[Journal logo]

Volume 69 
Part 4 
Pages o579-o580  
April 2013  

Received 4 February 2013
Accepted 19 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.005 Å
R = 0.038
wR = 0.093
Data-to-parameter ratio = 19.1
Details
Open access

1,3-Bis(2,3,5,6-tetrafluoro-4-iodophenoxy)-2,2-bis[(2,3,5,6-tetrafluoro-4-iodophenoxy)methyl]propane

aNFMLab, Department of Chemistry, Materials and Chemical Engineering, "G. Natta", Politecnico di Milano, Via Mancinelli, 7, I-20131 Milano, Italy
Correspondence e-mail: giancarlo.terraneo@polimi.it

In the crystal structure of the title compound, C29H8F16I4O4, short I...I and I...F contacts, which can be understood as halogen bonds (XBs), represent the strongest intermolecular interactions, consistent with the presence of I and F atoms, and the absence of H atoms, at the periphery of the molecule. In addition, [pi]-[pi] stacking interactions between tetrafluoroiodophenyl (TFIP) groups and five short F...F interactions are present.

Related literature

The title compound is a robust halogen-bonding (XB) donor tecton in supramolecular chemistry. For background to XB-based crystal engeneering, see: Guido et al. (2004[Guido, E., Metrangolo, P., Pilati, T. & Resnati, G. (2004). Acta Cryst. E60, o788-o790.], 2005[Guido, E., Metrangolo, P., Panzeri, W., Pilati, T., Resnati, G., Ursini, M. & Logothetis, T. A. (2005). J. Fluorine Chem. 126, 197-207.]); Lucassen et al. (2007[Lucassen, A. C. B., Karton, A., Leitus, G., Shimon, L. J. W., Martin, J. M. L. & van der Boom, M. E. (2007). Cryst. Growth Des. 7, 376-392.]); Metrangolo et al. (2007[Metrangolo, P., Meyer, F., Pilati, T., Proserpio, D. & Resnati, G. (2007). Chem. Eur. J. 13, 5765-5772.]). For the synthesis, see: Caronna et al. (2004[Caronna, T., Liantonio, R., Logothetis, T. A., Metrangolo, P., Pilati, T. & Resnati, G. (2004). J. Am. Chem. Soc. 126, 4500-4501.]). 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
  • C29H8F16I4O4

  • Mr = 1231.95

  • Monoclinic, P 21 /n

  • a = 7.9716 (9) Å

  • b = 20.665 (3) Å

  • c = 20.194 (4) Å

  • [beta] = 92.745 (12)°

  • V = 3322.8 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.88 mm-1

  • T = 90 K

  • 0.34 × 0.06 × 0.04 mm

Data collection
  • Bruker APEX 2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.742, Tmax = 1.000

  • 39668 measured reflections

  • 9728 independent reflections

  • 7975 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.093

  • S = 1.04

  • 9728 reflections

  • 510 parameters

  • 28 restraints

  • All H-atom parameters refined

  • [Delta][rho]max = 2.08 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Halogen bonds and C-F...F-C and [pi]-[pi] short interactions (Å, °)

The distances between the CNTRn of the four TFIP groups showing [pi]-[pi] interactions are also reported (CNTRn is the centroid of the benzene group linking the In iodine atom).

C-X...Y(-C) X...Y C-X...Y X...Y-C
C5-I1...I3i 3.7838 (6) 169.59 (11)  
C12-I2...F15ii 3.323 (3) 174.72 (11)  
C19-I3...F2iii 3.176 (3) 162.73 (11)  
C26-I4...F6iv 3.240 (3) 136.47 (11)  
C3-F1...(F12-C21)v 2.610 (3) 162.3 (2) 165.1 (3)
C4-F2...(F4-C7)v 2.790 (4) 150.2 (2) 149.5 (3)
C17-F9...(F11-C20)v 2.771 (4) 151.1 (2) 150.6 (3)
C10-F5...(F7-C13)v 2.679 (3) 158.8 (2) 157.2 (3)
C25-F14...(F16-C28)vi 2.821 (3) 147.6 (2) 149.2 (3)
CNTR1...CNTR4i 3.643 (6)    
C3...C27i 3.334 (5)    
C16...C11vii 3.317 (5)    
C18...C9vii 3.307 (5)    
F9...C13vii 3.156 (5)    
CNTR2...CNTR3vii 3.648 (6)    
Symmetry codes: (i) [{3\over 2}-x, -{1\over 2}+y, {3\over 2}-z]; (ii) 2-x, 2-y, 2-z; (iii) [-{3\over 2}+x, {3\over 2}-y, -{1\over 2}+z]; (iv) 1-x, 2-y, 2-z; (v) x+1, y, z; (vi) x-1, y, z; (vii) [-{1\over 2}+x, {3\over 2}-y, -{1\over 2}+z].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, 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: LH5584 ).


Acknowledgements

GC, PM, GR and GT thank 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 (1998). SMART, 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]
Caronna, T., Liantonio, R., Logothetis, T. A., Metrangolo, P., Pilati, T. & Resnati, G. (2004). J. Am. Chem. Soc. 126, 4500-4501.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Guido, E., Metrangolo, P., Pilati, T. & Resnati, G. (2004). Acta Cryst. E60, o788-o790.  [CSD] [CrossRef] [details]
Guido, E., Metrangolo, P., Panzeri, W., Pilati, T., Resnati, G., Ursini, M. & Logothetis, T. A. (2005). J. Fluorine Chem. 126, 197-207.  [ISI] [CSD] [CrossRef] [ChemPort]
Lucassen, A. C. B., Karton, A., Leitus, G., Shimon, L. J. W., Martin, J. M. L. & van der Boom, M. E. (2007). Cryst. Growth Des. 7, 376-392.  [CSD] [CrossRef]
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]
Metrangolo, P., Meyer, F., Pilati, T., Proserpio, D. & Resnati, G. (2007). Chem. Eur. J. 13, 5765-5772.  [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o579-o580   [ doi:10.1107/S1600536813007605 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.