Crystal structure and characterization of a new lanthanide coordination polymer, [Pr2(pydc)(phth)2(H2O)3]·H2O

Yotnoi, B.; Rujiwatra, A.

doi:10.1107/S2056989024000872

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ISSN: 2056-9890

Volume 80| Part 2| February 2024| Pages 228-231

https://doi.org/10.1107/S2056989024000872

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Crystal structure and characterization of a new lanthanide coordination polymer, [Pr₂(pydc)(phth)₂(H₂O)₃]·H₂O

Bunlawee Yotnoi ^a ^* and Apinpus Rujiwatra ^b

^aDepartment of Chemistry, School of Science, University of Phayao, Phayao, 56000, Thailand, and ^bDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
^*Correspondence e-mail: bunlawee.yo@up.ac.th

Edited by J. M. Delgado, Universidad de Los Andes, Venezuela (Received 6 November 2023; accepted 24 January 2024; online 31 January 2024)

A new lanthanide coordination polymer, poly[[triaquabis(μ₄-phthalato)(μ₃-pyridine-2,5-dicarboxylato)dipraseodymium] monohydrate], {[Pr₂(C₇H₃NO₄)₂(C₈H₄O₄)(H₂O)₃]·H₂O}_n or {[Pr₂(phth)₂(pydc)(H₂O)₃]·H₂O}_n, (pydc²⁻ = pyridine-2,5-dicarboxylate and phth²⁻ = phthalate) was synthesized and characterized, revealing the structure to be an assembly of di-periodic {Pr₂(pydc)(phth)₂(H₂O)₃}_n layers. Each layer is built up by edge-sharing {Pr₂N₂O₁₄} and {Pr₂O₁₆} dimers, which are connected through a new coordination mode of pydc²⁻ and phth²⁻. These layers are stabilized by internal hydrogen bonds and π–π interactions. In addition, a three-dimensional supramolecular framework is built by interlayer hydrogen-bonding interactions involving the non-coordinated water molecule. Thermogravimetric analysis shows that the title compound is thermally stable up to 400°C.

Keywords: crystal structure; coordination polymer; lanthanide; pyridine-2,5-dicarboxylate; phthalate..

CCDC reference: 2327873

1. Chemical context

Lanthanide coordination polymers (LnCPs) have attracted widespread interest because of their unique properties and wide range of potential applications, such as in luminescent temperature sensing (Rocha et al., 2016 ), catalysis (Sinchow et al., 2022 ), gas detection (Thammakan et al., 2023 ) and drug delivery (Wei et al., 2020 ). However, the high coordination numbers of the trivalent lanthanides (Ln^III) and the versatility in their coordination geometries complicates the control of intermolecular interactions and the prediction of coordination polymer frameworks. In addition, the synthesis of these frameworks is also influenced considerably by differences in synthetic procedures and conditions such as solvents, pH, reaction temperature and time, among other factors (Sinchow et al., 2019 ). Organic ligands are utilized as a template for the structural design, to direct the framework architecture. Among the organic ligands available, polycarboxylic acids are notably the most used because they are hard base ligands and can facilitate diverse coordination modes. In this work, pyridine-2,5-dicarboxylic acid (H₂pydc) and phthalic acid (H₂phth) were chosen to be the structure-directing ligands. Relevant structures include, for example, [Pr₃(phen)₂(phth)₄(NO₃)]·H₂O (phen = 1,10-phenanthroline) (refcode: LAXWOX; Thirumurugan & Natarajan, 2005 ), [Eu(phth)(OAc)(H₂O)] (OAc = acetate) (refcode: TAZDAD; Jittipiboonwat et al., 2022 ), [Pr(pydc)(pip)_1/2(H₂O] (pip = 2,5-piperazinedicarboxylate) (refcode: WUWBIB; Ay et al., 2016 ) and [Pr(pydc)(NA)H₂O]n (NA = nicotinic acid) (refcode: MEJNEY; Hu et al., 2022 ).

2. Structural commentary

The asymmetric unit of [Pr₂(pydc)(phth)₂(H₂O)₃]·H₂O is composed of two Pr^III metal centers, one molecule of pydc²⁻, two molecules of phth²⁻, three coordinated water molecules and a non-ligated water molecule (Fig. 1). The Pr1 ion is ninefold coordinated to one N atom from pydc²⁻ and eight O atoms from four phth²⁻, two pydc²⁻ and one water molecule to form a {Pr(1)NO₈} motif that can be described as a distorted tricapped trigonal prism. The Pr2 ion is also ninefold coordinated, being surrounded by nine O atoms from three phth²⁻, one pydc²⁻ and two water molecules in a distorted tricapped trigonal–prismatic {Pr(2)O₉} motif. The Pr—O bond lengths are in the range 2.413 (3)–2.691 (3) Å and the Pr—N bond is 2.696 (3) Å (Table 1), in accordance with a previous report for Pr^III frameworks of pydc²⁻ [2.390 (2)–2.717 (3) Å; Sinchow et al., 2019] and phth²⁻ [2.456 (4)–2.696 (4) Å; Thirumurugan & Natarajan, 2005]. The {Pr(1)NO₈} motif is linked to the adjacent Pr1, forming edge-sharing {Pr(1)₂N₂O₁₄} dimers, and two neighboring {Pr(1)₂N₂O₁₄} dimers are fused through the μ₄-η²:η¹:η¹: η¹ carboxyl group of phth²⁻ to form an infinite chain in the b-axis direction. In a similar fashion, two {Pr(2)O₉} motifs are linked to produce {Pr(2)₂O₁₆} dimers. These dimers are then connected by the carboxyl groups of phth²⁻ in a μ₃-η²:η¹:η¹:η¹ fashion to form a mono-periodic chain also extending in the b-axis direction. These chains are connected through a novel coordination mode for pydc^2- involving a μ₁-η¹:η¹ carboxyl group at one side and a μ₂-η¹:η¹ carboxyl group together with the pyridyl N atom coordinated on the other side to form a {[Pr₂(pydc)(phth)₂(H₂O)₃]}_n layer extending in the (101) plane (Fig. 2a).

Table 1
Selected bond lengths (Å)

Pr1—O7ⁱ	2.536 (3)	Pr2—O12^iv	2.514 (2)
Pr1—O2ⁱⁱ	2.580 (2)	Pr2—O15W	2.413 (3)
Pr1—O5ⁱⁱⁱ	2.473 (2)	Pr2—O9^v	2.691 (3)
Pr1—O8ⁱ	2.689 (2)	Pr2—O9	2.469 (2)
Pr1—O8^iv	2.473 (3)	Pr2—O4	2.526 (2)
Pr1—O6	2.446 (3)	Pr2—O10^v	2.510 (3)
Pr1—O1	2.439 (2)	Pr2—O3	2.575 (3)
Pr1—N1	2.696 (3)	Pr2—O14W	2.460 (2)
Pr1—O13W	2.571 (4)	Pr2—O11^iv	2.529 (3)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
Extended asymmetric unit of [Pr₂(pydc)(phth)₂(H₂O)₃]·H₂O drawn using 50% probability for ellipsoids (hydrogen atoms are omitted for clarity). Symmetry codes: (i) −x + 1, −y + 2, −z + 1; (ii) x, y + 1, z; (iii) −x + 1, −y + 1, −z + 1; (iv) x, y − 1, z; (v) −x + $[{3\over 2}]$ , −y + $[{3\over 2}]$ , −z + $[{1\over 2}]$ .

Figure 2
View of (a) the {Pr(1)₂N₂O₁₄} and {Pr(2)₂O₁₆} dimers in the (101) plane and (b) the hydrogen bonding and π–π interactions in the dimers.

3. Supramolecular features

The di-periodic supramolecular framework of the {[Pr₂(pydc)(phth)₂(H₂O)₃]}_n layers is further connected by intralayer hydrogen bonding, i.e. O13W—H13B⋯O2, O14W—H14A⋯O12, O14W—H14B⋯O4, O14W—H14B⋯O10, O15W—H15B⋯O4 and C11—H11⋯O14W interactions and π–π interactions (Fig. 2b and Table 2). The π–π interaction between two aromatic rings (pydc²⁻ and phth²-) is classified as a parallel stacked geometry (Banerjee et al., 2019 ), with an offset of 1.250 Å, interplanar angle of 5.96° and centroid-to-centroid distance of 3.892 (2) Å. In addition, the interlayer hydrogen-bonding interactions involve the coordinated water (O13W) and the hydrogen-bonded water (O16W). These interactions are O13W—H13A⋯O11, O13W—H13A⋯O16W, O15W—H15A⋯O16W, O16W—H16A⋯O7, O16W—H16B⋯O1 and O16W—H16B⋯O7 interactions (Fig. 3 and Table 2).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13W—H13A⋯O11^vi	0.85	2.57	3.003 (5)	113
O13W—H13A⋯O16W^vi	0.85	2.26	2.881 (5)	130
O13W—H13B⋯O2ⁱⁱ	0.86	2.52	2.820 (4)	102
O14W—H14A⋯O12^vii	0.85	1.95	2.766 (4)	160
O14W—H14B⋯O4ⁱⁱ	0.85	2.04	2.887 (4)	174
O14W—H14B⋯O10^vii	0.85	2.58	2.912 (4)	104
O15W—H15A⋯O16W	0.85	1.75	2.595 (4)	170
O15W—H15B⋯O4ⁱⁱ	0.85	1.92	2.725 (3)	158
O16W—H16B⋯O7^viii	0.85	2.31	2.709 (4)	109
O16W—H16B⋯O1^ix	0.85	2.13	2.938 (5)	158
C11—H11⋯O14W	0.93	2.51	3.375 (5)	156
Symmetry codes: (ii) ; (vi) $[-x+{\script{3\over 2}}, y-1, -z+1]$ ; (vii) $[-x+{\script{3\over 2}}, -y+{\script{5\over 2}}, -z+{\script{1\over 2}}]$ ; (viii) $[x+{\script{1\over 2}}, -y+2, z]$ ; (ix) $[-x+{\script{3\over 2}}, y+1, -z+1]$ .

Figure 3
Three-dimensional supramolecular framework of [Pr₂(pydc)(phth)₂(H₂O)₃]·H₂O.

4. Thermogravimetric analysis

The thermogravimetric curve of the title compound shows four steps of weight loss in the temperature range 30°C to 1000°C (Fig. 4). The first step occurs at 100–185°C with a 6.0% weight loss attributed to the removal of one hydrogen-bonded water and two coordinated water molecules (calc. 6.4%). The second step observed at 300–350°C is due to the loss of the other coordinated water molecule (exp. 2.5%, calc. 2.1%). This step is possibly due to the removal of O14W, which is held by both strong and weak hydrogen-bonding interactions. The next step of weight loss occurs in the temperature range 400–580°C and represents a higher weight loss of 37.3%. This step can be attributed to the pyrolysis of the organic ligands (two phth²⁻ ligands, calc. 38.7%). The last step of weight loss, from 580 to 1000°C, could be due to the elimination of the bridging pydc²⁻ ligand to form praseodymium oxide residues (exp. 14.7%, calc. 19.5%).

Figure 4
Thermogravimetric analysis of [Pr₂(pydc)(pth)₂(H₂O)₃]·H₂O.

5. Database survey

A search for the title compound in the Cambridge Structural Database (CSD version 5.44, April 2023; Groom et al., 2016 ) using CONQUEST software (version 2023.2.0; Bruno et al., 2002 ) did not match with any reported structures. Regarding organic ligands, there were 123 structures of lanthanide coordination polymers that included pydc²⁻. Among these structures, interestingly, there were none in which pydc²⁻ adopts the same coordination mode as in the title compound (Sinchow et al., 2019). This new mode of coordination acts as a μ₃-bridge to link three Pr^III ions and facilitates the formation of a di-periodic coordination framework. Regarding phth²⁻, there were 118 structures deposited in the CSD, none of which contains pydc²⁻ in the structure. However, there is a structure including both pydc²⁻ and phth²⁻ ligands that incorporates a first-row transition metal: [Gd₂(H₂O)₂Ni(H₂O)₂(phth)₂(pydc)₂]₃·8H₂O (refcode: XOZYER; Mahata et al., 2009 ).

6. Synthesis and crystallization

All chemicals were used as received without further purification: Pr₆O₁₁ (TJTM, 99.9%), pyridine-2,5-dicarboxylic acid (H₂pydc; Sigma-Aldrich, 98%), 1,2-benzenedicarboxylic acid (H₂phth; Sigma-Aldrich, 98%) and NaOH (QReC, 99%). The Pr(NO₃)₃·6H₂O precursor was prepared by crystallization from solution of the lanthanide oxide in nitric acid (RCI Labscan, 65%).

To synthesize [Pr₂(pydc)(phth)₂(H₂O)₃]·H₂O, a solution of H₂pydc (0.125 mmol, 20.8 mg) and H₂phth (0.25 mmol, 41.5 mg) was prepared in 8 mL of deionized water, then 1.35 mL of 0.5 M NaOH were added and the pH adjusted to 5. Pr(NO₃)·6H₂O (0.25 mmol, 146.6 mg) was dissolved in 2 mL of deionized water and mixed with the ligand solution. The reaction mixture was then transferred into a 23 mL Teflon-lined hydrothermal reactor and held at 423 K for 72 h. Green block-shaped crystals were collected and dried at room temperature. The crystals were characterized using FT–IR spectroscopy (Nicolet iS5 FTIR Spectrometer; iD5 ATR mode; cm⁻¹): 3243(br), 1615(w), 1575(m), 1543(m), 1517(m), 1481(m), 1450(w), 1391(m), 1354(m), 1283(w), 1143(w), 1088(w), 1028(w), 870(w), 840(m), 762(m), 670(m), 648(w). The FT–IR spectrum shows a broad band at 3243 cm⁻¹ attributed to the ν(O—H) stretching from the water molecules. The characteristic peak at 1615 cm⁻¹ corresponds to the C=O stretching vibrational mode of the carboxylate group. The peak at 1283 cm⁻¹ is due to the C—N stretching of the pydc²⁻ ligand.

Thermogravimetric analyses (TGA) were carried out using a Mettler Toledo TGA/DSC 3+, with a heating rate of 20°C min⁻¹, ramping from 30 to 1100°C under a nitrogen gas flow.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All hydrogen atoms of aromatic rings and water molecules were positioned geometrically and refined using a riding model with U_i_so(H) = 1.2–1.5U_eq(C,O).

Table 3
Experimental details

Crystal data
Chemical formula	[Pr₂(C₇H₃NO₄)₂(C₈H₄O₄)(H₂O)₃]·H₂O
M_r	847.21
Crystal system, space group	Monoclinic, I2/a
Temperature (K)	293
a, b, c (Å)	27.4898 (4), 5.9436 (1), 32.0473 (5)
β (°)	93.854 (1)
V (Å³)	5224.31 (14)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	3.77
Crystal size (mm)	0.3 × 0.2 × 0.08

Data collection
Diffractometer	SuperNova, Single source at offset/far, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.448, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	26747, 5561, 5004
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.05
No. of reflections	5561
No. of parameters	387
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −1.08
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2327873

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024000872/jw2002sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024000872/jw2002Isup3.hkl

checkCIF report

Computing details top

Poly[[triaquabis(µ₄-phthalato)(µ₃-pyridine-2,5-dicarboxylato)dipraseodymium] monohydrate] top

Crystal data top

[Pr₂(C₇H₃NO₄)₂(C₈H₄O₄)(H₂O)₃]·H₂O	F(000) = 3280
M_r = 847.21	D_x = 2.154 Mg m⁻³
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 27.4898 (4) Å	Cell parameters from 20454 reflections
b = 5.9436 (1) Å	θ = 2.0–27.3°
c = 32.0473 (5) Å	µ = 3.77 mm⁻¹
β = 93.854 (1)°	T = 293 K
V = 5224.31 (14) Å³	Block, clear light green
Z = 8	0.3 × 0.2 × 0.08 mm

Data collection top

SuperNova, Single source at offset/far, HyPix3000 diffractometer	5561 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	5004 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.062
Detector resolution: 10.0000 pixels mm^-1	θ_max = 27.4°, θ_min = 1.9°
ω scans	h = −32→34
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	k = −7→7
T_min = 0.448, T_max = 1.000	l = −40→40
26747 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0445P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.003
5561 reflections	Δρ_max = 1.03 e Å⁻³
387 parameters	Δρ_min = −1.08 e Å⁻³
0 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.

Refinement. The crystal structure was solved using the dual-space algorithm with the SHELXT program (Sheldrick, 2015a) and refined on F² by the full-matrix least-squares technique using the SHELXL program (Sheldrick, 2015b) via the Olex2 interface (Dolomanov et al., 2009).

