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

The title compound, C19H20O6, consists of a tetra-substituted benzene ring with one substituent being an α,β-unsaturated cinnamoyl group, which forms an extended conjugated system in the mol-ecule. In addition, two meth-oxy-meth-oxy and one hy-droxy group are bonded to the central benzene ring. The dihedral angle between eh rings is 10.22 (10)°. An intra-molecular hydrogen bond is observed between the hy-droxy group and the carbonyl O atom. One of the meth-oxy-meth-oxy substituents is conformationally disordered over two sets of sites with site-occupation factors of 0.831 (3) and 0.169 (3).

Related literature

For the preparation of the title compound, see: Sui et al. (2012 ▶). For general background to the biological activity of chalcones which posess more than one hy­droxy substituent, see: Jun et al. (2007 ▶); Jin et al. (2007 ▶); Urgaonkar et al. (2005 ▶); Nerya et al. (2004 ▶, 2003 ▶); Khatib et al. (2005 ▶).

Experimental

Crystal data

C19H20O6

M = 344.35

Monoclinic,

a = 8.7791 (2) Å

b = 9.7807 (2) Å

c = 20.2209 (4) Å

β = 96.792 (2)°

V = 1724.10 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.82 mm−1

T = 290 K

0.45 × 0.40 × 0.32 mm

Data collection

Agilent Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) ▶ T min = 0.709, T max = 0.779

5842 measured reflections

2964 independent reflections

2492 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.161

S = 1.02

2964 reflections

235 parameters

37 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009380/im2424sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009380/im2424Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009380/im2424Isup3.cml

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

C19H20O6	F(000) = 728
Mr = 344.35	Dx = 1.327 Mg m−3
Monoclinic, P21/n	Melting point: 351 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 8.7791 (2) Å	Cell parameters from 3081 reflections
b = 9.7807 (2) Å	θ = 4.4–69.7°
c = 20.2209 (4) Å	µ = 0.82 mm−1
β = 96.792 (2)°	T = 290 K
V = 1724.10 (6) Å3	Block, yellow
Z = 4	0.45 × 0.40 × 0.32 mm

Agilent Gemini S Ultra diffractometer	2964 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2492 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.045
Detector resolution: 15.9149 pixels mm-1	θmax = 65.8°, θmin = 4.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.709, Tmax = 0.779	l = −16→23
5842 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0915P)2 + 0.2682P] where P = (Fo2 + 2Fc2)/3
2964 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.21 e Å−3
37 restraints	Δρmin = −0.21 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
O4	−0.21800 (16)	0.09828 (14)	0.66097 (7)	0.0649 (4)
O1	0.0530 (2)	0.30639 (14)	0.87486 (8)	0.0750 (5)
H1	0.1167	0.3199	0.9073	0.112*
O3	−0.19754 (16)	−0.05558 (14)	0.74997 (6)	0.0626 (4)
O2	0.2224 (2)	0.25370 (14)	0.97783 (8)	0.0742 (5)
O5	0.12831 (19)	−0.15711 (14)	0.94560 (7)	0.0711 (4)
C8	0.3002 (2)	0.0383 (2)	1.01680 (9)	0.0574 (5)
H8	0.3110	−0.0535	1.0063	0.069*
C2	−0.0697 (2)	0.1321 (2)	0.81172 (9)	0.0563 (5)
H2	−0.1150	0.1973	0.7822	0.068*
C7	0.2076 (2)	0.12700 (19)	0.96934 (9)	0.0547 (5)
C3	0.0291 (2)	0.17122 (18)	0.86711 (9)	0.0541 (5)
C4	0.10277 (19)	0.07590 (18)	0.91324 (8)	0.0483 (4)
C6	−0.0300 (2)	−0.10263 (18)	0.84434 (9)	0.0526 (4)
H6	−0.0489	−0.1948	0.8356	0.063*
C10	0.4654 (2)	0.00877 (19)	1.12493 (8)	0.0507 (4)
C9	0.3686 (2)	0.0851 (2)	1.07405 (9)	0.0545 (4)
H9	0.3533	0.1771	1.0829	0.065*
C5	0.0665 (2)	−0.06416 (18)	0.89966 (8)	0.0489 (4)
C15	0.4845 (3)	−0.1320 (2)	1.12293 (10)	0.0659 (5)
H15	0.4331	−0.1819	1.0880	0.079*
C13	0.6568 (3)	−0.1276 (3)	1.22351 (11)	0.0702 (6)
H13	0.7208	−0.1732	1.2562	0.084*
C14	0.5784 (3)	−0.1987 (2)	1.17194 (12)	0.0745 (6)
H14	0.5887	−0.2932	1.1700	0.089*
C1	−0.0993 (2)	−0.00402 (19)	0.80133 (8)	0.0513 (4)
C16	−0.2928 (2)	0.0378 (2)	0.70981 (10)	0.0615 (5)
H16A	−0.3823	−0.0104	0.6889	0.074*
H16B	−0.3278	0.1086	0.7381	0.074*
C17	−0.1989 (3)	0.0086 (3)	0.60743 (12)	0.0811 (7)
H17A	−0.1626	0.0593	0.5718	0.122*
H17B	−0.2955	−0.0332	0.5919	0.122*
H17C	−0.1257	−0.0610	0.6224	0.122*
C12	0.6400 (3)	0.0115 (3)	1.22645 (10)	0.0722 (6)
H12	0.6932	0.0605	1.2612	0.087*
C11	0.5442 (3)	0.0794 (2)	1.17786 (10)	0.0639 (5)
H11	0.5326	0.1737	1.1807	0.077*
C18	0.0761 (3)	−0.2935 (2)	0.94163 (12)	0.0743 (6)	0.831 (3)
H18A	0.1002	−0.3362	0.9849	0.089*	0.831 (3)
H18B	−0.0346	−0.2934	0.9312	0.089*	0.831 (3)
O6	0.1357 (2)	−0.3676 (2)	0.89696 (10)	0.0789 (6)	0.831 (3)
C19	0.2932 (4)	−0.3990 (4)	0.9126 (2)	0.0947 (10)	0.831 (3)
H19A	0.3270	−0.4531	0.8776	0.142*	0.831 (3)
H19B	0.3079	−0.4493	0.9536	0.142*	0.831 (3)
H19C	0.3515	−0.3157	0.9174	0.142*	0.831 (3)
C18'	0.0761 (3)	−0.2935 (2)	0.94163 (12)	0.0743 (6)	0.169 (3)
H18C	−0.0085	−0.3037	0.9680	0.089*	0.169 (3)
H18D	0.0386	−0.3150	0.8958	0.089*	0.169 (3)
O6'	0.1929 (12)	−0.3852 (10)	0.9645 (5)	0.0789 (6)	0.169 (3)
C19'	0.342 (2)	−0.388 (2)	0.9489 (10)	0.0947 (10)	0.169 (3)
H19D	0.3972	−0.4599	0.9731	0.142*	0.169 (3)
H19E	0.3902	−0.3016	0.9608	0.142*	0.169 (3)
H19F	0.3408	−0.4027	0.9019	0.142*	0.169 (3)

	U11	U22	U33	U12	U13	U23
O4	0.0802 (9)	0.0532 (8)	0.0573 (8)	−0.0038 (6)	−0.0086 (7)	0.0012 (6)
O1	0.0951 (11)	0.0422 (7)	0.0783 (10)	0.0016 (7)	−0.0283 (8)	−0.0011 (6)
O3	0.0701 (8)	0.0561 (8)	0.0555 (7)	−0.0068 (6)	−0.0174 (6)	0.0021 (6)
O2	0.0957 (11)	0.0501 (8)	0.0688 (9)	−0.0009 (7)	−0.0232 (8)	−0.0067 (6)
O5	0.0916 (10)	0.0479 (8)	0.0657 (9)	−0.0043 (7)	−0.0244 (7)	0.0106 (6)
C8	0.0627 (10)	0.0522 (10)	0.0536 (10)	0.0056 (8)	−0.0086 (8)	−0.0059 (8)
C2	0.0620 (11)	0.0489 (10)	0.0540 (10)	0.0024 (8)	−0.0101 (8)	0.0026 (8)
C7	0.0598 (10)	0.0515 (10)	0.0506 (10)	0.0018 (8)	−0.0027 (8)	−0.0065 (8)
C3	0.0606 (10)	0.0419 (9)	0.0573 (10)	0.0025 (8)	−0.0037 (8)	−0.0011 (8)
C4	0.0516 (9)	0.0459 (9)	0.0459 (9)	0.0025 (7)	−0.0010 (7)	−0.0014 (7)
C6	0.0620 (10)	0.0434 (9)	0.0502 (10)	−0.0031 (8)	−0.0029 (8)	0.0007 (7)
C10	0.0521 (9)	0.0538 (10)	0.0449 (9)	−0.0048 (8)	0.0008 (7)	−0.0009 (7)
C9	0.0605 (10)	0.0500 (10)	0.0511 (10)	−0.0027 (8)	−0.0018 (8)	−0.0024 (8)
C5	0.0540 (9)	0.0459 (9)	0.0448 (9)	0.0026 (7)	−0.0023 (7)	0.0032 (7)
C15	0.0747 (13)	0.0573 (12)	0.0600 (11)	−0.0006 (10)	−0.0149 (9)	−0.0074 (9)
C13	0.0664 (12)	0.0832 (15)	0.0569 (11)	0.0044 (11)	−0.0099 (9)	0.0096 (10)
C14	0.0855 (15)	0.0600 (13)	0.0726 (13)	0.0104 (11)	−0.0126 (11)	0.0003 (10)
C1	0.0517 (9)	0.0534 (10)	0.0465 (9)	−0.0024 (8)	−0.0041 (7)	0.0003 (8)
C16	0.0578 (10)	0.0650 (12)	0.0575 (11)	0.0012 (9)	−0.0116 (8)	0.0018 (9)
C17	0.1038 (18)	0.0701 (14)	0.0687 (13)	0.0104 (13)	0.0078 (12)	−0.0033 (11)
C12	0.0782 (13)	0.0797 (15)	0.0529 (11)	−0.0131 (12)	−0.0155 (10)	−0.0021 (10)
C11	0.0804 (13)	0.0566 (11)	0.0510 (10)	−0.0110 (10)	−0.0075 (9)	−0.0017 (8)
C18	0.0887 (14)	0.0545 (11)	0.0760 (13)	−0.0065 (10)	−0.0060 (10)	0.0119 (9)
O6	0.0952 (13)	0.0614 (10)	0.0743 (11)	0.0005 (9)	−0.0151 (9)	0.0004 (8)
C19	0.102 (2)	0.0909 (19)	0.090 (2)	0.0088 (17)	0.0051 (17)	0.0009 (18)
C18'	0.0887 (14)	0.0545 (11)	0.0760 (13)	−0.0065 (10)	−0.0060 (10)	0.0119 (9)
O6'	0.0952 (13)	0.0614 (10)	0.0743 (11)	0.0005 (9)	−0.0151 (9)	0.0004 (8)
C19'	0.102 (2)	0.0909 (19)	0.090 (2)	0.0088 (17)	0.0051 (17)	0.0009 (18)

O4—C16	1.382 (2)	C15—C14	1.376 (3)
O4—C17	1.419 (3)	C15—H15	0.9300
O1—C3	1.345 (2)	C13—C14	1.369 (3)
O1—H1	0.8200	C13—C12	1.370 (3)
O3—C1	1.366 (2)	C13—H13	0.9300
O3—C16	1.426 (2)	C14—H14	0.9300
O2—C7	1.256 (2)	C16—H16A	0.9700
O5—C5	1.366 (2)	C16—H16B	0.9700
O5—C18	1.410 (3)	C17—H17A	0.9600
C8—C9	1.321 (3)	C17—H17B	0.9600
C8—C7	1.466 (3)	C17—H17C	0.9600
C8—H8	0.9300	C12—C11	1.385 (3)
C2—C1	1.368 (3)	C12—H12	0.9300
C2—C3	1.387 (3)	C11—H11	0.9300
C2—H2	0.9300	C18—O6	1.313 (3)
C7—C4	1.462 (2)	C18—H18A	0.9700
C3—C4	1.420 (3)	C18—H18B	0.9700
C4—C5	1.426 (3)	O6—C19	1.415 (4)
C6—C5	1.373 (2)	C19—H19A	0.9600
C6—C1	1.390 (3)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C10—C11	1.388 (3)	O6'—C19'	1.38 (2)
C10—C15	1.388 (3)	C19'—H19D	0.9600
C10—C9	1.460 (2)	C19'—H19E	0.9600
C9—H9	0.9300	C19'—H19F	0.9600
C16—O4—C17	112.95 (18)	O3—C1—C2	124.58 (16)
C3—O1—H1	109.5	O3—C1—C6	114.20 (17)
C1—O3—C16	118.14 (15)	C2—C1—C6	121.21 (17)
C5—O5—C18	119.41 (16)	O4—C16—O3	112.66 (16)
C9—C8—C7	121.84 (18)	O4—C16—H16A	109.1
C9—C8—H8	119.1	O3—C16—H16A	109.1
C7—C8—H8	119.1	O4—C16—H16B	109.1
C1—C2—C3	118.79 (17)	O3—C16—H16B	109.1
C1—C2—H2	120.6	H16A—C16—H16B	107.8
C3—C2—H2	120.6	O4—C17—H17A	109.5
O2—C7—C4	119.27 (17)	O4—C17—H17B	109.5
O2—C7—C8	117.02 (16)	H17A—C17—H17B	109.5
C4—C7—C8	123.70 (16)	O4—C17—H17C	109.5
O1—C3—C2	116.05 (17)	H17A—C17—H17C	109.5
O1—C3—C4	121.08 (17)	H17B—C17—H17C	109.5
C2—C3—C4	122.86 (17)	C13—C12—C11	120.3 (2)
C3—C4—C5	115.49 (16)	C13—C12—H12	119.8
C3—C4—C7	118.79 (16)	C11—C12—H12	119.8
C5—C4—C7	125.72 (16)	C12—C11—C10	120.9 (2)
C5—C6—C1	120.12 (17)	C12—C11—H11	119.5
C5—C6—H6	119.9	C10—C11—H11	119.5
C1—C6—H6	119.9	O6—C18—O5	114.1 (2)
C11—C10—C15	117.74 (18)	O6—C18—H18A	108.7
C11—C10—C9	118.97 (18)	O5—C18—H18A	108.7
C15—C10—C9	123.28 (17)	O6—C18—H18B	108.7
C8—C9—C10	127.34 (18)	O5—C18—H18B	108.7
C8—C9—H9	116.3	H18A—C18—H18B	107.6
C10—C9—H9	116.3	C18—O6—C19	115.0 (2)
O5—C5—C6	121.93 (16)	O6—C19—H19A	109.5
O5—C5—C4	116.55 (15)	O6—C19—H19B	109.5
C6—C5—C4	121.49 (16)	H19A—C19—H19B	109.5
C14—C15—C10	120.88 (19)	O6—C19—H19C	109.5
C14—C15—H15	119.6	H19A—C19—H19C	109.5
C10—C15—H15	119.6	H19B—C19—H19C	109.5
C14—C13—C12	119.4 (2)	O6'—C19'—H19D	109.5
C14—C13—H13	120.3	O6'—C19'—H19E	109.5
C12—C13—H13	120.3	H19D—C19'—H19E	109.5
C13—C14—C15	120.8 (2)	O6'—C19'—H19F	109.5
C13—C14—H14	119.6	H19D—C19'—H19F	109.5
C15—C14—H14	119.6	H19E—C19'—H19F	109.5
C9—C8—C7—O2	15.2 (3)	C3—C4—C5—C6	1.9 (3)
C9—C8—C7—C4	−165.70 (18)	C7—C4—C5—C6	−177.89 (17)
C1—C2—C3—O1	−179.65 (18)	C11—C10—C15—C14	0.1 (3)
C1—C2—C3—C4	0.9 (3)	C9—C10—C15—C14	179.39 (19)
O1—C3—C4—C5	179.44 (18)	C12—C13—C14—C15	0.6 (4)
C2—C3—C4—C5	−1.1 (3)	C10—C15—C14—C13	−0.8 (4)
O1—C3—C4—C7	−0.8 (3)	C16—O3—C1—C2	−9.5 (3)
C2—C3—C4—C7	178.66 (17)	C16—O3—C1—C6	169.82 (16)
O2—C7—C4—C3	4.6 (3)	C3—C2—C1—O3	177.95 (17)
C8—C7—C4—C3	−174.55 (17)	C3—C2—C1—C6	−1.3 (3)
O2—C7—C4—C5	−175.71 (18)	C5—C6—C1—O3	−177.26 (16)
C8—C7—C4—C5	5.2 (3)	C5—C6—C1—C2	2.1 (3)
C7—C8—C9—C10	−178.90 (17)	C17—O4—C16—O3	74.6 (2)
C11—C10—C9—C8	171.4 (2)	C1—O3—C16—O4	82.4 (2)
C15—C10—C9—C8	−7.9 (3)	C14—C13—C12—C11	0.2 (4)
C18—O5—C5—C6	−9.0 (3)	C13—C12—C11—C10	−1.0 (3)
C18—O5—C5—C4	168.81 (18)	C15—C10—C11—C12	0.8 (3)
C1—C6—C5—O5	175.31 (16)	C9—C10—C11—C12	−178.55 (18)
C1—C6—C5—C4	−2.4 (3)	C5—O5—C18—O6	79.7 (3)
C3—C4—C5—O5	−175.96 (16)	O5—C18—O6—C19	70.1 (3)
C7—C4—C5—O5	4.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.73	2.466 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.73	2.466 (2)	148