4,4′-(1,1,1,3,3,3-Hexafluoro­propane-2,2-diyl)dibenzoic acid

Tang, L.; Wu, Y.-P.; Fu, F.; Zhang, Z.-L.; Zheng, D.

doi:10.1107/S1600536810017745

Volume 66
Part 6
Page o1390
June 2010

Received 19 March 2010
Accepted 14 May 2010
Online 19 May 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.040
wR = 0.071
Data-to-parameter ratio = 11.8
Details

4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)dibenzoic acid

Long Tang,^a Ya-Pan Wu,^a Feng Fu,^a ^* Zhu-Lian Zhang ^a and Dan Zheng ^a

^aDepartment of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Shaanxi 716000, People's Republic of China
Correspondence e-mail: yadxgncl@126.com

In the title compound, C₁₇H₁₀F₆O₄, the two benzene rings are twisted with respect to each other, making a dihedral angle of 67.43 (12)°. In the crystal, adjacent molecules are linked by O-HO and C-HF hydrogen bonding, forming a wave-like layered supramolecular structure.

Related literature

For the use of bibenzoic acids as bridging ligands for the synthesis of novel solid-state architectures, see: Zou et al. (2007). For the structures of related dibenzoic acid compounds, see: Potts et al. (2007); Lian et al. (2007).

Experimental

Crystal data

C₁₇H₁₀F₆O₄
M_r = 392.25
Monoclinic, P 2₁ /c
a = 7.7523 (16) Å
b = 13.381 (3) Å
c = 16.134 (3) Å
= 102.294 (4)°
V = 1635.2 (6) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 293 K
0.35 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.963, T_max = 0.972
8113 measured reflections
2904 independent reflections
1339 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.071
S = 1.00
2904 reflections
246 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO4ⁱ	0.82	1.85	2.661 (2)	169
O3-H3AO1ⁱⁱ	0.82	1.80	2.603 (2)	165
C15-H15F1ⁱⁱⁱ	0.93	2.48	3.382 (3)	163
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2737 ).

Acknowledgements

This project was supported by the Natural Scientific Foundation of Shaanxi Province, China (grant No. SJ08B11), the Key Laboratory Foundation of Shaanxi Provincial Education Office, China (Nos. 08JZ82, 07 J K435, 08 J K490, 09 J K816, 09 J K826 and 09 J K815) and the Special Scientific Research Foundation of Yan'an University (No. D2009-139).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Lian, F.-Y., Yuan, D.-Q., Jiang, F.-L. & Hong, M.-C. (2007). Acta Cryst. E63, o2870.
Potts, S., Bredenkamp, M. W. & Gertenbach, J.-A. (2007). Acta Cryst. E63, o2887.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zou, R.-Q., Zhong, R.-Q., Du, M., Kiyobayashi, T. & Xu, Q. (2007). Chem. Commun. pp. 2467-2469.

organic compounds