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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108002692/sk3201sup1.cif
Contains datablocks global, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108002692/sk3201Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108002692/sk3201IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108002692/sk3201IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108002692/sk3201IVsup5.hkl
Contains datablock IV

CCDC references: 682816; 682817; 682818; 682819

Comment top

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 top

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).

Experimental top

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 (CC), 1323, 1124 (SO2 str), 976 (trans CC str). Analysis calculated for C17H16O4S2: C 58.60, H 4.63%; found: C 58.21, H 4.63%.

Refinement top

In (I), all H atoms were treated as riding, with C—H distances in the range 0.95–1.00 Å and Uiso(H) values of 1.2Ueq (for primary and secondary) or 1.5Ueq (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 top

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 top
[Figure 1] 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.
[Figure 2] 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
[Figure 3] 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.
[Figure 4] 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 top
Crystal data top
C15H23O5PSZ = 4
Mr = 346.36F(000) = 736
Triclinic, P1Dx = 1.329 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.933 (3) ÅCell parameters from 8053 reflections
b = 10.014 (3) Åθ = 2.3–27.5°
c = 22.059 (7) ŵ = 0.30 mm1
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) Å3
Data collection top
Bruker SMART 1000
diffractometer
7911 independent reflections
Radiation source: fine-focus sealed tube7462 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.3 pixels mm-1θmax = 27.5°, θmin = 0.9°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
k = 1312
Tmin = 0.853, Tmax = 0.895l = 2828
15459 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0394P)2 + 1.4392P]
where P = (Fo2 + 2Fc2)/3
7911 reflections(Δ/σ)max < 0.001
406 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C15H23O5PSγ = 63.533 (4)°
Mr = 346.36V = 1731.5 (10) Å3
Triclinic, P1Z = 4
a = 8.933 (3) ÅMo Kα radiation
b = 10.014 (3) ŵ = 0.30 mm1
c = 22.059 (7) ÅT = 90 K
α = 79.769 (4)°0.55 × 0.53 × 0.38 mm
β = 89.938 (4)°
Data collection top
Bruker SMART 1000
diffractometer
7911 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
7462 reflections with I > 2σ(I)
Tmin = 0.853, Tmax = 0.895Rint = 0.032
15459 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.06Δρmax = 0.71 e Å3
7911 reflectionsΔρmin = 0.43 e Å3
406 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.85678 (8)0.47936 (7)0.08729 (3)0.01641 (13)
S10.73714 (7)0.30153 (7)0.01997 (3)0.01515 (12)
C10.8855 (3)0.0767 (3)0.17566 (13)0.0205 (5)
H10.98690.00840.15090.025*
O10.5873 (2)0.3319 (2)0.05203 (8)0.0196 (4)
C20.8638 (3)0.0623 (3)0.23611 (12)0.0224 (5)
H20.95100.01460.25290.027*
O20.8852 (2)0.16304 (19)0.04341 (9)0.0205 (4)
C30.7167 (4)0.1592 (3)0.27155 (13)0.0253 (6)
H30.70090.14850.31270.030*
O30.7586 (2)0.4631 (2)0.13967 (9)0.0209 (4)
C40.5902 (4)0.2735 (3)0.24707 (13)0.0249 (6)
H40.48860.34150.27180.030*
O40.8635 (2)0.6376 (2)0.07013 (9)0.0191 (4)
C50.6118 (3)0.2885 (3)0.18692 (13)0.0212 (5)
H50.52480.36630.17040.025*
O51.0471 (2)0.3645 (2)0.09252 (8)0.0206 (4)
C60.7588 (3)0.1912 (3)0.15103 (13)0.0175 (5)
C70.7876 (3)0.2003 (3)0.08675 (12)0.0169 (5)
H70.88630.12050.06370.020*
C80.6891 (3)0.3096 (3)0.05745 (13)0.0169 (5)
H80.59100.39310.07920.020*
C90.7853 (3)0.4584 (3)0.01471 (12)0.0156 (5)
H9A0.68360.55330.00310.019*
H9B0.87310.44600.01430.019*
C100.7198 (3)0.7797 (3)0.07849 (13)0.0219 (5)
H100.61300.77210.07290.026*
C110.7410 (4)0.8038 (4)0.14296 (15)0.0319 (7)
H11A0.74590.71730.17330.048*
H11B0.64560.89750.14930.048*
H11C0.84530.81210.14810.048*
C120.7221 (4)0.9024 (3)0.02844 (15)0.0316 (6)
H12A0.83030.90430.03230.047*
H12B0.63161.00120.03260.047*
H12C0.70580.88150.01210.047*
C131.1462 (3)0.2955 (3)0.15203 (13)0.0229 (5)
H131.08390.25670.18200.028*
C141.3032 (3)0.1641 (3)0.13917 (14)0.0268 (6)
H14A1.27280.09920.11880.040*
H14B1.37100.10460.17820.040*
H14C1.36810.20300.11220.040*
C151.1817 (4)0.4112 (3)0.17673 (14)0.0315 (6)
H15A1.23790.45270.14630.047*
H15B1.25440.36200.21540.047*
H15C1.07580.49390.18440.047*
P210.83457 (8)0.48268 (7)0.41485 (3)0.01740 (14)
S210.56212 (8)0.68909 (7)0.48265 (3)0.01627 (12)
C210.4394 (3)0.9398 (3)0.67172 (12)0.0210 (5)
H210.46851.01030.64630.025*
O210.6023 (2)0.8142 (2)0.46114 (9)0.0223 (4)
C220.3910 (4)0.9609 (3)0.73062 (13)0.0262 (6)
H220.38661.04620.74520.031*
O220.4324 (2)0.6803 (2)0.44761 (9)0.0197 (4)
C230.3486 (3)0.8577 (3)0.76853 (13)0.0246 (6)
H230.31540.87310.80870.030*
O230.7133 (2)0.5293 (2)0.36264 (9)0.0233 (4)
C240.3552 (4)0.7317 (3)0.74746 (13)0.0253 (6)
H240.32690.66120.77320.030*
O240.9595 (2)0.5557 (2)0.40632 (9)0.0216 (4)
C250.4035 (3)0.7101 (3)0.68854 (13)0.0226 (5)
H250.40840.62430.67420.027*
O250.9505 (3)0.3076 (2)0.43597 (9)0.0268 (4)
C260.4452 (3)0.8145 (3)0.64990 (13)0.0186 (5)
C270.4937 (3)0.7995 (3)0.58649 (12)0.0189 (5)
H270.51400.87810.56310.023*
C280.5114 (3)0.6856 (3)0.55936 (12)0.0184 (5)
H280.49650.60250.58150.022*
C290.7466 (3)0.5160 (3)0.48798 (12)0.0180 (5)
H29A0.72150.43120.50590.022*
H29B0.83220.51500.51680.022*
C300.9264 (4)0.6907 (3)0.35856 (13)0.0256 (6)
H300.80290.74880.34650.031*
C310.9845 (4)0.7895 (3)0.38561 (14)0.0297 (6)
H31A0.93390.80940.42450.045*
H31B0.95040.88610.35640.045*
H31C1.10710.73720.39350.045*
C321.0158 (7)0.6371 (5)0.30299 (18)0.0643 (14)
H32A1.13590.57380.31530.096*
H32B0.99980.72540.27120.096*
H32C0.96970.57740.28630.096*
C331.0908 (4)0.2197 (4)0.40207 (16)0.0355 (7)
H331.17210.26370.39900.043*
C341.0363 (5)0.2164 (4)0.33954 (17)0.0457 (9)
H34A0.95600.17410.34250.069*
H34B1.13400.15290.31970.069*
H34C0.98270.32010.31490.069*
C351.1718 (4)0.0629 (4)0.44385 (17)0.0415 (8)
H35A1.22510.06770.48170.062*
H35B1.25670.00940.42220.062*
H35C1.08570.02950.45460.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0149 (3)0.0191 (3)0.0204 (3)0.0098 (3)0.0046 (2)0.0109 (2)
S10.0116 (3)0.0149 (2)0.0211 (3)0.0060 (2)0.0007 (2)0.0087 (2)
C10.0165 (12)0.0173 (11)0.0299 (14)0.0076 (10)0.0048 (10)0.0101 (10)
O10.0151 (8)0.0226 (9)0.0257 (10)0.0107 (7)0.0056 (7)0.0104 (7)
C20.0215 (13)0.0242 (12)0.0267 (13)0.0115 (11)0.0077 (11)0.0142 (10)
O20.0172 (9)0.0153 (8)0.0259 (10)0.0031 (7)0.0018 (7)0.0082 (7)
C30.0289 (15)0.0315 (14)0.0240 (14)0.0180 (12)0.0039 (11)0.0141 (11)
O30.0188 (9)0.0240 (9)0.0246 (10)0.0113 (8)0.0082 (8)0.0120 (8)
C40.0207 (13)0.0270 (14)0.0277 (14)0.0105 (11)0.0020 (11)0.0076 (11)
O40.0147 (8)0.0207 (9)0.0290 (10)0.0107 (7)0.0084 (7)0.0147 (8)
C50.0155 (12)0.0204 (12)0.0293 (14)0.0071 (10)0.0035 (11)0.0116 (10)
O50.0136 (8)0.0238 (9)0.0253 (9)0.0065 (7)0.0003 (7)0.0125 (7)
C60.0175 (12)0.0166 (11)0.0234 (13)0.0098 (10)0.0033 (10)0.0101 (10)
C70.0119 (11)0.0178 (11)0.0238 (13)0.0074 (9)0.0010 (9)0.0092 (9)
