1,3-Dihydr­oxy-2-methoxy­methyl-9,10-anthraquinone from Rennellia elliptica Korth.

Ismail, N.H.; Osman, C.P.; Ahmad, R.; Awang, K.; Ng, S.W.

doi:10.1107/S1600536809017607

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1433-o1434

doi:10.1107/S1600536809017607

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1,3-Dihydroxy-2-methoxymethyl-9,10-anthraquinone from Rennellia elliptica Korth.

Nor Hadiani Ismail,^a Che Puteh Osman,^a Rohaya Ahmad,^a Khalijah Awang ^b and Seik Weng Ng ^b ^*

^aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor Darul Ehsan, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 May 2009; accepted 11 May 2009; online 29 May 2009)

The title compound, C₁₆H₁₂O₅, common name: lucidin ω-methyl ether, exists as a planar molecule (r.m.s. deviation = 0.04 Å). Within the molecule, the 1-hydroxy group forms a hydrogen bond to the adjacent carbonyl O atom, and the 3-hydroxy group forms a hydrogen bond to the adjacent methoxy O atom. The methoxy O atom is disordered over two positions of equal occupancy.

Related literature

The title compound has been isolated from several plants: Rubia tinctorum L. (Boldizsar et al., 2004 ), taurina subsp. caucasica (Ozgen et al., 2006 ), Prismatomeris fragrans (Kanokmedhakul et al., 2005 ), Crucianella maritima L. (El-Lakany et al., 2004 ), Rubia wallichiana Decne (Wu et al., 2003 ), Morinda elliptica (Ali et al., 2000 ; Ismail et al., 1997 ; Ismail et al., 2002 ), Ophiorrhiza pumila (Kitajima et al., 1998 ), Morinda officinalis How. (Yoshikawa et al., 1995 ), Galiumspurium var. echinospermon (Koyama et al., 1993 ), Damnacanthus indicus (Koyama et al., 1992 ), Rubia cordifolia L. (Vidal-Tessier et al., 1987 ), Faramea cyanea (Ferrari et al., 1985 ), Morinda parvifolia (Chang & Lee, 1984 ) and Galium album (Kupier & Labadie, 1984 ).

Experimental

Crystal data

C₁₆H₁₂O₅
M_r = 284.26
Monoclinic, P 2₁ /n
a = 4.6725 (1) Å
b = 39.685 (1) Å
c = 6.9869 (2) Å
β = 107.654 (2)°
V = 1234.55 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.30 × 0.07 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
10046 measured reflections
2825 independent reflections
1888 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.156
S = 1.01
2825 reflections
201 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2	0.85 (1)	1.79 (2)	2.557 (2)	150 (3)
O4—H4o⋯O5	0.84 (1)	1.77 (2)	2.546 (7)	152 (4)
O4—H4o⋯O5′	0.84 (1)	1.77 (2)	2.539 (7)	152 (4)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017607/tk2447sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017607/tk2447Isup2.hkl

checkCIF report

Related literature top

The title compound has been isolated from several plants: Rubia tinctorum L. (Boldizsar et al., 2004) taurina subsp. caucasica (Ozgen et al., 2006), Prismatomeris fragrans (Kanokmedhakul et al., 2005), Crucianella maritima L. (El-Lakany et al., 2004), Rubia wallichiana Decne (Wu et al., 2003), Morinda elliptica (Ali et al., 2000; Ismail et al., 1997; Ismail et al., 2002), Ophiorrhiza pumila (Kitajima et al., 1998), Morinda officinalis How. (Yoshikawa et al., 1995), Galiumspurium var. echinospermon (Koyama et al., 1993), Damnacanthus indicus (Koyama et al., 1992); Rubia cordifolia L. (Vidal-Tessier et al., 1987), Faramea cyanea (Ferrari et al., 1985), Morinda parvifolia (Chang & Lee, 1984) and Galium album (Kupier & Labadie, 1984).

