organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2,4-Di-tert-butyl-6-[(R/S)-1-(3,5-di-tert-butyl-2-hy­dr­oxy­phen­yl)eth­yl]phenyl [(1R,4S)-7,7-di­methyl-2-oxobi­cyclo­[2.2.1]heptan-1-yl]methane­sulfonate

aDepartment of Thoracis Surgery, The Second Hospital of Lanzhou University, Lanzhou 730000, People's Republic of China, and bDepartment of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
*Correspondence e-mail: wujc@lzu.edu.cn

(Received 24 November 2011; accepted 7 December 2011; online 10 December 2011)

The asymmetric unit of the title compound, C40H60O5S, comprises two diastereomers related, except for the chiral camphor groups, by a pseudo-inversion centre. In both diasteromers, the camphor sulfate moiety maintained the absolute configuartion (R,S) of the precursor. However, the absolute configurations at the methine C atoms are of opposite chirality. Both mol­ecules reveal intra­molecular O—H⋯O hydrogen bonds, whereas van der Waals inter­actions define the crystal packing.

Related literature

The title compound is a potential ligand for the investigation of ring-opening polymerization of lactides. Poly(lactide) and poly(-caprolactone) and their copolymers are the most promising biodegradable and biocompatible synthetic macromolecules. Due to the advantages of well controlled mol­ecular weight and low polydispersity, many metal complexes have been used, see: Wu et al. (2006[Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.]).

[Scheme 1]

Experimental

Crystal data
  • C40H60O5S

  • Mr = 652.98

  • Monoclinic, P 21

  • a = 18.2082 (19) Å

  • b = 10.6028 (11) Å

  • c = 20.287 (2) Å

  • β = 93.003 (2)°

  • V = 3911.2 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 293 K

  • 0.32 × 0.28 × 0.23 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998)[Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 1, Tmax = 1

  • 21496 measured reflections

  • 13182 independent reflections

  • 7458 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 0.203

  • S = 1.08

  • 13182 reflections

  • 829 parameters

  • 53 restraints

  • H-atom parameters constrained

  • Δρmax = 0.88 e Å−3

  • Δρmin = −0.35 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 5058 Friedel pairs

  • Flack parameter: −0.12 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O3 0.82 2.23 2.974 (6) 152
O1A—H1AA⋯O3A 0.82 2.20 2.957 (6) 153

Data collection: SMART (Bruker, 1998[Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Poly(lactide) and poly(ε-caprolactone) and their copolymers are the most promising biodegradable and biocompatible synthetic macromolecules. Due to the advantages of well controlled molecular weight and low polydispersity (PDI), many metal complexes have been used (Wu et al., 2006). In the present study, we report a structure which is a potential ligand for the investigation of ring-opening polymerisation of lactides. Camphor sulfate moiety mentains R,S configuration and the chiral centre at methine atoms C7 and C7A are of opposite chirality. Thus, there are two diastereomers in one unsymmetrical unit with the absolute configurations (R, R, S) and (S, R, S) respectively (Scheme and Fig. 1). The bond lengths and angles are within normal range. There are two intramolecular hydrogen bonds of O2—H1a—O3 and O2a—H1aa—O3a (Table 1 and Fig. 1).

Related literature top

Poly(lactide) and poly(ε-caprolactone) and their copolymers are the most promising biodegradable and biocompatible synthetic macromolecules. Due to the advantages of well controlled molecular weight and low polydispersity, many metal complexes have been used, see: Wu et al. (2006).

Experimental top

6,6'-(ethane-1,1-diyl)bis(2,4-di-tert-butylphenol)(4.38 g, 10 mmol) and triethylamine (14 mL, 100 mmol) were dissolved in 100 mL of dichloromethane. (R,S)camphor sulfonyl chloride (2.76 g, 11 mmol) in dichloromethane (20 mL) was added dropwise into the above solution at 273 K for about 1 h. Then, the resulting mixture was stirred for 24 h while the temperature was increased to room temperature. The solution was filtered, and the filtrate was washed with 50 mL of water three times. The dichloromethane layer was collected and dried over anhydrous MgSO4 and filtered through Celite again to remove MgSO4. The resulting filtrate was then dried under vacuo, and the residue was recrystallised by slow cooling of a acetonitrile solution.

Refinement top

PLATON/ADDSYM (Spek, 2009) suggested an inversion symmetry. However, this was rejected, since the two molecules in one asymmetric unit are diastereomers and related by pseudo-inversion centre. Due to disorders of tert-butyl groups, 53 restrains were applied.

