catena-Poly[[[pentaaquadysprosium(III)]-μ-5-az­an­ium­ylisophthalato] dichloride monohydrate]

Boulkedid, A.L.; Boutebdja, M.; Ghallab, R.

doi:10.1107/S241431462501020X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 11| November 2025| x251020

https://doi.org/10.1107/S241431462501020X

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catena-Poly[[[pentaaquadysprosium(III)]-μ-5-azaniumylisophthalato] dichloride monohydrate]

Ahlem Linda Boulkedid,^a Mehdi Boutebdja ^b and Rochdi Ghallab ^b ^*

^aEnvironmental, Molecular and Structural Chemistry Research Unit, University of Constantine-1, 25000, Constantine, Algeria, and ^bLaboratoire de technologie des materiaux avances, Ecole Nationale Polytechnique de Constantine, Algeria
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 8 November 2025; accepted 13 November 2025; online 28 November 2025)

In the title compound, {[Dy(C₈H₆NO₄)(H₂O)₅]Cl₂·H₂O}_n the central Dy^III atom is nine-coordinated by four oxygen atoms from two symmetry-related chelating carboxylate groups and five water molecules, resulting in a distorted polyhedral geometry best described as ‘muffin'-type by continuous shape measure analysis. The bridging ligands generate infinite [10 $[\overline{1}]$ ] chains and the structure is consolidated by an extensive hydrogen-bonding network and weak π–π stacking interactions.

Keywords: crystal structure; dysprosium(III); 5-aminoisophtalic acid; polymeric chain.

CCDC reference: 2502795

Structure description

Single-crystal X-ray diffraction analysis reveals that the title compound, (I), crystallizes in the monoclinic space group P2₁/n. The asymmetric unit consists of one Dy³⁺ ion, one 5-azaniumylisophthalate ligand (C₈H₆NO₄⁻ or AIP⁻), five coordinating water molecules, two chloride anions and one water molecule of crystallization (O6W). Both carboxylate groups of the AIP ligand are deprotonated and the amino group is protonated.

The metal ion in (I) exhibits a DyO₉ coordination environment (Fig. 1): four oxygen atoms (O1 + O2 and O3 + O4) originate from symmetry-related chelating carboxylate groups of two AIP⁻ ligands and the remaining atoms (O1W–O5W) arise from coordinating water molecules. The Dy—O bond lengths range from 2.362 (3) to 2.4770 (19) Å (Table 1) and the O—Dy—O bond angles span the range 52.67 (6)° to 147.25 (9)°. An analysis of the DyO₉ coordination polyhedron using the continuous shape measure (CShM) approach, as implemented in the SHAPE program (Casanova et al., 2004 ), indicates that the DyO₉ environment in (I) is intermediate between several ideal polyhedra, with the lowest deviation corresponding to a muffin-type geometry with C_s local symmetry (Table 2 and Fig. 2).

Table 1
Selected geometric parameters (Å, °)

Dy1—O1	2.446 (2)	Dy1—O4W	2.449 (4)
Dy1—O1W	2.362 (3)	Dy1—O5W	2.367 (3)
Dy1—O2	2.407 (2)	Dy1—O3ⁱ	2.468 (2)
Dy1—O2W	2.396 (3)	Dy1—O4ⁱ	2.4770 (19)
Dy1—O3W	2.423 (2)

O1—Dy1—O2	53.71 (8)	O3ⁱ—Dy1—O4ⁱ	52.67 (6)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Analysis of the shapes of the coordination polyhedron of the Dy³⁺ ion performed by the SHAPE program

Shape	Deviation
Spherical-relaxed capped cube	9.13
Capped square antiprism	2.47
Spherical capped square antiprism	1.65
Tricapped trigonal prism	2.82
Spherical tricapped trigonal prism	1.62
Tridiminished icosahedron	11.27
Hula-hoop	10.29
Muffin	1.55

Figure 1
The asymmetric unit of (I) expanded to show the complete metal-ion coordination polyhedron with displacement ellipsoids for non-H atoms drawn at the 50% probability level. Symmetry code: (i) x − $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ .

Figure 2
Distorted muffin-type coordination polyhedron of the nine-coordinate Dy1 atom in (I).

