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

In the title mol-ecule, C18H18O4, the C=C bond of the central enone group adopts a trans conformation. The relative conformation of the C=O and C=C bonds is s-cisoid. The dihedral angle between the planes of the benzene rings is 29.49 (12)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Shenvi et al. (2013 ▶); Hsieh et al. (2012 ▶); Hwang et al. (2011 ▶); Jo et al. (2012 ▶); Sharma et al. (2012 ▶); Sashidhara et al. (2011 ▶). For related structures, see: Carvalho-Jr et al. (2011 ▶); Wu et al. (2012 ▶).

Experimental

Crystal data

C18H18O4

M = 298.32

Triclinic,

a = 8.2402 (12) Å

b = 9.1449 (14) Å

c = 10.8876 (16) Å

α = 95.395 (3)°

β = 107.667 (3)°

γ = 102.837 (3)°

V = 750.61 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.33 × 0.26 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.970, T max = 0.989

4383 measured reflections

2619 independent reflections

1531 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.115

S = 0.98

2619 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.26 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008982/lh5590sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008982/lh5590Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008982/lh5590Isup3.cml

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

C18H18O4	Z = 2
Mr = 298.32	F(000) = 316
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2402 (12) Å	Cell parameters from 1553 reflections
b = 9.1449 (14) Å	θ = 2.3–27.9°
c = 10.8876 (16) Å	µ = 0.09 mm−1
α = 95.395 (3)°	T = 200 K
β = 107.667 (3)°	Block, pale yellow
γ = 102.837 (3)°	0.33 × 0.26 × 0.12 mm
V = 750.61 (19) Å3

Bruker SMART CCD diffractometer	2619 independent reflections
Radiation source: fine-focus sealed tube	1531 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→9
Tmin = 0.970, Tmax = 0.989	k = −9→10
4383 measured reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0394P)2] where P = (Fo2 + 2Fc2)/3
2619 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.26 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
C1	0.0722 (3)	0.0058 (3)	0.7610 (2)	0.0354 (6)
O1	0.0527 (2)	−0.06317 (18)	0.65288 (16)	0.0503 (5)
C2	−0.0008 (3)	0.1386 (3)	0.7724 (2)	0.0385 (6)
H2	−0.0059	0.1771	0.8549	0.046*
C3	−0.0595 (3)	0.2054 (3)	0.6708 (2)	0.0355 (6)
H3	−0.0560	0.1615	0.5893	0.043*
C4	−0.1290 (3)	0.3399 (2)	0.6711 (2)	0.0338 (6)
C5	−0.1565 (3)	0.4081 (3)	0.7811 (2)	0.0413 (6)
H5	−0.1313	0.3665	0.8594	0.050*
C6	−0.2199 (3)	0.5353 (3)	0.7760 (2)	0.0435 (7)
H6	−0.2397	0.5798	0.8508	0.052*
C7	−0.2555 (3)	0.6000 (3)	0.6635 (2)	0.0407 (6)
H7	−0.2990	0.6879	0.6611	0.049*
C8	−0.2268 (3)	0.5343 (3)	0.5553 (2)	0.0359 (6)
O2	−0.2555 (2)	0.58787 (18)	0.43929 (15)	0.0456 (5)
C9	−0.3268 (3)	0.7168 (3)	0.4271 (2)	0.0462 (7)
H9A	−0.4436	0.6916	0.4371	0.069*
H9B	−0.3375	0.7444	0.3407	0.069*
H9C	−0.2481	0.8028	0.4952	0.069*
C10	−0.1656 (3)	0.4048 (2)	0.5588 (2)	0.0341 (6)
H10	−0.1485	0.3597	0.4831	0.041*
C11	0.1748 (3)	−0.0419 (3)	0.8812 (2)	0.0325 (6)
C12	0.2212 (3)	−0.1790 (2)	0.8674 (2)	0.0323 (6)
H12	0.1800	−0.2429	0.7842	0.039*
C13	0.3267 (3)	−0.2205 (2)	0.9747 (2)	0.0329 (6)
O3	0.3825 (2)	−0.35105 (17)	0.97449 (15)	0.0466 (5)
C14	0.3448 (4)	−0.4415 (3)	0.8493 (2)	0.0493 (7)
H14A	0.2167	−0.4794	0.8067	0.074*
H14B	0.3970	−0.5278	0.8611	0.074*
H14C	0.3951	−0.3791	0.7947	0.074*
C15	0.3874 (3)	−0.1279 (2)	1.0980 (2)	0.0342 (6)
H15	0.4604	−0.1577	1.1718	0.041*
C16	0.3407 (3)	0.0062 (3)	1.1115 (2)	0.0321 (6)
O4	0.3951 (2)	0.10519 (17)	1.22797 (15)	0.0441 (5)
C17	0.5018 (4)	0.0614 (3)	1.3408 (2)	0.0491 (7)
H17A	0.4375	−0.0362	1.3542	0.074*
H17B	0.5295	0.1393	1.4177	0.074*
H17C	0.6116	0.0510	1.3279	0.074*
C18	0.2335 (3)	0.0503 (3)	1.0033 (2)	0.0349 (6)
H18	0.2008	0.1428	1.0131	0.042*

