1-Hy-droxy-isoquinolin-2-ium hydrogen succinate.

In the title salt, C9H8NO(+)·C4H5O4 (-), the isoquinolinium ring system is approximately planar [r.m.s deviation = 0.011 (2) Å]. In the crystal, adjacent cations and anions are linked by O-H⋯O and N-H⋯O hydrogen bonds, forming columns along the b axis. The columns are connected by weak C-H⋯O inter-actions into a three-dimensional network.

Related literature

For the biological activity of quinoline derivatives, see: Hopkins et al. (2005 ▶); Musiol et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related quinoline structure, see: Loh et al. (2010 ▶).

Experimental

Crystal data

C9H8NO+·C4H5O4 −

M = 263.24

Monoclinic,

a = 9.553 (5) Å

b = 4.962 (3) Å

c = 12.706 (5) Å

β = 104.117 (5)°

V = 584.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.982

8297 measured reflections

3688 independent reflections

3289 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.169

S = 1.10

3688 reflections

181 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814006485/is5349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006485/is5349Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006485/is5349Isup3.cml

CCDC reference: 993415

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H8NO+·C4H5O4−	F(000) = 276
Mr = 263.24	Dx = 1.497 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4664 reflections
a = 9.553 (5) Å	θ = 2.2–32.6°
b = 4.962 (3) Å	µ = 0.12 mm−1
c = 12.706 (5) Å	T = 295 K
β = 104.117 (5)°	Block, colourless
V = 584.1 (5) Å3	0.22 × 0.18 × 0.16 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	3289 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 33.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
Tmin = 0.975, Tmax = 0.982	k = −6→7
8297 measured reflections	l = −19→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.1138P)2 + 0.0584P] where P = (Fo2 + 2Fc2)/3
3688 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.57 e Å−3
4 restraints	Δρmin = −0.55 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.28708 (17)	1.0029 (4)	0.15427 (13)	0.0248 (3)
C2	0.21024 (18)	1.0069 (4)	0.04383 (12)	0.0268 (3)
C3	0.3651 (2)	0.6470 (5)	0.01057 (17)	0.0378 (4)
H3	0.3901	0.5288	−0.0387	0.045*
C4	0.4391 (2)	0.6380 (4)	0.11717 (17)	0.0345 (4)
H4	0.5135	0.5146	0.1404	0.041*
C5	0.40134 (18)	0.8183 (4)	0.19153 (14)	0.0273 (3)
C6	0.4726 (2)	0.8221 (5)	0.30338 (15)	0.0352 (4)
H6	0.5492	0.7052	0.3300	0.042*
