6-Phenyl­oxane-2,4-dione

Slater, K.A.; Andersh, B.; Flint, E.B.; Ferrence, G.M.

doi:10.1107/S1600536812049781

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 (C-C) = 0.003 Å
R = 0.047
wR = 0.114
Data-to-parameter ratio = 14.2
Details

6-Phenyloxane-2,4-dione

Kara A. Slater,^a,^b Brad Andersh,^a Edward B. Flint ^a ^* and Gregory M. Ferrence ^c

^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) and of trans-5,6-diphenylperhydropyran-2,4-dione, see: de Souza et al. (2009). For the synthesis, see: Andersh et al. (2008). For the biological activity of the title compound and its derivatives, see: Aguiar Amaral et al. (2005); Souza et al. (2004); Tait et al. (1997); Wang et al. (1999). For a description of the Cambridge Structural Database, see: Allen (2002). A geometry check was performed using Mogul, see: Bruno et al. (2004). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₁H₁₀O₃
M_r = 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 radiation
= 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) T_min = 0.662, T_max = 0.746
17960 measured reflections
1804 independent reflections
1322 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.114
S = 1.06
1804 reflections
127 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.25 e Å^-3

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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

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organic compounds