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Volume 69 
Part 1 
Page o69  
January 2013  

Received 30 November 2012
Accepted 4 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.114
Data-to-parameter ratio = 14.2
Details
Open access

6-Phenyloxane-2,4-dione

aMund-Lagowski Department of Chemistry & Biochemistry, Bradley University, Peoria, IL 61625, USA,bDepartment of Chemistry, University of Iowa, Iowa City, IA 52242, USA, and cCB 4160, Department of Chemistry, Illinois State University, Normal, IL 61790, USA
Correspondence e-mail: eflint@fsmail.bradley.edu

The title compound, C11H10O3, is a phenyl-subsituted dihydropyrandione in which the heterocycle adopts a boat conformation with the phenyl substituent canted 72.14 (5)° relative to the mean plane of the heterocycle.

Related literature

For the crystal structure of methyl 4-methyl-3,5-dioxo-1-phenyl-2-oxaspiro[5.5]-4-carboxylate, see: Kirillov et al. (2010[Kirillov, N. F., Melekhin, V. S. & Aliev, Z. G. (2010). J. Struct. Chem, 51, 996-997.]) and of trans-5,6-diphenylperhydropyran-2,4-dione, see: de Souza et al. (2009[Souza, L. C. de, Imbroisi, D. de O., De Simone, C. A., Pereira, M. A. & Malta, V. R. S. (2009). Acta Cryst. E65, o250.]). For the synthesis, see: Andersh et al. (2008[Andersh, B., Gereg, J., Amanuel, M. & Stanley, C. (2008). Synth. Commun. 38, 482-488.]). For the biological activity of the title compound and its derivatives, see: Aguiar Amaral et al. (2005[Aguiar Amaral, P., Bergold, A. M. & Eifler-Lima, V. L. (2005). J. Pharm. Pharm. Sci. 8, 69-75.]); Souza et al. (2004[Souza, L. C., Soares de Araujo, A., Sant'Ana, A. E. G. & Oliveira Imbroisi, D. (2004). Bioorg. Med. Chem. 12, 865-869.]); Tait et al. (1997[Tait, B. D., Hagen, S., Domagala, J., Ellsworth, E. L., Gajda, C., Hamilton, H. W., Vara Prasad, J. V. N., Ferguson, D., Graham, N., Hupe, D., Nouhan, C., Tummino, P. J., Humblet, C., Lunney, E. A., Pavlovsky, A., Rubin, J., Gracheck, S. J., Baldwin, E. T., Bhat, T. N., Erickson, J. W., Gulnik, S. V. & Liu, B. (1997). J. Med. Chem. 40, 3782-3791.]); Wang et al. (1999[Wang, Y., Li, Z., Li, J., Li, S. & Zhang, S. (1999). Gaodeng Xuexiao Huaxue Xuebao, 20, 1559-1563.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). A geometry check was performed using Mogul, see: Bruno et al. (2004[Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133-2144.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10O3

  • Mr = 190.19

  • Orthorhombic, P b c a

  • a = 16.9888 (6) Å

  • b = 5.4501 (2) Å

  • c = 19.7350 (8) Å

  • V = 1827.28 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.17 × 0.14 × 0.03 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.662, Tmax = 0.746

  • 17960 measured reflections

  • 1804 independent reflections

  • 1322 reflections with I > 2[sigma](I)

  • Rint = 0.071

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.114

  • S = 1.06

  • 1804 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), 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: BX2433 ).


Acknowledgements

The authors thank the NSF-CHE (grant No. 1039689) for funding the X-ray diffractometer.

References

Aguiar Amaral, P., Bergold, A. M. & Eifler-Lima, V. L. (2005). J. Pharm. Pharm. Sci. 8, 69-75.  [PubMed]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Andersh, B., Gereg, J., Amanuel, M. & Stanley, C. (2008). Synth. Commun. 38, 482-488.  [ISI] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133-2144.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kirillov, N. F., Melekhin, V. S. & Aliev, Z. G. (2010). J. Struct. Chem, 51, 996-997.  [ISI] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Souza, L. C. de, Imbroisi, D. de O., De Simone, C. A., Pereira, M. A. & Malta, V. R. S. (2009). Acta Cryst. E65, o250.  [CSD] [CrossRef] [details]
Souza, L. C., Soares de Araujo, A., Sant'Ana, A. E. G. & Oliveira Imbroisi, D. (2004). Bioorg. Med. Chem. 12, 865-869.  [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tait, B. D., Hagen, S., Domagala, J., Ellsworth, E. L., Gajda, C., Hamilton, H. W., Vara Prasad, J. V. N., Ferguson, D., Graham, N., Hupe, D., Nouhan, C., Tummino, P. J., Humblet, C., Lunney, E. A., Pavlovsky, A., Rubin, J., Gracheck, S. J., Baldwin, E. T., Bhat, T. N., Erickson, J. W., Gulnik, S. V. & Liu, B. (1997). J. Med. Chem. 40, 3782-3791.  [CrossRef] [ISI]
Wang, Y., Li, Z., Li, J., Li, S. & Zhang, S. (1999). Gaodeng Xuexiao Huaxue Xuebao, 20, 1559-1563.  [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o69  [ doi:10.1107/S1600536812049781 ]

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