C80.0111 (11)0.0150 (11)0.0250 (13)0.0047 (9)0.0018 (9)0.0081 (10)
C90.0113 (11)0.0178 (11)0.0203 (13)0.0072 (9)0.0018 (9)0.0084 (9)
C100.0139 (12)0.0209 (12)0.0349 (14)0.0082 (10)0.0043 (11)0.0141 (10)
C110.0311 (16)0.0330 (16)0.0375 (17)0.0133 (13)0.0095 (13)0.0244 (14)
C120.0255 (14)0.0236 (14)0.0438 (18)0.0090 (12)0.0010 (13)0.0080 (13)
C130.0209 (13)0.0223 (12)0.0238 (13)0.0074 (11)0.0004 (10)0.0069 (10)
C140.0166 (13)0.0263 (13)0.0358 (15)0.0076 (11)0.0028 (11)0.0079 (11)
C150.0312 (16)0.0311 (14)0.0329 (16)0.0115 (13)0.0047 (13)0.0150 (12)
P210.0145 (3)0.0179 (3)0.0218 (3)0.0066 (2)0.0037 (2)0.0110 (2)
S210.0152 (3)0.0149 (2)0.0218 (3)0.0076 (2)0.0056 (2)0.0090 (2)
C210.0223 (13)0.0191 (11)0.0228 (13)0.0091 (10)0.0055 (11)0.0075 (10)
O210.0276 (10)0.0171 (8)0.0281 (10)0.0133 (8)0.0100 (8)0.0102 (7)
C220.0268 (14)0.0222 (12)0.0282 (14)0.0070 (11)0.0021 (12)0.0131 (11)
O220.0125 (8)0.0225 (9)0.0247 (9)0.0065 (7)0.0009 (7)0.0103 (7)
C230.0215 (13)0.0303 (14)0.0222 (13)0.0095 (11)0.0056 (11)0.0112 (11)
O230.0191 (9)0.0280 (10)0.0269 (10)0.0110 (8)0.0028 (8)0.0144 (8)
C240.0229 (14)0.0342 (15)0.0256 (14)0.0183 (12)0.0054 (11)0.0074 (12)
O240.0180 (9)0.0259 (9)0.0245 (9)0.0131 (8)0.0025 (7)0.0049 (7)
C250.0205 (13)0.0274 (13)0.0278 (14)0.0152 (11)0.0062 (11)0.0125 (11)
O250.0235 (10)0.0200 (9)0.0341 (11)0.0050 (8)0.0070 (9)0.0122 (8)
C260.0144 (11)0.0184 (12)0.0240 (14)0.0064 (9)0.0023 (10)0.0092 (10)
C270.0157 (12)0.0174 (11)0.0255 (13)0.0075 (10)0.0056 (10)0.0084 (9)
C280.0173 (12)0.0201 (12)0.0210 (13)0.0098 (10)0.0050 (10)0.0084 (10)
C290.0162 (12)0.0191 (11)0.0221 (14)0.0090 (10)0.0034 (10)0.0093 (10)
C300.0313 (15)0.0242 (13)0.0270 (14)0.0167 (12)0.0010 (12)0.0076 (11)
C310.0331 (16)0.0335 (15)0.0329 (15)0.0210 (13)0.0076 (13)0.0152 (12)
C320.132 (4)0.073 (3)0.040 (2)0.082 (3)0.046 (2)0.037 (2)
C330.0293 (16)0.0327 (16)0.0443 (18)0.0090 (13)0.0072 (14)0.0212 (14)
C340.049 (2)0.0373 (18)0.046 (2)0.0084 (16)0.0116 (17)0.0275 (16)
C350.0340 (17)0.0271 (15)0.051 (2)0.0006 (14)0.0002 (15)0.0152 (14)
Geometric parameters (Å, º) top
P1—O31.4794 (19)P21—O231.442 (2)
P1—O51.5614 (19)P21—O251.5673 (19)
P1—O41.5901 (19)P21—O241.5792 (19)
P1—C91.805 (3)P21—C291.813 (3)
S1—O21.4324 (18)S21—O221.4368 (19)
S1—O11.4480 (19)S21—O211.4539 (19)
S1—C81.741 (3)S21—C281.750 (3)
S1—C91.790 (2)S21—C291.765 (3)
C1—C21.389 (4)C21—C221.391 (4)
C1—C61.398 (3)C21—C261.402 (3)
C1—H10.9500C21—H210.9500
C2—C31.369 (4)C22—C231.397 (4)
C2—H20.9500C22—H220.9500
C3—C41.395 (4)C23—C241.398 (4)
C3—H30.9500C23—H230.9500
C4—C51.385 (4)C24—C251.392 (4)
C4—H40.9500C24—H240.9500
O4—C101.473 (3)O24—C301.471 (3)
C5—C61.374 (4)C25—C261.410 (4)
C5—H50.9500C25—H250.9500
O5—C131.456 (3)O25—C331.468 (3)
C6—C71.467 (4)C26—C271.477 (4)
C7—C81.335 (3)C27—C281.329 (3)
C7—H70.9500C27—H270.9500
C8—H80.9500C28—H280.9500
C9—H9A0.9900C29—H29A0.9900
C9—H9B0.9900C29—H29B0.9900
C10—C121.507 (4)C30—C311.508 (4)
C10—C111.510 (4)C30—C321.509 (4)
C10—H101.0000C30—H301.0000
C11—H11A0.9800C31—H31A0.9800
C11—H11B0.9800C31—H31B0.9800
C11—H11C0.9800C31—H31C0.9800
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
C13—C141.506 (4)C33—C341.474 (5)
C13—C151.514 (4)C33—C351.521 (5)
C13—H131.0000C33—H331.0000
C14—H14A0.9800C34—H34A0.9800
C14—H14B0.9800C34—H34B0.9800
C14—H14C0.9800C34—H34C0.9800
C15—H15A0.9800C35—H35A0.9800
C15—H15B0.9800C35—H35B0.9800
C15—H15C0.9800C35—H35C0.9800
O3—P1—O5117.92 (11)O23—P21—O25116.82 (11)
O3—P1—O4116.09 (10)O23—P21—O24114.32 (12)
O5—P1—O4101.29 (10)O25—P21—O24104.73 (11)
O3—P1—C9114.89 (11)O23—P21—C29115.16 (12)
O5—P1—C9101.08 (10)O25—P21—C2997.14 (11)
O4—P1—C9103.24 (11)O24—P21—C29106.77 (11)
O2—S1—O1117.76 (12)O22—S21—O21118.14 (12)
O2—S1—C8109.31 (11)O22—S21—C28107.76 (12)
O1—S1—C8108.37 (11)O21—S21—C28110.43 (12)
O2—S1—C9109.06 (11)O22—S21—C29107.97 (11)
O1—S1—C9109.56 (11)O21—S21—C29108.66 (12)
C8—S1—C9101.56 (12)C28—S21—C29102.76 (13)
C2—C1—C6120.3 (3)C22—C21—C26119.9 (3)
C2—C1—H1119.8C22—C21—H21120.0
C6—C1—H1119.8C26—C21—H21120.0
C3—C2—C1120.0 (2)C21—C22—C23120.5 (2)
C3—C2—H2120.0C21—C22—H22119.7
C1—C2—H2120.0C23—C22—H22119.7
C2—C3—C4119.8 (3)C22—C23—C24120.0 (3)
C2—C3—H3120.1C22—C23—H23120.0
C4—C3—H3120.1C24—C23—H23120.0
C5—C4—C3120.3 (3)C25—C24—C23119.7 (3)
C5—C4—H4119.8C25—C24—H24120.2
C3—C4—H4119.8C23—C24—H24120.2
C10—O4—P1120.72 (15)C30—O24—P21122.51 (17)
C6—C5—C4120.1 (2)C24—C25—C26120.6 (2)
C6—C5—H5119.9C24—C25—H25119.7
C4—C5—H5119.9C26—C25—H25119.7
C13—O5—P1121.69 (16)C33—O25—P21123.42 (19)
C5—C6—C1119.4 (3)C21—C26—C25119.3 (2)
C5—C6—C7122.5 (2)C21—C26—C27117.7 (2)
C1—C6—C7118.1 (2)C25—C26—C27123.0 (2)
C8—C7—C6126.5 (2)C28—C27—C26125.7 (2)
C8—C7—H7116.8C28—C27—H27117.2
C6—C7—H7116.8C26—C27—H27117.2
C7—C8—S1121.1 (2)C27—C28—S21119.8 (2)
C7—C8—H8119.5C27—C28—H28120.1
S1—C8—H8119.5S21—C28—H28120.1
S1—C9—P1114.68 (14)S21—C29—P21114.35 (15)
S1—C9—H9A108.6S21—C29—H29A108.7
P1—C9—H9A108.6P21—C29—H29A108.7
S1—C9—H9B108.6S21—C29—H29B108.7
P1—C9—H9B108.6P21—C29—H29B108.7
H9A—C9—H9B107.6H29A—C29—H29B107.6
O4—C10—C12105.5 (2)O24—C30—C31108.3 (2)
O4—C10—C11108.6 (2)O24—C30—C32108.0 (3)
C12—C10—C11113.3 (2)C31—C30—C32113.1 (3)
O4—C10—H10109.8O24—C30—H30109.1
C12—C10—H10109.8C31—C30—H30109.1
C11—C10—H10109.8C32—C30—H30109.1
C10—C11—H11A109.5C30—C31—H31A109.5
C10—C11—H11B109.5C30—C31—H31B109.5
H11A—C11—H11B109.5H31A—C31—H31B109.5
C10—C11—H11C109.5C30—C31—H31C109.5
H11A—C11—H11C109.5H31A—C31—H31C109.5
H11B—C11—H11C109.5H31B—C31—H31C109.5
C10—C12—H12A109.5C30—C32—H32A109.5
C10—C12—H12B109.5C30—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C10—C12—H12C109.5C30—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
O5—C13—C14104.7 (2)O25—C33—C34112.9 (3)
O5—C13—C15110.2 (2)O25—C33—C35103.0 (3)
C14—C13—C15112.8 (2)C34—C33—C35112.7 (3)
O5—C13—H13109.7O25—C33—H33109.4
C14—C13—H13109.7C34—C33—H33109.4
C15—C13—H13109.7C35—C33—H33109.4
C13—C14—H14A109.5C33—C34—H34A109.5
C13—C14—H14B109.5C33—C34—H34B109.5
H14A—C14—H14B109.5H34A—C34—H34B109.5
C13—C14—H14C109.5C33—C34—H34C109.5
H14A—C14—H14C109.5H34A—C34—H34C109.5
H14B—C14—H14C109.5H34B—C34—H34C109.5
C13—C15—H15A109.5C33—C35—H35A109.5
C13—C15—H15B109.5C33—C35—H35B109.5
H15A—C15—H15B109.5H35A—C35—H35B109.5
C13—C15—H15C109.5C33—C35—H35C109.5
H15A—C15—H15C109.5H35A—C35—H35C109.5
H15B—C15—H15C109.5H35B—C35—H35C109.5
C6—C1—C2—C31.0 (4)C26—C21—C22—C230.3 (4)
C1—C2—C3—C41.0 (4)C21—C22—C23—C240.2 (4)
C2—C3—C4—C50.7 (4)C22—C23—C24—C250.2 (4)
O3—P1—O4—C1032.6 (2)O23—P21—O24—C3016.9 (2)
O5—P1—O4—C10161.58 (18)O25—P21—O24—C30146.03 (19)
C9—P1—O4—C1094.05 (19)C29—P21—O24—C30111.6 (2)
C3—C4—C5—C60.4 (4)C23—C24—C25—C260.2 (4)
O3—P1—O5—C1329.6 (2)O23—P21—O25—C3374.5 (2)
O4—P1—O5—C1398.3 (2)O24—P21—O25—C3353.1 (2)
C9—P1—O5—C13155.65 (19)C29—P21—O25—C33162.6 (2)
C4—C5—C6—C10.3 (4)C22—C21—C26—C250.8 (4)
C4—C5—C6—C7179.1 (2)C22—C21—C26—C27178.6 (2)
C2—C1—C6—C50.6 (4)C24—C25—C26—C210.7 (4)
C2—C1—C6—C7179.4 (2)C24—C25—C26—C27178.6 (3)
C5—C6—C7—C88.1 (4)C21—C26—C27—C28177.5 (3)
C1—C6—C7—C8173.1 (3)C25—C26—C27—C283.2 (4)
C6—C7—C8—S1178.0 (2)C26—C27—C28—S21177.6 (2)
O2—S1—C8—C72.6 (3)O22—S21—C28—C27122.2 (2)
O1—S1—C8—C7132.1 (2)O21—S21—C28—C278.2 (3)
C9—S1—C8—C7112.6 (2)C29—S21—C28—C27123.9 (2)
