Crystal structure of tris­(2-methyl-1H-imidazol-3-ium) benzene-1,3,5-tri­carboxyl­ate

Łukaszczyk, W.; Lohse, A.; Leibing, J.; Yildizbas, S.; Rizvanovic, I.; Techert, S.; Velazquez-Garcia, J. de J.

doi:10.1107/S2056989025004748

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ISSN: 2056-9890

Volume 81| Part 7| July 2025| Pages 573-581

https://doi.org/10.1107/S2056989025004748

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Crystal structure of tris(2-methyl-1H-imidazol-3-ium) benzene-1,3,5-tricarboxylate

Weronika Łukaszczyk,^a Allegra Lohse,^b Julia Leibing,^c Sudem Yildizbas,^c Irwana Rizvanovic,^c Simone Techert ^d,^e and Jose de Jesus Velazquez-Garcia ^d ^*

^aFaculty of Chemistry, Jagiellonian University in Kraków, Gronostajowa 2, 30-387, Kraków, Poland, ^bGymnasium Altona, Hohenzollernring 57-61, 22763 Hamburg, Germany, ^cBS 06 Berufliche Schule Chemie, Biologie, Pharmazie, Agrarwirtschaft, Ladenbeker Furtweg 151, 21033 Hamburg, Germany, ^dDeutsches Elektronen-Synchrotron DESY, Notkestr. 85, 22607 Hamburg, Germany, and ^eInstitut für Röntgenphysik, Georg-August-Universität Göttingen, Friedrich-Hund-Platz 1, Göttingen, 37077, Germany
^*Correspondence e-mail: [email protected]

Edited by V. Jancik, Universidad Nacional Autónoma de México, México (Received 15 April 2025; accepted 26 May 2025; online 6 June 2025)

The structure of the title salt, 3C₄H₇N₂⁺·C₉H₃O₆³⁻ (1), is reported. The compound is formed with three 2-methylimidazolium cations and a fully deprotonated trimesic acid. The structure is disordered over two orientations, which were refined using a split model (90.99: 9.01occupancy ratio). Analysis of bond distances and angles reveals the differences and similarities between compound 1 and the previously published 2-methyl-1H-imidazol-3-ium 3,5-dicarboxybenzoate structure [Baletska et al., (2023 ). Acta Cryst. E79, 1088–1092] and tris(2-methyl-1H- imidazol-3-ium) 5-carboxybenzene-1,3-dicarboxylate 3,5-dicarboxybenzoate [Asprilla-Herrera et al. (2025 ). Acta Cryst. E81, 303–309], as well as the neutral counterparts of the ions [Tothadi et al. (2020 ). ACS Appl. Mater. Interfaces, 12, 15588–15594; Hachuła et al. (2010 ). J. Chem. Crystallogr. 40, 201–206]. The crystal packing analysis reveals the formation of hydrogen-bonded two-dimensional networks perpendicular to the [111] vector, where neighbouring planes interact via extensive π–π stacking.

Keywords: crystal structure; trimesic acid; 2-methylimidazolium.

CCDC reference: 2453953

1. Chemical context

Benzene-1,3,5-tricarboxylic acid (trimesic acid, H₃btc) is a planar organic molecule with three negatively ionizable carboxylic groups. Among its versatile applications, H₃btc has been used for self-assembled molecular monolayer investigations (MacLeod, 2020 ; Ha et al., 2010 ; Korolkov et al., 2012 ), as well as a surface functionalization agent (Lin et al., 2023 ; Chen et al., 2014 ; Iancu et al., 2013 ). Additionally, it has been used as a building block in the structure of several drug-delivery systems, including dendrimers (Salamończyk, 2021 ), polymers (Mat Yusuf et al., 2017 ), or hydrogels (Emani et al., 2023 ).

The compound 2-methylimidazole (2-mIm) is a heterocyclic aromatic molecule. It has been reported as a surface coating agent (Li et al., 2023 ), doping agent (Saghaei et al., 2015 ), intermediate in the synthesis of several drug compounds, as well as co-ligand in complexes of metal ions with anti-inflammatory compounds, presenting interesting bioactive properties (Alisir et al., 2021 ; Abuhijleh, 2010 ; Nnabuike et al., 2024 ).

Both compounds are also widely utilized as organic linkers in the preparation of metal–organic frameworks (MOFs). The 2-mIm acts as an organic linker in the most widely reported zeolitic imidazolate frameworks 8 and 67, ZIF-8 and ZIF-67, (Park et al., 2006 ; Banerjee et al., 2008 ), while H₃btc is used in the synthesis of MIL-100 (Férey et al., 2004 ) and HKUST-1 (Chui et al., 1999 ), to cite a few. Some btc-based MOFs and ZIFs have been used as gas adsorbents and separators, catalysts, and for drug-delivery purposes (Zhong et al., 2018a ,b ; Zhao et al., 2024 ; Huang et al., 2011 ; Song et al., 2024 ; Abdelhamid, 2021 ).

In previous studies, we have used 2-mIm and H₃btc to synthesize hexaaquacobalt bis(2-methyl-1H-imidazol-3-ium) tetraaquabis(benzene-1,3,5-tricarboxylato-κO)cobalt (Velazquez-Garcia & Techert, 2022 ), two Co^II mixed-ligand MOFs, mDESY-1 and mDESY-2, (Velazquez-Garcia et al., 2025 ), 2-methyl-1H-imidazol-3-ium 3,5-dicarboxybenzoate (Baletska et al., 2023), and tris(2-methyl-1H-imidazol-3-ium) 5-carboxybenzene-1,3-dicarboxylate 3,5-dicarboxybenzoate (Asprilla-Herrera et al., 2025). Here, we used the same organic compounds to synthesize the title compound.

2. Structural commentary

Compound 1 crystallizes in the P $[\overline{1}]$ space group. The asymmetric unit comprises one fully deprotonated benzene-1,3,5-tricarboxylate (btc³⁻) anion and three 2-methyl-1H-imidazol-3-ium (H2-mIm⁺) cations. The structure is disordered over two orientations, which were refined using a split model. The major fraction, comprising 90.99%, is labelled a, while the minor fraction, comprising 9.01%, is labelled b. For clarity, the three H2-mIm⁺ cations were labelled as Xa, Ya, and Za for component a and correspondingly as Xb, Yb, and Zb for component b. The ORTEP plot illustrating all ions in the major fraction of 1 is shown in Fig. 1.

Figure 1
The molecular structure of the major fraction of 1 with displacement ellipsoids drawn at the 50% probability level.

Selected bond lengths, angles, and torsions for the btc³⁻ ions are summarized in Table 1. In 1a, the C—C and C—O bond distances are in the ranges 1.391 (2)–1.516 (2) Å and 1.252 (2)–1.268 (2) Å, respectively. The longest bonds connect carbon atoms of the aromatic ring and carboxylic groups, with lengths ranging from 1.513 (2) to 1.516 (2) Å. In contrast, the C—C bonds within the aromatic ring are shorter, ranging from 1.391 (2) to 1.395 (2) Å. The highest difference between bond distances within a carboxylic group is exhibited by the O5—C3—O6 (0.016 Å) and the O3—C2—O4 (0.014 Å) groups. The shortest bond in the structure is formed by C3 and O6 [1.252 (2) Å]. In 1b, the C—C bond distances within the aromatic ring are consistent and within the range of 1.38 (2) to 1.39 (2) Å. The C—C bonds between the aromatic ring and carboxylic groups equal 1.52 (2) Å. The C—O bond distances within carboxylic groups are consistent, ranging from 1.24 (1) to 1.27 (2) Å. The C—C bond distances range in both 1a and 1b are similar to the corresponding C—C bond distance ranges in the reported structures of deprotonated H₂btc⁻ (Baletska et al., 2023), and H₂btc⁻ or Hbtc²⁻ (Asprilla-Herrera et al., 2025), for which they are 1.388 (2)–1.511 (2) Å, 1.389 (2)–1.519 (2) Å, and 1.388 (2)–1.510 (2) Å, respectively. The corresponding C—C bond lengths in the structure of neutral H₃btc molecule vary slightly less than in 1, with the range equal to 1.381 (6)–1.494 (9) Å. In contrast, the bond lengths for C—O in both 1a and 1b are significantly more uniform when compared to the range of 1.229 (5)–1.303 (5) Å for the neutral form (Tothadi et al., 2020), 1.224 (2)–1.320 (2) Å for H₂btc⁻ (Baletska et al., 2023), and 1.214 (2)–1.318 (2) Å and 1.214 (2)–1.338 (2) Å for H₂btc⁻ and Hbtc²⁻, respectively (Asprilla-Herrera et al., 2025).

Table 1
Selected bond lengths (Å), angles (°), and torsion angles (°) of the btc³⁻ ions

1a		1b
C4—C5	1.392 (2)	C4—C5	1.38 (2)
C5—C6	1.394 (2)	C5—C6	1.38 (2)
C6—C7	1.395 (2)	C6—C7	1.38 (2)
C7—C8	1.391 (2)	C7—C8	1.38 (2)
C8—C9	1.395 (2)	C8—C9	1.39 (2)
C9—C4	1.394 (2)	C9—C4	1.38 (2)
C1—C4	1.513 (2)	C1—C4	1.52 (2)
C2—C6	1.516 (2)	C2—C6	1.52 (1)
C3—C8	1.516 (2)	C3—C8	1.52 (2)
C1—O1	1.263 (2)	C1—O1	1.27 (1)
C1—O2	1.257 (2)	C1—O2	1.25 (2)
C2—O3	1.267 (2)	C2—O3	1.27 (2)
C2—O4	1.253 (2)	C2—O4	1.24 (1)
C3—O5	1.268 (2)	C3—O5	1.27 (2)
C3—O6	1.252 (2)	C3—O6	1.25 (1)
C4—C5—C6	121.0 (1)	C4—C5—C6	122 (1)
C5—C6—C7	119.0 (1)	C5—C6—C7	119 (1)
C6—C7—C8	121.0 (1)	C6—C7—C8	121 (1)
C7—C8—C9	119.1 (1)	C7—C8—C9	118 (1)
C8—C9—C4	120.8 (1)	C8—C9—C4	122 (1)
C9—C4—C5	119.1 (1)	C9—C4—C5	118 (1)
O1—C1—O2	124.9 (1)	O1—C1—O2	121 (1)
O3—C2—O4	125.0 (1)	O3—C2—O4	121 (1)
O5—C3—O6	124.6 (1)	O5—C3—O6	121 (1)
C5—C4—C1—O1	179.4 (1)	C5—C4—C1—O1	171 (1)
C5—C4—C1—O2	1.2 (2)	C5—C4—C1—O2	−4 (2)
C9—C4—C1—O1	−0.3 (2)	C9—C4—C1—O1	−4 (2)
C9—C4—C1—O2	−178.4 (1)	C9—C4—C1—O2	−180 (1)
C5—C6—C2—O3	4.3 (2)	C5—C6—C2—O3	−1 (2)
C5—C6—C2—O4	−176.8 (1)	C5—C6—C2—O4	−178 (1)
C7—C6—C2—O3	−173.2 (1)	C7—C6—C2—O3	−180 (1)
C7—C6—C2—O4	5.7 (2)	C7—C6—C2—O4	3 (2)
C7—C8—C3—O5	−4.4 (2)	C7—C8—C3—O5	2 (2)
C7—C8—C3—O6	174.7 (1)	C7—C8—C3—O6	−174 (1)
C9—C8—C3—O5	177.3 (1)	C9—C8—C3—O5	−179 (1)
C9—C8—C3—O6	−3.7 (2)	C9—C8—C3—O6	6 (2)

The C—C—C angles in 1 lie within the range 119.0 (2) to 121.0 (1)° for 1a and 118 (1)–122 (1)° for 1b. These values are consistent with the corresponding angles in H₃btc [119.0 (4)–121.1 (4)°], H₂btc⁻ [118.9 (2)–121.4 (4)° (Baletska et al., 2023) and 118.9 (2)–120.8 (2)° (Asprilla-Herrera et al., 2025)], and Hbtc²⁻ [119.4 (2)–120 (4)°; Asprilla-Herrera et al., 2025]. The O—C—O angles in 1a fall in the range 124.6 (1)–125.0 (1)° and are comparable to the corresponding angles in H₃btc [124.4 (4)–125.0 (4)°], singly deprotonated H₂btc⁻ [123.9 (2)–126.1 (2)° (Baletska et al., 2023) and 124.3 (2)–126.8 (2)° (Asprilla-Herrera et al., 2025)], and Hbtc²⁻ [123.2 (2)–125.4 (2)°] forms. In 1b, the O—C—O angles are consistent and equal to 121 (1)°.

Further comparison of btc³⁻ ions in 1 and the previously reported structures was conducted by analysing the torsion angles and performing molecular overlays. The torsion angles deviation from 0 or 180° are similar for both 1a and 1b [0.3 (2)–6.8 (1)° and 0 (1)–9 (1)°, respectively]. These values are significantly lower compared to the H₂btc⁻ structure published by Baletska et al. [4.2 (2)–16.6 (2)°] and doubly deprotonated Hbtc²⁻ structure published by Asprilla-Herrera et al. [12.6 (2)–17.1 (2)°]. Interestingly, in both 1a and 1b, the torsion angles resemble more the corresponding angles in fully protonated H₃btc [0 (4)–4.2 (4)°] and singly deprotonated H₂btc⁻ reported by Asprilla-Herrera et al. [0.6 (2)–7.0 (2)°]. This is further corroborated by molecular overlays of the btc³⁻ ions with other reported structures of btc (Fig. 2) and their respective root-mean-squared deviation (r.m.s.d.) and maximal deviation (max. d.) values (Table 2) generated with the Mercury software (Macrae et al., 2020 ). The r.m.s.d and max. d. values calculated for molecular overlays of btc³⁻ of 1a and 1b with H₃btc and H₂btc⁻ (Asprilla-Herrera et al., 2025) are notably lower (with the largest r.m.s.d. equal to 0.0776 Å and max. d. equal to 0.1626 Å for btc⁻ of 1b overlayed with H₂btc⁻ reported by Asprilla-Herrera et al.) compared to the overlays with the other reported btc structures (with the lowest r.m.s.d. equal to 0.1067 Å and max. d. equal to 0.2231 Å for 1b overlayed with H₂btc⁻ reported by Baletska et al.). Note that hydrogen atoms were excluded from the calculation.

Table 2
Root-mean-square-deviation and maximal deviation values calculated for molecular overlays of btc³⁻ in 1 and other reported btc structures

	1a		1b
	r.m.s.d	max. d.	r.m.s.d.	max. d.
H₃btc (Tothadi et al., 2020)	0.0695	0.1509	0.0643	0.1098
H₂btc⁻ (Baletska et al., 2023)	0.1067	0.2231	0.1383	0.3149
H₂btc⁻ (Asprilla-Herrera et al., 2025)	0.0592	0.1135	0.0776	0.1626
Hbtc²⁻ (Asprilla-Herrera et al., 2025)	0.1522	0.3301	0.1804	0.3712

Figure 2
Molecular overlay of btc³⁻ anions from 1a (light blue) and 1b (orange) with (a) neutral H₃btc molecule (dark blue; Tothadi et al., 2020

), (b) H₂btc⁻ anion (purple; Baletska et al., 2023

), (c) H₂btc⁻ anion (dark green; Asprilla-Herrera et al., 2025

), and (d) Hbtc²⁻ (red; Asprilla-Herrera et al., 2025

Table 3. presents selected bond lengths, angles, and torsions for the H2-mIm⁺ cations. The corresponding C—C and C—N bond distances are rather uniform across the individual cations. The C—C bond distances fall in the range of 1.349 (2)–1.480 (2) Å for 1a and 1.34 (2)–1.48 (2) Å for 1b. The C—N bond distances vary from 1.323 (2) to 1.382 (3) Å for 1a and from 1.31 (2) to 1.40 (3) Å for 1b. The distances of both aromatic C—C bonds and C—C bonds between the ring and the methyl group of H2-mIm⁺ cations of 1 are more similar to those observed in the structures of H2-mIm⁺ cations reported by Baletska et al. [1.345 (3) and 1.481 (3) Å, respectively] and Asprilla-Herrera et al. [ion a: 1.348 (2) and 1.483 (3) Å, respectively] than the neutral 2-mIm structure published by Hachuła et al., 2010 [1.367 (1) Å and 1.488 (1) Å, respectively]. Only a slight asymmetry of endocyclic N—C bonds was observed for the Xa and Za H2-mIm⁺ cations in the structure of 1, suggesting a greater double-bond character of the N1—C11 and N5—C19 bonds than the N2—C11 and N6—C19 bonds, accordingly. In 1a, the difference in distance is comparable (from 0.004 to 0.008 Å) to that of the structure from Baletska et al. (0.008 Å), and for 1b (from 0.02–0.03 Å), it is similar to that of the structure of the neutral 2-mIm molecule (0.022 Å).

Table 3
Selected bond lengths (Å), angles (°), and torsion angles (°C) of the H2-mIm⁺ ions

Xa		Ya		Za
C10—C11	1.480 (2)	C14—C15	1.476 (2)	C18—C19	1.473 (2)
C12—C13	1.349 (2)	C16—C17	1.352 (2)	C20—C21	1.349 (2)
N1—C11	1.323 (2)	N3—C15	1.329 (2)	N5—C19	1.324 (2)
N1—C13	1.376 (2)	N3—C16	1.375 (2)	N5—C21	1.378 (2)
N2—C11	1.331 (2)	N4—C15	1.333 (3)	N6—C19	1.336 (3)
N2—C12	1.381 (3)	N4—C17	1.380 (3)	N6—C20	1.382 (3)
C10—C11—N1	125.1 (1)	C14—C15—N3	125.3 (1)	C18—C19—N5	125.3 (1)
C11—N1—C13	108.5 (1)	C15—N3—C16	108.7 (1)	C19—N5—C21	108.6 (1)
N1—C13—C12	107.8 (1)	N3—C16—C17	107.5 (1)	N5—C21—C20	107.6 (2)
C13—C12—N2	106.3 (2)	C16—C17—N4	106.5 (2)	C21—C20—N6	106.6 (2)
C12—N2—C11	108.9 (2)	C17—N4—C15	109.0 (2)	C20—N6—C19	108.7 (2)
N2—C11—N1	108.6 (2)	N4—C15—N3	108.3 (2)	N6—C19—N5	108.5 (2)
N2—C11—C10	126.3 (2)	N4—C15—C14	126.4 (2)	N6—C19—C18	126.1 (2)
C13—N1—C11—C10	179.5 (2)	C16—N3—C15—C14	−178.4 (2)	C21—N5—C19—C18	178.3 (2)
C12—N2—C11—C10	−179.2 (2)	C17—N4—C15—C14	178.5 (2)	C20—N6—C19—C18	−178.1 (2)

Xb		Yb		Zb
C10—C11	1.48 (2)	C14—C15	1.47 (2)	C18—C19	1.47 (2)
C12—C13	1.34 (2)	C16—C17	1.35 (2)	C20—C21	1.34 (2)
N1—C11	1.31 (2)	N3—C15	1.32 (2)	N5—C19	1.32 (1)
N1—C13	1.36 (2)	N3—C16	1.36 (2)	N5—C21	1.37 (2)
N2—C11	1.34 (2)	N4—C15	1.34 (4)	N6—C19	1.34 (3)
N2—C12	1.39 (3)	N4—C17	1.39 (2)	N6—C20	1.40 (3)
C10—C11—N1	126 (1)	C14—C15—N3	126 (1)	C18—C19—N5	127 (1)
C11—N1—C13	108 (1)	C15—N3—C16	108 (1)	C19—N5—C21	108 (1)
N1—C13—C12	110 (1)	N3—C16—C17	109 (1)	N5—C21—C20	109 (1)
C13—C12—N2	104 (2)	C16—C17—N4	105 (2)	C21—C20—N6	105 (1)
C12—N2—C11	109 (2)	C17—N4—C15	109 (2)	C20—N6—C19	109 (2)
N2—C11—N1	109 (2)	N4—C15—N3	108 (2)	N6—C19—N5	108 (1)
N2—C11—C10	125 (2)	N4—C15—C14	125 (2)	N6—C19—C18	124 (2)
C13—N1—C11—C10	−177 (2)	C16—N3—C15—C14	178 (1)	C21—N5—C19—C18	179 (1)
C12—N2—C11—C10	178 (2)	C17—N4—C15—C14	−179 (2)	C20—N6—C19—C18	−178 (2)

Similar to other H2-mIm⁺ structures, protonation introduces more symmetry regarding the bond angles within the aromatic ring. The largest deviation from the ideal pentagon interior angle of 108° is 1.7° in fraction 1a (Xa ion) and 4° in fraction 1b (Xb ion). In comparison, the corresponding deviation in the structure of the neutral 2-mIm form is 3.4°. The methyl groups in cations of 1 show the maximal deviation from coplanarity with the aromatic ring in the Za (1.9°) and Xb (3°) ions. Compared to other reported structures, these values are the closest to those reported by Asprilla-Herrera et al. in one of the ions in the structure (for which the maximal deviation reported was 2.3°). In the other 2-mIm⁺ and 2-mIm structures, the corresponding maximal deviation from planarity was no higher than 0.9°.

The values of root-mean-squared deviation (r. m. s. d.) and maximal deviation (max. d.) values calculated by Mercury software for the molecular overlays of H2-mIm⁺ cations of 1 with the neutral H2-mIm molecule and the other H2-mIm⁺ cations are presented in Table 4. The molecular overlays are depicted in Fig. 3. The values suggest a higher resemblance of H2-mIm⁺ cations of 1 to other reported protonated forms, with the lowest value of r.m.s.d. and max. d. recorded for the overlay of Xa with the B ion from the structure reported by Asprilla-Herrera et al. (0.0050 and 0.0076 Å, respectively).

