Bindya S, Wong Wing-Tak, Ashok M A, Yathirajan H S, Rathore R S
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India.
Acta Crystallogr C. 2007 Sep;63(Pt 9):o546-8. doi: 10.1107/S0108270107037468. Epub 2007 Aug 17.
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.
在一种三环抗抑郁药的标题盐[系统名称：3-(10,11-二氢-5H-二苯并[a,d][7]环壬烯-5-亚基)-N,N-二甲基丙-1-铵 2,4,6-三硝基苯酚盐]结构中，C(20)H(24)N⁺·C(6)H(2)N(3)O(7)⁻，二甲基氨基丙基亚基存在典型的静态构象无序。中心环庚二烯环采取一种介于船式和椅式之间的弯曲构象，导致杂三环部分呈蝴蝶形状。以互补方式，阿米替林的供体和苦味酸盐的受体形成分子间C-H…O氢键和N-H…O盐桥。这些氢键将阿米替林和苦味酸根离子聚集成一个封闭的R4(4)(36)杂四聚体，而阿米替林离子之间的分子间C-H…π相互作用将它们聚集成同二聚体。在阿米替林和苦味酸盐的芳香环之间也观察到显著的π-π堆积相互作用，并且这些与C-H…π相互作用相结合，将分子沿[111]方向缔合成线性阵列。
