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Volume 69 
Part 5 
Page o690  
May 2013  

Received 19 February 2013
Accepted 29 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.066
wR = 0.191
Data-to-parameter ratio = 15.9
Details
Open access

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

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...[pi] 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 K[alpha] radiation

  • [mu] = 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 > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -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 D...A 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-H6B...Cgi 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5679 ).


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

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [CrossRef] [ChemPort] [ISI]
Csokai, V., Grün, A., Balázs, B., Simon, A., Tóth, G. & Bittera, I. (2006). Tetrahedron, 62, 10215-10222.  [ISI] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o690  [ doi:10.1107/S1600536813008684 ]

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