6-Hy-droxy-5,7,8-trimethyl-chroman-2-one.

The title compound, C(12)H(14)O(3), consists of a chromanone unit with an -OH substituent at the 4-position and methyl substituents on the remaining C atoms of the aromatic ring. The fused pyran-one ring adopts a distorted envelope conformation with the methyl-ene group adjacent to the carbonyl carbon as the flap atom. The crystal structure is stabilized by classical O-H⋯O hydrogen bonds and weak C-H⋯O and C-H⋯π inter-actions, generating a three-dimensional network.

Related literature

For the synthesis, see: Ong et al. (2008 ▶). For a related structure, see: Budzianowski & Katrusiak (2002 ▶). For current applications of this compound, see: Ong et al. (2008 ▶); Harada et al. (1987 ▶); Hernández-Torres et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H14O3

M = 206.23

Monoclinic,

a = 4.5339 (6) Å

b = 16.815 (2) Å

c = 13.302 (2) Å

β = 96.495 (8)°

V = 1007.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 89 K

0.38 × 0.11 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2009 ▶) T min = 0.809, T max = 1.00

12531 measured reflections

2021 independent reflections

1535 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.201

S = 1.13

2021 reflections

142 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker 2009 ▶); cell refinement: SAINT (Bruker 2009 ▶); data reduction: SAINT; program(s) used to solve structure: OLEX2 (Dolomanov et al., 2009 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); 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) I, global. DOI: 10.1107/S1600536811019982/hg5043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019982/hg5043Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019982/hg5043Isup3.cml

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

C12H14O3	F(000) = 440
Mr = 206.23	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1569 reflections
a = 4.5339 (6) Å	θ = 2.4–25.9°
b = 16.815 (2) Å	µ = 0.10 mm−1
c = 13.302 (2) Å	T = 89 K
β = 96.495 (8)°	Block, colourless
V = 1007.6 (2) Å3	0.38 × 0.11 × 0.06 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2021 independent reflections
Radiation source: fine-focus sealed tube	1535 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 26.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker 2009)	h = −5→5
Tmin = 0.809, Tmax = 1.00	k = −20→20
12531 measured reflections	l = −13→16

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0733P)2 + 1.6783P] where P = (Fo2 + 2Fc2)/3
2021 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.27 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	0.0748 (4)	0.96722 (11)	0.22522 (15)	0.0219 (5)
C1	−0.0405 (6)	0.89510 (16)	0.2597 (2)	0.0194 (6)
C2	−0.2136 (6)	0.90381 (17)	0.3392 (2)	0.0199 (6)
C21	−0.2918 (7)	0.98596 (17)	0.3742 (2)	0.0269 (7)
H21A	−0.4854	0.9843	0.4002	0.040*
H21B	−0.3003	1.0231	0.3171	0.040*
H21C	−0.1402	1.0037	0.4278	0.040*
C3	−0.3075 (6)	0.83491 (17)	0.3848 (2)	0.0207 (6)
C31	−0.4844 (7)	0.83761 (18)	0.4734 (2)	0.0253 (7)
H31A	−0.4523	0.8888	0.5082	0.038*
H31B	−0.4208	0.7944	0.5203	0.038*
H31C	−0.6957	0.8314	0.4496	0.038*
C4	−0.2276 (6)	0.76058 (17)	0.3479 (2)	0.0207 (6)
O4	−0.3260 (5)	0.69559 (12)	0.39722 (16)	0.0261 (5)
H4O	−0.292 (8)	0.6515 (14)	0.369 (2)	0.031*
C5	−0.0575 (6)	0.75268 (17)	0.2672 (2)	0.0210 (6)
C51	0.0261 (7)	0.67095 (17)	0.2340 (2)	0.0258 (7)
H51A	0.1317	0.6425	0.2916	0.039*
H51B	0.1550	0.6756	0.1799	0.039*
H51C	−0.1539	0.6415	0.2090	0.039*
C6	0.0368 (6)	0.82203 (17)	0.2215 (2)	0.0195 (6)
C7	0.2168 (6)	0.82110 (17)	0.1330 (2)	0.0209 (6)
H7A	0.1559	0.7753	0.0886	0.025*
H7B	0.4297	0.8148	0.1578	0.025*
C8	0.1714 (7)	0.89840 (18)	0.0725 (2)	0.0254 (7)
H8A	0.3188	0.9010	0.0231	0.031*
H8B	−0.0288	0.8980	0.0341	0.031*
C9	0.2022 (6)	0.97048 (17)	0.1380 (2)	0.0224 (6)
O9	0.3212 (5)	1.03231 (12)	0.11866 (16)	0.0283 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0275 (11)	0.0175 (10)	0.0222 (11)	−0.0005 (8)	0.0097 (8)	−0.0005 (8)
C1	0.0225 (14)	0.0163 (14)	0.0189 (14)	−0.0006 (11)	0.0010 (11)	0.0019 (11)
C2	0.0190 (14)	0.0215 (14)	0.0195 (14)	0.0027 (11)	0.0043 (11)	−0.0027 (11)
C21	0.0324 (16)	0.0215 (15)	0.0274 (16)	0.0017 (13)	0.0066 (13)	−0.0017 (12)
C3	0.0212 (14)	0.0230 (14)	0.0180 (14)	0.0017 (11)	0.0024 (11)	0.0004 (11)
C31	0.0302 (16)	0.0233 (15)	0.0241 (16)	0.0018 (12)	0.0100 (13)	−0.0006 (12)
C4	0.0200 (14)	0.0205 (14)	0.0211 (14)	−0.0006 (11)	0.0000 (11)	0.0012 (12)
O4	0.0331 (12)	0.0175 (10)	0.0296 (12)	−0.0004 (9)	0.0117 (9)	0.0031 (9)
C5	0.0230 (15)	0.0193 (15)	0.0210 (15)	0.0009 (11)	0.0033 (12)	0.0008 (11)
C51	0.0297 (16)	0.0200 (15)	0.0289 (16)	0.0031 (12)	0.0087 (13)	0.0007 (12)
C6	0.0172 (13)	0.0224 (14)	0.0188 (14)	0.0020 (11)	0.0020 (11)	0.0002 (11)
C7	0.0212 (14)	0.0206 (14)	0.0214 (15)	0.0012 (11)	0.0047 (12)	−0.0007 (12)
C8	0.0317 (17)	0.0247 (15)	0.0207 (15)	−0.0006 (13)	0.0065 (13)	−0.0012 (12)
C9	0.0231 (14)	0.0231 (15)	0.0214 (15)	0.0024 (12)	0.0042 (12)	0.0027 (12)
O9	0.0360 (12)	0.0206 (11)	0.0300 (12)	−0.0021 (9)	0.0111 (10)	0.0025 (9)

