(E)-1-(2-Hy-droxy-6-meth-oxy-phen-yl)-3-(2,4,6-tri-meth-oxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C19H20O6, the conformation about the C=C bond of the central enone group is E. The dihedral angle formed by the benzene rings is 11.6 (2)°. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond. 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: Shin et al. (2013 ▶); Yong et al. (2013 ▶); Hsieh et al. (2012 ▶); Sashidhara et al. (2011 ▶); Sharma et al. (2012 ▶). For related structures, see: Chantrapromma et al. (2013 ▶); Li et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H20O6

M = 344.35

Monoclinic,

a = 7.2509 (11) Å

b = 15.670 (2) Å

c = 14.529 (2) Å

β = 99.579 (3)°

V = 1627.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.32 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

11993 measured reflections

4062 independent reflections

1641 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.146

S = 0.83

4062 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031498/lh5668sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031498/lh5668Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031498/lh5668Isup3.cml

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

C19H20O6	F(000) = 728
Mr = 344.35	Dx = 1.405 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2416 reflections
a = 7.2509 (11) Å	θ = 2.6–26.0°
b = 15.670 (2) Å	µ = 0.11 mm−1
c = 14.529 (2) Å	T = 200 K
β = 99.579 (3)°	Block, yellow
V = 1627.8 (4) Å3	0.32 × 0.19 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1641 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −9→9
11993 measured reflections	k = −20→17
4062 independent reflections	l = −12→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 0.83	w = 1/[σ2(Fo2) + (0.0623P)2] where P = (Fo2 + 2Fc2)/3
4062 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 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	0.1235 (3)	0.18277 (14)	−0.17106 (17)	0.0341 (6)
O1	0.0997 (2)	0.25771 (9)	−0.20093 (12)	0.0470 (5)
C2	0.2322 (3)	0.16860 (14)	−0.07822 (16)	0.0348 (6)
H2	0.2615	0.1122	−0.0568	0.042*
C3	0.2905 (3)	0.23561 (14)	−0.02317 (17)	0.0342 (6)
H3	0.2559	0.2896	−0.0504	0.041*
C4	0.3967 (3)	0.23973 (13)	0.07012 (16)	0.0310 (6)
C5	0.4563 (3)	0.16888 (14)	0.12690 (17)	0.0349 (6)
O2	0.4201 (2)	0.09143 (9)	0.08508 (11)	0.0442 (5)
C6	0.4501 (4)	0.01601 (14)	0.14069 (19)	0.0481 (7)
H6A	0.5830	0.0115	0.1676	0.072*
H6B	0.4125	−0.0340	0.1016	0.072*
H6C	0.3755	0.0188	0.1910	0.072*
C7	0.5470 (3)	0.17725 (15)	0.21872 (17)	0.0386 (6)
H7	0.5846	0.1282	0.2556	0.046*
C8	0.5812 (3)	0.25842 (15)	0.25526 (17)	0.0377 (6)
O3	0.6695 (2)	0.27612 (10)	0.34409 (12)	0.0483 (5)
C9	0.7234 (4)	0.20637 (16)	0.40476 (18)	0.0547 (8)
H9A	0.6125	0.1731	0.4123	0.082*
H9B	0.7838	0.2278	0.4657	0.082*
H9C	0.8112	0.1700	0.3782	0.082*
C10	0.5288 (3)	0.33007 (14)	0.20224 (17)	0.0380 (6)
H10	0.5550	0.3853	0.2280	0.046*
C11	0.4386 (3)	0.32097 (14)	0.11176 (16)	0.0339 (6)
O4	0.3845 (2)	0.38954 (9)	0.05574 (11)	0.0415 (5)
C12	0.4042 (4)	0.47228 (13)	0.09820 (18)	0.0433 (7)
H12A	0.3354	0.4740	0.1508	0.065*
H12B	0.3538	0.5156	0.0521	0.065*
H12C	0.5369	0.4839	0.1207	0.065*
C13	0.0480 (3)	0.11226 (13)	−0.23419 (16)	0.0327 (6)
C14	−0.0110 (3)	0.13084 (14)	−0.32983 (17)	0.0354 (6)
O5	−0.0123 (3)	0.21060 (10)	−0.36318 (11)	0.0456 (5)
H5	0.0250	0.2445	−0.3192	0.068*
C15	−0.0686 (3)	0.06696 (15)	−0.39475 (17)	0.0401 (6)
H15	−0.1026	0.0807	−0.4590	0.048*
C16	−0.0759 (3)	−0.01563 (15)	−0.36553 (18)	0.0416 (7)
H16	−0.1145	−0.0591	−0.4102	0.050*
C17	−0.0285 (3)	−0.03734 (14)	−0.27249 (18)	0.0394 (6)
H17	−0.0370	−0.0950	−0.2534	0.047*
C18	0.0315 (3)	0.02531 (13)	−0.20719 (17)	0.0337 (6)
O6	0.0748 (2)	0.00753 (9)	−0.11397 (11)	0.0433 (5)
C19	0.0704 (4)	−0.07976 (14)	−0.08470 (18)	0.0453 (7)
H19A	−0.0563	−0.1025	−0.1028	0.068*
H19B	0.1065	−0.0830	−0.0167	0.068*
H19C	0.1580	−0.1134	−0.1145	0.068*

