Crystal structure of (E)-4,6-dimeth-oxy-2-(4-meth-oxy-styr-yl)-3-methyl-benzaldehyde.

In the title mol-ecule, C19H20O4, the central C=C double bond adopts an E configuration. The dihedral angle formed by the planes of the two benzene rings is 83.57 (12)°. The three meth-oxy groups are essentially coplanar with the benzene rings to which they are attached, with C C-O-C torsion angles of -0.2 (3), -2.3 (3) and -4.1 (3)°.

Related literature

For the synthesis and biological properties of resveratrol derivatives, see: Chen et al. (2015 ▸); Chillemi et al. (2015 ▸); Li et al. (2014 ▸); Shin et al. (2014 ▸); Huang et al. (2007 ▸). For related structures, see: Ge et al. (2013 ▸); Tang et al. (2011 ▸).

Experimental

Crystal data

C19H20O4

M = 312.35

Monoclinic,

a = 11.3632 (9) Å

b = 8.7159 (7) Å

c = 16.2382 (13) Å

β = 101.927 (2)°

V = 1573.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.26 × 0.20 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

11266 measured reflections

3904 independent reflections

1966 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.222

S = 0.99

3904 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 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/S2056989015017363/lh5786sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017363/lh5786Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017363/lh5786Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017363/lh5786fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015017363/lh5786fig2.tif

Synthetic scheme for preparation of resveratrol derivative compounds.

CCDC reference: 1425329

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H20O4	F(000) = 664
Mr = 312.35	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3256 reflections
a = 11.3632 (9) Å	θ = 2.7–28.2°
b = 8.7159 (7) Å	µ = 0.09 mm−1
c = 16.2382 (13) Å	T = 200 K
β = 101.927 (2)°	Block, light yellow
V = 1573.5 (2) Å3	0.26 × 0.20 × 0.13 mm
Z = 4

Bruker SMART CCD diffractometer	1966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −15→14
11266 measured reflections	k = −11→11
3904 independent reflections	l = −16→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1179P)2] where P = (Fo2 + 2Fc2)/3
3904 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.31 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	0.8260 (2)	0.0967 (3)	0.05627 (14)	0.0374 (5)
C2	0.7634 (2)	0.0081 (3)	−0.01021 (15)	0.0400 (6)
C3	0.7955 (2)	0.0212 (3)	−0.08861 (14)	0.0398 (6)
C4	0.8854 (2)	0.1179 (3)	−0.10269 (15)	0.0408 (6)
H4	0.9040	0.1253	−0.1569	0.049*
C5	0.9481 (2)	0.2042 (3)	−0.03599 (14)	0.0384 (6)
C6	0.9196 (2)	0.1962 (2)	0.04419 (14)	0.0368 (5)
C7	0.6658 (2)	−0.1046 (3)	−0.00234 (18)	0.0568 (7)
H7A	0.5871	−0.0586	−0.0248	0.085*
H7B	0.6718	−0.1308	0.0571	0.085*
H7C	0.6752	−0.1978	−0.0342	0.085*
O1	0.73156 (16)	−0.0693 (2)	−0.15023 (11)	0.0533 (5)
C8	0.7593 (3)	−0.0620 (3)	−0.23169 (15)	0.0582 (8)
H8A	0.7488	0.0435	−0.2529	0.087*
H8B	0.7054	−0.1304	−0.2700	0.087*
H8C	0.8429	−0.0940	−0.2283	0.087*
O2	1.03780 (16)	0.30232 (19)	−0.04472 (10)	0.0481 (5)
C9	1.0693 (2)	0.3103 (3)	−0.12493 (16)	0.0516 (7)
H9A	1.0958	0.2090	−0.1400	0.077*
H9B	1.1346	0.3846	−0.1229	0.077*
H9C	0.9991	0.3428	−0.1672	0.077*
O3	0.97338 (18)	0.3109 (2)	0.18130 (11)	0.0574 (5)
C10	0.9879 (2)	0.2931 (3)	0.10982 (16)	0.0477 (6)
H10	1.0519	0.3497	0.0950	0.057*
C11	0.7965 (2)	0.0880 (3)	0.14099 (14)	0.0404 (6)
H11	0.8607	0.0662	0.1871	0.049*
C12	0.6884 (2)	0.1081 (3)	0.15791 (15)	0.0417 (6)
H12	0.6232	0.1226	0.1114	0.050*
C13	0.6605 (2)	0.1098 (3)	0.24196 (15)	0.0414 (6)
C14	0.5693 (2)	0.2034 (3)	0.25915 (15)	0.0464 (6)
H14	0.5208	0.2594	0.2145	0.056*
C15	0.5475 (2)	0.2171 (3)	0.33950 (16)	0.0483 (6)
H15	0.4861	0.2839	0.3498	0.058*
C16	0.6156 (2)	0.1327 (3)	0.40527 (14)	0.0405 (6)
C17	0.7041 (2)	0.0355 (3)	0.38910 (15)	0.0441 (6)
H17	0.7495	−0.0247	0.4332	0.053*
C18	0.7270 (2)	0.0256 (3)	0.30880 (14)	0.0437 (6)
H18	0.7894	−0.0400	0.2989	0.052*
O4	0.58605 (15)	0.15293 (19)	0.48210 (10)	0.0480 (5)
C19	0.6468 (2)	0.0587 (3)	0.54938 (15)	0.0524 (7)
H19A	0.6389	−0.0492	0.5322	0.079*
H19B	0.6112	0.0739	0.5988	0.079*
H19C	0.7322	0.0867	0.5633	0.079*

