Methyl 4-{[(4-methylphenyl)sulfonyl]amino}benzoate

In the molecule of the title compound, C15H15NO4S, the dihedral angle between the two rings is 88.05 (7)°. The methyl ester group is nearly coplanar with the adjacent ring [dihedral angle = 2.81 (10)°], whereas it is oriented at 86.90 (9)° with respect to the plane of the ring attached to the –SO2– group. Weak intramolecular C—H⋯O hydrogen bonding completes S(5) and S(6) ring motifs. The molecules form one-dimensional polymeric C(8) chains along the [010] direction due to N—H⋯O hydrogen bonding and these chains are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.

In the molecule of the title compound, C 15 H 15 NO 4 S, the dihedral angle between the two rings is 88.05 (7) . The methyl ester group is nearly coplanar with the adjacent ring [dihedral angle = 2.81 (10) ], whereas it is oriented at 86.90 (9) with respect to the plane of the ring attached to the -SO 2 -group. Weak intramolecular C-HÁ Á ÁO hydrogen bonding completes S(5) and S(6) ring motifs. The molecules form one-dimensional polymeric C(8) chains along the [010] direction due to N-HÁ Á ÁO hydrogen bonding and these chains are linked by C-HÁ Á ÁO hydrogen bonds, forming a three-dimensional network.
There exist intramolecular H-bonding of C-H···O type (Table 1, Fig. 1) forming an S(5) and S(6) ring motifs (Bernstein et al., 1995). There exist also intermolecular H-bondings of N-H···O type (Table 1, Fig. 2) due to which the molecules form C(8) one-dimensional polymeric chains extending along the [010] direction. There exist R 2 2 (9) ring motifs due to intermolecular H-bondings of C-H···O and N-H···O types (Table 1, Fig. 2). The other intermolecular H-bondings of C -H···O type interlink these polymeric chains to stabilize the molecules in the form of three-dimensional polymeric network.
The pH of the solution was maintained strictly at 8 to 9 using 1 M Na 2 CO 3 solution. 4-Methyl sulfonyl chloride (1.906 g, 10 mmol) was then added to the solution while stirring at room temperature. On completion of the reaction the pH was adjusted to 1-2, using 1 N HCl while stirring. The precipitates obtained were filtered off, washed with distilled water, dried and subjected to re-crystallization using methanol to afford colorless prisms of (I). m.p. 343 K.

Refinement
The H atoms were positioned geometrically (N-H = 0.86 Å, C-H = 0.93-0.96 Å) and refined as riding with U iso (H) = xU eq (C, N), where x = 1.5 for methyl groups and x = 1.2 for all H atoms.

Figure 2
The partial packing (PLATON; Spek, 2009)  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.28 e Å −3 Δρ min = −0.27 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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 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.