Almutairi, Saud M.

Aouad, Mohamed Reda

Hughes, David L.

Messali, Mouslim

Said, Musa A.

University of East Anglia digital repository

Z. Kristallogr. NCS 2019; aopMusa A. Said*, David L. Hughes*, Saud M. Almutairi, Mohamed Reda Aouadand Mouslim Messali*Crystal structure of 1-nonylpyridazin-1-ium iodide,C13H23N2Ihttps://doi.org/10.1515/ncrs-2019-0024Received January 8, 2019; accepted March 6, 2019; availableonline May 17, 2019AbstractC13H23N2I, triclinic, P1¯ (no. 2), a= 5.6693(3) Å,b= 8.9457(4) Å, c= 16.2919(7) Å, α= 83.341(4)°,β= 89.534(4)°, γ= 82.491(4)°, V = 813.63(7) Å3, Z= 2,Rgt(F)=0.0446, wRref(F2)=0.0873, T= 295(2) K.CCDC no.: 1885499The molecular structure is shown in the figure. Table 1 con-tains crystallographic data and Table 2 contains the list ofthe atoms including atomic coordinates and displacementparameters.Source of materialAll chemicals were used without further purification. Thetitle ionic liquid was prepared by a method reported earlier[5, 6]. To a solution of pyridazine (1.00 g, 12.5 mmol in*Corresponding authors: Musa A. Said and Mouslim Messali,Chemistry Department, Taibah University, PO Box 30002, Code14177, Al-Madinah Al-Munawarah, Kingdom of Saudi Arabia,e-mail: musasaid04@gmail.com, musa_said04@yahoo.co.uk(M. A. Said); aboutasnim@yahoo.fr (M. Messali); and David L.Hughes, School of Chemistry, University of East Anglia, Norwich,NR4 7TJ, United Kingdom, e-mail: d.l.hughes@uea.ac.ukSaud M. Almutairi: King Abdulaziz City for Science and Technology,Riyadh 11442, PO Box 6086, Kingdom of Saudi ArabiaMohamed Reda Aouad: Chemistry Department, Taibah University,PO Box 30002, Code 14177, Al-Madinah Al-Munawarah, Kingdom ofSaudi ArabiaTable 1: Data collection and handling.Crystal: Yellow prismSize: 0.22×0.06×0.04 mmWavelength: Mo Kα radiation (0.71073 Å)µ: 1.95 mm−1Diffractometer, scan mode: Oxford Diffraction Xcalibur-3Sapphire-3, φ and ωθmax, completeness: 25.0°,>99%N(hkl)measured, N(hkl)unique, Rint: 10743, 2866, 0.059Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2345N(param)refined: 145Programs: CrysAlisPRO [1], SHELX [2, 3],WinGX/ORTEP [4]10 mL of toluene) was added dropwise 1-iodononane (3.18 g,12.5 mmol) and the mixture was placed in a closed containerand exposed to irradiation for 5 h at room temperature usinga sonication bath. Completion of the reaction was markedby the precipitation of a solid from the initially clear andhomogenous mixture in toluene. The pyridazinium-basedionic liquid was isolated by filtration and washed three timeswith ethyl acetate to remove any unreacted starting materi-als and solvent. Finally the 1-nonylpyridazin-1-ium iodidewasdried at a reduced pressure to remove all volatile organic com-pounds. (Yield 75%, yellow powder, m.p. 94−95 °C). Crys-tals were obtained from a mixture of dichloromethane andn-hexane (1:2). Elemental analysis: Anal. Calc. For C13H23IN2:C, 46.72%; H, 6.94%; N, 8.38%; Found: C, 46.80%; H, 6.99%;N, 8.32%. 1H-NMR (DMSO, 400 MHz): δ [p.p.m.]=0.85 (t, 3H),1.29 (m, 12H), 1.99 (quin, 2H), 4.82 (t, 2H), 8.63 (t, 1H), 8.76(t, 1H), 9.65 (d, 1H), 9.99 (d, 1H); 13C-NMR (DMSO, 100 MHz):δ [p.p.m.]= 14.1 (CH3), 22.6 (CH2), 26.1 (CH2), 28.9 (CH2), 29.1(CH2), 29.2 (CH2), 30.3 (CH2), 31.7 (CH2), 66.1 (CH2), 136.8 (CH),136.9 (CH), 149.9 (CH), 154.3 (CH).Experimental detailsThe non-hydrogen atoms were refined with anisotropic ther-mal parameters. Hydrogen atoms were included in idealisedpositions and their U iso values were set to ride on the parentcarbon atoms. In the final difference map, the highest peaks(to ca 0.6 e Å−3) were close to the iodide ion.Scattering factors for neutral atoms were taken from‘International Tables’ [7]. Computer programs used in thisOpen Access.