2-Hydr-oxy-1-methoxyxanthen-9-one monohydrate.

In the title compound, C(14)H(10)O(4)·H(2)O, isolated from the roots of Calophyllum membranaceum, the xanthene ring system is almost planar (r.m.s. deviation = 0.008 Å). In the crystal structure, inter-molecular O-H⋯O and O-H⋯(O,O) hydrogen bonds connect the mol-ecules.

Related literature

For medicinal and botanical background, see: Zou et al. (2005 ▶); Chen et al. (2008 ▶).

Experimental

Crystal data

C14H10O4·H2O

M = 260.24

Monoclinic,

a = 8.8008 (6) Å

b = 7.0856 (4) Å

c = 19.4596 (9) Å

β = 102.402 (4)°

V = 1185.16 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.38 × 0.26 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.959, T max = 0.974

8151 measured reflections

2919 independent reflections

2269 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.164

S = 1.04

2919 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 global, I. DOI: 10.1107/S1600536809039348/hb5095sup1.cif

Structure factors: contains datablocks . DOI: 10.1107/S1600536809039348/hb5095Isup2.hkl

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

C14H10O4·H2O	F(000) = 544
Mr = 260.24	Dx = 1.458 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2919 reflections
a = 8.8008 (6) Å	θ = 2.1–28.2°
b = 7.0856 (4) Å	µ = 0.11 mm−1
c = 19.4596 (9) Å	T = 295 K
β = 102.402 (4)°	Block, colourless
V = 1185.16 (12) Å3	0.38 × 0.26 × 0.24 mm
Z = 4

Bruker SMART CCD diffractometer	2919 independent reflections
Radiation source: fine-focus sealed tube	2269 reflections with I > 2σ(I)
graphite	Rint = 0.080
Detector resolution: 0 pixels mm-1	θmax = 28.2°, θmin = 2.1°
ω scans	h = −6→11
Absorption correction: multi-scan (SADABS; Bruker, 1997)	k = −8→9
Tmin = 0.959, Tmax = 0.974	l = −25→25
8151 measured reflections

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.0823P)2 + 0.2871P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2919 reflections	Δρmax = 0.26 e Å−3
181 parameters	Δρmin = −0.36 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: 0.095 (8)

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
O1	0.65861 (11)	0.14472 (16)	0.26194 (6)	0.0409 (3)
O2	0.24707 (14)	0.1457 (2)	0.33085 (6)	0.0577 (4)
O3	0.09211 (11)	0.10250 (16)	0.19163 (6)	0.0412 (3)
O4	0.11784 (12)	0.12437 (18)	0.05791 (5)	0.0459 (3)
H4A	0.1386	0.1122	0.0190	0.069*
O1W	0.16228 (15)	0.0842 (3)	−0.07501 (6)	0.0581 (4)
H1A	0.181 (3)	0.166 (4)	−0.1024 (17)	0.097 (10)*
H1B	0.080 (3)	0.039 (4)	−0.0954 (14)	0.079 (8)*
C1	0.65891 (18)	0.1459 (2)	0.33241 (8)	0.0377 (3)
C2	0.8053 (2)	0.1522 (2)	0.37783 (9)	0.0491 (4)
H2A	0.8955	0.1548	0.3602	0.059*
C3	0.8131 (2)	0.1546 (3)	0.44946 (10)	0.0577 (5)
H3A	0.9096	0.1575	0.4805	0.069*
C4	0.6771 (3)	0.1527 (3)	0.47583 (9)	0.0593 (5)
H4B	0.6837	0.1550	0.5242	0.071*
C5	0.5341 (2)	0.1475 (2)	0.43070 (9)	0.0497 (4)
H5A	0.4445	0.1464	0.4487	0.060*
C6	0.52170 (18)	0.1439 (2)	0.35728 (7)	0.0367 (3)
C7	0.36878 (17)	0.1408 (2)	0.30878 (7)	0.0360 (3)
C8	0.37350 (15)	0.13504 (18)	0.23329 (7)	0.0299 (3)
C9	0.23858 (15)	0.12734 (19)	0.17825 (7)	0.0316 (3)
C10	0.25162 (16)	0.12938 (19)	0.10794 (7)	0.0343 (3)
C11	0.39927 (17)	0.1332 (2)	0.09150 (7)	0.0374 (3)
H11A	0.4075	0.1331	0.0446	0.045*
C12	0.53188 (17)	0.1372 (2)	0.14382 (8)	0.0372 (3)
H12A	0.6293	0.1385	0.1325	0.045*
C13	0.51916 (16)	0.13944 (19)	0.21397 (7)	0.0318 (3)
C14	0.0097 (2)	0.2739 (3)	0.19948 (11)	0.0578 (5)
H14A	−0.0904	0.2434	0.2086	0.087*
H14B	−0.0035	0.3468	0.1570	0.087*
H14C	0.0681	0.3457	0.2381	0.087*

	U11	U22	U33	U12	U13	U23
O1	0.0304 (5)	0.0548 (7)	0.0354 (6)	−0.0022 (4)	0.0027 (4)	−0.0018 (4)
O2	0.0468 (6)	0.0962 (10)	0.0337 (6)	−0.0072 (6)	0.0163 (5)	−0.0084 (6)
O3	0.0315 (5)	0.0527 (7)	0.0412 (6)	−0.0061 (4)	0.0118 (4)	−0.0017 (4)
O4	0.0377 (6)	0.0689 (8)	0.0284 (5)	−0.0012 (5)	0.0010 (4)	0.0009 (4)
O1W	0.0456 (7)	0.0910 (11)	0.0357 (6)	−0.0150 (7)	0.0044 (5)	0.0005 (6)
C1	0.0426 (7)	0.0330 (7)	0.0337 (7)	−0.0023 (5)	0.0000 (6)	−0.0023 (5)
C2	0.0439 (8)	0.0466 (9)	0.0490 (9)	−0.0025 (7)	−0.0071 (7)	−0.0036 (7)
C3	0.0627 (11)	0.0509 (10)	0.0459 (9)	−0.0027 (8)	−0.0187 (8)	−0.0028 (7)
C4	0.0798 (13)	0.0582 (11)	0.0317 (8)	−0.0053 (9)	−0.0063 (8)	−0.0023 (7)
C5	0.0643 (10)	0.0517 (10)	0.0304 (7)	−0.0039 (7)	0.0042 (7)	−0.0028 (6)
C6	0.0453 (8)	0.0339 (7)	0.0285 (7)	−0.0035 (5)	0.0029 (5)	−0.0022 (5)
C7	0.0400 (7)	0.0387 (7)	0.0296 (7)	−0.0042 (5)	0.0082 (5)	−0.0030 (5)
C8	0.0315 (6)	0.0306 (6)	0.0276 (6)	−0.0029 (5)	0.0062 (5)	−0.0006 (5)
C9	0.0307 (6)	0.0333 (7)	0.0315 (7)	−0.0026 (5)	0.0081 (5)	−0.0002 (5)
C10	0.0347 (7)	0.0370 (7)	0.0298 (6)	−0.0018 (5)	0.0039 (5)	0.0014 (5)
C11	0.0415 (7)	0.0442 (8)	0.0286 (7)	−0.0004 (6)	0.0119 (6)	0.0021 (5)
C12	0.0341 (7)	0.0448 (8)	0.0355 (7)	−0.0009 (6)	0.0138 (5)	0.0008 (6)
C13	0.0302 (6)	0.0325 (7)	0.0324 (7)	−0.0016 (5)	0.0055 (5)	−0.0013 (5)
C14	0.0417 (8)	0.0675 (12)	0.0693 (11)	0.0063 (8)	0.0235 (8)	−0.0022 (9)