C7	0.4292 (2)	0.9972 (5)	0.37231 (14)	0.0381 (4)
H7	0.4749	0.9978	0.4459	0.046*
C8	0.3161 (2)	1.1745 (5)	0.33147 (14)	0.0342 (4)
H8	0.2870	1.2942	0.3783	0.041*
C9	0.24902 (16)	1.1760 (3)	0.22686 (11)	0.0219 (3)
H9	0.1742	1.2977	0.2021	0.026*
C10	−0.2126 (2)	1.2254 (4)	0.36224 (13)	0.0294 (4)
C11	−0.1045 (2)	0.9998 (5)	0.37431 (13)	0.0337 (4)
H11A	−0.1356	0.8529	0.4136	0.040*
H11B	−0.0122	1.0633	0.4174	0.040*
C12	−0.0841 (2)	0.8927 (4)	0.26675 (13)	0.0303 (3)
H12A	−0.1760	0.8251	0.2246	0.036*
H12B	−0.0559	1.0410	0.2266	0.036*
C13	0.02711 (18)	0.6711 (4)	0.27745 (12)	0.0258 (3)
N1	0.2522 (2)	0.8310 (5)	−0.02600 (14)	0.0423 (4)
H1	0.214 (3)	0.848 (9)	−0.0992 (9)	0.063*
O1	0.10057 (16)	1.1826 (3)	0.01569 (11)	0.0364 (3)
H1A	0.067 (3)	1.149 (7)	−0.0474 (11)	0.055*
O2	−0.23278 (17)	1.3291 (4)	0.45355 (11)	0.0410 (4)
H2A	−0.198 (3)	1.257 (7)	0.5134 (15)	0.061*
O3	−0.27879 (19)	1.3135 (5)	0.27647 (12)	0.0492 (5)
O4	0.04477 (15)	0.5692 (3)	0.19024 (9)	0.0332 (3)
O5	0.09610 (18)	0.5944 (4)	0.36893 (10)	0.0425 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0245 (7)	0.0250 (7)	0.0242 (6)	−0.0023 (6)	0.0042 (5)	0.0003 (6)
C2	0.0285 (8)	0.0263 (8)	0.0234 (6)	−0.0023 (7)	0.0023 (5)	−0.0009 (6)
C3	0.0405 (10)	0.0367 (10)	0.0375 (9)	0.0019 (8)	0.0118 (7)	−0.0097 (8)
C4	0.0335 (8)	0.0329 (10)	0.0371 (9)	0.0060 (7)	0.0088 (7)	0.0011 (7)
C5	0.0259 (7)	0.0275 (8)	0.0284 (6)	−0.0007 (7)	0.0064 (6)	0.0019 (6)
C6	0.0308 (8)	0.0414 (11)	0.0305 (7)	0.0065 (8)	0.0015 (6)	0.0067 (7)
C7	0.0390 (10)	0.0474 (12)	0.0246 (7)	0.0031 (9)	0.0010 (6)	0.0000 (8)
C8	0.0363 (9)	0.0406 (10)	0.0244 (7)	0.0025 (8)	0.0048 (6)	−0.0041 (7)
C9	0.0215 (6)	0.0236 (7)	0.0190 (5)	0.0008 (6)	0.0022 (5)	−0.0010 (5)
C10	0.0318 (8)	0.0310 (9)	0.0251 (6)	0.0048 (7)	0.0065 (6)	0.0020 (6)
C11	0.0425 (10)	0.0346 (9)	0.0219 (6)	0.0133 (8)	0.0038 (6)	0.0019 (6)
C12	0.0359 (9)	0.0322 (9)	0.0215 (6)	0.0067 (7)	0.0047 (6)	0.0013 (6)
C13	0.0290 (7)	0.0249 (8)	0.0220 (6)	0.0003 (6)	0.0036 (5)	−0.0006 (5)
N1	0.0468 (10)	0.0450 (11)	0.0331 (7)	−0.0002 (9)	0.0058 (7)	−0.0062 (8)
O1	0.0384 (7)	0.0378 (8)	0.0273 (6)	0.0087 (6)	−0.0031 (5)	−0.0047 (5)
O2	0.0439 (8)	0.0501 (9)	0.0283 (6)	0.0138 (7)	0.0077 (5)	−0.0033 (6)
O3	0.0540 (9)	0.0608 (12)	0.0310 (6)	0.0270 (9)	0.0069 (6)	0.0116 (7)
O4	0.0389 (7)	0.0384 (8)	0.0205 (5)	0.0064 (6)	0.0036 (4)	−0.0035 (5)
O5	0.0549 (9)	0.0469 (9)	0.0213 (5)	0.0213 (8)	0.0010 (5)	−0.0017 (5)

C1—C9	1.373 (2)	C8—H8	0.9300
C1—C5	1.415 (2)	C9—H9	0.9300
C1—C2	1.416 (2)	C10—O3	1.201 (2)
C2—O1	1.343 (2)	C10—O2	1.325 (2)
C2—N1	1.372 (2)	C10—C11	1.506 (3)
C3—C4	1.367 (3)	C11—C12	1.522 (2)
C3—N1	1.403 (3)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.410 (3)	C12—C13	1.512 (3)
C4—H4	0.9300	C12—H12A	0.9700
C5—C6	1.418 (2)	C12—H12B	0.9700
C6—C7	1.368 (3)	C13—O5	1.248 (2)
C6—H6	0.9300	C13—O4	1.266 (2)
C7—C8	1.392 (3)	N1—H1	0.917 (10)
C7—H7	0.9300	O1—H1A	0.806 (10)
C8—C9	1.327 (2)	O2—H2A	0.833 (10)
C9—C1—C5	119.31 (14)	C8—C9—H9	119.1
C9—C1—C2	119.92 (15)	C1—C9—H9	119.1
C5—C1—C2	120.77 (15)	O3—C10—O2	119.75 (18)
O1—C2—N1	124.95 (15)	O3—C10—C11	124.01 (17)
O1—C2—C1	117.06 (15)	O2—C10—C11	116.24 (15)
N1—C2—C1	117.98 (16)	C10—C11—C12	113.75 (14)
C4—C3—N1	121.27 (18)	C10—C11—H11A	108.8
C4—C3—H3	119.4	C12—C11—H11A	108.8
N1—C3—H3	119.4	C10—C11—H11B	108.8
C3—C4—C5	119.22 (18)	C12—C11—H11B	108.8
C3—C4—H4	120.4	H11A—C11—H11B	107.7
C5—C4—H4	120.4	C13—C12—C11	114.45 (14)
C4—C5—C1	119.27 (16)	C13—C12—H12A	108.6
C4—C5—C6	122.75 (18)	C11—C12—H12A	108.6
C1—C5—C6	117.98 (16)	C13—C12—H12B	108.6
C7—C6—C5	120.24 (18)	C11—C12—H12B	108.6
C7—C6—H6	119.9	H12A—C12—H12B	107.6
C5—C6—H6	119.9	O5—C13—O4	122.73 (17)
C6—C7—C8	119.46 (16)	O5—C13—C12	120.36 (14)
C6—C7—H7	120.3	O4—C13—C12	116.91 (14)
C8—C7—H7	120.3	C2—N1—C3	121.47 (16)
C9—C8—C7	121.22 (18)	C2—N1—H1	119 (3)
C9—C8—H8	119.4	C3—N1—H1	119 (2)
C7—C8—H8	119.4	C2—O1—H1A	103 (2)
C8—C9—C1	121.79 (17)	C10—O2—H2A	122 (2)
C9—C1—C2—O1	−0.7 (2)	C5—C6—C7—C8	−1.0 (3)
C5—C1—C2—O1	178.07 (16)	C6—C7—C8—C9	0.3 (3)
C9—C1—C2—N1	179.79 (17)	C7—C8—C9—C1	0.3 (3)
C5—C1—C2—N1	−1.5 (3)	C5—C1—C9—C8	−0.3 (3)
N1—C3—C4—C5	−0.2 (3)	C2—C1—C9—C8	178.46 (18)
C3—C4—C5—C1	0.4 (3)	O3—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	179.99 (19)	O2—C10—C11—C12	−178.94 (18)
C9—C1—C5—C4	179.17 (17)	C10—C11—C12—C13	178.42 (17)
C2—C1—C5—C4	0.4 (3)	C11—C12—C13—O5	−1.7 (3)
C9—C1—C5—C6	−0.4 (2)	C11—C12—C13—O4	177.79 (17)
C2—C1—C5—C6	−179.14 (17)	O1—C2—N1—C3	−177.81 (19)
C4—C5—C6—C7	−178.5 (2)	C1—C2—N1—C3	1.7 (3)
C1—C5—C6—C7	1.1 (3)	C4—C3—N1—C2	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.92 (1)	2.48 (2)	3.255 (3)	142 (3)
O1—H1A···O4ii	0.81 (1)	1.91 (1)	2.705 (2)	170 (3)
O2—H2A···O5iii	0.83 (1)	1.77 (1)	2.591 (2)	169 (3)
C4—H4···O3iv	0.93	2.50	3.360 (3)	154
C8—H8···O5v	0.93	2.34	3.078 (3)	137
C9—H9···O4v	0.93	1.81	2.718 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.92 (1)	2.48 (2)	3.255 (3)	142 (3)
O1—H1A⋯O4ii	0.81 (1)	1.91 (1)	2.705 (2)	170 (3)
O2—H2A⋯O5iii	0.83 (1)	1.77 (1)	2.591 (2)	169 (3)
C4—H4⋯O3iv	0.93	2.50	3.360 (3)	154
C8—H8⋯O5v	0.93	2.34	3.078 (3)	137
C9—H9⋯O4v	0.93	1.81	2.718 (2)	165

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