organic compounds
(E)-3-(2,3-Dimethoxyphenyl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one
aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dskoh@dongduk.ac.kr
In the title chalcone derivative, C18H18O5, the dihedral angle formed by the planes of the benzene rings is 29.6 (2)° and an intramolecular O—H⋯O hydrogen bond closes an S(6) ring. In the crystal, weak C—H⋯O hydrogen bonds link molecules into chains propagating along [001].
Keywords: crystal structure; chalcone; prop-2-en-1-one; hydrogen bonding.
CCDC reference: 1505582
Structure description
α,β-unsaturated carbonyl (enone) compounds that connect two aromatic components. They are one of the found in plants with a C6—C3—C6 skeleton. In this chalcone, the C3 skeleton is an open chain but in other metabolites such as flavones, the C3 skeleton is a closed chain. A variety of have been isolated from natural sources and synthesized due to their wide spectrum of biological activities (Singh et al., 2014). In a continuation of research to develop new that show a broad range of biological activities (Jung et al., 2015), the of title compound (Fig. 1) has been determined. The structure of a related substituted chalcone compound was reported by Srividya et al. (2015).
areThe trans conformation of the C9=C10 double bond in the central enone group is confirmed by the C1—C9=C10—C11 torsion angle of 173.37 (17)°. The dihedral angle between the planes of the benzene rings is 29.6 (2)°. The C1=O1 double bond [1.239 (2) Å] is longer than the normal value as this group accepts an intramolecular hydrogen bond from the hydroxy group, thereby forming an S(6) ring (Table 1). Among the three methoxy groups attached to the benzene rings, the two groups at meta positions to the central enone group are tilted slightly [C5—C6—O3—C8 = −1.2 (3)° and C14—C13—O5—C18 = −7.5 (2)°] from their attached ring. However, the C atom of the group at the ortho position is orthogonal to the benzene ring [C13—C12—O4—C17 = 90.7 (2)°].
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In the crystal, weak C—H⋯O hydrogen bonds link molecules into chains propagating along [001] (Fig. 2).
Synthesis and crystallization
