2-Hydr-oxy-1-methoxy-anthraquinone monohydrate.

The title compound, C(15)H(10)O(4)·H(2)O, also known as alizarin 1-methyl ether monohydrate, was isolated from Morinda officinalis How. The anthraquinone ring system is almost planar, the dihedral angle between the two outer benzene rings being 3.07 (4)°. In the crystal structure, O-H⋯O hydrogen bonds link the organic mol-ecules and the water mol-ecules, forming a three-dimensional network.

Related literature

For pharmacological properties of anthraquinone derivatives, see: Kim et al. (2005 ▶) and of 1-meth­oxy-2-hydroxy­anthraquinone, see: Ali et al. (2000 ▶); Jia et al. (2007 ▶); Wu et al. (2003 ▶). For related structures, see: Boonnak et al. (2005 ▶); Ng et al. (2005 ▶). For the structure of another compound isolated from Morinda officinalis How., see: Xu et al. (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H10O4·H2O

M = 272.25

Triclinic,

a = 7.9583 (19) Å

b = 8.269 (2) Å

c = 10.188 (2) Å

α = 102.462 (3)°

β = 102.364 (3)°

γ = 100.653 (3)°

V = 620.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.973, T max = 0.986

3218 measured reflections

2198 independent reflections

1488 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.147

S = 1.04

2198 reflections

191 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021254/bg2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021254/bg2258Isup2.hkl

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

C15H10O4·H2O	Z = 2
Mr = 272.25	F(000) = 284.0
Triclinic, P1	Dx = 1.457 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9583 (19) Å	Cell parameters from 1018 reflections
b = 8.269 (2) Å	θ = 2.6–26.2°
c = 10.188 (2) Å	µ = 0.11 mm−1
α = 102.462 (3)°	T = 298 K
β = 102.364 (3)°	Block, yellow
γ = 100.653 (3)°	0.30 × 0.20 × 0.15 mm
V = 620.4 (2) Å3

Bruker APEXII area-detector diffractometer	2198 independent reflections
Radiation source: fine-focus sealed tube	1488 reflections with I > 2σ(I)
graphite	Rint = 0.013
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.973, Tmax = 0.986	k = −9→9
3218 measured reflections	l = −12→9

