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

In the title compound, C(17)H(16)O(4), the dihedral angle between the mean planes of the hy-droxy-phenyl and dimeth-oxy-phenyl rings is 5.9 (6)°. The mean plane of the prop-2-en-1-one group makes dihedral angles of 3.6 (0) and 2.6 (7)° with the hy-droxy-phenyl and dimeth-oxy-phenyl rings, respectively. An intra-molecular O-H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak inter-molecular C-H⋯O contacts and π-π stacking inter-actions [centroid-centroid distance = 3.6571 (8) Å].

Related literature

For related structures, see: Butcher et al. (2006 ▶); Cao et al. (2005 ▶); Harrison et al. (2007 ▶); Jasinski et al. (2010 ▶, 2011a ▶,b ▶); Ngaini et al. (2009 ▶); Radha Krishna et al. (2005 ▶); Sharma et al. (1997 ▶); Wu et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16O4

M = 284.30

Monoclinic,

a = 14.2315 (2) Å

b = 8.0292 (1) Å

c = 13.6027 (2) Å

β = 110.0531 (14)°

V = 1460.11 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.76 mm−1

T = 295 K

0.51 × 0.47 × 0.35 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.065, T max = 1.000

6676 measured reflections

3014 independent reflections

2336 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.152

S = 1.12

3014 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 global, I. DOI: 10.1107/S1600536811008361/kp2312sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008361/kp2312Isup2.hkl

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

C17H16O4	F(000) = 600
Mr = 284.30	Dx = 1.293 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4075 reflections
a = 14.2315 (2) Å	θ = 5.5–77.1°
b = 8.0292 (1) Å	µ = 0.76 mm−1
c = 13.6027 (2) Å	T = 295 K
β = 110.0531 (14)°	Prism, pale yellow
V = 1460.11 (3) Å3	0.51 × 0.47 × 0.35 mm
Z = 4

Oxford Diffraction Gemini R diffractometer	3014 independent reflections
Radiation source: fine-focus sealed tube	2336 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.5081 pixels mm-1	θmax = 77.4°, θmin = 6.4°
φ and ω scans	h = −17→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→9
Tmin = 0.065, Tmax = 1.000	l = −15→17
6676 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0968P)2 + 0.0366P] where P = (Fo2 + 2Fc2)/3
3014 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.88704 (12)	0.7981 (2)	0.17236 (10)	0.0876 (4)
H1A	0.8351	0.7455	0.1617	0.131*
O2	0.76002 (8)	0.62603 (18)	0.21587 (8)	0.0737 (4)
O3	0.63965 (8)	0.32097 (14)	0.68696 (7)	0.0648 (3)
O4	0.47076 (8)	0.18452 (14)	0.59076 (8)	0.0638 (3)
C1	0.90537 (11)	0.71605 (18)	0.34900 (11)	0.0558 (3)
C2	0.94152 (13)	0.7937 (2)	0.27531 (14)	0.0670 (4)
C3	1.03495 (17)	0.8674 (3)	0.3086 (2)	0.0921 (6)
H3A	1.0588	0.9173	0.2601	0.110*
C4	1.09263 (17)	0.8676 (3)	0.4123 (2)	0.1082 (8)
H4A	1.1553	0.9177	0.4338	0.130*
C5	1.05822 (17)	0.7935 (3)	0.4855 (2)	0.1030 (8)
H5A	1.0979	0.7934	0.5559	0.124*
C6	0.96559 (14)	0.7203 (2)	0.45407 (14)	0.0744 (5)
H6A	0.9425	0.6726	0.5038	0.089*
C7	0.80752 (10)	0.63257 (19)	0.31157 (10)	0.0536 (3)
C8	0.76620 (10)	0.55612 (18)	0.38547 (10)	0.0545 (3)
H8A	0.8025	0.5598	0.4568	0.065*
C9	0.67732 (10)	0.48135 (18)	0.35199 (10)	0.0531 (3)
H9A	0.6448	0.4794	0.2799	0.064*
C10	0.62489 (10)	0.40250 (17)	0.41423 (10)	0.0502 (3)
C11	0.66334 (10)	0.40028 (17)	0.52433 (10)	0.0505 (3)
H11A	0.7254	0.4481	0.5593	0.061*
C12	0.61015 (10)	0.32804 (17)	0.58086 (10)	0.0497 (3)
C13	0.51638 (10)	0.25396 (17)	0.52792 (10)	0.0501 (3)
C14	0.47888 (10)	0.25475 (19)	0.41980 (11)	0.0553 (3)
H14A	0.4173	0.2058	0.3845	0.066*
C15	0.53281 (10)	0.3283 (2)	0.36387 (10)	0.0567 (4)
H15A	0.5068	0.3279	0.2911	0.068*
C16	0.73098 (14)	0.3979 (3)	0.74455 (12)	0.0755 (5)
H16A	0.7843	0.3472	0.7271	0.113*
H16B	0.7432	0.3845	0.8180	0.113*
H16C	0.7276	0.5144	0.7278	0.113*
C17	0.37373 (12)	0.1167 (2)	0.54210 (14)	0.0681 (4)
H17A	0.3287	0.2033	0.5056	0.102*
H17B	0.3505	0.0692	0.5944	0.102*
H17C	0.3763	0.0318	0.4934	0.102*

