4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide-4-nitrobenzoic acid

Smith, Graham & Wermuth, Urs D. (2012) 4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide-4-nitrobenzoic acid. Acta Crystallographica. Section E : Structure Reports Online, 68, o1649-o1650.

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In the asymmetric unit of the title co-crystal, C12H14N4O2S . C7H5NO4 there are two independent but conformationally similar heterodimers, which are formed through intermolecular N-H...O(carboxy) and carboxyl O-H...N hydrogen-bond pairs, giving a cyclic motif [graph set R2/2(8)]. The dihedral angles between the rings in the sulfonamide molecules are 78.77(8) and 82.33(9)deg. while the dihedral angles between the ring and the CO2H group in the acids are 2.19(9) and 7.02(10)deg. A two-dimensional structure parallel to the ab plane is generated from the heterodimer units through hydrogen-bonding associations between NH2 and sulfone groups. Between neighbouring two-dimensional arrays there are two types of aromatic pi-pi stacking interactions involving either one of the pyrimidine rings and a 4-nitrobenzoic acid molecule [minimum ring centroid separation = 3.5886(9)A] or two acid molecules [minimum ring centroid separation = 3.7236(10)A].

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ID Code: 50184
Item Type: Journal Article
Refereed: Yes
Keywords: crystal structure, cocrystal, hydrogen bonding, sulfamethazine
DOI: 10.1107/S1600536812019563
ISSN: 1600-5368
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)
Divisions: Current > QUT Faculties and Divisions > Chancellery
Current > QUT Faculties and Divisions > Division of International and Development
Copyright Owner: Copyright 2012 Graham Smith & Urs D. Wermuth
Copyright Statement: This open-access article is distributed under the terms of the Creative Commons Attribution Licence
http://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, and
reproduction in any medium, provided the original authors and source are cited.
Deposited On: 08 May 2012 22:12
Last Modified: 09 May 2012 15:58

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