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Article

Synthesis, Structure and Antimicrobial Activity of New Co(II) Complex with bis-Morpholino/Benzoimidazole-s-Triazine Ligand

by
Saied M. Soliman
1,*,
Eman M. Fathalla
1,
Mona M. Sharaf
2,
Ayman El-Faham
1,
Assem Barakat
3,
Matti Haukka
4,
Alexandra M. Z. Slawin
5,
John Derek Woollins
5,6 and
Morsy A. M. Abu-Youssef
1,*
1
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt
2
Protein Research Department, Genetic Engineering and Biotechnology Research Institute, City of Scientific Research and Technological Applications, Alexandria P.O. Box 21933, Egypt
3
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
4
Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland
5
School of Chemistry, University of St Andrews, St Andrews KY16 9ST, UK
6
Department of Chemistry, Khalifa University, Abu Dhabi P.O. Box 127788, United Arab Emirates
*
Authors to whom correspondence should be addressed.
Inorganics 2023, 11(7), 278; https://doi.org/10.3390/inorganics11070278
Submission received: 6 June 2023 / Revised: 19 June 2023 / Accepted: 25 June 2023 / Published: 29 June 2023
(This article belongs to the Special Issue 10th Anniversary of Inorganics: Bioinorganic Chemistry)
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Versions Notes

Abstract

:
A new Co(II) perchlorate complex of the bis-morpholino/benzoimidazole-s-triazine ligand, 4,4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl)dimorpholine (BMBIT), was synthesized and characterized. The structure of the new Co(II) complex was approved to be [Co(BMBIT)2(H2O)4](ClO4)2*H2O using single-crystal X-ray diffraction. The Co(II) complex was found crystallized in the monoclinic crystal system and P21/c space group. The unit cell parameters are a = 22.21971(11) Å, b = 8.86743(4) Å, c = 24.38673(12) Å and β = 113.4401(6)°. This heteroleptic complex has distorted octahedral coordination geometry with two monodenatate BMBIT ligand units via the benzoimidazole N-atom and four water molecules as monodentate ligands. The hydration water and perchlorate ions participated significantly in the supramolecular structure of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex. Analysis of dnorm map and a fingerprint plot indicated the importance of O···H, N···H, C···H, C···O, C···N and H···H contacts. Their percentages are 27.5, 7.9, 14.0, 0.9, 2.8 and 43.5%, respectively. The sensitivity of some harmful microbes towards the studied compounds was investigated. The Co(II) complex has good antifungal activity compared to the free BMBIT which has no antifungal activity. The Co(II) complex has good activity against B. subtilis, S. aureus, P. vulgaris and E. coli while the free BMBIT ligand has limited activity only towards B. subtilis and P. vulgaris. Hence, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has broad spectrum antimicrobial action compared to the free BMBIT ligand.

1. Introduction

Heterocyclic rings are the main constituent of many compounds in natural and synthetic drugs. Therefore, the scientific exploration of new heterocyclic molecular systems has attracted many chemists in the field of inorganic and organic chemistry [1,2,3,4,5]. In particular, s-triazine heterocycles are important nitrogen heterocyclic molecules. They are six-membered benzene rings incorporating three nitrogen atoms and three carbons. This interesting and exciting s-triazine scaffold has shown many possible applications which have been reviewed recently [6,7,8,9]. In the medical field, many representative examples incorporating the symmetrical rigid structure of the s-triazine scaffold have been synthesized, characterized and explored in pharmacological applications against different targets [10]. These applications include the use of s-triazine derivatives as anticancer [11,12], antimicrobial [13], antiviral [14], and antiprotozoal agents [15].
From this point of view, the incorporation of the benzimidazole scaffold as a very important pharmacophore with s-triazine in one molecule was explored and the results indicated the enhancement of biological activity in the case of the organic hybrid. Singa et al. reported a series of s-triazine molecules clubbed with benzimidazole scaffolds which were assessed against different cancer cells, including breast cancer, colon cancer, melanoma, leukemia, ovarian cancer, non-small cell lung cancer and central nervous system tumours. They exhibited a median growth inhibitory (GI50) in the range of 1.91–2.72 µM. The DNA intercalation and dihydrofolate reductase inhibition was optimized by the same research group [16,17]. Kumar et al. demonstrated the anticancer reactivity and SAR for a set of compounds based on s-triazine with different heterocycles, such as benzimidazole and benzothiazole scaffolds. Interestingly, a noticeable enhancement in the cytotoxic activity was found due to benzimidazole moity and the IC50 was found to be only 4.8 µM, indicating strong potency against breast cancer cell line MCF-7 [18]. Another example was presented by Singa et al. in the form of s-triazine-benzimidazole derivatives. They constructed and tested s-triazine-benzimidazole derivatives for antiproliferative potential against a panel of cancer cell lines and for investigating the bovine serum albumin interaction, which exhibited the highest inhibiting potency [19].
s-Triazines as ligands were studied extensively in coordination chemistry [9]. Refaat et al. designed a pincer ligand-based s-triazine with two arms of pyrazole scaffolds metalled with cobalt. They explored the cytotoxicity activity against two cancer cells including breast (MCF-7) and lung (A549). The results revealed that the Co(II)-pincer complexes exhibited good anticancer reactivity against the two cancer cell lines with IC50 = 15.31 ± 1.76 µM and 25.01 ± 2.29 for (MCF-7) and lung (A549), respectively [20]. Another example is the s-triazine-bridged calixarene explored in coordination chemistry with metal ions such as Co3+, Fe3+ and Cr3+ [21]. The same research group explored metal complex-based tetraoxocalix[2], arene[2] and triazine for thermal and magnetic properties [22]. Several examples were reported and showed the utilization of s-triazine ligands for complexation with cobalt. The s-triazine ligands and cobalt were also explored as a catalyst for chemical synthesis transformation or medical uses [23,24,25,26,27,28,29,30,31,32,33,34,35], but the cobalt metal complex-based s-triazine clubbed with the benzimidazole scaffold has not yet been explored.
Recently, we reported the X-ray structure studies of some metal(II) complexes with hydrazino-s-triazine ligands 2,4-bis(morpholin-4-yl)-6-[(E)-2-[1-(pyridin-2-yl) ethylidene]hydrazin-1-yl]-1,3,5-triazine (DMPT) [36,37] and (E)-2,4-di(piperidin-1-yl)-6-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)-1,3,5-triazine (DPPT) [38]. Their biological activities as antimicrobial agents against different harmful microbes were presented and compared with the corresponding free ligands. It was observed that the metal complexes of DMPT and DPPT have promising antibacterial and antifungal activities compared to the free DMPT and DPPT molecules. In extension to our work with the hydrazino-s-triazine ligands and based on the interesting bioactivity of both s-triazine and benzomidazole scaffolds, we designed a novel s-triazine-benzimidazole organic hybrid as a starting ligand for the preparation of a new Co(II) complex. Herein, we report the synthesis and antimicrobial evaluations of a new Co(II) complex with the hydrazino-s-triazine ligand, 4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl) dimorpholine, shown in Figure 1. The molecular and supramolecular architectures of the studied complex were investigated using single-crystal X-ray diffraction analysis. Antimicrobial evaluations of both compounds are presented.

2. Results

2.1. Synthesis and Characterizations

The new bis-morpholino/benzoimidazole s-triazine (BMBIT) ligand was synthesized following the reported method by Matsuno et al. [39] as indicated in Scheme 1. Cyanuric chloride 1 was first reacted with benzoimidazole 2 in an acetone–water mixture (1:1) in presence of NaHCO3 at 0 °C for two hours and crushed ice was added to obtain the dichlorobenzoimidazole s-triazine derivative 3 as a white solid in good yield and purity, as observed for its NMR spectra.
The target bis-morpholino/benzoimidazole s-triazine (BMBIT) ligand was obtained from the reaction of 3 with two equivalents of morpholine in the presence of K2CO3 using dimethylformamide as the solvent under heating conditions [39] (Scheme 1) to obtain the target product, 4,4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl)dimorpholine (BMBIT), in excellent yield and purity, which was used directly in the complexation process (Scheme 2). Following this, self-assembly of the ethanolic solutions of the bis-morpholino/benzoimidazole s-triazine (BMBIT) ligand and Co(ClO4)2.6H2O was used to obtain the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex as a single-crystalline product (Scheme 2). The elemental analysis of the target complex confirmed the purity of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex and its composition, which is further revealed by single-crystal X-ray structure analysis.
The structural aspects of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex were found in accordance with the FTIR spectra which confirm the coordination of the Co(II) ion with the azomethine nitrogen and also confirmed the involvement of the perchlorate ion in the structure (Figures S1 and S2 in Supplementary Materials). The FTIR spectra of the BMBIT ligand showed the ν(C=N) at 1600 and 1580 cm−1 and the ν(C=C) mode at 1498 cm−1. In the case of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex, the ν(C=N) mode was detected at lower wavenumbers of 1584 and 1575 cm−1. On the other hand, the ν(C=C) mode was detected almost at the same wavenumber as for the free ligand. The ν(C=C) mode for the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex was detected at 1498 cm−1. In addition, a broad splitted band at 1107 and 1073 cm−1 was assigned for the ν(Cl–O) vibrations, confirming the presence of the perchlorate anion.

2.2. X-ray Structure Description

The X-ray single-crystal structure of the newly synthesized complex was confirmed to be [Co(BMBIT)2(H2O)4](ClO4)2*H2O. The crystal system of this complex is monoclinic, and the space group is P21/c. The unit cell parameters are a = 22.21971(11) Å, b = 8.86743(4) Å, c = 24.38673(12) Å and β = 113.4401(6)°. The asymmetric formula of this complex is one [Co(BMBIT)2(H2O)4](ClO4)2*H2O formula. In the unit cell there are four [Co(BMBIT)2(H2O)4](ClO4)2*H2O molecules where the unit cell volume is 4408.44(4) Å3 and the crystal density is 1.631 Mg/m3. Presentation of the coordination sphere of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex is shown in Figure 2.
This heteroleptic complex has a hexa-coordinated Co(II) ion which is coordinated to six ligand groups where all are monodentate. The two N-donor ligand groups are coordinated with Co(II) via the N7 and N8 atoms of the benzoimidazole moiety, where both ligand units are trans to one another. The corresponding Co1-N7 and Co1-N8 distances are 2.1436(13) and 2.1267(13) Å, respectively, while the N7-Co1-N8 bond angle is 173.36(5)°, which is close to the ideal value of 180° for the perfect octahedron. On the other hand, four water molecules are found coordinated with the Co1 atom via O1, O2, O3 and O4 atoms. The corresponding Co-O distances are 2.0878(12), 2.1160(11), 2.0817(12) and 2.1831(12) Å, respectively. The angles between the cis Co-O bonds are in the range of 85.99(5)° to 95.65(5)°, while the two trans O3-Co1-O1 and O2-Co1-O4 angles are 173.42(5) and 176.91(5)°, respectively (Table 1). Hence, the coordination geometry of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex is a distorted octahedron.
It is worth noting that the structure of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex contains one hydration water molecule and two perchlorate counter anions which are not involved in the coordination with the Co(II) ion but are significantly involved in the molecular packing of this complex (Figure 3A). The packing view of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex along the crystallographic ac-direction is clearly seen from Figure 3B. In the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex, molecular packing is controlled by a number of O···H contacts. The coordinated and free water molecules are acting as H-bond donors while the perchlorate and the hydration water are H-bond acceptors. A list of the H-bond parameters is represented in Table 2. The majority of these intermolecular interactions are strong O-H···O hydrogen bonds, and the donor to acceptor distances are in the range of 2.7011(16) Å (O2-H2B···O6) to 3.082(3) Å (O4-H4A···O14). The respective hydrogen to acceptor distances are 1.91(3) and 2.18(4) Å.
The s-triazine ring from one complex molecule and the morpholine ring from another complex unit are found in close contact, whereas the C5···N3 and C6···N2 are the shortest contacts between the two ring systems (Figure 4). The respective contact distances are 3.247 and 3.222 Å.

