1,7-Dihydr-oxy-2,3,4-trimeth-oxy-9H-xanthen-9-one monohydrate from Halenia elliptica.

The title compound, C(16)H(14)O(7)·H(2)O, possesses a planar three-ring skeleton; its carbonyl, one of the two hydroxy and two of the three methoxy O atoms and the water mol-ecule form hydrogen bonds, giving rise to a layer structure.

Related literature

For the anti­depressant, anti­tumor, anti­microbial, anti­fungal, anti-inflammatory, anti­viral, cardiotonic, hypoglycemic, anti­hepatotoxic and immunomodulatory activities of simple xanthones, see: Basnet et al. (1994 ▶); Fernandes et al. (1995 ▶); Karan et al. (1999 ▶); Liou et al. (1993 ▶); Miura et al. (2001 ▶); Parmar et al. (1996 ▶); Pedro et al. (2002 ▶); Sousa et al. (2002 ▶). For the crystal structures of oxygenated xanthones, see: Evans et al. (2004 ▶); Gales et al. (2001 ▶); Jiang et al. (2004 ▶); Kabaleeswaran et al. (2003 ▶); Kato et al. (2005 ▶); Kijjoa et al. (1998 ▶); Shi et al. (2004 ▶, 2005 ▶); Stout et al. (1969 ▶); Vijayalakshmi et al. (1987 ▶).

Experimental

Crystal data

C16H14O7·H2O

M = 336.29

Monoclinic,

a = 10.9272 (9) Å

b = 10.4511 (8) Å

c = 14.0201 (11) Å

β = 111.6830 (10)°

V = 1487.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.2 × 0.1 × 0.05 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: none

8808 measured reflections

3563 independent reflections

2848 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.141

S = 1.06

3563 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004832/ng2424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004832/ng2424Isup2.hkl

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

C16H14O7·H2O	F000 = 704
Mr = 336.29	Dx = 1.501 Mg m−3
Monoclinic, P21/c	Melting point: 437 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 10.9272 (9) Å	Cell parameters from 3563 reflections
b = 10.4511 (8) Å	θ = 2.5–28.3º
c = 14.0201 (11) Å	µ = 0.12 mm−1
β = 111.6830 (10)º	T = 298 K
V = 1487.8 (2) Å3	Block, yellow
Z = 4	0.2 × 0.1 × 0.05 mm

Bruker SMART 1K CCD diffractometer	2848 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Monochromator: graphite	θmax = 28.3º
T = 298 K	θmin = 2.5º
Thin–slice ω scans	h = −14→14
Absorption correction: none	k = −8→13
8808 measured reflections	l = −18→18
3563 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0743P)2 + 0.2855P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.29 e Å−3
3563 reflections	Δρmin = −0.24 e Å−3
233 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0085 (18)
Secondary atom site location: difference Fourier map