© 2019 Musa A. Said et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution 4.0Public License.Brought to you by | University of East AngliaAuthenticatedDownload Date | 5/31/19 2:10 PM2 | Said et al.: C13H23N2ITable 2: Fractional atomic coordinates and isotropic or equivalentisotropic displacement parameters (Å2).Atom x y z Uiso*/UeqI 0.11316(6) 0.74147(3) 0.42796(2) 0.06645(16)N1 0.3798(7) 0.6652(4) 0.6368(2) 0.0559(10)N2 0.2229(7) 0.7671(4) 0.6679(3) 0.0639(11)C3 0.2714(10) 0.9060(6) 0.6580(3) 0.0751(15)H3 0.1651 0.9803 0.6789 0.090*C4 0.4726(10) 0.9501(6) 0.6180(3) 0.0725(15)H4 0.5005 1.0509 0.6124 0.087*C5 0.6252(9) 0.8435(7) 0.5878(3) 0.0702(14)H5 0.7635 0.8676 0.5613 0.084*C6 0.5710(9) 0.6964(6) 0.5972(3) 0.0651(13)H6 0.6706 0.6200 0.5754 0.078*C11 0.3125(10) 0.5107(5) 0.6461(3) 0.0749(15)H11A 0.4314 0.4441 0.6199 0.090*H11B 0.1618 0.5119 0.6180 0.090*C12 0.2904(11) 0.4490(7) 0.7349(4) 0.0850(17)H12A 0.2360 0.3502 0.7376 0.102*H12B 0.1708 0.5156 0.7608 0.102*C13 0.5189(11) 0.4337(7) 0.7827(4) 0.0915(18)H13A 0.5616 0.5342 0.7864 0.110*H13B 0.6436 0.3791 0.7525 0.110*C14 0.5080(12) 0.3514(8) 0.8698(4) 0.101(2)H14A 0.3866 0.4074 0.9007 0.121*H14B 0.4616 0.2516 0.8664 0.121*C15 0.7394(13) 0.3337(8) 0.9156(4) 0.111(2)H15A 0.7811 0.4338 0.9214 0.133*H15B 0.8623 0.2830 0.8829 0.133*C16 0.7371(13) 0.2453(9) 1.0001(4) 0.115(2)H16A 0.6902 0.1465 0.9945 0.138*H16B 0.6183 0.2979 1.0335 0.138*C17 0.9766(14) 0.2234(9) 1.0449(4) 0.120(2)H17A 1.0963 0.1747 1.0103 0.144*H17B 1.0201 0.3224 1.0522 0.144*C18 0.9802(14) 0.1309(11) 1.1273(4) 0.140(3)H18A 0.9368 0.0319 1.1200 0.168*H18B 0.8604 0.1795 1.1619 0.168*C19 1.2147(15) 0.1097(11) 1.1712(5) 0.159(4)H19A 1.2032 0.0494 1.2234 0.238*H19B 1.3340 0.0591 1.1382 0.238*H19C 1.2575 0.2069 1.1801 0.238*analysis have been noted above, andwere run throughWinGX[4] on a Dell Optiplex 780 PC at the University of EastAnglia.CommentIn recent decades, ionic liquids (ILs) appeared as an emerg-ing class of ecofriendly compounds alternative to volatileorganic compounds (VOCs) due to their outstanding physicaland chemical properties such as negligible vapor pressure,excellent thermal and chemical stability, outstanding dissolv-ing capacity, excellent ionic conductivity, non-flammability,and recyclability [8].These characteristics make ILs strongly attractive forapplications in a myriad different fields and these com-pounds have, therefore, been investigated for a broad rangeof applications including as potential corrosion inhibitors[9], as liquid crystals [10], in separation technology [11],in electrochemistry [12, 13], in pharmacology [14], andbio-catalysis [15].The synthesis of the title IL took place through thenucleophilic attack of the sp2-nitrogen pyridazine atom,which acts as a nucleophile in the nucleophilic displace-ment of halogen on the nonyl iodide to afford the corre-sponding 1-nonylpyridazin-1-ium iodide in 75% yield as solidmaterial.The structure of this newly synthesized IL was confirmedby 1H-NMR, 13C-NMR, single-crystal X-ray diffraction meth-ods and elemental analysis. The 1H-NMR spectrum showeda triplet around δ H 0.85 p.p.m. corresponding to three pro-tons of the methyl group (CH3). The protons of the variousmethylene groups (CH2) were observed at their usual chem-ical shifts. The signals of the pyridazinium protons appearedas two doublets and two triplets, respectively, around δ H 8and 9 p.p.m.. The 13C-NMR spectrum showed CH2 and CH3 attheir usual chemical shifts, and all the aromatic carbons andC=N gave the signals between δ C 136–154 p.p.m.There aremany similarities between this nonyl derivativeand the smaller heptyl compound recently reported [16]. Thetwo structure are essentially isostructural even though a dif-ferent