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

In the title compound, C(17)H(16)O(3), the carbonyl group is in an s-cis configuration with respect to the olefinic double bond. The dihedral angle between the two benzene rings is 2.85 (3)°. The prop-2-en-1-one bridge makes dihedral angles of 4.77 (4) and 4.15 (4)°, respectively, with the 2-hy-droxy-phenyl and 4-eth-oxy-phenyl rings. The eth-oxy group is coplanar with the attached phenyl ring [C(ar)-O-C-C = 179.72 (5)°]. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, mol-ecules are stacked in an anti-parallel manner to form columns along the b axis. The columnar structure is stabilized by C-H⋯π inter-actions involving the 2-hy-droxy-phenyl ring.

Related literature

For background on the applications of chalcones, see: Jun et al. (2007 ▶); Nowakowska (2007 ▶); Patil & Dharmaprakash (2008 ▶); Saydam et al. (2003 ▶); Svetlichny et al. (2007 ▶); Tewtrakul et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2008 ▶); Patil et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H16O3

M = 268.30

Triclinic,

a = 6.8305 (2) Å

b = 6.8790 (2) Å

c = 14.8188 (3) Å

α = 88.533 (1)°

β = 80.380 (1)°

γ = 77.469 (1)°

V = 670.11 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.60 × 0.38 × 0.36 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.948, T max = 0.969

24772 measured reflections

5849 independent reflections

5179 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.04

5848 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032514/ci5143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032514/ci5143Isup2.hkl

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

C17H16O3	Z = 2
Mr = 268.30	F(000) = 284
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -P 1	Melting point = 387–388 K
a = 6.8305 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.8790 (2) Å	Cell parameters from 5849 reflections
c = 14.8188 (3) Å	θ = 1.4–35.0°
α = 88.533 (1)°	µ = 0.09 mm−1
β = 80.380 (1)°	T = 100 K
γ = 77.469 (1)°	Block, yellow
V = 670.11 (3) Å3	0.60 × 0.38 × 0.36 mm

Bruker APEXII CCD area-detector diffractometer	5849 independent reflections
Radiation source: sealed tube	5179 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 35.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.948, Tmax = 0.969	k = −10→11
24772 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0744P)2 + 0.1118P] where P = (Fo2 + 2Fc2)/3
5848 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 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	1.46060 (7)	0.63044 (8)	0.13054 (3)	0.01858 (10)
O2	1.59166 (7)	0.61854 (8)	0.27959 (4)	0.01890 (11)
H1O2	1.589 (2)	0.614 (2)	0.2173 (11)	0.052 (4)*
O3	0.61756 (7)	0.84310 (8)	−0.23045 (3)	0.01749 (10)
C1	1.39580 (9)	0.65747 (9)	0.32040 (4)	0.01353 (11)
C2	1.35615 (10)	0.66707 (10)	0.41620 (4)	0.01724 (12)
H2A	1.4636	0.6474	0.4490	0.021*
C3	1.15843 (11)	0.70553 (11)	0.46221 (5)	0.02141 (13)
H3A	1.1333	0.7123	0.5258	0.026*
C4	0.99566 (11)	0.73437 (12)	0.41364 (5)	0.02221 (14)
H4A	0.8626	0.7594	0.4448	0.027*
C5	1.03359 (10)	0.72550 (10)	0.31877 (4)	0.01683 (12)
H5A	0.9248	0.7447	0.2869	0.020*
C6	1.23305 (9)	0.68816 (9)	0.26988 (4)	0.01237 (10)
C7	1.27920 (9)	0.67709 (9)	0.16865 (4)	0.01267 (10)
C8	1.11547 (9)	0.72198 (9)	0.11403 (4)	0.01350 (11)
H8A	0.9811	0.7630	0.1425	0.016*
C9	1.16056 (9)	0.70358 (9)	0.02217 (4)	0.01346 (11)
H9A	1.2972	0.6595	−0.0024	0.016*
C10	1.01927 (9)	0.74506 (9)	−0.04275 (4)	0.01229 (10)
C11	0.80665 (9)	0.79158 (9)	−0.01582 (4)	0.01357 (11)
H11A	0.7517	0.7999	0.0461	0.016*
C12	0.67867 (9)	0.82501 (9)	−0.08002 (4)	0.01398 (11)
H12A	0.5386	0.8566	−0.0611	0.017*
C13	0.75873 (9)	0.81164 (9)	−0.17369 (4)	0.01315 (10)
C14	0.96900 (9)	0.76806 (10)	−0.20234 (4)	0.01477 (11)
H14A	1.0233	0.7606	−0.2643	0.018*
C15	1.09656 (9)	0.73581 (9)	−0.13654 (4)	0.01429 (11)
H15A	1.2367	0.7074	−0.1555	0.017*
C16	0.68663 (9)	0.83005 (9)	−0.32736 (4)	0.01484 (11)
H16A	0.7685	0.6985	−0.3445	0.018*
H16B	0.7680	0.9278	−0.3465	0.018*
C17	0.49767 (11)	0.87050 (11)	−0.37121 (5)	0.01895 (12)
H17A	0.5358	0.8690	−0.4366	0.028*
H17B	0.4155	0.9986	−0.3514	0.028*
H17C	0.4217	0.7696	−0.3536	0.028*

