8-Hy-droxy-quinolin-1-ium nitrate.

In the title salt, C(9)H(8)NO(+)·NO(3) (-), the quinoline ring system is essentially planar with a maximum deviation of 0.043 (1) Å. In the crystal, an R(2) (2)(7) ring motif is formed by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds between the cation and the anion. In addition, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the two ions, generating an R(2) (2)(8) ring motif. These sets of ring motifs are further linked into a ribbon along the a axis via inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to and the biological activity of quinoline derivatives, see: Campbell et al. (1988 ▶); Markees et al. (1970 ▶); Michael (1997 ▶); Morimoto et al. (1991 ▶); Reux et al. (2009 ▶); Sasaki et al. (1998 ▶). For related structures, see: Loh et al. (2010a ▶,b ▶,c ▶,d ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H8NO+·NO3 −

M = 208.17

Monoclinic,

a = 11.3186 (2) Å

b = 6.7568 (1) Å

c = 14.5006 (2) Å

β = 128.882 (1)°

V = 863.27 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.33 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.959, T max = 0.981

9590 measured reflections

1978 independent reflections

1754 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.095

S = 1.08

1978 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039395/is2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039395/is2609Isup2.hkl

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

C9H8NO+·NO3−	F(000) = 432
Mr = 208.17	Dx = 1.602 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5491 reflections
a = 11.3186 (2) Å	θ = 3.5–37.4°
b = 6.7568 (1) Å	µ = 0.13 mm−1
c = 14.5006 (2) Å	T = 100 K
β = 128.882 (1)°	Block, colourless
V = 863.27 (2) Å3	0.33 × 0.21 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1978 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.959, Tmax = 0.981	k = −8→8
9590 measured reflections	l = −18→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.3584P] where P = (Fo2 + 2Fc2)/3
1978 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.07908 (9)	0.09986 (13)	0.12784 (7)	0.0167 (2)
N1	−0.13600 (11)	0.10475 (14)	0.15595 (8)	0.0139 (2)
C1	0.01506 (13)	0.11333 (16)	0.25398 (10)	0.0138 (2)
C2	−0.24612 (13)	0.10646 (17)	0.16438 (10)	0.0163 (2)
H2A	−0.3465	0.0953	0.0961	0.020*
C3	−0.21344 (13)	0.12476 (17)	0.27446 (10)	0.0171 (2)
H3A	−0.2913	0.1279	0.2795	0.021*
C4	−0.06498 (13)	0.13802 (17)	0.37464 (10)	0.0158 (2)
H4A	−0.0424	0.1546	0.4479	0.019*
C5	0.05450 (13)	0.12672 (16)	0.36803 (10)	0.0144 (2)
C6	0.21000 (13)	0.12812 (17)	0.46913 (10)	0.0171 (2)
H6A	0.2383	0.1339	0.5447	0.020*
C7	0.31841 (13)	0.12080 (18)	0.45453 (10)	0.0186 (3)
H7A	0.4204	0.1209	0.5210	0.022*
C8	0.27878 (13)	0.11312 (18)	0.34078 (11)	0.0177 (2)
H8A	0.3547	0.1114	0.3334	0.021*
C9	0.12859 (13)	0.10813 (16)	0.24054 (10)	0.0148 (2)
O2	0.52824 (10)	0.47945 (18)	0.24518 (8)	0.0321 (3)
O3	0.53907 (10)	0.42125 (15)	0.39694 (8)	0.0239 (2)
O4	0.74765 (9)	0.44023 (13)	0.41965 (7)	0.0179 (2)
N2	0.60151 (11)	0.44742 (16)	0.35208 (9)	0.0177 (2)
H1N1	−0.1627 (19)	0.091 (2)	0.0852 (16)	0.028 (4)*
H1O1	0.145 (2)	0.056 (3)	0.1211 (17)	0.042 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0159 (4)	0.0230 (4)	0.0140 (4)	0.0024 (3)	0.0108 (3)	0.0012 (3)
N1	0.0159 (5)	0.0145 (5)	0.0124 (4)	0.0001 (4)	0.0095 (4)	−0.0002 (3)
C1	0.0161 (5)	0.0114 (5)	0.0137 (5)	0.0003 (4)	0.0094 (4)	0.0003 (4)
C2	0.0153 (5)	0.0169 (5)	0.0167 (5)	−0.0007 (4)	0.0100 (4)	−0.0008 (4)
C3	0.0189 (5)	0.0183 (6)	0.0200 (5)	−0.0007 (4)	0.0150 (5)	−0.0012 (4)
C4	0.0216 (6)	0.0138 (5)	0.0150 (5)	0.0000 (4)	0.0130 (5)	−0.0003 (4)
C5	0.0183 (5)	0.0114 (5)	0.0146 (5)	−0.0001 (4)	0.0108 (5)	0.0000 (4)
C6	0.0198 (5)	0.0163 (5)	0.0133 (5)	0.0006 (4)	0.0095 (5)	−0.0004 (4)
C7	0.0152 (5)	0.0191 (6)	0.0160 (5)	0.0010 (4)	0.0071 (4)	−0.0004 (4)
C8	0.0163 (5)	0.0186 (6)	0.0203 (6)	0.0008 (4)	0.0126 (5)	0.0003 (4)
C9	0.0184 (5)	0.0132 (5)	0.0147 (5)	0.0010 (4)	0.0113 (5)	0.0010 (4)
O2	0.0186 (4)	0.0607 (7)	0.0157 (4)	0.0030 (4)	0.0101 (4)	0.0078 (4)
O3	0.0169 (4)	0.0395 (5)	0.0197 (4)	−0.0012 (4)	0.0137 (4)	0.0007 (4)
O4	0.0121 (4)	0.0260 (5)	0.0155 (4)	0.0000 (3)	0.0087 (3)	−0.0005 (3)
N2	0.0141 (4)	0.0238 (5)	0.0159 (5)	0.0002 (4)	0.0098 (4)	−0.0006 (4)

