Ethyl 1-[3-(1H-imidazol-1-yl)propyl]-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate

In the title compound, C22H21ClN4O2·2H2O, the almost-planar benzimidazole ring system [maximum deviation 0.014 (1) Å] is inclined at angles of 36.32 (5) and 74.75 (7)° with respect to the phenyl and imidazole rings, respectively. In the crystal structure, the water molecules are linked to the organic molecules to form a three-dimensional network via O—H⋯N and O—H⋯O hydrogen bonds. The packing is further consolidated by a pair of bifurcated C—H⋯O bonds, generating R 1 2(6) loops. C—H⋯π interactions are also observed.

In the title compound, C 22 H 21 ClN 4 O 2 Á2H 2 O, the almost-planar benzimidazole ring system [maximum deviation 0.014 (1) Å ] is inclined at angles of 36.32 (5) and 74.75 (7) with respect to the phenyl and imidazole rings, respectively. In the crystal structure, the water molecules are linked to the organic molecules to form a three-dimensional network via O-HÁ Á ÁN and O-HÁ Á ÁO hydrogen bonds. The packing is further consolidated by a pair of bifurcated C-HÁ Á ÁO bonds, generating R 1 2 (6) loops. C-HÁ Á Á interactions are also observed.

Related literature
For related structures and background to benzimidazoles, see: Eltayeb et al. (2009Eltayeb et al. ( , 2011. For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 Table 1 Hydrogen-bond geometry (Å , ).

Experimental
Ethyl 4-(3-(1H-imidazol-1-yl)propylamino)-3-aminobenzoate (0.84 mmol) and sodium metabisulfite adduct of chlorobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed at 403 K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na 2 SO 4 and then evaporated in vacuo to yield the product. The product was recrystallised from ethyl acetate to yield bronze blocks of (I).     Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.