(E)-1-(2-Hy­droxy-6-meth­oxy­phen­yl)-3-(2,3,4-tri­meth­oxy­phen­yl)prop-2-en-1-one

Lee, J.H.; Koh, D.

doi:10.1107/S2414314619001792

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190179

https://doi.org/10.1107/S2414314619001792

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(E)-1-(2-Hydroxy-6-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

Ji Hye Lee ^a and Dongsoo Koh ^a ^*

^aDepartment 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 23 January 2019; accepted 30 January 2019; online 5 February 2019)

In the title molecule, C₁₉H₂₀O₆, the dihedral angle formed by the benzene rings is 36.71 (2)°. The hydroxy group is involved in a weak intramolecular O—H⋯O hydrogen bond. In the crystal, two weak C—H⋯O hydrogen bonds link the molecules into chains along [001].

Keywords: crystal structure; chalcone; C—H⋯O hydrogen bonds; dihedral angle.

CCDC reference: 1894750

Structure description

Chalcones are secondary metabolites found in plants with a C6–C3–C6 skeleton, a C3 skeleton being an α,β-unsaturated carbonyl (enone). A variety of chalcones have been isolated from natural sources and synthesized because they have shown wide spectrum of biological activities with clinical potentials against various diseases (Zhuang et al., 2017 ). As part of our ongoing work in this area (Shin et al., 2019 ; Lee et al., 2016 ), the crystal structure of the title compound has been determined.

The molecular structure of the title compound is shown in Fig. 1. An intramolecular O5—H5⋯O1 hydrogen bond (Table 1) may cause the C1=O1 double bond [1.257 (5) Å] to be slightly longer than the normal value (Allen et al. 1987 ). The dihedral angle between the benzene rings is 36.71 (2)°. The trans configuration of the C2=C3 double bond is confirmed by the C1—C2=C3—C4 torsion angle of of −177.4 (4)°. The methoxy group on benzene ring A, which has a hydroxyl substituent, is almost coplanar with the ring plane [C17—C18—O6—C19 = −4.3 (5)°]. Of the three methoxy groups attached to benzene ring B, the two methoxy groups at the ortho and meta positions are significantly rotated from the ring plane [C4—C5—O2—C10 = 114.0 (4), C5—C6—O3—C11 = 113.9 (4)°] while the group in the para position is essentially coplanar [C6—C7—O4—C12 = −179.3 (3)°].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1	0.84	1.76	2.502 (3)	147
C19—H19A⋯O1ⁱ	0.98	2.53	3.490 (6)	167
C11—H11A⋯O3ⁱⁱ	0.98	2.55	3.363 (5)	140
Symmetry codes: (i) x, y, z-1; (ii) $[-x+2, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability level.

In the crystal, two weak C—H⋯O hydrogen bonds link the molecules into chains along [001] (Table 1, Fig. 2).

Figure 2
Part of the crystal structure with weak C19—H19A⋯O1ⁱ and C11—H11A⋯Oⁱⁱ hydrogen bonds shown as orange and blue dashed lines, respectively. For clarity only those H atoms involved in hydrogen bonding are shown.

Synthesis and crystallization

To a solution of 2-hydroxy-6-methoxyacetophenone (166 mg, 1 mmol) in 15 ml of anhydrous ethanol was added 2,3,4-trimethoxybenzaldehyde (196 mg, 1 mmol) and the temperature was adjusted to around 276–277 K in an ice-bath. To the cooled reaction mixture was added 1.5 ml of 50% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 24 h. After completion of the reaction (monitored by TLC), this mixture was poured into iced water (40 ml) and was acidified with a 6 N HCl solution until the pH was equal to 2 to produce a solid product. This solid was recrystallized from an ethanol solution to obtain single crystals of the title compound in 38% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₆
M_r	344.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	200
a, b, c (Å)	7.7143 (5), 28.907 (2), 7.5010 (5)
V (Å³)	1672.72 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.18 × 0.09 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area detector
No. of measured, independent and observed [I > 2σ(I)] reflections	11890, 4004, 2199
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.105, 0.95
No. of reflections	4004
No. of parameters	231
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1894750

