Crystal structure and void analysis of tris­(2-amino-1-methyl­benzimidazolium) hexa­kis­(nitrato-κ2O,O′)lanthanate(III)

Ruzieva, B.; Kunafiev, R.; Kadirova, Z.; Daminova, S.

doi:10.1107/S2056989022005163

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ISSN: 2056-9890

Volume 78| Part 6| June 2022| Pages 647-651

https://doi.org/10.1107/S2056989022005163

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Crystal structure and void analysis of tris(2-amino-1-methylbenzimidazolium) hexakis(nitrato-κ²O,O′)lanthanate(III)

Bakhtigul Ruzieva,^a,^b ^* Rishad Kunafiev,^a,^c Zukhra Kadirova ^a and Shahlo Daminova ^a,^b ^*

^aUzbekistan-Japan Innovation Center of Youth, University street 2B, Tashkent 100095, Uzbekistan, ^bNational University of Uzbekistan named after Mirzo Ulugbek, University street 4, Tashkent 100174, Uzbekistan, and ^cState Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: b.ruziyeva@nuu.uz, daminova_sh@mail.ru

Edited by M. Weil, Vienna University of Technology, Austria (Received 16 March 2022; accepted 12 May 2022; online 20 May 2022)

The organic–inorganic complex salt, (C₈H₁₀N₃)₃[La(NO₃)₆], comprises a network of N-protonated 2-amino-1-methylbenzimidazolium cations and hexakis(nitrato)lanthanate(III) anions. The La^III atom is twelve-coordinate within a distorted icosahedral environment. In the unit cell, each pair of the La^III atoms lie nearly on one of the crystallographic glide planes. In the crystal structure, there are several N—H⋯O hydrogen-bonding interactions between the cations and terminal oxygen atoms from the nitrate moieties of the [La(NO₃)₆]^3– anion. Additional weak C—H⋯O hydrogen bonds between the cations and anions consolidate the three-dimensional arrangement of the structure. A packing analysis was performed to check the strength of the crystal packing.

Keywords: benzimidazolium; lanthanum complex; crystal structure.

CCDC reference: 2132821

1. Chemical context

Layered lanthanide complexes in the solid state or in solution often represent an one-dimensional transition-metal self-assembly (Chen et al., 2017 ), frequently incorporated within functional groups from various ligand systems. These complexes not only provide excellent opportunities to widen the research scope of rare-earth compounds, but also feature a novel nuclear secondary building unit (SBU), forming porous and intrinsically electrically conductive structures (Skorupskii & Dincă, 2020 ). Although lanthanide ions have characteristic electronic configurations with their complexes being ideal candidates for new crystal structures and potential applications in superconductivity, magnetism, optics, electronics and catalysis (Eliseeva & Bünzli, 2010 ; Woodruff et al., 2013 ), lanthanide complexes, especially polynuclear clusters, are not well understood (Barry et al., 2016 ). Some reasons for this are the uncontrollable polynuclear arrangement of lanthanide complexes and the nature of lanthanide ions, with their high coordination numbers, kinetic instabilities, uncertain preferred stereochemistry, and the variable nature of their coordination spheres.

In this context, originally trying to isolate polynuclear mixed-ligand lanthanum complexes, we have isolated the title organic–inorganic complex lanthanum salt, 3C₈H₁₀N₃⁺·[La(NO₃)₆]^3-, tris(2-amino-1-methylbenzimidazolium)hexakis(nitrato-O,O′)-lanthanate(III), (1), and report here its crystal structure and void analysis.

2. Structural commentary

The La^III atom in (1) (Fig. 1) is twelve-coordinate by O atoms of the nitrato ligands with La—O bond lengths varying between 2.612 (2) and 2.707 (2) Å (Table 1). The nitrato ligands in the resulting [La(NO₃)₆]^3– anion surround the La^III atom in a highly distorted icosahedral environment. Bond lengths and angles in the [La(NO₃)₆]^3– anion show no significant deviations from those of other structures where the La^III atom is coordinated by nitrate anions and/or water molecules (Drew et al., 1998 ; Fowkes & Harrison, 2006 ; Skelton et al., 2019 ; Polyzou et al., 2012 ; Bezzubov et al., 2017 ).

Table 1
Selected geometric parameters (Å, °)

La1—O1	2.646 (2)	La1—O14	2.6551 (19)
La1—O2	2.707 (2)	La1—O16	2.674 (2)
La1—O4	2.650 (2)	La1—O17	2.662 (2)
La1—O5	2.661 (2)	N7—C6	1.387 (4)
La1—O7	2.699 (2)	N7—C7	1.335 (3)
La1—O8	2.6469 (18)	N8—C1	1.395 (3)
La1—O10	2.6520 (18)	N8—C7	1.341 (4)
La1—O11	2.631 (2)	N8—C8	1.455 (3)
La1—O13	2.612 (2)	N9—C7	1.313 (4)

O1—La1—O2	47.45 (6)	O11—La1—O10	47.98 (6)
O4—La1—O5	47.94 (6)	O13—La1—O14	48.26 (6)
O8—La1—O7	47.69 (6)	O17—La1—O16	47.80 (6)

Figure 1
The molecular structure of the [La(NO₃)₆]^3– anion and surrounding C₈H₁₀N₃⁺ cations in (1), showing the atom-labeling scheme. Atomic displacement parameters are drawn at the 30% probability level and H atoms are shown at small spheres of arbitrary radius. Hydrogen bonds are shown as blue dotted lines. [Symmetry codes: (i) x, −y + $[{1\over 2}]$ , z – 1/2; (ii) x − 1, −y + $[{1\over 2}]$ , z – 1/2.]

In the unit-cell of (1), each pair of La^III atoms nearly lie on each of the crystallographic glide planes [with deviations from the mean planes of 0.00 (7)–0.02 (1) Å]. The intersection between the La^III atoms lying on neighboring glide planes at distances of 12.676 and 14.212 Å, respectively, passes through the center of inversion of the unit-cell.

