5,7-Dihy­droxy-2-(3-hy­droxy-4,5-dimeth­oxy­phen­yl)-6-meth­oxy-4H-chromen-4-one

Adizov, S.M.; Mukhamathanova, R.F.; Turgunov, K.K.; Sham'yanov, I.D.; Tashkhodjaev, B.

doi:10.1107/S1600536813007381

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o578

doi:10.1107/S1600536813007381

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5,7-Dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

Shahobiddin M. Adizov,^a ^* Rimma F. Mukhamathanova,^a Kambarali K. Turgunov,^a Ildar D. Sham'yanov ^a and Bakhodir Tashkhodjaev ^a

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
^*Correspondence e-mail: adizovshahobiddin@yahoo.com

(Received 16 January 2013; accepted 18 March 2013; online 23 March 2013)

The title compound, C₁₈H₁₆O₈, was isolated from the plant Artemisia baldshuanica Krasch et Zarp. The molecule is approximately planar, with the exception of the terminal methyl groups, the C atoms of which devitate from their attached ring planes by 1.243 (5) and 1.168 (5) Å. The dihedral angle between the substituted benzopyran and benzene rings is 5.8 (1)°; this near planarity could be due to conjugation or a packing effect. Intramolecular O—H⋯O and C—H⋯O hydrogen bonds occur. In the crystal, molecules are connected by O—H⋯O hydrogen bonds involving the hydroxy and carbonyl groups, forming hydrogen-bonded chains along [001] and [1-10]. The chains are linked by C—H⋯O interactions.

Related literature

For the biological activity of flavonoids, see: Bodewes et al. (2011 ); Veitch & Grayer (2011 ). For related structures, see: Martinez-Vazquez et al. (1993 ).

Experimental

Crystal data

C₁₈H₁₆O₈
M_r = 360.31
Monoclinic, P c
a = 11.5837 (6) Å
b = 4.4677 (3) Å
c = 15.5521 (8) Å
β = 103.310 (6)°
V = 783.23 (8) Å³
Z = 2
Cu Kα radiation
μ = 1.04 mm⁻¹
T = 300 K
0.60 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.638, T_max = 0.813
2540 measured reflections
1841 independent reflections
1632 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.126
S = 1.07
1841 reflections
242 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	0.82	2.38	2.762 (4)	109
O2—H2A⋯O5ⁱ	0.82	1.96	2.713 (4)	152
O4—H4A⋯O5	0.82	1.85	2.579 (4)	148
O6—H6A⋯O4ⁱⁱ	0.82	2.20	2.954 (3)	153
O6—H6A⋯O7	0.82	2.31	2.734 (4)	113
C3—H3A⋯O2ⁱⁱⁱ	0.93	2.58	3.246 (5)	129
C12—H12B⋯O4^iv	0.96	2.55	3.459 (6)	157
C12—H12C⋯O8	0.96	2.32	2.927 (6)	122
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x+1, y-1, z; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iv) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813007381/zp2001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007381/zp2001Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007381/zp2001Isup3.cml

checkCIF report

Comment top

Among of biologically active natural compounds of plant origin flavonoids occupy an important place. Most important for practical medicine are flavonoids with antioxidant, antiinflammatory, antispasmodic and anticancer activity (Bodewes et al., 2011; Veitch et al., 2011).

Artemisia baldshuanica Krasch. et Zarp. (Asteraceae) - is a widespread in centralasia species of Artemisia and juice of leaves possesses a antihelmintic activity. The title compound, 5,7,3'-trihydroxy-6,4',5'-trimethoxyflavone (also named as 5,7,-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H- chromen-4-one) was isolated from the ethanol extract of above-ground part of Artemisia baldshuanica.

The molecule is nearly planar with exception of H₃C11- and H₃C12- terminal methyl groups. Substituted benzopyran and phenyl rings are planar with r.m.s. deviations of 0.020 Å and 0.026 Å, respectivily. The angle between ring planes equals to 5.8 (1)° thanks to conjugation of π-electronic systems of cycles. Terminal methyl group carbon atoms (C11 and C12) are deviated from their ring planes to 1.243 (5) Å and 1.168 (5) Å, respectively.

