Crystal structure and Hirshfeld surface analysis of poly[[tetra­aqua­(μ-1,3,4,7,8,10,12,13,16,17,19,22-dodeca­aza­tetra­cyclo­[8.8.4.13,17.18,12]tetra­cosane-5,6,14,15,20,21-hexaonato)iron(IV)dilithium] tetra­hydrate]

Plutenko, M.O.; Shova, S.; Pavlenko, V.A.; Golenya, I.A.; Fritsky, I.O.

doi:10.1107/S2056989023008587

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 79| Part 11| November 2023| Pages 1059-1062

https://doi.org/10.1107/S2056989023008587

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Crystal structure and Hirshfeld surface analysis of poly[[tetraaqua(μ-1,3,4,7,8,10,12,13,16,17,19,22-dodecaazatetracyclo[8.8.4.1^3,17.1^8,12]tetracosane-5,6,14,15,20,21-hexaonato)iron(IV)dilithium] tetrahydrate]

Maksym O. Plutenko,^a ^* Sergiu Shova,^b Vadim A. Pavlenko,^a Irina A. Golenya ^a and Igor O. Fritsky ^a,^c

^aDepartment of Chemistry, National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kyiv, Ukraine, ^bPetruPoni Institute of Macromolecular Chemistry, Aleea Gr. Ghica Voda, 41 A, Iasi 700487, Romania, and ^cInnovation development center ABN, Pirogov str.2/37, 01030 Kiev, Ukraine
^*Correspondence e-mail: plutenkom@gmail.com

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 5 September 2023; accepted 28 September 2023; online 19 October 2023)

The title compound, [FeLi₂(C₁₂H₁₂N₁₂O₆)(H₂O)₄]·4H₂O, consists of iron complex anions, lithium cations and water molecules. The complex anion shows a clathrochelate topology. The coordination geometry of the Fe^IV centre is intermediate between a trigonal prism and a trigonal antiprism. In the crystal, the complex anions are connected through two Li cations into dimers, which are connected by Li—O bonds, forming infinite chains along the b-axis direction.

Keywords: crystal structure; iron(IV) complex; clathrochelate; template reaction; macrocyclic ligand; hydrazide-based ligand; Hirshfeld surface analysis.

CCDC reference: 2298136

1. Chemical context

In 2017, a series of unprecedentedly stable iron(IV) complexes was described (Tomyn et al., 2017 ). The substances can be obtained by a one-pot template reaction between iron(III) salts, oxalodihydrazide and formaldehyde in the presence of atmospheric oxygen in alkaline aqueous media. All complexes possess the clathrochelate topology with very similar geometric parameters for the Fe^IV atom but different crystal packings. Further studies showed that these compounds are promising redox catalysts for photochemical water splitting (Shylin et al., 2019 ) and can be used as building blocks for obtaining new metal–organic frameworks (Xu et al., 2020a ,b , 2020 ).

Here, we report the synthesis, crystal structure and Hirshfeld surface analysis of the title compound Li₂[FeL]·8H₂O (H₆L = (1s,3s,8s,10s,12s,17s)-1,3,4,7,8,10,12,13,16,17,19,22- dodecaazatetracyclo[8.8.4.1^3,17.1^8,12]tetracosane-5,6,14,15,20,21-hexaone) (1) obtained as a result of a template reaction between oxalohydrazide, formaldehyde and iron(III) chloride in the presence of atmospheric oxygen (Fig. 1). Thus, the present work is devoted to the further study of the synthetic approach proposed by Tomyn and co-workers (Tomyn et al., 2017). This work is also a continuation of our research into template aldehyde–hydrazide interactions in the presence of 3d metal ions (Plutenko et al., 2021a ,b ).

Figure 1
The synthesis of the title compound.

2. Structural commentary

The title compound crystallizes in the C2/c space group. The unit cell contains eight complex anions [FeL]²⁻, 16 lithium cations and 64 water molecules (Fig. 2). The coordination geometry of the Fe^IV centre (Fig. 3) is intermediate between a trigonal prism (TP, distortion angle φ = 0°) and a trigonal antiprism (TAP, distortion angle φ = 60°); the distortion angle φ average value being 33.04 (5)°, which is quite close to those of the earlier published Fe^IV clathrochelates (28.0–31.9°) (Tomyn et al., 2017).

Figure 2
The asymmetric unit of the title compound with displacement ellipsoids shown at the 50% probability level.

Figure 3
TP–TAP distortion of the FeN₆ polyhedron in the complex anion.

The Fe1—N bond distances are in the range 1.9340 (17)–1.9572 (15) Å (Table 1). The N⋯N separations in the hydrazide apical groups vary from 2.670 (2) to 2.701 (3) Å. The height of the coordination polyhedron h is equal to 2.3557 (13) Å. The bite angle α (half of the chelate N—Fe—N′ angle) is equal to 40.53 (4)°, the chelate N—Fe—N′ angles being in the range 80.29 (6)–80.87 (6)°. Thus, all geometric parameters of the Fe^IV coordination polyhedron are close to those of the earlier published Fe^IV clathrochelates (Tomyn et al., 2017).

Table 1
Selected geometric parameters (Å, °)

Fe1—N1	1.9405 (15)	N5—Fe1—N6	80.87 (8)
Fe1—N2	1.9572 (15)	N1⋯N3	2.688 (3)
Fe1—N3	1.9516 (16)	N1⋯N3	2.672 (3)
Fe1—N4	1.9504 (16)	N3⋯N5	2.673 (2)
Fe1—N5	1.9340 (16)	N2⋯N4	2.689 (2)
Fe1—N6	1.9398 (15)	N2⋯N6	2.701 (3)
N1—Fe1—N2	80.43 (6)	N4⋯N6	2.670 (2)
N3—Fe1—N4	80.29 (6)

3. Supramolecular features

It is important to note that the [FeL]²⁻ complex anion is chiral. Both stereoisomers of the complex cation are included in the crystal packing, thus, 1 is a racemate. In the crystal, both chiral isomers are connected through two Li cations (by O4⋯Li2, N10⋯Li2, O1⋯Li2 and O2⋯Li2 interactions), forming a racemic dimer {Li₂[FeL]₂}²⁻. Such dimers are connected by Li2⋯O5 interactions, forming continuous chains along the b-axis direction (Fig. 4).

Figure 4
Crystal packing of the title compound. Hydrogen bonds are indicated by dashed lines.

In addition, the crystal structure is consolidated by an extensive system of hydrogen bonds (Table 2). Based on the results of recent studies (Lobato et al., 2021 ), the distance of 2.14 Å was used as a criterion for the demarcation of O—H⋯O hydrogen bonds and O⋯H van der Waals interactions. According to this criterion, 14 O⋯H contacts were identified as hydrogen bonds.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H00E⋯O10ⁱ	0.86	1.87	2.715 (2)	167
O7—H00F⋯O8ⁱⁱ	0.86	2.08	2.921 (2)	164
O8—H00C⋯O14ⁱⁱⁱ	0.86	1.90	2.759 (2)	175
O8—H00D⋯O13^iv	0.86	1.97	2.812 (2)	167
O9—H00G⋯O11^iv	0.86	1.97	2.827 (2)	176
O9—H00H⋯O14^v	0.86	2.02	2.881 (2)	177
O10—H00A⋯O6^vi	0.87	2.00	2.768 (2)	147
O10—H00B⋯O4^vii	0.87	1.97	2.8301 (18)	178
O11—H00O⋯O3	0.86	2.05	2.844 (2)	154
O12—H00S⋯O11	0.86	1.97	2.828 (2)	177
O13—H00Q⋯O12^iv	0.86	1.88	2.736 (3)	177
O13—H00R⋯O3	0.86	1.93	2.767 (2)	165
O14—H00M⋯O6	0.86	1.98	2.784 (2)	155
O14—H00N⋯O13^vii	0.86	2.01	2.867 (2)	176
Symmetry codes: (i) ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (vi) x, y+1, z; (vii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

4. Hirshfeld analysis

The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) were performed with CrystalExplorer17 (Turner et al., 2017 ). The Hirshfeld surfaces of the [FeL]²⁻ complex anion are colour-mapped with the normalized contact distance (d_norm) from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The Hirshfeld surface of the title compound mapped over d_norm is shown in Fig. 5. According to the Hirshfeld surface, the most noticeable intermolecular interaction are Li⋯O contacts (O1⋯Li1, N7⋯Li1, O1⋯Li2, O2⋯Li2, O4⋯Li2, O5⋯Li2, N10⋯Li2) and O–H⋯O hydrogen bonds (O10—H00B⋯O4, O13—H00R⋯O3, O11—H00O⋯O3, O14—H00M⋯O6, O10—H00A⋯O6).

Figure 5
The Hirshfeld surfaces of the complex anion mapped over d_norm.

A fingerprint plot delineated into specific interatomic contacts contains information related to specific intermolecular interactions. The blue colour refers to the frequency of occurrence of the (d_i, d_e) pair with the full fingerprint plot outlined in grey. Fig. 6 shows the two-dimensional fingerprint plot of the sum of the contacts contributing to the Hirshfeld surface. The most significant contributions to the Hirshfeld surface are from O⋯H/H⋯O (33.3%) and H⋯H (32.9%) contacts. In addition, N⋯H/H⋯N (8.9%) is also a highly significant contribution to the total Hirshfeld surface.

Figure 6
(a) Full two-dimensional fingerprint plot of the complex anion and delineated into (b) O⋯H/H⋯O (33.3%) (c) H⋯H (32.9%) and (d) N⋯H/H⋯N (8.9%) contacts.

5. Database survey

A search in the Cambridge Structural Database (CSD version 5.43, update of November 2022; Groom et al., 2016 ) resulted in nine hits dealing with hydrazide-based clathrochelates of 3d-metals. There are three structures of Mn^IV clathrochelates (Shylin et al., 2021 ; Xu et al., 2022), three structures of Fe^IV clathrochelates (Tomyn et al., 2017) and three hits dealing with Fe^IV clathrochelate-based metal-organic frameworks (MOFs). The MOFs reveal a 1D coordination polymer topology: the Fe^IV clathrochelate complex anions being connected by Mn²⁺ (Xu et al., 2020b) or Cu²⁺ (Xu et al., 2020a, 2022) cations, forming zigzag hetero-bimetallic chains, and being bimetallic helps to understand the link with Mn²⁺ and Cu²⁺.

6. Synthesis and crystallization

To a mixture of 0.354 g oxalodihydrazide (3 mmol) and 0.144 g LiOH (6 mmol), 10 ml of FeCl₃ aqueous solution (1 mmol) were added dropwise. Then an aqueous formaldehyde solution (37% in water, 0.73 ml, 9 mmol) was added. The reaction mixture was stirred for 2 h under slight warming (∼313 K), filtered off, and the solvent removed on a rotary evaporator. The crude product was dissolved in 5 ml of water and left for crystallization by slow diffusion of tetrahydrofuran vapour. Single crystals suitable for X-ray analysis were obtained after one month. Yield 0.124g (22%). IR (KBr, cm⁻¹): 3409 (O—H), 2942 (C—H), 1648 (C=O amide I). Analysis calculated for C₁₂H₂₈FeLi₂N₁₂O₁₄: C 22.73, H 4.45, N 26.51. Found: C 22.79, H 4.36, N 26.73.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The water hydrogen atoms were located in a difference-Fourier map and refined isotropically. Other hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.99 Å, and U_iso(H)= 1.2U_eq(parent atom).

Table 3
Experimental details

Crystal data
Chemical formula	[FeLi₂(C₁₂H₁₂N₁₂O₆)(H₂O)₄]·4H₂O
M_r	634.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	240
a, b, c (Å)	25.4076 (8), 9.9854 (2), 22.3570 (8)
β (°)	120.265 (5)
V (Å³)	4899.0 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.71
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Xcalibur, Eos
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Tokyo, Japan.]$ )
T_min, T_max	0.856, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15658, 5611, 4704
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.05
No. of reflections	5611
No. of parameters	370
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.50
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Tokyo, Japan.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2298136

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023008587/tx2074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023008587/tx2074Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023008587/tx2074Isup3.cdx

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.41.104a (Rigaku OD, 2021); cell refinement: CrysAlis PRO 1.171.41.104a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.41.104a (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.3-ac4 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3-ac4 (Dolomanov et al., 2009).

Poly[[tetraaqua(µ-1,3,4,7,8,10,12,13,16,17,19,22-dodecaazatetracyclo[8.8.4.1^3,17.1^8,12]tetracosane-5,6,14,15,20,21-hexaonato)iron(IV)dilithium] tetrahydrate] top

Crystal data top

[FeLi₂(C₁₂H₁₂N₁₂O₆)(H₂O)₄]·4H₂O	F(000) = 2624
M_r = 634.19	D_x = 1.720 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.4076 (8) Å	Cell parameters from 6976 reflections
b = 9.9854 (2) Å	θ = 2.3–29.0°
c = 22.3570 (8) Å	µ = 0.71 mm⁻¹
β = 120.265 (5)°	T = 240 K
V = 4899.0 (3) Å³	Plate, clear dark brown
Z = 8	0.35 × 0.25 × 0.15 mm

Data collection top

Xcalibur, Eos diffractometer	4704 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.028
ω scans	θ_max = 29.3°, θ_min = 1.9°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −31→34
T_min = 0.856, T_max = 1.000	k = −12→12
15658 measured reflections	l = −30→28
5611 independent reflections	3 standard reflections every 100 reflections

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0346P)² + 4.922P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
5611 reflections	Δρ_max = 0.36 e Å⁻³
370 parameters	Δρ_min = −0.50 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Fe1	0.46624 (2)	0.22908 (3)	0.38076 (2)	0.01262 (8)
Li1	0.31903 (16)	0.2166 (4)	0.4662 (2)	0.0285 (8)
Li2	0.51611 (16)	0.6998 (4)	0.36559 (18)	0.0247 (8)
O1	0.41814 (6)	0.20924 (15)	0.52715 (7)	0.0253 (3)
O2	0.53645 (6)	0.30502 (15)	0.58348 (7)	0.0235 (3)
O3	0.34175 (7)	0.45564 (14)	0.22349 (8)	0.0304 (4)
O4	0.45683 (6)	0.57917 (13)	0.28837 (7)	0.0210 (3)
O5	0.46493 (6)	−0.13454 (14)	0.30406 (7)	0.0224 (3)
O6	0.57720 (6)	−0.00286 (15)	0.34614 (8)	0.0271 (3)
O7	0.32263 (7)	0.33148 (17)	0.53909 (8)	0.0347 (4)
H00E	0.350462	0.317568	0.581392	0.052*
H00F	0.291147	0.354733	0.541452	0.052*
O8	0.28280 (7)	0.04068 (15)	0.46559 (8)	0.0301 (4)
H00C	0.286765	0.003240	0.502261	0.045*
H00D	0.272742	−0.023573	0.436200	0.045*
O9	0.25088 (7)	0.32555 (17)	0.39188 (8)	0.0368 (4)
H00G	0.222223	0.298288	0.352207	0.055*
H00H	0.237199	0.398879	0.399040	0.055*
O10	0.57787 (6)	0.72100 (14)	0.33567 (7)	0.0204 (3)
H00A	0.578172	0.803427	0.323940	0.031*
H00B	0.566542	0.676297	0.297930	0.031*
O11	0.33933 (7)	0.73725 (15)	0.24099 (8)	0.0291 (3)
H00O	0.349228	0.659621	0.233194	0.044*
H00P	0.373327	0.779521	0.263440	0.044*
O12	0.32125 (8)	0.6666 (2)	0.35183 (9)	0.0512 (5)
H00S	0.326163	0.685011	0.317356	0.077*
H00T	0.356921	0.676047	0.387626	0.077*
O13	0.25329 (7)	0.30629 (16)	0.11515 (8)	0.0351 (4)
H00Q	0.231203	0.261120	0.127006	0.053*
H00R	0.281584	0.340185	0.153255	0.053*
O14	0.69993 (7)	0.06720 (16)	0.41220 (8)	0.0307 (4)
H00M	0.660923	0.069494	0.386320	0.046*
H00N	0.712163	0.140947	0.403385	0.046*
N1	0.41463 (7)	0.22279 (16)	0.42162 (8)	0.0162 (3)
N2	0.52862 (7)	0.24332 (15)	0.47873 (8)	0.0150 (3)
N3	0.39332 (7)	0.27406 (16)	0.29324 (8)	0.0163 (3)
N4	0.48454 (7)	0.41507 (15)	0.37156 (8)	0.0148 (3)
N5	0.44518 (7)	0.04326 (16)	0.35575 (8)	0.0170 (3)
N6	0.53075 (7)	0.18096 (16)	0.36242 (8)	0.0154 (3)
N7	0.35514 (7)	0.16379 (17)	0.38745 (8)	0.0190 (3)
N8	0.58616 (7)	0.30474 (16)	0.50012 (8)	0.0165 (3)
N9	0.33731 (7)	0.20469 (16)	0.26972 (8)	0.0186 (3)
N10	0.54501 (7)	0.46721 (15)	0.40384 (8)	0.0162 (3)
N11	0.38492 (7)	−0.00511 (17)	0.32933 (8)	0.0197 (3)
N12	0.58700 (7)	0.25184 (16)	0.39290 (8)	0.0171 (3)
C1	0.44139 (8)	0.22632 (19)	0.49052 (10)	0.0161 (4)
C2	0.50845 (8)	0.26239 (19)	0.52339 (9)	0.0160 (4)
C3	0.38748 (9)	0.39944 (19)	0.27093 (9)	0.0184 (4)
C4	0.44690 (8)	0.47478 (19)	0.31130 (9)	0.0164 (4)
C5	0.47741 (8)	−0.02467 (19)	0.33310 (9)	0.0165 (4)
C6	0.53471 (8)	0.05244 (19)	0.34806 (9)	0.0165 (4)
C7	0.31630 (9)	0.2270 (2)	0.31928 (10)	0.0212 (4)
H01A	0.274787	0.191914	0.299432	0.025*
H01B	0.314716	0.323597	0.325917	0.025*
C8	0.57650 (8)	0.44681 (19)	0.47912 (9)	0.0176 (4)
H00I	0.552640	0.489220	0.497301	0.021*
H00J	0.616152	0.491800	0.500196	0.021*
C9	0.34453 (9)	0.0618 (2)	0.26241 (10)	0.0222 (4)
H01C	0.361326	0.049488	0.231784	0.027*
H01D	0.304373	0.018984	0.240460	0.027*
C10	0.57816 (9)	0.39403 (19)	0.37480 (10)	0.0189 (4)
H00K	0.555332	0.402670	0.324251	0.023*
H00L	0.618074	0.436027	0.391778	0.023*
C11	0.36310 (9)	0.0196 (2)	0.37765 (10)	0.0212 (4)
H01G	0.392110	−0.019496	0.422652	0.025*
H01H	0.323982	−0.026181	0.360628	0.025*
C12	0.61777 (8)	0.2364 (2)	0.46903 (10)	0.0186 (4)
H01E	0.620862	0.140837	0.480263	0.022*
H01F	0.659266	0.272030	0.489694	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01409 (13)	0.01225 (15)	0.01214 (13)	−0.00028 (10)	0.00707 (11)	−0.00015 (10)
Li1	0.0260 (18)	0.031 (2)	0.032 (2)	−0.0012 (16)	0.0170 (17)	−0.0024 (16)
Li2	0.0267 (18)	0.025 (2)	0.0242 (18)	−0.0035 (15)	0.0143 (16)	−0.0052 (14)
O1	0.0245 (7)	0.0362 (9)	0.0220 (7)	−0.0004 (6)	0.0166 (7)	−0.0002 (6)
O2	0.0234 (7)	0.0315 (9)	0.0153 (7)	−0.0010 (6)	0.0094 (6)	−0.0052 (6)
O3	0.0247 (8)	0.0209 (8)	0.0265 (8)	0.0012 (6)	−0.0012 (7)	0.0038 (6)
O4	0.0286 (7)	0.0152 (7)	0.0164 (7)	−0.0035 (6)	0.0093 (6)	0.0027 (5)
O5	0.0249 (7)	0.0157 (8)	0.0269 (8)	−0.0026 (6)	0.0133 (7)	−0.0063 (6)
O6	0.0240 (7)	0.0214 (8)	0.0427 (9)	−0.0018 (6)	0.0217 (7)	−0.0083 (7)
O7	0.0203 (7)	0.0529 (11)	0.0271 (8)	0.0073 (7)	0.0090 (7)	−0.0051 (7)
O8	0.0375 (9)	0.0247 (9)	0.0297 (8)	−0.0023 (7)	0.0182 (8)	−0.0007 (6)
O9	0.0380 (9)	0.0388 (10)	0.0264 (8)	0.0154 (8)	0.0109 (8)	−0.0026 (7)
O10	0.0254 (7)	0.0183 (7)	0.0179 (7)	−0.0010 (6)	0.0113 (6)	−0.0015 (5)
O11	0.0231 (7)	0.0243 (8)	0.0357 (9)	−0.0002 (6)	0.0117 (7)	−0.0024 (7)
O12	0.0307 (9)	0.0873 (15)	0.0284 (9)	−0.0030 (10)	0.0096 (8)	0.0016 (9)
O13	0.0319 (8)	0.0386 (10)	0.0213 (8)	−0.0010 (7)	0.0034 (7)	−0.0017 (7)
O14	0.0262 (8)	0.0350 (9)	0.0318 (8)	0.0028 (7)	0.0153 (7)	0.0035 (7)
N1	0.0129 (7)	0.0198 (9)	0.0160 (8)	−0.0002 (6)	0.0073 (7)	−0.0001 (6)
N2	0.0128 (7)	0.0172 (9)	0.0141 (8)	0.0001 (6)	0.0062 (7)	0.0005 (6)
N3	0.0153 (7)	0.0164 (9)	0.0132 (8)	−0.0040 (6)	0.0043 (7)	−0.0006 (6)
N4	0.0153 (7)	0.0130 (8)	0.0140 (8)	−0.0013 (6)	0.0058 (7)	−0.0003 (6)
N5	0.0180 (8)	0.0138 (9)	0.0211 (8)	−0.0028 (6)	0.0113 (7)	−0.0015 (6)
N6	0.0163 (7)	0.0144 (8)	0.0182 (8)	−0.0024 (6)	0.0107 (7)	−0.0024 (6)
N7	0.0146 (7)	0.0214 (9)	0.0222 (8)	−0.0026 (6)	0.0101 (7)	−0.0001 (7)
N8	0.0140 (7)	0.0182 (9)	0.0150 (8)	−0.0008 (6)	0.0057 (7)	−0.0008 (6)
N9	0.0152 (8)	0.0214 (9)	0.0161 (8)	−0.0038 (6)	0.0055 (7)	−0.0012 (6)
N10	0.0156 (7)	0.0152 (9)	0.0173 (8)	−0.0027 (6)	0.0078 (7)	−0.0017 (6)
N11	0.0179 (8)	0.0203 (9)	0.0219 (8)	−0.0037 (7)	0.0109 (7)	−0.0025 (7)
N12	0.0166 (8)	0.0172 (9)	0.0197 (8)	−0.0035 (6)	0.0107 (7)	−0.0022 (6)
C1	0.0193 (9)	0.0138 (10)	0.0174 (9)	0.0029 (7)	0.0108 (8)	0.0000 (7)
C2	0.0193 (9)	0.0151 (10)	0.0135 (9)	0.0045 (7)	0.0083 (8)	0.0029 (7)
C3	0.0214 (9)	0.0181 (11)	0.0129 (9)	0.0005 (8)	0.0067 (8)	−0.0010 (7)
C4	0.0219 (9)	0.0140 (10)	0.0146 (9)	0.0017 (7)	0.0102 (8)	−0.0016 (7)
C5	0.0198 (9)	0.0152 (10)	0.0144 (9)	0.0006 (7)	0.0085 (8)	0.0011 (7)
C6	0.0191 (9)	0.0167 (10)	0.0148 (9)	0.0001 (7)	0.0094 (8)	−0.0006 (7)
C7	0.0144 (9)	0.0254 (11)	0.0220 (10)	0.0000 (8)	0.0080 (8)	0.0003 (8)
C8	0.0177 (9)	0.0158 (10)	0.0151 (9)	−0.0025 (7)	0.0051 (8)	−0.0033 (7)
C9	0.0213 (10)	0.0228 (11)	0.0198 (10)	−0.0068 (8)	0.0085 (9)	−0.0051 (8)
C10	0.0218 (9)	0.0175 (11)	0.0208 (10)	−0.0036 (8)	0.0132 (9)	−0.0002 (8)
C11	0.0213 (10)	0.0207 (11)	0.0251 (10)	−0.0047 (8)	0.0143 (9)	0.0005 (8)
C12	0.0148 (9)	0.0197 (11)	0.0207 (10)	0.0024 (7)	0.0084 (8)	0.0013 (8)

Geometric parameters (Å, º) top

Fe1—N5	1.9340 (16)	N1—C1	1.334 (2)
Fe1—N6	1.9398 (15)	N1—N7	1.432 (2)
Fe1—N1	1.9405 (15)	N2—C2	1.346 (2)
Fe1—N4	1.9504 (15)	N2—N8	1.427 (2)
Fe1—N3	1.9516 (16)	N3—C3	1.328 (3)
Fe1—N2	1.9572 (15)	N3—N9	1.424 (2)
Li1—O7	1.957 (4)	N4—C4	1.336 (2)
Li1—O8	1.979 (4)	N4—N10	1.426 (2)
Li1—O9	2.011 (4)	N5—C5	1.343 (2)
Li1—O1	2.178 (4)	N5—N11	1.420 (2)
Li1—N7	2.419 (4)	N6—C6	1.339 (2)
Li2—O10	2.003 (4)	N6—N12	1.424 (2)
Li2—O4	2.020 (4)	N7—C7	1.476 (3)
Li2—O5ⁱ	2.125 (4)	N7—C11	1.486 (3)
Li2—O2ⁱⁱ	2.148 (4)	N8—C12	1.468 (2)
Li2—O1ⁱⁱ	2.308 (4)	N8—C8	1.476 (2)
Li2—N10	2.456 (4)	N9—C9	1.458 (3)
Li2—C4	2.732 (4)	N9—C7	1.469 (2)
O1—C1	1.239 (2)	N10—C8	1.469 (2)
O2—C2	1.236 (2)	N10—C10	1.489 (2)
O3—C3	1.244 (2)	N11—C11	1.462 (2)
O4—C4	1.242 (2)	N11—C9	1.480 (3)
O5—C5	1.232 (2)	N12—C10	1.462 (2)
O6—C6	1.232 (2)	N12—C12	1.480 (2)
O7—H00E	0.8601	C1—C2	1.520 (3)
O7—H00F	0.8598	C3—C4	1.512 (3)
O8—H00C	0.8596	C5—C6	1.528 (3)
O8—H00D	0.8599	C7—H01A	0.9800
O9—H00G	0.8602	C7—H01B	0.9800
O9—H00H	0.8595	C8—H00I	0.9800
O10—H00A	0.8651	C8—H00J	0.9800
O10—H00B	0.8656	C9—H01C	0.9800
O11—H00O	0.8595	C9—H01D	0.9800
O11—H00P	0.8598	C10—H00K	0.9800
O12—H00S	0.8604	C10—H00L	0.9800
O12—H00T	0.8600	C11—H01G	0.9800
O13—H00Q	0.8595	C11—H01H	0.9800
O13—H00R	0.8601	C12—H01E	0.9800
O14—H00M	0.8600	C12—H01F	0.9800
O14—H00N	0.8599

N5—Fe1—N6	80.87 (6)	C6—N6—Fe1	117.50 (12)
N5—Fe1—N1	87.19 (7)	N12—N6—Fe1	121.81 (11)
N6—Fe1—N1	159.22 (7)	N1—N7—C7	110.58 (15)
N5—Fe1—N4	158.28 (7)	N1—N7—C11	106.97 (14)
N6—Fe1—N4	86.67 (7)	C7—N7—C11	109.38 (15)
N1—Fe1—N4	109.51 (7)	N1—N7—Li1	101.98 (13)
N5—Fe1—N3	86.93 (7)	C7—N7—Li1	110.93 (14)
N6—Fe1—N3	108.74 (7)	C11—N7—Li1	116.64 (14)
N1—Fe1—N3	87.37 (7)	N2—N8—C12	110.73 (14)
N4—Fe1—N3	80.29 (6)	N2—N8—C8	109.18 (14)
N5—Fe1—N2	110.08 (7)	C12—N8—C8	109.81 (15)
N6—Fe1—N2	87.75 (6)	N3—N9—C9	111.01 (15)
N1—Fe1—N2	80.43 (6)	N3—N9—C7	108.86 (14)
N4—Fe1—N2	86.97 (6)	C9—N9—C7	110.30 (16)
N3—Fe1—N2	158.35 (7)	N4—N10—C8	110.79 (14)
O7—Li1—O8	110.66 (19)	N4—N10—C10	107.59 (14)
O7—Li1—O9	91.73 (17)	C8—N10—C10	109.30 (14)
O8—Li1—O9	105.70 (18)	N4—N10—Li2	96.45 (13)
O7—Li1—O1	86.84 (15)	C8—N10—Li2	115.13 (14)
O8—Li1—O1	111.20 (18)	C10—N10—Li2	116.61 (14)
O9—Li1—O1	141.0 (2)	N5—N11—C11	111.48 (15)
O7—Li1—N7	149.1 (2)	N5—N11—C9	108.65 (15)
O8—Li1—N7	98.46 (16)	C11—N11—C9	110.05 (15)
O9—Li1—N7	90.03 (15)	N6—N12—C10	111.91 (15)
O1—Li1—N7	72.83 (12)	N6—N12—C12	108.65 (14)
O10—Li2—O4	98.61 (16)	C10—N12—C12	109.73 (15)
O10—Li2—O5ⁱ	91.62 (15)	O1—C1—N1	128.60 (18)
O4—Li2—O5ⁱ	87.79 (15)	O1—C1—C2	120.30 (17)
O10—Li2—O2ⁱⁱ	168.6 (2)	N1—C1—C2	111.04 (16)
O4—Li2—O2ⁱⁱ	92.56 (15)	O2—C2—N2	128.98 (18)
O5ⁱ—Li2—O2ⁱⁱ	91.13 (14)	O2—C2—C1	119.85 (16)
O10—Li2—O1ⁱⁱ	91.53 (14)	N2—C2—C1	111.16 (16)
O4—Li2—O1ⁱⁱ	163.8 (2)	O3—C3—N3	128.68 (18)
O5ⁱ—Li2—O1ⁱⁱ	104.64 (15)	O3—C3—C4	120.46 (17)
O2ⁱⁱ—Li2—O1ⁱⁱ	77.06 (12)	N3—C3—C4	110.85 (16)
O10—Li2—N10	93.96 (15)	O4—C4—N4	126.82 (18)
O4—Li2—N10	72.34 (12)	O4—C4—C3	121.36 (17)
O5ⁱ—Li2—N10	159.95 (18)	N4—C4—C3	111.81 (16)
O2ⁱⁱ—Li2—N10	87.18 (13)	O4—C4—Li2	43.45 (12)
O1ⁱⁱ—Li2—N10	94.45 (14)	N4—C4—Li2	86.89 (13)
O10—Li2—C4	112.06 (15)	C3—C4—Li2	154.14 (15)
O4—Li2—C4	25.02 (7)	O5—C5—N5	127.19 (18)
O5ⁱ—Li2—C4	107.80 (15)	O5—C5—C6	121.85 (17)
O2ⁱⁱ—Li2—C4	77.53 (12)	N5—C5—C6	110.96 (16)
O1ⁱⁱ—Li2—C4	138.76 (16)	O6—C6—N6	127.65 (18)
N10—Li2—C4	52.36 (9)	O6—C6—C5	121.43 (17)
C1—O1—Li1	111.59 (16)	N6—C6—C5	110.92 (15)
C1—O1—Li2ⁱⁱ	107.21 (15)	N9—C7—N7	113.96 (15)
Li1—O1—Li2ⁱⁱ	129.77 (15)	N9—C7—H01A	108.8
C2—O2—Li2ⁱⁱ	113.40 (15)	N7—C7—H01A	108.8
C4—O4—Li2	111.52 (16)	N9—C7—H01B	108.8
C5—O5—Li2ⁱⁱⁱ	116.16 (15)	N7—C7—H01B	108.8
Li1—O7—H00E	119.2	H01A—C7—H01B	107.7
Li1—O7—H00F	123.7	N10—C8—N8	113.91 (15)
H00E—O7—H00F	104.5	N10—C8—H00I	108.8
Li1—O8—H00C	123.3	N8—C8—H00I	108.8
Li1—O8—H00D	128.7	N10—C8—H00J	108.8
H00C—O8—H00D	104.5	N8—C8—H00J	108.8
Li1—O9—H00G	127.6	H00I—C8—H00J	107.7
Li1—O9—H00H	124.6	N9—C9—N11	113.01 (16)
H00G—O9—H00H	104.5	N9—C9—H01C	109.0
Li2—O10—H00A	109.3	N11—C9—H01C	109.0
Li2—O10—H00B	109.8	N9—C9—H01D	109.0
H00A—O10—H00B	104.2	N11—C9—H01D	109.0
H00O—O11—H00P	104.5	H01C—C9—H01D	107.8
H00S—O12—H00T	104.5	N12—C10—N10	113.43 (15)
H00Q—O13—H00R	104.5	N12—C10—H00K	108.9
H00M—O14—H00N	104.5	N10—C10—H00K	108.9
C1—N1—N7	114.41 (15)	N12—C10—H00L	108.9
C1—N1—Fe1	118.07 (12)	N10—C10—H00L	108.9
N7—N1—Fe1	122.96 (11)	H00K—C10—H00L	107.7
C2—N2—N8	113.54 (15)	N11—C11—N7	113.76 (15)
C2—N2—Fe1	116.37 (12)	N11—C11—H01G	108.8
N8—N2—Fe1	121.41 (11)	N7—C11—H01G	108.8
C3—N3—N9	114.73 (15)	N11—C11—H01H	108.8
C3—N3—Fe1	117.61 (12)	N7—C11—H01H	108.8
N9—N3—Fe1	121.70 (12)	H01G—C11—H01H	107.7
C4—N4—N10	112.84 (15)	N8—C12—N12	113.46 (15)
C4—N4—Fe1	116.34 (12)	N8—C12—H01E	108.9
N10—N4—Fe1	123.19 (11)	N12—C12—H01E	108.9
C5—N5—N11	113.94 (15)	N8—C12—H01F	108.9
C5—N5—Fe1	117.46 (13)	N12—C12—H01F	108.9
N11—N5—Fe1	122.00 (12)	H01E—C12—H01F	107.7
C6—N6—N12	114.37 (15)

