Desipraminium picrate monohydrate

Harrison, William T. A.; Swamy, M. T.; Nagaraja, Padmarajaiah; Yathirajan, H. S.; Narayana, B.

doi:10.1107/s1600536807041219

Cited by 5 publications

(7 citation statements)

References 5 publications

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“…It is well known that picric acid is used primarily to prepare explosives, and as an intermediate to manufacture dyes. As a strong organic acid, picric acid forms salts with many N-containing organic bases (Smith et al, 2004;Harrison et al, 2007;Muthamizhchelvan et al, 2005). As an extension of our study concerning organic salts based on picric acid (Jin et al, 2010), we herein report the crystal structure of oxonium picrate.…”

Section: S1 Commentmentioning

confidence: 87%

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Oxonium picrate

Jin

Chen

et al. 2011

Acta Cryst E

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The title compound, H3O+·C6H2N3O7 −, consists of one picrate anion and one oxonium cation. The oxonium cation is located on a crystallographic twofold axis and both its H atoms are disordered, each over two symmetry-equivalent positions with occupancy ratios of 0.75. The picrate anions are also located on twofold axes bisecting the phenolate and p-nitro groups. π–π interactions between the rings of the picrates [centroid-to-centroid distances of 3.324 (2) Å] connect the anions to form stacks along the a-axis direction. The stacks are further joined together by the protonated water molecules through hydrogen bonds to form two-dimensional sheets extending parallel to the ab plane. The sheets are stacked on top of each other along the c-axis direction and connected through C—H⋯O interactions between the CH groups of the benzene rings and the picrate nitro groups, with C⋯O distances of 3.450 (2) Å.

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Section: S1 Commentmentioning

confidence: 87%

“…For general background to organic salts of picric acid, see Jin et al (2010); Harrison et al (2007); Muthamizhchelvan et al (2005); Smith et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

Oxonium picrate

Jin

Chen

et al. 2011

Acta Cryst E

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“…The crystal structures of imipramine hydrochloride (Post et al 1975), nortriptyline hydrochloride (Klein et al 1991), amitriptyline hydrochloride (Klein et al 1994), 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz [a,d][7]annulen-5o l derived from the hydrolysis of amitriptyline (Portalone et al, 2007) and amitriptylinium picrate (Bindya et al, 2007) have been reported. The crystal structures of desipraminium picrate and desipraminium picrate hydrate have also been recently reported (Swamy et al, 2007;Harrison et al, 2007). In continuation of our work on related pharmaceutical compounds (Butcher et al, 2007) and in view of the importance of desipramine, this paper reports the crystal structure of the title compound, C 18 H 23 N 2 + .…”

Section: Data Collectionmentioning

confidence: 74%

“…For related structures, see: Bindya et al (2007); Butcher et al (2007); Harrison et al (2007); Klein et al (1991Klein et al ( , 1994; Portalone et al (2007); Post et al (1975); Swamy et al (2007). For pharmaceutical uses of desipramine, see: Deupree et al (2007); Cohen et al (1990).…”

Section: Related Literaturementioning

confidence: 99%

Desipramine hydrochloride: a non-merohedrally twinned structure

et al. 2010

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The title compound, C18H23N2 +·Cl−, is a non-merohedrally twinned salt [domains 0.9288 (3) and 0.0712 (3)] which crystallizes with four independent cation–anion pairs in the asymmetric unit. The seven-membered ring in each of the cations adopts a boat conformation, thus creating a butterfly effect within the ring system. The average value of the dihedral angle between the two aromatic rings in the four cations is 57.1 (1)°. The crystal packing is stabilized only slightly by a collection of intermediate N—H⋯Cl hydrogen-bonding interactions, which produce a weak, but cooperative, infinite, one-dimensional, intermolecular hydrogen-bond network along the a axis. A MOPAC PM3 computational calculation gives support to these observations.

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“…Cocrystal strategy has been often used due to its application in the fields of drug chemistry, physical material chemistry and biological crystallography. Picric acid, as a strong organic acid, is very frequently adopted to facilitate the crystallization of some difficult-crystallized organic bases (Herbstein & Kaftory, 1976;Dubost et al, 1981;Harrison et al, 2007;Peng et al, 2011;Zeng et al, 2011;Dey et al, 2011). In this report, we report the 1:1 cocrystallized complex of 4-nitrophenylhydrazine and picric acid in 95% methanol solution.…”

Section: S1 Commentmentioning

confidence: 92%

4-Nitrophenylhydrazinium picrate monohydrate

Cai¹,

Liu²,

Qiao³

2013

Acta Cryst E

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In the crystal structure of the title compound, C6H8N3O2 +·C6H2N3O7 −·H2O, N—H⋯O and O—H⋯O hydrogen bonds link the components into a two-dimensional network parallel to (010). In addition, there are pairs of weak inversion-related C—H⋯O hydrogen bonds within the two-dimensional network. The three nitro groups are twisted by 1.6 (3), 7.8 (3) and 12.1 (3)° from the ring plane in the anion, while in the cation, the nitro group makes a dihedral angle of 4.6 (2)° with the ring.

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Desipraminium picrate monohydrate

Cited by 5 publications

References 5 publications

Oxonium picrate

Oxonium picrate

Desipramine hydrochloride: a non-merohedrally twinned structure

4-Nitrophenylhydrazinium picrate monohydrate

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