5-Hy­droxy-3,4′,6,7-tetra­meth­oxy­flavone

Geng, H.-W.; Wang, G.-C.; Li, G.-Q.; Jiang, R.-W.; Li, Y.-L.

doi:10.1107/S160053681103827X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2733

https://doi.org/10.1107/S160053681103827X

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5-Hydroxy-3,4′,6,7-tetramethoxyflavone

Hua-Wei Geng,^a Guo-Cai Wang,^a Guo-Qiang Li,^a Ren-Wang Jiang ^a and Yao-Lan Li ^a ^*

^aGuangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China
^*Correspondence e-mail: tliyl@jnu.edu.cn

(Received 4 September 2011; accepted 19 September 2011; online 30 September 2011)

The title compound, C₁₉H₁₈O₇ [systematic name 5-hydroxy-3,6,7-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one], is a flavonoid which was isolated from the traditional Chinese medicine Laggera alata. The benzene ring of the benzopyranone unit forms dihedral angles of 1.72 (3) and 37.39 (5)° with the pyran ring and the substituent benzene ring, respectively. The molecular conformation is stabilized by an intramolecular phenol O—H⋯O_ketone hydrogen bond.

Related literature

For general background to the synthesis and isolation of the title compound, see: Goldsworthy & Robert (1936 ); Sy & Brown (1998 ); Yang et al. (2007 ); Masateru et al. (2009 ). For its anti-hepatotoxic activity, see: Chhaya & Mishra (2007 ).

Experimental

Crystal data

C₁₉H₁₈O₇
M_r = 358.33
Monoclinic, P 2₁ /c
a = 16.6029 (3) Å
b = 7.40255 (12) Å
c = 14.8666 (3) Å
β = 110.487 (2)°
V = 1711.60 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.90 mm⁻¹
T = 295 K
0.26 × 0.21 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini Ultra CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.596, T_max = 1.000
5568 measured reflections
2681 independent reflections
2380 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.097
S = 1.03
2681 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5	0.82	1.89	2.6157 (16)	147

Data collection: CrysAlis PRO (Agilent, 2011); 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: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681103827X/zs2143sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103827X/zs2143Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103827X/zs2143Isup3.cml

checkCIF report

Comment top

The title compound, the flavonoid C₁₉H₁₈O₇ [systematic name 5-hydroxy-3,6,7-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one], (Fig. 1) was originally sythesised from trimethoxyacetophenone (Goldsworthy & Robert, 1936). It was also isolated from Artemisia annua (Sy & Brown, 1998), Laggera pterodonta (Yang et al., 2007) and Aites agnus-castus (Masateru et al., 2009). The flavonoid was also proved to possess significant anti-hepatotoxic activity (Chhaya et al., 2007). The present compound was isolated from the traditional Chinese medicine Laggera alata. In the crystal structure, the dihedral angle between the plane of the benzene ring A and the pyran plane C is 1.72 (3)°, while that between the benzene ring A and the phenyl ring B is 37.39 (5)°. The molecular conformation is stabilized by an intramolecular phenol O—H···O_ketone hydrogen-bonding interaction (Table 1).

Related literature top

For general background to the synthesis and isolation of the title compound, see: Goldsworthy & Robert (1936); Sy & Brown (1998); Yang et al. (2007); Masateru et al. (2009). For its anti-hepatotoxic activity, see: Chhaya & Mishra (2007).

Experimental top

The title compound was isolated from the herbs of the traditional Chinese medicine Laggera alata. The herbs of Laggera alata (5 kg) was extracted with 95% ethanol at room temperature and the extracted solution was concentrated by rotary evaporator. The crude extract was suspended in distilled water and partitioned with petroleum ether, ethyl acetate and n-butanol. The title compound (50 mg) was isolated from the petroleum ether fraction using silica gel column chromatography and crystals were obtained after slow evaporation of an ethyl acetate solution at room temperature.

Structure description top

For general background to the synthesis and isolation of the title compound, see: Goldsworthy & Robert (1936); Sy & Brown (1998); Yang et al. (2007); Masateru et al. (2009). For its anti-hepatotoxic activity, see: Chhaya & Mishra (2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.

