Crystal structure of (E)-4,6-dimeth­oxy-2-(4-meth­oxy­styr­yl)-3-methyl­benzaldehyde

Ahn, S.; Lim, Y.; Koh, D.

doi:10.1107/S2056989015017363

organic compounds

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Volume 71| Part 10| October 2015| Page o771

doi:10.1107/S2056989015017363

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Crystal structure of (E)-4,6-dimethoxy-2-(4-methoxystyryl)-3-methylbenzaldehyde

Seunghyun Ahn,^a Yoongho Lim ^a and Dongsoo Koh ^b ^*

^aDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea, and ^bDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by A. J. Lough, University of Toronto, Canada (Received 6 September 2015; accepted 17 September 2015; online 26 September 2015)

In the title molecule, 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 methoxy 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)°.

Keywords: crystal structure; benzaldehyde; resveratrol derivatives; biological properties.

CCDC reference: 1425329

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₉H₂₀O₄
M_r = 312.35
Monoclinic, P 2₁ /c
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

2.2. Data collection

Bruker SMART CCD diffractometer
11266 measured reflections
3904 independent reflections
1966 reflections with I > 2σ(I)
R_int = 0.037

2.3. Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.222
S = 0.99
3904 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −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.

Supporting information

CCDC reference: 1425329

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015017363/lh5786sup1.cif

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

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

checkCIF report

Introduction top

Resveratrol is part of a family of the stilbene polyphenols which has a general C6—C2—C6 carbon framework. Recent research has shown that resveratrol derivatives have diverse biological activities including anti-Alzheimer's disease (Li et al., 2014), anticancer (Chillemi et al., 2015), and anti-inflammatory (Chen et al., 2015). On our going research project of polyphenols (Shin et al., 2014), the title compound was synthesized and its crystal structure was determined.

After the methylation of hydroxyl groups in resveratrol, formylation of the resulting compound was performed (Fig 2). The Vilslmeier formylation reaction gave two products depending on reaction conditions (Huang et al., 2007). The title compound (I) contains one formyl group and one methyl group at each ortho position of the dimethoxy-substituted benzene ring. Whereas compound (II) has only a formyl group at the ortho position of the benzene ring. The crystal structure of compound (II) has been published recently (Ge et al. 2013). In this report, the title compound (I) was synthesized and its crystal structure was determined. According to the literature (Ge et al. 2013), compound (II) contains two independent molecules in the asymmetric unit and the dihedral angle between the two benzene rings in each are 23.54 (12)°, and 31.11 (12)°. However, in (I), dihedral angle between the two benzene rings is 83.57 (12)° (Fig. 1). The methoxy groups are essentially co-planar with the attached the benzene rings [C4—C3—O1—C8 = -0.2 (3)°, C4—C5—O2—C9 = -2.3 (3)° and C17—C16—O4—C19 = -4.1 (3)°].

Experimental top

For an outline of the synthesis see Fig. 2. Resveratrol (A, 30 mmol, 6.8 g) was dissolved in 75 mL of aq. NaOH (10%) under ice-water bath conditions. To the above solution, was added DMS (50 mL) and the reaction mixture was stirred at room temperature for 24 h. After completion of this reaction, the mixture was extracted with EtOAc (50 mL x 3) and the combined organic layer was dried under MgSO₄. Filtration and evaporation of the solvent gave a solid of compound B. To a solution of compound B (10 mmol, 2.7 g) in 20 mL of DMF was added 2 mL of POCl₃ in an ice-water bath, and was stirred at room temperature for 4 h. The reaction mixture was poured into ice-water and stirred for 2 h. The reaction mixture was extracted with EtOAc (30 mL x 3). Evaporation of the organic solvent afforded mixture of products (I) and (II), which was purified by column chromatography. Recrystallization of solid (I) from ethanol gave single crystals which were suitable for X-ray diffraction (m.p.: 391–392 K).

Refinement top

H atoms bonded to C atoms were placed in calculated positions, with C—H distances in the range 0.95–0.98 Å, and included in the refinement in a riding-model approximation, with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.5U_eq(C) otherwise.

Results and discussion top

Related literature top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Synthetic scheme for preparation of resveratrol derivative compounds.

(E)-4,6-Dimethoxy-2-(4-methoxystyryl)-3-methylbenzaldehyde top

Crystal data top

C₁₉H₂₀O₄	F(000) = 664
M_r = 312.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1179P)²] where P = (F_o² + 2F_c²)/3
3904 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₉H₂₀O₄	V = 1573.5 (2) Å³
M_r = 312.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.3632 (9) Å	µ = 0.09 mm⁻¹
b = 8.7159 (7) Å	T = 200 K
c = 16.2382 (13) Å	0.26 × 0.20 × 0.13 mm
β = 101.927 (2)°

Data collection top

Bruker SMART CCD diffractometer	1966 reflections with I > 2σ(I)
11266 measured reflections	R_int = 0.037
3904 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.222	H-atom parameters constrained
S = 0.99	Δρ_max = 0.24 e Å⁻³
3904 reflections	Δρ_min = −0.31 e Å⁻³
212 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₄
M_r	312.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	11.3632 (9), 8.7159 (7), 16.2382 (13)
β (°)	101.927 (2)
V (Å³)	1573.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11266, 3904, 1966
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.222, 0.99
No. of reflections	3904
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.31

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, W., Ge, X., Xu, F., Zhang, Y., Liu, Z., Pan, J., Song, J., Dai, Y., Zhou, J., Feng, J. & Liang, G. (2015). Bioorg. Med. Chem. Lett. 25, 2998–3004. CrossRef CAS PubMed Google Scholar
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Ge, X.-L., Guan, Q.-X., Deng, S.-S. & Ruan, B.-F. (2013). Acta Cryst. E69, o629. CSD CrossRef IUCr Journals Google Scholar
Huang, X.-F., Ruan, B.-F., Wang, X.-T., Xu, C., Ge, H.-M., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 263–267. Web of Science CrossRef PubMed CAS Google Scholar
Li, S.-Y., Wang, X.-B. & Kong, L.-Y. (2014). Eur. J. Med. Chem. 71, 36–45. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shin, S. Y., Lee, J. M., Lee, M. S., Koh, D., Jung, H., Lim, Y. & Lee, Y. H. (2014). Clin. Cancer Res. 20, 4302–4313. CrossRef CAS PubMed Google Scholar
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Volume 71| Part 10| October 2015| Page o771

doi:10.1107/S2056989015017363

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-4,6-dimeth­­oxy-2-(4-meth­­oxy­styr­yl)-3-methyl­benzaldehyde

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

References

organic compounds

Crystal structure of (E)-4,6-dimethoxy-2-(4-methoxystyryl)-3-methylbenzaldehyde