Ethyl N-[3-(N,N-dimethylcarbamoyl)pyridin-2-ylsulfonyl]carbamate

In the molecular structure of the title compound, C11H15N3O5S, the amide group is nearly perpendicular to the pyridine ring, making a dihedral angle of 86.30 (13)°. The terminal ethyl group is disordered over two sites of equal occupancy. Intermolecular N—H⋯O hydrogen bonding is present in the crystal structure.

In the molecular structure of the title compound, C 11 H 15 N 3 O 5 S, the amide group is nearly perpendicular to the pyridine ring, making a dihedral angle of 86.30 (13) . The terminal ethyl group is disordered over two sites of equal occupancy. Intermolecular N-HÁ Á ÁO hydrogen bonding is present in the crystal structure.
The molecular structure is shown in Fig. 1. In the molecular structure the amide group is nearly perpendicular to the pyridine ring, the dihedral angle being 86.30 (13)°. Intermolecular N-H···O hydrogen bonding (Table 1) helps to stabilize the crystal structure.

Experimental
To a solution of N,N-dimethyl-2-sulfamoylnicotinamide (10 mmol) and NaOH (12 mmol) in anhydrous toluene (50 ml) was added ethyl carbonochloridate (12 mmol). After stirring the mixture for 10 h at room temperature, the solvent was removed and 100 ml water was added. The oil after separation was concentrated under reduced pressure and the residue was recrystallized from methanol to give the title compound in a yield of 90% (Murai et al. 1992). Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from ethanol at room temperature in a yield of 60%.

Refinement
The ethyl group is disordered over two positions with 0.5 occupancy for each component. In the refinement. Imino H atom was located in a difference Fourier map and was refined isotropically. Other H atoms were placed in idealized positions with C-H = 0.96 (methyl), 0.97 (methylene) and 0.93 Å (aromatic), and refined in the riding-model approximation with U iso (H) = 1.5U eq (C) for methyl H atoms and 1.2U eq (C) for the others.  Ethyl N- [3-(N,N-dimethylcarbamoyl)

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 > σ(F 2 ) is used only for calculating Rfactors(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.