Four isostructural lanthanide(III) coordination compounds based on a new N-oxydic pyridyl naphthalenedi­imide ligand: synthesis and characterization

Xiang, Z.; Shan, Y.-B.; Li, T.; Huang, C.-C.; Huang, X.-H.; Lin, M.-J.

doi:10.1107/S2053229618017357

Four isostructural lanthanide(III) coordination compounds based on a new N-oxydic pyridyl naphthalenediimide ligand: synthesis and characterization

Z. Xiang, Y.-B. Shan, T. Li, C.-C. Huang, X.-H. Huang and M.-J. Lin

Naphthalenediimides, an attractive class of electron-deficient organic dyes with rich redox and photoredox properties, have been investigated extensively as building blocks for coordination networks or metal–organic frameworks in recent decades. However, most of the available work has focused on d-block metal cations rather than f-block lanthanide ions, whose complexes exhibit a large variability in coordination numbers. In this article, four coordination polymers composed of naphthalenediimides and lanthanide cations, namely catena-poly[[[tris(nitrato-κ²O,O′)lanthanide]-bis{μ-N,N′-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O′}-[tris(nitrato-κ²O,O′)lanthanide]-μ-N,N′-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O′] methanol disolvate], {[Ln(C₂₆H₁₆N₄O₄)_1.5(NO₃)₃]·CH₃OH}_n, with Ln = Eu, 1, Gd, 2, Dy, 3, and Er, 4, have been successfully synthesized under hydrothermal conditions. Single-crystal X-ray diffraction analyses revealed that the four compounds are isomorphic and that each asymmetric unit contains one nine-coordinated Ln centre, one and a half diimide ligands, three nitrate anions and one uncoordinated methanol molecule. In addition, each metal centre is surrounded by nine O atoms in a distorted tricapped trigonal–prismatic geometry. Two centres are bridged by two cis ligands to form a ring, which is further bridged by trans ligands to generate one-dimensional chains. Neighbouring chains are stacked via π–π interactions between pyridine rings to give a two-dimensional structure, which is stabilized by π–π interactions between naphthalene rings, forming the final three-dimensional supermolecular network. Solid-state optical diffuse-reflectance spectral studies indicate that compound 4 is a potential wide band gap semiconductor.

Keywords: coordination polymer; naphthalenediimide; lanthanide; crystal structure; nine-coordinate; semiconductor.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618017357/qf3018sup1.cif Contains datablocks Eu, Gd, Dy, Er, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017357/qf3018Eusup2.hkl Contains datablock Eu
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017357/qf3018Gdsup3.hkl Contains datablock Gd
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017357/qf3018Dysup4.hkl Contains datablock Dy
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017357/qf3018Ersup5.hkl Contains datablock Er

CCDC references: 1883662; 1883661; 1883660; 1883659

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for Eu, Gd, Dy; SHELXS97 (Sheldrick, 2008) for Er. Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for Eu, Gd, Dy; SHELXL97 (Sheldrick, 2008) for Er. For all structures, molecular graphics: OLEX2 (Dolomanov et al., 2009). Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for Eu, Gd, Dy; SHELXL97 (Sheldrick, 2008) for Er.

catena-Poly[[[tris(nitrato-κ²O,O')europium(III)]-bis{µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'}-[tris(nitrato-κ²O,O')europium(III)]-µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'] methanol disolvate] (Eu) top

Crystal data top

[Eu(C₂₆H₁₆N₄O₄)_1.5(NO₃)₃]·CH₄O	Z = 2
M_r = 1090.67	F(000) = 1092
Triclinic, P1	D_x = 1.789 Mg m⁻³
a = 9.8247 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.2829 (4) Å	Cell parameters from 18481 reflections
c = 15.9914 (4) Å	θ = 2.4–29.4°
α = 109.498 (2)°	µ = 1.65 mm⁻¹
β = 103.761 (2)°	T = 173 K
γ = 106.110 (2)°	Block, yellow
V = 2024.56 (9) Å³	0.15 × 0.13 × 0.11 mm

Data collection top

Rigaku Enhance (Mo) X-ray Source diffractometer	7596 reflections with I > 2σ(I)
Omiga scan	R_int = 0.032
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 26.4°, θ_min = 2.8°
T_min = 0.797, T_max = 1.000	h = −12→11
29383 measured reflections	k = −19→19
8248 independent reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.029P)² + 0.570P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
8248 reflections	Δρ_max = 0.64 e Å⁻³
624 parameters	Δρ_min = −0.55 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.

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

	x	y	z	U_iso*/U_eq
Eu1	0.23304 (2)	0.17623 (2)	0.36540 (2)	0.01755 (4)
O1	0.99602 (17)	0.84648 (12)	0.74558 (10)	0.0240 (3)
O2	1.0610 (2)	0.57604 (15)	0.92946 (16)	0.0476 (5)
O3	0.82530 (18)	0.78049 (11)	1.03917 (11)	0.0255 (3)
O4	0.12489 (18)	0.36038 (12)	0.82417 (13)	0.0338 (4)
O5	0.36525 (19)	0.15321 (11)	0.72898 (12)	0.0307 (4)
O6	0.06151 (18)	0.07713 (11)	0.40637 (10)	0.0239 (3)
O7	−0.36415 (18)	0.12907 (12)	0.29828 (11)	0.0285 (4)
O8	−0.30671 (19)	0.31525 (12)	0.13132 (12)	0.0293 (4)
O9	0.17730 (17)	0.30952 (11)	0.45667 (11)	0.0246 (3)
O10	0.38370 (17)	0.22572 (12)	0.53458 (11)	0.0274 (4)
O11	0.50562 (19)	0.28887 (12)	0.45849 (11)	0.0303 (4)
O12	0.6311 (2)	0.29761 (15)	0.59542 (13)	0.0424 (5)
O13	0.31826 (18)	0.16358 (11)	0.22915 (11)	0.0248 (3)
O14	0.30191 (19)	0.30595 (12)	0.29937 (12)	0.0293 (4)
O15	0.35490 (19)	0.27359 (13)	0.17011 (12)	0.0309 (4)
O16	0.37282 (19)	0.06388 (12)	0.37038 (12)	0.0306 (4)
O17	0.15888 (18)	−0.00257 (11)	0.25278 (11)	0.0251 (3)
O18	0.3045 (2)	−0.08657 (13)	0.25866 (13)	0.0394 (4)
N1	1.04557 (19)	0.87889 (13)	0.83965 (12)	0.0184 (4)
N2	0.9379 (2)	0.67891 (14)	0.97398 (13)	0.0220 (4)
N3	0.2454 (2)	0.25788 (13)	0.77498 (13)	0.0220 (4)
N4	−0.0024 (2)	0.10166 (13)	0.47121 (13)	0.0203 (4)
N5	−0.3514 (2)	0.22176 (14)	0.21306 (14)	0.0222 (4)
N6	0.1046 (2)	0.35926 (14)	0.42156 (13)	0.0230 (4)
N7	0.3266 (2)	0.24910 (14)	0.23121 (13)	0.0221 (4)
N8	0.5110 (2)	0.27178 (14)	0.53234 (14)	0.0270 (4)
N9	0.2801 (2)	−0.01049 (14)	0.29337 (14)	0.0252 (4)
C1	1.1122 (2)	0.97884 (16)	0.89547 (16)	0.0196 (4)
H1	1.1201	1.0252	0.8677	0.023*
C2	1.1687 (2)	1.01338 (17)	0.99281 (16)	0.0221 (5)
H2	1.2165	1.0838	1.0325	0.026*
C3	1.1557 (2)	0.94517 (16)	1.03318 (15)	0.0208 (5)
H3	1.1940	0.9689	1.1005	0.025*
C4	1.0867 (2)	0.84240 (16)	0.97508 (15)	0.0196 (4)
C5	1.0325 (2)	0.81071 (16)	0.87765 (15)	0.0196 (4)
H5	0.9855	0.7406	0.8366	0.023*
C6	1.0820 (3)	0.76817 (18)	1.01879 (17)	0.0279 (5)
H6A	1.1661	0.7454	1.0144	0.033*
H6B	1.1001	0.8034	1.0872	0.033*
C7	0.9423 (3)	0.58344 (18)	0.93153 (17)	0.0272 (5)
C8	0.7970 (2)	0.49520 (17)	0.89054 (16)	0.0220 (5)
C9	0.7899 (3)	0.39900 (18)	0.84329 (17)	0.0280 (5)
H9	0.8792	0.3895	0.8372	0.034*
C10	0.6520 (3)	0.31566 (17)	0.80437 (17)	0.0267 (5)
H10	0.6488	0.2499	0.7727	0.032*
C11	0.5211 (3)	0.32785 (16)	0.81139 (15)	0.0206 (5)
C12	0.3749 (3)	0.23915 (16)	0.76836 (15)	0.0229 (5)
C13	0.8118 (2)	0.69581 (16)	0.99117 (15)	0.0189 (4)
C14	0.6679 (2)	0.60659 (15)	0.94800 (14)	0.0168 (4)
C15	0.5364 (2)	0.61852 (16)	0.95508 (15)	0.0188 (4)
H15	0.5402	0.6840	0.9887	0.023*
C16	0.3968 (2)	0.53516 (16)	0.91321 (15)	0.0190 (4)
H16	0.3069	0.5445	0.9179	0.023*
C17	0.3908 (2)	0.44030 (16)	0.86557 (15)	0.0180 (4)
C18	0.2434 (3)	0.35281 (16)	0.82058 (16)	0.0224 (5)
C19	0.6637 (2)	0.50944 (16)	0.89910 (15)	0.0179 (4)
C20	0.5243 (2)	0.42534 (15)	0.85853 (14)	0.0175 (4)
C21	−0.1467 (3)	0.09464 (17)	0.44159 (17)	0.0269 (5)
H21	−0.2013	0.0732	0.3759	0.032*
C22	−0.2142 (3)	0.1186 (2)	0.50675 (19)	0.0350 (6)
H22	−0.3154	0.1152	0.4866	0.042*
C23	−0.1350 (3)	0.14790 (18)	0.60231 (18)	0.0300 (5)
H23	−0.1806	0.1663	0.6480	0.036*
C24	0.0114 (3)	0.15015 (16)	0.63061 (16)	0.0224 (5)
C25	0.0765 (2)	0.12768 (15)	0.56287 (15)	0.0204 (5)
H25	0.1776	0.1306	0.5811	0.024*
C26	0.0984 (3)	0.17107 (16)	0.73155 (16)	0.0252 (5)
H26A	0.0358	0.1843	0.7707	0.030*
H26B	0.1168	0.1106	0.7315	0.030*
C27	0.1847 (3)	0.44786 (19)	0.42465 (19)	0.0342 (6)
H27	0.2927	0.4756	0.4521	0.041*
C28	0.1103 (3)	0.4983 (2)	0.3881 (2)	0.0429 (7)
H28	0.1670	0.5613	0.3909	0.052*
C29	−0.0482 (3)	0.45749 (19)	0.3469 (2)	0.0380 (6)
H29	−0.1003	0.4915	0.3204	0.046*
C30	−0.1280 (3)	0.36611 (17)	0.34537 (16)	0.0258 (5)
C31	−0.0485 (3)	0.31901 (16)	0.38454 (15)	0.0228 (5)
H31	−0.1024	0.2574	0.3854	0.027*
C32	−0.2995 (3)	0.31546 (18)	0.30058 (17)	0.0268 (5)
H32A	−0.3401	0.2994	0.3471	0.032*
H32B	−0.3408	0.3626	0.2849	0.032*
C33	−0.3856 (2)	0.13046 (17)	0.22113 (16)	0.0223 (5)
C34	−0.4467 (2)	0.03778 (16)	0.13106 (16)	0.0200 (4)
C35	−0.4694 (2)	0.04442 (16)	0.04290 (16)	0.0192 (4)
C36	−0.4304 (2)	0.13889 (16)	0.03896 (16)	0.0205 (5)
C37	−0.3587 (2)	0.23226 (17)	0.12893 (17)	0.0228 (5)
C38	−0.4829 (2)	−0.05518 (17)	0.13293 (16)	0.0224 (5)
H38	−0.4661	−0.0595	0.1922	0.027*
C39	−0.4561 (2)	0.14298 (17)	−0.04837 (16)	0.0220 (5)
H39	−0.4318	0.2066	−0.0507	0.026*
O19	0.2938 (2)	0.41874 (16)	0.65577 (13)	0.0478 (5)
H19	0.2483	0.3763	0.5986	0.072*
C40	0.4438 (3)	0.4749 (2)	0.66977 (19)	0.0414 (7)
H40A	0.4434	0.4976	0.6192	0.062*
H40B	0.5032	0.4327	0.6681	0.062*
H40C	0.4897	0.5336	0.7318	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.01790 (7)	0.01794 (6)	0.01594 (6)	0.00514 (5)	0.00674 (5)	0.00737 (5)
O1	0.0259 (8)	0.0304 (8)	0.0158 (7)	0.0112 (7)	0.0072 (7)	0.0101 (7)
O2	0.0216 (9)	0.0462 (11)	0.0725 (15)	0.0136 (9)	0.0221 (10)	0.0188 (11)
O3	0.0257 (9)	0.0195 (8)	0.0241 (8)	0.0025 (7)	0.0069 (7)	0.0077 (7)
O4	0.0205 (9)	0.0269 (9)	0.0450 (11)	0.0037 (7)	0.0139 (8)	0.0084 (8)
O5	0.0382 (10)	0.0182 (8)	0.0299 (9)	0.0111 (7)	0.0054 (8)	0.0084 (7)
O6	0.0282 (9)	0.0222 (8)	0.0192 (8)	0.0051 (7)	0.0123 (7)	0.0079 (6)
O7	0.0278 (9)	0.0354 (9)	0.0273 (9)	0.0138 (8)	0.0098 (7)	0.0180 (7)
O8	0.0297 (9)	0.0244 (9)	0.0371 (10)	0.0102 (7)	0.0094 (8)	0.0192 (7)
O9	0.0250 (8)	0.0258 (8)	0.0200 (8)	0.0131 (7)	0.0038 (7)	0.0070 (7)
O10	0.0212 (8)	0.0312 (9)	0.0230 (8)	0.0028 (7)	0.0068 (7)	0.0108 (7)
O11	0.0277 (9)	0.0319 (9)	0.0258 (9)	0.0033 (7)	0.0091 (7)	0.0134 (7)
O12	0.0224 (9)	0.0507 (12)	0.0371 (11)	0.0041 (8)	−0.0030 (8)	0.0171 (9)
O13	0.0309 (9)	0.0233 (8)	0.0261 (8)	0.0111 (7)	0.0147 (7)	0.0141 (7)
O14	0.0368 (10)	0.0251 (8)	0.0318 (9)	0.0123 (7)	0.0192 (8)	0.0141 (7)
O15	0.0307 (9)	0.0373 (10)	0.0281 (9)	0.0070 (8)	0.0123 (8)	0.0219 (8)
O16	0.0292 (9)	0.0304 (9)	0.0294 (9)	0.0124 (8)	0.0069 (8)	0.0116 (8)
O17	0.0263 (9)	0.0232 (8)	0.0239 (8)	0.0076 (7)	0.0102 (7)	0.0092 (7)
O18	0.0568 (12)	0.0312 (10)	0.0463 (11)	0.0279 (9)	0.0312 (10)	0.0178 (9)
N1	0.0141 (9)	0.0244 (9)	0.0171 (9)	0.0078 (8)	0.0064 (7)	0.0088 (8)
N2	0.0153 (9)	0.0265 (10)	0.0226 (10)	0.0035 (8)	0.0049 (8)	0.0138 (8)
N3	0.0240 (10)	0.0179 (9)	0.0203 (9)	0.0028 (8)	0.0076 (8)	0.0085 (8)
N4	0.0232 (10)	0.0181 (9)	0.0205 (9)	0.0051 (8)	0.0100 (8)	0.0102 (8)
N5	0.0190 (9)	0.0239 (10)	0.0267 (10)	0.0098 (8)	0.0083 (8)	0.0133 (8)
N6	0.0228 (10)	0.0221 (10)	0.0206 (9)	0.0092 (8)	0.0064 (8)	0.0058 (8)
N7	0.0149 (9)	0.0272 (10)	0.0224 (10)	0.0046 (8)	0.0049 (8)	0.0130 (8)
N8	0.0233 (11)	0.0244 (10)	0.0243 (10)	0.0043 (8)	0.0041 (9)	0.0073 (8)
N9	0.0340 (11)	0.0243 (10)	0.0260 (10)	0.0118 (9)	0.0188 (9)	0.0146 (9)
C1	0.0145 (10)	0.0208 (11)	0.0266 (12)	0.0083 (9)	0.0091 (9)	0.0115 (9)
C2	0.0139 (10)	0.0234 (11)	0.0250 (12)	0.0070 (9)	0.0074 (9)	0.0058 (9)
C3	0.0136 (10)	0.0279 (12)	0.0187 (11)	0.0076 (9)	0.0068 (9)	0.0072 (9)
C4	0.0093 (10)	0.0279 (12)	0.0228 (11)	0.0062 (9)	0.0058 (9)	0.0130 (9)
C5	0.0149 (10)	0.0186 (10)	0.0220 (11)	0.0045 (9)	0.0055 (9)	0.0077 (9)
C6	0.0165 (11)	0.0340 (13)	0.0298 (13)	0.0022 (10)	0.0028 (10)	0.0199 (11)
C7	0.0226 (12)	0.0339 (13)	0.0304 (13)	0.0125 (10)	0.0123 (10)	0.0166 (11)
C8	0.0207 (11)	0.0286 (12)	0.0226 (11)	0.0118 (10)	0.0098 (10)	0.0147 (10)
C9	0.0282 (13)	0.0346 (13)	0.0301 (13)	0.0198 (11)	0.0146 (11)	0.0151 (11)
C10	0.0335 (13)	0.0239 (12)	0.0267 (12)	0.0166 (11)	0.0115 (11)	0.0107 (10)
C11	0.0251 (12)	0.0213 (11)	0.0171 (10)	0.0095 (9)	0.0065 (9)	0.0106 (9)
C12	0.0314 (13)	0.0199 (11)	0.0181 (11)	0.0092 (10)	0.0067 (10)	0.0112 (9)
C13	0.0193 (11)	0.0241 (12)	0.0162 (10)	0.0067 (9)	0.0061 (9)	0.0137 (9)
C14	0.0192 (11)	0.0190 (10)	0.0135 (10)	0.0063 (9)	0.0059 (9)	0.0096 (8)
C15	0.0218 (11)	0.0172 (10)	0.0193 (11)	0.0081 (9)	0.0072 (9)	0.0098 (9)
C16	0.0188 (11)	0.0211 (11)	0.0210 (11)	0.0086 (9)	0.0089 (9)	0.0116 (9)
C17	0.0177 (11)	0.0200 (11)	0.0180 (10)	0.0059 (9)	0.0063 (9)	0.0115 (9)
C18	0.0249 (12)	0.0223 (11)	0.0204 (11)	0.0080 (10)	0.0086 (10)	0.0102 (9)
C19	0.0199 (11)	0.0223 (11)	0.0161 (10)	0.0092 (9)	0.0076 (9)	0.0119 (9)
C20	0.0216 (11)	0.0194 (10)	0.0146 (10)	0.0087 (9)	0.0073 (9)	0.0098 (8)
C21	0.0255 (13)	0.0278 (12)	0.0265 (12)	0.0092 (10)	0.0057 (10)	0.0141 (10)
C22	0.0274 (13)	0.0442 (15)	0.0431 (16)	0.0186 (12)	0.0154 (12)	0.0245 (13)
C23	0.0330 (14)	0.0310 (13)	0.0357 (14)	0.0152 (11)	0.0214 (12)	0.0171 (11)
C24	0.0263 (12)	0.0158 (10)	0.0231 (11)	0.0027 (9)	0.0103 (10)	0.0098 (9)
C25	0.0182 (11)	0.0183 (11)	0.0210 (11)	0.0028 (9)	0.0037 (9)	0.0103 (9)
C26	0.0284 (12)	0.0187 (11)	0.0209 (11)	−0.0013 (9)	0.0095 (10)	0.0079 (9)
C27	0.0247 (13)	0.0279 (13)	0.0424 (15)	0.0050 (11)	0.0085 (12)	0.0131 (11)
C28	0.0333 (15)	0.0304 (14)	0.0612 (19)	0.0060 (12)	0.0112 (14)	0.0246 (14)
C29	0.0340 (15)	0.0305 (14)	0.0507 (17)	0.0134 (12)	0.0103 (13)	0.0215 (13)
C30	0.0253 (12)	0.0266 (12)	0.0254 (12)	0.0124 (10)	0.0094 (10)	0.0090 (10)
C31	0.0219 (12)	0.0204 (11)	0.0214 (11)	0.0059 (9)	0.0074 (10)	0.0058 (9)
C32	0.0233 (12)	0.0302 (12)	0.0291 (13)	0.0135 (10)	0.0091 (10)	0.0130 (10)
C33	0.0133 (10)	0.0305 (12)	0.0309 (13)	0.0117 (9)	0.0094 (10)	0.0186 (10)
C34	0.0127 (10)	0.0276 (12)	0.0264 (11)	0.0111 (9)	0.0082 (9)	0.0157 (10)
C35	0.0116 (10)	0.0266 (11)	0.0286 (12)	0.0102 (9)	0.0097 (9)	0.0184 (9)
C36	0.0142 (10)	0.0263 (11)	0.0312 (12)	0.0117 (9)	0.0115 (10)	0.0186 (10)
C37	0.0150 (11)	0.0285 (12)	0.0333 (13)	0.0128 (10)	0.0098 (10)	0.0186 (10)
C38	0.0180 (11)	0.0323 (12)	0.0288 (12)	0.0143 (10)	0.0114 (10)	0.0213 (10)
C39	0.0190 (11)	0.0249 (11)	0.0339 (13)	0.0123 (9)	0.0129 (10)	0.0208 (10)
O19	0.0452 (12)	0.0561 (13)	0.0268 (10)	0.0161 (10)	0.0092 (9)	0.0057 (9)
C40	0.0515 (18)	0.0320 (14)	0.0281 (14)	0.0104 (13)	0.0061 (13)	0.0093 (11)

