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The asymmetric unit of the title compound, C20H24N2OS, consists of two crystallographically independent mol­ecules. In each mol­ecule, an intra­molecular N—H...O hydrogen bond forms an S(6) ring motif. The dihedral angles between the terminal benzene rings in the two mol­ecules are 75.52 (7) and 42.80 (7)°. In the crystal, inter­molecular N—H...S inter­actions link the mol­ecules into a chain along the c axis.

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The title compound, C13H8Br2ClNO3S, exhibits whole-mol­ecule disorder over two orientations in a 0.805 (6):0.195 (6) ratio. The dihedral angles between the thio­phene ring [maximum deviations = 0.017 (4) and 0.033 (9) Å for the major and minor components, respectively] and the chloro-substituted phenyl ring are 32.1 (5) (major component) and 26.3 (18)° (minor component). In the crystal, C—H...Cl and C—H...O hydrogen bonds link the mol­ecules into sheets lying parallel to the bc plane. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.550 (7) Å] are also observed.

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In the title compound, C23H17F3N2O3, an intra­molecular C—H...F hydrogen bond generates an S(6) ring motif. The essentially planar 1H-benzimidazole ring system [maximum deviation = 0.021 (2) Å] forms dihedral angles of 25.00 (10) and 62.53 (11)° with the trifluoro­meth­oxy-substituted benzene and phenyl rings, respectively. The twist of the ethyl acetate group from the least-squares plane of the 1H-benzimidazole ring system is defined by a C(=O)—O—C—C torsion angle of 79.5 (3)°. In the crystal, mol­ecules are linked into a two-dimensional network parallel to the bc plane by weak C—H...N and C—H...O hydrogen bonds. Weak C—H...π inter­actions also observed.
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