1-(2-Hydr-oxy-4,5-dimeth-oxyphen-yl)propan-1-one.

In the title compound, C(11)H(14)O(4), isolated from the stems of Trigonostemon xyphophylloides, an intra-molecular O-H⋯O hydrogen bond helps to establish an essentially planar conformation for the mol-ecule (r.m.s. deviation = 0.044 Å).

Related literature

For botanical and biochemical background, see: Tempeam et al. (2005 ▶); Chen et al. (2009 ▶). For medicinal applications of this family of compounds, see: Chuakul et al. (1997 ▶); Tempeam et al. (2002 ▶).

Experimental

Crystal data

C11H14O4

M = 210.22

Monoclinic,

a = 7.1933 (7) Å

b = 9.4874 (12) Å

c = 17.198 (2) Å

β = 113.164 (5)°

V = 1079.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.31 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.066, T max = 0.185

7549 measured reflections

2673 independent reflections

1749 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.094

wR(F 2) = 0.295

S = 1.12

2673 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536809041798/hb5121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041798/hb5121Isup2.hkl

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

C11H14O4	F(000) = 448
Mr = 210.22	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1933 (7) Å	Cell parameters from 2673 reflections
b = 9.4874 (12) Å	θ = 2.5–28.4°
c = 17.198 (2) Å	µ = 0.10 mm−1
β = 113.164 (5)°	T = 293 K
V = 1079.1 (2) Å3	Block, colourless
Z = 4	0.31 × 0.16 × 0.14 mm

Bruker SMART CCD diffractometer	2673 independent reflections
Radiation source: fine-focus sealed tube	1749 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.066, Tmax = 0.185	k = −12→12
7549 measured reflections	l = −22→13

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)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.295	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.1225P)2 + 1.1131P] where P = (Fo2 + 2Fc2)/3
2673 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.41 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	0.3767 (5)	0.3553 (3)	0.52714 (19)	0.0723 (9)
H1	0.3323	0.3757	0.4768	0.080*
O2	0.1907 (5)	0.3117 (3)	0.36706 (18)	0.0763 (9)
O3	0.2687 (4)	−0.2066 (3)	0.58386 (15)	0.0600 (8)
O4	0.4475 (4)	−0.0386 (3)	0.71051 (14)	0.0581 (7)
C1	0.3465 (5)	0.2161 (4)	0.5358 (2)	0.0497 (8)
C2	0.2485 (5)	0.1275 (3)	0.4653 (2)	0.0435 (7)
C3	0.2245 (5)	−0.0169 (4)	0.48170 (19)	0.0437 (7)
H3	0.1624	−0.0776	0.4364	0.080*
C4	0.2907 (5)	−0.0694 (3)	0.5629 (2)	0.0432 (7)
C5	0.3876 (5)	0.0225 (4)	0.63263 (19)	0.0441 (7)
C6	0.4134 (5)	0.1631 (4)	0.6178 (2)	0.0499 (8)
H6	0.4764	0.2232	0.6633	0.080*
C7	0.1702 (5)	0.1852 (4)	0.3788 (2)	0.0509 (8)
C8	0.0636 (6)	0.0885 (4)	0.3045 (2)	0.0569 (9)
H8A	−0.0529	0.0476	0.3111	0.080*
H8B	0.1545	0.0120	0.3061	0.080*
C9	−0.0065 (8)	0.1589 (5)	0.2186 (3)	0.0801 (14)
H9A	−0.0699	0.0902	0.1752	0.080*
H9B	0.1077	0.1990	0.2110	0.080*
H9C	−0.1017	0.2319	0.2152	0.080*
C10	0.1800 (6)	−0.3028 (4)	0.5156 (2)	0.0600 (10)
H10A	0.1714	−0.3945	0.5376	0.080*
H10B	0.2621	−0.3079	0.4831	0.080*
H10C	0.0469	−0.2709	0.4801	0.080*
C11	0.5335 (7)	0.0537 (5)	0.7830 (2)	0.0699 (12)
H11A	0.5684	−0.0003	0.8340	0.080*
H11B	0.4364	0.1246	0.7809	0.080*
H11C	0.6527	0.0980	0.7821	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.107 (2)	0.0456 (15)	0.0605 (17)	−0.0084 (14)	0.0294 (16)	−0.0016 (13)
O2	0.115 (3)	0.0534 (17)	0.0561 (16)	−0.0070 (16)	0.0287 (17)	0.0092 (13)
O3	0.0858 (18)	0.0402 (13)	0.0372 (12)	−0.0007 (12)	0.0062 (12)	0.0020 (10)
O4	0.0790 (17)	0.0490 (14)	0.0347 (12)	−0.0005 (12)	0.0098 (11)	−0.0045 (10)
C1	0.0556 (19)	0.0434 (18)	0.0509 (18)	0.0009 (15)	0.0219 (15)	−0.0022 (14)
C2	0.0482 (17)	0.0395 (16)	0.0422 (16)	0.0051 (13)	0.0170 (13)	−0.0005 (13)
C3	0.0472 (17)	0.0426 (17)	0.0377 (15)	0.0044 (13)	0.0129 (13)	−0.0046 (13)
C4	0.0444 (16)	0.0399 (16)	0.0413 (16)	0.0072 (13)	0.0125 (13)	−0.0007 (13)
C5	0.0459 (16)	0.0452 (17)	0.0371 (15)	0.0061 (14)	0.0120 (12)	−0.0036 (13)
C6	0.0551 (19)	0.0473 (19)	0.0437 (17)	0.0005 (15)	0.0155 (15)	−0.0091 (14)
C7	0.058 (2)	0.048 (2)	0.0461 (18)	0.0053 (15)	0.0200 (15)	0.0048 (15)
C8	0.069 (2)	0.057 (2)	0.0405 (17)	0.0013 (17)	0.0162 (16)	0.0066 (15)
C9	0.107 (4)	0.073 (3)	0.045 (2)	0.001 (3)	0.013 (2)	0.012 (2)
C10	0.078 (3)	0.0443 (19)	0.0439 (18)	0.0030 (17)	0.0091 (17)	−0.0015 (15)
C11	0.098 (3)	0.065 (3)	0.0358 (17)	−0.002 (2)	0.0149 (19)	−0.0100 (17)

O1—C1	1.355 (4)	C6—H6	0.9300
O1—H1	0.8200	C7—C8	1.513 (5)
O2—C7	1.235 (4)	C8—C9	1.516 (5)
O3—C4	1.376 (4)	C8—H8A	0.9700
O3—C10	1.424 (4)	C8—H8B	0.9700
O4—C5	1.364 (4)	C9—H9A	0.9600
O4—C11	1.448 (4)	C9—H9B	0.9600
C1—C6	1.393 (5)	C9—H9C	0.9600
C1—C2	1.415 (5)	C10—H10A	0.9600
C2—C3	1.423 (5)	C10—H10B	0.9600
C2—C7	1.473 (5)	C10—H10C	0.9600
C3—C4	1.379 (4)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.423 (4)	C11—H11C	0.9600
C5—C6	1.385 (5)
C1—O1—H1	109.5	C7—C8—C9	114.8 (3)
C4—O3—C10	116.8 (3)	C7—C8—H8A	108.6
C5—O4—C11	116.8 (3)	C9—C8—H8A	108.6
O1—C1—C6	117.2 (3)	C7—C8—H8B	108.6
O1—C1—C2	122.2 (3)	C9—C8—H8B	108.6
C6—C1—C2	120.7 (3)	H8A—C8—H8B	107.5
C1—C2—C3	117.4 (3)	C8—C9—H9A	109.5
C1—C2—C7	120.5 (3)	C8—C9—H9B	109.5
C3—C2—C7	122.0 (3)	H9A—C9—H9B	109.5
C4—C3—C2	121.9 (3)	C8—C9—H9C	109.5
C4—C3—H3	119.1	H9A—C9—H9C	109.5
C2—C3—H3	119.1	H9B—C9—H9C	109.5
O3—C4—C3	125.3 (3)	O3—C10—H10A	109.5
O3—C4—C5	115.3 (3)	O3—C10—H10B	109.5
C3—C4—C5	119.4 (3)	H10A—C10—H10B	109.5
O4—C5—C6	125.2 (3)	O3—C10—H10C	109.5
O4—C5—C4	115.3 (3)	H10A—C10—H10C	109.5
C6—C5—C4	119.4 (3)	H10B—C10—H10C	109.5
C5—C6—C1	121.1 (3)	O4—C11—H11A	109.5
C5—C6—H6	119.4	O4—C11—H11B	109.5
C1—C6—H6	119.4	H11A—C11—H11B	109.5
O2—C7—C2	120.2 (3)	O4—C11—H11C	109.5
O2—C7—C8	120.3 (3)	H11A—C11—H11C	109.5
C2—C7—C8	119.5 (3)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.86	2.577 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.86	2.577 (4)	146