caa a22 4500 378882252 CHVBK 20180305123434.0 cr unu---uuuuu 161128e20031101xx s 000 0 eng 10.1524/zkri.218.11.753.20304 doi (NATIONALLICENCE)gruyter-10.1524/zkri.218.11.753.20304 The first crystal structure of a free neutral form of a nicotine derivative [Elektronische Daten] [Michel Evain, François-Xavier Felpin, Christian Laurence, Jacques Lebreton, Jean-Yves Le Questel] The single crystal X-ray diffraction analysis of a racemic form of a nicotine derivative, 5-(2-hydroxy-2-methylbut-3-ynyl)-3-(1-methyl-2-pyrrolidinyl)pyridine (2), provides structural information on molecular geometry and intermolecular interactions that could be relevant for the transport and docking of nicotine ligands to nicotinic acetylcholine receptors (nAChRs), since it is the first crystal structure of a free neutral form of a nicotine derivative. Each enantiomer of the two independent molecules of the asymmetric unit is characterized by (i) an anti orientation of the N2 methyl substituent with respect to the pyridine ring (ii) an envelope form of the pyrrolidine ring (iii) an orientation roughly perpendicular of the pyridine and pyrrolidine rings. The crystal packing is characterized by the formation of OH...N1 hydrogen-bond cyclic dimers that are packed through van der Waals interactions. This selectivity of hydrogen-bonding site in favor of the N1 pyridine nitrogen found in the solid state for (2) agrees with the greater hydrogen-bond acceptor strength of the N1 pyridine nitrogen compared to the N2 pyrrolidine one previously found in solution for nicotine (1). © 2003 Oldenbourg Wissenschaftsverlag GmbH Crystallography nationallicence Inorganic chemistry nationallicence Organic chemistry nationallicence Evain Michel aut Felpin François-Xavier aut Laurence Christian aut Lebreton Jacques aut Le Questel Jean-Yves aut Zeitschrift für Kristallographie - Crystalline Materials De Gruyter Oldenbourg 218/11(2003-11-01), 753-760 2194-4946 218:11<753 2003 218 zkri https://doi.org/10.1524/zkri.218.11.753.20304 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1524/zkri.218.11.753.20304 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Evain Michel aut NATIONALLICENCE 700 1- Felpin François-Xavier aut NATIONALLICENCE 700 1- Laurence Christian aut NATIONALLICENCE 700 1- Lebreton Jacques aut NATIONALLICENCE 700 1- Le Questel Jean-Yves aut NATIONALLICENCE 773 0- Zeitschrift für Kristallographie - Crystalline Materials De Gruyter Oldenbourg 218/11(2003-11-01), 753-760 2194-4946 218:11<753 2003 218 zkri CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter