organic compounds
8-Hydroxy-5,7-dimethylquinolin-1-ium chloride dihydrate
aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my
In the title hydrated salt, C11H12NO+·Cl−·2H2O, the quinoline ring system is essentially planar, with a maximum deviation of 0.005 (1) Å for all non-H atoms. In the crystal, the three components are linked by O—H⋯O, N—H⋯O, O—H⋯Cl and weak C—H⋯O hydrogen bonds, forming a layer structure parallel to the ac plane. The is further stabilized by π–π stacking interactions, with centroid–centroid distances of 3.5213 (6) and 3.7176 (6) Å.
Related literature
For background to and the biological activity of quinoline derivatives, see: Balasubramanian & Muthiah (1996a,b); Morimoto et al. (1991); Markees et al. (1970). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
https://doi.org/10.1107/S1600536812049495/is5226sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049495/is5226Isup2.hkl
To a hot methanol solution (20 ml) of 8-hydroxy-5,7-dimethylquinoline (36 mg, Aldrich) was added a few drops of hydrochloric acid. The solution was warmed over a heating magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly at room temperature and crystals of the title compound (I) appeared after a few days.
O- and N-bound H atoms were located in a difference Fourier map and were refined freely [O—H = 0.76 (2)–0.873 (19) Å and N—H = 0.828 (19) Å]. The rest of the hydrogen atoms were positioned geometrically (C—H = 0.95–0.98 Å) and were refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). A rotating-group model was used for the methyl group. Eight outliers were omitted (-3 1 0, 4 -6 2, -4 0 5, -4 -2 3, -4 -3 2, -4 1 5, -4 -3 3 and 3 4 1) in the final refinement.
Recently, much attention has been devoted to the design and synthesis of supramolecular architectures assembled via various weak noncovalent interactions in the crystal structures of oxines (8-hydroxyquinoline), their derivatives and their complexes in a variety of crystalline environments (Balasubramanian & Muthiah, 1996a,b). Oxine is widely used as analytical reagent. Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991) and biologically active compounds (Markees et al., 1970). In order to study potential hydrogen bonding interactions the
determination of the title compound (I) was carried out.The
of the title compound, (I) contains a 8-hydroxy-5,7-dimethylquinolin-1-ium cation, a chloride anion and two water molecules as shown in Fig. 1. One proton is transferred from the hydrochloric acid to the atom N1 of 8-hydroxy-5,7-dimethylquinoline during the crystallization, resulting the formation of salt. The quinoline ring system (N1/C1–C9) is planar with a maximum deviation of 0.005 (1) Å at atom C7. The bond lengths (Allen et al., 1987) and angles are normal.In the crystal packing (Fig. 2), the ion pairs and water molecules are linked via O2W—H2W2···Cl1, O1—H1O1···O1W, N1—H1N1···O1Wi, O1W—H2W1···Cl1i, O2W—H1W2···Cl1ii, O1W—H1W1···O2Wiii and weak C1—H1A···O2W hydrogen bonds (symmetry codes in Table 1), forming a layer. Furthermore, the π–π interactions: (a) between pyridine (N1/C1–C4/C9, centroid Cg1) and benzene (C4–C9, centroid Cg2) rings Cg1···Cg2 (1 - x, -y, 1 - z) 3.5213 (6) Å and (b) between benzene rings (C4–C9, centroid Cg2) Cg2···Cg2 (-x, -y, 1 - z) 3.7176 (6) Å.
is stabilized by the followingFor background to and the biological activity of quinoline derivatives, see: Balasubramanian & Muthiah (1996a,b); Morimoto et al. (1991); Markees et al. (1970). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with atom labels with 50% probability displacement ellipsoids. | |
Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity. |
C11H12NO+·Cl−·2H2O | Z = 2 |
Mr = 245.70 | F(000) = 260 |
Triclinic, P1 | Dx = 1.383 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7990 (5) Å | Cell parameters from 6250 reflections |
b = 9.2215 (6) Å | θ = 2.7–30.1° |
c = 10.2123 (7) Å | µ = 0.32 mm−1 |
α = 103.820 (1)° | T = 100 K |
β = 95.629 (1)° | Block, yellow |
γ = 105.517 (1)° | 0.38 × 0.20 × 0.14 mm |
V = 590.04 (7) Å3 |
Bruker APEXII DUO CCD area-detector diffractometer | 3410 independent reflections |
