	0.0260 (13)	−0.0021 (12)	0.0003 (11)	0.0053 (11)
C5	0.0255 (14)	0.0267 (14)	0.0215 (12)	−0.0056 (11)	0.0045 (10)	0.0000 (10)
C6	0.0191 (13)	0.0237 (13)	0.0210 (11)	−0.0071 (11)	0.0032 (10)	0.0020 (10)
C7	0.0264 (14)	0.0232 (13)	0.0194 (11)	−0.0068 (11)	−0.0042 (10)	0.0009 (10)
C8	0.0258 (14)	0.0207 (13)	0.0224 (12)	−0.0044 (11)	0.0012 (10)	0.0023 (10)
C9	0.0231 (13)	0.0225 (13)	0.0200 (11)	−0.0042 (11)	−0.0001 (10)	0.0035 (10)
C10	0.0193 (13)	0.0247 (14)	0.0251 (12)	0.0027 (11)	−0.0028 (10)	0.0029 (10)
C11	0.0232 (13)	0.0202 (13)	0.0196 (11)	−0.0003 (11)	−0.0023 (10)	−0.0012 (10)
C12	0.0284 (14)	0.0204 (14)	0.0205 (11)	0.0044 (11)	−0.0021 (10)	−0.0012 (10)
C13	0.0291 (15)	0.0283 (15)	0.0255 (13)	−0.0027 (12)	−0.0051 (11)	0.0045 (11)
C14	0.0460 (18)	0.0182 (14)	0.0298 (14)	−0.0027 (13)	−0.0115 (13)	0.0015 (11)
C15	0.0419 (18)	0.0239 (14)	0.0272 (13)	0.0068 (13)	−0.0021 (12)	−0.0044 (11)
C16	0.0281 (15)	0.0276 (14)	0.0283 (13)	0.0060 (12)	−0.0034 (11)	0.0014 (11)
S21	0.0182 (3)	0.0226 (3)	0.0160 (3)	−0.0011 (3)	−0.0002 (2)	−0.0011 (2)
C21	0.0229 (14)	0.0293 (15)	0.0197 (12)	0.0004 (11)	−0.0013 (10)	0.0015 (10)
O21	0.0213 (9)	0.0277 (10)	0.0158 (8)	−0.0016 (8)	−0.0025 (7)	−0.0005 (7)
C22	0.0243 (14)	0.0298 (14)	0.0250 (12)	0.0026 (12)	−0.0040 (11)	0.0025 (11)
O22	0.0205 (9)	0.0269 (9)	0.0205 (8)	−0.0045 (8)	−0.0007 (7)	0.0025 (7)
C23	0.0178 (13)	0.0329 (15)	0.0303 (13)	0.0001 (12)	−0.0035 (11)	−0.0015 (11)
C24	0.0235 (14)	0.0289 (15)	0.0291 (13)	−0.0092 (12)	0.0023 (11)	−0.0014 (11)
C25	0.0213 (13)	0.0199 (13)	0.0287 (13)	−0.0006 (11)	−0.0019 (10)	0.0000 (10)
C26	0.0196 (13)	0.0226 (13)	0.0194 (11)	−0.0013 (11)	−0.0014 (9)	−0.0057 (10)
C27	0.0216 (13)	0.0208 (13)	0.0196 (11)	−0.0016 (11)	0.0024 (10)	−0.0047 (10)
C28	0.0182 (12)	0.0183 (12)	0.0210 (11)	−0.0019 (10)	0.0035 (9)	−0.0033 (9)
C29	0.0172 (13)	0.0292 (14)	0.0169 (11)	−0.0022 (11)	0.0016 (9)	−0.0031 (10)
C30	0.0176 (13)	0.0264 (14)	0.0172 (11)	−0.0045 (11)	0.0026 (9)	−0.0009 (10)
C31	0.0158 (12)	0.0254 (14)	0.0225 (12)	−0.0038 (11)	0.0006 (10)	−0.0043 (10)
C32	0.0232 (14)	0.0290 (15)	0.0201 (11)	−0.0015 (11)	0.0024 (10)	−0.0002 (10)
C33	0.0325 (16)	0.0225 (14)	0.0332 (14)	0.0021 (12)	0.0028 (12)	0.0007 (11)
C34	0.0376 (17)	0.0246 (15)	0.0358 (14)	−0.0002 (13)	0.0021 (12)	−0.0071 (12)
C35	0.0376 (17)	0.0330 (16)	0.0232 (13)	−0.0011 (13)	−0.0025 (11)	−0.0059 (11)
C36	0.0227 (14)	0.0280 (14)	0.0250 (12)	0.0035 (11)	−0.0018 (10)	−0.0022 (11)
S41	0.0542 (5)	0.0268 (4)	0.0424 (4)	0.0074 (4)	0.0280 (4)	0.0097 (3)
C41	0.0473 (19)	0.057 (2)	0.0267 (14)	0.0289 (17)	0.0037 (13)	0.0058 (14)
O41	0.0526 (14)	0.0413 (12)	0.0430 (11)	0.0134 (11)	0.0285 (10)	0.0159 (9)
C42	0.061 (2)	0.051 (2)	0.0337 (16)	0.0333 (19)	−0.0093 (15)	−0.0028 (15)
O42	0.0601 (14)	0.0372 (11)	0.0313 (10)	−0.0231 (11)	0.0145 (10)	−0.0076 (9)
C43	0.046 (2)	0.061 (2)	0.0419 (18)	0.0135 (17)	−0.0097 (15)	−0.0085 (16)
C44	0.0297 (17)	0.082 (3)	0.0359 (16)	−0.0033 (18)	−0.0045 (13)	−0.0060 (16)
C45	0.0244 (16)	0.077 (2)	0.0223 (13)	−0.0019 (16)	−0.0021 (11)	−0.0044 (14)
C46	0.0273 (16)	0.058 (2)	0.0251 (13)	0.0135 (15)	−0.0022 (11)	0.0068 (13)
C47	0.0360 (17)	0.059 (2)	0.0238 (13)	0.0195 (16)	0.0100 (12)	0.0167 (13)
C48	0.0250 (15)	0.059 (2)	0.0282 (14)	0.0076 (14)	0.0105 (12)	0.0161 (13)
C49	0.024 (3)	0.019 (2)	0.017 (2)	−0.008 (2)	0.003 (2)	−0.0059 (19)
C50	0.030 (3)	0.021 (3)	0.017 (2)	−0.010 (2)	0.010 (2)	−0.009 (2)
C51	0.031 (4)	0.017 (3)	0.032 (4)	−0.014 (3)	0.008 (3)	0.000 (3)
C52	0.033 (6)	0.024 (3)	0.035 (4)	−0.012 (3)	0.008 (4)	−0.005 (3)
C53	0.028 (5)	0.040 (4)	0.038 (4)	−0.001 (3)	0.010 (3)	0.001 (3)
C54	0.053 (6)	0.012 (4)	0.055 (5)	−0.002 (4)	0.023 (5)	−0.006 (3)
C55	0.051 (5)	0.028 (4)	0.046 (5)	−0.009 (3)	0.016 (3)	−0.010 (3)
C56	0.034 (4)	0.032 (3)	0.041 (4)	−0.007 (3)	0.014 (3)	−0.006 (3)
C49B	0.051 (6)	0.034 (5)	0.032 (4)	−0.017 (4)	0.010 (4)	−0.001 (3)
C50B	0.031 (4)	0.043 (5)	0.027 (4)	−0.015 (4)	0.002 (3)	0.001 (3)
C51B	0.028 (6)	0.031 (5)	0.025 (5)	−0.007 (4)	0.008 (4)	−0.002 (4)
C52B	0.034 (6)	0.027 (4)	0.031 (5)	−0.006 (4)	0.009 (4)	−0.006 (4)
C53B	0.019 (5)	0.031 (5)	0.059 (7)	−0.001 (4)	0.008 (4)	0.011 (4)
