Synthesis and crystal structure of bis­[(1E,6E)-1,7-bis­(4-acet­yloxy-3-meth­oxy­phen­yl)hepta-1,6-diene-3,5-dionato(1−)-κ2O,O′](methanol)dioxidouranium(VI) toluene monosolvate

Nguyen, V.H.; Trieu, T.N.; Pham, C.T.

doi:10.1107/S2056989026002525

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 82| Part 5| May 2026| Pages 422-425

https://doi.org/10.1107/S2056989026002525

Open

access

Synthesis and crystal structure of bis[(1E,6E)-1,7-bis(4-acetyloxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dionato(1−)-κ²O,O′](methanol)dioxidouranium(VI) toluene monosolvate

Van Ha Nguyen,^a Thi Nguyet Trieu ^a and Chien Thang Pham ^a ^*

^aFaculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 19 Le Thanh Tong, Hanoi, Vietnam
^*Correspondence e-mail: [email protected]

Edited by G. Ferrence, Illinois State University, USA (Received 22 October 2025; accepted 10 March 2026; online 2 April 2026)

The first uranium–curcuminoid coordination compound has been synthesized and structurally characterized. The title complex, [U(O)₂(C₂₅H₂₃O₈)₂(CH₃OH)]·C₆H₅CH₃, crystallizes in the monoclinic space group C2/c. The neutral complex comprises a uranyl(VI) unit ({O=U=O}²⁺) coordinated by two monoanionic bidentate 4,4′-diacetylcurcuminato ligands (C₂₅H₂₃O₈) and one methanol co-ligand, resulting in a distorted pentagonal–bipyramidal coordination geometry. The O atoms from the β-diketonate moieties and the methanol molecule form the equatorial plane, while the uranyl O atoms occupy the axial positions. In the crystal, O—H⋯O hydrogen bonds generate R₂²(26) ring motifs, forming zigzag chains along the a-axis direction. Additional weak C—H⋯O interactions further consolidate the crystal packing through interchain aggregation.

Keywords: curcumin; 4,4′-diacetylcurcumin; uranyl complex; crystal structure.

CCDC reference: 2536300

1. Chemical context

Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione] is a major constituent of turmeric (Curcuma longa, Zingiberaceae) (Goel et al., 2008 ). Beyond its widespread use as a spice and natural food coloring, turmeric has been employed in traditional medicine to treat a broad spectrum of diseases (Goel et al., 2008; Esatbeyoglu et al., 2012 ). The therapeutic potential of curcumin has attracted considerable attention, and numerous studies have confirmed its antioxidant, anti-inflammatory (Menon et al., 2007 ; Dehzad et al., 2023 ), anticarcinogenic (Salem et al., 2014 ), and antimicrobial (Dai et al., 2022 ) properties. From a chemical perspective, curcumin and its structural analogues are natural β-diketone ligands capable of chelating and forming stable complexes with a wide range of metal ions, including main group, transition, and rare-earth metals (Bhagat et al., 2025 ). In recent decades, metal-curcumin complexes have gained significant interest because of their diverse biological activities (Banerjee et al., 2015 ; Prasad et al., 2021 ; Bhagat et al., 2025). However, their application is often limited by extremely poor solubility in water and in most common organic solvents (Wanninger et al., 2015 ; Prasad et al., 2021). To overcome this limitation, structural modifications such as etherification or esterification of curcumin have been developed, leading to various derivatives and a number of structurally characterized metal complexes (Wang et al., 2014 ; Meza-Morales et al., 2019 ; Pham et al., 2020 ; Meza-Morales et al., 2023a ). Nevertheless, comprehensive structural data on curcuminoid complexes remain limited, and no actinide-curcumin complex has hitherto been structurally characterized. Herein, we report the synthesis and crystal structure of the first uranyl complex with acetylated curcumin (4,4′-diacetylcurcumin, HL).

2. Structural commentary

The title compound crystallizes in the centrosymmetric monoclinic space group C2/c, with half of the molecule, [U(O)₂(L)₂(CH₃OH)]·C₆H₅CH₃, in the asymmetric unit (Fig. 1). The complex consists of one uranyl unit (UO₂²⁺), two monodeprotonated acetylated curcumin ligands {L}⁻, and one methanol co-ligand. The methanol molecule is disordered over two symmetry-related sites with equal occupancy factors of 0.5. The uranium atom adopts a distorted pentagonal–bipyramidal coordination geometry, with the oxido ligands occupying the axial positions. The {L}⁻ ligands equatorially coordinate through (O,O)-chelating β-diketonate moieties, while the equatorial plane is completed by a disordered methanol ligand. The uranium atom lies 0.064 (6) Å out of the mean equatorial plane. The U=O bond length [1.772 (6) Å] and O=U=O bond angle [179.5 (3)°] fall within the expected range (Ainscough et al., 1998 , Huuskonen et al., 2007 , Al-Anber et al., 2011 ). The equatorial U1—O bond distances [U1—O1 = 2.345 (5) Å and U1—O3 = 2.351 (5) Å] are comparable to those reported for pentagonal-bipyramidal β-diketonate uranyl complexes (Hernandez et al., 2022 ; Monzón González et al., 2024 ; Jabborova et al., 2024 ). The U—O_MeOH bond distance [U1—O4 = 2.567 (9) Å] is longer than the U—O_L bonds, indicating weaker coordination of the solvent molecule compared to the chelating β-diketonate ligands. The C—C and C—O bond lengths within the chelate rings are consistent with those observed in related complexes of HL with other divalent metal ions (Meza-Morales et al., 2019; Pham et al., 2020). The partial double-bond character of these bonds reflects the expected π-electron delocalization within the β-diketonate moieties. Peripheral portions of the {L}⁻ ligand are disordered over two positions, with refined occupancy factors of 0.5083 (1)/0.4916 (9) for one aromatic ring and its acetyl group, and 0.6046 (3)/0.3953 (7) for the acetyl group on the other ligand fragment.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms bonded to aromatic rings and methyl groups are omitted for clarity. Symmetry code: (§) −x + 1, y, −z + $[{1\over 2}]$ .

3. Supramolecular features

In the crystal structure, the complex does not form columnar packing or significant π–π stacking interactions. The molecules are arranged as discrete units, resulting in solvent-accessible voids. Void analysis performed using OLEX2 (Dolomanov et al., 2009 ) indicates that the structure occupies 3588.18 Å³ (63.31%) of the unit-cell volume, leaving void space that is occupied by toluene solvent molecules. These solvent molecules contribute to the overall cohesion of the crystal structure.

In the crystal, O—H⋯O hydrogen bonds between the hydroxyl groups of the disordered methanol molecules and the carbonyl O40 atoms of adjacent units link the molecules into inversion dimers via R₂²(26) hydrogen-bonding motifs (Fig. 2a, Table 1). These hydrogen bonds further connect the dimers into zigzag chains extending along the a-axis direction (Fig. 2b). In addition, weak C40A—H40D⋯O20B hydrogen bonds (Fig. 3a, Table 1) link the chains into a three-dimensional supramolecular network (Fig. 3b). A further weak intermolecular C30—H30⋯O2 contact also contributes to the consolidation of the crystal packing.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O40Aⁱ	0.84	2.33	2.99 (2)	136
O4—H4⋯O40Bⁱ	0.84	2.67	3.23 (4)	125
C40A—H40D⋯O20Bⁱⁱ	0.98	2.46	3.25 (4)	137
C30—H30⋯O2ⁱⁱ	0.95	2.58	3.436 (9)	150
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
(a) Molecular packing diagram showing the R₂²(26) hydrogen-bonding motif. (b) Polymeric chains extending along the a-axis direction. Hydrogen bonds are shown as dashed lines. Solvent molecules and hydrogen atoms not involved in hydrogen bonding have been omitted for clarity. Symmetry codes: (§) −x + 1, y, −z + $[{1\over 2}]$ ; (i) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ ; (iii) −x + $[{3\over 2}]$ , −y + $[{3\over 2}]$ , −z; (iv) −x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , −z + 1; (v) x − $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ; (vi) x + 1, y, z − 1; (vii) −x + 2, y, −z − $[{1\over 2}]$ .

Figure 3
(a) Molecular packing diagram showing weak C—H⋯O hydrogen bonds between units in adjacent chains. Symmetry codes: (§) −x + 1, y, −z + $[{1\over 2}]$ ; (iii) x, −y + 1, z + $[{1\over 2}]$ ; (viii) −x + 1, −y + 1, −z + 1. (b) Crystal packing viewed along the a-axis direction illustrating the aggregation of chains. The central chain is highlighted for clarity. Hydrogen bonds are shown as dashed lines. Solvent molecules and hydrogen atoms not involved in weak hydrogen bonds have been omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD version 6.00, update on August 2025; Groom et al., 2016 ) resulted in 25 entries describing homoleptic metal complexes of curcumin and its derivatives. Among these, ten structures correspond to coordination compounds derived from 4,4′-diacetylcurcumin, including HOBDUA, JOCQEA, JOCQUQ, JOCRAX, PEJREE (Meza-Morales et al., 2019), KUNTUL, KUNVAT, KUNVEX, KUNVIB (Pham et al., 2020) and YIHKIN (Meza-Morales et al., 2023b ). A separate search for uranyl complexes based on β-diketone ligands returned 93 entries exhibiting pentagonal–bipyramidal geometries similar to that observed in the title structure. Of these, fourteen structures have been reported within the past decade, including BUHDEP (Ma et al., 2015 ), NOVBUX (Kawasaki et al., 2015 ), VOWCUH (Vats et al., 2015 ), CIVVAH and CIVVEL (Carter et al., 2018 ), XEXZOS and XEXZUY (Kurzajewska et al., 2018 ), TAMTUA (Hernandez et al., 2022), EFOGOZ (Monzón González et al., 2024), GUGREJ (Jabborova et al., 2024), IMICEQ and IMICIU (Tafeenko et al., 2025 ), LAFKAJ and VACCAI (Clark et al., 2025 ).

5. Synthesis and crystallization

4,4′-Diacetylcurcumin (90.4 mg, 0.2 mmol) was added to 1.55 mL solution of UO₂(OAc)₂·2H₂O (42.4 mg, 0.1 mmol) in MeOH. The color of the reaction mixture immediately changed from yellow to red–orange. After stirring the reaction mixture for 15 min, two drops of Et₃N were added. Then, the temperature was increased to 313 K and kept for 1 h. During this process, a red–orange precipitate deposited, which was filtered off, washed with a small amount of MeOH and dried under vacuum. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the complex in a mixture of CH₂Cl₂, MeOH and toluene. Yield: ∼70% (82 mg).

IR (KBr, cm⁻¹): 3448 (br, m), 3005 (w), 2942 (w), 1764 (m), 1722 (m), 1627 (m), 1599 (m), 1511 (s), 1467 (m), 1394 (m), 1295 (m), 1259 (m), 1198 (m), 1156 (m), 1121 (m), 1031 (w), 985 (w), 905 (m), 849 (w), 606 (w), 466 (w).

¹H NMR (500 MHz, CDCl₃, ppm): 8.11 (br, d, J = 15.0 Hz, 2 H, CH), 7.62 (d, J = 16.0 Hz, 2 H, CH), 7.17–7.05 (m, 12 H, Ph), 6.98 (d, J = 15.5 Hz, 2 H, CH), 6.57 (d, J = 15.5 Hz, 2 H, CH), 6.01 (s, 1 H, C_αH), 5.87 (s, 1 H, C_αH), 3.88 (s, 6 H, OCH₃), 3.78 (s, 6 H, OCH₃), 2.36 (s, 6 H, CH₃COO), 2.33 (s, 6 H, CH₃).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The aromatic ring (C12–C17) and its acetyl group are disordered over two positions with refined occupancies of 0.5083 (1):0.4916 (9); another acetyl group is disordered in a 0.6046 (3):0.3953 (7) ratio. Aromatic C atoms of the toluene solvent were restrained to be approximately isotropic (ISOR) and planar (FLAT). Bond distances C11—C12A, C15A—O19A and those within the toluene ring were restrained using DFIX 1.4, while equivalent C—C distances in disordered acetyl groups and toluene ring were constrained using SADI. Displacement ellipsoids of disordered atom pairs including (C20A, C20B), (C39A, C39B), (C40A, C40B) and (O40A, O40B) were restrained to be similar (EADP). The U_ij values of disordered atoms and aromatic carbon atoms of the toluene solvent we restrained using RIGU. Hydrogen atoms were placed in calculated positions and refined using a riding model with isotropic displacement parameters based on those of the parent atom [C—H = 0.95 Å, U_iso(H) = 1.2U_eqC for CH; C—H = 0.98 Å, U_iso(H) = 1.5U_eqC for CH₃; O—H = 0.84 Å, U_iso(H) = 1.5U_eqO for OH]. Two reflections, (131) and (243), were omitted owing to poor agreement between observed and calculated intensities.

Table 2
Experimental details

Crystal data
Chemical formula	[U(C₂₅H₂₃O₈)₂O₂(CH₄O)]·C₇H₈
M_r	1297.07
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	170
a, b, c (Å)	15.392 (4), 23.149 (6), 15.907 (4)
β (°)	90.577 (9)
V (Å³)	5668 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.94
Crystal size (mm)	0.25 × 0.18 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.595, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	35282, 5389, 4061
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.147, 1.12
No. of reflections	5389
No. of parameters	519
No. of restraints	561
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.50, −0.85
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009).

