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Volume 69 
Part 7 
Pages o1009-o1010  
July 2013  

Received 28 May 2013
Accepted 29 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.059
wR = 0.172
Data-to-parameter ratio = 15.3
Details
Open access

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

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 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[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155].

Related literature

For a similar compound adopting a 1,3-alternate conformation, see: Xu et al. (2008[Xu, W.-N., Yuan, J.-M., Liu, Y., Ma, J.-P. & Guo, D.-S. (2008). Acta Cryst. C64, o349-o352.]). For background to thiacalix[4]arene derivatives, see: Kumagai et al. (1997[Kumagai, H., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Ueda, S., Kamiyama, H. & Miyano, S. (1997). Tetrahedron Lett. 38, 3971-3972.]); Morohashi et al. (2006[Morohashi, N., Narumi, F., Iki, N., Hattori, T. & Miyano, S. (2006). Chem. Rev. 106, 5291-5316.]); Yamato et al. (2006[Yamato, T., Casas, C. P., Yamamoto, H., Elsegood, M. R. J., Dale, S. H. & Redshaw, C. (2006). J. Incl. Phenom. Macro. 54, 261-269.]). For background to multidentate methylthioethers, see: Maye et al. (2005[Maye, M. M., Lim, I.-I. S., Luo, J., Rab, Z., Rabinovich, D., Liu, T. & Zhong, C. J. (2005). J. Am. Chem. Soc. 127, 1519-1529.]); Lim et al. (2007[Lim, I.-I. S., Vaiana, C., Zhang, Z. Y., Zhang, Y. J., An, D. L. & Zhong, C. J. (2007). J. Am. Chem. Soc. 129, 5368-5369.]); Yan et al. (2010[Yan, H., Lim, I.-I. S., Zhang, Y. J., Chen, Q., Mott, D., Wu, W. T., Zhou, S. Q., An, D. L. & Zhong, C. J. (2010). Chem. Commun. 46, 2218-2220.]). For the synthesis, see: Morohashi et al. (2003[Morohashi, N., Katagiri, H., Iki, N., Yamane, Y., Kabuto, C., Hattori, T. & Miyano, S. (2003). J. Org. Chem. 68, 2324-2333.]).

[Scheme 1]

Experimental

Crystal data
  • C72H80O4S8

  • Mr = 1265.84

  • Triclinic, [P \overline 1]

  • a = 15.1863 (10) Å

  • b = 15.5795 (11) Å

  • c = 16.9774 (12) Å

  • [alpha] = 75.473 (2)°

  • [beta] = 85.686 (2)°

  • [gamma] = 84.762 (2)°

  • V = 3866.4 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 293 K

  • 0.26 × 0.21 × 0.15 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.434, Tmax = 1.000

  • 14394 measured reflections

  • 14394 independent reflections

  • 9034 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.172

  • S = 0.96

  • 14394 reflections

  • 939 parameters

  • 244 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2608 ).


Acknowledgements

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

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kumagai, H., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Ueda, S., Kamiyama, H. & Miyano, S. (1997). Tetrahedron Lett. 38, 3971-3972.  [CrossRef] [ChemPort] [Web of Science]
Lim, I.-I. S., Vaiana, C., Zhang, Z. Y., Zhang, Y. J., An, D. L. & Zhong, C. J. (2007). J. Am. Chem. Soc. 129, 5368-5369.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Maye, M. M., Lim, I.-I. S., Luo, J., Rab, Z., Rabinovich, D., Liu, T. & Zhong, C. J. (2005). J. Am. Chem. Soc. 127, 1519-1529.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Morohashi, N., Katagiri, H., Iki, N., Yamane, Y., Kabuto, C., Hattori, T. & Miyano, S. (2003). J. Org. Chem. 68, 2324-2333.  [CSD] [CrossRef] [PubMed] [ChemPort]
Morohashi, N., Narumi, F., Iki, N., Hattori, T. & Miyano, S. (2006). Chem. Rev. 106, 5291-5316.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Xu, W.-N., Yuan, J.-M., Liu, Y., Ma, J.-P. & Guo, D.-S. (2008). Acta Cryst. C64, o349-o352.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Yamato, T., Casas, C. P., Yamamoto, H., Elsegood, M. R. J., Dale, S. H. & Redshaw, C. (2006). J. Incl. Phenom. Macro. 54, 261-269.  [CSD] [CrossRef] [ChemPort]
Yan, H., Lim, I.-I. S., Zhang, Y. J., Chen, Q., Mott, D., Wu, W. T., Zhou, S. Q., An, D. L. & Zhong, C. J. (2010). Chem. Commun. 46, 2218-2220.  [CrossRef] [ChemPort]


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

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