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Crystal structure of 4-(dimethylamino)pyridin-1-ium-2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-bis(olate) 4-dimethylaminopyridine (2:1) water undeca-solvate
Alebel Nibret Belay (1,*) , Johan Andries Venter (2) , Orbett Teboho Alexander (3)
(1) Department of Chemistry, Bahir Dar University, P.O. Box 79, Bahir Dar, Ethiopia
(2) Department of Chemistry, University of the Free State, P.O. Box 339, Bloemfontein 9300, South Africa
(3) Department of Chemistry, University of the Free State, P.O. Box 339, Bloemfontein 9300, South Africa
(*) Corresponding Author
Received: 06 Aug 2020 | Revised: 27 Aug 2020 | Accepted: 29 Aug 2020 | Published: 30 Sep 2020 | Issue Date: September 2020
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.
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DOI Link: https://doi.org/10.5155/eurjchem.11.3.255-260.2019
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