	U11	U22	U33	U12	U13	U23
C1	0.0339 (15)	0.0363 (14)	0.0369 (15)	0.0102 (12)	0.0112 (13)	0.0105 (12)
O1	0.0648 (14)	0.0511 (11)	0.0357 (11)	0.0269 (10)	0.0094 (10)	0.0079 (9)
C2	0.0385 (16)	0.0407 (15)	0.0398 (15)	0.0142 (13)	0.0146 (13)	0.0088 (12)
C3	0.0323 (15)	0.0366 (14)	0.0396 (15)	0.0115 (12)	0.0115 (13)	0.0117 (11)
C4	0.0272 (14)	0.0336 (14)	0.0406 (15)	0.0078 (11)	0.0114 (12)	0.0069 (11)
C5	0.0418 (16)	0.0444 (15)	0.0401 (15)	0.0131 (13)	0.0146 (14)	0.0118 (12)
C6	0.0485 (18)	0.0438 (16)	0.0443 (16)	0.0163 (14)	0.0213 (14)	0.0069 (13)
C7	0.0427 (17)	0.0354 (15)	0.0482 (16)	0.0174 (13)	0.0158 (14)	0.0078 (12)
C8	0.0330 (15)	0.0375 (15)	0.0388 (15)	0.0129 (12)	0.0102 (13)	0.0113 (12)
O2	0.0589 (13)	0.0466 (11)	0.0424 (11)	0.0297 (9)	0.0186 (10)	0.0166 (8)
C9	0.0516 (18)	0.0417 (16)	0.0501 (17)	0.0249 (14)	0.0123 (15)	0.0168 (13)
C10	0.0353 (15)	0.0354 (14)	0.0342 (14)	0.0126 (12)	0.0123 (12)	0.0081 (11)
C11	0.0292 (14)	0.0365 (14)	0.0313 (14)	0.0071 (11)	0.0101 (12)	0.0063 (11)
C12	0.0325 (14)	0.0287 (13)	0.0342 (14)	0.0077 (11)	0.0096 (12)	0.0040 (11)
C13	0.0361 (15)	0.0306 (13)	0.0360 (14)	0.0148 (12)	0.0117 (12)	0.0110 (11)
O3	0.0637 (13)	0.0386 (10)	0.0405 (10)	0.0267 (10)	0.0127 (10)	0.0056 (8)
C14	0.0572 (19)	0.0384 (15)	0.0497 (17)	0.0190 (14)	0.0129 (15)	−0.0035 (13)
C15	0.0348 (15)	0.0396 (15)	0.0300 (14)	0.0115 (12)	0.0107 (12)	0.0112 (11)
C16	0.0325 (14)	0.0352 (14)	0.0297 (13)	0.0101 (12)	0.0110 (12)	0.0051 (11)
O4	0.0544 (12)	0.0433 (10)	0.0340 (10)	0.0195 (9)	0.0105 (9)	0.0016 (8)
C17	0.0529 (18)	0.0585 (18)	0.0314 (15)	0.0178 (15)	0.0069 (14)	0.0031 (13)
C18	0.0347 (15)	0.0342 (14)	0.0412 (15)	0.0135 (12)	0.0158 (13)	0.0113 (12)

