2-氯-3-[（E）-（2-苯基肼叉基）甲基]喹啉的合成、晶体结构及 Hirshfeld 表面分析

Akhramez Soufiane, Hafid Abderrafia, Khouili Mostafa, Saadi Mohamed, El Ammari Lahcen, Ketatni El Mostafa

Laboratory of Organic and Analytical Chemistry, University Sultan Moulay Slimane, Faculty of Science and Technology, PO Box 523, Beni-Mellal, Morocco.

Laboratoire de Chimie Appliquée des Matériaux, Centre Sciences des Matériaux, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Batouta, BP 1014, Rabat, Morocco.

Acta Crystallogr E Crystallogr Commun. 2019 Jun 7;75(Pt 7):964-968. doi: 10.1107/S2056989019007692. eCollection 2019 Jul 1.

A new quinoline-based hydrazone, CHClN, was synthesized by a condensation reaction of 2-chloro-3-formyl-quinoline with phenyl-hydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The mol-ecule adopts an configuration with respect to the central C=N bond. In the crystal, mol-ecules are linked by a C-H⋯π-phenyl inter-action, forming zigzag chains propagating along the [10] direction. The N-H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent mol-ecule, so linking the chains weak N-H⋯π inter-actions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (35.5%), C⋯H/H⋯C (33.7%), Cl⋯H/H⋯Cl (12.3%), N⋯H/H⋯N (9.5%) contacts.

通过2-氯-3-甲酰基喹啉与苯肼的缩合反应合成了一种新型喹啉基腙CHClN。喹啉环系基本呈平面状（均方根偏差 = 0.012 Å），与苯环形成8.46 (10)°的二面角。分子相对于中心C=N键采取反式构型。在晶体中，分子通过C-H⋯π-苯相互作用连接，形成沿[10]方向传播的锯齿链。N-H氢原子不参与氢键形成，但指向相邻分子的苯环，从而通过弱的N-H⋯π相互作用连接这些链，形成三维结构。晶体结构的 Hirshfeld 表面分析表明，对晶体堆积最重要的贡献来自H⋯H（35.5%）、C⋯H/H⋯C（33.7%）、Cl⋯H/H⋯Cl（12.3%）、N⋯H/H⋯N（9.5%）接触。