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The title compound, 1-hydroxy-2,3,4,7-tetra­methoxy-9H-xanthen-9-one, C17H16O7, was isolated from Swertia Chirayita and is found to be planar with only two of the methoxy substituents lying out of the plane of the mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009171/su6088sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009171/su6088Isup2.hkl
Contains datablock I

CCDC reference: 239289

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.052
  • wR factor = 0.165
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc. PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg.
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.67 Sigma PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 SDP/VAX(Enraf-Nonius, 1989); cell refinement: CAD-4 SDP/VAX; data reduction: MolEN/PC (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL7 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Siemens, 1994); software used to prepare material for publication: SHELXTL/PC.

1-hydroxy-2,3,4,7-tetramethoxy-9H-xanthen-9-one top
Crystal data top
C17H16O7F(000) = 696
Mr = 332.30Dx = 1.460 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.151 (1) Åθ = 10–20°
b = 13.229 (3) ŵ = 0.12 mm1
c = 16.044 (3) ÅT = 293 K
β = 95.18 (3)°Block, colourless
V = 1511.6 (5) Å30.4 × 0.3 × 0.3 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.063
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.0°
Graphite monochromatorh = 08
ω/2θ scansk = 015
2885 measured reflectionsl = 1918
2661 independent reflections3 standard reflections every 60 min
923 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0547P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2661 reflectionsΔρmax = 0.22 e Å3
218 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0024 (9)
Special details top

Experimental. General procedures: Melting point was performed on an XRC1 micro-melting point apparatus and was uncorrected. NMR experiment was carried out on Varian INOVA-400 MHz s pectrometer. Chemical shifts(Δ) were given with TMS as an internal standard. EIMS was taken on a VG Auto Spec-3000 instrument. IR spectra were recorded on a Nicolet-Nexus 670-FT—IR spectrometer with KBr pellets. UV spectra were obtained on a UV-2001 spectrometer. Column chromatography was realised on silica gel (200–300 mesh, Qingdao Marine Chemical Inc., China).

