supplementary materials


su2608 scheme

Acta Cryst. (2013). E69, o1009-o1010    [ doi:10.1107/S1600536813014827 ]

1,3-Alternate conformer 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(4-methylsulfanylbenzyloxy)-2,8,14,20-tetrathiacalix[4]arene

Q. Gao, D. Xie and D. An

Abstract top

The title thiacalix[4]arene derivative, C72H80O4S8, adopts a 1,3-alternate conformation, where the four 4-methylsulfanylbenzyl groups are located alternately at the two sides of a virtual plane defined by the four bridging S atoms. In the crystal, there are no significant intermolecular interactions present. Some of the peripheral tert-butyl and methylsulfanyl groups are disordered over two positions. A region of disordered electron density, occupying voids of ca 700 Å3 for an electron count of 124, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148-155].

Comment top

Thiacalix[4]arenes are macrocyclic molecules made up of p-substituted phenolic units linked by sulfur atoms ortho to the OH functions (Kumagai et al., 1997). The ability of the parent phenolic thiacalix[4]arenes, as well as of their chemically modified derivatives obtained by the substitution of the phenolic H atoms with various types of ligating groups, to bind metal ions is well established (Morohashi et al., 2006). With thiacalix[4]arenes, the substituents frequently immobilize the molecule in a single conformation: cone, partial cone, 1,2- or 1,3-alternate. The ability to control inter-particle spatial properties of nanoparticle assemblies is one of the major challenges for the design and understanding of functional nanostructures. As a molecular linker, multidentate thioethers have been exploited for such control (Maye et al., 2005). The viability of inter-particle linkages via coordination of the methylthio groups of arylethynes to gold surfaces was demonstrated recently in our laboratory (Lim et al., 2007; Yan et al., 2010). Multi-functional groups is the common characteristic of these molecular linkers. The 1,3-alternate conformer thiacalixarene derivative is an ideal molecular linker for assembling nanoparticle clusters. With this in mind, we synthesized the title compound, the first example of a thiacalix[4]arene derivative containing multidentate methyithioethers, and we report herein on its crystal structure.

The molecular structure of the title molecule is shown in Fig 1. The macrocycle adopts a 1,3-alternate conformation in which four substituent groups are located alternately above and below the virtual plane defined by four bridging sulfur atoms, S1-S4. The 1,3-alternate conformation thus appears to be regular and two pairs of opposite phenolic units are almost parallel to each other, but the substituent groups are inclined to one another. Comparable conformations were found in methyl ester derivatives (Xu et al., 2008), whereas the title tetra-benzyl ether derivative is much more distorted as a result of increased steric hindrance.

The plane defined by the substitutional aromatic ring on O4 atom (r.m.s. deviation 0.0177 Å) was chosen as a reference plane. The plane defined by the other substitutional aromatic rings on O atoms (O1, O2 and O3) make dihedral angles of 87.83 (11), 76.84 (11) and 71.78 (13) °, respectively, with this reference plane, whereas the four aromatic rings on the skeleton make dihedral angles of 83.52 (8), 76.20 (8), 84.47 (8) and 83.09 (8) °, respectively, with this reference plane. The conformations of the benzyl ether chains are extended and deviate from the plane defined by four bridging sulfur atoms. Atoms C41, C49, C57 and C65 point towards the exterior of the macrocycle and the torsion angles around the O1—C41, C49—O2, C57—O3 and C65—O4 bonds deviate from ideal syn or anti values by more than 70°.

In the crystal, there are no significant intermolecular interactions present.

Related literature top

For a similar compound adopting a 1,3-alternate conformation, see: Xu et al. (2008). For background to thiacalix[4]arene derivatives, see: Kumagai et al. (1997); Morohashi et al. (2006); Yamato et al. (2006). For background to multidentate methylthioethers, see: Maye et al. (2005); Lim et al. (2007); Yan et al. (2010). For the synthesis, see: Morohashi et al. (2003). For related literature, see: Yamato et al. (2006).

Experimental top

A mixture of p-tetra-tert-butylthiacalix[4]arene (360 mg, 0.50 mmol) and Cs2CO3 (1.30 g, 4.00 mmol) in anhydrous acetone (50 ml) was heated at refluxed for 30 min. Then a solution of 4-methylthiobenzyl bromide (864 mg, 4.00 mmol) in acetone (10 ml) was added and the mixture heated at reflux for 2 h. After cooling the reaction mixture, it was filtered. The filtrate was concentrated and the residue was purified by column chromatography from petroleum ether/dichloromethane (4:1, v/v) to give 410 mg (65%) of compound I as a white solid: M.p. 513~516 K; MS(ESI) m/z: 1283.1 [M+H2O]+. Spectroscopic data for the title compound is available in the archived CIF. Colourless crystals of the title compound, suitable for X-ray diffraction analysis, were obtained by slow diffusion of petroleum ether into a chloroform solution at 298 K.

Refinement top

Some of the peripheral -SCH3 and t-butyl groups are disordered over two positions. These include the S-CH3 groups involving atoms S5-C48, S6-C56, S7-C64 and S8-C72, and the t-butyl groups involving atoms C18-C20, C28-C30 and C38-C40; details are available in the archived CIF. A region of disordered electron density occupying voids of ca. 700 Å3, for an electron count of 124, was treated using the SQUEEZE routine in PLATON (Spek, 2009). It was not taken into consideration during refinement. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major components of the disordered peripheral groups are shown.
5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis(4-methylsulfanylbenzyloxy)-2,8,14,20-tetrathiacalix[4]arene top
Crystal data top
C72H80O4S8Z = 2
Mr = 1265.84F(000) = 1344
Triclinic, P1Dx = 1.087 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 15.1863 (10) ÅCell parameters from 4356 reflections
b = 15.5795 (11) Åθ = 4.4–45.1°
c = 16.9774 (12) ŵ = 0.27 mm1
α = 75.473 (2)°T = 293 K
β = 85.686 (2)°Prismatic, colourless
γ = 84.762 (2)°0.26 × 0.21 × 0.15 mm
V = 3866.4 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
14394 independent reflections
Radiation source: fine-focus sealed tube9034 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
phi and ω scansθmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1818
Tmin = 0.434, Tmax = 1.000k = 1818
14394 measured reflectionsl = 020
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.1009P)2]
where P = (Fo2 + 2Fc2)/3
14394 reflections(Δ/σ)max = 0.004
939 parametersΔρmax = 0.40 e Å3
244 restraintsΔρmin = 0.29 e Å3
Crystal data top
C72H80O4S8γ = 84.762 (2)°
Mr = 1265.84V = 3866.4 (5) Å3
Triclinic, P1Z = 2
a = 15.1863 (10) ÅMo Kα radiation
b = 15.5795 (11) ŵ = 0.27 mm1
c = 16.9774 (12) ÅT = 293 K
α = 75.473 (2)°0.26 × 0.21 × 0.15 mm
β = 85.686 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
14394 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
9034 reflections with I > 2σ(I)
Tmin = 0.434, Tmax = 1.000Rint = 0.000
14394 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.172Δρmax = 0.40 e Å3
S = 0.96Δρmin = 0.29 e Å3
14394 reflectionsAbsolute structure: ?
939 parametersAbsolute structure parameter: ?
244 restraintsRogers parameter: ?
Special details top

Experimental. Spectroscopic data for the title compound:

1H NMR (400 MHz, CDCl3): 7.12 (s, 8H), 7.05 (d, J = 8.4 Hz, 8H), 6.92 (d, J = 8.4 Hz, 8H), 5.04 (s, 8H), 2.48 (s, 12H, SCH3), 0.86 (s, 36H); 13C NMR (100 MHz, CDCl3): 156.89 (C), 146.15 (C), 136.67 (C), 134.87 (C), 129.26 (CH), 128.57 (C), 127.69 (CH), 126.95 (CH), 70.65 (CH2), 33.86 (C), 30.73 (CH3), 16.31 (SCH3).

