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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o822.
Published online 2008 April 10. doi:  10.1107/S1600536808009355
PMCID: PMC2961195

5,3′-Dihydr­oxy-7,4′-dimethoxy­flavanone from Artemisia sphaerocephala Kraschen

Abstract

The title compound, C17H16O6, was isolated from the Chinese Tibetan medicinal plant Artemisia sphaerocephala Kraschen. The mol­ecular conformation is consolidated by two intra­molecular O—H(...)O hydrogen bonds. A further inter­molecular O—H(...)O hydrogen bond leads to chains along [010] in the crystal structure.

Related literature

For background, see: Zhao et al. (2007 [triangle]).

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Object name is e-64-0o822-scheme1.jpg

Experimental

Crystal data

  • C17H16O6
  • M r = 316.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o822-efi1.jpg
  • a = 5.4234 (12) Å
  • b = 9.293 (2) Å
  • c = 14.940 (3) Å
  • β = 91.039 (2)°
  • V = 752.9 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 296 (2) K
  • 0.22 × 0.18 × 0.12 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.977, T max = 0.987
  • 7958 measured reflections
  • 1581 independent reflections
  • 1489 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.077
  • S = 1.06
  • 1581 reflections
  • 212 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009355/hb2716sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009355/hb2716Isup2.hkl

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

supplementary crystallographic information

Comment

As part of the ongoing investigations of the Chinese Tibetan medicinal plant Artemisia sphaerocephala Kraschen (Zhao et al., 2007), we now report the isolation and structure of the flavone-related title compound, (I).

Compound (I) consists of three-ring system, including a phenyl ring and a benzopyrone fused ring (Fig.1). The C–O bond distances range from 1.239 (2) to 1.453 (2) Å, in which C4–O2 [1.239 (2) Å] is typical for a C=O double-bond. The S(6) ring of O1/C2/C3/C4/C9/C10 in (I) is nonplanar, charactrtized by a O1–C2–C3–C4 torsion angle of 52.9 (2) °. Atom C2 is chiral, but the absolute structure of (I) could not be established from the present experiment. The dihedral angle between the aromatic ring planes is 77.26 (9) °.

Two intramolecular O-H···O hydrogen bonds (Table 1) help to establish the molecular conformation, both constructing S(6) rings. In addition, an intermolecular O-H···O link leads to [010] chains in the crystal (Fig. 2).

Experimental

The air-dried whole plant (5.1 kg) was ground into powder and extracted three times with 95% EtOH for 3 h each time. The concentrated extract was dispersed in water and partitioned successively with petroleum ether, CHCl3, EtOAC and n-BuOH. The chloroform fraction (115 g) was subjected to silics gel with petroleum ether-acetone (9:1) to yield two fractions (Frs. 1–2). Fraction 2 (50 g) was subjected to silics gel with petroleum ether-EtOAC (50:1, 45:1, 40:1, 30:1) to yield six fractions. After a week, the crude title compound (20 mg) was crystallized from the fourth fraction. After recrystallization from petroleum ether-EtOAC, colourless blocks of (I) arose, with a melting point of 475 K. The molecular formula, C17H16O6, was established by ESIMS m/z:316(M+). Spectroscopic analysis, 1H NMR (400 MHz, DMSO-d6) δ: 12.15 (1H, s), 6.08 (1H, d, J=2.2 Hz), 6.05 (1H, d, J=2.2 Hz), 5.47 (1H, dd, J=12.6 Hz, 3.0 Hz), 3.20 (1H, dd, J=15.5 Hz, 12.6 Hz), 2.82 (1H, dd, J=15.5 Hz, 3.0 Hz); 13 C NMR (400 MHz, DMSO-d6) δ: 197.0 (C-4), 168.0 (C-7), 163.8 (C-5), 163.1 (C-9), 147.8 (C-4'), 146.7 (C-3'), 131.8 (C-1'), 117.9 (C-6'), 113.5 (C-5'), 111.3 (C-2'), 102.9 (C-10), 94.6 (C-6), 93.7 (C-8), 79.0 (C-2), 42.6 (C-3), 55.4 (4'-OCH3), 55.3 (7-OCH3).

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement.

The H atoms were geometrically placed (C-H = 0.93–0.98Å, O—H = 0.82 Å), and refined as riding with Uiso(H)=1.2Ueq(C) or Uiso(H)=1.5Ueq(O or methyl C).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 40% probability level. Hydrogen bonds are shown as double dashed lines.
Fig. 2.
Fragment of the one-dimensional chain structure of (I) with hydrogen bonds shown as dashed lines.