The C-bound H atoms were placed at calculated positions and were treated as riding on their parent C atoms with C—H= 0.95 Å. The O-bound H atom was located in a difference Fourier map, and refined with distance restraints of O—H = 0.84 (2) Å.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of (I) with the two molecules in an asymmetric unit showing displacement ellipsoids drawn at the 30% probability level. Intramolecular hydrogen bonds are shown (in dashed lines).
2,4-Di-tert-butyl-6-[(R/S)-1-(3,5-di-tert-butyl-2- hydroxyphenyl)ethyl]phenyl [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1- yl]methanesulfonate top
Crystal data top
C40H60O5SF(000) = 1424
Mr = 652.98Dx = 1.109 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5452 reflections
a = 18.2082 (19) Åθ = 2.2–24.4°
b = 10.6028 (11) ŵ = 0.12 mm1
c = 20.287 (2) ÅT = 293 K
β = 93.003 (2)°Block, colorless
V = 3911.2 (7) Å30.32 × 0.28 × 0.23 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
13182 independent reflections
Radiation source: fine-focus sealed tube7458 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
phi and ω scansθmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 2222
Tmin = 1, Tmax = 1k = 1312
21496 measured reflectionsl = 2125
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.203 w = 1/[σ2(Fo2) + (0.1P)2 + 0.020P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
13182 reflectionsΔρmax = 0.88 e Å3
829 parametersΔρmin = 0.35 e Å3
53 restraintsAbsolute structure: Flack (1983), 5058 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.12 (12)
Crystal data top
C40H60O5SV = 3911.2 (7) Å3
Mr = 652.98Z = 4
Monoclinic, P21Mo Kα radiation
a = 18.2082 (19) ŵ = 0.12 mm1
b = 10.6028 (11) ÅT = 293 K
c = 20.287 (2) Å0.32 × 0.28 × 0.23 mm
β = 93.003 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
13182 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
7458 reflections with I > 2σ(I)
Tmin = 1, Tmax = 1Rint = 0.045
21496 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.203Δρmax = 0.88 e Å3
S = 1.08Δρmin = 0.35 e Å3
13182 reflectionsAbsolute structure: Flack (1983), 5058 Friedel pairs
829 parametersAbsolute structure parameter: 0.12 (12)
53 restraints
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.58400 (7)0.22591 (15)0.10873 (6)0.0523 (4)
S1A0.41355 (7)0.73098 (15)0.38216 (6)0.0514 (4)
O10.76708 (19)0.0372 (4)0.04685 (18)0.0652 (11)
H1A0.73400.06960.06700.098*
O1A0.2269 (2)0.9138 (4)0.44606 (19)0.0638 (11)
H1AA0.26210.88450.42750.096*
O20.58858 (16)0.1566 (4)0.17932 (16)0.0459 (9)
O2A0.41002 (17)0.8119 (4)0.31519 (15)0.0467 (9)
O30.65558 (17)0.2260 (4)0.08357 (18)0.0631 (10)
O3A0.34352 (18)0.7361 (5)0.41029 (17)0.0657 (11)
O40.5475 (2)0.3416 (4)0.1151 (2)0.0698 (12)
O4A0.4438 (2)0.6103 (4)0.36803 (19)0.0666 (11)
O50.4662 (2)0.1248 (4)0.0597 (2)0.0716 (11)
O5A0.5466 (3)0.5991 (5)0.4890 (2)0.0851 (13)
C10.7841 (3)0.0787 (5)0.0738 (3)0.0455 (13)
C1A0.2110 (3)1.0324 (6)0.4213 (2)0.0443 (13)
C2A0.1521 (3)1.0967 (6)0.4489 (3)0.0519 (15)
C20.8419 (3)0.1448 (6)0.0475 (2)0.0458 (13)
C3A0.1357 (3)1.2142 (6)0.4228 (3)0.0535 (14)
H3AB0.09601.25730.43920.064*
C30.8601 (3)0.2618 (6)0.0753 (3)0.0527 (14)
H3B0.89770.30820.05770.063*
C4A0.1740 (3)1.2727 (6)0.3741 (3)0.0541 (16)
C40.8234 (3)0.3128 (5)0.1293 (3)0.0531 (15)
C5A0.2333 (3)1.2052 (6)0.3516 (3)0.0522 (15)
H5AA0.26101.24200.31950.063*
C50.7655 (3)0.2452 (6)0.1513 (2)0.0498 (14)
H5A0.73890.27890.18500.060*
C60.7448 (3)0.1282 (6)0.1255 (2)0.0436 (13)
C6A0.2533 (3)1.0865 (6)0.3742 (2)0.0441 (14)
C70.6795 (2)0.0552 (5)0.1519 (2)0.0444 (13)
H7A0.65450.01330.11400.053*
C7A0.3186 (2)1.0163 (6)0.3489 (2)0.0473 (14)
H7AA0.34160.96970.38630.057*
C80.7033 (3)0.0485 (6)0.2012 (2)0.0448 (13)
C8A0.2953 (2)0.9186 (6)0.2953 (2)0.0426 (13)
C9A0.2275 (3)0.9298 (6)0.2607 (2)0.0493 (14)
H9AA0.19520.99270.27260.059*
C90.7694 (3)0.0356 (6)0.2379 (3)0.0543 (15)
H9A0.80110.02920.22720.065*
C10A0.2070 (3)0.8494 (6)0.2088 (3)0.0533 (15)
C100.7897 (3)0.1141 (6)0.2888 (3)0.0624 (17)
C11A0.2559 (3)0.7603 (6)0.1921 (3)0.0538 (15)
H11A0.24210.70700.15730.065*
C110.7391 (3)0.2067 (6)0.3058 (3)0.0586 (16)
H11B0.75150.25880.34160.070*
C12A0.3261 (2)0.7417 (5)0.2230 (2)0.0438 (12)
C120.6708 (2)0.2249 (6)0.2719 (3)0.0485 (13)
C13A0.3409 (3)0.8213 (5)0.2777 (2)0.0427 (13)
C130.6567 (3)0.1452 (5)0.2174 (2)0.0440 (13)
C140.8834 (3)0.0946 (6)0.0104 (3)0.0592 (16)
C14A0.1073 (3)1.0395 (6)0.5042 (3)0.0560 (15)
C15A0.0478 (3)1.1307 (8)0.5263 (4)0.090 (2)
H15A0.01381.14840.48970.135*
H15B0.07041.20780.54160.135*
H15C0.02201.09290.56130.135*
C150.9220 (3)0.0290 (7)0.0098 (3)0.081 (2)
H15D0.95570.01390.04690.121*
H15E0.88600.09000.02150.121*
H15F0.94850.06030.02650.121*
C160.8286 (3)0.0746 (8)0.0706 (3)0.077 (2)
H16A0.80540.15330.08230.116*
H16B0.85470.04380.10720.116*