	U11	U22	U33	U12	U13	U23
C1	0.0382 (12)	0.0403 (12)	0.0348 (12)	0.0087 (10)	0.0102 (10)	0.0032 (10)
C2	0.0396 (13)	0.0408 (13)	0.0406 (13)	0.0040 (10)	0.0110 (10)	−0.0006 (10)
C3	0.0390 (13)	0.0406 (12)	0.0399 (13)	0.0023 (10)	0.0080 (10)	−0.0043 (11)
C4	0.0433 (13)	0.0454 (13)	0.0348 (12)	0.0052 (11)	0.0109 (10)	0.0012 (10)
C5	0.0375 (12)	0.0407 (12)	0.0389 (13)	0.0049 (10)	0.0124 (10)	0.0022 (10)
C6	0.0344 (12)	0.0388 (12)	0.0381 (12)	0.0048 (10)	0.0094 (10)	0.0046 (10)
C7	0.0569 (17)	0.0580 (16)	0.0592 (18)	−0.0107 (13)	0.0205 (14)	−0.0078 (14)
O1	0.0529 (11)	0.0631 (11)	0.0452 (10)	−0.0100 (9)	0.0130 (8)	−0.0147 (9)
C8	0.0631 (18)	0.0748 (19)	0.0369 (14)	−0.0077 (15)	0.0108 (12)	−0.0130 (13)
O2	0.0517 (10)	0.0557 (11)	0.0409 (10)	−0.0137 (8)	0.0193 (8)	−0.0016 (8)
C9	0.0583 (16)	0.0561 (15)	0.0462 (15)	−0.0048 (13)	0.0246 (13)	0.0014 (12)
O3	0.0725 (13)	0.0651 (12)	0.0353 (10)	−0.0099 (9)	0.0130 (9)	−0.0052 (9)
C10	0.0480 (15)	0.0541 (15)	0.0405 (14)	−0.0051 (12)	0.0077 (12)	−0.0004 (12)
C11	0.0437 (13)	0.0422 (12)	0.0370 (13)	0.0014 (10)	0.0121 (10)	0.0023 (10)
C12	0.0430 (14)	0.0477 (14)	0.0360 (12)	−0.0019 (11)	0.0116 (10)	0.0014 (11)
C13	0.0404 (13)	0.0461 (13)	0.0398 (13)	−0.0044 (10)	0.0136 (10)	0.0006 (11)
C14	0.0417 (14)	0.0613 (16)	0.0375 (13)	0.0047 (11)	0.0109 (11)	0.0046 (12)
C15	0.0411 (14)	0.0581 (15)	0.0479 (15)	0.0023 (12)	0.0146 (11)	−0.0002 (12)
C16	0.0406 (13)	0.0494 (13)	0.0339 (12)	−0.0095 (11)	0.0129 (10)	−0.0052 (11)
C17	0.0459 (14)	0.0482 (14)	0.0410 (13)	0.0013 (11)	0.0150 (11)	0.0058 (11)
C18	0.0432 (13)	0.0451 (13)	0.0454 (14)	0.0024 (11)	0.0150 (11)	0.0022 (11)
O4	0.0497 (10)	0.0588 (11)	0.0382 (9)	−0.0032 (8)	0.0154 (8)	−0.0025 (8)
C19	0.0594 (16)	0.0543 (15)	0.0431 (14)	−0.0127 (13)	0.0100 (12)	0.0003 (12)

C1—C2	1.396 (3)	C9—H9C	0.9800
C1—C6	1.417 (3)	O3—C10	1.215 (3)
C1—C11	1.484 (3)	C10—H10	0.9500
C2—C3	1.399 (3)	C11—C12	1.325 (3)
C2—C7	1.506 (3)	C11—H11	0.9500
C3—O1	1.360 (3)	C12—C13	1.463 (3)
C3—C4	1.379 (3)	C12—H12	0.9500
C4—C5	1.388 (3)	C13—C14	1.391 (3)
C4—H4	0.9500	C13—C18	1.396 (3)
C5—O2	1.360 (3)	C14—C15	1.383 (3)
C5—C6	1.407 (3)	C14—H14	0.9500
C6—C10	1.453 (3)	C15—C16	1.393 (3)
C7—H7A	0.9800	C15—H15	0.9500
C7—H7B	0.9800	C16—O4	1.369 (3)
C7—H7C	0.9800	C16—C17	1.381 (3)
O1—C8	1.423 (3)	C17—C18	1.384 (3)
C8—H8A	0.9800	C17—H17	0.9500
C8—H8B	0.9800	C18—H18	0.9500
C8—H8C	0.9800	O4—C19	1.426 (3)
O2—C9	1.422 (3)	C19—H19A	0.9800
C9—H9A	0.9800	C19—H19B	0.9800
C9—H9B	0.9800	C19—H19C	0.9800
C2—C1—C6	120.5 (2)	H9A—C9—H9C	109.5
C2—C1—C11	120.8 (2)	H9B—C9—H9C	109.5
C6—C1—C11	118.6 (2)	O3—C10—C6	128.1 (2)
C1—C2—C3	118.1 (2)	O3—C10—H10	115.9
C1—C2—C7	124.1 (2)	C6—C10—H10	115.9
C3—C2—C7	117.7 (2)	C12—C11—C1	125.6 (2)
O1—C3—C4	122.2 (2)	C12—C11—H11	117.2
O1—C3—C2	115.0 (2)	C1—C11—H11	117.2
C4—C3—C2	122.8 (2)	C11—C12—C13	125.7 (2)
C3—C4—C5	118.7 (2)	C11—C12—H12	117.1
C3—C4—H4	120.7	C13—C12—H12	117.1
C5—C4—H4	120.7	C14—C13—C18	117.3 (2)
O2—C5—C4	122.3 (2)	C14—C13—C12	120.4 (2)
O2—C5—C6	116.7 (2)	C18—C13—C12	122.2 (2)
C4—C5—C6	121.1 (2)	C15—C14—C13	121.7 (2)
C5—C6—C1	118.8 (2)	C15—C14—H14	119.1
C5—C6—C10	117.4 (2)	C13—C14—H14	119.1
C1—C6—C10	123.9 (2)	C14—C15—C16	119.9 (2)
C2—C7—H7A	109.5	C14—C15—H15	120.1
C2—C7—H7B	109.5	C16—C15—H15	120.1
H7A—C7—H7B	109.5	O4—C16—C17	125.3 (2)
C2—C7—H7C	109.5	O4—C16—C15	115.4 (2)
H7A—C7—H7C	109.5	C17—C16—C15	119.3 (2)
H7B—C7—H7C	109.5	C16—C17—C18	120.2 (2)
C3—O1—C8	118.1 (2)	C16—C17—H17	119.9
O1—C8—H8A	109.5	C18—C17—H17	119.9
O1—C8—H8B	109.5	C17—C18—C13	121.5 (2)
H8A—C8—H8B	109.5	C17—C18—H18	119.2
O1—C8—H8C	109.5	C13—C18—H18	119.2
H8A—C8—H8C	109.5	C16—O4—C19	116.92 (19)
H8B—C8—H8C	109.5	O4—C19—H19A	109.5
C5—O2—C9	117.52 (18)	O4—C19—H19B	109.5
O2—C9—H9A	109.5	H19A—C19—H19B	109.5
O2—C9—H9B	109.5	O4—C19—H19C	109.5
H9A—C9—H9B	109.5	H19A—C19—H19C	109.5
O2—C9—H9C	109.5	H19B—C19—H19C	109.5
C6—C1—C2—C3	−0.3 (3)	C4—C5—O2—C9	−2.2 (3)
C11—C1—C2—C3	−179.9 (2)	C6—C5—O2—C9	179.0 (2)
C6—C1—C2—C7	177.8 (2)	C5—C6—C10—O3	175.2 (2)
C11—C1—C2—C7	−1.9 (3)	C1—C6—C10—O3	−4.0 (4)
C1—C2—C3—O1	179.49 (19)	C2—C1—C11—C12	−53.9 (3)
C7—C2—C3—O1	1.3 (3)	C6—C1—C11—C12	126.4 (3)
C1—C2—C3—C4	−0.3 (3)	C1—C11—C12—C13	−175.6 (2)
C7—C2—C3—C4	−178.5 (2)	C11—C12—C13—C14	146.5 (3)
O1—C3—C4—C5	−178.7 (2)	C11—C12—C13—C18	−29.9 (4)
C2—C3—C4—C5	1.0 (3)	C18—C13—C14—C15	2.1 (4)
C3—C4—C5—O2	−179.9 (2)	C12—C13—C14—C15	−174.6 (2)
C3—C4—C5—C6	−1.2 (3)	C13—C14—C15—C16	−1.7 (4)
O2—C5—C6—C1	179.4 (2)	C14—C15—C16—O4	−179.2 (2)
C4—C5—C6—C1	0.7 (3)	C14—C15—C16—C17	−0.3 (4)
O2—C5—C6—C10	0.2 (3)	O4—C16—C17—C18	−179.3 (2)
C4—C5—C6—C10	−178.6 (2)	C15—C16—C17—C18	1.8 (4)
C2—C1—C6—C5	0.1 (3)	C16—C17—C18—C13	−1.4 (4)
C11—C1—C6—C5	179.75 (19)	C14—C13—C18—C17	−0.5 (3)
C2—C1—C6—C10	179.3 (2)	C12—C13—C18—C17	176.1 (2)
C11—C1—C6—C10	−1.0 (3)	C17—C16—O4—C19	−4.1 (3)
C4—C3—O1—C8	−0.2 (3)	C15—C16—O4—C19	174.8 (2)
C2—C3—O1—C8	−180.0 (2)