Crystal data

C17H16O6F000 = 332
Mr = 316.30Dx = 1.395 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2y bCell parameters from 4047 reflections
a = 5.4234 (12) Åθ = 2.6–27.5º
b = 9.293 (2) ŵ = 0.11 mm1
c = 14.940 (3) ÅT = 296 (2) K
β = 91.039 (2)ºBlock, colorless
V = 752.9 (3) Å30.22 × 0.18 × 0.12 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer1581 independent reflections
Radiation source: fine-focus sealed tube1489 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.019
T = 296(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −6→6
Tmin = 0.977, Tmax = 0.987k = −11→11
7958 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.077  w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0531P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1581 reflectionsΔρmax = 0.11 e Å3
212 parametersΔρmin = −0.14 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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.
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.

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

xyzUiso*/Ueq
O10.3993 (2)0.73089 (16)0.11833 (7)0.0443 (3)
O20.8292 (3)0.9824 (2)0.28305 (11)0.0697 (5)
O30.6055 (3)0.8761 (2)0.41875 (10)0.0703 (5)
H30.70860.92310.39190.105*
O4−0.0461 (3)0.54437 (19)0.35407 (9)0.0532 (4)
O50.5698 (3)0.79981 (18)−0.28802 (9)0.0582 (4)
O60.2587 (3)0.94212 (19)−0.18692 (9)0.0595 (4)
H50.27320.9377−0.24140.089*
C1'0.6333 (3)0.7757 (2)−0.01135 (12)0.0396 (4)
C20.6447 (3)0.7700 (2)0.08935 (12)0.0407 (4)
H20.76050.69420.10790.049*
C2'0.8030 (4)0.7024 (2)−0.06221 (12)0.0469 (5)
H2'0.92710.6494−0.03380.056*
C30.7244 (4)0.9111 (3)0.13314 (13)0.0509 (5)
H3A0.89460.93100.11850.061*
H3B0.62350.98890.10940.061*
C3'0.7904 (4)0.7070 (2)−0.15510 (13)0.0508 (5)
H3'0.90560.6574−0.18860.061*
C40.7001 (4)0.9053 (2)0.23342 (13)0.0485 (5)
C4'0.6070 (4)0.7852 (2)−0.19750 (12)0.0434 (4)
C50.4695 (4)0.7986 (2)0.35954 (12)0.0472 (5)
C5'0.4376 (3)0.8613 (2)−0.14645 (12)0.0415 (4)
C60.2845 (4)0.7110 (3)0.39144 (12)0.0490 (5)
H60.25600.70470.45250.059*
C6'0.4503 (3)0.8559 (2)−0.05446 (12)0.0439 (4)
H6'0.33590.9062−0.02100.053*
C70.1420 (3)0.6325 (2)0.33055 (12)0.0416 (4)
C7'0.7267 (6)0.7210 (3)−0.34504 (14)0.0701 (7)
H7'A0.89430.7509−0.33500.105*
H7'B0.67980.7386−0.40630.105*
H7'C0.71200.6201−0.33240.105*
C80.1841 (3)0.6390 (2)0.23879 (12)0.0410 (4)
H80.08820.58520.19890.049*
C90.3691 (3)0.7260 (2)0.20815 (11)0.0373 (4)
C100.5161 (3)0.8091 (2)0.26731 (12)0.0413 (4)
C11−0.1037 (5)0.5297 (3)0.44657 (14)0.0660 (7)
H11A0.03530.48930.47840.099*
H11B−0.24360.46730.45250.099*
H11C−0.14130.62250.47100.099*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0462 (7)0.0580 (8)0.0285 (6)−0.0111 (6)0.0003 (5)0.0007 (6)
O20.0826 (11)0.0731 (11)0.0531 (9)−0.0365 (10)−0.0075 (8)−0.0084 (8)
O30.0893 (12)0.0821 (12)0.0389 (7)−0.0298 (10)−0.0109 (7)−0.0116 (8)
O40.0558 (8)0.0709 (10)0.0330 (7)−0.0121 (7)0.0052 (6)0.0056 (7)
O50.0790 (10)0.0625 (9)0.0332 (7)0.0170 (8)0.0059 (6)−0.0006 (7)
O60.0639 (9)0.0755 (11)0.0391 (8)0.0270 (8)−0.0006 (7)0.0045 (8)
C1'0.0429 (9)0.0412 (10)0.0346 (9)−0.0019 (8)0.0026 (7)0.0034 (8)
C20.0407 (9)0.0457 (10)0.0357 (9)−0.0013 (8)−0.0004 (7)0.0048 (8)
C2'0.0465 (10)0.0504 (11)0.0438 (10)0.0109 (9)0.0036 (8)0.0073 (9)
C30.0557 (11)0.0530 (12)0.0440 (11)−0.0138 (10)0.0009 (9)0.0023 (9)
C3'0.0552 (11)0.0531 (12)0.0446 (11)0.0140 (10)0.0117 (9)0.0014 (10)
C40.0525 (11)0.0484 (11)0.0443 (10)−0.0106 (10)−0.0054 (9)−0.0026 (9)
C4'0.0561 (10)0.0409 (10)0.0334 (9)0.0030 (9)0.0069 (8)0.0024 (8)
C50.0568 (11)0.0521 (12)0.0326 (9)−0.0008 (10)−0.0075 (8)−0.0051 (8)
C5'0.0443 (9)0.0430 (10)0.0372 (9)0.0055 (8)0.0010 (8)0.0040 (8)
C60.0597 (11)0.0605 (12)0.0267 (8)−0.0003 (10)0.0001 (8)−0.0005 (9)
C6'0.0465 (10)0.0484 (10)0.0370 (9)0.0089 (9)0.0075 (8)0.0013 (8)
C70.0422 (10)0.0491 (11)0.0335 (9)0.0010 (8)0.0014 (7)0.0047 (8)
C7'0.1016 (19)0.0707 (16)0.0385 (11)0.0154 (15)0.0164 (11)−0.0066 (12)
C80.0409 (9)0.0494 (10)0.0326 (9)−0.0038 (8)−0.0039 (7)−0.0016 (8)
C90.0405 (9)0.0424 (10)0.0290 (8)0.0004 (8)−0.0028 (7)0.0007 (8)
C100.0450 (9)0.0443 (10)0.0346 (9)−0.0016 (8)−0.0031 (7)−0.0011 (8)
C110.0706 (15)0.0886 (18)0.0393 (11)−0.0062 (14)0.0133 (10)0.0150 (12)

