2-(2-Meth­oxy­phen­yl)-4,5-bis­(4-methyl­phen­yl)-1H-imidazol-3-ium 2,4,6-tri­nitro­phenolate

Solo, P.; Doss, M.A.; Pillay, M.; William Raja, T.R.; Lizhohrii, C.; Mi, A.; Shimray, N.

doi:10.1107/S2414314626005602

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 6| June 2026| x260560

https://doi.org/10.1107/S2414314626005602

Open

access

2-(2-Methoxyphenyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium 2,4,6-trinitrophenolate

Peter Solo,^a,^b ^* M. Arockia Doss,^c Michael Pillay,^d Tharsius Raja William Raja,^d,^e Cecillia Lizhohrii,^a Agnes Mi ^a and Nimchan Shimray ^a

^aDepartment of Chemistry, St. Joseph's College (A), Jakhama, Nagaland, 797001, India, ^bDepartment of Environmental Studies, St. Xavier College, Jalukie, Nagaland, India, ^cSchool of Science and Humanities, St. Joseph University, Emmanuel Educity, Tindivanam-604307, India, ^dDepartment of Life and Consumer Sciences, College of Agriculture and Environmental Sciences, Florida Campus, University of South Africa, Johannesburg 1709, South Africa, and ^ePostgraduate and Research Department of Biotechnology, Bishop Heber College (Autonomous), Tiruchirappalli, Tamil Nadu - 620 017, India
^*Correspondence e-mail: [email protected]

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 25 May 2026; accepted 27 May 2026; online 2 June 2026)

The title imidazolium picrate salt, C₂₄H₂₃N₂O⁺·C₆H₂N₃O₇⁻, crystallizes in the triclinic space group P1. The asymmetric unit consists of one imidazolium cation and one picrate anion. The molecular structure is consolidated by an intramolecular N—H⋯O hydrogen bond within the imidazolium cation and by an intermolecular N—H⋯O hydrogen bond between the imidazolium cation and the picrate anion. In the crystal, the ions are further associated through π–π stacking interactions, contributing to the supramolecular packing arrangement. Two nitro groups of the picrate anion were modelled as disordered over two positions.

Keywords: crystal structure; hydrogen bonds; π-stacking.

CCDC reference: 2555221

Structure description

Imidazole and its derivatives are an important class of heterocycles in medicinal chemistry and materials science because of their diverse biological properties and their ability to participate in supramolecular assembly (Li et al., 2023 ). Substituted imidazolium salts are of structural interest since their molecular conformations and crystal packing are often governed by non-covalent interactions such as hydrogen bonding and π–π stacking (Desiraju, 2002 ). Picric acid, 2,4,6-trinitrophenol, is a common acidic co-former for the formation of organic salts with nitrogen-containing bases (Bertolasi et al., 2011 ). Related imidazolium picrate structures have also been reported previously (Du & Zhao, 2003 ; Dutkiewicz et al., 2011 ; Solo et al., 2025 ). In the present study, the crystal structure of 2-(2-methoxyphenyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium 2,4,6-trinitrophenolate was determined in order to establish the molecular conformation of the imidazolium cation and to examine the hydrogen-bonding and π–π stacking interactions responsible for the crystal packing.

The asymmetric unit of the title salt, C₂₄H₂₃N₂O⁺·C₆H₂N₃O₇⁻, contains one 2-(2-methoxyphenyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium cation and one 2,4,6-trinitrophenolate anion (Fig. 1). Proton transfer from picric acid to the imidazole N atom gives the imidazolium cation and the picrate anion.

Figure 1
Asymmetric unit of the title imidazolium picrate salt, with displacement ellipsoids drawn at the 50% probability level. Dashed lines (magenta) indicate N—H⋯O hydrogen-bonding interactions. The split oxygen atoms of two nitro groups are coloured in green.

The molecular conformation is consolidated by an intramolecular N2—H2⋯O8 hydrogen bond within the imidazolium cation, involving the imidazolium N—H group and the methoxy O atom. In addition, an intermolecular N1—H1⋯O1 hydrogen bond links the imidazolium cation to the picrate anion. These N—H⋯O interactions help organize the cation–anion pairs and contribute to the crystal packing arrangement (Fig. 2). The hydrogen-bonding details are listed in Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.82	2.661 (2)	167
N2—H2⋯O8	0.86	2.05	2.601 (2)	122

Figure 2
Unit-cell packing diagram of the title imidazolium picrate salt, showing the arrangement of the imidazolium cations and picrate anions in the triclinic P $[\overline{1}]$ unit cell. Hydrogen-bonding interactions are shown as magenta dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

The packing is further consolidated by π–π stacking interactions between the picrate aromatic ring and an aromatic ring of the imidazolium cation (Fig. 3). The centroid–centroid separation is 3.712 (2) Å, the slippage is 0.69 Å and the dihedral angle between the interacting ring planes is 8.12 (14)°, indicating a nearly parallel arrangement of the aromatic rings (Janiak, 2000 ).

