(2E)-1-(2-Hy-droxy-5-methyl-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(17)H(16)O(3), the dihedral angle between the aromatic rings is 4.59 (7)° and an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, adjacent mol-ecules are linked by C-H⋯O hydrogen bonds, leading to the formation of [001] supra-molecular chains. Weak C-H⋯π inter-actions consolidate the packing.

Related literature

For a related structure and background references to chalcones, see: Fun et al. (2010 ▶). For related structures, see: Chantrapromma et al. (2009 ▶, 2010 ▶); Fun et al. (2009 ▶); Horkaew et al. (2010 ▶); Lu et al. (2009 ▶); Suwunwong et al. (2009 ▶); Wang et al. (2009 ▶, 2010 ▶); Jasinski et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H16O3

M = 268.30

Monoclinic,

a = 12.6990 (18) Å

b = 8.8022 (13) Å

c = 13.172 (2) Å

β = 105.565 (2)°

V = 1418.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.46 × 0.32 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.962, T max = 0.984

11493 measured reflections

4090 independent reflections

2608 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.02

4090 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811015054/hb5847sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015054/hb5847Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015054/hb5847Isup3.cml

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

C17H16O3	F(000) = 568
Mr = 268.30	Dx = 1.256 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2769 reflections
a = 12.6990 (18) Å	θ = 2.8–28.6°
b = 8.8022 (13) Å	µ = 0.09 mm−1
c = 13.172 (2) Å	T = 296 K
β = 105.565 (2)°	Block, orange
V = 1418.3 (4) Å3	0.46 × 0.32 × 0.18 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	4090 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 29.9°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.962, Tmax = 0.984	k = −10→12
11493 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.1652P] where P = (Fo2 + 2Fc2)/3
4090 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 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	0.13821 (11)	0.18686 (15)	0.32930 (8)	0.0794 (4)
O2	0.26594 (9)	0.35672 (14)	0.26545 (7)	0.0758 (3)
O3	0.51456 (8)	0.87081 (13)	−0.15126 (7)	0.0666 (3)
C1	0.03317 (10)	0.26022 (14)	0.04622 (10)	0.0486 (3)
H1A	0.0518	0.3125	−0.0078	0.058*
C2	−0.06268 (11)	0.17724 (16)	0.02260 (12)	0.0553 (3)
C3	−0.08898 (13)	0.10217 (19)	0.10552 (15)	0.0704 (4)
H3A	−0.1538	0.0472	0.0921	0.084*
C4	−0.02277 (15)	0.10664 (19)	0.20568 (15)	0.0728 (4)
H4A	−0.0427	0.0543	0.2590	0.087*
C5	0.07432 (12)	0.18853 (16)	0.22906 (11)	0.0581 (4)
