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Volume 69 
Part 3 
Page o424  
March 2013  

Received 4 February 2013
Accepted 17 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.066
wR = 0.220
Data-to-parameter ratio = 15.8
Details
Open access

5,17-Diformyl-25,26,27,28-tetrapropoxycalix[4]arene

aJiangsu Key Laboratory of Fine Petrochemical Engineering, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
Correspondence e-mail: chemsxq@yahoo.com.cn

The title compound, C42H48O6, was obtained via formylation of 25,26,27,28-tetrapropoxycalix[4]arene with dichloromethyl methyl ether and tin tetrachloride. It adopts a pinched cone conformation, which leads to an open cavity. The two opposite aromatic rings bearing formyl groups are almost parallel, making a dihedral angle of 29.1 (2)°. The other pair of opposite rings are close to being perpendicular, making a dihedral angle of 73.6 (1)°. Adjacent rings are almost perpendicular, making dihedral angles of 78.8 (2), 81.6 (1), 78.2 (1) and 74.7 (1)°.

Related literature

For general background to calix[4]arenes, see: Arduini et al. (1995[Arduini, A., Fanni, S., Manfredi, G., Pochini, A., Ungaro, R., Sicuri, A. R. & Ugozzoli, F. (1995). J. Org. Chem. 60, 1448-1453.]); Decken et al. (2004[Decken, A., Harvey, P. D. & Douville, J. (2004). Acta Cryst. E60, o1170-o1171.]); Seigle-Ferrand et al. (2006[Seigle-Ferrand, P., Sdira, S. B., Felix, C., Lamartine, R., Bavoux, C., Fenet, B., Bayard, F. & Vocanson, F. (2006). Mater. Sci. Eng. C, 26, 181-185.]); Kennedy et al. (2010[Kennedy, S., Teat, S. J. & Dalgarno, S. J. (2010). Dalton Trans. 39, 384-387.]).

[Scheme 1]

Experimental

Crystal data
  • C42H48O6

  • Mr = 648.80

  • Orthorhombic, P b c a

  • a = 14.7121 (15) Å

  • b = 17.5133 (19) Å

  • c = 28.912 (3) Å

  • V = 7449.5 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.985, Tmax = 0.989

  • 41325 measured reflections

  • 6924 independent reflections

  • 3908 reflections with I > 2[sigma](I)

  • Rint = 0.085

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.220

  • S = 1.00

  • 6924 reflections

  • 437 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: SMART (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. 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: FJ2615 ).


Acknowledgements

We gratefully acknowledge the financial support from the Natural Science Foundation of China (No. 21002009), the Major Program for Natural Science Research of Jiangsu Colleges and Universities (12 K J A150002), the Scientific and Technological Project of Changzhou (CJ20115019), and the Qing-Lan Project of Jiangsu Province.

References

Arduini, A., Fanni, S., Manfredi, G., Pochini, A., Ungaro, R., Sicuri, A. R. & Ugozzoli, F. (1995). J. Org. Chem. 60, 1448-1453.  [CrossRef] [ChemPort]
Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Decken, A., Harvey, P. D. & Douville, J. (2004). Acta Cryst. E60, o1170-o1171.  [CSD] [CrossRef] [details]
Kennedy, S., Teat, S. J. & Dalgarno, S. J. (2010). Dalton Trans. 39, 384-387.  [CSD] [CrossRef] [ChemPort]
Seigle-Ferrand, P., Sdira, S. B., Felix, C., Lamartine, R., Bavoux, C., Fenet, B., Bayard, F. & Vocanson, F. (2006). Mater. Sci. Eng. C, 26, 181-185.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o424  [ doi:10.1107/S1600536813004625 ]

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