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)
S10.94198 (4)0.90174 (4)0.09861 (4)0.05036 (19)
S20.92245 (5)0.55348 (5)0.07790 (5)0.0582 (2)
S30.55404 (5)0.59267 (5)0.09846 (5)0.0631 (2)
S40.57286 (4)0.93527 (5)0.13515 (4)0.0541 (2)
S51.3408 (4)0.7583 (4)0.0886 (7)0.1079 (15)0.70
S60.7412 (5)0.5926 (7)0.5541 (5)0.1038 (18)0.50
S70.7645 (7)0.8754 (7)0.3436 (5)0.101 (2)0.50
S80.5403 (5)1.1277 (5)0.4157 (3)0.0949 (13)0.55
C481.3875 (3)0.6516 (4)0.0944 (4)0.0867 (19)0.65
H48A1.37280.60890.04480.130*0.65
H48B1.45070.65260.10230.130*0.65
H48C1.36440.63550.13940.130*0.65
C560.7113 (9)0.7107 (9)0.5414 (10)0.122 (4)0.50
H56A0.76010.74380.51510.184*0.50
H56B0.69710.72270.59390.184*0.50
H56C0.66080.72790.50870.184*0.50
C640.6894 (8)0.9425 (8)0.4157 (6)0.118 (4)0.50
H64A0.66670.99410.39740.177*0.50
H64B0.64130.90840.42030.177*0.50
H64C0.72030.96060.46790.177*0.50
C720.5345 (9)1.2383 (7)0.3516 (8)0.119 (3)0.60
H72D0.59301.25840.33980.179*0.60
H72E0.49871.27720.37890.179*0.60
H72F0.50861.23850.30160.179*0.60
S5'1.3463 (11)0.7406 (12)0.0752 (17)0.1084 (16)0.30
S6'0.7109 (6)0.6042 (8)0.5530 (6)0.122 (3)0.50
S7'0.7480 (8)0.8905 (8)0.3466 (5)0.117 (3)0.50
S8'0.5571 (8)1.1460 (8)0.4075 (6)0.140 (4)0.45
C48'1.3332 (13)0.6556 (10)0.1267 (10)0.138 (5)0.35
H48D1.34090.59830.08940.207*0.35
H48E1.37660.65970.17140.207*0.35
H48F1.27490.66350.14700.207*0.35
C56'0.7588 (10)0.7043 (10)0.5410 (10)0.138 (5)0.50
H56D0.74280.74390.49010.208*0.50
H56E0.82200.69350.54120.208*0.50
H56F0.73790.73070.58500.208*0.50
C64'0.6973 (10)0.9922 (8)0.4005 (8)0.143 (5)0.50
H64D0.63410.99110.39220.215*0.50
H64E0.71361.00110.45760.215*0.50
H64F0.71641.03990.38120.215*0.50
C72'0.5716 (15)1.2563 (14)0.3432 (17)0.174 (11)0.40
H72A0.63051.27200.34720.260*0.40
H72B0.52941.29840.36070.260*0.40
H72C0.56271.25680.28770.260*0.40
O10.89430 (12)0.76024 (13)0.01849 (11)0.0584 (5)
O20.74105 (12)0.60108 (12)0.15708 (10)0.0515 (4)
O30.61701 (11)0.78218 (12)0.04810 (10)0.0482 (4)
O40.75495 (12)0.85942 (12)0.18907 (11)0.0554 (5)
C10.94462 (15)0.78558 (16)0.14019 (15)0.0422 (6)
C20.97394 (16)0.75315 (17)0.21775 (15)0.0475 (6)
H20.98650.79330.24700.057*
C30.98546 (16)0.66224 (18)0.25391 (15)0.0478 (6)
C40.96376 (16)0.60604 (17)0.20888 (16)0.0486 (6)
H40.96860.54510.23190.058*
C50.93484 (15)0.63659 (16)0.13047 (15)0.0433 (6)
C60.92664 (15)0.72676 (16)0.09419 (14)0.0410 (6)
C71.01959 (18)0.6293 (2)0.34044 (16)0.0604 (8)
C81.0129 (3)0.5297 (3)0.3732 (2)0.1042 (13)
H8A0.95200.51650.37660.156*
H8B1.03610.51100.42640.156*
H8C1.04650.49870.33720.156*
C91.1168 (2)0.6489 (3)0.3363 (2)0.1014 (13)
H9A1.15060.61660.30160.152*
H9B1.13870.63090.39000.152*
H9C1.12200.71150.31480.152*
C100.9657 (3)0.6748 (3)0.3990 (2)0.1032 (13)
H10A0.97070.73780.38140.155*
H10B0.98760.65290.45260.155*
H10C0.90480.66250.40040.155*
C110.81713 (17)0.57302 (16)0.03584 (16)0.0468 (6)
C120.81386 (18)0.56067 (17)0.04176 (16)0.0513 (7)
H120.86670.55130.07090.062*
C130.73439 (19)0.56175 (18)0.07774 (16)0.0536 (7)
C140.65774 (18)0.57739 (19)0.03304 (16)0.0545 (7)
H140.60350.57990.05590.065*
C150.65889 (17)0.58959 (17)0.04548 (16)0.0494 (6)
C160.73887 (17)0.58747 (16)0.08053 (15)0.0455 (6)
C170.7309 (2)0.5441 (2)0.16228 (19)0.0693 (9)
C180.8077 (14)0.5946 (9)0.2193 (10)0.079 (3)0.50
H18A0.86420.56920.19930.119*0.50
H18B0.80120.65650.21930.119*0.50
H18C0.80420.58850.27390.119*0.50
C190.7130 (6)0.4463 (7)0.1505 (7)0.099 (3)0.60
H19A0.70580.43480.20260.148*0.60
H19B0.65990.43400.11660.148*0.60
H19C0.76190.40890.12510.148*0.60
C200.6510 (10)0.6081 (7)0.2097 (9)0.081 (3)0.50
H20A0.66260.66920.21670.121*0.50
H20B0.59620.59660.17840.121*0.50
H20C0.64710.59620.26210.121*0.50
C18'0.8117 (15)0.5609 (9)0.2147 (12)0.095 (5)0.50
H18D0.80410.54750.26590.143*0.50
H18E0.86060.52390.18870.143*0.50
H18F0.82350.62220.22400.143*0.50
C19'0.7610 (10)0.4428 (12)0.1482 (11)0.112 (5)0.40
H19D0.75810.42490.19810.169*0.40
H19E0.72260.40890.10680.169*0.40
H19F0.82070.43250.13120.169*0.40
C20'0.6462 (10)0.5704 (7)0.1996 (9)0.087 (3)0.50
H20D0.63580.63390.21190.131*0.50
H20E0.59970.54380.16250.131*0.50
H20F0.64710.55070.24890.131*0.50
C210.55120 (16)0.67324 (18)0.15619 (15)0.0480 (6)
C220.51071 (17)0.64880 (19)0.23451 (16)0.0524 (7)
H220.49420.59100.25470.063*
C230.49475 (16)0.70917 (19)0.28255 (15)0.0506 (7)
