The title compounds, C26H28N2, (I), and C28H32N2, (II), were designed based on the structure of the potent 910 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1'-[[1,1'-biphen­yl]-4,4'-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bromide}. In order to improve the druglikeness properties of ZZ161C for potential oral administration, the title compounds (I) and (II) were prepared by coupling 4,4'-bis­(3-bromo­prop-1-yn-1-yl)-1,1'-biphenyl with pyrrol­idine, (I), and (S)-2-methyl­pyrrolidine, (II), respectively, in aceto­nitrile at room temperature. The asymmetric unit of (I) contains two half mol­ecules that each sit on sites of crystallographic inversion. As a result, the biphenyl ring systems in compound (I) are coplanar. The biphenyl ring system in compound (II), however, has a dihedral angle of 28.76 (11)°. In (I), the two independent mol­ecules differ in the orientation of the pyrrolidine ring (the nitro­gen lone pair points towards the biphenyl rings in one mol­ecule, but away from the rings in the other). The torsion angles about the ethynyl groups between the planes of the phenyl rings and the pyrrolidine ring N atoms are 84.15 (10) and -152.89 (10)°. In compound (II), the corresponding torsion angles are 122.0 (3) and 167.0 (3)°, with the nitro­gen lone pairs at both ends of the mol­ecule directed away from the central biphenyl rings.

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Published in Acta Crystallographica Section E: Cystallographic Communications, v. 71, part 10, p. 1147-1150.

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: 1421219; 1421218

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S2056989015016163/hg5457sup1.cif

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Structure factors: contains datablock II. DOI: 10.1107/S2056989015016163/hg5457IIsup3.hkl

Supporting information file. DOI: 10.1107/S2056989015016163/hg5457Isup4.cml

Supporting information file. DOI: 10.1107/S2056989015016163/hg5457IIsup5.cml

checkCIF report

3D view of crystallographic information

hg5457.pptx (234 kB)
PowerPoint slides

hg5457sup1.cif (894 kB)
Crystal structure: contains datablocks global, I, II.

hg5457Isup2.hkl (196 kB)
Structure factors: contains datablock I.

hg5457IIsup3.hkl (257 kB)
Structure factors: contains datablock II.

hg5457Isup4.cml (8 kB)
Supporting information file.

hg5457IIsup5.cml (8 kB)
Supporting information file.

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