In the title compound, the central zinc(II) ion coordinated by four 5-phenylimidazole ligands, with two nitrate anions providing charge balance·In the crystal, the nitrate ions occupy the voids formed by the [Zn(C9H8N2)4]2+ cations and function as counter-ions. The nitrate oxygen atoms participate in weak N—H⋯O hydrogen-bonding interactions.
Keywords: 5-phenyl-1H-imidazole, Zn-complex, crystal structure
Abstract
The title complex salt, [Zn(C9H8N2)4](NO3)2, features a central zinc(II) ion coordinated by four 5-phenylimidazole ligands, with two nitrate anions providing charge balance. It crystallizes in the monoclinic space group C2/c. In the crystal, the nitrate ions occupy the voids formed by the [Zn(C9H8N2)4]2+ cations and function as counter-ions. The nitrate oxygen atoms participate in strong N—H⋯O hydrogen-bonding interactions. The crystal studied was refined as a two-component twin.
1. Chemical context
The 5-phenyl-1H-imidazole scaffold is an important framework in medicinal chemistry due to its versatility and biological significance. It significantly contributes to the creation of pharmacologically active molecules, particularly in the fields of HIV, anticancer, and antibacterial research (Abu Almaaty et al., 2021 ▸; Rashamuse et al., 2020 ▸, 2021 ▸; Roy et al., 2005 ▸). The imidazole moiety is frequently included in a variety of medicinal drugs, and its pharmacokinetic and pharmacodynamic qualities are further improved by the addition of a phenyl group at the 5-position (Devi et al., 2024 ▸; Blass et al., 2000 ▸). 5-Phenyl-1H-imidazole is a structurally straightforward aromatic heterocycle composed of a five-membered imidazole ring with two non-adjacent nitrogen atoms substituted at the 5-position with a phenyl group. This basic structure has several functionalization sites, making it a promising starting point for drug discovery and synthetic modification. In addition to its biological value, imidazole derivatives, such as 5-phenyl-1H-imidazole, have shown great promise in coordination chemistry. These compounds readily form coordination complexes with a wide range of transition metals, including zinc, copper, ruthenium, and iron (Rashamuse et al., 2023 ▸; Baranoff et al., 2011 ▸; Magwa & Rashamuse, 2024 ▸; Bonomo et al., 1988 ▸; Carver et al., 2003 ▸; Li et al., 2024 ▸). In metal complexes, the nitrogen atom in the imidazole ring works as a σ-donor ligand, typically binding through the sp2-hybridized nitrogen atom (also known as the imine-type nitrogen at position 3 of the ring). This coordination stabilizes the metal center compared to its unligated or aqua-ligated state, and significantly affects the complex’s redox potential, geometry, and chemical reactivity. These metal–imidazole complexes are important in bioinorganic chemistry because they frequently serve as models for metalloenzymes (Roy et al., 2005 ▸). Enzymes such as carbonic anhydrase and cytochrome c oxidase rely on imidazole moieties for catalytic activity and electron transport, respectively (Roy et al., 2005 ▸; Maneeta et al., 2024 ▸). Thus, synthesized imidazole–metal complexes offer important insights into enzyme functions and are being investigated for therapeutic uses including as imaging probes, anticancer medicines, and antibacterial compounds.
