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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o899.
Published online 2008 April 23. doi:  10.1107/S1600536808010696
PMCID: PMC2961207

8-Hydr­oxy-5,6,7-trimeth­oxy-2-phenyl-4H-chromen-4-one

Abstract

In the title compound, C18H16O6, the benzopyran group is essentially planar, with the O atoms of the substituent groups lying close to its mean plane. The mol­ecular conformation is governed by intra­molecular inter­actions. The crystal packing is mainly determined by one classical inter­molecular hydrogen bond which gives rise to the formation of an infinite chain along the a axis.

Related literature

For related literature, see: Chebib & Johnston (2000 [triangle]); Medina et al. (1998 [triangle]).

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Object name is e-64-0o899-scheme1.jpg

Experimental

Crystal data

  • C18H16O6
  • M r = 328.32
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o899-efi1.jpg
  • a = 8.4536 (2) Å
  • b = 9.0878 (2) Å
  • c = 10.7832 (3) Å
  • α = 79.545 (2)°
  • β = 71.5640 (10)°
  • γ = 86.925 (2)°
  • V = 772.85 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 294 K
  • 0.22 × 0.19 × 0.11 mm

Data collection

  • Nonius Kappa CCD diffractometer
  • Absorption correction: none
  • 20499 measured reflections
  • 3153 independent reflections
  • 2512 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.123
  • S = 1.07
  • 3153 reflections
  • 218 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010696/bg2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010696/bg2176Isup2.hkl

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

Acknowledgments

The authors are grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) and Coordenação de Aperfeiçoamento de Pessoal de Ensino Superior (CAPES) for financial support.

supplementary crystallographic information

Comment

A number of differents flavones are known to have interesting modulatory activities at Gamma-aminobutyric acid receptors (GABA-A), an inhibitory neurotransmitter found in the nervous systems of widely divergent species. It is the main inhibitory neurotransmitter in the central nervous system (Medina et al., 1998; Chebib & Johnston, 2000).

Figure 1 shows an ORTEP view of thr title compound, 8-hydroxy-5,6,7-trymethoxy-2-phenylchromen-4-one (I) with atom labeling and 50% probability displacement ellipsoids. The benzopyran group in (I) is essentially planar, with the oxygen atoms of the substituent groups lying close to its mean plane. The ring forms angles of 113.8 (4)°, 117.8 (3)° and 114.4 (2)° with the O3—C16, O4—C17 and O5—C18 methoxy groups, respectively, and 34.61 (4)° with the phenyl ring.

The molecular conformation is fixed by intramolecular interactions (Table 1 and Figure 1). The crystal packing is mainly determined by one classical intermolecular H bond which gives rise to the formation of an infinite chain along the a axis (Table 1 and Figure 2).

Experimental

Selected parts of the Z. montana plant (Branches and leaves) were dried carefully by forced air at 40 °C and reduced to powder. The resulting material was macerated three times with hexane, followed with methanol at room temperature for 72 h each. After the evaporation of the solvent under reduced pressure, crude extracts were obtained. A well shaped single-crystal of the title compound was selected for the XRD experiments.

Refinement

All the hydrogen atoms were stereochemically positioned and refined with a riding model. Hydrogen atoms of the CH and CH2 groups were set isotropic with a thermal parameter 20% greater than the equivalent isotropic displacement parameter of the atom to which each one was bonded. This percentage was set to 50% for the hydrogen atoms of the CH3 and OH groups.

Figures

Fig. 1.
View of (I) (50% probability displacement ellipsoids)
Fig. 2.
View of the intermolecular interaction that gives rise to the formation of a chain along the a axis.

Crystal data

C18H16O6Z = 2
Mr = 328.32F000 = 344
Triclinic, P1Dx = 1.411 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.4536 (2) ÅCell parameters from 20513 reflections
b = 9.0878 (2) Åθ = 2.9–26.4º
c = 10.7832 (3) ŵ = 0.11 mm1
α = 79.545 (2)ºT = 294 K
β = 71.5640 (10)ºPrism, yellow
γ = 86.925 (2)º0.22 × 0.19 × 0.11 mm
V = 772.85 (3) Å3

Data collection

KappaCCD diffractometerRint = 0.049
[var phi] scans and ω scans winth κ offsetsθmax = 26.4º
Absorption correction: noneθmin = 3.3º
20499 measured reflectionsh = −10→10
3153 independent reflectionsk = −11→11
2512 reflections with I > 2σ(I)l = −13→13

Refinement

Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1467P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042(Δ/σ)max < 0.001
wR(F2) = 0.124Δρmax = 0.25 e Å3
S = 1.07Δρmin = −0.24 e Å3
3153 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
218 parametersExtinction coefficient: 0.043 (11)

Special details

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.

