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

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ISSN: 2056-9890

5,11,17,23-Tetra­kis(1,1-di­methyl­eth­yl)-26,28-di­hy­droxy­calix[4]arene-25,27-mono­thia­crown-3

aDepartment of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China
*Correspondence e-mail: deliean@hnu.edu.cn

(Received 19 February 2013; accepted 29 March 2013; online 10 April 2013)

The title calix[4]arene compound [systematic name: 3,9,15,34-tetra-tert-butyl-19,29-dioxa-24-thia­hexa­cyclo­[15.13.7.17,11.132,36.05,30.013,18]nona­triaconta-1(30),2,4,7,9,11(39),13,15,17,32,34,36(38)-dodeca­ene-38,39-diol], C52H70O4S, displays a cone-like conformation, the opposite arene rings bridged by the mono­thia­crown-3 unit are nearly parallel [dihedral angle = 16.01 (18)°], whereas the other opposite arene rings are twisted to each other at an angle of 74.41 (17)°. Intra­molecular O—H⋯O hydrogen bonds help to stabilize the mol­ecular structure. In the crystal, a C—H⋯π inter­action occurs. One of the tert-butyl groups is disordered over two sets of sites with a site-occupancy ratio of 0.70:0.30.

Related literature

For background to the title compound, see: Csokai et al. (2006[Csokai, V., Grün, A., Balázs, B., Simon, A., Tóth, G. & Bittera, I. (2006). Tetrahedron, 62, 10215-10222.]); Casnati et al. (1995[Casnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud-Neu, F., Fanni, S., Schwing, M.-J., Egberink, R. J. M., de Jong, F. & Reinhoudt, D. N. (1995). J. Am. Chem. Soc. 117, 2767-2777.]). For the synthesis, see: Li et al. (1999[Li, Z.-T., Ji, G.-Z., Zhao, C.-X., Yuan, S.-D., Ding, H., Huang, C., Du, A.-L. & Wei, M. (1999). J. Org. Chem. 64, 3572-3584.]).

[Scheme 1]

Experimental

Crystal data
  • C52H70O4S

  • Mr = 791.14

  • Orthorhombic, P 21 21 21

  • a = 10.6222 (8) Å

  • b = 18.4690 (14) Å

  • c = 24.5375 (18) Å

  • V = 4813.8 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.40 × 0.32 × 0.31 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • 25550 measured reflections

  • 8942 independent reflections

  • 5384 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.191

  • S = 0.93

  • 8942 reflections

  • 562 parameters

  • 78 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.33 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3232 Friedel pairs

  • Flack parameter: −0.09 (18)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C30–C35 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O1 0.80 (2) 2.02 (3) 2.764 (4) 154 (5)
O4—H4⋯O2 0.82 (2) 2.16 (4) 2.897 (4) 150 (7)
C6—H6BCgi 0.97 2.88 3.806 (6) 159
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In particular, Calix-Crown ethers in which the proper-sized crown rings are incorporated into the calixarene framework have attracted intense interest as a selective extractant for specific metal ions (Casnati et al., 1995; Csokai et al., 2006)). In this work, the title p-tert-butylcalixarene-thiacrown in the cone conformation was synthesized, and this is the first report of the crystal structure for the calixarene-thiacrown.

The title compound (I) is shown in Fig 1. The calixarene retains a distorted cone conformation in the solid state. The opposite arene rings A and C that bear the substituents are almost parallel to each other, whereas the other rings B and D include dihedral angles of 74.41 (17)°. Moreover, the plane defined by four methylenic bridges was chosen as a reference plane. The two rings bear the substituents are more vertical than the other two rings. The carbon atoms C1 and C5 in the alkyl chain points towards the exterior of the macrocycle and the torsion angles around the O1—C1, O2—C5 and bonds do not deviate from ideal syn values by about 5°. An additional close intramolecular hydrogen bonds between O4 and O2, O3 and O1 stabilize this conformation.

Related literature top

For background to the title compound, see: Csokai et al. (2006); Casnati et al. (1995). For the synthesis, see: Li et al. (1999).

Experimental top

A mixture of p-tert-butylcalix[4]arene dibromides (Li et al., 1999) (137 mg, 0.15 mmol) and Na2S.9H2O (48 mg, 0.20 mmol) in DMF (5 ml) was stirred at 333 K for 5 h. After cooling the reaction mixture to room temperature, it was quenched by water and extracted with dichloromethane. The organic layer was then washed with brine, dried over Na2SO4, and filtered. The solvent was evaporated in vacuo, and the residue was purified by column chromatography on silica gel from petroleum ether/dichloromethane. Petroleum ether/dichloromethane (5:1, v/v) to give 98 mg (83%) of compound I as white solid: mp 561~564 K; 1H NMR (400 MHz, CDCl3): d 7.92 (s, 2H), 7.05 (s, 4H), 6.85 (s, 4H), 4.26 (d, J = 12.8 Hz, 4H), 4.02 (t, J = 5.2 Hz, 4H), 3.32 (d, J = 12.8 Hz, 4H), 2.77 (brs, 4H), 2.31 (m, 4H), 2.06 (m, 4H), 1.28 (s, 18H), 1.00 (s, 18H); 13C NMR (100 MHz, CDCl3): d: 150.89 (C), 149.76 (C), 146.84 (C), 141.26 (C), 132.71 (C), 127.42 (C), 125.46 (CH), 125.03 (CH), 75.97 (CH2), 53.40 (CH2), 33.96 (C), 33.77 (C), 31.81 (CH2), 31.69 (CH3), 31.01 (CH3), 30.09 (CH2); MS(MALDI-TOF) m/z: 813.5 [M+Na]+.