2. Structural commentary
The title compound crystallizes in the monoclinic space group C2/c, with the zinc(II) atom occupying a special position on a symmetry element. As a result, the molecule’s intrinsic symmetry matches the crystallographic symmetry, so only a fraction of the molecule is present in the asymmetric unit. The zinc(II) atom is coordinated by four 5-phenyl-1H-imidazole ligands, forming a distorted tetrahedral geometry (Table 1 ▸, Fig. 1 ▸). This distortion is evident from the six N—Zn—N bond angles, which deviate slightly from the ideal tetrahedral angle of 109.5°. The Zn—N bond lengths are consistent, with symmetry-equivalent values averaged to 1.986 Å, confirming a relatively symmetrical coordination sphere. The nitrate anions act as counter-ions and exhibit slight distortions from an ideal trigonal planar geometry (Table 1 ▸). These deviations arise from hydrogen-bonding interactions with the imidazole ligands, which are discussed in the Supramolecular features section. Generally, the structural parameters and symmetry constraints define a stable, well-organized crystal structure, with the zinc center adopting a distorted tetrahedral coordination environment stabilized by both covalent and non-covalent interactions. These interactions arise from crystal packing and intermolecular forces, which slightly adjust bond angles and distances to optimize crystal stability. As a result, the coordination sphere deviates from an ideal tetrahedron, reflecting the combined influence of both strong covalent bonding and secondary non-covalent forces.
Table 1. Selected geometric parameters (Å, °).
| Zn1—N1 | 1.9882 (11) | O2—N5 | 1.2295 (19) |
| Zn1—N3 | 1.9828 (11) | O3—N5 | 1.2585 (18) |
| O1—N5 | 1.2606 (16) | ||
| N1i—Zn1—N1 | 105.44 (6) | O2—N5—O1 | 119.84 (14) |
| N3—Zn1—N1i | 110.19 (4) | O2—N5—O3 | 123.65 (14) |
| N3—Zn1—N1 | 111.70 (4) | O3—N5—O1 | 116.51 (13) |
| N3—Zn1—N3i | 107.68 (7) |
Symmetry code: (i) 
.
Figure 1.
Displacement ellipsoid plot of the title compound showing the atom-numbering scheme and the interactions between the nitrate ion and the 5-phenyl-1H-imidazole ligand (dashed lines). Displacement ellipsoids are drawn at the 50% probability level. Unlabelled atoms are generated by the symmetry operation −x + 1, y, −z + 
.
3. Supramolecular features
The molecular packing of the title compound is illustrated in Fig. 2 ▸, showing how the three-dimensional arrangement of [Zn(C9H8N2)4]2+ cations and nitrate anions defines the crystal structure. The nitrate ions play an active role in shaping the packing by accepting strong N—H⋯·O hydrogen bonds (Table 2 ▸) with hydrogen atoms from the imidazole moieties. Each nitrate anion accepts three hydrogen bonds from neighboring cations, while each cation interacts with two nitrate anions and several adjacent cations. In addition to hydrogen bonding, phenyl rings from adjacent cations exhibit notable π–π stacking and edge-to-face interactions, characterized by a parallel-displaced arrangement [centroid–centroid distance = 4.037 (2) Å, interplanar separation = 3.408 Å, slippage = 2.165 Å] and a T-shaped contact [centroid–centroid distance = 5.536 (2) Å, ring-normal angle = 69.9°, centroid-to-plane separations = 3.835 and 4.137 Å], highlighting non-covalent cation–cation contacts that contribute to the crystal cohesion. Together, these hydrogen bonds and aromatic interactions organize the crystal into a robust structure, integrating electrostatic forces, directional hydrogen bonding, and π–π stacking. to optimize the crystal stability.
Figure 2.
Packing diagram of the title compound showing the nitrate cations lying in the voids between the cationic complexes.
Table 2. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2—H2⋯O1 | 0.88 | 1.91 | 2.7425 (14) | 156 |
| N4—H4⋯O1ii | 0.88 | 2.30 | 2.9779 (16) | 134 |
| N4—H4⋯O3ii | 0.88 | 2.07 | 2.8326 (18) | 145 |
| C5—H5⋯O3iii | 0.95 | 2.46 | 3.3915 (19) | 166 |
| C6—H6⋯O2iv | 0.95 | 2.54 | 3.278 (2) | 135 |
Symmetry codes: (ii) 
; (iii) 
; (iv) 
.
