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

Islor, A.M.; Garudachari, B.; Shivananda, K.N.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812046417

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 (C-C) = 0.005 Å
R = 0.051
wR = 0.141
Data-to-parameter ratio = 17.7
Details

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

Arun M. Islor,^a B. Garudachari,^a K. N. Shivananda,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^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-HO, C-HN and C-HF 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); Vijesh et al. (2011); Ruanwasa et al. (2010). For pharmacological properties of quinoline-derived compounds, see: Chen et al. (2004); Kaur et al. (2010); Bekhit et al. (2004). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₄H₁₈BrF₃N₄O₄
M_r = 563.33
Monoclinic, P 2₁ /c
a = 5.2809 (2) Å
b = 24.5131 (10) Å
c = 18.3517 (7) Å
= 99.643 (1)°
V = 2342.08 (16) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.417, T_max = 0.889
22440 measured reflections
5775 independent reflections
3774 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.141
S = 1.02
5775 reflections
326 parameters
H-atom parameters constrained
_max = 0.61 e Å^-3
_min = -0.93 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AN2ⁱ	0.99	2.62	3.339 (4)	129
C3-H3N3ⁱ	0.95	2.65	3.288 (4)	125
C2-H2BF2ⁱⁱ	0.99	2.45	3.308 (3)	144
C5-H5AO3ⁱⁱⁱ	0.99	2.37	3.258 (4)	149
C26-H26O1^iv	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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

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