8-Hy-droxy-quinolinium 2-carb-oxy-acetate.

In the title compound, C(9)H(8)NO(+)·C(3)H(3)O(4) (-), the cation and anion are each essentially planar, with maximum deviations of 0.043 (1) and 0.060 (1) Å, respectively. The dihedral angle between these two planes is 2.20 (4)°. The conformation of the anion is stabilized by an intra-molecular O-H⋯O hydrogen bond, which forms an S(6) ring motif. The hy-droxy group of the oxine unit makes a hydrogen bond with the one of the O atoms of the carboxyl-ate group of the 2-carb-oxy-acetate anion. Two other carboxyl-ate O atoms form R(2) (2)(7) ring motifs via inter-molecular C-H⋯O and N-H⋯O hydrogen bonds. The crystal structure is consolidated by weak inter-molecular C-H⋯O inter-actions, which link the cations and anions into a three-dimensional network.

Related literature

For background to and the biological activity of oxines, see: Balasubramanian & Muthiah (1996a ▶,b ▶). For related structures, see: Banerjee et al. (1984 ▶); Loh et al. (2010 ▶). 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 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H8NO+·C3H3O4 −

M = 249.22

Monoclinic,

a = 8.7089 (4) Å

b = 5.2930 (2) Å

c = 23.4672 (9) Å

β = 90.999 (3)°

V = 1081.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.52 × 0.17 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.929, T max = 0.992

12061 measured reflections

3170 independent reflections

2552 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.04

3170 reflections

207 parameters

All H-atom parameters refined

Δρmax = 0.33 e Å−3

Δρmin = −0.29 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/S1600536810030990/bt5313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030990/bt5313Isup2.hkl

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

C9H8NO+·C3H3O4−	F(000) = 520
Mr = 249.22	Dx = 1.530 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3422 reflections
a = 8.7089 (4) Å	θ = 3.5–30.0°
b = 5.2930 (2) Å	µ = 0.12 mm−1
c = 23.4672 (9) Å	T = 100 K
β = 90.999 (3)°	Plate, yellow
V = 1081.58 (8) Å3	0.52 × 0.17 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3170 independent reflections
Radiation source: fine-focus sealed tube	2552 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→12
Tmin = 0.929, Tmax = 0.992	k = −7→7
12061 measured reflections	l = −33→32

