5-Hy­droxy-7-meth­oxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae)

Najmuldeen, I.A.; Abdul Hadi, A.H.; Awang, K.; Mohamad, K.; Ng, S.W.

doi:10.1107/S1600536810025146

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1883

https://doi.org/10.1107/S1600536810025146

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5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae)

Ibrahim A. Najmuldeen,^a Abdul Hamid Abdul Hadi,^a Khalijah Awang,^a Khalit Mohamad ^b and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 24 June 2010; accepted 26 June 2010; online 3 July 2010)

Both independent molecules in the asymmetric unit of the title compound, C₁₁H₁₀O₄, are almost planar (r.m.s. deviations = 0.011 and 0.033 Å). In both molecules, the hydroxy group is intramolecularly hydrogen bonded to the ketonic O atom. The independent molecules 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_r = 206.19
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.108
S = 1.02
4285 reflections
283 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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)

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025146/ci5120Isup2.hkl

checkCIF report

Comment top

Dysoxylum produces terpenes, terpenoids and other compounds, as noted in studies on Dysoxylum acutangulum, Dysoxylum beddomei, Dysoxylum binectariferum, Dysoxylum densiflorum, Dysoxylum malabaricum and Dysoxylum macranthum (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). A coumarin (Scheme I) is isolated from Dysoxylum macrocarpum in the present study. There are two independent molecules (Fig. 1). Both independent molecules are planar [r.m.s. deviations 0.011 and 0.033 Å); one is stacked over the other [dihedral angle between the planes 4.5 (1) °] but the distance between them exceeds 3.5 Å. The hydroxy group is intramolecularly hydrogen bonded to the ketonic oxygen atom.

Related literature top

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 top

Dried ground leaves of Dysoxylum macrocarpum (1.4 kg) were soaked in hexane for three days. The solvent was removed and the plant material was dried; the dried plant material was extracted with dichloromethane for another three days. The dichloromethane was removed by evaporation to give a crude material (30 g) that was subjected to column chromatography over silica gel. Separation was effected with hexane-dichloromethane (1:0 to 0:1v/v); the polarity was increased with methanol. One fraction was eluted with hexane-methanol (92:8 v/v) to give a compound that was further purified by silica gel column chromatography with hexane-ethyl acetate (70:30 v/v) to yield colourless crystals.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₁H₁₀O₄ at the 70% probability level. H atoms are drawn as spheres of arbitrary radii.

5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one top

Crystal data top

C₁₁H₁₀O₄	F(000) = 864
M_r = 206.19	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0679P)² + 0.4625P] where P = (F_o² + 2F_c²)/3
4285 reflections	(Δ/σ)_max = 0.001
283 parameters	Δρ_max = 0.34 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₁H₁₀O₄	V = 1870.57 (13) Å³
M_r = 206.19	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7393 (3) Å	µ = 0.11 mm⁻¹
b = 14.5373 (6) Å	T = 100 K
c = 16.8263 (7) Å	0.35 × 0.35 × 0.02 mm
β = 98.848 (1)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3795 reflections with I > 2σ(I)
17796 measured reflections	R_int = 0.017
4285 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.34 e Å⁻³
4285 reflections	Δρ_min = −0.28 e Å⁻³
283 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.95	2.47	3.3904 (12)	163
C20—H20···O6ⁱⁱⁱ	0.95	2.27	3.1995 (12)	166

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+2, y+1/2, −z+3/2; (iv) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀O₄
M_r	206.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.7393 (3), 14.5373 (6), 16.8263 (7)
β (°)	98.848 (1)
V (Å³)	1870.57 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.35 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17796, 4285, 3795
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.108, 1.02
No. of reflections	4285
No. of parameters	283
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

The authors thank the University of Malaya (PPP PS378/009B) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ismail, I. F., Nagakura, Y., Hirasawa, Y., Hosoya, T., Mohd Lazim, M. I., Hj Lajis, N. & Morita, H. (2009). Tetrahedron Lett. 50, 4830–4832. Web of Science CrossRef CAS Google Scholar
Lakshmi, V., Pandey, K., Kapil, A., Singh, N., Samant, M. & Dube, A. (2007). Phytomedicine, 14, 36–42. Web of Science CrossRef PubMed CAS Google Scholar
Mohamad, K., Martin, M. T., Litaudon, M. C., Gaspard, C., Sevenet, T. & Pais, M. (1999). Phytochemistry, 52, 1461–1468. Web of Science CrossRef CAS Google Scholar
Mohanakumara, P., Sreejayan, N., Priti, V., Ramesha, B. T., Ravikanth, G., Ganeshaiah, K. N., Vasudeva, R., Mohan, J., Santhoshkumar, T. R. & Shaanker, R. U. (2010). Fitoterapia, 81, 145–148. Web of Science CrossRef PubMed CAS Google Scholar
Senthil Nathan, S., Hisham, A. & Jayakumar, G. (2008). Fitoterapia, 79, 106–111. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, J.-B., Yang, S.-P. & Yue, J.-M. (2008). Phytochemistry, 69, 2993–2997. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-Hy­dr­oxy-7-meth­­oxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one from Dysoxylum macrocarpum (Meliaceae)