5,3′-Dihydr­oxy-7,4′-dimethoxy­flavanone from Artemisia sphaerocephala Kraschen

Yao, S.; Qing, W.

doi:10.1107/S1600536808009355

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o822

doi:10.1107/S1600536808009355

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5,3′-Dihydroxy-7,4′-dimethoxyflavanone from Artemisia sphaerocephala Kraschen

Sumei Yao ^a ^* and Weixia Qing ^a

^aMedical College of Henan University, Henan University, Kaifeng 475004, People's Republic of China
^*Correspondence e-mail: ysum@yahoo.cn

(Received 6 April 2008; accepted 6 April 2008; online 10 April 2008)

The title compound, C₁₇H₁₆O₆, was isolated from the Chinese Tibetan medicinal plant Artemisia sphaerocephala Kraschen. The molecular conformation is consolidated by two intramolecular O—H⋯O hydrogen bonds. A further intermolecular O—H⋯O hydrogen bond leads to chains along [010] in the crystal structure.

Related literature

For background, see: Zhao et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₆O₆
M_r = 316.30
Monoclinic, P 2₁
a = 5.4234 (12) Å
b = 9.293 (2) Å
c = 14.940 (3) Å
β = 91.039 (2)°
V = 752.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 (2) K
0.22 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.977, T_max = 0.987
7958 measured reflections
1581 independent reflections
1489 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.077
S = 1.06
1581 reflections
212 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.85	2.579 (2)	148
O6—H5⋯O5	0.82	2.18	2.640 (2)	116
O6—H5⋯O4ⁱ	0.82	2.29	2.892 (2)	130
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009355/hb2716sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009355/hb2716Isup2.hkl

checkCIF report

Comment top

As part of the ongoing investigations of the Chinese Tibetan medicinal plant Artemisia sphaerocephala Kraschen (Zhao et al., 2007), we now report the isolation and structure of the flavone-related title compound, (I).

Compound (I) consists of three-ring system, including a phenyl ring and a benzopyrone fused ring (Fig.1). The C–O bond distances range from 1.239 (2) to 1.453 (2) Å, in which C4–O2 [1.239 (2) Å] is typical for a C=O double-bond. The S(6) ring of O1/C2/C3/C4/C9/C10 in (I) is nonplanar, charactrtized by a O1–C2–C3–C4 torsion angle of 52.9 (2) °. Atom C2 is chiral, but the absolute structure of (I) could not be established from the present experiment. The dihedral angle between the aromatic ring planes is 77.26 (9) °.

Two intramolecular O-H···O hydrogen bonds (Table 1) help to establish the molecular conformation, both constructing S(6) rings. In addition, an intermolecular O-H···O link leads to [010] chains in the crystal (Fig. 2).

Related literature top

For background, see: Zhao et al. (2007).

Experimental top

The air-dried whole plant (5.1 kg) was ground into powder and extracted three times with 95% EtOH for 3 h each time. The concentrated extract was dispersed in water and partitioned successively with petroleum ether, CHCl₃, EtOAC and n-BuOH. The chloroform fraction (115 g) was subjected to silics gel with petroleum ether-acetone (9:1) to yield two fractions (Frs. 1–2). Fraction 2 (50 g) was subjected to silics gel with petroleum ether-EtOAC (50:1, 45:1, 40:1, 30:1) to yield six fractions. After a week, the crude title compound (20 mg) was crystallized from the fourth fraction. After recrystallization from petroleum ether-EtOAC, colourless blocks of (I) arose, with a melting point of 475 K. The molecular formula, C₁₇H₁₆O₆, was established by ESIMS m/z:316(M+). Spectroscopic analysis, 1H NMR (400 MHz, DMSO-d6) δ: 12.15 (1H, s), 6.08 (1H, d, J=2.2 Hz), 6.05 (1H, d, J=2.2 Hz), 5.47 (1H, dd, J=12.6 Hz, 3.0 Hz), 3.20 (1H, dd, J=15.5 Hz, 12.6 Hz), 2.82 (1H, dd, J=15.5 Hz, 3.0 Hz); 13 C NMR (400 MHz, DMSO-d6) δ: 197.0 (C-4), 168.0 (C-7), 163.8 (C-5), 163.1 (C-9), 147.8 (C-4'), 146.7 (C-3'), 131.8 (C-1'), 117.9 (C-6'), 113.5 (C-5'), 111.3 (C-2'), 102.9 (C-10), 94.6 (C-6), 93.7 (C-8), 79.0 (C-2), 42.6 (C-3), 55.4 (4'-OCH₃), 55.3 (7-OCH₃).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 40% probability level. Hydrogen bonds are shown as double dashed lines.
	Fig. 2. Fragment of the one-dimensional chain structure of (I) with hydrogen bonds shown as dashed lines.

