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

DOI: 10.1107/S2052520614001152
PMID: 24675607

Authors: Kinaan M. Tawfiq (Manchester Metropolitan University) , Gary J. Miller (Manchester Metropolitan University) , Mohamad J. Al-Jeboori (Imperial College London) , Paul S. Fennell (Imperial College London) , Simon J. Coles (University of Southampton) , Graham J. Tizzard (University of Southampton) , Claire Wilson (Diamond Light Source) , Herman Potgieter (Manchester Metropolitan University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Acta Crystallographica Section B Structural Science, Crystal Engineering And Materials , VOL 70 , PAGES 379 - 389

State: Published (Approved)
Published: April 2014
Diamond Proposal Number(s): 6916 , 8521

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.

Journal Keywords: Structural Motifs; Packing Arrangements; Polymorphism; Crystallization Behaviour; Supramolecular Synthons

Subject Areas: Chemistry


Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 25/03/2015 10:29

Discipline Tags:

Chemistry Organic Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)