(E)-3-(3,5-Dimeth-oxy-phen-yl)-1-(2-meth-oxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C18H18O4, the dihedral angle between the benzene rings is 52.52 (7)°. The C=C bond of the central enone group adopts a trans conformation. The relative conformation of the two double bonds in the enone group is s-transoid. In the crystal, mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Shin et al. (2012 ▶); Hwang et al. (2011 ▶). For related structures, see: Fun et al. (2012 ▶); Lee et al. (2012 ▶); Prasath et al. (2010 ▶).

Experimental

Crystal data

C18H18O4

M = 298.32

Monoclinic,

a = 12.0925 (18) Å

b = 8.4460 (12) Å

c = 15.109 (2) Å

β = 92.340 (3)°

V = 1541.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.24 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

11328 measured reflections

3865 independent reflections

1544 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.132

S = 0.81

3865 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006302/lh5589sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006302/lh5589Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006302/lh5589Isup3.cml

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

C18H18O4	F(000) = 632
Mr = 298.32	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2539 reflections
a = 12.0925 (18) Å	θ = 2.7–28.1°
b = 8.4460 (12) Å	µ = 0.09 mm−1
c = 15.109 (2) Å	T = 200 K
β = 92.340 (3)°	Block, colorless
V = 1541.9 (4) Å3	0.24 × 0.14 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	1544 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 28.5°, θmin = 1.7°
φ and ω scans	h = −16→14
11328 measured reflections	k = −11→10
3865 independent reflections	l = −20→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 0.81	w = 1/[σ2(Fo2) + (0.0575P)2] where P = (Fo2 + 2Fc2)/3
3865 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.40664 (18)	0.2012 (2)	0.41632 (14)	0.0370 (5)
O1	0.35034 (13)	0.11209 (19)	0.46017 (11)	0.0569 (5)
C2	0.52596 (18)	0.2050 (2)	0.43027 (13)	0.0366 (5)
H2	0.5597	0.1242	0.4658	0.044*
C3	0.59125 (17)	0.3144 (2)	0.39646 (13)	0.0359 (5)
H3	0.5557	0.3937	0.3609	0.043*
C4	0.71093 (17)	0.3259 (2)	0.40791 (14)	0.0352 (5)
C5	0.77006 (18)	0.2441 (2)	0.47412 (14)	0.0371 (5)
H5	0.7322	0.1807	0.5151	0.045*
C6	0.88426 (18)	0.2553 (2)	0.48006 (14)	0.0378 (5)
O2	0.93429 (13)	0.17546 (17)	0.54903 (10)	0.0498 (4)
C7	1.05199 (19)	0.1787 (3)	0.55712 (17)	0.0562 (7)
H7A	1.0827	0.1313	0.5043	0.084*
H7B	1.0770	0.1186	0.6097	0.084*
H7C	1.0773	0.2886	0.5630	0.084*
C8	0.94020 (17)	0.3433 (2)	0.41983 (14)	0.0384 (5)
H8	1.0187	0.3496	0.4239	0.046*
C9	0.88069 (18)	0.4234 (2)	0.35258 (15)	0.0379 (5)
O3	0.94471 (12)	0.50354 (18)	0.29569 (11)	0.0518 (5)
C10	0.8906 (2)	0.5865 (3)	0.22476 (16)	0.0587 (7)
H10A	0.8456	0.5124	0.1887	0.088*
H10B	0.9459	0.6359	0.1880	0.088*
H10C	0.8427	0.6685	0.2485	0.088*
C11	0.76750 (17)	0.4184 (2)	0.34780 (14)	0.0359 (5)
H11	0.7275	0.4778	0.3037	0.043*
C12	0.34924 (17)	0.3117 (2)	0.35221 (13)	0.0341 (5)
C13	0.26908 (18)	0.4123 (2)	0.38312 (14)	0.0392 (5)
H13	0.2521	0.4093	0.4439	0.047*
C14	0.21334 (18)	0.5168 (2)	0.32693 (15)	0.0427 (6)
H14	0.1595	0.5868	0.3490	0.051*
C15	0.23697 (18)	0.5181 (2)	0.23841 (15)	0.0426 (6)
H15	0.1986	0.5893	0.1994	0.051*
C16	0.31528 (18)	0.4178 (2)	0.20554 (14)	0.0399 (6)
H16	0.3303	0.4193	0.1443	0.048*
C17	0.37188 (17)	0.3148 (2)	0.26260 (14)	0.0351 (5)
O4	0.44767 (12)	0.20606 (17)	0.23581 (9)	0.0440 (4)
C18	0.4977 (2)	0.2339 (3)	0.15387 (16)	0.0613 (8)
H18A	0.4430	0.2171	0.1051	0.092*
H18B	0.5597	0.1605	0.1477	0.092*
H18C	0.5249	0.3431	0.1522	0.092*

