The title tetrahedral ZnII complex with 2-amino-6-fluoro-1,3-benzothiazole has been structurally characterized. The crystal packing is consolidated by N—H⋯O, bifurcated N—H⋯(O,F), C—H⋯π, O⋯π and offset π–π interactions.
Keywords: crystal structure; 2-amino-6-fluoro-1,3-benzothiazole; Hirshfeld surface; Void analysis; π–π stacking
Abstract
In the title zinc(II) complex, [Zn(C2H3O2)2(C7H5FN2S)2], the ZnII atom adopts a tetrahedral coordination geometry (τ4 = 0.96), defined by two nitrogen atoms from two neutral 2-amino-6-fluoro-1,3-benzothiazole ligands and two oxygen atoms from two monodentately coordinated acetate anions. The crystal packing is governed by classical N—H⋯O hydrogen bonds, which generate one-dimensional chains extending along the [011] direction. These chains are further reinforced by bifurcated N—H⋯(O,F) hydrogen bonds together with C—H⋯π, O⋯π, and offset π–π interactions, resulting in a robust three-dimensional supramolecular framework. Hirshfeld surface analysis reveals that H⋯H (31.5%), C⋯H/H⋯C (16.3%), O⋯H/H⋯O (13.0%), F⋯H/H⋯F (12.9%), and S⋯H/H⋯S (10.2%) contacts make the largest contributions to the crystal packing, while a void analysis confirms the efficient packing of the molecules within the crystal.
1. Chemical context
Benzothiazole derivatives constitute an important class of nitrogen- and sulfur-containing heterocyclic compounds owing to their structural diversity, coordination versatility and broad spectrum of biological and physicochemical properties (Keri et al., 2015 ▸). The presence of nitrogen and sulfur donor atoms within the fused aromatic framework provides favourable coordination sites for transition-metal ions, while substitution on the benzene ring enables systematic modulation of the electronic properties, molecular polarity and intermolecular interactions of the ligand. Consequently, substituted benzothiazoles have attracted considerable attention in coordination chemistry, crystal engineering and medicinal chemistry (Barbarossa et al., 2023 ▸).
Particular interest has been devoted to 2-aminobenzothiazole derivatives because the heterocyclic nitrogen atom readily coordinates to metal centres, whereas the exocyclic amino group usually remains non-coordinated and serves as an efficient hydrogen-bond donor. This dual functionality facilitates the formation of coordination compounds together with extended supramolecular architectures sustained by classical and non-classical intermolecular interactions. Previous structural investigations have demonstrated that ZnII complexes containing 2-aminobenzothiazole predominantly exhibit tetrahedral coordination environments in which the ligand binds through the ring nitrogen atom rather than the amino N atom (Davarski et al., 1996 ▸; Kim & Kang, 2012 ▸; Suh et al., 2009 ▸).
Fluorinated benzothiazole derivatives are considered particularly promising because fluorine substitution modifies the electronic distribution of the aromatic system without introducing significant steric effects. The strong electron-withdrawing character of fluorine influences the donor ability of the coordinating nitrogen atom and frequently contributes to crystal stabilization through weak intermolecular contacts, including N—H⋯F and C—H⋯F interactions. In addition, fluorination affects the π-electron density of the aromatic framework, thereby influencing aromatic stacking and other non-covalent interactions responsible for crystal packing (Li et al., 2013 ▸; Kumar et al., 2017 ▸).
The molecular structure of free 2-amino-6-fluoro-1,3-benzothiazole has previously shown that fluorine substitution preserves the near-planarity of the benzothiazole skeleton while allowing the formation of an extensive hydrogen-bonding network in the crystal. Such structural characteristics indicate that this ligand is well suited for the construction of coordination compounds in which both coordination and supramolecular interactions contribute to the overall crystal architecture (Jai-nhuknan et al., 1997a ▸,b ▸).
Mixed-ligand ZnII complexes containing nitrogen-donor heterocycles and carboxylate ligands have been widely investigated because of their structural diversity and their ability to generate robust supramolecular assemblies through hydrogen bonding and aromatic interactions. In many cases, acetate anions coordinate in a monodentate manner, leaving the second oxygen atom available for intermolecular hydrogen bonding, which plays an essential role in directing crystal packing (Guo et al., 2011 ▸). Moreover, benzothiazole-based ZnII complexes have attracted increasing attention owing to their potential biological activity and favourable structural characteristics arising from the combination of rigid aromatic ligands and flexible coordination environments (Babu et al., 2015 ▸; Reddy et al., 2014 ▸).
Motivated by these considerations, 2-amino-6-fluoro-1,3-benzothiazole was selected as a ligand combining a rigid aromatic framework, a strong nitrogen donor atom, an amino group capable of forming intermolecular hydrogen bonds and a fluorine substituent expected to influence crystal packing. Zinc acetate was employed as the metal precursor because acetate ions readily adopt monodentate coordination while simultaneously providing additional hydrogen-bond acceptor sites. As part of our continuing studies on coordination compounds of substituted benzothiazoles, the title compound, [Zn(C2H3O2)2(C7H5FN2S)2], (I), was synthesized and its crystal structure, supramolecular organization, Hirshfeld surface and crystal void distribution were investigated.