Single crystals of (I) suitable for X-ray diffraction analysis were obtained by slow diffusion of petroleum ether into a chloroform solution at 298 K.

Refinement top

Hydroxy H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically with C—H = 0.93–0.97 Å and allowed to ride on their parent atoms, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound.
3,9,15,34-Tetra-tert-butyl-19,29-dioxa-24-thiahexacyclo[15.13.7.17,11.132,36.05,30.013,18]nonatriaconta-1(30),2,4,7,9,11 (39),13,15,17,32,34,36 (38)-dodecaene-38,39-diol top
Crystal data top
C52H70O4SF(000) = 1720
Mr = 791.14Dx = 1.092 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4874 reflections
a = 10.6222 (8) Åθ = 2.2–19.9°
b = 18.4690 (14) ŵ = 0.11 mm1
c = 24.5375 (18) ÅT = 293 K
V = 4813.8 (6) Å3Prismatic, colorless
Z = 40.40 × 0.32 × 0.31 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
5384 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.5°, θmin = 2.0°
phi and ω scansh = 1212
25550 measured reflectionsk = 2222
8942 independent reflectionsl = 2923
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)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.1159P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.002
8942 reflectionsΔρmax = 0.56 e Å3
562 parametersΔρmin = 0.33 e Å3
78 restraintsAbsolute structure: Flack (1983), 3232 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.09 (18)
Crystal data top
C52H70O4SV = 4813.8 (6) Å3
Mr = 791.14Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.6222 (8) ŵ = 0.11 mm1
b = 18.4690 (14) ÅT = 293 K
c = 24.5375 (18) Å0.40 × 0.32 × 0.31 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
5384 reflections with I > 2σ(I)
25550 measured reflectionsRint = 0.048
8942 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.191Δρmax = 0.56 e Å3
S = 0.93Δρmin = 0.33 e Å3
8942 reflectionsAbsolute structure: Flack (1983), 3232 Friedel pairs
562 parametersAbsolute structure parameter: 0.09 (18)
78 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*/UeqOcc. (<1)
S10.0878 (2)0.94377 (10)0.90988 (9)0.1381 (7)
O10.2336 (2)0.69951 (12)0.81364 (10)0.0593 (6)
O20.1025 (2)0.69865 (13)0.93842 (10)0.0637 (7)
O30.0257 (3)0.69895 (14)0.82319 (10)0.0590 (6)
O40.1556 (3)0.65281 (13)0.92220 (11)0.0617 (7)
C10.3305 (4)0.74876 (19)0.7971 (2)0.0758 (12)
H1A0.31300.76670.76070.091*
H1B0.41100.72400.79640.091*
C20.3354 (7)0.8098 (3)0.8359 (4)0.159 (2)
H2A0.38040.79280.86780.191*
H2B0.38740.84700.81930.191*
C30.2230 (7)0.8448 (3)0.8550 (4)0.157 (2)
H3A0.16790.80690.86840.188*
H3B0.18210.86550.82330.188*
C40.2248 (8)0.9005 (3)0.8962 (4)0.164 (2)
H4A0.28620.93660.88530.196*
H4B0.25480.87890.92980.196*
C50.1742 (5)0.7463 (2)0.9726 (2)0.0911 (14)
H5A0.16180.73461.01070.109*
H5B0.26320.74310.96420.109*
C60.1213 (6)0.8256 (3)0.9591 (3)0.1138 (15)
H6A0.11370.83190.92000.137*
H6B0.17870.86210.97300.137*
C70.0010 (6)0.8333 (3)0.9843 (3)0.1219 (16)
H7A0.05670.79740.96990.146*
H7B0.00850.82571.02330.146*
C80.0510 (7)0.9105 (3)0.9730 (3)0.1232 (18)
H8A0.12680.91520.99480.148*
H8B0.00980.94390.98840.148*
C90.2391 (3)0.62980 (17)0.79171 (13)0.0477 (8)
C100.3048 (3)0.57645 (17)0.81889 (13)0.0477 (8)
C110.3061 (3)0.50807 (18)0.79627 (14)0.0545 (9)
H110.35210.47200.81370.065*
C120.2432 (4)0.49106 (18)0.74970 (15)0.0574 (9)
C130.1713 (4)0.5451 (2)0.72468 (14)0.0581 (9)
H130.12460.53370.69380.070*
C140.1680 (3)0.61492 (19)0.74485 (13)0.0515 (8)
C150.0867 (4)0.6714 (2)0.71783 (14)0.0605 (10)
H15A0.11500.71880.72960.073*
H15B0.09970.66860.67880.073*
C160.0521 (4)0.66559 (17)0.72893 (14)0.0534 (9)
C170.1379 (4)0.64985 (19)0.68798 (15)0.0604 (10)
H170.10710.64190.65300.072*