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
O5	0.62447 (9)	0.47253 (9)	0.17678 (8)	0.0374 (2)
O1	0.44791 (10)	0.90069 (10)	0.12081 (9)	0.0441 (3)
H1	0.3758	0.8590	0.0943	0.066*
C11	0.52749 (12)	0.68367 (13)	0.14635 (9)	0.0315 (3)
O6	0.29738 (10)	0.70239 (10)	0.06007 (9)	0.0492 (3)
O2	0.69716 (11)	0.99477 (10)	0.21570 (8)	0.0437 (3)
C2	0.67515 (14)	0.86433 (13)	0.20640 (10)	0.0361 (3)
C12	0.63679 (13)	0.60211 (13)	0.18592 (10)	0.0325 (3)
C10	0.39784 (13)	0.63185 (13)	0.09340 (10)	0.0343 (3)
C13	0.50227 (13)	0.41989 (13)	0.12579 (10)	0.0336 (3)
C4	0.76454 (13)	0.64776 (14)	0.23766 (11)	0.0370 (3)
C8	0.26918 (14)	0.43164 (14)	0.02687 (11)	0.0371 (3)
H8	0.1934	0.4798	−0.0049	0.045*
O3	0.89800 (11)	0.84290 (12)	0.29620 (11)	0.0599 (4)
C3	0.78279 (13)	0.78037 (15)	0.24786 (11)	0.0385 (3)
C9	0.38925 (13)	0.49338 (13)	0.08075 (10)	0.0331 (3)
C1	0.54949 (13)	0.81769 (13)	0.15801 (10)	0.0331 (3)
O7	0.14973 (11)	0.23466 (11)	−0.03034 (10)	0.0517 (3)
H7	0.0882	0.2864	−0.0560	0.078*
C7	0.26315 (14)	0.30003 (14)	0.02086 (11)	0.0386 (3)
O4	0.86845 (10)	0.56302 (11)	0.26990 (9)	0.0500 (3)
C5	0.49582 (15)	0.28688 (14)	0.12202 (11)	0.0398 (3)
H5	0.5711	0.2383	0.1543	0.048*
C6	0.37723 (16)	0.22793 (14)	0.07010 (11)	0.0421 (3)
H6	0.3727	0.1391	0.0677	0.051*
C15	1.02209 (16)	0.7842 (2)	0.32996 (18)	0.0673 (5)
H15A	1.0321	0.7309	0.3881	0.101*
H15B	1.0895	0.8486	0.3492	0.101*
H15C	1.0297	0.7329	0.2756	0.101*
C14	0.7299 (2)	1.04398 (18)	0.13328 (16)	0.0595 (5)
H14A	0.8034	0.9974	0.1290	0.089*
H14B	0.7526	1.1328	0.1453	0.089*
H14C	0.6557	1.0349	0.0700	0.089*
C16	0.8790 (2)	0.4892 (2)	0.35909 (16)	0.0701 (6)
H16A	0.8795	0.5457	0.4132	0.105*
H16B	0.9592	0.4406	0.3811	0.105*
H16C	0.8052	0.4321	0.3425	0.105*
O8	0.92795 (15)	0.37653 (18)	0.88918 (14)	0.0695 (4)
H15	0.862 (4)	0.361 (4)	0.905 (3)	0.123 (12)*
H16	0.912 (3)	0.436 (3)	0.860 (2)	0.104 (12)*

	U11	U22	U33	U12	U13	U23
O5	0.0319 (5)	0.0313 (5)	0.0448 (5)	0.0041 (4)	0.0093 (4)	0.0004 (4)
O1	0.0363 (5)	0.0311 (5)	0.0567 (6)	0.0041 (4)	0.0076 (5)	0.0031 (4)
C11	0.0310 (6)	0.0309 (6)	0.0311 (6)	0.0016 (5)	0.0098 (5)	0.0008 (5)
O6	0.0318 (5)	0.0347 (5)	0.0694 (7)	0.0041 (4)	0.0048 (5)	0.0046 (5)
O2	0.0460 (6)	0.0323 (5)	0.0512 (6)	−0.0056 (4)	0.0160 (5)	−0.0051 (4)
C2	0.0382 (7)	0.0318 (6)	0.0374 (7)	−0.0016 (5)	0.0128 (6)	−0.0024 (5)
C12	0.0329 (6)	0.0314 (6)	0.0328 (6)	0.0024 (5)	0.0116 (5)	−0.0001 (5)
C10	0.0322 (6)	0.0318 (6)	0.0359 (6)	0.0017 (5)	0.0089 (5)	0.0031 (5)
C13	0.0348 (7)	0.0328 (7)	0.0336 (6)	0.0019 (5)	0.0132 (5)	−0.0006 (5)
C4	0.0297 (6)	0.0379 (7)	0.0396 (7)	0.0051 (5)	0.0086 (5)	0.0001 (5)
C8	0.0352 (7)	0.0341 (7)	0.0393 (7)	−0.0005 (5)	0.0107 (6)	0.0001 (5)
O3	0.0317 (5)	0.0457 (7)	0.0854 (9)	−0.0031 (5)	0.0018 (5)	−0.0102 (6)
C3	0.0318 (6)	0.0401 (7)	0.0401 (7)	−0.0028 (5)	0.0091 (5)	−0.0042 (6)
C9	0.0345 (7)	0.0314 (6)	0.0328 (6)	0.0006 (5)	0.0119 (5)	0.0011 (5)
C1	0.0342 (6)	0.0310 (6)	0.0333 (6)	0.0024 (5)	0.0113 (5)	0.0014 (5)
O7	0.0443 (6)	0.0396 (6)	0.0659 (7)	−0.0102 (5)	0.0139 (5)	−0.0092 (5)
C7	0.0422 (7)	0.0356 (7)	0.0398 (7)	−0.0061 (6)	0.0175 (6)	−0.0047 (6)
O4	0.0329 (5)	0.0435 (6)	0.0661 (7)	0.0095 (4)	0.0095 (5)	0.0028 (5)
C5	0.0433 (7)	0.0315 (7)	0.0449 (7)	0.0061 (6)	0.0166 (6)	0.0003 (6)
C6	0.0519 (8)	0.0294 (6)	0.0483 (8)	−0.0010 (6)	0.0222 (7)	−0.0033 (6)
C15	0.0329 (8)	0.0638 (12)	0.0911 (14)	−0.0019 (8)	0.0063 (8)	−0.0113 (10)
C14	0.0677 (11)	0.0416 (9)	0.0790 (12)	−0.0009 (8)	0.0387 (10)	0.0066 (8)
C16	0.0575 (11)	0.0644 (12)	0.0714 (12)	0.0185 (9)	0.0038 (9)	0.0198 (10)
O8	0.0527 (8)	0.0662 (10)	0.0874 (11)	0.0122 (7)	0.0232 (7)	0.0162 (8)