2. Structural commentary
The asymmetric unit of (I) comprises one independent neutral complex molecule (Fig. 1 ▸). The title compound crystallizes in the non-centrosymmetric Sohncke space group Pna21. The refined Flack parameter of 0.002 (12) confirms that the absolute structure has been reliably established. The ZnII centre is coordinated by two nitrogen atoms from two 2-amino-6-fluoro-1,3-benzothiazole (AFBT) ligands and two oxygen atoms from two acetate (ac) anions, giving a four-coordinate ZnN2O2 environment.
Figure 1.
Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
The AFBT ligands coordinate exclusively through the endocyclic nitrogen atoms of the thiazole rings, whereas both ac anions adopt a monodentate coordination mode. The Zn—O and Zn—N bond lengths (Table 1 ▸) are consistent with those reported for structurally related ZnII complexes containing 2-aminobenzothiazole derivatives, in which the Zn—N and Zn—O bond distances generally fall within the ranges 2.02–2.05 and 1.94–1.98 Å, respectively (Tojiboyeva et al., 2025 ▸; Kim & Kang, 2012 ▸; Kim et al., 2009 ▸).
Table 1. Selected geometric parameters (Å, °).
| Zn1—O1 | 1.977 (3) | O1—C15 | 1.272 (5) |
| Zn1—O3 | 1.954 (2) | O3—C17 | 1.270 (4) |
| Zn1—N1 | 2.038 (3) | O4—C17 | 1.224 (5) |
| Zn1—N3 | 2.045 (3) | O2—C15 | 1.262 (5) |
| O3—Zn1—O1 | 119.78 (12) | N3—Zn1—O1 | 112.87 (11) |
| N1—Zn1—O1 | 104.15 (12) | N3—Zn1—O3 | 102.93 (10) |
| N1—Zn1—O3 | 109.13 (11) | N3—Zn1—N1 | 107.53 (11) |
The coordination geometry around the ZnII centre is best described as a slightly distorted tetrahedron. Quantitative evaluation using the four-coordinate geometry index τ4 proposed by Yang et al., 2007 ▸, defined as τ4 = [360 − (α + β)]/141, where α and β are the two largest coordination angles, gives a value of 0.96, indicating a tetrahedral geometry. The slight distortion from the ideal tetrahedron arises from the different donor characteristics of the nitrogen and oxygen atoms together with the spatial arrangement of the AFBT and ac ligands.
Although the ac anions coordinate in a monodentate fashion, short secondary contacts of Zn1⋯O2 = 2.674 (3) Å and Zn1⋯O4 = 2.819 (4) Å are observed. These separations are significantly longer than normal Zn—O coordination bonds and therefore cannot be regarded as additional coordination interactions. Nevertheless, they indicate the presence of weak secondary intramolecular Zn⋯O contacts, reflecting the spatial organization of the coordination environment.
Both AFBT ligands remain essentially planar after coordination. The root-mean-square (r.m.s.) deviations from the least-squares planes are 0.019 and 0.020 Å, confirming that the π-conjugated benzothiazole framework is well preserved upon coordination. Furthermore, the geometry of the coordinated ligands closely resembles that of the free AFBT molecule, indicating that coordination to the ZnII centre has little influence on the molecular structure of the heterocyclic fragment (Jai-nhuknan et al., 1997a ▸,b ▸).
The ac groups exhibit the characteristic asymmetry of the C—O bond lengths expected for monodentate carboxylate ligands. Coordination occurs through only one oxygen atom of each ac anion, while the second oxygen atom remains uncoordinated, resulting in the observed differentiation of the C—O bond lengths.
3. Supramolecular features
The crystal packing is governed by a combination of classical hydrogen bonds and weaker non-covalent interactions, which collectively generate a robust three-dimensional supramolecular architecture (Fig. 2 ▸). The principal contribution to the crystal packing arises from classical N—H⋯O hydrogen bonds formed between the amino groups of the AFBT ligands and the non-coordinating oxygen atoms of the ac anions (Table 2 ▸). In particular, the N2—H2B⋯O4 and N4—H4B⋯O2 hydrogen bonds link adjacent molecules into infinite chains propagating along the [011] direction.
Figure 2.
Crystal packing of the title compound viewed along the [011] direction, showing the network of N—H⋯O and N—H⋯F hydrogen bonds. Hydrogen bonds are shown as dashed lines.
Table 2. Hydrogen-bond geometry (Å, °).
Cg1 and Cg6 are the centroids of the Zn1/O1/C15/O2 and S1/N1/C1–C7 rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2—H2B⋯O4i | 0.86 (1) | 1.97 (1) | 2.806 (5) | 162 (1) |
| N4—H4B⋯F2ii | 0.86 (1) | 2.44 (1) | 2.910 (6) | 115 (1) |
| N4—H4B⋯O2iii | 0.86 (1) | 2.07 (1) | 2.890 (4) | 160 (1) |
| C18—H18B⋯Cg6iv | 0.96 (2) | 2.97 (2) | 3.565 (5) | 121 (1) |
| C17—O4⋯Cg1 | 1.22 (1) | 3.08 (1) | 3.234 (4) | 86 (1) |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
Besides forming classical hydrogen bonds, atom N4 also participates in a bifurcated hydrogen bond, where hydrogen atom H4B simultaneously interacts with atoms O2 and F2. The N4—H4B⋯F2 contact is considerably weaker than the corresponding N—H⋯O hydrogen bond; however, it plays an important structure-directing role. Although fluorine is generally regarded as a weak hydrogen-bond acceptor, the N—H⋯F interaction links adjacent hydrogen-bonded chains and reinforces the overall supramolecular framework. Thus, the fluorine substituents do not constitute the primary packing motif but act as secondary acceptors that enhance the connectivity and stability of the crystal structure.
