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The title polysubstituted pyridines, ethyl 4-hydroxy-2,6-diphenyl-5-(phenylsulfanyl)pyridine-3-carboxylate, C26H21NO3S, (I), and ethyl 2,6-bis(4-fluorophenyl)-4-hydroxy-5-(4-methylphenylsulfanyl)pyridine-3-carboxylate, C27H21F2NO3S, (II), adopt nearly planar structures. The crystal structure of (I) is stabilized by inter­molecular C—H...O and C—H...π inter­actions. The C—H...O hydrogen bonds generate rings of motifs R22(14) and R22(20). The crystal structure of (II) is stabilized by inter­molecular C—H...F and C—H...π inter­actions. The C—H...F bond generates a linear chain of motif C(14). In addition, in (I) and (II), intra­molecular O—H...O inter­actions generating a graph-set motif S(6) are found. No significant aryl–aryl or π–π inter­actions exist in these structures.
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