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Volume 68 
Part 12 
Pages o3387-o3388  
December 2012  

Received 26 October 2012
Accepted 9 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
R = 0.051
wR = 0.141
Data-to-parameter ratio = 17.7
Details
Open access

Ethyl 4-({1-[2-(4-bromophenyl)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}methoxy)-8-(trifluoromethyl)quinoline-3-carboxylate

aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India,bTechnion Israel Institute of Technology, Schulich Faculty of Chemistry, Haifa, 32000, Israel, 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 title compound, C24H18BrF3N4O4, is a 1,2,3-triazole derivative featuring, among others, a quinoline-derived substituent. In the crystal, C-H...O, C-H...N and C-H...F contacts connect the molecules into a three-dimensional network. The shortest centroid-centroid distance between two aromatic systems is 3.896 (2) Å and is found between the two different six-membered rings of the quinoline scaffold in neighbouring molecules.

Related literature

For background to the industrial importance of heterocyclic compounds, see: 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.]); Ruanwasa et al. (2010[Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padaki, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.]). For pharmacological properties of quinoline-derived compounds, see: Chen et al. (2004[Chen, Y. L., Hung, H. M., Lu, C. M., Li, K. C. & Tzeng, C. C. (2004). Bioorg. Med. Chem. 12, 6539-6546.]); Kaur et al. (2010[Kaur, K., Jain, M., Reddy, R. P. & Jain, R. (2010). Eur. J. Med. Chem. 45, 3245-3264.]); Bekhit et al. (2004[Bekhit, A. A., El-Sayed, O. A., Aboulmagd, E. & Park, J. Y. (2004). Eur. J. Med. Chem. 39, 249-255.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18BrF3N4O4

  • Mr = 563.33

  • Monoclinic, P 21 /c

  • a = 5.2809 (2) Å

  • b = 24.5131 (10) Å

  • c = 18.3517 (7) Å

  • [beta] = 99.643 (1)°

  • V = 2342.08 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.82 mm-1

  • T = 200 K

  • 0.58 × 0.16 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.417, Tmax = 0.889

  • 22440 measured reflections

  • 5775 independent reflections

  • 3774 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.141

  • S = 1.02

  • 5775 reflections

  • 326 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.61 e Å-3

  • [Delta][rho]min = -0.93 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...N2i 0.99 2.62 3.339 (4) 129
C3-H3...N3i 0.95 2.65 3.288 (4) 125
C2-H2B...F2ii 0.99 2.45 3.308 (3) 144
C5-H5A...O3iii 0.99 2.37 3.258 (4) 149
C26-H26...O1iv 0.95 2.57 3.354 (5) 140
Symmetry codes: (i) x-1, y, z; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) x+1, y, z; (iv) -x, -y+1, -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: IM2409 ).


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.
Chen, Y. L., Hung, H. M., Lu, C. M., Li, K. C. & Tzeng, C. C. (2004). Bioorg. Med. Chem. 12, 6539-6546.  [CrossRef] [PubMed] [ChemPort]
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]
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]
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padaki, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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, o3387-o3388   [ doi:10.1107/S1600536812046417 ]

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