C180.2676 (4)0.64519 (18)0.69618 (16)0.0607 (10)
C190.3085 (4)0.65502 (18)0.74975 (16)0.0625 (10)
H190.39390.65040.75720.075*
C200.2279 (3)0.67124 (17)0.79206 (14)0.0517 (8)
C210.1006 (4)0.67838 (17)0.78106 (13)0.0503 (8)
C220.2760 (4)0.6799 (2)0.84908 (15)0.0632 (10)
H22A0.36730.68070.84860.076*
H22B0.24710.72580.86370.076*
C230.2312 (3)0.61877 (19)0.88562 (14)0.0537 (9)
C240.1513 (3)0.63011 (19)0.92911 (13)0.0528 (9)
C250.1022 (4)0.5723 (2)0.95819 (14)0.0597 (9)
C260.1364 (4)0.5030 (2)0.94321 (16)0.0646 (10)
H260.10590.46430.96350.078*
C270.2141 (4)0.4887 (2)0.89929 (17)0.0649 (10)
C280.2613 (4)0.54823 (19)0.87183 (15)0.0580 (9)
H280.31590.54050.84280.070*
C290.0038 (4)0.5823 (2)1.00247 (15)0.0737 (11)
H29A0.03000.55731.03540.088*
H29B0.00570.63331.01090.088*
C300.1205 (4)0.5515 (2)0.98240 (14)0.0611 (10)
C310.1629 (4)0.4873 (2)1.00226 (15)0.0696 (11)
H310.11820.46561.03050.084*
C320.2693 (4)0.4524 (2)0.98259 (15)0.0681 (10)
C330.3335 (4)0.4875 (2)0.94081 (15)0.0625 (10)
H330.40470.46550.92620.075*
C340.2958 (3)0.55424 (18)0.91986 (13)0.0514 (8)
C350.1904 (4)0.58580 (18)0.94134 (13)0.0531 (8)
C360.3663 (3)0.58945 (19)0.87391 (14)0.0553 (9)
H36A0.45160.57070.87310.066*
H36B0.37110.64120.88050.066*
C370.2451 (5)0.4141 (2)0.7254 (2)0.0834 (13)
C380.3348 (10)0.3659 (3)0.7538 (4)0.211 (5)
H38A0.31050.36110.79130.317*
H38B0.41790.38610.75170.317*
H38C0.33430.31910.73670.317*
C390.2931 (8)0.4212 (3)0.6637 (3)0.148 (3)
H39A0.37010.44830.66290.222*
H39B0.23040.44560.64240.222*
H39C0.30740.37370.64890.222*
C400.1169 (6)0.3839 (3)0.7209 (3)0.129 (2)
H40A0.12110.33630.70530.194*
H40B0.06670.41460.69790.194*
H40C0.07940.38120.75640.194*
C410.3635 (5)0.6318 (3)0.65089 (19)0.0860 (14)
C420.4427 (6)0.5666 (4)0.6640 (3)0.139 (2)
H42A0.39040.52420.66460.208*
H42B0.50680.56100.63680.208*
H42C0.48130.57290.69910.208*
C430.3031 (6)0.6218 (3)0.5947 (2)0.1106 (18)
H43A0.25410.57820.59450.166*
H43B0.24950.66240.58690.166*
H43C0.36780.61870.56750.166*
C440.4535 (6)0.6987 (4)0.6479 (3)0.134 (2)
H44A0.51070.69280.61790.201*
H44B0.40470.74190.64260.201*
H44C0.50020.70250.68120.201*
C450.2315 (5)0.4123 (2)0.8778 (2)0.0913 (15)
C460.2322 (12)0.3563 (4)0.9232 (4)0.220 (5)
H46A0.27860.31450.91160.330*
H46B0.27130.37660.95500.330*
H46C0.14730.34260.93170.330*
C470.1257 (9)0.3966 (4)0.8396 (5)0.242 (7)
H47A0.13990.35080.82210.362*
H47B0.04800.39500.85950.362*
H47C0.12130.43410.81250.362*
C480.3565 (7)0.4035 (3)0.8463 (3)0.136 (2)
H48A0.35200.43000.81270.203*
H48B0.42460.42190.86800.203*
H48C0.37060.35320.83870.203*
C490.3076 (5)0.3784 (2)1.00480 (19)0.0905 (14)
C500.3172 (12)0.3800 (5)1.0656 (3)0.125 (3)0.70
H50A0.32390.33141.07920.188*0.70
H50B0.24350.40261.08060.188*0.70
H50C0.39050.40701.07610.188*0.70
C510.4261 (11)0.3498 (6)0.9809 (4)0.137 (3)0.70
H51A0.49360.38300.98800.206*0.70
H51B0.41590.34430.94220.206*0.70
H51C0.44520.30370.99690.206*0.70
C520.1961 (10)0.3227 (4)0.9911 (4)0.132 (3)0.70
H52A0.22040.27491.00210.198*0.70
H52B0.17990.32320.95260.198*0.70
H52C0.12140.33691.01040.198*0.70
C50'0.235 (2)0.3516 (12)1.0525 (9)0.132 (4)0.30
H50D0.17560.38861.06210.199*0.30
H50E0.28710.34091.08340.199*0.30
H50F0.19070.30871.04160.199*0.30
C51'0.4478 (18)0.3901 (11)1.0275 (10)0.132 (4)0.30
H51D0.43910.39641.06610.198*0.30
H51E0.48620.43251.01200.198*0.30
H51F0.49980.34871.02030.198*0.30
C52'0.333 (3)0.3288 (9)0.9581 (8)0.124 (4)0.30
H52D0.38450.28940.97010.185*0.30
H52E0.37490.35490.92970.185*0.30
H52F0.25420.31020.94450.185*0.30
H30.046 (2)0.713 (2)0.8223 (18)0.086 (16)*
H40.096 (5)0.674 (3)0.936 (3)0.17 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1379 (15)0.1169 (13)0.1593 (16)0.0001 (12)0.0094 (13)0.0160 (11)