Experimental top

About 1 kg of the root of Rennelia elliptica Korth., which was collected from the Kuala Keniam National Park, Malaysia, was extracted with dichloromethane. The solvent was removed to give a crude material (approx. 10 g) that was fractionated on a chromatography column (60 x 5 cm) packed with silica. The silica had been previously immersed in 4% oxalic acid and then activated by heating to 363 K. The fractions were eluted with hexane–dichloromethane and dichloromethane–methanol in increasing polarity. The fraction eluted with hexane–dichloromethane (2:8 v/v) was purified by thin layer chromatography (2 mm). The product was recrystallized from dichloromethane to furnish yellow crystals. The formulation was established by ¹H- and ¹³C-NMR spectroscopy.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 20010); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the molecule of C₁₆H₁₂O₅ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown

1,3-Dihydroxy-2-methoxymethyl-9,10-anthraquinone top

Crystal data top

C₁₆H₁₂O₅	F(000) = 592
M_r = 284.26	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1810 reflections
a = 4.6725 (1) Å	θ = 3.1–27.9°
b = 39.685 (1) Å	µ = 0.12 mm⁻¹
c = 6.9869 (2) Å	T = 100 K
β = 107.654 (2)°	Plate, yellow
V = 1234.55 (6) Å³	0.30 × 0.07 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1888 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 27.5°, θ_min = 1.0°
ω scans	h = −5→6
10046 measured reflections	k = −51→51
2825 independent reflections	l = −9→8

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0691P)² + 1.3159P] where P = (F_o² + 2F_c²)/3
2825 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.43 e Å⁻³
4 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₆H₁₂O₅	V = 1234.55 (6) Å³
M_r = 284.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.6725 (1) Å	µ = 0.12 mm⁻¹
b = 39.685 (1) Å	T = 100 K
c = 6.9869 (2) Å	0.30 × 0.07 × 0.02 mm
β = 107.654 (2)°

