Comparison of the Crystal Structures of 4,4′-bis­­[3-(4-methyl­piperidin-1-yl)prop-1-yn-1-yl]-1,1′-bi­phenyl and 4,4′-bis­­[3-(2,2,6,6-tetra­methyl­piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl

Authors

Anqi Wan, University of Arkansas for Medical Sciences
Narsimha Reddy Penthala, University of Arkansas for Medical Sciences
E. Kim Fifer, University of Arkansas for Medical Sciences
Sean Parkin, University of KentuckyFollow
Peter A. Crooks, University of Arkansas for Medical Sciences

Abstract

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.

Document Type

Article

Publication Date

10-2015

Notes/Citation Information

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.

Digital Object Identifier (DOI)

https://doi.org/10.1107/S2056989015015352

Funding Information

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

Related Content

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

Repository Citation

Wan, Anqi; Penthala, Narsimha Reddy; Fifer, E. Kim; Parkin, Sean; and Crooks, Peter A., "Comparison of the Crystal Structures of 4,4′-bis­­[3-(4-methyl­piperidin-1-yl)prop-1-yn-1-yl]-1,1′-bi­phenyl and 4,4′-bis­­[3-(2,2,6,6-tetra­methyl­piperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphen­yl" (2015). Chemistry Faculty Publications. 64.
https://uknowledge.uky.edu/chemistry_facpub/64