H16C0.79190.01430.05940.116*
C16A0.1590 (3)1.0149 (8)0.5649 (3)0.077 (2)
H16D0.19670.95660.55360.116*
H16E0.13150.97990.59960.116*
H16F0.18121.09280.57960.116*
C170.9419 (3)0.1892 (7)0.0329 (3)0.082 (2)
H17A0.97700.20540.00310.123*
H17B0.96660.15420.06930.123*
H17C0.91830.26670.04630.123*
C17A0.0702 (3)0.9203 (8)0.4818 (4)0.086 (2)
H17D0.03690.93770.44470.128*
H17E0.04340.88600.51710.128*
H17F0.10660.86050.46920.128*
C18A0.1533 (3)1.4015 (7)0.3465 (4)0.084 (2)
C180.8457 (4)0.4404 (6)0.1582 (3)0.0734 (19)
C190.9206 (4)0.4849 (9)0.1387 (5)0.147 (4)
H19A0.92070.49200.09150.221*
H19B0.93120.56570.15830.221*
H19C0.95740.42530.15380.221*
C19A0.0802 (5)1.4329 (13)0.3492 (7)0.199 (7)
H19D0.06821.44320.39440.299*
H19E0.05041.36690.32930.299*
H19F0.07081.51030.32570.299*
C20A0.1444 (8)1.3807 (13)0.2671 (5)0.229 (8)
H20A0.13151.45930.24600.344*
H20B0.10631.31990.25710.344*
H20C0.19001.35070.25130.344*
C200.8493 (6)0.4350 (10)0.2355 (4)0.152 (4)
H20D0.86330.51620.25300.228*
H20E0.80190.41230.25040.228*
H20F0.88500.37330.25050.228*
C21A0.2125 (5)1.4869 (10)0.3425 (7)0.190 (7)
H21A0.22661.51780.38580.285*
H21B0.19771.55630.31450.285*
H21C0.25351.44450.32450.285*
C210.7926 (7)0.5357 (8)0.1300 (8)0.237 (9)
H21D0.79290.53400.08270.355*
H21E0.74410.51630.14340.355*
H21F0.80660.61810.14570.355*
C22A0.1319 (4)0.8681 (8)0.1724 (4)0.092 (2)
C220.8636 (4)0.0962 (8)0.3285 (4)0.096 (2)
C26A0.3784 (3)0.6413 (5)0.1954 (3)0.0483 (14)
C260.6184 (3)0.3277 (6)0.2964 (3)0.0577 (16)
C270.6386 (4)0.3601 (7)0.3692 (3)0.088 (2)
H27A0.63440.28580.39580.132*
H27B0.60560.42370.38400.132*
H27C0.68810.39110.37330.132*
C27A0.3650 (4)0.5120 (6)0.2267 (3)0.0762 (19)
H27D0.37410.51750.27360.114*
H27E0.39750.45100.20900.114*
H27F0.31490.48680.21700.114*
C280.5395 (3)0.2814 (7)0.2945 (3)0.078 (2)
H28A0.53630.20770.32170.116*
H28B0.52380.26070.24990.116*
H28C0.50840.34640.31060.116*
C28A0.3630 (3)0.6246 (6)0.1206 (3)0.0613 (16)
H28D0.31240.60220.11190.092*
H28E0.39390.55900.10480.092*
H28F0.37330.70220.09850.092*
C290.6241 (4)0.4452 (7)0.2559 (4)0.086 (2)
H29A0.59110.50780.27140.128*
H29B0.61140.42650.21050.128*
H29C0.67360.47670.26000.128*
C29A0.4591 (3)0.6769 (7)0.2038 (3)0.0642 (18)
H29D0.47270.68630.24990.096*
H29E0.46720.75510.18140.096*
H29F0.48840.61190.18540.096*
C30A0.3769 (3)1.1011 (6)0.3224 (3)0.0581 (16)
H30A0.39281.16080.35570.087*
H30B0.35691.14520.28420.087*
H30C0.41801.05100.31040.087*
C300.6223 (3)0.1376 (6)0.1835 (3)0.0584 (16)
H30D0.60650.20290.15330.088*
H30E0.58090.08680.19400.088*
H30F0.64360.17490.22320.088*
C31A0.4783 (3)0.8208 (6)0.4313 (2)0.0544 (15)
H31A0.47050.90910.42060.065*
H31B0.46700.80980.47710.065*
C310.5272 (3)0.1199 (6)0.0610 (2)0.0492 (14)
H31C0.52870.14640.01530.059*
H31D0.55060.03770.06410.059*
C320.4471 (3)0.1005 (5)0.0746 (2)0.0444 (12)
C32A0.5587 (3)0.7926 (5)0.4255 (2)0.0467 (13)
C330.4250 (3)0.0370 (6)0.0623 (2)0.0551 (15)
C33A0.5840 (3)0.6752 (6)0.4638 (3)0.0588 (15)
C34A0.6670 (3)0.6802 (6)0.4688 (3)0.0732 (19)
H34A0.68830.61290.44360.088*
H34B0.68580.67500.51440.088*
C340.3416 (3)0.0379 (6)0.0536 (3)0.0641 (16)
H34C0.32540.07000.01050.077*
H34D0.32000.08840.08740.077*
C35A0.6822 (3)0.8079 (7)0.4393 (3)0.0636 (18)
H35A0.72960.84460.45430.076*
C350.3222 (3)0.1002 (6)0.0607 (3)0.0534 (14)
H35B0.27340.12340.04170.064*
C360.3349 (3)0.1308 (7)0.1342 (3)0.0657 (17)
H36A0.31550.21330.14420.079*
H36B0.31190.06820.16120.079*
C36A0.6711 (3)0.7949 (9)0.3634 (3)0.085 (2)
H36C0.69680.72200.34720.102*
H36D0.68690.87000.34090.102*
C37A0.5852 (3)0.7777 (8)0.3559 (3)0.076 (2)
H37A0.56330.84120.32670.091*
H37B0.57270.69490.33840.091*
C370.4186 (3)0.1280 (7)0.1457 (2)0.0642 (18)
H37C0.43380.06190.17660.077*
H37D0.43700.20830.16260.077*
C380.3871 (3)0.1672 (5)0.0291 (2)0.0490 (13)
C38A0.6147 (3)0.8865 (6)0.4576 (3)0.0592 (15)
C39A0.6112 (4)1.0181 (7)0.4278 (4)0.100 (2)
H39A0.61551.01260.38100.150*
H39B0.65071.06830.44690.150*
H39C0.56501.05650.43690.150*
C390.3850 (3)0.3113 (5)0.0368 (3)0.0627 (16)
H39D0.34690.34540.00750.094*
H39E0.43150.34620.02610.094*
H39F0.37520.33230.08150.094*
C400.3947 (3)0.1367 (6)0.0433 (2)0.0608 (16)
H40A0.35660.17860.06930.091*
H40B0.39070.04720.04970.091*
H40C0.44180.16490.05650.091*
C40A0.6072 (4)0.8998 (8)0.5330 (3)0.089 (2)
H40D0.60950.81790.55310.134*
H40E0.56090.93860.54120.134*
H40F0.64660.95120.55140.134*
C250.9098 (4)0.1968 (12)0.3206 (7)0.198 (5)
H25A0.92600.19730.27630.297*
H25B0.95160.18970.35120.297*
H25C0.88400.27380.32870.297*
C240.8491 (5)0.0934 (13)0.4060 (5)0.172 (4)
H24A0.89490.08150.43090.258*
H24B0.81630.02520.41500.258*
H24C0.82730.17180.41850.258*
C23A0.1126 (6)0.9961 (11)0.1625 (7)0.191 (5)
H23D0.14221.03170.12940.287*
H23E0.12111.04150.20320.287*
H23F0.06161.00200.14830.287*
C24A0.0731 (5)0.8508 (15)0.2237 (6)0.195 (5)
H24D0.02510.86060.20250.292*
