Lokaj Jan, Kettmann Viktor, Milata Viktor, Solčan Tomáš
Acta Crystallogr Sect E Struct Rep Online. 2009 Jul 8;65(Pt 8):o1788. doi: 10.1107/S1600536809025550.
The structure of the title compound, C(8)H(9)N(3), a potential anti-tumour drug, was determined in order to give more insight into its structure-function relationships. The benzimidazole core of the mol-ecule was found to be exactly planar, while the substituents are displaced slightly from the mol-ecular plane [C-C-N-C and C-C-C-N torsion angles of 0.8 (3) and 179.0 (1)° for the methyl and amino groups, respectively]. The bond lengths are analysed in detail and compared with those of the parent unsubstituted analogues. The results show that the lone-pair electrons on the amino N atom are involved in conjugation with the adjacent π system and hence affect the charge distribution in the heterocycle. Two inter-molecular N-H⋯N and C-H⋯N hydrogen bonds have been identified.
为了更深入了解其结构-功能关系,对潜在抗肿瘤药物标题化合物C₈H₉N₃的结构进行了测定。发现该分子的苯并咪唑核心完全呈平面状,而取代基相对于分子平面略有位移[甲基和氨基的C-C-N-C和C-C-C-N扭转角分别为0.8 (3)°和179.0 (1)°]。详细分析了键长,并与未取代母体类似物的键长进行了比较。结果表明,氨基N原子上的孤对电子参与了与相邻π体系的共轭,从而影响了杂环中的电荷分布。已确定了两个分子间的N-H⋯N和C-H⋯N氢键。