O1—C9	1.3558 (13)	C4—H4A	0.9300
O1—H1O1	0.86 (2)	C5—C6	1.4170 (15)
N1—C2	1.3266 (15)	C6—C7	1.3707 (16)
N1—C1	1.3770 (14)	C6—H6A	0.9300
N1—H1N1	0.874 (18)	C7—C8	1.4126 (16)
C1—C9	1.4160 (16)	C7—H7A	0.9300
C1—C5	1.4196 (15)	C8—C9	1.3790 (16)
C2—C3	1.3995 (16)	C8—H8A	0.9300
C2—H2A	0.9300	O2—N2	1.2343 (13)
C3—C4	1.3701 (16)	O3—N2	1.2372 (13)
C3—H3A	0.9300	O4—N2	1.2899 (12)
C4—C5	1.4166 (16)
C9—O1—H1O1	114.7 (13)	C4—C5—C1	117.82 (10)
C2—N1—C1	122.28 (10)	C6—C5—C1	118.93 (10)
C2—N1—H1N1	117.2 (11)	C7—C6—C5	119.40 (10)
C1—N1—H1N1	120.5 (11)	C7—C6—H6A	120.3
N1—C1—C9	120.19 (10)	C5—C6—H6A	120.3
N1—C1—C5	118.95 (10)	C6—C7—C8	121.52 (11)
C9—C1—C5	120.86 (10)	C6—C7—H7A	119.2
N1—C2—C3	120.99 (10)	C8—C7—H7A	119.2
N1—C2—H2A	119.5	C9—C8—C7	120.63 (11)
C3—C2—H2A	119.5	C9—C8—H8A	119.7
C4—C3—C2	119.03 (10)	C7—C8—H8A	119.7
C4—C3—H3A	120.5	O1—C9—C8	125.09 (10)
C2—C3—H3A	120.5	O1—C9—C1	116.28 (10)
C3—C4—C5	120.81 (10)	C8—C9—C1	118.62 (10)
C3—C4—H4A	119.6	O2—N2—O3	122.01 (10)
C5—C4—H4A	119.6	O2—N2—O4	119.39 (9)
C4—C5—C6	123.24 (10)	O3—N2—O4	118.60 (9)
C2—N1—C1—C9	179.06 (10)	C4—C5—C6—C7	−178.64 (11)
C2—N1—C1—C5	−0.72 (16)	C1—C5—C6—C7	1.38 (16)
C1—N1—C2—C3	2.44 (17)	C5—C6—C7—C8	0.40 (18)
N1—C2—C3—C4	−0.98 (17)	C6—C7—C8—C9	−1.52 (18)
C2—C3—C4—C5	−2.14 (17)	C7—C8—C9—O1	−179.71 (11)
C3—C4—C5—C6	−176.26 (11)	C7—C8—C9—C1	0.77 (17)
C3—C4—C5—C1	3.72 (16)	N1—C1—C9—O1	1.69 (15)
N1—C1—C5—C4	−2.31 (15)	C5—C1—C9—O1	−178.53 (10)
C9—C1—C5—C4	177.91 (10)	N1—C1—C9—C8	−178.75 (10)
N1—C1—C5—C6	177.67 (10)	C5—C1—C9—C8	1.03 (16)
C9—C1—C5—C6	−2.11 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4i	0.874 (18)	1.944 (18)	2.8112 (12)	171.6 (15)
O1—H1O1···O4ii	0.86 (3)	1.83 (3)	2.6794 (16)	169 (2)
C2—H2A···O3iii	0.93	2.53	3.106 (2)	120
C2—H2A···O3i	0.93	2.31	3.0247 (14)	133
C8—H8A···O2ii	0.93	2.40	3.249 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4i	0.874 (18)	1.944 (18)	2.8112 (12)	171.6 (15)
O1—H1O1⋯O4ii	0.86 (3)	1.83 (3)	2.6794 (16)	169 (2)
C2—H2A⋯O3iii	0.93	2.53	3.106 (2)	120
C2—H2A⋯O3i	0.93	2.31	3.0247 (14)	133
C8—H8A⋯O2ii	0.93	2.40	3.249 (2)	152

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