[Journal logo]

Volume 70 
Part 1 
Pages o9-o10  
January 2014  

Received 17 March 2013
Accepted 29 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.077
Data-to-parameter ratio = 25.7
Details
Open access

The 1:1 co-crystal of triphen­yl(2,3,5,6-tetra­fluoro­benz­yl)phospho­nium bromide and 1,1,2,2-tetra­fluoro-1,2-di­iodo­ethane

aNFMLab, Department of Chemistry, Materials and Chemical Engineering, "Giulio Natta", Politecnico di Milano, Via Mancinelli, 7, I-20131 Milano, Italy, and bLaboratory of Biopolymers and Supramolecular Nanomaterials, Universitè Libre de Bruxelles (ULB), Campus de la Plaine, Boulevard du Triomphe, B-1050 Bruxelles, Belgium
Correspondence e-mail: giancarlo.terraneo@polimi.it

The title compound, C25H18F4P+·Br-·C2F4I2, is a 1:1 co-crystal of triphen­yl(2,3,5,6-tetra­fluoro­benz­yl)phospho­nium (TTPB) bromide and 1,1,2,2-tetra­fluoro-1,2-di­iodo­ethane (TFDIE). The crystal structure consists of a framework of TTPB cations held together by C-H...Br inter­actions. In this framework, infinite channels along [100] are filled by TFDIE mol­ecules held together in infinite ribbons by short F...F [2.863 (2)-2.901 (2)Å] inter­actions. The structure contains halogen bonds (XB) and hydrogen bonds (HB) in the bromide coordination sphere. TFDIE functions as a monodentate XB donor as only one I atom is linked to the Br- anion and forms a short and directional inter­action [I...Br- 3.1798 (7) Å and C-I...Br- 177.76 (5)°]. The coordination sphere of the bromide anion is completed by two short HBs of about 2.8 Å (for H...Br) with the acidic methyl­ene H atoms and two longer HBs of about 3.0 Å with H atoms of the phenyl rings. Surprisingly neither the second iodine atom of TFDIE nor the H atom on the tetra­fluoro­phenyl group make any short contacts.

Related literature

For a general discussion on halogen bonds (XBs) involving anionic halogen-bonding acceptors, see: for oxyanions, Abate et al. (2011[Abate, A., Martì-Rujas, J., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2011). Cryst. Growth Des. 11, 4220-4226.]); for chloride and bromide, 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.]); for iodide, Metrangolo et al. (2008[Metrangolo, P., Meyer, F., Pilati, T., Resnati, G. & Terraneo, G. (2008). Chem. Commun. pp. 1635-1637.]). For examples of reliable XB donors in an ionic context, see: Cavallo et al. (2010[Cavallo, G., Biella, S., Lü, J., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2010). J. Fluorine Chem. 131, 1165-1172.]); Metrangolo et al. (2009[Metrangolo, P., Pilati, T., Terraneo, G., Biella, S. & Resnati, G. (2009). CrystEngComm, 11, 1187-1196.]); Logothetis et al. (2004[Logothetis, T. M., Meyer, F., Metrangolo, P., Pilati, T. & Resnati, G. (2004). New J. Chem. 28, 760-763.]). For different supra­molecular structures of halogen-bonded (poly)anions, see for: discrete adducts, Gattuso et al. (2007[Gattuso, G., Pappalardo, A., Parisi, M., Pisigatti, I., Crea, F., Liantonio, R., Metrangolo, P., Navarrini, W., Resnati, G., Pilati, T. & Pappalardo, S. (2007). Tetrahedron, 63, 4951-4958.]); infinite chains, Gattuso et al. (2006[Gattuso, G., Liantonio, R., Metrangolo, P., Meyer, F., Pappalardo, A., Parisi, M., Pilati, T., Pisagatti, I. & Resnati, G. (2006). Supramol. Chem. 18, 235-243.]); comb-like arrays, Biella et al. (2009[Biella, S., Gattuso, G., Notti, A., Metrangolo, P., Pappalardo, S., Parisi, M. F., Pilati, T., Resnati, G. & Terraneo, G. (2009). Supramol. Chem. 21, 149-156.]); 'ring and stick' one-dimensional chains, Gattuso et al. (2009[Gattuso, G., Notti, A., Pappalardo, S., Parisi, M. F., Pilati, T., Resnati, G. & Terraneo, G. (2009). CrystEngComm, 11, 1204-1206.]); two-dimensional layers showing Borromean inter­penetration, Liantonio et al. (2006[Liantonio, R., Metrangolo, P., Meyer, F., Pilati, T., Navarrini, W. & Resnati, G. (2006). Chem. Commun. pp. 1819-1821.]). For very short XBs in the presence of HBs, see: Cametti et al. (2012[Cametti, M., Raatikainen, K., Metrangolo, P., Pilati, T., Terraneo, G. & Resnati, G. (2012). Org. Biomol. Chem. 10, 1329-1333.]); Gattuso et al. (2007[Gattuso, G., Pappalardo, A., Parisi, M., Pisigatti, I., Crea, F., Liantonio, R., Metrangolo, P., Navarrini, W., Resnati, G., Pilati, T. & Pappalardo, S. (2007). Tetrahedron, 63, 4951-4958.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For van der Waals radii, see Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]).