	U11	U22	U33	U12	U13	U23
O1	0.1035 (10)	0.1039 (11)	0.0682 (8)	−0.0071 (8)	0.0458 (7)	0.0160 (7)
O2	0.0640 (6)	0.1134 (10)	0.0441 (5)	−0.0038 (6)	0.0193 (5)	0.0099 (5)
O3	0.0718 (6)	0.0810 (7)	0.0380 (5)	−0.0125 (5)	0.0142 (4)	0.0055 (4)
O4	0.0672 (6)	0.0759 (7)	0.0503 (5)	−0.0126 (5)	0.0226 (5)	0.0033 (5)
C1	0.0575 (7)	0.0584 (8)	0.0558 (8)	0.0092 (6)	0.0248 (6)	0.0038 (6)
C2	0.0745 (10)	0.0630 (9)	0.0739 (10)	0.0041 (7)	0.0389 (8)	0.0062 (7)
C3	0.0863 (13)	0.0863 (13)	0.1165 (18)	−0.0127 (10)	0.0514 (13)	0.0123 (12)
C4	0.0760 (13)	0.1022 (16)	0.141 (2)	−0.0257 (11)	0.0305 (14)	0.0055 (15)
C5	0.0775 (12)	0.1164 (18)	0.0948 (15)	−0.0212 (12)	0.0034 (11)	0.0067 (13)
C6	0.0695 (9)	0.0837 (11)	0.0647 (10)	−0.0050 (8)	0.0159 (8)	0.0055 (8)
C7	0.0538 (7)	0.0663 (8)	0.0440 (6)	0.0109 (6)	0.0210 (5)	0.0039 (6)
C8	0.0574 (7)	0.0671 (8)	0.0416 (6)	0.0069 (6)	0.0205 (5)	0.0025 (6)
C9	0.0590 (7)	0.0632 (8)	0.0407 (6)	0.0082 (6)	0.0218 (5)	0.0010 (6)
C10	0.0552 (7)	0.0572 (7)	0.0408 (6)	0.0063 (5)	0.0197 (5)	−0.0008 (5)
C11	0.0523 (7)	0.0570 (7)	0.0417 (6)	−0.0003 (5)	0.0154 (5)	−0.0014 (5)
C12	0.0572 (7)	0.0530 (7)	0.0377 (6)	0.0026 (5)	0.0145 (5)	0.0009 (5)
C13	0.0547 (7)	0.0526 (7)	0.0452 (7)	0.0027 (5)	0.0201 (5)	0.0008 (6)
C14	0.0495 (6)	0.0680 (8)	0.0471 (7)	−0.0012 (6)	0.0147 (5)	−0.0056 (6)
C15	0.0568 (7)	0.0755 (9)	0.0364 (6)	0.0049 (6)	0.0143 (5)	−0.0027 (6)
C16	0.0726 (10)	0.1061 (14)	0.0400 (7)	−0.0133 (9)	0.0094 (6)	−0.0028 (8)
C17	0.0642 (9)	0.0744 (10)	0.0710 (10)	−0.0079 (7)	0.0300 (7)	−0.0029 (8)

