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Volume 69 
Part 4 
Page o501  
April 2013  

Received 22 February 2013
Accepted 26 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.119
Data-to-parameter ratio = 14.2
Details
Open access

5-Chloroquinolin-8-yl furan-2-carboxylate

aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title compound, C14H8ClNO3, the central ester CO2 group is twisted away from the quinoline and furoyl rings by 57.46 (5) and 2.0 (1)°, respectively. In the crystal, molecules are linked by weak C-H...O interactions, forming chains in [001].

Related literature

For medicinal, antifungal, antibacterial, anticancer and luminiscent properties of the quinoline ring, see: Somvanshi et al. (2008[Somvanshi, R. K., Subashini, R., Dhanasekaran, V., Arulprakash, G., Das, S. N. & Dey, S. (2008). J. Chem. Crystallogr. 38, 381-386.]), Biavatti et al. (2002[Biavatti, M. W., Vieira, P. C., da Silva, M. F. G. F., Fernandes, J. B., Victor, S. R., Pagnocca, F. C., Albuquerque, S., Caracelli, I. & Zukerman-Schpector, J. (2002). J. Braz. Chem. Soc. 13, 66-70.]), Towers et al. (1981[Towers, G. H. N., Graham, E. A., Spenser, I. D. & Abramowski, Z. (1981). Planta Med. 41, 136-142.]), Shen et al. (1999[Shen, A. Y., Wu, S. N. & Chiu, C. T. (1999). J. Pharm. Pharmacol. 51, 543-548.]) and Montes et al. (2006[Montes, V. A., Pohl, R., Shinar, J. & Anzenbacher, P. Jr (2006). Chem. Eur. J. 12, 4523-4535.]), respectively. For similar structures, see: Lei (2006[Lei, G. (2006). Acta Cryst. E62, o4666-o4667.]; 2007[Lei, G. (2007). Acta Cryst. E63, o4304.]). For hydrogen-bonding notation, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]); Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

[Scheme 1]

Experimental

Crystal data
  • C14H8ClNO3

  • Mr = 273.66

  • Monoclinic, P 21 /c

  • a = 4.0714 (1) Å

  • b = 23.7463 (7) Å

  • c = 12.7698 (4) Å

  • [beta] = 102.113 (1)°

  • V = 1207.11 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 295 K

  • 0.35 × 0.09 × 0.09 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 4385 measured reflections

  • 2440 independent reflections

  • 1906 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.119

  • S = 1.03

  • 2440 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14...O2i 0.93 2.47 3.371 (2) 162
Symmetry code: (i) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2111 ).


Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database. RMF also thanks the Universidad del Valle, Colombia, for partial financial support.

References

Biavatti, M. W., Vieira, P. C., da Silva, M. F. G. F., Fernandes, J. B., Victor, S. R., Pagnocca, F. C., Albuquerque, S., Caracelli, I. & Zukerman-Schpector, J. (2002). J. Braz. Chem. Soc. 13, 66-70.  [CSD] [CrossRef] [ChemPort]
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lei, G. (2006). Acta Cryst. E62, o4666-o4667.  [CSD] [CrossRef] [details]
Lei, G. (2007). Acta Cryst. E63, o4304.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Montes, V. A., Pohl, R., Shinar, J. & Anzenbacher, P. Jr (2006). Chem. Eur. J. 12, 4523-4535.  [CSD] [CrossRef] [PubMed] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shen, A. Y., Wu, S. N. & Chiu, C. T. (1999). J. Pharm. Pharmacol. 51, 543-548.  [CrossRef] [PubMed] [ChemPort]
Somvanshi, R. K., Subashini, R., Dhanasekaran, V., Arulprakash, G., Das, S. N. & Dey, S. (2008). J. Chem. Crystallogr. 38, 381-386.  [ISI] [CSD] [CrossRef] [ChemPort]
Towers, G. H. N., Graham, E. A., Spenser, I. D. & Abramowski, Z. (1981). Planta Med. 41, 136-142.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2013). E69, o501  [ doi:10.1107/S1600536813005667 ]

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