3. Supramolecular features

In the crystal structure of (1) the nitrate groups coordinate bidentately to the La^III atom. The corresponding La—O—N—O planes are close to coplanar, i.e. deviate slightly from 180°. As illustrated in Fig. 2, adjacent benzimidazolium molecules stabilize the [La(NO₃)₆]^3– anion by N—H⋯O interactions (Fig. 1, Table 2). This arrangement is consolidated by slipped π⋯π interactions between neighbouring benzimidazolium cations [Cg5⋯Cg7 = 3.4515 (1) and Cg6⋯Cg9 = 3.5038 (1) Å with slippages of 0.649 and 0.219; Cg5 and Cg7 are the centroids of the C9–C14 and N13/C22/C17/N14/C23 rings, Cg6 and Cg9 are the centroids of the N10/C14–C9/N11/C15 and N13/C22–C17/N14/C23 rings; Fig. 2]. In the structure of (1), apart from the N—H⋯O interactions, there are two weak C—H⋯O interactions (Table 2) between adjacent [La(NO₃)₆]^3– anions and C₈H₁₀N₃⁺ cations (Fig. 3). The three-dimensional network of (1) is assembled from all these intermolecular contacts and interactions (Fig. 4).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O17	0.93	2.64	3.530 (5)	161
C24ⁱ—H24Cⁱ⋯O10	0.96	2.52	3.348 (5)	138
N7—H7⋯O1	0.86	2.01	2.819 (3)	157
N10—H4A⋯O4	0.86	2.05	2.889 (3)	164
N12—H6A⋯O6	0.86	2.10	2.944 (3)	165
N13—H7⋯O7	0.86	2.11	2.920 (4)	156
N15—H9B⋯O9	0.86	2.14	2.946 (3)	155
N15ⁱⁱ—H9Aⁱⁱ⋯O17	0.86	2.32	3.001 (3)	136
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
π—π stacking in the crystal structure of (1).

Figure 3
View of the crystal structure of (1) along [001], showing N—H⋯O and C—H⋯O hydrogen bonds drawn as blue dotted lines.

Figure 4
View of the crystal structure of (1) along [010], showing N—H⋯O and C—H⋯O hydrogen bonds drawn as blue dotted lines.

4. Void analysis

Molecular surfaces can be used to quite accurately define the size and shape of a molecule, and to visualize the space belonging to a molecule in a crystal. To check whether the title compound is densely packed or not, a void-space analysis was performed. Based on isosurfaces of the procrystal electron density and electron-density mapping (Fig. 5), we have used the conventional approach of mapping void space by rolling a probe sphere of variable radius over a fused-sphere representation to locate and visualize the void space in a crystalline material, as well as readily compute surface areas and void volumes (Spackman et al., 2021 ; Turner et al., 2011 ). Fig. 6 shows the unit-cell packing for the title complex with a 0.002 a.u. void surface, and a volume of 388.80 Å³ per unit cell. This result indicates that voids occupy 10.7% of the space and, hence, the molecules can be considered as densely packed in the crystal of (1).

Figure 5
The electron density map of (1) in a view along [001].

Figure 6
The void surface packing of (1) in a view along [001].

5. Database survey

The structure of the molecular [La(NO₃)₆]^3– anion was first reported by Drew et al. (1998). A search of the Cambridge Structural Database (CSD, version 5.42, update of September 2021; Groom et al., 2016 ) revealed that there are six other reports of this moiety. One was obtained from the synthesis of a dinuclear Ni^II/La^III complex containing the rare-earth metal in separate ions (Polyzou et al., 2012), the second in research into materials with luminescent properties for developing new drugs (Esteban-Parra et al., 2020 ), the third is a lanthanum/peptide heterometallic complex with interesting optical properties (Bezzubov et al., 2017), the forth was studied during synthesis and theoretical calculations at the DFT level of di-La complexes with a pendant-armed macrocycle (Fernández-Fernández et al., 2006 ), the fifth is a heteronuclear nitrato lanthanide complex with interesting magnetic properties (Thatipamula et al., 2019 ), and the sixth is a pyridine imidazolium lanthanum complex (Skelton et al., 2019). The crystal structure of the last compound comprises the anionic unit as ideal [La(NO₃)₆]^3–, i.e. oppositely faced nitrate moieties lie co-planar to the La^III atom, forming a paddle-wheel-shaped structure. The latter is one of the most closely related structures to (1), with the main difference being the number of cations.

6. Synthesis and crystallization

10 ml of an ethanol solution of La(NO₃)₃·6H₂O (216.8 mg, 0.0005 mmol) was stirred at room temperature for 1 h. Then a 10 ml ethanol solution of 2-amino-1-methylbenzimidazole (220.5 mg, 0.0015 mmol) was gradually added dropwise to the stirring mixture over 50 min at 303 K. Immediately after this, the mixture was heated in a reflux condenser at boiling temperature for 30 min. The solution was filtered and allowed to cool. The obtained yellowish single crystalline product was washed several times in pure acetone and allowed to air-dry at room temperature.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All hydrogen atoms were positioned geometrically with C—H = 0.93–0.96 Å and refined using a riding model with Uiso(H) = 1.5U_eq(C) for methyl groups and 1.2U_eq(C) for the other groups. Aromatic/amide hydrogen atoms were refined in a similar manner.

Table 3
Experimental details

Crystal data
Chemical formula	(C₈H₁₀N₃)₃[La(NO₃)₆]
M_r	955.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.78754 (10), 17.59536 (14), 17.79338 (15)
β (°)	99.4928 (8)
V (Å³)	3639.92 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	9.95
Crystal size (mm)	0.21 × 0.18 × 0.12

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.281, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21842, 7018, 6305
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.089, 1.05
No. of reflections	7018
No. of parameters	527
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.73
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ), OLEX2 (Dolomanov et al., 2009 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2132821

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022005163/wm5638sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022005163/wm5638Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989022005163/wm5638sup3.txt

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2020), publCIF (Westrip, 2010).

Tris(2-amino-1-methylbenzimidazolium) hexakis(nitrato-κ²O,O')lanthanate(III) top

Crystal data top

(C₈H₁₀N₃)₃[La(NO₃)₆]	F(000) = 1920
M_r = 955.54	D_x = 1.744 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.78754 (10) Å	Cell parameters from 13771 reflections
b = 17.59536 (14) Å	θ = 2.5–71.2°
c = 17.79338 (15) Å	µ = 9.95 mm⁻¹
β = 99.4928 (8)°	T = 293 K
V = 3639.92 (5) Å³	Block, yellow
Z = 4	0.21 × 0.18 × 0.12 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	7018 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	6305 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.4°, θ_min = 3.6°
ω scans	h = −14→10
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −21→21
T_min = 0.281, T_max = 1.000	l = −21→21
21842 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.054P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max = 0.002
S = 1.05	Δρ_max = 0.69 e Å⁻³
7018 reflections	Δρ_min = −0.73 e Å⁻³
527 parameters	Extinction correction: SHELXL (Sheldrick, 2015a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00063 (4)

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
La1	0.29343 (2)	0.24596 (2)	0.26399 (2)	0.03257 (8)
O1	0.13909 (18)	0.35278 (13)	0.21917 (11)	0.0522 (5)
O2	0.16522 (19)	0.33582 (13)	0.34071 (11)	0.0586 (5)
O3	0.0273 (2)	0.40812 (16)	0.28696 (17)	0.0880 (9)
O4	0.39500 (18)	0.38018 (12)	0.28782 (11)	0.0498 (5)
O5	0.35777 (17)	0.34828 (12)	0.16921 (10)	0.0482 (5)
O6	0.4493 (2)	0.45295 (14)	0.20134 (14)	0.0794 (7)
O7	0.4095 (2)	0.25349 (10)	0.40779 (14)	0.0475 (6)
O8	0.25431 (15)	0.18594 (12)	0.39370 (10)	0.0487 (5)
O9	0.37164 (18)	0.18384 (14)	0.50096 (11)	0.0627 (6)
O10	0.07926 (15)	0.19647 (12)	0.25603 (11)	0.0484 (5)
O11	0.20210 (16)	0.10968 (12)	0.24177 (11)	0.0483 (5)
O12	0.0197 (2)	0.08323 (15)	0.22181 (14)	0.0737 (7)
O13	0.19323 (18)	0.22778 (13)	0.12292 (12)	0.0480 (5)
O14	0.36267 (16)	0.17855 (13)	0.14595 (11)	0.0530 (5)
O15	0.2596 (2)	0.16638 (15)	0.03340 (11)	0.0679 (6)
O16	0.44669 (18)	0.13478 (12)	0.30224 (12)	0.0528 (5)
O17	0.52066 (19)	0.24035 (11)	0.27129 (13)	0.0468 (5)
O18	0.62845 (18)	0.14095 (15)	0.29585 (13)	0.0683 (6)
N1	0.1087 (2)	0.36713 (14)	0.28342 (15)	0.0511 (6)
N2	0.40091 (19)	0.39556 (13)	0.21858 (13)	0.0460 (5)
N3	0.34526 (18)	0.20720 (15)	0.43578 (12)	0.0435 (5)
N4	0.0971 (2)	0.12845 (15)	0.23923 (13)	0.0453 (6)
N5	0.27197 (19)	0.18996 (14)	0.09850 (12)	0.0426 (5)
N6	0.53406 (19)	0.17059 (14)	0.29008 (12)	0.0449 (5)
N7	−0.0092 (2)	0.40624 (14)	0.08932 (13)	0.0515 (6)
H1	0.029959	0.401296	0.134312	0.062*
N8	−0.0554 (2)	0.40492 (13)	−0.03455 (13)	0.0477 (5)
N9	0.1321 (2)	0.36555 (16)	0.01938 (17)	0.0666 (8)
H3A	0.181714	0.358860	0.060033	0.080*
H3B	0.150431	0.356204	−0.024523	0.080*
C1	−0.1515 (2)	0.43169 (16)	−0.00624 (16)	0.0457 (6)
C2	−0.2576 (3)	0.4554 (2)	−0.0427 (2)	0.0644 (9)
H2	−0.277566	0.454118	−0.095461	0.077*
C3	−0.3333 (3)	0.4813 (3)	0.0036 (3)	0.0831 (13)
H3	−0.405826	0.498305	−0.018592	0.100*
C4	−0.3035 (3)	0.4826 (3)	0.0817 (3)	0.0828 (12)
H4	−0.356791	0.500237	0.110746	0.099*
C5	−0.1968 (3)	0.4584 (2)	0.1188 (2)	0.0645 (9)
H5	−0.177024	0.459587	0.171542	0.077*
C6	−0.1216 (2)	0.43237 (16)	0.07252 (16)	0.0458 (6)
C7	0.0283 (3)	0.39002 (16)	0.02434 (16)	0.0485 (7)
C8	−0.0481 (3)	0.3937 (2)	−0.11461 (17)	0.0681 (10)
H8A	−0.123423	0.383637	−0.142553	0.102*
H8B	0.001541	0.351474	−0.119738	0.102*
H8C	−0.017603	0.438752	−0.134365	0.102*
N10	0.5796 (2)	0.43538 (14)	0.40202 (13)	0.0487 (6)
H4A	0.516816	0.419368	0.375155	0.058*
N11	0.7521 (2)	0.48326 (14)	0.43189 (14)	0.0476 (6)
N12	0.6710 (2)	0.47912 (16)	0.30120 (14)	0.0631 (7)
H6A	0.613623	0.466271	0.267181	0.076*
H6B	0.730645	0.499816	0.287798	0.076*
C9	0.7153 (3)	0.46337 (17)	0.50060 (18)	0.0475 (7)
C10	0.7675 (3)	0.4709 (2)	0.57513 (19)	0.0610 (8)
H10	0.840999	0.491168	0.588073	0.073*
C11	0.7050 (4)	0.4467 (2)	0.62983 (19)	0.0703 (10)
H11	0.736881	0.451331	0.681041	0.084*
C12	0.5960 (3)	0.4157 (2)	0.6103 (2)	0.0671 (9)
H12	0.556988	0.399753	0.648861	0.081*
C13	0.5436 (3)	0.40784 (18)	0.53563 (19)	0.0566 (7)
H13	0.470361	0.387121	0.522711	0.068*
C14	0.6059 (2)	0.43245 (16)	0.48098 (16)	0.0468 (6)
C15	0.6674 (2)	0.46703 (16)	0.37422 (16)	0.0468 (6)
C16	0.8664 (3)	0.5101 (2)	0.4250 (2)	0.0626 (8)
H16A	0.922846	0.475477	0.450741	0.094*
H16B	0.878371	0.559568	0.447659	0.094*
H16C	0.873705	0.512912	0.372153	0.094*
N13	0.6355 (2)	0.23763 (14)	0.50237 (16)	0.0445 (6)
H7	0.572120	0.228425	0.472247	0.053*
N14	0.7613 (2)	0.24800 (12)	0.60674 (17)	0.0454 (6)
N15	0.5738 (2)	0.21128 (17)	0.61913 (15)	0.0601 (7)
H9A	0.591261	0.208013	0.667896	0.072*
H9B	0.504897	0.201377	0.596973	0.072*
C17	0.8178 (3)	0.26746 (17)	0.54597 (19)	0.0428 (6)
C18	0.9309 (2)	0.28901 (19)	0.54492 (19)	0.0532 (7)
H18	0.985120	0.291954	0.589167	0.064*
C19	0.9581 (3)	0.30592 (19)	0.4736 (2)	0.0596 (8)
H19	1.032729	0.320673	0.469900	0.071*
