Direct synthesis and crystal structure of a novel tetranuclear Co2IIIFe2III Schiff base complex European Journal of Chemistry 11 (3) (2020) 250-254 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2020 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. http://dx.doi.org/10.5155/eurjchem.11.3.250-254.2014 European Journal of Chemistry View Journal Online View Article Online Direct synthesis and crystal structure of a novel tetranuclear Co2IIIFe2III Schiff base complex Eduard Nikolaevich Chygorin 1, Vladimir Nikolayevich Kokozay 2, Iryna Vasylivna Omelchenko 3 and Julia Anatoliyivna Rusanova 4,* 1 Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska str., Kyiv, 01601, Ukraine chygorin.eduard@gmail.com (E.N.Ch.) 2 Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska str., Kyiv, 01601, Ukraine kokozay@univ.kiev.ua (V.N.K.) 3 Scientific and Technological Center, Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 Nauky ave., Kharkiv, 61072, Ukraine irina@xray.isc.kharkov.com (I.V.O.) 4 Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska str., Kyiv, 01601, Ukraine rusanova_j@yahoo.com (J.A.R.) * Corresponding author at: Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska str., Kyiv, 01601, Ukraine. e-mail: usanova_j@chem.knu.ua (J.A. Rusanova). 10.5155/eurjchem.11.3.250-254.2014 Received: 02 August 2020 Received in revised form: 25 August 2020 Accepted: 26 August 2020 Published online: 30 September 2020 Printed: 30 September 2020 The title compound, tetra(µ-2-3-(2-oxybenzylideneamino)-1-hydroxypropan-2-olato)-4- nitrophenolatedi-cobalt(III)-di-iron(III) dimethylsulfoxidehexasolvate, crystallizes in the monoclinic space group P21/c and represent the first example of heterometallic CoIII-FeIII complex with 3-((5-nitro-2-hydroxybenzylidene)amino)propane-1,2-diol/2-(((2,3-dihydroxy propyl)iminio)methyl)-4-nitrophenolate) - a hydroxyl rich Schiff base ligand which was obtained in situ. Crystal data for C52H74Cl2Co2Fe2N8O26S6 (M = 1720.01 g/mol): monoclinic, space group P21/c (no. 14), a = 16.353(3) Å, b = 15.234(2) Å, c = 15.201(3) Å, β = 113.99(2)°, V = 3460.0(12) Å3, Z = 2, T = 173(2) K, μ(MoKα) = 1.225 mm-1, Dcalc = 1.651 g/cm3, 14130 reflections measured (5.7° ≤ 2Θ ≤ 57.266°), 7748 unique (Rint = 0.1051, Rsigma = 0.2148) which were used in all calculations. The final R1 was 0.0914 (I > 2σ(I)) and wR2 was 0.2279 (all data). The metal ions have distorted octahedral coordination geometry and are joined in a tetranuclear {Co2Fe2(µ-O)6} core by O-bridging atoms from the ligand. There are numerous intermolecular interactions occurring between the components of the crystal: π-hole interaction between NO2···NO2 groups of the ligands, short S···S, O···O and C··· C interactions and weak and strong hydrogen bonds. Iron Cobalt Schiff base Direct synthesis Crystal structure Heterometallic complexes Cite this: Eur. J. Chem. 2020, 11(3), 250-254 Journal website: www.eurjchem.com 1. Introduction During the past several decades, polynuclear complexes have attracted considerable interest due to their potential for a wide range of physicochemical properties such as magnetic [1], catalytic [2], and useful light- and/or redox-induced functions [3]. High-nuclearity solids may exist in a wide range of shapes and different arrangements of the metal atoms [4,5]. Iron is an important bioelement and is a part of heteronuclear cores in metallobiosites such as in purple acid phosphatase (FeZn) [6], humancalcineurin (FeZn) [7] and human protein phosphatase 1 (MnFe) [8]. Fe(III) oxo- and hydroxo-bridged complexes are promising materials in the field of bioinorganic chemistry owing to their relevance as models of the protein active sites [9,10] and their activity in important biological processes [11,12]. In recent years, one of the most widely utilized classes of ligands in metal coordination chemistry are the Schiff bases. Due to their synthetic flexibility, these compounds demonstrate exceptionally rich coordination chemistry and diverse properties in the areas of magnetism, luminescence, chirality, catalysis, cytotoxicity, and ferroelectricity [13-15]. Using of these multipurpose ligands in a synthetic approach named direct synthesis of coordination compounds (which based on spontaneous self-assembly of free metal ions with commonly simple and flexible ligands without significant geometrical restrictions) appears to be an extremely powerful tool for the construction of novel hetero-polynuclear complexes [16]. In this study, we have continued our investigations in the field of direct synthesis and present the synthesis and crystal structure of a novel tetranuclear heterometallic (Fe and Co) complex with a mixed N,O,O-donor hydroxyl rich Schiff base ligand derived from the condensation of 5-nitrosalicylaldehyde with 3-amino-1,2-propandiol and formed in situ. ABSTRACT RESEARCH ARTICLE KEYWORDS http://dx.doi.org/10.5155/eurjchem.11.3.250-254.2014 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.11.3.250-254.2014 mailto:chygorin.eduard@gmail.com mailto:kokozay@univ.kiev.ua mailto:irina@xray.isc.kharkov.com mailto:rusanova_j@yahoo.com mailto:usanova_j@chem.knu.ua http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.11.3.250-254.2014&domain=pdf&date_stamp=2020-09-30 Chygorin et al. / European Journal of Chemistry 11 (3) (2020) 250-254 251 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.3.250-254.2014 Table 1. Crystal data and details of the structure refinement for title compound. Parameters Title compound Empirical formula C52H74Cl2Co2Fe2N8O26S6 Formula weight 1720.01 Temperature (K) 173(2) Crystal system Monoclinic Space group P21/c a, (AÅ ) 16.353(3) b, (AÅ ) 15.234(2) c, (AÅ ) 15.201(3) β, (°) 113.99(2) Volume (Å3) 3460.0(12) Z 2 ρcalc (g/cm3) 1.651 μ (mm-1) 1.225 F(000) 1772.0 Crystal size (mm3) 0.100 × 0.100 × 0.050 Radiation MoKα (λ = 0.71073 Å) 2Θ range for data collection (°) 2.850 to 28.633 Index ranges -21 ≤ h ≤ 16, -17 ≤ k ≤ 20, -17 ≤ l ≤ 20 Reflections collected 14130 Independent reflections 7748 [Rint = 0.1051, Rsigma = 0.2148] Data/restraints/parameters 7748/0/442 Goodness-of-fit on F2 0.989 Final R indexes [I≥2σ (I)] R1 = 0.0914, wR2 = 0.1694 Final R indexes [all data] R1 = 0.2083, wR2 = 0.2279 Largest diff. peak/hole (e Å-3) 0.98/-0.63 O2N OH O H2N OH OH + Co0 FeCl2++ Co O O Fe O Fe O O O Co Scheme 1. Reaction scheme for the synthesis of the title compound. 2. Experimental 2.1. Materials and methods All reagents were of commercial quality and were used as received. Solvents were dried and purified using standard procedures [17]. The synthetic method, direct synthesis, has been intensively used and reported in literature [16,18-20]. Its basis lies in the oxidative dissolution of metal(s) during the synthesis. In our case of the synthesis of a heterometallic complex we use of one of the metals in a zero-valent state (Co0), with the other one in the form of a salt (FeCl2) (Scheme 1), which, in general, can be described by Reaction (1) M’0 + M’’Xy + [Ox] + L → [M’n+M’’m + LX] + [Red] (1) where ligand L is the product of the condensation of 5- nitrosalicylaldehyde with 3-amino-1,2-propandiol, formed in situ. 2.2. Measurements IR spectra were recorded on a Perkin-Elmer Spectrum BX spectrometer (KBr tablet). Elemental analyses for metals were performed with an ICP spectrometer (Fisons Instruments, ARL Model 3410+) and with a Perkin-Elmer 2400 analyzer for C, H, N and Cl. Quantitative determinations of the metals were performed by atomic absorption spectroscopy. 