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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1883.
Published online 2010 July 3. doi:  10.1107/S1600536810025146
PMCID: PMC3007310

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

Abstract

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 [triangle]); Lakshmi et al. (2007 [triangle]); Mohamad et al. (1999 [triangle]); Mohanakumara et al. (2010 [triangle]); Senthil Nathan et al. (2008 [triangle]); Xie et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1883-scheme1.jpg

Experimental

Crystal data

  • C11H10O4
  • M r = 206.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1883-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H = 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(C). The hydroxy H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H = 0.84 (1) Å; their Uiso parameters were freely refined.

Figures

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.

Crystal data

C11H10O4F(000) = 864
Mr = 206.19Dx = 1.464 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9622 reflections
a = 7.7393 (3) Åθ = 2.5–28.3°
b = 14.5373 (6) ŵ = 0.11 mm1
c = 16.8263 (7) ÅT = 100 K
β = 98.848 (1)°Plate, colourless
V = 1870.57 (13) Å30.35 × 0.35 × 0.02 mm
Z = 8

Data collection

Bruker SMART APEXII area-detector diffractometer3795 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
graphiteθmax = 27.5°, θmin = 1.9°
ω scansh = −10→10
17796 measured reflectionsk = −18→18
4285 independent reflectionsl = −20→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0679P)2 + 0.4625P] where P = (Fo2 + 2Fc2)/3
4285 reflections(Δ/σ)max = 0.001
283 parametersΔρmax = 0.34 e Å3
2 restraintsΔρmin = −0.28 e Å3