O2—S1—C9—P160.57 (16)O22—S21—C29—P2166.18 (16)
O1—S1—C9—P169.64 (16)O21—S21—C29—P2163.09 (16)
C8—S1—C9—P1175.90 (13)C28—S21—C29—P21179.90 (14)
O3—P1—C9—S144.73 (17)O23—P21—C29—S2138.84 (18)
O5—P1—C9—S183.36 (15)O25—P21—C29—S21162.98 (14)
O4—P1—C9—S1172.11 (12)O24—P21—C29—S2189.23 (15)
P1—O4—C10—C12148.57 (18)P21—O24—C30—C31141.7 (2)
P1—O4—C10—C1189.7 (2)P21—O24—C30—C3295.5 (3)
P1—O5—C13—C14164.82 (17)P21—O25—C33—C3463.5 (3)
P1—O5—C13—C1573.7 (3)P21—O25—C33—C35174.7 (2)
(II) diisopropyl {[2-(7-methoxy-1,3-benzodioxol-5- yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate top
Crystal data top
C18H27O10PS2Z = 4
Mr = 498.49F(000) = 1048
Triclinic, P1Dx = 1.465 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8656 (3) ÅCell parameters from 8381 reflections
b = 15.1481 (5) Åθ = 2.5–30.1°
c = 15.9024 (5) ŵ = 0.36 mm1
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) Å3
Data collection top
Bruker SMART ApexII
diffractometer
13151 independent reflections
Radiation source: fine-focus sealed tube11227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.3 pixels mm-1θmax = 30.0°, θmin = 1.9°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
k = 2121
Tmin = 0.845, Tmax = 0.976l = 2222
25647 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092Only H-atom coordinates refined
S = 1.03 w = 1/[σ2(Fo2) + (0.047P)2 + 1.1703P]
where P = (Fo2 + 2Fc2)/3
13151 reflections(Δ/σ)max = 0.001
623 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C18H27O10PS2γ = 72.267 (3)°
Mr = 498.49V = 2260.11 (12) Å3
Triclinic, P1Z = 4
a = 9.8656 (3) ÅMo Kα radiation
b = 15.1481 (5) ŵ = 0.36 mm1
c = 15.9024 (5) ÅT = 90 K
α = 86.929 (3)°0.49 × 0.08 × 0.07 mm
β = 89.893 (3)°
Data collection top
Bruker SMART ApexII
diffractometer
13151 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
11227 reflections with I > 2σ(I)
Tmin = 0.845, Tmax = 0.976Rint = 0.017
25647 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.092Only H-atom coordinates refined
S = 1.03Δρmax = 0.50 e Å3
13151 reflectionsΔρmin = 0.35 e Å3
623 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.65255 (4)0.10258 (2)0.47019 (2)0.01360 (7)
S10.62912 (3)0.32474 (2)0.670000 (19)0.01231 (6)
S20.59986 (3)0.13154 (2)0.65576 (2)0.01348 (7)
C10.45611 (15)0.38667 (9)1.03805 (8)0.0152 (2)
C1A0.56207 (16)0.40024 (9)1.08805 (8)0.0160 (2)
C1B0.21556 (17)0.38647 (12)1.02248 (10)0.0236 (3)
H1B10.20130.43280.97530.031 (5)*
H1B20.12800.39831.05500.038 (6)*
H1B30.23960.32431.00080.037 (6)*
O10.32935 (11)0.39229 (7)1.07565 (6)0.0195 (2)
C20.69185 (19)0.42878 (12)1.19243 (9)0.0250 (3)
H2A0.68150.49041.21440.041 (6)*
H2B0.73880.38051.23650.029 (5)*
O20.55400 (12)0.42121 (8)1.17103 (6)0.0219 (2)
C30.72719 (15)0.38276 (9)0.97283 (8)0.0150 (2)
H30.81730.38240.95150.024 (5)*
C3A0.69322 (15)0.39773 (9)1.05607 (8)0.0157 (2)
O30.77609 (12)0.41689 (8)1.11737 (6)0.0230 (2)
C40.62138 (14)0.36800 (9)0.92108 (8)0.0128 (2)
O40.74259 (10)0.36562 (7)0.65794 (6)0.01669 (19)
C50.48751 (14)0.36971 (9)0.95340 (8)0.0143 (2)
H50.41790.35920.91740.012 (4)*
O50.50574 (10)0.35581 (7)0.61487 (6)0.01783 (19)
C60.65474 (14)0.35408 (9)0.83223 (8)0.0132 (2)
H60.74300.36090.81410.024 (5)*
O60.48411 (11)0.16621 (7)0.71262 (6)0.0185 (2)
C70.57439 (14)0.33279 (9)0.77386 (8)0.0140 (2)
H70.48740.32210.78920.026 (5)*
O70.69319 (12)0.03822 (7)0.66989 (7)0.0208 (2)
C80.71192 (14)0.20422 (9)0.65489 (8)0.0146 (2)
H8A0.76120.19890.60030.032 (5)*
H8B0.78570.17950.69940.022 (5)*
O80.54777 (11)0.13553 (7)0.39322 (6)0.0189 (2)
C90.52568 (14)0.14409 (9)0.55293 (8)0.0145 (2)
H9A0.47500.21060.53990.026 (5)*
H9B0.45420.11030.55230.035 (6)*
O90.69009 (10)0.00627 (7)0.47599 (6)0.01584 (19)
C100.60148 (16)0.13119 (10)0.30599 (8)0.0183 (3)
H100.69900.08550.30520.029 (5)*
O100.77637 (11)0.13750 (7)0.47310 (6)0.0193 (2)
C110.6089 (3)0.22586 (13)0.27908 (12)0.0454 (6)
H11A0.51480.27150.28430.075 (9)*
H11B0.63890.22630.22030.042 (6)*
H11C0.67770.24170.31500.086 (11)*
C120.5027 (3)0.0984 (2)0.25415 (12)0.0612 (8)
H12A0.50120.03720.27670.076 (10)*
H12B0.53510.09400.19580.054 (7)*
H12C0.40660.14250.25580.085 (11)*
C130.83487 (14)0.06819 (10)0.49824 (9)0.0181 (3)
H130.89000.03270.52710.019 (4)*
C140.81785 (17)0.14531 (10)0.55724 (10)0.0228 (3)
H14A0.76030.11860.60530.034 (6)*
H14B0.91180.18450.57750.031 (5)*
H14C0.77040.18280.52730.032 (5)*
C150.90642 (18)0.10274 (14)0.41712 (11)0.0328 (4)
H15A0.84780.13280.38670.034 (6)*
H15B1.00010.14760.42980.050 (7)*
H15C0.91780.05030.38220.030 (5)*
P210.84887 (4)0.89444 (2)0.01877 (2)0.01329 (7)
S210.87260 (3)0.67349 (2)0.203910 (19)0.01180 (6)
S220.90315 (3)0.86631 (2)0.16972 (2)0.01342 (7)
O211.16970 (11)0.58996 (8)0.61561 (6)0.0213 (2)
O220.93511 (12)0.57667 (7)0.71458 (6)0.0207 (2)
O230.70836 (11)0.59387 (8)0.66088 (6)0.0210 (2)
O240.75916 (10)0.63298 (7)0.19439 (6)0.01615 (19)
O250.99720 (10)0.64304 (7)0.15231 (6)0.01645 (19)
O261.01940 (11)0.83121 (7)0.22947 (6)0.0188 (2)
O270.81100 (12)0.95983 (7)0.17469 (7)0.0210 (2)
O280.95287 (11)0.86026 (7)0.09272 (6)0.0184 (2)
O290.81183 (10)1.00328 (7)0.02489 (6)0.01557 (18)
O300.72443 (11)0.86023 (7)0.01101 (6)0.0185 (2)
C211.04116 (15)0.60162 (9)0.57723 (8)0.0153 (2)
C21A0.93154 (15)0.59304 (9)0.62872 (8)0.0156 (2)
C21B1.28095 (17)0.60337 (12)0.56322 (10)0.0245 (3)
H21A1.25280.66750.53940.030 (5)*
H21B1.29770.56060.51750.029 (5)*
H21C1.36840.59120.59700.041 (6)*
C220.80079 (17)0.55976 (11)0.73296 (9)0.0237 (3)
H22A0.81590.49250.74400.022 (5)*
H22B0.75800.59240.78340.037 (6)*
C230.76504 (14)0.61748 (9)0.51182 (8)0.0149 (2)
H230.67340.62160.49030.016 (4)*
C23A0.79757 (15)0.60222 (9)0.59673 (8)0.0152 (2)
C240.87513 (14)0.62661 (9)0.45857 (8)0.0127 (2)
C251.01130 (14)0.61896 (9)0.49098 (8)0.0140 (2)
H251.08350.62560.45380.015 (4)*
C260.84344 (14)0.64110 (9)0.36828 (8)0.0129 (2)
H260.75650.63320.34990.028 (5)*
C270.92482 (14)0.66438 (9)0.30883 (8)0.0134 (2)
H271.01070.67580.32410.028 (5)*
C280.79034 (14)0.79434 (9)0.17743 (8)0.0143 (2)
H28A0.73960.80010.12280.026 (5)*
H28B0.71770.81910.22030.029 (5)*
C290.97641 (14)0.85330 (9)0.06772 (8)0.0144 (2)
H29A1.02700.78670.06150.024 (5)*
H29B1.04790.88710.06300.037 (6)*
C300.89854 (16)0.86548 (10)0.18037 (8)0.0183 (3)
H300.80220.91260.18590.020 (4)*
C310.8875 (3)0.77142 (13)0.19814 (12)0.0435 (5)
H31A0.81600.75720.16150.084 (10)*
H31B0.97990.72440.18740.054 (7)*
H31C0.85920.77130.25720.056 (7)*
C321.0005 (3)0.8958 (2)0.23556 (11)0.0503 (6)
H32A1.00300.95710.22020.059 (8)*
H32B0.96970.89920.29450.046 (7)*
H32C1.09570.85100.22820.078 (10)*
C330.66698 (14)1.06512 (10)0.00853 (9)0.0173 (3)
H330.61201.02940.02380.022 (5)*
C340.68405 (17)1.14179 (10)0.04343 (10)0.0215 (3)
H34A0.74211.11460.09370.030 (5)*
H34B0.59021.18060.06040.027 (5)*
H34C0.73101.17990.00990.033 (5)*
C350.59535 (18)1.10003 (13)0.09271 (11)0.0293 (3)
H35A0.58491.04760.12280.032 (5)*
H35B0.65331.13090.12590.038 (6)*
H35C0.50121.14430.08410.037 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01522 (16)0.01506 (15)0.01169 (15)0.00611 (12)0.00153 (11)0.00241 (12)
S10.01125 (14)0.01576 (14)0.01087 (13)0.00527 (11)0.00094 (10)0.00223 (11)
S20.01464 (14)0.01453 (14)0.01182 (14)0.00497 (11)0.00171 (11)0.00260 (11)
