6-Hy-droxy-7,8-dimethyl-chroman-2-one.

The title compound, C(11)H(12)O(3), is essentially planar, with an r.m.s. deviation of 0.179 Å from the mean plane through the 14 non-H atoms in the mol-ecule. The benzene ring and the pyranone mean plane are inclined at 13.12 (6)° to one another and the pyran-one ring adopts a flattened chair conformation. In the crystal, O-H⋯O hydrogen bonds and C-H⋯O contacts form R(1) (2)(6) rings and link mol-ecules into chains along b. Additional C-H⋯O contacts generate inversion dimers, with R(2) (2)(8) ring motifs, and form sheets parallel to (-102) which are linked by C-H⋯π interactions.

Related literature

For the synthesis, see: Lecea et al. (2010 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶) and for related structures, see: Cameron et al. (2011 ▶); Goswami et al. (2011 ▶, 2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H12O3

M = 192.21

Triclinic,

a = 6.2808 (14) Å

b = 8.630 (2) Å

c = 9.389 (2) Å

α = 88.603 (6)°

β = 83.638 (5)°

γ = 69.088 (5)°

V = 472.40 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 92 K

0.34 × 0.32 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.656, T max = 0.747

9073 measured reflections

3963 independent reflections

3368 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.188

S = 1.11

3963 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: APEX2 (Bruker, 2011 ▶) and SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029704/lh5497sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029704/lh5497Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029704/lh5497Isup3.cml

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

C11H12O3	Z = 2
Mr = 192.21	F(000) = 204
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2808 (14) Å	Cell parameters from 4269 reflections
b = 8.630 (2) Å	θ = 2.5–35.1°
c = 9.389 (2) Å	µ = 0.10 mm−1
α = 88.603 (6)°	T = 92 K
β = 83.638 (5)°	Triangular plate, yellow
γ = 69.088 (5)°	0.34 × 0.32 × 0.12 mm
V = 472.40 (19) Å3

Bruker APEXII CCD area-detector diffractometer	3963 independent reflections
Radiation source: fine-focus sealed tube	3368 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 35.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −9→9
Tmin = 0.656, Tmax = 0.747	k = −13→12
9073 measured reflections	l = −14→15

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0874P)2 + 0.1584P] where P = (Fo2 + 2Fc2)/3
3963 reflections	(Δ/σ)max < 0.001
132 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
O1	0.26085 (18)	1.00639 (11)	0.13645 (11)	0.0271 (2)
C1	0.2601 (2)	0.86709 (14)	0.15707 (13)	0.0195 (2)
O2	0.44911 (14)	0.75378 (10)	0.20340 (9)	0.01890 (18)
C2	0.0627 (2)	0.81355 (14)	0.13980 (13)	0.0198 (2)
H2A	−0.0395	0.8915	0.0761	0.024*
H2B	−0.0265	0.8178	0.2344	0.024*
C3	0.14248 (19)	0.63811 (13)	0.07686 (12)	0.0175 (2)
H3A	0.0114	0.5993	0.0819	0.021*
H3B	0.2033	0.6378	−0.0251	0.021*
C4	0.32642 (18)	0.52366 (13)	0.15984 (11)	0.01564 (19)
C5	0.46469 (18)	0.58834 (13)	0.22549 (11)	0.01568 (19)
C6	0.63239 (18)	0.49425 (14)	0.31075 (11)	0.0165 (2)
C61	0.7683 (2)	0.57324 (16)	0.38576 (13)	0.0213 (2)
H61A	0.7096	0.6933	0.3707	0.032*
H61B	0.9300	0.5266	0.3468	0.032*
H61C	0.7538	0.5514	0.4886	0.032*
C7	0.66848 (19)	0.32489 (14)	0.32618 (12)	0.0179 (2)
C71	0.8441 (2)	0.21682 (16)	0.41777 (14)	0.0247 (2)
H71A	0.9982	0.1949	0.3685	0.037*
H71B	0.8197	0.1116	0.4349	0.037*
H71C	0.8290	0.2735	0.5096	0.037*
C8	0.53406 (19)	0.25683 (13)	0.25696 (12)	0.0181 (2)
O8	0.57401 (17)	0.09172 (11)	0.27400 (11)	0.0255 (2)
H8O	0.472 (4)	0.070 (3)	0.226 (2)	0.038*
C9	0.36335 (19)	0.35568 (13)	0.17644 (12)	0.0175 (2)
H9	0.2715	0.3080	0.1326	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0341 (5)	0.0165 (4)	0.0344 (5)	−0.0117 (3)	−0.0113 (4)	0.0055 (3)
C1	0.0231 (5)	0.0153 (4)	0.0197 (5)	−0.0058 (4)	−0.0048 (4)	0.0014 (3)
O2	0.0213 (4)	0.0159 (4)	0.0221 (4)	−0.0087 (3)	−0.0064 (3)	0.0024 (3)
C2	0.0190 (5)	0.0157 (4)	0.0241 (5)	−0.0046 (4)	−0.0059 (4)	0.0015 (4)
C3	0.0189 (5)	0.0166 (4)	0.0176 (4)	−0.0060 (4)	−0.0059 (4)	0.0012 (3)
C4	0.0162 (4)	0.0146 (4)	0.0159 (4)	−0.0048 (3)	−0.0028 (3)	−0.0008 (3)
C5	0.0172 (4)	0.0147 (4)	0.0154 (4)	−0.0058 (3)	−0.0028 (3)	0.0008 (3)
C6	0.0148 (4)	0.0193 (5)	0.0147 (4)	−0.0052 (3)	−0.0021 (3)	−0.0003 (3)
C61	0.0191 (5)	0.0271 (6)	0.0200 (5)	−0.0102 (4)	−0.0050 (4)	0.0002 (4)
C7	0.0165 (4)	0.0189 (5)	0.0162 (4)	−0.0036 (4)	−0.0034 (3)	0.0020 (3)
C71	0.0237 (5)	0.0241 (5)	0.0228 (5)	−0.0027 (4)	−0.0087 (4)	0.0046 (4)
C8	0.0191 (5)	0.0145 (4)	0.0194 (5)	−0.0041 (3)	−0.0026 (4)	0.0011 (3)
O8	0.0281 (5)	0.0139 (4)	0.0342 (5)	−0.0052 (3)	−0.0101 (4)	0.0039 (3)
C9	0.0177 (5)	0.0146 (4)	0.0197 (5)	−0.0048 (3)	−0.0038 (4)	−0.0001 (3)