H24E0.08020.91290.25780.292*
H24F0.07750.76800.24270.292*
C25A0.1163 (5)0.7756 (13)0.1255 (6)0.229 (6)
H25D0.15120.78050.09170.343*
H25E0.06760.78800.10620.343*
H25F0.11940.69410.14600.343*
C230.8891 (5)0.0331 (10)0.3281 (6)0.184 (5)
H23A0.89710.05830.28360.276*
H23B0.85280.08700.34600.276*
H23C0.93430.03990.35430.276*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0456 (8)0.0595 (10)0.0511 (8)0.0041 (8)0.0035 (6)0.0106 (8)
S1A0.0441 (8)0.0642 (10)0.0454 (7)0.0038 (8)0.0027 (6)0.0080 (8)
O10.061 (2)0.069 (3)0.067 (3)0.017 (2)0.013 (2)0.021 (2)
O1A0.060 (2)0.067 (3)0.067 (3)0.007 (2)0.0190 (19)0.011 (2)
O20.0339 (18)0.063 (2)0.0397 (19)0.0036 (17)0.0045 (14)0.0054 (18)
O2A0.0355 (19)0.066 (3)0.0376 (19)0.0005 (18)0.0038 (14)0.0018 (18)
O30.046 (2)0.079 (3)0.064 (2)0.008 (2)0.0015 (17)0.018 (2)
O3A0.049 (2)0.089 (3)0.059 (2)0.007 (2)0.0063 (17)0.021 (2)
O40.069 (3)0.063 (3)0.076 (3)0.014 (2)0.005 (2)0.006 (2)
O4A0.080 (3)0.057 (3)0.061 (2)0.013 (2)0.011 (2)0.007 (2)
O50.077 (3)0.058 (3)0.080 (3)0.016 (2)0.009 (2)0.015 (2)
O5A0.089 (3)0.088 (3)0.076 (3)0.001 (3)0.010 (2)0.026 (3)
C10.038 (3)0.047 (3)0.050 (3)0.003 (3)0.008 (2)0.004 (3)
C1A0.044 (3)0.054 (4)0.035 (3)0.002 (3)0.000 (2)0.004 (3)
C2A0.038 (3)0.063 (4)0.054 (3)0.006 (3)0.005 (3)0.002 (3)
C20.038 (3)0.059 (4)0.040 (3)0.001 (3)0.004 (2)0.006 (3)
C3A0.041 (3)0.062 (4)0.059 (3)0.009 (3)0.011 (2)0.002 (3)
C30.043 (3)0.060 (4)0.055 (3)0.000 (3)0.002 (2)0.001 (3)
C4A0.034 (3)0.071 (4)0.057 (3)0.004 (3)0.005 (3)0.011 (3)
C40.055 (3)0.053 (4)0.051 (3)0.012 (3)0.008 (3)0.005 (3)
C5A0.043 (3)0.070 (5)0.043 (3)0.001 (3)0.003 (2)0.003 (3)
C50.050 (3)0.061 (4)0.038 (3)0.003 (3)0.003 (2)0.007 (3)
C60.037 (3)0.060 (4)0.034 (3)0.006 (3)0.002 (2)0.002 (3)
C6A0.042 (3)0.060 (4)0.030 (3)0.001 (3)0.001 (2)0.006 (3)
C70.040 (3)0.054 (4)0.039 (3)0.006 (3)0.006 (2)0.005 (3)
C7A0.036 (3)0.068 (4)0.038 (3)0.004 (3)0.002 (2)0.004 (3)
C80.040 (3)0.050 (3)0.043 (3)0.003 (3)0.007 (2)0.004 (3)
C8A0.035 (3)0.055 (4)0.037 (3)0.001 (3)0.000 (2)0.003 (3)
C9A0.037 (3)0.057 (4)0.053 (3)0.008 (3)0.006 (2)0.009 (3)
C90.043 (3)0.056 (4)0.064 (4)0.007 (3)0.005 (3)0.010 (3)
C10A0.041 (3)0.058 (4)0.059 (3)0.001 (3)0.010 (3)0.016 (3)
C100.050 (4)0.066 (4)0.068 (4)0.004 (3)0.021 (3)0.006 (4)
C11A0.045 (3)0.053 (4)0.061 (3)0.002 (3)0.013 (3)0.018 (3)
C110.048 (3)0.063 (4)0.063 (3)0.005 (3)0.013 (3)0.016 (3)
C12A0.043 (3)0.038 (3)0.050 (3)0.001 (3)0.005 (2)0.003 (3)
C120.040 (3)0.048 (3)0.057 (3)0.003 (3)0.003 (2)0.002 (3)
C13A0.031 (3)0.059 (4)0.037 (3)0.004 (3)0.004 (2)0.003 (3)
C130.037 (3)0.045 (3)0.049 (3)0.002 (3)0.006 (2)0.004 (3)
C140.046 (3)0.074 (4)0.058 (4)0.006 (3)0.008 (3)0.007 (3)
C14A0.041 (3)0.069 (4)0.059 (4)0.001 (3)0.011 (3)0.010 (3)
C15A0.069 (4)0.106 (6)0.099 (5)0.004 (4)0.042 (4)0.008 (5)
C150.069 (4)0.092 (5)0.082 (5)0.016 (4)0.020 (3)0.016 (4)
C160.072 (4)0.110 (6)0.049 (3)0.011 (4)0.003 (3)0.022 (4)
C16A0.068 (4)0.114 (6)0.052 (4)0.018 (4)0.013 (3)0.017 (4)
C170.071 (4)0.105 (6)0.074 (4)0.016 (4)0.039 (3)0.026 (4)
C17A0.070 (4)0.092 (6)0.095 (5)0.022 (4)0.010 (4)0.012 (4)
C18A0.047 (4)0.077 (5)0.129 (6)0.014 (4)0.019 (4)0.047 (5)
C180.088 (5)0.064 (5)0.069 (4)0.013 (4)0.012 (4)0.012 (4)
C190.123 (7)0.108 (7)0.220 (11)0.063 (6)0.087 (7)0.078 (8)
C19A0.110 (7)0.196 (13)0.297 (16)0.058 (8)0.069 (8)0.172 (13)
C20A0.347 (19)0.207 (15)0.131 (10)0.137 (15)0.022 (11)0.076 (10)
C200.244 (12)0.133 (9)0.081 (6)0.052 (8)0.026 (7)0.034 (6)
C21A0.083 (6)0.110 (8)0.38 (2)0.002 (6)0.066 (9)0.100 (10)
C210.289 (16)0.034 (5)0.37 (2)0.009 (7)0.187 (15)0.035 (8)
C22A0.056 (4)0.099 (5)0.116 (5)0.031 (4)0.046 (3)0.041 (4)
C220.056 (4)0.093 (5)0.133 (5)0.012 (4)0.053 (4)0.051 (5)
C26A0.047 (3)0.046 (3)0.052 (3)0.001 (3)0.001 (2)0.001 (3)
C260.051 (4)0.051 (4)0.070 (4)0.003 (3)0.007 (3)0.014 (3)
C270.078 (4)0.095 (6)0.090 (5)0.023 (4)0.006 (4)0.046 (4)
C27A0.088 (5)0.051 (4)0.091 (5)0.003 (4)0.016 (4)0.002 (4)
C280.053 (4)0.095 (6)0.085 (5)0.006 (4)0.016 (3)0.027 (4)
C28A0.069 (4)0.066 (4)0.048 (3)0.002 (3)0.003 (3)0.016 (3)
C290.095 (5)0.060 (5)0.102 (6)0.001 (4)0.013 (4)0.013 (4)
C29A0.048 (3)0.082 (5)0.063 (4)0.002 (3)0.003 (3)0.011 (3)
C30A0.046 (3)0.075 (4)0.054 (3)0.005 (3)0.011 (3)0.015 (3)
C300.054 (4)0.073 (4)0.049 (3)0.016 (3)0.006 (3)0.020 (3)
C31A0.051 (3)0.073 (4)0.038 (3)0.021 (3)0.005 (2)0.002 (3)
C310.044 (3)0.063 (4)0.040 (3)0.004 (3)0.005 (2)0.004 (3)
C320.044 (3)0.057 (3)0.031 (2)0.004 (3)0.004 (2)0.007 (2)
C32A0.041 (3)0.062 (3)0.037 (3)0.006 (3)0.000 (2)0.001 (3)
C330.063 (4)0.063 (4)0.039 (3)0.012 (3)0.003 (2)0.016 (3)
C33A0.058 (4)0.070 (4)0.048 (3)0.014 (3)0.002 (3)0.003 (3)
C34A0.054 (4)0.092 (5)0.072 (4)0.029 (3)0.010 (3)0.001 (4)
C340.055 (3)0.063 (4)0.074 (4)0.006 (3)0.002 (3)0.016 (3)
C35A0.038 (3)0.091 (5)0.061 (4)0.004 (3)0.006 (3)0.010 (4)