C10.0196 (6)0.0113 (5)0.0139 (6)0.0036 (5)0.0038 (5)0.0007 (4)
C1A0.0258 (7)0.0111 (6)0.0099 (5)0.0037 (5)0.0011 (5)0.0003 (4)
C1B0.0236 (7)0.0292 (8)0.0205 (7)0.0118 (6)0.0042 (6)0.0016 (6)
O10.0220 (5)0.0248 (5)0.0132 (4)0.0093 (4)0.0063 (4)0.0024 (4)
C20.0382 (9)0.0268 (8)0.0148 (6)0.0167 (7)0.0012 (6)0.0024 (6)
O20.0325 (6)0.0230 (5)0.0102 (4)0.0079 (4)0.0015 (4)0.0028 (4)
C30.0172 (6)0.0133 (6)0.0137 (6)0.0035 (5)0.0002 (5)0.0016 (4)
C3A0.0218 (6)0.0116 (6)0.0132 (6)0.0041 (5)0.0031 (5)0.0013 (4)
O30.0255 (5)0.0310 (6)0.0141 (5)0.0101 (5)0.0031 (4)0.0054 (4)
C40.0168 (6)0.0096 (5)0.0115 (5)0.0031 (4)0.0014 (4)0.0016 (4)
O40.0160 (5)0.0229 (5)0.0147 (4)0.0111 (4)0.0016 (3)0.0018 (4)
C50.0175 (6)0.0130 (6)0.0123 (6)0.0047 (5)0.0020 (5)0.0017 (4)
O50.0147 (5)0.0222 (5)0.0160 (5)0.0050 (4)0.0035 (4)0.0002 (4)
C60.0136 (6)0.0124 (5)0.0134 (6)0.0033 (4)0.0028 (4)0.0020 (4)
O60.0184 (5)0.0237 (5)0.0158 (5)0.0094 (4)0.0066 (4)0.0052 (4)
C70.0157 (6)0.0152 (6)0.0116 (5)0.0051 (5)0.0037 (4)0.0037 (4)
O70.0253 (5)0.0152 (5)0.0190 (5)0.0020 (4)0.0010 (4)0.0006 (4)
C80.0112 (6)0.0179 (6)0.0156 (6)0.0049 (5)0.0016 (4)0.0050 (5)
O80.0199 (5)0.0240 (5)0.0117 (4)0.0050 (4)0.0011 (4)0.0006 (4)
C90.0153 (6)0.0164 (6)0.0130 (6)0.0061 (5)0.0005 (4)0.0037 (5)
O90.0141 (4)0.0146 (4)0.0189 (5)0.0039 (4)0.0002 (4)0.0038 (4)
C100.0247 (7)0.0204 (7)0.0116 (6)0.0094 (5)0.0031 (5)0.0005 (5)
O100.0196 (5)0.0227 (5)0.0190 (5)0.0113 (4)0.0045 (4)0.0041 (4)
C110.0868 (17)0.0212 (8)0.0284 (9)0.0170 (10)0.0228 (10)0.0004 (7)
C120.0697 (17)0.127 (2)0.0188 (9)0.0754 (18)0.0069 (9)0.0132 (11)
C130.0124 (6)0.0201 (6)0.0198 (6)0.0014 (5)0.0008 (5)0.0044 (5)
C140.0262 (7)0.0157 (6)0.0233 (7)0.0013 (6)0.0024 (6)0.0030 (5)
C150.0231 (8)0.0405 (10)0.0279 (8)0.0011 (7)0.0089 (6)0.0059 (7)
P210.01503 (15)0.01381 (15)0.01130 (14)0.00494 (12)0.00077 (11)0.00029 (11)
S210.01100 (13)0.01500 (14)0.00989 (13)0.00484 (11)0.00037 (10)0.00008 (10)
S220.01514 (14)0.01413 (14)0.01127 (14)0.00507 (11)0.00118 (11)0.00037 (11)
O210.0218 (5)0.0299 (6)0.0142 (5)0.0116 (4)0.0052 (4)0.0017 (4)
O220.0309 (6)0.0222 (5)0.0098 (4)0.0093 (4)0.0004 (4)0.0004 (4)
O230.0226 (5)0.0253 (5)0.0130 (5)0.0047 (4)0.0054 (4)0.0024 (4)
O240.0155 (4)0.0215 (5)0.0146 (4)0.0103 (4)0.0004 (3)0.0015 (4)
O250.0137 (4)0.0206 (5)0.0146 (4)0.0044 (4)0.0039 (3)0.0016 (4)
O260.0190 (5)0.0241 (5)0.0153 (5)0.0099 (4)0.0053 (4)0.0022 (4)
O270.0264 (5)0.0151 (5)0.0191 (5)0.0027 (4)0.0014 (4)0.0017 (4)
O280.0194 (5)0.0222 (5)0.0117 (4)0.0031 (4)0.0005 (4)0.0026 (4)
O290.0135 (4)0.0135 (4)0.0186 (5)0.0030 (3)0.0011 (3)0.0017 (4)
O300.0198 (5)0.0198 (5)0.0184 (5)0.0097 (4)0.0036 (4)0.0013 (4)
C210.0186 (6)0.0138 (6)0.0137 (6)0.0051 (5)0.0020 (5)0.0008 (5)
C21A0.0246 (7)0.0122 (6)0.0093 (5)0.0045 (5)0.0001 (5)0.0004 (4)
C21B0.0229 (7)0.0327 (8)0.0213 (7)0.0137 (6)0.0035 (6)0.0008 (6)
C220.0299 (8)0.0262 (7)0.0146 (6)0.0086 (6)0.0020 (6)0.0019 (5)
C230.0163 (6)0.0137 (6)0.0136 (6)0.0034 (5)0.0016 (5)0.0001 (4)
C23A0.0192 (6)0.0117 (6)0.0135 (6)0.0031 (5)0.0046 (5)0.0007 (4)
C240.0155 (6)0.0113 (5)0.0107 (5)0.0032 (4)0.0005 (4)0.0000 (4)
C250.0168 (6)0.0129 (6)0.0124 (6)0.0045 (5)0.0005 (4)0.0006 (4)
C260.0133 (6)0.0125 (6)0.0123 (6)0.0033 (4)0.0004 (4)0.0003 (4)
C270.0142 (6)0.0152 (6)0.0111 (5)0.0051 (5)0.0013 (4)0.0005 (4)
C280.0116 (6)0.0169 (6)0.0136 (6)0.0039 (5)0.0006 (4)0.0027 (5)
C290.0147 (6)0.0159 (6)0.0126 (6)0.0049 (5)0.0005 (4)0.0011 (5)
C300.0244 (7)0.0197 (6)0.0116 (6)0.0078 (5)0.0020 (5)0.0004 (5)
C310.0826 (16)0.0248 (9)0.0264 (9)0.0207 (10)0.0144 (10)0.0027 (7)
C320.0581 (14)0.0979 (19)0.0167 (8)0.0569 (14)0.0002 (8)0.0016 (9)
C330.0136 (6)0.0176 (6)0.0184 (6)0.0019 (5)0.0020 (5)0.0015 (5)
C340.0250 (7)0.0153 (6)0.0210 (7)0.0015 (5)0.0018 (5)0.0003 (5)
C350.0230 (8)0.0327 (9)0.0264 (8)0.0002 (7)0.0081 (6)0.0007 (7)
Geometric parameters (Å, º) top
P1—O101.4734 (10)P21—O301.4736 (10)
P1—O81.5623 (10)P21—O281.5623 (10)
P1—O91.5736 (10)P21—O291.5739 (10)
P1—C91.8156 (14)P21—C291.8167 (14)
S1—O41.4430 (10)S21—O241.4424 (10)
S1—O51.4431 (10)S21—O251.4452 (10)
S1—C71.7356 (13)S21—C271.7330 (13)
S1—C81.7877 (14)S21—C281.7891 (14)
S2—O71.4389 (11)S22—O271.4376 (11)
S2—O61.4420 (10)S22—O261.4420 (10)
S2—C91.7698 (13)S22—C291.7707 (13)
S2—C81.7816 (14)S22—C281.7795 (14)
C1—O11.3662 (16)O21—C211.3663 (16)
C1—C1A1.385 (2)O21—C21B1.4333 (19)
C1—C51.4004 (18)O22—C21A1.3730 (16)
C1A—O21.3702 (16)O22—C221.4506 (19)
C1A—C3A1.380 (2)O23—C23A1.3718 (16)
C1B—O11.4333 (18)O23—C221.4374 (18)
C1B—H1B10.9800O28—C301.4836 (16)
C1B—H1B20.9800O29—C331.4821 (16)
C1B—H1B30.9800C21—C21A1.3885 (19)
C2—O31.4409 (19)C21—C251.3974 (18)
C2—O21.442 (2)C21A—C23A1.381 (2)
C2—H2A0.9900C21B—H21A0.9800
C2—H2B0.9900C21B—H21B0.9800
C3—C3A1.3785 (18)C21B—H21C0.9800
C3—C41.4078 (18)C22—H22A0.9900
C3—H30.9500C22—H22B0.9900
C3A—O31.3714 (16)C23—C23A1.3793 (18)
C4—C51.4097 (18)C23—C241.4111 (18)
C4—C61.4619 (17)C23—H230.9500
C5—H50.9500C24—C251.4090 (18)
C6—C71.3359 (18)C24—C261.4607 (17)
C6—H60.9500C25—H250.9500
C7—H70.9500C26—C271.3405 (18)
C8—H8A0.9900C26—H260.9500
C8—H8B0.9900C27—H270.9500
O8—C101.4816 (16)C28—H28A0.9900
C9—H9A0.9900C28—H28B0.9900
C9—H9B0.9900C29—H29A0.9900
O9—C131.4817 (16)C29—H29B0.9900
C10—C121.490 (2)C30—C321.492 (2)
C10—C111.497 (2)C30—C311.503 (2)
C10—H101.0000C30—H301.0000
C11—H11A0.9800C31—H31A0.9800
C11—H11B0.9800C31—H31B0.9800
C11—H11C0.9800C31—H31C0.9800
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
C13—C141.508 (2)C33—C351.507 (2)
C13—C151.510 (2)C33—C341.511 (2)
C13—H131.0000C33—H331.0000
C14—H14A0.9800C34—H34A0.9800
C14—H14B0.9800C34—H34B0.9800
C14—H14C0.9800C34—H34C0.9800
C15—H15A0.9800C35—H35A0.9800
C15—H15B0.9800C35—H35B0.9800
C15—H15C0.9800C35—H35C0.9800
O10—P1—O8117.77 (6)O30—P21—O28117.77 (6)
O10—P1—O9114.75 (6)O30—P21—O29114.53 (6)
O8—P1—O9104.94 (6)O28—P21—O29105.13 (6)
O10—P1—C9113.38 (6)O30—P21—C29113.39 (6)
O8—P1—C998.04 (6)O28—P21—C2998.02 (6)
O9—P1—C9106.09 (6)O29—P21—C29106.17 (6)
O4—S1—O5118.93 (6)O24—S21—O25118.95 (6)
O4—S1—C7109.81 (6)O24—S21—C27109.91 (6)
O5—S1—C7109.18 (6)O25—S21—C27109.31 (6)
O4—S1—C8104.10 (6)O24—S21—C28103.98 (6)
O5—S1—C8107.37 (6)O25—S21—C28107.25 (6)
C7—S1—C8106.68 (6)C27—S21—C28106.64 (6)
O7—S2—O6119.22 (6)O27—S22—O26119.17 (6)
O7—S2—C9108.75 (6)O27—S22—C29108.77 (6)
O6—S2—C9107.35 (6)O26—S22—C29107.31 (6)
O7—S2—C8105.71 (6)O27—S22—C28105.81 (7)
O6—S2—C8109.27 (6)O26—S22—C28109.14 (6)
C9—S2—C8105.80 (6)C29—S22—C28105.93 (6)
O1—C1—C1A116.90 (12)C21—O21—C21B116.72 (11)
O1—C1—C5125.79 (13)C21A—O22—C22104.17 (11)
C1A—C1—C5117.30 (12)C23A—O23—C22104.67 (11)
O2—C1A—C3A110.70 (12)C30—O28—P21120.88 (9)
O2—C1A—C1127.59 (13)C33—O29—P21122.05 (9)
C3A—C1A—C1121.65 (12)O21—C21—C21A116.68 (12)
O1—C1B—H1B1109.5O21—C21—C25125.99 (13)
O1—C1B—H1B2109.5C21A—C21—C25117.31 (12)
H1B1—C1B—H1B2109.5O22—C21A—C23A110.39 (12)
O1—C1B—H1B3109.5O22—C21A—C21127.84 (13)
H1B1—C1B—H1B3109.5C23A—C21A—C21121.77 (12)
H1B2—C1B—H1B3109.5O21—C21B—H21A109.5
C1—O1—C1B117.02 (11)O21—C21B—H21B109.5
O3—C2—O2108.07 (11)H21A—C21B—H21B109.5
O3—C2—H2A110.1O21—C21B—H21C109.5
O2—C2—H2A110.1H21A—C21B—H21C109.5
O3—C2—H2B110.1H21B—C21B—H21C109.5
O2—C2—H2B110.1O23—C22—O22107.57 (11)
H2A—C2—H2B108.4O23—C22—H22A110.2
C1A—O2—C2105.36 (11)O22—C22—H22A110.2
C3A—C3—C4116.55 (13)O23—C22—H22B110.2
C3A—C3—H3121.7O22—C22—H22B110.2
C4—C3—H3121.7H22A—C22—H22B108.5
O3—C3A—C3127.20 (13)C23A—C23—C24116.45 (12)
O3—C3A—C1A110.01 (12)C23A—C23—H23121.8
C3—C3A—C1A122.70 (13)C24—C23—H23121.8
C3A—O3—C2105.74 (11)O23—C23A—C23127.45 (13)
C3—C4—C5121.11 (12)O23—C23A—C21A110.05 (12)
C3—C4—C6117.16 (12)C23—C23A—C21A122.51 (13)
C5—C4—C6121.70 (12)C25—C24—C23121.30 (12)
C1—C5—C4120.67 (12)C25—C24—C26121.44 (12)
C1—C5—H5119.7C23—C24—C26117.23 (12)
C4—C5—H5119.7C21—C25—C24120.63 (12)
C7—C6—C4126.94 (12)C21—C25—H25119.7
C7—C6—H6116.5C24—C25—H25119.7
C4—C6—H6116.5C27—C26—C24126.48 (12)
C6—C7—S1119.94 (10)C27—C26—H26116.8
C6—C7—H7120.0C24—C26—H26116.8
S1—C7—H7120.0C26—C27—S21119.69 (10)
S2—C8—S1117.24 (7)C26—C27—H27120.2
S2—C8—H8A108.0S21—C27—H27120.2
S1—C8—H8A108.0S22—C28—S21117.26 (7)
S2—C8—H8B108.0S22—C28—H28A108.0
S1—C8—H8B108.0S21—C28—H28A108.0
H8A—C8—H8B107.2S22—C28—H28B108.0
C10—O8—P1120.86 (9)S21—C28—H28B108.0
S2—C9—P1115.21 (7)H28A—C28—H28B107.2
S2—C9—H9A108.5S22—C29—P21115.28 (7)
P1—C9—H9A108.5S22—C29—H29A108.5
S2—C9—H9B108.5P21—C29—H29A108.5
P1—C9—H9B108.5S22—C29—H29B108.5
H9A—C9—H9B107.5P21—C29—H29B108.5
C13—O9—P1122.41 (9)H29A—C29—H29B107.5
O8—C10—C12106.87 (13)O28—C30—C32106.53 (12)
O8—C10—C11107.37 (12)O28—C30—C31107.63 (12)
C12—C10—C11114.31 (18)C32—C30—C31113.87 (17)
O8—C10—H10109.4O28—C30—H30109.6
C12—C10—H10109.4C32—C30—H30109.6
C11—C10—H10109.4C31—C30—H30109.6
C10—C11—H11A109.5C30—C31—H31A109.5
C10—C11—H11B109.5C30—C31—H31B109.5
H11A—C11—H11B109.5H31A—C31—H31B109.5
C10—C11—H11C109.5C30—C31—H31C109.5
H11A—C11—H11C109.5H31A—C31—H31C109.5
H11B—C11—H11C109.5H31B—C31—H31C109.5
C10—C12—H12A109.5C30—C32—H32A109.5
C10—C12—H12B109.5C30—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C10—C12—H12C109.5C30—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
O9—C13—C14107.19 (11)O29—C33—C35107.41 (12)
O9—C13—C15107.30 (12)O29—C33—C34107.16 (11)
C14—C13—C15112.90 (13)C35—C33—C34113.15 (13)
O9—C13—H13109.8O29—C33—H33109.7
C14—C13—H13109.8C35—C33—H33109.7
C15—C13—H13109.8C34—C33—H33109.7
C13—C14—H14A109.5C33—C34—H34A109.5
C13—C14—H14B109.5C33—C34—H34B109.5
H14A—C14—H14B109.5H34A—C34—H34B109.5
C13—C14—H14C109.5C33—C34—H34C109.5
H14A—C14—H14C109.5H34A—C34—H34C109.5
H14B—C14—H14C109.5H34B—C34—H34C109.5
C13—C15—H15A109.5C33—C35—H35A109.5
C13—C15—H15B109.5C33—C35—H35B109.5
H15A—C15—H15B109.5H35A—C35—H35B109.5
C13—C15—H15C109.5C33—C35—H35C109.5
H15A—C15—H15C109.5H35A—C35—H35C109.5
H15B—C15—H15C109.5H35B—C35—H35C109.5
O1—C1—C1A—O21.9 (2)O30—P21—O28—C3050.10 (12)
C5—C1—C1A—O2177.30 (13)O29—P21—O28—C3078.84 (11)
O1—C1—C1A—C3A178.82 (12)C29—P21—O28—C30171.92 (10)
C5—C1—C1A—C3A0.3 (2)O30—P21—O29—C3310.58 (12)
C1A—C1—O1—C1B174.64 (12)O28—P21—O29—C33141.42 (10)
C5—C1—O1—C1B4.4 (2)C29—P21—O29—C33115.35 (10)
C3A—C1A—O2—C22.20 (15)C21B—O21—C21—C21A176.98 (13)
C1—C1A—O2—C2179.44 (14)C21B—O21—C21—C254.8 (2)
O3—C2—O2—C1A3.39 (15)C22—O22—C21A—C23A9.79 (15)
C4—C3—C3A—O3177.47 (13)C22—O22—C21A—C21171.22 (14)
C4—C3—C3A—C1A1.2 (2)O21—C21—C21A—O222.0 (2)
O2—C1A—C3A—O30.12 (16)C25—C21—C21A—O22179.61 (13)
C1—C1A—C3A—O3177.56 (12)O21—C21—C21A—C23A179.14 (12)
O2—C1A—C3A—C3176.68 (12)C25—C21—C21A—C23A0.7 (2)
C1—C1A—C3A—C30.8 (2)C23A—O23—C22—O2217.55 (15)
C3—C3A—O3—C2178.64 (14)C21A—O22—C22—O2316.83 (15)
C1A—C3A—O3—C22.02 (15)C22—O23—C23A—C23168.34 (14)
O2—C2—O3—C3A3.34 (15)C22—O23—C23A—C21A11.66 (15)
C3A—C3—C4—C50.70 (19)C24—C23—C23A—O23177.88 (13)
C3A—C3—C4—C6178.68 (12)C24—C23—C23A—C21A2.1 (2)
O1—C1—C5—C4178.22 (12)O22—C21A—C23A—O231.14 (16)
C1A—C1—C5—C40.85 (19)C21—C21A—C23A—O23177.92 (12)
C3—C4—C5—C10.33 (19)O22—C21A—C23A—C23178.86 (12)
C6—C4—C5—C1177.56 (12)C21—C21A—C23A—C232.1 (2)
C3—C4—C6—C7175.05 (13)C23A—C23—C24—C250.96 (19)
C5—C4—C6—C77.0 (2)C23A—C23—C24—C26178.91 (12)
C4—C6—C7—S1176.81 (10)O21—C21—C25—C24177.84 (13)
O4—S1—C7—C614.21 (13)C21A—C21—C25—C240.41 (19)
O5—S1—C7—C6146.25 (11)C23—C24—C25—C210.3 (2)
C8—S1—C7—C698.02 (12)C26—C24—C25—C21177.58 (12)
O7—S2—C8—S1161.90 (8)C25—C24—C26—C2712.2 (2)
O6—S2—C8—S132.44 (10)C23—C24—C26—C27169.83 (13)
C9—S2—C8—S182.85 (9)C24—C26—C27—S21177.14 (10)
O4—S1—C8—S2174.59 (7)O24—S21—C27—C2613.10 (13)
O5—S1—C8—S247.64 (9)O25—S21—C27—C26145.35 (11)
C7—S1—C8—S269.30 (9)C28—S21—C27—C2699.01 (12)
O10—P1—O8—C1048.97 (12)O27—S22—C28—S21162.34 (7)
O9—P1—O8—C1080.09 (11)O26—S22—C28—S2132.96 (10)
C9—P1—O8—C10170.79 (10)C29—S22—C28—S2182.28 (9)
O7—S2—C9—P148.66 (9)O24—S21—C28—S22172.71 (7)
O6—S2—C9—P1178.91 (7)O25—S21—C28—S2245.87 (9)
C8—S2—C9—P164.49 (9)C27—S21—C28—S2271.14 (9)
O10—P1—C9—S249.50 (10)O27—S22—C29—P2149.17 (9)
O8—P1—C9—S2174.50 (7)O26—S22—C29—P21179.34 (7)
O9—P1—C9—S277.33 (8)C28—S22—C29—P2164.17 (9)
O10—P1—O9—C1310.69 (12)O30—P21—C29—S2249.00 (10)
O8—P1—O9—C13141.53 (10)O28—P21—C29—S22174.00 (8)
C9—P1—O9—C13115.31 (10)O29—P21—C29—S2277.62 (8)
P1—O8—C10—C12139.11 (17)P21—O28—C30—C32139.65 (15)
P1—O8—C10—C1197.83 (16)P21—O28—C30—C3197.84 (15)
P1—O9—C13—C14138.74 (10)P21—O29—C33—C35100.52 (13)
P1—O9—C13—C1599.73 (13)P21—O29—C33—C34137.61 (10)
(III) bis(trans-2-phenylethenyl) sulfone top
Crystal data top
C16H14O2SF(000) = 3408
Mr = 270.33Dx = 1.304 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5361 reflections
a = 10.1632 (7) Åθ = 2.3–25.5°
b = 23.6753 (16) ŵ = 0.23 mm1
c = 34.339 (2) ÅT = 90 K
V = 8262.5 (9) Å3Rod, colorless
Z = 240.51 × 0.09 × 0.06 mm
Data collection top
Bruker SMART 1000
diffractometer
9492 independent reflections
Radiation source: fine-focus sealed tube5497 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.085
Detector resolution: 8.3 pixels mm-1θmax = 27.5°, θmin = 1.7°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
k = 2730
Tmin = 0.892, Tmax = 0.987l = 4444
60803 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0624P)2]
where P = (Fo2 + 2Fc2)/3
9492 reflections(Δ/σ)max < 0.001
562 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 1.02 e Å3
Crystal data top
C16H14O2SV = 8262.5 (9) Å3
Mr = 270.33Z = 24
Orthorhombic, PbcaMo Kα radiation
a = 10.1632 (7) ŵ = 0.23 mm1
b = 23.6753 (16) ÅT = 90 K
c = 34.339 (2) Å0.51 × 0.09 × 0.06 mm
Data collection top
Bruker SMART 1000
diffractometer
9492 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
5497 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.987Rint = 0.085
60803 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.09Δρmax = 0.61 e Å3
9492 reflectionsΔρmin = 1.02 e Å3
562 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.73682 (6)0.00321 (3)0.232714 (17)0.02295 (15)
C10.4491 (2)0.16964 (11)0.27948 (7)0.0265 (6)
H10.49550.16550.30330.032*
O10.76152 (17)0.00309 (7)0.27387 (5)0.0286 (4)
C20.3564 (2)0.21182 (11)0.27595 (7)0.0274 (6)
H20.34070.23690.29700.033*
O20.84810 (16)0.00625 (7)0.20674 (5)0.0291 (4)
C30.2858 (3)0.21764 (11)0.24148 (7)0.0297 (6)
H30.22140.24650.23890.036*
C40.3107 (2)0.18070 (11)0.21066 (7)0.0282 (6)
H40.26250.18430.18710.034*
C50.4044 (2)0.13909 (10)0.21418 (7)0.0246 (6)
H50.42040.11430.19290.029*
C60.4765 (2)0.13276 (10)0.24868 (6)0.0213 (5)
C70.5756 (2)0.08836 (10)0.25336 (6)0.0230 (5)
