(2E)-1-[2-Hydr-oxy-4-(2-methyl-prop-oxy)phen-yl]-3-(4-methyl-phen-yl)prop-2-en-1-one.

The benzene rings in the title compound, C(20)H(22)O(3), form a dihedral angle of 10.39 (8)°. Overall, the mol-ecule is approximately planar with the exception of one of the terminal methyl groups; excluding this group, the r.m.s. deviation for the remaining 22 non-H atoms is 0.0968 Å. The conformation about the C=C bond is E, and an intra-molecular O-H⋯O hydrogen bond leads to the formation of an S(6) motif. In the crystal, linear supra-molecular chains are formed along the a axis via C-H⋯O contacts, and these are connected into double chains via C-H⋯π inter-actions.

Related literature

For the use of α,β-unsaturated ketones in organic synthesis, see: Marzinzik & Felder (1998 ▶); Srikanth et al. (2005 ▶); Nehad et al. (2007 ▶); Gaede & Mcdermott (1993 ▶); Shibata et al. (1993 ▶); Xu et al. (2001 ▶). For the biological activity of α,β-unsaturated ketones, see: Prasad et al. (2008 ▶); Zhao et al. (2007 ▶). Lambert et al. (2009 ▶); Jung et al. (2008 ▶); Reichwald et al. (2008 ▶); Boumendjel et al. (2008 ▶); Domínguez et al. (2005 ▶); Yun et al. (2006 ▶). For semi-empirical quantum chemical calculations, see: Stewart (2009 ▶).

Experimental

Crystal data

C20H22O3

M = 310.38

Triclinic,

a = 6.7795 (8) Å

b = 9.8830 (12) Å

c = 13.9064 (17) Å

α = 74.740 (2)°

β = 78.857 (2)°

γ = 74.103 (2)°

V = 857.12 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.932, T max = 0.991

9290 measured reflections

3530 independent reflections

2452 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.03

3530 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010809/pk2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010809/pk2236Isup2.hkl

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

C20H22O3	Z = 2
Mr = 310.38	F(000) = 332
Triclinic, P1	Dx = 1.203 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7795 (8) Å	Cell parameters from 3222 reflections
b = 9.8830 (12) Å	θ = 2.8–24.2°
c = 13.9064 (17) Å	µ = 0.08 mm−1
α = 74.740 (2)°	T = 293 K
β = 78.857 (2)°	Block, colourless
γ = 74.103 (2)°	0.30 × 0.20 × 0.20 mm
V = 857.12 (18) Å3

Bruker SMART APEX CCD diffractometer	3530 independent reflections
Radiation source: fine-focus sealed tube	2452 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω and φ scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.932, Tmax = 0.991	k = −12→12
9290 measured reflections	l = −17→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.067P)2 + 0.1242P] where P = (Fo2 + 2Fc2)/3
3530 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.36395 (17)	0.23227 (14)	0.54491 (10)	0.0693 (4)
O2	0.10785 (17)	0.36469 (16)	0.66378 (11)	0.0787 (4)
H2o	0.1506	0.3135	0.6228	0.118*
O3	0.34346 (17)	0.64303 (13)	0.82850 (9)	0.0630 (3)
C1	1.4896 (3)	−0.0477 (2)	0.18171 (15)	0.0735 (5)
H1A	1.4928	−0.1427	0.1753	0.110*
H1B	1.6102	−0.0506	0.2094	0.110*
H1C	1.4874	0.0170	0.1167	0.110*
C2	1.2985 (2)	0.00433 (18)	0.25032 (12)	0.0541 (4)
C3	1.2904 (2)	0.10836 (18)	0.30244 (13)	0.0571 (4)
H3	1.4053	0.1463	0.2947	0.069*
C4	1.1166 (2)	0.15668 (17)	0.36524 (12)	0.0531 (4)
H4	1.1164	0.2257	0.3997	0.064*
C5	0.9411 (2)	0.10332 (16)	0.37782 (11)	0.0460 (4)
C6	0.9496 (2)	−0.00067 (17)	0.32580 (12)	0.0529 (4)
H6	0.8345	−0.0381	0.3329	0.063*
C7	1.1248 (3)	−0.04960 (18)	0.26386 (12)	0.0565 (4)
H7	1.1264	−0.1202	0.2306	0.068*
C8	0.7507 (2)	0.15052 (17)	0.44205 (11)	0.0500 (4)
H8	0.6440	0.1072	0.4439	0.060*
C9	0.7096 (2)	0.24698 (16)	0.49809 (11)	0.0487 (4)
H9	0.8116	0.2920	0.5008	0.058*
C10	0.5048 (2)	0.28363 (17)	0.55592 (12)	0.0489 (4)
C11	0.4634 (2)	0.37884 (16)	0.62556 (11)	0.0443 (4)
C12	0.6143 (2)	0.43552 (16)	0.64662 (12)	0.0482 (4)
H12	0.7483	0.4135	0.6138	0.058*
C13	0.5715 (2)	0.52170 (18)	0.71343 (12)	0.0527 (4)
H13	0.6752	0.5579	0.7255	0.063*
C14	0.3717 (2)	0.55579 (16)	0.76392 (11)	0.0486 (4)
C15	0.2186 (2)	0.50210 (17)	0.74614 (12)	0.0519 (4)
H15	0.0856	0.5244	0.7799	0.062*
C16	0.2630 (2)	0.41471 (17)	0.67776 (12)	0.0500 (4)
C17	0.1455 (3)	0.6734 (2)	0.88789 (13)	0.0624 (5)
H17A	0.1109	0.5839	0.9265	0.075*
H17B	0.0400	0.7242	0.8444	0.075*
C18	0.1529 (3)	0.7644 (2)	0.95744 (15)	0.0725 (5)
H18	0.1876	0.8539	0.9162	0.087*
C19	0.3163 (5)	0.6912 (4)	1.0255 (2)	0.1396 (12)
H19A	0.2890	0.6010	1.0647	0.209*
H19B	0.3149	0.7519	1.0694	0.209*
H19C	0.4495	0.6738	0.9858	0.209*
C20	−0.0607 (4)	0.8042 (3)	1.01622 (17)	0.0974 (8)
H20A	−0.1597	0.8542	0.9702	0.146*
H20B	−0.0579	0.8656	1.0590	0.146*
H20C	−0.0992	0.7181	1.0565	0.146*

	U11	U22	U33	U12	U13	U23
O1	0.0475 (7)	0.0922 (9)	0.0841 (9)	−0.0267 (6)	−0.0001 (6)	−0.0423 (7)
O2	0.0374 (6)	0.1094 (11)	0.1091 (11)	−0.0264 (7)	0.0034 (6)	−0.0578 (9)
O3	0.0544 (7)	0.0737 (8)	0.0670 (7)	−0.0152 (6)	0.0014 (6)	−0.0326 (6)
C1	0.0640 (11)	0.0825 (13)	0.0680 (12)	−0.0107 (10)	0.0067 (9)	−0.0247 (10)
C2	0.0514 (9)	0.0575 (10)	0.0483 (9)	−0.0080 (7)	−0.0034 (7)	−0.0101 (8)
C3	0.0478 (9)	0.0617 (10)	0.0646 (10)	−0.0188 (8)	−0.0031 (8)	−0.0156 (9)
C4	0.0525 (9)	0.0551 (9)	0.0568 (9)	−0.0144 (7)	−0.0067 (7)	−0.0196 (8)
C5	0.0472 (8)	0.0487 (8)	0.0423 (8)	−0.0109 (7)	−0.0079 (6)	−0.0091 (7)
C6	0.0521 (9)	0.0585 (9)	0.0540 (9)	−0.0195 (8)	−0.0066 (7)	−0.0162 (8)
C7	0.0646 (10)	0.0572 (10)	0.0521 (9)	−0.0135 (8)	−0.0055 (8)	−0.0219 (8)
C8	0.0453 (8)	0.0576 (9)	0.0493 (9)	−0.0149 (7)	−0.0076 (7)	−0.0115 (8)
C9	0.0428 (8)	0.0539 (9)	0.0498 (9)	−0.0121 (7)	−0.0051 (7)	−0.0121 (7)
C10	0.0419 (8)	0.0538 (9)	0.0511 (9)	−0.0117 (7)	−0.0081 (7)	−0.0102 (7)
C11	0.0347 (7)	0.0486 (8)	0.0473 (8)	−0.0080 (6)	−0.0061 (6)	−0.0082 (7)
C12	0.0323 (7)	0.0557 (9)	0.0553 (9)	−0.0094 (6)	−0.0020 (6)	−0.0138 (7)
C13	0.0403 (8)	0.0615 (10)	0.0616 (10)	−0.0154 (7)	−0.0066 (7)	−0.0193 (8)
C14	0.0466 (8)	0.0492 (9)	0.0471 (8)	−0.0079 (7)	−0.0043 (7)	−0.0109 (7)
C15	0.0366 (8)	0.0591 (10)	0.0563 (9)	−0.0092 (7)	0.0022 (7)	−0.0148 (8)
C16	0.0347 (8)	0.0574 (9)	0.0587 (9)	−0.0123 (7)	−0.0051 (7)	−0.0136 (8)
C17	0.0605 (10)	0.0658 (11)	0.0568 (10)	−0.0118 (9)	0.0061 (8)	−0.0198 (9)
C18	0.0815 (13)	0.0665 (12)	0.0679 (12)	−0.0112 (10)	0.0004 (10)	−0.0262 (10)
C19	0.144 (3)	0.168 (3)	0.119 (2)	0.027 (2)	−0.0586 (19)	−0.088 (2)
C20	0.1058 (18)	0.0937 (16)	0.0830 (15)	−0.0119 (14)	0.0221 (13)	−0.0400 (13)

O1—C10	1.2474 (18)	C9—H9	0.9300
O2—C16	1.3429 (18)	C10—C11	1.460 (2)
O2—H2o	0.8200	C11—C12	1.401 (2)
O3—C14	1.3556 (19)	C11—C16	1.410 (2)
O3—C17	1.4332 (19)	C12—C13	1.360 (2)
C1—C2	1.506 (2)	C12—H12	0.9300
C1—H1A	0.9600	C13—C14	1.396 (2)
C1—H1B	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C14—C15	1.374 (2)
C2—C7	1.383 (2)	C15—C16	1.386 (2)
C2—C3	1.390 (2)	C15—H15	0.9300
C3—C4	1.376 (2)	C17—C18	1.499 (3)
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.393 (2)	C17—H17B	0.9700
C4—H4	0.9300	C18—C19	1.500 (3)
C5—C6	1.388 (2)	C18—C20	1.523 (3)
C5—C8	1.458 (2)	C18—H18	0.9800
C6—C7	1.377 (2)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—C9	1.325 (2)	C20—H20A	0.9600
C8—H8	0.9300	C20—H20B	0.9600
C9—C10	1.467 (2)	C20—H20C	0.9600
C16—O2—H2o	109.5	C13—C12—H12	118.9
C14—O3—C17	118.25 (13)	C11—C12—H12	118.9
C2—C1—H1A	109.5	C12—C13—C14	119.92 (14)
C2—C1—H1B	109.5	C12—C13—H13	120.0
H1A—C1—H1B	109.5	C14—C13—H13	120.0
C2—C1—H1C	109.5	O3—C14—C15	124.34 (14)
H1A—C1—H1C	109.5	O3—C14—C13	115.70 (14)
H1B—C1—H1C	109.5	C15—C14—C13	119.96 (14)
C7—C2—C3	117.53 (15)	C14—C15—C16	119.85 (14)
C7—C2—C1	121.29 (16)	C14—C15—H15	120.1
C3—C2—C1	121.18 (16)	C16—C15—H15	120.1
C4—C3—C2	121.64 (15)	O2—C16—C15	117.28 (13)
C4—C3—H3	119.2	O2—C16—C11	121.36 (14)
C2—C3—H3	119.2	C15—C16—C11	121.35 (14)
C3—C4—C5	120.67 (15)	O3—C17—C18	109.14 (15)
C3—C4—H4	119.7	O3—C17—H17A	109.9
C5—C4—H4	119.7	C18—C17—H17A	109.9
C6—C5—C4	117.58 (14)	O3—C17—H17B	109.9
C6—C5—C8	118.64 (14)	C18—C17—H17B	109.9
C4—C5—C8	123.78 (14)	H17A—C17—H17B	108.3
C7—C6—C5	121.43 (15)	C17—C18—C19	111.91 (17)
C7—C6—H6	119.3	C17—C18—C20	109.22 (18)
C5—C6—H6	119.3	C19—C18—C20	112.0 (2)
C6—C7—C2	121.14 (15)	C17—C18—H18	107.8
C6—C7—H7	119.4	C19—C18—H18	107.8
C2—C7—H7	119.4	C20—C18—H18	107.8
C9—C8—C5	128.63 (15)	C18—C19—H19A	109.5
C9—C8—H8	115.7	C18—C19—H19B	109.5
C5—C8—H8	115.7	H19A—C19—H19B	109.5
C8—C9—C10	120.73 (14)	C18—C19—H19C	109.5
C8—C9—H9	119.6	H19A—C19—H19C	109.5
C10—C9—H9	119.6	H19B—C19—H19C	109.5
O1—C10—C11	119.71 (14)	C18—C20—H20A	109.5
O1—C10—C9	119.01 (14)	C18—C20—H20B	109.5
C11—C10—C9	121.27 (13)	H20A—C20—H20B	109.5
C12—C11—C16	116.67 (14)	C18—C20—H20C	109.5
C12—C11—C10	123.71 (13)	H20A—C20—H20C	109.5
C16—C11—C10	119.59 (13)	H20B—C20—H20C	109.5
C13—C12—C11	122.25 (14)
C7—C2—C3—C4	−0.1 (3)	C16—C11—C12—C13	−0.4 (2)
C1—C2—C3—C4	179.96 (15)	C10—C11—C12—C13	−178.68 (14)
C2—C3—C4—C5	−0.7 (3)	C11—C12—C13—C14	0.3 (2)
C3—C4—C5—C6	0.7 (2)	C17—O3—C14—C15	4.8 (2)
C3—C4—C5—C8	−179.25 (14)	C17—O3—C14—C13	−175.59 (14)
C4—C5—C6—C7	0.0 (2)	C12—C13—C14—O3	−179.59 (13)
C8—C5—C6—C7	179.92 (14)	C12—C13—C14—C15	0.1 (2)
C5—C6—C7—C2	−0.7 (2)	O3—C14—C15—C16	179.37 (14)
C3—C2—C7—C6	0.7 (2)	C13—C14—C15—C16	−0.3 (2)
C1—C2—C7—C6	−179.29 (15)	C14—C15—C16—O2	179.65 (15)
C6—C5—C8—C9	179.72 (15)	C14—C15—C16—C11	0.1 (2)
C4—C5—C8—C9	−0.3 (3)	C12—C11—C16—O2	−179.30 (15)
C5—C8—C9—C10	178.15 (14)	C10—C11—C16—O2	−0.9 (2)
C8—C9—C10—O1	−6.2 (2)	C12—C11—C16—C15	0.2 (2)
C8—C9—C10—C11	173.89 (14)	C10—C11—C16—C15	178.55 (14)
O1—C10—C11—C12	176.62 (15)	C14—O3—C17—C18	176.86 (14)
C9—C10—C11—C12	−3.5 (2)	O3—C17—C18—C19	−58.7 (2)
O1—C10—C11—C16	−1.6 (2)	O3—C17—C18—C20	176.68 (15)
C9—C10—C11—C16	178.27 (13)

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1	0.82	1.77	2.499 (2)	148
C12—H12···O2i	0.93	2.55	3.268 (2)	135
C17—H17b···Cgii	0.97	2.82	3.705 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O1	0.82	1.77	2.499 (2)	148
C12—H12⋯O2i	0.93	2.55	3.268 (2)	135
C17—H17b⋯Cgii	0.97	2.82	3.705 (2)	153

Symmetry codes: (i) ; (ii) .