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Volume 69 
Part 3 
Pages o328-o329  
March 2013  

Received 23 November 2012
Accepted 18 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.007 Å
R = 0.039
wR = 0.114
Data-to-parameter ratio = 16.1
Details
Open access

The halogen-bonded adduct 1,4-bis(pyridin-4-yl)buta-1,3-diyne-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-1,8-diiodooctane (1/1)

aNFMLab, Department of Chemistry, Materials and Chemical Engineering, "G. Natta", Politecnico di Milano, Via Mancinelli, 7, I-20131 Milano, Italy, and bChemessentia Srl, via Bovio 6, I-28100 Novara, Italy
Correspondence e-mail: giancarlo.terraneo@polimi.it

In the crystal structure of the title compound, C8F16I2·C14H8N2, the molecules form infinite chains parallel to [2-11] through two symmetry-independent C-I...N halogen bonds (XBs). As commonly found, the perfluoroalkyl molecules segregate from the hydrocarbon ones, forming a layered structure. Apart from the XBs, the only contact below the sum of van der Waals radii is a weak H...F contact. The topology of the network is a nice example of the paradigm of the expansion of ditopic starting modules; the XB leads to the construction of infinite supramolecular chains along [2-11] formed by alternating XB donors and acceptors.

Related literature

For the use of bis-(4-pyridyl)buta-1,3-diine in crystal engeneering based on hydrogen bonding and transition metal binding, see: Nakamura et al. (2003[Nakamura, A., Sato, T. & Kuroda, R. (2003). CrystEngComm, 5, 318-325.]); Curtis et al. (2005[Curtis, S. M., Le, N., Fowler, F. W. & Lauher, J. W. (2005). Cryst. Growth Des. 5, 2313-2321.]); Maekawa et al. (2000[Maekawa, M., Konaka, H., Suenaga, Y., Takayoshi Kuroda-Sowa, T. & Munakata, M. (2000). J. Chem. Soc. Dalton Trans. pp. 4160-4166.]); Badruz Zaman et al. (2001[Badruz Zaman, M. D., Smith, M. D. & Zur Loye, H.-C. (2001). Chem. Mater. 13, 3534-3541.]); Allan et al. (1988[Allan, J. R., Barrow, M. J., Beaumont, P. C., Macindoe, L. A., Milburn, G. H. W. & Werninck, A. R. (1988). Inorg. Chim. Acta, 148, 85-90.]). For N...I halogen bonds based on [alpha],[omega]-diiodoperfluorocarbons, see: Neukirch et al. (2005[Neukirch, H., Guido, E., Liantonio, R., Metrangolo, P., Pilati, T. & Resnati, G. (2005). Chem. Commun. pp. 1534-1536.]); Navarrini et al. (2000[Navarrini, W., Metrangolo, P., Pilati, T. & Resnati, G. (2000). New J. Chem. 24, 777-780.]); Liantonio et al. (2003[Liantonio, R., Metrangolo, P., Pilati, T., Resnati, G. & Stevenazzi, A. (2003). Cryst. Growth Des. 3, 799-803.]); Bertani et al. (2002[Bertani, R., Metrangolo, P., Moiana, A., Perez, E., Pilati, T., Resnati, G., Rico-Lattes, I. & Sassi, A. (2002). Adv. Mater. 14, 1197-1201.]); Metrangolo et al. (2004[Metrangolo, P., Pilati, T., Resnati, G. & Stevenazzi, A. (2004). Chem. Commun. pp. 1492-1493.], 2008[Metrangolo, P., Meyer, F., Pilati, T. & Resnati, G. (2008). Chem. Commun. pp. 1635-1637.]); Fox et al. (2004[Fox, D. B., Liantonio, R., Metrangolo, P., Pilati, T. & Resnati, G. (2004). J. Fluorine Chem. 125, 271-281.]); Dey et al. (2009[Dey, A., Metrangolo, P., Pilati, T., Resnati, G., Terraneo, G. & Wlassics, I. (2009). J. Fluorine Chem. 130, 816-823.]). For segregation of perfluoroalkyl chains, see: Fox et al. (2008[Fox, D., Metrangolo, P., Pasini, D., Pilati, T., Resnati, G. & Terraneo, G. (2008). CrystEngComm, 10, 1132-1136.]). For chirality and order/disorder of long perfluoroalkyl chains, see: Monde et al. (2006[Monde, K., Miura, N., Hashimoto, M., Taniguchi, T. & Inabe, T. (2006). J. Am. Chem. Soc. 128, 6000-6001.]). For the synthesis of bis-(4-pyridyl)buta-1,3-diine, see: Della Ciana & Haim (1984[Della Ciana, L. & Haim, A. (1984). J. Heterocycl. Chem. 21, 607-608.]).

[Scheme 1]

Experimental

Crystal data
  • C8F16I2·C14H8N2

  • Mr = 858.10

  • Triclinic, [P \overline 1]

  • a = 5.4849 (11) Å

  • b = 14.302 (2) Å

  • c = 18.354 (3) Å

  • [alpha] = 111.40 (2)°

  • [beta] = 90.35 (2)°

  • [gamma] = 94.03 (2)°

  • V = 1336.4 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.48 mm-1

  • T = 295 K

  • 0.36 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.734, Tmax = 1.000

  • 15067 measured reflections

  • 6100 independent reflections

  • 4600 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.114

  • S = 1.02

  • 6100 reflections

  • 379 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.90 e Å-3

  • [Delta][rho]min = -0.57 e Å-3

Table 1
Halogen and hydrogen-bonding contacts (Å, °)

C-X...Y X...Y C-X...Y
C1-I1...N1 2.863 (4) 177.93 (16)
C8-I2...N2i 2.887 (4) 175.39 (16)
C1-F1...H9ii 2.60 145.3
Symmetry codes: (i) = -2 + x, 1 + y, -1 + z; (ii) = -x, 1 - y, 1 - z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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: SHELXL97 (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: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2080 ).


Acknowledgements

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

References

Allan, J. R., Barrow, M. J., Beaumont, P. C., Macindoe, L. A., Milburn, G. H. W. & Werninck, A. R. (1988). Inorg. Chim. Acta, 148, 85-90.  [CrossRef] [ChemPort] [ISI]
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Badruz Zaman, M. D., Smith, M. D. & Zur Loye, H.-C. (2001). Chem. Mater. 13, 3534-3541.
Bertani, R., Metrangolo, P., Moiana, A., Perez, E., Pilati, T., Resnati, G., Rico-Lattes, I. & Sassi, A. (2002). Adv. Mater. 14, 1197-1201.  [CrossRef] [ChemPort]
Bruker (2010). 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]
Curtis, S. M., Le, N., Fowler, F. W. & Lauher, J. W. (2005). Cryst. Growth Des. 5, 2313-2321.  [CSD] [CrossRef] [ChemPort]
Della Ciana, L. & Haim, A. (1984). J. Heterocycl. Chem. 21, 607-608.  [ChemPort]
Dey, A., Metrangolo, P., Pilati, T., Resnati, G., Terraneo, G. & Wlassics, I. (2009). J. Fluorine Chem. 130, 816-823.  [ISI] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fox, D. B., Liantonio, R., Metrangolo, P., Pilati, T. & Resnati, G. (2004). J. Fluorine Chem. 125, 271-281.  [ISI] [CSD] [CrossRef] [ChemPort]
Fox, D., Metrangolo, P., Pasini, D., Pilati, T., Resnati, G. & Terraneo, G. (2008). CrystEngComm, 10, 1132-1136.  [ISI] [CSD] [CrossRef] [ChemPort]
Liantonio, R., Metrangolo, P., Pilati, T., Resnati, G. & Stevenazzi, A. (2003). Cryst. Growth Des. 3, 799-803.  [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]
Maekawa, M., Konaka, H., Suenaga, Y., Takayoshi Kuroda-Sowa, T. & Munakata, M. (2000). J. Chem. Soc. Dalton Trans. pp. 4160-4166.  [CSD] [CrossRef]
Metrangolo, P., Meyer, F., Pilati, T. & Resnati, G. (2008). Chem. Commun. pp. 1635-1637.  [CSD] [CrossRef]
Metrangolo, P., Pilati, T., Resnati, G. & Stevenazzi, A. (2004). Chem. Commun. pp. 1492-1493.  [CSD] [CrossRef]
Monde, K., Miura, N., Hashimoto, M., Taniguchi, T. & Inabe, T. (2006). J. Am. Chem. Soc. 128, 6000-6001.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Nakamura, A., Sato, T. & Kuroda, R. (2003). CrystEngComm, 5, 318-325.  [ISI] [CSD] [CrossRef] [ChemPort]
Navarrini, W., Metrangolo, P., Pilati, T. & Resnati, G. (2000). New J. Chem. 24, 777-780.  [ISI] [CSD] [CrossRef] [ChemPort]
Neukirch, H., Guido, E., Liantonio, R., Metrangolo, P., Pilati, T. & Resnati, G. (2005). Chem. Commun. pp. 1534-1536.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o328-o329   [ doi:10.1107/S1600536813001888 ]

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