5,3'-Dihydroxy-7,4'-dimethoxyflavanone top

Crystal data top

C₁₇H₁₆O₆	F(000) = 332
M_r = 316.30	D_x = 1.395 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2y b	Cell parameters from 4047 reflections
a = 5.4234 (12) Å	θ = 2.6–27.5°
b = 9.293 (2) Å	µ = 0.11 mm⁻¹
c = 14.940 (3) Å	T = 296 K
β = 91.039 (2)°	Block, colorless
V = 752.9 (3) Å³	0.22 × 0.18 × 0.12 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	1581 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
T_min = 0.977, T_max = 0.987	k = −11→11
7958 measured reflections	l = −18→18

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0485P)² + 0.0531P] where P = (F_o² + 2F_c²)/3
1581 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.11 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₇H₁₆O₆	V = 752.9 (3) Å³
M_r = 316.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.4234 (12) Å	µ = 0.11 mm⁻¹
b = 9.293 (2) Å	T = 296 K
c = 14.940 (3) Å	0.22 × 0.18 × 0.12 mm
β = 91.039 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	1581 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1489 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.987	R_int = 0.019
7958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.077	H-atom parameters constrained
S = 1.06	Δρ_max = 0.11 e Å⁻³
1581 reflections	Δρ_min = −0.14 e Å⁻³
212 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