H70.60050.07870.27920.028*
C80.6335 (2)0.06054 (10)0.22464 (7)0.0230 (5)
H80.61800.07240.19860.028*
C90.6357 (2)0.05240 (10)0.21741 (6)0.0219 (5)
H90.55490.05880.23060.026*
C100.6681 (2)0.08582 (10)0.18800 (7)0.0230 (5)
H100.75070.07880.17590.028*
C110.5896 (2)0.13257 (10)0.17211 (6)0.0210 (5)
C120.4599 (2)0.14266 (10)0.18350 (6)0.0231 (5)
H120.41940.11890.20230.028*
C130.3896 (3)0.18732 (10)0.16748 (7)0.0276 (6)
H130.30180.19440.17560.033*
C140.4474 (3)0.22156 (10)0.13964 (7)0.0313 (6)
H140.39900.25200.12870.038*
C150.5750 (3)0.21166 (11)0.12773 (7)0.0310 (6)
H150.61390.23500.10840.037*
C160.6464 (3)0.16771 (10)0.14400 (7)0.0280 (6)
H160.73460.16140.13600.034*
S210.63705 (6)0.13450 (2)0.111526 (15)0.01896 (14)
C211.0923 (2)0.05528 (10)0.14105 (6)0.0240 (6)
H211.04440.03230.15870.029*
O210.57348 (16)0.13957 (7)0.07412 (4)0.0216 (4)
C221.2262 (2)0.04665 (11)0.13596 (7)0.0264 (6)
H221.27000.01790.15020.032*
O220.60780 (16)0.08544 (7)0.13483 (4)0.0226 (4)
C231.2962 (2)0.08001 (11)0.11002 (7)0.0270 (6)
H231.38730.07330.10600.032*
C241.2333 (2)0.12320 (11)0.08992 (7)0.0272 (6)
H241.28190.14670.07270.033*
C251.1003 (2)0.13195 (10)0.09502 (7)0.0233 (5)
H251.05770.16150.08120.028*
C261.0275 (2)0.09796 (10)0.12016 (6)0.0205 (5)
C270.8854 (2)0.10328 (10)0.12458 (6)0.0207 (5)
H270.84520.08030.14390.025*
C280.8063 (2)0.13697 (10)0.10438 (6)0.0192 (5)
H280.84240.16250.08590.023*
C290.6010 (2)0.19422 (10)0.13919 (6)0.0211 (5)
H290.63010.19620.16550.025*
C300.5334 (2)0.23709 (10)0.12411 (6)0.0204 (5)
H300.50720.23380.09770.024*
C310.4955 (2)0.28898 (10)0.14453 (6)0.0212 (5)
C320.4441 (2)0.33379 (10)0.12321 (7)0.0241 (6)
H320.43200.32980.09590.029*
C330.4102 (3)0.38435 (11)0.14113 (7)0.0294 (6)
H330.37630.41470.12610.035*
C340.4259 (3)0.39030 (11)0.18078 (7)0.0327 (6)
H340.40290.42480.19310.039*
C350.4754 (3)0.34574 (11)0.20264 (7)0.0313 (6)
H350.48570.34990.23000.038*
C360.5100 (2)0.29535 (11)0.18501 (7)0.0252 (6)
H360.54340.26510.20020.030*
S410.78425 (8)0.24464 (3)0.00204 (2)0.0411 (2)
C410.5670 (3)0.08760 (14)0.08228 (8)0.0438 (8)
H410.61990.10210.10280.053*
O410.8547 (2)0.25138 (8)0.03837 (5)0.0456 (6)
C420.4912 (3)0.03983 (14)0.08854 (8)0.0488 (9)
H420.49250.02170.11320.059*
O420.8609 (2)0.23348 (8)0.03280 (5)0.0429 (5)
C430.4144 (3)0.01861 (14)0.05919 (9)0.0497 (8)
H430.36310.01440.06340.060*
C440.4120 (3)0.04571 (15)0.02327 (8)0.0491 (8)
H440.35750.03140.00310.059*
C450.4874 (3)0.09283 (14)0.01668 (8)0.0412 (8)
H450.48570.11060.00810.049*
C460.5664 (3)0.11460 (13)0.04612 (7)0.0370 (7)
C470.6524 (3)0.16347 (13)0.03997 (7)0.0397 (8)
H470.70120.17630.06180.048*
C480.6689 (3)0.19161 (13)0.00679 (7)0.0373 (7)
H480.61550.18220.01500.045*
C490.6698 (6)0.29921 (19)0.00007 (13)0.0197 (9)0.57
H490.60460.30330.01950.024*0.57
C500.6761 (6)0.3361 (2)0.03064 (13)0.0227 (11)0.57
H500.74170.32880.04970.027*0.57
C510.5944 (5)0.3845 (2)0.03700 (13)0.0266 (15)0.57
C520.4818 (5)0.3946 (3)0.01514 (16)0.0306 (19)0.57
H520.45650.36890.00470.037*0.57
C530.4061 (7)0.4424 (3)0.0224 (2)0.0354 (18)0.57
H530.32910.44930.00740.043*0.57
C540.4430 (9)0.4800 (3)0.0515 (3)0.040 (2)0.57
H540.39130.51260.05640.048*0.57
C550.5557 (9)0.4698 (3)0.0733 (2)0.042 (2)0.57
H550.58100.49560.09320.050*0.57
C560.6314 (6)0.4221 (3)0.06609 (15)0.0358 (16)0.57
H560.70840.41510.08100.043*0.57
C49B0.7286 (8)0.3135 (4)0.0187 (3)0.0390 (18)0.43
H49B0.78380.33610.03470.047*0.43
C50B0.6152 (7)0.3278 (4)0.0102 (2)0.0335 (16)0.43
H50B0.56450.30260.00510.040*0.43
C51B0.5513 (7)0.3827 (3)0.02257 (19)0.028 (2)0.43
C52B0.4340 (8)0.3963 (4)0.0040 (2)0.030 (2)0.43
H52B0.39990.37210.01570.037*0.43
C53B0.3665 (9)0.4452 (5)0.0141 (3)0.036 (2)0.43
H53B0.28640.45440.00140.043*0.43
C54B0.4164 (12)0.4805 (5)0.0429 (4)0.046 (3)0.43
H54B0.37020.51390.04980.055*0.43
C55B0.5337 (12)0.4670 (4)0.0615 (3)0.047 (3)0.43
H55B0.56770.49110.08110.056*0.43
C56B0.6011 (8)0.4181 (4)0.0513 (2)0.042 (3)0.43
H56B0.68130.40880.06400.051*0.43
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0245 (3)0.0217 (3)0.0226 (3)0.0035 (3)0.0005 (3)0.0001 (2)
C10.0271 (14)0.0299 (15)0.0226 (12)0.0053 (12)0.0026 (11)0.0007 (11)
O10.0347 (10)0.0255 (9)0.0255 (9)0.0022 (9)0.0075 (8)0.0022 (7)
C20.0261 (15)0.0280 (14)0.0282 (13)0.0022 (12)0.0066 (11)0.0033 (11)
O20.0253 (10)0.0296 (10)0.0323 (9)0.0033 (8)0.0047 (8)0.0011 (8)
C30.0267 (15)0.0294 (15)0.0331 (14)0.0013 (12)0.0057 (11)0.0058 (11)
C40.0253 (14)0.0333 (16)0.0260 (13)0.0021 (12)0.0003 (11)0.0053 (11)
C50.0255 (14)0.0267 (14)0.0215 (12)0.0056 (11)0.0045 (10)0.0000 (10)
C60.0191 (13)0.0237 (13)0.0210 (11)0.0071 (11)0.0032 (10)0.0020 (10)
C70.0264 (14)0.0232 (13)0.0194 (11)0.0068 (11)0.0042 (10)0.0009 (10)
C80.0258 (14)0.0207 (13)0.0224 (12)0.0044 (11)0.0012 (10)0.0023 (10)
C90.0231 (13)0.0225 (13)0.0200 (11)0.0042 (11)0.0001 (10)0.0035 (10)
C100.0193 (13)0.0247 (14)0.0251 (12)0.0027 (11)0.0028 (10)0.0029 (10)
C110.0232 (13)0.0202 (13)0.0196 (11)0.0003 (11)0.0023 (10)0.0012 (10)
C120.0284 (14)0.0204 (14)0.0205 (11)0.0044 (11)0.0021 (10)0.0012 (10)
C130.0291 (15)0.0283 (15)0.0255 (13)0.0027 (12)0.0051 (11)0.0045 (11)
C140.0460 (18)0.0182 (14)0.0298 (14)0.0027 (13)0.0115 (13)0.0015 (11)
C150.0419 (18)0.0239 (14)0.0272 (13)0.0068 (13)0.0021 (12)0.0044 (11)
C160.0281 (15)0.0276 (14)0.0283 (13)0.0060 (12)0.0034 (11)0.0014 (11)
S210.0182 (3)0.0226 (3)0.0160 (3)0.0011 (3)0.0002 (2)0.0011 (2)
C210.0229 (14)0.0293 (15)0.0197 (12)0.0004 (11)0.0013 (10)0.0015 (10)
O210.0213 (9)0.0277 (10)0.0158 (8)0.0016 (8)0.0025 (7)0.0005 (7)
C220.0243 (14)0.0298 (14)0.0250 (12)0.0026 (12)0.0040 (11)0.0025 (11)
O220.0205 (9)0.0269 (9)0.0205 (8)0.0045 (8)0.0007 (7)0.0025 (7)
C230.0178 (13)0.0329 (15)0.0303 (13)0.0001 (12)0.0035 (11)0.0015 (11)
C240.0235 (14)0.0289 (15)0.0291 (13)0.0092 (12)0.0023 (11)0.0014 (11)
C250.0213 (13)0.0199 (13)0.0287 (13)0.0006 (11)0.0019 (10)0.0000 (10)
C260.0196 (13)0.0226 (13)0.0194 (11)0.0013 (11)0.0014 (9)0.0057 (10)
C270.0216 (13)0.0208 (13)0.0196 (11)0.0016 (11)0.0024 (10)0.0047 (10)
C280.0182 (12)0.0183 (12)0.0210 (11)0.0019 (10)0.0035 (9)0.0033 (9)
C290.0172 (13)0.0292 (14)0.0169 (11)0.0022 (11)0.0016 (9)0.0031 (10)
C300.0176 (13)0.0264 (14)0.0172 (11)0.0045 (11)0.0026 (9)0.0009 (10)
C310.0158 (12)0.0254 (14)0.0225 (12)0.0038 (11)0.0006 (10)0.0043 (10)
C320.0232 (14)0.0290 (15)0.0201 (11)0.0015 (11)0.0024 (10)0.0002 (10)
C330.0325 (16)0.0225 (14)0.0332 (14)0.0021 (12)0.0028 (12)0.0007 (11)
C340.0376 (17)0.0246 (15)0.0358 (14)0.0002 (13)0.0021 (12)0.0071 (12)
C350.0376 (17)0.0330 (16)0.0232 (13)0.0011 (13)0.0025 (11)0.0059 (11)
C360.0227 (14)0.0280 (14)0.0250 (12)0.0035 (11)0.0018 (10)0.0022 (11)
S410.0542 (5)0.0268 (4)0.0424 (4)0.0074 (4)0.0280 (4)0.0097 (3)
C410.0473 (19)0.057 (2)0.0267 (14)0.0289 (17)0.0037 (13)0.0058 (14)
O410.0526 (14)0.0413 (12)0.0430 (11)0.0134 (11)0.0285 (10)0.0159 (9)
C420.061 (2)0.051 (2)0.0337 (16)0.0333 (19)0.0093 (15)0.0028 (15)
O420.0601 (14)0.0372 (11)0.0313 (10)0.0231 (11)0.0145 (10)0.0076 (9)
C430.046 (2)0.061 (2)0.0419 (18)0.0135 (17)0.0097 (15)0.0085 (16)
C440.0297 (17)0.082 (3)0.0359 (16)0.0033 (18)0.0045 (13)0.0060 (16)
C450.0244 (16)0.077 (2)0.0223 (13)0.0019 (16)0.0021 (11)0.0044 (14)
