3,5-Dihydr-oxy-2-methyl-4H-pyran-4-one.

In the title compound, C(6)H(6)O(4), inter- and intra-molecular hydrogen bonds are observed which help to establish the crystal structure. There are weak π-π interactions between pyran rings separated by 3.5692 (9) Å.

Related literature

For general background, see: Shinoda et al. (2004 ▶). For related structures, see: Yao et al. (2005 ▶); Gibbons et al. (2000 ▶).

Experimental

Crystal data

C6H6O4

M = 142.11

Monoclinic,

a = 6.9400 (14) Å

b = 6.0648 (12) Å

c = 14.008 (3) Å

β = 92.77 (3)°

V = 588.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 113 (2) K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.981, T max = 0.986

3970 measured reflections

1381 independent reflections

1166 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.10

1381 reflections

115 parameters

All H-ataom parameters refined

Δρmax = 0.37 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010957/pv2074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010957/pv2074Isup2.hkl

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

C6H6O4	F000 = 296
Mr = 142.11	Dx = 1.603 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1620 reflections
a = 6.9400 (14) Å	θ = 1.5–27.9º
b = 6.0648 (12) Å	µ = 0.14 mm−1
c = 14.008 (3) Å	T = 113 (2) K
β = 92.77 (3)º	Block, colorless
V = 588.9 (2) Å3	0.14 × 0.12 × 0.10 mm
Z = 4

Rigaku Saturn diffractometer	1381 independent reflections
Radiation source: rotating anode	1166 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.025
T = 113(2) K	θmax = 27.9º
ω scans	θmin = 2.9º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	h = −9→9
Tmin = 0.981, Tmax = 0.986	k = −7→7
3970 measured reflections	l = −10→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	All H-atom parameters refined
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0654P)2] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1381 reflections	Δρmax = 0.37 e Å−3
115 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
O3	0.27997 (10)	1.01120 (11)	0.27250 (5)	0.0149 (2)
O1	0.76427 (10)	1.05517 (12)	0.44524 (5)	0.0157 (2)
O4	0.56909 (12)	0.69576 (12)	0.26153 (5)	0.0171 (2)
O2	0.32648 (11)	1.36372 (12)	0.40092 (5)	0.0173 (2)
C4	0.43152 (15)	1.02588 (15)	0.32615 (7)	0.0124 (2)
C5	0.46324 (15)	1.20540 (16)	0.39217 (7)	0.0132 (2)
C3	0.58183 (15)	0.86536 (16)	0.32479 (7)	0.0127 (2)
C2	0.74196 (15)	0.88197 (16)	0.38483 (7)	0.0139 (2)
C6	0.62774 (16)	1.21333 (17)	0.44749 (7)	0.0157 (2)
C1	0.90601 (15)	0.72547 (19)	0.39113 (8)	0.0174 (3)
H4	0.656 (2)	1.323 (2)	0.4929 (10)	0.021 (3)*
H3	0.871 (2)	0.582 (2)	0.3585 (10)	0.028 (3)*
H1	1.017 (2)	0.782 (2)	0.3616 (11)	0.037 (4)*
H2	0.940 (2)	0.689 (2)	0.4591 (10)	0.025 (3)*
H5	0.271 (3)	1.393 (3)	0.3397 (14)	0.054 (5)*
H6	0.454 (3)	0.669 (2)	0.2453 (11)	0.037 (4)*

	U11	U22	U33	U12	U13	U23
O3	0.0141 (4)	0.0150 (4)	0.0153 (4)	0.0004 (3)	−0.0022 (3)	−0.0013 (3)
O1	0.0155 (4)	0.0165 (4)	0.0148 (4)	−0.0005 (3)	−0.0020 (3)	−0.0020 (3)
O4	0.0136 (4)	0.0163 (4)	0.0211 (4)	0.0004 (3)	−0.0008 (3)	−0.0080 (3)
O2	0.0233 (4)	0.0142 (4)	0.0142 (4)	0.0058 (3)	−0.0018 (3)	−0.0018 (3)
C4	0.0142 (5)	0.0125 (5)	0.0105 (4)	−0.0022 (4)	0.0016 (4)	0.0017 (3)
C5	0.0177 (5)	0.0106 (5)	0.0116 (4)	0.0007 (4)	0.0021 (4)	0.0008 (3)
C3	0.0138 (5)	0.0118 (5)	0.0128 (5)	−0.0019 (4)	0.0023 (4)	−0.0011 (3)
C2	0.0145 (5)	0.0141 (5)	0.0132 (4)	−0.0017 (4)	0.0024 (4)	−0.0003 (3)
C6	0.0200 (6)	0.0133 (5)	0.0139 (5)	−0.0012 (4)	0.0006 (4)	−0.0020 (4)
C1	0.0126 (5)	0.0200 (6)	0.0195 (5)	0.0013 (4)	0.0001 (4)	−0.0010 (4)