O1—C1	1.3708 (18)	C4—H4B	0.9300
O1—C13	1.3737 (16)	C5—C6	1.409 (2)
O2—C7	1.2372 (17)	C5—H5A	0.9300
O3—C9	1.3801 (16)	C6—C7	1.469 (2)
O3—C14	1.439 (2)	C7—C8	1.4790 (18)
O4—C10	1.3576 (17)	C8—C13	1.4116 (18)
O4—H4A	0.8200	C8—C9	1.4191 (18)
O1W—H1A	0.83 (3)	C9—C10	1.3973 (19)
O1W—H1B	0.81 (3)	C10—C11	1.4036 (19)
C1—C6	1.394 (2)	C11—C12	1.375 (2)
C1—C2	1.398 (2)	C11—H11A	0.9300
C2—C3	1.381 (3)	C12—C13	1.3935 (19)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.400 (3)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.371 (3)	C14—H14C	0.9600
C1—O1—C13	119.30 (11)	C13—C8—C9	117.41 (12)
C9—O3—C14	115.13 (12)	C13—C8—C7	118.99 (12)
C10—O4—H4A	109.5	C9—C8—C7	123.59 (12)
H1A—O1W—H1B	104 (3)	O3—C9—C10	117.56 (12)
O1—C1—C6	122.10 (13)	O3—C9—C8	121.77 (12)
O1—C1—C2	115.87 (14)	C10—C9—C8	120.48 (12)
C6—C1—C2	122.02 (14)	O4—C10—C9	117.45 (12)
C3—C2—C1	118.55 (17)	O4—C10—C11	122.66 (13)
C3—C2—H2A	120.7	C9—C10—C11	119.88 (12)
C1—C2—H2A	120.7	C12—C11—C10	120.79 (12)
C2—C3—C4	120.59 (16)	C12—C11—H11A	119.6
C2—C3—H3A	119.7	C10—C11—H11A	119.6
C4—C3—H3A	119.7	C11—C12—C13	119.46 (12)
C5—C4—C3	120.29 (16)	C11—C12—H12A	120.3
C5—C4—H4B	119.9	C13—C12—H12A	120.3
C3—C4—H4B	119.9	O1—C13—C12	114.70 (12)
C4—C5—C6	120.70 (17)	O1—C13—C8	123.34 (12)
C4—C5—H5A	119.6	C12—C13—C8	121.95 (13)
C6—C5—H5A	119.6	O3—C14—H14A	109.5
C1—C6—C5	117.85 (14)	O3—C14—H14B	109.5
C1—C6—C7	121.30 (13)	H14A—C14—H14B	109.5
C5—C6—C7	120.84 (14)	O3—C14—H14C	109.5
O2—C7—C6	121.24 (13)	H14A—C14—H14C	109.5
O2—C7—C8	123.82 (13)	H14B—C14—H14C	109.5
C6—C7—C8	114.92 (12)
C13—O1—C1—C6	−0.65 (19)	C14—O3—C9—C10	−93.42 (16)
C13—O1—C1—C2	−179.73 (12)	C14—O3—C9—C8	91.70 (16)
O1—C1—C2—C3	179.71 (14)	C13—C8—C9—O3	173.03 (12)
C6—C1—C2—C3	0.6 (2)	C7—C8—C9—O3	−7.70 (19)
C1—C2—C3—C4	−0.7 (3)	C13—C8—C9—C10	−1.70 (18)
C2—C3—C4—C5	0.3 (3)	C7—C8—C9—C10	177.57 (12)
C3—C4—C5—C6	0.1 (3)	O3—C9—C10—O4	5.96 (18)
O1—C1—C6—C5	−179.30 (13)	C8—C9—C10—O4	−179.09 (12)
C2—C1—C6—C5	−0.3 (2)	O3—C9—C10—C11	−172.99 (12)
O1—C1—C6—C7	−0.2 (2)	C8—C9—C10—C11	1.96 (19)
C2—C1—C6—C7	178.83 (13)	O4—C10—C11—C12	−179.64 (13)
C4—C5—C6—C1	−0.1 (2)	C9—C10—C11—C12	−0.7 (2)
C4—C5—C6—C7	−179.18 (15)	C10—C11—C12—C13	−0.7 (2)
C1—C6—C7—O2	−177.43 (14)	C1—O1—C13—C12	−179.55 (12)
C5—C6—C7—O2	1.6 (2)	C1—O1—C13—C8	−0.03 (18)
C1—C6—C7—C8	1.57 (19)	C11—C12—C13—O1	−179.57 (12)
C5—C6—C7—C8	−179.36 (13)	C11—C12—C13—C8	0.9 (2)
O2—C7—C8—C13	176.82 (14)	C9—C8—C13—O1	−179.21 (12)
C6—C7—C8—C13	−2.15 (17)	C7—C8—C13—O1	1.49 (19)
O2—C7—C8—C9	−2.4 (2)	C9—C8—C13—C12	0.28 (19)
C6—C7—C8—C9	178.59 (12)	C7—C8—C13—C12	−179.03 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1W	0.82	1.90	2.7126 (16)	174
O1W—H1A···O2i	0.83 (3)	2.03 (3)	2.857 (2)	174 (3)
O1W—H1B···O4ii	0.81 (3)	2.34 (3)	2.9540 (19)	134 (2)
O1W—H1B···O3ii	0.81 (3)	2.37 (3)	3.1195 (17)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1W	0.82	1.90	2.7126 (16)	174
O1W—H1A⋯O2i	0.83 (3)	2.03 (3)	2.857 (2)	174 (3)
O1W—H1B⋯O4ii	0.81 (3)	2.34 (3)	2.9540 (19)	134 (2)
O1W—H1B⋯O3ii	0.81 (3)	2.37 (3)	3.1195 (17)	155 (2)

Symmetry codes: (i) ; (ii) .