Poly[[tetra­aqua­(μ3-4-hy­droxy­pyridine-2,6-di­carboxyl­ato)di-μ2-oxalato-dipraseodymium(III)] 4.29-hydrate]

Khurshid, A.; Rujiwatra, A.; Chuasaard, T.

doi:10.1107/S2414314625004560

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 5| May 2025| x250456

https://doi.org/10.1107/S2414314625004560

Open

access

Poly[[tetraaqua(μ₃-4-hydroxypyridine-2,6-dicarboxylato)di-μ₂-oxalato-dipraseodymium(III)] 4.29-hydrate]

Aaqib Khurshid,^a Apinpus Rujiwatra ^a,^b and Thammanoon Chuasaard ^a,^c ^*

^aDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand, ^bMaterials Science Research Center, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand, and ^cOffice of Research Administration, Chiang Mai University, Chiang Mai 50200, Thailand
^*Correspondence e-mail: thammanoon.chuasaard@cmu.ac.th

Edited by M. Zeller, Purdue University, USA (Received 10 May 2025; accepted 22 May 2025; online 30 May 2025)

The coordination polymer of crystal formula [Pr^III₂(C₇H₂NO₅)(C₂O₄)₂(H₂O)₄]·4.29H₂O or [Pr^III₂(HCAM)(ox)₂(H₂O)₄]·4.29H₂O was synthesized from praseodymium(III) nitrate in water using chelidamic acid (H₃CAM) and oxalic acid (H₂ox). There are two Pr^III atoms in the asymmetric unit. One metal ion has nine-fold coordination from one pyridyl nitrogen and eight oxygen atoms from one HCAM²⁻, two ox²⁻, and two coordinating water molecules leading to the formation of a tricapped trigonal {Pr^IIINO₈} prism. The other metal ion is coordinated by ten oxygen atoms from two HCAM²⁻, two ox²⁻, and two coordinating water molecules, forming a bicapped square {Pr^IIIO₁₀} unit. The HCAM²⁻ linker has a μ₂-κ²:κ¹ chelating coordination mode via its carboxylates and N-pyridyl donors, linking the {Pr^IIINO₈} and {Pr^IIIO₁₀} units into infinite chains. The μ₂-κ¹:κ¹:κ¹:κ¹ bridging carboxylates of the ox²⁻ linkers connect adjacent chains into sheets in the ac plane. Adjacent layers further aggregate through intermolecular hydrogen bonding, most of which involves the water molecules of crystallization, and π–π interactions to form a tri-periodic supramolecular framework. Some of the co-crystallizing water molecules as well as one of the metal-coordinating water molecules are disordered.

Keywords: praseodymium; chelidamic acid; coordination polymer; hydrogen bonding; crystal structure.

CCDC reference: 2448088

Structure description

A coordination polymer (CP) is a metal coordination compound with repeating coordination entities consisting of metal ions or clusters - the nodes - that are connected through coordinating ligands into an infinite solid-state assembly with different periodcities. Lanthanide–CPs (Ln^III–CPs) in which the metal nodes are lanthanide ions are of interest as they combine the characteristics of CPs such as an often high chemical and thermal stability and a capability to be tailor-made to include functional groups with the lanthanide's unique properties based on their various coordination geometries and characteristic optical and magnetic properties (Li et al., 2015 ; Bünzli, 2014 ). These merits can provide Ln^I^II–CPs with fascinating structures and functions. Their well-known applications include catalysis (Zhang et al., 2021 ), luminescent sensing (Wang et al., 2023 ) and gas adsorption (Roy et al., 2014 ), to name just a few. All Ln^III ions have a high oxophilicity, so organic polycarboxylates are commonly employed as organic linkers in Ln^III–CPs (Bünzli, 2014). The high coordination numbers and flexible coordination geometries of Ln^I^II, as well as a lack of directionality of Ln—O bonds do, however, make it difficult to predict the exact nature of the resultant polymeric framework, which is also greatly affected by the choice of solvent used during synthesis, which is often incorporated into the coordination polymer structure (Bünzli, 2014; Patra & Pal, 2025 ). Owing to their often labile nature, the solvent molecules tend to exhibit disorder, even though they can consolidate the framework structure by promoting intermolecular hydrogen-bonding interactions. The introduction of hydrogen-bond-promoting groups such as hydroxyl on an organic linker is therefore expected to support the framework structure of CPs by transfixing the solvent molecules. Chelidamic acid (H₃CAM) containing an –OH group on a pyridyl ring was selected to be the organic linker to bind with praseodymium(III) (Pr^III) in this work. Oxalic acid (H₂ox) was also used as another small organic linker to help prevent the coordination of labile solvent molecules to the coordination sphere of Pr^III and to provide the possibility of obtaining a new Pr^III–CP structure with high dimensionality.

The asymmetric unit of the title compound, i.e. [Pr^III₂(HCAM)(ox)₂(H₂O)₄]·4.29H₂O, is made up of two Pr^III ions (Pr1 and Pr2), one complete HCAM²⁻ dianion, two ox²⁻ dianions, four metal-coordinating water molecules (two at each Pr^III ion), and approximately four and a third co-crystallizing water molecules (Fig. 1a). One of the coordinating water molecules is disordered over two sites (O15A and O15B). Two of the four crystallizing water molecule are not disordered (O18 and O19), whilst O20 is hydrogen bonded to its own symmetry equivalent by inversion, inducing site disorder splitting to O20A and O20B, each of which exhibit 50% occupancy. The other co-crystallizing water molecules are extensively disordered and were refined over three partially occupied sites (O21A, O21B and O21C), which share a total site occupancy of 1.294 water molecules. The correlated disorder prevents their hydrogen atoms to be resolved.

Figure 1
A depiction of (a) an extended asymmetric unit of title compound drawn using 50% probability ellipsoids, (b) TPRS-{Pr^IIINO₈} building unit of Pr1, (c) SAPRS-{Pr^IIIO₁₀} building unit of Pr2, (d) coordination mode adopted by HCAM²⁻, and (e) coordination mode adopted by ox²⁻. [Symmetry codes: (i) −x, −y + 1, −z + 1; (ii) −x + 1, −y + 1, −z + 1].

The Pr1 and Pr2 ions show two different coordination environments. Pr1 has a nine-fold coordination environment defined by one pyridyl nitrogen atom of HCAM²⁻ and eight oxygen atoms from one HCAM²⁻, two ox²⁻, and two coordinating water molecules, leading to the formation of a tricapped trigonal–prismatic building unit, i.e. TPRS-{Pr^IIINO₈} (Fig. 1b). Pr2 is tenfold coordinated to oxygen atoms from two HCAM²⁻, two ox²⁻, and two coordinating water molecules, forming a bicapped square antiprism, i.e. SAPRS-{Pr^IIIO₁₀} (Fig. 1c). The Pr—O bond lengths are in the range of 2.478 (3)–2.550 (3) Å (Table 1), which agrees well with those for other reported Pr^III frameworks containing HCAM²⁻ and ox²⁻ (Chen et al., 2008 ; Zou et al., 2009 , 2010 , 2011 ; Zhao et al., 2009 ). The HCAM²⁻ linker has a μ₂-κ²:κ¹ chelating coordination mode via both carboxylate groups and the N-pyridyl donor, thus creating infinite chains made up from alternating and edge-sharing TPRS-{Pr^IIINO₈} and SAPRS-{Pr^IIIO₁₀} units that extend along [100]. The chains are connected to adjacent chains through bridging carboxylates of the ox²⁻ linkers that adopt the common μ₂-κ¹:κ¹:κ¹:κ¹ mode of coordination (Fig. 1e) along the c-axis, resulting in sheets in the ac plane. Neighboring sheets are connected to one another through both hydrogen-bonding interactions involving the coordinating and crystallizing water molecules (Table 2, Fig. 2a) and intermolecular π–π interactions between the pyridyl rings of the HCAM²⁻ ligands that protrude from the parallel sheets (Fig. 2b), leading to formation of a tri-periodic supramolecular network. The π–π interactions are slightly offset from each other (Banerjee et al., 2019 ; Yao et al., 2018 ) and have a centroid-to-centroid distance of ca 3.90 Å, an offset distance of ca 2.35 Å, and are exactly parallel (Fig. 2c). The interplanar stacking distance is 3.11 Å. The supramolecular architecture established by these stabilizing interactions has an interlayer distance between parallel sheets of ca 9.33 Å. Disregarding the co-crystallized not metal-coordinating water molecules, the total potential solvent area volume within the interlayer space is estimated to be ca 20% of the unit-cell volume, based on a calculation performed by PLATON software (Spek, 2020 ).

Table 1
Selected bond lengths (Å)

Pr1—O1	2.517 (3)	Pr2—O1ⁱ	2.746 (3)
Pr1—O3	2.526 (3)	Pr2—O2ⁱ	2.580 (3)
Pr1—O6	2.503 (3)	Pr2—O3ⁱⁱ	2.772 (3)
Pr1—O8	2.535 (3)	Pr2—O4ⁱⁱ	2.608 (3)
Pr1—O10	2.532 (3)	Pr2—O7	2.478 (3)
Pr1—O12	2.520 (3)	Pr2—O9	2.538 (3)
Pr1—O14	2.510 (3)	Pr2—O11ⁱⁱⁱ	2.519 (3)
Pr1—O15A	2.523 (16)	Pr2—O13ⁱⁱⁱ	2.550 (3)
Pr1—O15B	2.501 (16)	Pr2—O16	2.496 (4)
Pr1—N1	2.555 (4)	Pr2—O17	2.487 (3)
Symmetry codes: (i) ; (ii) ; (iii) .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O13^iv	0.82	1.81	2.626 (4)	170
O14—H14A⋯O11^v	0.82 (2)	1.92 (2)	2.735 (4)	173 (5)
O14—H14B⋯O18	0.83 (2)	1.93 (2)	2.755 (5)	175 (5)
O15A—H15A⋯O19^vi	0.83 (2)	2.16 (4)	2.81 (3)	135 (3)
O15A—H15A⋯O21A	0.83 (2)	2.26 (2)	2.89 (2)	134 (4)
O15A—H15B⋯O21B	0.84 (2)	2.02 (9)	2.71 (3)	138 (11)
O15B—H15C⋯O21C	0.84 (2)	2.15 (6)	2.93 (3)	155 (10)
O15B—H15D⋯O7ⁱⁱ	0.86 (2)	1.96 (4)	2.75 (2)	152 (5)
O16—H16A⋯O8ⁱ	0.86 (2)	1.85 (2)	2.705 (4)	179 (5)
O16—H16B⋯O20A^vii	0.83 (2)	2.17 (4)	2.96 (3)	159 (6)
O16—H16B⋯O20B	0.83 (2)	2.12 (3)	2.94 (2)	172 (5)
O17—H17A⋯O12ⁱⁱ	0.83 (2)	2.33 (4)	2.922 (4)	129 (4)
O17—H17A⋯O15Aⁱⁱ	0.83 (2)	2.13 (3)	2.892 (19)	153 (5)
O17—H17A⋯O15Bⁱⁱ	0.83 (2)	2.15 (3)	2.865 (18)	144 (4)
O17—H17B⋯O5^vii	0.83 (2)	2.09 (2)	2.914 (4)	171 (5)
O18—H18A⋯O4^viii	0.85 (2)	2.10 (2)	2.951 (6)	177 (6)
O18—H18B⋯O2^v	0.85 (2)	2.21 (3)	3.011 (6)	156 (7)
O19—H19A⋯O18^vi	0.83 (2)	2.56 (7)	3.161 (8)	130 (7)
O19—H19B⋯O9	0.83 (2)	2.15 (2)	2.904 (7)	151 (5)
O20A—H20A⋯O20B	0.87	2.17	2.901 (14)	141
O20A—H20B⋯O19^ix	0.85	2.13	2.87 (3)	146
O20B—H20C⋯O19ⁱ	0.85	2.13	2.87 (2)	145
Symmetry codes: (i) ; (ii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .

Figure 2
Views of (a) hydrogen-bonding interactions in the crystal structure of title compound (only hydrogen atoms involving the hydrogen bonding interactions are shown), (b) interlayer π–π interaction, and (c) displaced π–π stacking geometry.

Synthesis and crystallization

All chemicals used in this work were obtained commercially and used without purification: Pr₆O₁₁ (TJTM, 99.99%), chelidamic acid (H₃CAM; C₇H₅NO₅, Macklin, 98%), oxalic acid (H₂ox·2H₂O; C₂H₂O₄·2H₂O, Fluka Chemika, ≥99%), nitric acid (HNO₃, RCI Labscan, 65%). Pr^III(NO₃)₃·6H₂O was prepared by dissolving Pr₆O₁₁ in small amount of concentrated solution of nitric acid followed by slow crystallization.

