organic compounds
(E)-3-{4,6-Dimethoxy-2-[(E)-4-methoxystyryl]-3-methylphenyl}-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 compound, C28H28O6, the benzene rings in the resveratrol moiety are connected by a trans C=C double bond, and the hydroxyl group containing a benzene ring and the central benzene ring are linked through a C=(O)—C=C (enone) moiety to form a chalcone unit. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, pairs of C—H⋯O hydrogen bonds generate dimers and additional weak C—H⋯O interactions link the dimers into chains propagating along the b-axis direction.
Keywords: crystal structure; chalcone; resveratrol; C—H⋯O hydrogen bonds.
CCDC reference: 2009305
Structure description
Resveratrol is a secondary metabolite of plants. It has been shown to have phytoalexin abilities, which can be considered to be a self-defense system in the plants to protect from pathogen infections (Timperio et al., 2012). which are another essential of plants, have been shown to possess diverse biological activities in our previous studies (Gil et al., 2018; Lee et al., 2016). The title compound, (I), was designed to combine the chalcone and resveratrol units in order to explore its biological activities (Zhuang et al., 2017).
The molecular structure of (I) is shown in Fig. 1. The benzene ring (C1–C6) in the centre of the molecule participates in chalcone formation through the –C7=C8—C9=(O1)– (enone) linkage and participates in the resveratrol unit through the C16=C17 double bond. In the resveratrol unit, the dihedral angle between the central benzene ring (C1–C6) and the C18–C23 benzene ring is 84.8 (2)°, which indicates that the rings are almost orthogonal to each other. On the other hand, in the chalcone unit, the dihedral angle formed by the central benzene ring and the C15–C15 benzene ring is 9.34 (1)°, which make the two rings close to coplanar. There are four methoxy groups attached to carbon atoms C2, C4, C14 and C21 of the benzene rings in (I). The C26 atom of the methoxy group at C2 is almost co-planar with the benzene ring [C3—C4—O4—C26 = 0.8 (3)°], whereas atoms C25, C27 and C28 of the methoxy groups at C2, C14 and C21, respectively, are slightly twisted from the corresponding ring planes [C3—C2—O3—C25 = −5.3 (3); C13—C14—O5—C27 = −10.2 (4); C22—C21—O6—C28 = −10.6 (3)°]. The hydroxyl group attached to the C10–C15 benzene ring forms an intramolecular O2—H2⋯O1 hydrogen bond with carbonyl O atom of the chalcone unit (Table 1).
|
In the crystal, pairs of C—H⋯O hydrogen bonds generate inversion dimers (Table 1, Fig. 2) and another pair of C—H⋯O hydrogen bonds links the dimers into chains propagating along [010] (Fig. 3). Given their H⋯O lengths of greater than 2.60 Å, these hydrogen bonds are presumably very weak.
Synthesis and crystallization
The synthetic scheme for the preparation of the title compound is shown in Fig. 4. Using the previously reported method (Shin et al. 2019), the resveratrol aldehyde intermediates II and III were prepared in 30% and 15% yields, respectively, from trimethoxy resveratrol (I). The methylated resveratrol aldehyde intermediate III was reacted with 2-hydroxy-5-methoxy acetophenone (IV) under Claisen–Schmidt condensation conditions to give the desired title compound. Recrystallization of the final adduct from ethanol solution gave crystals of the title compound in the form of orange blocks.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2009305
https://doi.org/10.1107/S2414314620007920/hb4350sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620007920/hb4350Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620007920/hb4350Isup3.cml
Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (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).C28H28O6 | F(000) = 976 |
Mr = 460.50 | Dx = 1.294 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3197 reflections |
a = 9.9641 (9) Å | θ = 2.5–25.2° |
b = 10.2338 (9) Å | µ = 0.09 mm−1 |
c = 23.541 (2) Å | T = 200 K |
β = 100.086 (2)° | Block, orange |
V = 2363.4 (4) Å3 | 0.12 × 0.09 × 0.06 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2351 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
phi and ω scans | h = −11→12 |
14437 measured reflections | k = −9→12 |
4659 independent reflections | l = −28→29 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.038P)2] where P = (Fo2 + 2Fc2)/3 |
4659 reflections | (Δ/σ)max < 0.001 |
313 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.15 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 | 0.3422 (2) | 0.3627 (2) | 0.40004 (9) | 0.0406 (6) | |
C2 | 0.2593 (2) | 0.4124 (2) | 0.35097 (9) | 0.0394 (6) | |
C3 | 0.1584 (2) | 0.5038 (2) | 0.35435 (9) | 0.0408 (6) | |
H3 | 0.1026 | 0.5355 | 0.3203 | 0.049* | |
C4 | 0.1399 (2) | 0.5484 (2) | 0.40788 (9) | 0.0406 (6) | |
C5 | 0.2191 (2) | 0.5016 (2) | 0.45928 (9) | 0.0388 (6) | |
C6 | 0.3192 (2) | 0.4054 (2) | 0.45383 (9) | 0.0379 (5) | |
C7 | 0.2088 (2) | 0.5513 (2) | 0.51624 (9) | 0.0439 (6) | |
H7 | 0.2752 | 0.5181 | 0.5468 | 0.053* | |
C8 | 0.1215 (2) | 0.6356 (2) | 0.53234 (9) | 0.0527 (7) | |
H8 | 0.0514 | 0.6709 | 0.5039 | 0.063* | |