C350.043 (3)0.062 (4)0.054 (3)0.001 (3)0.005 (2)0.006 (3)
C360.050 (3)0.097 (5)0.051 (3)0.009 (3)0.009 (3)0.003 (3)
C36A0.055 (4)0.150 (7)0.051 (4)0.002 (4)0.007 (3)0.010 (4)
C37A0.058 (4)0.130 (7)0.038 (3)0.008 (4)0.004 (3)0.002 (3)
C370.059 (4)0.098 (5)0.036 (3)0.006 (3)0.006 (2)0.001 (3)
C380.042 (3)0.057 (3)0.047 (3)0.007 (3)0.007 (2)0.007 (3)
C38A0.054 (3)0.072 (4)0.052 (3)0.001 (3)0.004 (3)0.000 (3)
C39A0.091 (5)0.086 (6)0.123 (6)0.008 (5)0.003 (5)0.013 (5)
C390.057 (4)0.057 (4)0.074 (4)0.009 (3)0.001 (3)0.005 (3)
C400.074 (4)0.066 (4)0.041 (3)0.012 (3)0.013 (3)0.004 (3)
C40A0.094 (5)0.109 (6)0.062 (4)0.008 (5)0.018 (3)0.024 (4)
C250.073 (5)0.180 (9)0.330 (12)0.055 (6)0.090 (7)0.082 (10)
C240.128 (7)0.255 (12)0.124 (6)0.031 (7)0.066 (5)0.009 (7)
C23A0.162 (8)0.126 (7)0.267 (11)0.027 (7)0.154 (8)0.014 (7)
C24A0.068 (5)0.297 (13)0.215 (10)0.005 (7)0.023 (5)0.004 (9)
C25A0.136 (7)0.253 (10)0.279 (11)0.093 (8)0.158 (7)0.173 (10)
C230.149 (8)0.118 (6)0.267 (10)0.052 (6)0.158 (7)0.060 (7)
Geometric parameters (Å, º) top
S1—O41.404 (4)C21—H21D0.9600
S1—O31.424 (3)C21—H21E0.9600
S1—O21.608 (4)C21—H21F0.9600
S1—C311.780 (5)C22A—C25A1.386 (11)
S1A—O3A1.425 (3)C22A—C23A1.413 (13)
S1A—O4A1.428 (4)C22A—C24A1.542 (11)
S1A—O2A1.605 (4)C22—C251.374 (12)
S1A—C31A1.780 (5)C22—C231.448 (12)
O1—C11.374 (7)C22—C241.609 (13)
O1—H1A0.8200C26A—C29A1.519 (7)
O1A—C1A1.379 (7)C26A—C27A1.536 (9)
O1A—H1AA0.8200C26A—C28A1.537 (7)
O2—C131.431 (5)C26—C291.499 (9)
O2A—C13A1.440 (5)C26—C281.518 (8)
O5—C331.198 (6)C26—C271.543 (8)
O5A—C33A1.190 (7)C27—H27A0.9600
C1—C21.393 (7)C27—H27B0.9600
C1—C61.404 (7)C27—H27C0.9600
C1A—C6A1.383 (7)C27A—H27D0.9600
C1A—C2A1.410 (7)C27A—H27E0.9600
C2A—C3A1.380 (8)C27A—H27F0.9600
C2A—C14A1.546 (8)C28—H28A0.9600
C2—C31.394 (8)C28—H28B0.9600
C2—C141.526 (7)C28—H28C0.9600
C3A—C4A1.387 (8)C28A—H28D0.9600
C3A—H3AB0.9300C28A—H28E0.9600
C3—C41.420 (8)C28A—H28F0.9600
C3—H3B0.9300C29—H29A0.9600
C4A—C5A1.392 (8)C29—H29B0.9600
C4A—C18A1.516 (9)C29—H29C0.9600
C4—C51.368 (7)C29A—H29D0.9600
C4—C181.522 (9)C29A—H29E0.9600
C5A—C6A1.382 (8)C29A—H29F0.9600
C5A—H5AA0.9300C30A—H30A0.9600
C5—C61.390 (8)C30A—H30B0.9600
C5—H5A0.9300C30A—H30C0.9600
C6—C71.538 (7)C30—H30D0.9600
C6A—C7A1.515 (7)C30—H30E0.9600
C7—C301.525 (7)C30—H30F0.9600
C7—C81.533 (7)C31A—C32A1.505 (7)
C7—H7A0.9800C31A—H31A0.9700
C7A—C30A1.511 (7)C31A—H31B0.9700
C7A—C8A1.545 (7)C31—C321.511 (7)
C7A—H7AA0.9800C31—H31C0.9700
C8—C131.382 (7)C31—H31D0.9700
C8—C91.388 (6)C32—C331.529 (8)
C8A—C13A1.383 (7)C32—C381.562 (6)
C8A—C9A1.392 (6)C32—C371.586 (7)
C9A—C10A1.391 (7)C32A—C37A1.524 (7)
C9A—H9AA0.9300C32A—C33A1.525 (8)
C9—C101.362 (8)C32A—C38A1.544 (8)
C9—H9A0.9300C33—C341.519 (7)
C10A—C11A1.354 (7)C33A—C34A1.510 (8)
C10A—C22A1.533 (7)C34A—C35A1.511 (9)
C10—C111.403 (8)C34A—H34A0.9700
C10—C221.543 (8)C34A—H34B0.9700
C11A—C12A1.407 (6)C34—C351.514 (8)
C11A—H11A0.9300C34—H34C0.9700
C11—C121.403 (6)C34—H34D0.9700
C11—H11B0.9300C35A—C38A1.546 (8)
C12A—C13A1.408 (7)C35A—C36A1.549 (8)
C12A—C26A1.552 (7)C35A—H35A0.9800
C12—C131.404 (7)C35—C361.532 (7)
C12—C261.547 (8)C35—C381.546 (7)
C14—C151.533 (9)C35—H35B0.9800
C14—C171.549 (9)C36—C371.530 (7)
C14—C161.549 (7)C36—H36A0.9700
C14A—C17A1.493 (9)C36—H36B0.9700
C14A—C16A1.533 (8)C36A—C37A1.573 (7)
C14A—C15A1.537 (9)C36A—H36C0.9700
C15A—H15A0.9600C36A—H36D0.9700
C15A—H15B0.9600C37A—H37A0.9700
C15A—H15C0.9600C37A—H37B0.9700
C15—H15D0.9600C37—H37C0.9700
C15—H15E0.9600C37—H37D0.9700
C15—H15F0.9600C38—C401.518 (7)
C16—H16A0.9600C38—C391.536 (8)
C16—H16B0.9600C38A—C39A1.520 (10)
C16—H16C0.9600C38A—C40A1.549 (8)
C16A—H16D0.9600C39A—H39A0.9600
C16A—H16E0.9600C39A—H39B0.9600
C16A—H16F0.9600C39A—H39C0.9600
C17—H17A0.9600C39—H39D0.9600
C17—H17B0.9600C39—H39E0.9600
C17—H17C0.9600C39—H39F0.9600
C17A—H17D0.9600C40—H40A0.9600
C17A—H17E0.9600C40—H40B0.9600
C17A—H17F0.9600C40—H40C0.9600
C18A—C19A1.376 (9)C40A—H40D0.9600
C18A—C21A1.413 (10)C40A—H40E0.9600
C18A—C20A1.626 (11)C40A—H40F0.9600
C18—C211.493 (10)C25—H25A0.9600
C18—C191.515 (9)C25—H25B0.9600
C18—C201.566 (10)C25—H25C0.9600
C19—H19A0.9600C24—H24A0.9600
C19—H19B0.9600C24—H24B0.9600
C19—H19C0.9600C24—H24C0.9600
C19A—H19D0.9600C23A—H23D0.9600
C19A—H19E0.9600C23A—H23E0.9600
C19A—H19F0.9600C23A—H23F0.9600
C20A—H20A0.9600C24A—H24D0.9600
C20A—H20B0.9600C24A—H24E0.9600
C20A—H20C0.9600C24A—H24F0.9600
C20—H20D0.9600C25A—H25D0.9600
C20—H20E0.9600C25A—H25E0.9600
C20—H20F0.9600C25A—H25F0.9600
C21A—H21A0.9600C23—H23A0.9600
C21A—H21B0.9600C23—H23B0.9600
C21A—H21C0.9600C23—H23C0.9600
O4—S1—O3118.6 (3)C29A—C26A—C28A105.3 (4)
O4—S1—O2108.7 (2)C27A—C26A—C28A106.3 (5)
O3—S1—O2108.3 (2)C29A—C26A—C12A113.4 (5)
O4—S1—C31109.7 (2)C27A—C26A—C12A110.4 (4)
O3—S1—C31108.8 (3)C28A—C26A—C12A110.7 (4)
O2—S1—C31101.4 (2)C29—C26—C28110.4 (5)
O3A—S1A—O4A118.5 (3)C29—C26—C27108.6 (6)
