Hydrogen-bonded network of diethyl 2,5-diaminothiophene-3,4-dicarboxylate

Abstract

Key indicatorsSingle-crystal X-ray study T = 220 K Mean (C-C) = 0.002 Å R factor = 0.042 wR factor = 0.125 Data-to-parameter ratio = 14.6For details of how these key indicators were automatically derived from the article, see

Crystal structure of diethyl 2-amino-5-{4-[bis(4-methylphenyl)amino]benzamido}thiophene-3,4-dicarboxylate

“…In fact, two N-HÁ Á ÁO intramolecular hydrogen bonds occur, one each between the ester carbonyl and its adjacent nitrogen, forming rings of S(6) graph-set motif (Table 1). The intramolecular hydrogen bonds observed are consistent with those reported in other 2-amino-3-ester thiophenes (Dufresne & Skene, 2010a,b;Skene et al, 2006;Bourgeaux et al, 2006;Bolduc et al, 2010;Tshibaka et al, 2011;Furuyama et al, 2014). The crystal structure of I confirms the asymmetric substitution of thiophene by a primary amine and an amide.…”

Diethyl 2,5-bis[(E)-thiophen-2-ylmethyleneamino]thiophene-3,4-dicarboxylate

“…The longer bonds are consistent with the values in (I). However, the N1-C1 and N2-C4 bond distances in (III) are longer than the reported values for the corresponding bonds in (I) of 1.348 (2) and 1.350 (3) Å (Bourgeaux et al, 2006). The azomethine bond distances of N2-C10 and N1-C5 are statistically the same as in (II).…”

Ethyl 2-aminothiophene-3-carboxylate

“…The dihedral angles between the thiophene ring and ethyl ester mean plane are 3.40 (15) and 5.34 (7) for the S1-and S2-containing molecules, respectively. This is in contrast to the values of 26.16 (8) and 28.87 (9) found in compound (II) (Bourgeaux et al, 2006). The bond distances and angles for (I) are very similar to those of (II).…”