1,7-Dihydr­oxy-2,3,4-trimeth­oxy-9H-xanthen-9-one monohydrate from Halenia elliptica

Yu, P.; Shen, X.; Hu, C.; Meehan, E.J.; Chen, L.

doi:10.1107/S1600536808004832

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages o651-o652

doi:10.1107/S1600536808004832

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1,7-Dihydroxy-2,3,4-trimethoxy-9H-xanthen-9-one monohydrate from Halenia elliptica

Peizhong Yu,^a Xiaojuan Shen,^a Changqi Hu,^a Edward J. Meehan ^b and Liqing Chen ^b ^*

^aDepartment of Chemistry of Natural Drugs, School of Pharmacy, Fudan University, Shanghai 200032, People's Republic of China, and ^bLaboratory for Structural Biology, Department of Chemistry, Graduate Programs of Biotechnology, Chemistry and Materials Science, University of Alabama, Huntsville, AL 35899, USA
^*Correspondence e-mail: chenlq@uah.edu

(Received 24 January 2008; accepted 19 February 2008; online 5 March 2008)

The title compound, C₁₆H₁₄O₇·H₂O, possesses a planar three-ring skeleton; its carbonyl, one of the two hydroxy and two of the three methoxy O atoms and the water molecule 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_r = 336.29
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.141
S = 1.06
3563 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z-1.

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.

Supporting information

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

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

checkCIF report

Comment top

Xanthone compounds commonly occur in several higher plant families, such as Gentianaceae,Guttiferae, Moraceae and Polygalaceae. Simple oxygenated xanthones possess different biological activities such as antidepressant, antitumor, antimicrobial, antifungal, anti-inflammatory, antiviral, cardiotonic, hypoglycemic, antihepatotoxic and immunomodulatory (Liou et al., 1993; Basnet et al., 1994; Fernandes et al., 1995; Parmar et al., 1996; Karan et al., 1999; Miura et al., 2001; Pedro et al., 2002; Sousa et al., 2002). The majority of the xanthones isolated so far are hydroxyl or methoxy substituted in the xanthone skeleton. Up to present, only ten simple oxygenated xanthones were characterized by X-ray diffraction (Stout et al., 1969; Vijayalakshmi et al., 1987; Kijjoa et al., 1998; Gales et al., 2001; Kabaleeswaran et al., 2003; Jiang et al., 2004; Shi et al., 2004; Evans et al., 2004; Kato et al., 2005; Shi et al., 2005). 1,7-dihydroxy-2,3,4-trimethoxyxanthone (I) was first isolated from Halenia elliptica D. Don (Gentianaceae) and has antioxidant activity. Its crystal structure is reported for the first time in this paper. The structure of I (Figure 1) is similar to other xanthones reported with a planar three-ring skeleton. The asymmetric unit of crystal I contains one molecule I plus one water molecule. I forms hydrogen bonds with the water molecule through its carbonyl, one of the two hydroxyl and two of the three methoxyl O atoms (Table 1, Figure 2). The crystal structure is stabilized by the extensive hydrogen bond network.

Related literature top

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 top

Halenia elliptica D. Don was collected in DALI, Yunnan Province, in April 2005 and was identified by Professor Xiaokuang Ma, Department of Pharmacognosy, School of Pharmacy, DALI University, People's Republic of China.

Extraction and isolation: 1,7-dihydroxy-2,3,4-trimethoxyxanthone (I) was isolated from ethyl acetate fraction of the ethanol extract of the aerial parts of Halenia elliptica with other four 1,7-dihydroxy substituted xanthones by silica gel column chromatography with gradient mixtures of petroleum ether and ethyl acetate. Yellow crystals of I were obtained by slow evaporation of a solution in EtOH. M.p.164–165°C. ESI-MS m/z (rel. %): 319[M+H]^+.1H-NMR (400 MHz, CDCl₃), d12.60 (1H, s, OH-1), 7.60 (1H, d, J=3.0 Hz, H-8), 7.49 (1H, d, J=9.3 Hz, H-5), 7.34 (1H, dd, J=3.0, 9.0 Hz, H-6), 5.32 (1H, br. s, OH-7), 4.15 (3H, s, OCH₃), 3.96 (3H, s, OCH₃), 3.95 (3H, s, OCH₃).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. Arbitrary atom numbering.
	Fig. 2. The packing of (I), viewed down the b axis.

1,7-dihydroxy-2,3,4-trimethoxy-9H-xanthen-9-one monohydrate top

Crystal data top

C₁₆H₁₄O₇·H₂O	F(000) = 704
M_r = 336.29	D_x = 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 = 2.5–28.3°
c = 14.0201 (11) Å	µ = 0.12 mm⁻¹
β = 111.683 (1)°	T = 298 K
V = 1487.8 (2) Å³	Block, yellow
Z = 4	0.2 × 0.1 × 0.05 mm

Data collection top

Bruker SMART 1K CCD diffractometer	2848 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 28.3°, θ_min = 2.5°
Thin–slice ω scans	h = −14→14
8808 measured reflections	k = −8→13
3563 independent reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0743P)² + 0.2855P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3563 reflections	Δρ_max = 0.29 e Å⁻³
233 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	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)

Crystal data top

C₁₆H₁₄O₇·H₂O	V = 1487.8 (2) Å³
M_r = 336.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9272 (9) Å	µ = 0.12 mm⁻¹
b = 10.4511 (8) Å	T = 298 K
c = 14.0201 (11) Å	0.2 × 0.1 × 0.05 mm
β = 111.683 (1)°

Data collection top

Bruker SMART 1K CCD diffractometer	2848 reflections with I > 2σ(I)
8808 measured reflections	R_int = 0.053
3563 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.29 e Å⁻³
3563 reflections	Δρ_min = −0.24 e Å⁻³
233 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₇·H₂O
M_r	336.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.9272 (9), 10.4511 (8), 14.0201 (11)
β (°)	111.683 (1)
V (Å³)	1487.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.2 × 0.1 × 0.05

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8808, 3563, 2848
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.142, 1.06
No. of reflections	3563
No. of parameters	233
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	168.5

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1.

Acknowledgements

This work was supported in part by the NSF-EPSCoR, USA.

References

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Volume 64| Part 4| April 2008| Pages o651-o652

doi:10.1107/S1600536808004832

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

1,7-Dihydr­­oxy-2,3,4-trimeth­­oxy-9H-xanthen-9-one monohydrate from Halenia elliptica

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,7-Dihydroxy-2,3,4-trimethoxy-9H-xanthen-9-one monohydrate from Halenia elliptica