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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

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
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
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 center dot center dot center dot 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.
0108-7681
379-389
Tawfiq, Kinaan M.
1b5acc5d-c8a9-4113-9637-a8b91717912f
Miller, Gary J.
621e837e-5826-4838-a040-af65ea3f3de7
Al-Jeboori, Mohamad J.
180ff82a-635c-452f-925d-c2034b42765b
Fennell, Paul S.
947480ab-b6de-4406-98e4-e052c66f7f6b
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Wilson, Claire
6be18134-9a9f-4d19-8197-0593a648773f
Potgieter, Herman
4bc8214d-61fc-43f2-9492-3dcc4d2c8c02
Tawfiq, Kinaan M.
1b5acc5d-c8a9-4113-9637-a8b91717912f
Miller, Gary J.
621e837e-5826-4838-a040-af65ea3f3de7
Al-Jeboori, Mohamad J.
180ff82a-635c-452f-925d-c2034b42765b
Fennell, Paul S.
947480ab-b6de-4406-98e4-e052c66f7f6b
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Wilson, Claire
6be18134-9a9f-4d19-8197-0593a648773f
Potgieter, Herman
4bc8214d-61fc-43f2-9492-3dcc4d2c8c02

Tawfiq, Kinaan M., Miller, Gary J., Al-Jeboori, Mohamad J., Fennell, Paul S., Coles, Simon J., Tizzard, Graham J., Wilson, Claire and Potgieter, Herman (2014) 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. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 70 (2), 379-389. (doi:10.1107/S2052520614001152).

Record type: Article

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 center dot center dot center dot 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.

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More information

Published date: 1 April 2014
Organisations: Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 369251
URI: http://eprints.soton.ac.uk/id/eprint/369251
ISSN: 0108-7681
PURE UUID: dd130a06-c2e9-4107-be91-48a1cd8c9670
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779

Catalogue record

Date deposited: 30 Sep 2014 12:33
Last modified: 18 Feb 2021 16:57

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