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Volume 69 
Part 3 
Page o339  
March 2013  

Received 16 January 2013
Accepted 25 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 11.5
Details
Open access

Ethyl 5-methoxy-2-trifluoromethyl-1H-indole-3-carboxylate

aFribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 3, CH-1700 Fribourg, Switzerland, and bChemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland
Correspondence e-mail: aurelien.crochet@unifr.ch

The title compound, C13H12F3NO3, is almost planar if one excludes the F atoms of the -CF3 group [maximum deviation for the other hetero atoms = 0.069 (1) Å], and the dihedral angle between the pyrrole and benzene ring of the indole system is 2.54 (8)°. In the crystal, molecules are linked by N-H...O hydrogen bonds, forming chains propagating along the a-axis direction. These chains are linked via C-H...O and C-H...F hydrogen bonds, forming a three-dimensional network.

Related literature

For indoles, see: Kochanowska-Karamyan & Hamann (2010[Kochanowska-Karamyan, A. J. & Hamann, M. T. (2010). Chem. Rev. 110, 4489-4497.]); Debieux & Bochet (2009[Debieux, J.-L. & Bochet, C. G. (2009). J. Org. Chem.74, 4519-4524.]); Helgen & Bochet (2003[Helgen, C. & Bochet, C. G. (2003). J. Org. Chem. 68, 2483-2486.]); Oppolzer et al. (1994[Oppolzer, W., Spivey, A. C. & Bochet, C. G. (1994). J. Am. Chem. Soc. 116, 3139-3140.]), and for their synthesis, see: Chen et al. (2008[Chen, Y., Wang, Y., Sun, Z. & Ma, D. (2008). Org. Lett. 4, 625-628.]); Barton et al. (1977[Barton, D. H. R., Hesse, R. H., Jackman, G. P. & Pechet, M. M. (1977). J. Chem. Soc. Perkin Trans. 1, pp. 2604-2608.]). For photochemical methods for the synthesis of substituted indoles, see: Bochet & Blanc (2010[Bochet, C. G. & Blanc, A. (2010). In Handbook of Synthetic Photochemistry, edited by A. Albini & M. Fagnoni, pp. 417-447. Weinheim: Wiley-VCH.]); Bochet & Mercier (2009[Bochet, C. G. & Mercier, S. (2009). In Linker Strategies in Solid-Phase Organic Synthesis, edited by P. Scott, pp. 151-193. New York: John Wiley.]); Debieux & Bochet (2012[Debieux, J.-L. & Bochet, C. G. (2012). Chem. Sci. 3, 405-406.]); Streit & Bochet (2011[Streit, U. & Bochet, C. G. (2011). Beilstein J. Org. Chem. 7, 525-542.]); Alimi & Bochet (2013[Alimi, I. & Bochet, C. G. (2013). Unpublished data.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12F3NO3

  • Mr = 287.24

  • Orthorhombic, P b c a

  • a = 13.9211 (8) Å

  • b = 8.6383 (4) Å

  • c = 21.5316 (7) Å

  • V = 2589.3 (2) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 1.16 mm-1

  • T = 200 K

  • 0.74 × 0.39 × 0.14 mm

Data collection
  • Stoe IPDS 2T diffractometer

  • Absorption correction: integration (X-SHAPE; Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.]) Tmin = 0.610, Tmax = 0.850

  • 15525 measured reflections

  • 2130 independent reflections

  • 1894 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.09

  • 2130 reflections

  • 186 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.835 (19) 2.109 (19) 2.8623 (16) 149.8 (16)
C6-H6...O3ii 0.95 2.53 3.460 (2) 168
C11-H11B...F2iii 0.99 2.50 3.336 (2) 142
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) -x+2, -y+2, -z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.]); 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, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2553 ).


Acknowledgements

The authors thank the Swiss National Science Foundation and the Fribourg Center for Nanomaterials (FriMat) for generous support.

References

Alimi, I. & Bochet, C. G. (2013). Unpublished data.
Barton, D. H. R., Hesse, R. H., Jackman, G. P. & Pechet, M. M. (1977). J. Chem. Soc. Perkin Trans. 1, pp. 2604-2608.  [CrossRef]
Bochet, C. G. & Blanc, A. (2010). In Handbook of Synthetic Photochemistry, edited by A. Albini & M. Fagnoni, pp. 417-447. Weinheim: Wiley-VCH.
Bochet, C. G. & Mercier, S. (2009). In Linker Strategies in Solid-Phase Organic Synthesis, edited by P. Scott, pp. 151-193. New York: John Wiley.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chen, Y., Wang, Y., Sun, Z. & Ma, D. (2008). Org. Lett. 4, 625-628.  [ISI] [CrossRef]
Debieux, J.-L. & Bochet, C. G. (2009). J. Org. Chem.74, 4519-4524.
Debieux, J.-L. & Bochet, C. G. (2012). Chem. Sci. 3, 405-406.  [ChemPort]
Helgen, C. & Bochet, C. G. (2003). J. Org. Chem. 68, 2483-2486.  [CrossRef] [PubMed] [ChemPort]
Kochanowska-Karamyan, A. J. & Hamann, M. T. (2010). Chem. Rev. 110, 4489-4497.  [ISI] [ChemPort] [PubMed]
Oppolzer, W., Spivey, A. C. & Bochet, C. G. (1994). J. Am. Chem. Soc. 116, 3139-3140.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2001). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.
Streit, U. & Bochet, C. G. (2011). Beilstein J. Org. Chem. 7, 525-542.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o339  [ doi:10.1107/S1600536813002614 ]

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