Abstract
 C26H24CoN2O10, monoclinic, F2/d (equiv. to no. 15), a = 23.7125(7) Å, b = 10.7325(4) Å, c = 39.5740(15) Å, β = 90.324(3)°, V = 10071.2(6) Å3, Z = 16, R
 gt(F) = 0.0514, wR
 ref(F
 2) = 0.1048, T = 140(1) K.</jats:p

Hughes, David L.

Said, Musa A.

Shiekh, Rayees Ahmad

University of East Anglia digital repository

Z. Kristallogr. NCS 2018; aopMusa A. Said, David L. Hughes* and Rayees Ahmad Shiekh*Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(µ2-phthalato-κ2O:O′)cobalt(II)], C26H24CoN2O10https://doi.org/10.1515/ncrs-2018-0030Received January 25, 2018; accepted March 21, 2018; availableonline May 30, 2018AbstractC26H24CoN2O10, monoclinic, F2/d (equiv. to no. 15),a= 23.7125(7) Å, b= 10.7325(4) Å, c= 39.5740(15) Å,β= 90.324(3)°, V = 10071.2(6) Å3, Z= 16, Rgt(F)=0.0514,wRref(F2)=0.1048, T= 140(1) K.CCDC no.: 1830398Tables 1 and 2 contain details on crystal structure and mea-surement conditions and a list of the atoms including atomiccoordinates and displacement parameters.*Corresponding authors: David L. Hughes, School of Chemistry,University of East Anglia, Norwich, NR4 7TJ, United Kingdom,e-mail: d.l.hughes@uea.ac.uk; Rayees Ahmad Shiekh, ChemistryDepartment, Taibah University, P.O. Box 30002, Code 14177, Al-Madinah Al-Munawarah, Kingdom of Saudi Arabia; and GovernmentDegree College Pulwama, University of Kashmir, Srinagar 190006,India, e-mail: rayeeschem@gmail.comMusa A. Said: Chemistry Department, Taibah University, P.O. Box30002, Code 14177, Al-Madinah Al-Munawarah, Kingdom of SaudiArabiaTable 1: Data collection and handling.Crystal: Prism., purpleSize: 0.24×0.09×0.05 mmWavelength: Mo Kα radiation (0.71073 Å)µ: 0.75 mm−1Diffractometer, scan mode: Xcalibur 3/Sapphire3, φ andω-scansθmax, completeness: 29.9°,>99%N(hkl)measured, N(hkl)unique, Rint: 50446, 7337, 0.096Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4968N(param)refined: 377Programs: CrysAlisPRO [1], SHELX [2, 3],ORTEPII [4], WinGX and ORTEP [5]Source of materialsThe title compound was prepared from a mixure of cobaltchloride, phthalic acid and furfurylamine in equal propor-tions. Suitable crystals were grown by slow evaporation of thesolvent, CHCl3.Cobalt(II) chloride (2.38 g, 10 mmol) in 30 mL of ethanolwas added gradually to the ethanolic solution of phthalicacid (PA) (1.22 g, 10 mmol), and furfurylamine (FA) ligand(1.66 g, 10 mmol), in the molar ratio 1:1:1 (CoCl2:PA:FA) undercontinuous stirring. The mixture was kept undisturbed andirradiated at a stable medium power level (600 W) in amicrowave oven. The precipitated solid complexes were fil-tered, washed several times with 50% (v/v) ethanol–waterto remove any traces of unreacted starting materials. A pur-ple colored compound was then separated out. The synthe-sized complexes were found to be highly soluble in DMSOand DMF and slightly soluble in CHCl3. The evaporation ofsolvent yielded good quality crystals which were dried in avacuum desiccator over anhydrous CaCl2. Yield 65%, Mol. wt.583.40, M.p. >300 °C. UV-Vis (DMSO) cm−1, 12, 668−12,923,15,374−15,758, 22,333−22,827, IR (KBr, cm−1): 3475 (N–H),2987 (C–H), 1725 (C=O), 1396 (C–N), 1083 (NH2), 851, 728; FarIR (CsI, cm−1) 445 (Co–O). 1H NMR (300 MHz, δ p.p.m. fromTMS in CDCl3, 300 K): δ 9.97 (1H, br N–H, FA), δ 7.37−8.77(8H, phenyl ring), δ 2.90 (2H, HN–CH2). 