	U11	U22	U33	U12	U13	U23
C1	0.0341 (13)	0.0409 (13)	0.0364 (12)	−0.0028 (10)	0.0042 (10)	0.0045 (10)
O1	0.0405 (10)	0.0666 (11)	0.0637 (11)	−0.0077 (8)	0.0019 (8)	0.0290 (9)
C2	0.0336 (13)	0.0404 (13)	0.0357 (12)	0.0040 (10)	0.0005 (10)	0.0056 (10)
C3	0.0343 (13)	0.0366 (12)	0.0369 (12)	0.0016 (9)	0.0009 (10)	0.0009 (10)
C4	0.0357 (13)	0.0331 (11)	0.0371 (12)	0.0008 (10)	0.0051 (10)	−0.0023 (10)
C5	0.0377 (14)	0.0385 (12)	0.0350 (12)	0.0012 (10)	−0.0012 (10)	0.0049 (10)
C6	0.0405 (14)	0.0335 (12)	0.0388 (13)	0.0078 (10)	−0.0064 (11)	0.0005 (10)
O2	0.0446 (10)	0.0522 (10)	0.0517 (10)	0.0050 (8)	−0.0108 (8)	0.0071 (8)
C7	0.0429 (16)	0.0523 (15)	0.0717 (18)	0.0036 (12)	−0.0198 (13)	0.0017 (13)
C8	0.0283 (12)	0.0369 (12)	0.0497 (14)	0.0034 (10)	−0.0019 (10)	−0.0016 (11)
C9	0.0355 (13)	0.0327 (12)	0.0460 (14)	−0.0014 (10)	0.0087 (11)	0.0003 (10)
O3	0.0360 (10)	0.0558 (10)	0.0642 (11)	0.0011 (8)	0.0085 (8)	0.0177 (9)
C10	0.0510 (17)	0.0658 (17)	0.0600 (17)	0.0020 (13)	0.0098 (14)	0.0228 (14)
C11	0.0307 (13)	0.0341 (12)	0.0428 (13)	0.0019 (9)	0.0014 (10)	0.0018 (10)
C12	0.0317 (12)	0.0335 (11)	0.0374 (12)	−0.0039 (9)	0.0030 (10)	0.0025 (10)
C13	0.0375 (13)	0.0433 (13)	0.0370 (12)	−0.0041 (10)	0.0044 (10)	0.0006 (11)
C14	0.0348 (13)	0.0378 (13)	0.0555 (16)	0.0000 (10)	0.0036 (11)	−0.0028 (12)
C15	0.0350 (13)	0.0393 (13)	0.0530 (15)	−0.0023 (10)	−0.0050 (11)	0.0091 (11)
C16	0.0413 (14)	0.0417 (13)	0.0364 (13)	−0.0043 (11)	0.0002 (11)	0.0060 (11)
C17	0.0318 (12)	0.0348 (12)	0.0389 (13)	−0.0020 (10)	0.0040 (10)	−0.0005 (10)
O4	0.0471 (10)	0.0489 (9)	0.0363 (9)	0.0096 (7)	0.0061 (7)	0.0007 (7)
C18	0.0630 (19)	0.0699 (17)	0.0529 (16)	0.0118 (14)	0.0248 (14)	0.0074 (14)

