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)

Cavallo, G.; Marras, G.; Metrangolo, P.; Pilati, T.; Terraneo, G.

doi:10.1107/S1600536813001888

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 (C-C) = 0.007 Å
R = 0.039
wR = 0.114
Data-to-parameter ratio = 16.1
Details

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)

Gabriella Cavallo,^a Giovanni Marras,^b Pierangelo Metrangolo,^a Tullio Pilati ^a and Giancarlo Terraneo ^a ^*

^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-IN 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 HF 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); Curtis et al. (2005); Maekawa et al. (2000); Badruz Zaman et al. (2001); Allan et al. (1988). For NI halogen bonds based on [alpha] , [omega] -diiodoperfluorocarbons, see: Neukirch et al. (2005); Navarrini et al. (2000); Liantonio et al. (2003); Bertani et al. (2002); Metrangolo et al. (2004, 2008); Fox et al. (2004); Dey et al. (2009). For segregation of perfluoroalkyl chains, see: Fox et al. (2008). For chirality and order/disorder of long perfluoroalkyl chains, see: Monde et al. (2006). For the synthesis of bis-(4-pyridyl)buta-1,3-diine, see: Della Ciana & Haim (1984).

Experimental

Crystal data

C₈F₁₆I₂·C₁₄H₈N₂
M_r = 858.10
Triclinic, $[P \overline 1]$
a = 5.4849 (11) Å
b = 14.302 (2) Å
c = 18.354 (3) Å
= 111.40 (2)°
= 90.35 (2)°
= 94.03 (2)°
V = 1336.4 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.734, T_max = 1.000
15067 measured reflections
6100 independent reflections
4600 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.114
S = 1.02
6100 reflections
379 parameters
H-atom parameters constrained
_max = 0.90 e Å^-3
_min = -0.57 e Å^-3

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

C-XY	XY	C-XY
C1-I1N1	2.863 (4)	177.93 (16)
C8-I2N2ⁱ	2.887 (4)	175.39 (16)
C1-F1H9ⁱⁱ	2.60	145.3
Symmetry codes: (i) = -2 + x, 1 + y, -1 + z; (ii) = -x, 1 - y, 1 - z.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: enCIFer (Allen et al., 2004).

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

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organic compounds