13C NMR (CDCl3) (δ,p.p.m.): 169−176 (4 C=O, 2 phenyl ring), 130−153 (phenyl ring8 C), 130−137 (aromatic 5 C), 42 (CH2). Molar conductance, Λm(Ω−1cm−1 mol−1, 10−3 DMSO, r.t.): 16.Open Access.© 2018 Musa A. Said et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.Brought to you by | University of East AngliaAuthenticatedDownload Date | 6/15/18 1:47 PM2 | Said et al.: C26H24CoN2O10Table 2: Fractional atomic coordinates and isotropic or equivalentisotropic displacement parameters (Å2).Atom x y z Uiso*/UeqCo1 0.1250 0.05415(4) 0.3750 0.01133(11)O1 0.24728(7) 0.53498(15) 0.34884(5) 0.0241(4)O2 0.18789(6) 0.68087(14) 0.36767(5) 0.0165(4)O3 0.19255(6) 0.95690(14) 0.36320(4) 0.0163(4)O4 0.20981(7) 0.90369(15) 0.41709(5) 0.0196(4)C1 0.28453(9) 0.7346(2) 0.36133(6) 0.0118(5)C2 0.27795(9) 0.8526(2) 0.37562(6) 0.0131(5)C3 0.32501(9) 0.9282(2) 0.38051(7) 0.0174(5)H3 0.3207 1.0061 0.3905 0.021*C4 0.37794(9) 0.8889(2) 0.37076(7) 0.0184(5)H4 0.4092 0.9396 0.3745 0.022*C5 0.38446(9) 0.7735(2) 0.35529(7) 0.0171(5)H5 0.4199 0.7475 0.3482 0.020*C6 0.33781(9) 0.6976(2) 0.35060(6) 0.0139(5)H6 0.3421 0.6206 0.3401 0.017*C7 0.23644(9) 0.6425(2) 0.35870(6) 0.0138(5)C8 0.22204(9) 0.9049(2) 0.38693(7) 0.0141(5)Co2 0.1250 0.56179(4) 0.3750 0.01183(11)O11 0.14462(8) 0.59314(15) 0.44599(5) 0.0322(5)O12 0.14189(6) 0.43534(14) 0.40997(4) 0.0175(4)O13 0.22072(6) 0.20984(15) 0.40993(4) 0.0175(4)O14 0.13054(6) 0.15258(14) 0.41659(4) 0.0158(4)C11 0.16462(9) 0.3907(2) 0.46715(6) 0.0148(5)C12 0.17441(9) 0.2638(2) 0.46112(6) 0.0137(5)C13 0.18452(9) 0.1842(2) 0.48830(7) 0.0173(5)H13 0.1898 0.0996 0.4844 0.021*C14 0.18687(10) 0.2291(2) 0.52088(7) 0.0203(5)H14 0.1934 0.1749 0.5388 0.024*C15 0.17944(10) 0.3558(2) 0.52693(7) 0.0212(6)H15 0.1821 0.3871 0.5488 0.025*C16 0.16811(10) 0.4341(2) 0.50029(7) 0.0197(5)H16 0.1626 0.5185 0.5045 0.024*C17 0.14975(9) 0.4808(2) 0.43951(7) 0.0176(5)C18 0.17642(9) 0.2081(2) 0.42621(6) 0.0138(5)C21 0.11893(10) 0.8790(2) 0.24804(7) 0.0199(5)O22 0.13348(8) 0.92978(17) 0.21765(5) 0.0317(5)C23 0.09471(13) 0.8845(3) 0.19479(8) 0.0386(8)H23 0.0943 0.9041 0.1719 0.046*C24 0.05796(13) 0.8093(3) 0.20961(8) 0.0403(8)H24 0.0280 0.7677 0.1994 0.048*C25 0.07376(11) 0.8052(3) 0.24450(7) 0.0307(7)H25 0.0561 0.7599 0.2615 0.037*C26 0.15667(10) 0.9122(2) 0.27670(7) 0.0191(5)H26A 0.1956 0.8964 0.2706 0.023*H26B 0.1528 1.0001 0.2819 0.023*N27 0.14159(10) 0.8368(2) 0.30671(6) 0.0179(5)C31 0.25633(10) 0.2648(2) 0.28600(7) 0.0197(5)O32 0.21454(7) 0.20441(17) 0.26820(5) 0.0298(5)C33 0.21459(12) 0.2541(3) 0.23657(8) 0.0381(8)H33 0.1904 0.2302 0.2192 0.046*C34 0.25402(13) 0.3417(3) 0.23400(8) 0.0367(8)H34 0.2620 0.3892 0.2150 0.044*C35 0.28198(12) 0.3488(2) 0.26626(8) 0.0328(7)H35 0.3118 0.4009 0.2722 0.039*C36 0.26265(10) 0.2285(2) 0.32183(7) 0.0223(6)Table 2 (continued)Atom x y z Uiso*/UeqH36A 0.3000 0.2518 0.3297 0.027*H36B 0.2592 0.1387 0.3237 0.027*N37 0.21944(9) 0.28909(19) 0.34365(6) 0.0163(4)H27A 0.1640(11) 0.850(2) 0.3226(8) 0.025(8)*H27B 0.1384(13) 0.749(3) 0.3035(9) 0.066(11)*H27C 0.1067(12) 0.861(3) 0.3149(8) 0.035(8)*H37A 0.2206(10) 0.257(2) 0.3665(7) 0.022(7)*H37B 0.2255(12) 0.3724(17) 0.3460(8) 0.053(10)*H37C 0.1844(13) 0.272(3) 0.3369(8) 0.044(9)*Experimental crystallographic detailsThe space group F2/d is a non-standard setting of C2/c(no. 15). This was derived from the diffractometer-generatedI-centred cell with β= 118.141°; application of the transforma-tionmatrix: 1 0 1 / 0−1 0 / 1 0−1, yielded themore appropriatecell with β= 90.324°. The ammonium hydrogen atoms werelocated in difference maps and were refined freely, except forH(37b) for which the N(37)–H(37b) bond was restrained to0.87(2) Å. The remaining hydrogen atoms were included inidealised positions (C—H distances set to 0.93 Å) and theirU iso values were set to ride on the Ueq values of the parentcarbon atoms.CommentTransitionmetal complexeshavebeenamong themostwidelystudied coordination compounds in recent years because theyare becoming progressively more significant as biochemi-cal, analytical and antimicrobial reagents [6, 7]. The com-plexes containing metal ions are active in many biologi-cal processes and show immense biological activity such asallied with certain metal-proteins, complexes contributing inoxygen transport, electronic transfer reactions or the storageof ions [8, 9] and have generatedmassive interest in the studyof systems containing these metals [10]. Metal-based drugshave achieved much significance in medicinal fields and areused as medicines for the treatment of diabetes, cancer, anti-inflammatory and cardiovascular disease [11–13].The crystals analysed show a coordination polymer,[Co{C6H4(COO)2}2]n, 2n(C4H3OCH2NH3), a portion of which isshown by the Figure; symmetry codes are: (i) 1/4−x, y, 3/4−z;(ii) 1/4−x, y−1, 3/4−z; (iii) 1/4−x, 1+y, 3/4−z; (iv) x, 1+y, z; (v)x, y−1, z. Each cobalt atom is four-coordinate with a tetrahe-dral pattern. The cobalt atoms are bridged by pairs of phtha-late ions (related by twofold symmetry axes) and are linkedin a polymeric chain parallel to the b axis; the repeating unit,r.u., is from Co(1) to Co(1iv).The phthalate ligand has been shown to be versatile andflexible and able to coordinate metal atoms in a wide varietyBrought to you by | University of East AngliaAuthenticatedDownload Date | 6/15/18 1:47 PMSaid et al.: C26H24CoN2O10 | 3of patterns. In our sample, a pair of phthalate ligands bindtwo cobalt ions in a 14-membered ring, with the cobalt ligands5.448 and 5.284 Å apart, as shown in the Figure. The 14-membered ring is common inmetal-phthalate complexes, butis normally formed about a centre of symmetry, in contrastto the two-fold symmetry shown in this structure. Further-more, this coordination polymer is formed by a chain of –Co-(phthalate)2-Co– units along the two-fold symmetry axis,and we believe that this is a novel pattern in a phthalate poly-mer chain. We have, however, noted coordination polymersshowing some similar features in complexes of substitutedphthalates with copper [14] and zinc [15].There are two distinct furfurylammonium cations in thetitle structure. They differ in the orientation of the C—NH3groups with respect to the furan ring. They lie separate fromthe Co{C6H4(COO)2}2 polymer chains but the aminium hydro-gen atoms all form classical hydrogen bonds to the carboxy-late oxygen atoms. There are no hydrogen bonds between ther.u. and the adjacent units along the chain, and there are nohydrogen bonds between the chains.References1. Program CrysAlisPRO. Oxford Diffraction Ltd, Yarnton, Oxford(2011).2. Sheldrick, G. M.: SHELXT – Integrated space-group andcrystal-structure determination. Acta Crystallogr. A71 (2015)3–8.3. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr.A64 (2007) 112–122.4. Johnson, C. K.: ORTEPII. Report ORNL-5138. Oak Ridge NationalLaboratory, TN, USA (1976).5. Farrugia, L. J.: WinGX and ORTEP for Windows: an update.J. Appl. Cryst. 45 (2012) 849–854.6. Refat, M. S.; El-Sayed, M. Y.; Adam, A. M. A.: Cu(II), Co(II) andNi(II) complexes of new Schiff base ligand: synthesis, thermaland spectroscopic characterizations. J. Mol. Struct. 1038 (2013)62–72.7. Nejo, A. A.; Kolawole, G. A.; Nejo, A. O.: Synthesis, character-ization, antibacterial, and hermal studies of unsymmetricalSchiff-base complexes of cobalt(II). J. Coord. Chem. 63 (2010)4398–4410.8. Crans, D. C.; Woll, K. A.; Prusinskas, K.; Johnson, M. D.;Norkus, E.: Metal speciation in health and medicine rep-resented by iron and vanadium. Inorg. Chem. 52 (2013)12262–12275.9. Rehman, W.; Saman, F.; Ahmad, I.: Synthesis, characterization,and biological study of some biologically potent Schiff basetransition metal complexes. Russ. J. Coord. Chem. 34 (2008)678–682.10. Choudhary, A.; Sharma, R.; Nagar, M.: Synthesis, characteri-zation and antimicrobial activity of mixed ligand complexes ofCo(II) and Cu(II) with N, O/S donor ligands and amino acids.Int. Res. J. Pharm. Pharmacol. 1 (2011) 172–187.11. Cini, R.; Tamasi, G.; Defazio, S.; Hursthouse, M. B.: Unusualcoordinating behavior by three non-steroidal anti-inflammatorydrugs from the oxicam family towards copper(II). Synthesis,X-ray structure for copper(II)–isoxicam, –meloxicam and –cinnoxicam derivative complexes, and cytotoxic activity for acopper(II)–piroxicam Complex. J. Inorg. Biochem. 101 (2007)1140–1152.12. Crichton, R. R.; Dexter, D. T.; Ward, R. J.: Metal based neu-rodegenerative diseases – From molecular mechanismsto therapeutic strategies. Coord. Chem. Rev. 252 (2008)1189–1199.13. Fricker, S. P.: Metal based drugs: from serendipity to design.Dalton Trans. (2007) 4903–4917.14. Jiang, Z.-R.; Ge, J.; Zhou, Y.-X.; Wang, Z. U.; Chen, D.; Yu, S.-H.;Jiang, H.-L.: Coating sponge with a hydrophobic porous coordi-nation polymer containing a low-energy CF3-decorated surfacefor continuous pumping recovery of an oil spill from water. NPGAsia Materials 8 (2016) e253.15. Huang, J.-H.; Yu, J.-H.; Xu, J.-Q.: Structural characterizationof three semi-rigid tetracarboxylate-containing transition-metal coordination polymers. Polyhedron 117 (2016)126–132.Brought to you by | University of East AngliaAuthenticatedDownload Date | 6/15/18 1:47 PM

Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(μ2-phthalato-κ2O:O′)cobalt(II)], C26H24CoN2O10

Musa A. Said

David L. Hughes

Rayees Ahmad Shiekh

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Zeitschrift für Kristallographie - New Crystal Structures

Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(μ2-phthalato-κ2
 O:O′)cobalt(II)], C26H24CoN2O10

https://ueaeprints.uea.ac.uk/67373/1/Published_manuscript.pdf

Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(μ2-phthalato-κ2O:O′)cobalt(II)], C26H24CoN2O10

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