O10.0668 (16)0.0406 (12)0.0704 (15)0.0052 (11)0.0217 (13)0.0028 (11)
O20.0686 (16)0.0533 (14)0.0691 (16)0.0041 (13)0.0218 (13)0.0159 (12)
O30.0531 (17)0.0683 (16)0.0556 (15)0.0007 (14)0.0047 (13)0.0041 (12)
O40.0675 (18)0.0528 (15)0.0648 (16)0.0109 (13)0.0056 (13)0.0052 (12)
C10.078 (3)0.052 (2)0.098 (3)0.007 (2)0.027 (3)0.000 (2)
C20.148 (5)0.078 (3)0.250 (6)0.042 (3)0.060 (5)0.045 (4)
C30.159 (4)0.073 (3)0.238 (5)0.024 (3)0.053 (4)0.046 (3)
C40.170 (5)0.080 (3)0.241 (6)0.027 (4)0.038 (5)0.042 (4)
C50.091 (3)0.080 (3)0.102 (3)0.003 (2)0.033 (3)0.037 (2)
C60.119 (3)0.096 (3)0.126 (3)0.020 (3)0.006 (3)0.045 (3)
C70.131 (4)0.107 (3)0.128 (3)0.022 (3)0.005 (3)0.042 (3)
C80.139 (4)0.097 (3)0.133 (4)0.003 (3)0.004 (3)0.023 (3)
C90.051 (2)0.0442 (18)0.0479 (19)0.0015 (15)0.0128 (16)0.0030 (14)
C100.0425 (18)0.0474 (18)0.0532 (19)0.0031 (15)0.0033 (15)0.0011 (15)
C110.055 (2)0.0477 (19)0.061 (2)0.0068 (16)0.0048 (17)0.0014 (16)
C120.057 (2)0.0495 (19)0.066 (2)0.0027 (17)0.0008 (19)0.0092 (17)
C130.059 (2)0.064 (2)0.051 (2)0.0037 (19)0.0044 (17)0.0102 (17)
C140.049 (2)0.061 (2)0.0453 (19)0.0044 (16)0.0064 (16)0.0024 (16)
C150.067 (3)0.063 (2)0.051 (2)0.0097 (19)0.0092 (18)0.0158 (17)
C160.066 (2)0.0399 (18)0.054 (2)0.0108 (16)0.0034 (18)0.0111 (15)
C170.077 (3)0.056 (2)0.048 (2)0.0158 (18)0.002 (2)0.0001 (16)
C180.066 (3)0.051 (2)0.066 (2)0.0094 (17)0.008 (2)0.0015 (17)
C190.059 (2)0.054 (2)0.075 (3)0.0078 (17)0.004 (2)0.0038 (19)
C200.055 (2)0.0440 (18)0.056 (2)0.0085 (16)0.0009 (18)0.0057 (15)
C210.060 (2)0.0407 (18)0.050 (2)0.0088 (16)0.0002 (18)0.0035 (14)
C220.053 (2)0.064 (2)0.072 (2)0.0151 (18)0.0076 (19)0.0092 (19)
C230.048 (2)0.057 (2)0.056 (2)0.0056 (17)0.0177 (17)0.0003 (16)
C240.056 (2)0.057 (2)0.046 (2)0.0024 (17)0.0118 (17)0.0019 (16)
C250.059 (2)0.067 (2)0.053 (2)0.0043 (19)0.0160 (18)0.0014 (18)
C260.070 (3)0.064 (2)0.060 (2)0.0077 (19)0.014 (2)0.0148 (19)
C270.059 (2)0.052 (2)0.084 (3)0.0064 (18)0.017 (2)0.0058 (19)
C280.052 (2)0.061 (2)0.061 (2)0.0008 (18)0.0003 (17)0.0006 (17)
C290.074 (3)0.094 (3)0.053 (2)0.013 (2)0.006 (2)0.005 (2)
C300.071 (3)0.068 (2)0.0442 (19)0.010 (2)0.0014 (18)0.0040 (17)
C310.085 (3)0.077 (3)0.047 (2)0.009 (2)0.008 (2)0.0075 (19)
C320.089 (3)0.062 (2)0.054 (2)0.008 (2)0.002 (2)0.0046 (18)
C330.069 (2)0.065 (2)0.053 (2)0.0162 (19)0.0001 (19)0.0013 (18)
C340.056 (2)0.0507 (19)0.0477 (19)0.0047 (17)0.0074 (16)0.0087 (15)
C350.062 (2)0.0522 (19)0.0448 (19)0.0035 (17)0.0081 (17)0.0055 (16)
C360.053 (2)0.057 (2)0.056 (2)0.0015 (17)0.0019 (17)0.0028 (16)
C370.085 (3)0.058 (2)0.107 (4)0.001 (2)0.012 (3)0.029 (2)
C380.284 (11)0.081 (4)0.269 (10)0.087 (6)0.171 (9)0.087 (5)
C390.200 (8)0.101 (4)0.143 (5)0.021 (5)0.042 (5)0.072 (4)
C400.120 (5)0.087 (4)0.180 (6)0.015 (4)0.001 (5)0.038 (4)
C410.088 (3)0.091 (3)0.079 (3)0.005 (3)0.025 (3)0.007 (2)
C420.140 (6)0.148 (6)0.130 (5)0.058 (5)0.020 (4)0.024 (4)
C430.126 (5)0.133 (5)0.073 (3)0.008 (4)0.020 (3)0.016 (3)
C440.124 (5)0.157 (6)0.121 (4)0.049 (4)0.061 (4)0.028 (4)
C450.095 (4)0.051 (2)0.128 (4)0.009 (2)0.013 (3)0.009 (2)
C460.324 (14)0.076 (4)0.261 (10)0.048 (6)0.080 (10)0.046 (5)
C470.176 (9)0.143 (7)0.406 (16)0.032 (6)0.128 (10)0.149 (9)
C480.149 (6)0.076 (4)0.182 (6)0.018 (4)0.009 (5)0.037 (4)
C490.114 (4)0.072 (3)0.085 (3)0.024 (3)0.005 (3)0.016 (2)
C500.173 (8)0.102 (6)0.100 (5)0.024 (5)0.040 (5)0.036 (4)
C510.177 (8)0.105 (6)0.131 (7)0.066 (6)0.002 (6)0.028 (5)
C520.183 (8)0.072 (4)0.141 (6)0.011 (5)0.031 (6)0.018 (4)
C50'0.180 (10)0.093 (8)0.124 (8)0.013 (8)0.016 (8)0.036 (7)
