(E)-1-(4-Meth-oxy-phen-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

The title compound, C(19)H(20)O(5), was synthesized by reaction of 4-meth-oxy-acetophenone and 3,4,5-trimeth-oxy-benzaldehyde. The aromatic rings form a dihedral angle of 36.39 (7)°. Two intramolecular C-H⋯O hydrogen bonds occur. The crystal packing features weak C-H⋯O inter-actions.

Related literature

For background to chalcones and the biological activity and derivatives, see: Dhar (1981 ▶); Dimmock et al. (1999 ▶). For their applications as organic non-linear optical materials, see: Sarojini et al. (2006 ▶) and for their choleretic and hepatoprotective activity, see: Ni et al. (2004 ▶). For the synthesis of chalcones, see: Patil et al. (2009 ▶). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999 ▶). For related structures, see: Sathiya Moorthi et al. (2005 ▶); Cai et al. (2011 ▶); Vijay Kumar et al. (2011 ▶); Bibila Mayaya Bisseyou et al. (2007 ▶). The title compound wss prepared by an aldol Claisen–Schmidt condensation reaction, see: Bandgar et al. (2009 ▶, 2010 ▶); Hathaway (1987 ▶).

Experimental

Crystal data

C19H20O5

M = 328.35

Monoclinic,

a = 7.5770 (1) Å

b = 16.2530 (3) Å

c = 14.0850 (3) Å

β = 107.528 (1)°

V = 1654.02 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.2 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

27371 measured reflections

3733 independent reflections

2907 reflections with I > 2σ(I)

R int = 0.130

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.174

S = 1.02

3733 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028984/zj2014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028984/zj2014Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028984/zj2014Isup3.cml

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

C19H20O5	F(000) = 696
Mr = 328.35	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5770 (1) Å	Cell parameters from 14574 reflections
b = 16.2530 (3) Å	θ = 2.6–27.5°
c = 14.0850 (3) Å	µ = 0.10 mm−1
β = 107.528 (1)°	T = 293 K
V = 1654.02 (5) Å3	Prism, pale yellow
Z = 4	0.2 × 0.1 × 0.1 mm

Nonius KappaCCD diffractometer	2907 reflections with I > 2σ(I)
graphite	Rint = 0.130
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.8°
CCD scans	h = −9→8
27371 measured reflections	k = −20→21
3733 independent reflections	l = −18→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.115P)2 + 0.1311P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
3733 reflections	Δρmax = 0.27 e Å−3
222 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.085 (10)