Geometric parameters (Å, º) top

Eu1—O1ⁱ	2.3644 (15)	C7—C8	1.477 (3)
Eu1—O6	2.3094 (15)	C8—C9	1.383 (3)
Eu1—O9	2.3653 (15)	C8—C19	1.416 (3)
Eu1—O10	2.4879 (16)	C9—H9	0.9500
Eu1—O11	2.4871 (16)	C9—C10	1.399 (3)
Eu1—O13	2.4825 (15)	C10—H10	0.9500
Eu1—O14	2.5488 (16)	C10—C11	1.374 (3)
Eu1—O16	2.4877 (16)	C11—C12	1.484 (3)
Eu1—O17	2.4953 (15)	C11—C20	1.415 (3)
Eu1—N7	2.9422 (18)	C13—C14	1.474 (3)
Eu1—N8	2.9038 (19)	C14—C15	1.379 (3)
Eu1—N9	2.9112 (19)	C14—C19	1.412 (3)
O1—Eu1ⁱ	2.3644 (15)	C15—H15	0.9500
O1—N1	1.329 (2)	C15—C16	1.406 (3)
O2—C7	1.210 (3)	C16—H16	0.9500
O3—C13	1.214 (3)	C16—C17	1.371 (3)
O4—C18	1.214 (3)	C17—C18	1.480 (3)
O5—C12	1.217 (3)	C17—C20	1.416 (3)
O6—N4	1.338 (2)	C19—C20	1.412 (3)
O7—C33	1.210 (3)	C21—H21	0.9500
O8—C37	1.212 (3)	C21—C22	1.367 (4)
O9—N6	1.341 (2)	C22—H22	0.9500
O10—N8	1.269 (2)	C22—C23	1.388 (4)
O11—N8	1.284 (3)	C23—H23	0.9500
O12—N8	1.215 (3)	C23—C24	1.388 (3)
O13—N7	1.275 (2)	C24—C25	1.380 (3)
O14—N7	1.270 (2)	C24—C26	1.512 (3)
O15—N7	1.220 (2)	C25—H25	0.9500
O16—N9	1.263 (2)	C26—H26A	0.9900
O17—N9	1.272 (2)	C26—H26B	0.9900
O18—N9	1.227 (2)	C27—H27	0.9500
N1—C1	1.347 (3)	C27—C28	1.371 (4)
N1—C5	1.363 (3)	C28—H28	0.9500
N2—C6	1.474 (3)	C28—C29	1.395 (4)
N2—C7	1.407 (3)	C29—H29	0.9500
N2—C13	1.403 (3)	C29—C30	1.388 (3)
N3—C12	1.399 (3)	C30—C31	1.379 (3)
N3—C18	1.398 (3)	C30—C32	1.511 (3)
N3—C26	1.474 (3)	C31—H31	0.9500
N4—C21	1.345 (3)	C32—H32A	0.9900
N4—C25	1.344 (3)	C32—H32B	0.9900
N5—C32	1.479 (3)	C33—C34	1.482 (3)
N5—C33	1.399 (3)	C34—C35	1.416 (3)
N5—C37	1.395 (3)	C34—C38	1.378 (3)
N6—C27	1.342 (3)	C35—C35ⁱⁱ	1.414 (4)
N6—C31	1.345 (3)	C35—C36	1.414 (3)
C1—H1	0.9500	C36—C37	1.481 (3)
C1—C2	1.374 (3)	C36—C39	1.385 (3)
C2—H2	0.9500	C38—H38	0.9500
C2—C3	1.391 (3)	C38—C39ⁱⁱ	1.395 (3)
C3—H3	0.9500	C39—C38ⁱⁱ	1.395 (3)
C3—C4	1.387 (3)	C39—H39	0.9500
C4—C5	1.380 (3)	O19—H19	0.8400
C4—C6	1.514 (3)	O19—C40	1.405 (3)
C5—H5	0.9500	C40—H40A	0.9800
C6—H6A	0.9900	C40—H40B	0.9800
C6—H6B	0.9900	C40—H40C	0.9800

O1ⁱ—Eu1—O9	78.86 (5)	C5—C4—C6	121.6 (2)
O1ⁱ—Eu1—O10	147.22 (5)	N1—C5—C4	120.67 (19)
O1ⁱ—Eu1—O11	144.94 (6)	N1—C5—H5	119.7
O1ⁱ—Eu1—O13	81.87 (5)	C4—C5—H5	119.7
O1ⁱ—Eu1—O14	73.23 (5)	N2—C6—C4	114.45 (18)
O1ⁱ—Eu1—O16	132.34 (5)	N2—C6—H6A	108.6
O1ⁱ—Eu1—O17	81.14 (5)	N2—C6—H6B	108.6
O1ⁱ—Eu1—N7	75.11 (5)	C4—C6—H6A	108.6
O1ⁱ—Eu1—N8	160.18 (5)	C4—C6—H6B	108.6
O1ⁱ—Eu1—N9	106.79 (6)	H6A—C6—H6B	107.6
O6—Eu1—O1ⁱ	80.88 (5)	O2—C7—N2	120.3 (2)
O6—Eu1—O9	84.97 (5)	O2—C7—C8	122.8 (2)
O6—Eu1—O10	78.31 (5)	N2—C7—C8	116.93 (19)
O6—Eu1—O11	129.57 (5)	C9—C8—C7	120.6 (2)
O6—Eu1—O13	139.31 (5)	C9—C8—C19	119.8 (2)
O6—Eu1—O14	150.42 (6)	C19—C8—C7	119.6 (2)
O6—Eu1—O16	86.55 (6)	C8—C9—H9	119.8
O6—Eu1—O17	73.04 (5)	C8—C9—C10	120.4 (2)
O6—Eu1—N7	153.23 (5)	C10—C9—H9	119.8
O6—Eu1—N8	103.45 (5)	C9—C10—H10	119.6
O6—Eu1—N9	80.10 (5)	C11—C10—C9	120.7 (2)
O9—Eu1—O10	74.35 (5)	C11—C10—H10	119.6
O9—Eu1—O11	86.35 (5)	C10—C11—C12	120.3 (2)
O9—Eu1—O13	127.00 (5)	C10—C11—C20	120.2 (2)
O9—Eu1—O14	76.32 (5)	C20—C11—C12	119.43 (19)
O9—Eu1—O16	145.60 (5)	O5—C12—N3	120.3 (2)
O9—Eu1—O17	152.29 (5)	O5—C12—C11	122.6 (2)
O9—Eu1—N7	101.60 (5)	N3—C12—C11	117.06 (19)
O9—Eu1—N8	82.24 (5)	O3—C13—N2	119.90 (19)
O9—Eu1—N9	162.86 (5)	O3—C13—C14	123.81 (19)
O10—Eu1—O14	117.21 (5)	N2—C13—C14	116.29 (19)
O10—Eu1—O17	115.96 (5)	C15—C14—C13	119.55 (19)
O10—Eu1—N7	128.45 (5)	C15—C14—C19	119.95 (19)
O10—Eu1—N8	25.77 (5)	C19—C14—C13	120.50 (19)
O10—Eu1—N9	94.28 (5)	C14—C15—H15	119.5
O11—Eu1—O10	51.57 (5)	C14—C15—C16	120.9 (2)
O11—Eu1—O14	72.45 (5)	C16—C15—H15	119.5
O11—Eu1—O16	73.76 (6)	C15—C16—H16	120.1
O11—Eu1—O17	120.61 (5)	C17—C16—C15	119.86 (19)
O11—Eu1—N7	77.05 (5)	C17—C16—H16	120.1
O11—Eu1—N8	26.13 (5)	C16—C17—C18	119.74 (19)
O11—Eu1—N9	96.66 (6)	C16—C17—C20	120.57 (19)
O13—Eu1—O10	129.70 (5)	C20—C17—C18	119.69 (19)
O13—Eu1—O11	82.09 (5)	O4—C18—N3	120.0 (2)
O13—Eu1—O14	50.85 (5)	O4—C18—C17	123.0 (2)
O13—Eu1—O16	78.48 (5)	N3—C18—C17	116.98 (19)
O13—Eu1—O17	68.05 (5)	C14—C19—C8	121.1 (2)
O13—Eu1—N7	25.43 (5)	C20—C19—C8	119.66 (19)
O13—Eu1—N8	105.18 (5)	C20—C19—C14	119.29 (19)
O13—Eu1—N9	70.13 (5)	C11—C20—C17	121.46 (19)
O14—Eu1—N7	25.47 (5)	C19—C20—C11	119.16 (19)
O14—Eu1—N8	96.58 (5)	C19—C20—C17	119.38 (19)
O14—Eu1—N9	120.70 (5)	N4—C21—H21	120.3
O16—Eu1—O10	71.29 (5)	N4—C21—C22	119.5 (2)
O16—Eu1—O14	121.55 (5)	C22—C21—H21	120.3
O16—Eu1—O17	51.26 (5)	C21—C22—H22	120.0
O16—Eu1—N7	100.89 (5)	C21—C22—C23	120.0 (2)
O16—Eu1—N8	67.48 (5)	C23—C22—H22	120.0
O16—Eu1—N9	25.55 (5)	C22—C23—H23	120.2
O17—Eu1—O14	115.71 (5)	C22—C23—C24	119.5 (2)
O17—Eu1—N7	91.50 (5)	C24—C23—H23	120.2
O17—Eu1—N8	118.68 (5)	C23—C24—C26	122.4 (2)
O17—Eu1—N9	25.78 (5)	C25—C24—C23	118.5 (2)
N8—Eu1—N7	103.15 (5)	C25—C24—C26	119.0 (2)
N8—Eu1—N9	93.02 (6)	N4—C25—C24	120.4 (2)
N9—Eu1—N7	95.52 (5)	N4—C25—H25	119.8
N1—O1—Eu1ⁱ	132.01 (12)	C24—C25—H25	119.8
N4—O6—Eu1	131.22 (12)	N3—C26—C24	112.48 (18)
N6—O9—Eu1	125.14 (12)	N3—C26—H26A	109.1
N8—O10—Eu1	95.75 (12)	N3—C26—H26B	109.1
N8—O11—Eu1	95.36 (12)	C24—C26—H26A	109.1
N7—O13—Eu1	97.88 (12)	C24—C26—H26B	109.1
N7—O14—Eu1	94.86 (12)	H26A—C26—H26B	107.8
N9—O16—Eu1	96.31 (12)	N6—C27—H27	120.1
N9—O17—Eu1	95.69 (12)	N6—C27—C28	119.8 (2)
O1—N1—C1	119.06 (18)	C28—C27—H27	120.1
O1—N1—C5	119.52 (17)	C27—C28—H28	119.8
C1—N1—C5	121.39 (18)	C27—C28—C29	120.4 (2)
C7—N2—C6	118.20 (18)	C29—C28—H28	119.8
C13—N2—C6	115.96 (19)	C28—C29—H29	120.8
C13—N2—C7	124.99 (18)	C30—C29—C28	118.5 (2)
C12—N3—C26	118.05 (18)	C30—C29—H29	120.8
C18—N3—C12	125.35 (18)	C29—C30—C32	122.1 (2)
C18—N3—C26	116.60 (18)	C31—C30—C29	119.1 (2)
O6—N4—C21	118.66 (18)	C31—C30—C32	118.8 (2)
O6—N4—C25	119.22 (18)	N6—C31—C30	120.8 (2)
C25—N4—C21	122.04 (19)	N6—C31—H31	119.6
C33—N5—C32	118.00 (19)	C30—C31—H31	119.6
C37—N5—C32	116.77 (18)	N5—C32—C30	112.02 (18)
C37—N5—C33	125.21 (19)	N5—C32—H32A	109.2
O9—N6—C27	119.87 (19)	N5—C32—H32B	109.2
O9—N6—C31	118.75 (18)	C30—C32—H32A	109.2
C27—N6—C31	121.4 (2)	C30—C32—H32B	109.2
O13—N7—Eu1	56.70 (10)	H32A—C32—H32B	107.9
O14—N7—Eu1	59.68 (10)	O7—C33—N5	120.8 (2)
O14—N7—O13	116.21 (17)	O7—C33—C34	122.9 (2)
O15—N7—Eu1	174.94 (14)	N5—C33—C34	116.38 (19)
O15—N7—O13	121.36 (19)	C35—C34—C33	120.16 (19)
O15—N7—O14	122.42 (19)	C38—C34—C33	120.0 (2)
O10—N8—Eu1	58.48 (10)	C38—C34—C35	119.9 (2)
O10—N8—O11	115.88 (18)	C35ⁱⁱ—C35—C34	119.9 (2)
O11—N8—Eu1	58.51 (10)	C35ⁱⁱ—C35—C36	119.0 (2)
O12—N8—Eu1	169.35 (16)	C36—C35—C34	121.1 (2)
O12—N8—O10	122.5 (2)	C35—C36—C37	119.2 (2)
O12—N8—O11	121.6 (2)	C39—C36—C35	119.8 (2)
O16—N9—Eu1	58.14 (10)	C39—C36—C37	121.0 (2)
O16—N9—O17	116.44 (18)	O8—C37—N5	120.2 (2)
O17—N9—Eu1	58.53 (10)	O8—C37—C36	122.6 (2)
O18—N9—Eu1	175.15 (14)	N5—C37—C36	117.28 (19)
O18—N9—O16	122.4 (2)	C34—C38—H38	119.8
O18—N9—O17	121.2 (2)	C34—C38—C39ⁱⁱ	120.4 (2)
N1—C1—H1	120.2	C39ⁱⁱ—C38—H38	119.8
N1—C1—C2	119.7 (2)	C36—C39—C38ⁱⁱ	121.0 (2)
C2—C1—H1	120.2	C36—C39—H39	119.5
C1—C2—H2	120.0	C38ⁱⁱ—C39—H39	119.5
C1—C2—C3	119.9 (2)	C40—O19—H19	109.5
C3—C2—H2	120.0	O19—C40—H40A	109.5
C2—C3—H3	120.0	O19—C40—H40B	109.5
C4—C3—C2	120.0 (2)	O19—C40—H40C	109.5
C4—C3—H3	120.0	H40A—C40—H40B	109.5
C3—C4—C6	119.9 (2)	H40A—C40—H40C	109.5
C5—C4—C3	118.4 (2)	H40B—C40—H40C	109.5