Supporting information

CCDC reference: 2536300

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002525/ej2019sup1.cif

checkCIF report

Computing details top

Bis[(1E,6E)-1,7-bis(4-acetyloxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dionato(1-)-κ²O,O'](methanol)dioxidouranium(VI) toluene monosolvate top

Crystal data top

[U(C₂₅H₂₃O₈)₂O₂(CH₄O)]·C₇H₈	F(000) = 2600
M_r = 1297.07	D_x = 1.520 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.392 (4) Å	Cell parameters from 9952 reflections
b = 23.149 (6) Å	θ = 3.0–25.8°
c = 15.907 (4) Å	µ = 2.94 mm⁻¹
β = 90.577 (9)°	T = 170 K
V = 5668 (3) Å³	Block, dark orange
Z = 4	0.25 × 0.18 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	4061 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.080
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 25.8°, θ_min = 3.0°
T_min = 0.595, T_max = 0.745	h = −16→18
35282 measured reflections	k = −28→28
5389 independent reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0669P)² + 25.8409P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
5389 reflections	Δρ_max = 1.50 e Å⁻³
519 parameters	Δρ_min = −0.85 e Å⁻³
561 restraints

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	Occ. (<1)
U1	0.500000	0.50545 (2)	0.250000	0.05680 (18)
O2	0.4046 (4)	0.5058 (2)	0.1867 (3)	0.0668 (14)
O1	0.4467 (4)	0.42789 (19)	0.3290 (3)	0.0598 (13)
O3	0.4215 (4)	0.5436 (2)	0.3633 (3)	0.0702 (15)
O38	0.3369 (5)	0.8280 (3)	0.5497 (5)	0.101 (2)
C1	0.4172 (5)	0.4220 (3)	0.4034 (5)	0.0526 (16)
C3	0.4021 (5)	0.5249 (3)	0.4367 (4)	0.0518 (16)
C10	0.4020 (5)	0.3630 (3)	0.4337 (5)	0.065 (2)
H10	0.372203	0.359431	0.485431	0.078*
C31	0.3808 (5)	0.6236 (3)	0.4885 (5)	0.0565 (18)
H31	0.393299	0.635888	0.432905	0.068*
C2	0.3978 (6)	0.4674 (3)	0.4561 (5)	0.064 (2)
H2	0.379594	0.457766	0.511265	0.077*
C32	0.3639 (5)	0.6697 (3)	0.5490 (5)	0.0613 (19)
C30	0.3811 (5)	0.5683 (3)	0.5006 (5)	0.0573 (18)
H30	0.366567	0.554765	0.555099	0.069*
C33	0.3596 (6)	0.7257 (3)	0.5195 (6)	0.068 (2)
H33	0.368408	0.733321	0.461522	0.081*
C11	0.4247 (6)	0.3157 (3)	0.3977 (5)	0.067 (2)
H11	0.456935	0.317462	0.347134	0.081*	0.508 (10)
H11A	0.448394	0.321125	0.343338	0.081*	0.492 (10)
C37	0.3525 (6)	0.6591 (4)	0.6338 (5)	0.076 (2)
H37	0.356872	0.620859	0.654994	0.091*
C35	0.3296 (6)	0.7600 (4)	0.6582 (6)	0.087 (3)
C36	0.3347 (7)	0.7049 (5)	0.6883 (6)	0.092 (3)
H36	0.326007	0.697645	0.746387	0.110*
C34	0.3424 (6)	0.7714 (4)	0.5748 (6)	0.079 (2)
C38	0.3590 (8)	0.8419 (4)	0.4648 (9)	0.105 (3)
H38A	0.326945	0.816480	0.426151	0.158*
H38B	0.421559	0.836469	0.456974	0.158*
H38C	0.343645	0.882193	0.453055	0.158*
C13B	0.3955 (14)	0.2404 (9)	0.4996 (15)	0.068 (5)	0.492 (10)
H13B	0.379701	0.270341	0.537332	0.081*	0.492 (10)
C14A	0.4087 (18)	0.1541 (10)	0.423 (2)	0.082 (5)	0.508 (10)
C15A	0.3589 (15)	0.1477 (8)	0.4939 (16)	0.080 (5)	0.508 (10)
C14B	0.3915 (13)	0.1834 (8)	0.5236 (13)	0.067 (5)	0.492 (10)
C17A	0.3467 (18)	0.2500 (10)	0.4994 (17)	0.095 (7)	0.508 (10)
H17A	0.319308	0.282185	0.524921	0.114*	0.508 (10)
C13A	0.432 (2)	0.2090 (11)	0.3961 (18)	0.076 (6)	0.508 (10)
H13A	0.471153	0.211618	0.350243	0.091*	0.508 (10)
C12A	0.403 (3)	0.2611 (9)	0.432 (3)	0.076 (7)	0.508 (10)
O19A	0.3334 (13)	0.0913 (6)	0.5193 (13)	0.113 (6)	0.508 (10)
C15B	0.4158 (17)	0.1413 (9)	0.4687 (17)	0.071 (5)	0.492 (10)
C16B	0.4473 (15)	0.1547 (8)	0.3931 (16)	0.069 (5)	0.492 (10)
H16B	0.468259	0.124917	0.357690	0.083*	0.492 (10)
O19B	0.4177 (12)	0.0840 (6)	0.4973 (12)	0.105 (5)	0.492 (10)
O18A	0.4415 (11)	0.1047 (6)	0.3896 (10)	0.105 (5)	0.508 (10)
C18A	0.4869 (17)	0.1098 (10)	0.3160 (15)	0.112 (8)	0.508 (10)
H18A	0.467598	0.144500	0.285845	0.167*	0.508 (10)
H18B	0.476328	0.075701	0.280881	0.167*	0.508 (10)
H18C	0.549152	0.112882	0.328795	0.167*	0.508 (10)
O18B	0.3646 (12)	0.1657 (6)	0.6016 (10)	0.106 (6)	0.492 (10)
C12B	0.421 (3)	0.2523 (11)	0.425 (3)	0.067 (9)	0.492 (10)
C18B	0.3392 (17)	0.2079 (9)	0.6574 (14)	0.104 (8)	0.492 (10)
H18D	0.297215	0.233722	0.629780	0.156*	0.492 (10)
H18E	0.390035	0.230257	0.675735	0.156*	0.492 (10)
H18F	0.312142	0.189845	0.706314	0.156*	0.492 (10)
C16A	0.327 (2)	0.1922 (9)	0.5336 (18)	0.110 (8)	0.508 (10)
H16A	0.292933	0.187613	0.582515	0.132*	0.508 (10)
O20B	0.2817 (14)	0.0707 (10)	0.4557 (15)	0.144 (8)	0.492 (10)
O20A	0.4621 (13)	0.0733 (7)	0.5756 (13)	0.127 (6)	0.508 (10)
C19B	0.350 (2)	0.0521 (13)	0.491 (2)	0.115 (8)	0.492 (10)
C19A	0.389 (2)	0.0561 (10)	0.554 (2)	0.116 (8)	0.508 (10)
O39B	0.303 (3)	0.7992 (17)	0.722 (3)	0.089 (8)	0.40 (2)
O40B	0.169 (2)	0.7907 (13)	0.688 (2)	0.095 (4)	0.40 (2)
C39B	0.228 (3)	0.8160 (16)	0.730 (3)	0.086 (7)	0.40 (2)
C40B	0.212 (3)	0.8665 (18)	0.784 (3)	0.126 (9)	0.40 (2)
H40A	0.218743	0.854929	0.843348	0.189*	0.40 (2)
H40B	0.153465	0.881114	0.774306	0.189*	0.40 (2)
H40C	0.254641	0.896842	0.771628	0.189*	0.40 (2)
O4	0.5292 (8)	0.6146 (4)	0.2494 (12)	0.080 (5)	0.5
H4	0.575033	0.615103	0.221182	0.120*	0.5
C4	0.540 (2)	0.6518 (13)	0.3234 (19)	0.176 (16)	0.5
H4A	0.545639	0.692077	0.305402	0.264*	0.5
H4B	0.592321	0.640222	0.354705	0.264*	0.5
H4C	0.489167	0.647879	0.359607	0.264*	0.5
C40A	0.2551 (17)	0.8910 (12)	0.761 (2)	0.126 (9)	0.60 (2)
H40D	0.283804	0.884775	0.815389	0.189*	0.60 (2)
H40E	0.196377	0.906008	0.769702	0.189*	0.60 (2)
H40F	0.288578	0.918836	0.728014	0.189*	0.60 (2)
C17B	0.450 (3)	0.2140 (11)	0.364 (2)	0.078 (7)	0.492 (10)
H17B	0.469024	0.225407	0.310347	0.093*	0.492 (10)