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
C6	0.28843 (19)	0.01968 (8)	0.72913 (10)	0.0440 (3)
C3	0.2444 (2)	0.01579 (9)	0.91868 (10)	0.0478 (4)
O5	−0.33915 (16)	0.26263 (7)	0.32667 (8)	0.0592 (3)
C7	0.3073 (2)	0.01831 (8)	0.62695 (11)	0.0465 (3)
O1	0.21258 (17)	0.01994 (7)	1.00875 (8)	0.0613 (3)
O3	0.06505 (17)	0.22341 (7)	0.13696 (8)	0.0594 (3)
C13	−0.1306 (2)	0.24141 (9)	0.23514 (10)	0.0496 (4)
O2	0.41266 (17)	−0.03016 (7)	0.60508 (9)	0.0623 (3)
C14	0.0304 (2)	0.20629 (8)	0.22489 (9)	0.0472 (3)
C11	−0.0614 (2)	0.18197 (9)	0.39957 (10)	0.0478 (3)
H11	−0.0896	0.1757	0.459	0.057*
C1	0.3390 (2)	−0.04924 (8)	0.78977 (11)	0.0475 (3)
H1	0.3901	−0.0943	0.7669	0.057*
C9	0.21256 (19)	0.09013 (9)	0.46478 (10)	0.0464 (3)
H9	0.3105	0.0638	0.4504	0.056*
C15	0.1421 (2)	0.15689 (9)	0.29994 (10)	0.0471 (3)
H15	0.2474	0.1324	0.2917	0.057*
C10	0.09579 (19)	0.14423 (8)	0.38773 (9)	0.0451 (3)
C5	0.2205 (2)	0.08797 (9)	0.76692 (11)	0.0501 (4)
H5	0.1881	0.1351	0.728	0.06*
O4	−0.24822 (19)	0.28028 (7)	0.15454 (8)	0.0700 (4)
C12	−0.1763 (2)	0.22889 (9)	0.32326 (10)	0.0475 (4)
C4	0.2007 (2)	0.08672 (9)	0.86115 (11)	0.0528 (4)
H4	0.1583	0.1332	0.8861	0.063*
C2	0.3152 (2)	−0.05237 (9)	0.88338 (10)	0.0502 (4)
H2	0.3463	−0.0996	0.9221	0.06*
C8	0.1902 (2)	0.07561 (9)	0.55307 (10)	0.0503 (4)
H8	0.0955	0.103	0.5694	0.06*
C17	−0.2865 (3)	0.36460 (11)	0.16310 (12)	0.0693 (5)
H17A	−0.3621	0.3708	0.2064	0.104*
H17B	−0.3508	0.3863	0.0985	0.104*
H17C	−0.1724	0.394	0.1902	0.104*
C16	−0.3984 (2)	0.24404 (11)	0.41148 (12)	0.0602 (4)
H16A	−0.4186	0.1859	0.4141	0.09*
H16B	−0.5116	0.2728	0.4064	0.09*
H16C	−0.3049	0.261	0.4709	0.09*
C18	0.2381 (3)	0.19903 (12)	0.12726 (13)	0.0702 (5)
H18A	0.3358	0.22	0.1825	0.105*
H18B	0.2513	0.2205	0.0663	0.105*
H18C	0.2446	0.1401	0.1265	0.105*
C19	0.2388 (3)	−0.05277 (12)	1.06778 (12)	0.0666 (5)