O5—C12	1.3623 (16)	O3—C3	1.3567 (17)
O5—C13	1.3753 (17)	O3—C15	1.402 (2)
O1—C1	1.3523 (16)	O7—C7	1.3640 (17)
O1—H1	0.8561	O7—H7	0.8336
C11—C12	1.4040 (18)	C7—C6	1.401 (2)
C11—C1	1.4204 (19)	O4—C16	1.437 (2)
C11—C10	1.4402 (18)	C5—C6	1.375 (2)
O6—C10	1.2601 (16)	C5—H5	0.9300
O2—C2	1.3820 (17)	C6—H6	0.9300
O2—C14	1.426 (2)	C15—H15A	0.9600
C2—C1	1.3765 (19)	C15—H15B	0.9600
C2—C3	1.409 (2)	C15—H15C	0.9600
C12—C4	1.3979 (19)	C14—H14A	0.9600
C10—C9	1.4568 (19)	C14—H14B	0.9600
C13—C5	1.3919 (19)	C14—H14C	0.9600
C13—C9	1.3920 (19)	C16—H16A	0.9600
C4—O4	1.3779 (16)	C16—H16B	0.9600
C4—C3	1.400 (2)	C16—H16C	0.9600
C8—C7	1.3781 (19)	O8—H15	0.85 (4)
C8—C9	1.4057 (19)	O8—H16	0.73 (4)
C8—H8	0.9300
C12—O5—C13	119.33 (10)	O1—C1—C11	120.54 (12)
C1—O1—H1	109.5	C2—C1—C11	120.10 (12)
C12—C11—C1	118.04 (12)	C7—O7—H7	109.5
C12—C11—C10	120.44 (12)	O7—C7—C8	123.07 (14)
C1—C11—C10	121.51 (12)	O7—C7—C6	117.39 (13)
C2—O2—C14	111.49 (12)	C8—C7—C6	119.54 (13)
C1—C2—O2	120.20 (12)	C4—O4—C16	114.94 (13)
C1—C2—C3	120.75 (13)	C6—C5—C13	119.48 (14)
O2—C2—C3	119.05 (12)	C6—C5—H5	120.3
O5—C12—C4	115.67 (12)	C13—C5—H5	120.3
O5—C12—C11	121.75 (12)	C5—C6—C7	120.84 (13)
C4—C12—C11	122.58 (13)	C5—C6—H6	119.6
O6—C10—C11	121.83 (12)	C7—C6—H6	119.6
O6—C10—C9	121.87 (12)	O3—C15—H15A	109.5
C11—C10—C9	116.31 (12)	O3—C15—H15B	109.5
O5—C13—C5	116.43 (12)	H15A—C15—H15B	109.5
O5—C13—C9	122.92 (12)	O3—C15—H15C	109.5
C5—C13—C9	120.65 (13)	H15A—C15—H15C	109.5
O4—C4—C12	119.65 (13)	H15B—C15—H15C	109.5
O4—C4—C3	122.26 (12)	O2—C14—H14A	109.5
C12—C4—C3	117.91 (12)	O2—C14—H14B	109.5
C7—C8—C9	120.33 (13)	H14A—C14—H14B	109.5
C7—C8—H8	119.8	O2—C14—H14C	109.5
C9—C8—H8	119.8	H14A—C14—H14C	109.5
C3—O3—C15	124.13 (14)	H14B—C14—H14C	109.5
O3—C3—C4	126.78 (13)	O4—C16—H16A	109.5
O3—C3—C2	112.65 (13)	O4—C16—H16B	109.5
C4—C3—C2	120.57 (12)	H16A—C16—H16B	109.5
C13—C9—C8	119.08 (12)	O4—C16—H16C	109.5
C13—C9—C10	119.11 (12)	H16A—C16—H16C	109.5