	U11	U22	U33	U12	U13	U23
C1	0.0405 (15)	0.0230 (12)	0.0382 (15)	0.0022 (10)	0.0044 (12)	−0.0002 (11)
O1	0.0698 (13)	0.0252 (9)	0.0408 (11)	−0.0004 (8)	−0.0057 (9)	0.0021 (8)
C2	0.0411 (15)	0.0252 (12)	0.0363 (15)	0.0009 (11)	0.0010 (12)	0.0031 (11)
C3	0.0393 (15)	0.0252 (12)	0.0358 (15)	−0.0015 (10)	−0.0005 (12)	0.0015 (11)
C4	0.0351 (14)	0.0264 (12)	0.0305 (14)	0.0018 (10)	0.0027 (11)	0.0023 (10)
C5	0.0375 (15)	0.0302 (13)	0.0370 (15)	−0.0002 (11)	0.0059 (12)	−0.0011 (11)
O2	0.0609 (12)	0.0265 (9)	0.0422 (11)	0.0026 (8)	−0.0008 (9)	0.0057 (8)
C6	0.0554 (18)	0.0306 (14)	0.0558 (18)	0.0047 (12)	0.0019 (15)	0.0102 (13)
C7	0.0412 (16)	0.0349 (13)	0.0384 (16)	0.0049 (11)	0.0027 (12)	0.0068 (12)
C8	0.0378 (15)	0.0411 (15)	0.0315 (15)	0.0011 (11)	−0.0020 (12)	−0.0014 (12)
O3	0.0615 (13)	0.0421 (10)	0.0366 (11)	0.0061 (9)	−0.0054 (10)	0.0035 (9)
C9	0.071 (2)	0.0501 (17)	0.0406 (17)	0.0101 (15)	0.0033 (15)	0.0119 (14)
C10	0.0449 (16)	0.0313 (13)	0.0350 (15)	0.0016 (11)	−0.0013 (12)	−0.0009 (11)
C11	0.0375 (15)	0.0302 (13)	0.0324 (14)	0.0023 (11)	0.0011 (12)	0.0008 (11)
O4	0.0581 (12)	0.0245 (9)	0.0371 (10)	0.0012 (8)	−0.0060 (9)	−0.0023 (7)
C12	0.0537 (17)	0.0259 (13)	0.0454 (16)	−0.0018 (11)	−0.0060 (13)	−0.0065 (11)
C13	0.0372 (14)	0.0229 (12)	0.0354 (14)	0.0013 (10)	−0.0011 (11)	−0.0018 (10)
C14	0.0349 (15)	0.0276 (13)	0.0408 (16)	0.0012 (10)	−0.0018 (12)	0.0014 (12)
O5	0.0611 (13)	0.0325 (9)	0.0384 (11)	−0.0022 (8)	−0.0055 (9)	0.0050 (8)
C15	0.0433 (16)	0.0399 (15)	0.0340 (15)	0.0004 (12)	−0.0026 (12)	−0.0026 (12)
C16	0.0434 (16)	0.0380 (15)	0.0407 (16)	−0.0013 (12)	−0.0009 (13)	−0.0131 (13)
C17	0.0442 (16)	0.0250 (12)	0.0478 (17)	−0.0009 (11)	0.0042 (13)	−0.0060 (12)
C18	0.0363 (14)	0.0278 (13)	0.0365 (15)	0.0006 (10)	0.0045 (12)	−0.0013 (11)
O6	0.0681 (13)	0.0248 (9)	0.0366 (11)	−0.0036 (8)	0.0079 (9)	0.0018 (8)
C19	0.0591 (18)	0.0279 (13)	0.0495 (17)	−0.0022 (12)	0.0105 (14)	0.0075 (12)