H19A	0.1621	−0.096	1.0306	0.1*
H19B	0.2058	−0.0421	1.1273	0.1*
H19C	0.3663	−0.0692	1.0852	0.1*

	U11	U22	U33	U12	U13	U23
C6	0.0425 (7)	0.0436 (7)	0.0430 (7)	−0.0002 (5)	0.0086 (5)	0.0042 (5)
C3	0.0491 (8)	0.0517 (8)	0.0401 (7)	−0.0033 (6)	0.0098 (6)	0.0043 (5)
O5	0.0536 (7)	0.0738 (7)	0.0466 (6)	0.0147 (5)	0.0095 (5)	0.0039 (5)
C7	0.0463 (7)	0.0433 (7)	0.0502 (8)	0.0004 (6)	0.0150 (6)	0.0046 (5)
O1	0.0772 (8)	0.0628 (7)	0.0459 (6)	0.0058 (5)	0.0215 (5)	0.0096 (4)
O3	0.0722 (8)	0.0672 (7)	0.0393 (5)	0.0078 (5)	0.0175 (5)	0.0058 (4)
C13	0.0562 (9)	0.0490 (7)	0.0348 (7)	0.0022 (6)	0.0006 (6)	−0.0041 (5)
O2	0.0736 (8)	0.0566 (6)	0.0648 (7)	0.0189 (5)	0.0331 (6)	0.0119 (5)
C14	0.0581 (8)	0.0468 (7)	0.0336 (6)	−0.0044 (6)	0.0090 (6)	−0.0039 (5)
C11	0.0491 (8)	0.0547 (8)	0.0367 (6)	0.0003 (6)	0.0087 (5)	−0.0003 (5)
C1	0.0497 (8)	0.0413 (7)	0.0470 (7)	0.0024 (6)	0.0078 (6)	0.0017 (5)
C9	0.0444 (7)	0.0478 (7)	0.0452 (7)	0.0016 (5)	0.0109 (6)	0.0023 (5)
C15	0.0495 (7)	0.0492 (7)	0.0409 (7)	−0.0006 (6)	0.0112 (6)	−0.0008 (5)
C10	0.0459 (7)	0.0467 (7)	0.0382 (6)	−0.0028 (6)	0.0057 (5)	−0.0002 (5)
C5	0.0577 (8)	0.0432 (7)	0.0489 (7)	0.0076 (6)	0.0152 (6)	0.0092 (6)
O4	0.0862 (9)	0.0722 (8)	0.0379 (6)	0.0246 (6)	−0.0021 (5)	−0.0010 (5)
C12	0.0463 (8)	0.0503 (8)	0.0407 (7)	0.0023 (6)	0.0050 (6)	−0.0043 (5)
C4	0.0623 (9)	0.0463 (7)	0.0494 (8)	0.0075 (6)	0.0163 (7)	0.0041 (6)
C2	0.0556 (8)	0.0428 (7)	0.0462 (7)	0.0006 (6)	0.0062 (6)	0.0096 (5)
C8	0.0484 (8)	0.0562 (8)	0.0453 (7)	0.0087 (6)	0.0125 (6)	0.0053 (6)
C17	0.0765 (11)	0.0667 (10)	0.0584 (9)	0.0204 (9)	0.0110 (8)	0.0105 (8)
C16	0.0577 (9)	0.0657 (10)	0.0594 (9)	0.0082 (7)	0.0210 (8)	0.0027 (7)
C18	0.0911 (13)	0.0769 (11)	0.0506 (9)	0.0143 (9)	0.0333 (9)	0.0034 (7)
C19	0.0736 (11)	0.0730 (11)	0.0529 (9)	0.0016 (8)	0.0188 (8)	0.0205 (7)