C240.52130 (16)0.79369 (19)0.25020 (15)0.0485 (6)
H240.51210.83500.28170.058*
C250.56121 (15)0.81970 (17)0.17237 (15)0.0448 (6)
C260.57623 (15)0.75879 (17)0.12452 (14)0.0432 (6)
C270.4468 (2)0.6825 (2)0.36633 (17)0.0648 (8)
C280.4834 (8)0.5980 (8)0.4150 (7)0.078 (3)0.55
H28A0.44910.58210.46570.118*0.55
H28B0.54360.60330.42570.118*0.55
H28C0.48170.55280.38590.118*0.55
C290.4863 (8)0.7236 (9)0.4259 (8)0.120 (4)0.50
H29A0.46220.69880.48000.180*0.50
H29B0.47230.78670.41170.180*0.50
H29C0.54940.71130.42400.180*0.50
C300.3469 (7)0.6736 (6)0.3514 (6)0.063 (2)0.55
H30A0.34380.62650.32470.095*0.55
H30B0.32280.72840.31760.095*0.55
H30C0.31350.66040.40270.095*0.55
C28'0.4615 (12)0.5716 (11)0.4032 (12)0.107 (6)0.45
H28D0.52180.55190.39210.161*0.45
H28E0.42270.54280.37760.161*0.45
H28F0.44820.55690.46100.161*0.45
C29'0.4421 (7)0.7589 (7)0.4124 (7)0.096 (3)0.50
H29D0.41330.73930.46540.144*0.50
H29E0.40920.81050.38180.144*0.50
H29F0.50100.77350.41800.144*0.50
C30'0.3535 (11)0.7105 (9)0.3632 (10)0.100 (5)0.45
H30D0.32830.68870.32250.150*0.45
H30E0.34590.77430.34980.150*0.45
H30F0.32420.68720.41540.150*0.45
C310.67539 (16)0.94933 (16)0.07791 (16)0.0457 (6)
C320.67360 (17)1.00449 (17)0.00043 (17)0.0520 (7)
H320.61911.02640.02090.062*
C330.75021 (17)1.02849 (17)0.04684 (16)0.0506 (7)
C340.82966 (16)0.99078 (16)0.01344 (16)0.0465 (6)
H340.88231.00340.04430.056*
C350.83338 (15)0.93503 (15)0.06423 (16)0.0424 (6)
C360.75657 (16)0.91547 (15)0.11223 (15)0.0424 (6)
C370.7462 (2)1.0937 (2)0.13094 (19)0.0690 (9)
C380.8285 (5)1.1254 (7)0.1654 (6)0.100 (3)0.50
H38A0.86961.07590.16970.151*0.50
H38B0.85131.15790.13130.151*0.50
H38C0.82031.16370.21870.151*0.50
C390.6820 (5)1.1826 (4)0.1164 (4)0.0743 (19)0.50
H39A0.67601.22580.16750.112*0.50
H39B0.70861.20820.07900.112*0.50
H39C0.62451.16450.09440.112*0.50
C400.6885 (7)1.0612 (6)0.1841 (6)0.077 (3)0.60
H40A0.62911.05900.16050.116*0.60
H40B0.71091.00280.18840.116*0.60
H40C0.68881.10100.23740.116*0.60
C38'0.8304 (6)1.0565 (6)0.1917 (4)0.092 (2)0.50
H38D0.82470.99510.18980.138*0.50
H38E0.88671.06260.17220.138*0.50
H38F0.82661.09120.24690.138*0.50
C39'0.7743 (8)1.1786 (5)0.1287 (5)0.110 (3)0.50
H39D0.77491.21710.18260.166*0.50
H39E0.83271.17090.10870.166*0.50
H39F0.73391.20460.09330.166*0.50
C40'0.6673 (10)1.0938 (10)0.1712 (10)0.093 (5)0.40
H40D0.67771.11730.22880.140*0.40
H40E0.62101.13010.15090.140*0.40
H40F0.65001.03410.16110.140*0.40
C410.9429 (2)0.7617 (3)0.05348 (19)0.0923 (12)
H41A0.92340.81590.09240.111*
H41B0.92630.71250.07330.111*
C421.04093 (19)0.7569 (2)0.05638 (16)0.0562 (7)
C431.0881 (2)0.8287 (2)0.0609 (2)0.0734 (9)
H431.05710.88190.05700.088*
C441.1777 (2)0.8264 (2)0.0708 (2)0.0770 (9)
H441.20620.87800.07550.092*
C451.2255 (2)0.7502 (2)0.07393 (19)0.0663 (8)
C461.1828 (2)0.6758 (2)0.0680 (2)0.0847 (11)
H461.21490.62260.07020.102*
C471.0911 (2)0.6795 (2)0.0585 (2)0.0836 (10)
H471.06270.62780.05340.100*
C490.7374 (2)0.5227 (2)0.22128 (18)0.0722 (9)
H49A0.78840.48190.21580.087*
H49B0.68440.49350.21850.087*
C500.73654 (19)0.5463 (2)0.30111 (16)0.0590 (7)
C510.7421 (2)0.4787 (2)0.3715 (2)0.0797 (10)
H510.74690.41990.36790.096*
C520.7408 (3)0.4970 (3)0.4467 (2)0.0885 (11)
H520.74630.45040.49290.106*
C530.7316 (2)0.5822 (3)0.45457 (18)0.0762 (10)
C540.7265 (2)0.6505 (2)0.38446 (18)0.0738 (9)
H540.72150.70930.38840.089*
C550.7288 (2)0.6322 (2)0.30871 (17)0.0635 (8)
H550.72500.67890.26230.076*
C570.55681 (18)0.8144 (2)0.01567 (16)0.0621 (8)
H57A0.52630.87020.01010.074*
H57B0.51290.77180.01190.074*
C580.60755 (17)0.82777 (18)0.09687 (15)0.0498 (6)
C590.69751 (18)0.8091 (2)0.10537 (17)0.0595 (8)
H590.72970.78510.05940.071*
C600.7401 (2)0.8257 (2)0.18123 (18)0.0677 (9)
H600.80090.81210.18600.081*
C610.6942 (2)0.8625 (2)0.25093 (17)0.0671 (8)
C620.6036 (2)0.8789 (2)0.24219 (18)0.0712 (9)
H620.57100.90160.28810.085*
C630.56160 (19)0.8621 (2)0.16682 (18)0.0613 (8)
H630.50050.87390.16210.074*
C650.7901 (2)0.8914 (2)0.25194 (18)0.0726 (9)
H65A0.84290.92170.22960.087*
H65B0.80780.84080.29550.087*
C660.7271 (2)0.9535 (2)0.28716 (18)0.0674 (8)
C670.7308 (4)1.0429 (3)0.2639 (3)0.1251 (17)
H670.77251.06680.22330.150*
C680.6738 (4)1.1006 (3)0.2991 (3)0.1278 (18)
H680.67701.16170.28020.153*
C690.6153 (3)1.0692 (3)0.3591 (2)0.0833 (10)
