4-Methoxy-N-[(4-methylphenyl)sulfonyl]benzamide including an unknown solvate

In the title compound, C15H15NO4S, the dihedral angle between the benzene rings is 78.62 (16)°. In the crystal, adjacent molecules are linked along the c axis into C(4) chains through strong N—H⋯O hydrogen bonds. Molecules are further connected through C—H⋯O hydrogen bonds into a hexameric unit generating an R 6 6(66) motif. Another C—H⋯O interaction connects the molecules along the c axis, forming C(5) chains. A region of disordered electron density, most probably disordered methanol–water solvent molecules, was treated with the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. The formula mass and unit-cell characteristics do not take into account this disordered solvent.

In the title compound, C 15 H 15 NO 4 S, the dihedral angle between the benzene rings is 78.62 (16) . In the crystal, adjacent molecules are linked along the c axis into C(4) chains through strong N-HÁ Á ÁO hydrogen bonds. Molecules are further connected through C-HÁ Á ÁO hydrogen bonds into a hexameric unit generating an R 6 6 (66) motif. Another C-HÁ Á ÁO interaction connects the molecules along the c axis, forming C(5) chains. A region of disordered electron density, most probably disordered methanol-water solvent molecules, was treated with the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, [148][149][150][151][152][153][154][155]. The formula mass and unitcell characteristics do not take into account this disordered solvent.   Table 1 Hydrogen-bond geometry (Å , ).  and), we report herein on the crystal structure of the title compound.

Related literature
In the title compound, Fig. 1, the dihedral angle between the benzene rings is 78.62 (16)  In the crystal, adjacent molecules are linked along the c axis into C(4) chains via N-H···O hydrogen bonds (Table 1 and Fig. 2). Molecules are also connected through C-H···O hydrogen bonds into a hexameric unit generating an R 6 6 (66) motif (Table 1 and Fig. 3). Further C-H···O hydrogen bonds connect the molecules along the c axis forming C(5) chains (Table 1 and Fig. 4).

Experimental
The title compound was prepared by refluxing a mixture of 4-methoxybenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxychloride (POCl 3 ) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was then re-precipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and then dried (M.p. = 393 K). Colourless prism-like crystals of the title compound were obtained by slow evaporation of an water/methanol solution (1:1) at room temperature.

Refinement
The NH hydrogen atom was located in a difference Fourier map and refined with a distance restraint of N-H = 0.86 (2) Å. The C bound H atoms were positioned with idealized geometry and refined using a riding model: C-H = 0.93-0.96 Å with U eq = 1.5U eq (C-methyl) and = 1.2U eq (C) for other H atoms. The C7 methyl H atoms were refined with AFIX 127, viz., an idealized disordered methyl group with two positions rotated from each other by 60 °. The crystal did not diffract significantly beyond 22 ° in θ. A region of disordered electron density, probably disordered methanol/water solvent molecules, was treated with the SQUEEZE routine in PLATON (Spek, 2009); more details are given in "_platon_squeeze_details".

Figure 1
The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A view along the b axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1 for details; C bound hydrogen atoms have been omitted for clarity).  A view of the hexameric C-H···O hydrogen bonded R 6 6 (66) ring motif in the crystal structure of the title compound (see Table 1 for details; H atoms not involved in these hydrogen bonds have been omitted for clarity).  A view of the C-H···O hydrogen bonds linking molecules to form C(5) chains in the crystal structure of the title compound (see Table 1 for details; H atoms not involved in these hydrogen bonds have been omitted for clarity). 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.