5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[a,d][7]annulen-5-ol

Portalone, Gustavo; Colapietro, Marcello; Bindya, S.; Yathirajan, H. S.

doi:10.1107/s160053680700147x

Cited by 7 publications

(9 citation statements)

References 6 publications

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“…The bent transition state is an intermediate conformation state of a cycloheptane, between boat and chair, and is characterized in the ideal case by the following contiguous torsion angles as calculated by Bocian et al (1975) and Bocian & Strauss (1977): 75.1, À60.3, À1.8, 1.7, 60.3, À75.1 and 0.0 . Similar conformations of the tricyclic ring were also observed in nortriptyline and amitriptyline hydrochloride (Klein et al, 1991(Klein et al, , 1994 and related compounds (Vijay et al, 2005;Portalone et al, 2007).…”

Section: Commentsupporting

confidence: 64%

Amitriptylinium picrate: conformational disorder

Bindya¹,

Wong²,

Yathirajan³

et al. 2007

Acta Crystallogr C

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In the structure of the title salt [systematic name: 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-aminium 2,4,6-trinitrophenolate] of a tricyclic antidepressant, C(20)H(24)N+.C(6)H(2)N(3)O(7)-, the dimethylaminopropyl subunit possesses a classical static conformational disorder. The central cycloheptadiene ring adopts a bent conformation that is intermediate between boat and chair forms, leading to a butterfly shape for the hetero-tricyclic moiety. In a complementary fashion, donors from amitriptyline and acceptors from picrate form intermolecular C-H...O hydrogen bonds and N-H...O salt bridges. These hydrogen bonds cluster amitriptyline and picrate ions into a closed R4(4)(36) hetero-tetramer, whereas intermolecular C-H...pi interactions between amitriptyline ions cluster them into homo-dimers. Significant pi-pi stacking interactions are also observed between aromatic rings of amitriptyline and picrate, and these, combined with the C-H...pi interactions, associate molecules into linear arrays along the [111] direction.

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Section: Commentsupporting

confidence: 64%

Amitriptylinium picrate: conformational disorder

Bindya¹,

Wong²,

Yathirajan³

et al. 2007

Acta Crystallogr C

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“…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).…”

Section: Related Literaturementioning

confidence: 99%

“…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 + .…”

Section: Data Collectionmentioning

confidence: 99%

Cyclobenzaprinium chloride

et al. 2011

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In the title molecular salt [systematic name: 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropanaminium chloride], C20H22N+·Cl−, two cation–anion pairs make up the asymmetric unit. The dihedral angles between the mean planes of the two fused benzene rings of the cation are 49.5 (1) and 50.9 (1)°. The cystal packing is stabilized by N—H⋯Cl hydrogen bonds and weak C—H⋯Cl interactions.

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“…For related structures, see: Portalone et al (2007); ; Harrison, Bindya et al (2007). For background, see: Cohen et al (1990); Ahmed et al (2002).…”

Section: Related Literaturementioning

confidence: 99%

“…In continuation of our work on the picrate salts of pharmaceutical compounds (Portalone et al, 2007;Harrison, Bindya et al, 2007), we now report the structure of the title compound, (I).…”

Section: Data Collectionmentioning

confidence: 99%

Desipraminium picrate monohydrate

Harrison

Swamy²,

Nagaraja

et al. 2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 291 K; mean (C-C) = 0.004 Å; Hatom completeness 93%; disorder in main residue; R factor = 0.067; wR factor = 0.220; data-to-parameter ratio = 14.1. CommentDesipramine, 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f]azepine, C 18 H 22 N 2 , is a tricyclic antidepressant (TCA) and pain reliever that inhibits the reuptake of norepinephrine. Medical applications (Cohen et al., 1990) usually utilize desipramine as its hydrochloride salt, i.e. C 18 H 23 N 2

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5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[a,d][7]annulen-5-ol

Abstract: Key indicatorsSingle-crystal X-ray study T = 298 K Mean (C-C) = 0.002 Å R factor = 0.040 wR factor = 0.108 Data-to-parameter ratio = 14.7For details of how these key indicators were automatically derived from the article, see

Cited by 7 publications

References 6 publications

Amitriptylinium picrate: conformational disorder

Amitriptylinium picrate: conformational disorder

Cyclobenzaprinium chloride

Desipraminium picrate monohydrate

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