Gotoh Kazuma, Ishida Hiroyuki
Department of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan.
Acta Crystallogr E Crystallogr Commun. 2019 Oct 22;75(Pt 11):1694-1699. doi: 10.1107/S2056989019013896. eCollection 2019 Nov 1.
The structures of two isomeric com-pounds of 5-nitro-quinoline with chloro- and nitro-substituted benzoic acid, namely, 2-chloro-4-nitro-benzoic acid-5-nitro-quinoline (1/1), (I), and 5-chloro-2-nitro-benzoic acid-5-nitro-quinoline (1/1), (II), both CHClNO·CHNO, have been determined at 190 K. In each com-pound, the acid and base mol-ecules are held together by an O-H⋯N hydrogen bond. In the crystal of (I), the hydrogen-bonded acid-base units are linked by a C-H⋯O hydrogen bond, forming a tape structure along [10]. The tapes are stacked into a layer parallel to the plane N-O⋯π inter-actions between the nitro group of the base mol-ecule and the quinoline ring system. The layers are further linked by other C-H⋯O hydrogen bonds, forming a three-dimensional network. In the crystal of (II), the hydrogen-bonded acid-base units are linked into a wide ribbon structure running along [10] C-H⋯O hydrogen bonds. The ribbons are further linked another C-H⋯O hydrogen bond, forming a layer parallel to (110). Weak π-π inter-actions [centroid-centroid distances of 3.7080 (10) and 3.7543 (9) Å] are observed between the quinoline ring systems of adjacent layers. Hirshfeld surfaces for the 5-nitro-quinoline mol-ecules of the two com-pounds mapped over shape index and were generated to visualize the weak inter-molecular inter-actions.
已在190 K下测定了5-硝基喹啉与氯代和硝基取代苯甲酸的两种异构体化合物的结构，即2-氯-4-硝基苯甲酸-5-硝基喹啉(1/1)，(I)，以及5-氯-2-硝基苯甲酸-5-硝基喹啉(1/1)，(II)，二者均为CHClNO·CHNO。在每种化合物中，酸和碱分子通过O-H⋯N氢键结合在一起。在(I)的晶体中，氢键连接的酸碱单元通过C-H⋯O氢键相连，沿[10]方向形成带状结构。这些带堆叠成平行于 平面的层，碱基分子的硝基与喹啉环系统之间存在N-O⋯π相互作用。这些层通过其他C-H⋯O氢键进一步连接，形成三维网络。在(II)的晶体中，氢键连接的酸碱单元通过C-H⋯O氢键连接成沿[10]方向延伸的宽带状结构。这些带通过另一个C-H⋯O氢键进一步连接，形成平行于(110)的层。在相邻层的喹啉环系统之间观察到弱的π-π相互作用[质心-质心距离为3.7080 (10)和3.7543 (9) Å]。生成了两种化合物中5-硝基喹啉分子在形状指数和 上映射的 Hirshfeld 表面，以可视化弱分子间相互作用。