C460.0273 (16)0.058 (2)0.0251 (13)0.0135 (15)0.0022 (11)0.0068 (13)
C470.0360 (17)0.059 (2)0.0238 (13)0.0195 (16)0.0100 (12)0.0167 (13)
C480.0250 (15)0.059 (2)0.0282 (14)0.0076 (14)0.0105 (12)0.0161 (13)
C490.024 (3)0.019 (2)0.017 (2)0.008 (2)0.003 (2)0.0059 (19)
C500.030 (3)0.021 (3)0.017 (2)0.010 (2)0.010 (2)0.009 (2)
C510.031 (4)0.017 (3)0.032 (4)0.014 (3)0.008 (3)0.000 (3)
C520.033 (6)0.024 (3)0.035 (4)0.012 (3)0.008 (4)0.005 (3)
C530.028 (5)0.040 (4)0.038 (4)0.001 (3)0.010 (3)0.001 (3)
C540.053 (6)0.012 (4)0.055 (5)0.002 (4)0.023 (5)0.006 (3)
C550.051 (5)0.028 (4)0.046 (5)0.009 (3)0.016 (3)0.010 (3)
C560.034 (4)0.032 (3)0.041 (4)0.007 (3)0.014 (3)0.006 (3)
C49B0.051 (6)0.034 (5)0.032 (4)0.017 (4)0.010 (4)0.001 (3)
C50B0.031 (4)0.043 (5)0.027 (4)0.015 (4)0.002 (3)0.001 (3)
C51B0.028 (6)0.031 (5)0.025 (5)0.007 (4)0.008 (4)0.002 (4)
C52B0.034 (6)0.027 (4)0.031 (5)0.006 (4)0.009 (4)0.006 (4)
C53B0.019 (5)0.031 (5)0.059 (7)0.001 (4)0.008 (4)0.011 (4)
C54B0.045 (6)0.036 (7)0.057 (7)0.010 (5)0.031 (5)0.000 (6)
C55B0.069 (8)0.038 (6)0.034 (6)0.025 (6)0.014 (6)0.009 (4)
C56B0.038 (5)0.038 (6)0.051 (7)0.016 (5)0.008 (5)0.021 (6)
Geometric parameters (Å, º) top
S1—O21.4422 (17)C32—C331.389 (3)
S1—O11.4432 (16)C32—H320.9500
S1—C81.738 (2)C33—C341.378 (3)
S1—C91.751 (2)C33—H330.9500
C1—C21.379 (3)C34—C351.389 (4)
C1—C61.399 (3)C34—H340.9500
C1—H10.9500C35—C361.383 (3)
C2—C31.391 (3)C35—H350.9500
C2—H20.9500C36—H360.9500
C3—C41.396 (3)S41—O411.4473 (18)
C3—H30.9500S41—O421.452 (2)
C4—C51.375 (3)S41—C481.725 (3)
C4—H40.9500S41—C491.740 (6)
C5—C61.401 (3)S41—C49B1.868 (10)
C5—H50.9500C41—C421.385 (4)
C6—C71.465 (3)C41—C461.397 (4)
C7—C81.324 (3)C41—H410.9500
C7—H70.9500C42—C431.370 (4)
C8—H80.9500C42—H420.9500
C9—C101.325 (3)C43—C441.390 (4)
C9—H90.9500C43—H430.9500
C10—C111.469 (3)C44—C451.372 (4)
C10—H100.9500C44—H440.9500
C11—C121.396 (3)C45—C461.390 (4)
C11—C161.399 (3)C45—H450.9500
C12—C131.390 (3)C46—C471.465 (4)
C12—H120.9500C47—C481.330 (4)
C13—C141.384 (3)C47—H470.9500
C13—H130.9500C48—H480.9500
C14—C151.380 (4)C49—C501.367 (6)
C14—H140.9500C49—H490.9500
C15—C161.386 (3)C50—C511.431 (8)
C15—H150.9500C50—H500.9500
C16—H160.9500C51—C521.3900
S21—O221.4415 (16)C51—C561.3900
S21—O211.4428 (15)C52—C531.3900
S21—C281.739 (2)C52—H520.9500
S21—C291.742 (2)C53—C541.3900
C21—C221.387 (3)C53—H530.9500
C21—C261.404 (3)C54—C551.3900
C21—H210.9500C54—H540.9500
C22—C231.387 (3)C55—C561.3900
C22—H220.9500C55—H550.9500
C23—C241.389 (3)C56—H560.9500
C23—H230.9500C49B—C50B1.236 (11)
C24—C251.379 (3)C49B—H49B0.9500
C24—H240.9500C50B—C51B1.513 (12)
C25—C261.393 (3)C50B—H50B0.9500
C25—H250.9500C51B—C52B1.3900
C26—C271.457 (3)C51B—C56B1.3900
C27—C281.328 (3)C52B—C53B1.3900
C27—H270.9500C52B—H52B0.9500
C28—H280.9500C53B—C54B1.3900
C29—C301.331 (3)C53B—H53B0.9500
C29—H290.9500C54B—C55B1.3900
C30—C311.466 (3)C54B—H54B0.9500
C30—H300.9500C55B—C56B1.3900
C31—C321.391 (3)C55B—H55B0.9500
C31—C361.406 (3)C56B—H56B0.9500
O2—S1—O1118.33 (11)C31—C32—H32119.4
O2—S1—C8109.63 (11)C34—C33—C32119.8 (2)
O1—S1—C8109.99 (11)C34—C33—H33120.1
O2—S1—C9108.20 (11)C32—C33—H33120.1
O1—S1—C9108.57 (10)C33—C34—C35119.9 (2)
C8—S1—C9100.64 (11)C33—C34—H34120.1
C2—C1—C6121.4 (2)C35—C34—H34120.1
C2—C1—H1119.3C36—C35—C34120.7 (2)
C6—C1—H1119.3C36—C35—H35119.6
C1—C2—C3119.9 (2)C34—C35—H35119.6
C1—C2—H2120.0C35—C36—C31119.9 (2)
C3—C2—H2120.0C35—C36—H36120.0
C2—C3—C4119.3 (2)C31—C36—H36120.0
C2—C3—H3120.3O41—S41—O42117.69 (13)
C4—C3—H3120.3O41—S41—C48109.58 (13)
C5—C4—C3120.5 (2)O42—S41—C48108.06 (12)
C5—C4—H4119.7O41—S41—C49106.55 (16)
C3—C4—H4119.7O42—S41—C49117.35 (18)
C4—C5—C6120.9 (2)C48—S41—C4995.17 (19)
C4—C5—H5119.6O41—S41—C49B112.5 (2)
C6—C5—H5119.6O42—S41—C49B90.4 (3)
C1—C6—C5117.9 (2)C48—S41—C49B117.8 (3)
C1—C6—C7120.1 (2)C42—C41—C46120.6 (3)
C5—C6—C7122.0 (2)C42—C41—H41119.7
C8—C7—C6125.5 (2)C46—C41—H41119.7
C8—C7—H7117.2C43—C42—C41120.1 (3)
C6—C7—H7117.2C43—C42—H42119.9
C7—C8—S1122.54 (19)C41—C42—H42119.9
C7—C8—H8118.7C42—C43—C44119.6 (3)
S1—C8—H8118.7C42—C43—H43120.2
C10—C9—S1122.1 (2)C44—C43—H43120.2
C10—C9—H9118.9C45—C44—C43120.8 (3)
S1—C9—H9118.9C45—C44—H44119.6
C9—C10—C11126.7 (2)C43—C44—H44119.6
C9—C10—H10116.6C44—C45—C46120.3 (3)
C11—C10—H10116.6C44—C45—H45119.9
C12—C11—C16118.7 (2)C46—C45—H45119.9
C12—C11—C10122.5 (2)C45—C46—C41118.6 (3)
C16—C11—C10118.7 (2)C45—C46—C47122.2 (3)
C13—C12—C11120.3 (2)C41—C46—C47119.1 (3)
C13—C12—H12119.8C48—C47—C46126.4 (3)
C11—C12—H12119.8C48—C47—H47116.8
C14—C13—C12120.1 (2)C46—C47—H47116.8
C14—C13—H13120.0C47—C48—S41122.1 (2)
C12—C13—H13120.0C47—C48—H48119.0
C15—C14—C13120.3 (2)S41—C48—H48119.0
C15—C14—H14119.9C50—C49—S41118.4 (5)
C13—C14—H14119.9C50—C49—H49120.8
C14—C15—C16120.0 (2)S41—C49—H49120.8
C14—C15—H15120.0C49—C50—C51127.0 (6)
C16—C15—H15120.0C49—C50—H50116.5
C15—C16—C11120.6 (2)C51—C50—H50116.5
C15—C16—H16119.7C52—C51—C56120.0
C11—C16—H16119.7C52—C51—C50122.3 (4)
O22—S21—O21117.96 (10)C56—C51—C50117.7 (4)
O22—S21—C28108.03 (10)C51—C52—C53120.0
O21—S21—C28108.34 (10)C51—C52—H52120.0
O22—S21—C29107.93 (10)C53—C52—H52120.0
O21—S21—C29108.89 (10)C54—C53—C52120.0
C28—S21—C29104.94 (11)C54—C53—H53120.0
C22—C21—C26120.2 (2)C52—C53—H53120.0
C22—C21—H21119.9C55—C54—C53120.0
C26—C21—H21119.9C55—C54—H54120.0
C21—C22—C23120.0 (2)C53—C54—H54120.0
C21—C22—H22120.0C54—C55—C56120.0
C23—C22—H22120.0C54—C55—H55120.0
C22—C23—C24120.2 (2)C56—C55—H55120.0
C22—C23—H23119.9C55—C56—C51120.0
C24—C23—H23119.9C55—C56—H56120.0
C25—C24—C23119.9 (2)C51—C56—H56120.0
C25—C24—H24120.1C50B—C49B—S41115.6 (10)
C23—C24—H24120.1C50B—C49B—H49B122.2
C24—C25—C26120.9 (2)S41—C49B—H49B122.2
C24—C25—H25119.6C49B—C50B—C51B124.7 (10)
C26—C25—H25119.6C49B—C50B—H50B117.6
C25—C26—C21118.9 (2)C51B—C50B—H50B117.6
C25—C26—C27122.8 (2)C52B—C51B—C56B120.0
C21—C26—C27118.3 (2)C52B—C51B—C50B115.9 (6)
C28—C27—C26126.6 (2)C56B—C51B—C50B124.0 (6)
C28—C27—H27116.7C53B—C52B—C51B120.0
C26—C27—H27116.7C53B—C52B—H52B120.0
C27—C28—S21120.31 (19)C51B—C52B—H52B120.0
C27—C28—H28119.8C54B—C53B—C52B120.0
S21—C28—H28119.8C54B—C53B—H53B120.0
C30—C29—S21121.02 (18)C52B—C53B—H53B120.0
C30—C29—H29119.5C53B—C54B—C55B120.0
S21—C29—H29119.5C53B—C54B—H54B120.0
C29—C30—C31126.1 (2)C55B—C54B—H54B120.0
C29—C30—H30117.0C54B—C55B—C56B120.0
C31—C30—H30117.0C54B—C55B—H55B120.0
C32—C31—C36118.5 (2)C56B—C55B—H55B120.0
C32—C31—C30119.1 (2)C55B—C56B—C51B120.0
C36—C31—C30122.4 (2)C55B—C56B—H56B120.0
C33—C32—C31121.2 (2)C51B—C56B—H56B120.0
C33—C32—H32119.4
(IV) bis(trans-2-phenylethenylsulfonyl)methane top
Crystal data top
C17H16O4S2F(000) = 728
Mr = 348.42Dx = 1.466 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6102 reflections
a = 15.7551 (6) Åθ = 2.7–30.0°
b = 11.9609 (5) ŵ = 0.36 mm1
c = 8.6212 (3) ÅT = 90 K
β = 103.728 (1)°Block, colorless
V = 1578.21 (10) Å30.29 × 0.24 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 1000
diffractometer
2302 independent reflections
Radiation source: fine-focus sealed tube1978 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.3 pixels mm-1θmax = 30.0°, θmin = 2.2°
ω scansh = 2222
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
k = 1616
Tmin = 0.865, Tmax = 0.928l = 1212
8747 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093All H-atom parameters refined
S = 1.11 w = 1/[σ2(Fo2) + (0.0512P)2 + 1.1605P]
where P = (Fo2 + 2Fc2)/3
2302 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C17H16O4S2V = 1578.21 (10) Å3
Mr = 348.42Z = 4
Monoclinic, C2/cMo Kα radiation
a = 15.7551 (6) ŵ = 0.36 mm1
b = 11.9609 (5) ÅT = 90 K
c = 8.6212 (3) Å0.29 × 0.24 × 0.20 mm
β = 103.728 (1)°
Data collection top
Bruker SMART 1000
diffractometer
2302 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2006)
1978 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.928Rint = 0.023
8747 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.093All H-atom parameters refined
S = 1.11Δρmax = 0.42 e Å3
2302 reflectionsΔρmin = 0.31 e Å3
137 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.452903 (18)0.34291 (2)0.07337 (3)0.01471 (10)
O10.40271 (6)0.42586 (8)0.03276 (11)0.0194 (2)
O20.40895 (6)0.24615 (7)0.11488 (11)0.0187 (2)
C10.61794 (9)0.03714 (11)0.14792 (16)0.0200 (3)
H10.5772 (14)0.0113 (17)0.110 (2)0.037 (5)*
C20.67641 (10)0.00807 (11)0.22831 (17)0.0236 (3)
H20.6762 (13)0.0843 (17)0.245 (2)0.031 (5)*
C30.73257 (9)0.06147 (12)0.28548 (16)0.0221 (3)
H30.7717 (12)0.0315 (15)0.343 (2)0.027 (5)*
C40.73069 (9)0.17639 (12)0.26197 (17)0.0220 (3)
H40.7694 (12)0.2253 (16)0.301 (2)0.027 (5)*
C50.67275 (9)0.22206 (11)0.18012 (16)0.0197 (2)
H50.6694 (12)0.3043 (16)0.171 (2)0.027 (5)*
C60.61538 (8)0.15290 (10)0.12260 (14)0.0154 (2)
H60.5133 (13)0.1410 (16)0.008 (2)0.029 (5)*
C70.55115 (8)0.19662 (10)0.04009 (15)0.0165 (2)
H70.5725 (12)0.3661 (15)0.021 (2)0.027 (4)*
C80.54096 (8)0.30349 (10)0.00421 (15)0.0167 (2)
C90.50000.42087 (14)0.25000.0159 (3)
H90.5468 (12)0.4693 (15)0.229 (2)0.028 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01503 (16)0.01466 (15)0.01597 (16)0.00020 (9)0.00677 (11)0.00018 (9)
O10.0184 (4)0.0198 (4)0.0204 (4)0.0024 (3)0.0053 (3)0.0023 (3)
O20.0188 (4)0.0170 (4)0.0228 (4)0.0037 (3)0.0100 (3)0.0004 (3)
C10.0240 (6)0.0163 (5)0.0223 (6)0.0003 (4)0.0103 (5)0.0010 (4)
C20.0288 (7)0.0172 (6)0.0270 (7)0.0042 (5)0.0112 (5)0.0014 (5)
C30.0198 (6)0.0249 (6)0.0232 (6)0.0043 (5)0.0085 (5)0.0022 (5)
C40.0184 (6)0.0246 (6)0.0260 (6)0.0024 (5)0.0111 (5)0.0019 (5)
C50.0205 (6)0.0174 (5)0.0235 (6)0.0014 (5)0.0096 (5)0.0010 (5)
C60.0160 (5)0.0161 (5)0.0152 (5)0.0005 (4)0.0055 (4)0.0002 (4)
C70.0169 (5)0.0172 (5)0.0169 (5)0.0005 (4)0.0070 (4)0.0000 (4)
C80.0169 (5)0.0177 (5)0.0175 (5)0.0003 (4)0.0083 (4)0.0001 (4)
C90.0189 (8)0.0144 (7)0.0158 (7)0.0000.0069 (6)0.000
Geometric parameters (Å, º) top
S1—O21.4369 (9)C4—C51.3911 (18)
S1—O11.4502 (9)C4—H40.961 (19)
S1—C81.7422 (12)C5—C61.3999 (17)
S1—C91.7896 (9)C5—H50.989 (19)
C1—C21.3872 (18)C6—C71.4646 (16)
C1—C61.4038 (16)C7—C81.3337 (17)
C1—H10.98 (2)C7—H60.976 (19)
C2—C31.387 (2)C8—H70.928 (19)
C2—H20.92 (2)C9—S1i1.7896 (9)
C3—C41.3907 (19)C9—H90.987 (18)
C3—H30.951 (19)
O2—S1—O1119.03 (6)C5—C4—H4119.0 (11)
O2—S1—C8110.63 (6)C4—C5—C6120.28 (12)
O1—S1—C8107.92 (6)C4—C5—H5119.1 (11)
O2—S1—C9109.56 (5)C6—C5—H5120.5 (11)
O1—S1—C9103.55 (6)C5—C6—C1118.88 (12)
C8—S1—C9105.10 (4)C5—C6—C7122.66 (11)
C2—C1—C6120.61 (12)C1—C6—C7118.45 (11)
C2—C1—H1120.3 (12)C8—C7—C6126.15 (11)
C6—C1—H1119.1 (12)C8—C7—H6118.2 (11)
C1—C2—C3119.93 (12)C6—C7—H6115.7 (11)
C1—C2—H2118.9 (12)C7—C8—S1119.94 (10)
C3—C2—H2121.1 (12)C7—C8—H7129.7 (12)
C2—C3—C4120.22 (12)S1—C8—H7110.2 (12)
C2—C3—H3120.5 (11)S1—C9—S1i117.20 (9)
C4—C3—H3119.3 (11)S1—C9—H9109.1 (10)
C3—C4—C5120.08 (12)S1i—C9—H9106.5 (11)
C3—C4—H4120.9 (11)
C6—C1—C2—C30.5 (2)C1—C6—C7—C8178.81 (13)
C1—C2—C3—C40.2 (2)C6—C7—C8—S1172.46 (10)
C2—C3—C4—C50.4 (2)O2—S1—C8—C710.11 (13)
C3—C4—C5—C60.7 (2)O1—S1—C8—C7121.71 (11)
C4—C5—C6—C10.5 (2)C9—S1—C8—C7128.28 (11)
C4—C5—C6—C7178.03 (12)O2—S1—C9—S1i38.32 (4)
C2—C1—C6—C50.1 (2)O1—S1—C9—S1i166.30 (4)
C2—C1—C6—C7178.70 (12)C8—S1—C9—S1i80.58 (5)
C5—C6—C7—C82.7 (2)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC15H23O5PSC18H27O10PS2C16H14O2SC17H16O4S2
Mr346.36498.49270.33348.42
Crystal system, space groupTriclinic, P1Triclinic, P1Orthorhombic, PbcaMonoclinic, C2/c
Temperature (K)90909090
a, b, c (Å)8.933 (3), 10.014 (3), 22.059 (7)9.8656 (3), 15.1481 (5), 15.9024 (5)10.1632 (7), 23.6753 (16), 34.339 (2)15.7551 (6), 11.9609 (5), 8.6212 (3)
α, β, γ (°)79.769 (4), 89.938 (4), 63.533 (4)86.929 (3), 89.893 (3), 72.267 (3)90, 90, 9090, 103.728 (1), 90
V3)1731.5 (10)2260.11 (12)8262.5 (9)1578.21 (10)
Z44244
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.300.360.230.36
Crystal size (mm)0.55 × 0.53 × 0.380.49 × 0.08 × 0.070.51 × 0.09 × 0.060.29 × 0.24 × 0.20
Data collection
DiffractometerBruker SMART 1000
diffractometer
Bruker SMART ApexII
diffractometer
Bruker SMART 1000
diffractometer
Bruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2006)
Multi-scan
(SADABS; Sheldrick, 2006)
Multi-scan
(SADABS; Sheldrick, 2006)
Multi-scan
(SADABS; Sheldrick, 2006)
Tmin, Tmax0.853, 0.8950.845, 0.9760.892, 0.9870.865, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
15459, 7911, 7462 25647, 13151, 11227 60803, 9492, 5497 8747, 2302, 1978
Rint0.0320.0170.0850.023
(sin θ/λ)max1)0.6500.7030.6500.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.104, 1.06 0.034, 0.092, 1.03 0.051, 0.135, 1.09 0.032, 0.093, 1.11
No. of reflections79111315194922302
No. of parameters406623562137
H-atom treatmentH-atom parameters constrainedOnly H-atom coordinates refinedH-atom parameters constrainedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.71, 0.430.50, 0.350.61, 1.020.42, 0.31

Computer programs: SMART (Bruker, 2002), APEX2 (Bruker, 2006), SAINT (Version 7.23; Bruker, 2005), SAINT (Version 7.16b; Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Version 5.1; Sheldrick, 2008).

Selected bond lengths (Å) for (I) top
P1—O31.4794 (19)P21—O231.442 (2)
P1—O51.5614 (19)P21—O251.5673 (19)
P1—O41.5901 (19)P21—O241.5792 (19)
P1—C91.805 (3)P21—C291.813 (3)
S1—O21.4324 (18)S21—O221.4368 (19)
S1—O11.4480 (19)S21—O211.4539 (19)
S1—C81.741 (3)S21—C281.750 (3)
S1—C91.790 (2)S21—C291.765 (3)
Selected bond lengths (Å) for (II) top
P1—O101.4734 (10)P21—O301.4736 (10)
P1—O81.5623 (10)P21—O281.5623 (10)
P1—O91.5736 (10)P21—O291.5739 (10)
P1—C91.8156 (14)P21—C291.8167 (14)
S1—O41.4430 (10)S21—O241.4424 (10)
S1—O51.4431 (10)S21—O251.4452 (10)
S1—C71.7356 (13)S21—C271.7330 (13)
S1—C81.7877 (14)S21—C281.7891 (14)
S2—O71.4389 (11)S22—O271.4376 (11)
S2—O61.4420 (10)S22—O261.4420 (10)
S2—C91.7698 (13)S22—C291.7707 (13)
S2—C81.7816 (14)S22—C281.7795 (14)
Selected bond lengths (Å) for (III) top
S1—O21.4422 (17)S21—O221.4415 (16)
S1—O11.4432 (16)S21—O211.4428 (15)
S1—C81.738 (2)S21—C281.739 (2)
S1—C91.751 (2)S21—C291.742 (2)
Selected bond lengths (Å) for (IV) top
S1—O21.4369 (9)S1—C81.7422 (12)
S1—O11.4502 (9)S1—C91.7896 (9)
Table 5. Summary of structural parameters for (I)-(IV) (Å, °). top
S—C(C)S—CSOPOP—OP—CS—C—SS—C—P
1.741[4,9]1.780[7,9]1.443[4,20]1.467[10,4]1.571[7,8]1.813[3,4]117.23[17,3]114.9[3,4]
(a) In square brackets is given the average deviation from the mean value followed by the number of observations.
 

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