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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o155.
Published online 2008 December 17. doi:  10.1107/S1600536808042323
PMCID: PMC2968069

2,4-Di-tert-butyl-6-[1-(3,5-di-tert-butyl-2-hydroxy­phen­yl)eth­yl]phenyl 4-methyl­benzene­sulfonate

Abstract

The title compound, C37H52O4S, was obtained by the reaction of 6,6′-(ethane-1,1-di­yl)bis­(2,4-di-tert-butyl­phenol) and 4-methyl­benzene-1-sulfonyl chloride. The mol­ecular conformation is stabilized by an intra­molecular O—H(...)O hydrogen bond. Two of the tert-butyl groups are disordered over two sets of sites with occupancies 0.530 (15)/0.470 (15) and 0.615 (11)/0.385 (11).

Related literature

For the polymerization of cyclic esters, see: Endo et al. (1987 [triangle]); Wu et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o155-scheme1.jpg

Experimental

Crystal data

  • C37H52O4S
  • M r = 592.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o155-efi1.jpg
  • a = 13.893 (2) Å
  • b = 15.760 (2) Å
  • c = 17.525 (3) Å
  • β = 107.262 (3)°
  • V = 3664.3 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 298 (2) K
  • 0.32 × 0.28 × 0.25 mm

Data collection

  • Bruker SMART 1K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002 [triangle]) T min = 0.962, T max = 0.970
  • 18079 measured reflections
  • 6422 independent reflections
  • 4281 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.157
  • S = 1.06
  • 6422 reflections
  • 435 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042323/bt2830sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042323/bt2830Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are grateful for the financial support of the National Science Foundation of China (20601011) and Science Foundation of Gansu Province of China (0803RJZA103).

supplementary crystallographic information

Comment

In past decades, significant advance have been made in polymerization of cyclic esters, such as poly(e-caprolactone) (Endo et al., 1987) or poly(lactide) (Wu et al., 2006). A particularly convenient method for the synthesis of polylactides is the ring-opening polymerization (ROP) of lactides. Due to the advantages of well controlled molecular weight and low polydispersity, many metal complexes have been used. In the present study, we report a compound, which is a potential ligand for investigation of ring-opening polymerization of lactides. The bond lengths and angles are within normal ranges. There is a intramolecular hydrogen bond.

Experimental

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. 4-Methylbenzene-1-sulfonyl chloride (2.09 g, 11 mmol) in dichloromethane (20 ml) was added dropwise into the above solution at 0 °C for about 1 h. The resulting mixture was then 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 vacuum, and the residue was recrystallized by slow cooling of a acetonitrile solution.

Refinement

All H atoms were placed in calculated positions and refined using a riding model, with d(O—H)=0.82Å and Uiso(H)=1.2Ueq(O), d(C—H)=0.93Å and Uiso(H)=1.2Ueq(C) for Caromatic, d(C—H)=0.97Å and Uiso(H)=1.2Ueq(C) for methylene groups, and d(C—H)=0.96Å and Uiso(H)=1.5Ueq(C) for methyl groups. Two tert-butyl groups are disordered over two sites, with a site occupation factors of 0.530 (15) and 0.615 (11) for the major occupied site, respectively.

Figures

Fig. 1.
The structure of the title compound showing displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The formation of the title compound.

Crystal data

C37H52O4SF(000) = 1288
Mr = 592.85Dx = 1.075 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 20154 reflections
a = 13.893 (2) Åθ = 2.2–25.5°
b = 15.760 (2) ŵ = 0.12 mm1
c = 17.525 (3) ÅT = 298 K
β = 107.262 (3)°Block, colourless
V = 3664.3 (10) Å30.32 × 0.28 × 0.25 mm
Z = 4