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.2285P] where P = (Fo2 + 2Fc2)/3
3170 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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	0.09573 (11)	0.85826 (16)	0.23539 (4)	0.0178 (2)
N1	0.16598 (13)	0.89411 (19)	0.12400 (4)	0.0152 (2)
C1	0.23458 (14)	0.7104 (2)	0.15690 (5)	0.0142 (2)
C2	0.19403 (16)	0.9186 (2)	0.06877 (5)	0.0183 (3)
C3	0.29489 (16)	0.7560 (3)	0.04150 (5)	0.0204 (3)
C4	0.36509 (16)	0.5673 (2)	0.07247 (5)	0.0201 (3)
C5	0.33690 (14)	0.5386 (2)	0.13142 (5)	0.0165 (2)
C6	0.40592 (15)	0.3468 (2)	0.16573 (6)	0.0193 (3)
C7	0.37370 (15)	0.3379 (2)	0.22279 (6)	0.0193 (3)
C8	0.27372 (15)	0.5121 (2)	0.24808 (5)	0.0172 (2)
C9	0.19971 (14)	0.6941 (2)	0.21562 (5)	0.0144 (2)
O2	0.79886 (13)	0.74847 (19)	0.03808 (4)	0.0268 (2)
O3	0.66717 (12)	0.95987 (18)	0.10240 (4)	0.0237 (2)
O4	0.96190 (11)	0.38081 (17)	0.06705 (4)	0.0208 (2)
O5	0.97057 (11)	0.25359 (16)	0.15766 (3)	0.0177 (2)
C10	0.75145 (15)	0.7864 (2)	0.09062 (5)	0.0176 (2)
C11	0.80638 (16)	0.5972 (2)	0.13524 (5)	0.0195 (3)
C12	0.92134 (14)	0.3958 (2)	0.11786 (5)	0.0155 (2)
H1O1	0.073 (2)	0.817 (4)	0.2748 (9)	0.042 (5)*
H1O2	0.866 (3)	0.602 (4)	0.0417 (9)	0.057 (6)*
H1N1	0.098 (2)	1.015 (4)	0.1398 (8)	0.037 (5)*
H2A	0.141 (2)	1.051 (3)	0.0516 (7)	0.022 (4)*
H3A	0.3100 (19)	0.781 (3)	0.0005 (7)	0.023 (4)*
H4A	0.437 (2)	0.447 (3)	0.0560 (7)	0.027 (4)*
H6A	0.4720 (18)	0.226 (3)	0.1476 (7)	0.019 (4)*
H7A	0.4224 (19)	0.207 (3)	0.2466 (7)	0.024 (4)*
H8A	0.2547 (19)	0.505 (3)	0.2888 (7)	0.020 (4)*
H11A	0.716 (2)	0.510 (4)	0.1503 (8)	0.039 (5)*
H11B	0.852 (2)	0.689 (4)	0.1680 (8)	0.035 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0235 (5)	0.0173 (4)	0.0128 (4)	0.0039 (4)	0.0051 (3)	0.0010 (3)
N1	0.0187 (5)	0.0143 (4)	0.0128 (5)	−0.0006 (4)	0.0020 (4)	−0.0003 (4)
C1	0.0153 (6)	0.0129 (5)	0.0146 (5)	−0.0014 (4)	0.0013 (4)	−0.0008 (4)
C2	0.0229 (7)	0.0186 (6)	0.0135 (5)	−0.0009 (5)	0.0017 (4)	0.0008 (4)
C3	0.0242 (7)	0.0240 (6)	0.0130 (5)	−0.0009 (5)	0.0041 (5)	−0.0016 (5)
C4	0.0201 (7)	0.0213 (6)	0.0191 (6)	0.0009 (5)	0.0047 (5)	−0.0045 (5)
C5	0.0159 (6)	0.0160 (5)	0.0178 (6)	−0.0018 (4)	0.0017 (4)	−0.0016 (4)
C6	0.0170 (6)	0.0161 (5)	0.0248 (6)	0.0015 (5)	0.0016 (5)	−0.0018 (5)
C7	0.0180 (6)	0.0160 (5)	0.0239 (6)	0.0005 (5)	−0.0007 (5)	0.0035 (5)
C8	0.0186 (6)	0.0169 (5)	0.0160 (5)	−0.0024 (5)	0.0007 (4)	0.0019 (4)
C9	0.0161 (6)	0.0136 (5)	0.0137 (5)	−0.0022 (4)	0.0023 (4)	0.0002 (4)
O2	0.0417 (7)	0.0242 (5)	0.0146 (4)	0.0117 (4)	0.0046 (4)	0.0025 (4)
O3	0.0263 (5)	0.0216 (5)	0.0232 (5)	0.0067 (4)	0.0009 (4)	−0.0014 (4)
O4	0.0293 (5)	0.0205 (4)	0.0127 (4)	0.0049 (4)	0.0051 (3)	0.0001 (3)
O5	0.0228 (5)	0.0175 (4)	0.0128 (4)	0.0018 (3)	0.0023 (3)	0.0008 (3)
C10	0.0197 (6)	0.0170 (5)	0.0160 (5)	0.0001 (5)	0.0005 (4)	−0.0009 (4)
C11	0.0241 (7)	0.0211 (6)	0.0132 (5)	0.0055 (5)	0.0040 (5)	0.0008 (4)
C12	0.0178 (6)	0.0149 (5)	0.0139 (5)	−0.0023 (4)	0.0015 (4)	−0.0013 (4)

O1—C9	1.3434 (15)	C6—H6A	0.963 (17)
O1—H1O1	0.97 (2)	C7—C8	1.4066 (18)
N1—C2	1.3295 (15)	C7—H7A	0.981 (17)
N1—C1	1.3722 (15)	C8—C9	1.3811 (17)
N1—H1N1	0.95 (2)	C8—H8A	0.973 (16)
C1—C5	1.4132 (17)	O2—C10	1.3223 (15)
C1—C9	1.4187 (16)	O2—H1O2	0.97 (2)
C2—C3	1.3933 (18)	O3—C10	1.2107 (16)
C2—H2A	0.928 (17)	O4—C12	1.2521 (14)
C3—C4	1.3727 (19)	O5—C12	1.2683 (14)
C3—H3A	0.982 (16)	C10—C11	1.5198 (17)
C4—C5	1.4174 (17)	C11—C12	1.5231 (17)
C4—H4A	0.977 (18)	C11—H11A	0.98 (2)
C5—C6	1.4222 (17)	C11—H11B	0.990 (19)
C6—C7	1.3736 (18)
C9—O1—H1O1	109.3 (12)	C6—C7—C8	121.81 (12)
C2—N1—C1	122.14 (11)	C6—C7—H7A	119.1 (10)
C2—N1—H1N1	116.1 (11)	C8—C7—H7A	119.1 (10)
C1—N1—H1N1	121.7 (11)	C9—C8—C7	120.74 (11)
N1—C1—C5	119.31 (10)	C9—C8—H8A	118.7 (10)
N1—C1—C9	119.40 (10)	C7—C8—H8A	120.5 (10)
C5—C1—C9	121.28 (11)	O1—C9—C8	124.86 (11)
N1—C2—C3	121.04 (12)	O1—C9—C1	116.96 (10)
N1—C2—H2A	113.5 (10)	C8—C9—C1	118.17 (11)
C3—C2—H2A	125.5 (10)	C10—O2—H1O2	103.7 (13)
C4—C3—C2	119.00 (11)	O3—C10—O2	121.90 (12)
C4—C3—H3A	123.3 (10)	O3—C10—C11	121.81 (11)
C2—C3—H3A	117.6 (10)	O2—C10—C11	116.29 (11)
C3—C4—C5	120.77 (12)	C10—C11—C12	118.50 (10)
C3—C4—H4A	123.2 (10)	C10—C11—H11A	108.4 (12)
C5—C4—H4A	116.1 (10)	C12—C11—H11A	107.4 (12)
C1—C5—C4	117.72 (11)	C10—C11—H11B	109.3 (11)
C1—C5—C6	118.88 (11)	C12—C11—H11B	107.1 (11)
C4—C5—C6	123.40 (12)	H11A—C11—H11B	105.5 (16)
C7—C6—C5	119.01 (12)	O4—C12—O5	124.50 (11)
C7—C6—H6A	122.8 (9)	O4—C12—C11	119.80 (11)
C5—C6—H6A	118.2 (9)	O5—C12—C11	115.70 (10)
C2—N1—C1—C5	−0.90 (18)	C5—C6—C7—C8	0.37 (19)
C2—N1—C1—C9	−179.97 (11)	C6—C7—C8—C9	2.3 (2)
C1—N1—C2—C3	0.34 (19)	C7—C8—C9—O1	175.89 (11)
N1—C2—C3—C4	0.4 (2)	C7—C8—C9—C1	−3.83 (18)
C2—C3—C4—C5	−0.5 (2)	N1—C1—C9—O1	2.09 (16)
N1—C1—C5—C4	0.71 (17)	C5—C1—C9—O1	−176.97 (11)
C9—C1—C5—C4	179.77 (11)	N1—C1—C9—C8	−178.17 (11)
N1—C1—C5—C6	−179.22 (11)	C5—C1—C9—C8	2.77 (18)
C9—C1—C5—C6	−0.16 (18)	O3—C10—C11—C12	−175.64 (12)
C3—C4—C5—C1	−0.01 (19)	O2—C10—C11—C12	5.39 (18)
C3—C4—C5—C6	179.92 (13)	C10—C11—C12—O4	−3.81 (18)
C1—C5—C6—C7	−1.42 (18)	C10—C11—C12—O5	175.62 (11)
C4—C5—C6—C7	178.66 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O5i	0.97 (2)	1.67 (2)	2.6439 (12)	178.1 (14)
O2—H1O2···O4	0.97 (2)	1.55 (2)	2.4963 (14)	162 (2)
N1—H1N1···O5ii	0.95 (2)	1.74 (2)	2.6809 (14)	170.9 (17)
C2—H2A···O4ii	0.928 (16)	2.373 (17)	3.1735 (15)	144.4 (14)
C2—H2A···O2iii	0.928 (16)	2.423 (16)	3.0663 (15)	126.5 (13)
C6—H6A···O3iv	0.964 (16)	2.462 (16)	3.4202 (16)	172.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O5i	0.97 (2)	1.67 (2)	2.6439 (12)	178.1 (14)
O2—H1O2⋯O4	0.97 (2)	1.55 (2)	2.4963 (14)	162 (2)
N1—H1N1⋯O5ii	0.95 (2)	1.74 (2)	2.6809 (14)	170.9 (17)
C2—H2A⋯O4ii	0.928 (16)	2.373 (17)	3.1735 (15)	144.4 (14)
C2—H2A⋯O2iii	0.928 (16)	2.423 (16)	3.0663 (15)	126.5 (13)
C6—H6A⋯O3iv	0.964 (16)	2.462 (16)	3.4202 (16)	172.5 (13)

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