2.3. X-ray crystallography For the crystal structure determination, the single-crystal of the title compound was used for data collection on an Xcallibur Sapphire 3 diffractometer equipped with graphite monochro- matic MoKα radiation (λ = 0.71073 Å). The crystal data, data collection and structure refinement details are summarized in Table 1. The structure was solved by direct methods and refined by the full-matrix least-squares technique in the anisotropic approximation for non-hydrogen atoms. The hydrogen atoms were added geometrically and refined as riding, with Uiso = 1.2Ueq(C) for carbon atoms of the ligand and Uiso = 1.5Ueq(C) for methyl atoms of DMSO solvate molecules. For data collection: CrysAlisPro, Agilent Technologies, 2014 [21]; cell refinement: CrysAlisPro, Agilent Technologies, 2014 [21]; data reduction: CrysAlisPro, Agilent Technologies, 2014 [21]; program(s) used to solve structure: SHELXT [22]; program(s) used to refine structure: SHELXL [23]; molecular graphics: SHELXTL [24]. 2.4. Synthesis of title compound 3-Amino-1,2-propandiol (0.194 g, 2.5 mmol), 5-nitrosalicyl aldehyde (0.418 g, 2.5 mmol), and triethylamine (0.35 mL, 2.5 mmol) were dissolved in dimethylsulfoxide (DMSO, 25 mL) and magnetically stirred at 323-333 K (10 min). To the resulting hot yellow solution of the ligand, cobalt powder (0.074 g, 1.25 mmol) and FeCl2·4H2O (0.248 g, 1.25 mmol) were added and the mixture was stirred magnetically until the cobalt was fully dissolved (6 h). Brown crystals suitable for X-ray analysis were formed from the resulting dark colored solution after one month. The crystals were filtered off, washed with dry isopropyl alcohol, and finally dried at room temperature. Yield: 0.3 g, 54% (per iron). Anal. calcd. for C52H74N8O26S6Cl2Co2Fe2: C, 36.31; H, 4.34; N, 6.51. Found: C, 36.33; H, 4.41; N, 6.49%. FT-IR (KBr, ν, cm-1): 3100 br, 2998 w, 2863 w, 1640 m, 1595 vs, 1544 m, 1481 m, 1439 w, 1390 w, 1311 vs, 1250 m, 1200 w, 1125 w, 1100 m, 1015 m, 945 m, 920 w, 841 w, 794 w, 755 w, 731 w, 688 w, 662 w, 595 w, 544 w, 492 w, 442 w. In the high- frequency region, broad medium-intensity bands in the 3100- 2998 cm-1 range can be attributed to ν(CH) due to aromatic C-H stretching, strong bands appearing at 1595 cm-1 were assigned to ν(C=N) stretching vibrations, a very strong absorption at 1311 cm-1 was assigned to ν(NO2). The presence of the solvate molecules (DMSO) is shown by the medium-intensity bands at 1015 and 945 cm-1. The compound is sparingly soluble in DMF and DMSO and insoluble in water. 252 Chygorin et al. / European Journal of Chemistry 11 (3) (2020) 250-254 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.3.250-254.2014 Table 2. Selected bond lengths and angles *. Bond Length (Å) Bond Angles (°) Fe1-O9i 1.961 (5) O9i-Fe1-O9 71.2 (2) Fe1-O9 2.037 (5) O9-Fe1-O7 107.3 (2) Fe1-O7 2.041 (5) O7-Fe1-O10 74.9 (2) Fe1-O10 2.059 (5) O9i-Fe1-Cl1 104.85 (17) Fe1-O8 2.139 (5) O9-Fe1-Cl1 102.99 (17) Fe1-Cl1 2.303 (3) O7-Fe1-Cl1 141.69 (16) S1S-O1S 1.508 (7) O10-Fe1-Cl1 89.11 (17) S1S-C1S 1.753 (10) O8-Fe1-Cl1 85.14 (17) S1S-C2S 1.764 (10) O1-Co1-N1 96.2 (3) Co1-O1 1.863 (5) O1-Co1-O4 91.2 (2) Co1-N1 1.881 (7) O4-Co1-O7 92.5 (2) Co1-O4 1.891 (6) N1-Co1-N2 176.9 (3) Co1-O7 1.892 (5) O4-Co1-N2 92.8 (3) Co1-N2 1.915 (6) O7-Co1-N2 89.7 (2) Co1-O10 1.916 (5) O1-Co1-O10 95.0 (2) O1-C2 1.283 (9) N1-Co1-O10 85.3 (2) C1-C6 1.395 (11) O4-Co1-O10 170.8 (2) * Symmetry code: (i) -x+1, -y+1, -z+1. Figure 1. The molecular structure of the title compound, showing the atom numbering scheme, showing 50% probability displacement ellipsoids. 