NDLI: Hydrogen bonding in the anhydrous 1:1 proton-transfer compounds of isonipecotamide with nitro-substituted benzoic acids: the salts of the three isomeric mononitrobenzoic acids and of 3,5-dinitrobenzoic acid

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Hydrogen bonding in the anhydrous 1:1 proton-transfer compounds of isonipecotamide with nitro-substituted benzoic acids: the salts of the three isomeric mononitrobenzoic acids and of 3,5-dinitrobenzoic acid

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Smith, Graham Wermuth, Urs D.
Description	Country affiliation: Australia Author Affiliation: Smith G ( Faculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia. g.smith@qut.edu.au)
Abstract	The structures of the anhydrous 1:1 proton-transfer compounds of isonipecotamide (piperidine-4-carboxamide) with the three isomeric mononitro-substituted benzoic acids and with 3,5-dinitrobenzoic acid, namely 4-carbamoylpiperidinium 2-nitrobenzoate, (I), 4-carbamoylpiperidinium 3-nitrobenzoate, (II), and 4-carbamoylpiperidinium 4-nitrobenzoate, (III), all C $_{6}H$ $_{13}N$ $_{2}O$ $^{+}·C$ $_{7}H$ $_{4}NO$ $_{4}$ $^{-},$ and 4-carbamoylpiperidinium 3,5-dinitrobenzoate, C $_{6}H$ $_{13}N$ $_{2}O$ $_{8}$ $^{+}·C$ $_{7}H$ $_{3}N$ $_{2}O$ $_{6}$ $^{-},$ (IV), respectively, have been determined at 200 K. All the salts form hydrogen-bonded structures, viz. three-dimensional in (I), two-dimensional in (II) and (III), and one-dimensional in (IV). Featured in the hydrogen bonding of three of these [(I), (II) and (IV)] is the cyclic head-to-head amide-amide homodimer motif [graph set R $_{2}$ $^{2}(8)]$ through a duplex N-H O association, the dimer then giving structure extension via either piperidinium or amide H-atom donors and carboxylate O-atom and, in some examples [(II) and (IV)], nitro O-atom acceptors. In (I), the centrosymmetric amide-amide homodimers are expanded laterally through N-H O hydrogen bonds via cyclic R $_{4}$ $^{2}(8)$ interactions, forming ribbons which extend along the c cell direction. These ribbons incorporate the 2-nitrobenzoate cations through centrosymmetric cyclic piperidine-carboxylate N-H O associations [graph set R $_{4}$ $^{4}(12)],$ giving interconnected sheets in the three-dimensional structure. In (II), in which no amide-amide homodimer is present, duplex piperidinium-amide N-H O homomolecular hydrogen-bonding associations [graph set R $_{2}$ $^{2}(14)]$ give centrosymmetric head-to-tail dimers. Structure extension occurs through hydrogen-bonding associations between both the amide H-atom donors and carboxylate and nitro O-atom acceptors, as well as a three-centre piperidinium-carboxylate N-H O,O' cyclic R $_{1}$ $^{2}(4)$ association, giving the two-dimensional network structure. In (III), the centrosymmetric amide-amide dimers are linked through the two carboxylate O-atom acceptors of the anions via bridging piperidinium N-H O,O' H-N $_{amide}$ hydrogen bonds, giving the two-dimensional sheet structure which features centrosymmetric cyclic R $_{4}$ $^{4}(12)$ associations. In (IV), the amide-amide dimer is also centrosymmetric, with the dimers linked to the anions through amide-nitro N-H O interactions. The piperidinium groups extend the structure into one-dimensional ribbons via N-H O $_{carboxylate}$ hydrogen bonds. The structures reported here further demonstrate the utility of the isonipecotamide cation in molecular assembly. They also highlight the efficacy of the cyclic R $_{2}$ $^{2}(8)$ amide-amide hydrogen-bonding homodimer motif in this process and provide an additional homodimer motif type in the head-to-tail R $_{2}$ $^{2}(14)$ association.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 12
Volume Number	66
Language	English
Publisher	IUCr/Wiley
Publisher Date	2010-12-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography
Content Type	Text
Resource Type	Article

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