5-Hydroxy-3,6,7-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one top

Crystal data top

C₁₉H₁₈O₇	F(000) = 752
M_r = 358.33	D_x = 1.391 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
a = 16.6029 (3) Å	Cell parameters from 3031 reflections
b = 7.40255 (12) Å	θ = 3.2–62.6°
c = 14.8666 (3) Å	µ = 0.90 mm⁻¹
β = 110.487 (2)°	T = 295 K
V = 1711.60 (6) Å³	Block, colourless
Z = 4	0.26 × 0.21 × 0.18 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini Ultra CCD diffractometer	2681 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2380 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.016
Detector resolution: 16.0288 pixels mm^-1	θ_max = 62.7°, θ_min = 5.7°
ω scans	h = −19→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
T_min = 0.596, T_max = 1.000	l = −12→17
5568 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0545P)² + 0.2624P] where P = (F_o² + 2F_c²)/3
2681 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₉H₁₈O₇	V = 1711.60 (6) Å³
M_r = 358.33	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 16.6029 (3) Å	µ = 0.90 mm⁻¹
b = 7.40255 (12) Å	T = 295 K
c = 14.8666 (3) Å	0.26 × 0.21 × 0.18 mm
β = 110.487 (2)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini Ultra CCD diffractometer	2681 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2380 reflections with I > 2σ(I)
T_min = 0.596, T_max = 1.000	R_int = 0.016
5568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.14 e Å⁻³
2681 reflections	Δρ_min = −0.13 e Å⁻³
241 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.48173 (9)	0.62713 (18)	0.35189 (9)	0.0426 (3)
H1	0.4827	0.6247	0.4148	0.051*
C2	0.55652 (9)	0.65137 (18)	0.33208 (9)	0.0426 (3)
C3	0.55508 (9)	0.65911 (18)	0.23692 (10)	0.0437 (3)
C4	0.47856 (10)	0.63752 (18)	0.16217 (9)	0.0452 (4)
C5	0.40106 (9)	0.60851 (18)	0.18019 (9)	0.0425 (3)
C6	0.40584 (9)	0.60677 (17)	0.27555 (9)	0.0400 (3)
C7	0.31987 (10)	0.58282 (19)	0.10407 (10)	0.0470 (4)
C8	0.24726 (9)	0.55273 (19)	0.13451 (10)	0.0463 (4)
C9	0.25552 (9)	0.55542 (18)	0.22864 (9)	0.0426 (3)
C10	0.18754 (9)	0.54065 (19)	0.27030 (9)	0.0438 (3)
C11	0.19372 (9)	0.6426 (2)	0.35134 (10)	0.0471 (4)
H11	0.2413	0.7167	0.3786	0.057*
C12	0.13104 (9)	0.6358 (2)	0.39175 (10)	0.0512 (4)
H12	0.1363	0.7058	0.4455	0.061*
C13	0.05974 (9)	0.5249 (2)	0.35272 (10)	0.0502 (4)
C14	0.05317 (10)	0.4198 (2)	0.27362 (12)	0.0581 (4)
H14	0.0063	0.3432	0.2478	0.070*
C15	0.11659 (10)	0.4286 (2)	0.23276 (11)	0.0553 (4)
H15	0.1114	0.3581	0.1792	0.066*
C16	0.64117 (10)	0.6460 (3)	0.49839 (11)	0.0672 (5)
H16A	0.6228	0.5260	0.5065	0.101*
H16B	0.6050	0.7324	0.5140	0.101*
H16C	0.6996	0.6630	0.5402	0.101*
C17	0.67982 (12)	0.5470 (3)	0.21626 (15)	0.0744 (5)