C54B	0.045 (6)	0.036 (7)	0.057 (7)	0.010 (5)	0.031 (5)	0.000 (6)
C55B	0.069 (8)	0.038 (6)	0.034 (6)	−0.025 (6)	0.014 (6)	−0.009 (4)
C56B	0.038 (5)	0.038 (6)	0.051 (7)	−0.016 (5)	−0.008 (5)	0.021 (6)

Geometric parameters (Å, º)

S1—O2	1.4422 (17)	C32—C33	1.389 (3)
S1—O1	1.4432 (16)	C32—H32	0.9500
S1—C8	1.738 (2)	C33—C34	1.378 (3)
S1—C9	1.751 (2)	C33—H33	0.9500
C1—C2	1.379 (3)	C34—C35	1.389 (4)
C1—C6	1.399 (3)	C34—H34	0.9500
C1—H1	0.9500	C35—C36	1.383 (3)
C2—C3	1.391 (3)	C35—H35	0.9500
C2—H2	0.9500	C36—H36	0.9500
C3—C4	1.396 (3)	S41—O41	1.4473 (18)
C3—H3	0.9500	S41—O42	1.452 (2)
C4—C5	1.375 (3)	S41—C48	1.725 (3)
C4—H4	0.9500	S41—C49	1.740 (6)
C5—C6	1.401 (3)	S41—C49B	1.868 (10)
C5—H5	0.9500	C41—C42	1.385 (4)
C6—C7	1.465 (3)	C41—C46	1.397 (4)
C7—C8	1.324 (3)	C41—H41	0.9500
C7—H7	0.9500	C42—C43	1.370 (4)
C8—H8	0.9500	C42—H42	0.9500
C9—C10	1.325 (3)	C43—C44	1.390 (4)
C9—H9	0.9500	C43—H43	0.9500
C10—C11	1.469 (3)	C44—C45	1.372 (4)
C10—H10	0.9500	C44—H44	0.9500
C11—C12	1.396 (3)	C45—C46	1.390 (4)
C11—C16	1.399 (3)	C45—H45	0.9500
C12—C13	1.390 (3)	C46—C47	1.465 (4)
C12—H12	0.9500	C47—C48	1.330 (4)
C13—C14	1.384 (3)	C47—H47	0.9500
C13—H13	0.9500	C48—H48	0.9500
C14—C15	1.380 (4)	C49—C50	1.367 (6)
C14—H14	0.9500	C49—H49	0.9500
C15—C16	1.386 (3)	C50—C51	1.431 (8)
C15—H15	0.9500	C50—H50	0.9500
C16—H16	0.9500	C51—C52	1.3900
S21—O22	1.4415 (16)	C51—C56	1.3900
S21—O21	1.4428 (15)	C52—C53	1.3900
S21—C28	1.739 (2)	C52—H52	0.9500
S21—C29	1.742 (2)	C53—C54	1.3900
C21—C22	1.387 (3)	C53—H53	0.9500
C21—C26	1.404 (3)	C54—C55	1.3900
C21—H21	0.9500	C54—H54	0.9500
C22—C23	1.387 (3)	C55—C56	1.3900
C22—H22	0.9500	C55—H55	0.9500
C23—C24	1.389 (3)	C56—H56	0.9500
C23—H23	0.9500	C49B—C50B	1.236 (11)
C24—C25	1.379 (3)	C49B—H49B	0.9500
C24—H24	0.9500	C50B—C51B	1.513 (12)
C25—C26	1.393 (3)	C50B—H50B	0.9500
C25—H25	0.9500	C51B—C52B	1.3900
C26—C27	1.457 (3)	C51B—C56B	1.3900
C27—C28	1.328 (3)	C52B—C53B	1.3900
C27—H27	0.9500	C52B—H52B	0.9500
C28—H28	0.9500	C53B—C54B	1.3900
C29—C30	1.331 (3)	C53B—H53B	0.9500
C29—H29	0.9500	C54B—C55B	1.3900