Each AIP⁻ ligand chelates two symmetry-equivalent Dy³⁺ ions via its carboxylate groups, which leads to the formation of an infinite [10 $[\overline{1}]$ ] zigzag polymeric chain (Fig. 3). The shortest Dy⋯Dy separation within the chain is 9.8546 (5) Å while the shortest distance between chains is 6.2048 (4) Å. Otherwise, the geometrical parameters for (I) are consistent with reported values for similar compounds (Queirós et al., 2021 ; Kariem et al., 2017 ; Zhao et al., 2012 ; Yan et al., 2009 ; Ye et al., 2008 ).

Figure 3
View of a fragment of an infinite [10 $[\overline{1}]$ ] chain in (I) constructed by bridging AIP ligands and π–π stacking interactions represented as black dashed lines.

In the extended structure of (I), adjacent chains are cross-linked by an extensive hydrogen-bonding network featuring O—H⋯O, O—H⋯Cl, N—H⋯O and N—H⋯Cl interactions, some of which are bifurcated (Table 3) and slightly offset π–π stacking interactions between centrosymmetrically related phenyl rings [Cg1⋯Cg1 = 3.4693 (18) Å, slippage = 1.237 Å] also occur. Collectively, these interactions generate a three-dimensional supramolecular network. For packing views, see Figs. S1–S3 in the supporting information.

Table 3
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2ⁱⁱ	0.90 (5)	2.24 (5)	3.127 (4)	166 (4)
N1—H1B⋯Cl1	0.86 (3)	2.29 (4)	3.141 (4)	171 (3)
N1—H1C⋯O2ⁱⁱⁱ	0.94 (5)	1.97 (4)	2.870 (4)	158 (4)
O1W—H1WA⋯O4^iv	0.77 (5)	1.95 (5)	2.718 (3)	175 (5)
O1W—H1WB⋯Cl2^iv	0.77 (5)	2.36 (5)	3.097 (3)	162 (4)
O2W—H2WA⋯Cl1^v	0.85 (6)	2.38 (6)	3.209 (3)	163 (4)
O2W—H2WB⋯O6W^vi	0.69 (6)	2.57 (6)	3.128 (5)	141 (7)
O3W—H3WA⋯Cl1^v	0.77 (5)	2.44 (5)	3.186 (3)	163 (4)
O3W—H3WB⋯O3ⁱⁱⁱ	0.75 (5)	2.12 (5)	2.780 (3)	148 (4)
O4W—H4WA⋯O6W	0.77 (5)	1.95 (5)	2.721 (5)	178 (5)
O4W—H4WB⋯Cl2^vii	0.75 (6)	2.81 (5)	3.261 (4)	122 (4)
O4W—H4WB⋯Cl1^v	0.75 (6)	2.64 (6)	3.273 (4)	144 (5)
O5W—H5WA⋯Cl1^viii	0.77 (5)	2.32 (5)	3.085 (3)	170 (4)
O5W—H5WB⋯Cl2	0.87 (6)	2.21 (6)	3.075 (3)	171 (5)
O6W—H6WA⋯O1W^ix	0.85	2.52	3.039 (4)	120
O6W—H6WA⋯O3^x	0.85	2.49	3.161 (4)	137
O6W—H6WB⋯Cl2	0.85	2.32	3.126 (4)	158
Symmetry codes: (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vi) ; (vii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (viii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ix) ; (x) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Synthesis and crystallization

A methanolic solution of 5-aminoisophthalic acid (0.181 g, 1.00 mmol in 10 ml methanol) was added dropwise, under stirring, to a separate methanolic solution of DyCl₃·6H₂O (0.094 g, 0.25 mmol). Upon stirring for several minutes, the reaction mixture yielded a white precipitate, which was collected by filtration and discarded. The colourless filtrate was allowed to evaporate slowly at room temperature over the course of one week, resulting in the formation of colorless blocks of (I), suitable for X-ray diffraction analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4.

Table 4
Experimental details

Crystal data
Chemical formula	[Dy(C₈H₆NO₄)(H₂O)₅]Cl₂·H₂O
M_r	521.63
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.7274 (2), 11.9281 (3), 15.4697 (4)
β (°)	100.480 (1)
V (Å³)	1583.55 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	5.10
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.675, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	16994, 4086, 3470
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.052, 1.01
No. of reflections	4086
No. of parameters	266
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.63
Computer programs: APEX2 and SAINT (Bruker, 2013 ), OLEX2.solve (Bourhis et al., 2015 ), SHELXL2019/3 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2502795

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431462501020X/hb4543sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462501020X/hb4543Isup2.hkl

Packing views. DOI: https://doi.org/10.1107/S241431462501020X/hb4543sup3.docx

checkCIF report

Computing details top

catena-Poly[[[pentaaquadysprosium(III)]-µ-5-azaniumylisophthalato] dichloride monohydrate] top

Crystal data top

[Dy(C₈H₆NO₄)(H₂O)₅]Cl₂·H₂O	F(000) = 1012
M_r = 521.63	D_x = 2.188 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8978 reflections
a = 8.7274 (2) Å	θ = 2.7–34.0°
b = 11.9281 (3) Å	µ = 5.10 mm⁻¹
c = 15.4697 (4) Å	T = 296 K
β = 100.480 (1)°	Block, colourless
V = 1583.55 (7) Å³	0.13 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3470 reflections with I > 2σ(I)
ω scans	R_int = 0.042
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.7°, θ_min = 2.2°
T_min = 0.675, T_max = 0.747	h = −11→11
16994 measured reflections	k = −13→16
4086 independent reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.052	W = 1/[Σ²(FO²) + (0.0152P)² + 1.8767P] WHERE P = (FO² + 2FC²)/3
S = 1.01	(Δ/σ)_max < 0.001
4086 reflections	Δρ_max = 0.86 e Å⁻³
266 parameters	Δρ_min = −0.63 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
Dy1	0.29223 (2)	0.48158 (2)	0.14719 (2)	0.0189 (1)
Cl1	0.02552 (10)	0.70815 (8)	0.56158 (6)	0.0377 (3)
Cl2	0.64436 (11)	0.17687 (9)	0.24575 (6)	0.0430 (3)
O1	0.2208 (3)	0.4945 (2)	0.29260 (14)	0.0313 (7)
O1W	0.0349 (3)	0.5510 (2)	0.12853 (16)	0.0277 (7)
O2	0.4427 (3)	0.4136 (2)	0.28306 (12)	0.0295 (7)
O2W	0.2900 (3)	0.5851 (3)	0.01427 (17)	0.0365 (9)
O3	0.6343 (3)	0.18700 (19)	0.66052 (12)	0.0262 (6)
O3W	0.3298 (4)	0.6758 (2)	0.19189 (18)	0.0424 (9)
O4	0.6313 (2)	0.12560 (18)	0.52657 (12)	0.0216 (6)
O4W	0.5608 (4)	0.5387 (3)	0.1444 (3)	0.0608 (13)
O5W	0.4398 (3)	0.3280 (2)	0.11052 (18)	0.0356 (8)
N1	0.2551 (4)	0.5119 (3)	0.63105 (19)	0.0283 (9)
C1	0.3633 (3)	0.4088 (2)	0.42259 (16)	0.0197 (8)
C2	0.4623 (3)	0.3207 (3)	0.45410 (17)	0.0202 (8)
C3	0.4866 (3)	0.2926 (2)	0.54279 (17)	0.0188 (8)
C4	0.4162 (3)	0.3562 (3)	0.59983 (18)	0.0206 (8)
C5	0.3188 (3)	0.4431 (3)	0.56745 (18)	0.0205 (8)
C6	0.2882 (3)	0.4697 (3)	0.47899 (18)	0.0205 (8)
C7	0.3396 (4)	0.4414 (3)	0.32713 (17)	0.0225 (8)
C8	0.5899 (3)	0.1970 (2)	0.57829 (17)	0.0193 (8)
O6W	0.8027 (3)	0.3937 (3)	0.1901 (3)	0.0748 (16)
H1A	0.208 (5)	0.465 (4)	0.664 (3)	0.045 (12)*
H1B	0.188 (4)	0.561 (3)	0.607 (2)	0.026 (9)*
H1C	0.339 (5)	0.550 (4)	0.666 (3)	0.042 (11)*
H2	0.508 (4)	0.281 (3)	0.414 (2)	0.024 (8)*
H1WA	−0.007 (5)	0.574 (4)	0.084 (3)	0.045 (12)*
H4	0.431 (3)	0.340 (3)	0.659 (2)	0.021 (8)*
H1WB	0.007 (5)	0.578 (4)	0.168 (3)	0.048 (13)*
H4WA	0.631 (5)	0.499 (4)	0.157 (3)	0.034 (12)*
H6	0.223 (5)	0.532 (3)	0.458 (3)	0.040 (11)*
H3WA	0.368 (5)	0.716 (4)	0.163 (3)	0.057 (15)*
H3WB	0.309 (5)	0.700 (4)	0.233 (3)	0.058 (15)*
H4WB	0.590 (6)	0.597 (5)	0.141 (3)	0.070 (18)*
H5WA	0.437 (5)	0.301 (4)	0.065 (3)	0.058 (15)*
H5WB	0.490 (6)	0.287 (5)	0.153 (4)	0.09 (2)*
H2WA	0.351 (6)	0.641 (5)	0.015 (3)	0.09 (2)*
H2WB	0.255 (7)	0.562 (6)	−0.025 (4)	0.09 (2)*
H6WA	0.90093	0.40173	0.20341	0.1120*
H6WB	0.78481	0.33146	0.21305	0.1120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.0253 (1)	0.0155 (1)	0.0139 (1)	−0.0019 (1)	−0.0019 (1)	0.0003 (1)
Cl1	0.0421 (5)	0.0308 (5)	0.0412 (4)	0.0098 (4)	0.0102 (4)	0.0073 (4)
Cl2	0.0492 (5)	0.0431 (6)	0.0411 (5)	0.0161 (4)	0.0199 (4)	0.0112 (4)
O1	0.0359 (12)	0.0381 (15)	0.0179 (10)	0.0113 (10)	−0.0005 (9)	0.0068 (9)
O1W	0.0351 (12)	0.0284 (14)	0.0184 (11)	0.0103 (10)	0.0017 (9)	0.0028 (9)
O2	0.0401 (12)	0.0321 (14)	0.0146 (9)	0.0116 (10)	0.0005 (8)	−0.0006 (8)
O2W	0.0479 (15)	0.0388 (17)	0.0216 (12)	−0.0139 (13)	0.0031 (11)	0.0039 (11)
O3	0.0396 (12)	0.0226 (12)	0.0135 (9)	0.0113 (10)	−0.0025 (8)	−0.0010 (8)
O3W	0.080 (2)	0.0229 (15)	0.0264 (13)	−0.0117 (14)	0.0156 (13)	−0.0065 (11)
O4	0.0292 (10)	0.0184 (11)	0.0153 (9)	0.0058 (9)	−0.0009 (8)	−0.0009 (8)
O4W	0.0394 (17)	0.034 (2)	0.099 (3)	−0.0118 (15)	−0.0143 (16)	0.0201 (18)
O5W	0.0393 (14)	0.0370 (16)	0.0275 (13)	0.0097 (11)	−0.0022 (11)	−0.0086 (11)
N1	0.0331 (14)	0.0288 (17)	0.0247 (13)	0.0124 (13)	0.0099 (11)	0.0066 (11)
C1	0.0273 (14)	0.0151 (15)	0.0143 (12)	−0.0024 (11)	−0.0027 (10)	0.0011 (10)
C2	0.0289 (15)	0.0149 (15)	0.0154 (13)	0.0018 (12)	0.0006 (11)	−0.0013 (10)
C3	0.0233 (13)	0.0150 (15)	0.0170 (12)	−0.0010 (11)	0.0009 (10)	0.0019 (10)
C4	0.0238 (14)	0.0203 (16)	0.0174 (13)	−0.0007 (11)	0.0031 (10)	0.0040 (11)
C5	0.0199 (13)	0.0220 (16)	0.0201 (13)	0.0013 (11)	0.0053 (10)	0.0003 (11)
C6	0.0213 (13)	0.0164 (16)	0.0216 (13)	0.0026 (11)	−0.0019 (10)	0.0025 (11)
C7	0.0330 (15)	0.0125 (15)	0.0188 (13)	−0.0014 (12)	−0.0035 (11)	0.0001 (11)
C8	0.0239 (14)	0.0150 (15)	0.0176 (12)	0.0000 (11)	0.0004 (10)	0.0015 (10)
O6W	0.0356 (15)	0.035 (2)	0.156 (4)	0.0001 (14)	0.023 (2)	−0.004 (2)

Geometric parameters (Å, º) top

Dy1—O1	2.446 (2)	O4W—H4WB	0.75 (6)
Dy1—O1W	2.362 (3)	O4W—H4WA	0.77 (5)
Dy1—O2	2.407 (2)	O5W—H5WA	0.77 (5)
Dy1—O2W	2.396 (3)	O5W—H5WB	0.87 (6)
Dy1—O3W	2.423 (2)	N1—H1A	0.90 (5)
Dy1—O4W	2.449 (4)	N1—H1B	0.86 (3)
Dy1—O5W	2.367 (3)	N1—H1C	0.94 (5)
Dy1—O3ⁱ	2.468 (2)	C1—C6	1.388 (4)
Dy1—O4ⁱ	2.4770 (19)	C1—C7	1.505 (4)
O1—C7	1.249 (4)	C1—C2	1.391 (4)
O2—C7	1.268 (4)	C2—C3	1.391 (4)
O3—C8	1.266 (3)	C3—C8	1.495 (4)
O4—C8	1.265 (3)	C3—C4	1.389 (4)
N1—C5	1.466 (4)	C4—C5	1.376 (5)
O1W—H1WA	0.77 (5)	C5—C6	1.383 (4)
O1W—H1WB	0.77 (5)	C2—H2	0.93 (3)
O2W—H2WA	0.85 (6)	C4—H4	0.92 (3)
O2W—H2WB	0.69 (6)	C6—H6	0.96 (4)
O3W—H3WB	0.75 (5)	O6W—H6WA	0.8500
O3W—H3WA	0.77 (5)	O6W—H6WB	0.8500

O1—Dy1—O1W	72.21 (8)	Dy1—O2W—H2WB	119 (6)
O1—Dy1—O2	53.71 (8)	H2WA—O2W—H2WB	120 (7)
O1—Dy1—O2W	142.49 (10)	Dy1—O2W—H2WA	119 (3)
O1—Dy1—O3W	73.81 (9)	Dy1—O3W—H3WA	119 (3)
O1—Dy1—O4W	113.80 (12)	Dy1—O3W—H3WB	125 (4)
O1—Dy1—O5W	120.66 (9)	H3WA—O3W—H3WB	117 (5)
O1—Dy1—O3ⁱ	74.62 (7)	Dy1—O4W—H4WA	123 (3)
O1—Dy1—O4ⁱ	121.39 (7)	H4WA—O4W—H4WB	109 (5)
O1W—Dy1—O2	125.48 (8)	Dy1—O4W—H4WB	127 (4)
O1W—Dy1—O2W	81.68 (9)	H5WA—O5W—H5WB	113 (5)
O1W—Dy1—O3W	77.05 (10)	Dy1—O5W—H5WA	128 (3)
O1W—Dy1—O4W	142.40 (10)	Dy1—O5W—H5WB	118 (4)
O1W—Dy1—O5W	142.09 (9)	C6—C1—C7	119.0 (2)
O1W—Dy1—O3ⁱ	76.27 (8)	C2—C1—C6	120.6 (2)
O1W—Dy1—O4ⁱ	72.10 (7)	C2—C1—C7	120.3 (2)
O2—Dy1—O2W	147.25 (9)	C5—N1—H1B	114 (2)
O2—Dy1—O3W	92.80 (9)	C5—N1—H1C	108 (3)
O2—Dy1—O4W	74.77 (12)	H1A—N1—H1B	109 (4)
O2—Dy1—O5W	73.40 (9)	H1A—N1—H1C	111 (4)
O2—Dy1—O3ⁱ	82.93 (8)	H1B—N1—H1C	108 (4)
O2—Dy1—O4ⁱ	128.93 (7)	C5—N1—H1A	107 (3)
O2W—Dy1—O3W	74.44 (10)	C1—C2—C3	120.1 (3)
O2W—Dy1—O4W	72.53 (12)	C2—C3—C4	119.3 (3)
O2W—Dy1—O5W	96.49 (10)	C4—C3—C8	119.4 (2)
O2W—Dy1—O3ⁱ	125.05 (9)	C2—C3—C8	121.3 (2)
O2W—Dy1—O4ⁱ	72.81 (9)	C3—C4—C5	119.7 (3)
O3W—Dy1—O4W	70.05 (12)	C4—C5—C6	121.9 (3)
O3W—Dy1—O5W	139.22 (10)	N1—C5—C6	120.5 (3)
O3ⁱ—Dy1—O3W	143.51 (10)	N1—C5—C4	117.5 (3)
O3W—Dy1—O4ⁱ	137.50 (9)	C1—C6—C5	118.3 (3)
O4W—Dy1—O5W	69.32 (11)	O1—C7—C1	120.4 (3)
O3ⁱ—Dy1—O4W	141.18 (10)	O1—C7—O2	121.2 (3)
O4ⁱ—Dy1—O4W	122.94 (11)	O2—C7—C1	118.4 (3)
O3ⁱ—Dy1—O5W	74.09 (8)	O4—C8—C3	120.2 (2)
O4ⁱ—Dy1—O5W	71.26 (8)	O3—C8—O4	120.1 (2)
O3ⁱ—Dy1—O4ⁱ	52.67 (6)	O3—C8—C3	119.7 (2)
Dy1—O1—C7	91.76 (18)	C1—C2—H2	118 (2)
Dy1—O2—C7	93.07 (18)	C3—C2—H2	122 (2)
Dy1ⁱⁱ—O3—C8	93.80 (16)	C3—C4—H4	121 (2)
Dy1ⁱⁱ—O4—C8	93.39 (15)	C5—C4—H4	119 (2)
Dy1—O1W—H1WA	121 (3)	C1—C6—H6	121 (3)
Dy1—O1W—H1WB	119 (3)	C5—C6—H6	121 (3)
H1WA—O1W—H1WB	113 (5)	H6WA—O6W—H6WB	105.00

O1W—Dy1—O1—C7	169.7 (2)	O5W—Dy1—O4ⁱ—C8ⁱ	82.71 (16)
O2—Dy1—O1—C7	−2.97 (19)	Dy1—O1—C7—O2	5.3 (3)
O2W—Dy1—O1—C7	−142.2 (2)	Dy1—O1—C7—C1	−174.6 (3)
O3W—Dy1—O1—C7	−109.0 (2)	Dy1—O2—C7—O1	−5.4 (3)
O4W—Dy1—O1—C7	−50.1 (2)	Dy1—O2—C7—C1	174.5 (3)
O5W—Dy1—O1—C7	29.1 (2)	Dy1ⁱⁱ—O3—C8—O4	2.3 (3)
O3ⁱ—Dy1—O1—C7	89.5 (2)	Dy1ⁱⁱ—O3—C8—C3	−178.6 (2)
O4ⁱ—Dy1—O1—C7	114.8 (2)	Dy1ⁱⁱ—O4—C8—O3	−2.2 (3)
O1—Dy1—O2—C7	2.93 (19)	Dy1ⁱⁱ—O4—C8—C3	178.6 (2)
O1W—Dy1—O2—C7	−5.6 (2)	C6—C1—C2—C3	0.2 (4)
O2W—Dy1—O2—C7	135.6 (2)	C7—C1—C2—C3	178.5 (3)
O3W—Dy1—O2—C7	70.5 (2)	C2—C1—C6—C5	2.3 (4)
O4W—Dy1—O2—C7	138.9 (2)	C7—C1—C6—C5	−176.1 (3)
O5W—Dy1—O2—C7	−148.6 (2)	C2—C1—C7—O1	158.3 (3)
O3ⁱ—Dy1—O2—C7	−73.2 (2)	C2—C1—C7—O2	−21.6 (4)
O4ⁱ—Dy1—O2—C7	−100.8 (2)	C6—C1—C7—O1	−23.3 (4)
O1—Dy1—O3ⁱ—C8ⁱ	154.02 (19)	C6—C1—C7—O2	156.7 (3)
O1W—Dy1—O3ⁱ—C8ⁱ	79.03 (18)	C1—C2—C3—C4	−2.6 (4)
O2—Dy1—O3ⁱ—C8ⁱ	−151.75 (18)	C1—C2—C3—C8	178.8 (2)
O2W—Dy1—O3ⁱ—C8ⁱ	9.7 (2)	C2—C3—C4—C5	2.6 (4)
O3W—Dy1—O3ⁱ—C8ⁱ	123.13 (19)	C8—C3—C4—C5	−178.9 (3)
O4W—Dy1—O3ⁱ—C8ⁱ	−97.0 (2)	C2—C3—C8—O3	166.1 (3)
O5W—Dy1—O3ⁱ—C8ⁱ	−77.05 (18)	C2—C3—C8—O4	−14.8 (4)
O1—Dy1—O4ⁱ—C8ⁱ	−32.37 (18)	C4—C3—C8—O3	−12.5 (4)
O1W—Dy1—O4ⁱ—C8ⁱ	−87.40 (16)	C4—C3—C8—O4	166.7 (3)
O2—Dy1—O4ⁱ—C8ⁱ	34.15 (18)	C3—C4—C5—N1	−176.3 (3)
O2W—Dy1—O4ⁱ—C8ⁱ	−174.00 (17)	C3—C4—C5—C6	0.0 (5)
O3W—Dy1—O4ⁱ—C8ⁱ	−132.88 (18)	N1—C5—C6—C1	173.8 (3)
O4W—Dy1—O4ⁱ—C8ⁱ	131.09 (17)	C4—C5—C6—C1	−2.4 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱⁱⁱ	0.90 (5)	2.24 (5)	3.127 (4)	166 (4)
N1—H1B···Cl1	0.86 (3)	2.29 (4)	3.141 (4)	171 (3)
N1—H1C···O2^iv	0.94 (5)	1.97 (4)	2.870 (4)	158 (4)
O1W—H1WA···O4^v	0.77 (5)	1.95 (5)	2.718 (3)	175 (5)
O1W—H1WB···Cl2^v	0.77 (5)	2.36 (5)	3.097 (3)	162 (4)
O2W—H2WA···Cl1^vi	0.85 (6)	2.38 (6)	3.209 (3)	163 (4)
O2W—H2WB···O6W^vii	0.69 (6)	2.57 (6)	3.128 (5)	141 (7)
O3W—H3WA···Cl1^vi	0.77 (5)	2.44 (5)	3.186 (3)	163 (4)
O3W—H3WB···O3^iv	0.75 (5)	2.12 (5)	2.780 (3)	148 (4)
O4W—H4WA···O6W	0.77 (5)	1.95 (5)	2.721 (5)	178 (5)
O4W—H4WB···Cl2^viii	0.75 (6)	2.81 (5)	3.261 (4)	122 (4)
O4W—H4WB···Cl1^vi	0.75 (6)	2.64 (6)	3.273 (4)	144 (5)
O5W—H5WA···Cl1^ix	0.77 (5)	2.32 (5)	3.085 (3)	170 (4)
O5W—H5WB···Cl2	0.87 (6)	2.21 (6)	3.075 (3)	171 (5)
O6W—H6WA···O1W^x	0.85	2.52	3.039 (4)	120
O6W—H6WA···O3^xi	0.85	2.49	3.161 (4)	137
O6W—H6WB···Cl2	0.85	2.32	3.126 (4)	158

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

Analysis of the shapes of the coordination polyhedron of the Dy³⁺ ion performed by the SHAPE program top

Shape	Deviation
Spherical-relaxed capped cube	9.13
Capped square antiprism	2.47
Spherical capped square antiprism	1.65
Tricapped trigonal prism	2.82
Spherical tricapped trigonal prism	1.62
Tridiminished icosahedron	11.27
Hula-hoop	10.29
Muffin	1.55

Acknowledgements

The authors thank the Cambridge Crystallographic Data Center (CCDC) for access to the Cambridge Structural Database (CSD) through the FAIRE program.

Funding information

Funding for this research was provided by: Laboratoire de technologie des matériaux avancés, Ecole Nationale Polytechnique de Constantine, Algeria; Unité de recherche de chimie de l'environnement, moléculaire et structurale UR.CHEMS; DRSDT-Algeria.

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