Crystal structure of poly[[hexa­aqua­tris­(μ-3,6-di­oxo­cyclo­hexa-1,4-diene-1,4-diolato)dierbium(III)] octa­deca­hydrate]

Ponjan, N.; Kodchasanthong, K.; Jiajaroen, S.; Chainok, K.

doi:10.1107/S2056989018017516

research communications

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ISSN: 2056-9890

Volume 75| Part 1| January 2019| Pages 64-67

https://doi.org/10.1107/S2056989018017516

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Crystal structure of poly[[hexaaquatris(μ-3,6-dioxocyclohexa-1,4-diene-1,4-diolato)dierbium(III)] octadecahydrate]

Nutcha Ponjan,^a Kenika Kodchasanthong,^a Suwadee Jiajaroen ^b and Kittipong Chainok ^a ^*

^aMaterials and Textile Technology, Faculty of Science and Technology, Thammasat University, Khlong Luang, Pathum Thani 12121, Thailand, and ^bDivision of Chemistry, Faculty of Science and Technology, Thammasat University, Khlong Luang, Pathum Thani 12121, Thailand
^*Correspondence e-mail: kc@tu.ac.th

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 November 2018; accepted 11 December 2018; online 1 January 2019)

The title lanthanide complex, [Er₂(C₆H₂O₄)₃(H₂O)₆]·18H₂O, is isostructural with its La, Gd, Yb and Lu analogues. The Er³⁺ ion, located on a threefold rotation axis, is nine-coordinated in a distorted tricapped trigonal–prismatic geometry, which is completed by six oxygen atoms from three dhbq²⁻ ligands and three oxygen atoms from coordinated water molecules. Each dhbq²⁻ ligand acts in a μ₂-bis(bidentate) bridging mode to connect two Er³⁺ ions to form honeycomb (6,3) two-dimensional sheets extending in the ab plane, having an Er⋯Er separation of 8.7261 (2) Å. In the crystal, extensive O—H⋯O hydrogen-bonding interactions involving the coordinated water molecules and the water molecules of crystallization, as well as the oxygen atoms of the dhbq²⁻ ligands, generate an overall three-dimensional supramolecular network.

Keywords: crystal structure; coordination polymers; dioxybenzoquinone; erbium(III); lanthanide.

CCDC reference: 1884389

1. Chemical context

Over the past few decades, lanthanide-based coordination polymers (LnCPs) have attracted significant attention because their high photoluminescence efficiency and long luminescence lifetime in lighting and full-colour displays (Parker, 2000 ; Bünzli & Piguet, 2005 ; Cui et al., 2018 ). Besides transition metal ions, lanthanide ions feature high coordination numbers and flexible coordination geometries, which facilitate the formation of diverse extended structures. Since lanthanide(III) ions have a high affinity to hard donor atoms, ligands containing oxygen atoms such as carboxylic acids (Xu et al., 2016 ), phosphoric acids (Mao, 2007 ), calixarenes (Ovsyannikov et al., 2017 ) and β-diketones (Vigato et al., 2009 ) have been used extensively in the synthesis of new types of LnCPs. On the basis of the above considerations, we selected 2,5-dihydroxy-1,4-benzoquinone (H₂dhbq) as the ligand to react with erbium(III) nitrate hexahydrate under solvothermal conditions to construct a new erbium(III)-based CP, [Er₂(dhbq)₃(H₂O)₆]·18H₂O, (I), which is isotypic with its La, Gd, Yb and Lu analogues (Abrahams et al., 2002 ). Herein, we report its structure.

2. Structural commentary

The asymmetric unit of (I) contains one third of an Er³⁺ ion, half of a dhbq²⁻ ligand, one coordinated water molecule and three water molecules of crystallization. The Er³⁺ ion is located on a threefold rotation axis, whereas the complete dhbq²⁻ anion is generated by a crystallographic inversion center. As can be seen from Fig. 1, the Er³⁺ ion is nine-coordinated by six oxygen atoms from three different dhbq²⁻ ligands and three other oxygen atoms from three coordinated water molecules. The coordination polyhedron of the central Er³⁺ ion can best be described as having a distorted tricapped trigonal–prismatic geometry, as depicted in Fig. 2, in which the O—Er—O bond angles range from 65.01 (5) to 139.97 (7)°. The Er—O bond lengths in the title complex lie between 2.3577 (15) and 2.4567 (15) Å, mean 2.393 Å. The whole dhbq²⁻ anion is nearly planar: the r.m.s. deviation from the mean plane through all of the non-H atoms is 0.021 Å, with a maximum displacement from this plane of 0.033 (2) Å for atom C2. As can be seen from Fig. 3, the dhbq²⁻ ligand acts in a μ₂-bis(bidentate) bridging mode, connecting two Er³⁺ ions to form a honeycomb (6,3) sheet extending in the ab plane, having a Er⋯Er separation of 8.7261 (2) Å.

