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Volume 69 
Part 10 
Page o1566  
October 2013  

Received 9 September 2013
Accepted 13 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.065
wR = 0.180
Data-to-parameter ratio = 8.7
Details
Open access

Methyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C7H6F3NO2, all the non-H atoms except for one of the F atoms lie on a crystallographic mirror plane. In the crystal, the molecules are linked into inversion dimers by pairs of C-H...F interactions, forming R22(10) loops. These dimers are connected into C(6) chains along [001] through N-H...O hydrogen bonds. Aromatic [pi]-[pi] stacking interactions [centroid-centroid separation = 3.8416 (10) A°] connect the molecules into a three-dimensional network.

Related literature

For background to the pharmacological activity of pyrrole derivatives, see: Toja et al. (1987[Toja, E., Depaoli, A., Tuan, G. & Kettenring, J. (1987). Synthesis, pp. 272-274.]); Muchowski et al. (1985[Muchowski, J. M., Unger, S. H., Ackrell, J., Cheung, P., Cook, J., Gallegra, P., Halpern, O., Koehler, R. & Kluge, A. F. (1985). J. Med. Chem. 28, 1037-1049.]); Dannhardt et al. (2000[Dannhardt, G., Kiefer, W., Kramer, G., Maehrlein, S., Nowe, U. & Fiebich, B. (2000). Eur. J. Med. Chem. 35, 499-510.]); Burnham et al. (1998[Burnham, B. S., Gupton, J. T., Krumpe, K. E., Webb, T., Shuford, J., Bowers, B., Warren, A. E., Barnes, C. & Hall, I. H. (1998). Arch. Pharm. Pharm. Med. Chem. 331, 337-341.]); Krowicki et al. (1988[Krowicki, K., Jan Balzarini, T., Clercq, E. D., Robert, A., Newman, J. & Lawn, J. W. (1988). J. Med. Chem. 31, 341-345.]).

[Scheme 1]

Experimental

Crystal data
  • C7H6F3NO2

  • Mr = 193.13

  • Monoclinic, C 2/m

  • a = 16.643 (2) Å

  • b = 7.1118 (10) Å

  • c = 6.9618 (11) Å

  • [beta] = 98.903 (7)°

  • V = 814.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 293 K

  • 0.24 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.969

  • 3752 measured reflections

  • 707 independent reflections

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

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.180

  • S = 1.09

  • 707 reflections

  • 81 parameters

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

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N-H...O1i 0.83 (6) 2.03 (5) 2.810 (4) 156
C5-H5...F1ii 0.93 2.52 3.442 (4) 171
Symmetry codes: (i) x, y, z-1; (ii) -x+1, y, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7136 ).


Acknowledgements

The authors acknowledge the IOE X-ray diffractometer Facility, University of Mysore, Mysore, for collecting the data.

References

Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnham, B. S., Gupton, J. T., Krumpe, K. E., Webb, T., Shuford, J., Bowers, B., Warren, A. E., Barnes, C. & Hall, I. H. (1998). Arch. Pharm. Pharm. Med. Chem. 331, 337-341.  [CrossRef] [ChemPort]
Dannhardt, G., Kiefer, W., Kramer, G., Maehrlein, S., Nowe, U. & Fiebich, B. (2000). Eur. J. Med. Chem. 35, 499-510.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Krowicki, K., Jan Balzarini, T., Clercq, E. D., Robert, A., Newman, J. & Lawn, J. W. (1988). J. Med. Chem. 31, 341-345.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Muchowski, J. M., Unger, S. H., Ackrell, J., Cheung, P., Cook, J., Gallegra, P., Halpern, O., Koehler, R. & Kluge, A. F. (1985). J. Med. Chem. 28, 1037-1049.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Toja, E., Depaoli, A., Tuan, G. & Kettenring, J. (1987). Synthesis, pp. 272-274.  [CrossRef]


Acta Cryst (2013). E69, o1566  [ doi:10.1107/S160053681302549X ]

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