Data collection top

Bruker SMART APEX diffractometer	1888 reflections with I > 2σ(I)
10046 measured reflections	R_int = 0.041
2825 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.43 e Å⁻³
2825 reflections	Δρ_min = −0.46 e Å⁻³
201 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5327 (4)	0.35893 (4)	0.3196 (2)	0.0173 (4)
H1o	0.476 (7)	0.3392 (4)	0.338 (5)	0.039 (9)*
O2	0.2892 (4)	0.31121 (4)	0.4610 (3)	0.0200 (4)
O3	0.0049 (4)	0.39767 (4)	0.9709 (2)	0.0189 (4)
O4	0.5244 (4)	0.46858 (4)	0.5956 (3)	0.0202 (4)
H4o	0.601 (8)	0.4724 (9)	0.503 (4)	0.051 (11)*
O5	0.777 (3)	0.45857 (15)	0.3246 (15)	0.027 (2)	0.50
O5'	0.694 (3)	0.46028 (15)	0.2862 (15)	0.027 (2)	0.50
C1	0.4569 (5)	0.43535 (6)	0.5813 (3)	0.0144 (5)
C2	0.3075 (5)	0.42345 (6)	0.7145 (3)	0.0137 (5)
H2	0.2585	0.4386	0.8052	0.016*
C3	0.2318 (5)	0.38992 (6)	0.7142 (3)	0.0129 (5)
C4	0.0737 (5)	0.37804 (6)	0.8575 (3)	0.0135 (5)
C5	0.0051 (5)	0.34142 (6)	0.8590 (3)	0.0139 (5)
C6	−0.1291 (5)	0.32923 (6)	0.9985 (4)	0.0183 (5)
H6	−0.1774	0.3443	1.0900	0.022*
C7	−0.1917 (6)	0.29523 (6)	1.0034 (4)	0.0217 (5)
H7	−0.2798	0.2869	1.1001	0.026*
C8	−0.1268 (6)	0.27307 (6)	0.8677 (4)	0.0229 (6)
H8	−0.1728	0.2498	0.8707	0.028*
C9	0.0054 (6)	0.28509 (6)	0.7283 (4)	0.0203 (5)
H9	0.0490	0.2700	0.6352	0.024*
C10	0.0745 (5)	0.31922 (6)	0.7240 (3)	0.0146 (5)
C11	0.2280 (5)	0.33153 (6)	0.5794 (3)	0.0141 (5)
C12	0.3044 (5)	0.36698 (6)	0.5816 (3)	0.0132 (5)
C13	0.4545 (5)	0.37961 (6)	0.4486 (3)	0.0129 (5)
C14	0.5296 (5)	0.41375 (6)	0.4458 (3)	0.0131 (5)
C15	0.6804 (5)	0.42442 (6)	0.2919 (3)	0.0153 (5)
H15A	0.8555	0.4097	0.3022	0.018*	0.50
H15B	0.5378	0.4220	0.1551	0.018*	0.50
H15C	0.8858	0.4149	0.3277	0.018*	0.50
H15D	0.5654	0.4157	0.1578	0.018*	0.50
C16	0.8677 (6)	0.47240 (6)	0.1631 (4)	0.0221 (6)
H16A	0.9308	0.4958	0.1938	0.033*	0.50
H16B	0.6989	0.4716	0.0390	0.033*	0.50
H16C	1.0357	0.4592	0.1459	0.033*	0.50
H16D	0.9262	0.4958	0.1984	0.033*	0.50
H16E	0.7474	0.4711	0.0215	0.033*	0.50
H16F	1.0482	0.4585	0.1853	0.033*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0221 (9)	0.0145 (9)	0.0194 (9)	−0.0005 (7)	0.0124 (7)	−0.0022 (7)
O2	0.0264 (9)	0.0162 (8)	0.0209 (9)	−0.0008 (7)	0.0122 (8)	−0.0020 (7)
O3	0.0220 (9)	0.0190 (9)	0.0184 (9)	0.0000 (7)	0.0102 (7)	−0.0021 (7)
O4	0.0303 (10)	0.0136 (8)	0.0205 (9)	−0.0041 (7)	0.0134 (8)	−0.0010 (7)
O5	0.036 (6)	0.0142 (10)	0.043 (3)	0.0027 (18)	0.033 (4)	0.0050 (14)
O5'	0.036 (6)	0.0142 (10)	0.043 (3)	0.0027 (18)	0.033 (4)	0.0050 (14)
C1	0.0138 (11)	0.0130 (11)	0.0156 (11)	−0.0001 (9)	0.0032 (9)	0.0012 (8)
C2	0.0135 (11)	0.0143 (11)	0.0138 (11)	0.0003 (8)	0.0050 (9)	−0.0016 (8)
C3	0.0099 (11)	0.0171 (12)	0.0121 (11)	0.0005 (9)	0.0038 (9)	0.0006 (8)
C4	0.0122 (11)	0.0151 (11)	0.0131 (11)	0.0003 (9)	0.0040 (9)	0.0008 (9)
C5	0.0103 (11)	0.0164 (11)	0.0147 (11)	−0.0009 (8)	0.0032 (9)	0.0023 (9)
C6	0.0180 (12)	0.0196 (12)	0.0189 (12)	0.0006 (10)	0.0082 (10)	0.0024 (9)
C7	0.0217 (13)	0.0231 (13)	0.0230 (13)	−0.0038 (10)	0.0110 (10)	0.0064 (10)
C8	0.0245 (13)	0.0147 (12)	0.0308 (14)	−0.0030 (10)	0.0102 (11)	0.0037 (10)
C9	0.0217 (13)	0.0151 (12)	0.0248 (13)	−0.0005 (9)	0.0083 (11)	−0.0011 (10)
C10	0.0135 (11)	0.0144 (11)	0.0154 (12)	0.0015 (9)	0.0038 (9)	0.0023 (9)
C11	0.0116 (11)	0.0166 (11)	0.0137 (11)	0.0035 (9)	0.0031 (9)	0.0007 (9)
C12	0.0128 (11)	0.0136 (11)	0.0124 (11)	0.0008 (8)	0.0027 (9)	0.0002 (8)
C13	0.0098 (11)	0.0163 (11)	0.0114 (11)	0.0022 (8)	0.0015 (8)	−0.0008 (8)
C14	0.0104 (11)	0.0147 (11)	0.0143 (11)	0.0003 (8)	0.0036 (9)	0.0025 (9)
C15	0.0168 (12)	0.0146 (11)	0.0157 (11)	−0.0002 (9)	0.0068 (9)	0.0001 (9)
C16	0.0273 (14)	0.0184 (12)	0.0257 (14)	−0.0043 (10)	0.0156 (11)	0.0049 (10)

