N-(3-Chlorophenyl)-N′-(2-methylphenyl)succinamide monohydrate

In the title compound, C17H17ClN2O2·H2O, the dihedral angles formed by the aromatic rings of the chlorobenzene and methylbenzene groups with the mean planes of the attached NH–C(O)–CH2 fragments are 9.4 (4) and 62.9 (2)°, respectively. In the crystal, molecules are packed into layers parallel to the bc plane by O—H⋯O and N—H⋯O hydrogen-bond interactions.

In the title compound, C 17 H 17 ClN 2 O 2 ÁH 2 O, the dihedral angles formed by the aromatic rings of the chlorobenzene and methylbenzene groups with the mean planes of the attached NH-C(O)-CH 2 fragments are 9.4 (4) and 62.9 (2) , respectively. In the crystal, molecules are packed into layers parallel to the bc plane by O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen-bond interactions.

Experimental
Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with o-toluidine (0.01 mol) in toluene (20 ml) with constant stirring. The resulting mixture was stirred for one hour and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove unreacted o-toluidine.
The resultant solid N-(2-methylphenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The compound was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.
The N-(2-methylphenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of 3chloroaniline at room temperature with constant stirring. The resultant mixture was stirred for 4 h, kept aside for additional 6 h for completion of the reaction and poured slowly into crushed ice with constant stirring. It was kept aside for a day. The resultant solid, N-(3-chlorophenyl)-N'-(2-methylphenyl)succinamide monohydrate was filtered under suction, washed thoroughly with water, with a dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from an acetone/chloroform (1:1 v/v) solution. The purity of the compound was checked by elemental analysis, and supplementary materials sup-2 characterized by its infrared and NMR spectra. Needle-like colourless single crystals used for the X-ray diffraction studies were grown by slow evaporation of an acetone/chloroform (1:1 v/v) solution at room temperature.

Refinement
The amine and water H atoms were located in a difference Fourier map and refined with the N-H and O-H distances restrained to 0.86 (2) and 0.85 (2) Å, respectively. All other H atoms were positioned with idealized geometry using a riding model with the aromatic C-H = 0.93 Å, methyl C-H = 0.97 mÅ and methylene C-H = 0.97 Å, and with isotropic displacement parameters set to 1.2 times of the U eq of the parent atoms. The crystals available for X-ray analysis were of rather poor quality and weak scatterers at high theta value, resulting in relatively high R values. Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. The intermolecular O-H···O hydrogen bond involving the water molecule is drawn as a dashed line.