title: Comparison of the structural motifs and packing arrangements of six novel derivatives and one polymorph of 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine.
abstract: The crystal structures of a new polymorph and seven new derivatives of 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine have been characterized and examined along with three structures from the literature to identify trends in their intermolecular contact patterns and packing arrangements in order to develop an insight into the crystallization behaviour of this class of compound. Seven unique C-H···X contacts were identified in the structures and three of these are present in four or more structures, indicating that these are reliable supramolecular synthons. Analysis of the packing arrangements of the molecules using XPac identified two closely related supramolecular constructs that are present in eight of the 11 structures; in all cases, the structures feature at least one of the three most common intermolecular contacts, suggesting a clear relationship between the intermolecular contacts and the packing arrangements of the structures. Both the intermolecular contacts and packing arrangements appear to be remarkably consistent between structures featuring different functional groups, with the expected exception of the carboxylic acid derivative 4-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl) benzoic acid (L11), where the introduction of a strong hydrogen-bonding group results in a markedly different supramolecular structure being adopted. The occurrence of these structural features has been compared with the packing efficiency of the structures and their melting points in order to assess the relative favourability of the supramolecular structural features in stabilizing the crystal structures.
authors.affiliation: Division of Chemistry and Environmental Sciences, School of Science and the Environment, Manchester Metropolitan University, Chester Street, Manchester M1 5GD, England.
authors.forename: Kinaan M
authors.initials: KM
authors.lastname: Tawfiq
authors.affiliation: Analytical Sciences, Manchester Metropolitan University, Chester Street, Manchester M1 5GD, England.
authors.forename: Gary J
authors.initials: GJ
authors.lastname: Miller
authors.affiliation: Department of Chemical Engineering and Chemical Technology, Imperial College London, London SW7 2AZ, England.
authors.forename: Mohamad J
authors.initials: MJ
authors.lastname: Al-Jeboori
authors.affiliation: Department of Chemical Engineering and Chemical Technology, Imperial College London, London SW7 2AZ, England.
authors.forename: Paul S
authors.initials: PS
authors.lastname: Fennell
authors.affiliation: EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Southampton SO17 1BJ, England.
authors.forename: Simon J
authors.initials: SJ
authors.lastname: Coles
authors.affiliation: EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Southampton SO17 1BJ, England.
authors.forename: Graham J
authors.initials: GJ
authors.lastname: Tizzard
authors.affiliation: Diamond Light Source Ltd, Diamond House, Harwell Science and Innovation Campus, Didcot, Oxfordshire OX11 0DE, England.
authors.forename: Claire
authors.initials: C
authors.lastname: Wilson
authors.affiliation: School of Research, Enterprise and Innovation, Manchester Metropolitan University, Chester Street, Manchester M1 5GD, England.
authors.forename: Herman
authors.initials: H
authors.lastname: Potgieter
mesh_terms: D057930:Click Chemistry; D003460:Crystallization; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D008024:Ligands; D011725:Pyridines; D014230:Triazoles
keywords: crystallization behaviour; packing arrangements; polymorphism; structural motifs; supramolecular synthons