Crystal Engineering of Organic Salts: Hydrogen-Bonded Supramolecular Motifs in Trimethoprim Sorbate Dihydrate and Trimethoprim o-Nitrobenzoate

Autor:	R. Olla, Nithianantham Stanley, A. Cantoni, G. Bocelli, P. Thomas Muthiah, S. Baskar Raj
Rok vydání:	2003
Předmět:	biology Hydrogen bond Stereochemistry Supramolecular chemistry General Chemistry Crystal structure Condensed Matter Physics Crystal engineering Ring (chemistry) chemistry.chemical_compound Crystallography chemistry biology.protein Molecule General Materials Science Carboxylate Organic anion
Zdroj:	Crystal Growth & Design. 3:567-571
ISSN:	1528-7505 1528-7483
DOI:	10.1021/cg020043m
Popis:	In the crystal structures of two organic salts, namely, trimethoprim sorbate dihydrate (1) and trimethoprim o-nitrobenzoate (2), the pyrimidine moieties of trimethoprim are protonated at one of the ring nitrogens. In both the compounds, the carboxylate oxygens are hydrogen-bonded to the protonated pyrimidine rings to form the hydrogen-bonded cyclic bimolecular motif. These motifs further self-organize in two different ways to give different types of hydrogen-bonded networks in the two crystal structures. In compound 1, the two inversion related motifs pair through a pair of N−H···N hydrogen bonds involving an unprotonated ring nitrogen and 4-amino group. In addition to this pairing, one of the water oxygens bridges the 2- and 4-amino groups on both sides of pairing to form a complementary DADA (D refers to the hydrogen-bond donor and A refers to the hydrogen-bond acceptor) array of quadruple hydrogen bonds. In compound 2, there is no base-pairing, and the cyclic hydrogen-bonded bimolecular motifs self-ass...
Databáze:	OpenAIRE
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