The crystal packing is further reinforced by weak C—H⋯π and O⋯π interactions. The methyl group of the ac ligand forms a C18—H18B⋯Cg6 contact, where Cg6 is the centroid of the benzothiazole ring system (S1/C1/N1/C2/C3/C4/C5/C6/C7). The corresponding geometric parameters are H18B⋯Cg6 = 2.972 (19) Å, C18⋯Cg6 = 3.565 (5) Å and C18—H18B⋯Cg6 = 121.1 (13)°, which are typical of weak but significant C—H⋯π interactions. In addition, the carbonyl oxygen atom O4 is involved in an O⋯π interaction with the centroid Cg1 of the coordination plane (Zn1/O1/C15/O2), with an O4⋯Cg1 separation of 3.075 (4) Å (Fig. 3 ▸). Although individually weak, these contacts complement the hydrogen-bonding network and contribute to the efficient packing of the molecules within the crystal.
Figure 3.
View of the π-related intermolecular interactions in the crystal structure of the title compound, showing the offset π–π stacking interaction (Cg1⋯Cg3), the C18—H18B⋯Cg6 C—H⋯π interaction, and the C17—O4⋯Cg1 O⋯π contact. Selected interactions are shown as dashed lines.
A further characteristic feature of the crystal structure is the presence of a π–π interaction between centroids Cg1 and Cg3, where Cg3 corresponds to the thiazole ring (S2/C8/N3/C9/C14). The centroid-to-centroid distance of 3.7559 (19) Å falls within the range typically associated with offset π–π stacking interactions. This arrangement promotes favourable overlap of the π-electron systems while minimizing steric repulsion, thereby providing additional stabilization to the crystal packing.
4. Hirshfeld surface
To obtain a deeper insight into the intermolecular interactions governing the crystal packing, a Hirshfeld surface analysis was carried out using CrystalExplorer21.5 (Spackman et al., 2021 ▸). The Hirshfeld surface mapped over dnorm is shown in Fig. 4 ▸. The Hirshfeld surface has a total area of 444.97 Å2 and an enclosed volume of 517.52 Å3. The most intense red regions on the dnorm surface are localized around the non-coordinating oxygen atoms of the ac ligands and the amino groups of the benzothiazole molecules, corresponding to the shortest intermolecular N—H⋯O hydrogen bonds identified in the crystal structure. Less pronounced red spots are observed around the fluorine atoms, confirming their involvement in weaker N—H⋯F interactions that complement the classical hydrogen-bonding network.
Figure 4.
Hirshfeld surface of the title compound mapped over dnorm, showing the intermolecular contacts responsible for the crystal packing.
The two-dimensional fingerprint plots reveal that H⋯H contacts make the largest contribution to the Hirshfeld surface, accounting for 31.5% of the total surface area (Fig. 5 ▸). This predominance is characteristic of hydrogen-rich molecular crystals and mainly reflects the close packing of neighbouring molecules. The second-largest contribution arises from C⋯H/H⋯C contacts (16.3%), which are associated primarily with the C—H⋯π interactions between the acetate methyl groups and the aromatic benzothiazole fragments. Although individually weak, these interactions contribute significantly to the stabilization of the crystal packing.
Figure 5.
Two-dimensional fingerprint plots of the title compound showing the overall contacts and the individual contributions of H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, F⋯H/H⋯F and S⋯H/H⋯S interactions to the Hirshfeld surface.
The O⋯H/H⋯O contacts contribute 13.0% to the Hirshfeld surface and are directly associated with the classical N—H⋯O hydrogen bonds forming the principal supramolecular framework. Their characteristic sharp spikes on the fingerprint plots indicate the presence of strong directional hydrogen bonds. A comparable contribution is observed for F⋯H/H⋯F contacts (12.9%), demonstrating that the fluorine substituents participate actively in the intermolecular interaction network. Although fluorine is generally considered a weak hydrogen-bond acceptor, its involvement in the bifurcated N—H⋯(O,F) hydrogen bond highlights its important auxiliary role in reinforcing the hydrogen-bonded framework generated by the stronger N—H⋯O interactions.
The contribution of S⋯H/H⋯S contacts reaches 10.2%, reflecting numerous van der Waals contacts involving the sulfur atoms of the benzothiazole rings. The remaining interactions make considerably smaller contributions, including S⋯C/C⋯S (3.5%), C⋯C (2.6%), C⋯F/F⋯C (2.5%), O⋯S/S⋯O (1.9%), F⋯N/N⋯F (1.5%), F⋯O/O⋯F (1.3%), N⋯H/H⋯N and F⋯S/S⋯F (each 1.0%), N⋯S/S⋯N (0.6%), and C⋯N/N⋯C, C⋯O/O⋯C, and F⋯F (each 0.1%). Although individually insignificant, these weak contacts collectively contribute to the overall stabilization of the crystal packing.
