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The approximately planar title compound, C19H18O8, containing a benzopyran­one system, a benzene ring and four meth­oxy groups, is a natural flavone extracted from the herb Vitex trifolia L. Inter­molecular O—H...O and possible C—H...O inter­actions result in the formation of a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031175/hb2091sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031175/hb2091Isup2.hkl
Contains datablock I

CCDC reference: 621323

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.145
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

5,12-Dihydroxy-2,6,7,13-tetramethoxyflavone top
Crystal data top
C19H18O8F(000) = 1568
Mr = 374.33Dx = 1.458 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 750 reflections
a = 15.528 (4) Åθ = 2.3–17.6°
b = 12.446 (3) ŵ = 0.12 mm1
c = 17.672 (4) ÅT = 298 K
β = 92.565 (4)°Block, colourless
V = 3411.7 (13) Å30.24 × 0.21 × 0.19 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
3004 independent reflections
Radiation source: fine-focus sealed tube1569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 818
Tmin = 0.973, Tmax = 0.979k = 1414
8808 measured reflectionsl = 2021
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0629P)2 + 1.0805P]
where P = (Fo2 + 2Fc2)/3
3004 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Experimental. 1H NMR (DMSO-d6, 400 MHZ): δ: p.p.m. 12.59 (1H, s, 5-OH), 9.46 (1H, s, 12-OH), 6.85 (1H, s, 8-H), 7.57 (1H, d, 11-H), 7.08 (1H, d, 14-H), 7.56 (1H, d, 15-H), 3.71, 3.78, 3.85, 3.90 (12H, OMe×4). 13C NMR (DMSO-d6, 100 MHZ): δ: p.p.m. 157.23 (C-1), 143.42 (C-2), 183.72 (C-3), 111.03 (C-4), 157.11 (C-5), 137.02 (C-6), 164.13 (C-7), 96.76 (C-8), 161.07 (C-9), 125.86 (C-10), 120.49 (C-11), 151.80 (C-12), 155.76 (C-13), 117.26 (C-14), 127.64 (C-15), 65.49 (C-16), 65.16 (C-17), 61.92 (C-18), 61.08 (C-19).