C1—N1—N7—C7	147.87 (16)	Fe1—N4—C4—O4	−162.81 (15)
Fe1—N1—N7—C7	−56.60 (19)	N10—N4—C4—C3	167.76 (14)
C1—N1—N7—C11	−93.11 (18)	Fe1—N4—C4—C3	17.16 (19)
Fe1—N1—N7—C11	62.43 (18)	N10—N4—C4—Li2	−30.62 (15)
C1—N1—N7—Li1	29.85 (19)	Fe1—N4—C4—Li2	178.77 (11)
Fe1—N1—N7—Li1	−174.61 (12)	O3—C3—C4—O4	−18.6 (3)
C2—N2—N8—C12	155.31 (15)	N3—C3—C4—O4	160.73 (17)
Fe1—N2—N8—C12	−58.22 (18)	O3—C3—C4—N4	161.42 (18)
C2—N2—N8—C8	−83.67 (18)	N3—C3—C4—N4	−19.2 (2)
Fe1—N2—N8—C8	62.80 (17)	O3—C3—C4—Li2	27.6 (4)
C3—N3—N9—C9	149.01 (16)	N3—C3—C4—Li2	−153.0 (3)
Fe1—N3—N9—C9	−58.87 (18)	Li2ⁱⁱⁱ—O5—C5—N5	−104.0 (2)
C3—N3—N9—C7	−89.40 (19)	Li2ⁱⁱⁱ—O5—C5—C6	75.8 (2)
Fe1—N3—N9—C7	62.73 (18)	N11—N5—C5—O5	−14.6 (3)
C4—N4—N10—C8	154.71 (15)	Fe1—N5—C5—O5	−166.75 (16)
Fe1—N4—N10—C8	−57.00 (18)	N11—N5—C5—C6	165.57 (15)
C4—N4—N10—C10	−85.87 (17)	Fe1—N5—C5—C6	13.4 (2)
Fe1—N4—N10—C10	62.42 (17)	N12—N6—C6—O6	−14.4 (3)
C4—N4—N10—Li2	34.70 (17)	Fe1—N6—C6—O6	−167.09 (16)
Fe1—N4—N10—Li2	−177.01 (12)	N12—N6—C6—C5	165.63 (14)
C5—N5—N11—C11	151.14 (16)	Fe1—N6—C6—C5	13.0 (2)
Fe1—N5—N11—C11	−58.11 (19)	O5—C5—C6—O6	−16.4 (3)
C5—N5—N11—C9	−87.42 (19)	N5—C5—C6—O6	163.45 (18)
Fe1—N5—N11—C9	63.32 (18)	O5—C5—C6—N6	163.53 (17)
C6—N6—N12—C10	149.74 (16)	N5—C5—C6—N6	−16.6 (2)
Fe1—N6—N12—C10	−58.92 (18)	N3—N9—C7—N7	−67.7 (2)
C6—N6—N12—C12	−88.94 (18)	C9—N9—C7—N7	54.3 (2)
Fe1—N6—N12—C12	62.40 (17)	N1—N7—C7—N9	64.7 (2)
Li1—O1—C1—N1	−13.6 (3)	C11—N7—C7—N9	−52.8 (2)
Li2ⁱⁱ—O1—C1—N1	−161.0 (2)	Li1—N7—C7—N9	177.14 (15)
Li1—O1—C1—C2	163.46 (17)	N4—N10—C8—N8	64.37 (19)
Li2ⁱⁱ—O1—C1—C2	16.0 (2)	C10—N10—C8—N8	−54.02 (19)
N7—N1—C1—O1	−14.7 (3)	Li2—N10—C8—N8	172.47 (14)
Fe1—N1—C1—O1	−171.54 (16)	N2—N8—C8—N10	−67.39 (19)
N7—N1—C1—C2	168.01 (15)	C12—N8—C8—N10	54.19 (19)
Fe1—N1—C1—C2	11.2 (2)	N3—N9—C9—N11	66.1 (2)
Li2ⁱⁱ—O2—C2—N2	−175.26 (19)	C7—N9—C9—N11	−54.7 (2)
Li2ⁱⁱ—O2—C2—C1	6.0 (2)	N5—N11—C9—N9	−67.47 (19)
N8—N2—C2—O2	−13.0 (3)	C11—N11—C9—N9	54.8 (2)
Fe1—N2—C2—O2	−161.26 (17)	N6—N12—C10—N10	65.88 (19)
N8—N2—C2—C1	165.79 (15)	C12—N12—C10—N10	−54.8 (2)
Fe1—N2—C2—C1	17.5 (2)	N4—N10—C10—N12	−65.81 (19)
O1—C1—C2—O2	−16.8 (3)	C8—N10—C10—N12	54.6 (2)
N1—C1—C2—O2	160.70 (17)	Li2—N10—C10—N12	−172.70 (14)
O1—C1—C2—N2	164.26 (17)	N5—N11—C11—N7	66.5 (2)
N1—C1—C2—N2	−18.2 (2)	C9—N11—C11—N7	−54.2 (2)
N9—N3—C3—O3	−14.3 (3)	N1—N7—C11—N11	−66.78 (19)
Fe1—N3—C3—O3	−167.66 (17)	C7—N7—C11—N11	53.0 (2)
N9—N3—C3—C4	166.41 (15)	Li1—N7—C11—N11	179.90 (15)
Fe1—N3—C3—C4	13.1 (2)	N2—N8—C12—N12	66.67 (19)
Li2—O4—C4—N4	−27.3 (3)	C8—N8—C12—N12	−54.0 (2)
Li2—O4—C4—C3	152.74 (17)	N6—N12—C12—N8	−67.94 (19)
N10—N4—C4—O4	−12.2 (3)	C10—N12—C12—N8	54.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H00E···O10ⁱⁱ	0.86	1.87	2.715 (2)	167
O7—H00F···O8^iv	0.86	2.08	2.921 (2)	164
O8—H00C···O14^v	0.86	1.90	2.759 (2)	175
O8—H00D···O13^vi	0.86	1.97	2.812 (2)	167
O9—H00G···O11^vi	0.86	1.97	2.827 (2)	176
O9—H00H···O14^vii	0.86	2.02	2.881 (2)	177
O10—H00A···O6ⁱ	0.87	2.00	2.768 (2)	147
O10—H00B···O4^viii	0.87	1.97	2.8301 (18)	178
O11—H00O···O3	0.86	2.05	2.844 (2)	154
O12—H00S···O11	0.86	1.97	2.828 (2)	177
O13—H00Q···O12^vi	0.86	1.88	2.736 (3)	177
O13—H00R···O3	0.86	1.93	2.767 (2)	165
O14—H00M···O6	0.86	1.98	2.784 (2)	155
O14—H00N···O13^viii	0.86	2.01	2.867 (2)	176

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

Selected geometric parameters (Å, °) top

Fe1—N1	1.9405 (15)	N5—Fe1—N6	80.87 (8)
Fe1—N2	1.9572 (15)	N1···N3	2.688 (3)
Fe1—N3	1.9516 (16)	N1···N3	2.672 (3)
Fe1—N4	1.9504 (16)	N3···N5	2.673 (2)
Fe1—N5	1.9340 (16)	N2···N4	2.689 (2)
Fe1—N6	1.9398 (15)	N2···N6	2.701 (3)
N1—Fe1—N2	80.43 (6)	N4···N6	2.670 (2)
N3—Fe1—N4	80.29 (6)

Funding information

This work was supported by the Ministry of Education and Science of Ukraine (grants No. 22BF037–03 and 22BF037–09 at Taras Shevchenko National University of Kyiv). This project has received funding from the European Union's Horizon 2020 Research and Innovation Programme under the Marie Skłodowska-Curie grant agreement No. 778245.

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