	x	y	z	U_iso*/U_eq
O1	0.3993 (2)	0.73089 (16)	0.11833 (7)	0.0443 (3)
O2	0.8292 (3)	0.9824 (2)	0.28305 (11)	0.0697 (5)
O3	0.6055 (3)	0.8761 (2)	0.41875 (10)	0.0703 (5)
H3	0.7086	0.9231	0.3919	0.105*
O4	−0.0461 (3)	0.54437 (19)	0.35407 (9)	0.0532 (4)
O5	0.5698 (3)	0.79981 (18)	−0.28802 (9)	0.0582 (4)
O6	0.2587 (3)	0.94212 (19)	−0.18692 (9)	0.0595 (4)
H5	0.2732	0.9377	−0.2414	0.089*
C1'	0.6333 (3)	0.7757 (2)	−0.01135 (12)	0.0396 (4)
C2	0.6447 (3)	0.7700 (2)	0.08935 (12)	0.0407 (4)
H2	0.7605	0.6942	0.1079	0.049*
C2'	0.8030 (4)	0.7024 (2)	−0.06221 (12)	0.0469 (5)
H2'	0.9271	0.6494	−0.0338	0.056*
C3	0.7244 (4)	0.9111 (3)	0.13314 (13)	0.0509 (5)
H3A	0.8946	0.9310	0.1185	0.061*
H3B	0.6235	0.9889	0.1094	0.061*
C3'	0.7904 (4)	0.7070 (2)	−0.15510 (13)	0.0508 (5)
H3'	0.9056	0.6574	−0.1886	0.061*
C4	0.7001 (4)	0.9053 (2)	0.23342 (13)	0.0485 (5)
C4'	0.6070 (4)	0.7852 (2)	−0.19750 (12)	0.0434 (4)
C5	0.4695 (4)	0.7986 (2)	0.35954 (12)	0.0472 (5)
C5'	0.4376 (3)	0.8613 (2)	−0.14645 (12)	0.0415 (4)
C6	0.2845 (4)	0.7110 (3)	0.39144 (12)	0.0490 (5)
H6	0.2560	0.7047	0.4525	0.059*
C6'	0.4503 (3)	0.8559 (2)	−0.05446 (12)	0.0439 (4)
H6'	0.3359	0.9062	−0.0210	0.053*
C7	0.1420 (3)	0.6325 (2)	0.33055 (12)	0.0416 (4)
C7'	0.7267 (6)	0.7210 (3)	−0.34504 (14)	0.0701 (7)
H7'A	0.8943	0.7509	−0.3350	0.105*
H7'B	0.6798	0.7386	−0.4063	0.105*
H7'C	0.7120	0.6201	−0.3324	0.105*
C8	0.1841 (3)	0.6390 (2)	0.23879 (12)	0.0410 (4)
H8	0.0882	0.5852	0.1989	0.049*
C9	0.3691 (3)	0.7260 (2)	0.20815 (11)	0.0373 (4)
C10	0.5161 (3)	0.8091 (2)	0.26731 (12)	0.0413 (4)
C11	−0.1037 (5)	0.5297 (3)	0.44657 (14)	0.0660 (7)
H11A	0.0353	0.4893	0.4784	0.099*
H11B	−0.2436	0.4673	0.4525	0.099*
H11C	−0.1413	0.6225	0.4710	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0462 (7)	0.0580 (8)	0.0285 (6)	−0.0111 (6)	0.0003 (5)	0.0007 (6)
O2	0.0826 (11)	0.0731 (11)	0.0531 (9)	−0.0365 (10)	−0.0075 (8)	−0.0084 (8)
O3	0.0893 (12)	0.0821 (12)	0.0389 (7)	−0.0298 (10)	−0.0109 (7)	−0.0116 (8)
O4	0.0558 (8)	0.0709 (10)	0.0330 (7)	−0.0121 (7)	0.0052 (6)	0.0056 (7)
O5	0.0790 (10)	0.0625 (9)	0.0332 (7)	0.0170 (8)	0.0059 (6)	−0.0006 (7)
O6	0.0639 (9)	0.0755 (11)	0.0391 (8)	0.0270 (8)	−0.0006 (7)	0.0045 (8)
C1'	0.0429 (9)	0.0412 (10)	0.0346 (9)	−0.0019 (8)	0.0026 (7)	0.0034 (8)
C2	0.0407 (9)	0.0457 (10)	0.0357 (9)	−0.0013 (8)	−0.0004 (7)	0.0048 (8)
C2'	0.0465 (10)	0.0504 (11)	0.0438 (10)	0.0109 (9)	0.0036 (8)	0.0073 (9)
C3	0.0557 (11)	0.0530 (12)	0.0440 (11)	−0.0138 (10)	0.0009 (9)	0.0023 (9)
C3'	0.0552 (11)	0.0531 (12)	0.0446 (11)	0.0140 (10)	0.0117 (9)	0.0014 (10)
C4	0.0525 (11)	0.0484 (11)	0.0443 (10)	−0.0106 (10)	−0.0054 (9)	−0.0026 (9)
C4'	0.0561 (10)	0.0409 (10)	0.0334 (9)	0.0030 (9)	0.0069 (8)	0.0024 (8)
C5	0.0568 (11)	0.0521 (12)	0.0326 (9)	−0.0008 (10)	−0.0075 (8)	−0.0051 (8)
C5'	0.0443 (9)	0.0430 (10)	0.0372 (9)	0.0055 (8)	0.0010 (8)	0.0040 (8)
C6	0.0597 (11)	0.0605 (12)	0.0267 (8)	−0.0003 (10)	0.0001 (8)	−0.0005 (9)
C6'	0.0465 (10)	0.0484 (10)	0.0370 (9)	0.0089 (9)	0.0075 (8)	0.0013 (8)
C7	0.0422 (10)	0.0491 (11)	0.0335 (9)	0.0010 (8)	0.0014 (7)	0.0047 (8)
C7'	0.1016 (19)	0.0707 (16)	0.0385 (11)	0.0154 (15)	0.0164 (11)	−0.0066 (12)
C8	0.0409 (9)	0.0494 (10)	0.0326 (9)	−0.0038 (8)	−0.0039 (7)	−0.0016 (8)
C9	0.0405 (9)	0.0424 (10)	0.0290 (8)	0.0004 (8)	−0.0028 (7)	0.0007 (8)
C10	0.0450 (9)	0.0443 (10)	0.0346 (9)	−0.0016 (8)	−0.0031 (7)	−0.0011 (8)
C11	0.0706 (15)	0.0886 (18)	0.0393 (11)	−0.0062 (14)	0.0133 (10)	0.0150 (12)

