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

The title compound, C(19)H(20)O(5), is approximately planar; the dihedral angle between the benzene rings is 3.82 (8)°, and the central propenone C(=O)-C=C plane makes dihedral angles of 1.95 (10) and 3.17 (11)° with the two benzene rings. In the crystal structure, intra- and inter-molecular C-H⋯O hydrogen bonds are observed.

Related literature

For related structures, see: Huang et al. (2010 ▶); Peng et al. (2010 ▶); Yathirajan et al. (2006 ▶); Zhao et al. (2010 ▶). For background to and applications of chalcones, see: Liang et al. (2007 ▶); Liu et al. (2008 ▶); Mojzisa et al. (2008 ▶); Nielsen et al. (2005 ▶); Nowakowska (2007 ▶); Selvakumar et al. (2007 ▶); Wu et al. (2010 ▶); Wu, Chen et al. (2009 ▶); Wu, Qiu et al. (2009 ▶); Wu, Zhang et al. (2009 ▶).

Experimental

Crystal data

C19H20O5

M = 328.35

Monoclinic,

a = 9.031 (5) Å

b = 7.962 (5) Å

c = 23.631 (14) Å

β = 92.827 (10)°

V = 1697.0 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.47 × 0.35 × 0.31 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.958, T max = 0.972

8581 measured reflections

2981 independent reflections

2407 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.04

2981 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043606/is2604sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043606/is2604Isup2.hkl

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

C19H20O5	F(000) = 696
Mr = 328.35	Dx = 1.285 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3028 reflections
a = 9.031 (5) Å	θ = 2.4–25.4°
b = 7.962 (5) Å	µ = 0.09 mm−1
c = 23.631 (14) Å	T = 298 K
β = 92.827 (10)°	Block, colourless
V = 1697.0 (17) Å3	0.47 × 0.35 × 0.31 mm
Z = 4

Bruker APEX area-detector diffractometer	2981 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.958, Tmax = 0.972	k = −7→9
8581 measured reflections	l = −28→21

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.1943P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2981 reflections	Δρmax = 0.14 e Å−3
222 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (16)

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	0.28103 (12)	0.90184 (19)	0.42954 (5)	0.0819 (4)
O2	0.70723 (11)	0.80481 (15)	0.32588 (5)	0.0638 (3)
O3	1.12815 (14)	0.4756 (2)	0.43350 (6)	0.0919 (5)
O4	1.56960 (12)	0.36084 (15)	0.31617 (5)	0.0671 (4)
O5	1.51234 (12)	0.49882 (14)	0.21947 (5)	0.0609 (3)
C1	0.2027 (2)	0.8905 (3)	0.48040 (9)	0.0961 (7)
H1A	0.1911	0.7746	0.4905	0.144*
H1B	0.1068	0.9414	0.4746	0.144*
H1C	0.2574	0.9479	0.5104	0.144*
C2	0.42024 (16)	0.8369 (2)	0.42967 (7)	0.0580 (4)
C3	0.49109 (19)	0.7598 (3)	0.47532 (7)	0.0698 (5)
H3	0.4444	0.7487	0.5093	0.084*
C4	0.63289 (18)	0.6990 (2)	0.46998 (7)	0.0652 (5)
H4	0.6801	0.6467	0.5011	0.078*
C5	0.70830 (16)	0.71205 (19)	0.42044 (7)	0.0509 (4)
C6	0.63254 (15)	0.79194 (18)	0.37421 (6)	0.0482 (4)
C7	0.49051 (16)	0.8529 (2)	0.37918 (7)	0.0535 (4)
H7	0.4417	0.9052	0.3484	0.064*
C8	0.63986 (18)	0.8895 (2)	0.27838 (7)	0.0652 (5)
H8A	0.5486	0.8345	0.2670	0.098*
H8B	0.7055	0.8875	0.2476	0.098*
H8C	0.6199	1.0038	0.2884	0.098*
C9	0.85599 (16)	0.6388 (2)	0.41978 (7)	0.0556 (4)
H9	0.8906	0.5935	0.4542	0.067*
C10	0.94973 (16)	0.6258 (2)	0.37837 (7)	0.0560 (4)
H10	0.9239	0.6703	0.3429	0.067*
C11	1.09404 (17)	0.5415 (2)	0.38803 (7)	0.0577 (4)
C12	1.19894 (16)	0.53612 (18)	0.34148 (6)	0.0490 (4)
C13	1.17154 (16)	0.61029 (19)	0.28937 (7)	0.0534 (4)
H13	1.0832	0.6682	0.2822	0.064*
C14	1.27305 (17)	0.60041 (19)	0.24734 (7)	0.0557 (4)
H14	1.2519	0.6506	0.2123	0.067*
C15	1.40530 (16)	0.51638 (18)	0.25735 (7)	0.0504 (4)
C16	1.43577 (15)	0.44187 (18)	0.31052 (6)	0.0493 (4)
C17	1.33443 (16)	0.45188 (19)	0.35158 (7)	0.0515 (4)
H17	1.3555	0.4022	0.3867	0.062*
C18	1.61263 (19)	0.2977 (2)	0.37027 (8)	0.0669 (5)
H18A	1.6114	0.3869	0.3976	0.100*
H18B	1.7109	0.2520	0.3696	0.100*
H18C	1.5449	0.2111	0.3805	0.100*
C19	1.4842 (2)	0.5671 (3)	0.16424 (7)	0.0703 (5)
H19A	1.3940	0.5204	0.1478	0.105*
H19B	1.5650	0.5401	0.1409	0.105*
H19C	1.4745	0.6869	0.1668	0.105*