H17A	0.6467	0.4644	0.1676	0.112*
H17B	0.6983	0.4879	0.2776	0.112*
H17C	0.7292	0.5860	0.2020	0.112*
C18	0.15121 (13)	0.3816 (3)	0.00626 (14)	0.0818 (6)
H18A	0.1759	0.4002	−0.0425	0.123*
H18B	0.0905	0.3617	−0.0234	0.123*
H18C	0.1773	0.2782	0.0442	0.123*
C19	−0.07302 (12)	0.4180 (3)	0.36159 (15)	0.0807 (6)
H19A	−0.1054	0.4487	0.2961	0.121*
H19B	−0.1084	0.4341	0.4001	0.121*
H19C	−0.0549	0.2942	0.3650	0.121*
O1	0.33340 (6)	0.58608 (13)	0.29847 (6)	0.0426 (3)
O2	0.63532 (6)	0.67071 (15)	0.40059 (7)	0.0525 (3)
O3	0.62890 (7)	0.69783 (14)	0.21861 (7)	0.0529 (3)
O4	0.47794 (8)	0.64402 (17)	0.07088 (7)	0.0620 (3)
H4	0.4288	0.6281	0.0334	0.093*
O5	0.31225 (8)	0.58768 (17)	0.01722 (7)	0.0616 (3)
O6	0.16597 (7)	0.53866 (16)	0.06686 (7)	0.0587 (3)
O7	0.00047 (7)	0.53200 (18)	0.39654 (8)	0.0674 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0497 (8)	0.0430 (8)	0.0356 (7)	−0.0008 (6)	0.0155 (6)	0.0017 (6)
C2	0.0492 (8)	0.0354 (7)	0.0431 (7)	−0.0009 (6)	0.0160 (6)	0.0014 (6)
C3	0.0547 (8)	0.0332 (7)	0.0489 (8)	−0.0023 (6)	0.0253 (7)	0.0009 (6)
C4	0.0654 (9)	0.0362 (7)	0.0389 (7)	−0.0008 (6)	0.0243 (7)	0.0009 (6)
C5	0.0552 (8)	0.0343 (7)	0.0380 (7)	0.0016 (6)	0.0165 (6)	0.0008 (5)
C6	0.0486 (8)	0.0334 (7)	0.0396 (7)	0.0022 (6)	0.0175 (6)	0.0026 (5)
C7	0.0626 (9)	0.0394 (7)	0.0359 (7)	0.0056 (7)	0.0132 (6)	0.0033 (6)
C8	0.0513 (8)	0.0415 (8)	0.0394 (7)	0.0053 (6)	0.0074 (6)	0.0014 (6)
C9	0.0469 (8)	0.0343 (7)	0.0410 (7)	0.0030 (6)	0.0084 (6)	−0.0001 (6)
C10	0.0448 (7)	0.0396 (7)	0.0418 (7)	0.0011 (6)	0.0086 (6)	0.0013 (6)
C11	0.0455 (8)	0.0488 (8)	0.0424 (7)	−0.0076 (6)	0.0096 (6)	−0.0027 (6)
C12	0.0533 (8)	0.0552 (9)	0.0432 (7)	−0.0080 (7)	0.0143 (6)	−0.0058 (7)
C13	0.0476 (8)	0.0517 (9)	0.0487 (8)	−0.0052 (7)	0.0139 (6)	0.0020 (7)
C14	0.0525 (9)	0.0538 (9)	0.0633 (9)	−0.0156 (7)	0.0143 (7)	−0.0097 (8)
C15	0.0593 (9)	0.0490 (9)	0.0544 (8)	−0.0080 (7)	0.0159 (7)	−0.0123 (7)
C16	0.0522 (9)	0.0982 (14)	0.0450 (8)	−0.0076 (9)	0.0092 (7)	0.0153 (9)
C17	0.0725 (12)	0.0621 (11)	0.1037 (14)	0.0102 (9)	0.0500 (11)	0.0093 (10)
C18	0.0770 (12)	0.0918 (15)	0.0642 (11)	−0.0132 (11)	0.0088 (9)	−0.0287 (10)
C19	0.0579 (10)	0.0963 (15)	0.0901 (13)	−0.0257 (10)	0.0288 (9)	−0.0111 (12)
O1	0.0438 (5)	0.0456 (5)	0.0367 (5)	−0.0003 (4)	0.0121 (4)	0.0005 (4)
O2	0.0473 (6)	0.0639 (7)	0.0455 (5)	−0.0059 (5)	0.0154 (4)	0.0045 (5)
O3	0.0624 (6)	0.0430 (6)	0.0640 (6)	−0.0042 (5)	0.0357 (5)	0.0008 (5)
O4	0.0791 (8)	0.0728 (8)	0.0406 (5)	−0.0097 (6)	0.0290 (5)	−0.0025 (5)
O5	0.0754 (7)	0.0706 (8)	0.0348 (5)	0.0027 (6)	0.0141 (5)	0.0057 (5)
O6	0.0545 (6)	0.0664 (7)	0.0439 (6)	0.0046 (5)	0.0029 (5)	−0.0018 (5)
O7	0.0587 (7)	0.0816 (9)	0.0676 (7)	−0.0227 (6)	0.0294 (6)	−0.0130 (6)

