(2E)-1-(3,5-Di-hydroxy-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C16H14O4, the benzene rings are inclined to one another by 4.91 (7)°. The conformation about the C=O and C=C bonds is trans and cis, respectively. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. The dimers are linked via O-H⋯O and C-H⋯O hydrogen bonds, forming undulating two-dimensional networks lying parallel to (10-1). These networks are linked by further C-H⋯O hydrogen bonds, forming a three-dimensional structure.

Related literature

For the biological activity of chalcone derivatives, see: Shenvi et al. (2013 ▶); Sharma et al. (2012 ▶); Hsieh et al. (2012 ▶); Sashidhara et al. (2011 ▶). For related structures, see: Ahn et al. (2013 ▶); Jasinski et al. (2011 ▶). For standard bend lengths, see: Allen et al. (1987 ▶). For the synthesis, see: Shettigar et al. (2006 ▶); Patil et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H14O4

M = 270.28

Monoclinic,

a = 9.1920 (9) Å

b = 13.8931 (13) Å

c = 10.9299 (10) Å

β = 106.619 (2)°

V = 1337.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.979, T max = 0.981

13378 measured reflections

3402 independent reflections

2617 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.137

S = 0.91

3384 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 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/S1600536814009155/su2727sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009155/su2727Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009155/su2727Isup3.cml