The molecule has intramolecular hydrogen bond where O4-H4A···O5 hydroxylic and ketonic groups form six membered pseudocycle. (Table 1). Also it are observed O2-H2A···O3-CH₃ and O6-H6A···O7-CH₃ intramolecular hydrogen bonds between hydroxyl and methoxyl groups. In the crystal, molecules are interconnected via O2-H2A···O5 and O6-H6A···O4 hydrogen bonds observed between hydroxyl and carbonyl groups forming three dimensional H-bond chains. The molecules are further linked by a weak C2'-H2'A···O1, C3-H3A···O2, C12-H12B···O4 and C12-H12C···O8 intermolecular interactions (Table 1).

Related literature top

For the biological activity of flavonoids, see: Bodewes et al. (2011); Veitch & Grayer (2011). For related structures, see: Martinez-Vazquez et al. (1993).

Experimental top

Air dry powdered aerial part of Artemisia baldshuanica, collected prebudding period four time extracted with ethanol. The combined extracts were concentrated under vacuum on a rotary evaporator. Concentrated extract was fractionated with benzene, chloroform, ethylacetate and ethanol. Chloroformic fraction was chromatographed on a silica gel column. Eluting the column with chloroform-ethanol (50:1) was isolated dark-yellow crystals with m.p 244-245 ° C. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the compound in ethanol.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the title compound, displacement ellipsoids are drawn at the 50% probability level.

5,7-Dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one top

Crystal data top

C₁₈H₁₆O₈	F(000) = 376
M_r = 360.31	D_x = 1.528 Mg m⁻³
Monoclinic, Pc	Melting point: 517(1) K
Hall symbol: P -2yc	Cu Kα radiation, λ = 1.54184 Å
a = 11.5837 (6) Å	Cell parameters from 1516 reflections
b = 4.4677 (3) Å	θ = 3.9–75.1°
c = 15.5521 (8) Å	µ = 1.04 mm⁻¹
β = 103.310 (6)°	T = 300 K
V = 783.23 (8) Å³	Prismatic, yellow
Z = 2	0.60 × 0.40 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	1841 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.2576 pixels mm^-1	θ_max = 72.0°, θ_min = 3.9°
ω scans	h = −11→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −3→5
T_min = 0.638, T_max = 0.813	l = −19→19
2540 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0802P)² + 0.1369P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1841 reflections	Δρ_max = 0.16 e Å⁻³
242 parameters	Δρ_min = −0.19 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Crystal data top

C₁₈H₁₆O₈	V = 783.23 (8) Å³
M_r = 360.31	Z = 2
Monoclinic, Pc	Cu Kα radiation
a = 11.5837 (6) Å	µ = 1.04 mm⁻¹
b = 4.4677 (3) Å	T = 300 K
c = 15.5521 (8) Å	0.60 × 0.40 × 0.20 mm
β = 103.310 (6)°