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

xyzUiso*/Ueq
O10.49963 (9)0.31112 (5)0.80755 (4)0.01545 (16)
O20.54836 (10)0.03128 (5)0.81510 (5)0.02311 (18)
O30.66721 (11)0.03755 (5)0.67769 (5)0.02290 (18)
O40.71726 (10)0.32572 (5)0.55887 (4)0.01882 (17)
O51.05826 (9)0.38133 (5)0.70570 (4)0.01574 (16)
O61.12544 (10)0.10446 (5)0.73680 (5)0.02192 (17)
O71.00123 (11)0.11679 (5)0.87114 (5)0.02253 (18)
O80.82751 (10)0.40629 (5)0.95136 (4)0.01974 (17)
C10.39489 (14)0.32353 (7)0.93075 (6)0.0200 (2)
H1A0.35760.28640.97370.030*
H1B0.29640.36070.90490.030*
H1C0.49090.36410.95360.030*
C20.45527 (12)0.26180 (7)0.87004 (6)0.0163 (2)
C30.46768 (13)0.16950 (7)0.87405 (6)0.0184 (2)
H3A0.43290.13830.91860.022*
C40.53257 (12)0.11694 (7)0.81228 (6)0.0172 (2)
C50.58040 (12)0.17065 (6)0.74648 (6)0.0147 (2)
C60.64722 (12)0.12963 (7)0.68075 (6)0.0160 (2)
C70.69215 (12)0.18335 (7)0.61950 (6)0.0167 (2)
H7A0.73790.15590.57590.020*
C80.66943 (12)0.27902 (7)0.62233 (6)0.0148 (2)
C90.60437 (12)0.32217 (6)0.68517 (6)0.01419 (19)
H90.58950.38700.68640.017*
C100.56218 (12)0.26615 (6)0.74610 (5)0.01350 (19)
C110.69519 (14)0.42341 (7)0.55749 (6)0.0205 (2)
H11A0.72870.44830.50790.031*
H11B0.76930.45060.60410.031*
H11C0.57250.43830.55960.031*
C121.16596 (14)0.38672 (7)0.58240 (6)0.0200 (2)
H12A1.21530.34770.54400.030*
H12B1.25120.43400.60330.030*
H12C1.05900.41620.55530.030*
C131.12406 (12)0.32926 (7)0.65014 (6)0.0163 (2)
C141.14769 (13)0.23789 (7)0.65825 (6)0.0180 (2)
H141.19400.20470.61770.022*
C151.10416 (12)0.18917 (7)0.72722 (6)0.0164 (2)
C161.03515 (12)0.24579 (6)0.78581 (6)0.01414 (19)
C170.98490 (12)0.20810 (6)0.85677 (6)0.0159 (2)
C180.91807 (12)0.26380 (7)0.91094 (6)0.0167 (2)
H180.88580.23860.95860.020*
C190.89823 (12)0.35822 (7)0.89482 (6)0.0151 (2)
C200.94688 (12)0.39841 (6)0.82650 (6)0.01472 (19)
H200.93480.46260.81670.018*
C211.01372 (12)0.34029 (6)0.77342 (5)0.01377 (19)
C220.78973 (16)0.50156 (7)0.93552 (7)0.0250 (2)
H22A0.73440.52750.97910.038*
H22B0.71030.50770.88450.038*
H22C0.89860.53470.93210.038*
H30.634 (2)0.0179 (12)0.7204 (8)0.061 (6)*
H71.043 (3)0.0968 (13)0.8304 (9)0.070 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0181 (3)0.0157 (3)0.0134 (3)0.0013 (3)0.0054 (3)0.0001 (2)
O20.0254 (4)0.0153 (4)0.0293 (4)0.0011 (3)0.0063 (3)0.0063 (3)
O30.0307 (4)0.0125 (3)0.0266 (4)0.0021 (3)0.0078 (3)−0.0015 (3)
O40.0253 (4)0.0179 (4)0.0146 (3)0.0024 (3)0.0074 (3)0.0023 (3)
O50.0205 (3)0.0151 (3)0.0125 (3)−0.0002 (3)0.0055 (3)0.0011 (2)
O60.0276 (4)0.0138 (3)0.0246 (4)0.0010 (3)0.0045 (3)−0.0030 (3)
O70.0336 (4)0.0123 (3)0.0226 (4)0.0006 (3)0.0071 (3)0.0036 (3)
O80.0259 (4)0.0179 (4)0.0174 (4)0.0017 (3)0.0094 (3)−0.0009 (3)
C10.0191 (5)0.0263 (5)0.0152 (5)−0.0007 (4)0.0048 (4)−0.0019 (4)
C20.0131 (4)0.0229 (5)0.0129 (4)−0.0009 (4)0.0020 (3)0.0014 (4)
C30.0175 (5)0.0222 (5)0.0157 (5)−0.0006 (4)0.0033 (4)0.0049 (4)
C40.0141 (4)0.0171 (5)0.0198 (5)−0.0005 (3)0.0007 (3)0.0032 (4)
C50.0135 (4)0.0146 (4)0.0157 (5)0.0000 (3)0.0013 (3)0.0006 (3)
C60.0154 (4)0.0139 (4)0.0180 (5)0.0009 (3)0.0003 (3)−0.0022 (3)
C70.0176 (5)0.0173 (5)0.0151 (4)0.0018 (3)0.0024 (3)−0.0034 (3)
C80.0144 (4)0.0182 (5)0.0117 (4)−0.0005 (3)0.0014 (3)0.0012 (3)
C90.0152 (4)0.0126 (4)0.0146 (4)0.0004 (3)0.0016 (3)0.0008 (3)
C100.0127 (4)0.0152 (4)0.0127 (4)0.0008 (3)0.0020 (3)−0.0014 (3)
C110.0251 (5)0.0175 (5)0.0200 (5)0.0011 (4)0.0064 (4)0.0051 (4)
C120.0216 (5)0.0232 (5)0.0162 (5)−0.0034 (4)0.0059 (4)0.0006 (4)
C130.0143 (4)0.0209 (5)0.0136 (4)−0.0031 (3)0.0023 (3)−0.0024 (3)
C140.0178 (4)0.0206 (5)0.0164 (5)−0.0015 (4)0.0050 (4)−0.0049 (4)
C150.0144 (4)0.0157 (4)0.0186 (5)−0.0011 (3)0.0007 (3)−0.0030 (4)
C160.0140 (4)0.0137 (4)0.0143 (4)−0.0010 (3)0.0010 (3)−0.0002 (3)
C170.0165 (4)0.0137 (4)0.0170 (5)−0.0016 (3)0.0008 (3)0.0021 (3)
C180.0175 (5)0.0178 (5)0.0151 (4)−0.0023 (4)0.0029 (3)0.0032 (3)
C190.0142 (4)0.0175 (5)0.0139 (4)−0.0007 (3)0.0030 (3)−0.0022 (3)
C200.0164 (4)0.0126 (4)0.0152 (4)0.0000 (3)0.0025 (3)0.0004 (3)
C210.0135 (4)0.0156 (4)0.0120 (4)−0.0020 (3)0.0014 (3)0.0018 (3)
C220.0343 (6)0.0178 (5)0.0250 (5)0.0052 (4)0.0110 (4)−0.0019 (4)

Geometric parameters (Å, °)

O1—C21.3596 (11)C7—H7A0.95
O1—C101.3729 (11)C8—C91.3888 (13)
O2—C41.2514 (12)C9—C101.3870 (13)
O3—C61.3494 (11)C9—H90.95
O3—H30.850 (9)C11—H11A0.98
O4—C81.3637 (11)C11—H11B0.98
O4—C111.4302 (12)C11—H11C0.98
O5—C131.3611 (11)C12—C131.4886 (13)
O5—C211.3761 (11)C12—H12A0.98
O6—C151.2496 (12)C12—H12B0.98
O7—C171.3517 (11)C12—H12C0.98
O7—H70.852 (9)C13—C141.3450 (14)
O8—C191.3612 (11)C14—C151.4430 (14)
O8—C221.4319 (12)C14—H140.95
C1—C21.4880 (13)C15—C161.4480 (13)
C1—H1A0.98C16—C211.3956 (13)
C1—H1B0.98C16—C171.4212 (13)
C1—H1C0.98C17—C181.3780 (14)
C2—C31.3463 (14)C18—C191.4030 (13)
C3—C41.4412 (14)C18—H180.95
C3—H3A0.95C19—C201.3920 (13)
C4—C51.4486 (13)C20—C211.3862 (13)
C5—C101.3955 (13)C20—H200.95
C5—C61.4220 (13)C22—H22A0.98
C6—C71.3795 (14)C22—H22B0.98
C7—C81.4035 (13)C22—H22C0.98
C2—O1—C10119.45 (8)O4—C11—H11C109.5
C6—O3—H3104.5 (13)H11A—C11—H11C109.5
C8—O4—C11117.45 (7)H11B—C11—H11C109.5
C13—O5—C21119.70 (8)C13—C12—H12A109.5
C17—O7—H7103.2 (14)C13—C12—H12B109.5
C19—O8—C22117.32 (8)H12A—C12—H12B109.5
C2—C1—H1A109.5C13—C12—H12C109.5
C2—C1—H1B109.5H12A—C12—H12C109.5
H1A—C1—H1B109.5H12B—C12—H12C109.5
C2—C1—H1C109.5C14—C13—O5122.61 (9)
H1A—C1—H1C109.5C14—C13—C12126.13 (9)
H1B—C1—H1C109.5O5—C13—C12111.25 (8)
C3—C2—O1122.67 (9)C13—C14—C15121.42 (9)
C3—C2—C1126.45 (9)C13—C14—H14119.3
O1—C2—C1110.87 (8)C15—C14—H14119.3
C2—C3—C4121.49 (9)O6—C15—C14123.03 (9)
C2—C3—H3A119.3O6—C15—C16121.83 (9)
C4—C3—H3A119.3C14—C15—C16115.14 (9)
O2—C4—C3122.89 (9)C21—C16—C17117.60 (8)
O2—C4—C5122.03 (9)C21—C16—C15120.37 (9)
C3—C4—C5115.08 (9)C17—C16—C15122.02 (9)
C10—C5—C6117.53 (8)O7—C17—C18119.54 (9)
C10—C5—C4120.14 (9)O7—C17—C16119.91 (9)
C6—C5—C4122.32 (9)C18—C17—C16120.55 (9)
O3—C6—C7119.31 (9)C17—C18—C19119.21 (9)
O3—C6—C5120.21 (9)C17—C18—H18120.4
C7—C6—C5120.48 (9)C19—C18—H18120.4
C6—C7—C8119.23 (9)O8—C19—C20123.40 (9)
C6—C7—H7A120.4O8—C19—C18114.27 (8)
C8—C7—H7A120.4C20—C19—C18122.33 (9)
O4—C8—C9123.04 (8)C21—C20—C19116.84 (8)
O4—C8—C7114.59 (8)C21—C20—H20121.6
C9—C8—C7122.37 (9)C19—C20—H20121.6
C10—C9—C8116.85 (8)O5—C21—C20115.79 (8)
C10—C9—H9121.6O5—C21—C16120.75 (8)
C8—C9—H9121.6C20—C21—C16123.46 (8)
O1—C10—C9115.31 (8)O8—C22—H22A109.5
O1—C10—C5121.16 (8)O8—C22—H22B109.5
C9—C10—C5123.53 (8)H22A—C22—H22B109.5
O4—C11—H11A109.5O8—C22—H22C109.5
O4—C11—H11B109.5H22A—C22—H22C109.5
H11A—C11—H11B109.5H22B—C22—H22C109.5
C10—O1—C2—C3−0.95 (13)C21—O5—C13—C140.18 (14)
C10—O1—C2—C1178.64 (7)C21—O5—C13—C12−179.19 (7)
O1—C2—C3—C41.16 (15)O5—C13—C14—C15−0.03 (15)
C1—C2—C3—C4−178.35 (9)C12—C13—C14—C15179.24 (9)
C2—C3—C4—O2178.74 (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—C21179.72 (9)
C3—C4—C5—C100.00 (13)C14—C15—C16—C210.38 (13)
O2—C4—C5—C60.38 (15)O6—C15—C16—C17−1.11 (15)
C3—C4—C5—C6179.78 (8)C14—C15—C16—C17179.55 (8)
C10—C5—C6—O3−179.79 (8)C21—C16—C17—O7179.27 (8)
C4—C5—C6—O30.42 (14)C15—C16—C17—O70.08 (14)
C10—C5—C6—C70.16 (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—C8179.29 (9)O7—C17—C18—C19−178.73 (9)
C5—C6—C7—C8−0.66 (14)C16—C17—C18—C190.72 (14)
C11—O4—C8—C9−1.20 (13)C22—O8—C19—C205.00 (14)
C11—O4—C8—C7179.17 (8)C22—O8—C19—C18−174.86 (9)
C6—C7—C8—O4−179.82 (8)C17—C18—C19—O8178.59 (8)
C6—C7—C8—C90.55 (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—C100.08 (14)C18—C19—C20—C211.19 (14)
C2—O1—C10—C9−179.84 (8)C13—O5—C21—C20−179.66 (8)
C2—O1—C10—C50.26 (13)C13—O5—C21—C16−0.03 (13)
C8—C9—C10—O1179.48 (7)C19—C20—C21—O5178.99 (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—O10.19 (14)C15—C16—C21—O5−0.26 (14)
C6—C5—C10—C90.50 (14)C17—C16—C21—C200.13 (14)
C4—C5—C10—C9−179.71 (9)C15—C16—C21—C20179.34 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O20.85 (1)1.83 (1)2.618 (1)154 (2)
O7—H7···O60.85 (1)1.79 (1)2.595 (1)156 (2)
C7—H7A···O8i0.952.483.4222 (12)173
C9—H9···O2ii0.952.353.2614 (12)160
C12—H12B···O2iii0.982.373.3326 (13)166
C18—H18···O4iv0.952.473.3904 (12)163
C20—H20···O6iii0.952.273.1995 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5120).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
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