As part of a comprehensive program to discover α9α10 nicotinic acetyl­choline receptor antagonists, the title compounds C30H36N2, (I), and C36H48N2, (II), were synthesized by coupling 4,4′-bis­(3-bromo­prop-1-yn-1-yl)-1,1′-biphenyl with 4-methyl­piperidine and 2,2,6,6-tetra­methyl­piperidine, respectively, in aceto­nitrile at room temperature. In compound (I), the biphenyl system has a twisted conformation with a dihedral angle of 26.57 (6)° between the two phenyl rings of the biphenyl moiety, while in compound (II), the biphenyl moiety sits on a crystallographic inversion centre so the two phenyl rings are exactly coplanar. The terminal piperidine rings in both compound (I) and compound (II) are in the chair conformation. In compound (I), the dihedral angles about the ethynyl groups between the planes of the phenyl rings and the piperidine ring N atoms are 37.16 (16) and 14.20 (17)°. In compound (II), the corresponding dihedral angles are both 61.48 (17)°. There are no noteworthy inter­molecular inter­actions in (I), but in (II) there is a small π-overlap between inversion-related mol­ecules (1 − x, 1 − y, 1 − z), with an inter­planar spacing of 3.553 (3) Å and centroid-to-centroid separation of 3.859 (4) Å.

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Published in Acta Crystallographica Section E: Crystallographic Communications, v. 71, part 10, p. 1132-1135.

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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This investigation was supported by ARA (Arkansas Research Alliance).

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CCDC references: 1419252; 1419251

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S2056989015015352/rz5164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015015352/rz5164Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S2056989015015352/rz5164IIsup3.hkl

Supporting information file. DOI: 10.1107/S2056989015015352/rz5164Isup4.cml

Supporting information file. DOI: 10.1107/S2056989015015352/rz5164IIsup5.cml

checkCIF report

3D view of crystallographic information

rz5164.pptx (190 kB)
PowerPoint slides

rz5164sup1.cif (52 kB)
Crystal structure: contains datablocks global, I, II.

rz5164Isup2.hkl (304 kB)
Structure factors: contains datablock I.

rz5164IIsup3.hkl (153 kB)
Structure factors: contains datablock II.

rz5164Isup4.cml (9 kB)
Supporting information file.

rz5164IIsup5.cml (12 kB)
Supporting information file.

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