O1—C1	1.2145 (14)	C6—C61	1.5039 (16)
C1—O2	1.3489 (14)	C61—H61A	0.9800
C1—C2	1.4948 (17)	C61—H61B	0.9800
O2—C5	1.4076 (13)	C61—H61C	0.9800
C2—C3	1.5261 (16)	C7—C8	1.4051 (16)
C2—H2A	0.9900	C7—C71	1.5044 (16)
C2—H2B	0.9900	C71—H71A	0.9800
C3—C4	1.5049 (15)	C71—H71B	0.9800
C3—H3A	0.9900	C71—H71C	0.9800
C3—H3B	0.9900	C8—O8	1.3644 (14)
C4—C5	1.3882 (15)	C8—C9	1.3943 (15)
C4—C9	1.3916 (15)	O8—O1i	2.7788 (15)
C5—C6	1.3979 (15)	O8—H8O	0.89 (2)
C6—C7	1.4032 (16)	C9—H9	0.9500
O1—C1—O2	117.42 (11)	C7—C6—C61	120.86 (10)
O1—C1—C2	124.89 (11)	C6—C61—H61A	109.5
O2—C1—C2	117.65 (10)	C6—C61—H61B	109.5
C1—O2—C5	120.91 (9)	H61A—C61—H61B	109.5
C1—C2—C3	111.78 (9)	C6—C61—H61C	109.5
C1—C2—H2A	109.3	H61A—C61—H61C	109.5
C3—C2—H2A	109.3	H61B—C61—H61C	109.5
C1—C2—H2B	109.3	C6—C7—C8	119.04 (10)
C3—C2—H2B	109.3	C6—C7—C71	121.15 (10)
H2A—C2—H2B	107.9	C8—C7—C71	119.79 (10)
C4—C3—C2	109.49 (9)	C7—C71—H71A	109.5
C4—C3—H3A	109.8	C7—C71—H71B	109.5
C2—C3—H3A	109.8	H71A—C71—H71B	109.5
C4—C3—H3B	109.8	C7—C71—H71C	109.5
C2—C3—H3B	109.8	H71A—C71—H71C	109.5
H3A—C3—H3B	108.2	H71B—C71—H71C	109.5
C5—C4—C9	117.89 (10)	O8—C8—C9	121.51 (10)
C5—C4—C3	118.78 (9)	O8—C8—C7	117.50 (10)
C9—C4—C3	123.32 (10)	C9—C8—C7	120.98 (10)
C4—C5—C6	123.13 (10)	C8—O8—H8O	105.9 (13)
C4—C5—O2	120.75 (9)	C4—C9—C8	120.53 (10)
C6—C5—O2	116.05 (9)	C4—C9—H9	119.7
C5—C6—C7	118.36 (10)	C8—C9—H9	119.7
C5—C6—C61	120.77 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8O···O1i	0.89 (2)	1.89 (2)	2.7788 (15)	175 (2)
C9—H9···O1i	0.95	2.63	3.3371 (16)	132
C2—H2A···O1ii	0.99	2.52	3.4626 (16)	159
C3—H3B···Cgiii	0.99	2.54	3.4771 (15)	157
C61—H61C···Cgiv	0.98	2.79	3.6956 (16)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8O⋯O1i	0.89 (2)	1.89 (2)	2.7788 (15)	175 (2)
C9—H9⋯O1i	0.95	2.63	3.3371 (16)	132
C2—H2A⋯O1ii	0.99	2.52	3.4626 (16)	159
C3—H3B⋯Cg iii	0.99	2.54	3.4771 (15)	157
C61—H61C⋯Cg iv	0.98	2.79	3.6956 (16)	153

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