4-Nitrobenzoic acid–sulfathiazole (1/1)

Abstract

In the crystal structure of the title compound, C7H5NO4·C9H9N3O2S2, the sulfa­thia­zole and 4-nitro­benzoic acid mol­ecules are held together by short π–π contacts between the thia­zole and nitro­benzene rings, with a centroid–centroid distance of 3.8226 (7) Å. The sulfa­thia­zole mol­ecules form dimers via N—H⋯N hydrogen bonds involving the thia­zole and sulfonamide moieties, owing to the fact that sulfathizole exhibits amide–imide tautomerism. The N—H (amine) groups of two sulfathiazole molecules are linked to the two S=O groups of a sulfathiazole via N—H⋯O hydrogen bonds. Two mol­ecules of coformer are held together by O—H⋯O hydrogen bonds. These units self-assemble, forming a three-dimensional network stabilized by (acid)C—H⋯π(sulfa­thia­zole benzene ring) inter­actions.

In Pursuit of Multicomponent Crystals of the Sulfa Drugs Sulfapyridine, Sulfathiazole, and Sulfamethoxazole

“…These multicomponent crystals are presented together according to the sulfa drug present (ordered st , sm , and the sp ) and similarity of the coformer (for example, multicomponent crystals containing 2a3np , 2a5np , and 2a5clp were described and grouped together with 2ap since they are derivatives of 2ap ). It should be noted that the following combinations were obtained but are not presented in detail in this work since they have been reported and described in the literature previously: st + 4nba , sm + 4ap , sm + bipy , sm + 2hp , and sp + 4nba . However, the crystal structures of st + 2ap and st + 2a5clp were presented in another work recently; in this case, we present an alternative method for obtaining the same crystal form and additional characterization such as FTIR, TGA, and DSC data, which was not included in the previous work.…”

“…In particular, we wanted to expand the number of cocrystals or molecular salts of sp , as previously reported instances of multicomponent crystals consisting of sp are limited in most cases to solvates. , This work also includes an attempt to obtain multicomponent crystals containing different tautomers of st , sp , and sm , that if successful could yield some insight in solid-state tautomerism of sulfa drugs. Twenty-five coformers were chosen based on successes with other sulfonanilamide derivatives, having structural similarity with each other (isomers), having robust and well-defined hydrogen bond motifs, or being API/GRAS compounds. ,,,− The coformers chosen are listed and represented in Scheme .…”

Differences in Coformer Interactions of the 2,4-Diaminopyrimidines Pyrimethamine and Trimethoprim

“…80 By contrast, stz/3,5dinitrobenzoic acid, sulfamethoxazole/3,5-dinitrobenzoic acid, and sulfapyridine/2-chloro-4-nitrobenzoic acid all have different synthons. 70 In the stz•glutaric acid 81 and stz•4-nitrobenzoic acid 82 cocrystals, stz and the carboxylic acid both form homodimers. In stz•glutaric acid, the dimers are linked via a bifurcated H bond to the amino group and sulfonyl oxygen of two adjacent stz molecules.…”

Changes in the proportions of an active pharmaceutical through cocrystals

“…These facts intrigued us to explore possible changes in composition of a carboxylic acid salt of an API, utilizing second coordination sphere of a complex interacting with a guest molecule. Due to limited solubility of sulfa-drugs in water and also due to low bio-availability, some of those drugs were used in the form of their corresponding salts (Aitipamula, Chow, & Tan, 2012;Ghosh, Bag, & Reddy, 2011;Oruganti & Trivedi, 2014). Cocrystals and salts of sulfathiazole drugs have been well studied (Caira, 2007;Domingos, Fernandes, Duarte, Piedade, & Piedade, 2016;Pan et al, 2019;Samanta, Kanaujia, & Reddy, 2014;Tailor & Patel, 2015;Zhang et al, 2017).…”