4. Database survey
The title complex, represents a new addition to the family of zinc(II)–imidazole derivatives, a group known for their structural flexibility and diverse coordination behavior. Zinc(II) readily adopts various geometries, while imidazole ligands provide multiple coordination possibilities. A search of the Cambridge Structural Database (CSD, Version 5.45, March 2024 update; Groom et al., 2016 ▸) and Google Scholar found no prior example of a complex with the same formulation, [Zn(C9H8N2)4]2+·2NO3−, confirming its originality. Related zinc–imidazole complexes are rare but include Zn(C3H4N2)42+ (CCDC No. 639568; Huang et al., 2007 ▸), [Zn(dmit)4][BF4]2, and [Zn(dmit)4][NO3]2 (CCDC Nos. 772715 and 772716; William et al., 2010 ▸), helical frameworks [Zn(bdt)]2+ (CCDC Nos. 772872 and 772873; Liu et al., 2010 ▸), and Zn(C4H6N2)42+ (CDCC No. 861722; Reedijk et al., 2012 ▸). Structural comparison with these reported systems shows that Zn—N bond lengths in tetrahedral ZnII complexes generally range from 1.97–2.00 Å, consistent with the mean value of 1.986 Å in the present compound. Likewise, the observed N—Zn—N bond angles [105.44 (6)–111.70 (4)°] fall within the expected range of 104–113° reported for similar complexes in the CSD, confirming a slightly distorted tetrahedral environment. Such deviations from the ideal tetrahedral angle of 109.5° are common and have been attributed to steric effects of bulky substituents and hydrogen-bonding interactions (Huang et al., 2007 ▸; William et al., 2010 ▸; Reedijk et al., 2012 ▸). In this complex, the distortion likely arises from the phenyl-imidazole ligands and nitrate-mediated hydrogen bonding, in agreement with established structural trends for imidazole-based ZnII systems.
5. Synthesis and crystallization
To prepare the title compound, 0.14 g (0.485 mmol) of zinc nitrate hexahydrate were added to a stirred solution of 0.58 g (4 mmol) of 4-phenylimidazole in a solvent mixture of dichloromethane (DCM, 25 mL) and methanol (MeOH, 3 mL) in a round-bottom flask. The resulting slurry was stirred continuously for 5 h until a clear solution formed, after which the solution was filtered, and the filtrate was allowed to evaporate slowly at ambient temperatures (298–300 K). After 16 days, light-yellow crystals formed, which were collected by filtration and dried in air. The synthesis is shown in the scheme below.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. All C-bound H were placed in geometrically idealized positions and refined using the riding model, with isotropic displacement parameters set to 1.2 or 1.5 times those of the corresponding parent carbon atoms. The crystal studied was refined as a two-component twin, and an appropriate twin law was applied during the refinement process. A B-level PLAT910 alert indicates that low-angle reflections below θmin = 3.92° were omitted. This exclusion is intentional because the reflections at such low angles were either partially obscured by the beamstop or detector gap or severely overloaded. The omission prevents systematic errors in intensity data without affecting the completeness of the dataset or the refinement stability.