2.3. Analysis of Molecular Packing

The stability of the crystal structure is derived from many forces which keep the molecules arranged in a specific pattern to keep the crystal stable. The analysis of molecular packing with the help of Hirshfeld calculations provided all probable contacts in the crystal structure. The dnorm, curvedness and shape index surfaces for the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex are shown in Figure 5. The map of dnorm gavea summary of all short contacts, which appear as red and white regions, indicating shorter and equal interaction distances than the vdWs radii sum of the interacting atoms. The longer contacts than the vdWs radii sum of the interacting atoms appeared as blue colored regions. Inspection of the dnorm map indicated the importance of the O···H, N···H, C···H, C···O, C···N and H···H interactions in the molecular packing of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex. These non-covalent interactions are labelled by letters A to F, respectively, for better clarity. A list of the shortest O···H, N···H, C···H, C···O, C···N and H···H interactions are given in Table 3.
The Hirshfeld analysis predicts all possible intermolecular contacts and their percentages in the crystal structure of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex. Hence, it not only presents a qualitative summary of molecular packing but also quantitatively provides the percentages of these non-covalent interactions (Figure 6). The percentages of the O···H, N···H, C···H, C···O, C···N and H···H contacts are 27.5, 7.9, 14.0, 0.9, 2.8 and 43.5%, respectively. Hence, the intermolecular contacts involving hydrogen atom such as H···H, N···H, O···H and C···H are the most common in the crystal structure of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
The fingerprint plot shows a graphical representation of the distance between the surface and an atom inside the surface (di) against the distance between the surface and an atom outside the surface (di), which not only provides a quantitative summary for all possible intermolecular contacts (Figure 6) but also reveal their importance (Figure 7). It is clear that the decomposed fingerprint plots of the O···H, N···H, C···H, C···O, C···N and H···H contacts appear as sharp spikes. This pattern for the fingerprint plots is considered as strong evidence of a strong interaction occurring at short contact distances between the atoms.
The different contacts that occurred at short distances are presented in Table 3. Interestingly, the Hirshfeld analysis detected the presence of anion-π stacking interactions as revealed by the presence of short C25···O14 (3.040 Å) and C32···O16 (3.079 Å), which occur between the perchlorate O-atom with the aromatic π-system of the benzoimidazole and s-triazine rings, respectively. The O6···H2B (1.722 Å), N12···H15 (2.595 Å), H7B···H34B (2.175 Å), C14···H21 (2.566 Å), C6···N2 (3.222 Å) and C25···O14 (3.040 Å) are the shortest non-covalent contacts in the crystal structure of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.

2.4. Antimicrobial Assay

The sensitivity of selected bacteria as Staphylococcus aureus and Bacillus subtilis (gram-positive), Escherichia coli, Proteus vulgaris (gram-negative) and fungi such as Aspergillus fumigatus and Candida albicans towards the free ligand BMBIT and [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex were examined. Recently, the antimicrobial activity of the free ligands DMPT and DPPT were compared with their metal (II) complexes [36,37,38]. It was found that the majority of the studied metal (II) complexes have better antimicrobial activities than the free ligands [36,37,38]. In accordance with our previous studies, it was observed that the free ligand BMBIT has no effect on both fungal species Aspergillus fumigatus and Candida albicans. In contrast, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has good activity against both microbes. The inhibition zone diameters are 13 and 15 mm, respectively, while the MIC values are 312 and 156 μg/mL, respectively. The results are relatively close to the antifungal agent Ketoconazole (Table 4).
The free ligand showed some sensitivity towards the studied gram-positive and gram-negative bacteria. The free BMBIT ligand and the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex are active against the gram-positive bacteria B. subtilis and the gram-negative bacteria P. vulgaris. The inhibition zone diameters are 13 and 17 mm for the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex and 13 mm for BMBIT against both microbes. It is clear that both compounds showed the same sensitivity against B. subtilis as both gave the same inhibition zone diameters and the same MIC value (312 μg/mL). For the gram-negative bacteria P. vulgaris, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has better activity compared to the free ligand. The MIC value for the Co(II) complex is only 78 μg/mL. In addition, the free BMBIT ligand is not active against both S. aureus and E. coli. In contrast, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex showed inhibitions towards these microbes, with zone sizes of 16 and 15 mm, respectively. The respective MIC values are 156 μg/mL for both microbes. Hence, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has better antibacterial activity against all microbes than BMBIT. The antibacterial activity of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex could be described as moderate with respect to the antibacterial agent Gentamycin. In comparison with the studied metal (II) complexes of the DMPT and DPPT ligands [36,37,38], the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has more or less antibacterial activities. On the other hand, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has better antifungal activity against Aspergillus fumigatus and Candida albicans compared with the other metal (II) complexes. As a result, the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex is a broad-spectrum antimicrobial agent against the studied microbes. The interesting antimicrobial activity of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex compared to the free ligand BMBIT could be explained in terms of its ability to prevent the microbes from protein production, leading to the death of the treated microbes [40].

3. Materials and Methods

3.1. Physical Measurements

All chemicals were bought from their commercial sources and used without additional purifications (see Supplementary Materials).

3.2. Synthesis of 4,4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl)dimorpholine (BMBIT) Ligand [39]

First, dichlorobenzoimidazole 3 was synthesized as follows: benzimidazole (0.1 mole, 11.8 g) was dissolved in acetone (15 mL) and added to a solution of cyanuric chloride (0.1 mole, 18.4 g) in acetone (100 mL) at 0–5 °C, and sodium bicarbonate solution (0.12 mole in 100 mL water) was added over a period of 10 min to adjust the pH of the reaction mixture. The reaction mixture was continued stirring for 2 h at 0–5 °C, crushed ice was added and the solid obtained was filtered and dried. The product was recrystallized from ethanol and the pure product 3 was obtained as an off-white precipitate with an 88% yield, mp 118–120 °C.
1H-NMR (400 MHz, DMSO-d6, ppm): δ 7.39–7.45 (m, 2H, Ar-H), 7.76 (d, 1H, J = 7.6 Hz, Ar-H), 8.44 (d, 1H, J = 8.0 Hz, Ar-H), 9.16 (s, 1H, CH, Ar-H); 13C-NMR (100 MHz, DMSO-d6, ppm): δ 116.2, 119.8, 125.3, 131.1, 142.7, 143.6, 161.8, 163.4.
Compound 3 was reacted with morpholine to obtain the target product as follows: 2-(benzimidazol-1-yl)-4,6,-dichloro-s-triazine 3 (10 mmol) was stirred with morpholine (20 mmol) in 10 mL DMF in the presence of K2CO3 (22 mmol) at room temperature for 4 h and then heated at 80 °C overnight. The reaction mixture was poured into an ice-water mixture and the product was filtered, washed with ethanol and dried, to afford the target product BMBIT as a white solid with a 91% yield, mp. 223–225 °C (Lit. [39], yield 98%, mp.222–224 °C). Anal. Calc. C18H21N7O2: C, 58.84; H, 5.76; N, 26.69%. Found: C, 58.65; H, 5.64; N, 26.52%. IR (KBr, cm−1): 3126 ν(C–H), 3058 ν(C–H), 2994 ν(C–H), 2903 ν(C–H), 1600 ν(C=N), 1580 ν(C=N), 1498 ν(C=C).

3.3. Synthesis of [Co(BMBIT)2(H2O)4](ClO4)2*H2O Complex

Co(ClO4)2.6H2O (47.6 mg, 0.2 mmol) in 7 mL ethanol was mixed with an 8 mL ethanolic solution of organic ligand BMBIT (145.3 mg, 0.4 mmol). The resulting brown solution was allowed to evaporate slowly and crystallize at room temperature. After 1 week, reddish-brown crystals of [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex were collected by filtration.
[Co(BMBIT)2(H2O)4](ClO4)2*H2O complex: Anal. Calc. C36H52Cl2CoN14O17: C, 39.93; H, 4.84; N, 18.11; Co, 5.44%. Found: C, 39.70; H, 4.78; N, 17.98; Co, 5.37%. IR (KBr, cm−1): 3113 ν(C–H), 3000 ν(C–H), 2969 ν (C–H), 2912 ν (C–H), 1584 ν(C=N), 1571 ν(C=N), 1497 ν(C=C), 1107 ν(Cl–O), 1073 ν(Cl–O).