5. Database survey
A search of the Cambridge Structural Database (CSD, Version 2026.2.0; Groom et al., 2016 ▸) revealed only three structurally related transition-metal complexes containing benzothiazole-based ligands. Two entries, NOGZUG and NOHBAP (Sahoo et al., 2014 ▸), are CuII complexes featuring cyclometallated imidazolidine–benzothiazole ligands, while QAYKOU (Akhter et al., 2022 ▸) is a RuII η6-p-cymene complex containing an aminobenzothiazole derivative. All of these structures differ significantly from the title compound in both coordination mode and metal coordination geometry. To the best of our knowledge, no closely related ZnII complex containing two neutral AFBT ligands together with two monodentately coordinated acetate anions has previously been reported.
6. Synthesis and crystallization
The following solutions were prepared: (a) an ethanolic solution of a Zn(CH3COO)2·4H2O (1.0 mmol) and (b) an ethanolic solution of AFBT (2.0 mmol). Solution (a) was added to solution (b), and the resulting mixture was stirred at room temperature for 12 h using magnetic stirring. A crystalline precipitate was formed, filtered off, washed several times with ethanol and dried in air. Since the obtained material was readily soluble in dimethylformamide (DMF), it was recrystallized from this solvent. No poor solvent was used to induce crystallization; instead, the product precipitated directly from the ethanolic reaction mixture because of its limited solubility in ethanol, yielding well-formed whitish single crystals suitable for X-ray diffraction analysis and further physicochemical investigations. The reaction scheme is shown in Fig. 6 ▸.
Figure 6.
Reaction scheme.
7. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms bonded to carbon atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) for aromatic carbon atoms and 1.5Ueq(C) for methyl groups. Hydrogen atoms attached to nitrogen atoms were located from difference-Fourier maps and refined with restrained N—H distances of 0.86 Å, with Uiso(H) = 1.2Ueq(N).
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | [Zn(C2H3O2)2(C7H5FN2S)2] |
| M r | 519.88 |
| Crystal system, space group | Orthorhombic, Pna21 |
| Temperature (K) | 273 |
| a, b, c (Å) | 8.26379 (13), 27.6342 (3), 9.21400 (12) |
| V (Å3) | 2104.14 (5) |
| Z | 4 |
| Radiation type | Cu Kα |
| μ (mm−1) | 3.95 |
| Crystal size (mm) | 0.37 × 0.28 × 0.25 |
| Data collection | |
| Diffractometer | XtaLAB Synergy, Single source at home/near, HyPix3000 |
| Absorption correction | Multi-scan (CrysAlis PRO; Rigaku OD, 2023 ▸) |
| Tmin, Tmax | 0.336, 1.000 |
| No. of measured, independent and observed [I ≥ 2σ(I)] reflections | 19982, 4036, 3829 |
| R int | 0.063 |
| (sin θ/λ)max (Å−1) | 0.616 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.113, 1.03 |
| No. of reflections | 4036 |
| No. of parameters | 282 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.38, −0.60 |
| Absolute structure | Hooft et al. (2010 ▸) |
| Absolute structure parameter | 0.002 (12) |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026009163/jp2034sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026009163/jp2034Isup2.hkl
CCDC reference: 2584886
