Synthesis, Infrared and Molecular Structure of Adamantane-1-Ammonium Picrate Monohydrate: A Derivative of the Antiviral
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TRUCTURE OF ORGANIC COMPOUNDS
Synthesis, Infrared and Molecular Structure of Adamantane-1-Ammonium Picrate Monohydrate: A Derivative of the Antiviral Symmetrel F. M. Niquinia, A. L. S. Mouraa, P. H. Machadoa, K. M. Oliveiraa, and R. S. Correaa,* aDepartamento
de Química, ICEB, Universidade Federal de Ouro Preto, Ouro Preto, MG, CEP 35400-000 Brazil *e-mail: [email protected] Received April 28, 2020; revised June 17, 2020; accepted June 17, 2020
Abstract—The synthesis, infrared, and crystal structure investigations of adamantane-1-ammonium picrate monohydrate, (C10H21N)(C6H2N3O7) ⋅ H2O, were performed. The title compound crystallizes in the space group P21/n with the monoclinic unit cell parameters: a = 12.7211(9) Å, b = 6.8233(4) Å, c = 21.4130(14) Å and β = 105.950(7)°, V = 1787.1(2) Å3, Z = 4. The asymmetric unit of the studied compound consists of one Adamantane-1-ammonium cation, one water and one picrate anion with two disordered nitro groups. The molecules are connected by strong H-bonds. As can be seen, the ionic pair is linked through two bifurcate N–H⋅⋅⋅O hydrogen bonds, identified as N1–H1A⋅⋅⋅O1 and N1–H1A⋅⋅⋅O2, to form a dimer. Also, water molecule acts bridging two picrate molecules connected by O1w–H1w⋅⋅⋅O1 and O1w–H2w⋅⋅⋅O4. These interactions form an infinite chain extended along the [101] direction. Finally, the main intermolecular contacts were analyzed based on Hirshfeld surfaces and their fingerprint plot. DOI: 10.1134/S1063774520060231
INTRODUCTION In recent years, many studies related to design, preparation and characterization of molecular solidstate structures of organic mono- or multi-component with desired properties have been performed. The aim is to understand the use of intermolecular interactions as a strategy to form crystals with the desired organization and specific synthons [1, 2]. Many multi-component systems such as salts, co-crystals and solvate/hydrate forms have been prepared by solvent evaporation, forming stable solids [3, 4]. Also, there are some examples of monohydrate salts, in which water displays an important role to form strong hydrogen bonds stabilizing the ion-pair organization [5–7]. In the literature, there are many multi-component salts formed by nitro-benzene derivatives with interesting structural properties [8]. We highlight the picric acid (PA) [2,4,6-trinitrophenol], an example of a widely studied molecule, forming co-crystals [9] or salts by the transference of the phenolic hydrogen [10]. In general, nitro-aromatic compounds are widely used in manufacturing and blasting industries, and the PA is highly explosive with recognized behavior as an infamous threat to human health, in which can cause severe irritation, thus, water contamination can cause severe epidemic [11]. In this way, recent studies have aimed to obtain compounds able to exhibit high selectivity for the detection of picric acid as by colorimetric
methods [12] or, mainly, by fluorescence properties [13]. Fluorescent sensors have attracted extensive inquisitiveness in the last years due
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