4-(E)-(2,4-Difluorophenyl)(hydroxyimino)methyl]piperidinium picrate

Jasinski, Jerry P. and Butcher, Ray J. and Yathirajan, H. S. and Mallesha, L. and Mohana, K. N. (2009) 4-(E)-(2,4-Difluorophenyl)(hydroxyimino)methyl]piperidinium picrate. Acta Crystallographica Section E-Structure Reports Online, 65 (10). O2365+. ISSN 1600-5368

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Official URL: https://doi.org/10.1107/S1600536809035363

Abstract

The title compound, C(12)H(15)F(2)N(2)O(+)center dot C(6)H(2)N(3)O(7)(-), a picrate salt of 4-(E)-(2,4-difluorophenyl)(hydroxyimino)methyl]piperidine, crystallizes with two independent molecules in a cation - anion pair in the asymmetric unit. In the cation, a methyl group is trisubstituted by hydroxyimino, piperidin-4-yl and 2,4-difluorophenyl groups, the latter of which contains an F atom disordered over two positions in the ring occupancy ratio 0.631 (4):0.369 (4)]. The mean plane of the hydroxy group is in a synclinical conformation nearly orthogonal N-C-C-C = 72.44 (19)degrees] to the mean plane of the piperidine ring, which adopts a slightly distorted chair conformation. The dihedral angle between the mean plane of the 2,4- difluorophenyl and piperidin-4-yl groups is 60.2 (3)degrees. In the picrate anion, the mean planes of the two o-NO(2) and single p-NO(2) groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)degrees, respectively, with the attached planar benzene ring. The dihedral angle between the mean planes of the benzene ring in the picrate anion and those in the hydroxyimino, piperidin-4-yl and 2,4-difluorophenyl groups in the cation are 84.9 (7), 78.9 (4) and 65.1 (1)degrees, respectively. Extensive hydrogen-bond interactions occur between the cation - anion pair, which help to establish the crystal packing in the unit cell. This includes dual three-center hydrogen bonds with the piperidin-4-yl group, the phenolate and o-NO(2) O atoms of the picrate anion at different positions in the unit cell, which form separate N-H center dot center dot center dot(O,O) bifurcated intermolecular hydrogen-bond interactions. Also, the hydroxy group forms a separate hydrogen bond with a nearby piperidin-4-yl N atom, thus providing two groups of hydrogen bonds, which form an infinite two-dimensional network along (011).

Item Type: Article
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 14 Aug 2019 10:02
Last Modified: 14 Aug 2019 10:02
URI: http://eprints.uni-mysore.ac.in/id/eprint/6386

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