Figure 3
π–π stacking interaction between the picrate ring and the p-tolyl ring, showing a centroid–centroid distance of 3.712 (2) Å, and a dihedral angle of 8.12 (14)°.

Two nitro groups of the picrate anion are disordered over two positions. The disorder was modelled using two sets of oxygen positions, with refined occupancies of 0.69 (4):0.31 (4) and 0.74 (3):0.26 (3) for the major and minor components, respectively. The disordered nitro groups were restrained to maintain chemically reasonable N—O and O⋯O distances and acceptable displacement parameters.

Synthesis and crystallization

2-(2-Methoxyphenyl)-4,5-bis(4-methylphenyl)-1H-imidazol (4) was synthesized by a one-pot condensation reaction of 4,4-dimethylbenzil (1) (0.953 g, 0.004 mol), 2-methoxybenzaldehyde (3) (0.545 g, 0.004 mol), and ammonium acetate (2) (1.233 g, 0.016 mol) in the presence of ceric ammonium nitrate (CAN) as catalyst. Ethanol was used as the solvent and the reflux was carried out at 95°C. The progress of the reaction was monitored with TLC (hexane:ethyl acetate, 1:1) and at the completion of the reaction the mixture was poured into ice-cold water. The precipitate was collected and purified with multiple recrystallization in 90% ethanol. Equimolar amounts of 2-(2-methoxyphenyl)-4,5-bis(4-methylphenyl)-1H-imidazol (0.071 g, 0.0002 mol) and picric acid (0.046 g, 0.0002 mol) were dissolved in 100% ethanol and heated to 120°C. The solution was kept still in a dark environment for days until yellow crystals of imidazolium picrate (6) appeared (Fig. 4).

Figure 4
Synthesis of the title imidazolium picrate salt (6) from 4,4′-dimethylbenzil (1), ammonium acetate (2), 2-methoxybenzaldehyde (3) and picric acid (5). The imidazole intermediate (4) was obtained in ethanol/CAN under reflux at 95°C, followed by salt formation with picric acid.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were placed in calculated positions and refined using a riding model, with methyl groups treated as rotating groups. The picrate anion showed disorder affecting two nitro groups. The O6/O7 and O4/O5 nitro oxygen atoms were modelled over two sets of positions, with refined occupancies of 0.69 (4)(major):0.31 (4)(minor) and 0.74 (3)(major):0.26 (3)(minor), respectively. The corresponding disordered atoms were assigned to PART 1 and PART 2 using linked free variables. SADI restraints were applied to maintain chemically reasonable N—O and O⋯O distances within the disordered nitro groups, while SIMU and RIGU restraints were used to restrain the anisotropic displacement parameters of the nitro-group atoms. Similar ADP restraints were also applied to the remaining nitro group to account for enlarged displacement parameters. The final weighting scheme was applied and the refinement converged with low residual electron density.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₃N₂O⁺·C₆H₂N₃O₇⁻
M_r	583.55
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.4517 (19), 12.359 (3), 13.626 (3)
α, β, γ (°)	91.961 (6), 103.983 (6), 91.860 (7)
V (Å³)	1379.1 (5)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.18 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	58614, 6492, 3785
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.155, 1.00
No. of reflections	6492
No. of parameters	430
No. of restraints	206
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16
Computer programs: APEX2 (and SAINT (Bruker, 2018 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2025/1 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2555221

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626005602/bt4200sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626005602/bt4200Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626005602/bt4200Isup3.cml

checkCIF report

Computing details top

2-(2-Methoxyphenyl)-4,5-bis(4-methylphenyl)-1H-imidazol-3-ium 2,4,6-trinitrophenolate top

Crystal data top

C₂₄H₂₃N₂O⁺·C₆H₂N₃O₇⁻	Z = 2
M_r = 583.55	F(000) = 608
Triclinic, P1	D_x = 1.405 Mg m⁻³
a = 8.4517 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.359 (3) Å	Cell parameters from 5303 reflections
c = 13.626 (3) Å	θ = 2.3–21.5°
α = 91.961 (6)°	µ = 0.10 mm⁻¹
β = 103.983 (6)°	T = 296 K
γ = 91.860 (7)°	Block, clear yellowish orange
V = 1379.1 (5) Å³	0.25 × 0.18 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.079
φ and ω scans	θ_max = 27.8°, θ_min = 1.5°
58614 measured reflections	h = −11→11
6492 independent reflections	k = −16→16
3785 reflections with I > 2σ(I)	l = −17→17

Refinement top

Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.155	(Δ/σ)_max = 0.001
S = 1.00	Δρ_max = 0.25 e Å⁻³
6492 reflections	Δρ_min = −0.16 e Å⁻³
430 parameters	Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
206 restraints	Extinction coefficient: 0.0146 (18)
Primary atom site location: dual

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.

Refinement. The structure was solved with SHELXT 2018/2 (Sheldrick, 2015b) using intrinsic phasing in the triclinic space group P1 and refined by full-matrix least-squares on F² using SHELXL 2025/1 (Sheldrick, 2015a) within OLEX2. All non-hydrogen atoms were refined anisotropically.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4853 (2)	0.30529 (15)	0.09982 (13)	0.0363 (4)
C2	0.3818 (2)	0.39655 (15)	0.06932 (14)	0.0388 (4)
C3	0.3181 (3)	0.41538 (18)	−0.03149 (15)	0.0472 (5)
H3	0.340672	0.368829	−0.080982	0.057*
C4	0.2216 (3)	0.50208 (18)	−0.05992 (16)	0.0513 (6)
H4	0.179581	0.512070	−0.128498	0.062*
C5	0.1852 (3)	0.57407 (17)	0.00922 (17)	0.0470 (5)
C6	0.0801 (3)	0.66833 (19)	−0.0219 (2)	0.0636 (7)
H6A	0.080399	0.685042	−0.090154	0.095*
H6B	0.122080	0.730101	0.022492	0.095*
H6C	−0.029456	0.650259	−0.018000	0.095*
C7	0.2475 (3)	0.5545 (2)	0.10897 (18)	0.0699 (8)
H7	0.224295	0.601298	0.158085	0.084*
C8	0.3434 (3)	0.4682 (2)	0.13924 (17)	0.0684 (8)
H8	0.382946	0.457803	0.207963	0.082*
C9	0.5620 (2)	0.26805 (15)	0.19136 (13)	0.0371 (4)
C10	0.5798 (2)	0.30630 (15)	0.29722 (13)	0.0382 (4)
C11	0.6787 (3)	0.39536 (18)	0.33662 (16)	0.0588 (6)
H11	0.728526	0.435304	0.294933	0.071*
C12	0.7047 (4)	0.4261 (2)	0.43808 (17)	0.0694 (7)
H12	0.772396	0.486565	0.463553	0.083*
C13	0.6336 (3)	0.3698 (2)	0.50166 (15)	0.0592 (6)
C14	0.6675 (5)	0.4030 (3)	0.61299 (18)	0.0948 (11)
H14A	0.566647	0.403341	0.633654	0.142*
H14B	0.718963	0.474251	0.624110	0.142*
H14C	0.738340	0.352523	0.651819	0.142*
C15	0.5350 (3)	0.2809 (2)	0.46217 (17)	0.0644 (7)
H15	0.485591	0.241248	0.504209	0.077*
C16	0.5076 (3)	0.24905 (19)	0.36137 (16)	0.0546 (6)
H16	0.439959	0.188458	0.336301	0.065*
C17	0.6164 (2)	0.15653 (15)	0.07255 (13)	0.0347 (4)
C18	0.6833 (2)	0.06963 (15)	0.02284 (13)	0.0364 (4)