C700.6075 (3)0.9797 (3)0.3810 (2)0.0950 (12)
H700.56430.95670.42040.114*
C710.6625 (3)0.9227 (3)0.3458 (2)0.0841 (10)
H710.65560.86200.36230.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0351 (3)0.0425 (4)0.0712 (5)0.0045 (3)0.0091 (3)0.0073 (3)
S20.0531 (4)0.0521 (4)0.0765 (5)0.0083 (3)0.0126 (4)0.0308 (4)
S30.0511 (4)0.0731 (5)0.0756 (5)0.0196 (4)0.0114 (4)0.0365 (4)
S40.0399 (4)0.0493 (4)0.0695 (5)0.0021 (3)0.0070 (3)0.0126 (3)
S50.0590 (11)0.091 (3)0.175 (4)0.0079 (15)0.0024 (14)0.037 (3)
S60.135 (5)0.135 (3)0.0394 (16)0.007 (3)0.019 (3)0.0198 (15)
S70.095 (3)0.167 (5)0.043 (2)0.012 (4)0.0104 (16)0.031 (3)
S80.108 (2)0.119 (3)0.0641 (16)0.021 (3)0.0073 (16)0.0442 (16)
C480.039 (3)0.095 (4)0.123 (5)0.021 (3)0.015 (3)0.029 (3)
C560.137 (9)0.165 (9)0.080 (6)0.016 (7)0.008 (7)0.057 (6)
C640.134 (7)0.149 (8)0.054 (5)0.018 (7)0.003 (5)0.008 (5)
C720.137 (7)0.102 (6)0.127 (6)0.001 (5)0.010 (6)0.049 (5)
S5'0.0595 (13)0.092 (3)0.175 (4)0.0095 (18)0.0015 (16)0.037 (3)
S6'0.135 (5)0.177 (6)0.056 (2)0.021 (4)0.000 (3)0.029 (3)
S7'0.122 (5)0.152 (4)0.057 (2)0.019 (3)0.024 (2)0.005 (2)
S8'0.159 (6)0.146 (6)0.137 (5)0.001 (4)0.007 (3)0.083 (4)
C48'0.182 (10)0.106 (8)0.129 (9)0.016 (8)0.038 (8)0.048 (7)
C56'0.163 (10)0.179 (9)0.089 (7)0.013 (8)0.005 (8)0.064 (6)
C64'0.173 (9)0.127 (8)0.106 (8)0.023 (7)0.009 (6)0.013 (6)
C72'0.178 (14)0.166 (13)0.180 (13)0.000 (9)0.003 (9)0.056 (9)
O10.0476 (11)0.0799 (14)0.0445 (11)0.0093 (9)0.0129 (9)0.0113 (9)
O20.0602 (11)0.0554 (11)0.0418 (10)0.0062 (9)0.0020 (8)0.0172 (8)
O30.0394 (9)0.0626 (11)0.0409 (10)0.0054 (8)0.0035 (8)0.0106 (8)
O40.0515 (11)0.0623 (12)0.0476 (11)0.0014 (9)0.0024 (9)0.0056 (9)
C10.0311 (12)0.0451 (14)0.0496 (15)0.0011 (10)0.0043 (11)0.0101 (11)
C20.0410 (14)0.0534 (16)0.0506 (16)0.0024 (12)0.0082 (12)0.0160 (12)
C30.0381 (14)0.0607 (17)0.0433 (14)0.0025 (12)0.0055 (11)0.0117 (13)
C40.0439 (14)0.0442 (15)0.0536 (16)0.0030 (12)0.0050 (12)0.0059 (12)
C50.0381 (13)0.0429 (14)0.0500 (15)0.0031 (11)0.0071 (11)0.0143 (12)
C60.0313 (12)0.0483 (15)0.0429 (14)0.0001 (11)0.0041 (10)0.0110 (11)
C70.0507 (16)0.079 (2)0.0449 (16)0.0031 (15)0.0125 (13)0.0036 (14)
C80.126 (3)0.105 (3)0.066 (2)0.009 (2)0.021 (2)0.012 (2)
C90.066 (2)0.150 (4)0.078 (2)0.014 (2)0.0329 (19)0.004 (2)
C100.107 (3)0.147 (4)0.055 (2)0.019 (3)0.009 (2)0.033 (2)
C110.0506 (15)0.0406 (14)0.0527 (16)0.0048 (12)0.0048 (13)0.0171 (12)
C120.0526 (16)0.0503 (16)0.0545 (16)0.0058 (13)0.0058 (13)0.0213 (13)
C130.0592 (17)0.0534 (16)0.0524 (16)0.0065 (13)0.0007 (14)0.0210 (13)
C140.0511 (16)0.0656 (18)0.0531 (16)0.0071 (14)0.0069 (13)0.0242 (14)
C150.0513 (16)0.0484 (15)0.0513 (16)0.0064 (12)0.0015 (13)0.0178 (12)
C160.0523 (16)0.0412 (14)0.0448 (15)0.0061 (12)0.0003 (12)0.0138 (11)
C170.074 (2)0.085 (2)0.0605 (19)0.0099 (18)0.0001 (17)0.0375 (17)
C180.094 (6)0.100 (8)0.046 (4)0.006 (7)0.012 (4)0.030 (5)
C190.118 (6)0.102 (5)0.100 (5)0.004 (5)0.028 (5)0.065 (4)
C200.093 (5)0.095 (6)0.061 (5)0.002 (5)0.017 (4)0.029 (5)
C18'0.102 (7)0.110 (9)0.083 (7)0.019 (7)0.007 (5)0.041 (7)
C19'0.143 (10)0.117 (8)0.101 (8)0.020 (8)0.001 (8)0.071 (6)
C20'0.096 (6)0.108 (7)0.069 (5)0.015 (6)0.019 (4)0.038 (5)
C210.0399 (14)0.0571 (17)0.0487 (15)0.0077 (12)0.0011 (12)0.0156 (12)
C220.0465 (15)0.0551 (17)0.0519 (16)0.0114 (13)0.0041 (13)0.0057 (13)
C230.0389 (14)0.0682 (19)0.0425 (14)0.0038 (13)0.0006 (11)0.0105 (13)
C240.0389 (14)0.0627 (18)0.0449 (15)0.0000 (12)0.0012 (12)0.0172 (13)
C250.0329 (13)0.0538 (16)0.0464 (15)0.0013 (11)0.0017 (11)0.0107 (12)
C260.0306 (12)0.0554 (16)0.0407 (14)0.0043 (11)0.0049 (11)0.0083 (12)
C270.0577 (18)0.088 (2)0.0436 (16)0.0090 (16)0.0098 (14)0.0090 (15)
C280.075 (5)0.090 (6)0.051 (4)0.001 (5)0.007 (4)0.015 (4)
C290.143 (8)0.148 (9)0.070 (6)0.033 (7)0.037 (6)0.033 (6)
C300.042 (3)0.087 (6)0.049 (4)0.005 (4)0.010 (3)0.003 (4)
C28'0.118 (10)0.100 (9)0.084 (8)0.001 (7)0.015 (7)0.005 (6)
C29'0.110 (7)0.120 (7)0.064 (5)0.028 (5)0.030 (5)0.038 (5)
C30'0.083 (7)0.112 (9)0.085 (7)0.008 (7)0.018 (5)0.001 (6)
C310.0368 (13)0.0401 (14)0.0599 (17)0.0021 (11)0.0015 (12)0.0123 (12)
C320.0381 (14)0.0443 (15)0.0677 (18)0.0015 (12)0.0080 (13)0.0021 (13)
C330.0462 (15)0.0424 (15)0.0587 (17)0.0123 (12)0.0104 (13)0.0012 (12)
C340.0380 (13)0.0410 (14)0.0570 (16)0.0083 (11)0.0004 (12)0.0045 (12)
C350.0350 (13)0.0339 (13)0.0593 (16)0.0024 (10)0.0071 (12)0.0119 (12)
C360.0434 (14)0.0355 (13)0.0477 (15)0.0004 (11)0.0055 (12)0.0093 (11)
C370.0621 (19)0.065 (2)0.069 (2)0.0211 (16)0.0154 (16)0.0133 (16)
C380.061 (4)0.118 (6)0.089 (5)0.018 (5)0.000 (4)0.039 (5)
C390.093 (5)0.048 (3)0.071 (4)0.007 (3)0.021 (4)0.007 (3)
C400.107 (7)0.067 (4)0.054 (4)0.006 (4)0.016 (4)0.004 (3)
C38'0.095 (5)0.107 (6)0.061 (4)0.005 (5)0.013 (4)0.001 (4)
C39'0.161 (7)0.070 (5)0.085 (5)0.021 (5)0.000 (5)0.012 (4)
C40'0.065 (6)0.108 (9)0.089 (8)0.010 (6)0.021 (5)0.015 (7)
C410.062 (2)0.162 (4)0.0470 (19)0.015 (2)0.0070 (16)0.011 (2)
C420.0555 (17)0.071 (2)0.0429 (15)0.0130 (15)0.0041 (13)0.0116 (14)
C430.071 (2)0.069 (2)0.083 (2)0.0003 (18)0.0100 (18)0.0301 (17)
C440.067 (2)0.067 (2)0.106 (3)0.0133 (17)0.0039 (19)0.0374 (19)
C450.0644 (19)0.0563 (19)0.076 (2)0.0111 (16)0.0012 (16)0.0114 (15)
C460.070 (2)0.054 (2)0.132 (3)0.0011 (17)0.004 (2)0.030 (2)
C470.084 (3)0.060 (2)0.110 (3)0.0286 (19)0.007 (2)0.0222 (19)
C490.099 (3)0.061 (2)0.0546 (18)0.0098 (17)0.0013 (17)0.0103 (15)
C500.0586 (17)0.071 (2)0.0445 (16)0.0104 (15)0.0009 (13)0.0068 (14)
C510.104 (3)0.069 (2)0.060 (2)0.0149 (19)0.0018 (19)0.0024 (17)
C520.101 (3)0.103 (3)0.050 (2)0.021 (2)0.0058 (18)0.008 (2)
C530.076 (2)0.107 (3)0.0442 (18)0.013 (2)0.0002 (15)0.0153 (18)
C540.086 (2)0.083 (2)0.0519 (19)0.0030 (18)0.0057 (16)0.0177 (17)
C550.074 (2)0.070 (2)0.0438 (16)0.0010 (16)0.0058 (14)0.0099 (14)
C570.0465 (16)0.082 (2)0.0534 (17)0.0003 (15)0.0019 (13)0.0102 (15)
C580.0492 (16)0.0563 (16)0.0424 (15)0.0047 (13)0.0014 (12)0.0094 (12)
C590.0503 (17)0.077 (2)0.0464 (16)0.0027 (14)0.0018 (13)0.0093 (14)
C600.0531 (17)0.096 (2)0.0527 (18)0.0003 (16)0.0019 (14)0.0193 (16)
C610.075 (2)0.083 (2)0.0451 (17)0.0056 (17)0.0005 (15)0.0204 (15)
C620.078 (2)0.091 (2)0.0457 (17)0.0085 (18)0.0139 (16)0.0142 (16)
C630.0510 (16)0.074 (2)0.0609 (19)0.0034 (14)0.0106 (14)0.0180 (15)
C650.0573 (18)0.108 (3)0.0528 (18)0.0022 (18)0.0069 (15)0.0219 (17)
C660.066 (2)0.087 (2)0.0519 (18)0.0102 (18)0.0030 (15)0.0192 (17)
C670.159 (5)0.109 (4)0.104 (3)0.037 (3)0.060 (3)0.031 (3)
C680.178 (5)0.085 (3)0.115 (4)0.014 (3)0.039 (4)0.028 (3)
C690.092 (3)0.099 (3)0.066 (2)0.002 (2)0.009 (2)0.036 (2)
C700.087 (3)0.128 (4)0.071 (2)0.010 (3)0.018 (2)0.033 (2)
C710.093 (3)0.085 (2)0.072 (2)0.008 (2)0.011 (2)0.0201 (19)
Geometric parameters (Å, º) top
S1—C11.768 (3)C23—C241.378 (4)
S1—C351.779 (2)C23—C271.526 (4)
S2—C111.770 (3)C24—C251.390 (3)
S2—C51.777 (3)C24—H240.9300
S3—C151.772 (3)C25—C261.390 (4)
S3—C211.772 (3)C27—C30'1.445 (16)
S4—C251.773 (3)C27—C281.454 (12)
S4—C311.773 (3)C27—C291.510 (14)
S5—C451.762 (8)C27—C29'1.574 (12)
S5—C481.769 (8)C27—C301.580 (10)
S6—C531.756 (9)C27—C28'1.683 (17)
S6—C561.816 (14)C28—H28A0.9600
S7—C641.800 (12)C28—H28B0.9600
S7—C611.811 (9)C28—H28C0.9600
S8—C691.773 (7)C29—H29A0.9600
S8—C721.791 (11)C29—H29B0.9600
C48—H48A0.9600C29—H29C0.9600
C48—H48B0.9600C30—H30A0.9600
C48—H48C0.9600C30—H30B0.9600
C56—H56A0.9600C30—H30C0.9600
C56—H56B0.9600C28'—H28D0.9600
C56—H56C0.9600C28'—H28E0.9600
C64—H64A0.9600C28'—H28F0.9600
C64—H64B0.9600C29'—H29D0.9600
C64—H64C0.9600C29'—H29E0.9600
C72—H72D0.9600C29'—H29F0.9600
C72—H72E0.9600C30'—H30D0.9600
C72—H72F0.9600C30'—H30E0.9600
S5'—C48'1.792 (19)C30'—H30F0.9600
S5'—C451.827 (17)C31—C321.380 (3)
S6'—C56'1.740 (14)C31—C361.405 (3)
S6'—C531.787 (10)C32—C331.388 (4)
S7'—C611.734 (10)C32—H320.9300
S7'—C64'1.760 (13)C33—C341.389 (3)
S8'—C691.756 (10)C33—C371.532 (4)
S8'—C72'1.812 (17)C34—C351.387 (3)
C48'—H48D0.9600C34—H340.9300
C48'—H48E0.9600C35—C361.384 (3)
C48'—H48F0.9600C37—C381.416 (8)
C56'—H56D0.9600C37—C40'1.423 (16)
C56'—H56E0.9600C37—C39'1.437 (9)
C56'—H56F0.9600C37—C401.506 (11)
C64'—H64D0.9600C37—C391.678 (7)
C64'—H64E0.9600C37—C38'1.733 (9)
C64'—H64F0.9600C38—H38A0.9600
C72'—H72A0.9600C38—H38B0.9600
C72'—H72B0.9600C38—H38C0.9600
C72'—H72C0.9600C39—H39A0.9600
O1—C61.370 (3)C39—H39B0.9600
O1—C411.375 (4)C39—H39C0.9600
O2—C161.371 (3)C40—H40A0.9600
O2—C491.421 (3)C40—H40B0.9600
O3—C261.372 (3)C40—H40C0.9600
O3—C571.433 (3)C38'—H38D0.9600
O4—C361.376 (3)C38'—H38E0.9600
O4—C651.440 (4)C38'—H38F0.9600
C1—C21.379 (3)C39'—H39D0.9600
C1—C61.400 (3)C39'—H39E0.9600
C2—C31.396 (4)C39'—H39F0.9600