C9 | 0.1295 (2) | 0.6759 (2) | 0.59251 (10) | 0.0466 (6) | |
O1 | 0.20637 (17) | 0.62039 (17) | 0.63223 (7) | 0.0635 (5) | |
C10 | 0.0400 (2) | 0.7828 (2) | 0.60542 (9) | 0.0417 (6) | |
C11 | 0.0227 (2) | 0.8074 (2) | 0.66249 (10) | 0.0455 (6) | |
O2 | 0.09471 (17) | 0.74132 (18) | 0.70846 (6) | 0.0597 (5) | |
H2 | 0.1521 | 0.6923 | 0.6970 | 0.090* | |
C12 | −0.0714 (2) | 0.8998 (2) | 0.67300 (11) | 0.0528 (7) | |
H12 | −0.0858 | 0.9135 | 0.7114 | 0.063* | |
C13 | −0.1444 (2) | 0.9722 (2) | 0.62869 (11) | 0.0533 (7) | |
H13 | −0.2084 | 1.0354 | 0.6367 | 0.064* | |
C14 | −0.1245 (2) | 0.9527 (2) | 0.57248 (11) | 0.0508 (6) | |
C15 | −0.0335 (2) | 0.8589 (2) | 0.56154 (10) | 0.0469 (6) | |
H15 | −0.0203 | 0.8455 | 0.5230 | 0.056* | |
C16 | 0.4010 (2) | 0.3476 (2) | 0.50661 (9) | 0.0422 (6) | |
H16 | 0.4946 | 0.3709 | 0.5157 | 0.051* | |
C17 | 0.3536 (2) | 0.2669 (2) | 0.54151 (9) | 0.0459 (6) | |
H17 | 0.2607 | 0.2422 | 0.5308 | 0.055* | |
C18 | 0.4276 (2) | 0.2103 (2) | 0.59522 (9) | 0.0408 (6) | |
C19 | 0.5437 (2) | 0.2690 (2) | 0.62614 (9) | 0.0433 (6) | |
H19 | 0.5750 | 0.3489 | 0.6126 | 0.052* | |
C20 | 0.6147 (2) | 0.2142 (2) | 0.67603 (9) | 0.0439 (6) | |
H20 | 0.6942 | 0.2559 | 0.6962 | 0.053* | |
C21 | 0.5698 (2) | 0.0981 (2) | 0.69667 (9) | 0.0405 (6) | |
C22 | 0.4544 (2) | 0.0388 (2) | 0.66742 (9) | 0.0434 (6) | |
H22 | 0.4229 | −0.0406 | 0.6814 | 0.052* | |
C23 | 0.3837 (2) | 0.0955 (2) | 0.61703 (9) | 0.0456 (6) | |
H23 | 0.3035 | 0.0544 | 0.5972 | 0.055* | |
C24 | 0.4492 (2) | 0.2627 (2) | 0.39366 (10) | 0.0577 (7) | |
H24A | 0.4070 | 0.1896 | 0.3702 | 0.087* | |
H24B | 0.4913 | 0.2306 | 0.4319 | 0.087* | |
H24C | 0.5191 | 0.3028 | 0.3747 | 0.087* | |
O3 | 0.28463 (16) | 0.36458 (15) | 0.29960 (6) | 0.0508 (4) | |
C25 | 0.1959 (2) | 0.4029 (2) | 0.24813 (9) | 0.0553 (7) | |
H25A | 0.1021 | 0.3785 | 0.2507 | 0.083* | |
H25B | 0.2232 | 0.3589 | 0.2150 | 0.083* | |
H25C | 0.2014 | 0.4978 | 0.2433 | 0.083* | |
O4 | 0.04512 (16) | 0.64150 (15) | 0.41344 (6) | 0.0542 (5) | |
C26 | −0.0374 (3) | 0.6922 (2) | 0.36263 (10) | 0.0626 (8) | |
H26A | 0.0211 | 0.7301 | 0.3375 | 0.094* | |
H26B | −0.0980 | 0.7599 | 0.3733 | 0.094* | |
H26C | −0.0921 | 0.6215 | 0.3422 | 0.094* | |
O5 | −0.18961 (18) | 1.01996 (17) | 0.52486 (7) | 0.0685 (5) | |
C27 | −0.3001 (3) | 1.1009 (3) | 0.53203 (12) | 0.0764 (9) | |
H27A | −0.3682 | 1.0493 | 0.5476 | 0.115* | |
H27B | −0.3415 | 1.1378 | 0.4946 | 0.115* | |
H27C | −0.2673 | 1.1719 | 0.5589 | 0.115* | |
O6 | 0.64798 (16) | 0.05087 (16) | 0.74612 (6) | 0.0559 (5) | |
C28 | 0.5936 (3) | −0.0556 (2) | 0.77410 (10) | 0.0634 (7) | |
H28A | 0.5010 | −0.0341 | 0.7797 | 0.095* | |
H28B | 0.6513 | −0.0717 | 0.8116 | 0.095* | |
H28C | 0.5911 | −0.1342 | 0.7501 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0444 (14) | 0.0374 (13) | 0.0385 (13) | 0.0065 (11) | 0.0035 (11) | −0.0028 (11) |
C2 | 0.0446 (14) | 0.0410 (14) | 0.0322 (13) | −0.0025 (12) | 0.0057 (11) | −0.0050 (11) |
C3 | 0.0465 (14) | 0.0433 (14) | 0.0301 (13) | 0.0046 (12) | −0.0003 (11) | 0.0010 (10) |
C4 | 0.0431 (14) | 0.0390 (14) | 0.0383 (14) | 0.0096 (11) | 0.0033 (11) | 0.0007 (11) |
C5 | 0.0443 (14) | 0.0409 (14) | 0.0297 (13) | 0.0038 (11) | 0.0020 (11) | −0.0007 (10) |
C6 | 0.0420 (13) | 0.0368 (13) | 0.0332 (13) | 0.0038 (11) | 0.0024 (11) | 0.0013 (10) |
C7 | 0.0517 (15) | 0.0453 (14) | 0.0322 (13) | 0.0119 (12) | 0.0001 (11) | −0.0005 (11) |
C8 | 0.0569 (16) | 0.0656 (17) | 0.0331 (14) | 0.0220 (14) | 0.0013 (12) | −0.0053 (12) |
C9 | 0.0468 (15) | 0.0571 (16) | 0.0346 (14) | 0.0073 (13) | 0.0036 (12) | −0.0024 (12) |
O1 | 0.0732 (12) | 0.0785 (13) | 0.0345 (10) | 0.0290 (10) | −0.0025 (9) | −0.0017 (9) |
C10 | 0.0405 (14) | 0.0487 (15) | 0.0354 (13) | 0.0027 (12) | 0.0055 (11) | −0.0061 (11) |
C11 | 0.0477 (15) | 0.0524 (16) | 0.0357 (14) | −0.0025 (13) | 0.0051 (12) | −0.0064 (12) |
O2 | 0.0653 (12) | 0.0778 (13) | 0.0347 (9) | 0.0115 (10) | 0.0050 (9) | −0.0063 (9) |
C12 | 0.0548 (16) | 0.0628 (17) | 0.0435 (15) | −0.0002 (14) | 0.0158 (13) | −0.0153 (13) |
C13 | 0.0513 (16) | 0.0538 (17) | 0.0581 (17) | 0.0032 (13) | 0.0183 (14) | −0.0120 (14) |
C14 | 0.0493 (15) | 0.0523 (16) | 0.0510 (16) | 0.0082 (13) | 0.0096 (13) | −0.0006 (13) |
C15 | 0.0480 (15) | 0.0552 (16) | 0.0384 (14) | 0.0066 (13) | 0.0098 (12) | −0.0046 (12) |
C16 | 0.0397 (13) | 0.0439 (14) | 0.0403 (14) | 0.0059 (11) | −0.0001 (11) | 0.0023 (11) |
C17 | 0.0457 (15) | 0.0514 (15) | 0.0381 (14) | 0.0013 (12) | 0.0005 (12) | 0.0032 (12) |
C18 | 0.0475 (14) | 0.0403 (14) | 0.0336 (13) | 0.0047 (12) | 0.0045 (11) | 0.0001 (11) |
C19 | 0.0529 (15) | 0.0392 (14) | 0.0375 (14) | 0.0033 (12) | 0.0067 (12) | −0.0002 (11) |
C20 | 0.0473 (15) | 0.0466 (15) | 0.0354 (14) | 0.0008 (12) | 0.0008 (12) | 0.0001 (11) |
C21 | 0.0453 (14) | 0.0450 (15) | 0.0306 (13) | 0.0069 (12) | 0.0055 (11) | 0.0023 (11) |
C22 | 0.0498 (15) | 0.0430 (14) | 0.0390 (14) | 0.0038 (12) | 0.0126 (12) | 0.0045 (12) |
C23 | 0.0459 (14) | 0.0498 (15) | 0.0405 (14) | 0.0018 (12) | 0.0057 (12) | −0.0002 (12) |
C24 | 0.0645 (18) | 0.0603 (17) | 0.0475 (16) | 0.0204 (14) | 0.0074 (14) | −0.0043 (13) |
O3 | 0.0576 (11) | 0.0620 (11) | 0.0324 (9) | 0.0061 (9) | 0.0071 (8) | −0.0083 (8) |
C25 | 0.0583 (16) | 0.0779 (19) | 0.0280 (13) | −0.0043 (14) | 0.0028 (12) | −0.0054 (13) |
O4 | 0.0621 (11) | 0.0618 (11) | 0.0352 (9) | 0.0287 (9) | −0.0016 (8) | 0.0006 (8) |
C26 | 0.0670 (18) | 0.0717 (19) | 0.0444 (16) | 0.0338 (15) | −0.0030 (13) | 0.0097 (14) |
O5 | 0.0725 (13) | 0.0722 (13) | 0.0627 (12) | 0.0316 (11) | 0.0176 (10) | 0.0101 (10) |
C27 | 0.0694 (19) | 0.073 (2) | 0.087 (2) | 0.0320 (17) | 0.0160 (17) | 0.0081 (17) |
O6 | 0.0590 (11) | 0.0652 (12) | 0.0398 (10) | 0.0011 (9) | −0.0013 (8) | 0.0186 (9) |
C28 | 0.0746 (19) | 0.0636 (18) | 0.0492 (16) | −0.0003 (15) | 0.0034 (14) | 0.0242 (14) |
C1—C2 | 1.393 (3) | C17—C18 | 1.467 (3) |
C1—C6 | 1.396 (3) | C17—H17 | 0.9500 |
C1—C24 | 1.504 (3) | C18—C23 | 1.383 (3) |
C2—O3 | 1.368 (2) | C18—C19 | 1.391 (3) |
C2—C3 | 1.386 (3) | C19—C20 | 1.379 (3) |
C3—C4 | 1.383 (3) | C19—H19 | 0.9500 |
C3—H3 | 0.9500 | C20—C21 | 1.388 (3) |
C4—O4 | 1.364 (2) | C20—H20 | 0.9500 |
C4—C5 | 1.408 (3) | C21—O6 | 1.370 (2) |
C5—C6 | 1.423 (3) | C21—C22 | 1.374 (3) |
C5—C7 | 1.454 (3) | C22—C23 | 1.396 (3) |
C6—C16 | 1.484 (3) | C22—H22 | 0.9500 |
C7—C8 | 1.327 (3) | C23—H23 | 0.9500 |
C7—H7 | 0.9500 | C24—H24A | 0.9800 |
C8—C9 | 1.464 (3) | C24—H24B | 0.9800 |
C8—H8 | 0.9500 | C24—H24C | 0.9800 |
C9—O1 | 1.238 (3) | O3—C25 | 1.424 (2) |
C9—O1 | 1.238 (3) | C25—H25A | 0.9800 |
C9—C10 | 1.476 (3) | C25—H25B | 0.9800 |
C10—C15 | 1.395 (3) | C25—H25C | 0.9800 |
C10—C11 | 1.407 (3) | O4—C26 | 1.425 (2) |
C11—O2 | 1.368 (3) | C26—H26A | 0.9800 |
C11—C12 | 1.384 (3) | C26—H26B | 0.9800 |
O2—H2 | 0.8400 | C26—H26C | 0.9800 |
C12—C13 | 1.379 (3) | O5—C27 | 1.411 (3) |
C12—H12 | 0.9500 | C27—H27A | 0.9800 |
C13—C14 | 1.386 (3) | C27—H27B | 0.9800 |
C13—H13 | 0.9500 | C27—H27C | 0.9800 |
C14—C15 | 1.376 (3) | O6—C28 | 1.429 (3) |
C14—O5 | 1.377 (3) | C28—H28A | 0.9800 |
C15—H15 | 0.9500 | C28—H28B | 0.9800 |
C16—C17 | 1.310 (3) | C28—H28C | 0.9800 |
C16—H16 | 0.9500 | ||
C2—C1—C6 | 118.1 (2) | C18—C17—H17 | 116.3 |
C2—C1—C24 | 119.5 (2) | C23—C18—C19 | 117.4 (2) |
C6—C1—C24 | 122.4 (2) | C23—C18—C17 | 120.8 (2) |
O3—C2—C3 | 122.7 (2) | C19—C18—C17 | 121.8 (2) |
O3—C2—C1 | 115.3 (2) | C20—C19—C18 | 121.7 (2) |
C3—C2—C1 | 122.0 (2) | C20—C19—H19 | 119.2 |
C4—C3—C2 | 119.3 (2) | C18—C19—H19 | 119.2 |
C4—C3—H3 | 120.3 | C19—C20—C21 | 119.8 (2) |
C2—C3—H3 | 120.3 | C19—C20—H20 | 120.1 |
O4—C4—C3 | 121.6 (2) | C21—C20—H20 | 120.1 |
O4—C4—C5 | 116.66 (19) | O6—C21—C22 | 124.9 (2) |
C3—C4—C5 | 121.8 (2) | O6—C21—C20 | 115.4 (2) |
C4—C5—C6 | 117.02 (19) | C22—C21—C20 | 119.7 (2) |
C4—C5—C7 | 123.7 (2) | C21—C22—C23 | 119.7 (2) |
C6—C5—C7 | 119.2 (2) | C21—C22—H22 | 120.1 |
C1—C6—C5 | 121.8 (2) | C23—C22—H22 | 120.1 |
C1—C6—C16 | 118.8 (2) | C18—C23—C22 | 121.6 (2) |
C5—C6—C16 | 119.41 (19) | C18—C23—H23 | 119.2 |
C8—C7—C5 | 130.2 (2) | C22—C23—H23 | 119.2 |
C8—C7—H7 | 114.9 | C1—C24—H24A | 109.5 |
C5—C7—H7 | 114.9 | C1—C24—H24B | 109.5 |
C7—C8—C9 | 122.2 (2) | H24A—C24—H24B | 109.5 |
C7—C8—H8 | 118.9 | C1—C24—H24C | 109.5 |
C9—C8—H8 | 118.9 | H24A—C24—H24C | 109.5 |
O1—C9—C8 | 121.5 (2) | H24B—C24—H24C | 109.5 |
O1—C9—C8 | 121.5 (2) | C2—O3—C25 | 118.06 (17) |
O1—C9—C10 | 120.0 (2) | O3—C25—H25A | 109.5 |
O1—C9—C10 | 120.0 (2) | O3—C25—H25B | 109.5 |
C8—C9—C10 | 118.4 (2) | H25A—C25—H25B | 109.5 |
C15—C10—C11 | 118.1 (2) | O3—C25—H25C | 109.5 |
C15—C10—C9 | 121.3 (2) | H25A—C25—H25C | 109.5 |
C11—C10—C9 | 120.6 (2) | H25B—C25—H25C | 109.5 |
O2—C11—C12 | 118.3 (2) | C4—O4—C26 | 118.78 (17) |
O2—C11—C10 | 122.2 (2) | O4—C26—H26A | 109.5 |
C12—C11—C10 | 119.5 (2) | O4—C26—H26B | 109.5 |
C11—O2—H2 | 109.5 | H26A—C26—H26B | 109.5 |
C13—C12—C11 | 121.1 (2) | O4—C26—H26C | 109.5 |
C13—C12—H12 | 119.5 | H26A—C26—H26C | 109.5 |
C11—C12—H12 | 119.5 | H26B—C26—H26C | 109.5 |
C12—C13—C14 | 120.0 (2) | C14—O5—C27 | 117.51 (19) |
C12—C13—H13 | 120.0 | O5—C27—H27A | 109.5 |
C14—C13—H13 | 120.0 | O5—C27—H27B | 109.5 |
C15—C14—O5 | 115.4 (2) | H27A—C27—H27B | 109.5 |
C15—C14—C13 | 119.2 (2) | O5—C27—H27C | 109.5 |
O5—C14—C13 | 125.4 (2) | H27A—C27—H27C | 109.5 |
C14—C15—C10 | 121.9 (2) | H27B—C27—H27C | 109.5 |
C14—C15—H15 | 119.0 | C21—O6—C28 | 117.08 (18) |
C10—C15—H15 | 119.0 | O6—C28—H28A | 109.5 |
C17—C16—C6 | 124.8 (2) | O6—C28—H28B | 109.5 |
C17—C16—H16 | 117.6 | H28A—C28—H28B | 109.5 |
C6—C16—H16 | 117.6 | O6—C28—H28C | 109.5 |
C16—C17—C18 | 127.4 (2) | H28A—C28—H28C | 109.5 |
C16—C17—H17 | 116.3 | H28B—C28—H28C | 109.5 |
C6—C1—C2—O3 | −178.50 (18) | C9—C10—C11—O2 | 5.1 (3) |
C24—C1—C2—O3 | −0.5 (3) | C15—C10—C11—C12 | 3.7 (3) |
C6—C1—C2—C3 | 1.5 (3) | C9—C10—C11—C12 | −173.9 (2) |
C24—C1—C2—C3 | 179.5 (2) | O2—C11—C12—C13 | 178.2 (2) |
O3—C2—C3—C4 | −179.4 (2) | C10—C11—C12—C13 | −2.8 (4) |
C1—C2—C3—C4 | 0.6 (3) | C11—C12—C13—C14 | 0.2 (4) |
C2—C3—C4—O4 | 177.77 (19) | C12—C13—C14—C15 | 1.3 (4) |
C2—C3—C4—C5 | −1.2 (3) | C12—C13—C14—O5 | −179.0 (2) |
O4—C4—C5—C6 | −179.35 (18) | O5—C14—C15—C10 | −179.9 (2) |
C3—C4—C5—C6 | −0.3 (3) | C13—C14—C15—C10 | −0.2 (4) |
O4—C4—C5—C7 | −2.9 (3) | C11—C10—C15—C14 | −2.3 (3) |
C3—C4—C5—C7 | 176.1 (2) | C9—C10—C15—C14 | 175.4 (2) |
C2—C1—C6—C5 | −3.1 (3) | C1—C6—C16—C17 | −108.8 (3) |
C24—C1—C6—C5 | 179.0 (2) | C5—C6—C16—C17 | 70.8 (3) |
C2—C1—C6—C16 | 176.4 (2) | C6—C16—C17—C18 | −177.6 (2) |
C24—C1—C6—C16 | −1.5 (3) | C16—C17—C18—C23 | −157.3 (2) |
C4—C5—C6—C1 | 2.5 (3) | C16—C17—C18—C19 | 22.7 (4) |
C7—C5—C6—C1 | −174.1 (2) | C23—C18—C19—C20 | 1.3 (3) |
C4—C5—C6—C16 | −177.0 (2) | C17—C18—C19—C20 | −178.7 (2) |
C7—C5—C6—C16 | 6.4 (3) | C18—C19—C20—C21 | −0.5 (3) |
C4—C5—C7—C8 | 6.9 (4) | C19—C20—C21—O6 | 179.34 (19) |
C6—C5—C7—C8 | −176.8 (2) | C19—C20—C21—C22 | −0.4 (3) |
C5—C7—C8—C9 | −178.8 (2) | O6—C21—C22—C23 | −179.4 (2) |
C7—C8—C9—O1 | −9.8 (4) | C20—C21—C22—C23 | 0.3 (3) |
C7—C8—C9—O1 | −9.8 (4) | C19—C18—C23—C22 | −1.4 (3) |
C7—C8—C9—C10 | 172.0 (2) | C17—C18—C23—C22 | 178.6 (2) |
C8—C9—O1—O1 | 0.0 (3) | C21—C22—C23—C18 | 0.6 (3) |
C10—C9—O1—O1 | 0.0 (3) | C3—C2—O3—C25 | −5.3 (3) |
O1—C9—C10—C15 | 171.1 (2) | C1—C2—O3—C25 | 174.72 (19) |
O1—C9—C10—C15 | 171.1 (2) | C3—C4—O4—C26 | 0.8 (3) |
C8—C9—C10—C15 | −10.8 (3) | C5—C4—O4—C26 | 179.9 (2) |
O1—C9—C10—C11 | −11.4 (3) | C15—C14—O5—C27 | 169.4 (2) |
O1—C9—C10—C11 | −11.4 (3) | C13—C14—O5—C27 | −10.2 (4) |
C8—C9—C10—C11 | 166.8 (2) | C22—C21—O6—C28 | −10.6 (3) |
C15—C10—C11—O2 | −177.2 (2) | C20—C21—O6—C28 | 169.73 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.84 | 1.86 | 2.586 (2) | 144 |
C25—H25A···O2i | 0.98 | 2.63 | 3.556 (3) | 157 |
C28—H28B···O1ii | 0.98 | 2.64 | 3.247 (3) | 120 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+3/2. |
Funding information
The authors acknowledge financial support from Dongduk Women's University, Republic of Korea.
References
Bruker (2012). APEX2, SAINT and SADABS, Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Gil, H. N., Koh, D., Lim, Y., Lee, Y. H. & Shin, S. Y. (2018). Bioorg. Med. Chem. Lett. 28, 2969–2975. Web of Science CrossRef CAS PubMed Google Scholar
Lee, D. H., Jung Jung, Y., Koh, D., Lim, Y., Lee, Y. H. & Shin, S. Y. (2016). Cancer Lett. 372, 1–9. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shin, S. Y., Lee, J., Park, J., Lee, Y., Ahn, S., Lee, J. H., Koh, D., Lee, Y. H. & Lim, Y. (2019). Bioorg. Chem. 83, 438–449. Web of Science CrossRef CAS PubMed Google Scholar
Timperio, A. M., D'Alessandro, A., Fagioni, M., Magro, P. & Zolla, L. (2012). Plant Physiol. Biochem. 50, 65–71. Web of Science CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing, C. & Miao, Z. (2017). Chem. Rev. 117, 7762–7810. Web of Science CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.