C8—C9—C10	121.79 (12)	H16B—C16—H16C	109.5
O1—C1—C2	119.35 (12)	H15—O8—H16	106 (3)
C14—O2—C2—C1	−93.37 (16)	O5—C13—C9—C8	177.67 (12)
C14—O2—C2—C3	87.18 (17)	C5—C13—C9—C8	−3.1 (2)
C13—O5—C12—C4	−179.21 (11)	O5—C13—C9—C10	−4.2 (2)
C13—O5—C12—C11	1.25 (19)	C5—C13—C9—C10	175.03 (12)
C1—C11—C12—O5	−179.12 (11)	C7—C8—C9—C13	1.5 (2)
C10—C11—C12—O5	−0.6 (2)	C7—C8—C9—C10	−176.60 (13)
C1—C11—C12—C4	1.4 (2)	O6—C10—C9—C13	−175.33 (13)
C10—C11—C12—C4	179.86 (12)	C11—C10—C9—C13	4.52 (19)
C12—C11—C10—O6	177.61 (13)	O6—C10—C9—C8	2.7 (2)
C1—C11—C10—O6	−4.0 (2)	C11—C10—C9—C8	−177.40 (12)
C12—C11—C10—C9	−2.24 (18)	O2—C2—C1—O1	−0.8 (2)
C1—C11—C10—C9	176.19 (12)	C3—C2—C1—O1	178.70 (12)
C12—O5—C13—C5	−178.02 (12)	O2—C2—C1—C11	178.48 (12)
C12—O5—C13—C9	1.24 (19)	C3—C2—C1—C11	−2.1 (2)
O5—C12—C4—O4	3.85 (19)	C12—C11—C1—O1	179.59 (11)
C11—C12—C4—O4	−176.61 (12)	C10—C11—C1—O1	1.1 (2)
O5—C12—C4—C3	179.11 (12)	C12—C11—C1—C2	0.37 (19)
C11—C12—C4—C3	−1.4 (2)	C10—C11—C1—C2	−178.10 (12)
C15—O3—C3—C4	10.8 (3)	C9—C8—C7—O7	−179.92 (13)
C15—O3—C3—C2	−169.68 (17)	C9—C8—C7—C6	0.9 (2)
O4—C4—C3—O3	−5.7 (2)	C12—C4—O4—C16	−75.54 (18)
C12—C4—C3—O3	179.12 (14)	C3—C4—O4—C16	109.41 (18)
O4—C4—C3—C2	174.75 (13)	O5—C13—C5—C6	−178.43 (12)
C12—C4—C3—C2	−0.4 (2)	C9—C13—C5—C6	2.3 (2)
C1—C2—C3—O3	−177.47 (13)	C13—C5—C6—C7	0.2 (2)
O2—C2—C3—O3	1.98 (19)	O7—C7—C6—C5	179.03 (13)
C1—C2—C3—C4	2.1 (2)	C8—C7—C6—C5	−1.8 (2)
O2—C2—C3—C4	−178.45 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O8i—H16i···O2	0.73 (3)	2.58 (3)	3.091 (2)	129.4
O8i—H16i···O3	0.73 (3)	2.46 (3)	3.177 (2)	167.3
O8ii—H15ii···O6	0.84 (5)	2.08 (5)	2.923 (2)	172.3
O7—H7···O8iii	0.83	1.88	2.706 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8i—H16i⋯O2	0.73 (3)	2.58 (3)	3.091 (2)	129.4
O8i—H16i⋯O3	0.73 (3)	2.46 (3)	3.177 (2)	167.3
O8ii—H15ii⋯O6	0.84 (5)	2.08 (5)	2.923 (2)	172.3
O7—H7⋯O8iii	0.83	1.88	2.706 (2)	169

Symmetry codes: (i) ; (ii) ; (iii) .