C19	0.7747 (3)	−0.00823 (16)	0.08002 (15)	0.0433 (5)
H19	0.791751	−0.004604	0.150105	0.052*
C20	0.8400 (3)	−0.09065 (18)	0.03382 (17)	0.0518 (6)
H20	0.900649	−0.142369	0.072675	0.062*
C21	0.8156 (3)	−0.09635 (18)	−0.06953 (17)	0.0534 (6)
H21	0.860003	−0.152130	−0.100291	0.064*
C22	0.7263 (3)	−0.02068 (18)	−0.12814 (16)	0.0498 (5)
H22	0.710708	−0.025245	−0.198125	0.060*
C23	0.6596 (2)	0.06255 (16)	−0.08264 (14)	0.0401 (5)
C24	0.5352 (4)	0.1358 (3)	−0.24251 (17)	0.0837 (9)
H24A	0.470770	0.195726	−0.268477	0.126*
H24B	0.475928	0.069056	−0.268077	0.126*
H24C	0.635683	0.139146	−0.263578	0.126*
C25	0.8692 (3)	0.11473 (17)	0.41365 (14)	0.0450 (5)
C26	0.9880 (3)	0.20295 (19)	0.42170 (15)	0.0517 (6)
C27	1.0675 (3)	0.2554 (2)	0.51019 (17)	0.0627 (7)
H27	1.141307	0.312900	0.510247	0.075*
C28	1.0371 (3)	0.22234 (19)	0.59978 (16)	0.0628 (7)
C29	0.9290 (3)	0.13748 (18)	0.60059 (15)	0.0551 (6)
H29	0.910949	0.115200	0.661617	0.066*
C30	0.8483 (3)	0.08592 (16)	0.51213 (14)	0.0442 (5)
N1	0.6405 (2)	0.17613 (12)	0.17185 (11)	0.0380 (4)
H1	0.696996	0.137103	0.217506	0.046*
N2	0.52282 (19)	0.23449 (13)	0.02905 (11)	0.0380 (4)
H2	0.489733	0.240122	−0.035337	0.046*
N3	1.0314 (3)	0.2402 (2)	0.33090 (17)	0.0732 (6)
N4	1.1240 (4)	0.2754 (2)	0.69380 (17)	0.1012 (10)
N5	0.7348 (3)	−0.00302 (16)	0.51988 (14)	0.0564 (5)
O1	0.7905 (2)	0.06989 (12)	0.33241 (10)	0.0566 (4)
O2	1.0161 (3)	0.1779 (2)	0.25877 (16)	0.1128 (9)
O3	1.0822 (4)	0.3330 (2)	0.33096 (19)	0.1259 (10)
O4	1.2391 (12)	0.3402 (7)	0.6942 (9)	0.108 (2)	0.74 (3)
O5	1.070 (2)	0.2550 (9)	0.7706 (4)	0.120 (4)	0.74 (3)
O6	0.681 (2)	−0.0065 (12)	0.5949 (9)	0.095 (3)	0.69 (4)
O7	0.7000 (15)	−0.0726 (5)	0.4513 (5)	0.0689 (17)	0.69 (4)
O4A	1.189 (6)	0.366 (2)	0.687 (2)	0.133 (12)	0.26 (3)
O5A	1.157 (3)	0.2208 (14)	0.7717 (10)	0.087 (5)	0.26 (3)
O6A	0.743 (3)	−0.0316 (16)	0.6066 (8)	0.066 (4)	0.31 (4)
O7A	0.640 (5)	−0.045 (3)	0.4473 (8)	0.096 (8)	0.31 (4)
O8	0.5696 (2)	0.14085 (12)	−0.13492 (10)	0.0539 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0404 (11)	0.0385 (10)	0.0310 (9)	−0.0005 (8)	0.0114 (8)	−0.0056 (8)
C2	0.0404 (11)	0.0401 (11)	0.0361 (10)	0.0009 (9)	0.0100 (8)	−0.0016 (8)
C3	0.0547 (13)	0.0531 (13)	0.0370 (10)	0.0082 (11)	0.0162 (10)	0.0024 (9)
C4	0.0535 (14)	0.0588 (14)	0.0437 (11)	0.0080 (11)	0.0134 (10)	0.0161 (10)
C5	0.0401 (12)	0.0397 (11)	0.0611 (13)	−0.0011 (9)	0.0115 (10)	0.0080 (10)
C6	0.0535 (15)	0.0460 (13)	0.0926 (19)	0.0078 (11)	0.0175 (13)	0.0194 (13)
C7	0.0879 (19)	0.0646 (16)	0.0528 (14)	0.0339 (15)	0.0065 (13)	−0.0134 (12)
C8	0.0897 (19)	0.0739 (17)	0.0369 (11)	0.0383 (15)	0.0030 (12)	−0.0082 (11)
C9	0.0424 (11)	0.0370 (10)	0.0325 (9)	0.0002 (8)	0.0111 (8)	−0.0032 (8)