C51'0.172 (9)0.096 (7)0.129 (8)0.048 (7)0.026 (8)0.025 (7)
C52'0.178 (10)0.065 (6)0.128 (8)0.033 (8)0.017 (8)0.004 (7)
Geometric parameters (Å, º) top
S1—C41.694 (8)C30—C351.403 (5)
S1—C81.711 (7)C31—C321.387 (6)
O1—C91.397 (4)C31—H310.9300
O1—C11.433 (5)C32—C331.391 (5)
O2—C241.387 (4)C32—C491.527 (6)
O2—C51.435 (4)C33—C341.395 (5)
O3—C211.359 (4)C33—H330.9300
O3—H30.80 (2)C34—C351.367 (5)
O4—C351.374 (4)C34—C361.502 (5)
O4—H40.82 (2)C36—H36A0.9700
C1—C21.476 (7)C36—H36B0.9700
C1—H1A0.9700C37—C401.476 (7)
C1—H1B0.9700C37—C381.479 (8)
C2—C31.437 (8)C37—C391.603 (8)
C2—H2A0.9700C38—H38A0.9600
C2—H2B0.9700C38—H38B0.9600
C3—C41.441 (9)C38—H38C0.9600
C3—H3A0.9700C39—H39A0.9600
C3—H3B0.9700C39—H39B0.9600
C4—H4A0.9700C39—H39C0.9600
C4—H4B0.9700C40—H40A0.9600
C5—C61.602 (7)C40—H40B0.9600
C5—H5A0.9700C40—H40C0.9600
C5—H5B0.9700C41—C421.504 (7)
C6—C71.427 (8)C41—C431.532 (7)
C6—H6A0.9700C41—C441.563 (7)
C6—H6B0.9700C42—H42A0.9600
C7—C81.554 (8)C42—H42B0.9600
C7—H7A0.9700C42—H42C0.9600
C7—H7B0.9700C43—H43A0.9600
C8—H8A0.9700C43—H43B0.9600
C8—H8B0.9700C43—H43C0.9600
C9—C101.379 (5)C44—H44A0.9600
C9—C141.403 (5)C44—H44B0.9600
C10—C111.380 (4)C44—H44C0.9600
C10—C361.519 (5)C45—C471.492 (10)
C11—C121.361 (5)C45—C461.519 (9)
C11—H110.9300C45—C481.546 (8)
C12—C131.398 (5)C46—H46A0.9600
C12—C371.541 (5)C46—H46B0.9600
C13—C141.382 (5)C46—H46C0.9600
C13—H130.9300C47—H47A0.9600
C14—C151.508 (5)C47—H47B0.9600
C15—C161.503 (5)C47—H47C0.9600
C15—H15A0.9700C48—H48A0.9600
C15—H15B0.9700C48—H48B0.9600
C16—C171.387 (5)C48—H48C0.9600
C16—C211.399 (5)C49—C50'1.486 (16)
C17—C181.396 (5)C49—C511.486 (10)
C17—H170.9300C49—C52'1.491 (15)
C18—C191.396 (5)C49—C501.496 (9)
C18—C411.528 (6)C49—C521.604 (10)
C19—C201.378 (5)C49—C51'1.605 (16)
C19—H190.9300C50—H50A0.9600
C20—C211.386 (5)C50—H50B0.9600
C20—C221.498 (5)C50—H50C0.9600
C22—C231.519 (5)C50—H50E0.9032
C22—H22A0.9700C51—H51A0.9600
C22—H22B0.9700C51—H51B0.9600
C23—C241.379 (5)C51—H51C0.9600
C23—C281.384 (5)C52—H52A0.9600
C24—C251.386 (5)C52—H52B0.9600
C25—C261.380 (5)C52—H52C0.9600
C25—C291.518 (6)C50'—H50D0.9600
C26—C271.383 (6)C50'—H50E0.9600
C26—H260.9300C50'—H50F0.9600
C27—C281.383 (5)C51'—H51D0.9600
C27—C451.518 (6)C51'—H51E0.9600
C28—H280.9300C51'—H51F0.9600
C29—C301.520 (5)C52'—H52D0.9600
C29—H29A0.9700C52'—H52E0.9600
C29—H29B0.9700C52'—H52F0.9600
C30—C311.359 (5)
C4—S1—C8101.9 (4)C34—C36—H36B109.1
C9—O1—C1116.5 (3)C10—C36—H36B109.1
C24—O2—C5117.3 (3)H36A—C36—H36B107.8
C21—O3—H3129 (3)C40—C37—C38113.7 (6)
C35—O4—H4120 (5)C40—C37—C12111.5 (4)
O1—C1—C2109.1 (4)C38—C37—C12112.5 (4)
O1—C1—H1A109.9C40—C37—C39104.6 (5)
C2—C1—H1A109.9C38—C37—C39106.7 (6)
O1—C1—H1B109.9C12—C37—C39107.1 (4)
C2—C1—H1B109.9C37—C38—H38A109.5
H1A—C1—H1B108.3C37—C38—H38B109.5
C3—C2—C1121.7 (6)H38A—C38—H38B109.5
C3—C2—H2A106.9C37—C38—H38C109.5
C1—C2—H2A106.9H38A—C38—H38C109.5
C3—C2—H2B106.9H38B—C38—H38C109.5
C1—C2—H2B106.9C37—C39—H39A109.5
H2A—C2—H2B106.7C37—C39—H39B109.5
C2—C3—C4122.6 (7)H39A—C39—H39B109.5
C2—C3—H3A106.7C37—C39—H39C109.5
C4—C3—H3A106.7H39A—C39—H39C109.5
C2—C3—H3B106.7H39B—C39—H39C109.5
C4—C3—H3B106.7C37—C40—H40A109.5
H3A—C3—H3B106.6C37—C40—H40B109.5
C3—C4—S1117.7 (6)H40A—C40—H40B109.5
C3—C4—H4A107.9C37—C40—H40C109.5
S1—C4—H4A107.9H40A—C40—H40C109.5
C3—C4—H4B107.9H40B—C40—H40C109.5
S1—C4—H4B107.9C42—C41—C18110.2 (4)
H4A—C4—H4B107.2C42—C41—C43109.3 (5)
O2—C5—C6104.8 (4)C18—C41—C43113.2 (4)
O2—C5—H5A110.8C42—C41—C44107.5 (5)
C6—C5—H5A110.8C18—C41—C44108.3 (4)
O2—C5—H5B110.8C43—C41—C44108.0 (4)
C6—C5—H5B110.8C41—C42—H42A109.5
H5A—C5—H5B108.9C41—C42—H42B109.5
C7—C6—C5108.4 (5)H42A—C42—H42B109.5
C7—C6—H6A110.0C41—C42—H42C109.5
C5—C6—H6A110.0H42A—C42—H42C109.5
