Quinoline-2-sulfonamide.

In the title compound, C9H8N2O2S, the sulfamoyl -NH2 group is involved in inter-molecular hydrogen bonding with the sulfonamide O and quinoline N atoms. In the crystal, mol-ecules are linked into dimers via pairs of N-H⋯N hydrogen bonds, forming an R 2 (2)(10) motif. The dimers are further assembled into chains parallel to the b axis through N-H⋯O hydrogen bonds, generating a C(4) motif. The crystal packing is additionally stabilized by inter-molecular C-H⋯O inter-actions. The crystal studied was a non-merohedral twin with a domain ratio of 0.938 (2):0.062 (2). Density functional theory (DFT) calculations, at the B3LYP/6-31 G(d,p) level of theory, were used to optimize the mol-ecular structure and to determine inter-action energies for the title compound. The resulting inter-action energy is ∼4.4 kcal mol(-1) per bridge for the C(4) chain and ∼5.9 kcal mol(-1) per bridge for the R 2 (2)(10) motif.

Related literature

For the use of the quinoline­sulfamoyl unit in medicinal chemistry, see: Kim et al. (2005 ▶); Zajdel et al. (2012 ▶, 2013 ▶). For related structures, see: Marciniec et al. (2012 ▶). For the synthesis, see: Maślankiewicz et al. (2007 ▶). For hydrogen-bonding motifs in sufonamides, see: Adsmond & Grant (2001 ▶). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For general hydrogen-bond rules, see: Donohue (1952 ▶); Etter (1990 ▶). For details of theoretical calculations, see: Frisch et al. (2009 ▶4); Parr & Yang (1989 ▶). The twin matrix was been determined with ROTAX (Cooper et al., 2002 ▶).

Experimental

Crystal data

C9H8N2O2S

M = 208.23

Monoclinic,

a = 8.5907 (1) Å

b = 5.1716 (1) Å

c = 20.0375 (3) Å

β = 94.230 (1)°

V = 887.79 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.27 × 0.23 × 0.05 mm

Data collection

Agilent SuperNova diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.919, T max = 1.000

27311 measured reflections

1552 independent reflections

1530 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.12

1552 reflections

160 parameters

All H-atom parameters refined

Δρmax = 0.35 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 2012 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681302062X/gk2577sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302062X/gk2577Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302062X/gk2577Isup3.cml

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

C9H8N2O2S	F(000) = 432
Mr = 208.23	Dx = 1.558 Mg m−3
Monoclinic, P21/c	Melting point: 441.2 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.5907 (1) Å	Cell parameters from 14635 reflections
b = 5.1716 (1) Å	θ = 2.0–37.3°
c = 20.0375 (3) Å	µ = 0.34 mm−1
β = 94.230 (1)°	T = 100 K
V = 887.79 (2) Å3	Plate, colorless
Z = 4	0.27 × 0.23 × 0.05 mm

Agilent SuperNova diffractometer with an Atlas detector	1552 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1530 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
Detector resolution: 10.4498 pixels mm-1	θmax = 25.1°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −6→6
Tmin = 0.919, Tmax = 1.000	l = −23→23
27311 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	All H-atom parameters refined
S = 1.12	w = 1/[σ2(Fo2) + (0.0262P)2 + 0.9337P] where P = (Fo2 + 2Fc2)/3
1552 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.32 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	0.24131 (5)	0.61370 (8)	0.04453 (2)	0.01307 (14)
O1	0.18557 (15)	0.3614 (2)	0.06117 (6)	0.0193 (3)
O2	0.38294 (14)	0.7120 (3)	0.07708 (6)	0.0188 (3)
N1	0.19733 (16)	0.4337 (3)	−0.07942 (7)	0.0132 (3)
N2	0.10504 (19)	0.8125 (3)	0.05580 (8)	0.0164 (3)
C2	0.26951 (19)	0.6149 (3)	−0.04339 (8)	0.0129 (4)
C3	0.3627 (2)	0.8112 (4)	−0.06810 (9)	0.0153 (4)
C4	0.3835 (2)	0.8125 (4)	−0.13486 (9)	0.0156 (4)
C4A	0.31105 (19)	0.6202 (4)	−0.17656 (9)	0.0147 (4)
C5	0.3263 (2)	0.6090 (4)	−0.24669 (9)	0.0169 (4)
C6	0.2521 (2)	0.4209 (4)	−0.28441 (9)	0.0180 (4)
C7	0.1578 (2)	0.2367 (4)	−0.25488 (9)	0.0175 (4)
C8	0.1389 (2)	0.2425 (4)	−0.18758 (9)	0.0159 (4)
C8A	0.21642 (19)	0.4342 (3)	−0.14675 (8)	0.0129 (4)
H2N2	0.126 (3)	0.971 (5)	0.0528 (11)	0.027 (6)*
H1N2	0.019 (3)	0.751 (5)	0.0549 (12)	0.035 (7)*
H3	0.409 (2)	0.940 (4)	−0.0389 (11)	0.020 (5)*
H4	0.444 (2)	0.945 (4)	−0.1538 (10)	0.021 (5)*
H5	0.391 (2)	0.744 (4)	−0.2674 (9)	0.012 (5)*
H6	0.265 (3)	0.415 (4)	−0.3299 (12)	0.026 (6)*
H7	0.107 (2)	0.103 (4)	−0.2823 (11)	0.023 (6)*
H8	0.073 (2)	0.117 (4)	−0.1661 (11)	0.023 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0168 (2)	0.0096 (2)	0.0124 (2)	−0.00169 (17)	−0.00137 (16)	−0.00008 (16)
O1	0.0290 (7)	0.0112 (6)	0.0172 (6)	−0.0037 (6)	−0.0005 (5)	0.0013 (5)
O2	0.0188 (6)	0.0195 (7)	0.0172 (6)	−0.0019 (6)	−0.0046 (5)	−0.0012 (5)
N1	0.0128 (7)	0.0115 (7)	0.0152 (7)	0.0013 (6)	−0.0002 (6)	−0.0011 (6)
N2	0.0166 (8)	0.0106 (8)	0.0223 (8)	−0.0043 (7)	0.0030 (6)	−0.0020 (6)
C2	0.0114 (8)	0.0123 (9)	0.0146 (8)	0.0028 (7)	−0.0011 (6)	−0.0010 (7)
C3	0.0142 (8)	0.0135 (9)	0.0176 (9)	−0.0015 (7)	−0.0023 (7)	−0.0015 (7)
C4	0.0119 (8)	0.0144 (9)	0.0203 (9)	−0.0007 (7)	0.0007 (7)	0.0014 (7)
C4A	0.0116 (8)	0.0149 (9)	0.0176 (9)	0.0023 (7)	0.0002 (7)	0.0005 (7)
C5	0.0153 (8)	0.0187 (9)	0.0169 (9)	0.0017 (8)	0.0029 (7)	0.0015 (7)
C6	0.0164 (9)	0.0225 (10)	0.0149 (9)	0.0048 (8)	0.0006 (7)	−0.0015 (8)
C7	0.0167 (9)	0.0177 (9)	0.0173 (9)	0.0031 (8)	−0.0032 (7)	−0.0046 (7)
C8	0.0138 (8)	0.0146 (9)	0.0192 (9)	0.0006 (7)	−0.0005 (7)	−0.0010 (7)
C8A	0.0112 (8)	0.0116 (8)	0.0157 (9)	0.0033 (7)	−0.0010 (6)	−0.0004 (7)

S1—O2	1.4308 (13)	C4—H4	0.95 (2)
S1—O1	1.4376 (13)	C4A—C8A	1.419 (2)
S1—N2	1.5866 (16)	C4A—C5	1.422 (2)
S1—C2	1.7959 (18)	C5—C6	1.361 (3)
N1—C2	1.311 (2)	C5—H5	1.00 (2)
N1—C8A	1.371 (2)	C6—C7	1.409 (3)
N2—H2N2	0.84 (3)	C6—H6	0.93 (2)
N2—H1N2	0.80 (3)	C7—C8	1.370 (3)
C2—C3	1.406 (3)	C7—H7	0.97 (2)
C3—C4	1.363 (3)	C8—C8A	1.419 (2)
C3—H3	0.96 (2)	C8—H8	0.98 (2)
C4—C4A	1.414 (3)
O2—S1—O1	120.23 (8)	C4—C4A—C8A	117.98 (16)
O2—S1—N2	108.44 (8)	C4—C4A—C5	122.96 (17)
O1—S1—N2	107.06 (9)	C8A—C4A—C5	119.05 (16)
O2—S1—C2	105.91 (8)	C6—C5—C4A	120.28 (17)
O1—S1—C2	107.59 (8)	C6—C5—H5	121.3 (11)
N2—S1—C2	106.96 (8)	C4A—C5—H5	118.4 (11)
C2—N1—C8A	117.05 (15)	C5—C6—C7	120.69 (17)
S1—N2—H2N2	117.0 (16)	C5—C6—H6	118.9 (14)
S1—N2—H1N2	115.3 (19)	C7—C6—H6	120.4 (14)
H2N2—N2—H1N2	126 (3)	C8—C7—C6	120.79 (17)
N1—C2—C3	125.52 (17)	C8—C7—H7	119.6 (13)
N1—C2—S1	116.44 (13)	C6—C7—H7	119.6 (13)
C3—C2—S1	118.02 (13)	C7—C8—C8A	119.87 (17)
C4—C3—C2	117.95 (17)	C7—C8—H8	122.0 (13)
C4—C3—H3	121.2 (13)	C8A—C8—H8	118.1 (13)
C2—C3—H3	120.9 (13)	N1—C8A—C8	118.75 (16)
C3—C4—C4A	119.54 (17)	N1—C8A—C4A	121.94 (16)
C3—C4—H4	120.5 (13)	C8—C8A—C4A	119.31 (16)
C4A—C4—H4	119.9 (13)
C8A—N1—C2—C3	1.0 (3)	C4—C4A—C5—C6	−179.17 (17)
C8A—N1—C2—S1	179.28 (12)	C8A—C4A—C5—C6	−0.5 (3)
O2—S1—C2—N1	148.59 (13)	C4A—C5—C6—C7	0.7 (3)
O1—S1—C2—N1	18.84 (15)	C5—C6—C7—C8	−0.1 (3)
N2—S1—C2—N1	−95.88 (14)	C6—C7—C8—C8A	−0.7 (3)
O2—S1—C2—C3	−32.97 (16)	C2—N1—C8A—C8	−179.41 (15)
O1—S1—C2—C3	−162.72 (13)	C2—N1—C8A—C4A	0.6 (2)
N2—S1—C2—C3	82.55 (15)	C7—C8—C8A—N1	−179.13 (16)
N1—C2—C3—C4	−1.5 (3)	C7—C8—C8A—C4A	0.9 (3)
S1—C2—C3—C4	−179.75 (13)	C4—C4A—C8A—N1	−1.6 (2)
C2—C3—C4—C4A	0.4 (3)	C5—C4A—C8A—N1	179.74 (15)
C3—C4—C4A—C8A	1.0 (3)	C4—C4A—C8A—C8	178.43 (16)
C3—C4—C4A—C5	179.67 (17)	C5—C4A—C8A—C8	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O1i	0.84 (3)	2.09 (3)	2.922 (2)	171 (2)
N2—H1N2···N1ii	0.80 (3)	2.18 (3)	2.962 (2)	165 (2)
C3—H3···O2iii	0.96 (2)	2.68 (2)	3.308 (2)	123.5 (16)
C4—H4···O2iii	0.95 (2)	2.72 (2)	3.327 (2)	122.3 (15)
C6—H6···O1iv	0.93 (2)	2.66 (2)	3.431 (2)	141.5 (18)

	B3LYP/6-31G(d,p)
	Energy	ΔE
Asymmetric unit	-631075.7
2 units N1 = C(4)	-1262155.9	-4.4
2 units N1 = R22(10)	-1262163.3	-11.8
3 units N1 = C(4)R22(10)	-1893243.7	-16.6
4 units N2 = R44(14)	-2524335.0	-32.2

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N2⋯O1i	0.84 (3)	2.09 (3)	2.922 (2)	171 (2)
N2—H1N2⋯N1ii	0.80 (3)	2.18 (3)	2.962 (2)	165 (2)
C6—H6⋯O1iii	0.93 (2)	2.66 (2)	3.431 (2)	141.5 (18)

Symmetry codes: (i) ; (ii) ; (iii) .