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In methyl 4-(4-chloro­anilino)-3-nitro­benzoate, C14H11ClN2O4, (I), there is an intra­molecular N-H...O hydrogen bond and the intra­molecular distances provide evidence for electronic polarization of the o-quinonoid type. The mol­ecules are linked into sheets built from N-H...O, C-H...O and C-H...[pi](arene) hydrogen bonds, together with an aromatic [pi]-[pi] stacking inter­action. The mol­ecules of methyl 1-benzyl-2-(4-chloro­phenyl)-1H-benzimidazole-5-carboxyl­ate, C22H17ClN2O2, (II), are also linked into sheets, this time by a combination of C-H...[pi](arene) hydrogen bonds and aromatic [pi]-[pi] stacking inter­actions.
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