1-(2-Hy-droxy-4,5-dimeth-oxy-phen-yl)ethanone.

The mol-ecular structure of the title compound, C10H12O4, contains an intra-molecular hydrogen bond between the phenol and acetyl substituents. In the crystal, C-H⋯π inter-actions act between the mol-ecules in a cyclic manner to stabilize stacks of mol-ecules along the b axis. Several C-H⋯O inter-actions are present between the stacks.

Related literature

For a review on lamellarin alkaloids, see: Fan et al. (2008 ▶). The experimental procedure of Combes et al. (2002 ▶) for a related Fries rearrangement was adapted for the synthesis of the title compound. For alternative syntheses of the title compound by Fries rearrangement, see: Ploypradith et al. (2003 ▶); Nolan et al. (2009 ▶).

Experimental

Crystal data

C10H12O4

M = 196.20

Orthorhombic,

a = 19.1740 (12) Å

b = 5.5026 (3) Å

c = 8.9956 (5) Å

V = 949.10 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.41 × 0.32 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

4718 measured reflections

1214 independent reflections

1106 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.06

1214 reflections

134 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051057/nk2196sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051057/nk2196Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051057/nk2196Isup3.cml

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

C10H12O4	F(000) = 416
Mr = 196.20	Dx = 1.373 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2177 reflections
a = 19.1740 (12) Å	θ = 3.1–27.7°
b = 5.5026 (3) Å	µ = 0.11 mm−1
c = 8.9956 (5) Å	T = 173 K
V = 949.10 (9) Å3	Block, colourless
Z = 4	0.41 × 0.32 × 0.20 mm

Bruker APEXII CCD diffractometer	1106 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 28.0°, θmin = 2.1°
φ and ω scans	h = −25→24
4718 measured reflections	k = −7→7
1214 independent reflections	l = −11→10

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.0546P] where P = (Fo2 + 2Fc2)/3
1214 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.18 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
C1	0.34395 (9)	−0.0487 (3)	0.3973 (2)	0.0287 (4)
C2	0.30480 (9)	0.1288 (3)	0.4721 (2)	0.0322 (4)
C3	0.33683 (9)	0.2885 (3)	0.5713 (2)	0.0307 (4)
H3	0.3100	0.4093	0.6205	0.037*
C4	0.40755 (9)	0.2705 (3)	0.59765 (19)	0.0262 (4)
C5	0.44769 (8)	0.0884 (3)	0.5258 (2)	0.0248 (4)
C6	0.41609 (9)	−0.0644 (3)	0.4263 (2)	0.0271 (4)
H6	0.4432	−0.1829	0.3758	0.033*
C7	0.30942 (10)	−0.2140 (4)	0.2923 (2)	0.0346 (4)
C8	0.35122 (11)	−0.4047 (4)	0.2122 (3)	0.0395 (5)
H8A	0.3210	−0.4921	0.1425	0.059*
H8B	0.3706	−0.5194	0.2845	0.059*
H8C	0.3893	−0.3269	0.1573	0.059*
C9	0.40535 (10)	0.5915 (3)	0.7748 (3)	0.0357 (4)
H9A	0.3838	0.7080	0.7064	0.053*
H9B	0.4368	0.6778	0.8426	0.053*
H9C	0.3690	0.5091	0.8323	0.053*
C10	0.55610 (10)	−0.1202 (3)	0.5150 (3)	0.0364 (5)
H10A	0.5342	−0.2712	0.5491	0.055*
H10B	0.6036	−0.1097	0.5548	0.055*
H10C	0.5578	−0.1188	0.4061	0.055*
O1	0.23555 (7)	0.1547 (3)	0.4504 (2)	0.0469 (4)
O2	0.44429 (7)	0.4153 (2)	0.69134 (15)	0.0308 (3)
O3	0.51633 (6)	0.0824 (3)	0.56605 (17)	0.0321 (3)
O4	0.24611 (9)	−0.2002 (3)	0.2697 (2)	0.0501 (4)
H1	0.2231 (13)	0.032 (5)	0.385 (4)	0.061 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0269 (9)	0.0322 (9)	0.0270 (9)	−0.0045 (7)	−0.0010 (7)	0.0009 (8)
C2	0.0227 (8)	0.0382 (10)	0.0357 (10)	−0.0005 (8)	0.0018 (8)	0.0028 (9)
C3	0.0280 (8)	0.0334 (9)	0.0308 (10)	0.0027 (7)	0.0050 (8)	0.0000 (8)
C4	0.0297 (9)	0.0267 (8)	0.0222 (8)	−0.0035 (7)	0.0024 (7)	0.0010 (7)
C5	0.0214 (8)	0.0284 (8)	0.0247 (8)	−0.0017 (7)	0.0017 (7)	0.0017 (7)
C6	0.0278 (8)	0.0279 (8)	0.0257 (9)	−0.0015 (7)	0.0036 (7)	−0.0002 (7)
C7	0.0331 (10)	0.0384 (10)	0.0322 (10)	−0.0113 (8)	−0.0023 (8)	0.0015 (9)
C8	0.0439 (12)	0.0401 (11)	0.0345 (10)	−0.0141 (9)	0.0022 (9)	−0.0072 (9)
C9	0.0424 (11)	0.0304 (9)	0.0342 (9)	0.0044 (7)	0.0023 (9)	−0.0072 (8)
C10	0.0279 (8)	0.0346 (9)	0.0468 (12)	0.0064 (8)	−0.0022 (9)	−0.0067 (9)
O1	0.0229 (7)	0.0571 (9)	0.0608 (11)	0.0031 (7)	−0.0054 (7)	−0.0103 (9)
O2	0.0298 (7)	0.0323 (6)	0.0304 (7)	0.0003 (5)	−0.0003 (5)	−0.0072 (6)
O3	0.0235 (6)	0.0356 (6)	0.0371 (7)	0.0029 (5)	−0.0026 (5)	−0.0097 (6)
O4	0.0327 (7)	0.0585 (9)	0.0589 (10)	−0.0089 (7)	−0.0106 (8)	−0.0106 (9)