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

	x	y	z	U_iso*/U_eq
Pr1	0.57085 (2)	0.43694 (3)	0.52003 (2)	0.01775 (8)
Pr2	0.75715 (2)	0.65833 (3)	0.31515 (2)	0.01807 (8)
O7	0.45283 (10)	1.3428 (4)	0.41664 (9)	0.0278 (6)
O2	0.63896 (9)	−0.2639 (4)	0.52143 (8)	0.0258 (6)
O12	0.80011 (9)	1.3574 (4)	0.27660 (8)	0.0233 (6)
O5	0.48823 (9)	0.7809 (4)	0.44133 (8)	0.0245 (6)
O8	0.50558 (9)	1.2895 (4)	0.47057 (8)	0.0225 (6)
O15W	0.79900 (10)	0.9333 (4)	0.35981 (10)	0.0348 (7)
H15A	0.828906	0.931811	0.368452	0.052*
H15B	0.788865	1.062225	0.366759	0.052*
O9	0.79607 (10)	0.8562 (4)	0.25842 (8)	0.0247 (6)
O4	0.74925 (10)	0.3284 (4)	0.36394 (9)	0.0288 (7)
O10	0.82266 (10)	1.0318 (4)	0.20438 (9)	0.0285 (6)
O6	0.56535 (10)	0.6744 (4)	0.45754 (9)	0.0270 (6)
O3	0.71029 (11)	0.6308 (4)	0.38190 (9)	0.0332 (7)
O14W	0.70712 (9)	1.0001 (4)	0.30575 (9)	0.0272 (6)
H14A	0.711517	1.058376	0.282044	0.041*
H14B	0.717297	1.099306	0.323394	0.041*
O11	0.84297 (10)	1.5114 (5)	0.32951 (9)	0.0328 (7)
O1	0.59351 (10)	0.0418 (4)	0.52815 (9)	0.0314 (7)
N1	0.63969 (11)	0.2702 (5)	0.47251 (10)	0.0237 (7)
O16W	0.89141 (13)	0.9700 (6)	0.38119 (11)	0.0511 (9)
H16A	0.898260	0.843887	0.370560	0.077*
H16B	0.898930	0.954362	0.407190	0.077*
O13W	0.63638 (14)	0.3845 (6)	0.58034 (11)	0.0575 (10)
H13A	0.623288	0.331315	0.601685	0.086*
H13B	0.647446	0.512964	0.588387	0.086*
C15	0.49303 (14)	1.2686 (5)	0.43171 (12)	0.0201 (8)
C22	0.88149 (13)	1.2236 (6)	0.29160 (12)	0.0224 (8)
C17	0.87562 (14)	1.0344 (6)	0.26623 (12)	0.0226 (8)
C23	0.83927 (13)	1.3731 (6)	0.29984 (12)	0.0214 (8)
C6	0.66161 (14)	0.3836 (6)	0.44322 (12)	0.0236 (8)
H6	0.650321	0.527214	0.436258	0.028*
C16	0.82826 (14)	0.9752 (6)	0.24196 (12)	0.0209 (8)
C2	0.65666 (13)	0.0621 (5)	0.48235 (12)	0.0200 (8)
C8	0.53344 (13)	0.7948 (5)	0.43889 (12)	0.0192 (8)
C5	0.70056 (13)	0.2984 (6)	0.42248 (12)	0.0229 (8)
C1	0.62796 (14)	−0.0633 (5)	0.51323 (12)	0.0196 (8)
C14	0.52822 (13)	1.1759 (5)	0.40244 (12)	0.0194 (8)
C7	0.72085 (14)	0.4317 (6)	0.38760 (12)	0.0236 (9)
C18	0.91496 (15)	0.8966 (7)	0.26096 (15)	0.0364 (11)
H18	0.911010	0.769656	0.244119	0.044*
C21	0.92728 (15)	1.2708 (7)	0.31040 (14)	0.0347 (10)
H21	0.931630	1.397619	0.327226	0.042*
C4	0.71830 (15)	0.0895 (6)	0.43396 (13)	0.0299 (10)
H4	0.744967	0.029575	0.421450	0.036*
C11	0.59980 (15)	1.0454 (7)	0.35039 (14)	0.0355 (11)
H11	0.623695	1.001566	0.332856	0.043*
C3	0.69586 (14)	−0.0308 (6)	0.46450 (12)	0.0266 (9)
H3	0.707294	−0.172427	0.472697	0.032*
C10	0.58662 (14)	0.9040 (6)	0.38164 (13)	0.0271 (9)
H10	0.602064	0.765556	0.385436	0.033*
C9	0.55037 (13)	0.9663 (6)	0.40764 (12)	0.0213 (8)
C13	0.54177 (15)	1.3151 (6)	0.37105 (13)	0.0300 (10)
H13	0.526545	1.453984	0.367252	0.036*
C12	0.57745 (16)	1.2535 (7)	0.34501 (14)	0.0377 (11)
H12	0.586413	1.350458	0.324088	0.045*
C19	0.96019 (16)	0.9438 (8)	0.28028 (16)	0.0454 (13)
H19	0.986346	0.847910	0.276856	0.054*
C20	0.96632 (17)	1.1326 (8)	0.30449 (17)	0.0485 (13)
H20	0.996917	1.167448	0.316952	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.01815 (13)	0.01481 (12)	0.02073 (14)	0.00126 (7)	0.00452 (9)	0.00299 (8)
Pr2	0.01974 (13)	0.01567 (12)	0.01921 (14)	0.00040 (7)	0.00422 (9)	0.00159 (8)
O7	0.0247 (15)	0.0284 (14)	0.0302 (17)	0.0052 (12)	0.0009 (13)	−0.0047 (12)
O2	0.0305 (15)	0.0164 (12)	0.0310 (16)	0.0006 (11)	0.0054 (13)	0.0040 (11)
O12	0.0186 (14)	0.0230 (13)	0.0278 (16)	0.0040 (11)	−0.0032 (12)	0.0000 (11)
O5	0.0222 (14)	0.0220 (13)	0.0300 (16)	−0.0022 (11)	0.0078 (12)	0.0052 (12)
O8	0.0312 (15)	0.0179 (12)	0.0184 (15)	−0.0023 (11)	0.0024 (12)	−0.0003 (11)
O15W	0.0267 (16)	0.0304 (15)	0.046 (2)	0.0023 (12)	−0.0064 (15)	−0.0147 (14)
O9	0.0262 (15)	0.0207 (12)	0.0280 (16)	−0.0066 (11)	0.0077 (12)	0.0032 (11)
O4	0.0362 (17)	0.0229 (13)	0.0292 (17)	0.0071 (12)	0.0155 (14)	0.0060 (11)
O10	0.0278 (15)	0.0332 (15)	0.0245 (16)	−0.0063 (12)	0.0020 (12)	0.0058 (12)
O6	0.0262 (15)	0.0261 (14)	0.0288 (16)	0.0055 (11)	0.0032 (13)	0.0105 (12)
O3	0.052 (2)	0.0198 (13)	0.0305 (17)	0.0036 (13)	0.0216 (15)	0.0004 (12)
O14W	0.0332 (16)	0.0228 (13)	0.0256 (16)	0.0057 (12)	0.0024 (13)	0.0019 (11)
O11	0.0314 (16)	0.0359 (15)	0.0299 (17)	0.0070 (13)	−0.0053 (13)	−0.0145 (13)
O1	0.0379 (17)	0.0202 (13)	0.0386 (18)	0.0036 (12)	0.0206 (14)	0.0074 (12)
N1	0.0259 (17)	0.0156 (14)	0.0306 (19)	0.0024 (13)	0.0097 (15)	0.0037 (14)
O16W	0.046 (2)	0.059 (2)	0.046 (2)	0.0062 (18)	−0.0142 (18)	0.0038 (17)
O13W	0.072 (3)	0.054 (2)	0.044 (2)	0.0244 (19)	−0.0162 (19)	0.0018 (17)
C15	0.023 (2)	0.0133 (16)	0.024 (2)	−0.0063 (15)	0.0044 (17)	0.0010 (15)
C22	0.021 (2)	0.0225 (18)	0.023 (2)	0.0021 (16)	0.0008 (16)	0.0015 (16)
C17	0.023 (2)	0.0228 (18)	0.022 (2)	0.0010 (16)	0.0028 (16)	0.0041 (16)
C23	0.020 (2)	0.0191 (17)	0.025 (2)	0.0008 (15)	0.0029 (17)	0.0022 (16)
C6	0.030 (2)	0.0174 (16)	0.024 (2)	0.0029 (16)	0.0075 (18)	0.0038 (16)
C16	0.021 (2)	0.0173 (17)	0.025 (2)	0.0039 (15)	0.0078 (17)	0.0030 (16)
C2	0.020 (2)	0.0177 (17)	0.022 (2)	0.0009 (14)	0.0037 (16)	−0.0003 (15)
C8	0.022 (2)	0.0146 (16)	0.021 (2)	0.0011 (15)	0.0046 (16)	−0.0022 (15)
C5	0.024 (2)	0.0221 (18)	0.023 (2)	0.0001 (16)	0.0077 (17)	0.0028 (16)
C1	0.023 (2)	0.0170 (17)	0.019 (2)	−0.0009 (15)	0.0020 (16)	0.0020 (14)
C14	0.0198 (19)	0.0174 (17)	0.021 (2)	−0.0037 (14)	0.0003 (16)	0.0019 (14)
C7	0.028 (2)	0.0210 (19)	0.023 (2)	−0.0004 (16)	0.0091 (18)	0.0012 (16)
C18	0.027 (2)	0.035 (2)	0.047 (3)	0.0083 (19)	0.004 (2)	−0.007 (2)
C21	0.026 (2)	0.034 (2)	0.044 (3)	0.0017 (19)	−0.001 (2)	−0.009 (2)
C4	0.029 (2)	0.0241 (19)	0.039 (3)	0.0037 (17)	0.014 (2)	0.0032 (18)
C11	0.029 (2)	0.046 (3)	0.033 (3)	−0.0025 (19)	0.015 (2)	0.003 (2)
C3	0.032 (2)	0.0202 (18)	0.029 (2)	0.0065 (16)	0.0095 (18)	0.0060 (16)
C10	0.028 (2)	0.0261 (19)	0.028 (2)	0.0016 (17)	0.0112 (18)	0.0018 (17)
C9	0.0182 (19)	0.0225 (18)	0.024 (2)	−0.0012 (15)	0.0035 (16)	0.0002 (16)
C13	0.039 (3)	0.0239 (19)	0.027 (2)	0.0015 (17)	0.005 (2)	0.0052 (17)
C12	0.043 (3)	0.039 (2)	0.033 (3)	−0.006 (2)	0.018 (2)	0.014 (2)
C19	0.026 (2)	0.053 (3)	0.056 (3)	0.018 (2)	0.000 (2)	−0.010 (3)
C20	0.018 (2)	0.063 (3)	0.063 (4)	0.002 (2)	−0.008 (2)	−0.012 (3)

