Supramolecular interactions in a 1:1 co-crystal of acridine and 3-chlorothiophene-2-carboxylic acid

Abstract

The asymmetric unit comprises one 3-chloro­thio­phene-2-carb­oxy­lic acid (3TPC) and one acridine mol­ecule linked together via an O—H⋯N hydrogen bond.

Salt formation, hydrogen-bonding patterns and supramolecular architectures of acridine with salicylic and hippuric acid molecules

“…The intermolecular interactions in the crystal form a supramolecular ladder via O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonding, and these interactions form R 2 4 (8) and R 4 4 (14) ring motifs (Etter et al, 1990) involving the water molecule and the hippurate anions (Fig. S14 in the supporting information) (Prajina et al, 2016). The ladder motif has been observed in previously reported acridine structures (Attar Gharamaleki et al, 2010).…”

“…In acridinium hippurate monohydrate (salt III), the N1 atom of the pyridine ring of acridine is protonated. This increases the bond angle at N1 [C1-N1-C9 = 123.27 (17) ] when compared with the reported unprotonated structure (Aghabozorg et al, 2011;Binder & Karl, 1982;Prajina et al, 2016). In hippuric acid (Fig.…”

“…1(a) shows that the asymmetric unit of salt I contains an acridinium cation and a 4-aminosalicylate anion. The cation is protonated at atom N1 and this protonation is confirmed by the increase of the bond angle at N1 [C1-N1-C9 = 122.64 (10) ]; this angle is significantly wider compared with the corresponding bond angle [116.9 (7) ] of neutral acridine (Aghabozorg et al, 2011;Prajina et al, 2016). An intramolecular O-HÁ Á ÁO hydrogen bond occurs within the anion (Table 2).…”

Supramolecular interactions in the 1:2 co-crystal of 4,4′-bipyridine and 3-chlorothiophene-2-carboxylic acid

“…The two external bond angles at the carbon of the carboxyl group are 123.7 (3) and 112.4 (3) . The high discrepancy between these two angles is typical of an unionized carboxyl group, as are the C O distance of 1.219 (4) Å and C-OH distance of 1.3254 (5) Å (see for example Prajina et al, 2016;Atria et al, 2014;Jennifer & Muthiah, 2014;Qin, 2011). The bond distances and angles of the thiophene ring agree with those in structures reported earlier (Zhang et al, 2014).…”

“…1). This O-HÁ Á ÁN hydrogen bond is a frequently observed supramolecular synthon in crystal engineering involving a carboxylic acid and a pyridine system (Dubey & Desiraju, 2015;Lemmerer & Bernstein, 2010;Mukherjee et al, 2011Mukherjee et al, , 2013Prajina et al, 2016;Seaton, 2014;Thomas et al, 2010). This supramolecular synthon is also present in the co-crystal of 5-chlorothiophene-2-carboxylic acid with BPY (5TPC44BIPY) and in the co-crystal of thiophene-2-carboxylic acid with BPY reported from our laboratory (Jennifer & Muthiah, 2014).…”