6-Phenyl-oxane-2,4-dione.

The title compound, C11H10O3, is a phenyl-subsituted dihydro-pyran-dione 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 = 190.19

Orthorhombic,

a = 16.9888 (6) Å

b = 5.4501 (2) Å

c = 19.7350 (8) Å

V = 1827.28 (12) Å3

Z = 8

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.114

S = 1.06

1804 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049781/bx2433sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049781/bx2433Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049781/bx2433Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10O3	F(000) = 800
Mr = 190.19	Dx = 1.383 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2535 reflections
a = 16.9888 (6) Å	θ = 2.4–23.5°
b = 5.4501 (2) Å	µ = 0.10 mm−1
c = 19.7350 (8) Å	T = 100 K
V = 1827.28 (12) Å3	Prism, colourless
Z = 8	0.17 × 0.14 × 0.03 mm

Bruker APEXII CCD diffractometer	1322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→20
Tmin = 0.662, Tmax = 0.746	k = −6→6
17960 measured reflections	l = −24→24
1804 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.039P)2 + 1.8272P] where P = (Fo2 + 2Fc2)/3
1804 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.15992 (11)	0.2655 (4)	0.22819 (11)	0.0198 (5)
C2	0.13487 (12)	0.0646 (4)	0.27556 (11)	0.0208 (5)
H2A	0.1203	0.1376	0.3198	0.025*
H2B	0.1799	−0.0474	0.2833	0.025*
C3	0.06630 (12)	−0.0808 (4)	0.24883 (12)	0.0200 (5)
C4	0.06699 (12)	−0.1241 (4)	0.17377 (11)	0.0203 (5)
H4A	0.0222	−0.0357	0.1529	0.024*
H4B	0.0598	−0.3015	0.1649	0.024*
C5	0.14301 (12)	−0.0391 (4)	0.14093 (11)	0.0197 (5)
H5	0.1869	−0.1489	0.1557	0.024*
C6	0.13875 (12)	−0.0384 (4)	0.06490 (11)	0.0196 (5)
C7	0.17318 (12)	−0.2284 (4)	0.02863 (12)	0.0240 (5)
H7	0.2002	−0.3554	0.052	0.029*
C8	0.16830 (13)	−0.2336 (4)	−0.04141 (12)	0.0289 (6)
H8	0.1921	−0.364	−0.0659	0.035*
C9	0.12897 (13)	−0.0501 (4)	−0.07580 (12)	0.0283 (5)
H9	0.1257	−0.0542	−0.1238	0.034*
C10	0.09416 (13)	0.1406 (4)	−0.03986 (12)	0.0284 (6)
H10	0.0672	0.2673	−0.0634	0.034*
C11	0.09869 (12)	0.1464 (4)	0.03021 (11)	0.0242 (5)
H11	0.0745	0.2763	0.0546	0.029*
O1	0.17979 (9)	0.4702 (3)	0.24675 (8)	0.0240 (4)
O2	0.01417 (8)	−0.1540 (3)	0.28609 (8)	0.0237 (4)
O3	0.16073 (8)	0.2144 (3)	0.16170 (7)	0.0211 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0139 (10)	0.0164 (11)	0.0290 (13)	0.0004 (8)	−0.0010 (9)	−0.0005 (10)
C2	0.0213 (10)	0.0181 (11)	0.0230 (11)	0.0013 (8)	0.0009 (9)	−0.0004 (9)
C3	0.0190 (10)	0.0102 (9)	0.0307 (12)	0.0038 (8)	0.0010 (10)	0.0024 (9)
C4	0.0183 (10)	0.0147 (10)	0.0279 (12)	−0.0013 (9)	0.0001 (9)	−0.0002 (9)
C5	0.0193 (10)	0.0125 (10)	0.0274 (12)	0.0011 (8)	−0.0004 (9)	−0.0019 (9)
C6	0.0151 (10)	0.0168 (10)	0.0269 (12)	−0.0038 (8)	0.0001 (9)	−0.0007 (10)
C7	0.0221 (11)	0.0184 (11)	0.0314 (13)	−0.0003 (9)	0.0002 (9)	−0.0002 (10)
C8	0.0305 (12)	0.0234 (12)	0.0327 (14)	−0.0010 (10)	0.0030 (10)	−0.0079 (11)
C9	0.0332 (13)	0.0285 (13)	0.0232 (12)	−0.0066 (10)	−0.0002 (10)	−0.0006 (11)
C10	0.0315 (13)	0.0210 (12)	0.0326 (14)	−0.0021 (10)	−0.0039 (10)	0.0030 (11)
C11	0.0258 (11)	0.0179 (11)	0.0289 (13)	−0.0008 (9)	0.0017 (10)	−0.0029 (10)
O1	0.0257 (8)	0.0159 (7)	0.0303 (9)	−0.0028 (6)	−0.0007 (7)	−0.0015 (7)
O2	0.0230 (8)	0.0158 (7)	0.0324 (9)	−0.0014 (6)	0.0062 (7)	0.0014 (7)
O3	0.0229 (7)	0.0152 (7)	0.0253 (9)	−0.0048 (6)	−0.0002 (6)	0.0004 (7)

