1-Hy­droxy­isoquinolin-2-ium hydrogen succinate

Ambalatharasu, S.; Sankar, A.; Peramaiyan, G.; Chakkaravarthi, G.; Kanagadurai, R.

doi:10.1107/S1600536814006485

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o491

doi:10.1107/S1600536814006485

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1-Hydroxyisoquinolin-2-ium hydrogen succinate

S. Ambalatharasu,^a A. Sankar,^a G. Peramaiyan,^a G. Chakkaravarthi ^b ^* and R. Kanagadurai ^a ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, and ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, srkanagadurai@yahoo.co.in

(Received 18 March 2014; accepted 24 March 2014; online 29 March 2014)

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 interactions into a three-dimensional network.

CCDC reference: 993415

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_r = 263.24
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.169
S = 1.10
3688 reflections
181 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.55 e Å⁻³

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⋯O3^iv	0.93	2.50	3.360 (3)	154
C8—H8⋯O5^v	0.93	2.34	3.078 (3)	137
C9—H9⋯O4^v	0.93	1.81	2.718 (2)	165
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iv) x+1, y-1, z; (v) x, y+1, z.

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.

Supporting information

CCDC reference: 993415

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814006485/is5349sup1.cif

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

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

checkCIF report

Comment top

Quinolinium derivatives are known to exhibit interesting bioactivities and pharmacological activities (Hopkins et al., 2005; Musiol et al., 2006). We herewith report the crystal structure of the title compound (Fig. 1). The bond lengths of the anion are within normal range (Allen et al., 1987) and the bond lengths of cation are comparable with the reported similar structure (Loh et al., 2010).

In the cation, the isoquinolinium ring system is planar [r.m.s deviation = 0.011 (2) Å]. The adjacent cations and anions are linked by weak intermolecular O—H···O and N—H···O interactions (Table 1 and Fig. 2 ) to form a column along the b axis. Weak π–π [Cg1···Cg1 (1-x, 1/2+y, -z) distance = 4.994 (3) Å, Cg1···Cg2 (x, -1+y, z) distance = 4.673 (3) Å; Cg1 and Cg2 are the centroids of the rings (N1/C1–C5) and (C1/C5–C9), respectively] and C—H···O interactions are also observed in the crystal structure.

Related literature top

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 top

1-Hydroxyisoquinolin-2-ium succinate was synthesized using the raw materials 1-hydroxyisoquinoline (1.45 g) and succinic acid (1.18 g) in an equimolar ratio. These reactants were dissolved in 10 ml of ethanol solvent and yellow precipitate was obtained after some time. The precipitate was dissolved in the same solvent and it is kept at room temperature for crystallization. After a span of four days, rod like crystals for diffraction study were harvested.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title cpompound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing diagram of the title compound, viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

1-Hydroxyisoquinolin-2-ium 3-carboxypropionate top

Crystal data top

C₉H₈NO⁺·C₄H₅O₄⁻	F(000) = 276
M_r = 263.24	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1138P)² + 0.0584P] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.57 e Å⁻³
4 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₉H₈NO⁺·C₄H₅O₄⁻	V = 584.1 (5) Å³
M_r = 263.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.553 (5) Å	µ = 0.12 mm⁻¹
b = 4.962 (3) Å	T = 295 K
c = 12.706 (5) Å	0.22 × 0.18 × 0.16 mm
β = 104.117 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3688 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3289 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.028
8297 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	4 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.57 e Å⁻³
3688 reflections	Δρ_min = −0.55 e Å⁻³
181 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.93	2.50	3.360 (3)	154
C8—H8···O5^v	0.93	2.34	3.078 (3)	137
C9—H9···O4^v	0.93	1.81	2.718 (2)	165

Symmetry codes: (i) −x, y−1/2, −z; (ii) −x, y+1/2, −z; (iii) −x, y+1/2, −z+1; (iv) x+1, y−1, z; (v) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.917 (10)	2.48 (2)	3.255 (3)	142 (3)
O1—H1A···O4ⁱⁱ	0.806 (10)	1.908 (11)	2.705 (2)	170 (3)
O2—H2A···O5ⁱⁱⁱ	0.833 (10)	1.768 (12)	2.591 (2)	169 (3)
C4—H4···O3^iv	0.93	2.50	3.360 (3)	154
C8—H8···O5^v	0.93	2.34	3.078 (3)	137
C9—H9···O4^v	0.93	1.81	2.718 (2)	165

Symmetry codes: (i) −x, y−1/2, −z; (ii) −x, y+1/2, −z; (iii) −x, y+1/2, −z+1; (iv) x+1, y−1, z; (v) x, y+1, z.

Acknowledgements

The authors thank the SAIF, IIT, Madras, for the data collection.

References

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