Cinnarizinium dipicrate

Abstract

In the cinnarizinium dication of the title compound {systematic name: 1-diphenyl­methyl-4-[(2E)-3-phenyl­prop-2-en-1-yl]piperazine-1,4-diium bis­(2,4,6-trinitro­phenolate)}, C26H30N2 2+·2C6H2N3O7 −, the piperazine group is protonated at both N atoms and adopts a slightly distorted chair conformation. Strong N—H⋯Ohy­droxy cation–anion hydrogen bonds link the dication and two anions. In the cation, the (2E)-3-phenyl­prop-2-en-1-yl fragment is disordered over two positions in a ratio of 0.586 (4): 0.414 (4). Two nitro groups in one anion and three in the other one demonstrate rotational disorder. The crystal packing is stabilized by weak inter­molecular π–π [centroid–centroid distances = 3.844 (7), 3.677 (9), 3.825 (5), 3.634 (2) and 3.729 (7) Å], C—H⋯π and C—H⋯O inter­actions.

Cinnarizinium 3,5-dinitrosalicylate

“…For related structures, see: Bertolasi et al (1980);Smith et al (2001); Jasinski et al (2011). For puckering analysis, see: Cremer & Pople (1975).…”

“…A clinical evaluation of cinnarizine in various allergic disorders is published (Barrett & Zolov, 1960). The crystal structures of some related compounds such as cyclizine hydrochloride (Bertolasi et al, 1980), guanidinium 3,5-dinitrosalicylate (Smith et al, 2001) and cinnarizine dipicrate (Jasinski et al, 2011) have been reported.…”

Cinnarizinium picrate

“…For background to the anti-histamine cinnarizine, see: Towse (1980); Barrett & Zolov (1960). For related structures, see: Mouillé et al (1975); Bertolasi et al (1980); Jasinski et al (2011). For additional conformational analysis, see: Cremer & Pople (1975).…”

4-[Bis(4-fluorophenyl)methyl]piperazin-1-ium 2-(2-phenylethyl)benzoate

“…For the biological activity of piperazines, see: Brockunier et al (2004); Bogatcheva et al (2006). For related structures, see: Anilkumar et al (2005); Betz et al (2011); Fun et al (2011); Jasinski et al (2010Jasinski et al ( , 2011; Dutkiewicz et al (2011). For graphset analysis of hydrogen bonds, see: Etter et al (1990); Bernstein et al (1995).…”

“…They are found in biologically active compounds across a number of different therapeutic areas such as antifungal, antibacterial, antimalarial, antipsychotic, antidepressant and antitumour activity against colon, prostate, breast, lung and leukemia tumors (Brockunier et al, 2004;Bogatcheva et al, 2006). The crystal structures of some related compounds, viz., 2-(2phenylethyl)benzoic acid (Anilkumar et al, 2005), levocetirizinium dipicrate (Jasinski et al, 2010), cinnarizinium dipicrate (Jasinski et al, 2011), 1-methylpiperazine-1,4-diium dipicrate (Dutkiewicz et al, 2011) and 4-(4-chlorophenyl)-4-hydroxypipe ridinium 2-(2-phenylethyl)benzoate (Fun et al, 2011) have been reported. Recently, we have reported the crystal structure of 4-[bis(4-fluorophenyl) methyl]piperazin-1-ium picrate (Betz et al, 2011).…”