To synthesize the title compound, a mixture of Pr^III(NO₃)₃·6H₂O (43.5 mg, 0.100 mmol), H₃CAM (20.5 mg, 0.100 mmol) and oxalic acid (12.6 mg, 0.100 mmol) was prepared in 10.0 ml of deionized water. The mixture was then transferred to a Teflon lined autoclave and heated at 130°C for 5 d under autogenous pressure. After cooling down to room temperature, brown block-shaped crystals (34% yield based on Pr^III) were obtained, collected and washed with deionized water. The crystals were characterized using FT–IR spectroscopy (PerkinElmer/Frontier FT–IR instrument; ATR mode; cm⁻¹): 3675–2814(br), 1647(m), 1562(s), 1443(m), 1396(m), 1354(m), 1305(m), 1251(w), 1121(w), 1027(m), 750(m), 486(m).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	[Pr₂(C₇H₃NO₅)(C₂O₄)₂(H₂O)₄]·4.29H₂O
M_r	785.78
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	298
a, b, c (Å)	9.9236 (3), 10.3042 (4), 12.9748 (5)
α, β, γ (°)	66.684 (4), 80.942 (3), 66.660 (3)
V (Å³)	1118.69 (8)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	4.41
Crystal size (mm)	0.2 × 0.2 × 0.1

Data collection
Diffractometer	SuperNova, Single source at offset/far, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.768, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18710, 4715, 3799
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.085, 1.05
No. of reflections	4715
No. of parameters	399
No. of restraints	71
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.47, −1.78
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

The oxygen atom of a coordinating water molecule (O15) shows site disorder splitting to two sites of O15A and O15B with site occupancies of 0.45 (4) and 0.55 (4), respectively. A SIMU command with an effective standard deviation of 0.01 Å² was used to restrain O15A and O15B to have similar U^ij components. An oxygen atom of a crystallizing water molecule (O20) is hydrogen bonded to its symmetry-equivalent counterpart which across a nearby inversion center (0.5 0 0.5), inducing disorder and splitting into two sites (O20A and O20B). As O20A and O20B are too close to be compatible with each other, one of them was moved across the inversion center. A SIMU (s = 0.01, st = 0.01, d_max = 3) together with a ISOR (s = 0.01, st = 0.02) command were applied to O20A and O20B to restrain their U^ij components to approximate isotropic behavior. The region where O21A, O21B and O21C of water molecules of crystallization were placed originally contained several large electron densities, with O21B being in hydrogen-bonding distance to its own counterpart by inversion. The large number of permutations prevented an exact disorder modeling or placement of hydrogen atoms. However, the total number of site occupancies in this region was estimated to be about one and a third (1.294). A SIMU (s = 0.01, st = 0.02, d_max = 2) command was applied to O21A, O21B and O21C to restrain to have similar U^ij components.

The carbon-bound hydrogen atoms were positioned geometrically and refined isotropically using a riding model (AFIX 43). The C—H bond lengths in the pyridyl ring of HCAM²⁻ were constrained to 0.93 Å [U_iso(H) = 1.2U_iso(C)]. A hydrogen atom of an –OH group of HCAM²⁻ was positioned geometrically and refined isotropically with allowing a rotation with a tetrahedral C—O—H angle (AFIX 147) to best fit the experimental electron density. The O—H bond length of this –OH group was set to be 0.82 Å [U_iso(H) = 1.5U_iso(O)]. The hydrogen atoms of water molecules (both coordinating and crystallizing water) were refined isotropically, and the O—H bond lengths and H⋯H distances were restrained to 0.84 (2) Å and 1.36 (2) Å, respectively, [U_iso(H) = 1.5U_iso(O)]. There were some hydrogen atoms of water molecules that were additionally restrained based on hydrogen-bonding considerations, i.e. H19B⋯O9 and H20A⋯O20B distances were restrained to 2.15 (2) Å, and the H15A⋯O21A distance was restrained to 2.25 (2) Å. The hydrogen atoms of O20A and O20B were initially refined in the same manner while a damping factor was applied. In the final refinement cycles, the damping factor was removed and the hydrogen atoms were constrained to ride on their carrying oxygen atoms (AFIX 3).

Structural data

CCDC reference: 2448088

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625004560/zl4083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625004560/zl4083Isup2.hkl

checkCIF report

Computing details top

Poly[[tetraaqua(µ₃-4-hydroxypyridine-2,6-dicarboxylato)di-µ₂-oxalato-dipraseodymium(III)] 4.29-hydrate] top

Crystal data top

[Pr₂(C₇H₃NO₅)(C₂O₄)₂(H₂O)₄]·4.29H₂O	Z = 2
M_r = 785.78	F(000) = 757
Triclinic, P1	D_x = 2.333 Mg m⁻³
a = 9.9236 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3042 (4) Å	Cell parameters from 11399 reflections
c = 12.9748 (5) Å	θ = 2.3–27.2°
α = 66.684 (4)°	µ = 4.41 mm⁻¹
β = 80.942 (3)°	T = 298 K
γ = 66.660 (3)°	Block, clear brownish colourless
V = 1118.69 (8) Å³	0.2 × 0.2 × 0.1 mm

Data collection top

SuperNova, Single source at offset/far, HyPix3000 diffractometer	4715 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3799 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.088
ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −12→12
T_min = 0.768, T_max = 1.000	k = −12→12
18710 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: mixed
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0364P)²] where P = (F_o² + 2F_c²)/3
4715 reflections	(Δ/σ)_max < 0.001
399 parameters	Δρ_max = 1.47 e Å⁻³
71 restraints	Δρ_min = −1.78 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pr1	0.23196 (2)	0.77685 (3)	0.25657 (2)	0.01644 (9)
Pr2	0.23512 (2)	0.29264 (3)	0.76177 (2)	0.01623 (9)
O1	0.0556 (3)	0.6667 (3)	0.2380 (3)	0.0213 (7)
O2	−0.0132 (3)	0.5827 (4)	0.1307 (3)	0.0307 (8)
O3	0.5023 (3)	0.6898 (3)	0.2099 (3)	0.0216 (7)
O4	0.7077 (3)	0.5102 (4)	0.1918 (3)	0.0289 (8)
O5	0.4995 (3)	0.2189 (4)	0.0567 (3)	0.0259 (8)
H5	0.433892	0.212745	0.029681	0.039*
O6	0.3619 (3)	0.5268 (4)	0.4061 (3)	0.0304 (8)
O7	0.3719 (3)	0.3733 (4)	0.5863 (3)	0.0252 (8)
O8	0.0950 (3)	0.7142 (3)	0.4408 (3)	0.0256 (8)
O9	0.0969 (3)	0.5504 (4)	0.6168 (3)	0.0275 (8)
O10	0.1736 (3)	0.8820 (3)	0.0496 (2)	0.0213 (7)
O11	0.1805 (3)	1.0576 (3)	−0.1203 (2)	0.0216 (7)
O12	0.2910 (3)	1.0092 (3)	0.1385 (3)	0.0242 (7)
O13	0.3127 (3)	1.1706 (3)	−0.0329 (2)	0.0234 (7)
O14	−0.0079 (4)	0.9973 (4)	0.2305 (3)	0.0302 (8)
H14A	−0.066 (5)	0.983 (6)	0.201 (4)	0.045*
H14B	−0.016 (5)	1.088 (3)	0.200 (4)	0.045*
O15A	0.298 (3)	0.894 (3)	0.3700 (17)	0.028 (4)	0.45 (4)
H15A	0.234 (5)	0.956 (5)	0.395 (3)	0.043*	0.45 (4)
H15B	0.369 (8)	0.842 (8)	0.415 (8)	0.043*	0.45 (4)
O15B	0.342 (2)	0.828 (3)	0.3904 (16)	0.042 (4)	0.55 (4)
H15C	0.293 (5)	0.859 (12)	0.440 (6)	0.064*	0.55 (4)
H15D	0.427 (5)	0.767 (8)	0.420 (6)	0.064*	0.55 (4)
O16	0.1824 (4)	0.2134 (5)	0.6187 (3)	0.0400 (10)
H16A	0.094 (3)	0.236 (6)	0.601 (4)	0.060*
H16B	0.233 (5)	0.209 (7)	0.562 (3)	0.060*
O17	0.4416 (3)	0.0634 (4)	0.7485 (3)	0.0304 (9)
H17A	0.522 (3)	0.073 (5)	0.736 (4)	0.046*
H17B	0.454 (5)	−0.020 (3)	0.800 (3)	0.046*
O18	−0.0349 (5)	1.2962 (5)	0.1190 (4)	0.0638 (13)
H18A	−0.109 (5)	1.355 (6)	0.143 (5)	0.096*
H18B	−0.017 (7)	1.350 (6)	0.053 (3)	0.096*
O19	−0.1396 (7)	0.7992 (7)	0.6626 (6)	0.106 (2)
H19A	−0.150 (8)	0.811 (12)	0.724 (5)	0.159*
H19B	−0.055 (4)	0.743 (7)	0.655 (8)	0.159*
O20A	0.599 (3)	−0.1133 (16)	0.544 (2)	0.126 (6)	0.5
H20A	0.516875	−0.037798	0.542562	0.189*	0.5
H20B	0.661995	−0.098201	0.570062	0.189*	0.5
O20B	0.389 (3)	0.1898 (16)	0.4318 (19)	0.112 (5)	0.5
H20C	0.299245	0.227002	0.411383	0.168*	0.5
H20D	0.402974	0.255335	0.447541	0.168*	0.5
O21A	0.1227 (19)	0.9358 (19)	0.5629 (13)	0.131 (6)	0.488 (17)
O21C	0.214 (3)	0.838 (3)	0.608 (2)	0.108 (6)	0.253 (13)
O21B	0.3984 (11)	0.7322 (11)	0.5831 (8)	0.097 (5)	0.553 (15)
N1	0.3350 (4)	0.5635 (4)	0.1792 (3)	0.0188 (8)
C1	0.0848 (5)	0.5939 (5)	0.1735 (4)	0.0228 (11)
C2	0.2449 (4)	0.5154 (5)	0.1506 (4)	0.0171 (10)
C3	0.2935 (5)	0.4015 (5)	0.1089 (4)	0.0218 (10)
H3	0.226867	0.373002	0.088373	0.026*
C4	0.4425 (5)	0.3294 (5)	0.0978 (4)	0.0194 (10)
C5	0.5398 (5)	0.3766 (5)	0.1287 (4)	0.0237 (11)
H5A	0.640885	0.328970	0.123911	0.028*
C6	0.4805 (4)	0.4958 (5)	0.1664 (4)	0.0181 (10)
C7	0.5711 (5)	0.5680 (5)	0.1928 (4)	0.0193 (10)
C9	0.1529 (5)	0.5941 (5)	0.5226 (4)	0.0193 (10)
C8	0.3103 (5)	0.4884 (5)	0.5036 (4)	0.0202 (10)
C11	0.2745 (5)	1.0625 (5)	0.0363 (4)	0.0195 (10)
C10	0.2019 (5)	0.9932 (5)	−0.0159 (4)	0.0177 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.01715 (16)	0.01723 (16)	0.01250 (17)	−0.00734 (12)	0.00045 (11)	−0.00222 (12)
Pr2	0.01536 (16)	0.01812 (15)	0.01234 (16)	−0.00743 (12)	0.00053 (11)	−0.00168 (12)
O1	0.0189 (16)	0.0243 (18)	0.0231 (19)	−0.0089 (14)	0.0049 (13)	−0.0122 (15)
O2	0.0163 (17)	0.043 (2)	0.045 (2)	−0.0117 (16)	0.0039 (15)	−0.0283 (18)
O3	0.0233 (18)	0.0244 (18)	0.0215 (19)	−0.0128 (15)	0.0024 (14)	−0.0097 (15)
O4	0.0166 (18)	0.032 (2)	0.042 (2)	−0.0098 (15)	0.0002 (15)	−0.0170 (18)
O5	0.0178 (17)	0.0267 (18)	0.038 (2)	−0.0046 (15)	−0.0057 (15)	−0.0177 (16)
O6	0.0258 (19)	0.034 (2)	0.0159 (19)	−0.0058 (16)	0.0034 (14)	−0.0006 (16)
O7	0.0206 (17)	0.0287 (19)	0.0137 (18)	−0.0078 (15)	−0.0005 (13)	0.0034 (15)
O8	0.0241 (18)	0.0224 (18)	0.0198 (19)	−0.0068 (15)	0.0003 (14)	0.0008 (15)
O9	0.0251 (18)	0.033 (2)	0.0153 (19)	−0.0090 (15)	0.0067 (14)	−0.0035 (15)
O10	0.0301 (18)	0.0207 (17)	0.0138 (18)	−0.0158 (15)	−0.0012 (13)	−0.0001 (14)
O11	0.0257 (18)	0.0258 (18)	0.0132 (18)	−0.0136 (15)	−0.0039 (13)	−0.0016 (14)
O12	0.0335 (19)	0.0266 (18)	0.0133 (19)	−0.0168 (15)	−0.0052 (14)	−0.0004 (15)
O13	0.0284 (18)	0.0259 (18)	0.0181 (19)	−0.0177 (15)	−0.0024 (14)	−0.0017 (15)
O14	0.027 (2)	0.0250 (19)	0.040 (2)	−0.0093 (16)	−0.0066 (16)	−0.0112 (18)
O15A	0.029 (9)	0.042 (9)	0.023 (7)	−0.012 (7)	0.004 (5)	−0.023 (7)
O15B	0.028 (7)	0.060 (11)	0.046 (7)	−0.016 (7)	0.000 (5)	−0.027 (8)
O16	0.026 (2)	0.069 (3)	0.039 (3)	−0.019 (2)	0.0060 (18)	−0.034 (2)
O17	0.0188 (18)	0.0220 (19)	0.041 (2)	−0.0083 (15)	0.0046 (16)	−0.0036 (16)
O18	0.075 (4)	0.036 (3)	0.070 (4)	−0.012 (2)	0.003 (3)	−0.019 (2)
O19	0.098 (4)	0.087 (4)	0.116 (5)	−0.008 (4)	0.010 (4)	−0.049 (4)
O20A	0.125 (7)	0.110 (13)	0.150 (10)	−0.017 (11)	−0.032 (7)	−0.069 (11)
O20B	0.124 (7)	0.097 (12)	0.131 (10)	−0.017 (10)	−0.027 (7)	−0.071 (11)
O21A	0.160 (12)	0.094 (10)	0.119 (10)	−0.013 (8)	−0.012 (8)	−0.048 (8)
O21C	0.145 (11)	0.082 (9)	0.089 (9)	−0.011 (8)	−0.020 (8)	−0.047 (8)
O21B	0.115 (8)	0.081 (7)	0.063 (7)	−0.006 (6)	−0.017 (5)	−0.019 (5)
N1	0.015 (2)	0.021 (2)	0.019 (2)	−0.0091 (17)	0.0012 (16)	−0.0049 (17)
C1	0.019 (3)	0.018 (2)	0.029 (3)	−0.009 (2)	0.001 (2)	−0.004 (2)
C2	0.014 (2)	0.023 (2)	0.014 (2)	−0.0065 (19)	−0.0006 (18)	−0.007 (2)
C3	0.023 (3)	0.028 (3)	0.022 (3)	−0.014 (2)	−0.001 (2)	−0.011 (2)
C4	0.024 (3)	0.014 (2)	0.017 (3)	−0.007 (2)	−0.0011 (19)	−0.002 (2)
C5	0.015 (2)	0.026 (3)	0.027 (3)	−0.005 (2)	−0.005 (2)	−0.007 (2)
C6	0.018 (2)	0.017 (2)	0.018 (3)	−0.0061 (19)	−0.0011 (19)	−0.005 (2)
C7	0.018 (3)	0.023 (3)	0.016 (3)	−0.011 (2)	−0.0003 (19)	−0.002 (2)
C9	0.016 (2)	0.023 (3)	0.017 (3)	−0.006 (2)	0.0000 (19)	−0.007 (2)
C8	0.016 (2)	0.024 (3)	0.020 (3)	−0.008 (2)	0.001 (2)	−0.007 (2)
C11	0.015 (2)	0.023 (3)	0.019 (3)	−0.008 (2)	−0.0031 (19)	−0.004 (2)
C10	0.015 (2)	0.020 (2)	0.019 (3)	−0.0051 (19)	−0.0039 (18)	−0.007 (2)

