(E)-3-{4,6-Dimeth­oxy-2-[(E)-4-meth­oxy­styr­yl]-3-methyl­phen­yl}-1-(2-hy­droxy-5-meth­oxy­phen­yl)prop-2-en-1-one

Yoo, M.; Koh, D.

doi:10.1107/S2414314620007920

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 6| June 2020| x200792

https://doi.org/10.1107/S2414314620007920

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(E)-3-{4,6-Dimethoxy-2-[(E)-4-methoxystyryl]-3-methylphenyl}-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one

Miri Yoo ^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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 10 June 2020; accepted 11 June 2020; online 16 June 2020)

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 ). Chalcones, which are another essential secondary metabolites 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).

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

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.

Figure 2
A view of a dimer linked by pairwise C—H⋯O hydrogen bonds (dashed lines) in the crystal structure of (I). For clarity only those H atoms involved in hydrogen bonding are shown.

Figure 3
Part of the crystal structure of (I) with hydrogen bonds (blue dashed lines) shown. For clarity only those H atoms involved in hydrogen bonding are shown.

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.

Figure 4
Synthetic scheme for the preparation of (I).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₈O₆
M_r	460.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	9.9641 (9), 10.2338 (9), 23.541 (2)
β (°)	100.086 (2)
V (Å³)	2363.4 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.09 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	14437, 4659, 2351
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.112, 0.88
No. of reflections	4659
No. of parameters	313
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXS and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2009305

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314620007920/hb4350sup1.cif

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

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: 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).

(E)-3-{4,6-dimethoxy-2-[(E)-4-methoxystyryl]-3-methylphenyl}-1-(2-hydroxy-5-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₈H₂₈O₆	F(000) = 976
M_r = 460.50	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2351 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
phi and ω scans	h = −11→12
14437 measured reflections	k = −9→12
4659 independent reflections	l = −28→29

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.038P)²] where P = (F_o² + 2F_c²)/3
4659 reflections	(Δ/σ)_max < 0.001
313 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 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.

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

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