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

xyzUiso*/Ueq
O10.40508 (11)0.55938 (11)0.19334 (9)0.0343 (3)
O20.05483 (13)0.68927 (14)0.00920 (12)0.0550 (3)
O30.29650 (12)0.85689 (12)−0.19401 (10)0.0428 (3)
O40.63074 (13)0.94104 (12)−0.28518 (10)0.0441 (3)
O50.83892 (11)0.83118 (11)−0.14212 (9)0.0362 (3)
O60.71943 (11)0.63816 (12)0.09768 (9)0.0395 (3)
C10.16504 (16)0.64776 (16)0.06016 (15)0.0350 (3)
C20.13054 (16)0.54641 (16)0.18467 (14)0.0368 (3)
C30.24520 (16)0.50867 (15)0.24709 (13)0.0330 (3)
C40.45089 (16)0.65179 (15)0.07187 (13)0.0 (3)
C50.33896 (15)0.70155 (15)0.00135 (13)0.0301 (3)
C60.39952 (16)0.80083 (15)−0.12037 (13)0.0320 (3)
C70.56421 (16)0.84828 (15)−0.16628 (13)0.0313 (3)
C80.67300 (15)0.79300 (15)−0.09404 (13)0.0296 (3)
C90.61900 (15)0.69429 (15)0.02441 (13)0.0295 (3)
C100.21737 (17)0.41557 (16)0.37915 (13)0.0353 (3)
C110.30333 (19)0.44556 (19)0.46281 (16)0.0459 (4)
C120.2755 (2)0.3598 (2)0.58706 (16)0.0547 (5)
C130.1650 (2)0.2423 (2)0.62864 (17)0.0552 (5)
C140.0795 (2)0.2109 (2)0.54662 (17)0.0573 (5)
C150.1043 (2)0.29793 (19)0.42257 (16)0.0469 (4)
C160.2848 (3)0.7646 (3)−0.2840 (2)0.0738 (6)
C170.5601 (3)1.0840 (2)−0.3033 (2)0.0708 (6)
C180.8774 (2)0.96476 (19)−0.10671 (19)0.0514 (4)
H80.81390.6720.06060.059*
H8A0.02420.50520.22370.044*
H170.37990.52390.43460.055*
H180.33190.38160.64290.066*
H190.14770.18390.71210.066*
H200.00490.1310.57480.069*
H210.0450.27740.36820.056*
H22A0.99510.9838−0.14350.077*
H22B0.84510.9539−0.01180.077*
H22C0.8181.0469−0.14090.077*
H27A0.21160.8102−0.33210.111*
H27B0.24150.6682−0.23550.111*
H27C0.39340.753−0.34520.111*
H30A0.61761.1374−0.39020.106*
H30B0.57011.1381−0.23750.106*
H30C0.44441.074−0.29460.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0240 (5)0.0430 (6)0.0331 (5)−0.0036 (4)−0.0093 (4)0.0024 (4)
O20.0248 (5)0.0739 (8)0.0630 (7)−0.0045 (5)−0.0224 (5)0.0132 (6)
O30.0334 (5)0.0540 (6)0.0446 (6)0.0043 (5)−0.0228 (5)0.0007 (5)
O40.0364 (6)0.0472 (6)0.0381 (6)0.0029 (4)−0.0061 (4)0.0083 (5)
O50.0218 (5)0.0456 (6)0.0403 (5)−0.0040 (4)−0.0082 (4)−0.0067 (4)
O60.0240 (5)0.0570 (6)0.0364 (5)−0.0039 (4)−0.0151 (4)0.0057 (4)
C50.0227 (6)0.0339 (7)0.0350 (7)0.0019 (5)−0.0114 (5)−0.0058 (6)
C90.0233 (6)0.0362 (7)0.0309 (7)0.0014 (5)−0.0117 (5)−0.0051 (5)
C40.0239 (6)0.0336 (7)0.0302 (7)0.0006 (5)−0.0097 (5)−0.0036 (5)
C80.0216 (6)0.0345 (7)0.0328 (7)−0.0001 (5)−0.0081 (5)−0.0071 (5)
C10.0239 (6)0.0391 (7)0.0434 (8)0.0009 (5)−0.0134 (6)−0.0057 (6)
C60.0264 (6)0.0369 (7)0.0354 (7)0.0051 (5)−0.0153 (6)−0.0044 (6)
C20.0218 (6)0.0427 (8)0.0430 (8)−0.0027 (5)−0.0077 (6)−0.0039 (6)
C70.0281 (7)0.0336 (7)0.0307 (7)0.0020 (5)−0.0093 (5)−0.0024 (5)
C30.0247 (6)0.0361 (7)0.0355 (7)−0.0012 (5)−0.0057 (5)−0.0057 (6)
C100.0278 (7)0.0403 (8)0.0332 (7)0.0019 (6)−0.0047 (5)−0.0041 (6)
C110.0360 (8)0.0560 (10)0.0431 (8)−0.0103 (7)−0.0132 (7)0.0023 (7)
C120.0441 (9)0.0773 (12)0.0404 (9)−0.0070 (8)−0.0160 (7)0.0031 (8)
C130.0510 (10)0.0644 (11)0.0386 (9)−0.0040 (8)−0.0068 (7)0.0091 (8)
C140.0588 (11)0.0530 (10)0.0482 (10)−0.0184 (8)−0.0038 (8)0.0031 (8)
C150.0462 (9)0.0517 (9)0.0393 (8)−0.0123 (7)−0.0082 (7)−0.0052 (7)
C160.0701 (13)0.1072 (17)0.0656 (12)0.0106 (12)−0.0457 (11)−0.0277 (12)
C170.0703 (13)0.0491 (10)0.0732 (13)0.0092 (9)−0.0106 (10)0.0160 (9)
C180.0378 (8)0.0454 (9)0.0718 (11)−0.0098 (7)−0.0173 (8)−0.0089 (8)

