Quinoline-8-sulfonamide.

In the title compound, C(9)H(8)N(2)O(2)S, the sulfamoyl NH(2) group is involved in intra-molecular N-H⋯N and inter-molecular 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 inter-actions 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 = 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

Δρmax = 0.31 e Å−3

Δρmin = −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.

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

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

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

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

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

C9H8N2O2S	F(000) = 432
Mr = 208.23	Dx = 1.498 Mg m−3
Monoclinic, P21/n	Melting point: 457.2 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.9431 (3) Å	Cell parameters from 5251 reflections
b = 10.4542 (2) Å	θ = 3.1–34.5°
c = 10.4648 (2) Å	µ = 0.32 mm−1
β = 109.313 (2)°	T = 298 K
V = 923.33 (4) Å3	Polyhedron, colourless
Z = 4	0.34 × 0.21 × 0.18 mm

Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer	1636 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 16.0328 pixels mm-1	θmax = 25.1°, θmin = 3.1°
ω–scan	h = −8→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −12→11
Tmin = 0.898, Tmax = 0.944	l = −12→10
5936 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.075P)2 + 0.1368P] where P = (Fo2 + 2Fc2)/3
1636 reflections	(Δ/σ)max = 0.001
135 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.66396 (4)	0.87959 (4)	0.17318 (4)	0.03962 (18)
O1	0.69562 (15)	0.80754 (13)	0.29483 (13)	0.0560 (4)
O2	0.52811 (14)	0.84522 (13)	0.05984 (13)	0.0542 (4)
N1	0.98319 (16)	0.98818 (14)	0.31765 (14)	0.0438 (3)
N2	0.6409 (2)	1.02696 (16)	0.2070 (2)	0.0501 (4)
C2	1.1202 (2)	1.03811 (18)	0.3911 (2)	0.0556 (5)
H2	1.1242	1.0848	0.4678	0.067*
C3	1.2598 (2)	1.0245 (2)	0.3596 (2)	0.0637 (6)
H3	1.3541	1.0596	0.4160	0.076*
C4	1.2566 (2)	0.96016 (18)	0.2470 (2)	0.0568 (5)
H4	1.3485	0.9520	0.2245	0.068*
C4A	1.1134 (2)	0.90515 (16)	0.16339 (19)	0.0430 (4)
C5	1.0985 (2)	0.83950 (17)	0.0427 (2)	0.0513 (5)
H5	1.1871	0.8287	0.0161	0.062*
C6	0.9568 (2)	0.79162 (18)	−0.0357 (2)	0.0540 (5)
H6	0.9487	0.7495	−0.1161	0.065*
C7	0.8221 (2)	0.80560 (16)	0.00428 (17)	0.0448 (4)
H7	0.7254	0.7722	−0.0494	0.054*
C8	0.83294 (17)	0.86792 (14)	0.12156 (15)	0.0341 (4)
C8A	0.97904 (17)	0.92153 (14)	0.20522 (15)	0.0351 (3)
H1N	0.603 (3)	1.071 (2)	0.133 (3)	0.059 (6)*
H2N	0.722 (3)	1.057 (2)	0.263 (3)	0.065 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0313 (3)	0.0447 (3)	0.0465 (3)	−0.00383 (16)	0.01779 (19)	0.00320 (17)
O1	0.0532 (8)	0.0673 (9)	0.0553 (8)	−0.0052 (6)	0.0284 (6)	0.0151 (6)
O2	0.0352 (6)	0.0582 (8)	0.0648 (8)	−0.0102 (5)	0.0106 (6)	−0.0017 (6)
N1	0.0371 (7)	0.0500 (8)	0.0436 (8)	−0.0022 (6)	0.0122 (6)	−0.0040 (6)
N2	0.0378 (8)	0.0549 (10)	0.0613 (10)	0.0023 (7)	0.0215 (8)	−0.0066 (9)
C2	0.0484 (10)	0.0542 (11)	0.0545 (11)	−0.0042 (8)	0.0039 (8)	−0.0058 (8)
C3	0.0357 (10)	0.0557 (12)	0.0876 (16)	−0.0070 (8)	0.0040 (10)	0.0055 (11)
C4	0.0326 (8)	0.0488 (10)	0.0919 (15)	0.0036 (7)	0.0247 (9)	0.0119 (10)
C4A	0.0367 (9)	0.0358 (8)	0.0629 (11)	0.0066 (7)	0.0250 (8)	0.0120 (7)
C5	0.0562 (11)	0.0431 (9)	0.0718 (12)	0.0111 (8)	0.0443 (10)	0.0076 (9)
C6	0.0732 (13)	0.0457 (10)	0.0560 (10)	0.0069 (9)	0.0389 (10)	−0.0030 (8)
C7	0.0509 (10)	0.0404 (9)	0.0448 (9)	−0.0021 (7)	0.0181 (8)	−0.0018 (7)
C8	0.0337 (8)	0.0322 (8)	0.0396 (8)	0.0008 (6)	0.0166 (6)	0.0045 (6)
C8A	0.0333 (8)	0.0328 (8)	0.0418 (8)	0.0017 (6)	0.0161 (7)	0.0047 (6)

S1—O1	1.4247 (13)	C4—C4A	1.413 (3)
S1—O2	1.4348 (12)	C4—H4	0.9300
S1—N2	1.6092 (17)	C4A—C5	1.405 (3)
S1—C8	1.7693 (15)	C4A—C8A	1.419 (2)
N1—C2	1.320 (2)	C5—C6	1.357 (3)
N1—C8A	1.357 (2)	C5—H5	0.9300
N2—H1N	0.87 (2)	C6—C7	1.407 (2)
N2—H2N	0.83 (2)	C6—H6	0.9300
C2—C3	1.400 (3)	C7—C8	1.364 (2)
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.349 (3)	C8—C8A	1.425 (2)
C3—H3	0.9300
O1—S1—O2	118.03 (8)	C5—C4A—C4	123.55 (17)
O1—S1—N2	108.14 (10)	C5—C4A—C8A	119.89 (16)
O2—S1—N2	106.66 (9)	C4—C4A—C8A	116.54 (17)
O1—S1—C8	107.39 (7)	C6—C5—C4A	121.06 (15)
O2—S1—C8	107.79 (8)	C6—C5—H5	119.5
N2—S1—C8	108.52 (7)	C4A—C5—H5	119.5
C2—N1—C8A	117.50 (15)	C5—C6—C7	120.09 (16)
S1—N2—H1N	110.7 (15)	C5—C6—H6	120.0
S1—N2—H2N	112.0 (16)	C7—C6—H6	120.0
H1N—N2—H2N	115 (2)	C8—C7—C6	120.29 (16)
N1—C2—C3	123.47 (19)	C8—C7—H7	119.9
N1—C2—H2	118.3	C6—C7—H7	119.9
C3—C2—H2	118.3	C7—C8—C8A	121.20 (14)
C4—C3—C2	119.58 (17)	C7—C8—S1	119.61 (12)
C4—C3—H3	120.2	C8A—C8—S1	119.17 (12)
C2—C3—H3	120.2	N1—C8A—C4A	123.12 (15)
C3—C4—C4A	119.77 (17)	N1—C8A—C8	119.41 (13)
C3—C4—H4	120.1	C4A—C8A—C8	117.45 (15)
C4A—C4—H4	120.1
C8A—N1—C2—C3	−0.7 (3)	O1—S1—C8—C8A	−64.59 (13)
N1—C2—C3—C4	1.7 (3)	O2—S1—C8—C8A	167.26 (12)
C2—C3—C4—C4A	−1.2 (3)	N2—S1—C8—C8A	52.10 (15)
C3—C4—C4A—C5	178.30 (18)	C2—N1—C8A—C4A	−0.8 (2)
C3—C4—C4A—C8A	−0.2 (3)	C2—N1—C8A—C8	−178.87 (15)
C4—C4A—C5—C6	−178.12 (17)	C5—C4A—C8A—N1	−177.31 (15)
C8A—C4A—C5—C6	0.4 (3)	C4—C4A—C8A—N1	1.3 (2)
C4A—C5—C6—C7	−1.0 (3)	C5—C4A—C8A—C8	0.8 (2)
C5—C6—C7—C8	0.4 (3)	C4—C4A—C8A—C8	179.37 (14)
C6—C7—C8—C8A	0.8 (2)	C7—C8—C8A—N1	176.81 (15)
C6—C7—C8—S1	−177.78 (13)	S1—C8—C8A—N1	−4.61 (19)
O1—S1—C8—C7	114.02 (14)	C7—C8—C8A—C4A	−1.4 (2)
O2—S1—C8—C7	−14.14 (15)	S1—C8—C8A—C4A	177.22 (11)
N2—S1—C8—C7	−129.30 (14)

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)

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)

Symmetry code: (i) .