4-(2-Fluoro­benzo­yl)-1-[2-(4-hy­droxy­phen­yl)-2-oxoeth­yl]piperazin-1-ium trifluoro­acetate

Bian, F.; Jin, Y.; Chi, S.; Shi, G.; Xu, S.

doi:10.1107/S1600536812042857

Volume 68
Part 11
Page o3243
November 2012

Received 5 September 2012
Accepted 13 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
R = 0.073
wR = 0.240
Data-to-parameter ratio = 13.2
Details

4-(2-Fluorobenzoyl)-1-[2-(4-hydroxyphenyl)-2-oxoethyl]piperazin-1-ium trifluoroacetate

Fuyong Bian,^a Yi Jin,^a Shaoming Chi,^a Guojun Shi ^a and Sichuan Xu ^a ^*

^aCollege of Chemical Science and Technology, Yunnan University, Kunming City, People's Republic of China
Correspondence e-mail: sichuan@ynu.edu.cn

In the crystal structure of the title compound, C₁₉H₂₀FN₂O₃⁺·C₂F₃O₂^-, N-HO and O-HO hydrogen bonds link two cations and two anions into a 22-atom ring. These rings are further linked into a three dimensional network by weak C-HO contacts.

Related literature

For the preparation for the title compound, see: Hoff et al. (2005); Wallén et al. (2003); Stachulski et al. (2006). For similar structures, see: Luedtkea & Mach (2003); Rok et al. (2007); Friedel & Crafts (1932a,b). For the applications of similar compounds, see: Wise (1996).

Experimental

Crystal data

C₁₉H₂₀FN₂O₃⁺·C₂F₃O₂^-
M_r = 456.39
Monoclinic, P 2₁ /n
a = 10.055 (3) Å
b = 9.601 (2) Å
c = 21.946 (5) Å
= 91.960 (4)°
V = 2117.4 (9) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 298 K
0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.956, T_max = 0.971
12540 measured reflections
3824 independent reflections
1534 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.073
wR(F²) = 0.240
S = 1.03
3824 reflections
289 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO5ⁱ	0.91	1.87	2.710 (5)	152
O1-H1O5ⁱⁱ	0.82	1.95	2.697 (5)	151
C8-H8BO3ⁱ	0.97	2.22	2.996 (6)	136
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2083 ).

Acknowledgements

Support from the National Natural Science Foundation of China (21163024) is acknowledged.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Friedel, C. & Crafts, J. M. (1932a). Compt. Rend. 84, 1392-1395.
Friedel, C. & Crafts, J. M. (1932b). Compt. Rend. 84, 1450-1450.
Hoff, B., Strandberg, E., Ulrich, A. S., Tieleman, D. P. & Posten, C. (2005). Biophys. J. 88, 1818-1827.
Luedtkea, R. R. & Mach, R. H. (2003). Curr. Pharm. Des. 9, 643-671.
Rok, F., Stanislav, G. & Danijel, K. (2007). Tetrahedron, 63, 10698-10708.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stachulski, A. V., Berry, N. G., Low, A. C. L., Moores, S. L., Row, E., Warhurst, D. C., Adagu, I. S. & Rossignol, J.-F. (2006). J. Med. Chem. 49, 1450-1454.
Wallén, E. A. A., Christiaans, J. A. M., Jarho, E. M., Forsberg, M. M., Venäläinen, J. I., Mannisto, P. T. & Gynther, J. (2003). J. Med. Chem. 46, 4543-4551.
Wise, R. A. (1996). Curr Opin Neurobiol. 6, 243-251.

organic compounds