C30—C31	1.466 (3)	C54B—H54B	0.9500
C30—H30	0.9500	C55B—C56B	1.3900
C31—C32	1.391 (3)	C55B—H55B	0.9500
C31—C36	1.406 (3)	C56B—H56B	0.9500
O2—S1—O1	118.33 (11)	C31—C32—H32	119.4
O2—S1—C8	109.63 (11)	C34—C33—C32	119.8 (2)
O1—S1—C8	109.99 (11)	C34—C33—H33	120.1
O2—S1—C9	108.20 (11)	C32—C33—H33	120.1
O1—S1—C9	108.57 (10)	C33—C34—C35	119.9 (2)
C8—S1—C9	100.64 (11)	C33—C34—H34	120.1
C2—C1—C6	121.4 (2)	C35—C34—H34	120.1
C2—C1—H1	119.3	C36—C35—C34	120.7 (2)
C6—C1—H1	119.3	C36—C35—H35	119.6
C1—C2—C3	119.9 (2)	C34—C35—H35	119.6
C1—C2—H2	120.0	C35—C36—C31	119.9 (2)
C3—C2—H2	120.0	C35—C36—H36	120.0
C2—C3—C4	119.3 (2)	C31—C36—H36	120.0
C2—C3—H3	120.3	O41—S41—O42	117.69 (13)
C4—C3—H3	120.3	O41—S41—C48	109.58 (13)
C5—C4—C3	120.5 (2)	O42—S41—C48	108.06 (12)
C5—C4—H4	119.7	O41—S41—C49	106.55 (16)
C3—C4—H4	119.7	O42—S41—C49	117.35 (18)
C4—C5—C6	120.9 (2)	C48—S41—C49	95.17 (19)
C4—C5—H5	119.6	O41—S41—C49B	112.5 (2)
C6—C5—H5	119.6	O42—S41—C49B	90.4 (3)
C1—C6—C5	117.9 (2)	C48—S41—C49B	117.8 (3)
C1—C6—C7	120.1 (2)	C42—C41—C46	120.6 (3)
C5—C6—C7	122.0 (2)	C42—C41—H41	119.7
C8—C7—C6	125.5 (2)	C46—C41—H41	119.7
C8—C7—H7	117.2	C43—C42—C41	120.1 (3)
C6—C7—H7	117.2	C43—C42—H42	119.9
C7—C8—S1	122.54 (19)	C41—C42—H42	119.9
C7—C8—H8	118.7	C42—C43—C44	119.6 (3)
S1—C8—H8	118.7	C42—C43—H43	120.2
C10—C9—S1	122.1 (2)	C44—C43—H43	120.2
C10—C9—H9	118.9	C45—C44—C43	120.8 (3)
S1—C9—H9	118.9	C45—C44—H44	119.6
C9—C10—C11	126.7 (2)	C43—C44—H44	119.6
C9—C10—H10	116.6	C44—C45—C46	120.3 (3)
C11—C10—H10	116.6	C44—C45—H45	119.9
C12—C11—C16	118.7 (2)	C46—C45—H45	119.9
C12—C11—C10	122.5 (2)	C45—C46—C41	118.6 (3)
C16—C11—C10	118.7 (2)	C45—C46—C47	122.2 (3)
C13—C12—C11	120.3 (2)	C41—C46—C47	119.1 (3)
C13—C12—H12	119.8	C48—C47—C46	126.4 (3)
C11—C12—H12	119.8	C48—C47—H47	116.8
C14—C13—C12	120.1 (2)	C46—C47—H47	116.8
C14—C13—H13	120.0	C47—C48—S41	122.1 (2)
C12—C13—H13	120.0	C47—C48—H48	119.0
C15—C14—C13	120.3 (2)	S41—C48—H48	119.0
C15—C14—H14	119.9	C50—C49—S41	118.4 (5)
C13—C14—H14	119.9	C50—C49—H49	120.8
C14—C15—C16	120.0 (2)	S41—C49—H49	120.8
C14—C15—H15	120.0	C49—C50—C51	127.0 (6)
C16—C15—H15	120.0	C49—C50—H50	116.5
C15—C16—C11	120.6 (2)	C51—C50—H50	116.5
C15—C16—H16	119.7	C52—C51—C56	120.0
C11—C16—H16	119.7	C52—C51—C50	122.3 (4)
O22—S21—O21	117.96 (10)	C56—C51—C50	117.7 (4)
O22—S21—C28	108.03 (10)	C51—C52—C53	120.0
O21—S21—C28	108.34 (10)	C51—C52—H52	120.0
O22—S21—C29	107.93 (10)	C53—C52—H52	120.0
O21—S21—C29	108.89 (10)	C54—C53—C52	120.0
C28—S21—C29	104.94 (11)	C54—C53—H53	120.0
C22—C21—C26	120.2 (2)	C52—C53—H53	120.0
C22—C21—H21	119.9	C55—C54—C53	120.0
C26—C21—H21	119.9	C55—C54—H54	120.0
C21—C22—C23	120.0 (2)	C53—C54—H54	120.0
C21—C22—H22	120.0	C54—C55—C56	120.0
C23—C22—H22	120.0	C54—C55—H55	120.0
C22—C23—C24	120.2 (2)	C56—C55—H55	120.0
C22—C23—H23	119.9	C55—C56—C51	120.0
C24—C23—H23	119.9	C55—C56—H56	120.0
C25—C24—C23	119.9 (2)	C51—C56—H56	120.0
C25—C24—H24	120.1	C50B—C49B—S41	115.6 (10)
C23—C24—H24	120.1	C50B—C49B—H49B	122.2
C24—C25—C26	120.9 (2)	S41—C49B—H49B	122.2
C24—C25—H25	119.6	C49B—C50B—C51B	124.7 (10)
C26—C25—H25	119.6	C49B—C50B—H50B	117.6
C25—C26—C21	118.9 (2)	C51B—C50B—H50B	117.6
C25—C26—C27	122.8 (2)	C52B—C51B—C56B	120.0
C21—C26—C27	118.3 (2)	C52B—C51B—C50B	115.9 (6)
C28—C27—C26	126.6 (2)	C56B—C51B—C50B	124.0 (6)
C28—C27—H27	116.7	C53B—C52B—C51B	120.0
C26—C27—H27	116.7	C53B—C52B—H52B	120.0
C27—C28—S21	120.31 (19)	C51B—C52B—H52B	120.0
C27—C28—H28	119.8	C54B—C53B—C52B	120.0
S21—C28—H28	119.8	C54B—C53B—H53B	120.0
C30—C29—S21	121.02 (18)	C52B—C53B—H53B	120.0
C30—C29—H29	119.5	C53B—C54B—C55B	120.0
S21—C29—H29	119.5	C53B—C54B—H54B	120.0
C29—C30—C31	126.1 (2)	C55B—C54B—H54B	120.0
C29—C30—H30	117.0	C54B—C55B—C56B	120.0
C31—C30—H30	117.0	C54B—C55B—H55B	120.0
C32—C31—C36	118.5 (2)	C56B—C55B—H55B	120.0
C32—C31—C30	119.1 (2)	C55B—C56B—C51B	120.0
C36—C31—C30	122.4 (2)	C55B—C56B—H56B	120.0
C33—C32—C31	121.2 (2)	C51B—C56B—H56B	120.0
C33—C32—H32	119.4

(IV) bis(trans-2-phenylethenylsulfonyl)methane

Crystal data

C17H16O4S2	F(000) = 728
Mr = 348.42	Dx = 1.466 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6102 reflections
a = 15.7551 (6) Å	θ = 2.7–30.0°
b = 11.9609 (5) Å	µ = 0.36 mm^−1
c = 8.6212 (3) Å	T = 90 K
β = 103.728 (1)°	Block, colorless
V = 1578.21 (10) Å^3	0.29 × 0.24 × 0.20 mm
Z = 4

Data collection

Bruker SMART 1000 diffractometer	2302 independent reflections
Radiation source: fine-focus sealed tube	1978 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.3 pixels mm^-1	θmax = 30.0°, θmin = 2.2°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 2006)	k = −16→16
Tmin = 0.865, Tmax = 0.928	l = −12→12
8747 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	All H-atom parameters refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 1.1605P] where P = (Fo^2 + 2Fc^2)/3
2302 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.31 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
S1	0.452903 (18)	0.34291 (2)	0.07337 (3)	0.01471 (10)
O1	0.40271 (6)	0.42586 (8)	−0.03276 (11)	0.0194 (2)
O2	0.40895 (6)	0.24615 (7)	0.11488 (11)	0.0187 (2)
C1	0.61794 (9)	0.03714 (11)	−0.14792 (16)	0.0200 (3)
H1	0.5772 (14)	−0.0113 (17)	−0.110 (2)	0.037 (5)*
C2	0.67641 (10)	−0.00807 (11)	−0.22831 (17)	0.0236 (3)
H2	0.6762 (13)	−0.0843 (17)	−0.245 (2)	0.031 (5)*
C3	0.73257 (9)	0.06147 (12)	−0.28548 (16)	0.0221 (3)
H3	0.7717 (12)	0.0315 (15)	−0.343 (2)	0.027 (5)*
C4	0.73069 (9)	0.17639 (12)	−0.26197 (17)	0.0220 (3)
H4	0.7694 (12)	0.2253 (16)	−0.301 (2)	0.027 (5)*
C5	0.67275 (9)	0.22206 (11)	−0.18012 (16)	0.0197 (2)
H5	0.6694 (12)	0.3043 (16)	−0.171 (2)	0.027 (5)*
C6	0.61538 (8)	0.15290 (10)	−0.12260 (14)	0.0154 (2)
H6	0.5133 (13)	0.1410 (16)	−0.008 (2)	0.029 (5)*
C7	0.55115 (8)	0.19662 (10)	−0.04009 (15)	0.0165 (2)
H7	0.5725 (12)	0.3661 (15)	−0.021 (2)	0.027 (4)*
C8	0.54096 (8)	0.30349 (10)	−0.00421 (15)	0.0167 (2)
C9	0.5000	0.42087 (14)	0.2500	0.0159 (3)
H9	0.5468 (12)	0.4693 (15)	0.229 (2)	0.028 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01503 (16)	0.01466 (15)	0.01597 (16)	−0.00020 (9)	0.00677 (11)	−0.00018 (9)
O1	0.0184 (4)	0.0198 (4)	0.0204 (4)	0.0024 (3)	0.0053 (3)	0.0023 (3)
O2	0.0188 (4)	0.0170 (4)	0.0228 (4)	−0.0037 (3)	0.0100 (3)	−0.0004 (3)
C1	0.0240 (6)	0.0163 (5)	0.0223 (6)	−0.0003 (4)	0.0103 (5)	0.0010 (4)
C2	0.0288 (7)	0.0172 (6)	0.0270 (7)	0.0042 (5)	0.0112 (5)	−0.0014 (5)
C3	0.0198 (6)	0.0249 (6)	0.0232 (6)	0.0043 (5)	0.0085 (5)	−0.0022 (5)
C4	0.0184 (6)	0.0246 (6)	0.0260 (6)	−0.0024 (5)	0.0111 (5)	−0.0019 (5)
C5	0.0205 (6)	0.0174 (5)	0.0235 (6)	−0.0014 (5)	0.0096 (5)	−0.0010 (5)
C6	0.0160 (5)	0.0161 (5)	0.0152 (5)	0.0005 (4)	0.0055 (4)	−0.0002 (4)
C7	0.0169 (5)	0.0172 (5)	0.0169 (5)	−0.0005 (4)	0.0070 (4)	0.0000 (4)
C8	0.0169 (5)	0.0177 (5)	0.0175 (5)	−0.0003 (4)	0.0083 (4)	0.0001 (4)
C9	0.0189 (8)	0.0144 (7)	0.0158 (7)	0.000	0.0069 (6)	0.000

Geometric parameters (Å, º)

S1—O2	1.4369 (9)	C4—C5	1.3911 (18)
S1—O1	1.4502 (9)	C4—H4	0.961 (19)
S1—C8	1.7422 (12)	C5—C6	1.3999 (17)
S1—C9	1.7896 (9)	C5—H5	0.989 (19)
C1—C2	1.3872 (18)	C6—C7	1.4646 (16)
C1—C6	1.4038 (16)	C7—C8	1.3337 (17)
C1—H1	0.98 (2)	C7—H6	0.976 (19)
C2—C3	1.387 (2)	C8—H7	0.928 (19)
C2—H2	0.92 (2)	C9—S1^i	1.7896 (9)
C3—C4	1.3907 (19)	C9—H9	0.987 (18)
C3—H3	0.951 (19)
O2—S1—O1	119.03 (6)	C5—C4—H4	119.0 (11)
O2—S1—C8	110.63 (6)	C4—C5—C6	120.28 (12)
O1—S1—C8	107.92 (6)	C4—C5—H5	119.1 (11)
O2—S1—C9	109.56 (5)	C6—C5—H5	120.5 (11)
O1—S1—C9	103.55 (6)	C5—C6—C1	118.88 (12)
C8—S1—C9	105.10 (4)	C5—C6—C7	122.66 (11)
C2—C1—C6	120.61 (12)	C1—C6—C7	118.45 (11)
C2—C1—H1	120.3 (12)	C8—C7—C6	126.15 (11)
C6—C1—H1	119.1 (12)	C8—C7—H6	118.2 (11)
C1—C2—C3	119.93 (12)	C6—C7—H6	115.7 (11)
C1—C2—H2	118.9 (12)	C7—C8—S1	119.94 (10)
C3—C2—H2	121.1 (12)	C7—C8—H7	129.7 (12)
C2—C3—C4	120.22 (12)	S1—C8—H7	110.2 (12)
C2—C3—H3	120.5 (11)	S1—C9—S1^i	117.20 (9)
C4—C3—H3	119.3 (11)	S1—C9—H9	109.1 (10)
C3—C4—C5	120.08 (12)	S1^i—C9—H9	106.5 (11)
C3—C4—H4	120.9 (11)
C6—C1—C2—C3	−0.5 (2)	C1—C6—C7—C8	178.81 (13)
C1—C2—C3—C4	0.2 (2)	C6—C7—C8—S1	172.46 (10)
C2—C3—C4—C5	0.4 (2)	O2—S1—C8—C7	10.11 (13)
C3—C4—C5—C6	−0.7 (2)	O1—S1—C8—C7	−121.71 (11)
C4—C5—C6—C1	0.5 (2)	C9—S1—C8—C7	128.28 (11)
C4—C5—C6—C7	−178.03 (12)	O2—S1—C9—S1^i	38.32 (4)
C2—C1—C6—C5	0.1 (2)	O1—S1—C9—S1^i	166.30 (4)
C2—C1—C6—C7	178.70 (12)	C8—S1—C9—S1^i	−80.58 (5)
C5—C6—C7—C8	−2.7 (2)

Symmetry code: (i) −x+1, y, −z+1/2.