organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Tectorigenin monohydrate: an isoflavone from Belamcanda chinensis

aSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, bCollege of Grain and Food, Henan University of Technology, Zhengzhou 450052, People's Republic of China, and cJilin Key Laboratory for Biotechnology of Agricultural Products Processing, Changchun University, Changchun 130022, People's Republic of China
*Correspondence e-mail: benguoliu2008@yahoo.com.cn

(Received 20 September 2008; accepted 24 September 2008; online 4 October 2008)

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[Oh, K. B., Kang, H. & Matsuoka, H. (2001). Biosci. Biotechnol. Biochem. 65, 939-942.]). For a related structure, see: Gao et al. (2008[Gao, H., Li, G., Zhang, J. & Zeng, J. (2008). Acta Cryst. E64, o1538.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12O6·H2O

  • Mr = 318.27

  • Monoclinic, P 21 /c

  • 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.973, Tmax = 0.998

  • 9180 measured reflections

  • 2967 independent reflections

  • 2069 reflections with I > 2σ(I)

  • Rint = 0.085

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O7—H7B⋯O2i 0.77 (3) 2.57 (2) 2.971 (2) 114 (2)
O7—H7A⋯O6ii 0.95 (3) 1.95 (3) 2.884 (2) 167 (2)
O6—H6⋯O1iii 0.88 (2) 1.88 (2) 2.7368 (17) 167 (2)
O3—H3⋯O5 0.90 (2) 1.71 (2) 2.5658 (16) 159.6 (18)
O1—H1⋯O7iv 0.87 (2) 1.83 (2) 2.6630 (17) 160.4 (19)
Symmetry codes: (i) x, y, z+1; (ii) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) x+1, y, z+1; (iv) x, y, z-1.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

For general background, see: Oh et al. (2001). For related structures, see: Gao et al. (2008).

Experimental top

The title compound was isolated from Belamcanda chinensis.

Refinement top

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).

Computing details top

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

Figures top
[Figure 1] 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.
5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one monohydrate top
Crystal data top
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 top
Rigaku Saturn CCD area-detector
diffractometer
2967 independent reflections
Radiation source: rotating anode2069 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.085
Detector resolution: 7.31 pixels mm-1θmax = 27.1°, θmin = 1.6°
ω and ϕ scansh = 1616
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 1518
Tmin = 0.973, Tmax = 0.998l = 97
9180 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 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
Crystal data top
C16H12O6·H2OV = 1346.0 (5) Å3
Mr = 318.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.971 (3) ŵ = 0.13 mm1
b = 14.652 (3) ÅT = 113 K
c = 7.2930 (15) Å0.14 × 0.04 × 0.02 mm
β = 103.81 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
2967 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2069 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.998Rint = 0.085
9180 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.33 e Å3
2967 reflectionsΔρmin = 0.27 e Å3
224 parameters
Special details top

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
O10.15492 (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) top
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, º) top
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—C1110.33 (18)
C4—O4—C3—C2177.22 (16)O3—C8—C9—O25.6 (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—C72.2 (3)C7—C8—C9—C12.1 (3)
C3—O4—C4—C54.9 (3)O1—C1—C9—O26.3 (3)
O4—C4—C5—C62.7 (3)C2—C1—C9—O2173.97 (17)
O4—C4—C5—C11178.42 (17)O1—C1—C9—C8177.84 (17)
C4—C5—C6—O5177.81 (18)C2—C1—C9—C81.9 (3)
C11—C5—C6—O53.3 (3)C4—C5—C11—C16139.51 (19)
C4—C5—C6—C72.0 (3)C6—C5—C11—C1639.4 (3)
C11—C5—C6—C7176.86 (16)C4—C5—C11—C1239.3 (3)
O4—C3—C7—C8177.26 (17)C6—C5—C11—C12141.85 (18)
C2—C3—C7—C82.0 (3)C16—C11—C12—C130.7 (3)
O4—C3—C7—C62.6 (3)C5—C11—C12—C13179.49 (16)
C2—C3—C7—C6178.17 (18)C11—C12—C13—C140.5 (3)
O5—C6—C7—C3175.31 (19)C12—C13—C14—O6177.31 (16)
C5—C6—C7—C34.5 (3)C12—C13—C14—C152.1 (3)
O5—C6—C7—C84.8 (3)C13—C14—C15—C162.4 (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—O30.4 (3)C5—C11—C16—C15179.12 (17)
C3—C7—C8—C90.2 (3)C14—C15—C16—C111.2 (3)
C6—C7—C8—C9179.67 (17)
Hydrogen-bond geometry (Å, º) top
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) x1, y+3/2, z1/2; (iii) x+1, y, z+1; (iv) x, y, z1.

Experimental details

Crystal data
Chemical formulaC16H12O6·H2O
Mr318.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)12.971 (3), 14.652 (3), 7.2930 (15)
β (°) 103.81 (3)
V3)1346.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.14 × 0.04 × 0.02
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.973, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
9180, 2967, 2069
Rint0.085
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.117, 1.00
No. of reflections2967
No. of parameters224
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.27

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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) x1, y+3/2, z1/2; (iii) x+1, y, z+1; (iv) x, y, z1.
 

References

First citationGao, H., Li, G., Zhang, J. & Zeng, J. (2008). Acta Cryst. E64, o1538.  Web of Science CSD CrossRef IUCr Journals
First citationOh, K. B., Kang, H. & Matsuoka, H. (2001). Biosci. Biotechnol. Biochem. 65, 939–942.  Web of Science CrossRef PubMed CAS
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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