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Volume 69 
Part 5 
Pages m236-m237  
May 2013  

Received 6 March 2013
Accepted 20 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.095
Data-to-parameter ratio = 39.4
Details
Open access

[5,11,17,23-Tetra-tert-butyl-25,27-(3,6-dioxaoctan-1,8-dioxy)-26,28-bis(pyridin-2-ylmethoxy)calix[4]arene]sodium iodide-1,2,4,5-tetrafluoro-3,6-diiodobenzene-methanol (2/3/4)

aNFMLab, Department of Chemistry, Materials and Chemical Engineering, "G. Natta", Politecnico di Milano, Via Mancinelli, 7, I-20131 Milano, Italy, and bDipartimento di Chimica Organica e Biologica, Universitá di Messina, Salita Sperone 31, I-98166 Messina, Italy
Correspondence e-mail: giancarlo.terraneo@polimi.it

The title compound, [Na(C62H76N2O6)]I·1.5C6F4I2·2CH3OH, is composed of five components: a calix[4]arene derivative (hereinafter C4), a sodium cation, an iodide anion, a 1,2,4,5-tetrafluoro-3,6-diiodobenzene (tFdIB) molecule and a methanol molecule in a 1:1:1:1.5:2 ratio. The complex shows several interesting features: (i) the polyoxygenated loop of C4 effectively chelates a sodium cation in the form of a distorted octahedron and separates it from the iodide counter-ion, the shortest Na+...I- distance being greater than 6.5 Å; (ii) the cavity of C4 is filled by a methanol molecule; (iii) a second methanol molecule is hydrogen-bonded to the N atom of a pyridinyl substituent pendant of C4 and halogen-bonded to the I atom of a tFdIB molecule; (iv) the two I atoms of another tFdIB molecule are halogen-bonded to two iodide anions, which act as monodentate halogen-bond acceptorss; (v) one of the two tFdIB molecules is located about a centre of inversion.

Related literature

For applications of calix[4]arenes derivative, see: Dondoni & Marra (2010[Dondoni, A. & Marra, A. (2010). Chem. Rev. 110, 4949-4977.]). When calix-crown-arenes coordinate potassium (Gattuso et al., 2006[Gattuso, G., Liantonio, R., Metrangolo, P., Meyer, F., Pappalardo, A., Parisi, M. F., Pilati, T., Pisagatti, I. & Resnati, G. (2006). Supramol. Chem. 18, 235-243.]) or caesium cations (Gattuso et al., 2007[Gattuso, G., Pappalardo, A., Parisi, M. F., Pisagatti, I., Crea, F., Liantonio, R., Metrangolo, P., Navarrini, W., Resnati, G., Pilati, T. & Pappalardo, S. (2007). Tetrahedron, 63, 4951-4958.]), the resulting naked iodide anions form XBs with diiodoperfluoroalkanes. Alternatively, the N atoms of pyridyl pendants at the lower rim of calixarenes form halogen bonds with tetrafluoro-diiodobenzene (Messina et al., 2000[Messina, M. T., Metrangolo, P., Pappalardo, S., Parisi, M. F., Pilati, T. & Resnati, G. (2000). Chem. Eur. J. 6, 3495-3500.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [Na(C62H76N2O6)]I·1.5C6F4I2·2CH4O

  • Mr = 1762.01

  • Triclinic, [P \overline 1]

  • a = 13.4019 (12) Å

  • b = 14.2255 (12) Å

  • c = 21.022 (2) Å

  • [alpha] = 85.90 (2)°

  • [beta] = 84.61 (2)°

  • [gamma] = 65.75 (2)°

  • V = 3635.6 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.79 mm-1

  • T = 90 K

  • 0.42 × 0.30 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.866, Tmax = 1.000

  • 88833 measured reflections

  • 33353 independent reflections

  • 29534 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.095

  • S = 1.13

  • 33353 reflections

  • 847 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 2.33 e Å-3

  • [Delta][rho]min = -1.52 e Å-3

Table 1
Halogen and hydrogen-bond geometry (Å, °)

Z-X...Y Z-X X...Y Z...Y Z-X...Y
C63-I1...O7   2.75 (1)   179 (1)
C69-I3...I4   3.38 (1)   175 (1)
C66-I2...F6i   3.21 (1)   149 (1)
O7-H7O7...N2 0.84 2.00 2.809 (3) 161
Symmetry code: (i) x, y+1, z-1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL2012.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2501 ).


Acknowledgements

GC, PM, GR and GT acknowledge the Fondazione Cariplo (projects 2009-2550 and 2010-1351) for financial support.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Dondoni, A. & Marra, A. (2010). Chem. Rev. 110, 4949-4977.  [ISI] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gattuso, G., Liantonio, R., Metrangolo, P., Meyer, F., Pappalardo, A., Parisi, M. F., Pilati, T., Pisagatti, I. & Resnati, G. (2006). Supramol. Chem. 18, 235-243.  [ISI] [CrossRef] [ChemPort]
Gattuso, G., Pappalardo, A., Parisi, M. F., Pisagatti, I., Crea, F., Liantonio, R., Metrangolo, P., Navarrini, W., Resnati, G., Pilati, T. & Pappalardo, S. (2007). Tetrahedron, 63, 4951-4958.  [ISI] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Messina, M. T., Metrangolo, P., Pappalardo, S., Parisi, M. F., Pilati, T. & Resnati, G. (2000). Chem. Eur. J. 6, 3495-3500.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m236-m237   [ doi:10.1107/S1600536813007757 ]

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