Table 4
Root-mean-square-deviation and maximal deviation values calculated for molecular overlays of H2-mIm⁺ ions in 1 and other reported 2-mIm structures

	Xa		Ya		Za
	r.m.s.d.	max. d.	r.m.s.d.	max. d.	r.m.s.d.	max. d.
2-mIm (Hachuła et al., 2010)	0.0269	0.0430	0.0268	0.0430	0.0268	0.0385
H2-mIm⁺ (Baletska et al., 2023)	0.0102	0.0125	0.0093	0.0123	0.0141	0.0202
H2-mIm⁺ ion A (Asprilla-Herrera et al., 2025)	0.0123	0.0167	0.0094	0.0143	0.0111	0.0169
H2-mIm⁺ ion B (Asprilla-Herrera et al., 2025)	0.0050	0.0076	0.0064	0.0097	0.0075	0.0108
H2-mIm⁺ ion C (Asprilla-Herrera et al., 2025)	0.0075	0.0104	0.0091	0.0120	0.0103	0.0157

	Xb		Yb		Zb
2-mIm (Hachuła et al., 2010)	0.0265	0.0409	0.0298	0.0451	0.0419	0.0612
H2-mIm⁺ (Baletska et al., 2023)	0.0216	0.0352	0.0233	0.0390	0.0368	0.0468
H2-mIm⁺ ion A (Asprilla-Herrera et al., 2025)	0.0214	0.0351	0.0255	0.0462	0.0331	0.0437
H2-mIm⁺ ion B (Asprilla-Herrera et al., 2025)	0.0178	0.0317	0.0203	0.0372	0.0309	0.0431
H2-mIm⁺ ion C (Asprilla-Herrera et al., 2025)	0.0237	0.0404	0.0227	0.0342	0.0359	0.0470

Figure 3
Molecular overlay plot of H2-mIm⁺ cations of 1a (light green) and 1b (yellow) with (a) neutral 2-mIm molecule (dark green; Hachuła et al., 2010

), (b) H2-mIm⁺ cation (magenta; Baletska et al., 2023

) and H2-mIm⁺ cations adapted from Asprilla-Herrera et al. (blue; c, d, e – cations A, B, and C, respectively).

3. Supramolecular features

The primary intermolecular interactions contributing to the crystal packing include hydrogen bonds and π–π stacking. The hydrogen bonds form 2D network planes perpendicular to the [111] vector (Fig. 4), while the π–π stacking between the aromatic rings hold the planes together (Fig. 5). Table 5 displays the details of the π–π interactions between the planes, while Table 6 summarizes the geometrical details of the hydrogen-bond network. Note that half of the hydrogen bonds are charge-assisted and therefore, display an ionic character, confirmed by significantly shorter distances between acceptor and donor atoms (Mayer et al., 1992 ).

Table 5
Geometrical details of π–π interactions (Å) in 1

Ion	H2-mIm⁻	Centroid-to-centroid distance	Perpendicular distance	Offset
btc³⁻ (1a)	Xa	3.6855 (10)	3.3	1.629
btc³⁻ (1a)	Za	3.8392 (12)	3.4	1.771
Xa	Ya	3.4548 (12)	3.2	1.294
Ya	Za	3.5466 (13)	3.3	1.482
btc³⁻ (1b)	Xb	3.769 (11)	3.4	1.881
btc³⁻ (1b)	Zb	3.694 (10)	3.2	1.87
Xb	Yb	3.416 (13)	3.4	0.195
Yb	Zb	3.544 (13)	3.5	0.347

Table 6
Hydrogen-bond geometry (Å, °)

	Graph-set descriptor	Type	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯O1A^iv	D(2)	a	0.883 (9)	1.730 (10)	2.6101 (17)	174.4 (18)
N2A—H2A⋯O4A^v	D(2)	b	0.873 (9)	1.828 (10)	2.6888 (18)	168.5 (18)
N3A—H3A⋯O5A^vi	D(2)	c	0.881 (9)	1.755 (10)	2.6309 (16)	172.3 (18)
N4A—H4A⋯O2A	D(2)	d	0.877 (9)	1.815 (10)	2.682 (2)	169.8 (18)
N5A—H5AA⋯O3Aⁱ	D(2)	e	0.868 (9)	1.749 (10)	2.6131 (17)	173.2 (19)
N6A—H6A⋯O6A^vii	D(2)	f	0.873 (9)	1.857 (10)	2.713 (2)	166.7 (18)
N1B—H1B⋯O1Bⁱ	D(2)	a	0.88	1.64	2.510 (16)	169.2
N2B—H2B⋯O4B^vii	D(2)	b	0.88	1.75	2.606 (16)	164.9
N3B—H3B⋯O5Bⁱⁱⁱ	D(2)	c	0.88	1.66	2.522 (15)	167.6
N4B—H4B⋯O2Bⁱ	D(2)	d	0.88	1.75	2.598 (16)	161.8
N5B—H5BA⋯O3B^iv	D(2)	e	0.88	1.65	2.518 (15)	168.4
N6B—H6B⋯O6B^v	D(2)	f	0.88	1.83	2.648 (19)	153.2
C10A—H10C⋯O2A^iv			0.98	2.42	3.390 (2)	170.8
C12A—H12A⋯O5A^v			0.95	2.45	3.338 (2)	156
C14A—H14B⋯O6A^vi			0.98	2.43	3.3867 (19)	165
C17A—H17A⋯O3A			0.95	2.44	3.3202 (19)	154.5
C18A—H18A⋯O1A			0.98	2.63	3.462 (2)	143.2
C18A—H18C⋯O4Aⁱ			0.98	2.45	3.371 (2)	156.5
C20A—H20A⋯O1A^vii			0.95	2.38	3.2993 (19)	163.5
C10B—H10D⋯O2Bⁱ			0.98	2.61	3.51 (2)	151.4
C10B—H10E⋯O2Bⁱⁱ			0.98	2.05	2.85 (3)	136.8
C12B—H12B⋯O5B^vii			0.95	2.58	3.475 (15)	157.1
C17B—H17B⋯O3Bⁱ			0.95	2.52	3.442 (16)	164.3
Symmetry codes: (i) 1 − x, 1 − y, 2 − z; (ii) 1 + x, y, z; (iii) −x, −y, 2 − z; (iv) 1 − x, 1 − y, 1 − z; (v) 1 − x, −y, 2 − z; (vi) −1 + x, 1 + y, z; (vii) 2 − x, 1 − y, 1 − z.

Figure 4
View along the [111] vector showing a network of hydrogen bonds between btc³⁻ and H2-mIm⁺ ions in the a fraction. The first-level graph-set descriptors are labelled with letters a–f (see Table 6

). The colour coding indicates the direction of the C₂²(12) chains of the second-level graph-set descriptors.

Figure 5
Crystal packing in compound 1 viewed along the [ $[\overline{1}]$ 11] vector illustrating the stacking of the planes via π–π interactions (green lines).

To gain a deeper understanding of the intermolecular interaction patterns within 1, a graph-set analysis (Etter et al., 1990 ; Bernstein et al., 1995 ) was performed. The analysis reveals that 1 contains only six discrete D(2) motifs at the first-level graph set. The second-level graph set features three C₂²(12) and twelve D₂² (Table 7) motifs. No other types of patterns were identified during the graph-set analysis.

Table 7
Second-level graph sets in 1

C₂²(12)	>a<b	D²₂(9)	>b<c	D²₂(9)	>c<e
D²₂(9)	>a<c	D²₂(9)	>b<d	D²₂(5)	>c<f
D²₂(5)	>a<d	D²₂(5)	>b<e	D²₂(9)	>d<e
D²₂(9)	>a<e	D²₂(9)	>b<f	D²₂(9)	>d<f
D²₂(9)	>a<f	C₂²(12)	>c<d	C₂²(12)	>e<f

4. Hirshfeld surface analysis

Intermolecular interactions in both fractions of 1 were further quantified using Hirshfeld surface analysis with CrystalExplorer 17.5 (Turner et al. 2017 ). The three-dimensional d_norm surfaces were plotted with a standard resolution and a fixed colour scale ranging from −0.7640 (red) to 1.0884 (blue) a.u. for fraction a and from −0.8458 (red) to 1.0400 (blue) for the minor fraction b. The pale-red spots in Fig. 6 indicate short contacts and negative d_norm values on the surface, corresponding to the interactions previously described.

Figure 6
Hirshfeld surface for each ion in both fractions of 1 mapped over d_norm.

The two-dimensional fingerprint plots for fractions a and b are illustrated in Fig. 7 and Fig. 8, respectively, with the contributions per interaction per ion summarized in Table 8. In both fractions, the greatest contributions for the btc³⁻ ions are O⋯H (>50%) and H⋯H (> 15%), while for the three H2-mIm⁺ ions are the H⋯H (> 50%) and H⋯O (> 19%).

Table 8
Intermolecular interaction contribution (%) from Hirshfeld surface analysis of 1

	btc³⁻	btc³⁻	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺
	1a	1b	Xa	Ya	Za	Xb	Yb	Zb
O—O	0	1.3	–	–	–	–	–	–
O—C	2.2	2.8	–	–	–	–	–	–
O—H	56.2	52.8	–	–	–	–	–	–
O—N	0	0.1	–	–	–	–	–	–
C—O	2.7	2.9	0.3	0.2	0.5	0.6	0	0.8
C—C	5.3	6.9	5	2.7	5.2	6.5	4.7	6
C—H	12.2	9.8	3.7	5.1	3	0.4	0.5	0.9
C—N	2	2.4	1.1	2.3	1	2.3	4.2	2
H—N	1.3	1	1	2.3	1.3	0.6	1.1	0.6
H—H	15.2	17.5	50.2	55.4	49.3	54.6	62.9	53.4
H—C	1.4	0.1	7.5	3.6	7.1	3.9	1.1	5.1
H—O	1.4	2.4	24.5	21.8	26.1	24.6	19.2	24.7
N—O	–	–	0	0.1	0	0.1	0	0.1
N—C	–	–	2.8	2.1	2.7	4.3	4.2	3.9
N—H	–	–	3	2.6	2.8	1.8	1.2	2
N—N	–	–	0.9	2	1.1	0.4	1	0.6

Figure 7
Fingerprint plots of the Hirshfeld surfaces for fraction a of 1, showing the overall plot and three most significant intermolecular contributions.

Figure 8
Fingerprint plots of the Hirshfeld surfaces for fraction b of 1, showing the overall plot and three most significant intermolecular contributions.

5. Database survey

No reported structures of the title compound were found in the Cambridge Structural Database (CSD version 5.45, update of November 2023; Groom et al., 2016 ). The closest to 1 are the previously mentioned structures reported under the refcodes ZUQYOD (Asprilla-Herrera et al., 2025) and LODSUW (Baletska et al., 2023).

Some structures containing H2-mIm⁺ cation were reported under the refcodes BEZGEU (Dhanabal et al., 2013 ), BOTTEK, BOTTIO, BOTTOU (Meng et al., 2009 ), BOTTEK01, BOTTIO01, BOTTOU01, VURBUG, VURCAN, VURFAQ (Callear et al., 2010 ), DAMGIL (Hinokimoto et al., 2021 ), DOWVUI (Shi et al., 2014 ), FAMFIL, FAMFOR, FAMFUX (Zhang & Zhang, 2017 ), FETDAK (Aakeröy et al., 2005 ), HILSOL (Qu, 2007 ). However, these structures do not have the btc³⁻ ion.

Among the various reported structures containing fully deprotonated btc³⁻ ion with other organic cations, we highlight those with the following refcodes: HEGFOQ (Zhu et al., 2011 ), HOPZIX (Ndoye et al., 2013 ), IJEQIX (Lynch, 2003 ), LIDHIT, LIDJIV (Skala et al., 2023 ), MEKKES, MEKKIW, MEKKOC (Plaut et al., 2000 ), OSADOD (Singh et al., 2016 ), OTINUB (Gupta et al., 2011 ), TOZZUD, TUBBAT (Melendez et al., 1996 ), VABQOG (Liu et al., 2010 ), and WONVAX (Hayashi et al., 2008 ). However, these structures do not contain the H2-mIm⁺ cation.

Some compounds with low resemblance to the title compound were reported under the refcodes CUMQUX (Basu et al., 2009 ), HICSUJ (Lie et al., 2013 ), ILELAO (Li & Li, 2016 ), JOCBAH (Falek et al., 2019 ), LUBGUM, LUBHAT, LUBHEX, LUBHIB, LUBHOH, LUBHUN, LUBJAV (Singh et al., 2015 ), SUHRAR (Rajkumar et al., 2020 ), YOCSIT (Habib & Janiak, 2008 ), WOGBED (Sosa-Rivadeneyra et al., 2024 ).

6. Synthesis and crystallization

To synthesize the title compound, 120 µl of a 1.58 M ethanolic solution of 2-mIm was diluted with 2 ml of ethanol, followed by the addition of 100 µl of a 0.12 M ethanolic solution of H₃btc. The mixture was gently shaken and left to rest at 313 K. After one week, crystals of 1 were obtained.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 9. The structure is disordered over two orientations and was refined using a split model with restraint on bond lengths (SADI). SIMU and RIGU restraints were then applied across the minor fraction b. Constraints on the atomic displacement parameter (EADP) were also applied to C18B, C10B, C6B, C7B, N5B, and O6B of the minor component, with close by part a atoms. The most disagreeable reflection (1 0 5), with an error/s.u. of more than 10, was omitted using the OMIT instruction in SHELXL (Sheldrick, 2015b ). The positions of hydrogen atoms were refined with U_iso(H) = 1.2U_eq(C or N) for CH and NH groups and U_iso(H) = 1.5U_eq(C or O) for others. Hydrogen atoms attached to nitrogen atoms were refined with DFIX 0.86 0.01 instruction for the major component, while the HFIX command was applied for the minor component.

Table 9
Experimental details

Crystal data
Chemical formula	3C₄H₇N₂⁺·C₉H₃O₆³⁻
M_r	456.46
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.8634 (5), 10.3453 (7), 11.6777 (7)
α, β, γ (°)	74.199 (4), 79.749 (4), 87.580 (4)
V (Å³)	1013.85 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.1 × 0.08 × 0.07

Data collection
Diffractometer	Bruker P4
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.661, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	18775, 4693, 3780
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.05
No. of reflections	4693
No. of parameters	584
No. of restraints	1806
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b) and OLEX2 1.5 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2453953

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004748/jq2040sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004748/jq2040Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025004748/jq2040Isup3.cml

checkCIF report

Computing details top

Tris(2-methyl-1H-imidazol-3-ium) benzene-1,3,5-tricarboxylate top

Crystal data top

3C₄H₇N₂⁺·C₉H₃O₆³⁻	Z = 2
M_r = 456.46	F(000) = 480
Triclinic, P1	D_x = 1.495 Mg m⁻³
a = 8.8634 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3453 (7) Å	Cell parameters from 4963 reflections
c = 11.6777 (7) Å	θ = 2.7–27.6°
α = 74.199 (4)°	µ = 0.11 mm⁻¹
β = 79.749 (4)°	T = 296 K
γ = 87.580 (4)°	Irregular, clear light colourless
V = 1013.85 (11) Å³	0.1 × 0.08 × 0.07 mm

Data collection top

Bruker P4 diffractometer	R_int = 0.033
Graphite monochromator	θ_max = 27.6°, θ_min = 1.8°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
T_min = 0.661, T_max = 0.746	l = −15→15
18775 measured reflections	Standard reflections: not measured; every not measured reflections
4693 independent reflections	intensity decay: not measured
3780 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0501P)² + 0.3475P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4693 reflections	Δρ_max = 0.36 e Å⁻³
584 parameters	Δρ_min = −0.23 e Å⁻³
1806 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	Occ. (<1)
O1A	0.63437 (13)	0.63491 (11)	0.46926 (9)	0.0164 (2)	0.9099 (9)
O2A	0.43997 (12)	0.69982 (11)	0.59090 (10)	0.0191 (3)	0.9099 (9)
O3A	0.29536 (12)	0.41347 (12)	1.00672 (10)	0.0186 (3)	0.9099 (9)
O4A	0.44291 (12)	0.24354 (10)	1.08539 (9)	0.0176 (2)	0.9099 (9)
O5A	0.88019 (13)	0.11476 (11)	0.80957 (10)	0.0217 (3)	0.9099 (9)
O6A	0.92786 (12)	0.22264 (11)	0.61337 (9)	0.0190 (2)	0.9099 (9)
C1A	0.54608 (16)	0.62073 (15)	0.56953 (14)	0.0130 (3)	0.9099 (9)
C2A	0.41160 (18)	0.33842 (14)	1.00035 (14)	0.0127 (3)	0.9099 (9)
C3A	0.85593 (17)	0.20775 (15)	0.71862 (13)	0.0137 (3)	0.9099 (9)
C4A	0.57684 (18)	0.50083 (14)	0.67027 (14)	0.0118 (3)	0.9099 (9)
C5A	0.48727 (17)	0.47639 (15)	0.78478 (14)	0.0119 (3)	0.9099 (9)
H5A	0.405067	0.535044	0.799311	0.014*	0.9099 (9)
C6A	0.51636 (17)	0.36719 (16)	0.87845 (13)	0.0114 (3)	0.9099 (9)
C7A	0.63867 (18)	0.28287 (15)	0.85651 (14)	0.0115 (3)	0.9099 (9)
H7A	0.661151	0.209755	0.920485	0.014*	0.9099 (9)
C8A	0.72825 (16)	0.30428 (15)	0.74229 (14)	0.0117 (3)	0.9099 (9)
C9A	0.69628 (17)	0.41354 (15)	0.64951 (13)	0.0120 (3)	0.9099 (9)
H9A	0.756694	0.428611	0.571195	0.014*	0.9099 (9)
N1A	0.36212 (15)	0.17449 (12)	0.73067 (12)	0.0148 (3)	0.9099 (9)
H1A	0.367 (2)	0.2355 (15)	0.6605 (11)	0.022*	0.9099 (9)
N2A	0.4159 (3)	−0.0048 (2)	0.86170 (16)	0.0140 (4)	0.9099 (9)
H2A	0.4619 (19)	−0.0805 (12)	0.8884 (16)	0.021*	0.9099 (9)
C10A	0.5638 (2)	0.03092 (17)	0.65126 (16)	0.0202 (4)	0.9099 (9)
H10A	0.534175	−0.053945	0.639115	0.030*	0.9099 (9)
H10B	0.664662	0.021176	0.675921	0.030*	0.9099 (9)
H10C	0.568484	0.102221	0.575648	0.030*	0.9099 (9)
C11A	0.44916 (16)	0.06610 (14)	0.74657 (13)	0.0135 (3)	0.9099 (9)
C12A	0.30468 (17)	0.06181 (15)	0.92221 (14)	0.0162 (3)	0.9099 (9)
H12A	0.260489	0.034459	1.005449	0.019*	0.9099 (9)
C13A	0.27126 (19)	0.17348 (17)	0.83954 (15)	0.0167 (3)	0.9099 (9)
H13A	0.198107	0.239584	0.853903	0.020*	0.9099 (9)
N3A	0.06717 (14)	0.90954 (13)	0.81578 (12)	0.0147 (3)	0.9099 (9)
H3A	0.0060 (18)	0.9796 (14)	0.8066 (17)	0.022*	0.9099 (9)
N4A	0.2353 (4)	0.7711 (3)	0.7613 (2)	0.0136 (4)	0.9099 (9)
H4A	0.3034 (17)	0.7388 (18)	0.7122 (14)	0.020*	0.9099 (9)
C14A	0.1663 (2)	0.96187 (19)	0.59451 (15)	0.0167 (4)	0.9099 (9)
H14A	0.268061	1.003764	0.565408	0.025*	0.9099 (9)
H14B	0.087809	1.031841	0.589348	0.025*	0.9099 (9)
H14C	0.149788	0.903210	0.544569	0.025*	0.9099 (9)
C15A	0.15618 (17)	0.88171 (15)	0.72134 (13)	0.0130 (3)	0.9099 (9)
C16A	0.09140 (19)	0.81487 (18)	0.91902 (16)	0.0165 (4)	0.9099 (9)
H16A	0.043111	0.811425	0.999237	0.020*	0.9099 (9)
C17A	0.19652 (17)	0.72754 (15)	0.88554 (13)	0.0151 (3)	0.9099 (9)
H17A	0.235948	0.651262	0.937315	0.018*	0.9099 (9)
N5A	0.90654 (15)	0.58146 (13)	0.80199 (12)	0.0159 (3)	0.9099 (9)
H5AA	0.8356 (17)	0.5879 (19)	0.8618 (13)	0.024*	0.9099 (9)
N6A	1.0223 (4)	0.6183 (3)	0.61691 (17)	0.0158 (5)	0.9099 (9)
H6A	1.047 (2)	0.6590 (17)	0.5401 (9)	0.024*	0.9099 (9)
C18A	0.8036 (2)	0.77104 (17)	0.65572 (15)	0.0173 (4)	0.9099 (9)
H18A	0.775661	0.772415	0.577879	0.026*	0.9099 (9)
H18B	0.854750	0.855706	0.648619	0.026*	0.9099 (9)
H18C	0.710800	0.760067	0.717405	0.026*	0.9099 (9)
C19A	0.90804 (17)	0.65821 (15)	0.69068 (14)	0.0140 (3)	0.9099 (9)
C20A	1.09638 (18)	0.51212 (15)	0.68442 (14)	0.0183 (3)	0.9099 (9)
H20A	1.181907	0.464382	0.655269	0.022*	0.9099 (9)
C21A	1.0234 (2)	0.48953 (18)	0.79978 (15)	0.0186 (4)	0.9099 (9)
H21A	1.048088	0.422387	0.867299	0.022*	0.9099 (9)
O1B	0.3361 (14)	0.3467 (11)	1.0512 (9)	0.021 (2)	0.0901 (9)
O2B	0.2768 (12)	0.5341 (10)	0.9276 (9)	0.019 (2)	0.0901 (9)
O3B	0.5623 (13)	0.6743 (11)	0.5010 (11)	0.019 (2)	0.0901 (9)
O4B	0.7474 (12)	0.5493 (10)	0.4393 (8)	0.0185 (19)	0.0901 (9)
O5B	0.9052 (12)	0.1340 (12)	0.7314 (10)	0.022 (2)	0.0901 (9)
O6B	0.7760 (13)	0.0691 (10)	0.9168 (8)	0.0217 (3)	0.0901 (9)
C1B	0.3620 (15)	0.4349 (12)	0.9506 (10)	0.0154 (17)	0.0901 (9)
C2B	0.6491 (15)	0.5726 (12)	0.5215 (9)	0.0155 (17)	0.0901 (9)
C3B	0.8013 (15)	0.1528 (11)	0.8159 (9)	0.0155 (15)	0.0901 (9)
C4B	0.4914 (16)	0.4160 (15)	0.8519 (11)	0.0139 (15)	0.0901 (9)
C5B	0.5144 (17)	0.4987 (15)	0.7351 (10)	0.0130 (15)	0.0901 (9)
H5B	0.450408	0.574762	0.715534	0.016*	0.0901 (9)
C6B	0.6278 (17)	0.4738 (13)	0.6461 (9)	0.0118 (3)	0.0901 (9)
C7B	0.7185 (17)	0.3616 (13)	0.6748 (11)	0.0120 (3)	0.0901 (9)
H7B	0.795895	0.343054	0.613952	0.014*	0.0901 (9)
C8B	0.6991 (17)	0.2759 (13)	0.7898 (11)	0.0143 (14)	0.0901 (9)
C9B	0.5855 (17)	0.3057 (15)	0.8771 (12)	0.0140 (15)	0.0901 (9)
H9B	0.571941	0.248118	0.956982	0.017*	0.0901 (9)
N1B	0.8512 (14)	0.6448 (12)	0.7625 (10)	0.0162 (15)	0.0901 (9)
H1B	0.794429	0.643147	0.832866	0.019*	0.0901 (9)
N2B	1.022 (4)	0.596 (3)	0.6250 (14)	0.0151 (19)	0.0901 (9)
H2B	1.099861	0.555833	0.590398	0.018*	0.0901 (9)
C10B	1.027 (3)	0.459 (2)	0.8362 (16)	0.0186 (4)	0.0901 (9)
H10D	0.973669	0.462481	0.916474	0.028*	0.0901 (9)
H10E	1.136675	0.473684	0.829447	0.028*	0.0901 (9)
H10F	1.009621	0.370858	0.824488	0.028*	0.0901 (9)
C11B	0.9660 (16)	0.5645 (13)	0.7432 (11)	0.0172 (16)	0.0901 (9)
C12B	0.9386 (16)	0.7024 (13)	0.5652 (10)	0.0168 (18)	0.0901 (9)
H12B	0.951250	0.744914	0.481027	0.020*	0.0901 (9)
C13B	0.8361 (19)	0.7308 (16)	0.6542 (11)	0.0144 (18)	0.0901 (9)
H13B	0.763155	0.801145	0.643027	0.017*	0.0901 (9)
N3B	0.9101 (15)	0.0588 (12)	1.2644 (10)	0.020 (2)	0.0901 (9)
H3B	0.972182	−0.007821	1.255590	0.024*	0.0901 (9)
N4B	0.780 (5)	0.241 (3)	1.224 (2)	0.020 (3)	0.0901 (9)
H4B	0.741883	0.315890	1.182443	0.024*	0.0901 (9)
C14B	0.967 (2)	0.2003 (19)	1.0515 (11)	0.019 (3)	0.0901 (9)
H14D	0.990040	0.116708	1.028014	0.029*	0.0901 (9)
H14E	1.061878	0.250271	1.041044	0.029*	0.0901 (9)
H14F	0.897947	0.255024	1.000667	0.029*	0.0901 (9)
C15B	0.8916 (17)	0.1686 (14)	1.1790 (10)	0.019 (2)	0.0901 (9)
C16B	0.817 (2)	0.0660 (16)	1.3684 (11)	0.017 (3)	0.0901 (9)
H16B	0.811200	0.001269	1.444487	0.020*	0.0901 (9)
C17B	0.7345 (17)	0.1797 (14)	1.3463 (12)	0.021 (2)	0.0901 (9)
H17B	0.661054	0.210989	1.402322	0.025*	0.0901 (9)
N5B	0.4442 (13)	0.1450 (11)	0.6925 (9)	0.0148 (3)	0.0901 (9)
H5BA	0.437910	0.215239	0.631013	0.018*	0.0901 (9)
N6B	0.410 (3)	0.013 (3)	0.8728 (14)	0.016 (2)	0.0901 (9)
H6B	0.376045	−0.018373	0.950791	0.019*	0.0901 (9)
C18B	0.2189 (18)	0.1957 (19)	0.8343 (17)	0.0167 (3)	0.0901 (9)
H18D	0.236520	0.290934	0.791949	0.025*	0.0901 (9)
H18E	0.204232	0.184000	0.921700	0.025*	0.0901 (9)
H18F	0.127233	0.164192	0.813587	0.025*	0.0901 (9)
C19B	0.3520 (14)	0.1176 (14)	0.7978 (11)	0.0169 (16)	0.0901 (9)
C20B	0.5330 (16)	−0.0392 (13)	0.8061 (11)	0.0171 (18)	0.0901 (9)
H20B	0.590742	−0.117429	0.833557	0.021*	0.0901 (9)
C21B	0.5516 (18)	0.0457 (15)	0.6950 (11)	0.0161 (18)	0.0901 (9)
H21B	0.627299	0.038191	0.628490	0.019*	0.0901 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0192 (6)	0.0154 (6)	0.0093 (5)	0.0061 (5)	0.0031 (4)	0.0011 (5)
O2A	0.0218 (6)	0.0166 (5)	0.0133 (5)	0.0117 (4)	0.0018 (4)	0.0003 (4)
O3A	0.0199 (6)	0.0180 (6)	0.0116 (6)	0.0103 (5)	0.0034 (5)	0.0007 (5)
O4A	0.0213 (5)	0.0157 (5)	0.0098 (5)	0.0077 (4)	0.0022 (4)	0.0025 (4)
O5A	0.0259 (6)	0.0188 (6)	0.0132 (6)	0.0139 (5)	0.0021 (5)	0.0020 (5)
O6A	0.0214 (6)	0.0192 (5)	0.0115 (5)	0.0094 (4)	0.0033 (4)	−0.0011 (4)
C1A	0.0153 (7)	0.0112 (7)	0.0107 (8)	0.0028 (6)	−0.0008 (6)	−0.0015 (6)
C2A	0.0148 (7)	0.0111 (7)	0.0110 (7)	0.0030 (6)	−0.0009 (6)	−0.0023 (6)
C3A	0.0163 (7)	0.0117 (7)	0.0113 (7)	0.0037 (6)	−0.0015 (6)	−0.0012 (6)
C4A	0.0139 (8)	0.0098 (7)	0.0097 (7)	0.0027 (5)	−0.0005 (6)	−0.0009 (5)
C5A	0.0128 (7)	0.0110 (7)	0.0102 (8)	0.0041 (6)	−0.0001 (6)	−0.0020 (6)
C6A	0.0130 (7)	0.0102 (7)	0.0100 (7)	0.0019 (6)	−0.0001 (6)	−0.0024 (6)
C7A	0.0145 (8)	0.0085 (7)	0.0098 (7)	0.0029 (6)	−0.0020 (6)	0.0000 (5)
C8A	0.0119 (7)	0.0109 (7)	0.0111 (8)	0.0029 (6)	−0.0001 (6)	−0.0024 (6)
C9A	0.0140 (7)	0.0113 (7)	0.0081 (7)	0.0030 (6)	0.0006 (5)	−0.0005 (6)
N1A	0.0186 (6)	0.0116 (6)	0.0115 (6)	0.0030 (5)	−0.0014 (5)	0.0002 (5)
N2A	0.0175 (7)	0.0101 (9)	0.0123 (7)	0.0037 (6)	−0.0013 (6)	−0.0008 (6)
C10A	0.0218 (8)	0.0188 (8)	0.0145 (8)	0.0073 (6)	0.0036 (7)	−0.0006 (7)
C11A	0.0152 (7)	0.0114 (7)	0.0121 (7)	0.0019 (5)	−0.0016 (6)	−0.0007 (6)
C12A	0.0185 (7)	0.0139 (7)	0.0146 (7)	0.0016 (6)	0.0004 (6)	−0.0034 (6)
C13A	0.0185 (9)	0.0135 (8)	0.0149 (7)	0.0041 (6)	0.0020 (7)	−0.0024 (6)
N3A	0.0150 (6)	0.0129 (6)	0.0149 (7)	0.0057 (5)	−0.0006 (5)	−0.0036 (5)
N4A	0.0144 (10)	0.0119 (9)	0.0128 (9)	0.0046 (8)	0.0003 (7)	−0.0028 (6)
C14A	0.0193 (8)	0.0161 (9)	0.0114 (8)	0.0048 (6)	−0.0003 (7)	−0.0003 (7)
C15A	0.0128 (7)	0.0117 (7)	0.0140 (8)	0.0020 (6)	−0.0019 (6)	−0.0031 (6)
C16A	0.0174 (8)	0.0161 (8)	0.0135 (8)	0.0026 (7)	0.0006 (6)	−0.0024 (7)
C17A	0.0180 (7)	0.0137 (7)	0.0121 (7)	0.0027 (6)	−0.0022 (6)	−0.0014 (6)
N5A	0.0177 (7)	0.0157 (6)	0.0110 (6)	0.0033 (5)	0.0037 (5)	−0.0023 (5)
N6A	0.0184 (7)	0.0145 (13)	0.0105 (7)	0.0027 (8)	0.0032 (6)	−0.0008 (6)
C18A	0.0162 (8)	0.0148 (8)	0.0176 (8)	0.0039 (6)	−0.0001 (6)	−0.0010 (6)
C19A	0.0146 (7)	0.0130 (7)	0.0131 (7)	−0.0002 (6)	0.0009 (6)	−0.0036 (6)
C20A	0.0202 (8)	0.0145 (7)	0.0165 (8)	0.0056 (6)	0.0015 (6)	−0.0019 (6)
C21A	0.0225 (7)	0.0150 (9)	0.0137 (9)	0.0063 (7)	0.0004 (8)	0.0005 (7)
O1B	0.021 (4)	0.017 (4)	0.016 (4)	0.009 (4)	0.006 (4)	0.000 (3)
O2B	0.024 (4)	0.020 (4)	0.009 (4)	0.009 (3)	0.002 (3)	−0.002 (3)
O3B	0.022 (4)	0.019 (4)	0.007 (4)	0.004 (3)	0.003 (4)	0.005 (3)
O4B	0.025 (4)	0.016 (4)	0.007 (3)	0.004 (3)	0.002 (3)	0.004 (3)
O5B	0.027 (4)	0.014 (4)	0.015 (4)	0.010 (3)	0.001 (3)	0.007 (3)
O6B	0.0259 (6)	0.0188 (6)	0.0132 (6)	0.0139 (5)	0.0021 (5)	0.0020 (5)
C1B	0.018 (3)	0.014 (3)	0.012 (3)	0.003 (3)	0.001 (3)	−0.001 (3)
C2B	0.019 (3)	0.014 (3)	0.010 (3)	0.003 (3)	0.001 (2)	0.001 (2)
C3B	0.018 (3)	0.013 (2)	0.012 (2)	0.005 (2)	−0.001 (2)	0.001 (2)
C4B	0.017 (2)	0.012 (2)	0.009 (2)	0.006 (2)	0.001 (2)	0.001 (2)
C5B	0.017 (2)	0.011 (2)	0.008 (2)	0.003 (2)	0.000 (2)	0.001 (2)
C6B	0.0139 (8)	0.0098 (7)	0.0097 (7)	0.0027 (5)	−0.0005 (6)	−0.0009 (5)
C7B	0.0140 (7)	0.0113 (7)	0.0081 (7)	0.0030 (6)	0.0006 (5)	−0.0005 (6)
C8B	0.018 (2)	0.012 (2)	0.009 (2)	0.005 (2)	0.001 (2)	0.001 (2)
C9B	0.017 (2)	0.013 (2)	0.009 (2)	0.005 (2)	0.001 (2)	−0.001 (2)
N1B	0.020 (3)	0.015 (3)	0.009 (3)	0.003 (2)	0.001 (2)	0.002 (2)
N2B	0.019 (3)	0.013 (3)	0.010 (3)	0.003 (3)	0.003 (3)	−0.002 (3)
C10B	0.0225 (7)	0.0150 (9)	0.0137 (9)	0.0063 (7)	0.0004 (8)	0.0005 (7)
C11B	0.019 (3)	0.015 (3)	0.012 (3)	0.003 (2)	0.003 (2)	0.001 (2)
C12B	0.020 (3)	0.013 (3)	0.012 (3)	0.005 (3)	0.001 (3)	0.001 (3)
C13B	0.018 (3)	0.012 (3)	0.009 (3)	0.002 (3)	0.002 (3)	0.001 (3)
N3B	0.027 (5)	0.019 (4)	0.013 (4)	0.007 (4)	0.005 (4)	−0.009 (3)
N4B	0.023 (5)	0.015 (4)	0.018 (4)	0.009 (4)	0.002 (4)	−0.003 (4)
C14B	0.025 (6)	0.014 (5)	0.014 (4)	0.008 (5)	0.001 (4)	0.001 (4)
C15B	0.022 (4)	0.016 (4)	0.015 (4)	0.006 (3)	0.002 (3)	−0.006 (3)
C16B	0.021 (5)	0.016 (5)	0.013 (5)	0.008 (4)	0.000 (4)	−0.006 (4)
C17B	0.024 (5)	0.018 (4)	0.015 (4)	0.011 (4)	0.003 (4)	−0.001 (4)
N5B	0.0186 (6)	0.0116 (6)	0.0115 (6)	0.0030 (5)	−0.0014 (5)	0.0002 (5)
N6B	0.020 (3)	0.013 (3)	0.010 (3)	0.003 (3)	−0.001 (3)	0.003 (3)
C18B	0.0185 (9)	0.0135 (8)	0.0149 (7)	0.0041 (6)	0.0020 (7)	−0.0024 (6)
C19B	0.019 (3)	0.013 (3)	0.013 (3)	0.004 (2)	0.000 (2)	0.003 (2)
C20B	0.020 (3)	0.015 (3)	0.012 (3)	0.004 (3)	0.002 (3)	0.002 (3)
C21B	0.021 (3)	0.012 (3)	0.011 (3)	0.004 (3)	0.002 (3)	0.001 (3)

Geometric parameters (Å, º) top

O1A—C1A	1.2629 (18)	O1B—C1B	1.266 (9)
O2A—C1A	1.2565 (17)	O2B—C1B	1.246 (9)
O3A—C2A	1.2674 (17)	O3B—C2B	1.271 (9)
O4A—C2A	1.2534 (17)	O4B—C2B	1.245 (9)
O5A—C3A	1.2677 (18)	O5B—C3B	1.275 (9)
O6A—C3A	1.2519 (18)	O6B—C3B	1.247 (9)
C1A—C4A	1.513 (2)	C1B—C4B	1.522 (9)
C2A—C6A	1.516 (2)	C2B—C6B	1.518 (9)
C3A—C8A	1.5159 (19)	C3B—C8B	1.524 (8)
C4A—C5A	1.392 (2)	C4B—C5B	1.384 (9)
C4A—C9A	1.3936 (19)	C4B—C9B	1.381 (9)
C5A—H5A	0.9500	C5B—H5B	0.9500
C5A—C6A	1.394 (2)	C5B—C6B	1.382 (9)
C6A—C7A	1.395 (2)	C6B—C7B	1.383 (9)
C7A—H7A	0.9500	C7B—H7B	0.9500
C7A—C8A	1.391 (2)	C7B—C8B	1.379 (9)
C8A—C9A	1.395 (2)	C8B—C9B	1.388 (9)
C9A—H9A	0.9500	C9B—H9B	0.9500
N1A—H1A	0.883 (9)	N1B—H1B	0.8800
N1A—C11A	1.3234 (18)	N1B—C11B	1.313 (9)
N1A—C13A	1.376 (2)	N1B—C13B	1.360 (9)
N2A—H2A	0.873 (9)	N2B—H2B	0.8800
N2A—C11A	1.331 (2)	N2B—C11B	1.336 (10)
N2A—C12A	1.381 (2)	N2B—C12B	1.397 (10)
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C10A—C11A	1.480 (2)	C10B—C11B	1.473 (9)
C12A—H12A	0.9500	C12B—H12B	0.9500
C12A—C13A	1.349 (2)	C12B—C13B	1.341 (9)
C13A—H13A	0.9500	C13B—H13B	0.9500
N3A—H3A	0.881 (9)	N3B—H3B	0.8800
N3A—C15A	1.3287 (19)	N3B—C15B	1.318 (9)
N3A—C16A	1.375 (2)	N3B—C16B	1.360 (9)
N4A—H4A	0.877 (9)	N4B—H4B	0.8800
N4A—C15A	1.333 (2)	N4B—C15B	1.334 (9)
N4A—C17A	1.381 (3)	N4B—C17B	1.394 (10)
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C14A—C15A	1.476 (2)	C14B—C15B	1.472 (9)
C16A—H16A	0.9500	C16B—H16B	0.9500
C16A—C17A	1.352 (2)	C16B—C17B	1.347 (10)
C17A—H17A	0.9500	C17B—H17B	0.9500
N5A—H5AA	0.868 (9)	N5B—H5BA	0.8800
N5A—C19A	1.324 (2)	N5B—C19B	1.316 (9)
N5A—C21A	1.378 (2)	N5B—C21B	1.368 (9)
N6A—H6A	0.873 (9)	N6B—H6B	0.8800
N6A—C19A	1.337 (2)	N6B—C19B	1.343 (10)
N6A—C20A	1.383 (2)	N6B—C20B	1.400 (10)
C18A—H18A	0.9800	C18B—H18D	0.9800
C18A—H18B	0.9800	C18B—H18E	0.9800
C18A—H18C	0.9800	C18B—H18F	0.9800
C18A—C19A	1.473 (2)	C18B—C19B	1.468 (9)
C20A—H20A	0.9500	C20B—H20B	0.9500
C20A—C21A	1.349 (2)	C20B—C21B	1.341 (10)
C21A—H21A	0.9500	C21B—H21B	0.9500

O1A—C1A—C4A	115.95 (13)	O1B—C1B—C4B	120.2 (9)
O2A—C1A—O1A	124.87 (15)	O2B—C1B—O1B	121.0 (10)
O2A—C1A—C4A	119.16 (14)	O2B—C1B—C4B	118.6 (9)
O3A—C2A—C6A	115.77 (13)	O3B—C2B—C6B	119.9 (9)
O4A—C2A—O3A	124.98 (15)	O4B—C2B—O3B	120.8 (10)
O4A—C2A—C6A	119.24 (14)	O4B—C2B—C6B	119.2 (9)
O5A—C3A—C8A	116.00 (13)	O5B—C3B—C8B	119.0 (8)
O6A—C3A—O5A	124.60 (14)	O6B—C3B—O5B	121.5 (10)
O6A—C3A—C8A	119.40 (13)	O6B—C3B—C8B	119.4 (9)
C5A—C4A—C1A	120.71 (14)	C5B—C4B—C1B	123.5 (9)
C5A—C4A—C9A	119.10 (13)	C9B—C4B—C1B	118.8 (9)
C9A—C4A—C1A	120.20 (14)	C9B—C4B—C5B	117.7 (9)
C4A—C5A—H5A	119.5	C4B—C5B—H5B	119.1
C4A—C5A—C6A	121.00 (13)	C6B—C5B—C4B	121.8 (9)
C6A—C5A—H5A	119.5	C6B—C5B—H5B	119.1
C5A—C6A—C2A	119.89 (14)	C5B—C6B—C2B	118.4 (9)
C5A—C6A—C7A	118.99 (14)	C5B—C6B—C7B	118.7 (9)
C7A—C6A—C2A	121.08 (14)	C7B—C6B—C2B	122.9 (9)
C6A—C7A—H7A	119.5	C6B—C7B—H7B	119.2
C8A—C7A—C6A	120.96 (13)	C8B—C7B—C6B	121.5 (9)
C8A—C7A—H7A	119.5	C8B—C7B—H7B	119.2
C7A—C8A—C3A	120.22 (13)	C7B—C8B—C3B	119.2 (9)
C7A—C8A—C9A	119.10 (13)	C7B—C8B—C9B	118.0 (9)
C9A—C8A—C3A	120.67 (14)	C9B—C8B—C3B	122.8 (9)
C4A—C9A—C8A	120.84 (13)	C4B—C9B—C8B	122.3 (9)
C4A—C9A—H9A	119.6	C4B—C9B—H9B	118.8
C8A—C9A—H9A	119.6	C8B—C9B—H9B	118.8
C11A—N1A—H1A	123.1 (12)	C11B—N1B—H1B	126.2
C11A—N1A—C13A	108.45 (13)	C11B—N1B—C13B	107.6 (9)
C13A—N1A—H1A	128.4 (12)	C13B—N1B—H1B	126.2
C11A—N2A—H2A	121.3 (13)	C11B—N2B—H2B	125.5
C11A—N2A—C12A	108.88 (14)	C11B—N2B—C12B	109.0 (9)
C12A—N2A—H2A	129.8 (13)	C12B—N2B—H2B	125.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C11A—C10A—H10A	109.5	C11B—C10B—H10D	109.5
C11A—C10A—H10B	109.5	C11B—C10B—H10E	109.5
C11A—C10A—H10C	109.5	C11B—C10B—H10F	109.5
N1A—C11A—N2A	108.61 (14)	N1B—C11B—N2B	109.0 (8)
N1A—C11A—C10A	125.15 (14)	N1B—C11B—C10B	126.0 (11)
N2A—C11A—C10A	126.24 (14)	N2B—C11B—C10B	125.0 (11)
N2A—C12A—H12A	126.8	N2B—C12B—H12B	128.0
C13A—C12A—N2A	106.30 (15)	C13B—C12B—N2B	104.0 (9)
C13A—C12A—H12A	126.8	C13B—C12B—H12B	128.0
N1A—C13A—H13A	126.1	N1B—C13B—H13B	124.8
C12A—C13A—N1A	107.75 (14)	C12B—C13B—N1B	110.4 (9)
C12A—C13A—H13A	126.1	C12B—C13B—H13B	124.8
C15A—N3A—H3A	121.1 (12)	C15B—N3B—H3B	125.8
C15A—N3A—C16A	108.74 (13)	C15B—N3B—C16B	108.3 (9)
C16A—N3A—H3A	130.1 (12)	C16B—N3B—H3B	125.8
C15A—N4A—H4A	121.7 (13)	C15B—N4B—H4B	125.7
C15A—N4A—C17A	108.96 (15)	C15B—N4B—C17B	108.6 (9)
C17A—N4A—H4A	129.2 (13)	C17B—N4B—H4B	125.7
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C15A—C14A—H14A	109.5	C15B—C14B—H14D	109.5
C15A—C14A—H14B	109.5	C15B—C14B—H14E	109.5
C15A—C14A—H14C	109.5	C15B—C14B—H14F	109.5
N3A—C15A—N4A	108.31 (15)	N3B—C15B—N4B	108.7 (9)
N3A—C15A—C14A	125.30 (14)	N3B—C15B—C14B	126.4 (11)
N4A—C15A—C14A	126.38 (16)	N4B—C15B—C14B	124.5 (11)
N3A—C16A—H16A	126.2	N3B—C16B—H16B	125.5
C17A—C16A—N3A	107.51 (15)	C17B—C16B—N3B	109.1 (9)
C17A—C16A—H16A	126.2	C17B—C16B—H16B	125.5
N4A—C17A—H17A	126.8	N4B—C17B—H17B	127.4
C16A—C17A—N4A	106.47 (14)	C16B—C17B—N4B	105.1 (9)
C16A—C17A—H17A	126.8	C16B—C17B—H17B	127.4
C19A—N5A—H5AA	122.0 (13)	C19B—N5B—H5BA	125.8
C19A—N5A—C21A	108.61 (13)	C19B—N5B—C21B	108.4 (8)
C21A—N5A—H5AA	129.1 (13)	C21B—N5B—H5BA	125.8
C19A—N6A—H6A	123.4 (13)	C19B—N6B—H6B	125.7
C19A—N6A—C20A	108.66 (15)	C19B—N6B—C20B	108.6 (9)
C20A—N6A—H6A	127.8 (13)	C20B—N6B—H6B	125.7
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C19A—C18A—H18A	109.5	C19B—C18B—H18D	109.5
C19A—C18A—H18B	109.5	C19B—C18B—H18E	109.5
C19A—C18A—H18C	109.5	C19B—C18B—H18F	109.5
N5A—C19A—N6A	108.55 (14)	N5B—C19B—N6B	108.2 (9)
N5A—C19A—C18A	125.28 (14)	N5B—C19B—C18B	127.0 (11)
N6A—C19A—C18A	126.14 (15)	N6B—C19B—C18B	124.5 (11)
N6A—C20A—H20A	126.7	N6B—C20B—H20B	127.5
C21A—C20A—N6A	106.55 (14)	C21B—C20B—N6B	105.0 (9)
C21A—C20A—H20A	126.7	C21B—C20B—H20B	127.5
N5A—C21A—H21A	126.2	N5B—C21B—H21B	125.4
C20A—C21A—N5A	107.63 (13)	C20B—C21B—N5B	109.2 (9)
C20A—C21A—H21A	126.2	C20B—C21B—H21B	125.4

O1A—C1A—C4A—C5A	179.42 (14)	O1B—C1B—C4B—C5B	171.5 (18)
O1A—C1A—C4A—C9A	−0.3 (2)	O1B—C1B—C4B—C9B	−4 (3)
O2A—C1A—C4A—C5A	1.2 (2)	O2B—C1B—C4B—C5B	−4 (3)
O2A—C1A—C4A—C9A	−178.44 (14)	O2B—C1B—C4B—C9B	−179.6 (17)
O3A—C2A—C6A—C5A	4.3 (2)	O3B—C2B—C6B—C5B	−1 (3)
O3A—C2A—C6A—C7A	−173.16 (14)	O3B—C2B—C6B—C7B	−179.7 (16)
O4A—C2A—C6A—C5A	−176.84 (14)	O4B—C2B—C6B—C5B	−177.6 (16)
O4A—C2A—C6A—C7A	5.7 (2)	O4B—C2B—C6B—C7B	4 (3)
O5A—C3A—C8A—C7A	−4.4 (2)	O5B—C3B—C8B—C7B	2 (3)
O5A—C3A—C8A—C9A	177.30 (14)	O5B—C3B—C8B—C9B	−178.6 (18)
O6A—C3A—C8A—C7A	174.65 (14)	O6B—C3B—C8B—C7B	−174.1 (17)
O6A—C3A—C8A—C9A	−3.7 (2)	O6B—C3B—C8B—C9B	5 (3)
C1A—C4A—C5A—C6A	−179.09 (14)	C1B—C4B—C5B—C6B	−176.2 (17)
C1A—C4A—C9A—C8A	178.51 (14)	C1B—C4B—C9B—C8B	175.4 (17)
C2A—C6A—C7A—C8A	175.60 (14)	C2B—C6B—C7B—C8B	178.0 (17)
C3A—C8A—C9A—C4A	178.58 (14)	C3B—C8B—C9B—C4B	−178.6 (17)
C4A—C5A—C6A—C2A	−176.59 (14)	C4B—C5B—C6B—C2B	−177.7 (17)
C4A—C5A—C6A—C7A	0.9 (2)	C4B—C5B—C6B—C7B	1 (3)
C5A—C4A—C9A—C8A	−1.2 (2)	C5B—C4B—C9B—C8B	−1 (3)
C5A—C6A—C7A—C8A	−1.8 (2)	C5B—C6B—C7B—C8B	−1 (3)
C6A—C7A—C8A—C3A	−177.06 (14)	C6B—C7B—C8B—C3B	179.3 (16)
C6A—C7A—C8A—C9A	1.3 (2)	C6B—C7B—C8B—C9B	0 (3)
C7A—C8A—C9A—C4A	0.2 (2)	C7B—C8B—C9B—C4B	1 (3)
C9A—C4A—C5A—C6A	0.6 (2)	C9B—C4B—C5B—C6B	−1 (3)
N2A—C12A—C13A—N1A	−0.4 (2)	N2B—C12B—C13B—N1B	−2 (3)
C11A—N1A—C13A—C12A	−0.12 (19)	C11B—N1B—C13B—C12B	2 (2)
C11A—N2A—C12A—C13A	0.8 (3)	C11B—N2B—C12B—C13B	1 (4)
C12A—N2A—C11A—N1A	−0.8 (3)	C12B—N2B—C11B—N1B	0 (4)
C12A—N2A—C11A—C10A	179.21 (17)	C12B—N2B—C11B—C10B	−179 (2)
C13A—N1A—C11A—N2A	0.6 (2)	C13B—N1B—C11B—N2B	−1 (3)
C13A—N1A—C11A—C10A	−179.45 (16)	C13B—N1B—C11B—C10B	177 (2)
N3A—C16A—C17A—N4A	0.2 (3)	N3B—C16B—C17B—N4B	1 (3)
C15A—N3A—C16A—C17A	−0.52 (19)	C15B—N3B—C16B—C17B	3 (2)
C15A—N4A—C17A—C16A	0.3 (4)	C15B—N4B—C17B—C16B	−3 (5)
C16A—N3A—C15A—N4A	0.7 (3)	C16B—N3B—C15B—N4B	−5 (3)
C16A—N3A—C15A—C14A	−178.42 (16)	C16B—N3B—C15B—C14B	−178.0 (19)
C17A—N4A—C15A—N3A	−0.6 (4)	C17B—N4B—C15B—N3B	5 (5)
C17A—N4A—C15A—C14A	178.51 (19)	C17B—N4B—C15B—C14B	179 (2)
N6A—C20A—C21A—N5A	−0.1 (3)	N6B—C20B—C21B—N5B	0 (3)
C19A—N5A—C21A—C20A	0.1 (2)	C19B—N5B—C21B—C20B	−5 (2)
C19A—N6A—C20A—C21A	0.2 (3)	C19B—N6B—C20B—C21B	5 (3)
C20A—N6A—C19A—N5A	−0.1 (3)	C20B—N6B—C19B—N5B	−8 (4)
C20A—N6A—C19A—C18A	178.17 (19)	C20B—N6B—C19B—C18B	178 (2)
C21A—N5A—C19A—N6A	0.0 (3)	C21B—N5B—C19B—N6B	8 (3)
C21A—N5A—C19A—C18A	−178.26 (16)	C21B—N5B—C19B—C18B	−178.8 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1Aⁱ	0.88 (1)	1.73 (1)	2.6101 (17)	174 (2)
N2A—H2A···O4Aⁱⁱ	0.87 (1)	1.83 (1)	2.6888 (18)	169 (2)
C10A—H10C···O2Aⁱ	0.98	2.42	3.390 (2)	171
C12A—H12A···O5Aⁱⁱ	0.95	2.45	3.338 (2)	156
N3A—H3A···O5Aⁱⁱⁱ	0.88 (1)	1.76 (1)	2.6309 (16)	172 (2)
N4A—H4A···O2A	0.88 (1)	1.82 (1)	2.682 (2)	170 (2)
C14A—H14B···O6Aⁱⁱⁱ	0.98	2.43	3.3867 (19)	165
C17A—H17A···O3A	0.95	2.44	3.3202 (19)	155
N5A—H5AA···O3A^iv	0.87 (1)	1.75 (1)	2.6131 (17)	173 (2)
N6A—H6A···O6A^v	0.87 (1)	1.86 (1)	2.713 (2)	167 (2)
C18A—H18A···O1A	0.98	2.63	3.462 (2)	143
C18A—H18C···O4A^iv	0.98	2.45	3.371 (2)	157
C20A—H20A···O1A^v	0.95	2.38	3.2993 (19)	164
N1B—H1B···O1B^iv	0.88	1.64	2.510 (16)	169
N2B—H2B···O4B^v	0.88	1.75	2.606 (16)	165
C10B—H10D···O2B^iv	0.98	2.61	3.51 (2)	151
C10B—H10E···O2B^vi	0.98	2.05	2.85 (3)	137
C12B—H12B···O5B^v	0.95	2.58	3.475 (15)	157
N3B—H3B···O5B^vii	0.88	1.66	2.522 (15)	168
N4B—H4B···O2B^iv	0.88	1.75	2.598 (16)	162
C17B—H17B···O3B^iv	0.95	2.52	3.442 (16)	164
N5B—H5BA···O3Bⁱ	0.88	1.65	2.518 (15)	168
N6B—H6B···O6Bⁱⁱ	0.88	1.83	2.648 (19)	153

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

Selected bond lengths (Å), angles (°), and torsion angles (°) of the btc^3- ions top

1a		1b
C4—C5	1.392 (2)	C4—C5	1.38 (2)
C5—C6	1.394 (2)	C5—C6	1.38 (2)
C6—C7	1.395 (2)	C6—C7	1.38 (2)
C7—C8	1.391 (2)	C7—C8	1.38 (2)
C8—C9	1.395 (2)	C8—C9	1.39 (2)
C9—C4	1.394 (2)	C9—C4	1.38 (2)
C1—C4	1.513 (2)	C1—C4	1.52 (2)
C2—C6	1.516 (2)	C2—C6	1.52 (1)
C3—C8	1.516 (2)	C3—C8	1.52 (2)
C1—O1	1.263 (2)	C1—O1	1.27 (1)
C1—O2	1.257 (2)	C1—O2	1.25 (2)
C2—O3	1.267 (2)	C2—O3	1.27 (2)
C2—O4	1.253 (2)	C2—O4	1.24 (1)
C3—O5	1.268 (2)	C3—O5	1.27 (2)
C3—O6	1.252 (2)	C3—O6	1.25 (1)
C4—C5—C6	121.0 (1)	C4—C5—C6	122 (1)
C5—C6—C7	119.0 (1)	C5—C6—C7	119 (1)
C6—C7—C8	121.0 (1)	C6—C7—C8	121 (1)
C7—C8—C9	119.1 (1)	C7—C8—C9	118 (1)
C8—C9—C4	120.8 (1)	C8—C9—C4	122 (1)
C9—C4—C5	119.1 (1)	C9—C4—C5	118 (1)
O1—C1—O2	124.9 (1)	O1—C1—O2	121 (1)
O3—C2—O4	125.0 (1)	O3—C2—O4	121 (1)
O5—C3—O6	124.6 (1)	O5—C3—O6	121 (1)
C5—C4—C1—O1	179.4 (1)	C5—C4—C1—O1	171 (1)
C5—C4—C1—O2	1.2 (2)	C5—C4—C1—O2	-4 (2)
C9—C4—C1—O1	-0.3 (2)	C9—C4—C1—O1	-4 (2)
C9—C4—C1—O2	-178.4 (1)	C9—C4—C1—O2	-180 (1)
C5—C6—C2—O3	4.3 (2)	C5—C6—C2—O3	-1 (2)
C5—C6—C2—O4	-176.8 (1)	C5—C6—C2—O4	-178 (1)
C7—C6—C2—O3	-173.2 (1)	C7—C6—C2—O3	-180 (1)
C7—C6—C2—O4	5.7 (2)	C7—C6—C2—O4	3 (2)
C7—C8—C3—O5	-4.4 (2)	C7—C8—C3—O5	2 (2)
C7—C8—C3—O6	174.7 (1)	C7—C8—C3—O6	-174 (1)
C9—C8—C3—O5	177.3 (1)	C9—C8—C3—O5	-179 (1)
C9—C8—C3—O6	-3.7 (2)	C9—C8—C3—O6	6 (2)

