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Volume 69 
Part 5 
Page o662  
May 2013  

Received 25 March 2013
Accepted 29 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.097
Data-to-parameter ratio = 10.0
Details
Open access

3-[2-(3-Phenyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]-1,3-oxazolidin-2-one

aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétences, Pharmacochimie, Avenue Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: bal_daouda@yahoo.fr

The dihydroquinoxaline ring system of the title molecule, C19H17N3O3, is approximately planar [maximum deviation = 0.050 (2) Å], the dihedral angle between the planes through the two fused rings being 4.75 (8)°. The mean plane through the fused-ring system forms a dihedral angle of 30.72 (5)° with the attached phenyl ring. The molecular conformation is enforced by C-H...O hydrogen bonds. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming a three-dimensional network.

Related literature

For biochemical properties of quinoxaline derivatives, see: Seitz et al. (2002[Seitz, L. E., Suling, W. J. & Reynolds, R. C. (2002). J. Med. Chem. 45, 5604-5606.]); Monge et al. (1993[Monge, A., Palop, J. A., Del Castillo, J. C., Caldero, J. M., Roca, J., Romero, G., Del Rio, J. & Lasheras, B. (1993). J. Med. Chem. 36, 2745-2750.]); Kim et al. (2004[Kim, Y. B., Kim, Y. H., Park, J. Y. & Kim, S. K. (2004). Bioorg. Med. Chem. Lett. 14, 541-544.]); Bailly et al. (1999[Bailly, C., Echepare, S., Gago, F. & Waring, M. (1999). Anti-Cancer Drug Des. 14, 291-303.]). For a related structure, see: Caleb et al. (2009[Caleb, A. A., Bouhfid, R., Essassi, E. M. & El Ammari, L. (2009). Acta Cryst. E65, o2024-o2025.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17N3O3

  • Mr = 335.36

  • Monoclinic, C c

  • a = 9.6314 (5) Å

  • b = 16.6596 (9) Å

  • c = 10.0749 (5) Å

  • [beta] = 98.097 (3)°

  • V = 1600.46 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.43 × 0.31 × 0.19 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • 23600 measured reflections

  • 2249 independent reflections

  • 1897 reflections with I > 2[sigma](I)

  • Rint = 0.078

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.097

  • S = 1.03

  • 2249 reflections

  • 226 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O1 0.93 2.33 2.860 (3) 116
C17-H17B...O1 0.97 2.53 3.061 (2) 114
C2-H2...O1i 0.93 2.42 3.283 (3) 154
C5-H5...O3ii 0.93 2.50 3.244 (3) 137
C18-H18B...O1i 0.97 2.44 3.367 (3) 159
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+2, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5054 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Bailly, C., Echepare, S., Gago, F. & Waring, M. (1999). Anti-Cancer Drug Des. 14, 291-303.  [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Caleb, A. A., Bouhfid, R., Essassi, E. M. & El Ammari, L. (2009). Acta Cryst. E65, o2024-o2025.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kim, Y. B., Kim, Y. H., Park, J. Y. & Kim, S. K. (2004). Bioorg. Med. Chem. Lett. 14, 541-544.  [CrossRef] [PubMed] [ChemPort]
Monge, A., Palop, J. A., Del Castillo, J. C., Caldero, J. M., Roca, J., Romero, G., Del Rio, J. & Lasheras, B. (1993). J. Med. Chem. 36, 2745-2750.  [CrossRef] [ChemPort] [PubMed] [ISI]
Seitz, L. E., Suling, W. J. & Reynolds, R. C. (2002). J. Med. Chem. 45, 5604-5606.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o662  [ doi:10.1107/S1600536813008702 ]

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