choice of the unit cell is reported. The nonyl group, too,has an all-trans arrangement and is aligned about C(11) witha cis N(2)—N(1)—C(11)—C(12) torsion angle of −61.4(6)°; theN(2)—N(1)—C(11)—H(11a) angle is trans at 177.5°. The iodideion lies over the pyridazinium ring, 3.688 Å from N(1). Thereare five short H· · · I contacts in the range 3.03−3.14 Å, toneighboring cations, formingweakC—H· · · I hydrogenbonds.All the short inter-ion distances involve the iodide ion. Asobserved for the heptyl structure, the long alkyl chains arearranged in parallel/antiparallel stacks.Acknowledgements: Musa A. Said thanks the Alexandervon Humboldt foundation for the valuable and continuoussupport.References1. Oxford Diffraction: CrysAlis PRO. Oxford Diffraction Ltd.,Oxford, UK (2014).2. Sheldrick, G. M.: SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.3. Sheldrick, G. M.: Crystal structure refinement with SHELXL.Acta Crystallogr. C71 (2015) 3–8.4. Farrugia, L. J.: WinGX and ORTEP for Windows : an update.J. Appl. Crystallogr. 45 (2012) 849–854.Brought to you by | University of East AngliaAuthenticatedDownload Date | 5/31/19 2:10 PMSaid et al.: C13H23N2I | 35. Messali, M.; Aouad, M. R.; Ali, A. A.-S.; Rezki, N.; Ben Hadda,T.; Hammouti, B.: Synthesis, characterization, and POManalysis of novel bioactive imidazolium-based ionic liquids.Med. Chem. Res. 24 (2015) 1387–1395.6. Messali, M.: Eco-friendly synthesis of a new class ofpyridinium-based ionic liquids with attractive antimicrobialactivity. Molecules 20 (2015) 14936–14949.7. Prince, E. (Ed.): International tables for crystallography, Vol. C.The International Union of Crystallography, Kluwer AcademicPublishers (1992).8. Earle, M. J.; Esperança, J. M. S. S.; Gilea, M. A.; CanongiaLopes, J. N.; Rebelo, L. P. N.; Magee, J. W.; Seddon, K. R.; Wide-gren, J. A.: The distillation and volatility of ionic liquids. Nature439 (2006) 831–834.9. Lgaz, H.; Benali, O.; Salghi, R.; Jodeh, S.; Larouj, M.; Hamed,O.; Messali, M.; Samhan, S.; Zougagh, M.; Oudda, H.: Pyri-dinium derivatives as corrosion inhibitors for mild steel in 1 MHCl: electrochemical, surface and quantum chemical studies.Der Pharma Chem. 8 (2016) 172–190.10. Levillain, J.; Dubant, G.; Abrunhosa, I.; Gulea, M.; Gaumont,A.-C.: Synthesis and properties of thiazoline based ionicliquids derived from the chiral pool. Chem. Commun. 0 (2003)2914–2915.11. Qiu, H.; Jiang, S.; Liu, X.; Zhao, L.: Novel imidazolium sta-tionary phase for high-performance liquid chromatography.J. Chromatogr. A. 1116 (2006) 46–50.12. Armand, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati,B.: Ionic-liquid materials for the electrochemical challenges ofthe future. Nat. Mater. 8 (2009) 621–629.13. Al-Ghamdi, A. F.; Messali, M.; Ahmed, S. A.: Electrochemicalstudies of new pyridazinium-based ionic liquid and its deter-mination in different detergents. J. Mater. Environ. Sci. 2 (2011)215–224.14. Smiglak, M.; Pringle, J. M.; Lu, X.; Han, L.; Zhang, S.; Gao, H.;MacFarlane, D. R.; Rogers, R. D.: Ionic liquids for energy, mate-rials, and medicine. Chem. Commun. 50 (2014) 9228–9250.15. Sheldon, R. A.: Biocatalysis and biomass conversionin alternative reaction media. Chem. Eur. J. 22 (2016)12984–12999.16. Said, M. A.; Aouad, M. R.; Almutairi, S. M.; Hughes, D. L.; Mes-sali, M.: Crystal structure of 1-heptylpyridazin-1-ium iodide,C11H19N2I. Z. Kristallogr. NCS 233 (2018) 739–741.Brought to you by | University of East AngliaAuthenticatedDownload Date | 5/31/19 2:10 PM

Crystal structure of 1-nonylpyridazin-1-ium iodide, C13H23N2I

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Crystal structure of 1-nonylpyridazin-1-ium iodide, C13H23N2I

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