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Volume 64 
Part 1 
Page o154  
January 2008  

Received 27 August 2007
Accepted 13 September 2007
Online 6 December 2007


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© International Union of Crystallography 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.048
wR = 0.142
Data-to-parameter ratio = 15.9
Details

2-(4,5-Dihydro-1,3-oxazol-2-yl)quinoline

Pablo Machado,a Fernanda A. Rosa,a Rubia M. S. da Silva,b Robert A. Burrowb* and Marcos A. P. Martinsa*

aNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil, and bLaboratório de Materiais Inorgânicos, Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
Correspondence e-mail: rburrow@ewald.base.ufsm.br, mmartins@base.ufsm.br

The title compound, C12H10N2O, is approximately planar. The angle between the quinoline and 4,5-dihydrooxazole ring systems is 11.91 (12)°. The molecules pack into a herringbone array with no significant [pi]-[pi] interactions. The dihydrooxazole N and O atoms are disordered over two positions, with almost equal site occupancy factors.

Related literature

For related 2-substituted quinoline compounds, see: Mague et al. (1997[Mague, J. T., Vang, S., Berge, D. G. & Wacholtz, W. F. (1997). Acta Cryst. C53, 973-979.]); Yang et al. (2001[Yang, Q.-Y., Zhou, Z.-Y. & Qi, J.-Y. (2001). Acta Cryst. E57, o971-o972.]); Qi et al. (2003[Qi, J. Y., Qiu, L. Q., Yang, Q. Y., Zhou, Z. Y. & Chan, A. S. C. (2003). Acta Cryst. E59, o104-o105.]); Xu et al. (2006[Xu, R.-H., Zhou, J., Xu, Y., Qi, L., Shen, X. & Zhu, D.-R. (2006). Acta Cryst. E62, o5234-o5235.]). For the synthesis, see: Ishihara & Togo (2007[Ishihara, M. & Togo, H. (2007). Tetrahedron, 63, 1474-1480.]). For related literature, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Cunico et al. (2006[Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, M. A. P., Zanatta, N., de Souza, M. V. N., Freitas, I. O., Soares, R. P. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. Lett. 16, 649-653.]); Hartline et al. (2005[Hartline, C. B., Harden, E. A., Williams-Aziz, S. L., Kushner, N. L., Brideau, R. J. & Kern, E. R. (2005). Antiviral Res. 65, 97-105.]).

[Scheme 1]

Experimental

Crystal data

  • C12H10N2O

  • Mr = 198.22

  • Monoclinic, P 21 /c

  • a = 6.2240 (3) Å

  • b = 13.6649 (6) Å

  • c = 11.8186 (6) Å

  • [beta] = 102.097 (3)°

  • V = 982.86 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 273 (2) K

  • 0.24 × 0.21 × 0.13 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2 (Version 2.1), COSMO (Version 1.56), BIS (Version 2.0.1.9), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.])Tmin = 0.705, Tmax = 1 (expected range = 0.697-0.989)

  • 9874 measured reflections

  • 2183 independent reflections

  • 1128 reflections with I > 2[sigma](I)

  • Rint = 0.039
Refinement

  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.143

  • S = 1.00

  • 2183 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Data collection: APEX2/COSMO/BIS (Bruker, 2006[Bruker (2006). APEX2 (Version 2.1), COSMO (Version 1.56), BIS (Version 2.0.1.9), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 (Version 2.1), COSMO (Version 1.56), BIS (Version 2.0.1.9), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and SADABS (Bruker, 2006[Bruker (2006). APEX2 (Version 2.1), COSMO (Version 1.56), BIS (Version 2.0.1.9), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Bruker, 2001[Bruker (2001). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2007[Brandenburg, K. (2007). DIAMOND. Version 3.1e. 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: LH2491 ).

Acknowledgements

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq/PRONEX) and Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS) for financial support. Fellowships from CNPq and CAPES are also acknowledged. The diffractomer was funded by a CT-INFRA grant from the Financiadora de Estudos e Projetos (FINEP), Brazil.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [CrossRef] [details]
Brandenburg, K. (2007). DIAMOND. Version 3.1e. Crystal Impact Gbr, Bonn, Germany.
Bruker (2001). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2 (Version 2.1), COSMO (Version 1.56), BIS (Version 2.0.1.9), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.
Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, M. A. P., Zanatta, N., de Souza, M. V. N., Freitas, I. O., Soares, R. P. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. Lett. 16, 649-653.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [details]
Hartline, C. B., Harden, E. A., Williams-Aziz, S. L., Kushner, N. L., Brideau, R. J. & Kern, E. R. (2005). Antiviral Res. 65, 97-105.  [CrossRef] [PubMed] [ChemPort]
Ishihara, M. & Togo, H. (2007). Tetrahedron, 63, 1474-1480.  [CrossRef] [ChemPort]
Mague, J. T., Vang, S., Berge, D. G. & Wacholtz, W. F. (1997). Acta Cryst. C53, 973-979.  [CrossRef] [details]
Qi, J. Y., Qiu, L. Q., Yang, Q. Y., Zhou, Z. Y. & Chan, A. S. C. (2003). Acta Cryst. E59, o104-o105.  [CrossRef] [details]
Xu, R.-H., Zhou, J., Xu, Y., Qi, L., Shen, X. & Zhu, D.-R. (2006). Acta Cryst. E62, o5234-o5235.  [CrossRef] [details]
Yang, Q.-Y., Zhou, Z.-Y. & Qi, J.-Y. (2001). Acta Cryst. E57, o971-o972.  [CrossRef] [details]

Acta Cryst (2008). E64, o154  [ doi:10.1107/S1600536807045023 ]