C1—O1	1.227 (2)	O3—C10	1.418 (3)
C1—C2	1.450 (3)	C10—H10A	0.9800
C1—C12	1.496 (3)	C10—H10B	0.9800
C2—C3	1.331 (3)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.454 (3)	C12—C13	1.384 (3)
C3—H3	0.9500	C12—C17	1.392 (3)
C4—C5	1.390 (3)	C13—C14	1.381 (3)
C4—C11	1.398 (3)	C13—H13	0.9500
C5—C6	1.384 (3)	C14—C15	1.379 (3)
C5—H5	0.9500	C14—H14	0.9500
C6—O2	1.362 (2)	C15—C16	1.378 (3)
C6—C8	1.374 (3)	C15—H15	0.9500
O2—C7	1.424 (3)	C16—C17	1.386 (3)
C7—H7A	0.9800	C16—H16	0.9500
C7—H7B	0.9800	C17—O4	1.370 (2)
C7—H7C	0.9800	O4—C18	1.420 (2)
C8—C9	1.396 (3)	C18—H18A	0.9800
C8—H8	0.9500	C18—H18B	0.9800
C9—O3	1.361 (2)	C18—H18C	0.9800
C9—C11	1.368 (3)
O1—C1—C2	120.4 (2)	O3—C10—H10B	109.5
O1—C1—C12	118.7 (2)	H10A—C10—H10B	109.5
C2—C1—C12	120.86 (18)	O3—C10—H10C	109.5
C3—C2—C1	124.2 (2)	H10A—C10—H10C	109.5
C3—C2—H2	117.9	H10B—C10—H10C	109.5
C1—C2—H2	117.9	C9—C11—C4	119.8 (2)
C2—C3—C4	127.2 (2)	C9—C11—H11	120.1
C2—C3—H3	116.4	C4—C11—H11	120.1
C4—C3—H3	116.4	C13—C12—C17	119.01 (19)
C5—C4—C11	119.6 (2)	C13—C12—C1	118.51 (18)
C5—C4—C3	122.21 (19)	C17—C12—C1	122.46 (18)
C11—C4—C3	118.11 (19)	C14—C13—C12	121.0 (2)
C6—C5—C4	119.7 (2)	C14—C13—H13	119.5
C6—C5—H5	120.1	C12—C13—H13	119.5
C4—C5—H5	120.1	C15—C14—C13	119.1 (2)
O2—C6—C8	124.0 (2)	C15—C14—H14	120.5
O2—C6—C5	115.25 (19)	C13—C14—H14	120.5
C8—C6—C5	120.7 (2)	C16—C15—C14	121.1 (2)
C6—O2—C7	117.86 (18)	C16—C15—H15	119.4
O2—C7—H7A	109.5	C14—C15—H15	119.4
O2—C7—H7B	109.5	C15—C16—C17	119.4 (2)
H7A—C7—H7B	109.5	C15—C16—H16	120.3
O2—C7—H7C	109.5	C17—C16—H16	120.3
H7A—C7—H7C	109.5	O4—C17—C16	123.80 (18)
H7B—C7—H7C	109.5	O4—C17—C12	115.80 (18)
C6—C8—C9	119.4 (2)	C16—C17—C12	120.32 (19)
C6—C8—H8	120.3	C17—O4—C18	117.45 (17)
C9—C8—H8	120.3	O4—C18—H18A	109.5
O3—C9—C11	125.1 (2)	O4—C18—H18B	109.5
O3—C9—C8	114.3 (2)	H18A—C18—H18B	109.5
C11—C9—C8	120.6 (2)	O4—C18—H18C	109.5
C9—O3—C10	117.80 (18)	H18A—C18—H18C	109.5
O3—C10—H10A	109.5	H18B—C18—H18C	109.5
O1—C1—C2—C3	−168.7 (2)	C5—C4—C11—C9	2.3 (3)
C12—C1—C2—C3	7.7 (3)	C3—C4—C11—C9	−175.44 (19)
C1—C2—C3—C4	179.76 (19)	O1—C1—C12—C13	54.6 (3)
C2—C3—C4—C5	−16.2 (3)	C2—C1—C12—C13	−121.9 (2)
C2—C3—C4—C11	161.5 (2)	O1—C1—C12—C17	−124.0 (2)
C11—C4—C5—C6	0.2 (3)	C2—C1—C12—C17	59.4 (3)
C3—C4—C5—C6	177.85 (19)	C17—C12—C13—C14	−1.3 (3)
C4—C5—C6—O2	177.74 (18)	C1—C12—C13—C14	−180.0 (2)
C4—C5—C6—C8	−1.7 (3)	C12—C13—C14—C15	1.2 (3)
C8—C6—O2—C7	−2.4 (3)	C13—C14—C15—C16	−0.3 (3)
C5—C6—O2—C7	178.19 (18)	C14—C15—C16—C17	−0.5 (3)
O2—C6—C8—C9	−178.67 (19)	C15—C16—C17—O4	177.12 (19)
C5—C6—C8—C9	0.7 (3)	C15—C16—C17—C12	0.5 (3)
C6—C8—C9—O3	−178.56 (18)	C13—C12—C17—O4	−176.49 (17)
C6—C8—C9—C11	1.9 (3)	C1—C12—C17—O4	2.1 (3)
C11—C9—O3—C10	−1.2 (3)	C13—C12—C17—C16	0.4 (3)
C8—C9—O3—C10	179.24 (19)	C1—C12—C17—C16	179.03 (19)
O3—C9—C11—C4	177.11 (18)	C16—C17—O4—C18	21.6 (3)
C8—C9—C11—C4	−3.4 (3)	C12—C17—O4—C18	−161.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.51	3.457 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.51	3.457 (3)	172

Symmetry code: (i) .