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Institute of Bioorganic Chemistry of the Academy of Sciences of Uzbekistan for providing access to the XtaLAB Synergy-S X-ray diffractometer. They also acknowledge the Uzbek-Japan Innovation Center of Youth for providing access to the analytical instrumentation and research facilities used in this work.
supplementary crystallographic information
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Crystal data
| [Zn(C2H3O2)2(C7H5FN2S)2] | Dx = 1.641 Mg m−3 |
| Mr = 519.88 | Cu Kα radiation, λ = 1.54184 Å |
| Orthorhombic, Pna21 | Cell parameters from 4970 reflections |
| a = 8.26379 (13) Å | θ = 3.7–71.1° |
| b = 27.6342 (3) Å | µ = 3.95 mm−1 |
| c = 9.21400 (12) Å | T = 273 K |
| V = 2104.14 (5) Å3 | Rhombohedral, clear whiteish colourless |
| Z = 4 | 0.37 × 0.28 × 0.25 mm |
| F(000) = 1055.915 |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Data collection
| XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer | 3829 reflections with I≥ 2σ(I) |
| ω scans | Rint = 0.063 |
| Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023) | θmax = 71.7°, θmin = 3.2° |
| Tmin = 0.336, Tmax = 1.000 | h = −10→10 |
| 19982 measured reflections | k = −33→26 |
| 4036 independent reflections | l = −11→11 |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Refinement
| Refinement on F2 | Primary atom site location: dual |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0835P)2] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.113 | (Δ/σ)max = 0.001 |
| S = 1.03 | Δρmax = 0.38 e Å−3 |
| 4036 reflections | Δρmin = −0.60 e Å−3 |
| 282 parameters | Absolute structure: Hooft et al. (2010) |
| 1 restraint | Absolute structure parameter: 0.002 (12) |
| 26 constraints |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Special details
| Refinement. The structure was solved by direct methods and refined by full-matrix least-squares on F2. |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.63340 (5) | 0.623334 (12) | 0.39621 (5) | 0.03898 (13) | |
| S2 | 0.72351 (14) | 0.77996 (3) | 0.52443 (10) | 0.0590 (3) | |
| S1 | 0.72502 (15) | 0.48713 (3) | 0.66695 (11) | 0.0644 (3) | |
| O1 | 0.3990 (3) | 0.61134 (9) | 0.3732 (3) | 0.0533 (6) | |
| O3 | 0.7725 (3) | 0.62617 (8) | 0.2249 (3) | 0.0451 (5) | |
| N1 | 0.7101 (4) | 0.56872 (9) | 0.5279 (3) | 0.0432 (6) | |
| N3 | 0.6824 (3) | 0.68720 (9) | 0.4992 (3) | 0.0392 (5) | |
| F1 | 1.2953 (4) | 0.54886 (14) | 0.8032 (4) | 0.0932 (9) | |
| F2 | 0.4525 (8) | 0.75495 (15) | 1.0179 (4) | 0.1439 (19) | |
| O4 | 0.6401 (4) | 0.56292 (12) | 0.1497 (5) | 0.0902 (13) | |
| O2 | 0.4259 (4) | 0.67805 (10) | 0.2456 (3) | 0.0654 (7) | |
| N2 | 0.4771 (4) | 0.52090 (11) | 0.5138 (4) | 0.0626 (9) | |
| H2a | 0.4271 (4) | 0.54166 (11) | 0.4607 (4) | 0.0751 (11)* | |
| H2b | 0.4299 (4) | 0.49437 (11) | 0.5382 (4) | 0.0751 (11)* | |
| N4 | 0.8032 (4) | 0.72560 (10) | 0.2979 (4) | 0.0555 (8) | |
| H4a | 0.8114 (4) | 0.69899 (10) | 0.2500 (4) | 0.0667 (10)* | |
| H4b | 0.8368 (4) | 0.75225 (10) | 0.2603 (4) | 0.0667 (10)* | |
| C17 | 0.7393 (4) | 0.59503 (13) | 0.1281 (4) | 0.0479 (8) | |
| C8 | 0.7392 (4) | 0.72552 (10) | 0.4282 (4) | 0.0419 (7) | |
| C9 | 0.6236 (4) | 0.69968 (13) | 0.6361 (4) | 0.0452 (7) | |
| C2 | 0.8639 (4) | 0.56674 (12) | 0.5905 (4) | 0.0472 (8) | |
| C16 | 0.1759 (6) | 0.6390 (2) | 0.2183 (7) | 0.0813 (16) | |
| H16a | 0.114 (2) | 0.6150 (14) | 0.269 (4) | 0.122 (2)* | |
