Crystal structure of (2E)-3-(3-eth-oxy-4-hy-droxy-phen-yl)-1-(4-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C17H16O4, the dihedral angle between the benzene rings is 21.22 (1)° and the mean plane of the prop-2-en-1-one group makes dihedral angles of 10.60 (1) and 11.28 (1)°, respectively, with those of the hy-droxy-phenyl and eth-oxy-phenyl rings. The eth-oxy substituent forms a dihedral angle of 88.79 (2)° with the the prop-2-en-1-one group, which is found to be slightly twisted. In the crystal, phenolic O-H⋯O hydrogen bonds to the carbonyl O atom form a two-dimensional supra-molecular network structure lying parallel to (010).

Related literature

For the biological activity of chalcone derivatives, see: Nowakowska (2007 ▶); Ram et al. (2000 ▶); Khatib et al. (2005 ▶); Papo & Shai (2003 ▶). For related structures, see: Jasinski et al. (2011 ▶); Sathya et al. (2014 ▶); Joothamongkhon et al. (2010 ▶); Horkaew et al. (2010 ▶). For the synthesis, see: Sidharthan et al. (2012 ▶); Chitra et al. (2013 ▶); Sathya et al. (2014 ▶).

Experimental

Crystal data

C17H16O4

M = 284.30

Orthorhombic,

a = 16.3670 (4) Å

b = 10.5512 (3) Å

c = 16.6153 (4) Å

V = 2869.32 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.21 × 0.19 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.970, T max = 0.985

14416 measured reflections

3592 independent reflections

2619 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.215

S = 0.72

3592 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.43 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: SHELXS97 (Sheldrick, 2008 ▶); 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814023368/zs2316sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023368/zs2316Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023368/zs2316Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814023368/zs2316fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814023368/zs2316fig2.tif

The packing of the mol­ecules in the unit cell. Non-associative H-atoms are omitted and dashed lines indicate hydrogen bonds.

CCDC reference: 1030607

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

C17H16O4	F(000) = 1200
Mr = 284.30	Dx = 1.316 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3592 reflections
a = 16.3670 (4) Å	θ = 2.5–28.4°
b = 10.5512 (3) Å	µ = 0.09 mm−1
c = 16.6153 (4) Å	T = 293 K
V = 2869.32 (13) Å3	Block, colourless
Z = 8	0.22 × 0.21 × 0.19 mm

Bruker Kappa APEXII CCD diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
Tmin = 0.970, Tmax = 0.985	k = −11→14
14416 measured reflections	l = −21→22

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215	H-atom parameters constrained
S = 0.72	w = 1/[σ2(Fo2) + (0.189P)2 + 2.3286P] where P = (Fo2 + 2Fc2)/3
3592 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C8	0.4080 (2)	1.4090 (4)	0.5257 (2)	0.0948 (11)
H8A	0.4638	1.3812	0.5246	0.142*
H8B	0.4060	1.4969	0.5404	0.142*
H8C	0.3841	1.3980	0.4734	0.142*
C1	0.22651 (13)	1.3374 (2)	0.52630 (13)	0.0481 (5)
C2	0.14997 (13)	1.39834 (19)	0.52749 (12)	0.0459 (5)
C3	0.09113 (13)	1.3644 (2)	0.47328 (13)	0.0519 (5)
H3	0.0402	1.4036	0.4748	0.062*
C4	0.10695 (12)	1.2720 (2)	0.41605 (12)	0.0464 (5)
H4	0.0662	1.2491	0.3798	0.056*
C5	0.18244 (11)	1.21328 (18)	0.41214 (11)	0.0405 (4)
C6	0.24215 (12)	1.2466 (2)	0.46881 (13)	0.0491 (5)
H6	0.2929	1.2069	0.4676	0.059*
C7	0.19783 (11)	1.11972 (18)	0.34958 (11)	0.0405 (4)
H7	0.1538	1.0987	0.3169	0.049*
C9	0.26765 (11)	1.0613 (2)	0.33418 (12)	0.0424 (4)
H9	0.3122	1.0779	0.3673	0.051*
C10	0.27837 (10)	0.97178 (17)	0.26748 (11)	0.0353 (4)
C11	0.36197 (10)	0.93496 (16)	0.24468 (10)	0.0331 (4)
C12	0.37395 (11)	0.83378 (18)	0.19164 (12)	0.0404 (4)
H12	0.3289	0.7928	0.1695	0.048*
C13	0.45150 (11)	0.79391 (19)	0.17169 (12)	0.0439 (5)
H13	0.4586	0.7265	0.1363	0.053*
C14	0.51931 (10)	0.85457 (17)	0.20461 (11)	0.0369 (4)
C15	0.50858 (11)	0.95616 (18)	0.25631 (12)	0.0388 (4)
H15	0.5537	0.9978	0.2777	0.047*
C16	0.43087 (11)	0.99521 (17)	0.27588 (11)	0.0383 (4)
H16	0.4241	1.0634	0.3107	0.046*
C17	0.36220 (17)	1.3339 (3)	0.58491 (17)	0.0685 (7)
H17A	0.3649	1.2449	0.5706	0.082*
H17B	0.3866	1.3443	0.6377	0.082*
O1	0.13388 (11)	1.48915 (16)	0.58349 (10)	0.0614 (5)
H1	0.1742	1.4996	0.6120	0.092*
O2	0.27758 (11)	1.3744 (2)	0.58724 (11)	0.0693 (5)
O3	0.59416 (8)	0.81036 (15)	0.18410 (10)	0.0521 (4)
H3A	0.6294	0.8522	0.2071	0.078*
O4	0.21879 (8)	0.92718 (14)	0.23142 (9)	0.0459 (4)

	U11	U22	U33	U12	U13	U23
C8	0.073 (2)	0.102 (3)	0.109 (3)	−0.0156 (18)	0.0008 (18)	−0.020 (2)
C1	0.0428 (10)	0.0523 (11)	0.0490 (11)	0.0000 (8)	0.0078 (8)	−0.0092 (8)
C2	0.0484 (11)	0.0444 (9)	0.0447 (10)	0.0038 (8)	0.0164 (8)	0.0003 (8)
C3	0.0447 (11)	0.0565 (12)	0.0546 (12)	0.0179 (9)	0.0094 (9)	0.0036 (9)
C4	0.0383 (10)	0.0543 (11)	0.0468 (11)	0.0080 (8)	0.0016 (8)	0.0021 (9)
C5	0.0352 (9)	0.0435 (9)	0.0430 (10)	0.0025 (7)	0.0056 (7)	0.0001 (7)
C6	0.0351 (9)	0.0587 (12)	0.0536 (12)	0.0053 (8)	0.0009 (8)	−0.0135 (9)
C7	0.0327 (8)	0.0458 (9)	0.0429 (10)	0.0003 (7)	−0.0004 (7)	−0.0022 (7)
C9	0.0291 (8)	0.0559 (11)	0.0423 (10)	0.0000 (7)	−0.0010 (7)	−0.0087 (8)
C10	0.0264 (8)	0.0425 (9)	0.0370 (9)	−0.0010 (6)	0.0000 (6)	0.0016 (7)
C11	0.0265 (8)	0.0395 (8)	0.0334 (8)	−0.0017 (6)	−0.0007 (6)	−0.0007 (6)
C12	0.0300 (8)	0.0465 (10)	0.0447 (10)	−0.0037 (7)	−0.0052 (7)	−0.0093 (7)
C13	0.0347 (9)	0.0460 (9)	0.0510 (11)	0.0021 (7)	−0.0030 (7)	−0.0160 (8)
C14	0.0266 (8)	0.0411 (8)	0.0428 (9)	0.0009 (6)	0.0008 (6)	0.0003 (7)
C15	0.0262 (8)	0.0459 (9)	0.0444 (10)	−0.0062 (7)	−0.0030 (7)	−0.0063 (7)
C16	0.0302 (9)	0.0414 (9)	0.0433 (10)	−0.0036 (7)	0.0007 (7)	−0.0081 (7)
C17	0.0640 (16)	0.0714 (16)	0.0699 (16)	0.0077 (12)	−0.0186 (12)	−0.0210 (13)
O1	0.0625 (10)	0.0616 (9)	0.0600 (10)	0.0136 (8)	0.0132 (8)	−0.0155 (7)
O2	0.0556 (10)	0.0857 (12)	0.0666 (11)	0.0044 (9)	−0.0012 (8)	−0.0341 (10)
O3	0.0292 (7)	0.0553 (8)	0.0719 (10)	0.0039 (6)	0.0018 (6)	−0.0147 (7)
O4	0.0266 (6)	0.0603 (9)	0.0508 (8)	−0.0045 (6)	−0.0024 (5)	−0.0078 (6)

C8—C17	1.469 (5)	C9—H9	0.9300
C8—H8A	0.9600	C10—O4	1.237 (2)
C8—H8B	0.9600	C10—C11	1.472 (2)
C8—H8C	0.9600	C11—C16	1.394 (2)
C1—O2	1.370 (3)	C11—C12	1.398 (2)
C1—C6	1.377 (3)	C12—C13	1.378 (3)
C1—C2	1.408 (3)	C12—H12	0.9300
C2—O1	1.361 (2)	C13—C14	1.393 (3)
C2—C3	1.366 (3)	C13—H13	0.9300
C3—C4	1.387 (3)	C14—O3	1.354 (2)
C3—H3	0.9300	C14—C15	1.385 (3)
C4—C5	1.384 (3)	C15—C16	1.376 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.402 (3)	C16—H16	0.9300
C5—C7	1.455 (3)	C17—O2	1.450 (3)
C6—H6	0.9300	C17—H17A	0.9700
C7—C9	1.323 (3)	C17—H17B	0.9700
C7—H7	0.9300	O1—H1	0.8200
C9—C10	1.467 (3)	O3—H3A	0.8200
C17—C8—H8A	109.5	O4—C10—C9	121.10 (16)
C17—C8—H8B	109.5	O4—C10—C11	120.50 (16)
H8A—C8—H8B	109.5	C9—C10—C11	118.40 (15)
C17—C8—H8C	109.5	C16—C11—C12	117.97 (16)
H8A—C8—H8C	109.5	C16—C11—C10	122.39 (16)
H8B—C8—H8C	109.5	C12—C11—C10	119.61 (15)
O2—C1—C6	126.71 (19)	C13—C12—C11	120.93 (16)
O2—C1—C2	113.72 (18)	C13—C12—H12	119.5
C6—C1—C2	119.5 (2)	C11—C12—H12	119.5
O1—C2—C3	119.90 (19)	C12—C13—C14	119.96 (17)
O1—C2—C1	120.2 (2)	C12—C13—H13	120.0
C3—C2—C1	119.88 (18)	C14—C13—H13	120.0
C2—C3—C4	120.31 (19)	O3—C14—C15	122.50 (16)
C2—C3—H3	119.8	O3—C14—C13	117.62 (17)
C4—C3—H3	119.8	C15—C14—C13	119.88 (16)
C5—C4—C3	120.91 (19)	C16—C15—C14	119.71 (16)
C5—C4—H4	119.5	C16—C15—H15	120.1
C3—C4—H4	119.5	C14—C15—H15	120.1
C4—C5—C6	118.62 (18)	C15—C16—C11	121.54 (16)
C4—C5—C7	119.44 (18)	C15—C16—H16	119.2
C6—C5—C7	121.93 (17)	C11—C16—H16	119.2
C1—C6—C5	120.71 (19)	O2—C17—C8	110.3 (3)
C1—C6—H6	119.6	O2—C17—H17A	109.6
C5—C6—H6	119.6	C8—C17—H17A	109.6
C9—C7—C5	127.10 (18)	O2—C17—H17B	109.6
C9—C7—H7	116.4	C8—C17—H17B	109.6
C5—C7—H7	116.4	H17A—C17—H17B	108.1
C7—C9—C10	123.31 (17)	C2—O1—H1	109.5
C7—C9—H9	118.3	C1—O2—C17	118.63 (17)
C10—C9—H9	118.3	C14—O3—H3A	109.5
O2—C1—C2—O1	2.9 (3)	O4—C10—C11—C16	171.05 (18)
C6—C1—C2—O1	−179.4 (2)	C9—C10—C11—C16	−9.5 (3)
O2—C1—C2—C3	−175.8 (2)	O4—C10—C11—C12	−10.8 (3)
C6—C1—C2—C3	1.9 (3)	C9—C10—C11—C12	168.66 (18)
O1—C2—C3—C4	−179.95 (19)	C16—C11—C12—C13	0.8 (3)
C1—C2—C3—C4	−1.3 (3)	C10—C11—C12—C13	−177.40 (18)
C2—C3—C4—C5	−0.6 (3)	C11—C12—C13—C14	0.1 (3)
C3—C4—C5—C6	1.8 (3)	C12—C13—C14—O3	178.93 (19)
C3—C4—C5—C7	−177.92 (19)	C12—C13—C14—C15	−1.1 (3)
O2—C1—C6—C5	176.6 (2)	O3—C14—C15—C16	−178.90 (18)
C2—C1—C6—C5	−0.7 (3)	C13—C14—C15—C16	1.1 (3)
C4—C5—C6—C1	−1.1 (3)	C14—C15—C16—C11	−0.1 (3)
C7—C5—C6—C1	178.6 (2)	C12—C11—C16—C15	−0.8 (3)
C4—C5—C7—C9	175.3 (2)	C10—C11—C16—C15	177.37 (18)
C6—C5—C7—C9	−4.5 (3)	C6—C1—O2—C17	12.3 (4)
C5—C7—C9—C10	−177.43 (18)	C2—C1—O2—C17	−170.2 (2)
C7—C9—C10—O4	−14.2 (3)	C8—C17—O2—C1	76.2 (3)
C7—C9—C10—C11	166.32 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	2.25	2.958 (2)	145
O3—H3A···O4ii	0.82	1.95	2.766 (2)	171
C7—H7···O4	0.93	2.53	2.846 (2)	100

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O4i	0.82	2.25	2.958(2)	145
O3H3AO4ii	0.82	1.95	2.766(2)	171

Symmetry codes: (i) ; (ii) .