C20B	0.361 (10)	−0.003 (3)	0.534 (13)	0.17 (3)	0.37 (19)
H20A	0.324632	−0.003836	0.584783	0.258*	0.37 (19)
H20B	0.421930	−0.008150	0.550824	0.258*	0.37 (19)
H20C	0.343336	−0.034910	0.496940	0.258*	0.37 (19)
C53	0.2151 (14)	0.4419 (13)	0.242 (2)	0.170 (10)	0.5
H53	0.267406	0.454385	0.268713	0.203*	0.5
C54	0.173 (2)	0.4765 (10)	0.1843 (17)	0.169 (10)	0.5
H54	0.203863	0.506632	0.157169	0.203*	0.5
C55	0.087 (2)	0.4679 (12)	0.1655 (16)	0.187 (10)	0.5
H55	0.055147	0.495542	0.133126	0.224*	0.5
C56	0.0454 (15)	0.4182 (16)	0.195 (2)	0.216 (12)	0.5
H56	−0.015053	0.412627	0.184968	0.260*	0.5
C51	0.094 (2)	0.3768 (12)	0.238 (3)	0.214 (12)	0.5
C52	0.179 (2)	0.3887 (13)	0.261 (2)	0.206 (11)	0.5
H52	0.213200	0.360330	0.289331	0.247*	0.5
C20A	0.357 (6)	−0.0027 (18)	0.570 (9)	0.17 (3)	0.63 (19)
H20D	0.398901	−0.030934	0.549149	0.258*	0.63 (19)
H20E	0.300966	−0.008289	0.540742	0.258*	0.63 (19)
H20F	0.349027	−0.008060	0.630419	0.258*	0.63 (19)
O39A	0.3265 (15)	0.8105 (13)	0.7069 (18)	0.102 (8)	0.60 (2)
C39A	0.2499 (18)	0.8360 (11)	0.7152 (17)	0.086 (7)	0.60 (2)
O40A	0.1817 (15)	0.8166 (9)	0.6915 (14)	0.095 (4)	0.60 (2)
C50	0.051 (3)	0.3265 (17)	0.266 (3)	0.238 (18)	0.5
H50A	0.004228	0.337362	0.303933	0.358*	0.5
H50B	0.092790	0.301667	0.295870	0.358*	0.5
H50C	0.026877	0.305478	0.217622	0.358*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
U1	0.0993 (4)	0.0338 (2)	0.0371 (2)	0.000	−0.00774 (18)	0.000
O2	0.097 (4)	0.055 (3)	0.049 (3)	0.020 (3)	−0.009 (3)	−0.009 (2)
O1	0.082 (4)	0.039 (2)	0.059 (3)	−0.004 (2)	0.006 (3)	0.000 (2)
O3	0.113 (5)	0.045 (3)	0.052 (3)	0.007 (3)	0.006 (3)	−0.001 (2)
O38	0.117 (6)	0.062 (3)	0.123 (5)	0.021 (4)	−0.042 (5)	−0.034 (3)
C1	0.055 (5)	0.047 (3)	0.056 (4)	−0.006 (3)	−0.006 (3)	0.008 (3)
C3	0.054 (5)	0.055 (3)	0.046 (3)	0.007 (3)	−0.005 (3)	0.005 (3)
C10	0.070 (6)	0.057 (3)	0.067 (5)	−0.011 (4)	−0.001 (4)	0.008 (3)
C31	0.061 (5)	0.061 (3)	0.048 (4)	0.015 (3)	−0.002 (4)	−0.003 (3)
C2	0.080 (6)	0.054 (3)	0.058 (4)	0.001 (4)	0.002 (4)	0.006 (3)
C32	0.060 (5)	0.069 (4)	0.055 (4)	0.018 (4)	−0.018 (4)	−0.015 (3)
C30	0.063 (5)	0.059 (3)	0.050 (4)	0.007 (3)	−0.003 (4)	0.000 (3)
C33	0.070 (6)	0.063 (4)	0.069 (5)	0.017 (4)	−0.020 (4)	−0.019 (3)
C11	0.080 (6)	0.053 (3)	0.067 (5)	−0.009 (4)	−0.023 (4)	0.000 (3)
C37	0.082 (6)	0.087 (5)	0.059 (4)	0.033 (5)	−0.014 (4)	−0.016 (4)
C35	0.084 (6)	0.096 (5)	0.079 (5)	0.040 (5)	−0.036 (5)	−0.041 (4)
C36	0.103 (8)	0.113 (6)	0.059 (5)	0.043 (6)	−0.023 (5)	−0.031 (4)
C34	0.079 (6)	0.068 (4)	0.088 (5)	0.021 (4)	−0.032 (5)	−0.031 (4)
C38	0.106 (9)	0.063 (6)	0.147 (8)	0.001 (5)	−0.026 (8)	−0.006 (6)
C13B	0.069 (14)	0.054 (7)	0.080 (9)	0.006 (8)	−0.001 (10)	0.012 (7)
C14A	0.068 (17)	0.068 (7)	0.110 (16)	−0.024 (8)	−0.015 (10)	0.018 (8)
C15A	0.061 (13)	0.062 (7)	0.118 (13)	−0.025 (8)	−0.012 (9)	0.013 (7)
C14B	0.053 (11)	0.057 (7)	0.092 (9)	0.014 (8)	0.020 (9)	0.020 (6)
C17A	0.11 (2)	0.069 (9)	0.103 (15)	0.002 (11)	−0.014 (13)	0.016 (9)
C13A	0.085 (18)	0.057 (7)	0.085 (16)	−0.017 (8)	−0.035 (11)	0.017 (8)
C12A	0.065 (18)	0.058 (7)	0.103 (16)	−0.019 (11)	−0.044 (10)	0.010 (10)
O19A	0.118 (13)	0.067 (7)	0.153 (15)	−0.028 (7)	−0.005 (11)	0.038 (8)
C15B	0.056 (14)	0.057 (6)	0.100 (11)	−0.009 (7)	−0.002 (10)	0.002 (6)
C16B	0.057 (14)	0.051 (7)	0.098 (11)	−0.004 (8)	0.005 (9)	−0.011 (7)
O19B	0.118 (12)	0.052 (6)	0.146 (15)	−0.004 (6)	0.002 (11)	0.017 (7)
O18A	0.150 (14)	0.070 (7)	0.097 (10)	−0.021 (7)	0.009 (8)	0.012 (6)
C18A	0.13 (2)	0.091 (14)	0.109 (15)	−0.017 (13)	0.016 (12)	0.019 (11)
O18B	0.156 (15)	0.061 (7)	0.101 (9)	0.004 (8)	0.050 (10)	0.022 (6)
C12B	0.08 (2)	0.053 (6)	0.066 (10)	0.018 (9)	−0.015 (11)	0.001 (7)
C18B	0.13 (2)	0.089 (12)	0.092 (13)	0.014 (13)	0.050 (14)	0.024 (9)
C16A	0.13 (2)	0.067 (8)	0.129 (18)	−0.032 (11)	0.009 (14)	−0.003 (9)
O20B	0.128 (14)	0.147 (16)	0.156 (19)	−0.053 (12)	−0.006 (13)	0.021 (13)
O20A	0.145 (14)	0.092 (10)	0.142 (15)	−0.005 (9)	−0.031 (12)	0.019 (10)
C19B	0.135 (16)	0.086 (12)	0.12 (2)	−0.033 (11)	0.015 (15)	0.007 (13)
C19A	0.149 (16)	0.069 (10)	0.13 (2)	−0.013 (9)	−0.027 (16)	0.013 (12)
O39B	0.101 (13)	0.089 (13)	0.075 (11)	0.045 (12)	−0.023 (11)	−0.028 (10)
O40B	0.101 (8)	0.097 (13)	0.086 (6)	0.022 (10)	−0.016 (5)	−0.023 (10)
C39B	0.089 (11)	0.096 (13)	0.073 (11)	0.033 (8)	−0.020 (8)	−0.013 (11)
C40B	0.078 (17)	0.122 (17)	0.18 (2)	0.026 (10)	−0.012 (14)	−0.072 (17)
O4	0.120 (16)	0.048 (5)	0.074 (7)	−0.010 (5)	0.054 (12)	−0.004 (6)
C4	0.18 (3)	0.18 (3)	0.18 (2)	−0.10 (2)	0.11 (2)	−0.11 (2)
C40A	0.078 (17)	0.122 (17)	0.18 (2)	0.026 (10)	−0.012 (14)	−0.072 (17)
C17B	0.097 (19)	0.056 (8)	0.081 (15)	−0.003 (10)	0.002 (14)	−0.008 (8)
C20B	0.199 (19)	0.063 (7)	0.26 (7)	−0.015 (9)	0.03 (4)	0.021 (19)
C53	0.154 (18)	0.129 (17)	0.23 (3)	0.002 (13)	0.061 (17)	−0.079 (16)
C54	0.21 (2)	0.120 (16)	0.18 (2)	−0.029 (15)	0.033 (18)	−0.094 (14)
C55	0.19 (2)	0.17 (2)	0.20 (3)	−0.020 (17)	0.04 (2)	−0.035 (19)
C56	0.21 (2)	0.19 (2)	0.24 (3)	−0.054 (17)	−0.02 (2)	−0.01 (2)
C51	0.22 (2)	0.16 (2)	0.26 (3)	−0.051 (16)	−0.01 (2)	−0.019 (19)
C52	0.20 (2)	0.165 (19)	0.25 (3)	−0.029 (16)	0.01 (2)	−0.034 (19)
C20A	0.199 (19)	0.063 (7)	0.26 (7)	−0.015 (9)	0.03 (4)	0.021 (19)
O39A	0.085 (10)	0.117 (11)	0.104 (15)	0.027 (9)	−0.017 (9)	−0.069 (12)
C39A	0.089 (11)	0.096 (13)	0.073 (11)	0.033 (8)	−0.020 (8)	−0.013 (11)
O40A	0.101 (8)	0.097 (13)	0.086 (6)	0.022 (10)	−0.016 (5)	−0.023 (10)
C50	0.24 (3)	0.15 (3)	0.32 (5)	−0.05 (2)	0.01 (4)	−0.02 (3)

