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Volume 69 
Part 2 
Page o231  
February 2013  

Received 16 November 2012
Accepted 3 January 2013
Online 12 January 2013

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.102
Data-to-parameter ratio = 8.5
Details
Open access

4-Hydroxy-1-methyl-3-phenylquinolin-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, C16H13NO2, the quinoline system is approximately planar with a maximum deviation from the least-squares plane of 0.059 (1) Å for the N atom. The phenyl ring is rotated by 62.16 (4)° with respect to the plane of the quinoline system. In the crystal, O-H...O hydrogen bonds link molecules into infinite chains running along the b-axis direction.

Related literature

For the preparation of the title compound and other 4-hydroxyquinolin-2-ones, see: Baumgarten & Kärgel (1927[Baumgarten, P. & Kärgel, W. (1927). Ber. Dtsch Chem. Ges. B, 60, 832-842.]); Lange et al., (2001[Lange, J. H. M., Verveer, P. C., Osnabrug, S. J. M. & Visser, G. M. (2001). Tetrahedron Lett. 42, 1367-1369.]); Martensson & Nilsson (1960[Martensson, O. & Nilsson, E. (1960). Acta Chem. Scand. 14, 1129-1150.]); Bezuglyi et al. (1992[Bezuglyi, P. A., Ukrainets, I. V., Treskach, V. I. & Turov, A. V. (1992). Khim. Geterotsikl. Soedin. pp. 522-524.]). For synthetic utilization of the title compound, see: Kafka et al. (2002[Kafka, S., Klásek, A., Polis, J. & Kosmrlj, J. (2002). Heterocycles, 57, 1659-1682.]); Klásek et al. (2002[Klásek, A., Polis, J., Mrkvicka, V. & Kosmrlj, J. (2002). J. Heterocycl. Chem. 39, 1315-1320.]).

[Scheme 1]

Experimental

Crystal data

  • C16H13NO2

  • Mr = 251.27

  • Monoclinic, P 21

  • a = 6.1787 (2) Å

  • b = 8.2696 (2) Å

  • c = 12.3665 (4) Å

  • [beta] = 101.632 (2)°

  • V = 618.89 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.50 × 0.25 × 0.10 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 = 0.957, Tmax = 0.991

  • 2580 measured reflections

  • 1479 independent reflections

  • 1235 reflections with I > 2[sigma](I)

  • Rint = 0.017
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.102

  • S = 1.02

  • 1479 reflections

  • 174 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2O...O1i 0.82 1.89 2.655 (2) 156
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+2].

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, 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: FY2079 ).

Acknowledgements

This study was supported by the internal grant of the 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

Baumgarten, P. & Kärgel, W. (1927). Ber. Dtsch Chem. Ges. B, 60, 832-842.  [CrossRef]
Bezuglyi, P. A., Ukrainets, I. V., Treskach, V. I. & Turov, A. V. (1992). Khim. Geterotsikl. Soedin. pp. 522-524.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kafka, S., Klásek, A., Polis, J. & Kosmrlj, J. (2002). Heterocycles, 57, 1659-1682.  [ChemPort]
Klásek, A., Polis, J., Mrkvicka, V. & Kosmrlj, J. (2002). J. Heterocycl. Chem. 39, 1315-1320.
Lange, J. H. M., Verveer, P. C., Osnabrug, S. J. M. & Visser, G. M. (2001). Tetrahedron Lett. 42, 1367-1369.  [ISI] [CrossRef] [ChemPort]
Martensson, O. & Nilsson, E. (1960). Acta Chem. Scand. 14, 1129-1150.  [ChemPort]
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2013). E69, o231  [ doi:10.1107/S1600536813000226 ]

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