organic compounds
1-Hydroxyisoquinolin-2-ium hydrogen succinate
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
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
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Data collection: APEX2 (Bruker, 2004); cell 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
10.1107/S1600536814006485/is5349sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006485/is5349Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006485/is5349Isup3.cml
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.
H atoms for CaromaticH and CH2 were positioned geometrically and refined using riding model, with C—H = 0.93 and 0.97 Å, respectively, and with Uiso(H) = 1.2Ueq(C). H atoms bounded to N and O atoms were located in a difference Fourier map and refined with Uiso(H) = 1.5Ueq(N, O) and distance restraints of O—H = 0.82 (1) Å and N—H = 0.86 (1) Å. One reflection (0 0 1) was omited during
as it was showing poor agreement.Data collection: APEX2 (Bruker, 2004); cell
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).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. |
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 |
C9H8NO+·C4H5O4− | V = 584.1 (5) Å3 |
Mr = 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)° |
Bruker Kappa APEXII CCD diffractometer | 3688 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3289 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.982 | Rint = 0.028 |
8297 measured reflections |
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 | Δρmax = 0.57 e Å−3 |
3688 reflections | Δρmin = −0.55 e Å−3 |
181 parameters |
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 |
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. |
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···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) −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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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.