Data collection

Bruker SMART 1K CCD area-detector diffractometer6422 independent reflections
Radiation source: fine-focus sealed tube4281 reflections with I > 2σ(I)
graphiteRint = 0.033
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)h = −16→15
Tmin = 0.962, Tmax = 0.970k = −18→11
18079 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0922P)2] where P = (Fo2 + 2Fc2)/3
6422 reflections(Δ/σ)max < 0.001
435 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S1−0.12768 (4)0.86568 (4)0.82030 (3)0.0582 (2)
O1−0.03328 (10)0.65695 (9)0.72763 (9)0.0660 (4)
H1A−0.05230.70460.73510.099*
O2−0.08263 (10)0.92862 (9)0.76869 (8)0.0560 (4)
O3−0.19479 (13)0.91394 (13)0.84952 (9)0.0892 (6)
O4−0.16166 (11)0.79066 (10)0.77557 (8)0.0706 (5)
C10.04851 (14)0.66320 (13)0.69863 (11)0.0495 (5)
C20.08001 (15)0.58978 (13)0.66879 (13)0.0565 (5)
C30.16357 (16)0.59769 (14)0.64116 (13)0.0604 (6)
H3B0.18580.54960.62070.072*
C40.21551 (15)0.67205 (14)0.64218 (12)0.0544 (5)
C50.18127 (15)0.74257 (13)0.67293 (11)0.0519 (5)
H5A0.21530.79370.67480.062*
C60.09822 (14)0.73996 (12)0.70110 (10)0.0456 (5)
C70.05885 (14)0.81936 (12)0.73091 (11)0.0473 (5)
H7A0.03310.80200.77490.057*
C8−0.02946 (14)0.85829 (12)0.66655 (11)0.0446 (5)
C9−0.04110 (15)0.84412 (12)0.58635 (11)0.0481 (5)
H9A0.00240.80650.57240.058*
C10−0.11499 (16)0.88377 (13)0.52618 (12)0.0527 (5)
C11−0.17554 (16)0.94102 (14)0.54969 (12)0.0600 (6)
H11A−0.22500.96870.50990.072*
C12−0.16794 (16)0.96036 (14)0.62890 (13)0.0583 (6)
C13−0.09589 (14)0.91427 (12)0.68549 (11)0.0482 (5)
C14−0.02230 (15)0.84260 (14)0.90080 (11)0.0496 (5)
C150.03200 (17)0.90683 (15)0.94664 (13)0.0648 (6)
H15A0.01490.96320.93360.078*
C160.11210 (19)0.88714 (17)1.01221 (14)0.0746 (7)
H16A0.14970.93081.04250.089*
C170.13759 (18)0.80494 (18)1.03374 (13)0.0723 (7)
C180.08153 (19)0.74164 (16)0.98730 (14)0.0748 (7)
H18A0.09760.68531.00120.090*
C190.00230 (17)0.75959 (15)0.92091 (13)0.0638 (6)
H19A−0.03430.71590.88990.077*
C200.02661 (19)0.50438 (15)0.66815 (19)0.0798 (8)
C210.0425 (2)0.47584 (19)0.7540 (2)0.1130 (11)
H21A0.01660.51820.78200.169*
H21B0.11320.46810.77990.169*
H21C0.00780.42320.75420.169*
C22−0.0861 (2)0.51147 (19)0.6233 (2)0.1080 (11)
H22A−0.11640.55320.64880.162*
H22B−0.11790.45750.62390.162*
H22C−0.09440.52810.56900.162*
C230.0693 (2)0.43513 (19)0.6248 (3)0.1288 (14)
H23A0.13980.42770.65150.193*
H23B0.06000.45200.57050.193*
H23C0.03450.38270.62560.193*
C240.30546 (19)0.67786 (16)0.60915 (15)0.0708 (7)
C250.2779 (13)0.7341 (10)0.5397 (10)0.201 (11)0.530 (15)
H25A0.22080.71100.49980.402*0.530 (15)
H25B0.33370.73910.51830.402*0.530 (15)
H25C0.26110.78910.55550.402*0.530 (15)
C260.3269 (9)0.5914 (4)0.5741 (8)0.113 (4)0.530 (15)
H26A0.26900.57480.53120.227*0.530 (15)
H26B0.34090.54890.61520.227*0.530 (15)
H26C0.38400.59720.55430.227*0.530 (15)
C270.3962 (6)0.7038 (15)0.6763 (8)0.184 (10)0.530 (15)
H27A0.41780.65710.71250.369*0.530 (15)
H27B0.37900.75100.70440.369*0.530 (15)
H27C0.44970.72000.65500.369*0.530 (15)
C25'0.2691 (10)0.6693 (12)0.5187 (6)0.167 (10)0.470 (15)
H25D0.20030.65050.50220.335*0.470 (15)
H25E0.31030.62870.50200.335*0.470 (15)
H25F0.27380.72330.49470.335*0.470 (15)
C26'0.3858 (8)0.6148 (10)0.6495 (12)0.149 (9)0.470 (15)
H26D0.36680.55940.62730.298*0.470 (15)
H26E0.39340.61380.70570.298*0.470 (15)
H26F0.44860.63100.64120.298*0.470 (15)
C27'0.3555 (8)0.7668 (5)0.6201 (8)0.104 (4)0.470 (15)
H27D0.32060.80280.57640.209*0.470 (15)
H27E0.42470.76160.62130.209*0.470 (15)
H27F0.35200.79120.66940.209*0.470 (15)
C28−0.12671 (18)0.86591 (15)0.43838 (12)0.0649 (6)
C29−0.0325 (5)0.8900 (7)0.4209 (3)0.121 (4)0.615 (11)
H29A−0.03100.95040.41420.242*0.615 (11)
H29B−0.02980.86250.37270.242*0.615 (11)
H29C0.02440.87290.46440.242*0.615 (11)
C30−0.2182 (5)0.9135 (5)0.3822 (3)0.112 (4)0.615 (11)
H30D−0.22980.89370.32840.224*0.615 (11)
H30A−0.20450.97330.38450.224*0.615 (11)
H30B−0.27690.90300.39900.224*0.615 (11)
C31−0.1505 (8)0.7724 (4)0.4254 (4)0.115 (3)0.615 (11)
H31A−0.21840.76210.42600.230*0.615 (11)
H31B−0.10470.74020.46720.230*0.615 (11)
H31C−0.14350.75540.37470.230*0.615 (11)
C29'−0.1198 (11)0.9495 (6)0.3951 (5)0.113 (5)0.385 (11)
H29D−0.17340.98660.39790.225*0.385 (11)
H29E−0.12540.93790.34020.225*0.385 (11)
H29F−0.05610.97620.42030.225*0.385 (11)
C30'−0.2196 (15)0.8198 (14)0.3989 (6)0.195 (12)0.385 (11)
H30E−0.27640.85060.40520.389*0.385 (11)
H30F−0.21720.76460.42260.389*0.385 (11)
H30G−0.22620.81380.34310.389*0.385 (11)
C31'−0.0357 (13)0.8070 (12)0.4275 (5)0.145 (7)0.385 (11)
H31D−0.04930.74860.43600.289*0.385 (11)
H31E0.02660.82370.46570.289*0.385 (11)
H31F−0.03050.81390.37450.289*0.385 (11)
C32−0.2354 (2)1.02994 (19)0.64732 (17)0.0883 (9)
C33−0.2761 (3)1.0877 (3)0.5742 (2)0.165 (2)
H33A−0.31771.13110.58640.247*
H33B−0.31531.05460.52980.247*
H33C−0.22071.11350.56070.247*
C34−0.3234 (2)0.9887 (3)0.6664 (2)0.1381 (15)
H34A−0.36591.03180.67800.207*
H34B−0.29910.95230.71190.207*
H34C−0.36140.95590.62130.207*
C35−0.1797 (3)1.0870 (2)0.7152 (2)0.1520 (17)
H35A−0.22501.12930.72410.228*
H35B−0.12491.11420.70200.228*
H35C−0.15371.05380.76290.228*
C360.13897 (16)0.88649 (14)0.76382 (14)0.0673 (6)
H36A0.10910.93450.78180.101*
H36B0.16730.90410.72260.101*
H36C0.19120.86330.80780.101*
C370.2241 (2)0.7836 (2)1.10578 (17)0.1190 (12)
H37A0.23030.72311.11140.178*
H37B0.21220.80741.15260.178*
H37C0.28530.80671.09950.178*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0529 (3)0.0830 (5)0.0432 (3)0.0073 (3)0.0212 (2)0.0026 (3)
O10.0584 (9)0.0631 (10)0.0872 (11)−0.0002 (7)0.0381 (8)−0.0085 (8)
O20.0696 (9)0.0589 (9)0.0458 (7)0.0095 (7)0.0269 (7)−0.0021 (6)
O30.0729 (10)0.1432 (17)0.0623 (10)0.0428 (10)0.0366 (9)0.0113 (10)
O40.0677 (10)0.0892 (12)0.0520 (9)−0.0206 (8)0.0135 (8)−0.0033 (8)