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | [Zn(C9H8N2)4](NO3)2 |
| M r | 766.08 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 20.2757 (5), 8.5411 (2), 20.2328 (5) |
| β (°) | 94.908 (1) |
| V (Å3) | 3491.00 (15) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.77 |
| Crystal size (mm) | 0.33 × 0.28 × 0.21 |
| Data collection | |
| Diffractometer | Bruker D8 Venture Photon CCD area detector |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.676, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 37634, 4362, 3778 |
| R int | 0.039 |
| (sin θ/λ)max (Å−1) | 0.668 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.083, 1.08 |
| No. of reflections | 4131 |
| No. of parameters | 240 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.58, −0.54 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025010874/ev2022sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025010874/ev2022Isup3.hkl
CCDC reference: 2433548
Additional supporting information: crystallographic information; 3D view; checkCIF report
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Crystal data
| [Zn(C9H8N2)4](NO3)2 | F(000) = 1584 |
| Mr = 766.08 | Dx = 1.458 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 20.2757 (5) Å | Cell parameters from 9886 reflections |
| b = 8.5411 (2) Å | θ = 3.9–28.3° |
| c = 20.2328 (5) Å | µ = 0.77 mm−1 |
| β = 94.908 (1)° | T = 100 K |
| V = 3491.00 (15) Å3 | Block, colourless |
| Z = 4 | 0.33 × 0.28 × 0.21 mm |
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Data collection
| Bruker D8 Venture Photon CCD area detector diffractometer | 3778 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.039 |
| ω scans | θmax = 28.3°, θmin = 3.9° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −26→26 |
| Tmin = 0.676, Tmax = 0.746 | k = −11→11 |
| 37634 measured reflections | l = −26→26 |
| 4362 independent reflections |
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Refinement
| Refinement on F2 | Primary atom site location: iterative |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0364P)2 + 3.5607P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 4131 reflections | Δρmax = 0.58 e Å−3 |
| 240 parameters | Δρmin = −0.54 e Å−3 |
| 0 restraints |
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Special details
| 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. |
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.500000 | 0.49768 (2) | 0.250000 | 0.01768 (9) | |
| N1 | 0.53202 (5) | 0.63867 (13) | 0.32410 (5) | 0.0197 (2) | |