[Scheme 1]

Experimental

Crystal data
  • C25H18F4P+·Br-·C2F4I2

  • Mr = 859.09

  • Triclinic, [P \overline 1]

  • a = 9.6451 (10) Å

  • b = 10.9491 (12) Å

  • c = 13.8425 (15) Å

  • [alpha] = 78.07 (2)°

  • [beta] = 79.08 (2)°

  • [gamma] = 76.76 (2)°

  • V = 1376.7 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.87 mm-1

  • T = 90 K

  • 0.26 × 0.14 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.795, Tmax = 1.000

  • 21807 measured reflections

  • 10912 independent reflections

  • 9550 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.077

  • S = 1.04

  • 10912 reflections

  • 424 parameters

  • 153 restraints

  • All H-atom parameters refined

  • [Delta][rho]max = 1.33 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C19-H19A...Br1 0.92 (2) 2.80 (2) 3.6866 (19) 163 (2)
C19-H19B...Br1i 0.92 (2) 2.83 (2) 3.7263 (19) 166 (2)
C16-H16...Br1ii 0.94 (1) 2.99 (2) 3.910 (2) 168 (2)
C11-H11...Br1iii 0.93 (1) 3.03 (2) 3.725 (2) 133 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y+1, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: QK2057 ).


Acknowledgements

GC, PM, GR and GT acknowledge the Fondazione Cariplo (projects 2009-2550 and 2010-1351) and the "5x1000-2011 project" 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.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Abate, A., Martì-Rujas, J., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2011). Cryst. Growth Des. 11, 4220-4226.  [CSD] [CrossRef] [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Biella, S., Gattuso, G., Notti, A., Metrangolo, P., Pappalardo, S., Parisi, M. F., Pilati, T., Resnati, G. & Terraneo, G. (2009). Supramol. Chem. 21, 149-156.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Bondi, A. (1964). J. Phys. Chem. 68, 441-451.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2005). 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] [IUCr Journals]
Cametti, M., Raatikainen, K., Metrangolo, P., Pilati, T., Terraneo, G. & Resnati, G. (2012). Org. Biomol. Chem. 10, 1329-1333.  [CSD] [CrossRef] [ChemPort] [PubMed]
Cavallo, G., Biella, S., Lü, J., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2010). J. Fluorine Chem. 131, 1165-1172.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gattuso, G., Liantonio, R., Metrangolo, P., Meyer, F., Pappalardo, A., Parisi, M., Pilati, T., Pisagatti, I. & Resnati, G. (2006). Supramol. Chem. 18, 235-243.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Gattuso, G., Notti, A., Pappalardo, S., Parisi, M. F., Pilati, T., Resnati, G. & Terraneo, G. (2009). CrystEngComm, 11, 1204-1206.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Gattuso, G., Pappalardo, A., Parisi, M., Pisigatti, I., Crea, F., Liantonio, R., Metrangolo, P., Navarrini, W., Resnati, G., Pilati, T. & Pappalardo, S. (2007). Tetrahedron, 63, 4951-4958.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Liantonio, R., Metrangolo, P., Meyer, F., Pilati, T., Navarrini, W. & Resnati, G. (2006). Chem. Commun. pp. 1819-1821.  [CSD] [CrossRef]
Logothetis, T. M., Meyer, F., Metrangolo, P., Pilati, T. & Resnati, G. (2004). New J. Chem. 28, 760-763.  [Web of Science] [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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Metrangolo, P., Meyer, F., Pilati, T., Resnati, G. & Terraneo, G. (2008). Chem. Commun. pp. 1635-1637.  [CSD] [CrossRef]
Metrangolo, P., Pilati, T., Terraneo, G., Biella, S. & Resnati, G. (2009). CrystEngComm, 11, 1187-1196.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o9-o10   [ doi:10.1107/S1600536813032522 ]

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.