Figure 1
The molecular structure of the title complex, showing selected atom labels. Displacement ellipsoids are drawn at the 50% probability level. Symmetry codes: (i) 1 + y − x, 1 − x, z; (ii) 1 − y, x − y, z.

Figure 2
View of the distorted tricapped trigonal–prismatic geometry of the central Er^III ion in the title complex. Symmetry codes: (i) 1 + y − x, 1 − x, z; (ii) 1 − y, x − y, z.

Figure 3
View of the honeycomb (6,3) sheet extending normal to the c-axis direction.

3. Supramolecular features

In the crystal, extensive O—H⋯O hydrogen-bonding interactions (Table 1) are observed between the oxygen atoms of the coordinated (O3) and lattice (O4 and O5) water molecules as well as between the water (O5 and O6) molecules of crystallization. Other O—H⋯O hydrogen-bonding interactions involve O6 and the dhbq²⁻ oxygen atom, and this interaction further links neighbouring sheets into a three-dimensional supramolecular structure (Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O6ⁱ	0.83 (1)	1.94 (1)	2.769 (3)	174 (3)
O3—H3B⋯O5ⁱⁱ	0.84 (1)	1.94 (1)	2.758 (3)	165 (3)
O4—H4A⋯O2ⁱⁱⁱ	0.84 (1)	1.92 (1)	2.738 (3)	167 (4)
O4—H4B⋯O4^iv	0.84 (1)	1.98 (1)	2.803 (3)	164 (4)
O5—H5A⋯O1^v	0.85 (1)	2.09 (3)	2.870 (3)	153 (5)
O5—H5B⋯O6^vi	0.84 (1)	1.95 (1)	2.794 (3)	174 (5)
O6—H6A⋯O4^vii	0.85 (1)	1.88 (1)	2.725 (3)	174 (4)
O6—H6B⋯O5	0.84 (1)	1.91 (1)	2.747 (3)	169 (5)
Symmetry codes: (i) $[x-y+{\script{2\over 3}}, x+{\script{1\over 3}}, -z+{\script{4\over 3}}]$ ; (ii) $[-x+{\script{2\over 3}}, -y+{\script{1\over 3}}, -z+{\script{4\over 3}}]$ ; (iii) -x+y+1, -x+1, z; (iv) $[x-y+{\script{1\over 3}}, x-{\script{1\over 3}}, -z+{\script{2\over 3}}]$ ; (v) -y+1, x-y, z; (vi) y, -x+y, -z+1; (vii) -x+1, -y+1, -z+1.

Figure 4
View of the packing in the unit cell of the title complex along the c axis. Hydrogen-bonding interactions are shown as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (Version 5.39 update February 2018; Groom et al., 2016 ) for complexes of dhbq²⁻ ligand gave 94 hits. They include the isotypic crystal structures (Abrahams et al., 2002) with La (MIZXAU), Gd (MIZXEY), Yb (MIZXIC) and Lu (MIZXOI). In most cases, the dhbq²⁻ ligand acts in a μ₂-bis(bidentate) bridging mode to the central metal ions. Comparing the mean Ln—O bond length and the unit-cell volume for the title complex with the La, Gd, Yb and Lu analogues (Abrahams et al., 2002), the values decrease as the ionic radius of the Ln³⁺ ions decreases in the order La [La—O = 2.540 Å, V = 3289.3 (16) Å³] > Gd [Gd—O = 2.438 Å, V = 3162.7 (7) Å³] > Er [Er—O = 2.393 Å, V = 3107.18 (13) Å³] > Yb [Yb—O = 2.377 Å, V = 3087.1 (4) Å³] > Lu [Lu—O = 2.368 Å, V = 3074.2 (4) Å³], which is consistent with the lanthanide contraction effect.