Geometric parameters (Å, º) top

O1—C9	1.3555 (19)	C3'—C4'	1.377 (3)
O1—C2	1.453 (2)	C3'—H3'	0.9300
O2—C4	1.239 (2)	C4—C10	1.439 (3)
O3—C5	1.350 (2)	C4'—C5'	1.397 (3)
O3—H3	0.8200	C5—C6	1.383 (3)
O4—C7	1.359 (2)	C5—C10	1.409 (3)
O4—C11	1.429 (2)	C5'—C6'	1.376 (2)
O5—C4'	1.370 (2)	C6—C7	1.390 (3)
O5—C7'	1.419 (3)	C6—H6	0.9300
O6—C5'	1.360 (2)	C6'—H6'	0.9300
O6—H5	0.8200	C7—C8	1.395 (2)
C1'—C2'	1.383 (3)	C7'—H7'A	0.9600
C1'—C6'	1.390 (3)	C7'—H7'B	0.9600
C1'—C2	1.506 (2)	C7'—H7'C	0.9600
C2—C3	1.525 (3)	C8—C9	1.373 (3)
C2—H2	0.9800	C8—H8	0.9300
C2'—C3'	1.389 (3)	C9—C10	1.409 (2)
C2'—H2'	0.9300	C11—H11A	0.9600
C3—C4	1.507 (3)	C11—H11B	0.9600
C3—H3A	0.9700	C11—H11C	0.9600
C3—H3B	0.9700

C9—O1—C2	115.53 (13)	C6—C5—C10	121.46 (17)
C5—O3—H3	109.5	O6—C5'—C6'	119.12 (16)
C7—O4—C11	119.06 (17)	O6—C5'—C4'	120.52 (16)
C4'—O5—C7'	117.54 (18)	C6'—C5'—C4'	120.37 (17)
C5'—O6—H5	109.5	C5—C6—C7	118.79 (17)
C2'—C1'—C6'	119.09 (16)	C5—C6—H6	120.6
C2'—C1'—C2	121.06 (16)	C7—C6—H6	120.6
C6'—C1'—C2	119.86 (16)	C5'—C6'—C1'	120.31 (17)
O1—C2—C1'	106.57 (13)	C5'—C6'—H6'	119.8
O1—C2—C3	109.97 (16)	C1'—C6'—H6'	119.8
C1'—C2—C3	113.88 (16)	O4—C7—C6	123.92 (16)
O1—C2—H2	108.8	O4—C7—C8	114.67 (16)
C1'—C2—H2	108.8	C6—C7—C8	121.40 (17)
C3—C2—H2	108.8	O5—C7'—H7'A	109.5
C1'—C2'—C3'	120.83 (17)	O5—C7'—H7'B	109.5
C1'—C2'—H2'	119.6	H7'A—C7'—H7'B	109.5
C3'—C2'—H2'	119.6	O5—C7'—H7'C	109.5
C4—C3—C2	111.48 (16)	H7'A—C7'—H7'C	109.5
C4—C3—H3A	109.3	H7'B—C7'—H7'C	109.5
C2—C3—H3A	109.3	C9—C8—C7	119.13 (17)
C4—C3—H3B	109.3	C9—C8—H8	120.4
C2—C3—H3B	109.3	C7—C8—H8	120.4
H3A—C3—H3B	108.0	O1—C9—C8	116.84 (16)
C4'—C3'—C2'	119.86 (17)	O1—C9—C10	121.70 (16)
C4'—C3'—H3'	120.1	C8—C9—C10	121.44 (15)
C2'—C3'—H3'	120.1	C5—C10—C9	117.77 (17)
O2—C4—C10	122.49 (18)	C5—C10—C4	121.68 (17)
O2—C4—C3	121.02 (19)	C9—C10—C4	120.51 (16)
C10—C4—C3	116.47 (17)	O4—C11—H11A	109.5
O5—C4'—C3'	126.74 (17)	O4—C11—H11B	109.5
O5—C4'—C5'	113.72 (17)	H11A—C11—H11B	109.5
C3'—C4'—C5'	119.53 (16)	O4—C11—H11C	109.5
O3—C5—C6	118.64 (17)	H11A—C11—H11C	109.5
O3—C5—C10	119.90 (18)	H11B—C11—H11C	109.5