C20	0.8769 (3)	0.30138 (19)	0.40783 (19)	0.0573 (8)
H20	0.898241	0.313790	0.361311	0.069*
C21	0.7647 (3)	0.2788 (2)	0.40965 (18)	0.0520 (7)
H21	0.710398	0.275564	0.365475	0.062*
C22	0.7376 (3)	0.26148 (15)	0.4800 (2)	0.0423 (7)
C23	0.6521 (3)	0.23136 (18)	0.57861 (18)	0.0447 (6)
C24	0.8111 (4)	0.2469 (2)	0.6871 (2)	0.0665 (11)
H24A	0.849109	0.199223	0.699414	0.100*
H24B	0.751263	0.253337	0.717210	0.100*
H24C	0.865729	0.287569	0.697737	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.02761 (11)	0.04264 (11)	0.02672 (11)	−0.00091 (5)	0.00235 (7)	−0.00063 (5)
O1	0.0533 (12)	0.0610 (13)	0.0427 (11)	0.0138 (10)	0.0095 (9)	0.0013 (9)
O2	0.0657 (13)	0.0691 (14)	0.0419 (11)	0.0064 (11)	0.0119 (10)	−0.0032 (10)
O3	0.0832 (18)	0.0851 (19)	0.103 (2)	0.0438 (15)	0.0375 (16)	0.0091 (16)
O4	0.0563 (12)	0.0531 (12)	0.0378 (10)	−0.0101 (10)	0.0015 (9)	−0.0034 (9)
O5	0.0492 (11)	0.0588 (12)	0.0360 (10)	−0.0085 (10)	0.0051 (8)	−0.0045 (9)
O6	0.0942 (18)	0.0657 (15)	0.0731 (16)	−0.0359 (14)	−0.0013 (13)	0.0180 (12)
O7	0.0387 (12)	0.0676 (15)	0.0356 (12)	−0.0118 (8)	0.0045 (9)	0.0017 (8)
O8	0.0391 (10)	0.0704 (14)	0.0345 (9)	−0.0124 (9)	−0.0006 (8)	0.0021 (9)
O9	0.0600 (12)	0.0911 (17)	0.0328 (10)	−0.0130 (12)	−0.0048 (9)	0.0158 (10)
O10	0.0362 (10)	0.0572 (13)	0.0513 (11)	−0.0035 (9)	0.0059 (8)	−0.0069 (9)
O11	0.0439 (11)	0.0488 (12)	0.0517 (12)	−0.0018 (8)	0.0064 (9)	−0.0041 (8)
O12	0.0621 (14)	0.0842 (18)	0.0775 (16)	−0.0371 (13)	0.0193 (12)	−0.0255 (14)
O13	0.0387 (11)	0.0629 (12)	0.0410 (11)	0.0030 (10)	0.0027 (9)	−0.0057 (10)
O14	0.0379 (10)	0.0772 (15)	0.0426 (11)	0.0085 (10)	0.0027 (8)	−0.0074 (10)
O15	0.0750 (14)	0.0911 (18)	0.0375 (11)	−0.0059 (13)	0.0091 (10)	−0.0185 (11)
O16	0.0480 (12)	0.0536 (12)	0.0560 (12)	0.0014 (10)	0.0067 (9)	0.0066 (10)
O17	0.0366 (11)	0.0610 (13)	0.0425 (12)	0.0019 (8)	0.0053 (9)	0.0045 (8)
O18	0.0436 (11)	0.0835 (17)	0.0754 (15)	0.0232 (11)	0.0027 (10)	−0.0033 (13)
N1	0.0535 (15)	0.0479 (14)	0.0550 (15)	0.0062 (12)	0.0182 (12)	−0.0045 (11)
N2	0.0436 (12)	0.0445 (13)	0.0481 (13)	−0.0035 (10)	0.0023 (10)	0.0034 (10)
N3	0.0361 (11)	0.0619 (15)	0.0319 (11)	−0.0024 (11)	0.0041 (9)	0.0000 (10)
N4	0.0435 (13)	0.0570 (15)	0.0357 (12)	−0.0119 (11)	0.0073 (10)	−0.0055 (10)
N5	0.0425 (12)	0.0542 (14)	0.0312 (11)	−0.0076 (11)	0.0062 (9)	−0.0023 (9)
N6	0.0398 (12)	0.0600 (15)	0.0330 (11)	0.0067 (11)	0.0006 (9)	−0.0030 (10)
N7	0.0584 (14)	0.0567 (15)	0.0389 (12)	0.0078 (12)	0.0070 (11)	0.0049 (11)
N8	0.0585 (14)	0.0471 (13)	0.0398 (12)	0.0029 (11)	0.0149 (11)	−0.0002 (10)
N9	0.0623 (17)	0.0686 (18)	0.0737 (19)	0.0211 (14)	0.0248 (14)	0.0147 (15)
C1	0.0516 (16)	0.0414 (15)	0.0452 (15)	−0.0024 (12)	0.0106 (12)	−0.0032 (12)
C2	0.0538 (19)	0.075 (2)	0.062 (2)	−0.0026 (17)	0.0007 (16)	−0.0021 (18)
C3	0.045 (2)	0.097 (3)	0.108 (4)	0.010 (2)	0.013 (2)	0.002 (3)
C4	0.067 (2)	0.092 (3)	0.100 (3)	0.008 (2)	0.044 (2)	−0.003 (3)
C5	0.069 (2)	0.073 (2)	0.058 (2)	0.0051 (18)	0.0309 (17)	−0.0028 (17)
C6	0.0511 (16)	0.0450 (15)	0.0433 (15)	0.0008 (13)	0.0140 (12)	−0.0002 (12)
C7	0.0549 (17)	0.0433 (15)	0.0511 (16)	0.0071 (13)	0.0197 (14)	0.0069 (12)
C8	0.099 (3)	0.066 (2)	0.0451 (17)	−0.0033 (19)	0.0292 (18)	−0.0037 (15)
N10	0.0437 (12)	0.0484 (14)	0.0511 (14)	−0.0051 (11)	−0.0004 (10)	−0.0009 (11)
N11	0.0468 (13)	0.0479 (14)	0.0455 (13)	−0.0055 (11)	−0.0005 (10)	0.0030 (11)
N12	0.0683 (17)	0.0747 (19)	0.0436 (14)	−0.0184 (15)	0.0007 (12)	0.0021 (13)
C9	0.0527 (18)	0.0402 (15)	0.0479 (16)	0.0006 (13)	0.0035 (13)	0.0018 (12)
C10	0.064 (2)	0.063 (2)	0.0524 (18)	−0.0001 (17)	−0.0026 (15)	−0.0013 (15)
C11	0.097 (3)	0.066 (2)	0.0459 (18)	0.004 (2)	0.0034 (18)	0.0006 (16)
C12	0.083 (2)	0.061 (2)	0.062 (2)	0.0085 (19)	0.0247 (19)	0.0075 (16)
C13	0.0537 (17)	0.0481 (17)	0.070 (2)	0.0031 (14)	0.0154 (15)	0.0049 (15)
C14	0.0499 (15)	0.0374 (14)	0.0521 (16)	0.0049 (12)	0.0059 (13)	−0.0008 (12)
C15	0.0487 (15)	0.0430 (15)	0.0453 (15)	−0.0034 (12)	−0.0020 (12)	−0.0022 (12)
C16	0.0466 (16)	0.070 (2)	0.068 (2)	−0.0130 (16)	0.0000 (14)	0.0074 (17)
N13	0.0280 (12)	0.0551 (14)	0.0482 (15)	−0.0019 (10)	−0.0003 (11)	−0.0078 (11)
N14	0.0320 (13)	0.0571 (17)	0.0457 (15)	−0.0002 (9)	0.0028 (12)	−0.0058 (9)
N15	0.0407 (13)	0.087 (2)	0.0537 (15)	−0.0050 (14)	0.0110 (11)	−0.0069 (15)
C17	0.0326 (14)	0.0438 (14)	0.0507 (17)	0.0036 (12)	0.0032 (12)	−0.0056 (13)
C18	0.0317 (14)	0.060 (2)	0.0656 (19)	−0.0028 (13)	0.0024 (13)	−0.0112 (15)
C19	0.0440 (16)	0.061 (2)	0.076 (2)	−0.0082 (15)	0.0188 (16)	−0.0096 (17)
C20	0.0565 (18)	0.060 (2)	0.0582 (19)	−0.0075 (15)	0.0197 (15)	−0.0042 (15)
C21	0.0505 (17)	0.0574 (18)	0.0468 (17)	−0.0019 (15)	0.0038 (13)	−0.0063 (14)
C22	0.0318 (14)	0.0418 (15)	0.0535 (19)	0.0018 (11)	0.0073 (13)	−0.0078 (12)
C23	0.0335 (15)	0.0509 (15)	0.0484 (17)	0.0051 (13)	0.0032 (12)	−0.0047 (13)
C24	0.051 (2)	0.095 (3)	0.049 (2)	−0.0038 (16)	−0.0054 (17)	−0.0030 (15)