To a solution of 2,3-dimethoxybenzaldehyde (392 mg, 2 mmol) in 20 ml of anhydrous ethanol was added 2-hydroxy-5-methoxyacetophenone (332 mg, 2 mmol) and the temperature was adjusted to around 276–277 K in an ice bath. To the cooled reaction mixture was added 2 ml of 50% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 27 h. This mixture was poured into iced water (80 ml) and was acidified with 4 N HCl solution to give a precipitate. Filtration and washing with water afforded the crude solid of the title compound (yield 270 mg, 72%). Recrystallization of the solid from ethanol solution gave orange blocks (m.p. 370–371 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1505582
https://doi.org/10.1107/S2414314616014929/hb4081sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616014929/hb4081Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616014929/hb4081Isup3.cml
Data collection: APEX2 (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C18H18O5 | F(000) = 664 |
Mr = 314.32 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9647 reflections |
a = 4.6056 (3) Å | θ = 2.2–24.1° |
b = 24.7911 (13) Å | µ = 0.10 mm−1 |
c = 13.7523 (7) Å | T = 223 K |
β = 98.751 (3)° | Block, orange |
V = 1551.93 (15) Å3 | 0.15 × 0.12 × 0.07 mm |
Z = 4 |
Bruker PHOTON 100 CMOS diffractometer | 3870 independent reflections |
Radiation source: fine-focus sealed tube | 2340 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
φ and ω scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −6→6 |
Tmin = 0.985, Tmax = 0.993 | k = −33→33 |
68518 measured reflections | l = −18→18 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0465P)2 + 0.4891P] where P = (Fo2 + 2Fc2)/3 |
3870 reflections | (Δ/σ)max = 0.001 |
212 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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. |
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 > 2sigma(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 | 0.7490 (4) | 0.69540 (7) | 0.89539 (13) | 0.0489 (5) | |
O1 | 0.8227 (4) | 0.72888 (5) | 0.83684 (10) | 0.0707 (4) | |
C2 | 0.5807 (4) | 0.71236 (7) | 0.97281 (13) | 0.0463 (4) | |
C3 | 0.5374 (4) | 0.76761 (7) | 0.98920 (15) | 0.0547 (5) | |
O2 | 0.6399 (4) | 0.80615 (5) | 0.93304 (12) | 0.0727 (4) | |
H2 | 0.7084 | 0.7916 | 0.8871 | 0.109* | |
C4 | 0.3920 (5) | 0.78349 (8) | 1.06494 (18) | 0.0655 (6) | |
H4 | 0.3710 | 0.8205 | 1.0772 | 0.079* | |
C5 | 0.2771 (4) | 0.74642 (9) | 1.12297 (16) | 0.0628 (6) | |
H5 | 0.1766 | 0.7581 | 1.1737 | 0.075* | |
C6 | 0.3100 (4) | 0.69169 (8) | 1.10626 (15) | 0.0538 (5) | |
C7 | 0.4625 (4) | 0.67553 (7) | 1.03285 (13) | 0.0490 (5) | |
H7 | 0.4881 | 0.6384 | 1.0227 | 0.059* | |
O3 | 0.1997 (3) | 0.65114 (6) | 1.15815 (11) | 0.0715 (4) | |
C8 | 0.0446 (5) | 0.66650 (10) | 1.23604 (16) | 0.0731 (6) | |
H8A | 0.1769 | 0.6853 | 1.2865 | 0.110* | |
H8B | −0.0316 | 0.6345 | 1.2641 | 0.110* | |
H8C | −0.1170 | 0.6901 | 1.2105 | 0.110* | |
C9 | 0.8415 (4) | 0.63896 (7) | 0.88882 (13) | 0.0483 (4) | |
H9 | 0.7940 | 0.6139 | 0.9353 | 0.058* | |
C10 | 0.9897 (4) | 0.62256 (7) | 0.81934 (13) | 0.0459 (4) | |
H10 | 1.0146 | 0.6478 | 0.7703 | 0.055* | |
C11 | 1.1186 (4) | 0.56948 (6) | 0.81078 (12) | 0.0418 (4) | |
C12 | 1.2194 (4) | 0.55511 (6) | 0.72359 (12) | 0.0390 (4) | |
C13 | 1.3518 (4) | 0.50506 (6) | 0.71390 (12) | 0.0400 (4) | |
C14 | 1.3921 (4) | 0.46977 (7) | 0.79275 (13) | 0.0493 (4) | |
H14 | 1.4852 | 0.4364 | 0.7876 | 0.059* | |
C15 | 1.2936 (5) | 0.48418 (7) | 0.87926 (14) | 0.0572 (5) | |
H15 | 1.3200 | 0.4601 | 0.9327 | 0.069* | |
C16 | 1.1587 (5) | 0.53265 (8) | 0.88889 (14) | 0.0541 (5) | |
H16 | 1.0925 | 0.5413 | 0.9484 | 0.065* | |
O4 | 1.1979 (3) | 0.59122 (4) | 0.64707 (8) | 0.0437 (3) | |
C17 | 0.9323 (4) | 0.58633 (8) | 0.57896 (13) | 0.0519 (5) | |
H17A | 0.9226 | 0.5508 | 0.5493 | 0.078* | |
H17B | 0.9287 | 0.6135 | 0.5281 | 0.078* | |
H17C | 0.7653 | 0.5914 | 0.6133 | 0.078* | |
O5 | 1.4313 (3) | 0.49495 (5) | 0.62408 (9) | 0.0483 (3) | |
C18 | 1.5974 (4) | 0.44727 (7) | 0.61420 (15) | 0.0557 (5) | |
H18A | 1.7771 | 0.4482 | 0.6612 | 0.084* | |
H18B | 1.6454 | 0.4453 | 0.5480 | 0.084* | |
H18C | 1.4826 | 0.4159 | 0.6266 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0567 (11) | 0.0368 (9) | 0.0496 (11) | −0.0016 (8) | −0.0031 (9) | −0.0031 (8) |
O1 | 0.1060 (12) | 0.0399 (7) | 0.0672 (9) | 0.0002 (7) | 0.0168 (9) | 0.0057 (7) |
C2 | 0.0452 (10) | 0.0341 (9) | 0.0543 (11) | 0.0057 (8) | −0.0088 (8) | −0.0076 (8) |
C3 | 0.0497 (11) | 0.0340 (9) | 0.0739 (13) | 0.0046 (8) | −0.0110 (10) | −0.0083 (9) |
O2 | 0.0829 (11) | 0.0346 (7) | 0.0973 (12) | 0.0037 (7) | 0.0032 (9) | −0.0026 (7) |
C4 | 0.0552 (12) | 0.0403 (11) | 0.0957 (16) | 0.0130 (9) | −0.0056 (12) | −0.0230 (11) |
C5 | 0.0513 (12) | 0.0574 (12) | 0.0766 (14) | 0.0148 (10) | 0.0001 (10) | −0.0231 (11) |
C6 | 0.0468 (11) | 0.0481 (10) | 0.0635 (12) | 0.0122 (9) | −0.0009 (9) | −0.0082 (9) |
C7 | 0.0507 (11) | 0.0362 (9) | 0.0571 (11) | 0.0109 (8) | −0.0009 (9) | −0.0098 (8) |
O3 | 0.0770 (10) | 0.0630 (9) | 0.0802 (11) | 0.0197 (8) | 0.0303 (8) | −0.0026 (8) |
C8 | 0.0602 (13) | 0.0933 (17) | 0.0670 (14) | 0.0187 (12) | 0.0140 (11) | −0.0105 (12) |
C9 | 0.0577 (11) | 0.0348 (9) | 0.0524 (11) | −0.0001 (8) | 0.0084 (9) | 0.0014 (8) |
C10 | 0.0587 (11) | 0.0355 (9) | 0.0427 (10) | −0.0030 (8) | 0.0050 (8) | 0.0007 (7) |