Geometric parameters (Å, °)

O3—C61.3753 (15)C5—C61.4120 (19)
O3—C161.422 (2)C5—C11.4757 (18)
O2—C11.2341 (16)C9—C81.3798 (18)
O5—C81.3724 (15)C9—C41.3992 (18)
O5—C181.4193 (19)C8—C71.4024 (18)
C18—H22A0.9600C1—C21.438 (2)
C18—H22B0.9600C6—C71.3857 (19)
C18—H22C0.9600C2—C31.3430 (19)
C16—H27A0.9600C2—H8A0.9300
C16—H27B0.9600C3—C101.4735 (19)
C16—H27C0.9600C10—C151.386 (2)
O6—C91.3552 (15)C10—C111.393 (2)
O6—H80.8200C15—C141.384 (2)
O4—C71.3687 (16)C15—H210.9300
O4—C171.408 (2)C12—C131.372 (3)
C17—H30A0.9600C12—C111.378 (2)
C17—H30B0.9600C12—H180.9300
C17—H30C0.9600C11—H170.9300
O1—C31.3599 (16)C13—C141.380 (3)
O1—C41.3733 (16)C13—H190.9300
C5—C41.4009 (17)C14—H200.9300
C6—O3—C16113.82 (13)C9—C8—C7121.45 (12)
C8—O5—C18114.34 (11)O2—C1—C2121.77 (13)
O5—C18—H22A109.5O2—C1—C5123.02 (13)
O5—C18—H22B109.5C2—C1—C5115.18 (11)
H22A—C18—H22B109.5O3—C6—C7118.28 (12)
O5—C18—H22C109.5O3—C6—C5121.32 (12)
H22A—C18—H22C109.5C7—C6—C5120.36 (12)
H22B—C18—H22C109.5C3—C2—C1122.86 (12)
O3—C16—H27A109.5C3—C2—H8A118.6
O3—C16—H27B109.5C1—C2—H8A118.6
H27A—C16—H27B109.5O4—C7—C6122.84 (12)
O3—C16—H27C109.5O4—C7—C8117.18 (12)
H27A—C16—H27C109.5C6—C7—C8119.84 (12)
H27B—C16—H27C109.5C2—C3—O1121.83 (12)
C9—O6—H8109.5C2—C3—C10126.44 (12)
C7—O4—C17117.76 (13)O1—C3—C10111.69 (11)
O4—C17—H30A109.5C15—C10—C11119.00 (14)
O4—C17—H30B109.5C15—C10—C3120.60 (13)
H30A—C17—H30B109.5C11—C10—C3120.40 (13)
O4—C17—H30C109.5C14—C15—C10120.13 (15)
H30A—C17—H30C109.5C14—C15—H21119.9
H30B—C17—H30C109.5C10—C15—H21119.9
C3—O1—C4119.21 (10)C13—C12—C11120.27 (16)
C4—C5—C6117.91 (12)C13—C12—H18119.9
C4—C5—C1117.68 (12)C11—C12—H18119.9
C6—C5—C1124.41 (12)C12—C11—C10120.38 (15)
O6—C9—C8123.53 (11)C12—C11—H17119.8
O6—C9—C4118.48 (11)C10—C11—H17119.8
C8—C9—C4117.98 (11)C12—C13—C14119.99 (15)
O1—C4—C9114.47 (11)C12—C13—H19120.0
O1—C4—C5123.14 (11)C14—C13—H19120.0
C9—C4—C5122.39 (12)C13—C14—C15120.22 (16)
O5—C8—C9117.81 (11)C13—C14—H20119.9
O5—C8—C7120.68 (12)C15—C14—H20119.9
C3—O1—C4—C9−178.49 (11)C5—C1—C2—C33.3 (2)
C3—O1—C4—C52.30 (19)C17—O4—C7—C660.8 (2)
O6—C9—C4—O12.27 (18)C17—O4—C7—C8−123.44 (17)
C8—C9—C4—O1−176.89 (11)O3—C6—C7—O4−4.1 (2)
O6—C9—C4—C5−178.52 (12)C5—C6—C7—O4178.13 (12)
C8—C9—C4—C52.3 (2)O3—C6—C7—C8−179.74 (12)
C6—C5—C4—O1177.67 (12)C5—C6—C7—C82.4 (2)
C1—C5—C4—O1−1.7 (2)O5—C8—C7—O4−0.13 (19)
C6—C5—C4—C9−1.5 (2)C9—C8—C7—O4−177.50 (12)
C1—C5—C4—C9179.16 (12)O5—C8—C7—C6175.80 (12)
C18—O5—C8—C9−94.47 (15)C9—C8—C7—C6−1.6 (2)
C18—O5—C8—C788.06 (16)C1—C2—C3—O1−2.9 (2)
O6—C9—C8—O52.7 (2)C1—C2—C3—C10174.87 (13)
C4—C9—C8—O5−178.22 (11)C4—O1—C3—C20.0 (2)
O6—C9—C8—C7−179.89 (12)C4—O1—C3—C10−178.04 (11)
C4—C9—C8—C7−0.8 (2)C2—C3—C10—C1534.3 (2)
C4—C5—C1—O2176.96 (14)O1—C3—C10—C15−147.80 (14)
C6—C5—C1—O2−2.4 (2)C2—C3—C10—C11−145.11 (16)
C4—C5—C1—C2−0.99 (19)O1—C3—C10—C1132.83 (18)
C6—C5—C1—C2179.69 (13)C11—C10—C15—C14−0.8 (2)
C16—O3—C6—C794.31 (17)C3—C10—C15—C14179.80 (15)
C16—O3—C6—C5−87.89 (18)C13—C12—C11—C101.2 (3)
C4—C5—C6—O3−178.70 (12)C15—C10—C11—C12−0.3 (2)
C1—C5—C6—O30.6 (2)C3—C10—C11—C12179.07 (15)
C4—C5—C6—C7−1.0 (2)C11—C12—C13—C14−0.9 (3)
C1—C5—C6—C7178.37 (13)C12—C13—C14—C15−0.2 (3)
O2—C1—C2—C3−174.72 (15)C10—C15—C14—C131.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O6—H8···O50.822.352.770 (1)113
O6—H8···O2i0.821.942.727 (1)160

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2176).

References

  • Chebib, M. & Johnston, G. A. R. (2000). J. Med. Chem.43, 1427–1447. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Medina, J. H., Viola, H., Wolfman, C., Marder, M., Wasowski, C., Calvo, D. & Paladini, A. C. (1998). Phytomedicine, 5, 235–243. [PubMed]
  • Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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