Geometric parameters (Å, °)

O1—C91.3555 (19)C3'—C4'1.377 (3)
O1—C21.453 (2)C3'—H3'0.9300
O2—C41.239 (2)C4—C101.439 (3)
O3—C51.350 (2)C4'—C5'1.397 (3)
O3—H30.8200C5—C61.383 (3)
O4—C71.359 (2)C5—C101.409 (3)
O4—C111.429 (2)C5'—C6'1.376 (2)
O5—C4'1.370 (2)C6—C71.390 (3)
O5—C7'1.419 (3)C6—H60.9300
O6—C5'1.360 (2)C6'—H6'0.9300
O6—H50.8200C7—C81.395 (2)
C1'—C2'1.383 (3)C7'—H7'A0.9600
C1'—C6'1.390 (3)C7'—H7'B0.9600
C1'—C21.506 (2)C7'—H7'C0.9600
C2—C31.525 (3)C8—C91.373 (3)
C2—H20.9800C8—H80.9300
C2'—C3'1.389 (3)C9—C101.409 (2)
C2'—H2'0.9300C11—H11A0.9600
C3—C41.507 (3)C11—H11B0.9600
C3—H3A0.9700C11—H11C0.9600
C3—H3B0.9700
C9—O1—C2115.53 (13)C6—C5—C10121.46 (17)
C5—O3—H3109.5O6—C5'—C6'119.12 (16)
C7—O4—C11119.06 (17)O6—C5'—C4'120.52 (16)
C4'—O5—C7'117.54 (18)C6'—C5'—C4'120.37 (17)
C5'—O6—H5109.5C5—C6—C7118.79 (17)
C2'—C1'—C6'119.09 (16)C5—C6—H6120.6
C2'—C1'—C2121.06 (16)C7—C6—H6120.6
C6'—C1'—C2119.86 (16)C5'—C6'—C1'120.31 (17)
O1—C2—C1'106.57 (13)C5'—C6'—H6'119.8
O1—C2—C3109.97 (16)C1'—C6'—H6'119.8
C1'—C2—C3113.88 (16)O4—C7—C6123.92 (16)
O1—C2—H2108.8O4—C7—C8114.67 (16)
C1'—C2—H2108.8C6—C7—C8121.40 (17)
C3—C2—H2108.8O5—C7'—H7'A109.5
C1'—C2'—C3'120.83 (17)O5—C7'—H7'B109.5
C1'—C2'—H2'119.6H7'A—C7'—H7'B109.5
C3'—C2'—H2'119.6O5—C7'—H7'C109.5
C4—C3—C2111.48 (16)H7'A—C7'—H7'C109.5
C4—C3—H3A109.3H7'B—C7'—H7'C109.5
C2—C3—H3A109.3C9—C8—C7119.13 (17)
C4—C3—H3B109.3C9—C8—H8120.4
C2—C3—H3B109.3C7—C8—H8120.4
H3A—C3—H3B108.0O1—C9—C8116.84 (16)
C4'—C3'—C2'119.86 (17)O1—C9—C10121.70 (16)
C4'—C3'—H3'120.1C8—C9—C10121.44 (15)
C2'—C3'—H3'120.1C5—C10—C9117.77 (17)
O2—C4—C10122.49 (18)C5—C10—C4121.68 (17)
O2—C4—C3121.02 (19)C9—C10—C4120.51 (16)
C10—C4—C3116.47 (17)O4—C11—H11A109.5
O5—C4'—C3'126.74 (17)O4—C11—H11B109.5