C1—O1	1.222 (3)	C5—H5	1
C1—O3	1.342 (2)	C6—C7	1.388 (3)
C1—C2	1.501 (3)	C6—C11	1.395 (3)
C2—C3	1.505 (3)	C7—C8	1.385 (3)
C2—H2A	0.99	C7—H7	0.95
C2—H2B	0.99	C8—C9	1.381 (3)
C3—O2	1.218 (2)	C8—H8	0.95
C3—C4	1.500 (3)	C9—C10	1.391 (3)
C4—C5	1.517 (3)	C9—H9	0.95
C4—H4A	0.99	C10—C11	1.385 (3)
C4—H4B	0.99	C10—H10	0.95
C5—O3	1.472 (2)	C11—H11	0.95
C5—C6	1.502 (3)
O1—C1—O3	118.69 (19)	C6—C5—H5	109.2
O1—C1—C2	123.9 (2)	C4—C5—H5	109.2
O3—C1—C2	117.43 (18)	C7—C6—C11	119.4 (2)
C1—C2—C3	112.66 (18)	C7—C6—C5	119.53 (19)
C1—C2—H2A	109.1	C11—C6—C5	121.03 (19)
C3—C2—H2A	109.1	C8—C7—C6	120.3 (2)
C1—C2—H2B	109.1	C8—C7—H7	119.8
C3—C2—H2B	109.1	C6—C7—H7	119.8
H2A—C2—H2B	107.8	C9—C8—C7	120.3 (2)
O2—C3—C4	123.38 (19)	C9—C8—H8	119.9
O2—C3—C2	121.6 (2)	C7—C8—H8	119.9
C4—C3—C2	115.03 (18)	C8—C9—C10	119.8 (2)
C3—C4—C5	112.35 (17)	C8—C9—H9	120.1
C3—C4—H4A	109.1	C10—C9—H9	120.1
C5—C4—H4A	109.1	C11—C10—C9	120.2 (2)
C3—C4—H4B	109.1	C11—C10—H10	119.9
C5—C4—H4B	109.1	C9—C10—H10	119.9
H4A—C4—H4B	107.9	C10—C11—C6	120.0 (2)
O3—C5—C6	106.59 (17)	C10—C11—H11	120
O3—C5—C4	109.98 (16)	C6—C11—H11	120
C6—C5—C4	112.73 (17)	C1—O3—C5	117.72 (16)
O3—C5—H5	109.2
O1—C1—C2—C3	139.8 (2)	C11—C6—C7—C8	0.4 (3)
O3—C1—C2—C3	−40.6 (3)	C5—C6—C7—C8	178.5 (2)
C1—C2—C3—O2	−141.94 (19)	C6—C7—C8—C9	−0.1 (3)
C1—C2—C3—C4	37.3 (2)	C7—C8—C9—C10	0.0 (3)
O2—C3—C4—C5	−173.43 (19)	C8—C9—C10—C11	−0.2 (3)
C2—C3—C4—C5	7.4 (2)	C9—C10—C11—C6	0.5 (3)
C3—C4—C5—O3	−50.7 (2)	C7—C6—C11—C10	−0.6 (3)
C3—C4—C5—C6	−169.46 (17)	C5—C6—C11—C10	−178.68 (19)
O3—C5—C6—C7	137.70 (18)	O1—C1—O3—C5	174.97 (17)
C4—C5—C6—C7	−101.5 (2)	C2—C1—O3—C5	−4.6 (3)
O3—C5—C6—C11	−44.2 (2)	C6—C5—O3—C1	173.64 (17)
C4—C5—C6—C11	76.5 (2)	C4—C5—O3—C1	51.1 (2)