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Volume 69 
Part 5 
Pages m284-m285  
May 2013  

Received 14 March 2013
Accepted 17 April 2013
Online 24 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.009 Å
R = 0.041
wR = 0.119
Data-to-parameter ratio = 14.9
Details
Open access

(Tris{2-[2-(2,3,5,6-tetrafluoro-4-iodophenoxy)ethoxy]ethyl}amine)potassium iodide

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

The title adduct, [K(C30H24F12I3NO6)]I, gives an extended tape of cations linked through I...I- halogen bonds (XBs), two of them being quite short and one quite long. In the structure, the cation is hosted in a cavity formed by the arms of the podand which presents a closed conformation wherein two tetrafluoroiodobenzene rings are near parallel [dihedral angle = 15.8 (4)°; centroid-centroid distance = 3.908 (5) Å] and the third ring is closer to orthogonal [dihedral angles = 66.28 (14) and 75.20 (19)°] to the other two rings. The coordination sphere of the K+ cation is composed of the six O atoms, the N atom and an F atom in the ortho position of one of the rings.

Related literature

For the synthesis of tris{2-[2-(2,3,5,6-tetrafluoro-4-iodophenoxy)ethoxy]ethyl}amine and its NaI adduct, see: Mele et al. (2005[Mele, A., Metrangolo, P., Neukirch, H., Pilati, T. & Resnati, G. (2005). J. Am. Chem. Soc. 127, 14972-14973.]). For its HI salt, see: Abate et al. (2009[Abate, A., Biella, S., Cavallo, G., Meyer, F., Neukirch, H., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2009). J. Fluorine Chem. 130, 1171-1177.]).

[Scheme 1]

Experimental

Crystal data
  • [K(C30H24F12I3NO6)]I

  • Mr = 1269.20

  • Monoclinic, P 21 /n

  • a = 13.037 (2) Å

  • b = 23.355 (3) Å

  • c = 13.787 (2) Å

  • [beta] = 104.83 (3)°

  • V = 4058.0 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.27 mm-1

  • T = 295 K

  • 0.34 × 0.22 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.759, Tmax = 1.000

  • 24956 measured reflections

  • 7254 independent reflections

  • 5627 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.119

  • S = 1.06

  • 7254 reflections

  • 487 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 2.37 e Å-3

  • [Delta][rho]min = -1.25 e Å-3

Table 1
I...I- XBs and short F...F contacts (Å and °)

C-X...Y X...Y C-X...Y
C8-I1...I4 3.4106 (6) 179.30 (13)
C8-I2...I4i 3.4157 (6) 168.45 (13)
C8-I3...I4ii 3.9437 (7) 179.21 (18)
Symmetry codes: (i) -x, -y, -z; (ii) -x, -y, -z + 1.Note: for the sake of comparison, a Cambridge Structural Database (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) search for C-I...I- contacts gives 109 hits with a mean I...I- distance of 3.53 (3) Å, the lower and higher quartiles being 3.43 and 3.63 Å, respectively.

Table 2
Short contacts in receptor-metal cation system for KI and NaI adducts

  K+ Na+
N1 2.903 (4) 2.515 (15)
O1 2.744 (3) 2.388 (12)
O2 2.849 (3) 2.716 (12)
O3 2.707 (4) 2.463 (13)
O4 2.809 (4) 2.424 (12)
O5 2.756 (4) 2.371 (14)
O6 2.911 (4) 4.39 (2)
F4 3.041 (4) 3.124 (17)
Note: in the NaI adduct, Na+...F4 and Na+...O6 distances cannot be considered as bond lengths, thus they are only reported for the sake of comparison.

Data collection: APEX2 (Bruker, 1998[Bruker (1998). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). 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, 2012[Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (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: PK2473 ).


Acknowledgements

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

References

Abate, A., Biella, S., Cavallo, G., Meyer, F., Neukirch, H., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2009). J. Fluorine Chem. 130, 1171-1177.  [ISI] [CSD] [CrossRef] [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bruker (1998). 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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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]
Mele, A., Metrangolo, P., Neukirch, H., Pilati, T. & Resnati, G. (2005). J. Am. Chem. Soc. 127, 14972-14973.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2012). SHELXL2012. University of Göttingen, Germany.


Acta Cryst (2013). E69, m284-m285   [ doi:10.1107/S1600536813010532 ]

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