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.0805P] where P = (Fo2 + 2Fc2)/3
2198 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6640 (3)	0.3815 (2)	0.3121 (2)	0.0509 (5)
C2	0.7049 (3)	0.2214 (2)	0.30375 (19)	0.0476 (5)
C3	0.7720 (3)	−0.0406 (2)	0.1655 (2)	0.0485 (5)
C4	0.8497 (3)	−0.2806 (2)	0.0176 (2)	0.0555 (5)
H4	0.8772	−0.3219	0.0955	0.067*
C5	0.8632 (3)	−0.3695 (3)	−0.1086 (3)	0.0645 (6)
H5	0.8980	−0.4717	−0.1158	0.077*
C6	0.8257 (3)	−0.3093 (3)	−0.2248 (3)	0.0668 (6)
H6	0.8347	−0.3707	−0.3099	0.080*
C7	0.7746 (3)	−0.1565 (3)	−0.2142 (2)	0.0600 (6)
H7	0.7505	−0.1146	−0.2921	0.072*
C8	0.7044 (3)	0.0971 (2)	−0.07708 (19)	0.0500 (5)
C9	0.6444 (3)	0.3450 (2)	0.0710 (2)	0.0514 (5)
H9	0.6210	0.3853	−0.0078	0.062*
C10	0.6335 (3)	0.4407 (3)	0.1954 (2)	0.0542 (5)
H10	0.6054	0.5458	0.2006	0.065*
C11	0.7216 (2)	0.1254 (2)	0.17820 (19)	0.0438 (5)
C12	0.6896 (2)	0.1890 (2)	0.06001 (19)	0.0444 (5)
C13	0.7951 (2)	−0.1285 (2)	0.0293 (2)	0.0462 (5)
C14	0.7593 (2)	−0.0664 (2)	−0.08792 (19)	0.0472 (5)
C15	0.8905 (4)	0.2159 (3)	0.5181 (2)	0.0869 (8)
H15A	0.9726	0.1661	0.4763	0.130*
H15B	0.8843	0.1791	0.6005	0.130*
H15C	0.9298	0.3380	0.5425	0.130*
O1	0.6741 (2)	0.15409 (19)	−0.17812 (15)	0.0741 (5)
O2	0.7941 (3)	−0.10671 (19)	0.26171 (16)	0.0772 (5)
O3	0.6543 (2)	0.46790 (18)	0.43714 (14)	0.0679 (5)
H3	0.6315	0.5594	0.4317	0.102*
O4	0.7180 (2)	0.16259 (18)	0.42088 (14)	0.0616 (4)
O1W	0.5800 (3)	0.7728 (2)	0.44181 (19)	0.0829 (6)
H1W	0.597 (4)	0.844 (4)	0.393 (4)	0.162 (15)*
H2W	0.472 (2)	0.762 (4)	0.450 (4)	0.134 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0497 (12)	0.0517 (11)	0.0508 (11)	0.0118 (9)	0.0133 (9)	0.0132 (9)
C2	0.0446 (11)	0.0537 (11)	0.0457 (11)	0.0084 (9)	0.0097 (8)	0.0211 (9)
C3	0.0464 (11)	0.0500 (11)	0.0492 (11)	0.0071 (9)	0.0100 (9)	0.0196 (9)
C4	0.0493 (12)	0.0548 (12)	0.0635 (13)	0.0132 (9)	0.0144 (10)	0.0182 (10)
C5	0.0549 (14)	0.0588 (13)	0.0799 (16)	0.0187 (10)	0.0190 (11)	0.0134 (11)
C6	0.0577 (14)	0.0715 (15)	0.0633 (14)	0.0117 (12)	0.0181 (11)	0.0030 (11)
C7	0.0561 (13)	0.0671 (14)	0.0510 (12)	0.0073 (11)	0.0120 (10)	0.0128 (10)
C8	0.0450 (11)	0.0557 (11)	0.0432 (11)	0.0020 (9)	0.0041 (8)	0.0166 (9)
C9	0.0515 (12)	0.0506 (11)	0.0516 (11)	0.0082 (9)	0.0067 (9)	0.0226 (9)
C10	0.0557 (13)	0.0504 (11)	0.0565 (12)	0.0133 (9)	0.0096 (10)	0.0191 (10)
C11	0.0370 (10)	0.0449 (10)	0.0490 (11)	0.0051 (8)	0.0090 (8)	0.0179 (8)
C12	0.0384 (10)	0.0451 (10)	0.0462 (11)	0.0028 (8)	0.0060 (8)	0.0163 (8)
C13	0.0360 (10)	0.0464 (11)	0.0533 (11)	0.0039 (8)	0.0094 (8)	0.0146 (9)
C14	0.0382 (10)	0.0504 (11)	0.0468 (11)	0.0010 (8)	0.0082 (8)	0.0115 (8)
C15	0.100 (2)	0.0976 (19)	0.0591 (15)	0.0295 (16)	−0.0015 (14)	0.0303 (14)
O1	0.1049 (13)	0.0732 (10)	0.0481 (9)	0.0260 (9)	0.0141 (8)	0.0263 (7)
O2	0.1226 (15)	0.0696 (10)	0.0615 (10)	0.0433 (10)	0.0352 (9)	0.0355 (8)
O3	0.0926 (12)	0.0649 (10)	0.0561 (9)	0.0349 (9)	0.0257 (8)	0.0172 (7)
O4	0.0760 (10)	0.0684 (9)	0.0503 (8)	0.0229 (8)	0.0207 (7)	0.0277 (7)
O1W	0.1221 (18)	0.0768 (12)	0.0776 (12)	0.0454 (11)	0.0478 (11)	0.0384 (10)

C1—O3	1.345 (2)	C8—O1	1.218 (2)
C1—C10	1.373 (3)	C8—C12	1.479 (3)
C1—C2	1.410 (3)	C8—C14	1.486 (3)
C2—O4	1.374 (2)	C9—C10	1.371 (3)
C2—C11	1.399 (3)	C9—C12	1.390 (3)
C3—O2	1.218 (2)	C9—H9	0.9300
C3—C13	1.487 (3)	C10—H10	0.9300
C3—C11	1.487 (3)	C11—C12	1.408 (2)
C4—C5	1.373 (3)	C13—C14	1.395 (3)
C4—C13	1.394 (3)	C15—O4	1.437 (3)
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.377 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—C7	1.387 (3)	O3—H3	0.8200
C6—H6	0.9300	O1W—H1W	0.86 (3)
C7—C14	1.382 (3)	O1W—H2W	0.87 (3)
C7—H7	0.9300
O3—C1—C10	123.24 (18)	C12—C9—H9	119.2
O3—C1—C2	116.77 (17)	C9—C10—C1	120.01 (18)
C10—C1—C2	119.98 (18)	C9—C10—H10	120.0
O4—C2—C11	122.55 (17)	C1—C10—H10	120.0
O4—C2—C1	117.08 (17)	C2—C11—C12	118.56 (17)
C11—C2—C1	120.29 (16)	C2—C11—C3	122.38 (16)
O2—C3—C13	119.21 (18)	C12—C11—C3	119.06 (17)
O2—C3—C11	122.56 (18)	C9—C12—C11	119.58 (18)
C13—C3—C11	118.22 (16)	C9—C12—C8	117.85 (17)
C5—C4—C13	120.20 (19)	C11—C12—C8	122.57 (17)
C5—C4—H4	119.9	C4—C13—C14	118.95 (18)
C13—C4—H4	119.9	C4—C13—C3	118.85 (17)
C4—C5—C6	120.9 (2)	C14—C13—C3	122.18 (17)
C4—C5—H5	119.6	C7—C14—C13	120.27 (19)
C6—C5—H5	119.6	C7—C14—C8	119.88 (18)
C5—C6—C7	119.6 (2)	C13—C14—C8	119.85 (18)
C5—C6—H6	120.2	O4—C15—H15A	109.5
C7—C6—H6	120.2	O4—C15—H15B	109.5
C14—C7—C6	120.1 (2)	H15A—C15—H15B	109.5
C14—C7—H7	120.0	O4—C15—H15C	109.5
C6—C7—H7	119.9	H15A—C15—H15C	109.5
O1—C8—C12	121.26 (19)	H15B—C15—H15C	109.5
O1—C8—C14	120.74 (18)	C1—O3—H3	109.5
C12—C8—C14	117.99 (16)	C2—O4—C15	115.30 (16)
C10—C9—C12	121.52 (18)	H1W—O1W—H2W	107.3 (16)
C10—C9—H9	119.2
O3—C1—C2—O4	4.7 (3)	C3—C11—C12—C8	−0.1 (3)
C10—C1—C2—O4	−174.23 (17)	O1—C8—C12—C9	−1.6 (3)
O3—C1—C2—C11	−178.49 (17)	C14—C8—C12—C9	177.72 (16)
C10—C1—C2—C11	2.6 (3)	O1—C8—C12—C11	179.19 (17)
C13—C4—C5—C6	1.0 (3)	C14—C8—C12—C11	−1.5 (3)
C4—C5—C6—C7	0.3 (3)	C5—C4—C13—C14	−1.7 (3)
C5—C6—C7—C14	−0.7 (3)	C5—C4—C13—C3	176.53 (17)
C12—C9—C10—C1	−1.3 (3)	O2—C3—C13—C4	−3.0 (3)
O3—C1—C10—C9	−179.48 (18)	C11—C3—C13—C4	177.29 (16)
C2—C1—C10—C9	−0.6 (3)	O2—C3—C13—C14	175.24 (18)
O4—C2—C11—C12	174.08 (16)	C11—C3—C13—C14	−4.5 (3)
C1—C2—C11—C12	−2.5 (3)	C6—C7—C14—C13	−0.1 (3)
O4—C2—C11—C3	−6.0 (3)	C6—C7—C14—C8	−179.97 (18)
C1—C2—C11—C3	177.34 (16)	C4—C13—C14—C7	1.3 (3)
O2—C3—C11—C2	3.3 (3)	C3—C13—C14—C7	−176.93 (17)
C13—C3—C11—C2	−176.94 (16)	C4—C13—C14—C8	−178.80 (17)
O2—C3—C11—C12	−176.78 (18)	C3—C13—C14—C8	3.0 (3)
C13—C3—C11—C12	2.9 (3)	O1—C8—C14—C7	−0.7 (3)
C10—C9—C12—C11	1.3 (3)	C12—C8—C14—C7	179.92 (16)
C10—C9—C12—C8	−177.90 (17)	O1—C8—C14—C13	179.34 (18)
C2—C11—C12—C9	0.6 (3)	C12—C8—C14—C13	0.0 (3)
C3—C11—C12—C9	−179.25 (16)	C11—C2—O4—C15	95.3 (2)
C2—C11—C12—C8	179.82 (16)	C1—C2—O4—C15	−87.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2i	0.86 (3)	2.31 (2)	2.960 (3)	133 (3)
O1W—H2W···O4ii	0.87 (3)	2.30 (2)	3.072 (3)	149 (3)
O3—H3···O1W	0.82	1.87	2.687 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2i	0.86 (3)	2.31 (2)	2.960 (3)	133 (3)
O1W—H2W⋯O4ii	0.87 (3)	2.30 (2)	3.072 (3)	149 (3)
O3—H3⋯O1W	0.82	1.87	2.687 (2)	173

Symmetry codes: (i) ; (ii) .