O1—C9	1.354 (3)	C4—C5	1.398 (4)
O1—C1	1.417 (3)	O4—H4O	0.854 (18)
C1—C6	1.390 (4)	C5—C6	1.404 (4)
C1—C2	1.394 (4)	C5—C51	1.505 (4)
C2—C3	1.397 (4)	C51—H51A	0.9800
C2—C21	1.512 (4)	C51—H51B	0.9800
C21—H21A	0.9800	C51—H51C	0.9800
C21—H21B	0.9800	C6—C7	1.506 (4)
C21—H21C	0.9800	C7—C8	1.530 (4)
C3—C4	1.405 (4)	C7—H7A	0.9900
C3—C31	1.500 (4)	C7—H7B	0.9900
C31—H31A	0.9800	C8—C9	1.490 (4)
C31—H31B	0.9800	C8—H8A	0.9900
C31—H31C	0.9800	C8—H8B	0.9900
C4—O4	1.374 (3)	C9—O9	1.212 (4)
C9—O1—C1	121.4 (2)	C4—C5—C51	119.4 (3)
C6—C1—C2	123.9 (3)	C6—C5—C51	122.2 (3)
C6—C1—O1	121.3 (2)	C5—C51—H51A	109.5
C2—C1—O1	114.6 (2)	C5—C51—H51B	109.5
C1—C2—C3	117.9 (3)	H51A—C51—H51B	109.5
C1—C2—C21	120.1 (3)	C5—C51—H51C	109.5
C3—C2—C21	122.0 (3)	H51A—C51—H51C	109.5
C2—C21—H21A	109.5	H51B—C51—H51C	109.5
C2—C21—H21B	109.5	C1—C6—C5	118.3 (3)
H21A—C21—H21B	109.5	C1—C6—C7	118.5 (3)
C2—C21—H21C	109.5	C5—C6—C7	123.3 (2)
H21A—C21—H21C	109.5	C6—C7—C8	110.5 (2)
H21B—C21—H21C	109.5	C6—C7—H7A	109.6
C2—C3—C4	118.9 (3)	C8—C7—H7A	109.6
C2—C3—C31	122.2 (3)	C6—C7—H7B	109.6
C4—C3—C31	118.9 (3)	C8—C7—H7B	109.6
C3—C31—H31A	109.5	H7A—C7—H7B	108.1
C3—C31—H31B	109.5	C9—C8—C7	112.6 (2)
H31A—C31—H31B	109.5	C9—C8—H8A	109.1
C3—C31—H31C	109.5	C7—C8—H8A	109.1
H31A—C31—H31C	109.5	C9—C8—H8B	109.1
H31B—C31—H31C	109.5	C7—C8—H8B	109.1
O4—C4—C5	121.9 (2)	H8A—C8—H8B	107.8
O4—C4—C3	115.5 (2)	O9—C9—O1	117.4 (3)
C5—C4—C3	122.6 (3)	O9—C9—C8	126.0 (3)
C4—O4—H4O	113 (2)	O1—C9—C8	116.6 (2)
C4—C5—C6	118.4 (3)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O9i	0.85 (2)	2.02 (3)	2.754 (3)	144 (3)
C8—H8B···O9ii	0.99	2.58	3.395 (4)	140
C8—H8B···O4iii	0.99	2.66	3.440 (4)	136
C7—H7B···Cg2iv	0.99	2.61	3.505 (3)	150
C31—H31C···Cg2v	0.98	2.62	3.512 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O9i	0.85 (2)	2.02 (3)	2.754 (3)	144 (3)
C8—H8B⋯O9ii	0.99	2.58	3.395 (4)	140
C8—H8B⋯O4iii	0.99	2.66	3.440 (4)	136
C7—H7B⋯Cg2iv	0.99	2.61	3.505 (3)	150
C31—H31C⋯Cg2v	0.98	2.62	3.512 (3)	151

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