| H16b | 0.123 (3) | 0.6698 (6) | 0.226 (5) | 0.122 (2)* | |
| H16c | 0.1849 (6) | 0.6301 (19) | 0.1179 (16) | 0.122 (2)* | |
| C15 | 0.3419 (4) | 0.64213 (12) | 0.2842 (4) | 0.0474 (7) | |
| C5 | 1.1534 (5) | 0.5536 (2) | 0.7335 (5) | 0.0662 (11) | |
| C14 | 0.6342 (5) | 0.74928 (14) | 0.6671 (5) | 0.0546 (9) | |
| C4 | 1.1284 (5) | 0.5957 (2) | 0.6536 (6) | 0.0689 (12) | |
| H4 | 1.2085 (5) | 0.6192 (2) | 0.6478 (6) | 0.0827 (14)* | |
| C3 | 0.9818 (5) | 0.60183 (15) | 0.5827 (5) | 0.0595 (10) | |
| H3 | 0.9630 (5) | 0.62987 (15) | 0.5295 (5) | 0.0714 (11)* | |
| C7 | 0.8947 (5) | 0.52462 (13) | 0.6702 (4) | 0.0544 (9) | |
| C11 | 0.5019 (7) | 0.6876 (2) | 0.8684 (5) | 0.0823 (15) | |
| H11 | 0.4590 (7) | 0.6673 (2) | 0.9391 (5) | 0.0987 (18)* | |
| C10 | 0.5564 (5) | 0.66893 (14) | 0.7380 (5) | 0.0588 (9) | |
| H10 | 0.5480 (5) | 0.63597 (14) | 0.7190 (5) | 0.0705 (11)* | |
| C1 | 0.6246 (4) | 0.52965 (12) | 0.5575 (4) | 0.0463 (8) | |
| C12 | 0.5122 (8) | 0.7365 (2) | 0.8919 (6) | 0.0893 (16) | |
| C6 | 1.0398 (6) | 0.51766 (16) | 0.7425 (5) | 0.0659 (11) | |
| H6 | 1.0594 (6) | 0.48958 (16) | 0.7953 (5) | 0.0791 (14)* | |
| C13 | 0.5779 (8) | 0.76845 (16) | 0.7965 (5) | 0.0783 (14) | |
| H13 | 0.5848 (8) | 0.80134 (16) | 0.8171 (5) | 0.0940 (17)* | |
| C18 | 0.8288 (7) | 0.5981 (3) | −0.0116 (5) | 0.0884 (17) | |
| H18a | 0.925 (3) | 0.5785 (14) | −0.0062 (19) | 0.133 (2)* | |
| H18b | 0.761 (2) | 0.5866 (17) | −0.0889 (9) | 0.133 (2)* | |
| H18c | 0.859 (5) | 0.6311 (4) | −0.030 (3) | 0.133 (2)* |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.0520 (2) | 0.02471 (19) | 0.0402 (2) | −0.00300 (13) | 0.0056 (2) | 0.00357 (17) |
| S2 | 0.0945 (7) | 0.0323 (4) | 0.0502 (5) | −0.0112 (4) | 0.0182 (5) | −0.0093 (3) |
| S1 | 0.0973 (7) | 0.0342 (4) | 0.0616 (5) | 0.0019 (4) | 0.0018 (6) | 0.0195 (4) |
| O1 | 0.0536 (12) | 0.0375 (11) | 0.0689 (19) | 0.0022 (9) | 0.0021 (13) | 0.0025 (12) |
| O3 | 0.0573 (13) | 0.0375 (12) | 0.0404 (12) | −0.0056 (9) | 0.0056 (10) | −0.0060 (9) |
| N1 | 0.0580 (16) | 0.0279 (12) | 0.0437 (14) | 0.0009 (11) | 0.0044 (12) | 0.0064 (11) |
| N3 | 0.0520 (14) | 0.0313 (11) | 0.0343 (12) | −0.0046 (10) | 0.0064 (11) | 0.0016 (10) |
| F1 | 0.0766 (17) | 0.121 (3) | 0.0819 (19) | 0.0238 (17) | −0.0143 (16) | 0.020 (2) |
| F2 | 0.257 (5) | 0.100 (3) | 0.075 (2) | 0.020 (3) | 0.092 (3) | −0.0093 (19) |
| O4 | 0.104 (3) | 0.0625 (19) | 0.104 (3) | −0.0374 (18) | 0.022 (2) | −0.043 (2) |
| O2 | 0.0765 (18) | 0.0472 (14) | 0.0725 (19) | 0.0039 (13) | 0.0058 (17) | 0.0103 (13) |
| N2 | 0.078 (2) | 0.0347 (13) | 0.075 (2) | −0.0137 (14) | −0.0018 (19) | 0.0155 (15) |
| N4 | 0.091 (2) | 0.0297 (12) | 0.0464 (16) | −0.0151 (14) | 0.0216 (17) | −0.0044 (12) |
| C17 | 0.0562 (19) | 0.0389 (16) | 0.0485 (18) | 0.0035 (13) | 0.0039 (15) | −0.0134 (14) |
| C8 | 0.0596 (18) | 0.0242 (13) | 0.0418 (18) | −0.0048 (11) | 0.0059 (13) | −0.0026 (11) |
| C9 | 0.059 (2) | 0.0412 (16) | 0.0354 (16) | 0.0011 (13) | 0.0044 (14) | −0.0006 (13) |
| C2 | 0.068 (2) | 0.0344 (16) | 0.0388 (17) | 0.0100 (13) | 0.0079 (14) | 0.0065 (13) |
| C16 | 0.056 (2) | 0.081 (3) | 0.108 (4) | 0.006 (2) | −0.011 (3) | −0.039 (3) |
| C15 | 0.0567 (18) | 0.0388 (17) | 0.0466 (18) | 0.0095 (14) | 0.0070 (15) | −0.0027 (15) |
| C5 | 0.064 (2) | 0.084 (3) | 0.050 (2) | 0.018 (2) | −0.0005 (19) | 0.012 (2) |