O3A—S1A—O2A108.8 (2)C28—C26—C27105.9 (5)
O4A—S1A—O2A107.9 (2)C29—C26—C12110.4 (5)
O3A—S1A—C31A109.6 (3)C28—C26—C12111.3 (5)
O4A—S1A—C31A109.9 (2)C27—C26—C12110.2 (5)
O2A—S1A—C31A100.6 (2)C26—C27—H27A109.5
C1—O1—H1A109.5C26—C27—H27B109.5
C1A—O1A—H1AA109.5H27A—C27—H27B109.5
C13—O2—S1121.5 (3)C26—C27—H27C109.5
C13A—O2A—S1A118.7 (3)H27A—C27—H27C109.5
O1—C1—C2117.2 (5)H27B—C27—H27C109.5
O1—C1—C6121.2 (5)C26A—C27A—H27D109.5
C2—C1—C6121.5 (5)C26A—C27A—H27E109.5
O1A—C1A—C6A121.0 (5)H27D—C27A—H27E109.5
O1A—C1A—C2A116.6 (5)C26A—C27A—H27F109.5
C6A—C1A—C2A122.4 (5)H27D—C27A—H27F109.5
C3A—C2A—C1A116.1 (5)H27E—C27A—H27F109.5
C3A—C2A—C14A121.3 (5)C26—C28—H28A109.5
C1A—C2A—C14A122.6 (5)C26—C28—H28B109.5
C1—C2—C3117.4 (5)H28A—C28—H28B109.5
C1—C2—C14122.2 (5)C26—C28—H28C109.5
C3—C2—C14120.3 (5)H28A—C28—H28C109.5
C2A—C3A—C4A124.7 (5)H28B—C28—H28C109.5
C2A—C3A—H3AB117.7C26A—C28A—H28D109.5
C4A—C3A—H3AB117.7C26A—C28A—H28E109.5
C2—C3—C4122.6 (5)H28D—C28A—H28E109.5
C2—C3—H3B118.7C26A—C28A—H28F109.5
C4—C3—H3B118.7H28D—C28A—H28F109.5
C3A—C4A—C5A115.6 (6)H28E—C28A—H28F109.5
C3A—C4A—C18A122.7 (6)C26—C29—H29A109.5
C5A—C4A—C18A121.7 (5)C26—C29—H29B109.5
C5—C4—C3117.0 (5)H29A—C29—H29B109.5
C5—C4—C18122.4 (5)C26—C29—H29C109.5
C3—C4—C18120.6 (5)H29A—C29—H29C109.5
C6A—C5A—C4A123.7 (5)H29B—C29—H29C109.5
C6A—C5A—H5AA118.2C26A—C29A—H29D109.5
C4A—C5A—H5AA118.2C26A—C29A—H29E109.5
C4—C5—C6122.9 (5)H29D—C29A—H29E109.5
C4—C5—H5A118.5C26A—C29A—H29F109.5
C6—C5—H5A118.5H29D—C29A—H29F109.5
C5—C6—C1118.4 (5)H29E—C29A—H29F109.5
C5—C6—C7121.2 (5)C7A—C30A—H30A109.5
C1—C6—C7120.4 (5)C7A—C30A—H30B109.5
C5A—C6A—C1A117.4 (5)H30A—C30A—H30B109.5
C5A—C6A—C7A122.2 (5)C7A—C30A—H30C109.5
C1A—C6A—C7A120.4 (5)H30A—C30A—H30C109.5
C30—C7—C8108.2 (4)H30B—C30A—H30C109.5
C30—C7—C6114.5 (5)C7—C30—H30D109.5
C8—C7—C6113.0 (4)C7—C30—H30E109.5
C30—C7—H7A106.9H30D—C30—H30E109.5
C8—C7—H7A106.9C7—C30—H30F109.5
C6—C7—H7A106.9H30D—C30—H30F109.5
C30A—C7A—C6A114.0 (5)H30E—C30—H30F109.5
C30A—C7A—C8A108.7 (4)C32A—C31A—S1A117.9 (4)
C6A—C7A—C8A112.1 (4)C32A—C31A—H31A107.8
C30A—C7A—H7AA107.2S1A—C31A—H31A107.8
C6A—C7A—H7AA107.2C32A—C31A—H31B107.8
C8A—C7A—H7AA107.2S1A—C31A—H31B107.8
C13—C8—C9118.1 (5)H31A—C31A—H31B107.2
C13—C8—C7122.1 (4)C32—C31—S1121.7 (4)
C9—C8—C7119.1 (5)C32—C31—H31C106.9
C13A—C8A—C9A117.4 (5)S1—C31—H31C106.9
C13A—C8A—C7A122.4 (4)C32—C31—H31D106.9
C9A—C8A—C7A120.1 (5)S1—C31—H31D106.9
C10A—C9A—C8A121.7 (5)H31C—C31—H31D106.7
C10A—C9A—H9AA119.1C31—C32—C33110.4 (4)
C8A—C9A—H9AA119.1C31—C32—C38118.9 (4)
C10—C9—C8122.7 (5)C33—C32—C3899.5 (4)
C10—C9—H9A118.6C31—C32—C37120.3 (4)
C8—C9—H9A118.6C33—C32—C37103.2 (4)
C11A—C10A—C9A117.5 (4)C38—C32—C37101.6 (4)
C11A—C10A—C22A123.5 (5)C31A—C32A—C37A116.7 (4)
C9A—C10A—C22A118.9 (5)C31A—C32A—C33A113.1 (5)
C9—C10—C11117.3 (5)C37A—C32A—C33A106.5 (5)
C9—C10—C22121.1 (6)C31A—C32A—C38A117.5 (4)
C11—C10—C22121.5 (6)C37A—C32A—C38A102.9 (4)
C10A—C11A—C12A125.5 (5)C33A—C32A—C38A97.8 (4)
C10A—C11A—H11A117.2O5—C33—C34127.8 (6)
C12A—C11A—H11A117.2O5—C33—C32126.0 (5)
C10—C11—C12123.5 (5)C34—C33—C32106.1 (5)
C10—C11—H11B118.2O5A—C33A—C34A126.0 (6)
C12—C11—H11B118.2O5A—C33A—C32A127.5 (5)
C11A—C12A—C13A113.5 (5)C34A—C33A—C32A106.3 (5)
C11A—C12A—C26A119.6 (4)C33A—C34A—C35A102.0 (5)
C13A—C12A—C26A126.9 (4)C33A—C34A—H34A111.4
C11—C12—C13115.1 (5)C35A—C34A—H34A111.4
C11—C12—C26119.0 (5)C33A—C34A—H34B111.4
C13—C12—C26125.9 (4)C35A—C34A—H34B111.4
C8A—C13A—C12A124.0 (4)H34A—C34A—H34B109.2
C8A—C13A—O2A115.7 (4)C35—C34—C33102.7 (5)
C12A—C13A—O2A120.0 (4)C35—C34—H34C111.2
C8—C13—C12123.0 (4)C33—C34—H34C111.2
C8—C13—O2117.3 (4)C35—C34—H34D111.2
C12—C13—O2119.5 (4)C33—C34—H34D111.2
C2—C14—C15109.4 (5)H34C—C34—H34D109.1
C2—C14—C17112.1 (5)C34A—C35A—C38A103.0 (5)
C15—C14—C17108.6 (5)C34A—C35A—C36A107.3 (6)
C2—C14—C16109.3 (4)C38A—C35A—C36A102.8 (5)
C15—C14—C16111.1 (6)C34A—C35A—H35A114.2
C17—C14—C16106.3 (5)C38A—C35A—H35A114.2
C17A—C14A—C16A110.4 (6)C36A—C35A—H35A114.2
C17A—C14A—C15A107.9 (5)C34—C35—C36105.8 (5)
C16A—C14A—C15A106.6 (5)C34—C35—C38102.6 (5)
C17A—C14A—C2A111.0 (5)C36—C35—C38103.0 (4)
C16A—C14A—C2A109.0 (4)C34—C35—H35B114.7
C15A—C14A—C2A111.8 (5)C36—C35—H35B114.7
C14A—C15A—H15A109.5C38—C35—H35B114.7
C14A—C15A—H15B109.5C37—C36—C35104.2 (4)
H15A—C15A—H15B109.5C37—C36—H36A110.9
C14A—C15A—H15C109.5C35—C36—H36A110.9
H15A—C15A—H15C109.5C37—C36—H36B110.9
H15B—C15A—H15C109.5C35—C36—H36B110.9
C14—C15—H15D109.5H36A—C36—H36B108.9
C14—C15—H15E109.5C35A—C36A—C37A100.6 (4)
H15D—C15—H15E109.5C35A—C36A—H36C111.7
C14—C15—H15F109.5C37A—C36A—H36C111.7
H15D—C15—H15F109.5C35A—C36A—H36D111.7
H15E—C15—H15F109.5C37A—C36A—H36D111.7
C14—C16—H16A109.5H36C—C36A—H36D109.4
C14—C16—H16B109.5C32A—C37A—C36A105.0 (4)
H16A—C16—H16B109.5C32A—C37A—H37A110.7
C14—C16—H16C109.5C36A—C37A—H37A110.7
H16A—C16—H16C109.5C32A—C37A—H37B110.7
H16B—C16—H16C109.5C36A—C37A—H37B110.7
