1,10-Phenanthrolinium 2,3,4,5,6-penta­fluoro­benzoate–2,3,4,5,6-penta­fluoro­benzoic acid (1/2)

Zhang, X.; Men, Y.; Yan, X.; Ge, C.; Kong, Y.

doi:10.1107/S160053680903801X

Volume 65
Part 10
Page o2535
October 2009

Received 17 September 2009
Accepted 20 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
R = 0.078
wR = 0.276
Data-to-parameter ratio = 10.6
Details

1,10-Phenanthrolinium 2,3,4,5,6-pentafluorobenzoate-2,3,4,5,6-pentafluorobenzoic acid (1/2)

Xiangdong Zhang,^a ^* Yanmei Men,^a Xianghua Yan,^a Chunhua Ge ^a and Yuxia Kong ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
Correspondence e-mail: xdzhang@lnu.edu.cn

In the title compound, C₁₂H₉N₂⁺·C₇F₅O₂^-·2C₇HF₅O₂, the cation and anion are linked by an N-HO hydrogen bond. The neutral molecules bond to the anion via O-HO hydrogen bonds to form associations of one cation, one anion and two neutral molecules. Intermolecular C-HO, C-HF, FF [shortest contact = 2.768 (8) Å], F [pi] [shortest contact = 3.148 (13) Å] and [pi] - [pi] [shortest centroid-centroid separation = 3.689 (5) Å] interactions further link the components to form a three-dimensional network.

Related literature

For recent developments in the supramolecular chemistry of fluorine-containing compounds, see: Chopra & Row (2008); Choudhury & Row (2004); Gdaniec et al. (2003); Kawahara et al. (2004); Mori & Matsumoo (2007); Reddy et al. (2004).

Experimental

Crystal data

C₁₂H₉N₂⁺·C₇F₅O₂^-·2C₇HF₅O₂
M_r = 816.44
Triclinic, $[P \overline 1]$
a = 9.288 (2) Å
b = 11.099 (3) Å
c = 15.723 (6) Å
= 75.93 (3)°
= 79.45 (2)°
= 87.14 (2)°
V = 1545.6 (8) Å³
Z = 2
Mo K radiation
= 0.18 mm^-1
T = 293 K
0.30 × 0.25 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.934, T_max = 0.952
6444 measured reflections
5387 independent reflections
1611 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.078
wR(F²) = 0.276
S = 0.86
5387 reflections
508 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1	0.86	2.17	2.876 (8)	139
O3-H3AO1	0.82	1.72	2.526 (8)	166
O5-H5O2	0.82	1.80	2.572 (10)	157
C7-H7O6ⁱ	0.93	2.54	3.353 (12)	146
C8-H8O4ⁱⁱ	0.93	2.57	3.391 (11)	147
C2-H2F15ⁱⁱⁱ	0.93	2.51	3.357 (10)	151
C10-H10F7^iv	0.93	2.54	3.375 (11)	149
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x, y, z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5105 ).

Acknowledgements

This work was supported by the Project for Innovation Team of Liaoning Province, China (grant No. 2007T052), the Project for Provincial Key Laboratory of Liaoning Province, China (grant No. 2008S104) and the Startup Project of Doctor, Liaoning University, China.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chopra, D. & Row, T. N. G. (2008). CrystEngComm, 10, 54-67.
Choudhury, A. R. & Row, T. N. G. (2004). Cryst. Growth Des. 4, 47-52.
Gdaniec, M., Jankowski, W., Milewska, M. J. & Poloñski, T. (2003). Angew. Chem. Int. Ed. 42, 3903-3906.
Kawahara, S.-i., Tsuzuki, S. & Uchimaru, T. (2004). J. Phys. Chem. A, 108, 6744-6749.
Mori, Y. & Matsumoo, A. (2007). Cryst. Growth Des. 7, 377-385.
Reddy, L. S., Nangia, A. & Lynch, V. M. (2004). Cryst. Growth Des. 4, 89-94.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds