5-Hy-droxy-7-meth-oxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae).

Both independent mol-ecules in the asymmetric unit of the title compound, C(11)H(10)O(4), are almost planar (r.m.s. deviations = 0.011 and 0.033 Å). In both mol-ecules, the hy-droxy group is intra-molecularly hydrogen bonded to the ketonic O atom. The independent mol-ecules are stacked alternately along the a axis, with the centroids of their chromene ring separated by distances of 4.490 (1) and 3.621 (1) Å.

Related literature

For studies on other Dysoxylum species, see: Ismail et al. (2009 ▶); Lakshmi et al. (2007 ▶); Mohamad et al. (1999 ▶); Mohanakumara et al. (2010 ▶); Senthil Nathan et al. (2008 ▶); Xie et al. (2008 ▶).

Experimental

Crystal data

C11H10O4

M = 206.19

Monoclinic,

a = 7.7393 (3) Å

b = 14.5373 (6) Å

c = 16.8263 (7) Å

β = 98.848 (1)°

V = 1870.57 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.35 × 0.02 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

17796 measured reflections

4285 independent reflections

3795 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.108

S = 1.02

4285 reflections

283 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025146/ci5120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025146/ci5120Isup2.hkl

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

C11H10O4	F(000) = 864
Mr = 206.19	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9622 reflections
a = 7.7393 (3) Å	θ = 2.5–28.3°
b = 14.5373 (6) Å	µ = 0.11 mm−1
c = 16.8263 (7) Å	T = 100 K
β = 98.848 (1)°	Plate, colourless
V = 1870.57 (13) Å3	0.35 × 0.35 × 0.02 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	3795 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 27.5°, θmin = 1.9°
ω scans	h = −10→10
17796 measured reflections	k = −18→18
4285 independent reflections	l = −20→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.4625P] where P = (Fo2 + 2Fc2)/3
4285 reflections	(Δ/σ)max = 0.001
283 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.49963 (9)	0.31112 (5)	0.80755 (4)	0.01545 (16)
O2	0.54836 (10)	0.03128 (5)	0.81510 (5)	0.02311 (18)
O3	0.66721 (11)	0.03755 (5)	0.67769 (5)	0.02290 (18)
O4	0.71726 (10)	0.32572 (5)	0.55887 (4)	0.01882 (17)
O5	1.05826 (9)	0.38133 (5)	0.70570 (4)	0.01574 (16)
O6	1.12544 (10)	0.10446 (5)	0.73680 (5)	0.02192 (17)
O7	1.00123 (11)	0.11679 (5)	0.87114 (5)	0.02253 (18)
O8	0.82751 (10)	0.40629 (5)	0.95136 (4)	0.01974 (17)
C1	0.39489 (14)	0.32353 (7)	0.93075 (6)	0.0200 (2)
H1A	0.3576	0.2864	0.9737	0.030*
H1B	0.2964	0.3607	0.9049	0.030*
H1C	0.4909	0.3641	0.9536	0.030*
C2	0.45527 (12)	0.26180 (7)	0.87004 (6)	0.0163 (2)
C3	0.46768 (13)	0.16950 (7)	0.87405 (6)	0.0184 (2)
H3A	0.4329	0.1383	0.9186	0.022*
C4	0.53257 (12)	0.11694 (7)	0.81228 (6)	0.0172 (2)
C5	0.58040 (12)	0.17065 (6)	0.74648 (6)	0.0147 (2)
C6	0.64722 (12)	0.12963 (7)	0.68075 (6)	0.0160 (2)
C7	0.69215 (12)	0.18335 (7)	0.61950 (6)	0.0167 (2)
H7A	0.7379	0.1559	0.5759	0.020*
C8	0.66943 (12)	0.27902 (7)	0.62233 (6)	0.0148 (2)
C9	0.60437 (12)	0.32217 (6)	0.68517 (6)	0.01419 (19)
H9	0.5895	0.3870	0.6864	0.017*
C10	0.56218 (12)	0.26615 (6)	0.74610 (5)	0.01350 (19)
C11	0.69519 (14)	0.42341 (7)	0.55749 (6)	0.0205 (2)
H11A	0.7287	0.4483	0.5079	0.031*
H11B	0.7693	0.4506	0.6041	0.031*
H11C	0.5725	0.4383	0.5596	0.031*
C12	1.16596 (14)	0.38672 (7)	0.58240 (6)	0.0200 (2)
H12A	1.2153	0.3477	0.5440	0.030*
H12B	1.2512	0.4340	0.6033	0.030*
H12C	1.0590	0.4162	0.5553	0.030*
C13	1.12406 (12)	0.32926 (7)	0.65014 (6)	0.0163 (2)
C14	1.14769 (13)	0.23789 (7)	0.65825 (6)	0.0180 (2)
H14	1.1940	0.2047	0.6177	0.022*
C15	1.10416 (12)	0.18917 (7)	0.72722 (6)	0.0164 (2)
C16	1.03515 (12)	0.24579 (6)	0.78581 (6)	0.01414 (19)
C17	0.98490 (12)	0.20810 (6)	0.85677 (6)	0.0159 (2)
C18	0.91807 (12)	0.26380 (7)	0.91094 (6)	0.0167 (2)
H18	0.8858	0.2386	0.9586	0.020*
C19	0.89823 (12)	0.35822 (7)	0.89482 (6)	0.0151 (2)
C20	0.94688 (12)	0.39841 (6)	0.82650 (6)	0.01472 (19)
H20	0.9348	0.4626	0.8167	0.018*
C21	1.01372 (12)	0.34029 (6)	0.77342 (5)	0.01377 (19)
C22	0.78973 (16)	0.50156 (7)	0.93552 (7)	0.0250 (2)
H22A	0.7344	0.5275	0.9791	0.038*
H22B	0.7103	0.5077	0.8845	0.038*
H22C	0.8986	0.5347	0.9321	0.038*
H3	0.634 (2)	0.0179 (12)	0.7204 (8)	0.061 (6)*
H7	1.043 (3)	0.0968 (13)	0.8304 (9)	0.070 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0181 (3)	0.0157 (3)	0.0134 (3)	0.0013 (3)	0.0054 (3)	0.0001 (2)
O2	0.0254 (4)	0.0153 (4)	0.0293 (4)	0.0011 (3)	0.0063 (3)	0.0063 (3)
O3	0.0307 (4)	0.0125 (3)	0.0266 (4)	0.0021 (3)	0.0078 (3)	−0.0015 (3)
O4	0.0253 (4)	0.0179 (4)	0.0146 (3)	0.0024 (3)	0.0074 (3)	0.0023 (3)
O5	0.0205 (3)	0.0151 (3)	0.0125 (3)	−0.0002 (3)	0.0055 (3)	0.0011 (2)
O6	0.0276 (4)	0.0138 (3)	0.0246 (4)	0.0010 (3)	0.0045 (3)	−0.0030 (3)
O7	0.0336 (4)	0.0123 (3)	0.0226 (4)	0.0006 (3)	0.0071 (3)	0.0036 (3)
O8	0.0259 (4)	0.0179 (4)	0.0174 (4)	0.0017 (3)	0.0094 (3)	−0.0009 (3)
C1	0.0191 (5)	0.0263 (5)	0.0152 (5)	−0.0007 (4)	0.0048 (4)	−0.0019 (4)
C2	0.0131 (4)	0.0229 (5)	0.0129 (4)	−0.0009 (4)	0.0020 (3)	0.0014 (4)
C3	0.0175 (5)	0.0222 (5)	0.0157 (5)	−0.0006 (4)	0.0033 (4)	0.0049 (4)
C4	0.0141 (4)	0.0171 (5)	0.0198 (5)	−0.0005 (3)	0.0007 (3)	0.0032 (4)
C5	0.0135 (4)	0.0146 (4)	0.0157 (5)	0.0000 (3)	0.0013 (3)	0.0006 (3)
C6	0.0154 (4)	0.0139 (4)	0.0180 (5)	0.0009 (3)	0.0003 (3)	−0.0022 (3)
C7	0.0176 (5)	0.0173 (5)	0.0151 (4)	0.0018 (3)	0.0024 (3)	−0.0034 (3)
C8	0.0144 (4)	0.0182 (5)	0.0117 (4)	−0.0005 (3)	0.0014 (3)	0.0012 (3)
C9	0.0152 (4)	0.0126 (4)	0.0146 (4)	0.0004 (3)	0.0016 (3)	0.0008 (3)
C10	0.0127 (4)	0.0152 (4)	0.0127 (4)	0.0008 (3)	0.0020 (3)	−0.0014 (3)
C11	0.0251 (5)	0.0175 (5)	0.0200 (5)	0.0011 (4)	0.0064 (4)	0.0051 (4)
C12	0.0216 (5)	0.0232 (5)	0.0162 (5)	−0.0034 (4)	0.0059 (4)	0.0006 (4)
C13	0.0143 (4)	0.0209 (5)	0.0136 (4)	−0.0031 (3)	0.0023 (3)	−0.0024 (3)
C14	0.0178 (4)	0.0206 (5)	0.0164 (5)	−0.0015 (4)	0.0050 (4)	−0.0049 (4)
C15	0.0144 (4)	0.0157 (4)	0.0186 (5)	−0.0011 (3)	0.0007 (3)	−0.0030 (4)
C16	0.0140 (4)	0.0137 (4)	0.0143 (4)	−0.0010 (3)	0.0010 (3)	−0.0002 (3)
C17	0.0165 (4)	0.0137 (4)	0.0170 (5)	−0.0016 (3)	0.0008 (3)	0.0021 (3)
C18	0.0175 (5)	0.0178 (5)	0.0151 (4)	−0.0023 (4)	0.0029 (3)	0.0032 (3)
C19	0.0142 (4)	0.0175 (5)	0.0139 (4)	−0.0007 (3)	0.0030 (3)	−0.0022 (3)
C20	0.0164 (4)	0.0126 (4)	0.0152 (4)	0.0000 (3)	0.0025 (3)	0.0004 (3)
C21	0.0135 (4)	0.0156 (4)	0.0120 (4)	−0.0020 (3)	0.0014 (3)	0.0018 (3)
C22	0.0343 (6)	0.0178 (5)	0.0250 (5)	0.0052 (4)	0.0110 (4)	−0.0019 (4)

O1—C2	1.3596 (11)	C7—H7A	0.95
O1—C10	1.3729 (11)	C8—C9	1.3888 (13)
O2—C4	1.2514 (12)	C9—C10	1.3870 (13)
O3—C6	1.3494 (11)	C9—H9	0.95
O3—H3	0.850 (9)	C11—H11A	0.98
O4—C8	1.3637 (11)	C11—H11B	0.98
O4—C11	1.4302 (12)	C11—H11C	0.98
O5—C13	1.3611 (11)	C12—C13	1.4886 (13)
O5—C21	1.3761 (11)	C12—H12A	0.98
O6—C15	1.2496 (12)	C12—H12B	0.98
O7—C17	1.3517 (11)	C12—H12C	0.98
O7—H7	0.852 (9)	C13—C14	1.3450 (14)
O8—C19	1.3612 (11)	C14—C15	1.4430 (14)
O8—C22	1.4319 (12)	C14—H14	0.95
C1—C2	1.4880 (13)	C15—C16	1.4480 (13)
C1—H1A	0.98	C16—C21	1.3956 (13)
C1—H1B	0.98	C16—C17	1.4212 (13)
C1—H1C	0.98	C17—C18	1.3780 (14)
C2—C3	1.3463 (14)	C18—C19	1.4030 (13)
C3—C4	1.4412 (14)	C18—H18	0.95
C3—H3A	0.95	C19—C20	1.3920 (13)
C4—C5	1.4486 (13)	C20—C21	1.3862 (13)
C5—C10	1.3955 (13)	C20—H20	0.95
C5—C6	1.4220 (13)	C22—H22A	0.98
C6—C7	1.3795 (14)	C22—H22B	0.98
C7—C8	1.4035 (13)	C22—H22C	0.98
C2—O1—C10	119.45 (8)	O4—C11—H11C	109.5
C6—O3—H3	104.5 (13)	H11A—C11—H11C	109.5
C8—O4—C11	117.45 (7)	H11B—C11—H11C	109.5
C13—O5—C21	119.70 (8)	C13—C12—H12A	109.5
C17—O7—H7	103.2 (14)	C13—C12—H12B	109.5
C19—O8—C22	117.32 (8)	H12A—C12—H12B	109.5
C2—C1—H1A	109.5	C13—C12—H12C	109.5
C2—C1—H1B	109.5	H12A—C12—H12C	109.5
H1A—C1—H1B	109.5	H12B—C12—H12C	109.5
C2—C1—H1C	109.5	C14—C13—O5	122.61 (9)
H1A—C1—H1C	109.5	C14—C13—C12	126.13 (9)
H1B—C1—H1C	109.5	O5—C13—C12	111.25 (8)
C3—C2—O1	122.67 (9)	C13—C14—C15	121.42 (9)
C3—C2—C1	126.45 (9)	C13—C14—H14	119.3
O1—C2—C1	110.87 (8)	C15—C14—H14	119.3
C2—C3—C4	121.49 (9)	O6—C15—C14	123.03 (9)
C2—C3—H3A	119.3	O6—C15—C16	121.83 (9)
C4—C3—H3A	119.3	C14—C15—C16	115.14 (9)
O2—C4—C3	122.89 (9)	C21—C16—C17	117.60 (8)
O2—C4—C5	122.03 (9)	C21—C16—C15	120.37 (9)
C3—C4—C5	115.08 (9)	C17—C16—C15	122.02 (9)
C10—C5—C6	117.53 (8)	O7—C17—C18	119.54 (9)
C10—C5—C4	120.14 (9)	O7—C17—C16	119.91 (9)
C6—C5—C4	122.32 (9)	C18—C17—C16	120.55 (9)
O3—C6—C7	119.31 (9)	C17—C18—C19	119.21 (9)
O3—C6—C5	120.21 (9)	C17—C18—H18	120.4
C7—C6—C5	120.48 (9)	C19—C18—H18	120.4
C6—C7—C8	119.23 (9)	O8—C19—C20	123.40 (9)
C6—C7—H7A	120.4	O8—C19—C18	114.27 (8)
C8—C7—H7A	120.4	C20—C19—C18	122.33 (9)
O4—C8—C9	123.04 (8)	C21—C20—C19	116.84 (8)
O4—C8—C7	114.59 (8)	C21—C20—H20	121.6
C9—C8—C7	122.37 (9)	C19—C20—H20	121.6
C10—C9—C8	116.85 (8)	O5—C21—C20	115.79 (8)
