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Volume 69 
Part 2 
Page o231  
February 2013  

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

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

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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