Benaouida Mohamed Amine, Chetioui Souheyla, Bouaoud Salah Eddine
Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, 25000 Constantine, Algeria.
Acta Crystallogr Sect E Struct Rep Online. 2013 May 11;69(Pt 6):o867-8. doi: 10.1107/S1600536813012245. Print 2013 Jun 1.
In the title compound, C16H12N2O2·0.5CH3OH, the H atom of the -OH group has been transfered to the N atom in the azo group, forming a zwitterion. Hence, there is an intra-molecular N-H⋯O, rather than an O-H⋯N, hydrogen bond in the mol-ecule. The mol-ecule is almost planar, the dihedral angle between the benzene ring and the mean plane of the naphthalene ring system being 4.51 (6)°. In the crystal, mol-ecules are linked to and bridged by O-H⋯O hydrogen bonds involving the methanol mol-ecule, which is located about a twofold rotation axis, and hence half-occupied, forming zigzag chains along [001]. Mol-ecules are also linked via C-H⋯π and π-π inter-actions, the latter involving adjacent benzene and naphthalene rings and having a centroid-centroid distance of 3.6616 (13) Å, forming a three-dimensional network.
在标题化合物C₁₆H₁₂N₂O₂·0.5CH₃OH中，-OH基团的H原子转移到偶氮基团的N原子上，形成一个两性离子。因此，分子内存在一个N-H⋯O氢键，而非O-H⋯N氢键。分子几乎是平面的，苯环与萘环体系平均平面之间的二面角为4.51 (6)°。在晶体中，分子通过涉及甲醇分子的O-H⋯O氢键相连并桥连，甲醇分子位于一个二重旋转轴上，因此占有率为一半，沿[001]形成锯齿链。分子还通过C-H⋯π和π-π相互作用相连，后者涉及相邻的苯环和萘环，质心-质心距离为3.6616 (13) Å，形成三维网络。