Geometric parameters (Å, º) top

Pr1—O1	2.517 (3)	O11—C10	1.260 (5)
Pr1—O3	2.526 (3)	O12—C11	1.227 (5)
Pr1—O6	2.503 (3)	O13—C11	1.275 (5)
Pr1—O8	2.535 (3)	O14—H14A	0.821 (19)
Pr1—O10	2.532 (3)	O14—H14B	0.832 (19)
Pr1—O12	2.520 (3)	O15A—H15A	0.830 (19)
Pr1—O14	2.510 (3)	O15A—H15B	0.84 (2)
Pr1—O15A	2.523 (16)	O15B—H15C	0.84 (2)
Pr1—O15B	2.501 (16)	O15B—H15D	0.86 (2)
Pr1—N1	2.555 (4)	O16—H16A	0.856 (19)
Pr2—O1ⁱ	2.746 (3)	O16—H16B	0.826 (19)
Pr2—O2ⁱ	2.580 (3)	O17—H17A	0.826 (18)
Pr2—O3ⁱⁱ	2.772 (3)	O17—H17B	0.832 (19)
Pr2—O4ⁱⁱ	2.608 (3)	O18—H18A	0.85 (2)
Pr2—O7	2.478 (3)	O18—H18B	0.85 (2)
Pr2—O9	2.538 (3)	O19—H19A	0.83 (2)
Pr2—O11ⁱⁱⁱ	2.519 (3)	O19—H19B	0.831 (19)
Pr2—O13ⁱⁱⁱ	2.550 (3)	O20A—H20A	0.8688
Pr2—O16	2.496 (4)	O20A—H20B	0.8471
Pr2—O17	2.487 (3)	O20B—H20C	0.8540
Pr2—C1ⁱ	3.025 (4)	O20B—H20D	0.8435
Pr2—C7ⁱⁱ	3.054 (4)	N1—C2	1.336 (5)
O1—C1	1.263 (5)	N1—C6	1.348 (5)
O2—C1	1.256 (5)	C1—C2	1.513 (6)
O3—C7	1.259 (5)	C2—C3	1.370 (6)
O4—C7	1.247 (5)	C3—H3	0.9300
O5—H5	0.8200	C3—C4	1.381 (6)
O5—C4	1.333 (5)	C4—C5	1.407 (6)
O6—C8	1.256 (5)	C5—H5A	0.9300
O7—C8	1.248 (5)	C5—C6	1.381 (6)
O8—C9	1.256 (5)	C6—C7	1.519 (6)
O9—C9	1.247 (5)	C9—C8	1.559 (7)
O10—C10	1.235 (5)	C11—C10	1.559 (6)

O1—Pr1—O3	125.52 (9)	O16—Pr2—O9	79.58 (12)
O1—Pr1—O8	71.98 (10)	O16—Pr2—O11ⁱⁱⁱ	77.00 (11)
O1—Pr1—O10	73.53 (9)	O16—Pr2—O13ⁱⁱⁱ	137.51 (12)
O1—Pr1—O12	134.40 (10)	O16—Pr2—C1ⁱ	92.58 (12)
O1—Pr1—O15A	144.9 (4)	O16—Pr2—C7ⁱⁱ	142.54 (11)
O1—Pr1—N1	63.08 (10)	O17—Pr2—O1ⁱ	123.96 (10)
O3—Pr1—O8	131.86 (10)	O17—Pr2—O2ⁱ	150.18 (10)
O3—Pr1—O10	89.35 (9)	O17—Pr2—O3ⁱⁱ	70.95 (10)
O3—Pr1—N1	62.46 (10)	O17—Pr2—O4ⁱⁱ	119.01 (10)
O6—Pr1—O1	88.21 (10)	O17—Pr2—O9	133.08 (10)
O6—Pr1—O3	71.33 (10)	O17—Pr2—O11ⁱⁱⁱ	70.13 (10)
O6—Pr1—O8	64.40 (10)	O17—Pr2—O13ⁱⁱⁱ	82.94 (11)
O6—Pr1—O10	138.63 (11)	O17—Pr2—O16	69.13 (12)
O6—Pr1—O12	135.43 (9)	O17—Pr2—C1ⁱ	142.91 (10)
O6—Pr1—O14	138.35 (11)	O17—Pr2—C7ⁱⁱ	95.28 (11)
O6—Pr1—O15A	85.8 (7)	C1ⁱ—Pr2—C7ⁱⁱ	116.61 (12)
O6—Pr1—N1	68.80 (11)	Pr1—O1—Pr2ⁱ	144.80 (13)
O8—Pr1—N1	114.36 (10)	C1—O1—Pr1	120.3 (3)
O10—Pr1—O8	137.05 (9)	C1—O1—Pr2ⁱ	90.1 (2)
O10—Pr1—N1	69.83 (10)	C1—O2—Pr2ⁱ	98.1 (3)
O12—Pr1—O3	72.10 (10)	Pr1—O3—Pr2ⁱⁱ	143.18 (13)
O12—Pr1—O8	131.56 (10)	C7—O3—Pr1	123.1 (3)
O12—Pr1—O10	64.34 (9)	C7—O3—Pr2ⁱⁱ	90.4 (2)
O12—Pr1—O15A	66.4 (5)	C7—O4—Pr2ⁱⁱ	98.6 (3)
O12—Pr1—N1	114.05 (10)	C4—O5—H5	109.5
O14—Pr1—O1	78.28 (10)	C8—O6—Pr1	121.4 (3)
O14—Pr1—O3	146.68 (10)	C8—O7—Pr2	121.3 (3)
O14—Pr1—O8	73.95 (10)	C9—O8—Pr1	120.6 (3)
O14—Pr1—O10	74.65 (11)	C9—O9—Pr2	119.4 (3)
O14—Pr1—O12	74.62 (10)	C10—O10—Pr1	120.7 (3)
O14—Pr1—O15A	83.6 (6)	C10—O11—Pr2^iv	123.2 (3)
O14—Pr1—N1	133.09 (11)	C11—O12—Pr1	120.1 (3)
O15A—Pr1—O3	84.8 (5)	C11—O13—Pr2^iv	121.0 (3)
O15A—Pr1—O8	74.3 (4)	Pr1—O14—H14A	108 (4)
O15A—Pr1—O10	129.7 (6)	Pr1—O14—H14B	124 (3)
O15A—Pr1—N1	143.2 (6)	H14A—O14—H14B	110 (5)
O15B—Pr1—O1	144.6 (4)	Pr1—O15A—H15A	122 (3)
O15B—Pr1—O3	76.7 (5)	Pr1—O15A—H15B	121 (3)
O15B—Pr1—O6	72.4 (7)	H15A—O15A—H15B	109 (3)
O15B—Pr1—O8	72.9 (4)	Pr1—O15B—H15C	123 (3)
O15B—Pr1—O10	139.4 (5)	Pr1—O15B—H15D	121 (3)
O15B—Pr1—O12	75.1 (6)	H15C—O15B—H15D	105 (3)
O15B—Pr1—O14	96.5 (6)	Pr2—O16—H16A	121 (3)
O15B—Pr1—N1	130.4 (6)	Pr2—O16—H16B	124 (3)
O1ⁱ—Pr2—O3ⁱⁱ	164.06 (9)	H16A—O16—H16B	107 (6)
O1ⁱ—Pr2—C1ⁱ	24.67 (10)	Pr2—O17—H17A	114 (4)
O1ⁱ—Pr2—C7ⁱⁱ	140.12 (11)	Pr2—O17—H17B	119 (3)
O2ⁱ—Pr2—O1ⁱ	48.86 (9)	H17A—O17—H17B	107 (3)
O2ⁱ—Pr2—O3ⁱⁱ	115.62 (9)	H18A—O18—H18B	106 (3)
O2ⁱ—Pr2—O4ⁱⁱ	72.16 (9)	H19A—O19—H19B	112 (4)
O2ⁱ—Pr2—C1ⁱ	24.28 (11)	H20A—O20A—H20B	105.4
O2ⁱ—Pr2—C7ⁱⁱ	93.86 (11)	H20C—O20B—H20D	107.1
O3ⁱⁱ—Pr2—C1ⁱ	139.57 (11)	C2—N1—Pr1	120.4 (3)
O3ⁱⁱ—Pr2—C7ⁱⁱ	24.35 (10)	C2—N1—C6	118.0 (4)
O4ⁱⁱ—Pr2—O1ⁱ	116.38 (9)	C6—N1—Pr1	121.6 (3)
O4ⁱⁱ—Pr2—O3ⁱⁱ	48.16 (9)	O1—C1—Pr2ⁱ	65.2 (2)
O4ⁱⁱ—Pr2—C1ⁱ	93.52 (11)	O1—C1—C2	117.6 (4)
O4ⁱⁱ—Pr2—C7ⁱⁱ	23.81 (11)	O2—C1—Pr2ⁱ	57.6 (2)
O7—Pr2—O1ⁱ	122.36 (9)	O2—C1—O1	122.4 (4)
O7—Pr2—O2ⁱ	137.91 (11)	O2—C1—C2	120.0 (4)
O7—Pr2—O3ⁱⁱ	64.97 (9)	C2—C1—Pr2ⁱ	172.1 (3)
O7—Pr2—O4ⁱⁱ	84.16 (10)	N1—C2—C1	113.6 (4)
O7—Pr2—O9	64.76 (10)	N1—C2—C3	123.1 (4)
O7—Pr2—O11ⁱⁱⁱ	136.21 (10)	C3—C2—C1	123.2 (4)
O7—Pr2—O13ⁱⁱⁱ	131.51 (9)	C2—C3—H3	120.4
O7—Pr2—O16	69.72 (11)	C2—C3—C4	119.2 (4)
O7—Pr2—O17	71.87 (10)	C4—C3—H3	120.4
O7—Pr2—C1ⁱ	133.16 (11)	O5—C4—C3	123.3 (4)
O7—Pr2—C7ⁱⁱ	73.09 (11)	O5—C4—C5	117.9 (4)
O9—Pr2—O1ⁱ	70.34 (9)	C3—C4—C5	118.8 (4)
O9—Pr2—O2ⁱ	75.37 (10)	C4—C5—H5A	121.1
O9—Pr2—O3ⁱⁱ	104.33 (9)	C6—C5—C4	117.9 (4)
O9—Pr2—O4ⁱⁱ	74.22 (10)	C6—C5—H5A	121.1
O9—Pr2—O13ⁱⁱⁱ	140.30 (10)	N1—C6—C5	123.0 (4)
O9—Pr2—C1ⁱ	69.61 (11)	N1—C6—C7	113.3 (4)
O9—Pr2—C7ⁱⁱ	88.79 (11)	C5—C6—C7	123.7 (4)
O11ⁱⁱⁱ—Pr2—O1ⁱ	66.23 (9)	O3—C7—Pr2ⁱⁱ	65.2 (2)
O11ⁱⁱⁱ—Pr2—O2ⁱ	82.52 (10)	O3—C7—C6	117.1 (4)
O11ⁱⁱⁱ—Pr2—O3ⁱⁱ	119.82 (9)	O4—C7—Pr2ⁱⁱ	57.6 (2)
O11ⁱⁱⁱ—Pr2—O4ⁱⁱ	133.81 (10)	O4—C7—O3	122.8 (4)
O11ⁱⁱⁱ—Pr2—O9	135.73 (9)	O4—C7—C6	120.0 (4)
O11ⁱⁱⁱ—Pr2—O13ⁱⁱⁱ	63.37 (9)	C6—C7—Pr2ⁱⁱ	177.2 (3)
O11ⁱⁱⁱ—Pr2—C1ⁱ	74.49 (10)	O8—C9—C8	116.4 (4)
O11ⁱⁱⁱ—Pr2—C7ⁱⁱ	131.07 (11)	O9—C9—O8	126.7 (4)
O13ⁱⁱⁱ—Pr2—O1ⁱ	106.12 (9)	O9—C9—C8	116.9 (4)
O13ⁱⁱⁱ—Pr2—O2ⁱ	74.10 (10)	O6—C8—C9	116.7 (4)
O13ⁱⁱⁱ—Pr2—O3ⁱⁱ	67.88 (9)	O7—C8—O6	126.5 (4)
O13ⁱⁱⁱ—Pr2—O4ⁱⁱ	72.69 (10)	O7—C8—C9	116.8 (4)
O13ⁱⁱⁱ—Pr2—C1ⁱ	91.14 (12)	O12—C11—O13	125.7 (4)
O13ⁱⁱⁱ—Pr2—C7ⁱⁱ	68.71 (10)	O12—C11—C10	118.3 (4)
O16—Pr2—O1ⁱ	68.24 (10)	O13—C11—C10	115.9 (4)
O16—Pr2—O2ⁱ	116.84 (10)	O10—C10—O11	128.1 (4)
O16—Pr2—O3ⁱⁱ	126.51 (10)	O10—C10—C11	116.3 (4)
O16—Pr2—O4ⁱⁱ	149.02 (12)	O11—C10—C11	115.6 (4)

Pr1—O1—C1—Pr2ⁱ	−161.4 (3)	Pr2^iv—O11—C10—C11	−3.7 (5)
Pr1—O1—C1—O2	−154.6 (3)	Pr2^iv—O13—C11—O12	−170.6 (4)
Pr1—O1—C1—C2	26.9 (5)	Pr2^iv—O13—C11—C10	9.8 (5)
Pr1—O3—C7—Pr2ⁱⁱ	−163.8 (3)	O1—C1—C2—N1	−15.8 (6)
Pr1—O3—C7—O4	−165.4 (3)	O1—C1—C2—C3	161.7 (4)
Pr1—O3—C7—C6	17.9 (5)	O2—C1—C2—N1	165.7 (4)
Pr1—O6—C8—O7	−173.3 (3)	O2—C1—C2—C3	−16.9 (6)
Pr1—O6—C8—C9	7.5 (5)	O5—C4—C5—C6	177.0 (4)
Pr1—O8—C9—O9	−179.6 (3)	O8—C9—C8—O6	−4.7 (6)
Pr1—O8—C9—C8	−0.3 (5)	O8—C9—C8—O7	176.0 (4)
Pr1—O10—C10—O11	179.5 (3)	O9—C9—C8—O6	174.6 (4)
Pr1—O10—C10—C11	0.1 (5)	O9—C9—C8—O7	−4.6 (6)
Pr1—O12—C11—O13	−173.4 (3)	O12—C11—C10—O10	−4.2 (7)
Pr1—O12—C11—C10	6.1 (6)	O12—C11—C10—O11	176.3 (4)
Pr1—N1—C2—C1	−2.4 (5)	O13—C11—C10—O10	175.3 (4)
Pr1—N1—C2—C3	−179.9 (3)	O13—C11—C10—O11	−4.1 (6)
Pr1—N1—C6—C5	177.6 (3)	N1—C2—C3—C4	1.5 (7)
Pr1—N1—C6—C7	−4.8 (5)	N1—C6—C7—O3	−8.1 (6)
Pr2ⁱ—O1—C1—O2	6.8 (4)	N1—C6—C7—O4	175.1 (4)
Pr2ⁱ—O1—C1—C2	−171.7 (3)	C1—C2—C3—C4	−175.7 (4)
Pr2ⁱ—O2—C1—O1	−7.3 (5)	C2—N1—C6—C5	−2.1 (6)
Pr2ⁱ—O2—C1—C2	171.2 (3)	C2—N1—C6—C7	175.5 (4)
Pr2ⁱⁱ—O3—C7—O4	−1.6 (4)	C2—C3—C4—O5	−179.1 (4)
Pr2ⁱⁱ—O3—C7—C6	−178.3 (3)	C2—C3—C4—C5	−0.6 (6)
Pr2ⁱⁱ—O4—C7—O3	1.7 (5)	C3—C4—C5—C6	−1.5 (6)
Pr2ⁱⁱ—O4—C7—C6	178.3 (3)	C4—C5—C6—N1	3.0 (7)
Pr2—O7—C8—O6	−168.6 (3)	C4—C5—C6—C7	−174.4 (4)
Pr2—O7—C8—C9	10.6 (5)	C5—C6—C7—O3	169.5 (4)
Pr2—O9—C9—O8	175.9 (3)	C5—C6—C7—O4	−7.3 (7)
Pr2—O9—C9—C8	−3.3 (5)	C6—N1—C2—C1	177.3 (4)
Pr2^iv—O11—C10—O10	176.9 (3)	C6—N1—C2—C3	−0.2 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O13^v	0.82	1.81	2.626 (4)	170
O14—H14A···O11^vi	0.82 (2)	1.92 (2)	2.735 (4)	173 (5)
O14—H14B···O18	0.83 (2)	1.93 (2)	2.755 (5)	175 (5)
O15A—H15A···O19^vii	0.83 (2)	2.16 (4)	2.81 (3)	135 (3)
O15A—H15A···O21A	0.83 (2)	2.26 (2)	2.89 (2)	134 (4)
O15A—H15B···O21B	0.84 (2)	2.02 (9)	2.71 (3)	138 (11)
O15B—H15C···O21C	0.84 (2)	2.15 (6)	2.93 (3)	155 (10)
O15B—H15D···O7ⁱⁱ	0.86 (2)	1.96 (4)	2.75 (2)	152 (5)
O16—H16A···O8ⁱ	0.86 (2)	1.85 (2)	2.705 (4)	179 (5)
O16—H16B···O20A^viii	0.83 (2)	2.17 (4)	2.96 (3)	159 (6)
O16—H16B···O20B	0.83 (2)	2.12 (3)	2.94 (2)	172 (5)
O17—H17A···O12ⁱⁱ	0.83 (2)	2.33 (4)	2.922 (4)	129 (4)
O17—H17A···O15Aⁱⁱ	0.83 (2)	2.13 (3)	2.892 (19)	153 (5)
O17—H17A···O15Bⁱⁱ	0.83 (2)	2.15 (3)	2.865 (18)	144 (4)
O17—H17B···O5^viii	0.83 (2)	2.09 (2)	2.914 (4)	171 (5)
O18—H18A···O4^ix	0.85 (2)	2.10 (2)	2.951 (6)	177 (6)
O18—H18B···O2^vi	0.85 (2)	2.21 (3)	3.011 (6)	156 (7)
O19—H19A···O18^vii	0.83 (2)	2.56 (7)	3.161 (8)	130 (7)
O19—H19B···O9	0.83 (2)	2.15 (2)	2.904 (7)	151 (5)
O20A—H20A···O20B	0.87	2.17	2.901 (14)	141
O20A—H20B···O19^x	0.85	2.13	2.87 (3)	146
O20B—H20C···O19ⁱ	0.85	2.13	2.87 (2)	145