	U11	U22	U33	U12	U13	U23
O1	0.0504 (7)	0.1228 (11)	0.0734 (9)	0.0280 (7)	0.0114 (6)	−0.0078 (8)
O2	0.0466 (6)	0.0894 (9)	0.0563 (7)	0.0110 (5)	0.0110 (5)	0.0148 (6)
O3	0.0720 (8)	0.1376 (13)	0.0679 (9)	0.0480 (8)	0.0213 (7)	0.0313 (8)
O4	0.0547 (7)	0.0841 (8)	0.0635 (8)	0.0250 (6)	0.0118 (6)	0.0059 (6)
O5	0.0566 (7)	0.0690 (7)	0.0584 (7)	0.0066 (5)	0.0163 (5)	0.0010 (5)
C1	0.0587 (12)	0.152 (2)	0.0797 (14)	0.0236 (12)	0.0227 (10)	−0.0226 (14)
C2	0.0426 (8)	0.0710 (10)	0.0609 (10)	0.0082 (7)	0.0086 (7)	−0.0105 (8)
C3	0.0573 (10)	0.0980 (14)	0.0555 (10)	0.0150 (9)	0.0167 (8)	0.0014 (9)
C4	0.0584 (10)	0.0837 (12)	0.0541 (10)	0.0146 (9)	0.0096 (8)	0.0066 (9)
C5	0.0459 (8)	0.0538 (9)	0.0534 (9)	0.0033 (7)	0.0081 (7)	−0.0011 (7)
C6	0.0417 (8)	0.0509 (8)	0.0526 (9)	−0.0013 (6)	0.0072 (7)	−0.0032 (7)
C7	0.0446 (8)	0.0592 (9)	0.0564 (9)	0.0043 (7)	0.0001 (7)	−0.0016 (7)
C8	0.0560 (10)	0.0859 (12)	0.0536 (10)	0.0003 (9)	0.0032 (8)	0.0061 (9)
C9	0.0493 (9)	0.0599 (9)	0.0578 (10)	0.0071 (7)	0.0041 (7)	0.0040 (7)
C10	0.0471 (9)	0.0633 (10)	0.0578 (10)	0.0086 (7)	0.0059 (7)	0.0015 (8)
C11	0.0508 (9)	0.0665 (10)	0.0561 (10)	0.0120 (7)	0.0068 (7)	0.0032 (8)
C12	0.0435 (8)	0.0489 (8)	0.0548 (9)	0.0034 (6)	0.0044 (7)	−0.0046 (7)
C13	0.0450 (8)	0.0538 (9)	0.0616 (10)	0.0088 (7)	0.0045 (7)	0.0006 (7)
C14	0.0555 (9)	0.0579 (9)	0.0539 (9)	0.0054 (7)	0.0050 (7)	0.0048 (7)
C15	0.0486 (9)	0.0483 (8)	0.0549 (9)	−0.0010 (6)	0.0103 (7)	−0.0056 (7)
C16	0.0437 (8)	0.0475 (8)	0.0570 (9)	0.0067 (6)	0.0059 (7)	−0.0046 (7)
C17	0.0491 (8)	0.0540 (9)	0.0515 (9)	0.0065 (7)	0.0032 (7)	−0.0009 (7)
C18	0.0581 (10)	0.0706 (11)	0.0717 (12)	0.0165 (8)	0.0009 (8)	0.0029 (9)
C19	0.0722 (11)	0.0831 (12)	0.0566 (10)	0.0015 (10)	0.0141 (8)	0.0019 (9)