C7—C6—H6B110.0H42B—C42—H42C109.5
C5—C6—H6B110.0C41—C43—H43A109.5
H6A—C6—H6B108.4C41—C43—H43B109.5
C6—C7—C8109.4 (5)H43A—C43—H43B109.5
C6—C7—H7A109.8C41—C43—H43C109.5
C8—C7—H7A109.8H43A—C43—H43C109.5
C6—C7—H7B109.8H43B—C43—H43C109.5
C8—C7—H7B109.8C41—C44—H44A109.5
H7A—C7—H7B108.2C41—C44—H44B109.5
C7—C8—S1124.9 (4)H44A—C44—H44B109.5
C7—C8—H8A106.1C41—C44—H44C109.5
S1—C8—H8A106.1H44A—C44—H44C109.5
C7—C8—H8B106.1H44B—C44—H44C109.5
S1—C8—H8B106.1C47—C45—C27107.9 (4)
H8A—C8—H8B106.3C47—C45—C46109.5 (7)
C10—C9—O1119.6 (3)C27—C45—C46112.3 (5)
C10—C9—C14121.9 (3)C47—C45—C48108.2 (6)
O1—C9—C14118.3 (3)C27—C45—C48112.0 (4)
C9—C10—C11117.7 (3)C46—C45—C48106.9 (6)
C9—C10—C36122.3 (3)C45—C46—H46A109.5
C11—C10—C36119.8 (3)C45—C46—H46B109.5
C12—C11—C10123.0 (3)H46A—C46—H46B109.5
C12—C11—H11118.5C45—C46—H46C109.5
C10—C11—H11118.5H46A—C46—H46C109.5
C11—C12—C13118.2 (3)H46B—C46—H46C109.5
C11—C12—C37122.1 (3)C45—C47—H47A109.5
C13—C12—C37119.7 (3)C45—C47—H47B109.5
C14—C13—C12121.5 (3)H47A—C47—H47B109.5
C14—C13—H13119.2C45—C47—H47C109.5
C12—C13—H13119.2H47A—C47—H47C109.5
C13—C14—C9117.5 (3)H47B—C47—H47C109.5
C13—C14—C15120.2 (3)C45—C48—H48A109.5
C9—C14—C15122.2 (3)C45—C48—H48B109.5
C16—C15—C14115.6 (3)H48A—C48—H48B109.5
C16—C15—H15A108.4C45—C48—H48C109.5
C14—C15—H15A108.4H48A—C48—H48C109.5
C16—C15—H15B108.4H48B—C48—H48C109.5
C14—C15—H15B108.4C50'—C49—C51129.2 (10)
H15A—C15—H15B107.4C50'—C49—C52'119.5 (14)
C17—C16—C21117.1 (3)C51—C49—C52'47.7 (11)
C17—C16—C15121.9 (3)C50'—C49—C5042.0 (10)
C21—C16—C15121.0 (3)C51—C49—C50110.1 (7)
C16—C17—C18123.9 (3)C52'—C49—C50140.0 (9)
C16—C17—H17118.1C50'—C49—C32116.2 (10)
C18—C17—H17118.1C51—C49—C32113.8 (5)
C17—C18—C19115.8 (4)C52'—C49—C32108.9 (8)
C17—C18—C41124.3 (4)C50—C49—C32110.9 (5)
C19—C18—C41119.9 (4)C50'—C49—C5264.5 (11)
C20—C19—C18123.0 (4)C51—C49—C52108.3 (7)
C20—C19—H19118.5C52'—C49—C5264.9 (12)
C18—C19—H19118.5C50—C49—C52105.8 (7)
C19—C20—C21118.7 (3)C32—C49—C52107.6 (4)
C19—C20—C22121.0 (3)C50'—C49—C51'104.7 (14)
C21—C20—C22120.3 (3)C51—C49—C51'53.1 (10)
O3—C21—C20116.8 (3)C52'—C49—C51'100.6 (15)
O3—C21—C16121.8 (3)C50—C49—C51'65.7 (10)
C20—C21—C16121.4 (3)C32—C49—C51'104.5 (8)
C20—C22—C23111.4 (3)C52—C49—C51'147.6 (8)
C20—C22—H22A109.4C49—C50—H50A109.5
C23—C22—H22A109.4C49—C50—H50B109.5
C20—C22—H22B109.4C49—C50—H50C109.5
C23—C22—H22B109.4C49—C50—H50D82.9
H22A—C22—H22B108.0H50A—C50—H50D101.0
C24—C23—C28118.3 (3)H50B—C50—H50D33.5
C24—C23—C22122.5 (3)H50C—C50—H50D140.0
C28—C23—C22118.9 (3)C49—C50—H50E116.3
C23—C24—C25120.9 (3)H50A—C50—H50E27.1
C23—C24—O2119.7 (3)H50B—C50—H50E82.7
C25—C24—O2118.5 (3)H50C—C50—H50E125.0
C26—C25—C24118.5 (4)H50D—C50—H50E76.1
C26—C25—C29118.9 (4)C49—C50—H51D94.6
C24—C25—C29122.3 (4)H50A—C50—H51D97.9
C25—C26—C27122.8 (4)H50B—C50—H51D133.8
C25—C26—H26118.6H50C—C50—H51D24.4
C27—C26—H26118.6H50D—C50—H51D160.6
C28—C27—C26116.4 (4)H50E—C50—H51D121.5
C28—C27—C45121.7 (4)C49—C51—H51A109.5
C26—C27—C45121.4 (4)C49—C51—H51B109.5
C27—C28—C23123.0 (4)C49—C51—H51C109.5
C27—C28—H28118.5C49—C51—H51F103.4
C23—C28—H28118.5H51A—C51—H51F53.0
C25—C29—C30108.7 (3)H51B—C51—H51F146.8
C25—C29—H29A109.9H51C—C51—H51F62.3
C30—C29—H29A109.9C49—C52—H52A109.5
C25—C29—H29B109.9C49—C52—H52B109.5
C30—C29—H29B109.9C49—C52—H52C109.5
H29A—C29—H29B108.3C49—C52—H50F87.7
C31—C30—C35118.5 (3)H52A—C52—H50F63.1
C31—C30—C29119.8 (4)H52B—C52—H50F162.8
C35—C30—C29121.6 (3)H52C—C52—H50F62.4
C30—C31—C32123.3 (4)C49—C50'—H50D107.2
C30—C31—H31118.3C49—C50'—H50E113.1
C32—C31—H31118.3H50D—C50'—H50E109.5
C31—C32—C33116.1 (3)C49—C50'—H50F108.0
C31—C32—C49120.5 (4)H50D—C50'—H50F109.5
C33—C32—C49123.3 (4)H50E—C50'—H50F109.5