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

catena-poly[[[tris(nitrato-κ²O,O')gadolinium(III)]-bis{µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'}-[tris(nitrato-κ²O,O')gadolinium(III)]-µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'] methanol disolvate] (Gd) top

Crystal data top

[Gd(C₂₆H₁₆N₄O₄)_1.5(NO₃)₃]·CH₄O	Z = 2
M_r = 1095.96	F(000) = 1094
Triclinic, P1	D_x = 1.787 Mg m⁻³
a = 9.8335 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.3314 (9) Å	Cell parameters from 10074 reflections
c = 16.0227 (13) Å	θ = 2.4–30.7°
α = 109.641 (6)°	µ = 1.73 mm⁻¹
β = 103.642 (6)°	T = 173 K
γ = 106.064 (5)°	Block, yellow
V = 2036.8 (3) Å³	0.2 × 0.18 × 0.15 mm

Data collection top

Multiwire proportional diffractometer	5945 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −11→11
T_min = 0.292, T_max = 1.000	k = −18→14
14631 measured reflections	l = −18→18
6910 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
S = 0.90	(Δ/σ)_max < 0.001
6910 reflections	Δρ_max = 1.36 e Å⁻³
624 parameters	Δρ_min = −2.19 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
Gd1	0.23239 (2)	0.17600 (2)	0.36473 (2)	0.01846 (8)
O1	0.1770 (3)	0.3085 (2)	0.45580 (18)	0.0265 (7)
O2	−0.3064 (3)	0.3151 (2)	0.1306 (2)	0.0321 (7)
O3	−0.3643 (3)	0.1289 (2)	0.2983 (2)	0.0307 (7)
O4	0.0622 (3)	0.0771 (2)	0.40593 (18)	0.0253 (7)
O5	0.3655 (3)	0.1529 (2)	0.7282 (2)	0.0322 (7)
O6	0.1248 (3)	0.3601 (2)	0.8236 (2)	0.0369 (8)
O7	1.0606 (3)	0.5753 (3)	0.9290 (3)	0.0503 (10)
O8	0.8246 (3)	0.7801 (2)	1.03881 (19)	0.0273 (7)
O9	0.9962 (3)	0.8466 (2)	0.74533 (18)	0.0246 (7)
O11	0.3821 (3)	0.2249 (2)	0.53326 (19)	0.0308 (7)
O12	0.5033 (3)	0.2885 (2)	0.4566 (2)	0.0325 (7)
O13	0.6294 (3)	0.2976 (3)	0.5940 (2)	0.0464 (9)
O14	0.3716 (3)	0.0641 (2)	0.3699 (2)	0.0326 (7)
O15	0.3025 (4)	−0.0868 (2)	0.2585 (2)	0.0425 (9)
O16	0.1572 (3)	−0.0022 (2)	0.25286 (19)	0.0277 (7)
O17	0.3179 (3)	0.1634 (2)	0.22908 (19)	0.0267 (7)
O18	0.3005 (3)	0.3056 (2)	0.2992 (2)	0.0335 (8)
O19	0.3551 (3)	0.2731 (2)	0.1701 (2)	0.0323 (7)
N1	−0.0008 (4)	0.1019 (3)	0.4712 (2)	0.0220 (8)
N2	0.2454 (4)	0.2578 (3)	0.7744 (2)	0.0228 (8)
N3	0.9379 (4)	0.6786 (3)	0.9740 (2)	0.0244 (8)
N4	1.0456 (3)	0.8795 (3)	0.8399 (2)	0.0195 (8)
N5	0.1046 (4)	0.3586 (3)	0.4214 (2)	0.0267 (9)
N6	−0.3508 (4)	0.2216 (3)	0.2134 (2)	0.0219 (8)
N7	0.2786 (4)	−0.0104 (3)	0.2930 (3)	0.0284 (9)
N8	0.5089 (4)	0.2715 (3)	0.5305 (3)	0.0316 (9)
N9	0.3266 (4)	0.2487 (3)	0.2311 (2)	0.0253 (8)
C1	0.1840 (5)	0.4471 (4)	0.4232 (3)	0.0368 (12)
H1	0.2919	0.4742	0.4495	0.044*
C2	0.1106 (5)	0.4981 (4)	0.3874 (4)	0.0469 (14)
H2	0.1671	0.5613	0.3908	0.056*
C3	−0.0476 (5)	0.4568 (4)	0.3461 (3)	0.0407 (12)
H3	−0.0999	0.4901	0.3190	0.049*
C4	−0.1272 (5)	0.3662 (3)	0.3453 (3)	0.0261 (10)
C5	−0.0480 (4)	0.3186 (3)	0.3839 (3)	0.0236 (10)
H5	−0.1021	0.2568	0.3840	0.028*
C6	−0.2984 (4)	0.3152 (3)	0.3005 (3)	0.0300 (11)
H6A	−0.3388	0.2995	0.3471	0.036*
H6B	−0.3398	0.3620	0.2847	0.036*
C7	−0.3587 (4)	0.2319 (4)	0.1286 (3)	0.0250 (10)
C8	−0.4302 (4)	0.1394 (3)	0.0388 (3)	0.0208 (9)
C9	−0.4691 (4)	0.0447 (3)	0.0429 (3)	0.0203 (9)
C10	−0.4467 (4)	0.0376 (3)	0.1311 (3)	0.0205 (9)
C11	−0.3855 (4)	0.1303 (3)	0.2207 (3)	0.0232 (10)
C12	−0.4552 (4)	0.1434 (3)	−0.0481 (3)	0.0233 (10)
H12	−0.4303	0.2068	−0.0504	0.028*
C13	−0.4828 (4)	−0.0548 (3)	0.1334 (3)	0.0240 (10)
H13	−0.4659	−0.0588	0.1927	0.029*
C14	−0.1446 (5)	0.0952 (4)	0.4418 (3)	0.0314 (11)
H14	−0.1985	0.0741	0.3763	0.038*
C15	−0.2132 (5)	0.1187 (4)	0.5064 (3)	0.0368 (12)
H15	−0.3143	0.1151	0.4861	0.044*
C16	−0.1337 (5)	0.1480 (4)	0.6022 (3)	0.0334 (11)
H16	−0.1792	0.1661	0.6480	0.040*
C17	0.0124 (5)	0.1504 (3)	0.6300 (3)	0.0227 (9)
C18	0.0776 (4)	0.1280 (3)	0.5623 (3)	0.0207 (9)
H18	0.1787	0.1311	0.5804	0.025*
C19	0.0995 (5)	0.1715 (3)	0.7311 (3)	0.0283 (10)
H19A	0.0368	0.1847	0.7702	0.034*
H19B	0.1181	0.1112	0.7310	0.034*
C20	0.2438 (5)	0.3526 (3)	0.8202 (3)	0.0229 (9)
C21	0.3906 (4)	0.4402 (3)	0.8646 (3)	0.0185 (9)
C22	0.3965 (4)	0.5342 (3)	0.9120 (3)	0.0178 (9)
H22	0.3064	0.5435	0.9163	0.021*
C23	0.5363 (4)	0.6179 (3)	0.9548 (3)	0.0188 (9)
H23	0.5400	0.6830	0.9890	0.023*
C24	0.6672 (4)	0.6060 (3)	0.9473 (3)	0.0170 (9)
C25	0.8114 (4)	0.6956 (3)	0.9912 (3)	0.0209 (9)
C26	0.9420 (5)	0.5831 (3)	0.9314 (3)	0.0275 (10)
C27	0.7966 (4)	0.4952 (3)	0.8899 (3)	0.0231 (10)
C28	0.7902 (5)	0.3992 (3)	0.8431 (3)	0.0295 (11)
H28	0.8799	0.3899	0.8377	0.035*
C29	0.6525 (5)	0.3155 (3)	0.8036 (3)	0.0271 (10)
H29	0.6494	0.2501	0.7713	0.032*
C30	0.5208 (4)	0.3277 (3)	0.8114 (3)	0.0210 (9)
C31	0.3754 (5)	0.2386 (3)	0.7678 (3)	0.0234 (10)
C32	0.5240 (4)	0.4250 (3)	0.8580 (2)	0.0166 (9)
C33	0.6638 (4)	0.5090 (3)	0.8986 (3)	0.0181 (9)
C34	1.1120 (4)	0.9788 (3)	0.8956 (3)	0.0198 (9)
H34	1.1202	1.0251	0.8680	0.024*
C35	1.1683 (4)	1.0130 (3)	0.9930 (3)	0.0222 (10)
H35	1.2159	1.0832	1.0329	0.027*
C36	1.1554 (4)	0.9451 (3)	1.0328 (3)	0.0230 (10)
H36	1.1938	0.9689	1.1000	0.028*
C37	1.0860 (4)	0.8414 (3)	0.9746 (3)	0.0209 (9)
C38	1.0322 (4)	0.8109 (3)	0.8770 (3)	0.0209 (9)
H38	0.9855	0.7412	0.8354	0.025*
C39	1.0814 (4)	0.7676 (3)	1.0186 (3)	0.0278 (10)
H39A	1.1655	0.7449	1.0142	0.033*
H39B	1.0994	0.8030	1.0869	0.033*
O10	0.2945 (4)	0.4192 (3)	0.6552 (2)	0.0532 (10)
H10	0.2486	0.3779	0.5978	0.080*
C40	0.4447 (6)	0.4761 (4)	0.6692 (3)	0.0468 (14)
H40A	0.4436	0.4999	0.6196	0.070*
H40B	0.5040	0.4339	0.6661	0.070*
H40C	0.4907	0.5338	0.7318	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Gd1	0.01943 (12)	0.01984 (13)	0.01803 (13)	0.00657 (9)	0.00842 (8)	0.01007 (10)
O1	0.0251 (15)	0.0304 (18)	0.0273 (16)	0.0160 (14)	0.0081 (12)	0.0128 (14)
O2	0.0336 (18)	0.0248 (19)	0.0441 (19)	0.0108 (15)	0.0120 (14)	0.0239 (16)
O3	0.0309 (17)	0.0353 (19)	0.0308 (18)	0.0133 (15)	0.0121 (13)	0.0190 (16)
O4	0.0333 (16)	0.0261 (17)	0.0221 (15)	0.0092 (14)	0.0156 (13)	0.0149 (14)
O5	0.0436 (19)	0.0176 (17)	0.0307 (18)	0.0120 (15)	0.0067 (14)	0.0097 (15)
O6	0.0219 (16)	0.0310 (19)	0.051 (2)	0.0067 (15)	0.0168 (14)	0.0104 (16)
O7	0.0251 (18)	0.048 (2)	0.079 (3)	0.0178 (17)	0.0257 (17)	0.020 (2)
O8	0.0296 (16)	0.0194 (17)	0.0270 (16)	0.0038 (14)	0.0076 (12)	0.0100 (14)
O9	0.0282 (15)	0.0326 (18)	0.0150 (15)	0.0128 (14)	0.0070 (11)	0.0122 (14)
O11	0.0206 (16)	0.038 (2)	0.0279 (17)	0.0020 (14)	0.0091 (12)	0.0142 (15)
O12	0.0315 (17)	0.036 (2)	0.0273 (17)	0.0038 (15)	0.0128 (13)	0.0169 (16)
O13	0.0248 (18)	0.059 (3)	0.0381 (19)	0.0035 (17)	−0.0024 (15)	0.0213 (19)
O14	0.0331 (17)	0.0291 (19)	0.0336 (18)	0.0141 (15)	0.0104 (14)	0.0107 (16)
O15	0.059 (2)	0.035 (2)	0.052 (2)	0.0283 (18)	0.0345 (17)	0.0209 (17)
O16	0.0279 (16)	0.0269 (18)	0.0307 (17)	0.0111 (14)	0.0128 (13)	0.0135 (14)
O17	0.0371 (17)	0.0211 (17)	0.0313 (17)	0.0138 (14)	0.0175 (13)	0.0164 (14)
O18	0.0410 (19)	0.0288 (19)	0.0394 (19)	0.0147 (16)	0.0235 (15)	0.0173 (16)
O19	0.0334 (17)	0.042 (2)	0.0318 (17)	0.0123 (15)	0.0149 (14)	0.0278 (17)
N1	0.0249 (19)	0.022 (2)	0.0247 (19)	0.0076 (16)	0.0135 (15)	0.0140 (17)
N2	0.0261 (19)	0.018 (2)	0.0192 (18)	0.0024 (16)	0.0090 (14)	0.0070 (16)
N3	0.0194 (18)	0.031 (2)	0.0277 (19)	0.0075 (17)	0.0099 (14)	0.0184 (18)
N4	0.0186 (17)	0.026 (2)	0.0184 (18)	0.0102 (16)	0.0084 (14)	0.0123 (17)
N5	0.0238 (19)	0.029 (2)	0.027 (2)	0.0111 (17)	0.0093 (15)	0.0107 (18)
N6	0.0212 (18)	0.024 (2)	0.027 (2)	0.0125 (16)	0.0102 (14)	0.0143 (17)
N7	0.046 (2)	0.023 (2)	0.031 (2)	0.0164 (19)	0.0261 (18)	0.0176 (19)
N8	0.028 (2)	0.027 (2)	0.029 (2)	0.0067 (18)	0.0068 (17)	0.0069 (19)
N9	0.0175 (18)	0.035 (2)	0.025 (2)	0.0066 (17)	0.0081 (15)	0.0181 (19)
C1	0.025 (2)	0.026 (3)	0.049 (3)	0.001 (2)	0.008 (2)	0.015 (2)
C2	0.035 (3)	0.032 (3)	0.073 (4)	0.007 (2)	0.014 (3)	0.029 (3)
C3	0.036 (3)	0.032 (3)	0.058 (3)	0.016 (2)	0.014 (2)	0.025 (3)
C4	0.025 (2)	0.026 (3)	0.027 (2)	0.012 (2)	0.0101 (18)	0.009 (2)
C5	0.024 (2)	0.021 (2)	0.023 (2)	0.0062 (19)	0.0094 (17)	0.008 (2)
C6	0.023 (2)	0.030 (3)	0.039 (3)	0.013 (2)	0.0115 (19)	0.014 (2)
C7	0.019 (2)	0.037 (3)	0.038 (3)	0.020 (2)	0.0149 (19)	0.027 (2)
C8	0.015 (2)	0.028 (3)	0.034 (2)	0.0121 (19)	0.0140 (17)	0.023 (2)
C9	0.011 (2)	0.030 (3)	0.033 (2)	0.0108 (19)	0.0134 (17)	0.022 (2)
C10	0.0131 (19)	0.030 (3)	0.030 (2)	0.0130 (19)	0.0107 (17)	0.020 (2)
C11	0.014 (2)	0.033 (3)	0.035 (3)	0.0122 (19)	0.0116 (18)	0.024 (2)
C12	0.018 (2)	0.028 (3)	0.039 (3)	0.0135 (19)	0.0170 (18)	0.024 (2)
C13	0.017 (2)	0.038 (3)	0.033 (2)	0.017 (2)	0.0138 (18)	0.027 (2)
C14	0.027 (2)	0.039 (3)	0.035 (3)	0.013 (2)	0.008 (2)	0.025 (2)
C15	0.030 (3)	0.047 (3)	0.043 (3)	0.022 (2)	0.016 (2)	0.023 (3)
C16	0.037 (3)	0.035 (3)	0.041 (3)	0.018 (2)	0.027 (2)	0.020 (2)
C17	0.029 (2)	0.016 (2)	0.024 (2)	0.0048 (19)	0.0122 (18)	0.0114 (19)
C18	0.019 (2)	0.019 (2)	0.023 (2)	0.0029 (18)	0.0071 (17)	0.0123 (19)
C19	0.033 (2)	0.021 (2)	0.025 (2)	−0.001 (2)	0.0123 (19)	0.010 (2)
C20	0.026 (2)	0.019 (2)	0.022 (2)	0.0055 (19)	0.0099 (17)	0.0091 (19)
C21	0.022 (2)	0.022 (2)	0.019 (2)	0.0092 (19)	0.0096 (16)	0.0147 (19)
C22	0.019 (2)	0.025 (2)	0.017 (2)	0.0089 (18)	0.0091 (16)	0.0155 (19)
C23	0.025 (2)	0.018 (2)	0.018 (2)	0.0089 (18)	0.0091 (16)	0.0118 (18)
C24	0.019 (2)	0.021 (2)	0.013 (2)	0.0056 (18)	0.0041 (15)	0.0124 (18)
C25	0.022 (2)	0.027 (3)	0.017 (2)	0.0069 (19)	0.0069 (16)	0.016 (2)
C26	0.027 (2)	0.037 (3)	0.028 (2)	0.015 (2)	0.0133 (18)	0.020 (2)
C27	0.025 (2)	0.031 (3)	0.024 (2)	0.014 (2)	0.0141 (18)	0.018 (2)
C28	0.031 (2)	0.039 (3)	0.034 (3)	0.023 (2)	0.017 (2)	0.021 (2)
C29	0.035 (3)	0.026 (3)	0.027 (2)	0.018 (2)	0.0122 (19)	0.013 (2)
C30	0.029 (2)	0.022 (2)	0.018 (2)	0.012 (2)	0.0067 (17)	0.0143 (19)
C31	0.034 (2)	0.023 (3)	0.020 (2)	0.011 (2)	0.0081 (18)	0.018 (2)
C32	0.022 (2)	0.022 (2)	0.0114 (19)	0.0093 (18)	0.0057 (15)	0.0131 (18)
C33	0.021 (2)	0.025 (2)	0.017 (2)	0.0123 (19)	0.0093 (16)	0.0162 (19)
C34	0.015 (2)	0.022 (2)	0.026 (2)	0.0088 (18)	0.0082 (17)	0.013 (2)
C35	0.014 (2)	0.021 (2)	0.026 (2)	0.0060 (18)	0.0080 (17)	0.004 (2)
C36	0.013 (2)	0.036 (3)	0.024 (2)	0.0109 (19)	0.0100 (17)	0.014 (2)
C37	0.0123 (19)	0.030 (3)	0.024 (2)	0.0085 (18)	0.0072 (16)	0.015 (2)
C38	0.014 (2)	0.021 (2)	0.026 (2)	0.0053 (18)	0.0056 (16)	0.011 (2)
C39	0.016 (2)	0.038 (3)	0.027 (2)	0.003 (2)	0.0038 (17)	0.020 (2)
O10	0.048 (2)	0.065 (3)	0.0319 (19)	0.021 (2)	0.0116 (16)	0.0081 (19)
C40	0.053 (3)	0.039 (3)	0.037 (3)	0.012 (3)	0.007 (2)	0.014 (3)

