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Volume 68 
Part 11 
Page o3198  
November 2012  

Received 15 October 2012
Accepted 17 October 2012
Online 24 October 2012

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.077
wR = 0.272
Data-to-parameter ratio = 15.9
Details
Open access

3-Ethyl-4-hydroxy-8-methoxyquinolin-2(1H)-one

Stanislav Kafka,a Andrej Pevec,b* Karel Proisl,a Roman Kimmela and Janez Kosmrljb

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Zlin 76272, Czech Republic, and bFaculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000 Ljubljana, Slovenia
Correspondence e-mail: andrej.pevec@fkkt.uni-lj.si

In the title compound, C12H13NO3, the quinoline ring system is approximately planar with a maximum deviation from the least-squares plane of 0.058 (2) Å. In the crystal, N-H...O and O-H...O hydrogen bonds link the molecules into chains running along the b-axis direction. The chains also feature [pi]-[pi] interactions between pyridine and benzene rings of inversion-related molecules [centroid-centroid distance = 3.609 (2) Å].

Related literature

For naturally occurring 3-alkyl-4-hydroxyquinolin-2-ones, see: Paul & Bose (1968[Paul, B. D. & Bose, P. K. (1968). J. Indian Chem. Soc. 45, 552-553.]); Faizutdinova et al. (1969[Faizutdinova, Z. Sh., Bessonova, I. A. & Yunusov, S. Yu. (1969). Khim. Prir. Soedin. 5, 455-456.]); Jurd et al. (1983[Jurd, L., Benson, M. & Wong, R. Y. (1983). Aust. J. Chem. 36, 759-768.]); Chen et al. (1994[Chen, I. S., Wu, S. J., Lin, Y. C., Tsai, I. L., Seki, H., Ko, F. N. & Teng, C. M. (1994). Phytochemistry, 36, 237-240.]); Yamamoto & Harimaya (2004[Yamamoto, Y. & Harimaya, K. (2004). Chem. Lett. 33, 238-239.]); Jain et al. (2006[Jain, S. C., Pandey, M. K., Upadhyay, R. K., Kumar, R., Hundal, G. & Hundal, M. S. (2006). Phytochemistry, 67, 1005-1010.]). For the first published synthesis of the title compound, see: Rapoport & Holden (1959[Rapoport, H. & Holden, K. G. (1959). J. Am. Chem. Soc. 81, 3738-3743.]). For recent synthetic utilization of 3-alkyl-4-hydroxyquinolin-2-ones, see, for example: Kimmel et al. (2010[Kimmel, R., Kafka, S. & Kosmrlj, J. (2010). Carbohydr. Res. 345, 768-779.]).

[Scheme 1]

Experimental

Crystal data

  • C12H13NO3

  • Mr = 219.23

  • Monoclinic, P 21 /c

  • a = 11.4824 (4) Å

  • b = 6.9072 (2) Å

  • c = 14.4978 (5) Å

  • [beta] = 113.1283 (15)°

  • V = 1057.42 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.35 × 0.25 × 0.08 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (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.]) Tmin = 0.966, Tmax = 0.992

  • 4558 measured reflections

  • 2403 independent reflections

  • 1734 reflections with I > 2[sigma](I)

  • Rint = 0.025
Refinement

  • R[F2 > 2[sigma](F2)] = 0.077

  • wR(F2) = 0.272

  • S = 1.14

  • 2403 reflections

  • 151 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.37 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
N1-H1N...O1i 0.85 (2) 2.27 (3) 2.976 (4) 140 (3)
O2-H2...O1ii 0.82 1.94 2.665 (4) 147
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and 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 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5161 ).

Acknowledgements

This study was supported by the internal grant of TBU in Zlin (No. IGA/FT/2012/043), funded from the resources of specific university research, and the Slovenian Research Agency (Project P1-0230-0103 and Joint Project BI-CZ/07-08-018). This work was also partly supported through the infrastructure of the EN-FIST Centre of Excellence, Ljubljana.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chen, I. S., Wu, S. J., Lin, Y. C., Tsai, I. L., Seki, H., Ko, F. N. & Teng, C. M. (1994). Phytochemistry, 36, 237-240.  [CrossRef] [ChemPort] [ISI]
Faizutdinova, Z. Sh., Bessonova, I. A. & Yunusov, S. Yu. (1969). Khim. Prir. Soedin. 5, 455-456.  [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Jain, S. C., Pandey, M. K., Upadhyay, R. K., Kumar, R., Hundal, G. & Hundal, M. S. (2006). Phytochemistry, 67, 1005-1010.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Jurd, L., Benson, M. & Wong, R. Y. (1983). Aust. J. Chem. 36, 759-768.  [CrossRef] [ChemPort]
Kimmel, R., Kafka, S. & Kosmrlj, J. (2010). Carbohydr. Res. 345, 768-779.  [ISI] [CrossRef] [ChemPort] [PubMed]
Nonius (1998). 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.
Paul, B. D. & Bose, P. K. (1968). J. Indian Chem. Soc. 45, 552-553.  [ChemPort]
Rapoport, H. & Holden, K. G. (1959). J. Am. Chem. Soc. 81, 3738-3743.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yamamoto, Y. & Harimaya, K. (2004). Chem. Lett. 33, 238-239.  [ISI] [CrossRef] [ChemPort]

Acta Cryst (2012). E68, o3198  [ doi:10.1107/S1600536812043279 ]

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