(E)-3-(4-Hy-droxy-3-meth-oxy-phen-yl)-1-(4-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C16H14O4, there is an intra-molecular O-H⋯O hydrogen bond. The benzene rings are inclined to one another by 13.89 (9)°. The prop-2-en-1-one group is twisted slightly, the O=C-Car-Car (ar = aromatic) and C=C-C=O torsion angles being -10.4 (3) and -7.4 (3)°, respectively. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains along [100]. These chains are further linked by O-H⋯O hydrogen bonds, forming corrugated sheets lying parallel to (010). There are C-H⋯π inter-actions present within the sheets.

Related literature

For the biological activity of chalcones and chalcone derivatives, see: Marais et al. (2005 ▶); Di Carlo et al. (1999 ▶); Troeberg et al. (2000 ▶); Ni et al. (2004 ▶). For a related structure, see: Jasinski et al. (2011 ▶). For the synthesis, see: Sidharthan et al. (2012 ▶); Chitra et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14O4

M = 270.27

Orthorhombic,

a = 16.2808 (8) Å

b = 10.4348 (5) Å

c = 16.2905 (7) Å

V = 2767.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.968, T max = 0.977

12921 measured reflections

3441 independent reflections

1935 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.128

S = 1.05

3344 reflections

189 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814008757/su2713sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008757/su2713Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008757/su2713Isup3.cml

CCDC reference: 991699

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H14O4	F(000) = 1136
Mr = 270.27	Dx = 1.297 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3441 reflections
a = 16.2808 (8) Å	θ = 2.5–28.3°
b = 10.4348 (5) Å	µ = 0.09 mm−1
c = 16.2905 (7) Å	T = 293 K
V = 2767.5 (2) Å3	Block, yellow
Z = 8	0.35 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	3441 independent reflections
Radiation source: fine-focus sealed tube	1935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→17
Tmin = 0.968, Tmax = 0.977	k = −13→7
12921 measured reflections	l = −21→21

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.8783P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.004
3344 reflections	Δρmax = 0.18 e Å−3
189 parameters	Δρmin = −0.20 e Å−3
2 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: 0.0024 (6)

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	0.21682 (7)	0.58070 (13)	0.26522 (8)	0.0532 (4)
O2	0.59318 (7)	0.69018 (13)	0.32421 (9)	0.0594 (4)
H2O	0.6310 (12)	0.649 (2)	0.2968 (14)	0.089*
O3	0.28796 (9)	0.08570 (16)	−0.06956 (10)	0.0762 (5)
O4	0.13699 (9)	−0.00902 (16)	−0.07979 (10)	0.0708 (5)
H4O	0.1798 (13)	−0.024 (3)	−0.1090 (16)	0.106*
C1	0.43059 (10)	0.50808 (17)	0.22500 (11)	0.0431 (4)
H1	0.4245	0.4397	0.1889	0.052*
C2	0.50835 (10)	0.54733 (17)	0.24660 (11)	0.0445 (4)
H2	0.5541	0.5065	0.2246	0.053*
C3	0.51802 (10)	0.64693 (17)	0.30075 (11)	0.0423 (4)
C4	0.44972 (11)	0.70803 (18)	0.33262 (12)	0.0511 (5)
H4	0.4562	0.7759	0.3690	0.061*
C5	0.37224 (10)	0.66855 (17)	0.31058 (11)	0.0461 (4)
H5	0.3267	0.7097	0.3327	0.055*
C6	0.36105 (9)	0.56830 (15)	0.25593 (10)	0.0366 (4)
C7	0.27741 (10)	0.53112 (17)	0.23093 (10)	0.0400 (4)
C8	0.26703 (10)	0.43695 (18)	0.16605 (11)	0.0453 (4)
H8	0.3133	0.4132	0.1362	0.054*
C9	0.19621 (11)	0.38287 (17)	0.14669 (11)	0.0459 (4)
H9	0.1504	0.4111	0.1755	0.055*
C10	0.18214 (10)	0.28457 (17)	0.08558 (11)	0.0444 (4)
C11	0.10435 (11)	0.2317 (2)	0.07729 (12)	0.0523 (5)
H11	0.0613	0.2625	0.1092	0.063*
C12	0.09021 (12)	0.1337 (2)	0.02206 (12)	0.0570 (5)
H12	0.0378	0.0990	0.0174	0.068*
C13	0.15256 (12)	0.08717 (19)	−0.02586 (11)	0.0505 (5)
C14	0.23128 (11)	0.13987 (18)	−0.01877 (12)	0.0496 (5)
C15	0.24529 (11)	0.23674 (18)	0.03604 (11)	0.0494 (5)
H15	0.2977	0.2714	0.0405	0.059*
C16	0.37141 (14)	0.1250 (3)	−0.0603 (2)	0.1069 (11)
H16A	0.4061	0.0719	−0.0937	0.160*
H16B	0.3873	0.1169	−0.0038	0.160*
H16C	0.3770	0.2128	−0.0772	0.160*

