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Volume 68 
Part 12 
Pages o3304-o3305  
December 2012  

Received 25 October 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.116
Data-to-parameter ratio = 16.1
Details
Open access

Ethyl 4-oxo-8-trifluoromethyl-1,4-dihydroquinoline-3-carboxylate

aNational Institute of Technology-Karnataka, Department of Chemistry, Organic Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bNational Institute of Technology-Karnataka, Department of Physics, Surathkal, Mangalore 575 025, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The asymmetric unit of the title compound, C13H10F3NO3, contains two independent molecules with similar conformations. In the crystal, N-H...O hydrogen bonds link alternating independent molecules into chains in [-110]. In the chain, the quinoline planes of the independent molecules are almost perpendicular to each other, forming a dihedral angle of 89.8 (1)°. [pi]-[pi] interactions between the aromatic rings of quinoline bicycles related by inversion centres [for two independent centrosymmetric dimers, the shortest centroid-centroid distances are 3.495 (1) and 3.603 (1) Å] link the hydrogen-bonded chains into layers parallel to (110). Weak C-H...F and C-H...O interactions further consolidate the crystal packing.

Related literature

For background information about the pharmacological properties of quinoline derivatives, see: Holla et al. (2006[Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akbarali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040-2047.]); Bekhit et al. (2004[Bekhit, A. A., El-Sayed, O. A., Aboulmagd, E. & Park, J. Y. (2004). Eur. J. Med. Chem. 39, 249-255.]); Kaur et al. (2010[Kaur, K., Jain, M., Reddy, R. P. & Jain, R. (2010). Eur. J. Med. Chem. 45, 3245-3264.]); Isloor et al. (2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]); Vijesh et al. (2011[Vijesh, A. M., Isloor, A. M., Peethambar, S. K., Shivananda, K. N., Arulmoli, T. & Isloor, N. A. (2011). Eur. J. Med. Chem. 46, 5591-5597.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the synthesis of the title compound, see: Thomas et al. (2011[Thomas, K. D., Adhikari, A. V., Telkar, S., Chowdhury, I. H., Mahmood, R., Pal, N. K., Row, G. & Sumesh, E. (2011). Eur. J. Med. Chem. 46, 5283-5292.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10F3NO3

  • Mr = 285.22

  • Triclinic, [P \overline 1]

  • a = 9.8248 (3) Å

  • b = 11.0222 (3) Å

  • c = 12.3450 (4) Å

  • [alpha] = 72.934 (1)°

  • [beta] = 74.167 (1)°

  • [gamma] = 74.059 (1)°

  • V = 1201.67 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 200 K

  • 0.53 × 0.38 × 0.32 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.928, Tmax = 0.956

  • 21419 measured reflections

  • 5963 independent reflections

  • 5051 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.116

  • S = 1.04

  • 5963 reflections

  • 371 parameters

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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O21i 0.892 (19) 1.875 (19) 2.6588 (13) 145.5 (16)
N2-H2...O11ii 0.851 (18) 2.011 (17) 2.7178 (13) 139.9 (16)
N2-H2...O12ii 0.851 (18) 2.487 (17) 3.0380 (15) 123.2 (14)
C212-H21B...F22iii 0.99 2.46 3.0909 (18) 121
C204-H204...O13iv 0.95 2.60 3.4691 (18) 153
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) x+1, y, z; (iv) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5354 ).


Acknowledgements

AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award.

References

Bekhit, A. A., El-Sayed, O. A., Aboulmagd, E. & Park, J. Y. (2004). Eur. J. Med. Chem. 39, 249-255.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akbarali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040-2047.  [CrossRef] [PubMed] [ChemPort]
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kaur, K., Jain, M., Reddy, R. P. & Jain, R. (2010). Eur. J. Med. Chem. 45, 3245-3264.  [ISI] [CrossRef] [ChemPort] [PubMed]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thomas, K. D., Adhikari, A. V., Telkar, S., Chowdhury, I. H., Mahmood, R., Pal, N. K., Row, G. & Sumesh, E. (2011). Eur. J. Med. Chem. 46, 5283-5292.  [ISI] [CrossRef] [ChemPort] [PubMed]
Vijesh, A. M., Isloor, A. M., Peethambar, S. K., Shivananda, K. N., Arulmoli, T. & Isloor, N. A. (2011). Eur. J. Med. Chem. 46, 5591-5597.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o3304-o3305   [ doi:10.1107/S1600536812045321 ]

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