C1—O1	1.254 (2)	C10—C11	1.375 (3)
C1—C2	1.461 (3)	C10—H10	0.9500
C1—C13	1.481 (3)	C11—O4	1.365 (2)
C2—C3	1.345 (3)	O4—C12	1.433 (2)
C2—H2	0.9500	C12—H12A	0.9800
C3—C4	1.445 (3)	C12—H12B	0.9800
C3—H3	0.9500	C12—H12C	0.9800
C4—C5	1.408 (3)	C13—C14	1.414 (3)
C4—C11	1.420 (3)	C13—C18	1.428 (3)
C5—O2	1.363 (2)	C14—O5	1.340 (2)
C5—C7	1.392 (3)	C14—C15	1.391 (3)
O2—C6	1.428 (3)	O5—H5	0.8400
C6—H6A	0.9800	C15—C16	1.366 (3)
C6—H6B	0.9800	C15—H15	0.9500
C6—H6C	0.9800	C16—C17	1.381 (3)
C7—C8	1.385 (3)	C16—H16	0.9500
C7—H7	0.9500	C17—C18	1.384 (3)
C8—O3	1.370 (3)	C17—H17	0.9500
C8—C10	1.379 (3)	C18—O6	1.367 (3)
O3—C9	1.418 (3)	O6—C19	1.434 (2)
C9—H9A	0.9800	C19—H19A	0.9800
C9—H9B	0.9800	C19—H19B	0.9800
C9—H9C	0.9800	C19—H19C	0.9800
O1—C1—C2	118.9 (2)	C8—C10—H10	120.2
O1—C1—C13	118.0 (2)	O4—C11—C10	122.1 (2)
C2—C1—C13	123.03 (19)	O4—C11—C4	115.58 (19)
C3—C2—C1	119.9 (2)	C10—C11—C4	122.3 (2)
C3—C2—H2	120.1	C11—O4—C12	117.22 (18)
C1—C2—H2	120.1	O4—C12—H12A	109.5
C2—C3—C4	131.2 (2)	O4—C12—H12B	109.5
C2—C3—H3	114.4	H12A—C12—H12B	109.5
C4—C3—H3	114.4	O4—C12—H12C	109.5
C5—C4—C11	115.7 (2)	H12A—C12—H12C	109.5
C5—C4—C3	125.3 (2)	H12B—C12—H12C	109.5
C11—C4—C3	118.84 (19)	C14—C13—C18	116.1 (2)
O2—C5—C7	122.4 (2)	C14—C13—C1	118.37 (19)
O2—C5—C4	115.1 (2)	C18—C13—C1	125.5 (2)
C7—C5—C4	122.5 (2)	O5—C14—C15	116.3 (2)
C5—O2—C6	119.01 (19)	O5—C14—C13	122.0 (2)
O2—C6—H6A	109.5	C15—C14—C13	121.7 (2)
O2—C6—H6B	109.5	C14—O5—H5	109.5
H6A—C6—H6B	109.5	C16—C15—C14	119.6 (2)
O2—C6—H6C	109.5	C16—C15—H15	120.2
H6A—C6—H6C	109.5	C14—C15—H15	120.2
H6B—C6—H6C	109.5	C15—C16—C17	121.4 (2)
C8—C7—C5	118.7 (2)	C15—C16—H16	119.3
C8—C7—H7	120.7	C17—C16—H16	119.3
C5—C7—H7	120.7	C16—C17—C18	119.7 (2)
O3—C8—C10	113.8 (2)	C16—C17—H17	120.2