C2—H20.9300C40'—H40D0.9600
C3—C41.373 (4)C40'—H40E0.9600
C3—C71.542 (4)C40'—H40F0.9600
C4—C51.387 (3)C41—C421.482 (4)
C4—H40.9300C41—H41A0.9700
C5—C61.384 (3)C41—H41B0.9700
C7—C101.512 (5)C42—C431.366 (4)
C7—C81.522 (5)C42—C471.373 (4)
C7—C91.527 (4)C43—C441.357 (4)
C8—H8A0.9600C43—H430.9300
C8—H8B0.9600C44—C451.345 (4)
C8—H8C0.9600C44—H440.9300
C9—H9A0.9600C45—C461.357 (4)
C9—H9B0.9600C46—C471.388 (5)
C9—H9C0.9600C46—H460.9300
C10—H10A0.9600C47—H470.9300
C10—H10B0.9600C49—C501.489 (4)
C10—H10C0.9600C49—H49A0.9700
C11—C121.383 (4)C49—H49B0.9700
C11—C161.393 (4)C50—C551.371 (4)
C12—C131.390 (4)C50—C511.382 (4)
C12—H120.9300C51—C521.374 (5)
C13—C141.378 (4)C51—H510.9300
C13—C171.533 (4)C52—C531.361 (5)
C14—C151.395 (4)C52—H520.9300
C14—H140.9300C53—C541.385 (5)
C15—C161.386 (4)C54—C551.383 (4)
C17—C20'1.457 (14)C54—H540.9300
C17—C18'1.46 (2)C55—H550.9300
C17—C191.534 (11)C57—C581.504 (4)
C17—C19'1.566 (18)C57—H57A0.9700
C17—C181.592 (18)C57—H57B0.9700
C17—C201.624 (13)C58—C591.375 (4)
C18—H18A0.9600C58—C631.386 (4)
C18—H18B0.9600C59—C601.372 (4)
C18—H18C0.9600C59—H590.9300
C19—H19A0.9600C60—C611.388 (4)
C19—H19B0.9600C60—H600.9300
C19—H19C0.9600C61—C621.380 (4)
C20—H20A0.9600C62—C631.361 (4)
C20—H20B0.9600C62—H620.9300
C20—H20C0.9600C63—H630.9300
C18'—H18D0.9600C65—C661.498 (4)
C18'—H18E0.9600C65—H65A0.9700
C18'—H18F0.9600C65—H65B0.9700
C19'—H19D0.9600C66—C671.354 (5)
C19'—H19E0.9600C66—C711.373 (5)
C19'—H19F0.9600C67—C681.402 (6)
C20'—H20D0.9600C67—H670.9300
C20'—H20E0.9600C68—C691.325 (6)
C20'—H20F0.9600C68—H680.9300
C21—C261.383 (4)C69—C701.364 (5)
C21—C221.399 (4)C70—C711.376 (5)
C22—C231.386 (4)C70—H700.9300
C22—H220.9300C71—H710.9300
C1—S1—C35106.14 (11)C27—C30—H30B109.5
C11—S2—C5108.71 (11)C27—C30—H30C109.5
C15—S3—C21108.63 (12)C27—C28'—H28D109.5
C25—S4—C31108.22 (11)C27—C28'—H28E109.5
C45—S5—C48106.3 (4)H28D—C28'—H28E109.5
C53—S6—C56100.8 (7)C27—C28'—H28F109.5
C64—S7—C61100.0 (6)H28D—C28'—H28F109.5
C69—S8—C72102.6 (6)H28E—C28'—H28F109.5
C48'—S5'—C4582.1 (9)C27—C29'—H29D109.5
C56'—S6'—C53102.5 (8)C27—C29'—H29E109.5
C61—S7'—C64'107.7 (8)H29D—C29'—H29E109.5
C69—S8'—C72'107.6 (11)C27—C29'—H29F109.5
S5'—C48'—H48D109.5H29D—C29'—H29F109.5
S5'—C48'—H48E109.5H29E—C29'—H29F109.5
H48D—C48'—H48E109.5C27—C30'—H30D109.5
S5'—C48'—H48F109.5C27—C30'—H30E109.5
H48D—C48'—H48F109.5H30D—C30'—H30E109.5
H48E—C48'—H48F109.5C27—C30'—H30F109.5
S6'—C56'—H56D109.5H30D—C30'—H30F109.5
S6'—C56'—H56E109.5H30E—C30'—H30F109.5
H56D—C56'—H56E109.5C32—C31—C36120.3 (2)
S6'—C56'—H56F109.5C32—C31—S4117.03 (18)
H56D—C56'—H56F109.5C36—C31—S4122.17 (19)
H56E—C56'—H56F109.5C31—C32—C33122.4 (2)
S7'—C64'—H64D109.5C31—C32—H32118.8
S7'—C64'—H64E109.5C33—C32—H32118.8
H64D—C64'—H64E109.5C32—C33—C34116.4 (2)
S7'—C64'—H64F109.5C32—C33—C37121.2 (2)
H64D—C64'—H64F109.5C34—C33—C37122.5 (2)
H64E—C64'—H64F109.5C35—C34—C33122.4 (2)
S8'—C72'—H72A109.5C35—C34—H34118.8
S8'—C72'—H72B109.5C33—C34—H34118.8
H72A—C72'—H72B109.5C36—C35—C34120.5 (2)
S8'—C72'—H72C109.5C36—C35—S1124.13 (19)
H72A—C72'—H72C109.5C34—C35—S1115.11 (18)
H72B—C72'—H72C109.5O4—C36—C35123.7 (2)
C6—O1—C41124.3 (2)O4—C36—C31118.2 (2)
C16—O2—C49114.5 (2)C35—C36—C31117.9 (2)
C26—O3—C57113.88 (18)C38—C37—C40'128.2 (8)
C36—O4—C65116.4 (2)C38—C37—C39'56.3 (6)
C2—C1—C6120.1 (2)C40'—C37—C39'117.1 (7)
C2—C1—S1117.5 (2)C38—C37—C40117.8 (7)
C6—C1—S1122.04 (19)C40'—C37—C4025.5 (7)
C1—C2—C3122.3 (2)C39'—C37—C40135.4 (5)
C1—C2—H2118.8C38—C37—C33115.0 (4)
C3—C2—H2118.8C40'—C37—C33114.3 (7)
C4—C3—C2116.4 (2)C39'—C37—C33110.9 (4)
C4—C3—C7123.2 (2)C40—C37—C33110.3 (4)
C2—C3—C7120.3 (3)C38—C37—C39106.5 (6)
C3—C4—C5122.6 (2)C40'—C37—C3974.4 (6)
C3—C4—H4118.7C39'—C37—C3952.7 (5)
C5—C4—H4118.7C40—C37—C3999.8 (4)
C6—C5—C4120.4 (2)C33—C37—C39105.5 (3)
C6—C5—S2123.38 (19)C38—C37—C38'45.7 (5)
C4—C5—S2115.79 (18)C40'—C37—C38'105.0 (7)
O1—C6—C5122.5 (2)C39'—C37—C38'101.7 (6)
O1—C6—C1119.2 (2)C40—C37—C38'82.6 (5)
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C10—C7—C8107.3 (3)C39—C37—C38'145.1 (4)
C10—C7—C9110.5 (3)C37—C38—H38A109.5
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H8B—C8—H8C109.5C37—C38'—H38E109.5
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C7—C9—H9B109.5C37—C38'—H38F109.5
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H9B—C9—H9C109.5C37—C39'—H39E109.5