	U11	U22	U33	U12	U13	U23
O1	0.01206 (19)	0.0280 (3)	0.0151 (2)	−0.00354 (17)	−0.00144 (15)	−0.00028 (17)
O2	0.01199 (19)	0.0265 (2)	0.0186 (2)	−0.00291 (17)	−0.00501 (16)	−0.00171 (18)
O3	0.01373 (19)	0.0271 (3)	0.01164 (19)	−0.00273 (17)	−0.00437 (14)	0.00013 (16)
C1	0.0135 (2)	0.0129 (2)	0.0151 (2)	−0.00301 (18)	−0.00482 (18)	0.00005 (18)
C2	0.0209 (3)	0.0179 (3)	0.0145 (2)	−0.0041 (2)	−0.0076 (2)	0.00091 (19)
C3	0.0244 (3)	0.0268 (3)	0.0130 (2)	−0.0054 (2)	−0.0034 (2)	0.0009 (2)
C4	0.0174 (3)	0.0329 (4)	0.0149 (3)	−0.0044 (2)	−0.0001 (2)	0.0007 (2)
C5	0.0130 (2)	0.0228 (3)	0.0145 (2)	−0.0035 (2)	−0.00232 (19)	0.0006 (2)
C6	0.0120 (2)	0.0133 (2)	0.0122 (2)	−0.00281 (17)	−0.00315 (17)	0.00025 (17)
C7	0.0127 (2)	0.0131 (2)	0.0129 (2)	−0.00335 (17)	−0.00318 (17)	0.00039 (17)
C8	0.0128 (2)	0.0150 (2)	0.0130 (2)	−0.00247 (18)	−0.00374 (18)	−0.00015 (18)
C9	0.0138 (2)	0.0146 (2)	0.0129 (2)	−0.00401 (18)	−0.00363 (17)	0.00107 (18)
C10	0.0129 (2)	0.0128 (2)	0.0116 (2)	−0.00302 (17)	−0.00291 (17)	0.00046 (17)
C11	0.0136 (2)	0.0159 (2)	0.0113 (2)	−0.00358 (18)	−0.00181 (17)	0.00037 (17)
C12	0.0124 (2)	0.0167 (2)	0.0125 (2)	−0.00295 (18)	−0.00149 (17)	−0.00021 (18)
C13	0.0127 (2)	0.0145 (2)	0.0126 (2)	−0.00236 (18)	−0.00379 (17)	0.00019 (18)
C14	0.0134 (2)	0.0191 (3)	0.0111 (2)	−0.00229 (19)	−0.00181 (17)	−0.00019 (18)
C15	0.0122 (2)	0.0177 (3)	0.0124 (2)	−0.00208 (18)	−0.00191 (17)	−0.00048 (18)
C16	0.0169 (2)	0.0151 (2)	0.0129 (2)	−0.00269 (19)	−0.00430 (18)	0.00006 (18)
C17	0.0206 (3)	0.0204 (3)	0.0173 (3)	−0.0031 (2)	−0.0091 (2)	0.0003 (2)