C10.0447 (11)0.0573 (13)0.0483 (11)0.0084 (9)0.0165 (9)0.0009 (9)
C20.0515 (12)0.0550 (13)0.0647 (13)0.0076 (10)0.0199 (10)−0.0038 (10)
C30.0670 (14)0.0532 (14)0.0674 (14)0.0132 (11)0.0298 (12)−0.0062 (11)
C40.0554 (12)0.0608 (14)0.0536 (12)0.0128 (10)0.0262 (10)0.0066 (10)
C50.0558 (12)0.0528 (13)0.0522 (12)0.0065 (9)0.0237 (10)0.0053 (9)
C60.0477 (10)0.0506 (12)0.0398 (10)0.0088 (9)0.0148 (9)0.0015 (8)
C70.0511 (11)0.0501 (12)0.0420 (10)0.0069 (9)0.0158 (9)−0.0015 (9)
C80.0483 (11)0.0445 (11)0.0437 (11)0.0027 (8)0.0176 (9)0.0000 (8)
C90.0552 (12)0.0479 (12)0.0442 (11)0.0043 (9)0.0192 (9)−0.0031 (9)
C100.0602 (12)0.0543 (13)0.0459 (11)−0.0002 (10)0.0193 (10)0.0049 (9)
C110.0600 (13)0.0702 (15)0.0490 (12)0.0160 (11)0.0148 (10)0.0140 (10)
C120.0623 (13)0.0631 (14)0.0562 (13)0.0179 (11)0.0278 (11)0.0134 (10)
C130.0570 (12)0.0524 (12)0.0400 (10)0.0059 (9)0.0215 (9)−0.0001 (9)
C140.0541 (11)0.0599 (14)0.0394 (10)0.0031 (10)0.0212 (9)−0.0012 (9)
C150.0745 (15)0.0609 (15)0.0578 (13)0.0039 (12)0.0177 (12)−0.0068 (11)
C160.0768 (16)0.0788 (18)0.0601 (15)−0.0001 (13)0.0081 (13)−0.0181 (13)
C170.0730 (15)0.0880 (19)0.0522 (13)0.0146 (14)0.0129 (12)−0.0052 (13)
C180.0925 (18)0.0661 (16)0.0597 (15)0.0127 (14)0.0131 (14)0.0066 (12)
C190.0744 (15)0.0620 (15)0.0535 (13)−0.0027 (11)0.0168 (12)−0.0002 (11)
C200.0681 (15)0.0557 (15)0.125 (2)−0.0031 (11)0.0424 (16)−0.0167 (15)
C210.110 (2)0.075 (2)0.168 (3)−0.0019 (17)0.062 (2)0.028 (2)
C220.0727 (17)0.094 (2)0.159 (3)−0.0192 (15)0.0376 (19)−0.045 (2)
C230.110 (2)0.070 (2)0.226 (4)−0.0109 (17)0.079 (3)−0.055 (2)
C240.0775 (16)0.0733 (17)0.0801 (17)0.0113 (13)0.0518 (14)0.0063 (13)
C250.28 (2)0.192 (13)0.220 (19)0.124 (14)0.219 (18)0.136 (13)
C260.130 (7)0.097 (5)0.157 (9)0.036 (5)0.111 (7)0.021 (5)
C270.069 (5)0.35 (3)0.165 (10)−0.054 (10)0.075 (6)−0.077 (15)
C25'0.164 (12)0.27 (2)0.106 (8)−0.091 (15)0.100 (9)−0.078 (12)
C26'0.094 (7)0.170 (11)0.22 (2)0.069 (8)0.100 (11)0.106 (14)
C27'0.109 (7)0.101 (6)0.141 (10)−0.029 (5)0.095 (7)−0.023 (5)
C280.0802 (16)0.0712 (16)0.0409 (12)0.0019 (12)0.0142 (11)−0.0007 (10)
C290.114 (5)0.210 (12)0.058 (3)−0.048 (7)0.054 (3)−0.026 (5)
C300.126 (6)0.154 (7)0.045 (2)0.044 (5)0.007 (3)0.016 (3)
C310.194 (9)0.091 (4)0.052 (3)−0.003 (4)0.024 (4)−0.030 (3)
C29'0.181 (17)0.108 (7)0.062 (5)−0.003 (7)0.056 (7)0.017 (4)
C30'0.233 (18)0.28 (3)0.056 (6)−0.18 (2)0.016 (9)−0.015 (11)
C31'0.225 (15)0.164 (13)0.063 (5)0.077 (12)0.069 (7)0.002 (6)
C320.099 (2)0.100 (2)0.0807 (18)0.0581 (17)0.0498 (16)0.0325 (16)
C330.230 (5)0.167 (4)0.133 (3)0.152 (4)0.110 (3)0.081 (3)
C340.095 (2)0.196 (4)0.145 (3)0.067 (2)0.069 (2)0.044 (3)
C350.209 (4)0.106 (3)0.141 (3)0.082 (3)0.053 (3)−0.027 (2)
C360.0584 (13)0.0668 (15)0.0723 (15)0.0026 (11)0.0125 (12)−0.0159 (12)
C370.107 (2)0.146 (3)0.0741 (19)0.041 (2)−0.0190 (17)−0.0131 (19)

