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Volume 68 
Part 12 
Page o3472  
December 2012  

Received 17 September 2012
Accepted 25 October 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.102
Data-to-parameter ratio = 14.9
Details
Open access

5-(Trifluoromethoxy)isatin

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9301, South Africa
Correspondence e-mail: schuttem@ufs.ac.za

The title compound [systematic name: 5-(trifluoromethoxy)-1H-indole-2,3-dione], C9H4F3NO3, crystallized with two molecules in the asymmetric unit. Intermolecular N-H...O hydrogen bonds link the molecules to form layers parallel to the ab plane. In addition, [pi]-[pi] stacking interactions are observed with a centroid-centroid distance of 3.721 (1) Å. The near planarity of the two isatin ring systems is illustrated by by the maximum deviations of 0.023 (1) and 0.025 (1) Å for the N atom in each case.

Related literature

For similar structures and background information on isatin as a biological agent, see Schutte et al. (2012[Schutte, M., Visser, H. G., Roodt, A. & Braband, H. (2012). Acta Cryst. E68, o777.]); Garden et al. (2006[Garden, S. J., Pinto, A. C., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o321-o323.]); Goldschmidt & Llewellyn (1950[Goldschmidt, G. H. & Llewellyn, F. J. (1950). Acta Cryst. 3, 294-305.]); Frolova et al. (1988[Frolova, N. A., Kravtsov, V. Kh., Biyushkin, V. N., Chumakov, Yu. M., Bel'kova, O. N. & Malinovskii, T. I. (1988). Zh. Strukt. Khim. 29, 155-158.]); Wei et al. (2004[Wei, H.-X., Zhou, C., Ham, S., White, J. M. & Birney, D. M. (2004). Org. Lett. 6, 4289-4292.]); Palmer et al. (1987[Palmer, M. H., Blake, A. J. & Gould, R. O. (1987). Chem. Phys. 115, 219-227.]); Akkurt et al. (2006[Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.]). For reaction kinetic data on similar structures, see: Schutte et al. (2011[Schutte, M., Kemp, G., Visser, H. G. & Roodt, A. (2011). Inorg. Chem. 50, 12486-12498.]).

[Scheme 1]

Experimental

Crystal data
  • C9H4F3NO3

  • Mr = 231.13

  • Monoclinic, P 21 /n

  • a = 14.329 (5) Å

  • b = 6.082 (5) Å

  • c = 20.401 (5) Å

  • [beta] = 91.608 (5)°

  • V = 1777.2 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 100 K

  • 0.51 × 0.18 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.152, Tmax = 0.394

  • 26198 measured reflections

  • 4428 independent reflections

  • 3513 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.102

  • S = 1.04

  • 4418 reflections

  • 297 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O4i 0.84 (2) 1.99 (2) 2.7615 (18) 152.8 (18)
N2-H2...O1ii 0.89 (2) 2.03 (2) 2.8776 (18) 157.4 (19)
N2-H2...O4iii 0.89 (2) 2.55 (2) 2.9850 (18) 111.2 (16)
C16-H16...F3i 0.93 2.39 3.171 (2) 142
C18-H18...O2iv 0.93 2.47 3.327 (3) 153
Symmetry codes: (i) x, y-1, z; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2072 ).


Acknowledgements

The University of the Free State, the Chemistry Department, the NRF and SASOL Ltd are acknowledged for funding.

References

Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.  [CSD] [CrossRef] [details]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Frolova, N. A., Kravtsov, V. Kh., Biyushkin, V. N., Chumakov, Yu. M., Bel'kova, O. N. & Malinovskii, T. I. (1988). Zh. Strukt. Khim. 29, 155-158.  [ChemPort]
Garden, S. J., Pinto, A. C., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o321-o323.  [CrossRef] [details]
Goldschmidt, G. H. & Llewellyn, F. J. (1950). Acta Cryst. 3, 294-305.  [CrossRef] [ChemPort] [details]
Palmer, M. H., Blake, A. J. & Gould, R. O. (1987). Chem. Phys. 115, 219-227.  [CrossRef] [ChemPort] [ISI]
Schutte, M., Kemp, G., Visser, H. G. & Roodt, A. (2011). Inorg. Chem. 50, 12486-12498.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Schutte, M., Visser, H. G., Roodt, A. & Braband, H. (2012). Acta Cryst. E68, o777.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wei, H.-X., Zhou, C., Ham, S., White, J. M. & Birney, D. M. (2004). Org. Lett. 6, 4289-4292.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3472  [ doi:10.1107/S1600536812044297 ]

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