Geometric parameters (Å, º) top

Gd1—O1	2.355 (3)	C7—C8	1.475 (6)
Gd1—O4	2.308 (3)	C8—C9	1.424 (6)
Gd1—O9ⁱ	2.360 (2)	C8—C12	1.381 (5)
Gd1—O11	2.485 (3)	C9—C9ⁱⁱ	1.420 (8)
Gd1—O12	2.477 (3)	C9—C10	1.424 (5)
Gd1—O14	2.483 (3)	C10—C11	1.479 (6)
Gd1—O16	2.488 (3)	C10—C13	1.378 (6)
Gd1—O17	2.477 (3)	C12—H12	0.9500
Gd1—O18	2.549 (3)	C12—C13ⁱⁱ	1.409 (6)
Gd1—N7	2.906 (4)	C13—C12ⁱⁱ	1.409 (6)
Gd1—N8	2.892 (4)	C13—H13	0.9500
Gd1—N9	2.942 (4)	C14—H14	0.9500
O1—N5	1.343 (4)	C14—C15	1.366 (6)
O2—C7	1.221 (5)	C15—H15	0.9500
O3—C11	1.219 (5)	C15—C16	1.395 (6)
O4—N1	1.338 (4)	C16—H16	0.9500
O5—C31	1.215 (5)	C16—C17	1.386 (6)
O6—C20	1.219 (4)	C17—C18	1.381 (5)
O7—C26	1.213 (5)	C17—C19	1.517 (6)
O8—C25	1.215 (5)	C18—H18	0.9500
O9—Gd1ⁱ	2.360 (2)	C19—H19A	0.9900
O9—N4	1.338 (4)	C19—H19B	0.9900
O11—N8	1.274 (4)	C20—C21	1.481 (6)
O12—N8	1.286 (4)	C21—C22	1.362 (6)
O13—N8	1.224 (4)	C21—C32	1.416 (5)
O14—N7	1.266 (4)	C22—H22	0.9500
O15—N7	1.231 (4)	C22—C23	1.413 (5)
O16—N7	1.276 (4)	C23—H23	0.9500
O17—N9	1.275 (4)	C23—C24	1.375 (5)
O18—N9	1.278 (4)	C24—C25	1.481 (6)
O19—N9	1.221 (4)	C24—C33	1.415 (5)
N1—C14	1.343 (5)	C26—C27	1.479 (6)
N1—C18	1.338 (5)	C27—C28	1.384 (6)
N2—C19	1.467 (5)	C27—C33	1.410 (5)
N2—C20	1.398 (5)	C28—H28	0.9500
N2—C31	1.409 (5)	C28—C29	1.403 (6)
N3—C25	1.408 (5)	C29—H29	0.9500
N3—C26	1.409 (5)	C29—C30	1.386 (5)
N3—C39	1.472 (5)	C30—C31	1.485 (6)
N4—C34	1.342 (5)	C30—C32	1.414 (5)
N4—C38	1.363 (5)	C32—C33	1.417 (5)
N5—C1	1.352 (6)	C34—H34	0.9500
N5—C5	1.344 (5)	C34—C35	1.379 (5)
N6—C6	1.476 (5)	C35—H35	0.9500
N6—C7	1.407 (5)	C35—C36	1.385 (6)
N6—C11	1.398 (5)	C36—H36	0.9500
C1—H1	0.9500	C36—C37	1.401 (6)
C1—C2	1.372 (7)	C37—C38	1.388 (5)
C2—H2	0.9500	C37—C39	1.518 (6)
C2—C3	1.395 (6)	C38—H38	0.9500
C3—H3	0.9500	C39—H39A	0.9900
C3—C4	1.388 (6)	C39—H39B	0.9900
C4—C5	1.383 (6)	O10—H10	0.8400
C4—C6	1.512 (5)	O10—C40	1.411 (6)
C5—H5	0.9500	C40—H40A	0.9800
C6—H6A	0.9900	C40—H40B	0.9800
C6—H6B	0.9900	C40—H40C	0.9800

O1—Gd1—O9ⁱ	78.81 (9)	C5—C4—C6	118.3 (4)
O1—Gd1—O11	74.37 (9)	N5—C5—C4	120.8 (4)
O1—Gd1—O12	86.21 (10)	N5—C5—H5	119.6
O1—Gd1—O14	145.39 (9)	C4—C5—H5	119.6
O1—Gd1—O16	151.94 (10)	N6—C6—C4	112.6 (3)
O1—Gd1—O17	127.01 (10)	N6—C6—H6A	109.1
O1—Gd1—O18	76.15 (10)	N6—C6—H6B	109.1
O1—Gd1—N7	162.60 (10)	C4—C6—H6A	109.1
O1—Gd1—N8	82.10 (9)	C4—C6—H6B	109.1
O1—Gd1—N9	101.64 (10)	H6A—C6—H6B	107.8
O4—Gd1—O1	85.14 (10)	O2—C7—N6	120.3 (4)
O4—Gd1—O9ⁱ	81.00 (10)	O2—C7—C8	122.0 (4)
O4—Gd1—O11	77.98 (9)	N6—C7—C8	117.6 (4)
O4—Gd1—O12	129.68 (10)	C9—C8—C7	118.8 (4)
O4—Gd1—O14	86.13 (10)	C12—C8—C7	121.3 (4)
O4—Gd1—O16	72.54 (9)	C12—C8—C9	119.9 (4)
O4—Gd1—O17	139.39 (10)	C9ⁱⁱ—C9—C8	119.3 (4)
O4—Gd1—O18	150.53 (10)	C9ⁱⁱ—C9—C10	119.2 (5)
O4—Gd1—N7	79.66 (10)	C10—C9—C8	121.5 (4)
O4—Gd1—N8	103.39 (10)	C9—C10—C11	119.6 (4)
O4—Gd1—N9	153.53 (9)	C13—C10—C9	120.5 (4)
O9ⁱ—Gd1—O11	147.03 (9)	C13—C10—C11	119.9 (4)
O9ⁱ—Gd1—O12	144.68 (11)	O3—C11—N6	120.4 (4)
O9ⁱ—Gd1—O14	132.48 (10)	O3—C11—C10	122.6 (4)
O9ⁱ—Gd1—O16	81.04 (9)	N6—C11—C10	117.0 (4)
O9ⁱ—Gd1—O17	82.13 (9)	C8—C12—H12	119.5
O9ⁱ—Gd1—O18	73.24 (10)	C8—C12—C13ⁱⁱ	121.0 (4)
O9ⁱ—Gd1—N7	106.82 (10)	C13ⁱⁱ—C12—H12	119.5
O9ⁱ—Gd1—N8	159.99 (10)	C10—C13—C12ⁱⁱ	120.1 (4)
O9ⁱ—Gd1—N9	75.40 (9)	C10—C13—H13	120.0
O11—Gd1—O16	115.76 (10)	C12ⁱⁱ—C13—H13	120.0
O11—Gd1—O18	117.35 (10)	N1—C14—H14	120.1
O11—Gd1—N7	94.09 (10)	N1—C14—C15	119.9 (4)
O11—Gd1—N8	26.02 (10)	C15—C14—H14	120.1
O11—Gd1—N9	128.47 (9)	C14—C15—H15	120.2
O12—Gd1—O11	51.99 (9)	C14—C15—C16	119.5 (4)
O12—Gd1—O14	74.02 (10)	C16—C15—H15	120.2
O12—Gd1—O16	121.07 (10)	C15—C16—H16	120.3
O12—Gd1—O17	81.80 (9)	C17—C16—C15	119.4 (4)
O12—Gd1—O18	72.18 (10)	C17—C16—H16	120.3
O12—Gd1—N7	96.99 (11)	C16—C17—C19	122.1 (4)
O12—Gd1—N8	26.28 (10)	C18—C17—C16	118.7 (4)
O12—Gd1—N9	76.62 (9)	C18—C17—C19	119.0 (4)
O14—Gd1—O11	71.06 (10)	N1—C18—C17	120.4 (4)
O14—Gd1—O16	51.49 (9)	N1—C18—H18	119.8
O14—Gd1—O18	121.92 (10)	C17—C18—H18	119.8
O14—Gd1—N7	25.66 (9)	N2—C19—C17	112.6 (3)
O14—Gd1—N8	67.53 (10)	N2—C19—H19A	109.1
O14—Gd1—N9	101.01 (10)	N2—C19—H19B	109.1
O16—Gd1—O18	116.15 (9)	C17—C19—H19A	109.1
O16—Gd1—N7	25.91 (9)	C17—C19—H19B	109.1
O16—Gd1—N8	118.96 (10)	H19A—C19—H19B	107.8
O16—Gd1—N9	91.88 (10)	O6—C20—N2	119.7 (4)
O17—Gd1—O11	129.68 (9)	O6—C20—C21	123.0 (4)
O17—Gd1—O14	78.65 (10)	N2—C20—C21	117.3 (3)
O17—Gd1—O16	68.48 (9)	C22—C21—C20	119.9 (3)
O17—Gd1—O18	51.02 (9)	C22—C21—C32	120.6 (4)
O17—Gd1—N7	70.37 (10)	C32—C21—C20	119.5 (4)
O17—Gd1—N8	105.00 (10)	C21—C22—H22	119.9
O17—Gd1—N9	25.40 (9)	C21—C22—C23	120.1 (4)
O18—Gd1—N7	121.14 (9)	C23—C22—H22	119.9
O18—Gd1—N8	96.43 (11)	C22—C23—H23	119.7
O18—Gd1—N9	25.65 (9)	C24—C23—C22	120.7 (4)
N7—Gd1—N9	95.73 (10)	C24—C23—H23	119.7
N8—Gd1—N7	93.19 (10)	C23—C24—C25	119.4 (4)
N8—Gd1—N9	102.88 (10)	C23—C24—C33	120.2 (4)
N5—O1—Gd1	125.4 (2)	C33—C24—C25	120.5 (3)
N1—O4—Gd1	131.0 (2)	O8—C25—N3	119.8 (4)
N4—O9—Gd1ⁱ	131.6 (2)	O8—C25—C24	124.1 (4)
N8—O11—Gd1	95.2 (2)	N3—C25—C24	116.1 (4)
N8—O12—Gd1	95.2 (2)	O7—C26—N3	120.4 (4)
N7—O14—Gd1	96.2 (2)	O7—C26—C27	122.6 (4)
N7—O16—Gd1	95.7 (2)	N3—C26—C27	117.0 (3)
N9—O17—Gd1	98.1 (2)	C28—C27—C26	120.4 (4)
N9—O18—Gd1	94.6 (2)	C28—C27—C33	119.8 (4)
O4—N1—C14	118.3 (3)	C33—C27—C26	119.8 (4)
O4—N1—C18	119.6 (3)	C27—C28—H28	119.7
C18—N1—C14	122.0 (3)	C27—C28—C29	120.6 (4)
C20—N2—C19	116.9 (3)	C29—C28—H28	119.7
C20—N2—C31	125.4 (3)	C28—C29—H29	119.8
C31—N2—C19	117.8 (3)	C30—C29—C28	120.5 (4)
C25—N3—C26	124.8 (4)	C30—C29—H29	119.8
C25—N3—C39	116.0 (3)	C29—C30—C31	119.8 (4)
C26—N3—C39	118.4 (3)	C29—C30—C32	120.1 (4)
O9—N4—C34	119.3 (3)	C32—C30—C31	120.1 (4)
O9—N4—C38	118.9 (3)	O5—C31—N2	120.4 (4)
C34—N4—C38	121.8 (3)	O5—C31—C30	123.3 (4)
O1—N5—C1	120.5 (3)	N2—C31—C30	116.3 (4)
O1—N5—C5	118.8 (4)	C21—C32—C33	119.5 (4)
C5—N5—C1	120.6 (4)	C30—C32—C21	121.4 (4)
C7—N6—C6	116.6 (4)	C30—C32—C33	119.1 (3)
C11—N6—C6	118.6 (3)	C24—C33—C32	118.9 (3)
C11—N6—C7	124.8 (3)	C27—C33—C24	121.1 (4)
O14—N7—Gd1	58.12 (19)	C27—C33—C32	120.0 (4)
O14—N7—O16	116.3 (3)	N4—C34—H34	120.2
O15—N7—Gd1	175.4 (3)	N4—C34—C35	119.5 (4)
O15—N7—O14	122.4 (4)	C35—C34—H34	120.2
O15—N7—O16	121.4 (4)	C34—C35—H35	120.0
O16—N7—Gd1	58.40 (18)	C34—C35—C36	120.0 (4)
O11—N8—Gd1	58.83 (18)	C36—C35—H35	120.0
O11—N8—O12	116.3 (3)	C35—C36—H36	119.8
O12—N8—Gd1	58.55 (18)	C35—C36—C37	120.4 (4)
O13—N8—Gd1	169.4 (3)	C37—C36—H36	119.8
O13—N8—O11	121.7 (4)	C36—C37—C39	120.0 (3)
O13—N8—O12	121.9 (4)	C38—C37—C36	117.4 (4)
O17—N9—Gd1	56.48 (19)	C38—C37—C39	122.5 (4)
O17—N9—O18	116.1 (3)	N4—C38—C37	120.9 (4)
O18—N9—Gd1	59.7 (2)	N4—C38—H38	119.5
O19—N9—Gd1	174.9 (3)	C37—C38—H38	119.5
O19—N9—O17	121.6 (3)	N3—C39—C37	114.4 (3)
O19—N9—O18	122.3 (4)	N3—C39—H39A	108.7
N5—C1—H1	119.6	N3—C39—H39B	108.7
N5—C1—C2	120.7 (4)	C37—C39—H39A	108.7
C2—C1—H1	119.6	C37—C39—H39B	108.7
C1—C2—H2	120.2	H39A—C39—H39B	107.6
C1—C2—C3	119.6 (5)	C40—O10—H10	109.5
C3—C2—H2	120.2	O10—C40—H40A	109.5
C2—C3—H3	120.6	O10—C40—H40B	109.5
C4—C3—C2	118.8 (4)	O10—C40—H40C	109.5
C4—C3—H3	120.6	H40A—C40—H40B	109.5
C3—C4—C6	122.3 (4)	H40A—C40—H40C	109.5
C5—C4—C3	119.4 (4)	H40B—C40—H40C	109.5