Geometric parameters (Å, º) top

O1—C13	1.349 (3)	C7—C8	1.392 (4)
O1—H1o	0.848 (10)	C7—H7	0.9500
O2—C11	1.249 (3)	C8—C9	1.387 (3)
O3—C4	1.222 (3)	C8—H8	0.9500
O4—C1	1.353 (3)	C9—C10	1.395 (3)
O4—H4o	0.842 (10)	C9—H9	0.9500
O5—C15	1.425 (6)	C10—C11	1.488 (3)
O5—C16	1.431 (6)	C11—C12	1.450 (3)
O5'—C15	1.426 (6)	C12—C13	1.415 (3)
O5'—C16	1.432 (6)	C13—C14	1.401 (3)
C1—C14	1.393 (3)	C14—C15	1.514 (3)
C1—C2	1.404 (3)	C15—H15A	0.9900
C2—C3	1.377 (3)	C15—H15B	0.9900
C2—H2	0.9500	C15—H15C	0.9900
C3—C12	1.412 (3)	C15—H15D	0.9900
C3—C4	1.490 (3)	C16—H16A	0.9800
C4—C5	1.489 (3)	C16—H16B	0.9800
C5—C6	1.396 (3)	C16—H16C	0.9800
C5—C10	1.399 (3)	C16—H16D	0.9800
C6—C7	1.383 (3)	C16—H16E	0.9800
C6—H6	0.9500	C16—H16F	0.9800

C13—O1—H1o	107 (2)	C3—C12—C13	117.9 (2)
C1—O4—H4o	105 (2)	C3—C12—C11	121.7 (2)
C15—O5—C16	113.1 (5)	C13—C12—C11	120.4 (2)
C15—O5'—C16	113.0 (5)	O1—C13—C14	117.32 (19)
O4—C1—C14	123.4 (2)	O1—C13—C12	120.8 (2)
O4—C1—C2	115.5 (2)	C14—C13—C12	121.9 (2)
C14—C1—C2	121.1 (2)	C1—C14—C13	118.1 (2)
C3—C2—C1	120.2 (2)	C1—C14—C15	124.9 (2)
C3—C2—H2	119.9	C13—C14—C15	116.92 (19)
C1—C2—H2	119.9	O5—C15—C14	110.1 (3)
C2—C3—C12	120.8 (2)	O5'—C15—C14	109.5 (3)
C2—C3—C4	119.0 (2)	O5—C15—H15A	109.6
C12—C3—C4	120.3 (2)	O5'—C15—H15A	123.2
O3—C4—C5	121.2 (2)	C14—C15—H15A	109.6
O3—C4—C3	121.1 (2)	O5—C15—H15B	109.6
C5—C4—C3	117.73 (19)	C14—C15—H15B	109.6
C6—C5—C10	119.8 (2)	H15A—C15—H15B	108.2
C6—C5—C4	119.1 (2)	O5'—C15—H15C	109.8
C10—C5—C4	121.0 (2)	C14—C15—H15C	109.8
C7—C6—C5	119.9 (2)	O5'—C15—H15D	109.8
C7—C6—H6	120.0	C14—C15—H15D	109.8
C5—C6—H6	120.0	H15C—C15—H15D	108.2
C6—C7—C8	120.5 (2)	O5—C16—H16A	109.5
C6—C7—H7	119.7	O5—C16—H16B	109.5
C8—C7—H7	119.7	H16A—C16—H16B	109.5
C9—C8—C7	119.8 (2)	O5—C16—H16C	109.5
C9—C8—H8	120.1	H16A—C16—H16C	109.5
C7—C8—H8	120.1	H16B—C16—H16C	109.5
C8—C9—C10	120.3 (2)	O5—C16—H16D	107.0
C8—C9—H9	119.9	O5'—C16—H16D	109.5
C10—C9—H9	119.9	H16B—C16—H16D	110.0
C9—C10—C5	119.7 (2)	H16C—C16—H16D	111.3
C9—C10—C11	119.7 (2)	O5'—C16—H16E	109.5
C5—C10—C11	120.6 (2)	H16D—C16—H16E	109.5
O2—C11—C12	121.9 (2)	O5'—C16—H16F	109.5
O2—C11—C10	119.5 (2)	H16D—C16—H16F	109.5
C12—C11—C10	118.62 (19)	H16E—C16—H16F	109.5

