Abstract
The title compounds, 8-{1-[3-(cyclo-pent-1-en-1-yl)benz-yl]piperidin-4-yl}-2-meth-oxy-quinoline, C27H30N2O (I), and 8-{4-[3-(cyclo-pent-1-en-1-yl)benz-yl]piperazin-1-yl}-2-meth-oxy-quinoline, C26H29N3O (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 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 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, mol-ecules are linked by C-H⋯π inter-actions, 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 inter-molecular inter-actions in the crystals is from dispersion forces (E dis), reflecting the absence of classical hydrogen bonds.
Highlights
The title compounds, 8-{1-[3-(cyclopent-1-en-1-yl)benzyl]piperidin-4-yl}-2methoxyquinoline, C27H30N2O (I), and 8-{4-[3-(cyclopent-1-en-1-yl)benzyl]piperazin-1-yl}-2-methoxyquinoline, C26H29N3O (II), differ only in the nature of the central six-membered ring: piperidine in I and piperazine in II
The phenyl ring is inclined to the cyclopentene mean plane (r.m.s. deviations = 0.089 Afor I and 0.082 Afor 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 Afor I and 0.038 Afor II)
In the crystals of both compounds, molecules are linked by C—HÁ Á Á interactions, forming chains in I and ribbons in II, both propagating along the b-axis direction
Summary
Compounds combining dopamine D2 receptor blockade with serotonin 5-HT1A receptor activation rather than antagonism for the treatment of Schizophrenia have been developed by a number of researchers (Newman-Tancredi et al, 2007; Jones & McCreary, 2008). One such drug, Adoprazine(c), was found to combine both dopamine D2 antagonist (blockade) and serotonin 5-HT1A agonist (activation) properties (Feenstra et al, 2001, 2006). Ullah and collaborators have synthesized a series of compounds that are analogues of Adoprazine(c) and Bifeprunox(c) (Ullah, 2012, 2014a,b; Ullah & Al-Shaheri, 2012) They have examined rat-cloned dopamine D2 and humancloned serotonin 5-HT1A receptor properties of more than. The crystal structure of II is compared to that of 8-[4-([1,10biphenyl]-3-ylmethyl)piperazin-1-yl]-2-methoxyquinoline (III), where the 3-(cyclopent-1-en-1-yl)benzyl unit in II has been replaced by a 1,10-biphenyl unit in III (Ullah & Altaf, 2014)
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