O1—C7	1.2491 (7)	C9—C10	1.4543 (8)
O2—C1	1.3452 (8)	C9—H9A	0.93
O2—H1O2	0.928 (16)	C10—C15	1.3998 (8)
O3—C13	1.3621 (7)	C10—C11	1.4078 (8)
O3—C16	1.4334 (7)	C11—C12	1.3791 (8)
C1—C2	1.4006 (9)	C11—H11A	0.93
C1—C6	1.4174 (8)	C12—C13	1.4019 (8)
C2—C3	1.3803 (10)	C12—H12A	0.93
C2—H2A	0.93	C13—C14	1.3960 (8)
C3—C4	1.3993 (10)	C14—C15	1.3957 (8)
C3—H3A	0.93	C14—H14A	0.93
C4—C5	1.3868 (9)	C15—H15A	0.93
C4—H4A	0.93	C16—C17	1.5102 (9)
C5—C6	1.4053 (8)	C16—H16A	0.97
C5—H5A	0.93	C16—H16B	0.97
C6—C7	1.4808 (8)	C17—H17A	0.96
C7—C8	1.4632 (8)	C17—H17B	0.96
C8—C9	1.3475 (8)	C17—H17C	0.96
C8—H8A	0.93
C1—O2—H1O2	105.5 (10)	C15—C10—C9	118.97 (5)
C13—O3—C16	118.56 (5)	C11—C10—C9	123.04 (5)
O2—C1—C2	117.49 (5)	C12—C11—C10	120.91 (5)
O2—C1—C6	122.28 (5)	C12—C11—H11A	119.5
C2—C1—C6	120.23 (6)	C10—C11—H11A	119.5
C3—C2—C1	120.32 (6)	C11—C12—C13	120.33 (5)
C3—C2—H2A	119.8	C11—C12—H12A	119.8
C1—C2—H2A	119.8	C13—C12—H12A	119.8
C2—C3—C4	120.34 (6)	O3—C13—C14	125.05 (5)
C2—C3—H3A	119.8	O3—C13—C12	114.98 (5)
C4—C3—H3A	119.8	C14—C13—C12	119.97 (5)
C5—C4—C3	119.71 (6)	C15—C14—C13	119.03 (5)
C5—C4—H4A	120.1	C15—C14—H14A	120.5
C3—C4—H4A	120.1	C13—C14—H14A	120.5
C4—C5—C6	121.34 (6)	C14—C15—C10	121.76 (5)
C4—C5—H5A	119.3	C14—C15—H15A	119.1
C6—C5—H5A	119.3	C10—C15—H15A	119.1
C5—C6—C1	118.06 (5)	O3—C16—C17	106.17 (5)
C5—C6—C7	122.80 (5)	O3—C16—H16A	110.5
C1—C6—C7	119.14 (5)	C17—C16—H16A	110.5
O1—C7—C8	120.46 (5)	O3—C16—H16B	110.5
O1—C7—C6	118.86 (5)	C17—C16—H16B	110.5
C8—C7—C6	120.67 (5)	H16A—C16—H16B	108.7
C9—C8—C7	119.61 (5)	C16—C17—H17A	109.5
C9—C8—H8A	120.2	C16—C17—H17B	109.5
C7—C8—H8A	120.2	H17A—C17—H17B	109.5
C8—C9—C10	127.21 (5)	C16—C17—H17C	109.5
C8—C9—H9A	116.4	H17A—C17—H17C	109.5
C10—C9—H9A	116.4	H17B—C17—H17C	109.5
C15—C10—C11	117.98 (5)
O2—C1—C2—C3	−179.69 (6)	C7—C8—C9—C10	−178.73 (5)
C6—C1—C2—C3	0.31 (10)	C8—C9—C10—C15	173.80 (6)
C1—C2—C3—C4	0.31 (11)	C8—C9—C10—C11	−7.18 (10)
C2—C3—C4—C5	−0.43 (12)	C15—C10—C11—C12	0.63 (9)
C3—C4—C5—C6	−0.06 (11)	C9—C10—C11—C12	−178.39 (5)
C4—C5—C6—C1	0.65 (10)	C10—C11—C12—C13	0.49 (9)
C4—C5—C6—C7	179.82 (6)	C16—O3—C13—C14	0.40 (9)
O2—C1—C6—C5	179.22 (6)	C16—O3—C13—C12	−179.35 (5)
C2—C1—C6—C5	−0.78 (9)	C11—C12—C13—O3	178.52 (5)
O2—C1—C6—C7	0.03 (9)	C11—C12—C13—C14	−1.24 (9)
C2—C1—C6—C7	−179.97 (5)	O3—C13—C14—C15	−178.90 (6)
C5—C6—C7—O1	−175.37 (6)	C12—C13—C14—C15	0.83 (9)
C1—C6—C7—O1	3.79 (9)	C13—C14—C15—C10	0.32 (10)
C5—C6—C7—C8	5.26 (9)	C11—C10—C15—C14	−1.04 (9)
C1—C6—C7—C8	−175.59 (5)	C9—C10—C15—C14	178.03 (6)
O1—C7—C8—C9	3.15 (9)	C13—O3—C16—C17	179.71 (5)
C6—C7—C8—C9	−177.48 (5)

Cg1 is the centroid of the O2,C1–C6 ring?

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.93 (2)	1.66 (2)	2.5113 (7)	151 (1)
C16—H16A···Cg1i	0.97	2.70	3.5762 (7)	151
C16—H16B···Cg1ii	0.97	2.66	3.5339 (7)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.93 (2)	1.66 (2)	2.5113 (7)	151 (1)
C16—H16A⋯Cg1i	0.97	2.70	3.5762 (7)	151
C16—H16B⋯Cg1ii	0.97	2.66	3.5339 (7)	151

Symmetry codes: (i) ; (ii) .