Geometric parameters (Å, °)

S1—O31.4118 (15)C25—H25A0.9600
S1—O41.4197 (16)C25—H25B0.9600
S1—O21.5905 (14)C25—H25C0.9600
S1—C141.744 (2)C26—H26A0.9600
O1—C11.379 (2)C26—H26B0.9600
O1—H1A0.8200C26—H26C0.9600
O2—C131.432 (2)C27—H27A0.9600
C1—C61.387 (3)C27—H27B0.9600
C1—C21.393 (3)C27—H27C0.9600
C2—C31.390 (3)C25'—H25D0.9600
C2—C201.535 (3)C25'—H25E0.9600
C3—C41.374 (3)C25'—H25F0.9600
C3—H3B0.9300C26'—H26D0.9600
C4—C51.380 (3)C26'—H26E0.9600
C4—C241.528 (3)C26'—H26F0.9600
C5—C61.384 (3)C27'—H27D0.9600
C5—H5A0.9300C27'—H27E0.9600
C6—C71.519 (3)C27'—H27F0.9600
C7—C361.520 (3)C28—C30'1.464 (11)
C7—C81.527 (3)C28—C291.480 (5)
C7—H7A0.9800C28—C311.513 (7)
C8—C91.384 (3)C28—C29'1.537 (8)
C8—C131.386 (3)C28—C301.551 (5)
C9—C101.383 (3)C28—C31'1.625 (11)
C9—H9A0.9300C29—H29A0.9600
C10—C111.377 (3)C29—H29B0.9600
C10—C281.525 (3)C29—H29C0.9600
C11—C121.394 (3)C30—H30D0.9600
C11—H11A0.9300C30—H30A0.9600
C12—C131.387 (3)C30—H30B0.9600
C12—C321.538 (3)C31—H31A0.9600
C14—C151.371 (3)C31—H31B0.9600
C14—C191.371 (3)C31—H31C0.9600
C15—C161.377 (3)C29'—H29D0.9600
C15—H15A0.9300C29'—H29E0.9600
C16—C171.366 (3)C29'—H29F0.9600
C16—H16A0.9300C30'—H30E0.9600
C17—C181.374 (3)C30'—H30F0.9600
C17—C371.501 (3)C30'—H30G0.9600
C18—C191.373 (3)C31'—H31D0.9600
C18—H18A0.9300C31'—H31E0.9600
C19—H19A0.9300C31'—H31F0.9600
C20—C211.522 (4)C32—C341.507 (4)
C20—C221.533 (4)C32—C351.509 (5)
C20—C231.544 (4)C32—C331.537 (4)
C21—H21A0.9600C33—H33A0.9600
C21—H21B0.9600C33—H33B0.9600
C21—H21C0.9600C33—H33C0.9600
C22—H22A0.9600C34—H34A0.9600
C22—H22B0.9600C34—H34B0.9600
C22—H22C0.9600C34—H34C0.9600
C23—H23A0.9600C35—H35A0.9600
C23—H23B0.9600C35—H35B0.9600
C23—H23C0.9600C35—H35C0.9600
C24—C251.461 (9)C36—H36A0.9600
C24—C271.504 (9)C36—H36B0.9600
C24—C26'1.505 (8)C36—H36C0.9600
C24—C25'1.521 (10)C37—H37A0.9600
C24—C27'1.552 (7)C37—H37B0.9600
C24—C261.560 (7)C37—H37C0.9600
O3—S1—O4120.11 (11)C24—C27—H27A109.5
O3—S1—O2106.49 (10)C24—C27—H27B109.5
O4—S1—O2109.14 (8)H27A—C27—H27B109.5
O3—S1—C14107.78 (9)C24—C27—H27C109.5
O4—S1—C14109.56 (10)H27A—C27—H27C109.5
O2—S1—C14102.28 (9)H27B—C27—H27C109.5
C1—O1—H1A109.5C24—C25'—H25D109.5
C13—O2—S1121.80 (12)C24—C25'—H25E109.5
O1—C1—C6120.51 (17)H25D—C25'—H25E109.5
O1—C1—C2117.64 (18)C24—C25'—H25F109.5
