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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 [sigma](C-C) = 0.007 Å
R = 0.073
wR = 0.240
Data-to-parameter ratio = 13.2
Details
Open access

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

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-H...O and O-H...O 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-H...O contacts.

Related literature

For the preparation for the title compound, see: Hoff et al. (2005[Hoff, B., Strandberg, E., Ulrich, A. S., Tieleman, D. P. & Posten, C. (2005). Biophys. J. 88, 1818-1827.]); Wallén et al. (2003[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.]); Stachulski et al. (2006[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.]). For similar structures, see: Luedtkea & Mach (2003[Luedtkea, R. R. & Mach, R. H. (2003). Curr. Pharm. Des. 9, 643-671.]); Rok et al. (2007[Rok, F., Stanislav, G. & Danijel, K. (2007). Tetrahedron, 63, 10698-10708.]); Friedel & Crafts (1932a[Friedel, C. & Crafts, J. M. (1932a). Compt. Rend. 84, 1392-1395.],b[Friedel, C. & Crafts, J. M. (1932b). Compt. Rend. 84, 1450-1450.]). For the applications of similar compounds, see: Wise (1996[Wise, R. A. (1996). Curr Opin Neurobiol. 6, 243-251.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20FN2O3+·C2F3O2-

  • Mr = 456.39

  • Monoclinic, P 21 /n

  • a = 10.055 (3) Å

  • b = 9.601 (2) Å

  • c = 21.946 (5) Å

  • [beta] = 91.960 (4)°

  • V = 2117.4 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.956, Tmax = 0.971

  • 12540 measured reflections

  • 3824 independent reflections

  • 1534 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.240

  • S = 1.03

  • 3824 reflections

  • 289 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O5i 0.91 1.87 2.710 (5) 152
O1-H1...O5ii 0.82 1.95 2.697 (5) 151
C8-H8B...O3i 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[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
Luedtkea, R. R. & Mach, R. H. (2003). Curr. Pharm. Des. 9, 643-671.  [PubMed]
Rok, F., Stanislav, G. & Danijel, K. (2007). Tetrahedron, 63, 10698-10708.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
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.  [PubMed]
Wise, R. A. (1996). Curr Opin Neurobiol. 6, 243-251.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3243  [ doi:10.1107/S1600536812042857 ]

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