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(searched for: (10.5155/eurjchem.11.3.255-260.2019))
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Published: 30 September 2020
European Journal of Chemistry, Volume 11, pp 255-260; https://doi.org/10.5155/eurjchem.11.3.255-260.2019

Abstract:
The structure of the title compound, 4-(dimethylamino)pyridin-1-ium-2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-bis(olate) 4-dimethylaminopyridine water undeca-solvate, C57H87Cl5N12O21, obtained from interaction between chloranilic acid (caH2), and dimethyl aminopyridine (DMAP) has been determined by single crystal X-ray diffraction. The title compound, (DMAPH)5(ca)2.5·(DMAP)·11H2O, crystallized in the triclinic crystal system with space group, P (no. 2), a = 13.3824(15) Å, b = 13.4515(17) Å, c = 19.048(2) Å, α = 86.014(4)°, β = 88.821(4)°, γ = 86.367(4)°, V = 3413.3(7) Å3, Z = 2, T = 100(2) K, μ(MoKα) = 0.294 mm-1, Dcalc = 1.414 g/cm3, 59413 reflections measured (3.76° ≤ 2Θ ≤ 56°), 16405 unique (Rint = 0.0517, Rsigma = 0.0589) which were used in all calculations. The final R1 was 0.0460 (I ≥ 2σ(I)) and wR2 was 0.1271 (all data). Using supramolecular chemistry principles, proton donors (chloranilic acid) and acceptor (DMAP) were combined to generate a multicomponent hydrogen-bonded system. Due to the presence of protonated bases (DMAPH+), the dominant interactions are the N+-H···O hydrogen bonds, whereas the negative charges of an acceptor from the chloranilate dianion (ca2-) are delocalized. Additionally, three sets of water clusters in the title compound were identified, namely a cyclic pentamer, a linear, and an acute-shaped trimer water cluster. It was further observed that strong hydrogen bond interactions occurred between the solvated aqua molecule(s) acting as a proton donor and the neutral DMAP acting as a proton acceptor. The crystal packing is further stabilized by O-H···Cl and C-H···Cl weak halogen interactions. The lattice metric strength is further held by observed π-π stacking interactions (centroid-centroid) with inter centroid distances between sets of the DMAPH rings of 3.624(3), 3.642(4), 3.739(3), 3.863(3) and 3.898(3) Å, respectively.
Huang Yuanyuan, Bai Fang, Gao Guowei, Men Jian
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Riya Dattaa, Ramya Vittalacharya, Bubbly S Gudennavar
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Ikram Dhouib, Philippe Guionneau, Stanislav Pechev, Tahar Mhiri, Zakaria Elaoud
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S. Saeed, N. Rashid, P. Jones, R. Hussain
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E.A. El-Sawi, T.B. Mostafa, H.A. Radwan
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A. Saeed, H. Rafique, U. Florke
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Z.Z. Donia, H. Boughzala, A. Driss
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A. Saeed, A. Mumtaz, U. Florke
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J.N. Low, L.M.N.B.F. Santos, C.F.R.A.C. Lima, P. Brandao, L.R. Gomes
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John Nicholson Low
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M.A. Mohamed, E.K.A. Abdelall, Y.H. Zaki, A.O. Abdelhamid
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M.A. El-Apasery, S.M. Al-Mousawi, M.H. Elnagdi
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G. Binzet, U. Florke, N. Kulcu, H. Arslan
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A. Hameed, A. Anwar, S. Yousaf, K.M. Khan, F.Z. Basha
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A. Hameed, A. Anwar, S. Yousaf, K.M. Khan, F.Z. Basha
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G. Binzet, U. Florke, N. Kulcu, H. Arslan
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M. Ziaulla, M.N. Manjunatha, K.R. Nagasundra, N.S. Begum
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S. Saeed, N. Rashid, M. Ali, R. Hussain, P. Jones
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Vitor H. Rodrigues, Maria M. R. R. Costa, Etelvina M. Gomes, Dmitry Isakov, Michael S. Belsley
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Susma Das, Shilpika Khanikar, Shunan Kaping, Jayanti Datta Roy, Arnab Sen, Philippe Helissey
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Kazuki Ogata, Atsushi Nagasawa, Noriyuki Yonezawa, Akiko Okamoto
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Anastasiia M. Mishura, Anna S. Sklyarova, Dmitriy I. Sharapa, Igor’ A. Levandovsky, Michael Serafin, Andrey A. Fokin, Vladimir N. Rodionov
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Ikram Dhouib, Philippe Guionneau, Tahar Mhiri, Zakaria Elaoud
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Federica Castriconi, Marco Paolino, Germano Giuliani, Maurizio Anzini, Giuseppe Campiani, Laura Mennuni, Chiara Sabatini, Marco Lanza, Gianfranco Caselli, Francesca De Rienzo, et al.