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

catena-poly[[[tris(nitrato-κ²O,O')dysprosium(III)]-bis{µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'}-[tris(nitrato-κ²O,O')dysprosium(III)]-µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'] methanol disolvate] (Dy) top

Crystal data top

[Dy(C₂₆H₁₆N₄O₄)_1.5(NO₃)₃]·CH₄O	Z = 2
M_r = 1100.20	F(000) = 1096
Triclinic, P1	D_x = 1.812 Mg m⁻³
a = 9.8244 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.2522 (7) Å	Cell parameters from 5987 reflections
c = 15.9247 (7) Å	θ = 2.8–31.0°
α = 109.461 (4)°	µ = 1.95 mm⁻¹
β = 103.600 (4)°	T = 173 K
γ = 106.050 (4)°	Block, yellow
V = 2016.25 (18) Å³	0.18 × 0.15 × 0.12 mm

Data collection top

Multiwire proportional diffractometer	5554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
phi and ω scans	θ_max = 24.7°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −11→11
T_min = 0.954, T_max = 1.000	k = −17→17
14386 measured reflections	l = −18→18
6647 independent reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0371P)² + 1.037P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
6647 reflections	Δρ_max = 1.34 e Å⁻³
624 parameters	Δρ_min = −0.83 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
Dy1	0.76935 (3)	0.82379 (2)	0.63607 (2)	0.02135 (10)
O1	0.0059 (4)	0.1539 (3)	0.2559 (2)	0.0260 (8)
O2	−0.0601 (4)	0.4254 (3)	0.0713 (3)	0.0522 (12)
O3	0.1757 (4)	0.2205 (3)	−0.0385 (2)	0.0298 (9)
O4	0.6327 (4)	0.8479 (3)	0.2729 (3)	0.0347 (9)
O5	0.8742 (4)	0.6404 (3)	0.1764 (3)	0.0376 (10)
O6	0.9351 (4)	0.9223 (3)	0.5956 (2)	0.0269 (8)
O7	0.8239 (4)	0.6929 (3)	0.5445 (2)	0.0284 (9)
O8	1.3053 (4)	0.6844 (3)	0.8694 (3)	0.0351 (9)
O9	1.3646 (4)	0.8709 (3)	0.7012 (3)	0.0309 (9)
O10	0.5024 (4)	0.7124 (3)	0.5470 (3)	0.0362 (10)
O11	0.6224 (4)	0.7748 (3)	0.4690 (2)	0.0337 (9)
O12	0.3740 (4)	0.7020 (3)	0.4085 (3)	0.0493 (12)
O13	0.8452 (4)	1.0010 (3)	0.7477 (3)	0.0280 (9)
O14	0.6313 (4)	0.9343 (3)	0.6309 (3)	0.0336 (9)
O15	0.7002 (5)	1.0857 (3)	0.7419 (3)	0.0423 (10)
O16	0.7035 (4)	0.6946 (3)	0.7013 (3)	0.0330 (9)
O17	0.6825 (4)	0.8368 (3)	0.7698 (3)	0.0287 (9)
O18	0.6438 (4)	0.7259 (3)	0.8291 (3)	0.0334 (9)
N1	−0.0460 (4)	0.1211 (3)	0.1608 (3)	0.0220 (10)
N2	0.0623 (4)	0.3219 (3)	0.0269 (3)	0.0242 (10)
N3	1.0002 (5)	0.8986 (3)	0.5304 (3)	0.0240 (10)
N4	0.7532 (5)	0.7430 (3)	0.2257 (3)	0.0234 (10)
N5	0.8957 (5)	0.6424 (3)	0.5797 (3)	0.0274 (11)
N6	1.3516 (5)	0.7776 (3)	0.7867 (3)	0.0260 (10)
N7	0.4950 (6)	0.7290 (4)	0.4722 (3)	0.0346 (12)
N8	0.7251 (6)	1.0095 (4)	0.7083 (3)	0.0301 (11)
N9	0.6754 (5)	0.7517 (4)	0.7682 (3)	0.0271 (11)
C1	−0.1117 (5)	0.0210 (4)	0.1050 (4)	0.0223 (12)
H1	−0.1188	−0.0256	0.1328	0.027*
C2	−0.1681 (5)	−0.0129 (4)	0.0077 (4)	0.0224 (12)
H2	−0.2164	−0.0832	−0.0322	0.027*
C3	−0.1547 (5)	0.0555 (4)	−0.0321 (4)	0.0247 (12)
H3	−0.1935	0.0319	−0.0995	0.030*
C4	−0.0855 (5)	0.1579 (4)	0.0253 (3)	0.0214 (12)
C5	−0.0320 (5)	0.1899 (4)	0.1232 (4)	0.0224 (12)
H5	0.0147	0.2600	0.1643	0.027*
C6	−0.0806 (6)	0.2328 (4)	−0.0183 (4)	0.0320 (14)
H6A	−0.0977	0.1980	−0.0869	0.038*
H6B	−0.1651	0.2554	−0.0141	0.038*
C7	0.0576 (6)	0.4174 (4)	0.0694 (4)	0.0307 (13)
C8	0.2039 (5)	0.5060 (4)	0.1111 (4)	0.0220 (12)
C9	0.2102 (6)	0.6014 (4)	0.1576 (4)	0.0328 (14)
H9	0.1202	0.6106	0.1627	0.039*
C10	0.3471 (6)	0.6853 (4)	0.1975 (4)	0.0273 (13)
H10	0.3499	0.7509	0.2297	0.033*
C11	0.4785 (5)	0.6726 (4)	0.1900 (3)	0.0220 (12)
C12	0.6239 (6)	0.7616 (4)	0.2328 (4)	0.0263 (12)
C13	0.7554 (6)	0.6485 (4)	0.1800 (4)	0.0262 (12)
C14	0.6083 (5)	0.5600 (4)	0.1352 (3)	0.0196 (11)
C15	0.6029 (5)	0.4656 (4)	0.0879 (3)	0.0198 (11)
H15	0.6930	0.4561	0.0838	0.024*
C16	0.4632 (5)	0.3822 (4)	0.0454 (3)	0.0210 (11)
H16	0.4591	0.3167	0.0111	0.025*
C17	0.3332 (5)	0.3948 (4)	0.0530 (3)	0.0191 (11)
C18	0.1887 (6)	0.3054 (4)	0.0092 (4)	0.0241 (12)
C19	0.3365 (5)	0.4912 (4)	0.1018 (3)	0.0186 (11)
C20	0.4752 (6)	0.5760 (4)	0.1428 (3)	0.0201 (11)
C21	1.1432 (6)	0.9040 (4)	0.5585 (4)	0.0329 (14)
H21	1.1974	0.9245	0.6242	0.039*
C22	1.2118 (7)	0.8803 (5)	0.4937 (4)	0.0385 (15)
H22	1.3126	0.8831	0.5137	0.046*
C23	1.1326 (6)	0.8522 (4)	0.3988 (4)	0.0337 (14)
H23	1.1782	0.8341	0.3527	0.040*
C24	0.9876 (6)	0.8504 (4)	0.3706 (4)	0.0241 (12)
C25	0.9211 (6)	0.8730 (4)	0.4382 (4)	0.0228 (12)
H25	0.8203	0.8705	0.4199	0.027*
C26	0.8997 (6)	0.8294 (4)	0.2691 (4)	0.0287 (13)
H26A	0.8814	0.8901	0.2694	0.034*
H26B	0.9622	0.8162	0.2295	0.034*
C27	0.8158 (7)	0.5545 (4)	0.5769 (4)	0.0374 (15)
H27	0.7080	0.5276	0.5504	0.045*
C28	0.8897 (7)	0.5026 (5)	0.6126 (5)	0.0489 (17)
H28	0.8325	0.4395	0.6098	0.059*
C29	1.0474 (7)	0.5421 (5)	0.6529 (5)	0.0436 (16)
H29	1.0991	0.5072	0.6785	0.052*
C30	1.1276 (6)	0.6337 (4)	0.6548 (4)	0.0279 (13)
C31	1.0492 (6)	0.6819 (4)	0.6161 (4)	0.0266 (13)
H31	1.1036	0.7434	0.6151	0.032*
C32	1.2987 (6)	0.6837 (4)	0.6992 (4)	0.0317 (13)
H32A	1.3393	0.6362	0.7150	0.038*
H32B	1.3393	0.6992	0.6522	0.038*
C33	1.3575 (6)	0.7677 (4)	0.8713 (4)	0.0268 (13)
C34	1.4299 (5)	0.8605 (4)	0.9616 (4)	0.0228 (12)
C35	1.4686 (5)	0.9552 (4)	0.9570 (4)	0.0235 (12)
C36	1.4469 (5)	0.9622 (4)	0.8684 (4)	0.0231 (12)
C37	1.3850 (6)	0.8689 (4)	0.7785 (4)	0.0269 (13)
C38	1.4556 (6)	0.8576 (4)	1.0485 (4)	0.0277 (13)
H38	1.4313	0.7940	1.0510	0.033*
C39	1.4837 (5)	1.0554 (4)	0.8663 (4)	0.0249 (12)
H39	1.4677	1.0601	0.8071	0.030*
O19	0.7050 (5)	0.5802 (4)	0.3450 (3)	0.0541 (12)
H19	0.7509	0.6231	0.4020	0.081*
C40	0.5541 (7)	0.5245 (5)	0.3320 (4)	0.0495 (18)
H40A	0.5549	0.5022	0.3831	0.074*
H40B	0.5076	0.4655	0.2700	0.074*
H40C	0.4954	0.5672	0.3339	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.02247 (15)	0.02356 (15)	0.01946 (14)	0.00803 (11)	0.00974 (11)	0.01007 (11)
O1	0.025 (2)	0.038 (2)	0.0189 (19)	0.0120 (17)	0.0074 (15)	0.0168 (17)
O2	0.027 (2)	0.051 (3)	0.080 (3)	0.018 (2)	0.025 (2)	0.023 (3)
O3	0.029 (2)	0.028 (2)	0.026 (2)	0.0058 (17)	0.0082 (17)	0.0105 (19)
O4	0.044 (2)	0.025 (2)	0.032 (2)	0.0162 (19)	0.0089 (19)	0.0099 (19)
O5	0.028 (2)	0.029 (2)	0.048 (3)	0.0076 (18)	0.0174 (19)	0.008 (2)
O6	0.033 (2)	0.029 (2)	0.0220 (19)	0.0108 (17)	0.0155 (17)	0.0110 (17)
O7	0.029 (2)	0.031 (2)	0.027 (2)	0.0173 (18)	0.0086 (17)	0.0110 (18)
O8	0.037 (2)	0.029 (2)	0.043 (2)	0.0135 (19)	0.0123 (19)	0.020 (2)
O9	0.027 (2)	0.041 (2)	0.029 (2)	0.0148 (18)	0.0107 (17)	0.0190 (19)
O10	0.031 (2)	0.044 (3)	0.034 (2)	0.0058 (18)	0.0137 (18)	0.023 (2)
O11	0.030 (2)	0.039 (2)	0.027 (2)	0.0028 (18)	0.0122 (17)	0.0142 (19)
O12	0.024 (2)	0.060 (3)	0.042 (3)	0.001 (2)	−0.003 (2)	0.019 (2)
O13	0.028 (2)	0.031 (2)	0.030 (2)	0.0137 (18)	0.0153 (17)	0.0136 (18)
O14	0.033 (2)	0.038 (2)	0.032 (2)	0.0181 (19)	0.0107 (19)	0.014 (2)
O15	0.065 (3)	0.034 (3)	0.049 (3)	0.033 (2)	0.037 (2)	0.021 (2)
O16	0.039 (2)	0.032 (2)	0.036 (2)	0.0157 (19)	0.0214 (19)	0.0159 (19)
O17	0.033 (2)	0.028 (2)	0.033 (2)	0.0105 (17)	0.0187 (17)	0.0180 (18)
O18	0.035 (2)	0.045 (3)	0.031 (2)	0.0145 (19)	0.0167 (18)	0.027 (2)
N1	0.016 (2)	0.029 (3)	0.020 (2)	0.0063 (19)	0.0083 (18)	0.010 (2)
N2	0.018 (2)	0.029 (3)	0.027 (2)	0.005 (2)	0.0081 (19)	0.017 (2)
N3	0.021 (3)	0.025 (3)	0.026 (3)	0.006 (2)	0.011 (2)	0.012 (2)
N4	0.028 (3)	0.017 (2)	0.022 (2)	0.003 (2)	0.0101 (19)	0.009 (2)
N5	0.024 (3)	0.026 (3)	0.024 (2)	0.006 (2)	0.007 (2)	0.006 (2)
N6	0.021 (2)	0.027 (3)	0.034 (3)	0.011 (2)	0.009 (2)	0.016 (2)
N7	0.033 (3)	0.033 (3)	0.033 (3)	0.011 (2)	0.011 (3)	0.011 (2)
N8	0.042 (3)	0.027 (3)	0.031 (3)	0.014 (2)	0.025 (3)	0.015 (2)
N9	0.020 (2)	0.035 (3)	0.027 (3)	0.009 (2)	0.011 (2)	0.016 (2)
C1	0.016 (3)	0.021 (3)	0.031 (3)	0.006 (2)	0.013 (2)	0.010 (3)
C2	0.009 (3)	0.029 (3)	0.031 (3)	0.007 (2)	0.012 (2)	0.011 (3)
C3	0.019 (3)	0.038 (3)	0.016 (3)	0.011 (2)	0.006 (2)	0.008 (3)
C4	0.010 (3)	0.034 (3)	0.020 (3)	0.007 (2)	0.006 (2)	0.012 (3)
C5	0.016 (3)	0.018 (3)	0.031 (3)	0.002 (2)	0.012 (2)	0.009 (2)
C6	0.027 (3)	0.039 (4)	0.030 (3)	0.008 (3)	0.007 (3)	0.021 (3)
C7	0.025 (3)	0.044 (4)	0.036 (3)	0.019 (3)	0.016 (3)	0.024 (3)
C8	0.021 (3)	0.029 (3)	0.023 (3)	0.010 (2)	0.010 (2)	0.016 (2)
C9	0.035 (3)	0.039 (4)	0.033 (3)	0.023 (3)	0.017 (3)	0.015 (3)
C10	0.036 (3)	0.024 (3)	0.023 (3)	0.016 (3)	0.007 (2)	0.009 (2)
C11	0.021 (3)	0.028 (3)	0.020 (3)	0.010 (2)	0.007 (2)	0.014 (2)
C12	0.037 (3)	0.027 (3)	0.019 (3)	0.013 (3)	0.011 (2)	0.015 (3)
C13	0.030 (3)	0.026 (3)	0.023 (3)	0.008 (3)	0.012 (2)	0.012 (3)
C14	0.022 (3)	0.023 (3)	0.018 (3)	0.010 (2)	0.007 (2)	0.013 (2)
C15	0.020 (3)	0.025 (3)	0.025 (3)	0.011 (2)	0.011 (2)	0.018 (2)
C16	0.024 (3)	0.025 (3)	0.021 (3)	0.012 (2)	0.011 (2)	0.014 (2)
C17	0.022 (3)	0.022 (3)	0.017 (3)	0.008 (2)	0.007 (2)	0.012 (2)
C18	0.030 (3)	0.025 (3)	0.016 (3)	0.008 (3)	0.006 (2)	0.012 (3)
C19	0.019 (3)	0.023 (3)	0.017 (3)	0.009 (2)	0.006 (2)	0.012 (2)
C20	0.027 (3)	0.023 (3)	0.017 (3)	0.011 (2)	0.012 (2)	0.013 (2)
C21	0.027 (3)	0.038 (4)	0.034 (3)	0.011 (3)	0.006 (3)	0.020 (3)
C22	0.030 (3)	0.048 (4)	0.047 (4)	0.020 (3)	0.015 (3)	0.027 (3)
C23	0.030 (3)	0.041 (4)	0.042 (4)	0.018 (3)	0.023 (3)	0.021 (3)
C24	0.031 (3)	0.017 (3)	0.026 (3)	0.006 (2)	0.012 (2)	0.012 (2)
C25	0.021 (3)	0.020 (3)	0.023 (3)	0.003 (2)	0.007 (2)	0.010 (2)
C26	0.032 (3)	0.025 (3)	0.025 (3)	0.002 (2)	0.012 (2)	0.011 (3)
C27	0.031 (3)	0.031 (4)	0.043 (4)	0.009 (3)	0.008 (3)	0.014 (3)
C28	0.045 (4)	0.031 (4)	0.071 (5)	0.012 (3)	0.020 (4)	0.026 (4)
C29	0.046 (4)	0.036 (4)	0.056 (4)	0.021 (3)	0.017 (3)	0.025 (3)
C30	0.027 (3)	0.028 (3)	0.030 (3)	0.013 (3)	0.011 (2)	0.011 (3)
C31	0.030 (3)	0.021 (3)	0.024 (3)	0.007 (2)	0.012 (2)	0.005 (2)
C32	0.030 (3)	0.035 (4)	0.032 (3)	0.017 (3)	0.014 (3)	0.011 (3)
C33	0.016 (3)	0.036 (4)	0.043 (4)	0.016 (3)	0.015 (3)	0.027 (3)
C34	0.014 (3)	0.025 (3)	0.035 (3)	0.008 (2)	0.009 (2)	0.018 (3)
C35	0.011 (3)	0.036 (3)	0.035 (3)	0.011 (2)	0.012 (2)	0.023 (3)
C36	0.013 (3)	0.031 (3)	0.029 (3)	0.011 (2)	0.008 (2)	0.016 (3)
C37	0.019 (3)	0.035 (3)	0.034 (3)	0.016 (3)	0.011 (2)	0.018 (3)
C38	0.027 (3)	0.032 (3)	0.040 (3)	0.018 (3)	0.018 (3)	0.025 (3)
C39	0.018 (3)	0.036 (3)	0.035 (3)	0.015 (2)	0.015 (2)	0.025 (3)
O19	0.051 (3)	0.063 (3)	0.033 (2)	0.019 (3)	0.012 (2)	0.008 (2)
C40	0.057 (5)	0.045 (4)	0.032 (4)	0.010 (3)	0.009 (3)	0.013 (3)

Geometric parameters (Å, º) top

Dy1—O1ⁱ	2.315 (3)	C7—C8	1.488 (7)
Dy1—O6	2.260 (3)	C8—C9	1.371 (7)
Dy1—O7	2.328 (3)	C8—C19	1.415 (7)
Dy1—O10	2.440 (4)	C9—H9	0.9500
Dy1—O11	2.448 (4)	C9—C10	1.399 (8)
Dy1—O13	2.466 (4)	C10—H10	0.9500
Dy1—O14	2.448 (4)	C10—C11	1.383 (7)
Dy1—O16	2.521 (4)	C11—C12	1.483 (7)
Dy1—O17	2.444 (3)	C11—C20	1.401 (7)
Dy1—N7	2.861 (5)	C13—C14	1.488 (7)
Dy1—N8	2.878 (5)	C14—C15	1.364 (7)
Dy1—N9	2.895 (4)	C14—C20	1.419 (7)
O1—Dy1ⁱ	2.315 (3)	C15—H15	0.9500
O1—N1	1.339 (5)	C15—C16	1.408 (7)
O2—C7	1.202 (6)	C16—H16	0.9500
O3—C18	1.215 (6)	C16—C17	1.369 (7)
O4—C12	1.225 (6)	C17—C18	1.480 (7)
O5—C13	1.219 (6)	C17—C19	1.403 (7)
O6—N3	1.346 (5)	C19—C20	1.414 (7)
O7—N5	1.345 (5)	C21—H21	0.9500
O8—C33	1.219 (6)	C21—C22	1.365 (8)
O9—C37	1.211 (6)	C22—H22	0.9500
O10—N7	1.287 (6)	C22—C23	1.380 (8)
O11—N7	1.277 (6)	C23—H23	0.9500
O12—N7	1.223 (6)	C23—C24	1.379 (7)
O13—N8	1.262 (6)	C24—C25	1.382 (7)
O14—N8	1.274 (6)	C24—C26	1.519 (7)
O15—N8	1.225 (6)	C25—H25	0.9500
O16—N9	1.274 (5)	C26—H26A	0.9900
O17—N9	1.272 (5)	C26—H26B	0.9900
O18—N9	1.234 (5)	C27—H27	0.9500
N1—C1	1.349 (6)	C27—C28	1.378 (8)
N1—C5	1.363 (6)	C28—H28	0.9500
N2—C6	1.467 (6)	C28—C29	1.391 (8)
N2—C7	1.406 (7)	C29—H29	0.9500
N2—C18	1.406 (7)	C29—C30	1.388 (8)
N3—C21	1.340 (7)	C30—C31	1.379 (7)
N3—C25	1.352 (6)	C30—C32	1.510 (7)
N4—C12	1.397 (7)	C31—H31	0.9500
N4—C13	1.390 (7)	C32—H32A	0.9900
N4—C26	1.471 (6)	C32—H32B	0.9900
N5—C27	1.334 (7)	C33—C34	1.477 (8)
N5—C31	1.351 (7)	C34—C35	1.420 (7)
N6—C32	1.477 (7)	C34—C38	1.366 (7)
N6—C33	1.396 (7)	C35—C35ⁱⁱ	1.419 (10)
N6—C37	1.397 (7)	C35—C36	1.421 (7)
C1—H1	0.9500	C36—C37	1.483 (7)
C1—C2	1.370 (7)	C36—C39	1.379 (7)
C2—H2	0.9500	C38—H38	0.9500
C2—C3	1.383 (7)	C38—C39ⁱⁱ	1.392 (7)
C3—H3	0.9500	C39—C38ⁱⁱ	1.392 (7)
C3—C4	1.380 (7)	C39—H39	0.9500
C4—C5	1.381 (7)	O19—H19	0.8400
C4—C6	1.519 (7)	O19—C40	1.416 (7)
C5—H5	0.9500	C40—H40A	0.9800
C6—H6A	0.9900	C40—H40B	0.9800
C6—H6B	0.9900	C40—H40C	0.9800

O1ⁱ—Dy1—O7	79.16 (12)	C5—C4—C6	121.1 (5)
O1ⁱ—Dy1—O10	144.36 (13)	N1—C5—C4	120.1 (5)
O1ⁱ—Dy1—O11	146.61 (12)	N1—C5—H5	120.0
O1ⁱ—Dy1—O13	80.66 (12)	C4—C5—H5	120.0
O1ⁱ—Dy1—O14	132.53 (13)	N2—C6—C4	114.4 (4)
O1ⁱ—Dy1—O16	73.18 (12)	N2—C6—H6A	108.7
O1ⁱ—Dy1—O17	82.97 (12)	N2—C6—H6B	108.7
O1ⁱ—Dy1—N7	160.05 (13)	C4—C6—H6A	108.7
O1ⁱ—Dy1—N8	106.40 (14)	C4—C6—H6B	108.7
O1ⁱ—Dy1—N9	75.82 (12)	H6A—C6—H6B	107.6
O6—Dy1—O1ⁱ	81.05 (12)	O2—C7—N2	120.6 (5)
O6—Dy1—O7	85.31 (13)	O2—C7—C8	122.7 (5)
O6—Dy1—O10	130.24 (12)	N2—C7—C8	116.8 (4)
O6—Dy1—O11	78.02 (12)	C9—C8—C7	120.3 (5)
O6—Dy1—O13	71.96 (12)	C9—C8—C19	120.2 (5)
O6—Dy1—O14	85.75 (13)	C19—C8—C7	119.5 (5)
O6—Dy1—O16	150.62 (12)	C8—C9—H9	119.6
O6—Dy1—O17	138.97 (12)	C8—C9—C10	120.9 (5)
O6—Dy1—N7	103.64 (13)	C10—C9—H9	119.6
O6—Dy1—N8	79.04 (12)	C9—C10—H10	120.0
O6—Dy1—N9	153.69 (12)	C11—C10—C9	120.0 (5)
O7—Dy1—O10	86.27 (13)	C11—C10—H10	120.0
O7—Dy1—O11	73.47 (13)	C10—C11—C12	119.9 (5)
O7—Dy1—O13	151.62 (12)	C10—C11—C20	120.3 (5)
O7—Dy1—O14	144.88 (13)	C20—C11—C12	119.8 (4)
O7—Dy1—O16	76.33 (12)	O4—C12—N4	120.5 (5)
O7—Dy1—O17	128.08 (12)	O4—C12—C11	122.5 (5)
O7—Dy1—N7	81.89 (13)	N4—C12—C11	116.9 (5)
O7—Dy1—N8	162.21 (12)	O5—C13—N4	120.3 (5)
O7—Dy1—N9	102.26 (13)	O5—C13—C14	122.4 (5)
O10—Dy1—O11	52.62 (12)	N4—C13—C14	117.4 (4)
O10—Dy1—O13	121.32 (13)	C15—C14—C13	120.1 (4)
O10—Dy1—O14	74.04 (13)	C15—C14—C20	121.1 (4)
O10—Dy1—O16	71.83 (12)	C20—C14—C13	118.8 (5)
O10—Dy1—O17	80.82 (12)	C14—C15—H15	120.1
O10—Dy1—N7	26.61 (12)	C14—C15—C16	119.8 (4)
O10—Dy1—N8	97.36 (14)	C16—C15—H15	120.1
O10—Dy1—N9	75.79 (12)	C15—C16—H16	119.7
O11—Dy1—O13	116.40 (12)	C17—C16—C15	120.5 (5)
O11—Dy1—O16	117.17 (12)	C17—C16—H16	119.7
O11—Dy1—N7	26.39 (12)	C16—C17—C18	119.3 (5)
O11—Dy1—N8	94.85 (13)	C16—C17—C19	120.5 (4)
O11—Dy1—N9	128.26 (12)	C19—C17—C18	120.2 (4)
O13—Dy1—O16	116.27 (12)	O3—C18—N2	119.7 (5)
O13—Dy1—N7	119.29 (13)	O3—C18—C17	123.7 (5)
O13—Dy1—N8	25.88 (12)	N2—C18—C17	116.6 (5)
O13—Dy1—N9	91.85 (12)	C17—C19—C8	121.6 (4)
O14—Dy1—O11	71.46 (13)	C17—C19—C20	119.6 (4)
O14—Dy1—O13	51.93 (12)	C20—C19—C8	118.9 (5)
O14—Dy1—O16	122.17 (12)	C11—C20—C14	121.8 (4)
O14—Dy1—N7	67.42 (13)	C11—C20—C19	119.8 (4)
O14—Dy1—N8	26.13 (13)	C19—C20—C14	118.4 (5)
O14—Dy1—N9	100.70 (13)	N3—C21—H21	119.7
O16—Dy1—N7	96.34 (13)	N3—C21—C22	120.6 (5)
O16—Dy1—N8	121.38 (12)	C22—C21—H21	119.7
O16—Dy1—N9	26.04 (12)	C21—C22—H22	120.5
O17—Dy1—O11	129.26 (12)	C21—C22—C23	119.0 (5)
O17—Dy1—O13	68.28 (12)	C23—C22—H22	120.5
O17—Dy1—O14	77.83 (12)	C22—C23—H23	119.9
O17—Dy1—O16	51.83 (12)	C24—C23—C22	120.2 (5)
O17—Dy1—N7	104.16 (13)	C24—C23—H23	119.9
O17—Dy1—N8	69.70 (12)	C23—C24—C25	119.0 (5)
O17—Dy1—N9	25.83 (12)	C23—C24—C26	122.8 (5)
N7—Dy1—N8	93.55 (14)	C25—C24—C26	118.1 (5)
N7—Dy1—N9	102.37 (13)	N3—C25—C24	119.6 (5)
N8—Dy1—N9	95.51 (13)	N3—C25—H25	120.2
N1—O1—Dy1ⁱ	132.6 (3)	C24—C25—H25	120.2
N3—O6—Dy1	131.2 (3)	N4—C26—C24	112.9 (4)
N5—O7—Dy1	124.5 (3)	N4—C26—H26A	109.0
N7—O10—Dy1	95.3 (3)	N4—C26—H26B	109.0
N7—O11—Dy1	95.2 (3)	C24—C26—H26A	109.0
N8—O13—Dy1	95.6 (3)	C24—C26—H26B	109.0
N8—O14—Dy1	96.1 (3)	H26A—C26—H26B	107.8
N9—O16—Dy1	93.6 (3)	N5—C27—H27	120.0
N9—O17—Dy1	97.3 (3)	N5—C27—C28	120.0 (5)
O1—N1—C1	119.2 (4)	C28—C27—H27	120.0
O1—N1—C5	119.0 (4)	C27—C28—H28	119.8
C1—N1—C5	121.8 (4)	C27—C28—C29	120.3 (6)
C7—N2—C6	118.5 (4)	C29—C28—H28	119.8
C7—N2—C18	124.7 (4)	C28—C29—H29	120.8
C18—N2—C6	115.9 (4)	C30—C29—C28	118.4 (5)
O6—N3—C25	118.9 (4)	C30—C29—H29	120.8
C21—N3—O6	119.5 (4)	C29—C30—C32	122.1 (5)
C21—N3—C25	121.5 (4)	C31—C30—C29	119.3 (5)
C12—N4—C26	118.3 (4)	C31—C30—C32	118.6 (5)
C13—N4—C12	125.3 (4)	N5—C31—C30	120.6 (5)
C13—N4—C26	116.5 (4)	N5—C31—H31	119.7
O7—N5—C31	118.6 (4)	C30—C31—H31	119.7
C27—N5—O7	120.1 (4)	N6—C32—C30	112.3 (4)
C27—N5—C31	121.3 (5)	N6—C32—H32A	109.1
C33—N6—C32	116.9 (4)	N6—C32—H32B	109.1
C33—N6—C37	124.7 (5)	C30—C32—H32A	109.1
C37—N6—C32	118.3 (4)	C30—C32—H32B	109.1
O10—N7—Dy1	58.1 (2)	H32A—C32—H32B	107.9
O11—N7—Dy1	58.4 (2)	O8—C33—N6	120.1 (5)
O11—N7—O10	115.4 (4)	O8—C33—C34	122.1 (5)
O12—N7—Dy1	169.9 (4)	N6—C33—C34	117.9 (5)
O12—N7—O10	122.2 (5)	C35—C34—C33	118.6 (5)
O12—N7—O11	122.5 (5)	C38—C34—C33	122.0 (5)
O13—N8—Dy1	58.5 (2)	C38—C34—C35	119.4 (5)
O13—N8—O14	116.0 (4)	C34—C35—C36	121.5 (5)
O14—N8—Dy1	57.8 (3)	C35ⁱⁱ—C35—C34	119.1 (6)
O15—N8—Dy1	175.7 (3)	C35ⁱⁱ—C35—C36	119.4 (6)
O15—N8—O13	122.2 (5)	C35—C36—C37	119.5 (5)
O15—N8—O14	121.7 (5)	C39—C36—C35	120.1 (5)
O16—N9—Dy1	60.3 (2)	C39—C36—C37	120.4 (5)
O17—N9—Dy1	56.9 (2)	O9—C37—N6	121.0 (5)
O17—N9—O16	117.1 (4)	O9—C37—C36	122.1 (5)
O18—N9—Dy1	175.9 (4)	N6—C37—C36	116.9 (5)
O18—N9—O16	121.5 (5)	C34—C38—H38	118.8
O18—N9—O17	121.4 (4)	C34—C38—C39ⁱⁱ	122.3 (5)
N1—C1—H1	120.3	C39ⁱⁱ—C38—H38	118.8
N1—C1—C2	119.3 (5)	C36—C39—C38ⁱⁱ	119.7 (5)
C2—C1—H1	120.3	C36—C39—H39	120.1
C1—C2—H2	120.1	C38ⁱⁱ—C39—H39	120.1
C1—C2—C3	119.8 (5)	C40—O19—H19	109.5
C3—C2—H2	120.1	O19—C40—H40A	109.5
C2—C3—H3	119.7	O19—C40—H40B	109.5
C4—C3—C2	120.6 (5)	O19—C40—H40C	109.5
C4—C3—H3	119.7	H40A—C40—H40B	109.5
C3—C4—C5	118.3 (5)	H40A—C40—H40C	109.5
C3—C4—C6	120.4 (4)	H40B—C40—H40C	109.5

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

catena-poly[[[tris(nitrato-κ²O,O')erbium(III)]-bis{µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'}-[tris(nitrato-κ²O,O')erbium(III)]-µ-N,N'-bis[(1-oxidopyridin-1-ium-3-yl)methyl]-1,8:4,5-naphthalenetetracarboxdiimide-κ²O:O'] methanol disolvate] (Er) top

Crystal data top

[Er(C₂₆H₁₆N₄O₄)_1.5(NO₃)₃]·CH₄O	Z = 2
M_r = 1105.97	F(000) = 1102
Triclinic, P1	D_x = 1.826 Mg m⁻³
a = 9.8242 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.2333 (3) Å	Cell parameters from 18978 reflections
c = 15.8956 (4) Å	θ = 2.4–30.1°
α = 109.532 (2)°	µ = 2.18 mm⁻¹
β = 103.449 (2)°	T = 173 K
γ = 106.019 (2)°	Block, yellow
V = 2011.59 (8) Å³	0.5 × 0.3 × 0.2 mm

Data collection top

Multiwire proportional diffractometer	8170 independent reflections
Radiation source: fine-focus sealed tube	7631 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −10→12
T_min = 0.664, T_max = 1.000	k = −19→19
28106 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0316P)² + 0.6579P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
8170 reflections	Δρ_max = 1.02 e Å⁻³
624 parameters	Δρ_min = −0.72 e Å⁻³
0 restraints

Special details top

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	0.22946 (2)	0.17565 (2)	0.36282 (2)	0.01769 (4)
O1	0.99472 (18)	0.84675 (12)	0.74378 (11)	0.0230 (3)
O2	1.0602 (2)	0.57422 (16)	0.92877 (18)	0.0495 (6)
O3	0.82346 (19)	0.77957 (12)	1.03827 (12)	0.0258 (4)
O4	0.3666 (2)	0.15172 (12)	0.72605 (13)	0.0316 (4)
O5	0.12580 (19)	0.35943 (13)	0.82364 (14)	0.0340 (4)
O6	0.06495 (18)	0.07741 (12)	0.40385 (11)	0.0232 (3)
O7	0.17572 (18)	0.30551 (12)	0.45406 (11)	0.0242 (4)
O8	−0.3054 (2)	0.31558 (12)	0.13102 (13)	0.0303 (4)
O9	−0.36415 (19)	0.12900 (13)	0.29931 (12)	0.0286 (4)
O10	0.49477 (19)	0.28587 (13)	0.45017 (12)	0.0295 (4)
O11	0.37604 (18)	0.22434 (12)	0.52846 (12)	0.0266 (4)
O12	0.6227 (2)	0.29777 (15)	0.58844 (14)	0.0417 (5)
O13	0.15268 (19)	0.00023 (12)	0.25146 (11)	0.0242 (4)
O14	0.3666 (2)	0.06619 (13)	0.36790 (12)	0.0292 (4)
O15	0.2962 (2)	−0.08570 (13)	0.25710 (14)	0.0371 (4)
O16	0.31656 (19)	0.16296 (12)	0.23051 (12)	0.0245 (4)
O17	0.2956 (2)	0.30459 (12)	0.29839 (12)	0.0281 (4)
O18	0.3569 (2)	0.27318 (13)	0.17117 (12)	0.0296 (4)
N1	1.0442 (2)	0.87895 (14)	0.83843 (13)	0.0182 (4)
N2	0.9366 (2)	0.67765 (14)	0.97257 (14)	0.0227 (4)
N3	0.0016 (2)	0.10215 (13)	0.46947 (13)	0.0204 (4)
N4	0.2470 (2)	0.25651 (14)	0.77338 (13)	0.0221 (4)
N5	0.1036 (2)	0.35643 (14)	0.41982 (14)	0.0229 (4)
N6	−0.3507 (2)	0.22229 (15)	0.21369 (15)	0.0232 (4)
N7	0.5023 (2)	0.27039 (15)	0.52505 (15)	0.0271 (5)
N8	0.2730 (2)	−0.00866 (15)	0.29151 (15)	0.0254 (5)
N9	0.3248 (2)	0.24828 (14)	0.23171 (14)	0.0215 (4)
C1	1.1114 (2)	0.97919 (17)	0.89431 (17)	0.0205 (5)
H1	1.1193	1.0259	0.8665	0.025*
C2	1.1685 (2)	1.01298 (17)	0.99206 (17)	0.0219 (5)
H2	1.2172	1.0834	1.0321	0.026*
C3	1.1550 (2)	0.94468 (18)	1.03216 (16)	0.0212 (5)
H3	1.1933	0.9683	1.0997	0.025*
C4	1.0853 (2)	0.84149 (17)	0.97382 (17)	0.0208 (5)
C5	1.0310 (2)	0.81015 (17)	0.87589 (16)	0.0200 (5)
H5	0.9841	0.7401	0.8345	0.024*
C6	1.0800 (3)	0.76660 (19)	1.01728 (18)	0.0277 (5)
H6A	1.1639	0.7435	1.0124	0.033*
H6B	1.0979	0.8017	1.0861	0.033*
C7	0.9418 (3)	0.58218 (19)	0.93045 (18)	0.0281 (5)
C8	0.7964 (3)	0.49367 (18)	0.88884 (17)	0.0227 (5)
C9	0.7899 (3)	0.39722 (19)	0.84103 (18)	0.0282 (5)
H9	0.8792	0.3876	0.8349	0.034*
C10	0.6528 (3)	0.31411 (18)	0.80189 (18)	0.0275 (5)
H10	0.6500	0.2482	0.7699	0.033*
C11	0.5217 (3)	0.32636 (16)	0.80900 (16)	0.0211 (5)
C12	0.3759 (3)	0.23780 (17)	0.76629 (16)	0.0234 (5)
C13	0.2439 (3)	0.35158 (17)	0.81951 (16)	0.0224 (5)
C14	0.3911 (3)	0.43918 (16)	0.86410 (15)	0.0188 (5)
C15	0.3966 (3)	0.53435 (16)	0.91258 (16)	0.0189 (5)
H15	0.3069	0.5440	0.9179	0.023*
C16	0.5365 (3)	0.61767 (17)	0.95440 (16)	0.0197 (5)
H16	0.5405	0.6834	0.9884	0.024*
C17	0.6666 (3)	0.60535 (16)	0.94685 (15)	0.0180 (4)
C18	0.8109 (3)	0.69465 (17)	0.98993 (16)	0.0198 (5)
C19	0.6637 (3)	0.50820 (16)	0.89768 (15)	0.0177 (4)
C20	0.5244 (3)	0.42394 (16)	0.85681 (15)	0.0181 (5)
C21	−0.1423 (3)	0.09616 (19)	0.44062 (18)	0.0280 (5)
H21	−0.1965	0.0753	0.3749	0.034*
C22	−0.2101 (3)	0.1203 (2)	0.5064 (2)	0.0352 (6)
H22	−0.3105	0.1180	0.4867	0.042*
C23	−0.1317 (3)	0.14807 (19)	0.60191 (19)	0.0306 (6)
H23	−0.1774	0.1659	0.6481	0.037*
C24	0.0138 (3)	0.14965 (16)	0.62946 (16)	0.0230 (5)
C25	0.0791 (3)	0.12728 (16)	0.56094 (16)	0.0208 (5)
H25	0.1798	0.1298	0.5789	0.025*
C26	0.1005 (3)	0.16960 (17)	0.73045 (17)	0.0258 (5)
H26A	0.0382	0.1828	0.7703	0.031*
H26B	0.1190	0.1088	0.7298	0.031*
C27	0.1846 (3)	0.44537 (19)	0.4232 (2)	0.0336 (6)
H27	0.2923	0.4723	0.4501	0.040*
C28	0.1114 (3)	0.4971 (2)	0.3875 (2)	0.0419 (7)
H28	0.1684	0.5602	0.3903	0.050*
C29	−0.0457 (3)	0.4574 (2)	0.3475 (2)	0.0375 (6)
H29	−0.0970	0.4924	0.3218	0.045*
C30	−0.1267 (3)	0.36572 (18)	0.34546 (18)	0.0262 (5)
C31	−0.0486 (3)	0.31749 (17)	0.38357 (16)	0.0233 (5)
H31	−0.1031	0.2558	0.3843	0.028*
C32	−0.2978 (3)	0.31633 (18)	0.30159 (18)	0.0271 (5)
H32A	−0.3382	0.3007	0.3487	0.033*
H32B	−0.3381	0.3641	0.2861	0.033*
C33	−0.3579 (3)	0.23246 (18)	0.12875 (18)	0.0226 (5)
C34	−0.4299 (2)	0.13881 (17)	0.03847 (17)	0.0205 (5)
C35	−0.4696 (2)	0.04465 (17)	0.04302 (17)	0.0205 (5)
C36	−0.4470 (2)	0.03785 (17)	0.13134 (17)	0.0211 (5)
C37	−0.3855 (2)	0.13082 (18)	0.22191 (18)	0.0226 (5)
C38	−0.4545 (3)	0.14337 (18)	−0.04859 (18)	0.0222 (5)
H38	−0.4294	0.2072	−0.0508	0.027*
C39	−0.4839 (3)	−0.05512 (18)	0.13403 (18)	0.0228 (5)
H39	−0.4677	−0.0593	0.1936	0.027*
O19	0.2943 (2)	0.41900 (17)	0.65389 (14)	0.0473 (5)
H19	0.2513	0.3739	0.5975	0.071*
C40	0.4443 (3)	0.4755 (2)	0.6678 (2)	0.0415 (7)
H40A	0.4440	0.4995	0.6178	0.062*
H40B	0.5033	0.4329	0.6648	0.062*
H40C	0.4901	0.5335	0.7306	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.01824 (6)	0.01705 (6)	0.01630 (6)	0.00431 (4)	0.00666 (4)	0.00712 (4)
O1	0.0252 (9)	0.0278 (9)	0.0145 (8)	0.0098 (7)	0.0054 (7)	0.0089 (7)
O2	0.0228 (10)	0.0448 (12)	0.0780 (16)	0.0129 (9)	0.0243 (11)	0.0187 (11)
O3	0.0264 (9)	0.0190 (8)	0.0239 (9)	0.0023 (7)	0.0065 (7)	0.0068 (7)
O4	0.0392 (11)	0.0191 (9)	0.0315 (10)	0.0119 (8)	0.0055 (8)	0.0092 (7)
O5	0.0190 (9)	0.0273 (9)	0.0448 (11)	0.0022 (7)	0.0126 (8)	0.0075 (8)
O6	0.0264 (9)	0.0227 (8)	0.0203 (8)	0.0054 (7)	0.0124 (7)	0.0095 (7)
O7	0.0259 (9)	0.0236 (8)	0.0207 (8)	0.0119 (7)	0.0050 (7)	0.0072 (7)
O8	0.0303 (10)	0.0235 (9)	0.0395 (10)	0.0096 (7)	0.0095 (8)	0.0189 (8)
O9	0.0265 (9)	0.0350 (10)	0.0278 (9)	0.0120 (8)	0.0090 (8)	0.0178 (8)
O10	0.0279 (9)	0.0313 (9)	0.0267 (9)	0.0042 (8)	0.0106 (8)	0.0147 (8)
O11	0.0210 (9)	0.0285 (9)	0.0235 (9)	0.0024 (7)	0.0061 (7)	0.0103 (7)
O12	0.0228 (10)	0.0483 (12)	0.0367 (11)	0.0021 (9)	−0.0020 (9)	0.0162 (9)
O13	0.0258 (9)	0.0214 (8)	0.0235 (8)	0.0069 (7)	0.0094 (7)	0.0087 (7)
O14	0.0285 (9)	0.0285 (9)	0.0275 (9)	0.0105 (8)	0.0073 (8)	0.0104 (8)
O15	0.0530 (12)	0.0279 (10)	0.0424 (11)	0.0231 (9)	0.0269 (10)	0.0159 (8)
O16	0.0307 (9)	0.0218 (8)	0.0260 (9)	0.0103 (7)	0.0143 (7)	0.0130 (7)
O17	0.0345 (10)	0.0248 (9)	0.0293 (9)	0.0113 (8)	0.0160 (8)	0.0136 (7)
O18	0.0301 (10)	0.0356 (10)	0.0274 (9)	0.0070 (8)	0.0123 (8)	0.0216 (8)
N1	0.0155 (9)	0.0220 (10)	0.0166 (9)	0.0068 (8)	0.0058 (8)	0.0080 (8)
N2	0.0171 (10)	0.0243 (10)	0.0254 (10)	0.0029 (8)	0.0065 (8)	0.0139 (8)
N3	0.0241 (10)	0.0164 (9)	0.0206 (10)	0.0039 (8)	0.0096 (8)	0.0100 (8)
N4	0.0253 (10)	0.0162 (9)	0.0195 (10)	0.0013 (8)	0.0077 (8)	0.0073 (8)
N5	0.0238 (11)	0.0196 (10)	0.0220 (10)	0.0081 (8)	0.0075 (9)	0.0059 (8)
N6	0.0197 (10)	0.0229 (10)	0.0286 (11)	0.0089 (8)	0.0080 (9)	0.0128 (9)
N7	0.0230 (11)	0.0230 (10)	0.0246 (11)	0.0029 (9)	0.0039 (9)	0.0057 (9)
N8	0.0340 (12)	0.0214 (10)	0.0276 (11)	0.0102 (9)	0.0187 (10)	0.0135 (9)
N9	0.0174 (10)	0.0247 (10)	0.0213 (10)	0.0053 (8)	0.0052 (8)	0.0119 (8)
C1	0.0160 (11)	0.0199 (11)	0.0287 (12)	0.0087 (9)	0.0093 (10)	0.0118 (10)
C2	0.0147 (11)	0.0213 (11)	0.0241 (12)	0.0060 (9)	0.0070 (10)	0.0041 (9)
C3	0.0144 (11)	0.0285 (12)	0.0170 (11)	0.0077 (9)	0.0053 (9)	0.0062 (9)
C4	0.0113 (10)	0.0286 (12)	0.0247 (12)	0.0064 (9)	0.0078 (9)	0.0140 (10)
C5	0.0168 (11)	0.0183 (11)	0.0225 (11)	0.0046 (9)	0.0060 (9)	0.0083 (9)
C6	0.0173 (12)	0.0316 (13)	0.0290 (13)	0.0004 (10)	0.0033 (10)	0.0176 (11)
C7	0.0235 (13)	0.0345 (14)	0.0316 (14)	0.0120 (11)	0.0131 (11)	0.0172 (11)
C8	0.0224 (12)	0.0271 (12)	0.0237 (12)	0.0113 (10)	0.0095 (10)	0.0145 (10)
C9	0.0290 (13)	0.0335 (14)	0.0311 (13)	0.0195 (11)	0.0157 (11)	0.0146 (11)
C10	0.0356 (14)	0.0231 (12)	0.0266 (13)	0.0157 (11)	0.0119 (11)	0.0098 (10)
C11	0.0277 (13)	0.0187 (11)	0.0180 (11)	0.0096 (10)	0.0075 (10)	0.0089 (9)
C12	0.0323 (13)	0.0190 (12)	0.0198 (11)	0.0092 (10)	0.0068 (10)	0.0117 (9)
C13	0.0234 (13)	0.0201 (11)	0.0213 (12)	0.0043 (10)	0.0071 (10)	0.0100 (9)
C14	0.0198 (11)	0.0187 (11)	0.0167 (11)	0.0040 (9)	0.0054 (9)	0.0098 (9)
C15	0.0190 (11)	0.0219 (11)	0.0211 (11)	0.0086 (9)	0.0102 (9)	0.0127 (9)
C16	0.0230 (12)	0.0179 (11)	0.0198 (11)	0.0077 (9)	0.0086 (10)	0.0094 (9)
C17	0.0208 (11)	0.0185 (11)	0.0154 (10)	0.0051 (9)	0.0062 (9)	0.0103 (9)
C18	0.0198 (11)	0.0223 (12)	0.0176 (11)	0.0050 (9)	0.0054 (9)	0.0124 (9)
C19	0.0201 (11)	0.0224 (11)	0.0161 (10)	0.0096 (9)	0.0082 (9)	0.0122 (9)
C20	0.0217 (12)	0.0187 (11)	0.0161 (11)	0.0071 (9)	0.0076 (9)	0.0100 (9)
C21	0.0256 (13)	0.0313 (13)	0.0291 (13)	0.0100 (11)	0.0071 (11)	0.0179 (11)
C22	0.0284 (14)	0.0449 (16)	0.0439 (16)	0.0195 (12)	0.0170 (13)	0.0250 (14)
C23	0.0324 (14)	0.0321 (14)	0.0354 (14)	0.0136 (11)	0.0210 (12)	0.0166 (12)
C24	0.0280 (13)	0.0139 (10)	0.0218 (12)	0.0004 (9)	0.0096 (10)	0.0073 (9)
C25	0.0184 (11)	0.0179 (11)	0.0225 (12)	0.0018 (9)	0.0052 (10)	0.0102 (9)
C26	0.0288 (13)	0.0194 (11)	0.0223 (12)	−0.0007 (10)	0.0103 (10)	0.0084 (9)
C27	0.0242 (13)	0.0263 (13)	0.0406 (16)	0.0033 (11)	0.0079 (12)	0.0109 (12)
C28	0.0341 (16)	0.0279 (14)	0.0602 (19)	0.0048 (12)	0.0116 (14)	0.0241 (14)
C29	0.0359 (15)	0.0289 (14)	0.0499 (17)	0.0135 (12)	0.0121 (14)	0.0207 (13)
C30	0.0244 (13)	0.0247 (12)	0.0274 (13)	0.0089 (10)	0.0090 (11)	0.0094 (10)
C31	0.0227 (12)	0.0206 (11)	0.0216 (12)	0.0058 (10)	0.0070 (10)	0.0059 (9)
C32	0.0235 (13)	0.0270 (13)	0.0314 (13)	0.0126 (10)	0.0097 (11)	0.0108 (11)
C33	0.0153 (11)	0.0283 (13)	0.0313 (13)	0.0123 (10)	0.0092 (10)	0.0171 (10)
C34	0.0130 (11)	0.0234 (11)	0.0315 (13)	0.0093 (9)	0.0095 (10)	0.0161 (10)
C35	0.0128 (11)	0.0276 (12)	0.0303 (12)	0.0105 (9)	0.0106 (10)	0.0189 (10)
C36	0.0144 (11)	0.0284 (12)	0.0298 (12)	0.0123 (9)	0.0097 (10)	0.0186 (10)
C37	0.0136 (11)	0.0299 (12)	0.0314 (13)	0.0112 (9)	0.0100 (10)	0.0176 (11)
C38	0.0181 (11)	0.0260 (12)	0.0340 (13)	0.0115 (10)	0.0124 (10)	0.0213 (11)
C39	0.0186 (11)	0.0315 (13)	0.0304 (13)	0.0147 (10)	0.0122 (10)	0.0208 (11)
O19	0.0457 (13)	0.0535 (13)	0.0262 (10)	0.0148 (10)	0.0097 (9)	0.0037 (9)
C40	0.0477 (18)	0.0337 (15)	0.0282 (14)	0.0080 (13)	0.0032 (13)	0.0094 (12)

Geometric parameters (Å, º) top

Er1—O1ⁱ	2.3024 (16)	C7—C8	1.482 (3)
Er1—O6	2.2550 (15)	C8—C9	1.385 (3)
Er1—O7	2.3043 (16)	C8—C19	1.411 (3)
Er1—O10	2.4255 (17)	C9—H9	0.9500
Er1—O11	2.4283 (16)	C9—C10	1.395 (4)
Er1—O13	2.4386 (16)	C10—H10	0.9500
Er1—O14	2.4249 (17)	C10—C11	1.376 (4)
Er1—O16	2.4186 (16)	C11—C12	1.483 (3)
Er1—O17	2.5059 (16)	C11—C20	1.414 (3)
Er1—N7	2.842 (2)	C13—C14	1.483 (3)
Er1—N8	2.848 (2)	C14—C15	1.374 (3)
Er1—N9	2.8851 (19)	C14—C20	1.415 (3)
O1—Er1ⁱ	2.3024 (16)	C15—H15	0.9500
O1—N1	1.332 (2)	C15—C16	1.411 (3)
O2—C7	1.207 (3)	C16—H16	0.9500
O3—C18	1.217 (3)	C16—C17	1.368 (3)
O4—C12	1.218 (3)	C17—C18	1.480 (3)
O5—C13	1.214 (3)	C17—C19	1.412 (3)
O6—N3	1.336 (2)	C19—C20	1.415 (3)
O7—N5	1.344 (3)	C21—H21	0.9500
O8—C33	1.213 (3)	C21—C22	1.370 (4)
O9—C37	1.210 (3)	C22—H22	0.9500
O10—N7	1.278 (3)	C22—C23	1.387 (4)
O11—N7	1.269 (3)	C23—H23	0.9500
O12—N7	1.217 (3)	C23—C24	1.385 (4)
O13—N8	1.272 (3)	C24—C25	1.382 (3)
O14—N8	1.263 (3)	C24—C26	1.513 (3)
O15—N8	1.227 (3)	C25—H25	0.9500
O16—N9	1.273 (2)	C26—H26A	0.9900
O17—N9	1.270 (3)	C26—H26B	0.9900
O18—N9	1.220 (2)	C27—H27	0.9500
N1—C1	1.349 (3)	C27—C28	1.371 (4)
N1—C5	1.359 (3)	C28—H28	0.9500
N2—C6	1.471 (3)	C28—C29	1.387 (4)
N2—C7	1.404 (3)	C29—H29	0.9500
N2—C18	1.399 (3)	C29—C30	1.390 (4)
N3—C21	1.348 (3)	C30—C31	1.374 (3)
N3—C25	1.339 (3)	C30—C32	1.511 (3)
N4—C12	1.394 (3)	C31—H31	0.9500
N4—C13	1.400 (3)	C32—H32A	0.9900
N4—C26	1.476 (3)	C32—H32B	0.9900
N5—C27	1.345 (3)	C33—C34	1.482 (3)
N5—C31	1.342 (3)	C34—C35	1.410 (3)
N6—C32	1.479 (3)	C34—C38	1.377 (3)
N6—C33	1.398 (3)	C35—C35ⁱⁱ	1.416 (5)
N6—C37	1.398 (3)	C35—C36	1.413 (3)
C1—H1	0.9500	C36—C37	1.484 (3)
C1—C2	1.376 (3)	C36—C39	1.380 (3)
C2—H2	0.9500	C38—H38	0.9500
C2—C3	1.383 (3)	C38—C39ⁱⁱ	1.402 (3)
C3—H3	0.9500	C39—C38ⁱⁱ	1.402 (3)
C3—C4	1.391 (3)	C39—H39	0.9500
C4—C5	1.383 (3)	O19—H19	0.8400
C4—C6	1.514 (3)	O19—C40	1.408 (4)
C5—H5	0.9500	C40—H40A	0.9800
C6—H6A	0.9900	C40—H40B	0.9800
C6—H6B	0.9900	C40—H40C	0.9800

O1ⁱ—Er1—O7	79.09 (6)	C5—C4—C6	121.5 (2)
O1ⁱ—Er1—O10	144.60 (6)	N1—C5—C4	120.4 (2)
O1ⁱ—Er1—O11	146.51 (6)	N1—C5—H5	119.8
O1ⁱ—Er1—O13	80.18 (6)	C4—C5—H5	119.8
O1ⁱ—Er1—O14	132.67 (6)	N2—C6—C4	114.53 (19)
O1ⁱ—Er1—O16	83.62 (6)	N2—C6—H6A	108.6
O1ⁱ—Er1—O17	73.72 (6)	N2—C6—H6B	108.6
O1ⁱ—Er1—N7	159.94 (6)	C4—C6—H6A	108.6
O1ⁱ—Er1—N8	106.49 (6)	C4—C6—H6B	108.6
O1ⁱ—Er1—N9	76.58 (5)	H6A—C6—H6B	107.6
O6—Er1—O1ⁱ	80.84 (6)	O2—C7—N2	120.6 (2)
O6—Er1—O7	85.34 (6)	O2—C7—C8	122.6 (2)
O6—Er1—O10	130.32 (6)	N2—C7—C8	116.8 (2)
O6—Er1—O11	78.07 (6)	C9—C8—C7	120.5 (2)
O6—Er1—O13	71.92 (6)	C9—C8—C19	119.9 (2)
O6—Er1—O14	85.66 (6)	C19—C8—C7	119.5 (2)
O6—Er1—O16	139.20 (5)	C8—C9—H9	119.8
O6—Er1—O17	150.89 (6)	C8—C9—C10	120.4 (2)
O6—Er1—N7	103.73 (6)	C10—C9—H9	119.8
O6—Er1—N8	78.78 (6)	C9—C10—H10	119.6
O6—Er1—N9	154.22 (6)	C11—C10—C9	120.8 (2)
O7—Er1—O10	86.52 (6)	C11—C10—H10	119.6
O7—Er1—O11	73.55 (6)	C10—C11—C12	120.5 (2)
O7—Er1—O13	151.31 (6)	C10—C11—C20	120.2 (2)
O7—Er1—O14	144.70 (6)	C20—C11—C12	119.3 (2)
O7—Er1—O16	128.14 (6)	O4—C12—N4	120.3 (2)
O7—Er1—O17	76.28 (6)	O4—C12—C11	122.4 (2)
O7—Er1—N7	81.80 (6)	N4—C12—C11	117.25 (19)
O7—Er1—N8	161.93 (6)	O5—C13—N4	120.3 (2)
O7—Er1—N9	102.23 (6)	O5—C13—C14	123.0 (2)
O10—Er1—O11	52.69 (5)	N4—C13—C14	116.6 (2)
O10—Er1—O13	121.47 (6)	C15—C14—C13	119.6 (2)
O10—Er1—O17	71.50 (6)	C15—C14—C20	120.7 (2)
O10—Er1—N7	26.61 (6)	C20—C14—C13	119.8 (2)
O10—Er1—N8	97.17 (6)	C14—C15—H15	120.3
O10—Er1—N9	75.15 (5)	C14—C15—C16	119.5 (2)
O11—Er1—O13	116.76 (6)	C16—C15—H15	120.3
O11—Er1—O17	116.84 (6)	C15—C16—H16	119.5
O11—Er1—N7	26.39 (6)	C17—C16—C15	121.1 (2)
O11—Er1—N8	94.58 (6)	C17—C16—H16	119.5
O11—Er1—N9	127.67 (5)	C16—C17—C18	119.6 (2)
O13—Er1—O17	116.25 (5)	C16—C17—C19	120.4 (2)
O13—Er1—N7	119.87 (6)	C19—C17—C18	119.9 (2)
O13—Er1—N8	26.41 (6)	O3—C18—N2	120.1 (2)
O13—Er1—N9	91.95 (5)	O3—C18—C17	123.3 (2)
O14—Er1—O10	73.77 (6)	N2—C18—C17	116.6 (2)
O14—Er1—O11	71.20 (6)	C8—C19—C17	121.4 (2)
O14—Er1—O13	52.53 (6)	C8—C19—C20	119.6 (2)
O14—Er1—O17	122.11 (6)	C17—C19—C20	118.9 (2)
O14—Er1—N7	67.39 (6)	C11—C20—C14	121.5 (2)
O14—Er1—N8	26.18 (6)	C11—C20—C19	119.1 (2)
O14—Er1—N9	100.60 (6)	C19—C20—C14	119.4 (2)
O16—Er1—O10	80.21 (6)	N3—C21—H21	120.1
O16—Er1—O11	128.73 (6)	N3—C21—C22	119.8 (2)
O16—Er1—O13	68.36 (5)	C22—C21—H21	120.1
O16—Er1—O14	77.73 (6)	C21—C22—H22	120.1
O16—Er1—O17	51.93 (5)	C21—C22—C23	119.8 (3)
O16—Er1—N7	103.69 (6)	C23—C22—H22	120.1
O16—Er1—N8	69.91 (5)	C22—C23—H23	120.2
O16—Er1—N9	25.91 (5)	C24—C23—C22	119.5 (2)
O17—Er1—N7	95.86 (6)	C24—C23—H23	120.2
O17—Er1—N8	121.68 (5)	C23—C24—C26	122.4 (2)
O17—Er1—N9	26.04 (5)	C25—C24—C23	118.6 (2)
N7—Er1—N8	93.57 (6)	C25—C24—C26	118.9 (2)
N7—Er1—N9	101.74 (6)	N3—C25—C24	120.6 (2)
N8—Er1—N9	95.80 (6)	N3—C25—H25	119.7
N1—O1—Er1ⁱ	131.48 (13)	C24—C25—H25	119.7
N3—O6—Er1	130.55 (12)	N4—C26—C24	112.06 (18)
N5—O7—Er1	124.98 (12)	N4—C26—H26A	109.2
N7—O10—Er1	95.21 (13)	N4—C26—H26B	109.2
N7—O11—Er1	95.33 (13)	C24—C26—H26A	109.2
N8—O13—Er1	95.07 (12)	C24—C26—H26B	109.2
N8—O14—Er1	95.95 (13)	H26A—C26—H26B	107.9
N9—O16—Er1	97.97 (12)	N5—C27—H27	120.1
N9—O17—Er1	93.90 (12)	N5—C27—C28	119.8 (2)
O1—N1—C1	118.84 (18)	C28—C27—H27	120.1
O1—N1—C5	119.23 (18)	C27—C28—H28	120.0
C1—N1—C5	121.88 (19)	C27—C28—C29	120.1 (3)
C7—N2—C6	117.9 (2)	C29—C28—H28	120.0
C18—N2—C6	116.1 (2)	C28—C29—H29	120.5
C18—N2—C7	125.04 (19)	C28—C29—C30	118.9 (3)
O6—N3—C21	118.69 (19)	C30—C29—H29	120.5
O6—N3—C25	119.57 (19)	C29—C30—C32	122.3 (2)
C25—N3—C21	121.7 (2)	C31—C30—C29	118.9 (2)
C12—N4—C13	125.53 (19)	C31—C30—C32	118.7 (2)
C12—N4—C26	118.17 (19)	N5—C31—C30	120.9 (2)
C13—N4—C26	116.3 (2)	N5—C31—H31	119.6
O7—N5—C27	119.6 (2)	C30—C31—H31	119.6
C31—N5—O7	119.01 (19)	N6—C32—C30	112.0 (2)
C31—N5—C27	121.3 (2)	N6—C32—H32A	109.2
C33—N6—C32	116.89 (19)	N6—C32—H32B	109.2
C33—N6—C37	125.0 (2)	C30—C32—H32A	109.2
C37—N6—C32	118.1 (2)	C30—C32—H32B	109.2
O10—N7—Er1	58.19 (11)	H32A—C32—H32B	107.9
O11—N7—Er1	58.28 (11)	O8—C33—N6	119.9 (2)
O11—N7—O10	115.45 (19)	O8—C33—C34	122.7 (2)
O12—N7—Er1	170.18 (17)	N6—C33—C34	117.4 (2)
O12—N7—O10	122.1 (2)	C35—C34—C33	119.0 (2)
O12—N7—O11	122.5 (2)	C38—C34—C33	120.7 (2)
O13—N8—Er1	58.52 (10)	C38—C34—C35	120.3 (2)
O14—N8—Er1	57.87 (11)	C34—C35—C35ⁱⁱ	118.9 (3)
O14—N8—O13	116.22 (19)	C34—C35—C36	121.5 (2)
O15—N8—Er1	175.74 (16)	C36—C35—C35ⁱⁱ	119.6 (3)
O15—N8—O13	121.4 (2)	C35—C36—C37	120.1 (2)
O15—N8—O14	122.4 (2)	C39—C36—C35	120.4 (2)
O16—N9—Er1	56.12 (10)	C39—C36—C37	119.5 (2)
O17—N9—Er1	60.06 (11)	O9—C37—N6	121.0 (2)
O17—N9—O16	116.09 (18)	O9—C37—C36	122.6 (2)
O18—N9—Er1	175.51 (15)	N6—C37—C36	116.3 (2)
O18—N9—O16	121.5 (2)	C34—C38—H38	119.5
O18—N9—O17	122.42 (19)	C34—C38—C39ⁱⁱ	120.9 (2)
N1—C1—H1	120.4	C39ⁱⁱ—C38—H38	119.5
N1—C1—C2	119.2 (2)	C36—C39—C38ⁱⁱ	119.8 (2)
C2—C1—H1	120.4	C36—C39—H39	120.1
C1—C2—H2	119.9	C38ⁱⁱ—C39—H39	120.1
C1—C2—C3	120.1 (2)	C40—O19—H19	109.5
C3—C2—H2	119.9	O19—C40—H40A	109.5
C2—C3—H3	119.9	O19—C40—H40B	109.5
C2—C3—C4	120.2 (2)	O19—C40—H40C	109.5
C4—C3—H3	119.9	H40A—C40—H40B	109.5
C3—C4—C6	120.2 (2)	H40A—C40—H40C	109.5
C5—C4—C3	118.2 (2)	H40B—C40—H40C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O19—H19···O7	0.84	2.01	2.816 (2)	161

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Four isostructural lanthanide(III) coordination compounds based on a new N-oxydic pyridyl naphthalenedi­imide ligand: synthesis and characterization

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Four isostructural lanthanide(III) coordination compounds based on a new N-oxydic pyridyl naphthalenediimide ligand: synthesis and characterization