Data collection top

Oxford Diffraction Xcalibur Ruby diffractometer	1841 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1632 reflections with I > 2σ(I)
T_min = 0.638, T_max = 0.813	R_int = 0.018
2540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	Δρ_max = 0.16 e Å⁻³
1841 reflections	Δρ_min = −0.19 e Å⁻³
242 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	0.4704 (2)	0.1567 (6)	0.32058 (17)	0.0446 (6)
O5	0.2167 (2)	0.7371 (7)	0.19407 (19)	0.0537 (7)
O4	0.1091 (2)	0.6830 (6)	0.32115 (18)	0.0499 (6)
H4A	0.1203	0.7391	0.2735	0.075*
O3	0.1066 (2)	0.4181 (6)	0.48320 (16)	0.0507 (7)
O2	0.2852 (2)	0.0185 (7)	0.55401 (18)	0.0544 (7)
H2A	0.2481	0.1197	0.5825	0.082*
C2	0.4798 (3)	0.2888 (8)	0.2441 (2)	0.0391 (7)
C3	0.3979 (3)	0.4806 (9)	0.2006 (2)	0.0443 (8)
H3A	0.4071	0.5636	0.1478	0.053*
C4	0.2961 (3)	0.5607 (8)	0.2339 (2)	0.0405 (7)
C5	0.1957 (3)	0.4917 (8)	0.3591 (2)	0.0395 (7)
C6	0.1942 (3)	0.3556 (8)	0.4387 (2)	0.0412 (7)
C7	0.2850 (3)	0.1563 (8)	0.4774 (2)	0.0426 (8)
C8	0.3774 (3)	0.0899 (9)	0.4375 (2)	0.0454 (8)
H8A	0.4373	−0.0424	0.4635	0.054*
C9	0.3774 (3)	0.2264 (8)	0.3583 (2)	0.0385 (7)
C10	0.2897 (3)	0.4242 (8)	0.3162 (2)	0.0378 (7)
O8	0.7492 (3)	0.3071 (7)	0.03979 (19)	0.0587 (8)
O7	0.9075 (2)	−0.0387 (6)	0.1554 (2)	0.0518 (7)
O6	0.8517 (2)	−0.2462 (7)	0.3062 (2)	0.0561 (7)
H6A	0.9159	−0.2482	0.2925	0.084*
C1'	0.5891 (3)	0.1945 (8)	0.2175 (2)	0.0397 (7)
C2'	0.6697 (3)	0.0105 (8)	0.2724 (2)	0.0420 (8)
H2'A	0.6530	−0.0633	0.3241	0.050*
C3'	0.7758 (3)	−0.0643 (8)	0.2503 (2)	0.0432 (8)
C4'	0.8016 (3)	0.0457 (8)	0.1735 (2)	0.0413 (8)
C5'	0.7192 (3)	0.2219 (9)	0.1170 (2)	0.0443 (8)
C6'	0.6126 (3)	0.3017 (8)	0.1387 (2)	0.0445 (8)
H6'A	0.5582	0.4241	0.1014	0.053*
C11	0.0019 (4)	0.2442 (10)	0.4528 (3)	0.0587 (10)
H11A	−0.0520	0.2790	0.4903	0.088*
H11B	0.0225	0.0358	0.4544	0.088*
H11C	−0.0351	0.3008	0.3933	0.088*
C12	0.9874 (4)	0.2038 (10)	0.1495 (4)	0.0619 (11)
H12A	1.0519	0.1304	0.1262	0.093*
H12B	1.0180	0.2864	0.2073	0.093*
H12C	0.9455	0.3563	0.1112	0.093*
C13	0.6770 (4)	0.5095 (10)	−0.0170 (3)	0.0563 (10)
H13A	0.7116	0.5524	−0.0661	0.085*
H13B	0.6701	0.6913	0.0143	0.085*
H13C	0.5997	0.4236	−0.0382	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0371 (12)	0.0586 (14)	0.0446 (12)	0.0102 (11)	0.0227 (10)	0.0024 (11)
O5	0.0449 (14)	0.0703 (16)	0.0533 (14)	0.0189 (13)	0.0266 (12)	0.0137 (13)
O4	0.0382 (12)	0.0658 (15)	0.0526 (14)	0.0148 (12)	0.0246 (11)	0.0045 (12)
O3	0.0449 (13)	0.0656 (15)	0.0509 (15)	0.0012 (13)	0.0304 (11)	−0.0103 (12)
O2	0.0553 (16)	0.0686 (17)	0.0462 (14)	0.0087 (14)	0.0258 (12)	0.0061 (12)
C2	0.0319 (16)	0.0484 (17)	0.0413 (17)	0.0022 (14)	0.0170 (13)	−0.0078 (14)
C3	0.0415 (17)	0.055 (2)	0.0429 (18)	0.0064 (17)	0.0233 (15)	0.0006 (15)
C4	0.0316 (15)	0.0505 (18)	0.0423 (18)	0.0038 (15)	0.0146 (14)	−0.0026 (15)
C5	0.0321 (15)	0.0503 (17)	0.0409 (16)	0.0003 (14)	0.0183 (13)	−0.0065 (14)
C6	0.0329 (16)	0.0533 (17)	0.0421 (16)	0.0009 (14)	0.0184 (13)	−0.0092 (15)
C7	0.0464 (19)	0.0498 (17)	0.0359 (17)	−0.0032 (16)	0.0181 (14)	−0.0067 (14)
C8	0.0381 (17)	0.0547 (19)	0.0459 (18)	0.0058 (15)	0.0147 (14)	−0.0003 (16)
C9	0.0336 (15)	0.0479 (17)	0.0383 (16)	0.0012 (14)	0.0170 (13)	−0.0071 (13)
C10	0.0319 (15)	0.0469 (16)	0.0390 (16)	0.0024 (13)	0.0171 (13)	−0.0069 (13)
O8	0.0532 (16)	0.082 (2)	0.0504 (15)	0.0173 (15)	0.0314 (13)	0.0131 (14)
O7	0.0425 (14)	0.0519 (14)	0.0716 (18)	0.0116 (12)	0.0354 (13)	0.0020 (13)
O6	0.0440 (14)	0.0678 (16)	0.0636 (16)	0.0180 (13)	0.0272 (12)	0.0145 (14)
C1'	0.0313 (15)	0.0485 (17)	0.0437 (17)	−0.0019 (14)	0.0175 (13)	−0.0074 (14)
C2'	0.0397 (17)	0.0483 (17)	0.0439 (18)	0.0043 (15)	0.0219 (15)	0.0025 (14)
C3'	0.0368 (17)	0.0447 (17)	0.0509 (19)	0.0060 (14)	0.0155 (15)	−0.0016 (15)
C4'	0.0335 (16)	0.0448 (16)	0.0529 (19)	0.0055 (13)	0.0250 (15)	−0.0057 (15)
C5'	0.0423 (18)	0.0553 (19)	0.0421 (18)	0.0015 (15)	0.0235 (15)	−0.0037 (15)
C6'	0.0370 (16)	0.0566 (19)	0.0445 (18)	0.0085 (16)	0.0188 (15)	0.0026 (15)
C11	0.042 (2)	0.076 (3)	0.065 (2)	−0.0034 (18)	0.0269 (18)	0.001 (2)
C12	0.0394 (19)	0.060 (2)	0.093 (3)	0.0001 (17)	0.029 (2)	0.002 (2)
C13	0.056 (2)	0.066 (2)	0.051 (2)	−0.0023 (19)	0.0207 (18)	0.0105 (18)

Geometric parameters (Å, º) top

O1—C2	1.354 (4)	O8—C13	1.399 (5)
O1—C9	1.376 (4)	O7—C4'	1.373 (4)
O5—C4	1.260 (4)	O7—C12	1.441 (5)
O4—C5	1.346 (4)	O6—C3'	1.355 (5)
O4—H4A	0.8200	O6—H6A	0.8200
O3—C6	1.382 (4)	C1'—C2'	1.382 (5)
O3—C11	1.425 (5)	C1'—C6'	1.399 (5)
O2—C7	1.341 (4)	C2'—C3'	1.391 (5)
O2—H2A	0.8200	C2'—H2'A	0.9300
C2—C3	1.340 (5)	C3'—C4'	1.387 (5)
C2—C1'	1.482 (4)	C4'—C5'	1.385 (5)
C3—C4	1.438 (4)	C5'—C6'	1.399 (5)
C3—H3A	0.9300	C6'—H6'A	0.9300
C4—C10	1.436 (5)	C11—H11A	0.9600
C5—C6	1.383 (5)	C11—H11B	0.9600
C5—C10	1.434 (4)	C11—H11C	0.9600
C6—C7	1.403 (5)	C12—H12A	0.9600
C7—C8	1.387 (5)	C12—H12B	0.9600
C8—C9	1.374 (5)	C12—H12C	0.9600
C8—H8A	0.9300	C13—H13A	0.9600
C9—C10	1.391 (5)	C13—H13B	0.9600
O8—C5'	1.378 (4)	C13—H13C	0.9600

C2—O1—C9	120.3 (3)	C2'—C1'—C2	119.7 (3)
C5—O4—H4A	109.5	C6'—C1'—C2	119.9 (3)
C6—O3—C11	113.0 (3)	C1'—C2'—C3'	120.0 (3)
C7—O2—H2A	109.5	C1'—C2'—H2'A	120.0
C3—C2—O1	122.1 (3)	C3'—C2'—H2'A	120.0
C3—C2—C1'	126.3 (3)	O6—C3'—C4'	121.9 (3)
O1—C2—C1'	111.6 (3)	O6—C3'—C2'	117.7 (3)
C2—C3—C4	121.4 (3)	C4'—C3'—C2'	120.4 (3)
C2—C3—H3A	119.3	O7—C4'—C5'	123.0 (3)
C4—C3—H3A	119.3	O7—C4'—C3'	117.3 (3)
O5—C4—C10	121.5 (3)	C5'—C4'—C3'	119.6 (3)
O5—C4—C3	123.1 (3)	O8—C5'—C4'	115.8 (3)
C10—C4—C3	115.5 (3)	O8—C5'—C6'	123.6 (3)
O4—C5—C6	120.7 (3)	C4'—C5'—C6'	120.6 (3)
O4—C5—C10	119.9 (3)	C5'—C6'—C1'	119.0 (3)
C6—C5—C10	119.4 (3)	C5'—C6'—H6'A	120.5
O3—C6—C5	121.4 (3)	C1'—C6'—H6'A	120.5
O3—C6—C7	118.6 (3)	O3—C11—H11A	109.5
C5—C6—C7	120.0 (3)	O3—C11—H11B	109.5
O2—C7—C8	117.1 (3)	H11A—C11—H11B	109.5
O2—C7—C6	121.3 (3)	O3—C11—H11C	109.5
C8—C7—C6	121.6 (3)	H11A—C11—H11C	109.5
C9—C8—C7	117.7 (3)	H11B—C11—H11C	109.5
C9—C8—H8A	121.1	O7—C12—H12A	109.5
C7—C8—H8A	121.1	O7—C12—H12B	109.5
C8—C9—O1	116.3 (3)	H12A—C12—H12B	109.5
C8—C9—C10	123.6 (3)	O7—C12—H12C	109.5
O1—C9—C10	120.1 (3)	H12A—C12—H12C	109.5
C9—C10—C5	117.7 (3)	H12B—C12—H12C	109.5
C9—C10—C4	120.5 (3)	O8—C13—H13A	109.5
C5—C10—C4	121.7 (3)	O8—C13—H13B	109.5
C5'—O8—C13	119.7 (3)	H13A—C13—H13B	109.5
C4'—O7—C12	115.0 (3)	O8—C13—H13C	109.5
C3'—O6—H6A	109.5	H13A—C13—H13C	109.5
C2'—C1'—C6'	120.4 (3)	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.82	2.38	2.762 (4)	109
O2—H2A···O5ⁱ	0.82	1.96	2.713 (4)	152
O4—H4A···O5	0.82	1.85	2.579 (4)	148
O6—H6A···O4ⁱⁱ	0.82	2.20	2.954 (3)	153
O6—H6A···O7	0.82	2.31	2.734 (4)	113
C2′—H2′A···O1	0.93	2.32	2.667 (4)	101
C3—H3A···O2ⁱⁱⁱ	0.93	2.58	3.246 (5)	129
C12—H12B···O4^iv	0.96	2.55	3.459 (6)	157
C12—H12C···O8	0.96	2.32	2.927 (6)	122

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆O₈
M_r	360.31
Crystal system, space group	Monoclinic, Pc
Temperature (K)	300
a, b, c (Å)	11.5837 (6), 4.4677 (3), 15.5521 (8)
β (°)	103.310 (6)
V (Å³)	783.23 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.60 × 0.40 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.638, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	2540, 1841, 1632
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.126, 1.07
No. of reflections	1841
No. of parameters	242
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.82	2.38	2.762 (4)	109.0
O2—H2A···O5ⁱ	0.82	1.96	2.713 (4)	152.0
O4—H4A···O5	0.82	1.85	2.579 (4)	148.0
O6—H6A···O4ⁱⁱ	0.82	2.20	2.954 (3)	153.0
O6—H6A···O7	0.82	2.31	2.734 (4)	113.0
C3—H3A···O2ⁱⁱⁱ	0.93	2.58	3.246 (5)	129.0
C12—H12B···O4^iv	0.96	2.55	3.459 (6)	157.0
C12—H12C···O8	0.96	2.32	2.927 (6)	122.0

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

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant No. FA-F7-T185)

References

Bodewes, T. C. F., Luttikhold, J., van Stijn, M. F. M., Visser, M., van Norren, K., Vermeulen, M. A. R. & van Leeuwen, P. A. M. (2011). Curr. Org. Chem. 15, 2616–2626. CAS Google Scholar
Martinez-Vazquez, M., Vazquez Garcia, H. M., Toscano, R. A. & Perez, G. E. (1993). J. Nat. Prod. 56, 1410–1415. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Veitch, N. C. & Grayer, R. J. (2011). Nat. Prod. Rep. 28, 626–1695. Web of Science CrossRef Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page o578

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

5,7-Dihy­dr­oxy-2-(3-hy­dr­oxy-4,5-dimeth­­oxy­phen­yl)-6-meth­­oxy-4H-chromen-4-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,7-Dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one