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H10B—C10—H10C109.5C37—C40'—H40E109.5
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C11—C12—C13122.3 (2)H40E—C40'—H40F109.5
C11—C12—H12118.8O1—C41—C42120.6 (3)
C13—C12—H12118.8O1—C41—H41A107.2
C14—C13—C12116.9 (2)C42—C41—H41A107.2
C14—C13—C17120.9 (3)O1—C41—H41B107.2
C12—C13—C17122.2 (3)C42—C41—H41B107.2
C13—C14—C15122.1 (3)H41A—C41—H41B106.8
C13—C14—H14119.0C43—C42—C47115.1 (3)
C15—C14—H14119.0C43—C42—C41123.2 (3)
C16—C15—C14120.1 (2)C47—C42—C41121.6 (3)
C16—C15—S3124.2 (2)C44—C43—C42123.4 (3)
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C20'—C17—C18'117.9 (10)C43—C44—H44119.8
C20'—C17—C13114.7 (6)C44—C45—C46119.1 (3)
C18'—C17—C13115.0 (8)C44—C45—S5115.1 (3)
C20'—C17—C1989.3 (6)C46—C45—S5125.7 (3)
C18'—C17—C19108.1 (7)C44—C45—S5'122.0 (6)
C13—C17—C19108.0 (5)C46—C45—S5'118.5 (6)
C20'—C17—C19'114.6 (8)S5—C45—S5'10.0 (10)
C18'—C17—C19'86.7 (8)C45—C46—C47119.6 (3)
C13—C17—C19'103.6 (7)C45—C46—H46120.2
C19—C17—C19'27.2 (6)C47—C46—H46120.2
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C18'—C17—C1818.6 (9)C42—C47—H47118.9
C13—C17—C18107.7 (7)C46—C47—H47118.9
C19—C17—C18126.3 (7)O2—C49—C50109.5 (3)
C19'—C17—C18105.3 (9)O2—C49—H49A109.8
C20'—C17—C2020.8 (7)C50—C49—H49A109.8
C18'—C17—C20107.1 (9)O2—C49—H49B109.8
C13—C17—C20108.8 (5)C50—C49—H49B109.8
C19—C17—C20109.9 (6)H49A—C49—H49B108.2
C19'—C17—C20134.2 (8)C55—C50—C51117.9 (3)
C18—C17—C2094.8 (9)C55—C50—C49123.2 (3)
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C17—C18—H18B109.5C52—C51—C50121.2 (4)
C17—C18—H18C109.5C52—C51—H51119.4
C17—C19—H19A109.5C50—C51—H51119.4
C17—C19—H19B109.5C53—C52—C51121.2 (3)
C17—C19—H19C109.5C53—C52—H52119.4
C17—C20—H20A109.5C51—C52—H52119.4
C17—C20—H20B109.5C52—C53—C54118.2 (3)
C17—C20—H20C109.5C52—C53—S6114.4 (4)
C17—C18'—H18D109.5C54—C53—S6126.9 (5)
C17—C18'—H18E109.5C52—C53—S6'120.3 (5)
H18D—C18'—H18E109.5C54—C53—S6'120.9 (5)
C17—C18'—H18F109.5S6—C53—S6'15.5 (5)
H18D—C18'—H18F109.5C55—C54—C53120.7 (3)
H18E—C18'—H18F109.5C55—C54—H54119.7
C17—C19'—H19D109.5C53—C54—H54119.7
C17—C19'—H19E109.5C50—C55—C54120.9 (3)
H19D—C19'—H19E109.5C50—C55—H55119.5
C17—C19'—H19F109.5C54—C55—H55119.5
H19D—C19'—H19F109.5O3—C57—C58109.3 (2)
H19E—C19'—H19F109.5O3—C57—H57A109.8
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H20D—C20'—H20E109.5C58—C57—H57B109.8
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H20D—C20'—H20F109.5C59—C58—C63118.2 (2)
H20E—C20'—H20F109.5C59—C58—C57123.4 (2)
C26—C21—C22120.6 (2)C63—C58—C57118.4 (2)
C26—C21—S3123.6 (2)C60—C59—C58120.4 (3)
C22—C21—S3115.3 (2)C60—C59—H59119.8
C23—C22—C21121.2 (3)C58—C59—H59119.8
C23—C22—H22119.4C59—C60—C61121.2 (3)
C21—C22—H22119.4C59—C60—H60119.4
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C24—C23—C27122.4 (3)C62—C61—C60118.1 (3)
C22—C23—C27120.4 (3)C62—C61—S7'120.1 (4)
C23—C24—C25122.7 (3)C60—C61—S7'121.8 (4)
C23—C24—H24118.7C62—C61—S7128.9 (4)
C25—C24—H24118.7C60—C61—S7112.9 (4)
C26—C25—C24119.6 (2)S7'—C61—S710.2 (7)
C26—C25—S4123.81 (19)C63—C62—C61120.4 (3)
C24—C25—S4115.7 (2)C63—C62—H62119.8
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C21—C26—C25118.7 (2)C62—C63—H63119.2
C30'—C27—C28124.7 (8)C58—C63—H63119.2
C30'—C27—C29108.4 (8)O4—C65—C66114.4 (2)
C28—C27—C2985.6 (7)O4—C65—H65A108.7
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C28—C27—C23112.3 (5)O4—C65—H65B108.7
C29—C27—C23110.4 (5)C66—C65—H65B108.7
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C29—C27—C29'31.4 (5)C67—C66—C65122.3 (3)
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C29'—C27—C30104.2 (6)C69—C68—H68119.6
C30'—C27—C28'110.4 (9)C67—C68—H68119.6
C28—C27—C28'21.6 (9)C68—C69—C70118.0 (4)
C29—C27—C28'106.3 (8)C68—C69—S8'117.1 (6)
C23—C27—C28'109.6 (7)C70—C69—S8'124.8 (5)
C29'—C27—C28'129.6 (8)C68—C69—S8129.1 (5)
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C27—C28—H28B109.5C69—C70—C71121.3 (4)
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C6—C1—C2—C31.1 (4)C65—O4—C36—C31115.1 (3)
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C4—C5—C6—C12.7 (3)C34—C33—C37—C39'72.7 (7)
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C12—C13—C14—C151.5 (4)C48—S5—C45—S5'47 (6)
C17—C13—C14—C15177.0 (3)C48'—S5'—C45—C44153.6 (7)
C13—C14—C15—C160.9 (4)C48'—S5'—C45—C4632.9 (13)