C10	0.0475 (12)	0.0381 (10)	0.0293 (9)	0.0041 (9)	0.0100 (8)	−0.0004 (8)
C11	0.0873 (18)	0.0495 (13)	0.0396 (11)	−0.0147 (12)	0.0188 (11)	−0.0049 (10)
C12	0.102 (2)	0.0575 (15)	0.0433 (13)	−0.0169 (14)	0.0124 (13)	−0.0134 (11)
C13	0.0885 (18)	0.0581 (14)	0.0312 (10)	0.0170 (13)	0.0135 (11)	−0.0031 (10)
C14	0.144 (3)	0.102 (2)	0.0364 (13)	0.022 (2)	0.0182 (16)	−0.0132 (14)
C15	0.093 (2)	0.0669 (16)	0.0419 (12)	0.0014 (14)	0.0328 (13)	0.0026 (11)
C16	0.0678 (15)	0.0568 (14)	0.0425 (11)	−0.0085 (12)	0.0222 (11)	−0.0029 (10)
C17	0.0370 (11)	0.0362 (10)	0.0306 (9)	−0.0013 (8)	0.0081 (8)	−0.0023 (7)
C18	0.0388 (11)	0.0368 (10)	0.0346 (9)	−0.0024 (8)	0.0124 (8)	−0.0044 (8)
C19	0.0491 (12)	0.0409 (11)	0.0411 (11)	0.0014 (9)	0.0133 (9)	0.0017 (9)
C20	0.0585 (14)	0.0431 (12)	0.0576 (13)	0.0089 (11)	0.0205 (11)	0.0024 (10)
C21	0.0632 (15)	0.0449 (12)	0.0590 (14)	0.0029 (11)	0.0293 (12)	−0.0069 (10)
C22	0.0617 (14)	0.0504 (13)	0.0410 (11)	−0.0039 (11)	0.0220 (10)	−0.0091 (9)
C23	0.0449 (12)	0.0409 (11)	0.0346 (10)	−0.0028 (9)	0.0113 (8)	−0.0029 (8)
C24	0.129 (3)	0.093 (2)	0.0289 (11)	0.0286 (19)	0.0165 (14)	0.0052 (12)
C25	0.0578 (13)	0.0454 (12)	0.0332 (10)	0.0175 (10)	0.0115 (9)	0.0047 (9)
C26	0.0612 (14)	0.0579 (14)	0.0376 (11)	0.0083 (11)	0.0131 (10)	0.0123 (10)
C27	0.0765 (18)	0.0567 (14)	0.0510 (13)	−0.0060 (13)	0.0083 (12)	0.0081 (11)
C28	0.0904 (19)	0.0514 (14)	0.0396 (12)	−0.0066 (13)	0.0034 (12)	0.0000 (10)
C29	0.0822 (17)	0.0513 (13)	0.0317 (10)	0.0077 (12)	0.0130 (11)	0.0030 (9)
C30	0.0558 (13)	0.0423 (11)	0.0353 (10)	0.0087 (10)	0.0113 (9)	0.0040 (8)
N1	0.0464 (10)	0.0380 (9)	0.0298 (8)	0.0029 (7)	0.0095 (7)	−0.0004 (6)
N2	0.0437 (9)	0.0429 (9)	0.0269 (7)	0.0040 (7)	0.0080 (7)	−0.0017 (7)
N3	0.0733 (15)	0.0994 (18)	0.0508 (12)	−0.0016 (13)	0.0207 (11)	0.0201 (12)
N4	0.161 (3)	0.0768 (17)	0.0483 (13)	−0.0366 (18)	−0.0017 (15)	−0.0009 (12)
N5	0.0672 (13)	0.0601 (12)	0.0426 (10)	0.0042 (10)	0.0139 (9)	0.0065 (9)
O1	0.0793 (11)	0.0561 (9)	0.0316 (7)	0.0080 (8)	0.0072 (7)	0.0024 (7)
O2	0.130 (2)	0.162 (2)	0.0567 (12)	−0.0289 (17)	0.0489 (13)	−0.0078 (13)
O3	0.173 (3)	0.117 (2)	0.1001 (18)	−0.0324 (18)	0.0585 (17)	0.0345 (15)
O4	0.143 (4)	0.078 (3)	0.078 (3)	−0.036 (3)	−0.020 (3)	0.005 (3)
O5	0.199 (8)	0.110 (5)	0.0367 (16)	−0.044 (5)	0.011 (3)	−0.0088 (19)
O6	0.114 (7)	0.118 (5)	0.066 (3)	−0.033 (5)	0.051 (4)	−0.009 (3)
O7	0.086 (4)	0.061 (2)	0.0554 (19)	−0.008 (2)	0.0120 (19)	−0.0028 (15)
O4A	0.21 (3)	0.086 (9)	0.071 (8)	−0.071 (14)	−0.008 (12)	−0.001 (7)
O5A	0.119 (13)	0.086 (7)	0.047 (4)	−0.017 (6)	0.007 (5)	0.005 (4)
O6A	0.071 (8)	0.080 (7)	0.046 (3)	−0.012 (5)	0.015 (3)	0.020 (3)
O7A	0.105 (12)	0.124 (14)	0.048 (4)	−0.051 (11)	0.005 (5)	0.002 (5)
O8	0.0731 (11)	0.0602 (9)	0.0280 (7)	0.0123 (8)	0.0106 (7)	−0.0008 (6)