CCDC reference: 998945

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

C16H14O4	F(000) = 568
Mr = 270.28	Dx = 1.342 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3402 reflections
a = 9.1920 (9) Å	θ = 2.4–28.5°
b = 13.8931 (13) Å	µ = 0.10 mm−1
c = 10.9299 (10) Å	T = 293 K
β = 106.619 (2)°	Block, colourless
V = 1337.5 (2) Å3	0.22 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3402 independent reflections
Radiation source: fine-focus sealed tube	2617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scan	θmax = 28.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→12
Tmin = 0.979, Tmax = 0.981	k = −18→18
13378 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0868P)2 + 0.2822P] where P = (Fo2 + 2Fc2)/3
3384 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.17 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	0.24996 (15)	0.22432 (10)	0.12529 (12)	0.0470 (3)
H1	0.2457	0.2550	0.1998	0.056*
C2	0.15728 (15)	0.25425 (10)	0.00768 (12)	0.0447 (3)
C3	0.16469 (14)	0.20929 (10)	−0.10413 (11)	0.0429 (3)
H3	0.1017	0.2292	−0.1827	0.051*
C4	0.26647 (14)	0.13466 (9)	−0.09755 (11)	0.0404 (3)
C5	0.35787 (15)	0.10425 (10)	0.01976 (11)	0.0431 (3)
H5	0.4258	0.0538	0.0243	0.052*
C6	0.34818 (14)	0.14885 (10)	0.13033 (11)	0.0427 (3)
C7	0.28664 (15)	0.08504 (10)	−0.21300 (12)	0.0455 (3)
C8	0.18574 (15)	0.10638 (10)	−0.33903 (11)	0.0440 (3)
H8	0.1070	0.1502	−0.3473	0.053*
C9	0.20462 (15)	0.06396 (10)	−0.44272 (12)	0.0456 (3)
H9	0.2855	0.0212	−0.4289	0.055*
C10	0.11515 (14)	0.07605 (9)	−0.57409 (11)	0.0414 (3)
C11	0.14639 (15)	0.01784 (10)	−0.66808 (12)	0.0461 (3)
H11	0.2250	−0.0267	−0.6448	0.055*
C12	0.06338 (16)	0.02522 (10)	−0.79376 (12)	0.0474 (3)
H12	0.0849	−0.0147	−0.8547	0.057*
C13	−0.05233 (15)	0.09213 (10)	−0.82969 (11)	0.0423 (3)
C14	−0.08502 (16)	0.15125 (11)	−0.73877 (12)	0.0477 (3)
H14	−0.1623	0.1967	−0.7627	0.057*
C15	−0.00197 (16)	0.14207 (10)	−0.61259 (12)	0.0474 (3)
H15	−0.0252	0.1812	−0.5517	0.057*
C16	−0.24683 (19)	0.16157 (14)	−0.99921 (14)	0.0642 (4)
H16A	−0.2893	0.1554	−1.0899	0.096*
H16B	−0.2083	0.2257	−0.9792	0.096*
H16C	−0.3240	0.1492	−0.9578	0.096*
O1	0.39025 (14)	0.02703 (10)	−0.19868 (9)	0.0712 (4)
O2	0.43646 (11)	0.11864 (8)	0.24713 (8)	0.0539 (3)
H2	0.4898	0.0736	0.2377	0.081*
O3	0.06007 (13)	0.32813 (8)	0.00670 (10)	0.0626 (3)
H3A	0.0110	0.3399	−0.0671	0.094*
O4	−0.12717 (12)	0.09454 (8)	−0.95602 (9)	0.0559 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0550 (7)	0.0512 (8)	0.0324 (6)	−0.0020 (6)	0.0088 (5)	−0.0046 (5)
C2	0.0490 (7)	0.0439 (7)	0.0394 (6)	−0.0002 (5)	0.0098 (5)	−0.0002 (5)
C3	0.0462 (6)	0.0460 (7)	0.0327 (6)	−0.0006 (5)	0.0052 (5)	0.0019 (5)
C4	0.0452 (6)	0.0422 (7)	0.0303 (5)	−0.0040 (5)	0.0051 (5)	−0.0014 (4)
C5	0.0463 (6)	0.0459 (7)	0.0321 (6)	0.0004 (5)	0.0033 (5)	−0.0018 (5)
C6	0.0462 (6)	0.0480 (7)	0.0290 (5)	−0.0075 (5)	0.0027 (5)	−0.0010 (5)
C7	0.0523 (7)	0.0479 (7)	0.0312 (6)	0.0038 (5)	0.0035 (5)	−0.0010 (5)
C8	0.0495 (7)	0.0465 (7)	0.0312 (6)	0.0022 (5)	0.0036 (5)	0.0003 (5)
C9	0.0508 (7)	0.0479 (7)	0.0336 (6)	0.0053 (5)	0.0048 (5)	−0.0008 (5)
C10	0.0479 (6)	0.0437 (7)	0.0302 (5)	0.0002 (5)	0.0073 (5)	−0.0022 (5)
C11	0.0519 (7)	0.0478 (7)	0.0378 (6)	0.0087 (6)	0.0116 (5)	−0.0020 (5)
C12	0.0592 (7)	0.0504 (8)	0.0337 (6)	0.0040 (6)	0.0149 (5)	−0.0068 (5)
C13	0.0503 (7)	0.0463 (7)	0.0282 (5)	−0.0033 (5)	0.0081 (5)	−0.0024 (5)
C14	0.0536 (7)	0.0487 (8)	0.0366 (6)	0.0107 (6)	0.0062 (5)	−0.0043 (5)
C15	0.0574 (8)	0.0496 (7)	0.0322 (6)	0.0086 (6)	0.0079 (5)	−0.0079 (5)
C16	0.0666 (10)	0.0746 (11)	0.0406 (7)	0.0090 (8)	−0.0018 (6)	0.0036 (7)
O1	0.0817 (8)	0.0862 (9)	0.0363 (5)	0.0398 (7)	0.0017 (5)	−0.0036 (5)
O2	0.0619 (6)	0.0627 (6)	0.0286 (4)	0.0080 (5)	−0.0006 (4)	−0.0031 (4)
O3	0.0747 (7)	0.0664 (7)	0.0434 (5)	0.0224 (5)	0.0116 (5)	−0.0024 (5)
O4	0.0678 (6)	0.0644 (7)	0.0293 (4)	0.0076 (5)	0.0036 (4)	−0.0044 (4)

C1—C6	1.374 (2)	C10—C15	1.3850 (18)
C1—C2	1.3873 (18)	C10—C11	1.4002 (17)
C1—H1	0.9300	C11—C12	1.3712 (17)
C2—O3	1.3589 (16)	C11—H11	0.9300
C2—C3	1.3913 (18)	C12—C13	1.3823 (19)
C3—C4	1.3846 (18)	C12—H12	0.9300
C3—H3	0.9300	C13—O4	1.3555 (14)
C4—C5	1.3829 (16)	C13—C14	1.3868 (18)
C4—C7	1.4952 (18)	C14—C15	1.3780 (17)
C5—C6	1.3835 (17)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—O2	1.3681 (14)	C16—O4	1.4152 (19)
C7—O1	1.2230 (16)	C16—H16A	0.9600
C7—C8	1.4542 (16)	C16—H16B	0.9600
C8—C9	1.3320 (18)	C16—H16C	0.9600
C8—H8	0.9300	O2—H2	0.8200
C9—C10	1.4460 (16)	O3—H3A	0.8200
C9—H9	0.9300
C6—C1—C2	119.21 (12)	C15—C10—C11	117.67 (11)
C6—C1—H1	120.4	C15—C10—C9	123.40 (11)
C2—C1—H1	120.4	C11—C10—C9	118.93 (12)
O3—C2—C1	117.50 (12)	C12—C11—C10	121.31 (12)
O3—C2—C3	121.97 (12)	C12—C11—H11	119.3
C1—C2—C3	120.53 (12)	C10—C11—H11	119.3
C4—C3—C2	119.52 (11)	C11—C12—C13	119.83 (12)
C4—C3—H3	120.2	C11—C12—H12	120.1
C2—C3—H3	120.2	C13—C12—H12	120.1
C5—C4—C3	119.95 (12)	O4—C13—C12	115.54 (11)
C5—C4—C7	116.91 (12)	O4—C13—C14	124.36 (12)
C3—C4—C7	123.12 (11)	C12—C13—C14	120.10 (11)
C4—C5—C6	119.95 (12)	C15—C14—C13	119.39 (12)
C4—C5—H5	120.0	C15—C14—H14	120.3
C6—C5—H5	120.0	C13—C14—H14	120.3
O2—C6—C1	118.62 (11)	C14—C15—C10	121.69 (12)
O2—C6—C5	120.56 (12)	C14—C15—H15	119.2
C1—C6—C5	120.82 (11)	C10—C15—H15	119.2
O1—C7—C8	121.19 (12)	O4—C16—H16A	109.5
O1—C7—C4	118.41 (11)	O4—C16—H16B	109.5
C8—C7—C4	120.40 (12)	H16A—C16—H16B	109.5
C9—C8—C7	120.85 (12)	O4—C16—H16C	109.5
C9—C8—H8	119.6	H16A—C16—H16C	109.5
C7—C8—H8	119.6	H16B—C16—H16C	109.5
C8—C9—C10	128.17 (13)	C6—O2—H2	109.5
C8—C9—H9	115.9	C2—O3—H3A	109.5
C10—C9—H9	115.9	C13—O4—C16	118.40 (11)
C6—C1—C2—O3	179.03 (12)	C4—C7—C8—C9	178.67 (13)
C6—C1—C2—C3	−0.8 (2)	C7—C8—C9—C10	179.53 (13)
O3—C2—C3—C4	179.68 (12)	C8—C9—C10—C15	5.0 (2)
C1—C2—C3—C4	−0.6 (2)	C8—C9—C10—C11	−174.38 (14)
C2—C3—C4—C5	1.14 (19)	C15—C10—C11—C12	−0.5 (2)
C2—C3—C4—C7	−177.38 (12)	C9—C10—C11—C12	178.91 (13)
C3—C4—C5—C6	−0.4 (2)	C10—C11—C12—C13	0.9 (2)
C7—C4—C5—C6	178.19 (12)	C11—C12—C13—O4	179.54 (12)
C2—C1—C6—O2	−178.54 (12)	C11—C12—C13—C14	−0.4 (2)
C2—C1—C6—C5	1.5 (2)	O4—C13—C14—C15	179.57 (13)
C4—C5—C6—O2	179.12 (12)	C12—C13—C14—C15	−0.5 (2)
C4—C5—C6—C1	−0.9 (2)	C13—C14—C15—C10	0.9 (2)
C5—C4—C7—O1	−6.2 (2)	C11—C10—C15—C14	−0.4 (2)
C3—C4—C7—O1	172.31 (14)	C9—C10—C15—C14	−179.79 (14)
C5—C4—C7—C8	174.30 (12)	C12—C13—O4—C16	−179.90 (14)
C3—C4—C7—C8	−7.1 (2)	C14—C13—O4—C16	0.0 (2)
O1—C7—C8—C9	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.90	2.7196 (15)	174
O3—H3A···O2ii	0.82	2.03	2.8361 (14)	167
C3—H3···O2ii	0.93	2.59	3.2875 (17)	132
C5—H5···O1i	0.93	2.43	3.1498 (17)	134
C12—H12···O4iii	0.93	2.47	3.3926 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.90	2.7196 (15)	174
O3—H3A⋯O2ii	0.82	2.03	2.8361 (14)	167
C3—H3⋯O2ii	0.93	2.59	3.2875 (17)	132
C5—H5⋯O1i	0.93	2.43	3.1498 (17)	134
C12—H12⋯O4iii	0.93	2.47	3.3926 (16)	169

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