Geometric parameters (Å, º) top

C1—H1	0.9300	C12—C13	1.390 (2)
C1—C2	1.3845 (19)	C13—C14	1.382 (2)
C1—C6	1.3774 (19)	C13—O7	1.3580 (18)
C2—C3	1.408 (2)	C14—H14	0.9300
C2—O2	1.3552 (17)	C14—C15	1.389 (2)
C3—C4	1.373 (2)	C15—H15	0.9300
C3—O3	1.3755 (17)	C16—H16A	0.9600
C4—C5	1.419 (2)	C16—H16B	0.9600
C4—O4	1.3543 (17)	C16—H16C	0.9600
C5—C6	1.3920 (19)	C16—O2	1.4347 (18)
C5—C7	1.437 (2)	C17—H17A	0.9600
C6—O1	1.3685 (16)	C17—H17B	0.9600
C7—C8	1.446 (2)	C17—H17C	0.9600
C7—O5	1.2531 (17)	C17—O3	1.408 (2)
C8—C9	1.358 (2)	C18—H18A	0.9600
C8—O6	1.3761 (17)	C18—H18B	0.9600
C9—C10	1.469 (2)	C18—H18C	0.9600
C9—O1	1.3644 (16)	C18—O6	1.438 (2)
C10—C11	1.395 (2)	C19—H19A	0.9600
C10—C15	1.388 (2)	C19—H19B	0.9600
C11—H11	0.9300	C19—H19C	0.9600
C11—C12	1.373 (2)	C19—O7	1.424 (2)
C12—H12	0.9300	O4—H4	0.8200

C2—C1—H1	121.0	O7—C13—C14	125.10 (14)
C6—C1—H1	121.0	C13—C14—H14	120.0
C6—C1—C2	117.96 (12)	C13—C14—C15	119.95 (14)
C1—C2—C3	121.20 (13)	C15—C14—H14	120.0
O2—C2—C1	123.76 (12)	C10—C15—C14	121.25 (14)
O2—C2—C3	115.04 (12)	C10—C15—H15	119.4
C4—C3—C2	119.61 (13)	C14—C15—H15	119.4
C4—C3—O3	120.00 (12)	H16A—C16—H16B	109.5
O3—C3—C2	120.30 (13)	H16A—C16—H16C	109.5
C3—C4—C5	120.51 (12)	H16B—C16—H16C	109.5
O4—C4—C3	119.16 (13)	O2—C16—H16A	109.5
O4—C4—C5	120.33 (13)	O2—C16—H16B	109.5
C4—C5—C7	122.26 (12)	O2—C16—H16C	109.5
C6—C5—C4	117.47 (13)	H17A—C17—H17B	109.5
C6—C5—C7	120.26 (13)	H17A—C17—H17C	109.5
C1—C6—C5	123.22 (13)	H17B—C17—H17C	109.5
O1—C6—C1	115.93 (11)	O3—C17—H17A	109.5
O1—C6—C5	120.85 (12)	O3—C17—H17B	109.5
C5—C7—C8	115.41 (12)	O3—C17—H17C	109.5
O5—C7—C5	122.41 (14)	H18A—C18—H18B	109.5
O5—C7—C8	122.18 (13)	H18A—C18—H18C	109.5
C9—C8—C7	121.73 (13)	H18B—C18—H18C	109.5
C9—C8—O6	118.29 (14)	O6—C18—H18A	109.5
O6—C8—C7	119.66 (12)	O6—C18—H18B	109.5
C8—C9—C10	128.17 (13)	O6—C18—H18C	109.5
C8—C9—O1	120.90 (13)	H19A—C19—H19B	109.5
O1—C9—C10	110.79 (11)	H19A—C19—H19C	109.5
C11—C10—C9	119.26 (12)	H19B—C19—H19C	109.5
C15—C10—C9	122.96 (13)	O7—C19—H19A	109.5
C15—C10—C11	117.78 (14)	O7—C19—H19B	109.5
C10—C11—H11	119.3	O7—C19—H19C	109.5
C12—C11—C10	121.36 (13)	C9—O1—C6	120.71 (10)
C12—C11—H11	119.3	C2—O2—C16	116.96 (11)
C11—C12—H12	119.9	C3—O3—C17	115.09 (12)
C11—C12—C13	120.29 (14)	C4—O4—H4	109.5
C13—C12—H12	119.9	C8—O6—C18	115.31 (13)
C14—C13—C12	119.34 (14)	C13—O7—C19	118.32 (13)
O7—C13—C12	115.55 (13)