| N2 | 0.59820 (5) | 0.73921 (13) | 0.40463 (5) | 0.0200 (2) | |
| H2 | 0.631233 | 0.748065 | 0.435560 | 0.024* | |
| N3 | 0.42707 (6) | 0.36069 (13) | 0.27471 (5) | 0.0200 (2) | |
| N4 | 0.34930 (6) | 0.27794 (14) | 0.33445 (6) | 0.0259 (3) | |
| H4 | 0.319267 | 0.278378 | 0.363381 | 0.031* | |
| C1 | 0.58505 (7) | 0.61404 (16) | 0.36617 (6) | 0.0207 (3) | |
| H1 | 0.610201 | 0.520057 | 0.368544 | 0.025* | |
| C2 | 0.51038 (6) | 0.78840 (15) | 0.33734 (6) | 0.0193 (2) | |
| H2A | 0.473079 | 0.838709 | 0.315000 | 0.023* | |
| C3 | 0.55109 (6) | 0.85247 (15) | 0.38757 (6) | 0.0180 (2) | |
| C4 | 0.55155 (7) | 1.00688 (14) | 0.41913 (6) | 0.0181 (2) | |
| C5 | 0.61083 (7) | 1.07279 (17) | 0.44644 (7) | 0.0243 (3) | |
| H5 | 0.651257 | 1.017424 | 0.444524 | 0.029* | |
| C6 | 0.61072 (8) | 1.21885 (17) | 0.47632 (8) | 0.0295 (3) | |
| H6 | 0.651080 | 1.262996 | 0.495073 | 0.035* | |
| C7 | 0.55174 (8) | 1.30109 (17) | 0.47897 (8) | 0.0291 (3) | |
| H7 | 0.551861 | 1.401404 | 0.499269 | 0.035* | |
| C8 | 0.49274 (7) | 1.23615 (17) | 0.45189 (7) | 0.0255 (3) | |
| H8 | 0.452460 | 1.292215 | 0.453632 | 0.031* | |
| C9 | 0.49242 (6) | 1.08976 (16) | 0.42230 (6) | 0.0211 (3) | |
| H9 | 0.451869 | 1.045539 | 0.404097 | 0.025* | |
| C10 | 0.38769 (7) | 0.39837 (16) | 0.32101 (7) | 0.0243 (3) | |
| H10 | 0.386876 | 0.497897 | 0.341889 | 0.029* | |
| C11 | 0.41252 (6) | 0.20659 (15) | 0.25808 (6) | 0.0198 (2) | |
| H11 | 0.432820 | 0.147352 | 0.225633 | 0.024* | |
| C12 | 0.36429 (6) | 0.15292 (15) | 0.29572 (6) | 0.0190 (2) | |
| C13 | 0.33328 (6) | −0.00064 (14) | 0.30077 (7) | 0.0186 (3) | |
| C14 | 0.33421 (6) | −0.10875 (16) | 0.24892 (7) | 0.0218 (3) | |
| H14 | 0.354879 | −0.082393 | 0.210011 | 0.026* | |
| C15 | 0.30492 (7) | −0.25450 (17) | 0.25434 (7) | 0.0252 (3) | |
| H15 | 0.305487 | −0.327515 | 0.218969 | 0.030* | |
| C16 | 0.27481 (7) | −0.29434 (17) | 0.31107 (7) | 0.0262 (3) | |
| H16 | 0.255042 | −0.394519 | 0.314562 | 0.031* | |
| C17 | 0.27360 (7) | −0.18784 (18) | 0.36261 (7) | 0.0276 (3) | |
| H17 | 0.252828 | −0.215062 | 0.401350 | 0.033* | |
| C18 | 0.30266 (7) | −0.04139 (18) | 0.35785 (7) | 0.0242 (3) | |
| H18 | 0.301760 | 0.031187 | 0.393345 | 0.029* | |
| O1 | 0.67549 (5) | 0.73031 (12) | 0.52263 (5) | 0.0244 (2) | |
| O2 | 0.71165 (7) | 0.51909 (14) | 0.48003 (8) | 0.0457 (4) | |
| O3 | 0.74061 (6) | 0.5820 (2) | 0.58356 (6) | 0.0526 (4) | |
| N5 | 0.70964 (6) | 0.60692 (15) | 0.52796 (6) | 0.0258 (3) |
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.01953 (12) | 0.01818 (12) | 0.01528 (12) | 0.000 | 0.00119 (8) | 0.000 |