C6—C1—C2121.83 (18)H25D—C25'—H25F109.5
C3—C2—C1116.4 (2)H25E—C25'—H25F109.5
C3—C2—C20121.87 (19)C24—C26'—H26D109.5
C1—C2—C20121.75 (19)C24—C26'—H26E109.5
C4—C3—C2124.19 (19)H26D—C26'—H26E109.5
C4—C3—H3B117.9C24—C26'—H26F109.5
C2—C3—H3B117.9H26D—C26'—H26F109.5
C3—C4—C5116.85 (18)H26E—C26'—H26F109.5
C3—C4—C24122.12 (19)C24—C27'—H27D109.5
C5—C4—C24121.0 (2)C24—C27'—H27E109.5
C4—C5—C6122.4 (2)H27D—C27'—H27E109.5
C4—C5—H5A118.8C24—C27'—H27F109.5
C6—C5—H5A118.8H27D—C27'—H27F109.5
C5—C6—C1118.35 (18)H27E—C27'—H27F109.5
C5—C6—C7121.44 (18)C30'—C28—C29137.7 (6)
C1—C6—C7120.16 (16)C30'—C28—C3147.4 (9)
C6—C7—C36113.96 (16)C29—C28—C31112.7 (5)
C6—C7—C8111.68 (15)C30'—C28—C10112.5 (5)
C36—C7—C8109.75 (17)C29—C28—C10109.0 (3)
C6—C7—H7A107.0C31—C28—C10106.6 (3)
C36—C7—H7A107.0C30'—C28—C29'111.6 (9)
C8—C7—H7A107.0C29—C28—C29'59.2 (5)
C9—C8—C13117.40 (17)C31—C28—C29'143.5 (4)
C9—C8—C7120.74 (16)C10—C28—C29'109.6 (3)
C13—C8—C7121.66 (16)C30'—C28—C3059.9 (9)
C10—C9—C8122.53 (18)C29—C28—C30110.7 (4)
C10—C9—H9A118.7C31—C28—C30105.9 (4)
C8—C9—H9A118.7C10—C28—C30111.9 (2)
C11—C10—C9116.66 (18)C29'—C28—C3055.4 (5)
C11—C10—C28122.07 (19)C30'—C28—C31'105.6 (10)
C9—C10—C28121.25 (18)C29—C28—C31'49.9 (6)
C10—C11—C12124.64 (19)C31—C28—C31'64.4 (7)
C10—C11—H11A117.7C10—C28—C31'111.7 (4)
C12—C11—H11A117.7C29'—C28—C31'105.5 (7)
C13—C12—C11115.01 (18)C30—C28—C31'136.2 (4)
C13—C12—C32125.37 (19)C28—C29—H29A109.5
C11—C12—C32119.61 (19)C28—C29—H29B109.5
C8—C13—C12123.54 (17)H29A—C29—H29B109.5
C8—C13—O2116.77 (16)C28—C29—H29C109.5
C12—C13—O2119.52 (16)H29A—C29—H29C109.5
C15—C14—C19120.1 (2)H29B—C29—H29C109.5
C15—C14—S1120.26 (17)C28—C30—H30D109.5
C19—C14—S1119.49 (16)C28—C30—H30A109.5
C14—C15—C16119.4 (2)H30D—C30—H30A109.5
C14—C15—H15A120.3C28—C30—H30B109.5
C16—C15—H15A120.3H30D—C30—H30B109.5
C17—C16—C15121.6 (2)H30A—C30—H30B109.5
C17—C16—H16A119.2C28—C31—H31A109.5
C15—C16—H16A119.2C28—C31—H31B109.5
C16—C17—C18118.0 (2)H31A—C31—H31B109.5
C16—C17—C37121.5 (3)C28—C31—H31C109.5
C18—C17—C37120.5 (3)H31A—C31—H31C109.5
C19—C18—C17121.6 (2)H31B—C31—H31C109.5
C19—C18—H18A119.2C28—C29'—H29D109.5
C17—C18—H18A119.2C28—C29'—H29E109.5
C14—C19—C18119.4 (2)H29D—C29'—H29E109.5
C14—C19—H19A120.3C28—C29'—H29F109.5
C18—C19—H19A120.3H29D—C29'—H29F109.5
C21—C20—C22110.8 (3)H29E—C29'—H29F109.5
C21—C20—C2108.9 (2)C28—C30'—H30E109.5
C22—C20—C2110.9 (2)C28—C30'—H30F109.5
C21—C20—C23108.2 (3)H30E—C30'—H30F109.5
C22—C20—C23106.4 (2)C28—C30'—H30G109.5
C2—C20—C23111.6 (2)H30E—C30'—H30G109.5
C20—C21—H21A109.5H30F—C30'—H30G109.5
C20—C21—H21B109.5C28—C31'—H31D109.5
H21A—C21—H21B109.5C28—C31'—H31E109.5
C20—C21—H21C109.5H31D—C31'—H31E109.5
H21A—C21—H21C109.5C28—C31'—H31F109.5
H21B—C21—H21C109.5H31D—C31'—H31F109.5
C20—C22—H22A109.5H31E—C31'—H31F109.5
C20—C22—H22B109.5C34—C32—C35110.0 (3)
H22A—C22—H22B109.5C34—C32—C33108.6 (3)
C20—C22—H22C109.5C35—C32—C33106.3 (3)
H22A—C22—H22C109.5C34—C32—C12108.9 (3)
H22B—C22—H22C109.5C35—C32—C12112.9 (2)
C20—C23—H23A109.5C33—C32—C12110.1 (2)
C20—C23—H23B109.5C32—C33—H33A109.5
H23A—C23—H23B109.5C32—C33—H33B109.5
C20—C23—H23C109.5H33A—C33—H33B109.5
H23A—C23—H23C109.5C32—C33—H33C109.5
H23B—C23—H23C109.5H33A—C33—H33C109.5
C25—C24—C27116.0 (10)H33B—C33—H33C109.5
C26'—C24—C25'113.7 (9)C32—C34—H34A109.5
C25—C24—C4108.1 (5)C32—C34—H34B109.5
C27—C24—C4108.0 (3)H34A—C34—H34B109.5
C26'—C24—C4111.0 (3)C32—C34—H34C109.5
C25'—C24—C4109.5 (5)H34A—C34—H34C109.5
C26'—C24—C27'107.2 (6)H34B—C34—H34C109.5
C25'—C24—C27'102.0 (6)C32—C35—H35A109.5
C4—C24—C27'113.2 (3)C32—C35—H35B109.5
C25—C24—C26103.6 (6)H35A—C35—H35B109.5
C27—C24—C26109.4 (7)C32—C35—H35C109.5
C4—C24—C26111.7 (3)H35A—C35—H35C109.5
C27'—C24—C26135.1 (4)H35B—C35—H35C109.5
C24—C25—H25A109.5C7—C36—H36A109.5
C24—C25—H25B109.5C7—C36—H36B109.5
H25A—C25—H25B109.5H36A—C36—H36B109.5
C24—C25—H25C109.5C7—C36—H36C109.5
H25A—C25—H25C109.5H36A—C36—H36C109.5
H25B—C25—H25C109.5H36B—C36—H36C109.5
C24—C26—H26A109.5C17—C37—H37A109.5
C24—C26—H26B109.5C17—C37—H37B109.5
H26A—C26—H26B109.5H37A—C37—H37B109.5
C24—C26—H26C109.5C17—C37—H37C109.5
H26A—C26—H26C109.5H37A—C37—H37C109.5
H26B—C26—H26C109.5H37B—C37—H37C109.5
O3—S1—O2—C13−119.82 (15)O4—S1—C14—C19−12.53 (19)
O4—S1—O2—C1311.22 (16)O2—S1—C14—C19−128.22 (16)
C14—S1—O2—C13127.21 (14)C19—C14—C15—C160.9 (3)
O1—C1—C2—C3−178.99 (18)S1—C14—C15—C16176.94 (17)
C6—C1—C2—C3−0.4 (3)C14—C15—C16—C17−1.4 (4)
O1—C1—C2—C20−0.3 (3)C15—C16—C17—C180.8 (4)
C6—C1—C2—C20178.3 (2)C15—C16—C17—C37−179.3 (3)
C1—C2—C3—C40.4 (3)C16—C17—C18—C190.2 (4)
C20—C2—C3—C4−178.4 (2)C37—C17—C18—C19−179.7 (3)
C2—C3—C4—C50.1 (3)C15—C14—C19—C180.1 (3)