C1—C2—C3—C4	−1.7 (2)	C8—C9—C10—C11	−142.84 (15)
C1—C2—C3—O3	174.72 (12)	C8—C9—C10—C15	37.3 (2)
C1—C2—O2—C16	6.5 (2)	C8—C9—O1—C6	−2.98 (19)
C1—C6—O1—C9	−176.54 (12)	C9—C8—O6—C18	−119.21 (16)
C2—C1—C6—C5	0.3 (2)	C9—C10—C11—C12	178.80 (13)
C2—C1—C6—O1	−178.99 (12)	C9—C10—C15—C14	−179.31 (14)
C2—C3—C4—C5	0.3 (2)	C10—C9—O1—C6	−179.13 (11)
C2—C3—C4—O4	−179.58 (13)	C10—C11—C12—C13	0.5 (2)
C2—C3—O3—C17	88.51 (17)	C11—C10—C15—C14	0.8 (2)
C3—C2—O2—C16	−174.02 (14)	C11—C12—C13—C14	0.9 (2)
C3—C4—C5—C6	1.3 (2)	C11—C12—C13—O7	−178.28 (14)
C3—C4—C5—C7	−179.12 (13)	C12—C13—C14—C15	−1.4 (2)
C4—C3—O3—C17	−95.05 (17)	C12—C13—O7—C19	−178.35 (16)
C4—C5—C6—C1	−1.7 (2)	C13—C14—C15—C10	0.5 (3)
C4—C5—C6—O1	177.63 (11)	C14—C13—O7—C19	2.6 (2)
C4—C5—C7—C8	179.28 (13)	C15—C10—C11—C12	−1.3 (2)
C4—C5—C7—O5	−1.3 (2)	O1—C9—C10—C11	32.96 (17)
C5—C6—O1—C9	4.11 (18)	O1—C9—C10—C15	−146.90 (14)
C5—C7—C8—C9	2.3 (2)	O2—C2—C3—C4	178.76 (12)
C5—C7—C8—O6	175.71 (12)	O2—C2—C3—O3	−4.78 (19)
C6—C1—C2—C3	1.4 (2)	O3—C3—C4—C5	−176.13 (12)
C6—C1—C2—O2	−179.15 (13)	O3—C3—C4—O4	4.0 (2)
C6—C5—C7—C8	−1.2 (2)	O4—C4—C5—C6	−178.79 (13)
C6—C5—C7—O5	178.25 (13)	O4—C4—C5—C7	0.8 (2)
C7—C5—C6—C1	178.74 (12)	O5—C7—C8—C9	−177.12 (14)
C7—C5—C6—O1	−2.0 (2)	O5—C7—C8—O6	−3.7 (2)
C7—C8—C9—C10	175.13 (13)	O6—C8—C9—C10	1.6 (2)
C7—C8—C9—O1	−0.3 (2)	O6—C8—C9—O1	−173.81 (12)
C7—C8—O6—C18	67.14 (19)	O7—C13—C14—C15	177.69 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5	0.82	1.89	2.6157 (16)	147

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O₇
M_r	358.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	16.6029 (3), 7.40255 (12), 14.8666 (3)
β (°)	110.487 (2)
V (Å³)	1711.60 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.26 × 0.21 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini Ultra CCD
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.596, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5568, 2681, 2380
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.03
No. of reflections	2681
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5	0.82	1.89	2.6157 (16)	147.2

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (No. 81072535) and the Team Project of the Natural Science Foundation of Guangdong Province (No. 8351063201000003).

References

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