Kettmann Viktor, Světlík Jan, Veizerová Lucia
Faculty of Pharmacy, Comenius University, Odbojarov 10, SK-83232 Bratislava, Slovakia.
Acta Crystallogr Sect E Struct Rep Online. 2010 May 22;66(Pt 6):o1402. doi: 10.1107/S1600536810017848.
The title compound, C(12)H(13)NO(2), represents a conformationally restricted 2-pyridone analogue of 1,4-dihydro-pyridine-type calcium antagonists and was selected for a crystal structure determination in order to explore some aspects of drug-receptor inter-action. In the mol-ecule, two stereogenic centres are of opposite chirality, whereas a racemate occurs in the crystal. It was found that the formally aminic N atom of the heterocycle is essentially sp(2)-hybridized with the lone-pair electrons partially delocalized through conjugation with the adjacent carbonyl bond. As a result, the central pyridone ring assumes an unsymmetrical half-chair conformation. The critical 4-phenyl ring is fixed in a pseudo-axial and perpendicular orientation [dihedral angle 85.8 (1)°] with respect to the pyridone ring via an oxygen bridge. In the crystal a pair of centrosymmetric N-H⋯O hydrogen bonds connect mol-ecules of opposite chirality into a dimer. The dimers are packed by hydrophobic van der Waals inter-actions.
标题化合物C(12)H(13)NO(2)是一种构象受限的1,4-二氢吡啶类钙拮抗剂的2-吡啶酮类似物，为探索药物-受体相互作用的某些方面而选择进行晶体结构测定。在分子中，两个手性中心具有相反的手性，而晶体中存在外消旋体。研究发现，杂环中形式上的氨基N原子基本上是sp(2)杂化的，孤对电子通过与相邻羰基键共轭而部分离域。结果，中心吡啶酮环呈现出不对称的半椅构象。关键的4-苯基环通过氧桥相对于吡啶酮环以假轴向和垂直方向固定[二面角85.8 (1)°]。在晶体中，一对中心对称的N-H⋯O氢键将相反手性的分子连接成二聚体。二聚体通过疏水范德华相互作用堆积。