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
O10.10356 (13)0.44679 (14)0.22719 (11)0.0550 (6)
O20.17214 (16)0.18400 (16)0.35130 (11)0.0680 (7)
O30.19328 (15)0.38447 (15)0.41468 (11)0.0580 (6)
O40.13031 (15)0.06439 (15)0.23538 (12)0.0664 (7)
H40.14870.07900.27840.100*
O50.06966 (14)0.05375 (15)0.08820 (12)0.0628 (6)
O60.01535 (16)0.23009 (17)0.01637 (11)0.0689 (7)
O70.10626 (19)0.83047 (17)0.22261 (12)0.0933 (9)
H70.11800.89180.23650.140*
O80.18948 (15)0.90225 (15)0.34888 (11)0.0644 (6)
C10.14122 (19)0.4598 (2)0.29820 (16)0.0480 (8)
C20.1642 (2)0.3729 (2)0.34099 (16)0.0484 (8)
C30.1526 (2)0.2643 (2)0.31198 (16)0.0504 (8)
C40.11760 (19)0.2561 (2)0.23601 (16)0.0485 (8)
C50.1063 (2)0.1553 (2)0.19902 (17)0.0508 (8)
C60.0737 (2)0.1504 (2)0.12589 (18)0.0525 (8)
C70.0477 (2)0.2451 (2)0.08770 (17)0.0536 (8)
C80.0565 (2)0.3440 (2)0.12257 (17)0.0533 (8)
H80.03890.40670.09770.064*
C90.0923 (2)0.3469 (2)0.19569 (17)0.0493 (8)
C100.15109 (19)0.5750 (2)0.31604 (16)0.0466 (7)
C110.1225 (2)0.6522 (2)0.26386 (16)0.0562 (9)
H110.09430.63000.21910.067*
C120.1348 (2)0.7597 (2)0.27640 (16)0.0539 (8)
C130.1771 (2)0.7936 (2)0.34253 (17)0.0503 (8)
C140.2050 (2)0.7194 (2)0.39501 (18)0.0733 (11)
H140.23300.74200.43980.088*
C150.1918 (2)0.6109 (2)0.38198 (18)0.0703 (10)
H150.21090.56140.41840.084*
C160.2811 (2)0.3524 (3)0.43013 (19)0.0726 (10)
H16A0.29620.36340.48280.109*
H16B0.31840.39470.40000.109*
H16C0.28750.27780.41790.109*
C170.0089 (2)0.0032 (2)0.09907 (19)0.0712 (10)
H17A0.00820.07010.07200.107*
H17B0.05690.03930.08040.107*
H17C0.01440.01710.15210.107*
C180.0157 (3)0.3214 (3)0.02592 (19)0.0772 (11)
H18A0.03640.29870.07540.116*
H18B0.03020.37220.03070.116*
H18C0.06190.35450.00010.116*
C190.2268 (2)0.9419 (2)0.41854 (18)0.0703 (10)
H19A0.23241.01860.41570.106*
H19B0.28270.91030.42770.106*
H19C0.19040.92360.45910.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0704 (15)0.0368 (11)0.0568 (13)0.0033 (10)0.0070 (11)0.0081 (9)
O20.1003 (19)0.0421 (12)0.0609 (13)0.0122 (12)0.0050 (13)0.0049 (10)
O30.0742 (16)0.0501 (12)0.0495 (13)0.0019 (11)0.0004 (12)0.0012 (10)
O40.0964 (18)0.0389 (12)0.0633 (13)0.0078 (12)0.0026 (13)0.0017 (10)
O50.0716 (16)0.0448 (12)0.0727 (14)0.0058 (11)0.0100 (13)0.0199 (10)
O60.0910 (19)0.0577 (14)0.0571 (14)0.0039 (12)0.0082 (13)0.0114 (11)
O70.170 (3)0.0467 (13)0.0603 (14)0.0082 (15)0.0285 (16)0.0019 (11)
O80.0873 (17)0.0373 (12)0.0674 (14)0.0047 (11)0.0107 (13)0.0111 (10)
C10.056 (2)0.0422 (17)0.0467 (17)0.0059 (15)0.0061 (16)0.0072 (14)
C20.058 (2)0.0418 (16)0.0458 (17)0.0083 (15)0.0039 (16)0.0054 (14)
C30.058 (2)0.0398 (17)0.0541 (18)0.0084 (15)0.0056 (16)0.0007 (14)
C40.054 (2)0.0380 (16)0.0533 (17)0.0077 (14)0.0053 (15)0.0057 (14)
C50.060 (2)0.0353 (17)0.058 (2)0.0053 (15)0.0080 (17)0.0012 (14)
C60.058 (2)0.0407 (18)0.060 (2)0.0063 (15)0.0109 (17)0.0112 (15)
C70.056 (2)0.0508 (19)0.0533 (18)0.0076 (16)0.0003 (16)0.0075 (15)
C80.058 (2)0.0427 (18)0.058 (2)0.0036 (15)0.0042 (17)0.0026 (14)
C90.056 (2)0.0374 (17)0.0552 (19)0.0020 (14)0.0047 (16)0.0088 (14)