O5—C4'—C5'113.72 (17)H11A—C11—H11B109.5
C3'—C4'—C5'119.53 (16)O4—C11—H11C109.5
O3—C5—C6118.64 (17)H11A—C11—H11C109.5
O3—C5—C10119.90 (18)H11B—C11—H11C109.5
C9—O1—C2—C1'−177.36 (16)C2'—C1'—C6'—C5'0.5 (3)
C9—O1—C2—C3−53.5 (2)C2—C1'—C6'—C5'−179.73 (18)
C2'—C1'—C2—O1−128.91 (19)C11—O4—C7—C6−0.2 (3)
C6'—C1'—C2—O151.3 (2)C11—O4—C7—C8179.76 (19)
C2'—C1'—C2—C3109.7 (2)C5—C6—C7—O4−179.2 (2)
C6'—C1'—C2—C3−70.1 (2)C5—C6—C7—C80.8 (3)
C6'—C1'—C2'—C3'−0.8 (3)O4—C7—C8—C9179.50 (18)
C2—C1'—C2'—C3'179.46 (18)C6—C7—C8—C9−0.6 (3)
O1—C2—C3—C452.9 (2)C2—O1—C9—C8−155.13 (17)
C1'—C2—C3—C4172.44 (16)C2—O1—C9—C1026.5 (3)
C1'—C2'—C3'—C4'0.0 (3)C7—C8—C9—O1−178.69 (17)
C2—C3—C4—O2154.3 (2)C7—C8—C9—C10−0.3 (3)
C2—C3—C4—C10−27.3 (3)O3—C5—C10—C9180.00 (19)
C7'—O5—C4'—C3'3.6 (3)C6—C5—C10—C9−0.6 (3)
C7'—O5—C4'—C5'−177.3 (2)O3—C5—C10—C4−2.5 (3)
C2'—C3'—C4'—O5−179.8 (2)C6—C5—C10—C4176.9 (2)
C2'—C3'—C4'—C5'1.1 (3)O1—C9—C10—C5179.19 (17)
O5—C4'—C5'—O6−0.8 (3)C8—C9—C10—C50.9 (3)
C3'—C4'—C5'—O6178.4 (2)O1—C9—C10—C41.6 (3)
O5—C4'—C5'—C6'179.39 (18)C8—C9—C10—C4−176.67 (19)
C3'—C4'—C5'—C6'−1.4 (3)O2—C4—C10—C50.9 (3)
O3—C5—C6—C7179.2 (2)C3—C4—C10—C5−177.44 (19)
C10—C5—C6—C7−0.2 (3)O2—C4—C10—C9178.4 (2)
O6—C5'—C6'—C1'−179.19 (19)C3—C4—C10—C90.0 (3)
C4'—C5'—C6'—C1'0.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.852.579 (2)148
O6—H5···O50.822.182.640 (2)116
O6—H5···O4i0.822.292.892 (2)130

Symmetry codes: (i) −x, y+1/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2716).

References

  • Bruker (2001). SAINT-Plus (Version 6.45), SMART and SADABS Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Zhao, D. B., Li, L. X., Liu, X. H., Li, M. J. & Wang, W. L. (2007). Chin. Chem. Lett.18, 551–557.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography