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, 65 (10). o2365-o2366. ISSN 2056-9890

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


The title compound, C12H15F2N2O+·C6H2N3O7−, 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)°] 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)°. In the picrate anion, the mean planes of the two o-NO2 and single p-NO2 groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)°, 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)°, 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-NO2 O atoms of the picrate anion at different positions in the unit cell, which form separate N—H⋯(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: C Swapna Library Assistant
Date Deposited: 25 Oct 2019 06:17
Last Modified: 25 Oct 2019 06:17
URI: http://eprints.uni-mysore.ac.in/id/eprint/9693

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