| N1 | 0.0211 (5) | 0.0212 (5) | 0.0165 (5) | 0.0007 (4) | 0.0007 (4) | −0.0006 (4) |
| N2 | 0.0191 (5) | 0.0229 (5) | 0.0175 (5) | 0.0024 (4) | −0.0015 (4) | −0.0007 (4) |
| N3 | 0.0213 (5) | 0.0199 (5) | 0.0190 (5) | 0.0001 (4) | 0.0016 (4) | 0.0005 (4) |
| N4 | 0.0234 (6) | 0.0241 (6) | 0.0320 (6) | −0.0023 (4) | 0.0123 (5) | −0.0067 (5) |
| C1 | 0.0220 (6) | 0.0218 (6) | 0.0182 (6) | 0.0025 (5) | 0.0013 (5) | 0.0002 (5) |
| C2 | 0.0190 (6) | 0.0220 (6) | 0.0169 (6) | 0.0023 (5) | 0.0009 (4) | 0.0007 (5) |
| C3 | 0.0172 (5) | 0.0218 (6) | 0.0153 (5) | 0.0011 (5) | 0.0028 (4) | 0.0014 (5) |
| C4 | 0.0198 (6) | 0.0205 (6) | 0.0141 (5) | 0.0000 (4) | 0.0024 (4) | 0.0016 (4) |
| C5 | 0.0200 (6) | 0.0241 (7) | 0.0287 (7) | −0.0002 (5) | 0.0021 (5) | −0.0006 (5) |
| C6 | 0.0274 (7) | 0.0246 (7) | 0.0359 (8) | −0.0054 (6) | −0.0001 (6) | −0.0027 (6) |
| C7 | 0.0381 (8) | 0.0195 (6) | 0.0300 (7) | 0.0001 (6) | 0.0039 (6) | −0.0025 (5) |
| C8 | 0.0281 (7) | 0.0257 (7) | 0.0233 (6) | 0.0072 (5) | 0.0051 (5) | 0.0017 (5) |
| C9 | 0.0200 (6) | 0.0265 (7) | 0.0169 (6) | 0.0017 (5) | 0.0012 (4) | 0.0012 (5) |
| C10 | 0.0232 (6) | 0.0202 (6) | 0.0302 (7) | −0.0007 (5) | 0.0062 (5) | −0.0043 (5) |
| C11 | 0.0207 (6) | 0.0207 (6) | 0.0181 (6) | −0.0005 (5) | 0.0020 (5) | −0.0018 (5) |
| C12 | 0.0171 (5) | 0.0206 (6) | 0.0190 (6) | 0.0014 (5) | 0.0000 (4) | −0.0020 (5) |
| C13 | 0.0153 (6) | 0.0199 (6) | 0.0201 (6) | 0.0004 (4) | −0.0004 (5) | 0.0006 (5) |
| C14 | 0.0187 (6) | 0.0237 (6) | 0.0231 (6) | 0.0024 (5) | 0.0024 (5) | −0.0015 (5) |
| C15 | 0.0236 (6) | 0.0226 (6) | 0.0287 (7) | 0.0006 (5) | −0.0009 (5) | −0.0059 (5) |
| C16 | 0.0253 (7) | 0.0212 (6) | 0.0311 (7) | −0.0039 (5) | −0.0038 (5) | 0.0023 (6) |
| C17 | 0.0287 (7) | 0.0310 (7) | 0.0230 (7) | −0.0067 (6) | 0.0013 (5) | 0.0033 (6) |
| C18 | 0.0256 (7) | 0.0267 (7) | 0.0203 (6) | −0.0042 (5) | 0.0022 (5) | −0.0021 (5) |
| O1 | 0.0228 (5) | 0.0292 (5) | 0.0207 (5) | 0.0060 (4) | −0.0011 (4) | −0.0020 (4) |
| O2 | 0.0471 (8) | 0.0277 (6) | 0.0664 (9) | −0.0079 (5) | 0.0281 (7) | −0.0178 (6) |
| O3 | 0.0389 (7) | 0.0844 (11) | 0.0365 (7) | 0.0302 (7) | 0.0154 (5) | 0.0324 (7) |
| N5 | 0.0219 (5) | 0.0271 (6) | 0.0299 (6) | 0.0007 (5) | 0.0111 (5) | 0.0059 (5) |
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Geometric parameters (Å, º)
| Zn1—N1i | 1.9881 (11) | C7—H7 | 0.9500 |
| Zn1—N1 | 1.9882 (11) | C7—C8 | 1.388 (2) |
| Zn1—N3i | 1.9829 (11) | C8—H8 | 0.9500 |
| Zn1—N3 | 1.9828 (11) | C8—C9 | 1.386 (2) |
