(E)-1-(2,4-Dihy-droxy-phen-yl)-3-(4-hydroxy-phen-yl)prop-2-en-1-one monohydrate.

In the title compound, C(15)H(12)O(4)·H(2)O, the two benzene rings are not coplanar, making a dihedral angle of 7.24 (16)°. An intra-molecular hy-droxy-carbonyl O-H⋯O hydrogen bond occurs. In the crystal, four inter-molecular O-H⋯O hydrogen bonds involving the hy-droxy residues, the carbonyl group and the water mol-ecule lead to the formation of a three-dimensional network. The supra-molecular structure is further stabilized by weak C-H⋯O inter-actions.

Related literature

For the biological activity of the title compound, see: Jang et al. (2008 ▶); Liu et al. (2008 ▶). For a related structure, see: Ma et al. (2005 ▶).

Experimental

Crystal data

C15H12O4·H2O

M = 274.26

Monoclinic,

a = 11.489 (2) Å

b = 9.5903 (17) Å

c = 12.498 (2) Å

β = 103.649 (3)°

V = 1338.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.988, T max = 0.990

8297 measured reflections

2625 independent reflections

2115 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.144

S = 1.09

2625 reflections

196 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.19 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 I, global. DOI: 10.1107/S1600536811006271/go2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006271/go2004Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

Enhanced figure: interactive version of Fig. 2

C15H12O4·H2O	F(000) = 576
Mr = 274.26	Dx = 1.361 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2288 reflections
a = 11.489 (2) Å	θ = 2.7–25.3°
b = 9.5903 (17) Å	µ = 0.10 mm−1
c = 12.498 (2) Å	T = 298 K
β = 103.649 (3)°	Block, yellow
V = 1338.2 (4) Å3	0.12 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	2115 reflections with I > 2σ(I)
graphite	Rint = 0.031
phi and ω scans	θmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.988, Tmax = 0.990	k = −11→9
8297 measured reflections	l = −15→15

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.499P] where P = (Fo2 + 2Fc2)/3
2625 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.33 e Å−3
5 restraints	Δρmin = −0.19 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	0.19653 (18)	1.0001 (2)	0.07068 (17)	0.0402 (5)
C2	0.10947 (18)	1.1026 (2)	0.07420 (17)	0.0412 (5)
C3	0.0605 (2)	1.1156 (2)	0.16459 (19)	0.0475 (6)
H3	0.0037	1.1844	0.1655	0.057*
C4	0.0950 (2)	1.0275 (2)	0.25329 (18)	0.0452 (5)
C5	0.1818 (2)	0.9256 (3)	0.25306 (19)	0.0500 (6)
H5	0.2061	0.8663	0.3131	0.060*
C6	0.2309 (2)	0.9138 (2)	0.16359 (19)	0.0473 (6)
H6	0.2892	0.8462	0.1644	0.057*
C7	0.24678 (19)	0.9881 (2)	−0.02538 (18)	0.0437 (5)
C8	0.3403 (2)	0.8856 (3)	−0.02910 (19)	0.0494 (6)
H8	0.3588	0.8183	0.0258	0.059*
C9	0.3990 (2)	0.8858 (3)	−0.10772 (19)	0.0493 (6)
H9	0.3751	0.9540	−0.1613	0.059*
C10	0.49523 (19)	0.7959 (2)	−0.12387 (17)	0.0431 (5)
C11	0.5467 (2)	0.6925 (3)	−0.05077 (19)	0.0566 (7)
H11	0.5169	0.6760	0.0111	0.068*
C12	0.6406 (2)	0.6134 (3)	−0.0672 (2)	0.0635 (7)
H12	0.6750	0.5458	−0.0161	0.076*
C13	0.68407 (19)	0.6350 (3)	−0.16102 (18)	0.0474 (6)
C14	0.6341 (2)	0.7353 (3)	−0.23509 (18)	0.0486 (6)
H14	0.6628	0.7498	−0.2978	0.058*
C15	0.5412 (2)	0.8148 (3)	−0.21662 (19)	0.0518 (6)
H15	0.5080	0.8832	−0.2675	0.062*
O1	0.07099 (15)	1.19360 (19)	−0.01001 (14)	0.0589 (5)
H1A	0.107 (3)	1.171 (3)	−0.061 (2)	0.088*
O2	0.04269 (18)	1.0443 (2)	0.33756 (14)	0.0649 (5)
H2A	0.069 (3)	0.988 (3)	0.387 (2)	0.097*
O3	0.21067 (14)	1.06876 (19)	−0.10709 (13)	0.0565 (5)
O4	0.77775 (17)	0.5545 (2)	−0.17385 (14)	0.0668 (6)
H4A	0.784 (3)	0.563 (4)	−0.2384 (17)	0.100*
O5	0.12061 (17)	0.6281 (2)	0.00416 (14)	0.0587 (5)
H5A	0.072 (2)	0.687 (3)	0.017 (3)	0.088*
H5B	0.149 (3)	0.586 (3)	0.0630 (19)	0.088*

	U11	U22	U33	U12	U13	U23
C1	0.0381 (11)	0.0444 (12)	0.0430 (12)	−0.0015 (9)	0.0192 (9)	−0.0060 (10)
C2	0.0413 (11)	0.0446 (12)	0.0415 (11)	−0.0002 (10)	0.0174 (9)	0.0015 (10)
C3	0.0457 (12)	0.0512 (14)	0.0524 (13)	0.0090 (11)	0.0251 (10)	−0.0011 (11)
C4	0.0502 (12)	0.0514 (13)	0.0409 (12)	0.0005 (10)	0.0247 (10)	−0.0039 (10)
C5	0.0583 (14)	0.0530 (14)	0.0436 (12)	0.0078 (11)	0.0217 (11)	0.0070 (10)
C6	0.0485 (12)	0.0485 (13)	0.0497 (13)	0.0086 (10)	0.0213 (10)	−0.0007 (10)
C7	0.0400 (11)	0.0520 (14)	0.0432 (12)	−0.0049 (10)	0.0183 (9)	−0.0041 (10)
C8	0.0513 (13)	0.0551 (14)	0.0483 (13)	0.0061 (11)	0.0249 (10)	−0.0017 (11)
C9	0.0475 (12)	0.0576 (15)	0.0485 (13)	0.0041 (11)	0.0229 (10)	0.0008 (11)
C10	0.0404 (11)	0.0506 (13)	0.0431 (12)	−0.0005 (10)	0.0193 (10)	−0.0044 (10)
C11	0.0605 (15)	0.0757 (18)	0.0437 (13)	0.0113 (13)	0.0323 (12)	0.0049 (12)
C12	0.0690 (16)	0.0791 (19)	0.0495 (14)	0.0290 (15)	0.0285 (12)	0.0156 (13)
C13	0.0425 (12)	0.0596 (15)	0.0446 (12)	0.0065 (11)	0.0193 (10)	−0.0039 (11)
C14	0.0493 (13)	0.0617 (15)	0.0427 (12)	0.0062 (11)	0.0267 (10)	0.0028 (11)
C15	0.0528 (13)	0.0586 (15)	0.0507 (14)	0.0097 (11)	0.0254 (11)	0.0083 (11)
O1	0.0648 (11)	0.0665 (12)	0.0538 (10)	0.0202 (9)	0.0307 (8)	0.0141 (9)
O2	0.0793 (13)	0.0756 (13)	0.0531 (10)	0.0183 (10)	0.0424 (10)	0.0072 (9)
O3	0.0571 (10)	0.0710 (12)	0.0492 (9)	0.0108 (8)	0.0284 (8)	0.0084 (8)
O4	0.0654 (11)	0.0920 (14)	0.0512 (10)	0.0355 (10)	0.0302 (9)	0.0110 (10)
O5	0.0702 (12)	0.0605 (12)	0.0539 (10)	0.0151 (9)	0.0315 (9)	0.0043 (9)

C1—C6	1.405 (3)	C9—H9	0.9300
C1—C2	1.410 (3)	C10—C11	1.383 (3)
C1—C7	1.454 (3)	C10—C15	1.394 (3)
C2—O1	1.359 (3)	C11—C12	1.374 (3)
C2—C3	1.382 (3)	C11—H11	0.9300
C3—C4	1.375 (3)	C12—C13	1.393 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—O2	1.340 (3)	C13—C14	1.364 (3)
C4—C5	1.397 (3)	C13—O4	1.364 (3)
C5—C6	1.371 (3)	C14—C15	1.375 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—O3	1.270 (3)	O1—H1A	0.867 (18)
C7—C8	1.465 (3)	O2—H2A	0.819 (18)
C8—C9	1.316 (3)	O4—H4A	0.829 (18)
C8—H8	0.9300	O5—H5A	0.836 (18)
C9—C10	1.453 (3)	O5—H5B	0.836 (18)
C6—C1—C2	116.61 (18)	C8—C9—H9	115.0
C6—C1—C7	123.2 (2)	C10—C9—H9	115.0
C2—C1—C7	120.24 (19)	C11—C10—C15	117.1 (2)
O1—C2—C3	117.03 (19)	C11—C10—C9	123.66 (19)
O1—C2—C1	121.81 (18)	C15—C10—C9	119.2 (2)
C3—C2—C1	121.2 (2)	C12—C11—C10	121.7 (2)
C4—C3—C2	120.5 (2)	C12—C11—H11	119.1
C4—C3—H3	119.7	C10—C11—H11	119.1
C2—C3—H3	119.7	C11—C12—C13	119.6 (2)
O2—C4—C3	117.5 (2)	C11—C12—H12	120.2
O2—C4—C5	122.6 (2)	C13—C12—H12	120.2
C3—C4—C5	119.90 (19)	C14—C13—O4	122.43 (19)
C6—C5—C4	119.4 (2)	C14—C13—C12	119.9 (2)
C6—C5—H5	120.3	O4—C13—C12	117.6 (2)
C4—C5—H5	120.3	C13—C14—C15	119.7 (2)
C5—C6—C1	122.4 (2)	C13—C14—H14	120.1
C5—C6—H6	118.8	C15—C14—H14	120.1
C1—C6—H6	118.8	C14—C15—C10	121.9 (2)
O3—C7—C1	119.85 (19)	C14—C15—H15	119.0
O3—C7—C8	119.07 (19)	C10—C15—H15	119.0
C1—C7—C8	121.1 (2)	C2—O1—H1A	107 (2)
C9—C8—C7	122.1 (2)	C4—O2—H2A	111 (3)
C9—C8—H8	119.0	C13—O4—H4A	108 (2)
C7—C8—H8	119.0	H5A—O5—H5B	107 (3)
C8—C9—C10	130.0 (2)
C6—C1—C2—O1	178.7 (2)	C2—C1—C7—C8	177.9 (2)
C7—C1—C2—O1	−0.9 (3)	O3—C7—C8—C9	8.8 (4)
C6—C1—C2—C3	−0.5 (3)	C1—C7—C8—C9	−170.2 (2)
C7—C1—C2—C3	179.9 (2)	C7—C8—C9—C10	178.4 (2)
O1—C2—C3—C4	−179.8 (2)	C8—C9—C10—C11	−3.0 (4)
C1—C2—C3—C4	−0.6 (3)	C8—C9—C10—C15	178.3 (3)
C2—C3—C4—O2	−179.0 (2)	C15—C10—C11—C12	1.3 (4)
C2—C3—C4—C5	1.1 (4)	C9—C10—C11—C12	−177.5 (2)
O2—C4—C5—C6	179.5 (2)	C10—C11—C12—C13	−1.5 (4)
C3—C4—C5—C6	−0.6 (4)	C11—C12—C13—C14	0.7 (4)
C4—C5—C6—C1	−0.5 (4)	C11—C12—C13—O4	179.7 (2)
C2—C1—C6—C5	1.1 (3)	O4—C13—C14—C15	−178.9 (2)
C7—C1—C6—C5	−179.4 (2)	C12—C13—C14—C15	0.1 (4)
C6—C1—C7—O3	179.3 (2)	C13—C14—C15—C10	−0.3 (4)
C2—C1—C7—O3	−1.1 (3)	C11—C10—C15—C14	−0.4 (4)
C6—C1—C7—C8	−1.7 (3)	C9—C10—C15—C14	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3	0.87 (2)	1.74 (2)	2.530 (2)	150 (3)
O2—H2A···O5i	0.82 (2)	1.83 (2)	2.644 (3)	175 (4)
O4—H4A···O3ii	0.83 (2)	1.95 (2)	2.776 (2)	175 (4)
O5—H5A···O1iii	0.84 (2)	1.99 (2)	2.802 (2)	164 (3)
O5—H5B···O4iv	0.84 (2)	1.97 (2)	2.785 (3)	165 (3)
C9—H9···O4v	0.93	2.56	3.402 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3	0.87 (2)	1.74 (2)	2.530 (2)	150 (3)
O2—H2A⋯O5i	0.82 (2)	1.83 (2)	2.644 (3)	175 (4)
O4—H4A⋯O3ii	0.83 (2)	1.95 (2)	2.776 (2)	175 (4)
O5—H5A⋯O1iii	0.84 (2)	1.99 (2)	2.802 (2)	164 (3)
O5—H5B⋯O4iv	0.84 (2)	1.97 (2)	2.785 (3)	165 (3)
C9—H9⋯O4v	0.93	2.56	3.402 (3)	151

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