5. Synthesis and crystallization

A mixture of Er(NO₃)₃·6H₂O (46.2 mg, 0.1 mmol) and H₂dhbq (14.2 mg, 0.1 mmol) in distilled H₂O (4 ml) and DMF (1 ml) was placed in a 20 ml vial and stirred at room temperature for 10 min. The mixture was sealed tightly, placed in an oven and then heated to 358 K under autogenous pressure for 12 h. After the reactor was cooled to room temperature, block-shaped dark-red crystals were filtered off, washed with deionized H₂O and dried in air at room temperature. Yield: 57% based on Er^III source.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The carbon-bound H atoms were placed in geometrically calculated positions and refined as riding with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). The hydrogen atoms of the water molecules were located from difference-Fourier maps but were refined with distance restraints of O—H = 0.84 Å and U_iso(H) = 1.5U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	[Er₂(C₆H₂O₄)₃(H₂O)₆]·18H₂O
M_r	1181.13
Crystal system, space group	Trigonal, R $[\overline{3}]$
Temperature (K)	296
a, c (Å)	14.0947 (3), 18.0603 (5)
V (Å³)	3107.18 (13)
Z	3
Radiation type	Mo Kα
μ (mm⁻¹)	4.13
Crystal size (mm)	0.28 × 0.22 × 0.2

Data collection
Diffractometer	Bruker D8 QUEST CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.677, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	32360, 2522, 2108
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.042, 1.08
No. of reflections	2522
No. of parameters	118
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.67, −1.39
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 1884389

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018017516/hb7788sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018017516/hb7788Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018017516/hb7788Isup3.cdx

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[hexaaquatris(µ-3,6-dioxocyclohexa-1,4-diene-1,4-diolato)dierbium(III)] octadecahydrate] top

Crystal data top

[Er₂(C₆H₂O₄)₃(H₂O)₆]·18H₂O	D_x = 1.894 Mg m⁻³
M_r = 1181.13	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 8655 reflections
a = 14.0947 (3) Å	θ = 2.8–31.7°
c = 18.0603 (5) Å	µ = 4.13 mm⁻¹
V = 3107.18 (13) Å³	T = 296 K
Z = 3	Hexagonal prism, dark red
F(000) = 1758	0.28 × 0.22 × 0.2 mm

Data collection top

Bruker D8 QUEST CMOS diffractometer	2522 independent reflections
Radiation source: microfocus sealed x-ray tube, Incoatec Iµus	2108 reflections with I > 2σ(I)
GraphiteDouble Bounce Multilayer Mirror monochromator	R_int = 0.065
Detector resolution: 10.5 pixels mm^-1	θ_max = 32.6°, θ_min = 2.8°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −19→21
T_min = 0.677, T_max = 0.746	l = −27→27
32360 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.042	w = 1/[σ²(F_o²) + (0.0042P)² + 10.2637P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2522 reflections	Δρ_max = 1.67 e Å⁻³
118 parameters	Δρ_min = −1.39 e Å⁻³
8 restraints	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.00020 (2)

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
Er1	0.6667	0.3333	0.587213 (10)	0.01773 (5)
O1	0.65928 (12)	0.50374 (13)	0.58327 (9)	0.0236 (3)
O2	0.54678 (13)	0.33698 (13)	0.49769 (9)	0.0247 (3)
O3	0.54011 (16)	0.33067 (15)	0.67424 (11)	0.0355 (4)
H3A	0.557 (3)	0.3878 (16)	0.6975 (16)	0.055 (10)*
H3B	0.4856 (17)	0.2781 (17)	0.6941 (15)	0.046 (9)*
O4	0.7266 (2)	0.52214 (19)	0.37540 (12)	0.0455 (5)
H4A	0.736 (3)	0.494 (3)	0.4136 (13)	0.075 (13)*
H4B	0.6643 (16)	0.489 (3)	0.356 (2)	0.079 (14)*
O5	0.29245 (18)	0.15371 (19)	0.57009 (14)	0.0452 (5)
H5A	0.354 (2)	0.167 (5)	0.587 (3)	0.15 (2)*
H5B	0.285 (4)	0.138 (4)	0.5247 (8)	0.103 (17)*
O6	0.18028 (19)	0.2663 (2)	0.57759 (14)	0.0470 (5)
H6A	0.213 (3)	0.3315 (15)	0.594 (2)	0.091 (16)*
H6B	0.222 (3)	0.240 (4)	0.576 (2)	0.104 (18)*
C1	0.58618 (18)	0.50816 (18)	0.54547 (12)	0.0212 (4)
C2	0.51755 (18)	0.40906 (18)	0.49646 (12)	0.0216 (4)
C3	0.43354 (19)	0.40401 (19)	0.45415 (13)	0.0256 (5)
H3	0.3902	0.3424	0.4255	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.01570 (6)	0.01570 (6)	0.02179 (9)	0.00785 (3)	0.000	0.000
O1	0.0218 (8)	0.0214 (8)	0.0293 (8)	0.0121 (7)	−0.0056 (6)	−0.0019 (6)
O2	0.0270 (8)	0.0222 (8)	0.0309 (8)	0.0168 (7)	−0.0069 (7)	−0.0050 (6)
O3	0.0371 (11)	0.0239 (9)	0.0394 (11)	0.0106 (8)	0.0163 (8)	−0.0025 (8)
O4	0.0474 (13)	0.0517 (13)	0.0376 (12)	0.0249 (11)	−0.0043 (10)	0.0091 (10)
O5	0.0335 (11)	0.0505 (13)	0.0505 (14)	0.0202 (10)	0.0094 (10)	0.0035 (11)
O6	0.0434 (13)	0.0436 (14)	0.0534 (14)	0.0212 (11)	0.0057 (10)	0.0082 (11)
C1	0.0202 (10)	0.0208 (10)	0.0221 (10)	0.0099 (9)	0.0003 (8)	0.0004 (8)
C2	0.0215 (10)	0.0217 (10)	0.0226 (10)	0.0115 (9)	0.0011 (8)	0.0015 (8)
C3	0.0259 (11)	0.0216 (11)	0.0318 (12)	0.0137 (10)	−0.0077 (9)	−0.0069 (9)