C100.0492 (19)0.0404 (16)0.0503 (17)0.0026 (14)0.0023 (15)0.0064 (13)
C110.075 (2)0.0461 (19)0.0472 (17)0.0054 (16)0.0036 (17)0.0071 (14)
C120.073 (2)0.0414 (17)0.0464 (17)0.0006 (16)0.0028 (17)0.0015 (14)
C130.057 (2)0.0363 (16)0.0579 (18)0.0025 (15)0.0009 (17)0.0108 (15)
C140.105 (3)0.045 (2)0.068 (2)0.0086 (19)0.030 (2)0.0133 (17)
C150.100 (3)0.0432 (19)0.066 (2)0.0105 (18)0.025 (2)0.0049 (16)
C160.084 (3)0.062 (2)0.070 (2)0.004 (2)0.013 (2)0.0025 (17)
C170.079 (3)0.052 (2)0.082 (2)0.0181 (19)0.005 (2)0.0177 (17)
C180.091 (3)0.075 (2)0.064 (2)0.004 (2)0.010 (2)0.0012 (19)
C190.078 (3)0.050 (2)0.081 (2)0.0056 (17)0.020 (2)0.0264 (17)
Geometric parameters (Å, º) top
O1—C91.370 (3)C8—C91.384 (4)
O1—C11.370 (3)C8—H80.9300
O2—C31.247 (3)C10—C151.375 (4)
O3—C21.367 (3)C10—C111.390 (4)
O3—C161.436 (4)C11—C121.369 (4)
O4—C51.346 (3)C11—H110.9300
O4—H40.8200C12—C131.381 (4)
O5—C61.375 (3)C13—C141.365 (4)
O5—C171.432 (4)C14—C151.384 (4)
O6—C71.349 (3)C14—H140.9300
O6—C181.432 (4)C15—H150.9300
O7—C121.355 (3)C16—H16A0.9600
O7—H70.8200C16—H16B0.9600
O8—C131.369 (3)C16—H16C0.9600
O8—C191.425 (3)C17—H17A0.9600
C1—C21.358 (4)C17—H17B0.9600
C1—C101.475 (4)C17—H17C0.9600
C2—C31.454 (4)C18—H18A0.9600
C3—C41.429 (4)C18—H18B0.9600
C4—C91.384 (4)C18—H18C0.9600
C4—C51.422 (4)C19—H19A0.9600
C5—C61.368 (4)C19—H19B0.9600
C6—C71.408 (4)C19—H19C0.9600
C7—C81.382 (4)
C9—O1—C1121.4 (2)C12—C11—H11119.0
C2—O3—C16115.0 (2)C10—C11—H11119.0
C5—O4—H4109.5O7—C12—C11118.9 (3)
C6—O5—C17112.9 (2)O7—C12—C13121.6 (3)
C7—O6—C18118.8 (2)C11—C12—C13119.5 (3)
C12—O7—H7109.5C14—C13—O8125.0 (3)
C13—O8—C19117.6 (2)C14—C13—C12119.5 (3)
C2—C1—O1120.4 (2)O8—C13—C12115.5 (3)
C2—C1—C10129.3 (3)C13—C14—C15120.5 (3)
O1—C1—C10110.3 (2)C13—C14—H14119.8
C1—C2—O3120.9 (2)C15—C14—H14119.8
C1—C2—C3121.3 (3)C10—C15—C14121.1 (3)
O3—C2—C3117.7 (2)C10—C15—H15119.5
O2—C3—C4122.6 (3)C14—C15—H15119.5
O2—C3—C2121.7 (3)O3—C16—H16A109.5
C4—C3—C2115.7 (3)O3—C16—H16B109.5
C9—C4—C5117.2 (3)H16A—C16—H16B109.5
C9—C4—C3120.8 (2)O3—C16—H16C109.5
C5—C4—C3121.9 (3)H16A—C16—H16C109.5
O4—C5—C6119.8 (2)H16B—C16—H16C109.5
O4—C5—C4119.8 (3)O5—C17—H17A109.5
C6—C5—C4120.4 (3)O5—C17—H17B109.5
C5—C6—O5120.2 (3)H17A—C17—H17B109.5
C5—C6—C7120.1 (3)O5—C17—H17C109.5
O5—C6—C7119.6 (3)H17A—C17—H17C109.5
O6—C7—C8124.4 (3)H17B—C17—H17C109.5
O6—C7—C6114.8 (3)O6—C18—H18A109.5
C8—C7—C6120.8 (3)O6—C18—H18B109.5
C7—C8—C9117.8 (3)H18A—C18—H18B109.5
C7—C8—H8121.1O6—C18—H18C109.5
C9—C8—H8121.1H18A—C18—H18C109.5
O1—C9—C4120.2 (3)H18B—C18—H18C109.5
O1—C9—C8116.2 (2)O8—C19—H19A109.5
C4—C9—C8123.5 (3)O8—C19—H19B109.5
C15—C10—C11117.3 (3)H19A—C19—H19B109.5
C15—C10—C1122.4 (3)O8—C19—H19C109.5
C11—C10—C1120.2 (3)H19A—C19—H19C109.5
C12—C11—C10122.0 (3)H19B—C19—H19C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O4i0.822.162.942 (3)161
C17—H17A···O6ii0.962.533.482 (4)171
C19—H19A···O2i0.962.513.334 (4)144
O4—H4···O20.821.862.591 (3)148
O7—H7···O80.822.242.681 (3)115
Symmetry codes: (i) x, y+1, z; (ii) x, y, z.
 

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