| C14 | 0.074 (3) | 0.0451 (19) | 0.044 (2) | −0.0015 (16) | 0.0128 (17) | −0.0036 (16) |
| C4 | 0.059 (2) | 0.079 (3) | 0.069 (3) | −0.0004 (19) | 0.005 (2) | 0.015 (3) |
| C3 | 0.063 (2) | 0.0509 (19) | 0.065 (2) | 0.0026 (16) | 0.0052 (18) | 0.0197 (18) |
| C7 | 0.084 (2) | 0.0404 (17) | 0.0386 (18) | 0.0153 (16) | 0.0086 (17) | 0.0085 (15) |
| C11 | 0.118 (4) | 0.078 (3) | 0.051 (3) | 0.007 (3) | 0.032 (3) | 0.018 (2) |
| C10 | 0.076 (3) | 0.0508 (19) | 0.0498 (19) | 0.0034 (18) | 0.0124 (19) | 0.0103 (16) |
| C1 | 0.068 (2) | 0.0300 (15) | 0.0408 (17) | −0.0015 (13) | 0.0076 (15) | 0.0037 (13) |
| C12 | 0.136 (5) | 0.081 (3) | 0.051 (2) | 0.017 (3) | 0.029 (3) | −0.011 (3) |
| C6 | 0.086 (3) | 0.062 (2) | 0.049 (2) | 0.027 (2) | 0.005 (2) | 0.0136 (18) |
| C13 | 0.132 (4) | 0.054 (2) | 0.049 (2) | 0.008 (3) | 0.026 (3) | −0.0112 (19) |
| C18 | 0.101 (4) | 0.116 (5) | 0.048 (2) | 0.002 (4) | 0.013 (3) | −0.025 (3) |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Geometric parameters (Å, º)
| Zn1—O1 | 1.977 (3) | C9—C14 | 1.403 (5) |
| Zn1—O3 | 1.954 (2) | C9—C10 | 1.383 (5) |
| Zn1—N1 | 2.038 (3) | C2—C3 | 1.377 (5) |
| Zn1—N3 | 2.045 (3) | C2—C7 | 1.399 (5) |
| S2—C8 | 1.751 (3) | C16—H16a | 0.9600 |
| S2—C14 | 1.729 (4) | C16—H16b | 0.9600 |
| S1—C7 | 1.744 (4) | C16—H16c | 0.9600 |
| S1—C1 | 1.757 (4) | C16—C15 | 1.503 (6) |
| O1—C15 | 1.272 (5) | C5—C4 | 1.392 (7) |
| O3—C17 | 1.270 (4) | C5—C6 | 1.369 (7) |
| N1—C2 | 1.397 (5) | C14—C13 | 1.386 (6) |
| N1—C1 | 1.319 (4) | C4—H4 | 0.9300 |
| N3—C8 | 1.330 (4) | C4—C3 | 1.387 (6) |
| N3—C9 | 1.395 (4) | C3—H3 | 0.9300 |
| F1—C5 | 1.343 (5) | C7—C6 | 1.386 (6) |
| F2—C12 | 1.361 (6) | C11—H11 | 0.9300 |
| O4—C17 | 1.224 (5) | C11—C10 | 1.383 (6) |
| O2—C15 | 1.262 (5) | C11—C12 | 1.371 (8) |
| N2—H2a | 0.8600 | C10—H10 | 0.9300 |
| N2—H2b | 0.8600 | C12—C13 | 1.358 (8) |
| N2—C1 | 1.306 (5) | C6—H6 | 0.9300 |
| N4—H4a | 0.8600 | C13—H13 | 0.9300 |
| N4—H4b | 0.8600 | C18—H18a | 0.9600 |
| N4—C8 | 1.312 (5) | C18—H18b | 0.9600 |
| C17—C18 | 1.487 (6) | C18—H18c | 0.9600 |
| Cg1···Cg3 | 3.7559 (19) | ||
| O3—Zn1—O1 | 119.78 (12) | C16—C15—O1 | 124.1 (4) |
| N1—Zn1—O1 | 104.15 (12) | C16—C15—O2 | 115.7 (4) |
| N1—Zn1—O3 | 109.13 (11) | C4—C5—F1 | 117.6 (5) |
| N3—Zn1—O1 | 112.87 (11) | C6—C5—F1 | 119.9 (4) |
| N3—Zn1—O3 | 102.93 (10) | C6—C5—C4 | 122.4 (4) |
| N3—Zn1—N1 | 107.53 (11) | C9—C14—S2 | 110.5 (3) |
| C14—S2—C8 | 89.73 (17) | C13—C14—S2 | 127.6 (3) |
| C1—S1—C7 | 89.56 (17) | C13—C14—C9 | 121.9 (4) |
| C15—O1—Zn1 | 108.7 (2) | H4—C4—C5 | 120.6 (3) |
| C17—O3—Zn1 | 114.4 (2) | C3—C4—C5 | 118.8 (4) |
| C2—N1—Zn1 | 123.9 (2) | C3—C4—H4 | 120.6 (3) |
| C1—N1—Zn1 | 124.3 (2) | C4—C3—C2 | 120.5 (4) |
| C1—N1—C2 | 111.7 (3) | H3—C3—C2 | 119.8 (2) |
| C8—N3—Zn1 | 121.9 (2) | H3—C3—C4 | 119.8 (3) |
| C9—N3—Zn1 | 124.3 (2) | C2—C7—S1 | 109.8 (3) |
| C9—N3—C8 | 111.8 (3) | C6—C7—S1 | 128.4 (3) |
| H2b—N2—H2a | 120.0 | C6—C7—C2 | 121.7 (4) |
| C1—N2—H2a | 120.0 | C10—C11—H11 | 120.5 (3) |
| C1—N2—H2b | 120.0 | C12—C11—H11 | 120.5 (3) |
| H4b—N4—H4a | 120.0 | C12—C11—C10 | 119.0 (4) |
| C8—N4—H4a | 120.0 | C11—C10—C9 | 119.4 (4) |
| C8—N4—H4b | 120.0 | H10—C10—C9 | 120.3 (2) |
| O4—C17—O3 | 121.5 (4) | H10—C10—C11 | 120.3 (3) |
| C18—C17—O3 | 117.5 (4) | N1—C1—S1 | 114.4 (3) |
