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4-(3-Fluoro-anilino)thieno[2,3-b]pyridine-6-carb-oxy-lic acid.

ABSTRACT: In the title compound, C(14)H(9)FN(2)O(2)S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194?Å), with the carb-oxy-lic acid group [dihedral angle = 11.9?(3)°] and the benzene ring [71.1?(4)°] being twisted out of this plane to different extents. An intra-molecular N-H?O(carbon-yl) hydrogen bond closes an S(6) ring. Supra-molecular chains along [01-1] mediated by O-H?N(pyridine) hydrogen bonds feature in the crystal. A three-dimensional architecture is completed by ?-? inter-actions 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)].

SUBMITTER: Pinheiro LC

PROVIDER: S-EPMC3394012 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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4-(3-Fluoro-anilino)thieno[2,3-b]pyridine-6-carb-oxy-lic acid.

Pinheiro Luiz C S LC Bernardino Alice M R AM Wardell Solange M S V SM Wardell James L JL Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20120627 Pt 7

In the title compound, C(14)H(9)FN(2)O(2)S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194 Å), with the carb-oxy-lic acid group [dihedral angle = 11.9 (3)°] and the benzene ring [71.1 (4)°] being twisted out of this plane to different extents. An intra-molecular N-H⋯O(carbon-yl) hydrogen bond closes an S(6) ring. Supra-molecular chains along [01-1] mediated by O-H⋯N(pyridine) hydrogen bonds feature in the crystal. A three-dimensional architecture is completed by π- ...[more]

PMID: 22798877

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