Root-mean-square-deviation and maximal deviation values calculated for molecular overlays of btc^3- in 1 and other reported btc structures top

	1a		1b
	r.m.s.d	max. d.	r.m.s.d.	max. d.
H₃btc (Tothadi et al., 2020)	0.0695	0.1509	0.0643	0.1098
H₂btc^- (Baletska et al., 2023)	0.1067	0.2231	0.1383	0.3149
H₂btc^- (Asprilla-Herrera et al., 2025)	0.0592	0.1135	0.0776	0.1626
Hbtc^2- (Asprilla-Herrera et al., 2025)	0.1522	0.3301	0.1804	0.3712

Selected bond lengths (Å), angles (°), and torsion angles (°C) of the H2-mIm⁺ ions top

Xa		Ya		Za
C10—C11	1.480 (2)	C14—C15	1.476 (2)	C18—C19	1.473 (2)
C12—C13	1.349 (2)	C16—C17	1.352 (2)	C20—C21	1.349 (2)
N1—C11	1.323 (2)	N3—C15	1.329 (2)	N5—C19	1.324 (2)
N1—C13	1.376 (2)	N3—C16	1.375 (2)	N5—C21	1.378 (2)
N2—C11	1.331 (2)	N4—C15	1.333 (3)	N6—C19	1.336 (3)
N2—C12	1.381 (3)	N4—C17	1.380 (3)	N6—C20	1.382 (3)
C10—C11—N1	125.1 (1)	C14—C15—N3	125.3 (1)	C18—C19—N5	125.3 (1)
C11—N1—C13	108.5 (1)	C15—N3—C16	108.7 (1)	C19—N5—C21	108.6 (1)
N1—C13—C12	107.8 (1)	N3—C16—C17	107.5 (1)	N5—C21—C20	107.6 (2)
C13—C12—N2	106.3 (2)	C16—C17—N4	106.5 (2)	C21—C20—N6	106.6 (2)
C12—N2—C11	108.9 (2)	C17—N4—C15	109.0 (2)	C20—N6—C19	108.7 (2)
N2—C11—N1	108.6 (2)	N4—C15—N3	108.3 (2)	N6—C19—N5	108.5 (2)
N2—C11—C10	126.3 (2)	N4—C15—C14	126.4 (2)	N6—C19—C18	126.1 (2)
C13—N1—C11—C10	179.5 (2)	C16—N3—C15—C14	-178.4 (2)	C21—N5—C19—C18	178.3 (2)
C12—N2—C11—C10	-179.2 (2)	C17—N4—C15—C14	178.5 (2)	C20—N6—C19—C18	-178.1 (2)

Xb		Yb		Zb
C10—C11	1.48 (2)	C14—C15	1.47 (2)	C18—C19	1.47 (2)
C12—C13	1.34 (2)	C16—C17	1.35 (2)	C20—C21	1.34 (2)
N1—C11	1.31 (2)	N3—C15	1.32 (2)	N5—C19	1.32 (1)
N1—C13	1.36 (2)	N3—C16	1.36 (2)	N5—C21	1.37 (2)
N2—C11	1.34 (2)	N4—C15	1.34 (4)	N6—C19	1.34 (3)
N2—C12	1.39 (3)	N4—C17	1.39 (2)	N6—C20	1.40 (3)
C10—C11—N1	126 (1)	C14—C15—N3	126 (1)	C18—C19—N5	127 (1)
C11—N1—C13	108 (1)	C15—N3—C16	108 (1)	C19—N5—C21	108 (1)
N1—C13—C12	110 (1)	N3—C16—C17	109 (1)	N5—C21—C20	109 (1)
C13—C12—N2	104 (2)	C16—C17—N4	105 (2)	C21—C20—N6	105 (1)
C12—N2—C11	109 (2)	C17—N4—C15	109 (2)	C20—N6—C19	109 (2)
N2—C11—N1	109 (2)	N4—C15—N3	108 (2)	N6—C19—N5	108 (1)
N2—C11—C10	125 (2)	N4—C15—C14	125 (2)	N6—C19—C18	124 (2)
C13—N1—C11—C10	-177 (2)	C16—N3—C15—C14	178 (1)	C21—N5—C19—C18	179 (1)
C12—N2—C11—C10	178 (2)	C17—N4—C15—C14	-179 (2)	C20—N6—C19—C18	-178 (2)

Root-mean-square-deviation and maximal deviation values calculated for molecular overlays of H2-mIm⁺ ions in 1 and other reported 2-mIm structures top

	Xa		Ya		Za
	r.m.s.d.	max. d.	r.m.s.d.	max. d.	r.m.s.d.	max. d.
2-mIm (Hachuła et al., 2010)	0.0269	0.0430	0.0268	0.0430	0.0268	0.0385
H2-mIm⁺ (Baletska et al., 2023)	0.0102	0.0125	0.0093	0.0123	0.0141	0.0202
H2-mIm⁺ ion A (Asprilla-Herrera et al., 2025)	0.0123	0.0167	0.0094	0.0143	0.0111	0.0169
H2-mIm⁺ ion B (Asprilla-Herrera et al., 2025)	0.0050	0.0076	0.0064	0.0097	0.0075	0.0108
H2-mIm⁺ ion C (Asprilla-Herrera et al., 2025)	0.0075	0.0104	0.0091	0.0120	0.0103	0.0157

	Xb		Yb		Zb
2-mIm (Hachuła et al., 2010)	0.0265	0.0409	0.0298	0.0451	0.0419	0.0612
H2-mIm⁺ (Baletska et al., 2023)	0.0216	0.0352	0.0233	0.0390	0.0368	0.0468
H2-mIm⁺ ion A (Asprilla-Herrera et al., 2025)	0.0214	0.0351	0.0255	0.0462	0.0331	0.0437
H2-mIm⁺ ion B (Asprilla-Herrera et al., 2025)	0.0178	0.0317	0.0203	0.0372	0.0309	0.0431
H2-mIm⁺ ion C (Asprilla-Herrera et al., 2025)	0.0237	0.0404	0.0227	0.0342	0.0359	0.0470

Geometrical details of π–π interactions (Å) in 1 top

Ion	H2-mIm^-	Centroid-to-centroid distance	Perpendicular distance	Offset
btc^3- (1a)	Xa	3.6855 (10)	3.3	1.629
btc^3- (1a)	Za	3.8392 (12)	3.4	1.771
Xa	Ya	3.4548 (12)	3.2	1.294
Ya	Za	3.5466 (13)	3.3	1.482
btc^3- (1b)	Xb	3.769 (11)	3.4	1.881
btc^3- (1b)	Zb	3.694 (10)	3.2	1.87
Xb	Yb	3.416 (13)	3.4	0.195
Yb	Zb	3.544 (13)	3.5	0.347

Hydrogen-bond geometry (Å, °) top

	Graph-set descriptor	Type	D—H	H···A	D···A	D—H···A
N1A—H1AA···O1A^iv	D(2)	a	0.883 (9)	1.730 (10)	2.6101 (17)	174.4 (18)
N2A—H2A···O4A^v	D(2)	b	0.873 (9)	1.828 (10)	2.6888 (18)	168.5 (18)
N3A—H3A···O5A^vi	D(2)	c	0.881 (9)	1.755 (10)	2.6309 (16)	172.3 (18)
N4A—H4A···O2A	D(2)	d	0.877 (9)	1.815 (10)	2.682 (2)	169.8 (18)
N5A—H5AA···O3Aⁱ	D(2)	e	0.868 (9)	1.749 (10)	2.6131 (17)	173.2 (19)
N6A—H6A···O6A^vii	D(2)	f	0.873 (9)	1.857 (10)	2.713 (2)	166.7 (18)
N1B—H1B···O1Bⁱ	D(2)	a	0.88	1.64	2.510 (16)	169.2
N2B—H2B···O4B^vii	D(2)	b	0.88	1.75	2.606 (16)	164.9
N3B—H3B···O5Bⁱⁱⁱ	D(2)	c	0.88	1.66	2.522 (15)	167.6
N4B—H4B···O2Bⁱ	D(2)	d	0.88	1.75	2.598 (16)	161.8
N5B—H5BA···O3B^iv	D(2)	e	0.88	1.65	2.518 (15)	168.4
N6B—H6B···O6B^v	D(2)	f	0.88	1.83	2.648 (19)	153.2
C10A—H10C···O2A^iv			0.98	2.42	3.390 (2)	170.8
C12A—H12A···O5A^v			0.95	2.45	3.338 (2)	156
C14A—H14B···O6A^vi			0.98	2.43	3.3867 (19)	165
C17A—H17A···O3A			0.95	2.44	3.3202 (19)	154.5
C18A—H18A···O1A			0.98	2.63	3.462 (2)	143.2
C18A—H18C···O4Aⁱ			0.98	2.45	3.371 (2)	156.5
C20A—H20A···O1A^vii			0.95	2.38	3.2993 (19)	163.5
C10B—H10D···O2Bⁱ			0.98	2.61	3.51 (2)	151.4
C10B—H10E···O2Bⁱⁱ			0.98	2.05	2.85 (3)	136.8
C12B—H12B···O5B^vii			0.95	2.58	3.475 (15)	157.1
C17B—H17B···O3Bⁱ			0.95	2.52	3.442 (16)	164.3

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

Second-level graph sets in 1 top

C²₂(12)	>a<b	D²₂(9)	>b<c	D²₂(9)	>c<e
D²₂(9)	>a<c	D²₂(9)	>b<d	D²₂(5)	>c<f
D²₂(5)	>a<d	D²₂(5)	>b<e	D²₂(9)	>d<e
D²₂(9)	>a<e	D²₂(9)	>b<f	D²₂(9)	>d<f
D²₂(9)	>a<f	C²₂(12)	>c<d	C²₂(12)	>e<f

Intermolecular interaction contribution (%) from Hirshfeld surface analysis of 1 top

	btc^3-	btc^3-	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺	H2-mIm⁺
	1a	1b	Xa	Ya	Za	Xb	Yb	Zb
O—O	0	1.3	–	–	–	–	–	–
O—C	2.2	2.8	–	–	–	–	–	–
O—H	56.2	52.8	–	–	–	–	–	–
O—N	0	0.1	–	–	–	–	–	–
C—O	2.7	2.9	0.3	0.2	0.5	0.6	0	0.8
C—C	5.3	6.9	5	2.7	5.2	6.5	4.7	6
C—H	12.2	9.8	3.7	5.1	3	0.4	0.5	0.9
C—N	2	2.4	1.1	2.3	1	2.3	4.2	2
H—N	1.3	1	1	2.3	1.3	0.6	1.1	0.6
H—H	15.2	17.5	50.2	55.4	49.3	54.6	62.9	53.4
H—C	1.4	0.1	7.5	3.6	7.1	3.9	1.1	5.1
H—O	1.4	2.4	24.5	21.8	26.1	24.6	19.2	24.7
N—O	–	–	0	0.1	0	0.1	0	0.1
N—C	–	–	2.8	2.1	2.7	4.3	4.2	3.9
N—H	–	–	3	2.6	2.8	1.8	1.2	2
N—N	–	–	0.9	2	1.1	0.4	1	0.6

Acknowledgements

Funding for this research was provided by: HG-recruitment, HG-Innovation ECRAPS, HG-Innovation DSF/DASHH and CMWS (grant to ST). WŁ thanks the DESY-Helmholtz-Summer student fund for financial support.

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