Geometric parameters (Å, º) top

Er1—O1ⁱ	2.4567 (15)	O3—H3B	0.836 (10)
Er1—O1	2.4567 (15)	O4—H4A	0.838 (10)
Er1—O1ⁱⁱ	2.4567 (15)	O4—H4B	0.842 (10)
Er1—O2ⁱⁱ	2.3578 (15)	O5—H5A	0.845 (10)
Er1—O2ⁱ	2.3577 (15)	O5—H5B	0.844 (10)
Er1—O2	2.3578 (15)	O6—H6A	0.848 (10)
Er1—O3	2.3636 (18)	O6—H6B	0.843 (10)
Er1—O3ⁱ	2.3636 (18)	C1—C2	1.523 (3)
Er1—O3ⁱⁱ	2.3637 (18)	C1—C3ⁱⁱⁱ	1.398 (3)
O1—C1	1.263 (3)	C2—C3	1.381 (3)
O2—C2	1.273 (3)	C3—C1ⁱⁱⁱ	1.398 (3)
O3—H3A	0.831 (10)	C3—H3	0.9300

O1ⁱ—Er1—O1	119.917 (4)	O3—Er1—O1ⁱⁱ	139.97 (6)
O1ⁱⁱ—Er1—O1ⁱ	119.917 (4)	O3—Er1—O1	68.54 (6)
O1ⁱⁱ—Er1—O1	119.916 (4)	O3ⁱⁱ—Er1—O1ⁱⁱ	68.54 (6)
O2ⁱ—Er1—O1ⁱ	65.01 (5)	O3ⁱ—Er1—O1ⁱⁱ	70.00 (6)
O2ⁱⁱ—Er1—O1	69.91 (5)	O3ⁱ—Er1—O1ⁱ	68.54 (6)
O2ⁱⁱ—Er1—O1ⁱⁱ	65.01 (5)	O3—Er1—O1ⁱ	70.00 (6)
O2—Er1—O1	65.01 (5)	O3ⁱ—Er1—O3ⁱⁱ	80.60 (8)
O2—Er1—O1ⁱⁱ	134.93 (5)	O3ⁱ—Er1—O3	80.60 (8)
O2ⁱ—Er1—O1ⁱⁱ	69.91 (5)	O3—Er1—O3ⁱⁱ	80.60 (8)
O2ⁱⁱ—Er1—O1ⁱ	134.93 (5)	C1—O1—Er1	119.88 (14)
O2—Er1—O1ⁱ	69.91 (5)	C2—O2—Er1	123.42 (14)
O2ⁱ—Er1—O1	134.93 (5)	Er1—O3—H3A	118 (2)
O2ⁱ—Er1—O2ⁱⁱ	78.15 (6)	Er1—O3—H3B	131 (2)
O2ⁱ—Er1—O2	78.15 (6)	H3A—O3—H3B	109 (3)
O2ⁱⁱ—Er1—O2	78.15 (6)	H4A—O4—H4B	117 (4)
O2ⁱⁱ—Er1—O3ⁱⁱ	85.01 (7)	H5A—O5—H5B	112 (5)
O2—Er1—O3ⁱⁱ	134.96 (6)	H6A—O6—H6B	112 (4)
O2ⁱ—Er1—O3ⁱⁱ	138.45 (6)	O1—C1—C2	115.38 (19)
O2ⁱ—Er1—O3	134.96 (6)	O1—C1—C3ⁱⁱⁱ	124.7 (2)
O2—Er1—O3	85.01 (7)	C3ⁱⁱⁱ—C1—C2	119.92 (19)
O2ⁱⁱ—Er1—O3	138.45 (6)	O2—C2—C1	114.28 (19)
O2ⁱ—Er1—O3ⁱ	85.01 (7)	O2—C2—C3	125.4 (2)
O2ⁱⁱ—Er1—O3ⁱ	134.96 (6)	C3—C2—C1	120.26 (19)
O2—Er1—O3ⁱ	138.46 (6)	C1ⁱⁱⁱ—C3—H3	120.1
O3ⁱⁱ—Er1—O1ⁱ	139.97 (7)	C2—C3—C1ⁱⁱⁱ	119.8 (2)
O3ⁱ—Er1—O1	139.97 (6)	C2—C3—H3	120.1
O3ⁱⁱ—Er1—O1	70.00 (6)

