Research Article: 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Luiz C. S. Pinheiro, Alice M. R. Bernardino, Solange M. S. V. Wardell, James L. Wardell, Edward R. T. Tiekink.

http://doi.org/10.1107/S1600536812027195

Abstract

In the title compound, C14H9FN2O2S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194 Å), with the carb­oxy­lic acid group [dihedral angle = 11.9 (3)°] and the benzene ring [71.1 (4)°] being twisted out of this plane to different extents. An intra­molecular N—H⋯O(carbon­yl) hydrogen bond closes an S(6) ring. Supra­molecular chains along [01-1] mediated by O—H⋯N(pyridine) hydrogen bonds feature in the crystal. A three-dimensional architecture is completed by π–π inter­actions occurring between the benzene ring and the two rings of the thieno[2,3-b]pyridine residue [centroid–centroid distances = 3.6963 (13) and 3.3812 (13) Å]. The F atom is disordered over the two meta sites in a near statistical ratio [0.545 (5):0.455 (5)].

Partial Text

For the biological activity of 4-(aryl­amino)­thieno[2,3-b]pyridine-5-carb­oxy­lic acids, see: Bernardino et al. (2007 ▶); Pinheiro et al. (2008 ▶). For the synthesis, see: Leal et al. (2008 ▶).

Source:

http://doi.org/10.1107/S1600536812027195