Cyclobenzaprinium salicylate

Abstract

In the title molecular salt [systematic name: 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanaminium 2-hydroxybenzoate], C20H22N+·C7H5O3−, the benzene rings of the cyclobenzaprinium cation are inclined with a dihedral angle of 61.66 (7)°. An intramolecular O—H...O hydrogen bond occurs within the salicylate anion, generating an S(6) ring. In the crystal, the cation and anion are linked by an N—H...O interaction

2,5-Dimethylanilinium 4-hydroxybenzoate–2,5-dimethylaniline–4-hydroxybenzoic acid (1/1/1)

“…The benzene rings of the cation (C1-C6) and anion (C17-C22) are inclined at an angle of 15.00 (9) Å while the benzene rings of the neutral molecules (C9-C14) and (C24-C29) are inclined at an angle of 11.08 (9) Å . The bond lengths of the ions and molecules are comparable with those in previously reported structures (Fun et al, 2011;Mani et al, 2015;Mathlouthi et al, 2014).…”

Cyclobenzaprinium chloride

“…For structurally related tricyclic antidepressants, see: Cimolai (2009); Commissiong et al (1981); Katz & Dube (1988). For related structures, see: Bindya et al (2007); Fun et al (2011); Portalone et al (2007). For standard bond lengths, see Allen et al (1987).…”

“…Cyclobenzaprine has been considered structurally related to the first-generation tricyclic antidepressants (Commissiong et al, 1981;Katz & Dube, 1988;Cimolai, 2009). The crystal structures of amitriptylinium picrate (Bindya et al, 2007), 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz [a,d][7]annulen-5-ol (Portalone et al, 2007) and cyclobenzaprinium salicylate (Fun et al, 2011) have been reported. In view of the importance of yclobenzaprine, this paper reports the crystal structure of the title compound, C 20 H 22 N + .…”

[3-(5-Hydroxy-5H-dibenzo[a,d]cyclohepten-5-yl)propyl]dimethylammonium 3-carboxyprop-2-enoate

“…For its structural relationships to first-generation tricyclic antidepressants, see: Commissiong et al (1981); Katz & Dube (1988); Cimolai (2009). For related structures, see: Bindya et al (2007); Jasinski, Pek et al (2010); Jasinski, Butcher et al (2010); Fun et al (2011); Siddegowda et al (2011). For standard bond lengths, see: Allen et al (1987).…”