Geometric parameters (Å, º) top

C1—C9	1.362 (3)	C19—C20	1.378 (3)
C1—N2	1.380 (2)	C19—H19	0.9300
C1—C2	1.459 (3)	C20—C21	1.372 (3)
C2—C3	1.380 (3)	C20—H20	0.9300
C2—C8	1.381 (3)	C21—C22	1.374 (3)
C3—C4	1.377 (3)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.387 (3)
C4—C5	1.369 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—O8	1.362 (2)
C5—C7	1.367 (3)	C24—O8	1.423 (2)
C5—C6	1.498 (3)	C24—H24A	0.9600
C6—H6A	0.9600	C24—H24B	0.9600
C6—H6B	0.9600	C24—H24C	0.9600
C6—H6C	0.9600	C25—O1	1.246 (2)
C7—C8	1.375 (3)	C25—C26	1.441 (3)
C7—H7	0.9300	C25—C30	1.450 (3)
C8—H8	0.9300	C26—C27	1.361 (3)
C9—N1	1.384 (2)	C26—N3	1.458 (3)
C9—C10	1.473 (2)	C27—C28	1.379 (3)
C10—C11	1.372 (3)	C27—H27	0.9300
C10—C16	1.382 (3)	C28—C29	1.370 (3)
C11—C12	1.384 (3)	C28—N4	1.438 (3)
C11—H11	0.9300	C29—C30	1.359 (3)
C12—C13	1.365 (3)	C29—H29	0.9300
C12—H12	0.9300	C30—N5	1.459 (3)
C13—C15	1.368 (4)	N1—H1	0.8600
C13—C14	1.514 (3)	N2—H2	0.8600
C14—H14A	0.9600	N3—O2	1.207 (3)
C14—H14B	0.9600	N3—O3	1.211 (3)
C14—H14C	0.9600	N4—O4	1.238 (7)
C15—C16	1.378 (3)	N4—O4A	1.249 (12)
C15—H15	0.9300	N4—O5A	1.256 (9)
C16—H16	0.9300	N4—O5	1.268 (6)
C17—N2	1.329 (2)	N5—O7A	1.199 (9)
C17—N1	1.331 (2)	N5—O7	1.223 (5)
C17—C18	1.452 (3)	N5—O6	1.218 (5)
C18—C19	1.392 (3)	N5—O6A	1.231 (9)
C18—C23	1.402 (3)