C6	0.10376 (10)	0.26897 (14)	0.14840 (10)	0.0468 (3)
C7	0.20644 (11)	0.35632 (16)	0.17338 (10)	0.0502 (3)
C8	0.23943 (10)	0.44232 (15)	0.09183 (10)	0.0488 (3)
H8A	0.1929	0.4469	0.0240	0.059*
C9	0.33518 (10)	0.51410 (15)	0.11356 (10)	0.0478 (3)
H9A	0.3790	0.5037	0.1822	0.057*
C10	0.38013 (9)	0.60674 (14)	0.04375 (9)	0.0442 (3)
C11	0.48166 (10)	0.67433 (16)	0.08326 (10)	0.0501 (3)
H11A	0.5188	0.6589	0.1536	0.060*
C12	0.52938 (10)	0.76377 (16)	0.02169 (10)	0.0504 (3)
H12A	0.5973	0.8081	0.0504	0.060*
C13	0.47519 (10)	0.78657 (15)	−0.08275 (9)	0.0477 (3)
C14	0.37276 (11)	0.72165 (17)	−0.12373 (10)	0.0581 (4)
H14A	0.3355	0.7385	−0.1939	0.070*
C15	0.32612 (10)	0.63348 (16)	−0.06231 (10)	0.0542 (3)
H15A	0.2577	0.5907	−0.0912	0.065*
C16	−0.13460 (12)	0.16543 (19)	−0.08791 (14)	0.0704 (4)
H16A	−0.1021	0.2204	−0.1347	0.106*
H16B	−0.2051	0.2077	−0.0911	0.106*
H16C	−0.1427	0.0606	−0.1086	0.106*
C17	0.61893 (12)	0.93974 (19)	−0.11419 (12)	0.0645 (4)
H17A	0.6362	0.9942	−0.1708	0.097*
H17B	0.6731	0.8627	−0.0886	0.097*
H17C	0.6181	1.0090	−0.0581	0.097*
H1O1	0.2008 (17)	0.245 (2)	0.3290 (16)	0.107 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.1019 (9)	0.0879 (9)	0.0533 (6)	−0.0055 (7)	0.0295 (6)	0.0145 (6)
O2	0.0760 (7)	0.1013 (9)	0.0451 (5)	−0.0174 (6)	0.0078 (5)	0.0079 (5)
O3	0.0642 (6)	0.0840 (8)	0.0509 (5)	−0.0187 (5)	0.0142 (5)	0.0088 (5)
C1	0.0523 (7)	0.0438 (7)	0.0542 (7)	0.0022 (6)	0.0222 (6)	−0.0008 (6)
C2	0.0514 (7)	0.0456 (8)	0.0729 (9)	0.0012 (6)	0.0239 (6)	−0.0062 (6)
C3	0.0651 (9)	0.0595 (10)	0.0961 (13)	−0.0098 (7)	0.0380 (9)	−0.0011 (9)
C4	0.0863 (11)	0.0626 (10)	0.0845 (11)	−0.0079 (9)	0.0488 (10)	0.0088 (8)
C5	0.0756 (9)	0.0509 (8)	0.0567 (8)	0.0042 (7)	0.0331 (7)	0.0038 (6)
C6	0.0552 (7)	0.0413 (7)	0.0496 (7)	0.0036 (6)	0.0241 (6)	−0.0015 (5)
C7	0.0570 (7)	0.0503 (8)	0.0454 (6)	0.0025 (6)	0.0172 (6)	−0.0010 (5)
C8	0.0537 (7)	0.0499 (7)	0.0428 (6)	−0.0015 (6)	0.0130 (5)	−0.0013 (5)
C9	0.0503 (6)	0.0489 (7)	0.0435 (6)	0.0024 (6)	0.0114 (5)	−0.0028 (5)
C10	0.0445 (6)	0.0453 (7)	0.0427 (6)	0.0028 (5)	0.0113 (5)	−0.0040 (5)
C11	0.0458 (6)	0.0617 (9)	0.0395 (6)	0.0009 (6)	0.0058 (5)	0.0004 (6)
C12	0.0400 (6)	0.0621 (9)	0.0462 (6)	−0.0029 (6)	0.0065 (5)	−0.0027 (6)
C13	0.0483 (6)	0.0521 (8)	0.0434 (6)	−0.0004 (6)	0.0135 (5)	−0.0012 (5)
C14	0.0554 (7)	0.0723 (10)	0.0401 (6)	−0.0100 (7)	0.0016 (6)	0.0034 (6)
C15	0.0465 (7)	0.0632 (9)	0.0481 (7)	−0.0098 (6)	0.0042 (5)	−0.0018 (6)
C16	0.0544 (8)	0.0657 (10)	0.0876 (11)	−0.0045 (7)	0.0131 (8)	−0.0117 (8)
C17	0.0614 (8)	0.0662 (10)	0.0707 (9)	−0.0104 (7)	0.0257 (7)	−0.0025 (7)

O1—C5	1.3517 (18)	C9—C10	1.4554 (17)
O1—H1O1	0.94 (2)	C9—H9A	0.9300
O2—C7	1.2449 (15)	C10—C11	1.3881 (17)
O3—C13	1.3624 (15)	C10—C15	1.4011 (17)
O3—C17	1.4198 (17)	C11—C12	1.3814 (18)
C1—C2	1.3815 (18)	C11—H11A	0.9300
C1—C6	1.4048 (18)	C12—C13	1.3778 (17)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.392 (2)	C13—C14	1.3903 (18)
C2—C16	1.500 (2)	C14—C15	1.3656 (19)
C3—C4	1.361 (2)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.390 (2)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.4082 (18)	C16—H16C	0.9600
C6—C7	1.4729 (18)	C17—H17A	0.9600
C7—C8	1.4641 (18)	C17—H17B	0.9600
C8—C9	1.3315 (17)	C17—H17C	0.9600
C8—H8A	0.9300
C5—O1—H1O1	106.0 (13)	C11—C10—C9	119.05 (11)
C13—O3—C17	118.65 (11)	C15—C10—C9	123.64 (11)
C2—C1—C6	122.82 (12)	C12—C11—C10	122.26 (11)
C2—C1—H1A	118.6	C12—C11—H11A	118.9
C6—C1—H1A	118.6	C10—C11—H11A	118.9
C1—C2—C3	117.18 (14)	C13—C12—C11	119.26 (11)
C1—C2—C16	121.70 (13)	C13—C12—H12A	120.4
C3—C2—C16	121.11 (14)	C11—C12—H12A	120.4
C4—C3—C2	122.06 (15)	O3—C13—C12	124.53 (11)
C4—C3—H3A	119.0	O3—C13—C14	115.97 (11)
C2—C3—H3A	119.0	C12—C13—C14	119.50 (12)
C3—C4—C5	120.69 (14)	C15—C14—C13	120.86 (12)
C3—C4—H4A	119.7	C15—C14—H14A	119.6
C5—C4—H4A	119.7	C13—C14—H14A	119.6
O1—C5—C4	118.37 (13)	C14—C15—C10	120.80 (12)
O1—C5—C6	122.08 (14)	C14—C15—H15A	119.6
C4—C5—C6	119.54 (14)	C10—C15—H15A	119.6
C1—C6—C5	117.70 (12)	C2—C16—H16A	109.5
C1—C6—C7	122.80 (11)	C2—C16—H16B	109.5
C5—C6—C7	119.49 (12)	H16A—C16—H16B	109.5
O2—C7—C8	119.66 (12)	C2—C16—H16C	109.5
O2—C7—C6	119.25 (12)	H16A—C16—H16C	109.5
C8—C7—C6	121.09 (11)	H16B—C16—H16C	109.5
C9—C8—C7	120.81 (12)	O3—C17—H17A	109.5
C9—C8—H8A	119.6	O3—C17—H17B	109.5
C7—C8—H8A	119.6	H17A—C17—H17B	109.5
C8—C9—C10	128.35 (12)	O3—C17—H17C	109.5
C8—C9—H9A	115.8	H17A—C17—H17C	109.5
C10—C9—H9A	115.8	H17B—C17—H17C	109.5
C11—C10—C15	117.30 (12)
C6—C1—C2—C3	1.0 (2)	O2—C7—C8—C9	3.8 (2)
C6—C1—C2—C16	−177.83 (13)	C6—C7—C8—C9	−176.22 (12)
C1—C2—C3—C4	−1.3 (2)	C7—C8—C9—C10	−178.59 (12)
C16—C2—C3—C4	177.45 (14)	C8—C9—C10—C11	178.78 (13)
C2—C3—C4—C5	0.5 (3)	C8—C9—C10—C15	−0.7 (2)
C3—C4—C5—O1	−178.70 (15)	C15—C10—C11—C12	−0.5 (2)
C3—C4—C5—C6	0.7 (2)	C9—C10—C11—C12	−179.97 (12)
C2—C1—C6—C5	0.22 (19)	C10—C11—C12—C13	−0.4 (2)
C2—C1—C6—C7	179.43 (12)	C17—O3—C13—C12	0.6 (2)
O1—C5—C6—C1	178.32 (12)	C17—O3—C13—C14	−179.83 (13)
C4—C5—C6—C1	−1.1 (2)	C11—C12—C13—O3	−179.21 (13)
O1—C5—C6—C7	−0.9 (2)	C11—C12—C13—C14	1.2 (2)
C4—C5—C6—C7	179.72 (13)	O3—C13—C14—C15	179.21 (13)
C1—C6—C7—O2	−178.73 (13)	C12—C13—C14—C15	−1.2 (2)
C5—C6—C7—O2	0.47 (19)	C13—C14—C15—C10	0.3 (2)
C1—C6—C7—C8	1.27 (19)	C11—C10—C15—C14	0.5 (2)
C5—C6—C7—C8	−179.54 (12)	C9—C10—C15—C14	179.98 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A···O3i	0.93	2.60	3.4317 (17)	149.
C16—H16C···Cg1ii	0.96	2.81	3.5800 (18)	138

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
O1—H1O1⋯O2	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A⋯O3i	0.93	2.60	3.4317 (17)	149
C16—H16C⋯Cg1ii	0.96	2.81	3.5800 (18)	138

Symmetry codes: (i) ; (ii) .