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (v) x, y−1, z; (vi) −x, −y+2, −z; (vii) −x, −y+2, −z+1; (viii) −x+1, −y, −z+1; (ix) x−1, y+1, z; (x) x+1, y−1, z.

Acknowledgements

AK is thankful to Chiang Mai University for a Presidential Scholarship. TC thanks Chiang Mai University for the support under the Proactive Researcher Scheme.

Funding information

Funding for this research was provided by: the National Research Council of Thailand (NRCT) and Chiang Mai University (Contract Number N42A670317), (award to A. Rujiwatra).

References

Banerjee, A., Saha, A. & Saha, B. K. (2019). Cryst. Growth Des. 19, 2245–2252. Web of Science CrossRef CAS Google Scholar
Bünzli, J. G. (2014). J. Coord. Chem. 67, 3706–3733. Google Scholar
Chen, Z., Fang, M., Ren, P., Li, X., Zhao, B., Wei, S. & Cheng, P. (2008). Z. Anorg. Allg. Chem. 634, 382–386. CrossRef CAS 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
Li, B., Wen, H.-M., Cui, Y., Qian, G. & Chen, B. (2015). Prog. Polym. Sci. 48, 40–84. Web of Science CrossRef Google Scholar
Patra, K. & Pal, H. (2025). RSC Sustainability 3, 629–660. CrossRef CAS Google Scholar
Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Roy, S., Chakraborty, A. & Maji, T. K. (2014). Coord. Chem. Rev. 273–274, 139–164. 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
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Wang, X., Jiang, Y., Tissot, A. & Serre, C. (2023). Coord. Chem. Rev. 497, 215454. CrossRef Google Scholar
Yao, Z., Wang, J. & Pei, J. (2018). Cryst. Growth Des. 18, 7–15. CrossRef CAS Google Scholar
Zhang, Y., Liu, S., Zhao, Z.-S., Wang, Z., Zhang, R., Liu, L. & Han, Z.-B. (2021). Inorg. Chem. Front. 8, 590–619. CrossRef CAS Google Scholar
Zhao, X., Zhao, B., Wei, S. & Cheng, P. (2009). Inorg. Chem. 48, 11048–11057. CrossRef PubMed CAS Google Scholar
Zou, J., Chen, M., Li, M., Xing, Q., Zhang, A. & Peng, Q. (2010). J. Coord. Chem. 63, 3576–3588. CrossRef CAS Google Scholar
Zou, J., Chen, M., Zhang, L., Xing, Q. & Xiong, Z. (2011). J. Chem. Crystallogr. 41, 1820–1833. CrossRef CAS Google Scholar
Zou, J., Wen, Z., Peng, Q., Zeng, G., Xing, Q. & Chen, M. (2009). J. Coord. Chem. 62, 3324–3331. CrossRef CAS 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.