C9—C1—N2	105.23 (16)	C20—C19—H19	119.7
C9—C1—C2	133.45 (17)	C18—C19—H19	119.7
N2—C1—C2	121.32 (16)	C21—C20—C19	120.0 (2)
C3—C2—C8	116.81 (19)	C21—C20—H20	120.0
C3—C2—C1	121.19 (17)	C19—C20—H20	120.0
C8—C2—C1	122.00 (18)	C20—C21—C22	120.8 (2)
C4—C3—C2	120.98 (19)	C20—C21—H21	119.6
C4—C3—H3	119.5	C22—C21—H21	119.6
C2—C3—H3	119.5	C21—C22—C23	119.80 (19)
C5—C4—C3	122.3 (2)	C21—C22—H22	120.1
C5—C4—H4	118.8	C23—C22—H22	120.1
C3—C4—H4	118.8	O8—C23—C22	123.66 (17)
C7—C5—C4	116.5 (2)	O8—C23—C18	116.19 (16)
C7—C5—C6	121.3 (2)	C22—C23—C18	120.16 (19)
C4—C5—C6	122.2 (2)	O8—C24—H24A	109.5
C5—C6—H6A	109.5	O8—C24—H24B	109.5
C5—C6—H6B	109.5	H24A—C24—H24B	109.5
H6A—C6—H6B	109.5	O8—C24—H24C	109.5
C5—C6—H6C	109.5	H24A—C24—H24C	109.5
H6A—C6—H6C	109.5	H24B—C24—H24C	109.5
H6B—C6—H6C	109.5	O1—C25—C26	124.71 (19)
C5—C7—C8	122.3 (2)	O1—C25—C30	123.6 (2)
C5—C7—H7	118.9	C26—C25—C30	111.63 (18)
C8—C7—H7	118.9	C27—C26—C25	124.5 (2)
C7—C8—C2	121.1 (2)	C27—C26—N3	115.8 (2)
C7—C8—H8	119.4	C25—C26—N3	119.7 (2)
C2—C8—H8	119.4	C26—C27—C28	119.2 (2)
C1—C9—N1	106.68 (15)	C26—C27—H27	120.4
C1—C9—C10	134.34 (18)	C28—C27—H27	120.4
N1—C9—C10	118.94 (16)	C29—C28—C27	120.9 (2)
C11—C10—C16	118.21 (18)	C29—C28—N4	119.6 (2)
C11—C10—C9	120.59 (18)	C27—C28—N4	119.4 (2)
C16—C10—C9	121.02 (18)	C30—C29—C28	119.9 (2)
C10—C11—C12	120.3 (2)	C30—C29—H29	120.0
C10—C11—H11	119.8	C28—C29—H29	120.0
C12—C11—H11	119.8	C29—C30—C25	123.8 (2)
C13—C12—C11	121.6 (2)	C29—C30—N5	116.31 (19)
C13—C12—H12	119.2	C25—C30—N5	119.84 (18)
C11—C12—H12	119.2	C17—N1—C9	110.54 (16)
C12—C13—C15	117.9 (2)	C17—N1—H1	124.7
C12—C13—C14	120.7 (3)	C9—N1—H1	124.7
C15—C13—C14	121.4 (2)	C17—N2—C1	111.74 (15)
C13—C14—H14A	109.5	C17—N2—H2	124.1
C13—C14—H14B	109.5	C1—N2—H2	124.1
H14A—C14—H14B	109.5	O2—N3—O3	122.4 (2)
C13—C14—H14C	109.5	O2—N3—C26	119.1 (3)
H14A—C14—H14C	109.5	O3—N3—C26	118.4 (2)
H14B—C14—H14C	109.5	O4A—N4—O5A	123.9 (13)
C13—C15—C16	121.3 (2)	O4—N4—O5	124.7 (6)
C13—C15—H15	119.3	O4—N4—C28	119.3 (6)
C16—C15—H15	119.3	O4A—N4—C28	115.9 (13)
C15—C16—C10	120.6 (2)	O5A—N4—C28	118.5 (7)
C15—C16—H16	119.7	O5—N4—C28	116.0 (4)
C10—C16—H16	119.7	O7—N5—O6	122.4 (5)
N2—C17—N1	105.81 (16)	O7A—N5—O6A	122.8 (11)
N2—C17—C18	127.47 (16)	O7A—N5—C30	122.4 (8)
N1—C17—C18	126.70 (17)	O7—N5—C30	118.5 (4)
C19—C18—C23	118.59 (17)	O6—N5—C30	119.1 (4)
C19—C18—C17	120.09 (16)	O6A—N5—C30	114.8 (8)
C23—C18—C17	121.32 (17)	C23—O8—C24	119.02 (17)
C20—C19—C18	120.67 (19)