3.4. Crystal Structure Determination

The crystal of the Co(II) complex was determined as described Method S1 in Supplementary Materials [41,42,43,44]. The crystallographic details are summarized in Table 5.

3.5. Hirshfeld Analysis

The Crystal Explorer Ver. 3.1 program [45] was used to perform this analysis.

3.6. Antimicrobial Assay

The antibacterial activity is declared in Supplementary Materials (Method S1) [46].

4. Conclusions

A new [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex was synthesized by self-assembly of Co(II) perchlorate and 4,4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl) dimorpholine (BMBIT) in ethanol. The three-dimensional structure and crystal-packing structure aspects of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex were analyzed using single-crystal X-ray diffraction. The Co(II) is hexa-coordinated with a CoN2O4 coordination sphere. All ligand groups (BMBIT and H2O) are monodentate and the cationic complex is monomeric with a distorted octahedral coordination geometry in the coordination sphere. The O···H, N···H, C···H, C···O, C···N and H···H intermolecular contacts contributed by 27.5, 7.9, 14.0, 0.9, 2.8 and 43.5%, respectively, in the supramolecular structure of the Co(II) complex. The [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex has broad-spectrum antimicrobial action compared to the free BMBIT ligand. Mechanistic investigation of the biological activity will be considered in our future work.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/inorganics11070278/s1, Method S1: Crystal structure determination; Figure S1: FTIR spectra of BMBIT; Figure S2: FTIR spectra of [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex; Figure S3: 1H NMR spectra of 3; Figure S4: 13C NMR spectra of 3.

Author Contributions

Conceptualization, M.A.M.A.-Y. and S.M.S.; formal analysis, E.M.F., M.M.S., M.H., A.M.Z.S. and J.D.W.; investigation, E.M.F. and M.M.S.; methodology, E.M.F., M.M.S. and A.B.; software, M.H., S.M.S., A.M.Z.S. and J.D.W.; supervision, M.A.M.A.-Y., A.B. and S.M.S.; validation, A.E.-F. and A.B.; visualization, A.E.-F.; funding acquisition: A.B.; writing—original draft, S.M.S.; writing—review and editing, M.A.M.A.-Y., A.E.-F. and A.B. All authors have read and agreed to the published version of the manuscript.

Funding

The authors would like to extend their sincere appreciation to the Researchers Supporting Project (RSP2023R64), King Saud University, Riyadh, Saudi Arabia.

Data Availability Statement

Not applicable.

Acknowledgments

The authors would like to extend their sincere appreciation to the Researchers Supporting Project (RSP2023R64), King Saud University, Riyadh, Saudi Arabia.

Conflicts of Interest

The authors declare no conflict of interest.