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001792/lh4043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001792/lh4043Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619001792/lh4043Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(E)-1-(2-Hydroxy-6-methoxyphenyl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₂₀O₆	D_x = 1.367 Mg m⁻³
M_r = 344.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 3178 reflections
a = 7.7143 (5) Å	θ = 2.7–27.3°
b = 28.907 (2) Å	µ = 0.10 mm⁻¹
c = 7.5010 (5) Å	T = 200 K
V = 1672.72 (19) Å³	Block, yellow
Z = 4	0.18 × 0.09 × 0.08 mm
F(000) = 728

Data collection top

Bruker APEXII CCD area detector diffractometer	R_int = 0.053
/f and /w scans	θ_max = 28.3°, θ_min = 2.7°
11890 measured reflections	h = −10→10
4004 independent reflections	k = −38→29
2199 reflections with I > 2σ(I)	l = −10→9

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0334P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
4004 reflections	Δρ_max = 0.18 e Å⁻³
231 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.8643 (4)	0.25927 (8)	0.3218 (4)	0.0524 (7)
C1	0.7768 (5)	0.27219 (13)	0.1895 (6)	0.0411 (9)
C2	0.7215 (5)	0.32059 (13)	0.1845 (5)	0.0418 (10)
H2	0.6322	0.3295	0.1045	0.050*
C3	0.7932 (4)	0.35234 (12)	0.2894 (5)	0.0405 (10)
H3	0.8853	0.3422	0.3638	0.049*
C4	0.7459 (4)	0.40117 (12)	0.3028 (5)	0.0350 (8)
C5	0.8519 (4)	0.43163 (12)	0.3987 (5)	0.0352 (9)
C6	0.8156 (4)	0.47884 (12)	0.4073 (5)	0.0343 (9)
C7	0.6691 (4)	0.49594 (11)	0.3223 (5)	0.0351 (9)
C8	0.5596 (5)	0.46635 (12)	0.2301 (5)	0.0401 (10)
H8	0.4590	0.4780	0.1725	0.048*
C9	0.5984 (5)	0.41971 (12)	0.2229 (5)	0.0411 (10)
H9	0.5218	0.3996	0.1613	0.049*
O2	0.9906 (3)	0.41348 (8)	0.4897 (4)	0.0460 (7)
C10	1.1582 (5)	0.42676 (14)	0.4274 (6)	0.0555 (12)
H10A	1.1545	0.4312	0.2979	0.083*
H10B	1.2422	0.4025	0.4564	0.083*
H10C	1.1930	0.4557	0.4850	0.083*
O3	0.9171 (3)	0.50681 (8)	0.5123 (4)	0.0419 (6)
C11	1.0189 (5)	0.54028 (12)	0.4170 (6)	0.0446 (10)
H11A	1.0929	0.5244	0.3302	0.067*
H11B	1.0915	0.5575	0.5013	0.067*
H11C	0.9418	0.5618	0.3546	0.067*
O4	0.6431 (3)	0.54259 (8)	0.3408 (4)	0.0414 (6)
C12	0.4934 (5)	0.56240 (13)	0.2583 (6)	0.0484 (10)
H12A	0.4955	0.5558	0.1302	0.073*
H12B	0.4936	0.5960	0.2770	0.073*
H12C	0.3886	0.5490	0.3112	0.073*
C13	0.7259 (5)	0.23817 (13)	0.0556 (5)	0.0400 (10)
C14	0.7381 (5)	0.19086 (14)	0.0973 (6)	0.0466 (11)
O5	0.7991 (4)	0.17618 (8)	0.2566 (5)	0.0603 (9)
H5	0.8340	0.1990	0.3160	0.090*
C15	0.6852 (5)	0.15690 (14)	−0.0206 (7)	0.0594 (13)
H15	0.6941	0.1252	0.0111	0.071*
C16	0.6202 (6)	0.16929 (15)	−0.1831 (8)	0.0672 (13)
H16	0.5820	0.1459	−0.2628	0.081*
C17	0.6087 (5)	0.21516 (15)	−0.2341 (6)	0.0584 (12)
H17	0.5643	0.2232	−0.3481	0.070*
C18	0.6626 (5)	0.24917 (14)	−0.1170 (6)	0.0481 (11)
O6	0.6613 (4)	0.29485 (9)	−0.1609 (4)	0.0586 (8)
C19	0.6133 (8)	0.30746 (16)	−0.3385 (7)	0.0826 (17)
H19A	0.6803	0.2890	−0.4238	0.124*
H19B	0.6375	0.3404	−0.3574	0.124*
H19C	0.4894	0.3016	−0.3560	0.124*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0626 (18)	0.0431 (16)	0.0514 (18)	0.0019 (13)	−0.0090 (16)	−0.0047 (15)
C1	0.039 (2)	0.042 (2)	0.042 (2)	−0.0028 (18)	0.006 (2)	−0.006 (2)
C2	0.047 (2)	0.039 (2)	0.040 (2)	0.0012 (18)	0.001 (2)	−0.001 (2)
C3	0.042 (2)	0.037 (2)	0.043 (3)	−0.0040 (17)	0.003 (2)	−0.0014 (19)
C4	0.036 (2)	0.036 (2)	0.033 (2)	−0.0061 (16)	0.0016 (18)	−0.0017 (17)
C5	0.037 (2)	0.041 (2)	0.028 (2)	−0.0014 (17)	−0.0005 (17)	−0.0006 (18)
C6	0.037 (2)	0.036 (2)	0.030 (2)	−0.0041 (16)	−0.0009 (18)	−0.0071 (18)
C7	0.038 (2)	0.035 (2)	0.032 (2)	−0.0035 (16)	0.0050 (19)	−0.0024 (19)
C8	0.036 (2)	0.046 (2)	0.038 (2)	−0.0007 (18)	−0.0035 (19)	0.001 (2)
C9	0.038 (2)	0.042 (2)	0.043 (3)	−0.0083 (17)	0.002 (2)	−0.0042 (19)
O2	0.0443 (16)	0.0426 (16)	0.0510 (17)	−0.0010 (12)	−0.0114 (15)	0.0046 (14)
C10	0.042 (2)	0.068 (3)	0.056 (3)	0.007 (2)	−0.005 (2)	−0.005 (2)
O3	0.0495 (15)	0.0412 (15)	0.0350 (16)	−0.0090 (13)	−0.0047 (13)	−0.0037 (13)
C11	0.048 (2)	0.037 (2)	0.049 (3)	−0.0103 (18)	−0.001 (2)	0.002 (2)
O4	0.0450 (15)	0.0356 (14)	0.0435 (16)	0.0039 (11)	−0.0025 (14)	−0.0022 (13)
C12	0.047 (2)	0.049 (2)	0.049 (3)	0.010 (2)	−0.004 (2)	0.001 (2)
C13	0.040 (2)	0.037 (2)	0.044 (3)	−0.0010 (17)	0.0049 (19)	−0.003 (2)
C14	0.047 (3)	0.042 (3)	0.051 (3)	−0.003 (2)	0.002 (2)	−0.006 (2)
O5	0.070 (2)	0.0420 (17)	0.069 (2)	−0.0001 (15)	−0.0086 (18)	0.0004 (17)
C15	0.066 (3)	0.035 (2)	0.077 (4)	−0.005 (2)	−0.003 (3)	−0.010 (3)
C16	0.079 (3)	0.047 (3)	0.076 (4)	−0.007 (2)	−0.007 (3)	−0.022 (3)
C17	0.072 (3)	0.058 (3)	0.046 (3)	−0.002 (2)	−0.005 (2)	−0.016 (2)
C18	0.052 (3)	0.042 (2)	0.050 (3)	0.001 (2)	0.011 (2)	−0.004 (2)
O6	0.088 (2)	0.0452 (18)	0.0424 (18)	0.0033 (15)	0.0042 (18)	−0.0045 (15)
C19	0.148 (5)	0.067 (3)	0.033 (3)	0.025 (3)	0.003 (3)	0.010 (3)

Geometric parameters (Å, º) top

O1—O1	0.000 (8)	O3—C11	1.437 (4)
O1—C1	1.257 (5)	C11—H11A	0.9800
C1—O1	1.257 (5)	C11—H11B	0.9800
C1—C13	1.460 (5)	C11—H11C	0.9800
C1—C2	1.463 (5)	O4—C12	1.430 (4)
C2—C3	1.329 (5)	C12—H12A	0.9800
C2—H2	0.9500	C12—H12B	0.9800
C3—C4	1.462 (5)	C12—H12C	0.9800
C3—H3	0.9500	C13—C14	1.406 (5)
C4—C9	1.393 (5)	C13—C18	1.420 (6)
C4—C5	1.401 (5)	C14—O5	1.353 (5)
C5—O2	1.373 (4)	C14—C15	1.383 (5)
C5—C6	1.395 (5)	O5—H5	0.8400
C6—O3	1.374 (4)	C15—C16	1.366 (6)
C6—C7	1.388 (5)	C15—H15	0.9500
C7—O4	1.370 (4)	C16—C17	1.383 (6)
C7—C8	1.387 (5)	C16—H16	0.9500
C8—C9	1.382 (4)	C17—C18	1.382 (5)
C8—H8	0.9500	C17—H17	0.9500
C9—H9	0.9500	C18—O6	1.361 (5)
O2—C10	1.428 (4)	O6—C19	1.430 (5)
C10—H10A	0.9800	C19—H19A	0.9800
C10—H10B	0.9800	C19—H19B	0.9800
C10—H10C	0.9800	C19—H19C	0.9800

O1—C1—C13	119.2 (4)	O3—C11—H11B	109.5
O1—C1—C13	119.2 (4)	H11A—C11—H11B	109.5
O1—C1—C2	117.4 (4)	O3—C11—H11C	109.5
O1—C1—C2	117.4 (4)	H11A—C11—H11C	109.5
C13—C1—C2	123.2 (4)	H11B—C11—H11C	109.5
C3—C2—C1	121.6 (4)	C7—O4—C12	117.9 (3)
C3—C2—H2	119.2	O4—C12—H12A	109.5
C1—C2—H2	119.2	O4—C12—H12B	109.5
C2—C3—C4	127.1 (4)	H12A—C12—H12B	109.5
C2—C3—H3	116.4	O4—C12—H12C	109.5
C4—C3—H3	116.4	H12A—C12—H12C	109.5
C9—C4—C5	117.1 (3)	H12B—C12—H12C	109.5
C9—C4—C3	123.1 (3)	C14—C13—C18	116.4 (4)
C5—C4—C3	119.8 (3)	C14—C13—C1	118.9 (4)
O2—C5—C6	120.5 (3)	C18—C13—C1	124.7 (4)
O2—C5—C4	118.0 (3)	O5—C14—C15	116.4 (4)
C6—C5—C4	121.4 (3)	O5—C14—C13	121.7 (4)
O3—C6—C7	121.2 (3)	C15—C14—C13	121.9 (4)
O3—C6—C5	119.2 (3)	C14—O5—H5	109.5
C7—C6—C5	119.4 (3)	C16—C15—C14	119.5 (4)
O4—C7—C8	124.6 (3)	C16—C15—H15	120.2
O4—C7—C6	115.0 (3)	C14—C15—H15	120.2
C8—C7—C6	120.3 (3)	C15—C16—C17	121.4 (4)
C9—C8—C7	119.3 (3)	C15—C16—H16	119.3
C9—C8—H8	120.4	C17—C16—H16	119.3
C7—C8—H8	120.4	C18—C17—C16	119.1 (4)
C8—C9—C4	122.4 (3)	C18—C17—H17	120.4
C8—C9—H9	118.8	C16—C17—H17	120.4
C4—C9—H9	118.8	O6—C18—C17	122.3 (4)
C5—O2—C10	116.1 (3)	O6—C18—C13	116.1 (4)
O2—C10—H10A	109.5	C17—C18—C13	121.6 (4)
O2—C10—H10B	109.5	C18—O6—C19	118.3 (3)
H10A—C10—H10B	109.5	O6—C19—H19A	109.5
O2—C10—H10C	109.5	O6—C19—H19B	109.5
H10A—C10—H10C	109.5	H19A—C19—H19B	109.5
H10B—C10—H10C	109.5	O6—C19—H19C	109.5
C6—O3—C11	115.0 (3)	H19A—C19—H19C	109.5
O3—C11—H11A	109.5	H19B—C19—H19C	109.5

O1—O1—C1—C13	0.0 (4)	C7—C6—O3—C11	−71.8 (4)
O1—O1—C1—C2	0.0 (6)	C5—C6—O3—C11	113.9 (4)
O1—C1—C2—C3	16.0 (6)	C8—C7—O4—C12	−0.5 (5)
O1—C1—C2—C3	16.0 (6)	C6—C7—O4—C12	−179.3 (3)
C13—C1—C2—C3	−168.1 (3)	O1—C1—C13—C14	15.3 (5)
C1—C2—C3—C4	−177.4 (4)	O1—C1—C13—C14	15.3 (5)
C2—C3—C4—C9	9.7 (6)	C2—C1—C13—C14	−160.5 (4)
C2—C3—C4—C5	−169.9 (4)	O1—C1—C13—C18	−165.1 (4)
C9—C4—C5—O2	175.1 (3)	O1—C1—C13—C18	−165.1 (4)
C3—C4—C5—O2	−5.2 (5)	C2—C1—C13—C18	19.1 (6)
C9—C4—C5—C6	−2.8 (5)	C18—C13—C14—O5	178.9 (4)
C3—C4—C5—C6	176.9 (3)	C1—C13—C14—O5	−1.4 (6)
O2—C5—C6—O3	−2.0 (5)	C18—C13—C14—C15	−2.4 (6)
C4—C5—C6—O3	175.9 (3)	C1—C13—C14—C15	177.3 (4)
O2—C5—C6—C7	−176.4 (3)	O5—C14—C15—C16	179.2 (4)
C4—C5—C6—C7	1.4 (5)	C13—C14—C15—C16	0.4 (6)
O3—C6—C7—O4	4.7 (5)	C14—C15—C16—C17	1.2 (7)
C5—C6—C7—O4	179.0 (3)	C15—C16—C17—C18	−0.7 (7)
O3—C6—C7—C8	−174.1 (3)	C16—C17—C18—O6	177.4 (4)
C5—C6—C7—C8	0.2 (5)	C16—C17—C18—C13	−1.4 (6)
O4—C7—C8—C9	−179.1 (3)	C14—C13—C18—O6	−176.0 (3)
C6—C7—C8—C9	−0.4 (5)	C1—C13—C18—O6	4.4 (6)
C7—C8—C9—C4	−1.1 (6)	C14—C13—C18—C17	2.9 (6)
C5—C4—C9—C8	2.6 (5)	C1—C13—C18—C17	−176.8 (4)
C3—C4—C9—C8	−177.0 (4)	C17—C18—O6—C19	−4.3 (6)
C6—C5—O2—C10	−68.1 (4)	C13—C18—O6—C19	174.6 (4)
C4—C5—O2—C10	114.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O1ⁱ	0.98	2.53	3.490 (6)	167
C11—H11A···O3ⁱⁱ	0.98	2.55	3.363 (5)	140
O5—H5···O1	0.84	1.76	2.502 (3)	147

Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y+1, z−1/2.

Funding information

The authors acknowledge financial support from the Basic Science Research Program (award No. NRF– 2016R1D1A1B03931623).

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