3. Results and discussion The X-ray investigation of the title complex showed the molecular structure as determined in the crystalline phase. The crystal and the refinement data are shown in Table 1. It crystallizes in the monoclinic space group P21/c. The centrosymmetric unit consists of a complex molecule {[Co2Fe2(HL)2(L)2Cl2]·6DMSO} in which metal atoms are joined by O bridging atoms from the deprotonated Schiff base ligands in the tetranuclear core {Co2Fe2(µ-O)6} forming a nonlinear CoIII···FeIII···FeIII···CoIII chain-like arrangement. The structure also contains six DMSO solvent molecules of crystallization (Figure 1). The inversion center is situated at the mid-point of the Fe2O2 unit. The Schiff base ligands, which contains a tetradentate {NOOO} donor set with three hydroxyl groups that provide their chelating and bridging capabilities, compensate for the charges on the metal ions by existing in two forms, doubly deprotonated (dianionic) and triply deprotonated (trianionic). Each ligand spanning the cobalt atom meridionally; thus, the coordination geometry around the CoIII ion is slightly distorted octahedral with an N2O4 coordination sphere: two oxygen atoms and one nitrogen atom of the dianionic ligand and one nitrogen atom of the trianionic ligand are in the equatorial plane, apical positions are filled by two oxygen atoms of the trianionic ligand. The chelating fragments coordinated to the CoIII ion are twisted, as defined by the dihedral angles of 70.24(2)° between the mean planes of atoms O4/N2/C9/ C8/C14 and O1/N1/C7/C1/C2. The Co-O and Co-N bond lengths are within the ranges 1.863(5) - 1.916(5) Å and 1.881(7) - 1.915(6) Å (Table 2), respectively, which are compa- rable with those for previously reported related compounds (CSD Refcodes: JIJGUH and PENVIQ) [25,26] (CoIII-O/N distances which fall in the range 1.880(4) - 1.995(4) Å). The coordination of the FeIII ion is a highly distorted octahedral O5Cl geometry. Three of the four coordination sites in the equatorial plane are occupied by oxygen atoms of the trianionic Schiff base ligand, one of which is symmetry related (O10, O9, O9 (-x+1, -y+1, -z+1)), and the fourth site is filled by an oxygen atom of the dianionic ligand (O8); octahedral environment being completed with chlorine atom and one oxygen atom of the dianionic ligand in apical positions with an O7Fe1Cl1 angle of 141.69(16)°. (Figure 2) The Fe-O bond lengths are in the range 1.961(5) - 2.139(5) Å, and the Fe-Cl distance is 2.3033(25) Å. These data are in good agreement with analogous data for previously reported related structures (CSD Refcodes: CINSUQ, QIMVEN, and TOJDED) [27-29]. The separation between the CoIII and FeIII ions within the binuclear fragment is 3.0321(16) Å and between two symmetry-related FeIII ions is 3.2513(24) Å. Those distances as well as all bonding parameters and the dimensions of the angles in the title complex are in good agreement with those encountered in related complexes [30,31]. As it has been noted [29], one of the forces that make supramolecular system binding blocks stick to one another is π- hole contacts. The shortest reported contact of that type is 2.80 Å [33]. Chygorin et al. / European Journal of Chemistry 11 (3) (2020) 250-254 253 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.3.250-254.2014 Table 3. Hydrogen geometric parameters (Å, °) of the title compound *. D-H···A D-H H···A D···A ∠D-H···A O8-H8-O3S i 0.82 11.74 22.562(8) 1173.9 C4-H4-Cl1 ii 0.95 2.89 3.762(9) 153.1 C6-H6-O1S iii 0.95 2.40 3.283(12) 154.5 C7-H7-O1S iii 0.95 2.46 3.326(11) 152.0 C14-H14-O2S iv 0.95 2.49 3.274(11) 139.7 C15-H15B-S3S v 0.99 2.85 3.758(9) 152.7 C18-H18A-O3S vi 0.99 2.48 3.279(9) 138.0 C1S-H1SB-O3 0.98 2.42 3.289(12) 147.0 C2S-H2SC-O3 0.98 2.20 3.101(12) 152.4 C4S-H4SC-O2 vii 0.98 2.39 3.357(13) 168.0 2 C5S-H5SA-O2 viii 0.98 2.45 3.192(11) 132.5 * Symmetry codes: (i) -x+1, y+1/2, -z+1/2; (ii) x, -y+1/2, z-1/2; (iii) -x, y+1/2, -z-1/2; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y+1, -z; (vi) x, -y+1/2, z+1/2; (vii) -x, y+1/2, -z+1/2; (viii) x+1, -y+1/2, z+1/2. Figure 2. The crystal packing of the title compound (along a axis). Several C-H···O hydrogen bonds and C-H···Cl, C-H···S, C-H···N contacts that link the components in the crystal