C32—C33—C34122.8 (4)C49—C51'—H51D105.6
C32—C33—H33118.6C49—C51'—H51E111.5
C34—C33—H33118.6H51D—C51'—H51E109.5
C35—C34—C33118.0 (3)C49—C51'—H51F111.2
C35—C34—C36120.9 (3)H51D—C51'—H51F109.5
C33—C34—C36121.1 (3)H51E—C51'—H51F109.5
C34—C35—O4118.2 (3)C49—C52'—H52D109.5
C34—C35—C30121.2 (3)C49—C52'—H52E109.5
O4—C35—C30120.7 (3)H52D—C52'—H52E109.5
C34—C36—C10112.6 (3)C49—C52'—H52F109.5
C34—C36—H36A109.1H52D—C52'—H52F109.5
C10—C36—H36A109.1H52E—C52'—H52F109.5
C9—O1—C1—C2162.1 (5)C24—C25—C26—C272.3 (6)
O1—C1—C2—C344.2 (9)C29—C25—C26—C27172.5 (3)
C1—C2—C3—C4174.8 (7)C25—C26—C27—C282.7 (5)
C2—C3—C4—S1173.2 (7)C25—C26—C27—C45169.1 (4)
C8—S1—C4—C3108.8 (7)C26—C27—C28—C231.9 (5)
C24—O2—C5—C6161.3 (4)C45—C27—C28—C23169.9 (4)
O2—C5—C6—C774.7 (5)C24—C23—C28—C270.7 (5)
C5—C6—C7—C8178.7 (4)C22—C23—C28—C27173.2 (3)
C6—C7—C8—S163.8 (7)C26—C25—C29—C3064.3 (5)
C4—S1—C8—C774.8 (6)C24—C25—C29—C30110.2 (4)
C1—O1—C9—C1090.5 (4)C25—C29—C30—C31105.5 (4)
C1—O1—C9—C1494.9 (4)C25—C29—C30—C3570.9 (5)
O1—C9—C10—C11179.0 (3)C35—C30—C31—C322.5 (6)
C14—C9—C10—C114.6 (5)C29—C30—C31—C32174.0 (4)
O1—C9—C10—C363.4 (5)C30—C31—C32—C330.7 (6)
C14—C9—C10—C36171.0 (3)C30—C31—C32—C49176.8 (4)
C9—C10—C11—C121.8 (5)C31—C32—C33—C340.9 (6)
C36—C10—C11—C12173.8 (3)C49—C32—C33—C34178.3 (4)
C10—C11—C12—C131.8 (6)C32—C33—C34—C350.5 (5)
C10—C11—C12—C37179.5 (4)C32—C33—C34—C36178.7 (3)
C11—C12—C13—C142.9 (5)C33—C34—C35—O4177.6 (3)
C37—C12—C13—C14179.4 (4)C36—C34—C35—O44.2 (5)
C12—C13—C14—C90.3 (5)C33—C34—C35—C301.4 (5)
C12—C13—C14—C15178.3 (3)C36—C34—C35—C30176.8 (3)
C10—C9—C14—C133.5 (5)C31—C30—C35—C342.8 (5)
O1—C9—C14—C13178.0 (3)C29—C30—C35—C34173.6 (3)
C10—C9—C14—C15174.4 (3)C31—C30—C35—O4176.1 (3)
O1—C9—C14—C150.1 (5)C29—C30—C35—O47.4 (5)
C13—C14—C15—C1675.5 (4)C35—C34—C36—C1079.9 (4)
C9—C14—C15—C16102.3 (4)C33—C34—C36—C1098.2 (4)
C14—C15—C16—C17114.8 (4)C9—C10—C36—C34106.0 (4)
C14—C15—C16—C2167.4 (4)C11—C10—C36—C3469.5 (4)
C21—C16—C17—C180.9 (5)C11—C12—C37—C40121.3 (5)
C15—C16—C17—C18178.8 (3)C13—C12—C37—C4056.3 (6)
C16—C17—C18—C192.2 (5)C11—C12—C37—C387.8 (8)
C16—C17—C18—C41176.6 (4)C13—C12—C37—C38174.6 (6)
C17—C18—C19—C202.5 (5)C11—C12—C37—C39124.8 (5)
C41—C18—C19—C20176.3 (3)C13—C12—C37—C3957.6 (6)
C18—C19—C20—C210.2 (5)C17—C18—C41—C42124.3 (5)
C18—C19—C20—C22178.9 (3)C19—C18—C41—C4256.9 (6)
C19—C20—C21—O3175.9 (3)C17—C18—C41—C431.5 (6)
C22—C20—C21—O35.0 (4)C19—C18—C41—C43179.7 (4)
C19—C20—C21—C163.6 (5)C17—C18—C41—C44118.2 (5)
C22—C20—C21—C16175.5 (3)C19—C18—C41—C4460.5 (6)
C17—C16—C21—O3175.5 (3)C28—C27—C45—C4787.1 (8)
C15—C16—C21—O32.4 (5)C26—C27—C45—C4784.2 (8)
C17—C16—C21—C203.9 (5)C28—C27—C45—C46152.2 (6)
C15—C16—C21—C20178.2 (3)C26—C27—C45—C4636.5 (8)
C19—C20—C22—C23111.3 (4)C28—C27—C45—C4831.9 (6)
C21—C20—C22—C2367.7 (4)C26—C27—C45—C48156.8 (5)
C20—C22—C23—C24115.1 (4)C31—C32—C49—C50'7.6 (14)
C20—C22—C23—C2858.4 (4)C33—C32—C49—C50'175.1 (13)
C28—C23—C24—C250.2 (5)C31—C32—C49—C51177.9 (7)
C22—C23—C24—C25173.4 (3)C33—C32—C49—C514.8 (8)
C28—C23—C24—O2169.2 (3)C31—C32—C49—C52'130.9 (13)
C22—C23—C24—O24.4 (5)C33—C32—C49—C52'46.4 (14)
C5—O2—C24—C2389.4 (4)C31—C32—C49—C5053.2 (8)
C5—O2—C24—C25101.3 (4)C33—C32—C49—C50129.5 (7)
C23—C24—C25—C261.0 (5)C31—C32—C49—C5262.0 (6)
O2—C24—C25—C26170.2 (3)C33—C32—C49—C52115.3 (6)
C23—C24—C25—C29173.6 (3)C31—C32—C49—C51'122.3 (11)
O2—C24—C25—C294.4 (5)C33—C32—C49—C51'60.4 (11)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C30–C35 benzene ring.
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.80 (2)2.02 (3)2.764 (4)154 (5)
O4—H4···O20.82 (2)2.16 (4)2.897 (4)150 (7)
C6—H6B···Cgi0.972.883.806 (6)159
Symmetry code: (i) x1/2, y+3/2, z+2.