C1—O1	1.229 (2)	C10—H10	0.9500
C1—C2	1.481 (3)	C11—C18	1.390 (3)
C1—C11	1.489 (3)	C11—C12	1.397 (3)
C2—C3	1.329 (3)	C12—C13	1.371 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.467 (3)	C13—O3	1.371 (2)
C3—H3	0.9500	C13—C15	1.400 (3)
C4—C10	1.389 (3)	O3—C14	1.433 (2)
C4—C5	1.401 (3)	C14—H14A	0.9800
C5—C6	1.376 (3)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—C7	1.390 (3)	C15—C16	1.373 (3)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.379 (3)	C16—O4	1.373 (2)
C7—H7	0.9500	C16—C18	1.395 (3)
C8—O2	1.370 (2)	O4—C17	1.426 (3)
C8—C10	1.385 (3)	C17—H17A	0.9800
O2—C9	1.429 (2)	C17—H17B	0.9800
C9—H9A	0.9800	C17—H17C	0.9800
C9—H9B	0.9800	C18—H18	0.9500
C9—H9C	0.9800
O1—C1—C2	120.5 (2)	C4—C10—H10	119.4
O1—C1—C11	119.6 (2)	C18—C11—C12	120.0 (2)
C2—C1—C11	119.9 (2)	C18—C11—C1	121.7 (2)
C3—C2—C1	122.0 (2)	C12—C11—C1	118.1 (2)
C3—C2—H2	119.0	C13—C12—C11	119.5 (2)
C1—C2—H2	119.0	C13—C12—H12	120.2
C2—C3—C4	126.9 (2)	C11—C12—H12	120.2
C2—C3—H3	116.6	C12—C13—O3	125.4 (2)
C4—C3—H3	116.6	C12—C13—C15	120.8 (2)
C10—C4—C5	118.3 (2)	O3—C13—C15	113.8 (2)
C10—C4—C3	118.9 (2)	C13—O3—C14	116.83 (18)
C5—C4—C3	122.7 (2)	O3—C14—H14A	109.5
C6—C5—C4	120.1 (2)	O3—C14—H14B	109.5
C6—C5—H5	120.0	H14A—C14—H14B	109.5
C4—C5—H5	120.0	O3—C14—H14C	109.5
C5—C6—C7	121.2 (2)	H14A—C14—H14C	109.5
C5—C6—H6	119.4	H14B—C14—H14C	109.5
C7—C6—H6	119.4	C16—C15—C13	119.6 (2)
C8—C7—C6	118.9 (2)	C16—C15—H15	120.2
C8—C7—H7	120.5	C13—C15—H15	120.2
C6—C7—H7	120.5	C15—C16—O4	123.8 (2)
O2—C8—C7	124.4 (2)	C15—C16—C18	120.3 (2)
O2—C8—C10	115.29 (19)	O4—C16—C18	115.8 (2)
C7—C8—C10	120.3 (2)	C16—O4—C17	117.02 (18)
C8—O2—C9	118.08 (17)	O4—C17—H17A	109.5
O2—C9—H9A	109.5	O4—C17—H17B	109.5
O2—C9—H9B	109.5	H17A—C17—H17B	109.5
H9A—C9—H9B	109.5	O4—C17—H17C	109.5
O2—C9—H9C	109.5	H17A—C17—H17C	109.5
H9A—C9—H9C	109.5	H17B—C17—H17C	109.5
H9B—C9—H9C	109.5	C11—C18—C16	119.7 (2)
C8—C10—C4	121.2 (2)	C11—C18—H18	120.2
C8—C10—H10	119.4	C16—C18—H18	120.2
O1—C1—C2—C3	−12.8 (4)	O1—C1—C11—C12	−10.3 (3)
C11—C1—C2—C3	165.3 (2)	C2—C1—C11—C12	171.6 (2)
C1—C2—C3—C4	−177.9 (2)	C18—C11—C12—C13	−0.8 (3)
C2—C3—C4—C10	172.7 (2)	C1—C11—C12—C13	175.2 (2)
C2—C3—C4—C5	−5.9 (4)	C11—C12—C13—O3	−179.6 (2)
C10—C4—C5—C6	0.6 (4)	C11—C12—C13—C15	0.4 (3)
C3—C4—C5—C6	179.2 (2)	C12—C13—O3—C14	7.9 (3)
C4—C5—C6—C7	−0.9 (4)	C15—C13—O3—C14	−172.10 (19)
C5—C6—C7—C8	0.2 (4)	C12—C13—C15—C16	0.0 (3)
C6—C7—C8—O2	−179.5 (2)	O3—C13—C15—C16	−180.0 (2)
C6—C7—C8—C10	0.9 (4)	C13—C15—C16—O4	−179.33 (19)
C7—C8—O2—C9	−2.6 (4)	C13—C15—C16—C18	0.0 (3)
C10—C8—O2—C9	177.0 (2)	C15—C16—O4—C17	−2.0 (3)
O2—C8—C10—C4	179.2 (2)	C18—C16—O4—C17	178.7 (2)
C7—C8—C10—C4	−1.2 (4)	C12—C11—C18—C16	0.8 (3)
C5—C4—C10—C8	0.4 (4)	C1—C11—C18—C16	−175.1 (2)
C3—C4—C10—C8	−178.2 (2)	C15—C16—C18—C11	−0.4 (3)
O1—C1—C11—C18	165.7 (2)	O4—C16—C18—C11	178.96 (19)
C2—C1—C11—C18	−12.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4i	0.95	2.55	3.405 (3)	151
C9—H9C···O1ii	0.98	2.50	3.388 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O4i	0.95	2.55	3.405 (3)	151
C9—H9C⋯O1ii	0.98	2.50	3.388 (3)	150

Symmetry codes: (i) ; (ii) .