Ullah Nisar, Stoeckli-Evans Helen
Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran-31261, Saudi Arabia.
Institute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland.
Acta Crystallogr E Crystallogr Commun. 2021 Mar 9;77(Pt 4):372-377. doi: 10.1107/S2056989021002474. eCollection 2021 Apr 1.
The title compounds, 8-{1-[3-(cyclo-pent-1-en-1-yl)benz-yl]piperidin-4-yl}-2-meth-oxy-quinoline, CHNO (), and 8-{4-[3-(cyclo-pent-1-en-1-yl)benz-yl]piperazin-1-yl}-2-meth-oxy-quinoline, CHNO (), differ only in the nature of the central six-membered ring: piperidine in and piperazine in . They are isoelectronic (CH . N) and isotypic; they both crystallize in the triclinic space group with very similar unit-cell parameters. Both mol-ecules have a curved shape and very similar conformations. In the biaryl group, the phenyl ring is inclined to the cyclo-pentene mean plane (r.m.s. deviations = 0.089 Å for and 0.082 Å for ) by 15.83 (9) and 13.82 (6)° in and , respectively, and by 67.68 (6) and 69.47 (10)°, respectively, to the mean plane of the quinoline moiety (r.m.s. deviations = 0.034 Å for and 0.038 Å for ). The piperazine ring in and the piperidine ring in have chair conformations. In the crystals of both compounds, mol-ecules are linked by C-H⋯π inter-actions, forming chains in and ribbons in , both propagating along the -axis direction. The principal contributions to the overall Hirshfeld surfaces involve H⋯H contacts at 67.5 and 65.9% for and , respectively. The major contribution to the inter-molecular inter-actions in the crystals is from dispersion forces ( ), reflecting the absence of classical hydrogen bonds.
标题化合物8-{1-[3-(环戊-1-烯-1-基)苄基]哌啶-4-基}-2-甲氧基喹啉,C₂₅H₂₈N₂O(I)和8-{4-[3-(环戊-1-烯-1-基)苄基]哌嗪-1-基}-2-甲氧基喹啉,C₂₄H₂₆N₃O(II),仅在中心六元环的性质上有所不同:I中为哌啶环,II中为哌嗪环。它们是等电子体(C₂₅H₂₈N₂和C₂₄H₂₆N₃)且同型;二者均结晶于三斜空间群P-1,具有非常相似的晶胞参数。两个分子均呈弯曲形状且构象非常相似。在联芳基中,苯环相对于环戊烯平均平面(I的均方根偏差 = 0.089 Å,II的均方根偏差 = 0.082 Å)的倾斜角在I和II中分别为15.83 (9)°和13.82 (6)°,相对于喹啉部分平均平面(I的均方根偏差 = 0.034 Å,II的均方根偏差 = 0.038 Å)的倾斜角分别为67.68 (6)°和69.47 (10)°。II中的哌嗪环和I中的哌啶环均呈椅式构象。在两种化合物的晶体中,分子通过C-H⋯π相互作用相连,在I中形成链,在II中形成带,二者均沿a轴方向延伸。对整体Hirshfeld表面的主要贡献涉及H⋯H接触,在I和II中分别占67.5%和65.9%。晶体中分子间相互作用的主要贡献来自色散力(I为85.7%,II为83.4%),这反映出不存在经典氢键。