Experimental details

Crystal data
Chemical formulaC52H70O4S
Mr791.14
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)10.6222 (8), 18.4690 (14), 24.5375 (18)
V3)4813.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.40 × 0.32 × 0.31
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25550, 8942, 5384
Rint0.048
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.191, 0.93
No. of reflections8942
No. of parameters562
No. of restraints78
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.56, 0.33
Absolute structureFlack (1983), 3232 Friedel pairs
Absolute structure parameter0.09 (18)

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

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C30–C35 benzene ring.
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.80 (2)2.02 (3)2.764 (4)154 (5)
O4—H4···O20.82 (2)2.16 (4)2.897 (4)150 (7)
C6—H6B···Cgi0.972.883.806 (6)159
Symmetry code: (i) x1/2, y+3/2, z+2.
 

Acknowledgements

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

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCasnati, A., Pochini, A., Ungaro, R., Ugozzoli, F., Arnaud-Neu, F., Fanni, S., Schwing, M.-J., Egberink, R. J. M., de Jong, F. & Reinhoudt, D. N. (1995). J. Am. Chem. Soc. 117, 2767–2777.  CrossRef CAS Web of Science
First citationCsokai, V., Grün, A., Balázs, B., Simon, A., Tóth, G. & Bittera, I. (2006). Tetrahedron, 62, 10215–10222.  Web of Science CrossRef CAS
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationLi, Z.-T., Ji, G.-Z., Zhao, C.-X., Yuan, S.-D., Ding, H., Huang, C., Du, A.-L. & Wei, M. (1999). J. Org. Chem. 64, 3572–3584.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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