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Inorganics 11 00278 g001 550
Figure 1. Structure of 2,4-bis(morpholin-4-yl)-6-[(E)-2-[1-(pyridin-2-yl)ethylidene] hydrazin-1-yl]-1,3,5-triazine, (DMPT) [36,37], (E)-2,4-di(piperidin-1-yl)-6-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)-1,3,5-triazine (DPPT) [38] and the new 4,4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl) dimorpholine (BMBIT).
Figure 1. Structure of 2,4-bis(morpholin-4-yl)-6-[(E)-2-[1-(pyridin-2-yl)ethylidene] hydrazin-1-yl]-1,3,5-triazine, (DMPT) [36,37], (E)-2,4-di(piperidin-1-yl)-6-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)-1,3,5-triazine (DPPT) [38] and the new 4,4′-(6-(1H-benzo[d]imidazol-1-yl)-1,3,5-triazine-2,4-diyl) dimorpholine (BMBIT).
Inorganics 11 00278 g001
Inorganics 11 00278 sch001 550
Scheme 1. Synthesis of the BMBIT.
Scheme 1. Synthesis of the BMBIT.
Inorganics 11 00278 sch001
Inorganics 11 00278 sch002 550
Scheme 2. Synthesis of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Scheme 2. Synthesis of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Inorganics 11 00278 sch002
Inorganics 11 00278 g002 550
Figure 2. Structure of the coordination sphere of [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex. One of the two perchlorate anions showed disorder and was omitted from this figure for better clarity.
Figure 2. Structure of the coordination sphere of [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex. One of the two perchlorate anions showed disorder and was omitted from this figure for better clarity.
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Inorganics 11 00278 g003 550
Figure 3. Packing views of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Figure 3. Packing views of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
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Inorganics 11 00278 g004 550
Figure 4. The shortest C···C contacts in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Figure 4. The shortest C···C contacts in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
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Inorganics 11 00278 g005 550
Figure 5. Hirshfeld surfaces for the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Figure 5. Hirshfeld surfaces for the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
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Inorganics 11 00278 g006 550
Figure 6. Intermolecular interactions in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Figure 6. Intermolecular interactions in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
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Inorganics 11 00278 g007 550
Figure 7. Fingerprint plots for the relevant contacts in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Figure 7. Fingerprint plots for the relevant contacts in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
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Table
Table 1. Bond distances and angles (Å and °) for the coordination environment of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Table 1. Bond distances and angles (Å and °) for the coordination environment of the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
BondDistanceBondDistance
Co(1)-O(3)2.0817(12)Co(1)-N(8)2.1267(13)
Co(1)-O(1)2.0878(12)Co(1)-N(7)2.1436(13)
Co(1)-O(2)2.1160(11)Co(1)-O(4)2.1831(12)
BondsAngleBondsAngle
O(3)-Co(1)-O(1)173.42(5)O(2)-Co(1)-N(7)85.59(5)
O(3)-Co(1)-O(2)90.88(5)N(8)-Co(1)-N(7)173.36(5)
O(1)-Co(1)-O(2)95.65(5)O(3)-Co(1)-O(4)87.45(5)
O(3)-Co(1)-N(8)93.49(5)O(1)-Co(1)-O(4)85.99(5)
O(1)-Co(1)-N(8)86.56(5)O(2)-Co(1)-O(4)176.91(5)
O(2)-Co(1)-N(8)96.50(5)N(8)-Co(1)-O(4)86.21(5)
O(3)-Co(1)-N(7)92.77(5)N(7)-Co(1)-O(4)91.88(5)
O(1)-Co(1)-N(7)86.96(5)
Table
Table 2. Hydrogen bond geometric parameters in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Table 2. Hydrogen bond geometric parameters in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
D-H…AD-HH···AD···AD-H···A
C7-H7A···O3 #10.982.43.292(6)150.6
O(1)-H(1A)···O(12)0.78(2)1.98(2)2.7418(19)168(2)
O(1)-H(1B)···O(8) #10.85(3)1.93(3)2.7533(18)165(3)
O(2)-H(2A)···O(5) #20.82(3)2.06(3)2.8337(16)159(2)
O(2)-H(2B)···O(6) #30.79(3)1.91(3)2.7011(16)174(3)
O(3)-H(3A)···O(7) #40.82(3)1.92(3)2.7209(17)166(3)
O(3)-H(3B)···O(17)0.86(3)1.89(3)2.7436(18)174(3)
O(4)-H(4A)···O(14) #50.92(4)2.18(4)3.082(3)168(3)
O(4)-H(4B)···O(15) #10.87(3)2.01(3)2.806(4)153(3)
C(25)-H(25)···O(17)0.952.433.286(2)150
O(17)-H(17B)···O(13)0.932.032.914(4)157.4
O(17)-H(17A)···O(15) #10.94(4)1.98(5)2.797(5)143(4)
#1 −x + 1, y + 1/2, −z + 1/2; #2 −x + 2, y − 1/2, −z + 1/2; #3 −x + 2, −y + 1, −z + 1; #4 −x + 1, −y + 1, −z; #5 x, y + 1, z.
Table
Table 3. The short intermolecular interactions in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
Table 3. The short intermolecular interactions in the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex.
ContactDistanceContactDistance
O5···H2A1.902C8···H2B2.653
O7···H3A1.760C9···H2B2.696
O6···H2B1.722C17···H8A2.709
O15···H4B1.904C14···H4C2.713
O16···H152.588C14···H212.566
O11···H1C2.557C20···H3D2.761
O10···H2C2.445C14···H212.566
O12···H1A1.777C35···H1B2.665
O8···H1B1.795C25···H28A2.651
O15···H17A1.956C19···H29A2.683
O14···H4A2.116C20···H29A2.680
O14···H35A2.448C29···H3A2.647
O15···H17B2.481C30···H3A2.711
O13···H17B1.985C2···H2A2.768
O13···H28B2.574C6···N23.222
O12···H7A2.560C5···N33.247
O13···H28B2.574C25···O143.040
N12···H152.595C32···O163.079
H7B···H34B2.175
Table
Table 4. Antimicrobial activities of BMBIT and the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex a.
Table 4. Antimicrobial activities of BMBIT and the [Co(BMBIT)2(H2O)4](ClO4)2*H2O complex a.
MicroorganismBMBIT[Co(BMBIT)2(H2O)4](ClO4)2*H2OControl
A. fumigatusNA b (ND) c13(312)17(156) d
C. albicansNA b (ND) c15(156)20(312) d
S. aureusNA b (ND) c16(156)24(9.7) e
B. subtilis13 (312)13(312)26(4.8) e
E. coliNA b (ND) c15(156) c30(4.8) e
P. vulgaris13 (ND) c17(78) c25(4.8) e
a Inhibition zone diameter; mm (MIC; μg/mL) b NA: no activity; c ND: not determined; d Ketoconazole and e Gentamycin.
Table
Table 5. Crystal data and refinement parameters.
Table 5. Crystal data and refinement parameters.
CCDC2266666
empirical formulaC36H52Cl2CoN14O17
fw1082.74
temp (K)120(2)
λ(Å)1.54184
cryst systMonoclinic
space groupP21/c
a (Å)22.21971(11)
b (Å)8.86743(4)
c (Å)24.38673(12)
β (deg)113.4401(6)
V (Å3)4408.44(4)
Z4
ρcalc (Mg/m3)1.631
μ(Mo Kα) (mm−1)4.967
No. reflns.125499
Unique reflns.9260
Completeness to θ = 67.684°99.9%
GOOF (F2)1.036
Rint0.0300
R1a (I ≥ 2σ)0.0314
wR2b (I ≥ 2σ)0.0841
a R1 = Σ||Fo| − |Fc||/Σ|Fo|. b wR2 = {Σ[w(Fo2 − Fc2)2]/Σ[w(Fo2)2]}1/2.
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Soliman, S.M.; Fathalla, E.M.; Sharaf, M.M.; El-Faham, A.; Barakat, A.; Haukka, M.; Slawin, A.M.Z.; Woollins, J.D.; Abu-Youssef, M.A.M. Synthesis, Structure and Antimicrobial Activity of New Co(II) Complex with bis-Morpholino/Benzoimidazole-s-Triazine Ligand. Inorganics 2023, 11, 278. https://doi.org/10.3390/inorganics11070278

AMA Style

Soliman SM, Fathalla EM, Sharaf MM, El-Faham A, Barakat A, Haukka M, Slawin AMZ, Woollins JD, Abu-Youssef MAM. Synthesis, Structure and Antimicrobial Activity of New Co(II) Complex with bis-Morpholino/Benzoimidazole-s-Triazine Ligand. Inorganics. 2023; 11(7):278. https://doi.org/10.3390/inorganics11070278

Chicago/Turabian Style

Soliman, Saied M., Eman M. Fathalla, Mona M. Sharaf, Ayman El-Faham, Assem Barakat, Matti Haukka, Alexandra M. Z. Slawin, John Derek Woollins, and Morsy A. M. Abu-Youssef. 2023. "Synthesis, Structure and Antimicrobial Activity of New Co(II) Complex with bis-Morpholino/Benzoimidazole-s-Triazine Ligand" Inorganics 11, no. 7: 278. https://doi.org/10.3390/inorganics11070278

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