Geometric parameters (Å, º) top

Pr1—Pr1ⁱ	4.0877 (4)	N1—C2	1.352 (4)
Pr1—O7ⁱⁱ	2.536 (3)	O16W—H16A	0.8495
Pr1—O2ⁱⁱⁱ	2.580 (2)	O16W—H16B	0.8500
Pr1—O5ⁱ	2.473 (2)	O13W—H13A	0.8548
Pr1—O8ⁱⁱ	2.689 (2)	O13W—H13B	0.8552
Pr1—O8^iv	2.473 (3)	C15—C14	1.497 (5)
Pr1—O6	2.446 (3)	C22—C17	1.391 (5)
Pr1—O1	2.439 (2)	C22—C23	1.499 (5)
Pr1—N1	2.696 (3)	C22—C21	1.387 (5)
Pr1—O13W	2.571 (4)	C17—C16	1.513 (5)
Pr1—C15ⁱⁱ	2.984 (4)	C17—C18	1.376 (5)
Pr2—O12^iv	2.514 (2)	C6—H6	0.9300
Pr2—O15W	2.413 (3)	C6—C5	1.393 (5)
Pr2—O9^v	2.691 (3)	C2—C1	1.504 (5)
Pr2—O9	2.469 (2)	C2—C3	1.370 (5)
Pr2—O4	2.526 (2)	C8—C9	1.523 (5)
Pr2—O10^v	2.510 (3)	C5—C7	1.507 (5)
Pr2—O3	2.575 (3)	C5—C4	1.375 (5)
Pr2—O14W	2.460 (2)	C14—C9	1.392 (5)
Pr2—O11^iv	2.529 (3)	C14—C13	1.373 (5)
Pr2—C23^iv	2.891 (4)	C18—H18	0.9300
Pr2—C16^v	2.986 (4)	C18—C19	1.380 (6)
O7—C15	1.256 (5)	C21—H21	0.9300
O2—C1	1.254 (4)	C21—C20	1.374 (6)
O12—C23	1.271 (4)	C4—H4	0.9300
O5—C8	1.253 (4)	C4—C3	1.390 (5)
O8—C15	1.276 (4)	C11—H11	0.9300
O15W—H15A	0.8498	C11—C10	1.375 (5)
O15W—H15B	0.8499	C11—C12	1.386 (5)
O9—C16	1.274 (4)	C3—H3	0.9300
O4—C7	1.281 (4)	C10—H10	0.9300
O10—C16	1.250 (4)	C10—C9	1.391 (5)
O6—C8	1.252 (4)	C13—H13	0.9300
O3—C7	1.229 (4)	C13—C12	1.379 (5)
O14W—H14A	0.8511	C12—H12	0.9300
O14W—H14B	0.8512	C19—H19	0.9300
O11—C23	1.256 (4)	C19—C20	1.368 (6)
O1—C1	1.255 (4)	C20—H20	0.9300
N1—C6	1.332 (4)