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) top
xyzUiso*/Ueq
O10.0973 (5)0.3180 (2)0.3868 (2)0.0671 (10)
O20.2618 (4)0.0110 (2)0.61283 (17)0.0476 (8)
O30.2537 (4)0.0606 (2)0.36408 (19)0.0591 (10)
O40.3341 (4)0.2452 (2)0.40539 (18)0.0582 (10)
H4A0.30980.19450.37370.080*
O50.3204 (4)0.1269 (3)0.73401 (17)0.0569 (9)
O60.4087 (5)0.3157 (3)0.69958 (19)0.0676 (10)
O70.4167 (4)0.3822 (2)0.52787 (19)0.0590 (10)
C10.0824 (7)0.3002 (4)0.2991 (3)0.0684 (16)
H1A0.05200.36210.26970.080*
H1B0.19980.27480.28320.080*
H1C0.01460.25130.28520.080*
C20.1707 (6)0.1404 (4)0.4101 (3)0.0485 (12)
H2A0.16290.12600.35130.080*
C30.1403 (6)0.2365 (4)0.4374 (3)0.0514 (13)
C40.1527 (6)0.2565 (4)0.5234 (3)0.0531 (13)
H4B0.13280.32420.54220.080*
C50.1933 (6)0.1814 (4)0.5808 (3)0.0491 (13)
H5A0.19980.19510.63980.080*
C60.2235 (6)0.0837 (4)0.5528 (3)0.0435 (12)
C70.2144 (6)0.0618 (4)0.4675 (3)0.0407 (11)
C80.2543 (6)0.0392 (4)0.4398 (3)0.0456 (12)
C90.2942 (6)0.1130 (3)0.5051 (3)0.0412 (11)
C100.3331 (6)0.2140 (4)0.4859 (3)0.0448 (12)
C110.3702 (6)0.2854 (4)0.5489 (3)0.0458 (12)
C120.3722 (6)0.2552 (4)0.6320 (3)0.0453 (12)
C130.3326 (6)0.1551 (4)0.6519 (3)0.0418 (12)
C140.2970 (6)0.0857 (3)0.5888 (3)0.0424 (11)
C150.4946 (7)0.0997 (4)0.7787 (3)0.0722 (17)
H15A0.47560.08030.83500.080*
H15B0.57710.15710.77980.080*
H15C0.54960.04440.75090.080*
C160.4285 (9)0.4203 (4)0.6965 (3)0.0858 (19)
H16A0.45250.44610.75240.080*
H16B0.31540.45000.67050.080*
H16C0.53170.43680.66470.080*
C170.2627 (7)0.4419 (4)0.4919 (3)0.0788 (18)
H17A0.30630.50840.47930.080*
H17B0.17020.44690.53150.080*
H17C0.20780.41060.44150.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.080 (2)0.057 (2)0.065 (2)0.007 (2)0.0123 (19)0.011 (2)
O20.052 (2)0.052 (2)0.0386 (18)0.0056 (17)0.0046 (15)0.0039 (17)
O30.078 (3)0.058 (2)0.0406 (19)0.0020 (19)0.0054 (18)0.0011 (17)
O40.072 (2)0.060 (2)0.042 (2)0.0013 (18)0.0019 (17)0.0050 (17)
O50.061 (2)0.075 (2)0.0353 (19)0.0071 (19)0.0057 (16)0.0022 (17)
O60.087 (3)0.061 (3)0.054 (2)0.017 (2)0.0031 (19)0.011 (2)
O70.057 (2)0.056 (2)0.063 (2)0.0091 (19)0.0004 (18)0.0084 (19)
C10.075 (4)0.069 (4)0.063 (4)0.014 (3)0.018 (3)0.017 (3)
C20.047 (3)0.051 (3)0.047 (3)0.002 (3)0.007 (2)0.008 (3)
C30.044 (3)0.049 (4)0.062 (4)0.004 (2)0.010 (3)0.013 (3)
C40.054 (3)0.048 (3)0.058 (3)0.000 (3)0.013 (3)0.001 (3)
C50.046 (3)0.049 (3)0.052 (3)0.000 (3)0.007 (2)0.005 (3)
C60.036 (3)0.047 (3)0.047 (3)0.004 (2)0.002 (2)0.001 (3)
C70.035 (3)0.050 (3)0.038 (3)0.002 (2)0.008 (2)0.001 (2)
C80.044 (3)0.056 (4)0.037 (3)0.013 (3)0.009 (2)0.009 (3)
C90.038 (3)0.046 (3)0.040 (3)0.004 (2)0.007 (2)0.003 (2)
C100.035 (3)0.060 (4)0.039 (3)0.002 (2)0.000 (2)0.010 (3)
C110.039 (3)0.040 (3)0.057 (3)0.004 (2)0.002 (2)0.003 (3)
C120.037 (3)0.058 (4)0.040 (3)0.008 (2)0.001 (2)0.005 (3)
C130.040 (3)0.054 (3)0.032 (3)0.006 (2)0.006 (2)0.002 (2)
C140.034 (3)0.047 (3)0.045 (3)0.001 (2)0.001 (2)0.003 (3)
C150.081 (4)0.074 (4)0.058 (3)0.007 (3)0.008 (3)0.009 (3)
C160.130 (5)0.062 (4)0.063 (4)0.010 (4)0.004 (4)0.012 (3)
C170.085 (4)0.054 (4)0.094 (4)0.011 (3)0.014 (4)0.020 (3)
Geometric parameters (Å, º) top
O1—C31.368 (5)C4—H4B0.9599
O1—C11.421 (5)C5—C61.391 (6)
O2—C141.365 (5)C5—H5A0.9602