Er1—O1—C1—C2	−8.1 (2)	O2ⁱⁱ—Er1—O1—C1	96.59 (16)
Er1—O1—C1—C3ⁱⁱⁱ	172.37 (18)	O2ⁱⁱ—Er1—O2—C2	−86.3 (2)
Er1—O2—C2—C1	13.9 (3)	O2ⁱ—Er1—O2—C2	−166.47 (17)
Er1—O2—C2—C3	−167.71 (18)	O2—C2—C3—C1ⁱⁱⁱ	−176.2 (2)
O1ⁱⁱ—Er1—O1—C1	139.76 (13)	O3ⁱⁱ—Er1—O1—C1	−171.43 (17)
O1ⁱ—Er1—O1—C1	−34.5 (2)	O3ⁱ—Er1—O1—C1	−126.15 (16)
O1ⁱⁱ—Er1—O2—C2	−121.30 (16)	O3—Er1—O1—C1	−83.94 (16)
O1—Er1—O2—C2	−13.10 (16)	O3ⁱⁱ—Er1—O2—C2	−15.9 (2)
O1ⁱ—Er1—O2—C2	126.04 (18)	O3—Er1—O2—C2	55.53 (17)
O1—C1—C2—O2	−3.1 (3)	O3ⁱ—Er1—O2—C2	125.30 (17)
O1—C1—C2—C3	178.4 (2)	C1—C2—C3—C1ⁱⁱⁱ	2.1 (4)
O2ⁱ—Er1—O1—C1	48.94 (18)	C3ⁱⁱⁱ—C1—C2—O2	176.4 (2)
O2—Er1—O1—C1	10.65 (15)	C3ⁱⁱⁱ—C1—C2—C3	−2.1 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O6^iv	0.83 (1)	1.94 (1)	2.769 (3)	174 (3)
O3—H3B···O5^v	0.84 (1)	1.94 (1)	2.758 (3)	165 (3)
O4—H4A···O2ⁱⁱ	0.84 (1)	1.92 (1)	2.738 (3)	167 (4)
O4—H4B···O4^vi	0.84 (1)	1.98 (1)	2.803 (3)	164 (4)
O5—H5A···O1ⁱ	0.85 (1)	2.09 (3)	2.870 (3)	153 (5)
O5—H5B···O6^vii	0.84 (1)	1.95 (1)	2.794 (3)	174 (5)
O6—H6A···O4ⁱⁱⁱ	0.85 (1)	1.88 (1)	2.725 (3)	174 (4)
O6—H6B···O5	0.84 (1)	1.91 (1)	2.747 (3)	169 (5)

Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iii) −x+1, −y+1, −z+1; (iv) x−y+2/3, x+1/3, −z+4/3; (v) −x+2/3, −y+1/3, −z+4/3; (vi) x−y+1/3, x−1/3, −z+2/3; (vii) y, −x+y, −z+1.

Acknowledgements

The authors thank the Faculty of Science and Technology, Thammasat University, for funds to purchase the X-ray diffractometer.

Funding information

Funding for this research was provided by: Thailand Research Fund (grant No. RSA5780056). NP acknowledges the NSTDA STEM Workforce (SCA-CO-2560–3565-TH).

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