O3—C8—C7	125.0 (2)	C18—C17—H17	120.2
C10—C8—C7	121.2 (2)	O6—C18—C17	121.9 (2)
C8—O3—C9	117.82 (19)	O6—C18—C13	116.8 (2)
O3—C9—H9A	109.5	C17—C18—C13	121.3 (2)
O3—C9—H9B	109.5	C18—O6—C19	118.38 (17)
H9A—C9—H9B	109.5	O6—C19—H19A	109.5
O3—C9—H9C	109.5	O6—C19—H19B	109.5
H9A—C9—H9C	109.5	H19A—C19—H19B	109.5
H9B—C9—H9C	109.5	O6—C19—H19C	109.5
C11—C10—C8	119.5 (2)	H19A—C19—H19C	109.5
C11—C10—H10	120.2	H19B—C19—H19C	109.5
O1—C1—C2—C3	5.9 (4)	C3—C4—C11—C10	175.9 (2)
C13—C1—C2—C3	−177.5 (2)	C10—C11—O4—C12	−7.6 (3)
C1—C2—C3—C4	179.5 (2)	C4—C11—O4—C12	172.9 (2)
C2—C3—C4—C5	−3.3 (4)	O1—C1—C13—C14	13.0 (3)
C2—C3—C4—C11	−179.9 (3)	C2—C1—C13—C14	−163.5 (2)
C11—C4—C5—O2	−178.1 (2)	O1—C1—C13—C18	−167.9 (2)
C3—C4—C5—O2	5.2 (3)	C2—C1—C13—C18	15.5 (4)
C11—C4—C5—C7	1.3 (3)	C18—C13—C14—O5	176.3 (2)
C3—C4—C5—C7	−175.3 (2)	C1—C13—C14—O5	−4.6 (4)
C7—C5—O2—C6	9.7 (3)	C18—C13—C14—C15	−4.6 (4)
C4—C5—O2—C6	−170.9 (2)	C1—C13—C14—C15	174.5 (2)
O2—C5—C7—C8	178.8 (2)	O5—C14—C15—C16	−178.2 (2)
C4—C5—C7—C8	−0.6 (4)	C13—C14—C15—C16	2.7 (4)
C5—C7—C8—O3	−179.7 (2)	C14—C15—C16—C17	0.4 (4)
C5—C7—C8—C10	−0.6 (4)	C15—C16—C17—C18	−1.3 (4)
C10—C8—O3—C9	178.1 (2)	C16—C17—C18—O6	178.0 (2)
C7—C8—O3—C9	−2.7 (4)	C16—C17—C18—C13	−0.9 (4)
O3—C8—C10—C11	−179.9 (2)	C14—C13—C18—O6	−175.3 (2)
C7—C8—C10—C11	0.9 (4)	C1—C13—C18—O6	5.7 (4)
C8—C10—C11—O4	−179.6 (2)	C14—C13—C18—C17	3.7 (4)
C8—C10—C11—C4	−0.1 (4)	C1—C13—C18—C17	−175.3 (2)
C5—C4—C11—O4	178.5 (2)	C17—C18—O6—C19	4.6 (3)
C3—C4—C11—O4	−4.6 (3)	C13—C18—O6—C19	−176.4 (2)
C5—C4—C11—C10	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1	0.84	1.73	2.475 (2)	147
C17—H17···O1i	0.95	2.42	3.265 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1	0.84	1.73	2.475 (2)	147
C17—H17⋯O1i	0.95	2.42	3.265 (3)	148

Symmetry code: (i) .