O7ⁱⁱ—Pr1—Pr1ⁱ	82.31 (6)	C23^iv—Pr2—C16^v	109.32 (10)
O7ⁱⁱ—Pr1—O2ⁱⁱⁱ	81.68 (8)	C15—O7—Pr1ⁱⁱ	98.1 (2)
O7ⁱⁱ—Pr1—O8ⁱⁱ	49.76 (8)	C1—O2—Pr1^iv	119.2 (2)
O7ⁱⁱ—Pr1—N1	150.37 (10)	C23—O12—Pr2ⁱⁱⁱ	93.8 (2)
O7ⁱⁱ—Pr1—O13W	70.46 (10)	C8—O5—Pr1ⁱ	138.9 (2)
O7ⁱⁱ—Pr1—C15ⁱⁱ	24.63 (10)	Pr1ⁱⁱⁱ—O8—Pr1ⁱⁱ	104.62 (8)
O2ⁱⁱⁱ—Pr1—Pr1ⁱ	123.65 (6)	C15—O8—Pr1ⁱⁱⁱ	142.8 (2)
O2ⁱⁱⁱ—Pr1—O8ⁱⁱ	98.79 (7)	C15—O8—Pr1ⁱⁱ	90.4 (2)
O2ⁱⁱⁱ—Pr1—N1	74.17 (8)	Pr2—O15W—H15A	126.8
O2ⁱⁱⁱ—Pr1—C15ⁱⁱ	92.20 (8)	Pr2—O15W—H15B	127.9
O5ⁱ—Pr1—Pr1ⁱ	67.00 (6)	H15A—O15W—H15B	104.5
O5ⁱ—Pr1—O7ⁱⁱ	69.95 (8)	Pr2—O9—Pr2^v	113.13 (9)
O5ⁱ—Pr1—O2ⁱⁱⁱ	148.44 (9)	C16—O9—Pr2	156.4 (3)
O5ⁱ—Pr1—O8ⁱⁱ	73.52 (7)	C16—O9—Pr2^v	90.4 (2)
O5ⁱ—Pr1—N1	126.85 (8)	C7—O4—Pr2	94.3 (2)
O5ⁱ—Pr1—O13W	90.61 (11)	C16—O10—Pr2^v	99.7 (2)
O5ⁱ—Pr1—C15ⁱⁱ	67.57 (8)	C8—O6—Pr1	136.3 (2)
O8^iv—Pr1—Pr1ⁱ	39.54 (6)	C7—O3—Pr2	93.4 (2)
O8ⁱⁱ—Pr1—Pr1ⁱ	35.83 (6)	Pr2—O14W—H14A	109.5
O8^iv—Pr1—O7ⁱⁱ	118.78 (9)	Pr2—O14W—H14B	109.6
O8^iv—Pr1—O2ⁱⁱⁱ	138.56 (8)	H14A—O14W—H14B	104.5
O8^iv—Pr1—O5ⁱ	70.29 (9)	C23—O11—Pr2ⁱⁱⁱ	93.5 (2)
O8^iv—Pr1—O8ⁱⁱ	75.37 (8)	C1—O1—Pr1	129.2 (2)
O8ⁱⁱ—Pr1—N1	150.31 (9)	C6—N1—Pr1	125.4 (2)
O8^iv—Pr1—N1	90.82 (9)	C6—N1—C2	117.5 (3)
O8^iv—Pr1—O13W	151.68 (10)	C2—N1—Pr1	116.7 (2)
O8^iv—Pr1—C15ⁱⁱ	96.50 (10)	H16A—O16W—H16B	104.5
O8ⁱⁱ—Pr1—C15ⁱⁱ	25.31 (9)	Pr1—O13W—H13A	109.6
O6—Pr1—Pr1ⁱ	68.41 (6)	Pr1—O13W—H13B	109.6
O6—Pr1—O7ⁱⁱ	110.62 (9)	H13A—O13W—H13B	104.4
O6—Pr1—O2ⁱⁱⁱ	67.76 (9)	O7—C15—Pr1ⁱⁱ	57.32 (19)
O6—Pr1—O5ⁱ	134.86 (9)	O7—C15—O8	121.0 (3)
O6—Pr1—O8^iv	71.19 (9)	O7—C15—C14	118.5 (3)
O6—Pr1—O8ⁱⁱ	74.76 (8)	O8—C15—Pr1ⁱⁱ	64.34 (18)
O6—Pr1—N1	75.93 (9)	O8—C15—C14	120.2 (3)
O6—Pr1—O13W	133.39 (12)	C14—C15—Pr1ⁱⁱ	165.5 (2)
O6—Pr1—C15ⁱⁱ	94.57 (9)	C17—C22—C23	121.4 (3)
O1—Pr1—Pr1ⁱ	116.18 (7)	C21—C22—C17	118.9 (3)
O1—Pr1—O7ⁱⁱ	119.27 (9)	C21—C22—C23	119.6 (3)
O1—Pr1—O2ⁱⁱⁱ	118.80 (9)	C22—C17—C16	123.4 (3)
O1—Pr1—O5ⁱ	67.30 (8)	C18—C17—C22	119.5 (4)
O1—Pr1—O8ⁱⁱ	140.00 (8)	C18—C17—C16	117.1 (3)
O1—Pr1—O8^iv	84.05 (9)	O12—C23—Pr2ⁱⁱⁱ	60.15 (18)
O1—Pr1—O6	130.10 (9)	O12—C23—C22	119.2 (3)
O1—Pr1—N1	61.47 (8)	O11—C23—Pr2ⁱⁱⁱ	60.80 (19)
O1—Pr1—O13W	69.03 (11)	O11—C23—O12	121.0 (3)
O1—Pr1—C15ⁱⁱ	131.64 (9)	O11—C23—C22	119.8 (4)
N1—Pr1—Pr1ⁱ	125.47 (7)	C22—C23—Pr2ⁱⁱⁱ	179.4 (3)
N1—Pr1—C15ⁱⁱ	165.50 (9)	N1—C6—H6	118.3
O13W—Pr1—Pr1ⁱ	149.66 (8)	N1—C6—C5	123.4 (3)
O13W—Pr1—O2ⁱⁱⁱ	66.39 (11)	C5—C6—H6	118.3
O13W—Pr1—O8ⁱⁱ	120.15 (9)	O9—C16—Pr2^v	64.3 (2)
O13W—Pr1—N1	84.09 (11)	O9—C16—C17	120.9 (3)
O13W—Pr1—C15ⁱⁱ	95.07 (11)	O10—C16—Pr2^v	56.0 (2)
C15ⁱⁱ—Pr1—Pr1ⁱ	58.24 (8)	O10—C16—O9	120.3 (4)
O12^iv—Pr2—O9^v	78.00 (8)	O10—C16—C17	118.6 (3)
O12^iv—Pr2—O4	79.32 (8)	C17—C16—Pr2^v	172.4 (2)
O12^iv—Pr2—O3	129.85 (8)	N1—C2—C1	114.8 (3)
O12^iv—Pr2—O11^iv	51.70 (9)	N1—C2—C3	122.7 (3)
O12^iv—Pr2—C23^iv	26.01 (9)	C3—C2—C1	122.5 (3)
O12^iv—Pr2—C16^v	83.43 (9)	O5—C8—C9	115.7 (3)
O15W—Pr2—O12^iv	123.55 (9)	O6—C8—O5	126.7 (3)
O15W—Pr2—O9^v	138.66 (9)	O6—C8—C9	117.5 (3)
O15W—Pr2—O9	84.33 (10)	C6—C5—C7	119.8 (3)
O15W—Pr2—O4	102.48 (10)	C4—C5—C6	118.1 (3)
O15W—Pr2—O10^v	145.79 (9)	C4—C5—C7	122.1 (3)
O15W—Pr2—O3	78.21 (10)	O2—C1—O1	124.8 (3)
O15W—Pr2—O14W	75.74 (9)	O2—C1—C2	118.6 (3)
O15W—Pr2—O11^iv	73.99 (9)	O1—C1—C2	116.5 (3)
O15W—Pr2—C23^iv	98.70 (10)	C9—C14—C15	123.4 (3)
O15W—Pr2—C16^v	150.18 (9)	C13—C14—C15	117.1 (3)
O9—Pr2—O12^iv	74.68 (8)	C13—C14—C9	119.3 (3)
O9—Pr2—O9^v	66.86 (9)	O4—C7—C5	117.2 (3)
O9—Pr2—O4	152.26 (8)	O3—C7—O4	121.4 (3)
O9—Pr2—O10^v	116.47 (9)	O3—C7—C5	121.4 (3)
O9—Pr2—O3	155.19 (8)	C17—C18—H18	119.5
O9—Pr2—O11^iv	81.57 (9)	C17—C18—C19	121.1 (4)
O9^v—Pr2—C23^iv	102.54 (10)	C19—C18—H18	119.5
O9—Pr2—C23^iv	76.84 (9)	C22—C21—H21	119.6
O9—Pr2—C16^v	92.12 (10)	C20—C21—C22	120.9 (4)
O9^v—Pr2—C16^v	25.27 (8)	C20—C21—H21	119.6
O4—Pr2—O9^v	116.93 (9)	C5—C4—H4	120.4
O4—Pr2—O3	50.80 (8)	C5—C4—C3	119.2 (3)
O4—Pr2—O11^iv	74.77 (9)	C3—C4—H4	120.4
O4—Pr2—C23^iv	75.56 (9)	C10—C11—H11	120.0
O4—Pr2—C16^v	94.37 (10)	C10—C11—C12	120.0 (4)
O10^v—Pr2—O12^iv	89.35 (8)	C12—C11—H11	120.0
O10^v—Pr2—O9^v	49.64 (8)	C2—C3—C4	119.0 (3)
O10^v—Pr2—O4	72.22 (9)	C2—C3—H3	120.5
O10^v—Pr2—O3	72.59 (9)	C4—C3—H3	120.5
O10^v—Pr2—O11^iv	132.78 (8)	C11—C10—H10	119.7
O10^v—Pr2—C23^iv	111.90 (10)	C11—C10—C9	120.5 (4)
O10^v—Pr2—C16^v	24.37 (8)	C9—C10—H10	119.7
O3—Pr2—O9^v	116.93 (9)	C14—C9—C8	121.8 (3)
O3—Pr2—C23^iv	122.92 (10)	C10—C9—C8	118.6 (3)
O3—Pr2—C16^v	94.34 (10)	C10—C9—C14	119.5 (3)
O14W—Pr2—O12^iv	143.58 (9)	C14—C13—H13	119.2
O14W—Pr2—O9^v	69.69 (8)	C14—C13—C12	121.5 (4)
O14W—Pr2—O9	77.46 (8)	C12—C13—H13	119.2
O14W—Pr2—O4	130.24 (8)	C11—C12—H12	120.4
O14W—Pr2—O10^v	82.48 (9)	C13—C12—C11	119.3 (3)
O14W—Pr2—O3	81.23 (9)	C13—C12—H12	120.4
O14W—Pr2—O11^iv	144.54 (9)	C18—C19—H19	120.2
O14W—Pr2—C23^iv	154.13 (9)	C20—C19—C18	119.6 (4)
O14W—Pr2—C16^v	74.59 (9)	C20—C19—H19	120.2
O11^iv—Pr2—O9^v	126.43 (8)	C21—C20—H20	120.0
O11^iv—Pr2—O3	109.85 (9)	C19—C20—C21	120.0 (4)
O11^iv—Pr2—C23^iv	25.69 (10)	C19—C20—H20	120.0
O11^iv—Pr2—C16^v	134.86 (9)

