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The crystal structures, Hirshfeld surface analyses and energy frameworks of 8-{1-[3-(cyclo­pent-1-en-1-yl)benz­yl]piperidin-4-yl}-2-meth­oxy­quinoline and 8-{4-[3-(cyclo­pent-1-en-1-yl)benz­yl]piperazin-1-yl}-2-meth­oxy­quinoline

The title compounds, 8-{1-[3-(cyclo­pent-1-en-1-yl)benz­yl]piperidin-4-yl}-2-meth­oxy­quinoline, C(27)H(30)N(2)O (I), and 8-{4-[3-(cyclo­pent-1-en-1-yl)benz­yl]piperazin-1-yl}-2-meth­oxy­quinoline, C(26)H(29)N(3)O (II), differ only in the nature of the central six-membered ring: piperidine in I and...

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Detalles Bibliográficos
Autores principales: Ullah, Nisar, Stoeckli-Evans, Helen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8025868/
https://www.ncbi.nlm.nih.gov/pubmed/33936760
http://dx.doi.org/10.1107/S2056989021002474
Descripción
Sumario:The title compounds, 8-{1-[3-(cyclo­pent-1-en-1-yl)benz­yl]piperidin-4-yl}-2-meth­oxy­quinoline, C(27)H(30)N(2)O (I), and 8-{4-[3-(cyclo­pent-1-en-1-yl)benz­yl]piperazin-1-yl}-2-meth­oxy­quinoline, C(26)H(29)N(3)O (II), differ only in the nature of the central six-membered ring: piperidine in I and piperazine in II. They are isoelectronic (CH cf. N) and isotypic; they both crystallize in the triclinic space group P [Image: see text] with very similar unit-cell parameters. Both mol­ecules have a curved shape and very similar conformations. In the biaryl group, the phenyl ring is inclined to the cyclo­pentene mean plane (r.m.s. deviations = 0.089 Å for I and 0.082 Å for II) by 15.83 (9) and 13.82 (6)° in I and II, 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 I and 0.038 Å for II). The piperazine ring in I and the piperidine ring in II have chair conformations. In the crystals of both compounds, mol­ecules are linked by C—H⋯π inter­actions, forming chains in I and ribbons in II, both propagating along the b-axis direction. The principal contributions to the overall Hirshfeld surfaces involve H⋯H contacts at 67.5 and 65.9% for I and II, respectively. The major contribution to the inter­molecular inter­actions in the crystals is from dispersion forces (E (dis)), reflecting the absence of classical hydrogen bonds.