Geometric parameters (Å, º) top

U1—O2	1.772 (6)	C15B—O19B	1.40 (2)
U1—O2ⁱ	1.772 (6)	C16B—H16B	0.9500
U1—O1ⁱ	2.345 (5)	C16B—C17B	1.45 (3)
U1—O1	2.345 (5)	O19B—C19B	1.28 (3)
U1—O3ⁱ	2.351 (5)	O18A—C18A	1.37 (2)
U1—O3	2.351 (5)	C18A—H18A	0.9800
U1—O4ⁱ	2.567 (9)	C18A—H18B	0.9800
U1—O4	2.567 (9)	C18A—H18C	0.9800
O1—C1	1.279 (8)	O18B—C18B	1.38 (2)
O3—C3	1.283 (9)	C12B—C17B	1.39 (3)
O38—C34	1.372 (12)	C18B—H18D	0.9800
O38—C38	1.434 (14)	C18B—H18E	0.9800
C1—C10	1.468 (10)	C18B—H18F	0.9800
C1—C2	1.379 (11)	C16A—H16A	0.9500
C3—C2	1.370 (11)	O20B—C19B	1.26 (4)
C3—C30	1.468 (10)	O20A—C19A	1.24 (3)
C10—H10	0.9500	C19B—C20B	1.47 (5)
C10—C11	1.286 (11)	C19A—C20A	1.47 (5)
C31—H31	0.9500	O39B—C39B	1.23 (4)
C31—C32	1.462 (10)	O40B—C39B	1.26 (4)
C31—C30	1.295 (10)	C39B—C40B	1.48 (2)
C2—H2	0.9500	C40B—H40A	0.9800
C32—C33	1.380 (11)	C40B—H40B	0.9800
C32—C37	1.384 (11)	C40B—H40C	0.9800
C30—H30	0.9500	O4—H4	0.8400
C33—H33	0.9500	O4—C4	1.47 (3)
C33—C34	1.403 (11)	C4—H4A	0.9800
C11—H11	0.9500	C4—H4B	0.9800
C11—H11A	0.9500	C4—H4C	0.9800
C11—C12A	1.418 (18)	C40A—H40D	0.9800
C11—C12B	1.53 (3)	C40A—H40E	0.9800
C37—H37	0.9500	C40A—H40F	0.9800
C37—C36	1.398 (11)	C40A—C39A	1.466 (19)
C35—C36	1.364 (15)	C17B—H17B	0.9500
C35—C34	1.369 (14)	C20B—H20A	0.9800
C35—O39B	1.42 (4)	C20B—H20B	0.9800
C35—O39A	1.40 (3)	C20B—H20C	0.9800
C36—H36	0.9500	C53—H53	0.9500
C38—H38A	0.9800	C53—C54	1.378 (10)
C38—H38B	0.9800	C53—C52	1.383 (10)
C38—H38C	0.9800	C54—H54	0.9500
C13B—H13B	0.9500	C54—C55	1.375 (10)
C13B—C14B	1.38 (3)	C55—H55	0.9500
C13B—C12B	1.28 (4)	C55—C56	1.395 (10)
C14A—C15A	1.38 (3)	C56—H56	0.9500
C14A—C13A	1.39 (3)	C56—C51	1.392 (10)
C14A—O18A	1.36 (3)	C51—C52	1.391 (10)
C15A—O19A	1.423 (15)	C51—C50	1.41 (4)
C15A—C16A	1.31 (3)	C52—H52	0.9500
C14B—C15B	1.36 (3)	C20A—H20D	0.9800
C14B—O18B	1.37 (2)	C20A—H20E	0.9800
C17A—H17A	0.9500	C20A—H20F	0.9800
C17A—C12A	1.41 (4)	O39A—C39A	1.33 (3)
C17A—C16A	1.48 (3)	C39A—O40A	1.20 (3)
C13A—H13A	0.9500	C50—H50A	0.9800
C13A—C12A	1.41 (4)	C50—H50B	0.9800
O19A—C19A	1.30 (3)	C50—H50C	0.9800
C15B—C16B	1.34 (3)

O2—U1—O2ⁱ	179.5 (3)	C16B—C15B—C14B	121 (2)
O2ⁱ—U1—O1ⁱ	90.9 (2)	C16B—C15B—O19B	120 (2)
O2ⁱ—U1—O1	89.5 (2)	C15B—C16B—H16B	119.5
O2—U1—O1ⁱ	89.5 (2)	C15B—C16B—C17B	121 (2)
O2—U1—O1	90.9 (2)	C17B—C16B—H16B	119.5
O2—U1—O3ⁱ	89.5 (2)	C19B—O19B—C15B	120 (2)
O2ⁱ—U1—O3	89.5 (2)	C14A—O18A—C18A	117.0 (19)
O2ⁱ—U1—O3ⁱ	90.3 (2)	O18A—C18A—H18A	109.5
O2—U1—O3	90.3 (2)	O18A—C18A—H18B	109.5
O2ⁱ—U1—O4	81.6 (4)	O18A—C18A—H18C	109.5
O2ⁱ—U1—O4ⁱ	97.9 (4)	H18A—C18A—H18B	109.5
O2—U1—O4ⁱ	81.6 (4)	H18A—C18A—H18C	109.5
O2—U1—O4	97.9 (4)	H18B—C18A—H18C	109.5
O1ⁱ—U1—O1	80.0 (2)	C14B—O18B—C18B	117.4 (15)
O1—U1—O3ⁱ	152.09 (18)	C13B—C12B—C11	119 (2)
O1—U1—O3	72.05 (17)	C13B—C12B—C17B	128 (2)
O1ⁱ—U1—O3ⁱ	72.05 (17)	C17B—C12B—C11	113 (2)
O1ⁱ—U1—O3	152.09 (18)	O18B—C18B—H18D	109.5
O1ⁱ—U1—O4ⁱ	144.9 (4)	O18B—C18B—H18E	109.5
O1—U1—O4	144.9 (4)	O18B—C18B—H18F	109.5
O1ⁱ—U1—O4	133.6 (3)	H18D—C18B—H18E	109.5
O1—U1—O4ⁱ	133.6 (3)	H18D—C18B—H18F	109.5
O3ⁱ—U1—O3	135.9 (2)	H18E—C18B—H18F	109.5
O3ⁱ—U1—O4ⁱ	74.0 (3)	C15A—C16A—C17A	117 (3)
O3ⁱ—U1—O4	62.4 (3)	C15A—C16A—H16A	121.4
O3—U1—O4	74.0 (3)	C17A—C16A—H16A	121.4
O3—U1—O4ⁱ	62.4 (3)	O19B—C19B—C20B	112 (7)
O4—U1—O4ⁱ	20.2 (6)	O20B—C19B—O19B	121 (3)
C1—O1—U1	135.0 (4)	O20B—C19B—C20B	127 (6)
C3—O3—U1	134.2 (5)	O19A—C19A—C20A	116 (4)
C34—O38—C38	118.3 (8)	O20A—C19A—O19A	121 (2)
O1—C1—C10	117.5 (7)	O20A—C19A—C20A	124 (4)
O1—C1—C2	124.3 (6)	C39B—O39B—C35	123 (3)
C2—C1—C10	118.2 (7)	O39B—C39B—O40B	118 (3)
O3—C3—C2	123.1 (7)	O39B—C39B—C40B	118 (4)
O3—C3—C30	117.1 (6)	O40B—C39B—C40B	124 (3)
C2—C3—C30	119.8 (7)	C39B—C40B—H40A	109.5
C1—C10—H10	116.5	C39B—C40B—H40B	109.5
C11—C10—C1	126.9 (8)	C39B—C40B—H40C	109.5
C11—C10—H10	116.5	H40A—C40B—H40B	109.5
C32—C31—H31	115.7	H40A—C40B—H40C	109.5
C30—C31—H31	115.7	H40B—C40B—H40C	109.5
C30—C31—C32	128.5 (8)	U1—O4—H4	99.4
C1—C2—H2	116.8	C4—O4—U1	126.4 (17)
C3—C2—C1	126.3 (7)	C4—O4—H4	109.5
C3—C2—H2	116.8	O4—C4—O4ⁱ	30.1 (9)
C33—C32—C31	118.0 (7)	O4ⁱ—C4—H4A	108.8
C33—C32—C37	119.5 (7)	O4—C4—H4A	109.5
C37—C32—C31	122.6 (7)	O4ⁱ—C4—H4B	132.8
C3—C30—H30	117.5	O4—C4—H4B	109.5
C31—C30—C3	125.0 (7)	O4—C4—H4C	109.5
C31—C30—H30	117.5	O4ⁱ—C4—H4C	82.1
C32—C33—H33	119.9	H4A—C4—H4B	109.5
C32—C33—C34	120.2 (9)	H4A—C4—H4C	109.5
C34—C33—H33	119.9	H4B—C4—H4C	109.5
C10—C11—H11	119.2	H40D—C40A—H40E	109.5
C10—C11—H11A	113.7	H40D—C40A—H40F	109.5
C10—C11—C12A	121.6 (17)	H40E—C40A—H40F	109.5
C10—C11—C12B	132.6 (15)	C39A—C40A—H40D	109.5
C12A—C11—H11	119.2	C39A—C40A—H40E	109.5
C12B—C11—H11A	113.7	C39A—C40A—H40F	109.5
C32—C37—H37	120.1	C16B—C17B—H17B	124.0
C32—C37—C36	119.9 (9)	C12B—C17B—C16B	112 (2)
C36—C37—H37	120.1	C12B—C17B—H17B	124.0
C36—C35—C34	120.8 (8)	C19B—C20B—H20A	109.5
C36—C35—O39B	111 (2)	C19B—C20B—H20B	109.5
C36—C35—O39A	125.9 (16)	C19B—C20B—H20C	109.5
C34—C35—O39B	127.8 (19)	H20A—C20B—H20B	109.5
C34—C35—O39A	112.4 (17)	H20A—C20B—H20C	109.5
C37—C36—H36	119.9	H20B—C20B—H20C	109.5
C35—C36—C37	120.1 (10)	C54—C53—H53	120.8
C35—C36—H36	119.9	C54—C53—C52	118.4 (10)
O38—C34—C33	123.3 (10)	C52—C53—H53	120.8
C35—C34—O38	117.2 (8)	C53—C54—H54	119.7
C35—C34—C33	119.5 (9)	C55—C54—C53	120.6 (10)
O38—C38—H38A	109.5	C55—C54—H54	119.7
O38—C38—H38B	109.5	C54—C55—H55	120.4
O38—C38—H38C	109.5	C54—C55—C56	119.3 (10)
H38A—C38—H38B	109.5	C56—C55—H55	120.4
H38A—C38—H38C	109.5	C55—C56—H56	120.4
H38B—C38—H38C	109.5	C51—C56—C55	119.2 (10)
C14B—C13B—H13B	120.7	C51—C56—H56	120.4
C12B—C13B—H13B	120.7	C56—C51—C50	118 (3)
C12B—C13B—C14B	119 (2)	C52—C51—C56	119.7 (10)
C15A—C14A—C13A	120 (3)	C52—C51—C50	121 (3)
O18A—C14A—C15A	116 (2)	C53—C52—C51	119.8 (10)
O18A—C14A—C13A	123 (3)	C53—C52—H52	120.1
C14A—C15A—O19A	119 (2)	C51—C52—H52	120.1
C16A—C15A—C14A	122 (2)	C19A—C20A—H20D	109.5
C16A—C15A—O19A	119 (2)	C19A—C20A—H20E	109.5
C15B—C14B—C13B	120 (2)	C19A—C20A—H20F	109.5
C15B—C14B—O18B	116.9 (18)	H20D—C20A—H20E	109.5
O18B—C14B—C13B	123.5 (19)	H20D—C20A—H20F	109.5
C12A—C17A—H17A	117.4	H20E—C20A—H20F	109.5
C12A—C17A—C16A	125 (2)	C39A—O39A—C35	117.5 (19)
C16A—C17A—H17A	117.4	O39A—C39A—C40A	113 (2)
C14A—C13A—H13A	117.5	O40A—C39A—C40A	122 (2)
C14A—C13A—C12A	125 (3)	O40A—C39A—O39A	125 (2)
C12A—C13A—H13A	117.5	C51—C50—H50A	109.5
C17A—C12A—C11	127 (3)	C51—C50—H50B	109.5
C13A—C12A—C11	122 (3)	C51—C50—H50C	109.5
C13A—C12A—C17A	110.6 (18)	H50A—C50—H50B	109.5
C19A—O19A—C15A	121 (2)	H50A—C50—H50C	109.5
C14B—C15B—O19B	118 (2)	H50B—C50—H50C	109.5

U1—O1—C1—C10	−171.1 (5)	C14A—C15A—O19A—C19A	74 (3)
U1—O1—C1—C2	9.9 (12)	C14A—C15A—C16A—C17A	0 (4)
U1—O3—C3—C2	−24.7 (12)	C14A—C13A—C12A—C11	−176 (3)
U1—O3—C3—C30	157.3 (5)	C14A—C13A—C12A—C17A	1 (5)
U1—O4—C4—O4ⁱ	−81.2 (15)	C15A—C14A—C13A—C12A	−6 (5)
O1—C1—C10—C11	9.0 (12)	C15A—C14A—O18A—C18A	176 (2)
O1—C1—C2—C3	3.7 (13)	C15A—O19A—C19A—O20A	10 (4)
O3—C3—C2—C1	3.5 (13)	C15A—O19A—C19A—C20A	−174 (6)
O3—C3—C30—C31	−0.1 (12)	C14B—C13B—C12B—C11	179 (3)
C1—C10—C11—C12A	−177 (2)	C14B—C13B—C12B—C17B	−3 (7)
C1—C10—C11—C12B	173 (3)	C14B—C15B—C16B—C17B	−5 (4)
C10—C1—C2—C3	−175.3 (7)	C14B—C15B—O19B—C19B	90 (3)
C10—C11—C12A—C17A	9 (6)	C13A—C14A—C15A—O19A	178 (3)
C10—C11—C12A—C13A	−176 (3)	C13A—C14A—C15A—C16A	5 (4)
C10—C11—C12B—C13B	−4 (6)	C13A—C14A—O18A—C18A	−13 (4)
C10—C11—C12B—C17B	178 (2)	C12A—C17A—C16A—C15A	−6 (5)
C31—C32—C33—C34	179.2 (8)	O19A—C15A—C16A—C17A	−173 (2)
C31—C32—C37—C36	−178.6 (8)	C15B—C14B—O18B—C18B	−179 (2)
C2—C1—C10—C11	−171.9 (8)	C15B—C16B—C17B—C12B	3 (5)
C2—C3—C30—C31	−178.1 (8)	C15B—O19B—C19B—O20B	3 (5)
C32—C31—C30—C3	−177.6 (7)	C15B—O19B—C19B—C20B	−172 (9)
C32—C33—C34—O38	−179.7 (8)	C16B—C15B—O19B—C19B	−98 (3)
C32—C33—C34—C35	−0.1 (14)	O19B—C15B—C16B—C17B	−177 (3)
C32—C37—C36—C35	−0.9 (15)	O18A—C14A—C15A—O19A	−10 (3)
C30—C3—C2—C1	−178.6 (8)	O18A—C14A—C15A—C16A	177 (2)
C30—C31—C32—C33	−174.3 (8)	O18A—C14A—C13A—C12A	−177 (3)
C30—C31—C32—C37	6.0 (14)	O18B—C14B—C15B—C16B	−176 (2)
C33—C32—C37—C36	1.7 (13)	O18B—C14B—C15B—O19B	−5 (3)
C11—C12B—C17B—C16B	179 (3)	C12B—C13B—C14B—C15B	1 (4)
C37—C32—C33—C34	−1.2 (13)	C12B—C13B—C14B—O18B	−180 (3)
C35—O39B—C39B—O40B	12 (7)	C16A—C15A—O19A—C19A	−113 (3)
C35—O39B—C39B—C40B	−166 (4)	C16A—C17A—C12A—C11	−179 (3)
C35—O39A—C39A—C40A	−175 (2)	C16A—C17A—C12A—C13A	5 (5)
C35—O39A—C39A—O40A	8 (5)	O39B—C35—C36—C37	174.6 (19)
C36—C35—C34—O38	−179.5 (9)	O39B—C35—C34—O38	6 (3)
C36—C35—C34—C33	0.9 (15)	O39B—C35—C34—C33	−173 (2)
C36—C35—O39B—C39B	−98 (4)	C53—C54—C55—C56	−11 (2)
C36—C35—O39A—C39A	−103 (3)	C54—C53—C52—C51	−15 (5)
C34—C35—C36—C37	−0.4 (16)	C54—C55—C56—C51	−4 (2)
C34—C35—O39B—C39B	76 (5)	C55—C56—C51—C52	8 (5)
C34—C35—O39A—C39A	88 (3)	C55—C56—C51—C50	−180 (4)
C38—O38—C34—C33	−6.9 (14)	C56—C51—C52—C53	1 (5)
C38—O38—C34—C35	173.5 (9)	C52—C53—C54—C55	20 (4)
C13B—C14B—C15B—C16B	3 (3)	O39A—C35—C36—C37	−168.9 (14)
C13B—C14B—C15B—O19B	175 (2)	O39A—C35—C34—O38	−9.5 (16)
C13B—C14B—O18B—C18B	1 (3)	O39A—C35—C34—C33	170.8 (12)
C13B—C12B—C17B—C16B	1 (7)	C50—C51—C52—C53	−171 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O40Aⁱⁱ	0.84	2.33	2.99 (2)	136
O4—H4···O40Bⁱⁱ	0.84	2.67	3.23 (4)	125
C40A—H40D···O20Bⁱⁱⁱ	0.98	2.46	3.25 (4)	137
C30—H30···O2ⁱⁱⁱ	0.95	2.58	3.436 (9)	150

Symmetry codes: (ii) x+1/2, −y+3/2, z−1/2; (iii) x, −y+1, z+1/2.

Funding information

Funding for this research was provided by: Vietnam National University, Hanoi (grant No. QG.23.76 to Van Ha Nguyen).

References

Ainscough, E. W., Brodie, A. M., Cresswell, R. J. & Waters, J. M. (1998). Inorg. Chim. Acta 277, 37–45. Web of Science CSD CrossRef CAS Google Scholar
Al-Anber, M. A., Daoud, H. M., Rüffer, T. & Lang, H. (2011). J. Mol. Struct. 997, 1–6. CAS Google Scholar
Banerjee, S. & Chakravarty, A. R. (2015). Acc. Chem. Res. 48, 2075–2083. Web of Science CrossRef CAS PubMed Google Scholar
Bhagat, K. K., Cheke, R. S., Gavali, V. D., Kharkar, P. S. & Arote, N. D. (2025). Discov. Chem. 2, 119. CrossRef Google Scholar
Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carter, K. P., Kerr, A. T., Taydakov, I. V. & Cahill, C. L. (2018). Solid State Sci. 76, 20–32. Web of Science CSD CrossRef CAS Google Scholar
Clark, C. B., Burnett, N. L., Ruhren, A. N., Talbott, E. D., Eyubova, E., Besson, C., Panetier, J. A. & Swierk, J. R. (2025). Dalton Trans. 54, 12667–12677. Web of Science CSD CrossRef CAS PubMed Google Scholar
Dai, C., Lin, J., Li, H., Shen, Z., Wang, Y., Velkov, T. & Shen, J. (2022). Antioxidants 11, 459. Web of Science CrossRef PubMed Google Scholar
Dehzad, M. J., Ghalandari, H., Nouri, M. & Askarpour, M. (2023). Cytokine 164, 156144. Web of Science CrossRef PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Esatbeyoglu, T., Huebbe, P., Ernst, I. M. A., Chin, D., Wagner, A. E. & Rimbach, G. (2012). Angew. Chem. Int. Ed. 51, 5308–5332. Web of Science CrossRef CAS Google Scholar
Goel, A., Kunnumakkara, A. B. & Aggarwal, B. B. (2008). Biochem. Pharmacol. 75, 787–809. Web of Science CrossRef PubMed CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hernandez, A., Chakraborty, I., Ortega, G. & Dares, C. J. (2022). Acta Cryst. E78, 40–43. Web of Science CSD CrossRef IUCr Journals Google Scholar
Huuskonen, J., Raatikainen, K. & Rissanen, K. (2007). Acta Cryst. E63, m413–m414. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jabborova, X., Tursinboyeva, X., Ruzieva, B., Turgunov, K., Ashurov, J., Tojiboev, A. & Daminova, S. (2024). Acta Cryst. E80, 1250–1254. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kawasaki, T. & Kitazawa, T. (2015). Acta Cryst. E71, 42–44. CSD CrossRef IUCr Journals Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Kurzajewska, M., Kwiatek, D., Kubicki, M., Brzezinski, B. & Hnatejko, Z. (2018). Polyhedron 148, 1–8. Web of Science CSD CrossRef CAS Google Scholar
Ma, Z., Sutradhar, M., Gurbanov, A. V., Maharramov, A. M., Aliyeva, R. A., Aliyeva, F. S., Bahmanova, F. N., Mardanova, V. I., Chyragov, F. M. & Mahmudov, K. T. (2015). Polyhedron 101, 14–22. Web of Science CSD CrossRef CAS Google Scholar
Menon, V. P. & Sudheer, A. R. (2007). The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease edited by B. B. Aggarwal, Y.-J. Surh & S. Shishodia, pp. 105–125. Boston: Springer US. Google Scholar
Meza-Morales, W., Alvarez-Ricardo, Y., Obregón-Mendoza, M. A., Arenaza-Corona, A., Ramírez-Apan, M. T., Toscano, R. A., Poveda-Jaramillo, J. C. & Enríquez, R. G. (2023b). RSC Adv. 13, 8577–8585. Web of Science CAS PubMed Google Scholar
Meza-Morales, W., Alvarez-Ricardo, Y., Pérez-González, L. L., Tavera-Hernández, R., Ramírez-Apan, M. T., Toscano, R. A., Sánchez-Obregón, R., Obregón-Mendoza, M. A. & Enríquez, R. G. (2023a). Int. J. Mol. Sci. 24, 16324. Web of Science PubMed Google Scholar
Meza-Morales, W., Estévez-Carmona, M. M., Alvarez-Ricardo, Y., Obregón-Mendoza, M. A., Cassani, J., Ramírez-Apan, M. T., Escobedo-Martínez, C., Soriano-García, M., Reynolds, W. F. & Enríquez, R. G. (2019). Molecules 24, 1598. Web of Science PubMed Google Scholar
Monzón González, C. R., Sánchez Vergara, M. E., Elías-Espinosa, M. C., Rodríguez-Valencia, S. A., López-Mayorga, B. J., Castillo-Arroyave, J. L., Toscano, R. A., Flores, O. L. & Álvarez Toledano, C. (2024). ChemistryOpen 13, e202300219. Web of Science PubMed Google Scholar
Pham, C. T., Pham, T. T., Nguyen, H. H. & Trieu, T. N. (2020). Z. Anorg. Allg. Chem. 646, 495–499. Web of Science CSD CrossRef CAS Google Scholar
Prasad, S., DuBourdieu, D., Srivastava, A., Kumar, P. & Lall, R. (2021). Int. J. Mol. Sci. 22, 7094. Web of Science CrossRef PubMed Google Scholar
Salem, M., Rohani, S. & Gillies, E. R. (2014). RSC Adv. 4, 10815–10829. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tafeenko, V. A., Chernyshev, V. V., Kochetov, A. N., Sergeenkova, A. A., Nosikova, L. A., Kudryashova, Z. A. & Tsivadze, A. Yu. (2025). CSD Communication (refcodes IMICEQ and IMICIU). CCDC, Cambridge, England. Google Scholar
Vats, B. G., Kannan, S., Parvathi, K., Maity, D. K. & Drew, M. G. B. (2015). Polyhedron 89, 116–121. Web of Science CSD CrossRef CAS Google Scholar
Wang, J., Wei, D., Jiang, B., Liu, T., Ni, J. & Zhou, S. (2014). Transition Met. Chem. 39, 553–558. Web of Science CSD CrossRef CAS Google Scholar
Wanninger, S., Lorenz, V., Subhan, A. & Edelmann, F. T. (2015). Chem. Soc. Rev. 44, 4986–5002. 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.