C13—C14—C15—S3171.2 (2)C48'—S5'—C45—S5105 (7)
C21—S3—C15—C1646.1 (3)C44—C45—C46—C470.3 (6)
C21—S3—C15—C14142.2 (2)S5—C45—C46—C47178.3 (5)
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C49—O2—C16—C1192.3 (3)C43—C42—C47—C462.6 (5)
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S3—C15—C16—O29.9 (4)C45—C46—C47—C421.3 (6)
C14—C15—C16—C110.0 (4)C16—O2—C49—C50177.7 (2)
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C12—C11—C16—C150.3 (4)C49—C50—C51—C52179.4 (3)
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C14—C13—C17—C20'17.0 (7)C51—C52—C53—C542.1 (6)
C12—C13—C17—C20'164.6 (6)C51—C52—C53—S6174.7 (4)
C14—C13—C17—C18'158.5 (7)C51—C52—C53—S6'169.2 (4)
C12—C13—C17—C18'23.1 (8)C56—S6—C53—C52173.0 (5)
C14—C13—C17—C1980.8 (5)C56—S6—C53—C5415.2 (8)
C12—C13—C17—C1997.6 (5)C56—S6—C53—S6'57 (3)
C14—C13—C17—C19'108.7 (7)C56'—S6'—C53—C52150.9 (6)
C12—C13—C17—C19'69.7 (7)C56'—S6'—C53—C5438.0 (8)
C14—C13—C17—C18140.1 (7)C56'—S6'—C53—S679 (3)
C12—C13—C17—C1841.5 (7)C52—C53—C54—C551.4 (5)
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C12—C13—C17—C20143.1 (6)S6'—C53—C54—C55169.8 (4)
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C15—S3—C21—C22138.9 (2)C49—C50—C55—C54178.6 (3)
C26—C21—C22—C230.2 (4)C53—C54—C55—C500.3 (5)
S3—C21—C22—C23172.4 (2)C26—O3—C57—C58173.4 (2)
C21—C22—C23—C240.7 (4)O3—C57—C58—C591.3 (4)
C21—C22—C23—C27177.2 (2)O3—C57—C58—C63177.6 (2)
C22—C23—C24—C251.0 (4)C63—C58—C59—C601.1 (5)
C27—C23—C24—C25176.8 (2)C57—C58—C59—C60177.8 (3)
C23—C24—C25—C260.6 (4)C58—C59—C60—C610.7 (5)
C23—C24—C25—S4169.39 (19)C59—C60—C61—C622.4 (5)
C31—S4—C25—C2647.7 (2)C59—C60—C61—S7'175.8 (5)
C31—S4—C25—C24142.83 (19)C59—C60—C61—S7178.5 (4)
C57—O3—C26—C2189.2 (3)C64'—S7'—C61—C6238.4 (9)
C57—O3—C26—C2592.4 (3)C64'—S7'—C61—C60139.8 (7)
C22—C21—C26—O3179.1 (2)C64'—S7'—C61—S7171 (4)
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C22—C21—C26—C250.7 (4)C64—S7—C61—C60169.4 (5)
S3—C21—C26—C25172.24 (18)C64—S7—C61—S7'17 (3)
C24—C25—C26—O3178.8 (2)C60—C61—C62—C632.3 (5)
S4—C25—C26—O312.1 (3)S7'—C61—C62—C63176.0 (5)
C24—C25—C26—C210.3 (4)S7—C61—C62—C63177.6 (5)
S4—C25—C26—C21169.42 (18)C61—C62—C63—C580.4 (5)
C24—C23—C27—C30'80.8 (7)C59—C58—C63—C621.3 (5)
C22—C23—C27—C30'97.1 (7)C57—C58—C63—C62177.7 (3)
C24—C23—C27—C28133.6 (6)C36—O4—C65—C6681.3 (3)
C22—C23—C27—C2848.6 (6)O4—C65—C66—C6799.8 (4)
C24—C23—C27—C2939.9 (6)O4—C65—C66—C7181.0 (4)
C22—C23—C27—C29142.3 (6)C71—C66—C67—C681.7 (7)
C24—C23—C27—C29'6.3 (6)C65—C66—C67—C68177.6 (4)
C22—C23—C27—C29'175.9 (5)C66—C67—C68—C692.2 (8)
C24—C23—C27—C30107.0 (5)C67—C68—C69—C705.1 (7)
C22—C23—C27—C3070.8 (5)C67—C68—C69—S8'172.1 (6)
C24—C23—C27—C28'156.6 (7)C67—C68—C69—S8177.0 (5)
C22—C23—C27—C28'25.6 (7)C72'—S8'—C69—C6815.4 (12)
C25—S4—C31—C32128.5 (2)C72'—S8'—C69—C70167.7 (10)
C25—S4—C31—C3659.2 (2)C72'—S8'—C69—S8147 (3)
C36—C31—C32—C330.4 (4)C72—S8—C69—C6819.2 (8)
S4—C31—C32—C33172.8 (2)C72—S8—C69—C70158.8 (6)
C31—C32—C33—C342.8 (4)C72—S8—C69—S8'39 (2)
C31—C32—C33—C37176.8 (3)C68—C69—C70—C714.2 (6)
C32—C33—C34—C352.7 (4)S8'—C69—C70—C71172.7 (5)
C37—C33—C34—C35176.9 (3)S8—C69—C70—C71177.6 (4)
C33—C34—C35—C360.6 (4)C67—C66—C71—C702.6 (6)
C33—C34—C35—S1174.7 (2)C65—C66—C71—C70176.7 (3)
C1—S1—C35—C3653.0 (2)C69—C70—C71—C660.3 (6)

Experimental details

Crystal data
Chemical formulaC72H80O4S8
Mr1265.84
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)15.1863 (10), 15.5795 (11), 16.9774 (12)
α, β, γ (°)75.473 (2), 85.686 (2), 84.762 (2)
V3)3866.4 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.26 × 0.21 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.434, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14394, 14394, 9034
Rint0.000
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.172, 0.96
No. of reflections14394
No. of parameters939
No. of restraints244
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.29

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements top

The work was supported financially by National Natural Science Foundation of China (No. 21072052), the National Basic Research Program of China (No. 2009CB421601) and Hunan Provincial Science and Technology Department Program (Nos. 2011 W K4007 and 06 F J4115).

references
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