Quinoline-8-sulfonamide

Krzysztof Marciniec; Andrzej Maślankiewicz; Maria Nowak; Joachim Kusz

doi:10.1107/S1600536812036963

. 2012 Sep 1;68(Pt 10):o2826. doi: 10.1107/S1600536812036963

Quinoline-8-sulfonamide¹

Krzysztof Marciniec ^a,^*, Andrzej Maślankiewicz ^a, Maria Nowak ^b, Joachim Kusz ^b

PMCID: PMC3470188 PMID: 23125632

Abstract

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.

Related literature

For the use of the quinolinesulfamoyl unit in medicinal chemistry, see: Borras et al. (1999 ▶); Eveloch et al. (1981 ▶); Zajdel et al. (2011 ▶, 2012 ▶). For the synthesis, see: Maślankiewicz et al. (2007 ▶). For hydrogen-bonding motifs in sufonamides, see: Adsmond & Grant (2001 ▶). For graph-set notation of hydrgen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₉H₈N₂O₂S
M _r = 208.23
Monoclinic,
a = 8.9431 (3) Å
b = 10.4542 (2) Å
c = 10.4648 (2) Å
β = 109.313 (2)°
V = 923.33 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 K
0.34 × 0.21 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.898, T _max = 0.944
5936 measured reflections
1636 independent reflections
1446 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.095
S = 0.97
1636 reflections
135 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; 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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036963/gk2515sup1.cif

e-68-o2826-sup1.cif^{(18.9KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536812036963/gk2515Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036963/gk2515Isup3.hkl

e-68-o2826-Isup3.hkl^{(79KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036963/gk2515Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O2ⁱ	0.87 (2)	2.15 (3)	3.013 (2)	169 (2)
N2—H2N⋯N1	0.83 (2)	2.33 (2)	2.921 (2)	129 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This study was supported by the Medical University of Silesia, grant No. KNW-1–073/P/1/0.

supplementary crystallographic information

Comment

Quinolinesulfamoyl moiety is being more and more frequently incorporated into molecules of biologically active compounds such as carbonic anhydrase inhibitors (Borras et al., 1999) and 5-HT receptors ligands (Zajdel et al., 2011; Zajdel et al., 2012). Since the quinoline drugs as well as sulfonamides strongly interact with enzymatic receptors via their nitrogen atoms (Eveloch et al., 1981) we studied the crystal structure of the title compound, to evaluate the spatial environment of the nitrogen atoms.

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 Adsmond &Grant (2001) consing of S=O···H—N chains (50 occurrences in 39 different sulfonamide structures) is absent in the title compound.

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.