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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2056.
Published online 2008 October 4. doi:  10.1107/S1600536808030833
PMCID: PMC2959614

Tectorigenin monohydrate: an isoflavone from Belamcanda chinensis

Abstract

The title compound [systematic name: 5,7-dihydr­oxy-3-(4-hydroxy­phen­yl)-6-meth­oxy-4H-chromen-4-one monohydrate], C16H12O6·H2O, is isolated from Belamcanda chinensis and is said to have anti­microbiotic and anti-inflammatory effects. The chromen-4-one system and the benzene ring are inclined at a dihedral angle of 36.79 (6)°. Molecules are linked by inter- and intramolecular O—H(...)O hydrogen bonds.

Related literature

For general background, see: Oh et al. (2001 [triangle]). For a related structure, see: Gao et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2056-scheme1.jpg

Experimental

Crystal data

  • C16H12O6·H2O
  • M r = 318.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2056-efi1.jpg
  • a = 12.971 (3) Å
  • b = 14.652 (3) Å
  • c = 7.2930 (15) Å
  • β = 103.81 (3)°
  • V = 1346.0 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 113 (2) K
  • 0.14 × 0.04 × 0.02 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.973, T max = 0.998
  • 9180 measured reflections
  • 2967 independent reflections
  • 2069 reflections with I > 2σ(I)
  • R int = 0.085

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.117
  • S = 1.00
  • 2967 reflections
  • 224 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030833/bt2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030833/bt2795Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound [systematic name: 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one] was isolated from Belamcanda chinensis and is said to have antimicrobiotic and anti-inflammatory effects. We report here the crystal structure of its monohydrate. The two aromatic ring systems rings are inclined at a dihedral angle of 36.79 (6)°. The molecules are linked by intermolecular O—H···O hydrogen bonds (Table 1).

Experimental

The title compound was isolated from Belamcanda chinensis.

Refinement

H atoms bonded to C were positioned geometrically (C—H=0.95–0.98 Å), and refined as riding with Uiso(H)=1.2Ueq(C) or 1.5eq(Cmethyl). The coordinates of the H atoms bonded to O were refined with Uiso(H)=1.5Ueq(O).

Figures

Fig. 1.
A view of the title compound. Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Crystal data

C16H12O6·H2OF(000) = 664
Mr = 318.27Dx = 1.571 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2562 reflections
a = 12.971 (3) Åθ = 1.6–27.1°
b = 14.652 (3) ŵ = 0.13 mm1
c = 7.2930 (15) ÅT = 113 K
β = 103.81 (3)°Block, colorless
V = 1346.0 (5) Å30.14 × 0.04 × 0.02 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer2967 independent reflections
Radiation source: rotating anode2069 reflections with I > 2σ(I)
confocalRint = 0.085
Detector resolution: 7.31 pixels mm-1θmax = 27.1°, θmin = 1.6°
ω and [var phi] scansh = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −15→18
Tmin = 0.973, Tmax = 0.998l = −9→7
9180 measured reflections

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0629P)2] where P = (Fo2 + 2Fc2)/3
2967 reflections(Δ/σ)max = 0.001
224 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = −0.27 e Å3

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
O10.15492 (10)0.72865 (7)−0.00354 (17)0.0204 (3)
H10.1297 (17)0.6740 (14)−0.033 (3)0.031*
O20.26095 (9)0.56579 (7)0.09198 (16)0.0191 (3)
O30.45733 (10)0.56828 (7)0.34259 (17)0.0193 (3)
H30.5174 (18)0.5889 (13)0.420 (3)0.029*
O40.45077 (9)0.89559 (7)0.32487 (17)0.0173 (3)
O50.61065 (9)0.66388 (7)0.53713 (16)0.0188 (3)
O61.02531 (10)0.87836 (8)0.95714 (18)0.0221 (3)
H61.0680 (18)0.8325 (15)0.952 (3)0.033*
C10.25505 (13)0.72879 (10)0.1088 (2)0.0159 (4)
C20.30232 (13)0.81198 (9)0.1645 (2)0.0161 (4)
H20.26600.86760.12540.019*
C30.40402 (13)0.81206 (9)0.2788 (2)0.0142 (4)
C40.55224 (13)0.89830 (10)0.4301 (2)0.0157 (4)
H40.58500.95660.45200.019*
C50.61050 (13)0.82575 (10)0.5063 (2)0.0141 (4)
C60.56447 (13)0.73485 (10)0.4688 (2)0.0142 (4)
C70.45876 (13)0.73227 (10)0.3443 (2)0.0141 (4)
C80.40834 (13)0.64784 (9)0.2855 (2)0.0148 (4)
C90.30772 (14)0.64647 (9)0.1659 (2)0.0155 (4)
C100.22428 (15)0.50987 (11)0.2257 (3)0.0243 (5)
H10A0.16890.54250.27020.036*
H10B0.28380.49630.33320.036*
H10C0.19520.45270.16480.036*
C110.71993 (13)0.83905 (9)0.6228 (2)0.0153 (4)
C120.74392 (14)0.91262 (9)0.7482 (2)0.0157 (4)
H120.68950.95410.75950.019*
C130.84645 (14)0.92549 (9)0.8561 (2)0.0172 (4)
H130.86220.97590.94010.021*
C140.92533 (13)0.86514 (10)0.8412 (2)0.0165 (4)
C150.90422 (14)0.79282 (10)0.7145 (2)0.0197 (4)
H150.95940.75260.70100.024*
C160.80091 (14)0.78018 (10)0.6076 (2)0.0185 (4)
H160.78570.73020.52250.022*
O70.04211 (12)0.58284 (9)0.8508 (2)0.0333 (4)
H7A0.033 (2)0.5862 (15)0.718 (4)0.050*
H7B0.076 (2)0.5390 (18)0.876 (4)0.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0144 (7)0.0182 (6)0.0251 (7)0.0000 (4)−0.0024 (5)−0.0017 (4)
O20.0203 (7)0.0157 (5)0.0204 (6)−0.0030 (4)0.0031 (5)−0.0024 (4)
O30.0178 (7)0.0122 (5)0.0247 (7)0.0012 (4)−0.0012 (5)0.0003 (4)
O40.0142 (6)0.0122 (5)0.0233 (6)0.0001 (4)0.0001 (5)0.0003 (4)
O50.0170 (6)0.0151 (5)0.0228 (6)0.0026 (4)0.0018 (5)0.0022 (4)
O60.0142 (7)0.0193 (6)0.0287 (7)0.0001 (5)−0.0033 (5)−0.0036 (4)
C10.0118 (8)0.0211 (8)0.0142 (8)0.0007 (6)0.0023 (7)−0.0008 (5)
C20.0150 (9)0.0167 (7)0.0167 (8)0.0031 (6)0.0039 (7)0.0011 (5)
C30.0144 (8)0.0137 (7)0.0156 (8)−0.0020 (6)0.0060 (7)−0.0013 (5)
C40.0135 (8)0.0167 (7)0.0169 (8)−0.0019 (6)0.0038 (7)−0.0018 (5)
C50.0129 (8)0.0162 (7)0.0144 (8)0.0003 (6)0.0054 (7)−0.0015 (5)
C60.0142 (9)0.0158 (7)0.0135 (8)0.0009 (6)0.0052 (7)0.0000 (5)
C70.0118 (8)0.0161 (7)0.0149 (8)0.0013 (6)0.0043 (7)0.0006 (5)
C80.0165 (9)0.0141 (7)0.0146 (8)0.0008 (6)0.0053 (7)0.0006 (5)
C90.0182 (9)0.0141 (7)0.0149 (8)−0.0021 (6)0.0054 (7)−0.0012 (5)
C100.0250 (10)0.0205 (8)0.0285 (10)−0.0043 (7)0.0090 (8)0.0021 (6)
C110.0152 (9)0.0140 (7)0.0159 (8)−0.0019 (6)0.0023 (7)0.0016 (5)
C120.0162 (9)0.0136 (7)0.0181 (8)0.0019 (6)0.0056 (7)0.0015 (5)
C130.0199 (10)0.0125 (7)0.0186 (8)−0.0029 (6)0.0033 (7)−0.0018 (5)
C140.0132 (8)0.0169 (7)0.0181 (8)−0.0018 (6)0.0013 (7)0.0022 (5)
C150.0153 (9)0.0183 (7)0.0253 (9)0.0030 (6)0.0045 (7)−0.0031 (6)
C160.0177 (9)0.0179 (7)0.0192 (9)−0.0006 (6)0.0030 (7)−0.0047 (5)
O70.0329 (9)0.0253 (6)0.0358 (9)0.0005 (6)−0.0037 (7)−0.0060 (5)

Geometric parameters (Å, °)

O1—C11.3602 (18)C5—C111.483 (2)
O1—H10.87 (2)C6—C71.453 (2)
O2—C91.3784 (16)C7—C81.4171 (19)
O2—C101.439 (2)C8—C91.386 (2)
O3—C81.3453 (17)C10—H10A0.9800
O3—H30.90 (2)C10—H10B0.9800
O4—C41.3568 (18)C10—H10C0.9800
O4—C31.3717 (16)C11—C161.384 (2)
O5—C61.2434 (17)C11—C121.400 (2)
O6—C141.3823 (18)C12—C131.387 (2)
O6—H60.88 (2)C12—H120.9500
C1—C21.381 (2)C13—C141.376 (2)
C1—C91.400 (2)C13—H130.9500
C2—C31.382 (2)C14—C151.390 (2)
C2—H20.9500C15—C161.393 (2)
C3—C71.3917 (19)C15—H150.9500
C4—C51.345 (2)C16—H160.9500
C4—H40.9500O7—H7A0.95 (3)
C5—C61.458 (2)O7—H7B0.77 (3)
C1—O1—H1113.5 (13)O2—C9—C8121.26 (13)
C9—O2—C10114.16 (13)O2—C9—C1118.99 (13)
C8—O3—H3100.2 (12)C8—C9—C1119.62 (13)
C4—O4—C3118.50 (11)O2—C10—H10A109.5
C14—O6—H6112.1 (13)O2—C10—H10B109.5
O1—C1—C2118.13 (13)H10A—C10—H10B109.5
O1—C1—C9120.40 (13)O2—C10—H10C109.5
C2—C1—C9121.47 (13)H10A—C10—H10C109.5
C1—C2—C3118.09 (13)H10B—C10—H10C109.5
C1—C2—H2121.0C16—C11—C12118.55 (14)
C3—C2—H2121.0C16—C11—C5120.86 (13)
O4—C3—C2116.81 (12)C12—C11—C5120.58 (15)
O4—C3—C7120.39 (13)C13—C12—C11120.59 (15)
C2—C3—C7122.80 (13)C13—C12—H12119.7
C5—C4—O4125.74 (13)C11—C12—H12119.7
C5—C4—H4117.1C14—C13—C12119.88 (14)
O4—C4—H4117.1C14—C13—H13120.1
C4—C5—C6118.67 (14)C12—C13—H13120.1
C4—C5—C11119.95 (13)C13—C14—O6117.93 (14)
C6—C5—C11121.36 (13)C13—C14—C15120.68 (14)
O5—C6—C7121.41 (13)O6—C14—C15121.39 (15)
O5—C6—C5123.52 (14)C14—C15—C16118.98 (16)
C7—C6—C5115.08 (12)C14—C15—H15120.5
C3—C7—C8117.94 (13)C16—C15—H15120.5
C3—C7—C6121.37 (13)C11—C16—C15121.29 (14)
C8—C7—C6120.69 (13)C11—C16—H16119.4
O3—C8—C9119.11 (12)C15—C16—H16119.4
O3—C8—C7120.86 (13)H7A—O7—H7B102 (2)
C9—C8—C7120.03 (13)
O1—C1—C2—C3179.92 (17)C10—O2—C9—C873.9 (2)
C9—C1—C2—C30.2 (3)C10—O2—C9—C1−110.33 (18)
C4—O4—C3—C2−177.22 (16)O3—C8—C9—O2−5.6 (3)
C4—O4—C3—C72.1 (3)C7—C8—C9—O2173.72 (17)
C1—C2—C3—O4177.11 (17)O3—C8—C9—C1178.63 (17)
C1—C2—C3—C7−2.2 (3)C7—C8—C9—C1−2.1 (3)
C3—O4—C4—C5−4.9 (3)O1—C1—C9—O26.3 (3)
O4—C4—C5—C62.7 (3)C2—C1—C9—O2−173.97 (17)
O4—C4—C5—C11−178.42 (17)O1—C1—C9—C8−177.84 (17)
C4—C5—C6—O5−177.81 (18)C2—C1—C9—C81.9 (3)
C11—C5—C6—O53.3 (3)C4—C5—C11—C16−139.51 (19)
C4—C5—C6—C72.0 (3)C6—C5—C11—C1639.4 (3)
C11—C5—C6—C7−176.86 (16)C4—C5—C11—C1239.3 (3)
O4—C3—C7—C8−177.26 (17)C6—C5—C11—C12−141.85 (18)
C2—C3—C7—C82.0 (3)C16—C11—C12—C13−0.7 (3)
O4—C3—C7—C62.6 (3)C5—C11—C12—C13−179.49 (16)
C2—C3—C7—C6−178.17 (18)C11—C12—C13—C14−0.5 (3)
O5—C6—C7—C3175.31 (19)C12—C13—C14—O6−177.31 (16)
C5—C6—C7—C3−4.5 (3)C12—C13—C14—C152.1 (3)
O5—C6—C7—C8−4.8 (3)C13—C14—C15—C16−2.4 (3)
C5—C6—C7—C8175.30 (17)O6—C14—C15—C16176.94 (16)
C3—C7—C8—O3179.49 (17)C12—C11—C16—C150.3 (3)
C6—C7—C8—O3−0.4 (3)C5—C11—C16—C15179.12 (17)
C3—C7—C8—C90.2 (3)C14—C15—C16—C111.2 (3)
C6—C7—C8—C9−179.67 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7B···O2i0.77 (3)2.57 (2)2.971 (2)114 (2)
O7—H7A···O6ii0.95 (3)1.95 (3)2.884 (2)167 (2)
O6—H6···O1iii0.88 (2)1.88 (2)2.7368 (17)167 (2)
O3—H3···O50.90 (2)1.71 (2)2.5658 (16)159.6 (18)
O1—H1···O7iv0.87 (2)1.83 (2)2.6630 (17)160.4 (19)

Symmetry codes: (i) x, y, z+1; (ii) x−1, −y+3/2, z−1/2; (iii) x+1, y, z+1; (iv) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2795).

References

  • Gao, H., Li, G., Zhang, J. & Zeng, J. (2008). Acta Cryst. E64, o1538. [PMC free article] [PubMed]
  • Oh, K. B., Kang, H. & Matsuoka, H. (2001). Biosci. Biotechnol. Biochem.65, 939–942. [PubMed]
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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