C9—C1—C2—C3	−179.6 (2)	O1—C25—C26—C27	176.4 (2)
N2—C1—C2—C3	−0.1 (3)	C30—C25—C26—C27	−1.9 (3)
C9—C1—C2—C8	0.6 (4)	O1—C25—C26—N3	−4.5 (3)
N2—C1—C2—C8	−179.9 (2)	C30—C25—C26—N3	177.2 (2)
C8—C2—C3—C4	0.3 (3)	C25—C26—C27—C28	1.3 (4)
C1—C2—C3—C4	−179.5 (2)	N3—C26—C27—C28	−177.8 (2)
C2—C3—C4—C5	0.7 (3)	C26—C27—C28—C29	0.3 (4)
C3—C4—C5—C7	−1.2 (3)	C26—C27—C28—N4	178.3 (3)
C3—C4—C5—C6	−180.0 (2)	C27—C28—C29—C30	−1.1 (4)
C4—C5—C7—C8	0.7 (4)	N4—C28—C29—C30	−179.0 (2)
C6—C5—C7—C8	179.6 (3)	C28—C29—C30—C25	0.3 (4)
C5—C7—C8—C2	0.2 (5)	C28—C29—C30—N5	−179.6 (2)
C3—C2—C8—C7	−0.7 (4)	O1—C25—C30—C29	−177.2 (2)
C1—C2—C8—C7	179.1 (2)	C26—C25—C30—C29	1.1 (3)
N2—C1—C9—N1	−0.7 (2)	O1—C25—C30—N5	2.6 (3)
C2—C1—C9—N1	178.9 (2)	C26—C25—C30—N5	−179.02 (19)
N2—C1—C9—C10	176.9 (2)	N2—C17—N1—C9	−0.4 (2)
C2—C1—C9—C10	−3.5 (4)	C18—C17—N1—C9	177.88 (18)
C1—C9—C10—C11	−72.6 (3)	C1—C9—N1—C17	0.7 (2)
N1—C9—C10—C11	104.8 (2)	C10—C9—N1—C17	−177.36 (17)
C1—C9—C10—C16	112.4 (3)	N1—C17—N2—C1	−0.1 (2)
N1—C9—C10—C16	−70.3 (3)	C18—C17—N2—C1	−178.31 (18)
C16—C10—C11—C12	0.1 (4)	C9—C1—N2—C17	0.5 (2)
C9—C10—C11—C12	−175.1 (2)	C2—C1—N2—C17	−179.13 (17)
C10—C11—C12—C13	−0.2 (4)	C27—C26—N3—O2	153.3 (3)
C11—C12—C13—C15	0.2 (4)	C25—C26—N3—O2	−25.9 (4)
C11—C12—C13—C14	178.3 (3)	C27—C26—N3—O3	−26.5 (4)
C12—C13—C15—C16	−0.2 (4)	C25—C26—N3—O3	154.3 (3)
C14—C13—C15—C16	−178.3 (3)	C29—C28—N4—O4	168.8 (7)
C13—C15—C16—C10	0.2 (4)	C27—C28—N4—O4	−9.2 (8)
C11—C10—C16—C15	−0.1 (3)	C29—C28—N4—O4A	−163 (3)
C9—C10—C16—C15	175.1 (2)	C27—C28—N4—O4A	19 (3)
N2—C17—C18—C19	−177.60 (19)	C29—C28—N4—O5A	30.6 (17)
N1—C17—C18—C19	4.5 (3)	C27—C28—N4—O5A	−147.4 (17)
N2—C17—C18—C23	3.1 (3)	C29—C28—N4—O5	−14.3 (10)
N1—C17—C18—C23	−174.78 (18)	C27—C28—N4—O5	167.7 (10)
C23—C18—C19—C20	−0.1 (3)	C29—C30—N5—O7A	169 (3)
C17—C18—C19—C20	−179.47 (19)	C25—C30—N5—O7A	−11 (3)
C18—C19—C20—C21	0.1 (3)	C29—C30—N5—O7	−156.8 (6)
C19—C20—C21—C22	0.0 (3)	C25—C30—N5—O7	23.4 (7)
C20—C21—C22—C23	−0.1 (3)	C29—C30—N5—O6	21.8 (14)
C21—C22—C23—O8	−180.0 (2)	C25—C30—N5—O6	−158.1 (13)
C21—C22—C23—C18	0.1 (3)	C29—C30—N5—O6A	−10.5 (14)
C19—C18—C23—O8	−179.89 (17)	C25—C30—N5—O6A	169.7 (14)
C17—C18—C23—O8	−0.6 (3)	C22—C23—O8—C24	2.7 (3)
C19—C18—C23—C22	0.0 (3)	C18—C23—O8—C24	−177.4 (2)
C17—C18—C23—C22	179.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.82	2.661 (2)	167
N2—H2···O8	0.86	2.05	2.601 (2)	122

Acknowledgements

The authors are grateful to the Department of Chemistry, St. Joseph's College (A) Jakhama and the Department of Life and Consumer Sciences, College of Agriculture and Environmental Sciences, Florida Campus, University of South Africa, Johannesburg, for all the help received in carrying out the research work. The authors are also grateful to SAIC Tezpur University, India, for the high-quality single-crystal XRD data collection.

References

Bertolasi, V., Gilli, P. & Gilli, G. (2011). Cryst. Growth Des. 11, 2724–2735. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2018). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565–573. Web of Science CrossRef PubMed CAS 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
Du, M. & Zhao, X.-J. (2003). Acta Cryst. E59, o1898–o1900. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o235. Web of Science CrossRef IUCr Journals Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Li, S.-R., Tan, Y.-M., Zhang, L. & Zhou, C.-H. (2023). Pharmaceutics 15, 1348. CrossRef PubMed 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
Sheldrick, G. M. (2015a). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Solo, P., Pillay, M., Arockia doss, M. & William Raja, T. R. (2025). IUCrData 10, x250877. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.