C2—C3—C4—C24−178.5 (2)S1—C14—C19—C18−175.96 (17)
C3—C4—C5—C6−0.5 (3)C17—C18—C19—C14−0.7 (4)
C24—C4—C5—C6178.05 (19)C3—C2—C20—C21112.6 (3)
C4—C5—C6—C10.5 (3)C1—C2—C20—C21−66.1 (3)
C4—C5—C6—C7−176.95 (17)C3—C2—C20—C22−125.2 (2)
O1—C1—C6—C5178.56 (17)C1—C2—C20—C2256.1 (3)
C2—C1—C6—C50.0 (3)C3—C2—C20—C23−6.8 (4)
O1—C1—C6—C7−4.0 (3)C1—C2—C20—C23174.5 (3)
C2—C1—C6—C7177.45 (17)C3—C4—C24—C25114.6 (10)
C5—C6—C7—C36−27.5 (3)C5—C4—C24—C25−63.9 (10)
C1—C6—C7—C36155.09 (19)C3—C4—C24—C27−119.2 (10)
C5—C6—C7—C897.5 (2)C5—C4—C24—C2762.3 (10)
C1—C6—C7—C8−79.8 (2)C3—C4—C24—C26'−56.7 (10)
C6—C7—C8—C9−24.8 (3)C5—C4—C24—C26'124.9 (10)
C36—C7—C8—C9102.6 (2)C3—C4—C24—C25'69.7 (8)
C6—C7—C8—C13160.55 (17)C5—C4—C24—C25'−108.8 (8)
C36—C7—C8—C13−72.1 (2)C3—C4—C24—C27'−177.3 (7)
C13—C8—C9—C100.4 (3)C5—C4—C24—C27'4.2 (7)
C7—C8—C9—C10−174.48 (18)C3—C4—C24—C261.2 (7)
C8—C9—C10—C112.1 (3)C5—C4—C24—C26−177.3 (6)
C8—C9—C10—C28−179.19 (19)C11—C10—C28—C30'−70.0 (12)
C9—C10—C11—C12−0.8 (3)C9—C10—C28—C30'111.4 (12)
C28—C10—C11—C12−179.6 (2)C11—C10—C28—C29118.1 (5)
C10—C11—C12—C13−2.8 (3)C9—C10—C28—C29−60.6 (5)
C10—C11—C12—C32175.9 (2)C11—C10—C28—C31−120.0 (5)
C9—C8—C13—C12−4.5 (3)C9—C10—C28—C3161.3 (5)
C7—C8—C13—C12170.40 (19)C11—C10—C28—C29'54.9 (6)
C9—C8—C13—O2−179.71 (16)C9—C10—C28—C29'−123.8 (6)
C7—C8—C13—O2−4.9 (3)C11—C10—C28—C30−4.7 (5)
C11—C12—C13—C85.5 (3)C9—C10—C28—C30176.6 (4)
C32—C12—C13—C8−173.1 (2)C11—C10—C28—C31'171.4 (9)
C11—C12—C13—O2−179.38 (18)C9—C10—C28—C31'−7.2 (9)
C32—C12—C13—O22.0 (3)C13—C12—C32—C34−81.7 (3)
S1—O2—C13—C8−82.7 (2)C11—C12—C32—C3499.8 (3)
S1—O2—C13—C12101.8 (2)C13—C12—C32—C3540.8 (4)
O3—S1—C14—C15−56.30 (19)C11—C12—C32—C35−137.8 (3)
O4—S1—C14—C15171.40 (16)C13—C12—C32—C33159.3 (3)
O2—S1—C14—C1555.71 (17)C11—C12—C32—C33−19.2 (4)
O3—S1—C14—C19119.77 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···O40.822.303.036 (2)150

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2830).

References

  • Bruker (1997). SMART andSAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Endo, M., Aida, T. & Inoue, S. (1987). Macromolecules, 20, 2982–2988.
  • Sheldrick, G. M. (2002). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev 250, 602–626.

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