5,6-Dihy-droxy-7,8-di-meth-oxy-flavone.

THE TITLE COMPOUND (SYSTEMATIC NAME: 5,6-dihy-droxy-7,8-dimeth-oxy-2-phenyl-chromen-4-one), C17H14O6, is a flavone that was isolated from the petroleum ether-soluble fraction of the rare traditional Chinese medicinal herb Saussurea involucrata. The flavone mol-ecule is almost planar, with a dihedral angle between the planes of the benzo-pyran-4-one group and the attached phenyl group of 1.89 (6)°. The 5-hy-droxy group forms a strong intra-molecular hydrogen bond with the carbonyl group, resulting in a six-membered hydrogen-bonded ring. The 6-hy-droxy group also forms an intra-molecular O-H⋯O contact. In the crystal, the molecules are linked by O-H⋯O and C-H⋯O hydrogen bonds and π-π inter-actions [3.37 (2)-3.39 (2) Å], which build up a three-dimensional network.

Related literature

For biological activity of Saussurea involucrata, see: Zheng et al. (1993 ▶); Gao et al. (2005 ▶); Tao et al.(2010 ▶); Ma et al. (2011 ▶); Jia et al. (2005 ▶); Liu et al. (1985 ▶). For related structures, see: Xiong et al. (2009 ▶); Vijayalakshmi et al. (1986 ▶); Paula et al. (2002 ▶).

Experimental

Crystal data

C17H14O6

M = 314.28

Triclinic,

a = 7.953 (6) Å

b = 8.548 (6) Å

c = 10.951 (8) Å

α = 96.602 (8)°

β = 92.282 (8)°

γ = 100.279 (7)°

V = 726.3 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.21 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

5252 measured reflections

3368 independent reflections

1786 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.236

S = 1.03

3368 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014451/rk2401sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014451/rk2401Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014451/rk2401Isup3.cml

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

C17H14O6	Z = 2
Mr = 314.28	F(000) = 328
Triclinic, P1	Dx = 1.437 Mg m−3
a = 7.953 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.548 (6) Å	Cell parameters from 1607 reflections
c = 10.951 (8) Å	θ = 2.4–28.0°
α = 96.602 (8)°	µ = 0.11 mm−1
β = 92.282 (8)°	T = 295 K
γ = 100.279 (7)°	Block, orange
V = 726.3 (9) Å3	0.21 × 0.16 × 0.09 mm

Bruker APEXII CCD diffractometer	1786 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 28.3°, θmin = 2.4°
φ and ω scans	h = −9→10
5252 measured reflections	k = −10→11
3368 independent reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1286P)2] where P = (Fo2 + 2Fc2)/3
3368 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
O1	0.6956 (2)	0.4357 (2)	0.24860 (16)	0.0386 (5)
O2	0.3542 (3)	0.1892 (2)	−0.02333 (18)	0.0489 (6)
O3	0.1717 (2)	0.4078 (2)	0.00746 (18)	0.0450 (5)
H3	0.1947	0.3212	−0.0196	0.067*
O4	0.1217 (3)	0.6852 (2)	0.14665 (19)	0.0512 (6)
H4	0.0594	0.6291	0.0909	0.077*
O5	0.3574 (3)	0.8349 (2)	0.32644 (18)	0.0528 (6)
O6	0.6457 (2)	0.7095 (2)	0.38048 (16)	0.0450 (5)
C1	0.7247 (3)	0.2981 (3)	0.1857 (2)	0.0354 (6)
C2	0.6135 (4)	0.2132 (3)	0.0965 (3)	0.0405 (7)
H2	0.6368	0.1175	0.0576	0.049*
C3	0.4604 (3)	0.2653 (3)	0.0593 (2)	0.0359 (6)
C4	0.4325 (3)	0.4143 (3)	0.1259 (2)	0.0303 (6)
C5	0.2887 (3)	0.4797 (3)	0.1000 (2)	0.0334 (6)
C6	0.2615 (3)	0.6188 (3)	0.1678 (2)	0.0367 (6)
C7	0.3817 (4)	0.6939 (3)	0.2618 (2)	0.0377 (7)
C8	0.5273 (3)	0.6333 (3)	0.2885 (2)	0.0360 (6)
C9	0.5500 (3)	0.4924 (3)	0.2197 (2)	0.0338 (6)
C10	0.8873 (3)	0.2593 (3)	0.2294 (2)	0.0362 (6)
C11	0.9879 (4)	0.3551 (4)	0.3266 (3)	0.0457 (7)
H11	0.9524	0.4461	0.3637	0.055*
C12	1.1388 (4)	0.3168 (4)	0.3683 (3)	0.0555 (9)
H12	1.2037	0.3809	0.4340	0.067*
C13	1.1942 (4)	0.1838 (4)	0.3130 (3)	0.0558 (9)
H13	1.2969	0.1584	0.3407	0.067*
C14	1.0974 (4)	0.0895 (4)	0.2172 (3)	0.0569 (9)
H14	1.1342	−0.0010	0.1805	0.068*
C15	0.9459 (4)	0.1264 (4)	0.1742 (3)	0.0492 (8)
H15	0.8826	0.0620	0.1079	0.059*
C16	0.2964 (6)	0.8185 (5)	0.4437 (4)	0.0927 (14)
H16A	0.1833	0.7547	0.4353	0.139*
H16B	0.2929	0.9224	0.4862	0.139*
H16C	0.3712	0.7671	0.4897	0.139*
C17	0.7790 (5)	0.8185 (4)	0.3370 (3)	0.0655 (10)
H17A	0.8386	0.7615	0.2774	0.098*
H17B	0.8575	0.8694	0.4048	0.098*
H17C	0.7313	0.8982	0.2995	0.098*

	U11	U22	U33	U12	U13	U23
O1	0.0383 (11)	0.0392 (11)	0.0415 (10)	0.0216 (9)	−0.0029 (8)	−0.0015 (8)
O2	0.0437 (12)	0.0463 (12)	0.0544 (12)	0.0171 (9)	−0.0080 (9)	−0.0127 (9)
O3	0.0383 (12)	0.0452 (12)	0.0511 (12)	0.0182 (9)	−0.0083 (9)	−0.0080 (9)
O4	0.0429 (13)	0.0525 (13)	0.0612 (14)	0.0296 (10)	−0.0074 (10)	−0.0096 (10)
O5	0.0668 (15)	0.0453 (12)	0.0497 (12)	0.0305 (11)	0.0005 (10)	−0.0101 (9)
O6	0.0451 (12)	0.0519 (12)	0.0370 (11)	0.0143 (10)	−0.0040 (9)	−0.0044 (9)
C1	0.0384 (16)	0.0329 (14)	0.0393 (15)	0.0161 (12)	0.0063 (12)	0.0063 (11)
C2	0.0404 (17)	0.0367 (15)	0.0476 (16)	0.0201 (13)	0.0026 (13)	−0.0020 (12)
C3	0.0344 (15)	0.0381 (15)	0.0365 (14)	0.0121 (12)	0.0019 (11)	0.0009 (11)
C4	0.0321 (14)	0.0321 (14)	0.0290 (13)	0.0118 (11)	0.0047 (10)	0.0031 (10)
C5	0.0310 (15)	0.0388 (15)	0.0315 (13)	0.0112 (12)	0.0005 (11)	0.0027 (10)
C6	0.0340 (15)	0.0395 (15)	0.0406 (15)	0.0186 (12)	0.0018 (11)	0.0035 (11)
C7	0.0423 (17)	0.0371 (15)	0.0376 (14)	0.0198 (13)	0.0069 (12)	−0.0001 (11)
C8	0.0402 (16)	0.0409 (15)	0.0277 (13)	0.0140 (12)	0.0011 (11)	−0.0017 (10)
C9	0.0320 (15)	0.0403 (15)	0.0329 (14)	0.0166 (12)	0.0016 (11)	0.0052 (11)
C10	0.0338 (15)	0.0364 (15)	0.0433 (15)	0.0141 (12)	0.0069 (12)	0.0121 (11)
C11	0.0458 (18)	0.0488 (18)	0.0464 (16)	0.0202 (14)	0.0006 (13)	0.0051 (13)
C12	0.046 (2)	0.068 (2)	0.0549 (19)	0.0154 (17)	−0.0082 (15)	0.0124 (16)
C13	0.0407 (19)	0.065 (2)	0.071 (2)	0.0237 (17)	0.0030 (16)	0.0252 (18)
C14	0.048 (2)	0.0475 (19)	0.082 (2)	0.0252 (16)	0.0080 (17)	0.0113 (17)
C15	0.0446 (18)	0.0439 (17)	0.0628 (19)	0.0200 (14)	0.0016 (14)	0.0043 (14)
C16	0.134 (4)	0.090 (3)	0.066 (2)	0.055 (3)	0.041 (2)	−0.006 (2)
C17	0.064 (2)	0.063 (2)	0.060 (2)	−0.0004 (18)	0.0005 (17)	−0.0104 (16)

O1—C1	1.355 (3)	C7—C8	1.384 (4)
O1—C9	1.372 (3)	C8—C9	1.389 (4)
O2—C3	1.250 (3)	C10—C11	1.393 (4)
O3—H3	0.8200	C10—C15	1.388 (4)
O3—C5	1.360 (3)	C11—H11	0.9300
O4—H4	0.8200	C11—C12	1.374 (4)
O4—C6	1.359 (3)	C12—H12	0.9300
O5—C7	1.375 (3)	C12—C13	1.377 (5)
O5—C16	1.404 (4)	C13—H13	0.9300
O6—C8	1.372 (3)	C13—C14	1.365 (4)
O6—C17	1.417 (4)	C14—H14	0.9300
C1—C2	1.343 (4)	C14—C15	1.378 (4)
C1—C10	1.467 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—H16A	0.9600
C2—C3	1.429 (4)	C16—H16B	0.9600
C3—C4	1.450 (4)	C16—H16C	0.9600
C4—C5	1.393 (4)	C17—H17A	0.9600
C4—C9	1.385 (4)	C17—H17B	0.9600
C5—C6	1.384 (4)	C17—H17C	0.9600
C6—C7	1.391 (4)
C1—O1—C9	119.6 (2)	C4—C9—C8	121.7 (2)
C5—O3—H3	109.5	C11—C10—C1	121.1 (2)
C6—O4—H4	109.5	C15—C10—C1	120.8 (3)
C7—O5—C16	114.1 (3)	C15—C10—C11	118.1 (3)
C8—O6—C17	112.7 (2)	C10—C11—H11	119.6
O1—C1—C10	111.1 (2)	C12—C11—C10	120.8 (3)
C2—C1—O1	121.9 (2)	C12—C11—H11	119.6
C2—C1—C10	127.0 (2)	C11—C12—H12	119.9
C1—C2—H2	119.0	C11—C12—C13	120.2 (3)
C1—C2—C3	122.1 (2)	C13—C12—H12	119.9
C3—C2—H2	119.0	C12—C13—H13	120.2
O2—C3—C2	123.7 (2)	C14—C13—C12	119.5 (3)
O2—C3—C4	120.9 (2)	C14—C13—H13	120.2
C2—C3—C4	115.4 (2)	C13—C14—H14	119.5
C5—C4—C3	121.9 (2)	C13—C14—C15	121.0 (3)
C9—C4—C3	119.3 (2)	C15—C14—H14	119.5
C9—C4—C5	118.8 (2)	C10—C15—H15	119.8
O3—C5—C4	120.6 (2)	C14—C15—C10	120.3 (3)
O3—C5—C6	118.5 (2)	C14—C15—H15	119.8
C6—C5—C4	120.9 (2)	O5—C16—H16A	109.5
O4—C6—C5	122.7 (2)	O5—C16—H16B	109.5
O4—C6—C7	118.5 (2)	O5—C16—H16C	109.5
C5—C6—C7	118.8 (2)	H16A—C16—H16B	109.5
O5—C7—C6	118.7 (2)	H16A—C16—H16C	109.5
O5—C7—C8	119.5 (2)	H16B—C16—H16C	109.5
C8—C7—C6	121.7 (2)	O6—C17—H17A	109.5
O6—C8—C7	121.1 (2)	O6—C17—H17B	109.5
O6—C8—C9	120.8 (2)	O6—C17—H17C	109.5
C7—C8—C9	118.1 (2)	H17A—C17—H17B	109.5
O1—C9—C4	121.7 (2)	H17A—C17—H17C	109.5
O1—C9—C8	116.6 (2)	H17B—C17—H17C	109.5
O1—C1—C2—C3	2.1 (4)	C3—C4—C9—C8	−178.3 (2)
O1—C1—C10—C11	2.1 (4)	C4—C5—C6—O4	−179.0 (2)
O1—C1—C10—C15	−177.4 (3)	C4—C5—C6—C7	0.8 (4)
O2—C3—C4—C5	−0.7 (4)	C5—C4—C9—O1	−179.0 (2)
O2—C3—C4—C9	177.8 (2)	C5—C4—C9—C8	0.3 (4)
O3—C5—C6—O4	0.9 (4)	C5—C6—C7—O5	177.9 (2)
O3—C5—C6—C7	−179.3 (2)	C5—C6—C7—C8	0.3 (4)
O4—C6—C7—O5	−2.3 (4)	C6—C7—C8—O6	179.2 (2)
O4—C6—C7—C8	−179.9 (3)	C6—C7—C8—C9	−1.0 (4)
O5—C7—C8—O6	1.6 (4)	C7—C8—C9—O1	−180.0 (2)
O5—C7—C8—C9	−178.6 (2)	C7—C8—C9—C4	0.7 (4)
O6—C8—C9—O1	−0.2 (4)	C9—O1—C1—C2	−1.1 (4)
O6—C8—C9—C4	−179.5 (2)	C9—O1—C1—C10	179.3 (2)
C1—O1—C9—C4	−1.3 (4)	C9—C4—C5—O3	179.1 (2)
C1—O1—C9—C8	179.4 (2)	C9—C4—C5—C6	−1.1 (4)
C1—C2—C3—O2	180.0 (3)	C10—C1—C2—C3	−178.3 (2)
C1—C2—C3—C4	−0.9 (4)	C10—C11—C12—C13	1.0 (5)
C1—C10—C11—C12	179.0 (3)	C11—C10—C15—C14	1.5 (5)
C1—C10—C15—C14	−178.9 (3)	C11—C12—C13—C14	−0.6 (5)
C2—C1—C10—C11	−177.5 (3)	C12—C13—C14—C15	0.7 (5)
C2—C1—C10—C15	3.0 (4)	C13—C14—C15—C10	−1.2 (5)
C2—C3—C4—C5	−179.9 (2)	C15—C10—C11—C12	−1.5 (5)
C2—C3—C4—C9	−1.3 (4)	C16—O5—C7—C6	103.2 (4)
C3—C4—C5—O3	−2.4 (4)	C16—O5—C7—C8	−79.2 (4)
C3—C4—C5—C6	177.5 (2)	C17—O6—C8—C7	−92.6 (3)
C3—C4—C9—O1	2.4 (4)	C17—O6—C8—C9	87.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	2.05	2.764 (4)	146
C12—H12···O6ii	0.93	2.58	3.234 (4)	128
O3—H3···O2	0.82	1.84	2.564 (3)	146
O4—H4···O3	0.82	2.34	2.767 (3)	113
C11—H11···O1	0.93	2.34	2.675 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	2.05	2.764 (4)	146
C12—H12⋯O6ii	0.93	2.58	3.234 (4)	128
O3—H3⋯O2	0.82	1.84	2.564 (3)	146
O4—H4⋯O3	0.82	2.34	2.767 (3)	113

Symmetry codes: (i) ; (ii) .