O2—C61.372 (5)C6—C71.394 (5)
O3—C81.247 (5)C7—C81.444 (6)
O4—C101.357 (5)C8—C91.442 (6)
O4—H4A0.8499C9—C141.389 (5)
O5—C131.379 (5)C9—C101.404 (6)
O5—C151.426 (5)C10—C111.391 (6)
O6—C121.354 (5)C11—C121.389 (6)
O6—C161.392 (5)C12—C131.397 (6)
O7—C111.373 (5)C13—C141.375 (6)
O7—C171.434 (5)C15—H15A0.9601
C1—H1A0.9598C15—H15B0.9600
C1—H1B0.9600C15—H15C0.9599
C1—H1C0.9600C16—H16A0.9600
C2—C31.368 (6)C16—H16B0.9600
C2—C71.406 (6)C16—H16C0.9599
C2—H2A0.9602C17—H17A0.9601
C3—C41.400 (6)C17—H17B0.9600
C4—C51.368 (6)C17—H17C0.9601
C3—O1—C1116.8 (4)C10—C9—C8121.0 (4)
C14—O2—C6119.3 (3)O4—C10—C11117.9 (4)
C10—O4—H4A108.2O4—C10—C9121.1 (4)
C13—O5—C15114.9 (3)C11—C10—C9121.0 (4)
C12—O6—C16124.9 (4)O7—C11—C12121.5 (4)
C11—O7—C17114.8 (4)O7—C11—C10119.3 (4)
O1—C1—H1A109.8C12—C11—C10119.1 (4)
O1—C1—H1B109.3O6—C12—C11125.7 (5)
H1A—C1—H1B109.5O6—C12—C13113.9 (4)
O1—C1—H1C109.3C11—C12—C13120.5 (4)
H1A—C1—H1C109.5C14—C13—O5119.9 (4)
H1B—C1—H1C109.5C14—C13—C12119.5 (4)
C3—C2—C7120.7 (5)O5—C13—C12120.5 (4)
C3—C2—H2A120.2O2—C14—C13116.4 (4)
C7—C2—H2A119.1O2—C14—C9122.0 (4)
C2—C3—O1125.2 (5)C13—C14—C9121.6 (4)
C2—C3—C4119.6 (5)O5—C15—H15A110.4
O1—C3—C4115.2 (5)O5—C15—H15B108.5
C5—C4—C3121.1 (5)H15A—C15—H15B109.5
C5—C4—H4B119.7O5—C15—H15C109.5
C3—C4—H4B119.2H15A—C15—H15C109.5
C4—C5—C6119.1 (5)H15B—C15—H15C109.5
C4—C5—H5A121.0O6—C16—H16A109.3
C6—C5—H5A119.9O6—C16—H16B109.8
O2—C6—C5116.8 (4)H16A—C16—H16B109.5
O2—C6—C7122.1 (4)O6—C16—H16C109.3
C5—C6—C7121.0 (4)H16A—C16—H16C109.5
C6—C7—C2118.5 (4)H16B—C16—H16C109.5
C6—C7—C8120.1 (4)O7—C17—H17A109.7
C2—C7—C8121.4 (4)O7—C17—H17B108.7
O3—C8—C9122.5 (4)H17A—C17—H17B109.5
O3—C8—C7121.8 (4)O7—C17—H17C110.0
C9—C8—C7115.7 (4)H17A—C17—H17C109.5
C14—C9—C10118.3 (4)H17B—C17—H17C109.5
C14—C9—C8120.7 (4)
C7—C2—C3—O1179.9 (4)C17—O7—C11—C12110.1 (5)
C7—C2—C3—C40.0 (7)C17—O7—C11—C1074.5 (5)
C1—O1—C3—C20.4 (7)O4—C10—C11—O73.7 (6)
C1—O1—C3—C4179.6 (4)C9—C10—C11—O7176.8 (4)
C2—C3—C4—C50.6 (7)O4—C10—C11—C12179.2 (4)
O1—C3—C4—C5179.5 (4)C9—C10—C11—C121.3 (7)
C3—C4—C5—C60.3 (7)C16—O6—C12—C118.0 (8)
C14—O2—C6—C5178.5 (4)C16—O6—C12—C13171.4 (5)
C14—O2—C6—C71.7 (6)O7—C11—C12—O63.6 (7)
C4—C5—C6—O2179.3 (4)C10—C11—C12—O6179.0 (4)
C4—C5—C6—C70.5 (6)O7—C11—C12—C13177.1 (4)
O2—C6—C7—C2178.8 (4)C10—C11—C12—C131.7 (7)
C5—C6—C7—C21.1 (6)C15—O5—C13—C1496.4 (5)
O2—C6—C7—C82.9 (6)C15—O5—C13—C1286.7 (5)
C5—C6—C7—C8177.3 (4)O6—C12—C13—C14178.7 (4)
C3—C2—C7—C60.8 (6)C11—C12—C13—C141.9 (7)
C3—C2—C7—C8177.5 (4)O6—C12—C13—O54.4 (6)
C6—C7—C8—O3177.5 (4)C11—C12—C13—O5175.0 (4)
C2—C7—C8—O30.8 (7)C6—O2—C14—C13179.4 (4)
C6—C7—C8—C92.6 (6)C6—O2—C14—C90.4 (6)
C2—C7—C8—C9179.1 (4)O5—C13—C14—O23.9 (6)
O3—C8—C9—C14178.7 (4)C12—C13—C14—O2179.2 (4)
C7—C8—C9—C141.3 (6)O5—C13—C14—C9175.2 (4)
O3—C8—C9—C100.6 (7)C12—C13—C14—C91.8 (7)
C7—C8—C9—C10179.3 (4)C10—C9—C14—O2179.6 (4)
C14—C9—C10—O4179.4 (4)C8—C9—C14—O20.3 (6)
C8—C9—C10—O40.0 (6)C10—C9—C14—C131.4 (6)
C14—C9—C10—C111.1 (6)C8—C9—C14—C13179.2 (4)
C8—C9—C10—C11179.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O30.851.822.582 (4)148
C16—H16C···O70.962.392.746 (6)102
C17—H17A···O7i0.962.463.302 (6)146
C17—H17C···O40.962.463.014 (6)117
Symmetry code: (i) x+1, y1, z+1.
 

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