C9—O1—C2—C1'	−177.36 (16)	C2'—C1'—C6'—C5'	0.5 (3)
C9—O1—C2—C3	−53.5 (2)	C2—C1'—C6'—C5'	−179.73 (18)
C2'—C1'—C2—O1	−128.91 (19)	C11—O4—C7—C6	−0.2 (3)
C6'—C1'—C2—O1	51.3 (2)	C11—O4—C7—C8	179.76 (19)
C2'—C1'—C2—C3	109.7 (2)	C5—C6—C7—O4	−179.2 (2)
C6'—C1'—C2—C3	−70.1 (2)	C5—C6—C7—C8	0.8 (3)
C6'—C1'—C2'—C3'	−0.8 (3)	O4—C7—C8—C9	179.50 (18)
C2—C1'—C2'—C3'	179.46 (18)	C6—C7—C8—C9	−0.6 (3)
O1—C2—C3—C4	52.9 (2)	C2—O1—C9—C8	−155.13 (17)
C1'—C2—C3—C4	172.44 (16)	C2—O1—C9—C10	26.5 (3)
C1'—C2'—C3'—C4'	0.0 (3)	C7—C8—C9—O1	−178.69 (17)
C2—C3—C4—O2	154.3 (2)	C7—C8—C9—C10	−0.3 (3)
C2—C3—C4—C10	−27.3 (3)	O3—C5—C10—C9	180.00 (19)
C7'—O5—C4'—C3'	3.6 (3)	C6—C5—C10—C9	−0.6 (3)
C7'—O5—C4'—C5'	−177.3 (2)	O3—C5—C10—C4	−2.5 (3)
C2'—C3'—C4'—O5	−179.8 (2)	C6—C5—C10—C4	176.9 (2)
C2'—C3'—C4'—C5'	1.1 (3)	O1—C9—C10—C5	179.19 (17)
O5—C4'—C5'—O6	−0.8 (3)	C8—C9—C10—C5	0.9 (3)
C3'—C4'—C5'—O6	178.4 (2)	O1—C9—C10—C4	1.6 (3)
O5—C4'—C5'—C6'	179.39 (18)	C8—C9—C10—C4	−176.67 (19)
C3'—C4'—C5'—C6'	−1.4 (3)	O2—C4—C10—C5	0.9 (3)
O3—C5—C6—C7	179.2 (2)	C3—C4—C10—C5	−177.44 (19)
C10—C5—C6—C7	−0.2 (3)	O2—C4—C10—C9	178.4 (2)
O6—C5'—C6'—C1'	−179.19 (19)	C3—C4—C10—C9	0.0 (3)
C4'—C5'—C6'—C1'	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.85	2.579 (2)	148
O6—H5···O5	0.82	2.18	2.640 (2)	116
O6—H5···O4ⁱ	0.82	2.29	2.892 (2)	130

Symmetry code: (i) −x, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₆
M_r	316.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	5.4234 (12), 9.293 (2), 14.940 (3)
β (°)	91.039 (2)
V (Å³)	752.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.977, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7958, 1581, 1489
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.077, 1.06
No. of reflections	1581
No. of parameters	212
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.85	2.579 (2)	148
O6—H5···O5	0.82	2.18	2.640 (2)	116
O6—H5···O4ⁱ	0.82	2.29	2.892 (2)	130

Symmetry code: (i) −x, y+1/2, −z.

References

Bruker (2001). SAINT-Plus (Version 6.45), SMART and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, D. B., Li, L. X., Liu, X. H., Li, M. J. & Wang, W. L. (2007). Chin. Chem. Lett. 18, 551–557. Web of Science CrossRef CAS Google Scholar

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Volume 64| Part 5| May 2008| Page o822

doi:10.1107/S1600536808009355

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

5,3′-Dihydr­­oxy-7,4′-di­meth­oxy­flavanone from Artemisia sphaerocephala Kraschen

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Refinement

Supporting information

References

organic compounds

5,3′-Dihydroxy-7,4′-dimethoxyflavanone from Artemisia sphaerocephala Kraschen