Geometric parameters (Å, º) top

La1—O1	2.646 (2)	C5—C6	1.383 (4)
La1—O2	2.707 (2)	C8—H8A	0.9600
La1—O4	2.650 (2)	C8—H8B	0.9600
La1—O5	2.661 (2)	C8—H8C	0.9600
La1—O7	2.699 (2)	N10—H4A	0.8600
La1—O8	2.6469 (18)	N10—C14	1.389 (4)
La1—O10	2.6520 (18)	N10—C15	1.339 (4)
La1—O11	2.631 (2)	N11—C9	1.407 (4)
La1—O13	2.612 (2)	N11—C15	1.339 (4)
La1—O14	2.6551 (19)	N11—C16	1.452 (4)
La1—O16	2.674 (2)	N12—H6A	0.8600
La1—O17	2.662 (2)	N12—H6B	0.8600
O1—N1	1.278 (3)	N12—C15	1.324 (4)
O2—N1	1.250 (3)	C9—C10	1.373 (4)
O3—N1	1.210 (3)	C9—C14	1.390 (4)
O4—N2	1.274 (3)	C10—H10	0.9300
O5—N2	1.255 (3)	C10—C11	1.381 (5)
O6—N2	1.223 (3)	C11—H11	0.9300
O7—N3	1.269 (3)	C11—C12	1.387 (5)
O8—N3	1.259 (3)	C12—H12	0.9300
O9—N3	1.221 (3)	C12—C13	1.377 (5)
O10—N4	1.260 (3)	C13—H13	0.9300
O11—N4	1.275 (3)	C13—C14	1.382 (4)
O12—N4	1.212 (3)	C16—H16A	0.9600
O13—N5	1.275 (3)	C16—H16B	0.9600
O14—N5	1.264 (3)	C16—H16C	0.9600
O15—N5	1.216 (3)	N13—H7	0.8600
O16—N6	1.256 (3)	N13—C22	1.393 (4)
O17—N6	1.275 (3)	N13—C23	1.343 (4)
O18—N6	1.218 (3)	N14—C17	1.403 (4)
N7—H1	0.8600	N14—C23	1.335 (4)
N7—C6	1.387 (4)	N14—C24	1.453 (5)
N7—C7	1.335 (3)	N15—H9A	0.8600
N8—C1	1.395 (3)	N15—H9B	0.8600
N8—C7	1.341 (4)	N15—C23	1.310 (4)
N8—C8	1.455 (3)	C17—C18	1.389 (4)
N9—H3A	0.8600	C17—C22	1.385 (5)
N9—H3B	0.8600	C18—H18	0.9300
N9—C7	1.313 (4)	C18—C19	1.392 (4)
C1—C2	1.375 (4)	C19—H19	0.9300
C1—C6	1.388 (4)	C19—C20	1.386 (5)
C2—H2	0.9300	C20—H20	0.9300
C2—C3	1.388 (5)	C20—C21	1.386 (4)
C3—H3	0.9300	C21—H21	0.9300
C3—C4	1.376 (6)	C21—C22	1.376 (5)
C4—H4	0.9300	C24—H24A	0.9600
C4—C5	1.386 (6)	C24—H24B	0.9600
C5—H5	0.9300	C24—H24C	0.9600

O1—La1—O2	47.45 (6)	H3A—N9—H3B	120.0
O1—La1—O4	71.65 (6)	C7—N9—H3A	120.0
O1—La1—O5	65.29 (6)	C7—N9—H3B	120.0
O1—La1—O7	117.83 (6)	C2—C1—N8	131.4 (3)
O1—La1—O8	109.65 (6)	C2—C1—C6	122.2 (3)
O1—La1—O10	67.42 (7)	C6—C1—N8	106.3 (3)
O1—La1—O14	111.39 (6)	C1—C2—H2	121.8
O1—La1—O16	177.08 (6)	C1—C2—C3	116.3 (4)
O1—La1—O17	132.64 (6)	C3—C2—H2	121.8
O4—La1—O2	70.97 (7)	C2—C3—H3	119.2
O4—La1—O5	47.94 (6)	C4—C3—C2	121.5 (4)
O4—La1—O7	70.09 (6)	C4—C3—H3	119.2
O4—La1—O10	134.59 (6)	C3—C4—H4	118.8
O4—La1—O14	109.57 (6)	C3—C4—C5	122.4 (3)
O4—La1—O16	110.05 (6)	C5—C4—H4	118.8
O4—La1—O17	66.47 (6)	C4—C5—H5	122.0
O5—La1—O2	99.53 (7)	C6—C5—C4	116.1 (3)
O5—La1—O7	114.50 (6)	C6—C5—H5	122.0
O5—La1—O16	113.90 (6)	N7—C6—C1	106.8 (2)
O5—La1—O17	70.51 (6)	C5—C6—N7	131.6 (3)
O7—La1—O2	74.41 (7)	C5—C6—C1	121.5 (3)
O8—La1—O2	66.50 (7)	N7—C7—N8	109.2 (2)
O8—La1—O4	110.80 (6)	N9—C7—N7	125.0 (3)
O8—La1—O5	158.64 (6)	N9—C7—N8	125.8 (3)
O8—La1—O7	47.69 (6)	N8—C8—H8A	109.5
O8—La1—O10	67.32 (6)	N8—C8—H8B	109.5
O8—La1—O14	129.20 (7)	N8—C8—H8C	109.5
O8—La1—O16	72.16 (6)	H8A—C8—H8B	109.5
O8—La1—O17	105.15 (6)	H8A—C8—H8C	109.5
O10—La1—O2	67.23 (6)	H8B—C8—H8C	109.5
O10—La1—O5	123.81 (6)	C14—N10—H4A	125.3
O10—La1—O7	113.34 (6)	C15—N10—H4A	125.3
O10—La1—O14	103.01 (6)	C15—N10—C14	109.4 (2)
O10—La1—O16	111.76 (6)	C9—N11—C16	125.3 (3)
O10—La1—O17	158.71 (6)	C15—N11—C9	108.4 (2)
O11—La1—O1	110.99 (6)	C15—N11—C16	126.2 (3)
O11—La1—O2	111.06 (6)	H6A—N12—H6B	120.0
O11—La1—O4	177.33 (6)	C15—N12—H6A	120.0
O11—La1—O5	132.34 (6)	C15—N12—H6B	120.0
O11—La1—O7	108.55 (6)	C10—C9—N11	131.5 (3)
O11—La1—O8	69.00 (6)	C10—C9—C14	122.0 (3)
O11—La1—O10	47.98 (6)	C14—C9—N11	106.6 (3)
O11—La1—O14	69.24 (6)	C9—C10—H10	121.8
O11—La1—O16	67.30 (6)	C9—C10—C11	116.4 (3)
O11—La1—O17	110.92 (6)	C11—C10—H10	121.8
O13—La1—O1	67.53 (7)	C10—C11—H11	119.2
O13—La1—O2	110.77 (7)	C10—C11—C12	121.6 (3)
O13—La1—O4	112.56 (7)	C12—C11—H11	119.2
O13—La1—O5	66.72 (7)	C11—C12—H12	119.0
O13—La1—O7	174.63 (6)	C13—C12—C11	122.1 (3)
O13—La1—O8	132.30 (6)	C13—C12—H12	119.0
O13—La1—O10	68.46 (6)	C12—C13—H13	121.9
O13—La1—O11	68.59 (7)	C12—C13—C14	116.2 (3)
O13—La1—O14	48.26 (6)	C14—C13—H13	121.9
O13—La1—O16	109.55 (7)	N10—C14—C9	106.4 (2)
O13—La1—O17	109.53 (7)	C13—C14—N10	131.9 (3)
O14—La1—O2	158.41 (7)	C13—C14—C9	121.7 (3)
O14—La1—O5	69.15 (6)	N10—C15—N11	109.2 (2)
O14—La1—O7	126.73 (7)	N12—C15—N10	125.5 (3)
O14—La1—O16	65.90 (7)	N12—C15—N11	125.2 (3)
O14—La1—O17	65.41 (6)	N11—C16—H16A	109.5
O16—La1—O2	135.15 (7)	N11—C16—H16B	109.5
O16—La1—O7	65.09 (7)	N11—C16—H16C	109.5
O17—La1—O2	129.64 (7)	H16A—C16—H16B	109.5
O17—La1—O7	66.84 (7)	H16A—C16—H16C	109.5
O17—La1—O16	47.80 (6)	H16B—C16—H16C	109.5
N1—O1—La1	98.69 (16)	C22—N13—H7	125.5
N1—O2—La1	96.49 (15)	C23—N13—H7	125.5
N2—O4—La1	97.46 (15)	C23—N13—C22	109.0 (3)
N2—O5—La1	97.46 (15)	C17—N14—C24	126.6 (3)
N3—O7—La1	95.65 (15)	C23—N14—C17	108.4 (3)
N3—O8—La1	98.41 (14)	C23—N14—C24	125.0 (3)
N4—O10—La1	97.48 (14)	H9A—N15—H9B	120.0
N4—O11—La1	98.06 (16)	C23—N15—H9A	120.0
N5—O13—La1	98.75 (15)	C23—N15—H9B	120.0
N5—O14—La1	96.95 (14)	C18—C17—N14	131.0 (3)
N6—O16—La1	97.36 (15)	C22—C17—N14	106.9 (3)
N6—O17—La1	97.39 (16)	C22—C17—C18	122.1 (3)
O2—N1—O1	116.9 (2)	C17—C18—H18	122.1
O3—N1—O1	120.4 (3)	C17—C18—C19	115.9 (3)
O3—N1—O2	122.7 (3)	C19—C18—H18	122.1
O5—N2—O4	117.1 (2)	C18—C19—H19	119.1
O6—N2—O4	121.3 (2)	C20—C19—C18	121.8 (3)
O6—N2—O5	121.6 (2)	C20—C19—H19	119.1
O8—N3—O7	117.5 (2)	C19—C20—H20	119.2
O9—N3—O7	120.9 (2)	C19—C20—C21	121.7 (3)
O9—N3—O8	121.5 (2)	C21—C20—H20	119.2
O10—N4—O11	115.9 (2)	C20—C21—H21	121.6
O12—N4—O10	122.5 (2)	C22—C21—C20	116.8 (3)
O12—N4—O11	121.7 (3)	C22—C21—H21	121.6
O14—N5—O13	116.0 (2)	C17—C22—N13	106.4 (3)
O15—N5—O13	121.5 (2)	C21—C22—N13	131.9 (3)
O15—N5—O14	122.5 (2)	C21—C22—C17	121.7 (3)
O16—N6—O17	117.3 (2)	N14—C23—N13	109.4 (3)
O18—N6—O16	122.3 (3)	N15—C23—N13	125.4 (3)
O18—N6—O17	120.4 (3)	N15—C23—N14	125.2 (3)
C6—N7—H1	125.5	N14—C24—H24A	109.5
C7—N7—H1	125.5	N14—C24—H24B	109.5
C7—N7—C6	109.0 (2)	N14—C24—H24C	109.5
C1—N8—C8	125.6 (3)	H24A—C24—H24B	109.5
C7—N8—C1	108.7 (2)	H24A—C24—H24C	109.5
C7—N8—C8	125.7 (3)	H24B—C24—H24C	109.5

La1—O1—N1—O2	7.3 (3)	N11—C9—C10—C11	178.4 (3)
La1—O1—N1—O3	−171.3 (3)	N11—C9—C14—N10	−0.7 (3)
La1—O2—N1—O1	−7.1 (3)	N11—C9—C14—C13	−179.0 (3)
La1—O2—N1—O3	171.5 (3)	C9—N11—C15—N10	−2.1 (3)
La1—O4—N2—O5	2.2 (2)	C9—N11—C15—N12	179.1 (3)
La1—O4—N2—O6	−175.9 (2)	C9—C10—C11—C12	0.7 (5)
La1—O5—N2—O4	−2.2 (2)	C10—C9—C14—N10	178.5 (3)
La1—O5—N2—O6	175.9 (2)	C10—C9—C14—C13	0.2 (5)
La1—O7—N3—O8	−8.4 (2)	C10—C11—C12—C13	−0.5 (6)
La1—O7—N3—O9	171.0 (2)	C11—C12—C13—C14	0.1 (5)
La1—O8—N3—O7	8.7 (3)	C12—C13—C14—N10	−177.8 (3)
La1—O8—N3—O9	−170.7 (2)	C12—C13—C14—C9	0.0 (4)
La1—O10—N4—O11	7.7 (2)	C14—N10—C15—N11	1.7 (3)
La1—O10—N4—O12	−172.4 (2)	C14—N10—C15—N12	−179.5 (3)
La1—O11—N4—O10	−7.8 (2)	C14—C9—C10—C11	−0.6 (5)
La1—O11—N4—O12	172.4 (2)	C15—N10—C14—C9	−0.6 (3)
La1—O13—N5—O14	−2.3 (2)	C15—N10—C14—C13	177.5 (3)
La1—O13—N5—O15	177.5 (2)	C15—N11—C9—C10	−177.4 (3)
La1—O14—N5—O13	2.3 (2)	C15—N11—C9—C14	1.7 (3)
La1—O14—N5—O15	−177.6 (2)	C16—N11—C9—C10	7.8 (5)
La1—O16—N6—O17	4.3 (2)	C16—N11—C9—C14	−173.1 (3)
La1—O16—N6—O18	−175.8 (2)	C16—N11—C15—N10	172.6 (3)
La1—O17—N6—O16	−4.3 (2)	C16—N11—C15—N12	−6.2 (5)
La1—O17—N6—O18	175.8 (2)	N14—C17—C18—C19	−178.9 (3)
N8—C1—C2—C3	−177.9 (3)	N14—C17—C22—N13	−0.8 (3)
N8—C1—C6—N7	0.0 (3)	N14—C17—C22—C21	178.2 (3)
N8—C1—C6—C5	177.9 (3)	C17—N14—C23—N13	1.2 (3)
C1—N8—C7—N7	−0.3 (3)	C17—N14—C23—N15	−179.4 (3)
C1—N8—C7—N9	−178.4 (3)	C17—C18—C19—C20	0.0 (5)
C1—C2—C3—C4	−0.5 (6)	C18—C17—C22—N13	179.0 (3)
C2—C1—C6—N7	−179.1 (3)	C18—C17—C22—C21	−2.0 (4)
C2—C1—C6—C5	−1.1 (5)	C18—C19—C20—C21	−0.8 (5)
C2—C3—C4—C5	0.2 (7)	C19—C20—C21—C22	0.3 (5)
C3—C4—C5—C6	−0.3 (6)	C20—C21—C22—N13	179.8 (3)
C4—C5—C6—N7	178.1 (3)	C20—C21—C22—C17	1.0 (5)
C4—C5—C6—C1	0.8 (5)	C22—N13—C23—N14	−1.7 (3)
C6—N7—C7—N8	0.3 (3)	C22—N13—C23—N15	178.9 (3)
C6—N7—C7—N9	178.4 (3)	C22—C17—C18—C19	1.4 (4)
C6—C1—C2—C3	0.9 (5)	C23—N13—C22—C17	1.5 (3)
C7—N7—C6—C1	−0.2 (3)	C23—N13—C22—C21	−177.4 (3)
C7—N7—C6—C5	−177.8 (3)	C23—N14—C17—C18	−180.0 (3)
C7—N8—C1—C2	179.1 (3)	C23—N14—C17—C22	−0.2 (3)
C7—N8—C1—C6	0.1 (3)	C24—N14—C17—C18	0.9 (5)
C8—N8—C1—C2	−1.9 (5)	C24—N14—C17—C22	−179.3 (3)
C8—N8—C1—C6	179.1 (3)	C24—N14—C23—N13	−179.7 (3)
C8—N8—C7—N7	−179.2 (3)	C24—N14—C23—N15	−0.3 (5)
C8—N8—C7—N9	2.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O17	0.93	2.64	3.530 (5)	161
C24ⁱ—H24Cⁱ···O10	0.96	2.52	3.348 (5)	138
N7—H7···O1	0.86	2.01	2.819 (3)	157
N10—H4A···O4	0.86	2.05	2.889 (3)	164
N12—H6A···O6	0.86	2.10	2.944 (3)	165
N13—H7···O7	0.86	2.11	2.920 (4)	156
N15—H9B···O9	0.86	2.14	2.946 (3)	155
N15ⁱⁱ—H9Aⁱⁱ···O17	0.86	2.32	3.001 (3)	136

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

Acknowledgements

The authors acknowledge support from the MIRAI FUND (JICA) and technical equipment support provided by the Institute of bioorganic chemistry of Uzbek Academy of Sciences.

Funding information

Funding for this research was provided by: Japan International Cooperation Agency.

References

Fernández-Fernández, M. del C., Bastida, R., Macias, A., Pérez-Lourido, P., Platas-Iglesias, C. & Valencia, L. (2006). Inorg. Chem. 45, 4484–4496. PubMed Google Scholar
Barry, D. E., Caffrey, D. F. & Gunnlaugsson, T. (2016). Chem. Soc. Rev. 45, 3244–3274. CrossRef CAS PubMed Google Scholar
Bezzubov, S. I., Bilyalova, A. A., Zharinova, I. S., Lavrova, M. A., Kiselev, Y. M. & Dolzhenko, V. D. (2017). Russ. J. Inorg. Chem. 62, 1197–1201. CSD CrossRef CAS Google Scholar
Chen, W., Tang, X., Dou, W., Wang, B., Guo, L., Ju, Z. & Liu, W. (2017). Chem. Eur. J. 23, 9804–9811. CSD CrossRef CAS PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Drew, M. G. B., Hudson, M. J., Iveson, P. B., Russell, M. L., Liljenzin, J.-O., Sklberg, M., Spjuth, L. & Madic, C. (1998). J. Chem. Soc. Dalton Trans. pp. 2973–2980. CSD CrossRef Google Scholar
Eliseeva, S. V. & Bünzli, J. G. (2010). Chem. Soc. Rev. 39, 189–227. Web of Science CrossRef CAS PubMed Google Scholar
Esteban-Parra, G. M., Moscoso, I., Cepeda, J., García, J. A., Sánchez–Moreno, M., Rodríguez–Diéguez, A. & Quirós, M. (2020). Eur. J. Inorg. Chem. pp. 308–317. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fowkes, A. & Harrison, W. T. A. (2006). Acta Cryst. E62, m1301–m1303. CSD CrossRef IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Polyzou, C. D., Nikolaou, H., Papatriantafyllopoulou, C., Psycharis, V., Terzis, A., Raptopoulou, C. P., Escuer, A. & Perlepes, S. P. (2012). Dalton Trans. 41, 13755–13764. CSD CrossRef CAS PubMed Google Scholar
Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Skelton, B. W., Kokozay, V. N., Vassilyeva, O. Yu. & Buvaylo, E. A. (2019). Private communication (refcode: GOWVIA). CCDC, Cambridge, England. Google Scholar
Skorupskii, G. & Dincă, M. (2020). J. Am. Chem. Soc. 142, 6920–6924. CSD CrossRef CAS PubMed Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Thatipamula, K. C., Bhargavi, G. & Rajasekharan, M. V. (2019). Chem. Sel. 4, 3450–3458. CAS Google Scholar
Turner, M. J., McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2011). CrystEngComm, 13, 1804–1813. Web of Science CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Woodruff, D. N., Winpenny, R. E. & Layfield, R. A. (2013). Chem. Rev. 113, 5110–5148. CrossRef CAS PubMed Google Scholar

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