C14A—C16A—H16D109.5H37A—C37A—H37B108.8
C14A—C16A—H16E109.5C36—C37—C32103.6 (4)
H16D—C16A—H16E109.5C36—C37—H37C111.0
C14A—C16A—H16F109.5C32—C37—H37C111.0
H16D—C16A—H16F109.5C36—C37—H37D111.0
H16E—C16A—H16F109.5C32—C37—H37D111.0
C14—C17—H17A109.5H37C—C37—H37D109.0
C14—C17—H17B109.5C40—C38—C39108.3 (5)
H17A—C17—H17B109.5C40—C38—C35114.4 (5)
C14—C17—H17C109.5C39—C38—C35113.1 (5)
H17A—C17—H17C109.5C40—C38—C32112.2 (4)
H17B—C17—H17C109.5C39—C38—C32114.3 (5)
C14A—C17A—H17D109.5C35—C38—C3294.2 (4)
C14A—C17A—H17E109.5C39A—C38A—C32A114.3 (5)
H17D—C17A—H17E109.5C39A—C38A—C35A114.7 (5)
C14A—C17A—H17F109.5C32A—C38A—C35A93.8 (4)
H17D—C17A—H17F109.5C39A—C38A—C40A107.7 (6)
H17E—C17A—H17F109.5C32A—C38A—C40A112.6 (5)
C19A—C18A—C21A126.2 (9)C35A—C38A—C40A113.4 (5)
C19A—C18A—C4A115.2 (7)C38A—C39A—H39A109.5
C21A—C18A—C4A115.0 (6)C38A—C39A—H39B109.5
C19A—C18A—C20A91.4 (8)H39A—C39A—H39B109.5
C21A—C18A—C20A93.8 (8)C38A—C39A—H39C109.5
C4A—C18A—C20A104.7 (7)H39A—C39A—H39C109.5
C21—C18—C19105.2 (8)H39B—C39A—H39C109.5
C21—C18—C4107.4 (5)C38—C39—H39D109.5
C19—C18—C4113.7 (6)C38—C39—H39E109.5
C21—C18—C20113.7 (9)H39D—C39—H39E109.5
C19—C18—C20106.4 (7)C38—C39—H39F109.5
C4—C18—C20110.5 (6)H39D—C39—H39F109.5
C18—C19—H19A109.5H39E—C39—H39F109.5
C18—C19—H19B109.5C38—C40—H40A109.5
H19A—C19—H19B109.5C38—C40—H40B109.5
C18—C19—H19C109.5H40A—C40—H40B109.5
H19A—C19—H19C109.5C38—C40—H40C109.5
H19B—C19—H19C109.5H40A—C40—H40C109.5
C18A—C19A—H19D109.5H40B—C40—H40C109.5
C18A—C19A—H19E109.5C38A—C40A—H40D109.5
H19D—C19A—H19E109.5C38A—C40A—H40E109.5
C18A—C19A—H19F109.5H40D—C40A—H40E109.5
H19D—C19A—H19F109.5C38A—C40A—H40F109.5
H19E—C19A—H19F109.5H40D—C40A—H40F109.5
C18A—C20A—H20A109.5H40E—C40A—H40F109.5
C18A—C20A—H20B109.5C22—C25—H25A109.5
H20A—C20A—H20B109.5C22—C25—H25B109.5
C18A—C20A—H20C109.5H25A—C25—H25B109.5
H20A—C20A—H20C109.5C22—C25—H25C109.5
H20B—C20A—H20C109.5H25A—C25—H25C109.5
C18—C20—H20D109.5H25B—C25—H25C109.5
C18—C20—H20E109.5C22—C24—H24A109.5
H20D—C20—H20E109.5C22—C24—H24B109.5
C18—C20—H20F109.5H24A—C24—H24B109.5
H20D—C20—H20F109.5C22—C24—H24C109.5
H20E—C20—H20F109.5H24A—C24—H24C109.5
C18A—C21A—H21A109.5H24B—C24—H24C109.5
C18A—C21A—H21B109.5C22A—C23A—H23D109.5
H21A—C21A—H21B109.5C22A—C23A—H23E109.5
C18A—C21A—H21C109.5H23D—C23A—H23E109.5
H21A—C21A—H21C109.5C22A—C23A—H23F109.5
H21B—C21A—H21C109.5H23D—C23A—H23F109.5
C18—C21—H21D109.5H23E—C23A—H23F109.5
C18—C21—H21E109.5C22A—C24A—H24D109.5
H21D—C21—H21E109.5C22A—C24A—H24E109.5
C18—C21—H21F109.5H24D—C24A—H24E109.5
H21D—C21—H21F109.5C22A—C24A—H24F109.5
H21E—C21—H21F109.5H24D—C24A—H24F109.5
C25A—C22A—C23A122.9 (9)H24E—C24A—H24F109.5
C25A—C22A—C10A112.6 (6)C22A—C25A—H25D109.5
C23A—C22A—C10A113.6 (7)C22A—C25A—H25E109.5
C25A—C22A—C24A104.8 (10)H25D—C25A—H25E109.5
C23A—C22A—C24A92.0 (9)C22A—C25A—H25F109.5
C10A—C22A—C24A107.0 (6)H25D—C25A—H25F109.5
C25—C22—C23122.4 (8)H25E—C25A—H25F109.5
C25—C22—C10111.4 (7)C22—C23—H23A109.5
C23—C22—C10112.6 (6)C22—C23—H23B109.5
C25—C22—C24105.2 (9)H23A—C23—H23B109.5
C23—C22—C2493.3 (9)C22—C23—H23C109.5
C10—C22—C24109.3 (6)H23A—C23—H23C109.5
C29A—C26A—C27A110.4 (5)H23B—C23—H23C109.5
O4—S1—O2—C13108.5 (4)C3A—C4A—C18A—C20A126.3 (8)
O3—S1—O2—C1321.5 (4)C5A—C4A—C18A—C20A53.6 (9)
C31—S1—O2—C13135.9 (4)C5—C4—C18—C2177.5 (10)
O3A—S1A—O2A—C13A29.8 (4)C3—C4—C18—C2199.1 (9)
O4A—S1A—O2A—C13A99.9 (4)C5—C4—C18—C19166.5 (7)
C31A—S1A—O2A—C13A144.9 (4)C3—C4—C18—C1916.8 (9)
O1A—C1A—C2A—C3A178.7 (4)C5—C4—C18—C2047.0 (9)
C6A—C1A—C2A—C3A4.3 (7)C3—C4—C18—C20136.4 (7)
O1A—C1A—C2A—C14A0.4 (7)C11A—C10A—C22A—C25A6.6 (13)
C6A—C1A—C2A—C14A176.6 (5)C9A—C10A—C22A—C25A175.3 (10)
O1—C1—C2—C3179.1 (4)C11A—C10A—C22A—C23A138.8 (10)
C6—C1—C2—C31.0 (7)C9A—C10A—C22A—C23A39.3 (12)
O1—C1—C2—C142.2 (7)C11A—C10A—C22A—C24A121.3 (9)
C6—C1—C2—C14177.7 (5)C9A—C10A—C22A—C24A60.6 (10)
C1A—C2A—C3A—C4A2.1 (8)C9—C10—C22—C25115.3 (10)
C14A—C2A—C3A—C4A178.8 (5)C11—C10—C22—C2568.4 (11)
C1—C2—C3—C41.5 (8)C9—C10—C22—C2326.7 (12)
C14—C2—C3—C4179.8 (5)C11—C10—C22—C23149.6 (9)
C2A—C3A—C4A—C5A0.5 (8)C9—C10—C22—C24128.9 (8)
C2A—C3A—C4A—C18A179.3 (6)C11—C10—C22—C2447.4 (10)
C2—C3—C4—C53.7 (8)C11A—C12A—C26A—C29A147.1 (5)
C2—C3—C4—C18179.5 (5)C13A—C12A—C26A—C29A32.4 (7)
C3A—C4A—C5A—C6A1.3 (8)C11A—C12A—C26A—C27A88.4 (6)
C18A—C4A—C5A—C6A178.6 (5)C13A—C12A—C26A—C27A92.2 (6)
C3—C4—C5—C63.6 (8)C11A—C12A—C26A—C28A29.0 (7)
C18—C4—C5—C6179.6 (5)C13A—C12A—C26A—C28A150.4 (5)
C4—C5—C6—C11.3 (8)C11—C12—C26—C2999.1 (6)
C4—C5—C6—C7179.8 (5)C13—C12—C26—C2980.9 (7)
O1—C1—C6—C5179.0 (4)C11—C12—C26—C28138.1 (6)
C2—C1—C6—C51.1 (7)C13—C12—C26—C2842.0 (8)
O1—C1—C6—C72.1 (7)C11—C12—C26—C2720.9 (8)
C2—C1—C6—C7177.8 (4)C13—C12—C26—C27159.1 (6)
C4A—C5A—C6A—C1A0.8 (8)O3A—S1A—C31A—C32A158.8 (4)
C4A—C5A—C6A—C7A179.5 (5)O4A—S1A—C31A—C32A26.9 (5)
O1A—C1A—C6A—C5A179.5 (4)O2A—S1A—C31A—C32A86.7 (4)
C2A—C1A—C6A—C5A3.6 (7)O4—S1—C31—C3247.6 (5)