O1—C2	1.3593 (19)	C8—H8B	0.9600
O1—C1	1.427 (2)	C8—H8C	0.9600
O2—C6	1.3586 (18)	C9—C10	1.329 (2)
O2—C8	1.420 (2)	C9—H9	0.9300
O3—C11	1.222 (2)	C10—C11	1.473 (2)
O4—C16	1.3707 (18)	C10—H10	0.9300
O4—C18	1.410 (2)	C11—C12	1.487 (2)
O5—C15	1.3567 (17)	C12—C13	1.377 (2)
O5—C19	1.425 (2)	C12—C17	1.405 (2)
C1—H1A	0.9600	C13—C14	1.387 (2)
C1—H1B	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C14—C15	1.379 (2)
C2—C3	1.372 (3)	C14—H14	0.9300
C2—C7	1.385 (2)	C15—C16	1.404 (2)
C3—C4	1.381 (2)	C16—C17	1.369 (2)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.387 (2)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.412 (2)	C18—H18C	0.9600
C5—C9	1.456 (2)	C19—H19A	0.9600
C6—C7	1.382 (2)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—H8A	0.9600
C2—O1—C1	118.09 (15)	C9—C10—C11	120.80 (15)
C6—O2—C8	119.28 (12)	C9—C10—H10	119.6
C16—O4—C18	117.28 (12)	C11—C10—H10	119.6
C15—O5—C19	117.65 (13)	O3—C11—C10	120.98 (14)
O1—C1—H1A	109.5	O3—C11—C12	119.72 (14)
O1—C1—H1B	109.5	C10—C11—C12	119.30 (14)
H1A—C1—H1B	109.5	C13—C12—C17	118.23 (14)
O1—C1—H1C	109.5	C13—C12—C11	123.79 (14)
H1A—C1—H1C	109.5	C17—C12—C11	117.98 (14)
H1B—C1—H1C	109.5	C12—C13—C14	121.35 (14)
O1—C2—C3	124.58 (15)	C12—C13—H13	119.3
O1—C2—C7	115.21 (15)	C14—C13—H13	119.3
C3—C2—C7	120.21 (14)	C15—C14—C13	120.14 (15)
C2—C3—C4	118.93 (16)	C15—C14—H14	119.9
C2—C3—H3	120.5	C13—C14—H14	119.9
C4—C3—H3	120.5	O5—C15—C14	125.17 (15)
C3—C4—C5	123.17 (16)	O5—C15—C16	115.61 (13)
C3—C4—H4	118.4	C14—C15—C16	119.23 (13)
C5—C4—H4	118.4	C17—C16—O4	125.14 (14)
C4—C5—C6	116.59 (14)	C17—C16—C15	120.09 (14)
C4—C5—C9	117.84 (14)	O4—C16—C15	114.77 (12)
C6—C5—C9	125.54 (14)	C16—C17—C12	120.96 (15)
O2—C6—C7	123.12 (14)	C16—C17—H17	119.5
O2—C6—C5	116.28 (13)	C12—C17—H17	119.5
C7—C6—C5	120.60 (14)	O4—C18—H18A	109.5
C6—C7—C2	120.51 (15)	O4—C18—H18B	109.5
C6—C7—H7	119.7	H18A—C18—H18B	109.5
C2—C7—H7	119.7	O4—C18—H18C	109.5
O2—C8—H8A	109.5	H18A—C18—H18C	109.5
O2—C8—H8B	109.5	H18B—C18—H18C	109.5
H8A—C8—H8B	109.5	O5—C19—H19A	109.5
O2—C8—H8C	109.5	O5—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19B	109.5
H8B—C8—H8C	109.5	O5—C19—H19C	109.5
C10—C9—C5	131.00 (16)	H19A—C19—H19C	109.5
C10—C9—H9	114.5	H19B—C19—H19C	109.5
C5—C9—H9	114.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3i	0.93	2.46	3.363 (3)	162
C8—H8B···O4ii	0.96	2.60	3.537 (3)	166
C10—H10···O2	0.93	2.25	2.846 (3)	121
C19—H19A···O1iii	0.96	2.54	3.443 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.93	2.46	3.363 (3)	162
C8—H8B⋯O4ii	0.96	2.60	3.537 (3)	166
C10—H10⋯O2	0.93	2.25	2.846 (3)	121
C19—H19A⋯O1iii	0.96	2.54	3.443 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) .