O3—C4	1.2659 (13)	C4—C5	1.4386 (13)
O1—C6	1.3497 (13)	C5—C6	1.3494 (16)
O1—C2	1.3531 (12)	C3—C2	1.3646 (15)
O4—C3	1.3577 (12)	C2—C1	1.4816 (15)
O4—H6	0.838 (18)	C6—H4	0.936 (14)
O2—C5	1.3598 (12)	C1—H3	1.005 (15)
O2—H5	0.94 (2)	C1—H1	0.956 (17)
C4—C3	1.4276 (14)	C1—H2	0.996 (15)
C6—O1—C2	120.47 (8)	O1—C2—C3	120.53 (9)
C3—O4—H6	110.7 (11)	O1—C2—C1	113.31 (9)
C5—O2—H5	107.9 (12)	C3—C2—C1	126.15 (9)
O3—C4—C3	122.06 (9)	C5—C6—O1	122.45 (9)
O3—C4—C5	122.13 (9)	C5—C6—H4	124.0 (8)
C3—C4—C5	115.82 (9)	O1—C6—H4	113.5 (8)
C6—C5—O2	119.86 (9)	C2—C1—H3	111.1 (8)
C6—C5—C4	119.68 (10)	C2—C1—H1	112.2 (9)
O2—C5—C4	120.44 (9)	H3—C1—H1	107.1 (13)
O4—C3—C2	118.92 (9)	C2—C1—H2	110.3 (8)
O4—C3—C4	120.04 (9)	H3—C1—H2	106.4 (12)
C2—C3—C4	121.01 (9)	H1—C1—H2	109.5 (13)
O3—C4—C5—C6	−179.79 (9)	C6—O1—C2—C1	179.47 (9)
C3—C4—C5—C6	0.12 (14)	O4—C3—C2—O1	176.47 (9)
O3—C4—C5—O2	1.94 (15)	C4—C3—C2—O1	−1.93 (15)
C3—C4—C5—O2	−178.15 (8)	O4—C3—C2—C1	−2.39 (16)
O3—C4—C3—O4	3.12 (15)	C4—C3—C2—C1	179.21 (9)
C5—C4—C3—O4	−176.78 (8)	O2—C5—C6—O1	176.71 (9)
O3—C4—C3—C2	−178.50 (9)	C4—C5—C6—O1	−1.58 (15)
C5—C4—C3—C2	1.59 (14)	C2—O1—C6—C5	1.32 (15)
C6—O1—C2—C3	0.47 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H6···O3i	0.838 (18)	1.89 (2)	2.6902 (12)	159.6 (13)
O2—H5···O3ii	0.94 (2)	1.75 (2)	2.6596 (12)	162.6 (17)
O4—H6···O3	0.838 (18)	2.44 (2)	2.7820 (12)	105.4 (10)
C1—H3···O4	1.005 (15)	2.537 (14)	2.8957 (15)	100.5 (9)
C6—H4···O2iii	0.936 (14)	2.412 (13)	3.3354 (14)	169.4 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H6⋯O3i	0.838 (18)	1.89 (2)	2.6902 (12)	159.6 (13)
O2—H5⋯O3ii	0.94 (2)	1.75 (2)	2.6596 (12)	162.6 (17)
O4—H6⋯O3	0.838 (18)	2.44 (2)	2.7820 (12)	105.4 (10)
C1—H3⋯O4	1.005 (15)	2.537 (14)	2.8957 (15)	100.5 (9)
C6—H4⋯O2iii	0.936 (14)	2.412 (13)	3.3354 (14)	169.4 (12)

Symmetry codes: (i) ; (ii) ; (iii) .