Quinoline-8-sulfonamide1

In the title compound, C9H8N2O2S, the sulfamoyl NH2 group is involved in intramolecular N—H⋯N and intermolecular N—H⋯O hydrogen bonding. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers, which are further associated through π–π stacking interactions between the quinoline benzene rings [centroid–centroid distance = 3.649 (1) Å] into a one-dimensional polymeric structure extending along the a axis.

In the title compound, C 9 H 8 N 2 O 2 S, the sulfamoyl NH 2 group is involved in intramolecular N-HÁ Á ÁN and intermolecular N-HÁ Á ÁO hydrogen bonding. In the crystal, molecules are linked via pairs of N-HÁ Á ÁO hydrogen bonds, forming inversion dimers, which are further associated throughstacking interactions between the quinoline benzene rings [centroid-centroid distance = 3.649 (1) Å ] into a one-dimensional polymeric structure extending along the a axis.
The molecular conformation of quinoline-8-sulfonamide with the adopted atomic numbering is presented in Fig.1. The sulfonamide group participates in both intra-and intermolecular hydrogen bonding. The H2 atom of the sulfamoyl group shows an intramolecular contact with the N1 atom of the quinoline ring system (Table 1) resulting in the graph-set motif of S(6) (Bernstein et al., 1995). In the crystal, the molecules form dimers through N2-H1···O2 hydrogen bonds (Table   1). It is interesting to note that the most commonly observed hydrogen bonding in sulfonamides in the studies reported by A π-π stacking interaction is observed between the benzene C4A/C5-C8/C8A rings of neighboring dimers with the centroid-to-centroid distance, Cg···Cg (1 -x, 2 -y, -z) of 3.649 (1) Å and interplanar spacing of 3.373 (1) Å (Fig. 2). The π-π stacking interaction connects the dimers along the [100] direction forming one-dimesional polymeric structure.

Experimental
The title compound was prepared by the reaction of 8-quinolinesulfonylchloride with an excess ammonia at temperature of 45°C according to the procedure reported by Maślankiewicz et al. (2007). Single crystals of the title compound suitable for X-ray structure determination were obtained by recrystallization from an ethanolic solution.

Refinement
The hydrogen atoms participating in hydrogen bonding were located in a difference Fourier map and freely refined. Other hydrogen atoms were introduced in geometrically idealized positions and refined using a riding-model approximation with C-H distances of 0.93 Å and with U iso (H)= 1.2U eq (C).

Computing details
Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Jmol (Hanson, 2010) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).    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.