are shown as dashed lines. In the title complex π-hole interaction occur between NO2 groups of the ligands forming O···N and O···C contacts with, respectively distances for [O5-N3] and [O5-C5] distances of 3.0226(108) Å and 3.0894(110) Å, respectively. These are in a good agreement with previously reported for analogous contacts [32]. In addition, in the crystal, all units are connected by a number of short connections and hydrogen bonds (Table 3, Figure 2). Thus, the solvent DMSO molecules connected with each other by short S···S (1-x, 0.5+y, 0.5-z) contact [S2S···S3S = 3.4878(38) Å] which is essentially shorter than the sum of the Van der Waals radii for the atoms involved. There are also connections with the complex units through strong O-H···O [O8···O3S (1-x, 0.5+y, 0.5-z) = 2.562(8) Å], O-H···S [O8···S3S(1- x, 0.5+y, 0.5-z) = 3.596(6) Å] and a number of weak C-H···O, C- H···N, C-H···Cl and C-H···C hydrogen bonds (Table 3). These data are in good agreement with previously published data [33-36]. 4. Conclusion The direct synthesis method for preparation of coor- dination compounds was successfully used for the open-air preparation of the novel tetranuclear heterometallic complex with polydentate Schiff base ligands formed in situ as a product of condensation between 5-nitrosalicylaldehyde and 3-amino- 1,2-propandiol. The molecular structure of the newly tetra- nuclear heterometallic (Fe and Co) complex with a mixed N, O, O-donor hydroxyl rich Schiff base ligand was examined by spectroscopic (IR) and X-ray crystallography techniques. Acknowledgements Support is acknowledged from the Ministry of Education and Science of Ukraine (Project No. 19BF037-05). Supporting information CCDC-2019437 contains the supplementary crystallo- graphic data for this paper. These data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/, or by e- mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033. Disclosure statement Conflict of interests: The authors declare that they have no conflict of interest. Author contributions: All authors contributed equally to this work. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. Funding The Ministry of Education and Science of Ukraine (Project No. 19BF037-05), Ukraine. https://www.ccdc.cam.ac.uk/structures/ mailto:data_request@ccdc.cam.ac.uk 254 Chygorin et al. / European Journal of Chemistry 11 (3) (2020) 250-254 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.3.250-254.2014 ORCID Eduard Nikolaevich Chygorin http://orcid.org/0000-0001-5648-0451 Vladimir Nikolayevich Kokozay http://orcid.org/0000-0003-1834-3020 Iryna Vasylivna Omelchenko http://orcid.org/0000-0002-6882-6832 Julia Anatoliyivna Rusanova http://orcid.org/0000-0002-0801-1690 References [1]. Gheorghe, R.; Madalan, A. M.; Costes, J. P.; Wernsdorfer, W.; Andruh, M. Dalton Trans. 2010, 39, 4734-4736. [2]. Trettenhahn, G.; Nagl, M.; Neuwirth, N.; Arion, V. B.; Jary, W.; Poöchlauer, P.; Schmid, W. Angew. Chem. Int. Ed. 2006, 45, 2794-2798. [3]. Balzani, V.; Bergamini, G.; Ceroni, P. Nanoparticles and Nanodevices in Biological Applications, Springer, 2009. [4]. McInnes, E. J. 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This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). http://orcid.org/0000-0001-5648-0451 http://orcid.org/0000-0003-1834-3020 http://orcid.org/0000-0002-6882-6832 http://orcid.org/0000-0002-0801-1690 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms http://creativecommons.org/licenses/by-nc/4.0 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms 1. Introduction 2. Experimental 2.1. Materials and methods 2.2. Measurements 2.3. X-ray crystallography 2.4. Synthesis of title compound 3. Results and discussion 4. Conclusion Acknowledgements Supporting information Disclosure statement Funding ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: