Ethyl 3-(2-eth­oxy-2-oxoeth­oxy)-6-(tri­fluoro­meth­yl)furo[3,2-c]quinoline-2-carboxyl­ate

Garudachari, B.; Islor, A.M.; Vijesh, A.M.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812046843

Volume 68
Part 12
Pages o3389-o3390
December 2012

Received 31 October 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.034
wR = 0.096
Data-to-parameter ratio = 17.0
Details

Ethyl 3-(2-ethoxy-2-oxoethoxy)-6-(trifluoromethyl)furo[3,2-c]quinoline-2-carboxylate

B. Garudachari,^a Arun M. Islor,^a A. M. Vijesh,^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,^bGITAM University, Department of Engineering Chemistry, GIT, Rushikonda, Visakhapatnam, A.P. 530 045, 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

In the title compound, C₁₉H₁₆F₃NO₆, a quinoline derivative featuring an annealated furan substituent, the mean planes of the carboxy substituents are at an angle of 74.3 (2)°. In the crystal, C-HO contacts result in undulating chains along [110]. C-HF contacts also occur. The shortest centroid-centroid distance between rings is 3.3376 (7) Å, involving two furan rings of neighbouring molecules.

Related literature

For background to the pharmacological activity of heterocyclic compounds, see: Isloor et al. (2000, 2009); Caprio et al. (2000); Kaur et al. (2010); Chou et al. (2010); Chen et al. (2004); Garudachari et al. (2012); Shingalapur et al. (2009). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₉H₁₆F₃NO₆
M_r = 411.33
Triclinic, $[P \overline 1]$
a = 8.9167 (3) Å
b = 8.9223 (3) Å
c = 13.4125 (5) Å
= 102.895 (1)°
= 97.098 (2)°
= 116.035 (1)°
V = 904.22 (5) Å³
Z = 2
Mo K radiation
= 0.13 mm^-1
T = 200 K
0.56 × 0.38 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.918, T_max = 0.980
19743 measured reflections
4499 independent reflections
4019 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.096
S = 1.04
4499 reflections
264 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O3ⁱ	0.95	2.44	3.2556 (13)	144
C13-H13BF1ⁱⁱ	0.99	2.46	3.2829 (12)	141
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z.

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: FJ2605 ).

Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for a Young Scientist award.

References

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organic compounds