| N1—C1 | 1.3297 (17) | C9—H9 | 0.9500 |
| N1—C2 | 1.3856 (17) | C10—H10 | 0.9500 |
| N2—H2 | 0.8800 | C11—H11 | 0.9500 |
| N2—C1 | 1.3357 (17) | C11—C12 | 1.3689 (18) |
| N2—C3 | 1.3824 (16) | C12—C13 | 1.4618 (17) |
| N3—C10 | 1.3217 (18) | C13—C14 | 1.3990 (19) |
| N3—C11 | 1.3841 (17) | C13—C18 | 1.4012 (19) |
| N4—H4 | 0.8800 | C14—H14 | 0.9500 |
| N4—C10 | 1.3320 (18) | C14—C15 | 1.388 (2) |
| N4—C12 | 1.3739 (17) | C15—H15 | 0.9500 |
| C1—H1 | 0.9500 | C15—C16 | 1.388 (2) |
| C2—H2A | 0.9500 | C16—H16 | 0.9500 |
| C2—C3 | 1.3675 (18) | C16—C17 | 1.386 (2) |
| C3—C4 | 1.4649 (18) | C17—H17 | 0.9500 |
| C4—C5 | 1.3975 (19) | C17—C18 | 1.389 (2) |
| C4—C9 | 1.3985 (18) | C18—H18 | 0.9500 |
| C5—H5 | 0.9500 | O1—N5 | 1.2606 (16) |
| C5—C6 | 1.386 (2) | O2—N5 | 1.2295 (19) |
| C6—H6 | 0.9500 | O3—N5 | 1.2585 (18) |
| C6—C7 | 1.392 (2) | ||
| N1i—Zn1—N1 | 105.44 (6) | C8—C7—H7 | 120.1 |
| N3—Zn1—N1i | 110.19 (4) | C7—C8—H8 | 119.9 |
| N3—Zn1—N1 | 111.70 (4) | C9—C8—C7 | 120.20 (13) |
| N3i—Zn1—N1 | 110.18 (4) | C9—C8—H8 | 119.9 |
| N3i—Zn1—N1i | 111.70 (4) | C4—C9—H9 | 119.9 |
| N3—Zn1—N3i | 107.68 (7) | C8—C9—C4 | 120.27 (13) |
| C1—N1—Zn1 | 125.51 (9) | C8—C9—H9 | 119.9 |
| C1—N1—C2 | 105.92 (11) | N3—C10—N4 | 110.84 (12) |
| C2—N1—Zn1 | 128.06 (9) | N3—C10—H10 | 124.6 |
| C1—N2—H2 | 125.8 | N4—C10—H10 | 124.6 |
| C1—N2—C3 | 108.39 (11) | N3—C11—H11 | 125.3 |
| C3—N2—H2 | 125.8 | C12—C11—N3 | 109.31 (11) |
| C10—N3—Zn1 | 122.94 (9) | C12—C11—H11 | 125.3 |
| C10—N3—C11 | 105.94 (11) | N4—C12—C13 | 122.68 (12) |
| C11—N3—Zn1 | 130.38 (9) | C11—C12—N4 | 105.10 (11) |
| C10—N4—H4 | 125.6 | C11—C12—C13 | 132.17 (12) |
| C10—N4—C12 | 108.79 (11) | C14—C13—C12 | 120.42 (12) |
| C12—N4—H4 | 125.6 | C14—C13—C18 | 119.31 (12) |
| N1—C1—N2 | 110.88 (12) | C18—C13—C12 | 120.27 (12) |
| N1—C1—H1 | 124.6 | C13—C14—H14 | 120.0 |
| N2—C1—H1 | 124.6 | C15—C14—C13 | 119.98 (12) |
| N1—C2—H2A | 125.3 | C15—C14—H14 | 120.0 |
| C3—C2—N1 | 109.40 (11) | C14—C15—H15 | 119.8 |
| C3—C2—H2A | 125.3 | C14—C15—C16 | 120.45 (13) |
| N2—C3—C4 | 122.87 (11) | C16—C15—H15 | 119.8 |
| C2—C3—N2 | 105.41 (11) | C15—C16—H16 | 120.0 |
| C2—C3—C4 | 131.70 (12) | C17—C16—C15 | 119.92 (13) |
| C5—C4—C3 | 120.55 (12) | C17—C16—H16 | 120.0 |
| C5—C4—C9 | 119.31 (12) | C16—C17—H17 | 119.9 |
| C9—C4—C3 | 120.14 (12) | C16—C17—C18 | 120.27 (13) |
| C4—C5—H5 | 119.9 | C18—C17—H17 | 119.9 |
| C6—C5—C4 | 120.10 (13) | C13—C18—H18 | 120.0 |
| C6—C5—H5 | 119.9 | C17—C18—C13 | 120.07 (13) |
| C5—C6—H6 | 119.9 | C17—C18—H18 | 120.0 |
| C5—C6—C7 | 120.28 (14) | O2—N5—O1 | 119.84 (14) |
| C7—C6—H6 | 119.9 | O2—N5—O3 | 123.65 (14) |
| C6—C7—H7 | 120.1 | O3—N5—O1 | 116.51 (13) |
| C8—C7—C6 | 119.83 (13) | ||
| Zn1—N1—C1—N2 | 171.98 (9) | C4—C5—C6—C7 | −0.4 (2) |
| Zn1—N1—C2—C3 | −172.01 (9) | C5—C4—C9—C8 | 0.38 (19) |
| Zn1—N3—C10—N4 | −171.23 (9) | C5—C6—C7—C8 | 0.3 (2) |
| Zn1—N3—C11—C12 | 169.66 (9) | C6—C7—C8—C9 | 0.1 (2) |
| N1—C2—C3—N2 | 0.22 (14) | C7—C8—C9—C4 | −0.4 (2) |
| N1—C2—C3—C4 | 178.14 (12) | C9—C4—C5—C6 | 0.0 (2) |
| N2—C3—C4—C5 | 26.89 (19) | C10—N3—C11—C12 | −0.57 (15) |
| N2—C3—C4—C9 | −152.98 (12) | C10—N4—C12—C11 | −1.02 (16) |
| N3—C11—C12—N4 | 0.97 (15) | C10—N4—C12—C13 | 176.80 (12) |
| N3—C11—C12—C13 | −176.56 (13) | C11—N3—C10—N4 | −0.09 (16) |
| N4—C12—C13—C14 | 160.74 (13) | C11—C12—C13—C14 | −22.1 (2) |
| N4—C12—C13—C18 | −19.7 (2) | C11—C12—C13—C18 | 157.50 (15) |
| C1—N1—C2—C3 | 0.08 (14) | C12—N4—C10—N3 | 0.71 (17) |
| C1—N2—C3—C2 | −0.44 (14) | C12—C13—C14—C15 | 179.68 (12) |
| C1—N2—C3—C4 | −178.59 (12) | C12—C13—C18—C17 | −179.60 (13) |
| C2—N1—C1—N2 | −0.37 (15) | C13—C14—C15—C16 | −0.2 (2) |
| C2—C3—C4—C5 | −150.72 (14) | C14—C13—C18—C17 | 0.0 (2) |
| C2—C3—C4—C9 | 29.4 (2) | C14—C15—C16—C17 | 0.3 (2) |
| C3—N2—C1—N1 | 0.52 (15) | C15—C16—C17—C18 | −0.2 (2) |
| C3—C4—C5—C6 | −179.86 (13) | C16—C17—C18—C13 | 0.1 (2) |
| C3—C4—C9—C8 | −179.74 (12) | C18—C13—C14—C15 | 0.1 (2) |
Symmetry code: (i) −x+1, y, −z+1/2.
Tetrakis(5-phenyl-1H-imidazole-κN3)zinc(II) dinitrate . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1 | 0.88 | 1.91 | 2.7425 (14) | 156 |
| N4—H4···O1ii | 0.88 | 2.30 | 2.9779 (16) | 134 |
| N4—H4···O3ii | 0.88 | 2.07 | 2.8326 (18) | 145 |
| C5—H5···O3iii | 0.95 | 2.46 | 3.3915 (19) | 166 |
| C6—H6···O2iv | 0.95 | 2.54 | 3.278 (2) | 135 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, −y+3/2, −z+1; (iv) x, y+1, z.
Funding Statement
The author gratefully acknowledges the financial support provided by the College of Science, Engineering and Technology at the University of South Africa (UNISA), as well as the National Research Foundation (NRF) of South Africa through the Thuthuka funding programme (grant No. UID: 129744).
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025010874/ev2022sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025010874/ev2022Isup3.hkl
CCDC reference: 2433548
Additional supporting information: crystallographic information; 3D view; checkCIF report
Additional supporting information: crystallographic information; 3D view; checkCIF report