C1—C2	1.403 (3)	C7—C8	1.504 (3)
C1—C6	1.410 (2)	C8—H8A	0.9800
C1—C7	1.469 (3)	C8—H8B	0.9800
C2—O1	1.349 (2)	C8—H8C	0.9800
C2—C3	1.395 (3)	C9—O2	1.436 (2)
C3—C4	1.380 (2)	C9—H9A	0.9800
C3—H3	0.9500	C9—H9B	0.9800
C4—O2	1.357 (2)	C9—H9C	0.9800
C4—C5	1.419 (2)	C10—O3	1.426 (2)
C5—O3	1.365 (2)	C10—H10A	0.9800
C5—C6	1.370 (2)	C10—H10B	0.9800
C6—H6	0.9500	C10—H10C	0.9800
C7—O4	1.233 (2)	O1—H1	0.93 (3)
C2—C1—C6	118.60 (16)	C7—C8—H8A	109.5
C2—C1—C7	119.87 (16)	C7—C8—H8B	109.5
C6—C1—C7	121.53 (16)	H8A—C8—H8B	109.5
O1—C2—C3	117.31 (18)	C7—C8—H8C	109.5
O1—C2—C1	122.06 (18)	H8A—C8—H8C	109.5
C3—C2—C1	120.63 (15)	H8B—C8—H8C	109.5
C4—C3—C2	119.84 (16)	O2—C9—H9A	109.5
C4—C3—H3	120.1	O2—C9—H9B	109.5
C2—C3—H3	120.1	H9A—C9—H9B	109.5
O2—C4—C3	125.10 (16)	O2—C9—H9C	109.5
O2—C4—C5	114.56 (15)	H9A—C9—H9C	109.5
C3—C4—C5	120.33 (16)	H9B—C9—H9C	109.5
O3—C5—C6	125.79 (15)	O3—C10—H10A	109.5
O3—C5—C4	114.79 (15)	O3—C10—H10B	109.5
C6—C5—C4	119.42 (15)	H10A—C10—H10B	109.5
C5—C6—C1	121.15 (15)	O3—C10—H10C	109.5
C5—C6—H6	119.4	H10A—C10—H10C	109.5
C1—C6—H6	119.4	H10B—C10—H10C	109.5
O4—C7—C1	120.76 (19)	C2—O1—H1	105.6 (16)
O4—C7—C8	119.24 (18)	C4—O2—C9	116.82 (14)
C1—C7—C8	120.00 (17)	C5—O3—C10	116.68 (14)
C6—C1—C2—O1	−179.90 (19)	O3—C5—C6—C1	177.32 (16)
C7—C1—C2—O1	−0.3 (3)	C4—C5—C6—C1	−2.0 (2)
C6—C1—C2—C3	0.9 (3)	C2—C1—C6—C5	0.5 (2)
C7—C1—C2—C3	−179.47 (17)	C7—C1—C6—C5	−179.13 (17)
O1—C2—C3—C4	−179.95 (18)	C2—C1—C7—O4	−0.6 (3)
C1—C2—C3—C4	−0.7 (3)	C6—C1—C7—O4	178.99 (19)
C2—C3—C4—O2	179.97 (17)	C2—C1—C7—C8	−179.90 (17)
C2—C3—C4—C5	−0.8 (3)	C6—C1—C7—C8	−0.3 (3)
O2—C4—C5—O3	2.1 (2)	C3—C4—O2—C9	3.5 (3)
C3—C4—C5—O3	−177.21 (16)	C5—C4—O2—C9	−175.75 (15)
O2—C4—C5—C6	−178.53 (15)	C6—C5—O3—C10	−8.9 (3)
C3—C4—C5—C6	2.2 (2)	C4—C5—O3—C10	170.47 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.93 (3)	1.71 (3)	2.549 (2)	150 (2)
C8—H8C···O3i	0.98	2.40	3.365 (2)	168
C9—H9B···O3ii	0.98	2.57	3.513 (3)	162
C10—H10C···O2i	0.98	2.53	3.334 (3)	139
C8—H8B···Cg1iii	0.98	2.80	3.738 (3)	160
C9—H9A···Cg1iv	0.98	2.90	3.828 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.93 (3)	1.71 (3)	2.549 (2)	150 (2)
C8—H8C⋯O3i	0.98	2.40	3.365 (2)	168
C9—H9B⋯O3ii	0.98	2.57	3.513 (3)	162
C10—H10C⋯O2i	0.98	2.53	3.334 (3)	139
C8—H8B⋯Cg1iii	0.98	2.80	3.738 (3)	160
C9—H9A⋯Cg1iv	0.98	2.90	3.828 (3)	158

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