Pr1ⁱⁱ—O7—C15—O8	10.0 (3)	N1—C2—C1—O1	−3.9 (5)
Pr1ⁱⁱ—O7—C15—C14	−163.8 (2)	N1—C2—C3—C4	−2.2 (6)
Pr1^iv—O2—C1—O1	46.5 (5)	C15—C14—C9—C8	11.8 (6)
Pr1^iv—O2—C1—C2	−131.6 (3)	C15—C14—C9—C10	−172.9 (4)
Pr1ⁱ—O5—C8—O6	3.6 (6)	C15—C14—C13—C12	173.7 (4)
Pr1ⁱ—O5—C8—C9	179.2 (2)	C22—C17—C16—O9	−88.4 (4)
Pr1ⁱⁱⁱ—O8—C15—Pr1ⁱⁱ	−115.2 (3)	C22—C17—C16—O10	96.6 (4)
Pr1ⁱⁱⁱ—O8—C15—O7	−124.5 (4)	C22—C17—C18—C19	−0.3 (6)
Pr1ⁱⁱ—O8—C15—O7	−9.3 (3)	C22—C21—C20—C19	−0.9 (8)
Pr1ⁱⁱ—O8—C15—C14	164.4 (3)	C17—C22—C23—O12	−15.5 (5)
Pr1ⁱⁱⁱ—O8—C15—C14	49.2 (5)	C17—C22—C23—O11	164.4 (4)
Pr1—O6—C8—O5	−21.5 (6)	C17—C22—C21—C20	−0.5 (6)
Pr1—O6—C8—C9	162.9 (2)	C17—C18—C19—C20	−1.1 (7)
Pr1—O1—C1—O2	174.8 (3)	C23—C22—C17—C16	5.7 (6)
Pr1—O1—C1—C2	−7.1 (5)	C23—C22—C17—C18	−177.2 (4)
Pr1—N1—C6—C5	173.0 (3)	C23—C22—C21—C20	177.9 (4)
Pr1—N1—C2—C1	11.0 (4)	C6—N1—C2—C1	−175.6 (3)
Pr1—N1—C2—C3	−171.3 (3)	C6—N1—C2—C3	2.1 (6)
Pr1ⁱⁱ—C15—C14—C9	161.5 (9)	C6—C5—C7—O4	−165.8 (4)
Pr1ⁱⁱ—C15—C14—C13	−13.1 (13)	C6—C5—C7—O3	13.7 (6)
Pr2ⁱⁱⁱ—O12—C23—O11	−0.1 (4)	C6—C5—C4—C3	2.2 (6)
Pr2ⁱⁱⁱ—O12—C23—C22	179.8 (3)	C16—C17—C18—C19	176.9 (4)
Pr2—O9—C16—Pr2^v	−176.4 (6)	C2—N1—C6—C5	0.2 (6)
Pr2^v—O9—C16—O10	1.1 (3)	C5—C4—C3—C2	0.0 (6)
Pr2—O9—C16—O10	−175.3 (4)	C1—C2—C3—C4	175.3 (4)
Pr2—O9—C16—C17	9.8 (8)	C14—C13—C12—C11	0.7 (7)
Pr2^v—O9—C16—C17	−173.8 (3)	C7—C5—C4—C3	−175.8 (4)
Pr2—O4—C7—O3	−4.0 (4)	C18—C17—C16—O9	94.5 (4)
Pr2—O4—C7—C5	175.5 (3)	C18—C17—C16—O10	−80.5 (5)
Pr2^v—O10—C16—O9	−1.2 (4)	C18—C19—C20—C21	1.8 (8)
Pr2^v—O10—C16—C17	173.8 (3)	C21—C22—C17—C16	−175.8 (4)
Pr2—O3—C7—O4	3.9 (4)	C21—C22—C17—C18	1.2 (6)
Pr2—O3—C7—C5	−175.5 (3)	C21—C22—C23—O12	166.1 (4)
Pr2ⁱⁱⁱ—O11—C23—O12	0.1 (4)	C21—C22—C23—O11	−14.0 (6)
Pr2ⁱⁱⁱ—O11—C23—C22	−179.8 (3)	C4—C5—C7—O4	12.2 (6)
O7—C15—C14—C9	−129.3 (4)	C4—C5—C7—O3	−168.4 (4)
O7—C15—C14—C13	56.1 (5)	C11—C10—C9—C8	173.9 (4)
O5—C8—C9—C14	39.7 (5)	C11—C10—C9—C14	−1.5 (6)
O5—C8—C9—C10	−135.6 (4)	C3—C2—C1—O2	−3.4 (6)
O8—C15—C14—C9	56.9 (5)	C3—C2—C1—O1	178.4 (4)
O8—C15—C14—C13	−117.7 (4)	C10—C11—C12—C13	−0.6 (7)
O6—C8—C9—C14	−144.3 (4)	C9—C14—C13—C12	−1.2 (6)
O6—C8—C9—C10	40.4 (5)	C13—C14—C9—C8	−173.7 (4)
N1—C6—C5—C7	175.6 (4)	C13—C14—C9—C10	1.6 (6)
N1—C6—C5—C4	−2.4 (6)	C12—C11—C10—C9	1.0 (7)
N1—C2—C1—O2	174.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13W—H13A···O11^vi	0.85	2.57	3.003 (5)	113
O13W—H13A···O16W^vi	0.85	2.26	2.881 (5)	130
O13W—H13B···O2ⁱⁱⁱ	0.86	2.52	2.820 (4)	102
O14W—H14A···O12^vii	0.85	1.95	2.766 (4)	160
O14W—H14B···O4ⁱⁱⁱ	0.85	2.04	2.887 (4)	174
O14W—H14B···O10^vii	0.85	2.58	2.912 (4)	104
O15W—H15A···O16W	0.85	1.75	2.595 (4)	170
O15W—H15B···O4ⁱⁱⁱ	0.85	1.92	2.725 (3)	158
O16W—H16B···O7^viii	0.85	2.31	2.709 (4)	109
O16W—H16B···O1^ix	0.85	2.13	2.938 (5)	158
C11—H11···O14W	0.93	2.51	3.375 (5)	156

Symmetry codes: (iii) x, y+1, z; (vi) −x+3/2, y−1, −z+1; (vii) −x+3/2, −y+5/2, −z+1/2; (viii) x+1/2, −y+2, z; (ix) −x+3/2, y+1, −z+1.

Funding information

This work was supported financially by the Fundamental Fund (FF65-RIM055) of the University of Phayao, Thailand, and by the School of Science, University of Phayao (funding No. PBTSC66046).

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