1,3-Dihydr-oxy-2-methoxy-methyl-9,10-anthraquinone from Rennellia elliptica Korth.

The title compound, C(16)H(12)O(5), common name: lucidin ω-methyl ether, exists as a planar mol-ecule (r.m.s. deviation = 0.04 Å). Within the mol-ecule, the 1-hydr-oxy group forms a hydrogen bond to the adjacent carbonyl O atom, and the 3-hydr-oxy group forms a hydrogen bond to the adjacent meth-oxy O atom. The meth-oxy 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 = 284.26

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.156

S = 1.01

2825 reflections

201 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.46 e Å−3

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 ▶).

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

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

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

C16H12O5	F(000) = 592
Mr = 284.26	Dx = 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

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

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(Fo2) + (0.0691P)2 + 1.3159P] where P = (Fo2 + 2Fc2)/3
2825 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.43 e Å−3
4 restraints	Δρmin = −0.46 e Å−3

	x	y	z	Uiso*/Ueq	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

	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)

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)

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)

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)