C6—C1	1.3906 (19)	C9—C10	1.4682 (19)
C6—C5	1.395 (2)	C9—H9	0.93
C6—C7	1.4889 (19)	C15—C10	1.3986 (19)
C3—O1	1.3626 (17)	C15—H15	0.93
C3—C2	1.387 (2)	C5—C4	1.380 (2)
C3—C4	1.3906 (19)	C5—H5	0.93
O5—C12	1.3645 (18)	O4—C17	1.413 (2)
O5—C16	1.4294 (19)	C4—H4	0.93
C7—O2	1.2249 (18)	C2—H2	0.93
C7—C8	1.4771 (19)	C8—H8	0.93
O1—C19	1.4240 (19)	C17—H17A	0.96
O3—C14	1.3699 (16)	C17—H17B	0.96
O3—C18	1.415 (2)	C17—H17C	0.96
C13—O4	1.3685 (17)	C16—H16A	0.96
C13—C14	1.393 (2)	C16—H16B	0.96
C13—C12	1.400 (2)	C16—H16C	0.96
C14—C15	1.393 (2)	C18—H18A	0.96
C11—C12	1.390 (2)	C18—H18B	0.96
C11—C10	1.394 (2)	C18—H18C	0.96
C11—H11	0.93	C19—H19A	0.96
C1—C2	1.384 (2)	C19—H19B	0.96
C1—H1	0.93	C19—H19C	0.96
C9—C8	1.326 (2)
C1—C6—C5	118.15 (13)	O5—C12—C11	123.77 (13)
C1—C6—C7	119.52 (12)	O5—C12—C13	116.13 (12)
C5—C6—C7	122.33 (12)	C11—C12—C13	120.06 (13)
O1—C3—C2	124.72 (12)	C5—C4—C3	119.79 (13)
O1—C3—C4	115.06 (13)	C5—C4—H4	120.1
C2—C3—C4	120.22 (13)	C3—C4—H4	120.1
C12—O5—C16	117.36 (12)	C1—C2—C3	119.18 (12)
O2—C7—C8	121.82 (14)	C1—C2—H2	120.4
O2—C7—C6	120.82 (12)	C3—C2—H2	120.4
C8—C7—C6	117.33 (12)	C9—C8—C7	123.60 (13)
C3—O1—C19	118.02 (13)	C9—C8—H8	118.2
C14—O3—C18	117.77 (12)	C7—C8—H8	118.2
O4—C13—C14	118.37 (13)	O4—C17—H17A	109.5
O4—C13—C12	121.95 (14)	O4—C17—H17B	109.5
C14—C13—C12	119.36 (12)	H17A—C17—H17B	109.5
O3—C14—C15	124.40 (13)	O4—C17—H17C	109.5
O3—C14—C13	115.01 (12)	H17A—C17—H17C	109.5
C15—C14—C13	120.59 (13)	H17B—C17—H17C	109.5
C12—C11—C10	120.51 (12)	O5—C16—H16A	109.5
C12—C11—H11	119.7	O5—C16—H16B	109.5
C10—C11—H11	119.7	H16A—C16—H16B	109.5
C2—C1—C6	121.57 (13)	O5—C16—H16C	109.5
C2—C1—H1	119.2	H16A—C16—H16C	109.5
C6—C1—H1	119.2	H16B—C16—H16C	109.5
C8—C9—C10	125.52 (13)	O3—C18—H18A	109.5
C8—C9—H9	117.2	O3—C18—H18B	109.5
C10—C9—H9	117.2	H18A—C18—H18B	109.5
C14—C15—C10	119.90 (13)	O3—C18—H18C	109.5
C14—C15—H15	120	H18A—C18—H18C	109.5
C10—C15—H15	120	H18B—C18—H18C	109.5
C11—C10—C15	119.49 (12)	O1—C19—H19A	109.5
C11—C10—C9	121.44 (12)	O1—C19—H19B	109.5
C15—C10—C9	119.06 (13)	H19A—C19—H19B	109.5
C4—C5—C6	120.99 (12)	O1—C19—H19C	109.5
C4—C5—H5	119.5	H19A—C19—H19C	109.5
C6—C5—H5	119.5	H19B—C19—H19C	109.5
C13—O4—C17	118.42 (12)
C1—C6—C7—O2	−21.4 (2)	C1—C6—C5—C4	−1.2 (2)
C5—C6—C7—O2	158.90 (15)	C7—C6—C5—C4	178.5 (2)
C1—C6—C7—C8	156.7 (2)	C14—C13—O4—C17	−120.1 (2)
C5—C6—C7—C8	−23.0 (2)	C12—C13—O4—C17	66.4 (2)
C2—C3—O1—C19	−5.5 (2)	C16—O5—C12—C11	−3.9 (2)
C4—C3—O1—C19	174.5 (2)	C16—O5—C12—C13	173.9 (2)
C18—O3—C14—C15	−9.2 (2)	C10—C11—C12—O5	175.0 (2)
C18—O3—C14—C13	171.6 (2)	C10—C11—C12—C13	−2.6 (2)
O4—C13—C14—O3	7.7 (2)	O4—C13—C12—O5	−4.4 (2)
C12—C13—C14—O3	−178.7 (2)	C14—C13—C12—O5	−177.7 (2)
O4—C13—C14—C15	−171.4 (2)	O4—C13—C12—C11	173.5 (2)
C12—C13—C14—C15	2.1 (2)	C14—C13—C12—C11	0.1 (2)
C5—C6—C1—C2	3.0 (2)	C6—C5—C4—C3	−1.7 (2)
C7—C6—C1—C2	−176.6 (2)	O1—C3—C4—C5	−177.3 (2)
O3—C14—C15—C10	179.0 (2)	C2—C3—C4—C5	2.8 (2)
C13—C14—C15—C10	−1.9 (2)	C6—C1—C2—C3	−2.0 (2)
C12—C11—C10—C15	2.9 (2)	O1—C3—C2—C1	179.1 (2)
C12—C11—C10—C9	−176.0 (2)	C4—C3—C2—C1	−1.0 (2)
C14—C15—C10—C11	−0.6 (2)	C10—C9—C8—C7	177.7 (2)
C14—C15—C10—C9	178.3 (2)	O2—C7—C8—C9	−12.8 (2)
C8—C9—C10—C11	−4.4 (2)	C6—C7—C8—C9	169.1 (2)
C8—C9—C10—C15	176.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2i	0.93	2.51	3.415 (2)	165
C16—H16A···O2ii	0.96	2.55	3.484 (2)	165
C18—H18C···O1iii	0.96	2.53	3.332 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2	0.93	2.51	3.415 (2)	165
C16—H16A⋯O2	0.96	2.55	3.484 (2)	165
C18—H18C⋯O1i	0.96	2.53	3.332 (2)	142

Symmetry code: (i) .