O4—C1—C2—C3	−179.2 (2)	C2—C3—C12—C11	179.7 (2)
C14—C1—C2—C3	0.5 (3)	C4—C3—C12—C11	0.2 (3)
C1—C2—C3—C12	0.4 (3)	O2—C11—C12—C3	179.3 (2)
C1—C2—C3—C4	179.9 (2)	C10—C11—C12—C3	−1.2 (3)
C2—C3—C4—O3	1.7 (3)	O2—C11—C12—C13	−0.5 (3)
C12—C3—C4—O3	−178.8 (2)	C10—C11—C12—C13	179.0 (2)
C2—C3—C4—C5	−177.7 (2)	C3—C12—C13—O1	179.4 (2)
C12—C3—C4—C5	1.8 (3)	C11—C12—C13—O1	−0.9 (3)
O3—C4—C5—C6	−2.7 (3)	C3—C12—C13—C14	−0.3 (3)
C3—C4—C5—C6	176.8 (2)	C11—C12—C13—C14	179.5 (2)
O3—C4—C5—C10	177.7 (2)	O4—C1—C14—C13	178.4 (2)
C3—C4—C5—C10	−2.9 (3)	C2—C1—C14—C13	−1.2 (3)
C10—C5—C6—C7	0.3 (3)	O4—C1—C14—C15	−2.6 (4)
C4—C5—C6—C7	−179.4 (2)	C2—C1—C14—C15	177.8 (2)
C5—C6—C7—C8	−1.1 (4)	O1—C13—C14—C1	−178.5 (2)
C6—C7—C8—C9	0.8 (4)	C12—C13—C14—C1	1.1 (3)
C7—C8—C9—C10	0.3 (4)	O1—C13—C14—C15	2.4 (3)
C8—C9—C10—C5	−1.1 (4)	C12—C13—C14—C15	−178.0 (2)
C8—C9—C10—C11	177.4 (2)	C16—O5—C15—O5'	−77.9 (18)
C6—C5—C10—C9	0.8 (3)	C16—O5—C15—C14	−168.5 (6)
C4—C5—C10—C9	−179.5 (2)	C16—O5'—C15—O5	77.2 (17)
C6—C5—C10—C11	−177.7 (2)	C16—O5'—C15—C14	172.5 (6)
C4—C5—C10—C11	2.0 (3)	C1—C14—C15—O5	8.4 (6)
C9—C10—C11—O2	1.1 (3)	C13—C14—C15—O5	−172.6 (6)
C5—C10—C11—O2	179.6 (2)	C1—C14—C15—O5'	−8.8 (6)
C9—C10—C11—C12	−178.4 (2)	C13—C14—C15—O5'	170.2 (6)
C5—C10—C11—C12	0.1 (3)	C15—O5—C16—O5'	77.8 (18)
C2—C3—C12—C13	−0.5 (3)	C15—O5'—C16—O5	−77.3 (17)
C4—C3—C12—C13	179.98 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.85 (1)	1.79 (2)	2.557 (2)	150 (3)
O4—H4o···O5	0.84 (1)	1.77 (2)	2.546 (7)	152 (4)
O4—H4o···O5′	0.84 (1)	1.77 (2)	2.539 (7)	152 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₅
M_r	284.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	4.6725 (1), 39.685 (1), 6.9869 (2)
β (°)	107.654 (2)
V (Å³)	1234.55 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.07 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10046, 2825, 1888
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.156, 1.01
No. of reflections	2825
No. of parameters	201
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.46

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 20010), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.85 (1)	1.79 (2)	2.557 (2)	150 (3)
O4—H4o···O5	0.84 (1)	1.77 (2)	2.546 (7)	152 (4)
O4—H4o···O5'	0.84 (1)	1.77 (2)	2.539 (7)	152 (4)

Acknowledgements

We thank Universiti Teknologi MARA and the University of Malaya for supporting this study.

References

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Volume 65| Part 6| June 2009| Pages o1433-o1434

doi:10.1107/S1600536809017607

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

1,3-Dihydr­­oxy-2-meth­oxy­methyl-9,10-anthra­quinone from Rennellia elliptica Korth.

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,3-Dihydroxy-2-methoxymethyl-9,10-anthraquinone from Rennellia elliptica Korth.