O1A—C1A—C6A—C7A0.3 (7)O3—S1—C31—C32178.8 (4)
C2A—C1A—C6A—C7A176.6 (4)O2—S1—C31—C3267.2 (4)
C5—C6—C7—C3025.0 (6)S1—C31—C32—C33144.4 (4)
C1—C6—C7—C30153.9 (5)S1—C31—C32—C38101.6 (5)
C5—C6—C7—C899.5 (6)S1—C31—C32—C3724.5 (7)
C1—C6—C7—C881.6 (6)S1A—C31A—C32A—C37A45.6 (7)
C5A—C6A—C7A—C30A25.3 (6)S1A—C31A—C32A—C33A78.5 (5)
C1A—C6A—C7A—C30A154.9 (5)S1A—C31A—C32A—C38A168.6 (4)
C5A—C6A—C7A—C8A98.7 (6)C31—C32—C33—O518.7 (7)
C1A—C6A—C7A—C8A81.1 (6)C38—C32—C33—O5144.4 (5)
C30—C7—C8—C1369.5 (7)C37—C32—C33—O5111.1 (6)
C6—C7—C8—C13162.6 (5)C31—C32—C33—C34160.8 (4)
C30—C7—C8—C9101.0 (6)C38—C32—C33—C3435.0 (5)
C6—C7—C8—C926.9 (7)C37—C32—C33—C3469.4 (5)
C30A—C7A—C8A—C13A70.8 (7)C31A—C32A—C33A—O5A10.3 (8)
C6A—C7A—C8A—C13A162.2 (5)C37A—C32A—C33A—O5A119.2 (7)
C30A—C7A—C8A—C9A106.3 (6)C38A—C32A—C33A—O5A134.7 (6)
C6A—C7A—C8A—C9A20.7 (7)C31A—C32A—C33A—C34A164.8 (4)
C13A—C8A—C9A—C10A2.2 (8)C37A—C32A—C33A—C34A65.7 (6)
C7A—C8A—C9A—C10A175.1 (5)C38A—C32A—C33A—C34A40.3 (5)
C13—C8—C9—C100.1 (9)O5A—C33A—C34A—C35A169.2 (6)
C7—C8—C9—C10170.8 (5)C32A—C33A—C34A—C35A5.9 (6)
C8A—C9A—C10A—C11A1.1 (9)O5—C33—C34—C35178.7 (5)
C8A—C9A—C10A—C22A179.3 (6)C32—C33—C34—C350.8 (5)
C8—C9—C10—C113.3 (9)C33A—C34A—C35A—C38A31.1 (5)
C8—C9—C10—C22179.7 (7)C33A—C34A—C35A—C36A77.0 (5)
C9A—C10A—C11A—C12A0.2 (9)C33—C34—C35—C3673.0 (5)
C22A—C10A—C11A—C12A178.4 (6)C33—C34—C35—C3834.6 (5)
C9—C10—C11—C122.4 (10)C34—C35—C36—C3770.8 (6)
C22—C10—C11—C12178.8 (7)C38—C35—C36—C3736.5 (6)
C10A—C11A—C12A—C13A3.6 (8)C34A—C35A—C36A—C37A69.9 (7)
C10A—C11A—C12A—C26A175.9 (6)C38A—C35A—C36A—C37A38.2 (7)
C10—C11—C12—C131.7 (9)C31A—C32A—C37A—C36A161.6 (6)
C10—C11—C12—C26178.3 (6)C33A—C32A—C37A—C36A71.1 (7)
C9A—C8A—C13A—C12A6.6 (8)C38A—C32A—C37A—C36A31.3 (7)
C7A—C8A—C13A—C12A170.6 (5)C35A—C36A—C37A—C32A4.1 (8)
C9A—C8A—C13A—O2A179.2 (5)C35—C36—C37—C322.2 (7)
C7A—C8A—C13A—O2A3.6 (7)C31—C32—C37—C36165.8 (5)
C11A—C12A—C13A—C8A7.1 (8)C33—C32—C37—C3670.8 (6)
C26A—C12A—C13A—C8A172.3 (5)C38—C32—C37—C3632.1 (6)
C11A—C12A—C13A—O2A178.9 (5)C34—C35—C38—C4061.7 (5)
C26A—C12A—C13A—O2A1.6 (8)C36—C35—C38—C40171.4 (5)
S1A—O2A—C13A—C8A87.8 (5)C34—C35—C38—C39173.7 (5)
S1A—O2A—C13A—C12A97.8 (5)C36—C35—C38—C3963.9 (6)
C9—C8—C13—C124.6 (8)C34—C35—C38—C3255.0 (5)
C7—C8—C13—C12165.9 (5)C36—C35—C38—C3254.7 (5)
C9—C8—C13—O2179.7 (5)C31—C32—C38—C4054.8 (7)
C7—C8—C13—O29.1 (8)C33—C32—C38—C4064.9 (5)
C11—C12—C13—C85.3 (8)C37—C32—C38—C40170.6 (5)
C26—C12—C13—C8174.7 (5)C31—C32—C38—C3969.0 (6)
C11—C12—C13—O2179.8 (5)C33—C32—C38—C39171.3 (5)
C26—C12—C13—O20.2 (8)C37—C32—C38—C3965.6 (6)
S1—O2—C13—C881.8 (6)C31—C32—C38—C35173.3 (5)
S1—O2—C13—C12103.0 (5)C33—C32—C38—C3553.6 (4)
C1—C2—C14—C1562.8 (7)C37—C32—C38—C3552.1 (5)
C3—C2—C14—C15118.5 (6)C31A—C32A—C38A—C39A63.3 (7)
C1—C2—C14—C17176.6 (5)C37A—C32A—C38A—C39A66.4 (6)
C3—C2—C14—C172.0 (7)C33A—C32A—C38A—C39A175.5 (5)
C1—C2—C14—C1659.0 (7)C31A—C32A—C38A—C35A177.4 (5)
C3—C2—C14—C16119.6 (6)C37A—C32A—C38A—C35A52.9 (5)
C3A—C2A—C14A—C17A118.2 (6)C33A—C32A—C38A—C35A56.2 (5)
C1A—C2A—C14A—C17A60.9 (7)C31A—C32A—C38A—C40A60.0 (7)
C3A—C2A—C14A—C16A120.0 (6)C37A—C32A—C38A—C40A170.2 (5)
C1A—C2A—C14A—C16A61.0 (7)C33A—C32A—C38A—C40A61.2 (6)
C3A—C2A—C14A—C15A2.4 (8)C34A—C35A—C38A—C39A174.1 (5)
C1A—C2A—C14A—C15A178.6 (5)C36A—C35A—C38A—C39A62.7 (7)
C3A—C4A—C18A—C19A27.6 (11)C34A—C35A—C38A—C32A55.1 (5)
C5A—C4A—C18A—C19A152.3 (9)C36A—C35A—C38A—C32A56.3 (6)
C3A—C4A—C18A—C21A132.3 (9)C34A—C35A—C38A—C40A61.6 (6)
C5A—C4A—C18A—C21A47.8 (11)C36A—C35A—C38A—C40A173.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.822.232.974 (6)152
O1A—H1AA···O3A0.822.202.957 (6)153

Experimental details

Crystal data
Chemical formulaC40H60O5S
Mr652.98
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)18.2082 (19), 10.6028 (11), 20.287 (2)
β (°) 93.003 (2)
V3)3911.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.32 × 0.28 × 0.23
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax1, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
21496, 13182, 7458
Rint0.045
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.203, 1.08
No. of reflections13182
No. of parameters829
No. of restraints53
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.88, 0.35
Absolute structureFlack (1983), 5058 Friedel pairs
Absolute structure parameter0.12 (12)

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.822.232.974 (6)151.8
O1A—H1AA···O3A0.822.202.957 (6)153.0
 

Acknowledgements

We thank the National Natural Science Foundation of China (No. 21071069) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, for financial support.

References

First citationBruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationWu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602–626.  Web of Science CrossRef CAS

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