C11 | 0.0469 (10) | 0.0359 (8) | 0.0419 (9) | −0.0021 (7) | 0.0047 (7) | 0.0024 (7) |
C12 | 0.0413 (9) | 0.0348 (8) | 0.0401 (9) | −0.0066 (7) | 0.0034 (7) | 0.0050 (7) |
C13 | 0.0420 (9) | 0.0360 (9) | 0.0422 (9) | −0.0046 (7) | 0.0068 (7) | 0.0007 (7) |
C14 | 0.0580 (11) | 0.0399 (9) | 0.0498 (11) | 0.0061 (8) | 0.0070 (9) | 0.0059 (8) |
C15 | 0.0801 (14) | 0.0472 (11) | 0.0450 (11) | 0.0117 (10) | 0.0120 (10) | 0.0145 (9) |
C16 | 0.0717 (13) | 0.0512 (11) | 0.0414 (10) | 0.0073 (10) | 0.0146 (9) | 0.0058 (8) |
O4 | 0.0487 (7) | 0.0368 (6) | 0.0453 (7) | −0.0061 (5) | 0.0065 (5) | 0.0096 (5) |
C17 | 0.0515 (11) | 0.0540 (11) | 0.0491 (11) | 0.0026 (9) | 0.0034 (9) | 0.0118 (9) |
O5 | 0.0586 (8) | 0.0430 (7) | 0.0455 (7) | 0.0042 (6) | 0.0150 (6) | 0.0017 (5) |
C18 | 0.0568 (12) | 0.0503 (11) | 0.0611 (12) | 0.0078 (9) | 0.0122 (10) | −0.0054 (9) |
C1—O1 | 1.239 (2) | C10—C11 | 1.456 (2) |
C1—O1 | 1.239 (2) | C10—H10 | 0.9400 |
C1—C9 | 1.470 (2) | C11—C12 | 1.396 (2) |
C1—C2 | 1.470 (3) | C11—C16 | 1.401 (2) |
C2—C7 | 1.396 (3) | C12—O4 | 1.3735 (18) |
C2—C3 | 1.407 (2) | C12—C13 | 1.398 (2) |
C3—O2 | 1.358 (2) | C13—O5 | 1.3638 (19) |
C3—C4 | 1.378 (3) | C13—C14 | 1.384 (2) |
O2—H2 | 0.8300 | C14—C15 | 1.383 (3) |
C4—C5 | 1.375 (3) | C14—H14 | 0.9400 |
C4—H4 | 0.9400 | C15—C16 | 1.368 (3) |
C5—C6 | 1.388 (3) | C15—H15 | 0.9400 |
C5—H5 | 0.9400 | C16—H16 | 0.9400 |
C6—O3 | 1.374 (2) | O4—C17 | 1.428 (2) |
C6—C7 | 1.374 (3) | C17—H17A | 0.9700 |
C7—H7 | 0.9400 | C17—H17B | 0.9700 |
O3—C8 | 1.427 (2) | C17—H17C | 0.9700 |
C8—H8A | 0.9700 | O5—C18 | 1.426 (2) |
C8—H8B | 0.9700 | C18—H18A | 0.9700 |
C8—H8C | 0.9700 | C18—H18B | 0.9700 |
C9—C10 | 1.320 (2) | C18—H18C | 0.9700 |
C9—H9 | 0.9400 | ||
O1—C1—C9 | 119.15 (18) | C9—C10—H10 | 116.6 |
O1—C1—C9 | 119.15 (18) | C11—C10—H10 | 116.6 |
O1—C1—C2 | 120.38 (16) | C12—C11—C16 | 118.04 (16) |
O1—C1—C2 | 120.38 (16) | C12—C11—C10 | 119.54 (15) |
C9—C1—C2 | 120.43 (16) | C16—C11—C10 | 122.35 (16) |
C7—C2—C3 | 117.66 (18) | O4—C12—C11 | 119.81 (14) |
C7—C2—C1 | 122.50 (15) | O4—C12—C13 | 119.15 (14) |
C3—C2—C1 | 119.83 (18) | C11—C12—C13 | 121.01 (15) |
O2—C3—C4 | 118.67 (17) | O5—C13—C14 | 124.84 (15) |
O2—C3—C2 | 121.58 (19) | O5—C13—C12 | 115.50 (14) |
C4—C3—C2 | 119.7 (2) | C14—C13—C12 | 119.67 (16) |
C3—O2—H2 | 109.5 | C15—C14—C13 | 119.24 (16) |
C5—C4—C3 | 121.45 (18) | C15—C14—H14 | 120.4 |
C5—C4—H4 | 119.3 | C13—C14—H14 | 120.4 |
C3—C4—H4 | 119.3 | C16—C15—C14 | 121.55 (17) |
C4—C5—C6 | 119.7 (2) | C16—C15—H15 | 119.2 |
C4—C5—H5 | 120.1 | C14—C15—H15 | 119.2 |
C6—C5—H5 | 120.1 | C15—C16—C11 | 120.47 (17) |
O3—C6—C7 | 116.04 (16) | C15—C16—H16 | 119.8 |
O3—C6—C5 | 124.80 (19) | C11—C16—H16 | 119.8 |
C7—C6—C5 | 119.2 (2) | C12—O4—C17 | 113.69 (13) |
C6—C7—C2 | 122.20 (17) | O4—C17—H17A | 109.5 |
C6—C7—H7 | 118.9 | O4—C17—H17B | 109.5 |
C2—C7—H7 | 118.9 | H17A—C17—H17B | 109.5 |
C6—O3—C8 | 117.49 (17) | O4—C17—H17C | 109.5 |
O3—C8—H8A | 109.5 | H17A—C17—H17C | 109.5 |
O3—C8—H8B | 109.5 | H17B—C17—H17C | 109.5 |
H8A—C8—H8B | 109.5 | C13—O5—C18 | 117.41 (13) |
O3—C8—H8C | 109.5 | O5—C18—H18A | 109.5 |
H8A—C8—H8C | 109.5 | O5—C18—H18B | 109.5 |
H8B—C8—H8C | 109.5 | H18A—C18—H18B | 109.5 |
C10—C9—C1 | 121.63 (17) | O5—C18—H18C | 109.5 |
C10—C9—H9 | 119.2 | H18A—C18—H18C | 109.5 |
C1—C9—H9 | 119.2 | H18B—C18—H18C | 109.5 |
C9—C10—C11 | 126.80 (17) | ||
C9—C1—O1—O1 | 0.0 (7) | O1—C1—C9—C10 | −3.1 (3) |
C2—C1—O1—O1 | 0.0 (7) | C2—C1—C9—C10 | 179.19 (17) |
O1—C1—C2—C7 | 172.15 (17) | C1—C9—C10—C11 | 173.37 (17) |
O1—C1—C2—C7 | 172.15 (17) | C9—C10—C11—C12 | 167.80 (18) |
C9—C1—C2—C7 | −10.2 (3) | C9—C10—C11—C16 | −15.2 (3) |
O1—C1—C2—C3 | −8.7 (3) | C16—C11—C12—O4 | −176.65 (16) |
O1—C1—C2—C3 | −8.7 (3) | C10—C11—C12—O4 | 0.4 (2) |
C9—C1—C2—C3 | 168.97 (16) | C16—C11—C12—C13 | 1.1 (3) |
C7—C2—C3—O2 | −178.73 (16) | C10—C11—C12—C13 | 178.18 (16) |
C1—C2—C3—O2 | 2.0 (3) | O4—C12—C13—O5 | −4.5 (2) |
C7—C2—C3—C4 | 2.4 (3) | C11—C12—C13—O5 | 177.70 (15) |
C1—C2—C3—C4 | −176.83 (17) | O4—C12—C13—C14 | 175.79 (15) |
O2—C3—C4—C5 | 178.46 (19) | C11—C12—C13—C14 | −2.0 (3) |
C2—C3—C4—C5 | −2.6 (3) | O5—C13—C14—C15 | −178.06 (17) |
C3—C4—C5—C6 | 0.8 (3) | C12—C13—C14—C15 | 1.6 (3) |
C4—C5—C6—O3 | −178.65 (19) | C13—C14—C15—C16 | −0.3 (3) |
C4—C5—C6—C7 | 1.2 (3) | C14—C15—C16—C11 | −0.5 (3) |
O3—C6—C7—C2 | 178.49 (16) | C12—C11—C16—C15 | 0.2 (3) |
C5—C6—C7—C2 | −1.4 (3) | C10—C11—C16—C15 | −176.85 (19) |
C3—C2—C7—C6 | −0.4 (3) | C11—C12—O4—C17 | −91.57 (18) |
C1—C2—C7—C6 | 178.80 (17) | C13—C12—O4—C17 | 90.65 (19) |
C7—C6—O3—C8 | 178.92 (17) | C14—C13—O5—C18 | −7.5 (2) |
C5—C6—O3—C8 | −1.2 (3) | C12—C13—O5—C18 | 172.89 (15) |
O1—C1—C9—C10 | −3.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.83 | 1.81 | 2.543 (2) | 146 |
C4—H4···O4i | 0.94 | 2.57 | 3.468 (2) | 161 |
Symmetry code: (i) x−1, −y+3/2, z+1/2. |
Acknowledgements
This work was supported by a Dongduk Women's University grant.
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