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Volume 69 
Part 10 
Page o1536  
October 2013  

Received 20 August 2013
Accepted 27 August 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.143
Data-to-parameter ratio = 11.3
Details
Open access

2-Trifluoromethyl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, India
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

In the molecule of the title compound, C11H6F3N3O, the three fused rings of the benzo[4,5]imidazo[1,2-a]pyrimidine unit are essentially coplanar, the maximum deviation from the mean plane being 0.096 (2) Å. In the crystal, N-H...O hydrogen bonds link the molecules into chains running along the b-axis direction.

Related literature

For the bioactivity of benzo[4,5] imidazo[1,2-a]-pyrimidine derivatives, see: Abdel-Hafez (2007[Abdel-Hafez, A. A. M. (2007). Arch. Pharm. Res. 30, 678-684.]); Nunes et al. (2005[Nunes, J. J., Zhu, X. T., Amouzegh, P., Ghiron, C., Johnston, D. N. & Power, E. C. (2005). WO Patent No. 2 005 009 443.]); Duval et al. (2005[Duval, E., Case, A., Stein, R. L. & Cuny, G. D. (2005). Bioorg. Med. Chem. Lett. 15, 1885-1889.]); Palacios et al. (2007[Palacios, F., Alonso, C., Aparicio, D., Rubiales, G. & Santos, J. M. (2007). Tetrahedron, 63, 523-575.]); Teimouria & Bazhrang (2006[Teimouria, M. B. & Bazhrang, R. (2006). Bioorg. Med. Chem. Lett. 16, 3697-3701.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H6F3N3O

  • Mr = 253.19

  • Monoclinic, C 2/c

  • a = 20.940 (3) Å

  • b = 13.760 (3) Å

  • c = 7.2852 (11) Å

  • [beta] = 96.369 (4)°

  • V = 2086.2 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 273 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 9665 measured reflections

  • 1846 independent reflections

  • 1603 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.143

  • S = 1.06

  • 1846 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O15i 0.86 1.88 2.734 (2) 174
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2117 ).


Acknowledgements

Chandra would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009-2010/10.07.2012.

References

Abdel-Hafez, A. A. M. (2007). Arch. Pharm. Res. 30, 678-684.  [CrossRef] [PubMed] [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Duval, E., Case, A., Stein, R. L. & Cuny, G. D. (2005). Bioorg. Med. Chem. Lett. 15, 1885-1889.  [CrossRef] [PubMed] [ChemPort]
Nunes, J. J., Zhu, X. T., Amouzegh, P., Ghiron, C., Johnston, D. N. & Power, E. C. (2005). WO Patent No. 2 005 009 443.
Palacios, F., Alonso, C., Aparicio, D., Rubiales, G. & Santos, J. M. (2007). Tetrahedron, 63, 523-575.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Teimouria, M. B. & Bazhrang, R. (2006). Bioorg. Med. Chem. Lett. 16, 3697-3701.  [PubMed]


Acta Cryst (2013). E69, o1536  [ doi:10.1107/S160053681302401X ]

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