1-{2-(4-Chlorobenzyloxy)-2-[4-(morpholin-4-yl)phenyl]ethyl}-1H-benzimidazole propan-2-ol monosolvate

In the title compound, C26H26ClN3O2·C3H7OH, the benzimidazole ring system is essentially planar [maximum deviation = −0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent molecule links with the benzimidazole ring via an O—H⋯N hydrogen bond. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into inversion dimers with an R 2 2(28) motif. π–π stacking occurs between the parallel chlorobenzene rings [centroid–centroid distance = 3.792 (1) Å]. Weak C—H⋯π interactions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.

In the title compound, C 26 H 26 ClN 3 O 2 ÁC 3 H 7 OH, the benzimidazole ring system is essentially planar [maximum deviation = À0.018 (2) Å ] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6) , and the dihedral angle between the two benzene rings is 59.11 (7) . The morpholine ring displays a chair conformation. The propan-2-ol solvent molecule links with the benzimidazole ring via an O-HÁ Á ÁN hydrogen bond. In the crystal, weak intermolecular C-HÁ Á ÁO hydrogen bonds link the molecules into inversion dimers with an R 2 2 (28) motif.stacking occurs between the parallel chlorobenzene rings [centroid-centroid distance = 3.792 (1) Å ]. Weak C-HÁ Á Á interactions and short ClÁ Á ÁCl [3.2037 (10) Å ] contacts are also observed.

Comment
Econazole, miconazole, ketoconazole, fluconazole and itraconazole possessing imidazole or triazole ring in their structures have been known as antifungal agents and used in clinics. The crystal structures of econazole (Freer et al., 1986), miconazole (Peeters et al., 1979a), ketoconazole (Peeters et al., 1979b, fluconazole (Caira et al., 2004) and itraconazole (Peeters et al., 1996) have been reported, previously. Then, similar ether structures possessing benzimidazole ring in their structures have been reported to show antibacterial activity more than antifungal ativity (Özel Güven et al., 2007a,b) and the crystal structures of these compounds have been reported (Özel Güven et al., 2008a,b,c,d). Lately, the crystal structure of a similar new compound has been reported (Özel Güven et al., 2013). Now, we report herein the crystal structure of the title compound, (I), which is another benzimidazole derivative.

Experimental
The title compound, (I), was synthesized by the reaction of 2-(1H-benzimidazol-1-yl)-1-(4-morpholinophenyl)ethanol with aryl halide using sodium hydride. NaH (0.022 g, 0.557 mmol) was added to a solution of alcohol (0.180 g, 0.557 mmol) in DMF (4 ml) in small fractions. After stirring the mixture a few minutes, 4-chlorobenzylbromide (0.114 g, 0.557 mmol) was added. Then, the reaction mixture was stirred additional 4 h at room temperature. The reaction was stopped by adding a small amount of methyl alcohol. After evaporation of the solvent, dichloromethane was added to the reaction mixture and extracted with water. The organic phase was separated and dried with anhydrous magnesium sulfate, then evaporated to dryness. The residue was purified by column chromatography using chloroform and crystallized from isopropyl alcohol to obtain colorless crystals suitable for X-ray analysis (yield; 0.127 g, 51%).

Refinement
Atom H3A (for OH group) was located in a difference Fourier map and was freely refined. The C-bound H-atoms were positioned geometrically with C-H = 0.98, 0.93, 0.97 and 0.96 Å for methine, aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = k × U eq (C), where k = 1.5 for methyl H-atoms and k = 1.2 for all other H-atoms.

Figure 1
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.  A partial packing diagram. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Special details
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.