O1—C2	1.349 (2)	C8—C9	1.331 (2)
O1—H1A	0.8200	C8—H8A	0.9300
O2—C7	1.2454 (16)	C9—C10	1.4517 (19)
O3—C12	1.3591 (15)	C9—H9A	0.9300
O3—C16	1.4094 (19)	C10—C15	1.388 (2)
O4—C13	1.3578 (16)	C10—C11	1.4073 (17)
O4—C17	1.4193 (19)	C11—C12	1.3784 (19)
C1—C6	1.392 (2)	C11—H11A	0.9300
C1—C2	1.418 (2)	C12—C13	1.4121 (19)
C1—C7	1.470 (2)	C13—C14	1.3820 (18)
C2—C3	1.382 (3)	C14—C15	1.384 (2)
C3—C4	1.367 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.386 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.371 (3)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.4623 (19)	C17—H17C	0.9600
C2—O1—H1A	109.5	C15—C10—C11	118.47 (12)
C12—O3—C16	117.53 (12)	C15—C10—C9	119.11 (12)
C13—O4—C17	117.57 (11)	C11—C10—C9	122.41 (12)
C6—C1—C2	118.03 (15)	C12—C11—C10	120.76 (12)
C6—C1—C7	122.90 (14)	C12—C11—H11A	119.6
C2—C1—C7	119.06 (13)	C10—C11—H11A	119.6
O1—C2—C3	118.35 (17)	O3—C12—C11	125.54 (12)
O1—C2—C1	121.78 (15)	O3—C12—C13	114.69 (12)
C3—C2—C1	119.88 (18)	C11—C12—C13	119.77 (12)
C4—C3—C2	120.5 (2)	O4—C13—C14	125.33 (13)
C4—C3—H3A	119.7	O4—C13—C12	115.10 (11)
C2—C3—H3A	119.7	C14—C13—C12	119.56 (12)
C3—C4—C5	120.4 (2)	C13—C14—C15	120.15 (13)
C3—C4—H4A	119.8	C13—C14—H14A	119.9
C5—C4—H4A	119.8	C15—C14—H14A	119.9
C6—C5—C4	119.9 (2)	C14—C15—C10	121.29 (12)
C6—C5—H5A	120.1	C14—C15—H15A	119.4
C4—C5—H5A	120.1	C10—C15—H15A	119.4
C5—C6—C1	121.2 (2)	O3—C16—H16A	109.5
C5—C6—H6A	119.4	O3—C16—H16B	109.5
C1—C6—H6A	119.4	H16A—C16—H16B	109.5
O2—C7—C8	119.91 (13)	O3—C16—H16C	109.5
O2—C7—C1	119.43 (13)	H16A—C16—H16C	109.5
C8—C7—C1	120.65 (12)	H16B—C16—H16C	109.5
C9—C8—C7	120.86 (12)	O4—C17—H17A	109.5
C9—C8—H8A	119.6	O4—C17—H17B	109.5
C7—C8—H8A	119.6	H17A—C17—H17B	109.5
C8—C9—C10	127.97 (12)	O4—C17—H17C	109.5
C8—C9—H9A	116.0	H17A—C17—H17C	109.5
C10—C9—H9A	116.0	H17B—C17—H17C	109.5
C6—C1—C2—O1	−178.66 (16)	C8—C9—C10—C11	2.0 (2)
C7—C1—C2—O1	2.4 (2)	C15—C10—C11—C12	−0.9 (2)
C6—C1—C2—C3	1.4 (2)	C9—C10—C11—C12	178.26 (12)
C7—C1—C2—C3	−177.60 (16)	C16—O3—C12—C11	1.9 (2)
O1—C2—C3—C4	179.4 (2)	C16—O3—C12—C13	−177.80 (14)
C1—C2—C3—C4	−0.6 (3)	C10—C11—C12—O3	−179.11 (12)
C2—C3—C4—C5	0.1 (4)	C10—C11—C12—C13	0.6 (2)
C3—C4—C5—C6	−0.4 (4)	C17—O4—C13—C14	−4.4 (2)
C4—C5—C6—C1	1.1 (4)	C17—O4—C13—C12	176.45 (13)
C2—C1—C6—C5	−1.6 (3)	O3—C12—C13—O4	−1.09 (18)
C7—C1—C6—C5	177.29 (19)	C11—C12—C13—O4	179.19 (12)
C6—C1—C7—O2	−176.19 (15)	O3—C12—C13—C14	179.70 (13)
C2—C1—C7—O2	2.7 (2)	C11—C12—C13—C14	0.0 (2)
C6—C1—C7—C8	3.2 (2)	O4—C13—C14—C15	−179.36 (13)
C2—C1—C7—C8	−177.88 (13)	C12—C13—C14—C15	−0.2 (2)
O2—C7—C8—C9	−1.0 (2)	C13—C14—C15—C10	−0.1 (2)
C1—C7—C8—C9	179.55 (13)	C11—C10—C15—C14	0.6 (2)
C7—C8—C9—C10	−178.80 (13)	C9—C10—C15—C14	−178.54 (13)
C8—C9—C10—C15	−178.87 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.77	2.5021 (18)	147
C14—H14A···O2i	0.93	2.51	3.4250 (19)	170

CgI···CgJ	Cg···Cg (Å)	CgI Perp (Å)	Cgj Perp (Å)	Slippage (Å)
Cg2···Cg2i	3.6571 (8)	3.5389 (6)	3.5389 (6)	0.92 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	1.77	2.5021 (18)	147
C14—H14A⋯O2i	0.93	2.51	3.4250 (19)	170

Symmetry code: (i) .