	U11	U22	U33	U12	U13	U23
O1	0.0284 (7)	0.0681 (9)	0.0632 (8)	0.0049 (6)	0.0022 (5)	−0.0101 (7)
O2	0.0294 (7)	0.0634 (9)	0.0855 (10)	−0.0054 (6)	−0.0028 (6)	−0.0207 (8)
O3	0.0523 (9)	0.0907 (12)	0.0856 (11)	−0.0047 (8)	−0.0006 (8)	−0.0401 (9)
O4	0.0661 (10)	0.0756 (10)	0.0707 (10)	−0.0206 (8)	−0.0097 (7)	−0.0194 (8)
C1	0.0338 (9)	0.0456 (10)	0.0500 (10)	0.0044 (7)	−0.0024 (7)	−0.0103 (8)
C2	0.0275 (9)	0.0510 (10)	0.0550 (10)	0.0064 (7)	0.0007 (7)	−0.0087 (9)
C3	0.0290 (9)	0.0447 (10)	0.0530 (10)	−0.0026 (7)	−0.0014 (7)	−0.0011 (8)
C4	0.0373 (10)	0.0531 (11)	0.0629 (12)	−0.0020 (8)	0.0042 (8)	−0.0216 (9)
C5	0.0310 (9)	0.0517 (10)	0.0555 (11)	0.0030 (8)	0.0083 (7)	−0.0108 (9)
C6	0.0287 (8)	0.0403 (9)	0.0407 (9)	0.0004 (7)	0.0005 (6)	0.0004 (8)
C7	0.0303 (9)	0.0444 (9)	0.0452 (9)	0.0018 (7)	0.0005 (7)	0.0033 (8)
C8	0.0307 (9)	0.0561 (11)	0.0491 (10)	0.0000 (8)	−0.0005 (7)	−0.0049 (9)
C9	0.0342 (10)	0.0514 (10)	0.0520 (10)	−0.0002 (8)	−0.0001 (8)	0.0006 (9)
C10	0.0347 (9)	0.0494 (10)	0.0490 (10)	−0.0053 (8)	−0.0055 (8)	0.0043 (8)
C11	0.0390 (10)	0.0655 (12)	0.0524 (11)	−0.0099 (9)	−0.0016 (8)	0.0033 (10)
C12	0.0441 (11)	0.0695 (13)	0.0575 (12)	−0.0221 (10)	−0.0100 (9)	0.0057 (10)
C13	0.0516 (12)	0.0526 (11)	0.0475 (10)	−0.0106 (9)	−0.0139 (9)	0.0030 (9)
C14	0.0426 (11)	0.0545 (11)	0.0518 (10)	−0.0028 (9)	−0.0076 (8)	−0.0008 (9)
C15	0.0361 (9)	0.0552 (11)	0.0568 (11)	−0.0071 (8)	−0.0065 (8)	−0.0035 (9)
C16	0.0457 (14)	0.139 (3)	0.136 (3)	−0.0060 (15)	0.0096 (14)	−0.076 (2)

O1—C7	1.2461 (19)	C7—C8	1.453 (2)
O2—C3	1.359 (2)	C8—C9	1.322 (2)
O2—H2O	0.871 (16)	C8—H8	0.9300
O3—C14	1.362 (2)	C9—C10	1.448 (2)
O3—C16	1.427 (3)	C9—H9	0.9300
O4—C13	1.358 (2)	C10—C11	1.388 (2)
O4—H4O	0.857 (17)	C10—C15	1.399 (2)
C1—C2	1.376 (2)	C11—C12	1.381 (3)
C1—C6	1.389 (2)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.370 (3)
C2—C3	1.372 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.399 (2)
C3—C4	1.383 (2)	C14—C15	1.368 (3)
C4—C5	1.375 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.386 (2)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.473 (2)
C3—O2—H2O	109.3 (16)	C8—C9—C10	127.20 (17)
C14—O3—C16	117.46 (16)	C8—C9—H9	116.4
C13—O4—H4O	110 (2)	C10—C9—H9	116.4
C2—C1—C6	121.48 (16)	C11—C10—C15	118.20 (17)
C2—C1—H1	119.3	C11—C10—C9	119.54 (17)
C6—C1—H1	119.3	C15—C10—C9	122.21 (15)
C3—C2—C1	119.68 (16)	C12—C11—C10	120.65 (18)
C3—C2—H2	120.2	C12—C11—H11	119.7
C1—C2—H2	120.2	C10—C11—H11	119.7
O2—C3—C2	122.38 (15)	C13—C12—C11	120.68 (17)
O2—C3—C4	117.73 (16)	C13—C12—H12	119.7
C2—C3—C4	119.88 (15)	C11—C12—H12	119.7
C5—C4—C3	120.11 (17)	O4—C13—C12	119.51 (17)
C5—C4—H4	119.9	O4—C13—C14	120.99 (19)
C3—C4—H4	119.9	C12—C13—C14	119.50 (18)
C4—C5—C6	120.98 (16)	O3—C14—C15	126.17 (17)
C4—C5—H5	119.5	O3—C14—C13	114.04 (17)
C6—C5—H5	119.5	C15—C14—C13	119.79 (18)
C5—C6—C1	117.86 (15)	C14—C15—C10	121.17 (17)
C5—C6—C7	119.86 (15)	C14—C15—H15	119.4
C1—C6—C7	122.26 (15)	C10—C15—H15	119.4
O1—C7—C8	120.98 (15)	O3—C16—H16A	109.5
O1—C7—C6	119.90 (15)	O3—C16—H16B	109.5
C8—C7—C6	119.12 (14)	H16A—C16—H16B	109.5
C9—C8—C7	124.31 (16)	O3—C16—H16C	109.5
C9—C8—H8	117.8	H16A—C16—H16C	109.5
C7—C8—H8	117.8	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C11	175.35 (19)
C1—C2—C3—O2	−179.82 (17)	C8—C9—C10—C15	−2.2 (3)
C1—C2—C3—C4	−0.7 (3)	C15—C10—C11—C12	0.6 (3)
O2—C3—C4—C5	179.66 (17)	C9—C10—C11—C12	−177.03 (17)
C2—C3—C4—C5	0.5 (3)	C10—C11—C12—C13	−0.3 (3)
C3—C4—C5—C6	−0.5 (3)	C11—C12—C13—O4	−179.87 (18)
C4—C5—C6—C1	0.8 (3)	C11—C12—C13—C14	−0.2 (3)
C4—C5—C6—C7	−177.68 (17)	C16—O3—C14—C15	5.9 (3)
C2—C1—C6—C5	−1.0 (3)	C16—O3—C14—C13	−173.8 (2)
C2—C1—C6—C7	177.44 (16)	O4—C13—C14—O3	−0.3 (3)
C5—C6—C7—O1	−7.4 (3)	C12—C13—C14—O3	−179.98 (18)
C1—C6—C7—O1	174.18 (16)	O4—C13—C14—C15	179.99 (17)
C5—C6—C7—C8	172.36 (16)	C12—C13—C14—C15	0.3 (3)
C1—C6—C7—C8	−6.0 (2)	O3—C14—C15—C10	−179.67 (18)
O1—C7—C8—C9	−10.4 (3)	C13—C14—C15—C10	0.0 (3)
C6—C7—C8—C9	169.82 (17)	C11—C10—C15—C14	−0.5 (3)
C7—C8—C9—C10	−176.97 (17)	C9—C10—C15—C14	177.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3	0.86 (2)	2.20 (3)	2.655 (2)	113 (2)
O2—H2O···O1i	0.87 (2)	1.87 (2)	2.7349 (18)	173 (2)
O4—H4O···O1ii	0.86 (2)	2.22 (2)	2.937 (2)	141 (3)
C16—H16A···Cgii	0.96	2.86	3.747 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3	0.86 (2)	2.20 (3)	2.655 (2)	113 (2)
O2—H2O⋯O1i	0.87 (2)	1.87 (2)	2.7349 (18)	173 (2)
O4—H4O⋯O1ii	0.86 (2)	2.22 (2)	2.937 (2)	141 (3)
C16—H16A⋯Cg ii	0.96	2.86	3.747 (3)	155

Symmetry codes: (i) ; (ii) .