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Masaki Ichitani, Soh-Ichi Kitoh, Keiko Tanaka, Shuhei Fujinami, Mitsuhiro Suda, Mitsunori Honda, Akio Kuwae, Kazuhiko Hanai, Ko-Ki Kunimoto
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Iryna O. Lebedyeva, Sean M. Sileno, Kunal Patel, Ion Ghivririga, Peter J. Steel, Alan R. Katritzky
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K. Ramalingam, R. Thiruneelakandan, G. Bocelli, L. Righi
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Z. Repicka, M. Puchonova, L. Husarikova, J. Moncol, M. Koman, M. Mazur, D. Valigura
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M. Ghandi, P. Asgari, A. Taheri, A. Abbasi
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Patrick Ferland, Kathleen E. Prosser, Jeremy L. Bourque, Ian C. Edwards, Nathan S. Hamilton, Lori E. Joyce, Mathew C. Finniss, Scott R. Yorke, Christopher M. Vogels, Frédéric-Georges Fontaine, et al.
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Patrick Ferland, Kathleen E. Prosser, Jeremy L. Bourque, Ian C. Edwards, Nathan S. Hamilton, Lori E. Joyce, Mathew C. Finniss, Scott R. Yorke, Christopher M. Vogels, Frédéric-Georges Fontaine, et al.
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Andrii Vakulka, Evgeny Goreshnik
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Andrii Vakulka, Evgeny Goreshnik
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E.S. Aazam, M.P. Coles
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K.A. Al-Farhan, I. Warad, S.I. Al-Resayes, M.M. Fouda, M. Ghazzali
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J.L.S. Doimeadios
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S. Saeed, N. Rashid, P.G. Jones, R. Hussain, M.H. Bhatti
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W. Ginzinger, V.B. Arion, G. Giester, M. Galanski, B.K. Keppler
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P.T. Todorov, R.N. Petrova, E.D. Naydenova, B.L. Shivachev
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Agnieszka Chylewska, Artur Sikorski, Aleksandra Dąbrowska, Lech Chmurzyński
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M. Toma, A. Sanchez, M.S. Gracia-Tasende, J.S. Casas, J. Sordo, E.E. Castellano, J. Ellena
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M. Toma, A. Sanchez, M.S. Gracia-Tasende, J.S. Casas, J. Sordo, E.E. Castellano, J. Ellena
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Yu.M. Chumakov, Yu.A. Simonov, M. Grozav, M. Crisan, G. Bocelli, A.A. Yakovenko, D. Lyubetsky
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Yu.M. Chumakov, Yu.A. Simonov, M. Grozav, M. Crisan, G. Bocelli, A.A. Yakovenko, D. Lyubetsky
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M. Sladkovicova, P. Mach, L. Smrcok, H. Rundlof
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A. Ahmedova, M.G.F. Vaz, S. Ciattini, G. Gochev, A. Caneschi, M. Mitewa
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M. Toma, A. Sanchez, J.S. Casas, J. Sordo, M.S. Garcia-Tasende, E.E. Castellano, J. Ellena, I. Berdan
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Matthew Wood, Ivan Bernal, Roger Lalancette
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