| C18—C17—O4 | 121.0 (4) | N2—C1—S1 | 119.6 (3) |
| N3—C8—S2 | 114.1 (2) | N2—C1—N1 | 126.0 (3) |
| N4—C8—S2 | 119.5 (2) | C11—C12—F2 | 118.8 (5) |
| N4—C8—N3 | 126.4 (3) | C13—C12—F2 | 117.0 (5) |
| C14—C9—N3 | 113.8 (3) | C13—C12—C11 | 124.3 (4) |
| C10—C9—N3 | 127.0 (3) | C7—C6—C5 | 117.6 (4) |
| C10—C9—C14 | 119.2 (3) | H6—C6—C5 | 121.2 (2) |
| C3—C2—N1 | 126.5 (3) | H6—C6—C7 | 121.2 (2) |
| C7—C2—N1 | 114.5 (3) | C12—C13—C14 | 116.3 (4) |
| C7—C2—C3 | 119.0 (4) | H13—C13—C14 | 121.9 (3) |
| H16b—C16—H16a | 109.5 | H13—C13—C12 | 121.9 (3) |
| H16c—C16—H16a | 109.5 | H18a—C18—C17 | 109.5 |
| H16c—C16—H16b | 109.5 | H18b—C18—C17 | 109.5 |
| C15—C16—H16a | 109.5 | H18b—C18—H18a | 109.5 |
| C15—C16—H16b | 109.5 | H18c—C18—C17 | 109.5 |
| C15—C16—H16c | 109.5 | H18c—C18—H18a | 109.5 |
| O2—C15—O1 | 120.2 (4) | H18c—C18—H18b | 109.5 |
| Zn1—O1—C15—O2 | −11.6 (3) | F1—C5—C6—C7 | 179.2 (4) |
| Zn1—O1—C15—C16 | 168.2 (3) | F2—C12—C11—C10 | 177.4 (6) |
| Zn1—O3—C17—O4 | −7.8 (3) | F2—C12—C13—C14 | −178.3 (6) |
| Zn1—O3—C17—C18 | 174.0 (3) | N2—C1—S1—C7 | 179.5 (3) |
| Zn1—N1—C2—C3 | 4.9 (4) | N2—C1—N1—C2 | −179.7 (4) |
| Zn1—N1—C2—C7 | −176.3 (3) | N4—C8—S2—C14 | 179.6 (4) |
| Zn1—N1—C1—S1 | 176.9 (2) | N4—C8—N3—C9 | 179.6 (4) |
| Zn1—N1—C1—N2 | −3.4 (3) | C8—S2—C14—C9 | 1.1 (2) |
| Zn1—N3—C8—S2 | 164.4 (2) | C8—S2—C14—C13 | −178.8 (4) |
| Zn1—N3—C8—N4 | −15.8 (3) | C8—N3—C9—C14 | 1.1 (3) |
| Zn1—N3—C9—C14 | −163.0 (3) | C8—N3—C9—C10 | −180.0 (3) |
| Zn1—N3—C9—C10 | 15.9 (4) | C9—C14—C13—C12 | 0.1 (5) |
| S2—C8—N3—C9 | −0.2 (3) | C9—C10—C11—C12 | 1.6 (6) |
| S2—C14—C9—N3 | −1.5 (3) | C2—C3—C4—C5 | −0.5 (5) |
| S2—C14—C9—C10 | 179.5 (3) | C2—C7—S1—C1 | 0.7 (3) |
| S2—C14—C13—C12 | 180.0 (6) | C2—C7—C6—C5 | −0.0 (4) |
| S1—C7—C2—N1 | −0.5 (3) | C14—C9—C10—C11 | −0.3 (5) |
| S1—C7—C2—C3 | 178.4 (3) | C14—C13—C12—C11 | 1.3 (8) |
| S1—C7—C6—C5 | −177.2 (4) | C4—C5—C6—C7 | −1.0 (6) |
| S1—C1—N1—C2 | 0.7 (3) | C4—C3—C2—C7 | −0.5 (5) |
| N1—C2—C3—C4 | 178.3 (4) | C3—C2—N1—C1 | −178.9 (4) |
| N1—C2—C7—C6 | −178.1 (3) | C3—C2—C7—C6 | 0.7 (4) |
| N1—C1—S1—C7 | −0.8 (3) | C3—C4—C5—C6 | 1.2 (6) |
| N3—C8—S2—C14 | −0.5 (3) | C7—C2—N1—C1 | −0.1 (4) |
| N3—C9—C14—C13 | 178.4 (4) | C10—C9—C14—C13 | −0.6 (5) |
| N3—C9—C10—C11 | −179.2 (5) | C10—C11—C12—C13 | −2.3 (7) |
| F1—C5—C4—C3 | −178.9 (4) | C1—S1—C7—C6 | 178.1 (3) |
Diacetatobis(2-amino-6-fluoro-1,3-benzothiazole-κN3)zinc(II) . Hydrogen-bond geometry (Å, º)
Cg1 and Cg6 are the centroids of the Zn1/O1/C15/O2 and S1/N1/C1–C7 rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2B···O4i | 0.86 (1) | 1.97 (1) | 2.806 (5) | 162 (1) |
| N4—H4B···F2ii | 0.86 (1) | 2.44 (1) | 2.910 (6) | 115 (1) |
| N4—H4B···O2iii | 0.86 (1) | 2.07 (1) | 2.890 (4) | 160 (1) |
| C18—H18B···Cg6iv | 0.96 (2) | 2.97 (2) | 3.565 (5) | 121 (1) |
| C17—O4···Cg1 | 1.22 (1) | 3.08 (1) | 3.234 (4) | 86 (1) |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x+1/2, −y+3/2, z−1; (iii) x+1/2, −y+3/2, z; (iv) x, y, z−1.
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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/S2056989026009163/jp2034sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026009163/jp2034Isup2.hkl
CCDC reference: 2584886
Additional supporting information: crystallographic information; 3D view; checkCIF report