C10—C9—H9	121.6	O5—C21—C16	120.75 (8)
C8—C9—H9	121.6	C20—C21—C16	123.46 (8)
O1—C10—C9	115.31 (8)	O8—C22—H22A	109.5
O1—C10—C5	121.16 (8)	O8—C22—H22B	109.5
C9—C10—C5	123.53 (8)	H22A—C22—H22B	109.5
O4—C11—H11A	109.5	O8—C22—H22C	109.5
O4—C11—H11B	109.5	H22A—C22—H22C	109.5
H11A—C11—H11B	109.5	H22B—C22—H22C	109.5
C10—O1—C2—C3	−0.95 (13)	C21—O5—C13—C14	0.18 (14)
C10—O1—C2—C1	178.64 (7)	C21—O5—C13—C12	−179.19 (7)
O1—C2—C3—C4	1.16 (15)	O5—C13—C14—C15	−0.03 (15)
C1—C2—C3—C4	−178.35 (9)	C12—C13—C14—C15	179.24 (9)
C2—C3—C4—O2	178.74 (10)	C13—C14—C15—O6	−179.58 (9)
C2—C3—C4—C5	−0.66 (14)	C13—C14—C15—C16	−0.25 (14)
O2—C4—C5—C10	−179.40 (9)	O6—C15—C16—C21	179.72 (9)
C3—C4—C5—C10	0.00 (13)	C14—C15—C16—C21	0.38 (13)
O2—C4—C5—C6	0.38 (15)	O6—C15—C16—C17	−1.11 (15)
C3—C4—C5—C6	179.78 (8)	C14—C15—C16—C17	179.55 (8)
C10—C5—C6—O3	−179.79 (8)	C21—C16—C17—O7	179.27 (8)
C4—C5—C6—O3	0.42 (14)	C15—C16—C17—O7	0.08 (14)
C10—C5—C6—C7	0.16 (14)	C21—C16—C17—C18	−0.18 (14)
C4—C5—C6—C7	−179.63 (8)	C15—C16—C17—C18	−179.37 (8)
O3—C6—C7—C8	179.29 (9)	O7—C17—C18—C19	−178.73 (9)
C5—C6—C7—C8	−0.66 (14)	C16—C17—C18—C19	0.72 (14)
C11—O4—C8—C9	−1.20 (13)	C22—O8—C19—C20	5.00 (14)
C11—O4—C8—C7	179.17 (8)	C22—O8—C19—C18	−174.86 (9)
C6—C7—C8—O4	−179.82 (8)	C17—C18—C19—O8	178.59 (8)
C6—C7—C8—C9	0.55 (14)	C17—C18—C19—C20	−1.27 (14)
O4—C8—C9—C10	−179.53 (8)	O8—C19—C20—C21	−178.65 (8)
C7—C8—C9—C10	0.08 (14)	C18—C19—C20—C21	1.19 (14)
C2—O1—C10—C9	−179.84 (8)	C13—O5—C21—C20	−179.66 (8)
C2—O1—C10—C5	0.26 (13)	C13—O5—C21—C16	−0.03 (13)
C8—C9—C10—O1	179.48 (7)	C19—C20—C21—O5	178.99 (8)
C8—C9—C10—C5	−0.61 (14)	C19—C20—C21—C16	−0.62 (14)
C6—C5—C10—O1	−179.60 (8)	C17—C16—C21—O5	−179.46 (8)
C4—C5—C10—O1	0.19 (14)	C15—C16—C21—O5	−0.26 (14)
C6—C5—C10—C9	0.50 (14)	C17—C16—C21—C20	0.13 (14)
C4—C5—C10—C9	−179.71 (9)	C15—C16—C21—C20	179.34 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.85 (1)	1.83 (1)	2.618 (1)	154 (2)
O7—H7···O6	0.85 (1)	1.79 (1)	2.595 (1)	156 (2)
C7—H7A···O8i	0.95	2.48	3.4222 (12)	173
C9—H9···O2ii	0.95	2.35	3.2614 (12)	160
C12—H12B···O2iii	0.98	2.37	3.3326 (13)	166
C18—H18···O4iv	0.95	2.47	3.3904 (12)	163
C20—H20···O6iii	0.95	2.27	3.1995 (12)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.85 (1)	1.83 (1)	2.618 (1)	154 (2)
O7—H7⋯O6	0.85 (1)	1.79 (1)	2.595 (1)	156 (2)