Radiation source: fine-focus sealed tube | 3153 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 30.1°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.889, Tmax = 0.958 | k = −12→12 |
9368 measured reflections | l = −14→14 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.058P)2 + 0.1137P] where P = (Fo2 + 2Fc2)/3 |
3410 reflections | (Δ/σ)max = 0.001 |
171 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C11H12NO+·Cl−·2H2O | γ = 105.517 (1)° |
Mr = 245.70 | V = 590.04 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7990 (5) Å | Mo Kα radiation |
b = 9.2215 (6) Å | µ = 0.32 mm−1 |
c = 10.2123 (7) Å | T = 100 K |
α = 103.820 (1)° | 0.38 × 0.20 × 0.14 mm |
β = 95.629 (1)° |
Bruker APEXII DUO CCD area-detector diffractometer | 3410 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3153 reflections with I > 2σ(I) |
Tmin = 0.889, Tmax = 0.958 | Rint = 0.018 |
9368 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.43 e Å−3 |
3410 reflections | Δρmin = −0.26 e Å−3 |
171 parameters |
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 | ||
Cl1 | 0.22874 (4) | 0.70417 (3) | 0.91682 (2) | 0.01867 (8) | |
O1W | 0.49841 (12) | 0.45266 (8) | 0.25460 (7) | 0.01707 (15) | |
O1 | 0.34288 (12) | 0.31466 (8) | 0.43983 (7) | 0.01753 (15) | |
O2W | 0.22470 (13) | 0.42047 (10) | 1.03561 (8) | 0.02223 (16) | |
N1 | 0.35726 (12) | 0.22535 (9) | 0.66748 (8) | 0.01260 (15) | |
C1 | 0.36928 (14) | 0.19382 (11) | 0.78767 (9) | 0.01493 (17) | |
H1A | 0.4133 | 0.2770 | 0.8699 | 0.018* | |
C2 | 0.31746 (15) | 0.03900 (11) | 0.79353 (9) | 0.01541 (17) | |
H2A | 0.3259 | 0.0159 | 0.8793 | 0.018* | |
C3 | 0.25385 (14) | −0.08005 (11) | 0.67341 (9) | 0.01452 (17) | |
H3A | 0.2176 | −0.1858 | 0.6769 | 0.017* | |
C4 | 0.24166 (13) | −0.04734 (10) | 0.54510 (9) | 0.01229 (16) | |
C5 | 0.17880 (14) | −0.16484 (10) | 0.41697 (9) | 0.01365 (17) | |
C6 | 0.17410 (14) | −0.11634 (10) | 0.29989 (9) | 0.01398 (17) | |
H6A | 0.1328 | −0.1942 | 0.2143 | 0.017* | |
C7 | 0.22731 (13) | 0.04326 (10) | 0.29896 (9) | 0.01296 (17) | |
C8 | 0.29038 (13) | 0.15788 (10) | 0.42249 (9) | 0.01246 (16) | |
C9 | 0.29632 (13) | 0.11195 (10) | 0.54492 (9) | 0.01168 (16) | |
C10 | 0.11810 (16) | −0.33626 (11) | 0.41114 (10) | 0.01908 (19) | |
H10A | 0.0812 | −0.3994 | 0.3153 | 0.029* | |
H10B | −0.0012 | −0.3613 | 0.4573 | 0.029* | |
H10C | 0.2348 | −0.3595 | 0.4569 | 0.029* | |
C11 | 0.21195 (15) | 0.08368 (11) | 0.16520 (9) | 0.01676 (18) | |
H11A | 0.1307 | 0.1572 | 0.1680 | 0.025* | |
H11B | 0.1439 | −0.0118 | 0.0908 | 0.025* | |
H11C | 0.3513 | 0.1320 | 0.1494 | 0.025* | |
H1N1 | 0.389 (3) | 0.318 (2) | 0.6664 (18) | 0.037 (4)* | |
H2W1 | 0.584 (3) | 0.411 (2) | 0.2240 (19) | 0.040 (5)* | |
H2W2 | 0.228 (3) | 0.497 (2) | 1.001 (2) | 0.050 (5)* | |
H1O1 | 0.385 (3) | 0.347 (2) | 0.3707 (19) | 0.038 (4)* | |
H1W2 | 0.115 (3) | 0.390 (2) | 1.0495 (18) | 0.036 (4)* | |
H1W1 | 0.416 (3) | 0.446 (2) | 0.1895 (19) | 0.038 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02078 (13) | 0.01844 (12) | 0.01979 (13) | 0.00704 (9) | 0.00619 (9) | 0.00844 (9) |
O1W | 0.0219 (3) | 0.0155 (3) | 0.0134 (3) | 0.0053 (3) | 0.0038 (3) | 0.0035 (2) |
O1 | 0.0275 (4) | 0.0127 (3) | 0.0126 (3) | 0.0050 (3) | 0.0048 (3) | 0.0046 (2) |
O2W | 0.0205 (4) | 0.0251 (4) | 0.0262 (4) | 0.0094 (3) | 0.0057 (3) | 0.0130 (3) |
N1 | 0.0138 (3) | 0.0131 (3) | 0.0105 (3) | 0.0039 (3) | 0.0020 (3) | 0.0027 (3) |
C1 | 0.0157 (4) | 0.0183 (4) | 0.0103 (4) | 0.0050 (3) | 0.0021 (3) | 0.0032 (3) |
C2 | 0.0165 (4) | 0.0192 (4) | 0.0119 (4) | 0.0058 (3) | 0.0029 (3) | 0.0061 (3) |
C3 | 0.0146 (4) | 0.0160 (4) | 0.0143 (4) | 0.0048 (3) | 0.0033 (3) | 0.0061 (3) |
C4 | 0.0112 (4) | 0.0142 (4) | 0.0120 (4) | 0.0044 (3) | 0.0021 (3) | 0.0040 (3) |
C5 | 0.0134 (4) | 0.0131 (4) | 0.0140 (4) | 0.0040 (3) | 0.0025 (3) | 0.0029 (3) |
C6 | 0.0140 (4) | 0.0147 (4) | 0.0118 (4) | 0.0040 (3) | 0.0019 (3) | 0.0015 (3) |
C7 | 0.0123 (4) | 0.0158 (4) | 0.0110 (4) | 0.0046 (3) | 0.0022 (3) | 0.0038 (3) |
C8 | 0.0133 (4) | 0.0134 (4) | 0.0114 (4) | 0.0044 (3) | 0.0028 (3) | 0.0041 (3) |
C9 | 0.0108 (3) | 0.0142 (4) | 0.0100 (4) | 0.0041 (3) | 0.0022 (3) | 0.0028 (3) |
C10 | 0.0241 (5) | 0.0128 (4) | 0.0187 (4) | 0.0039 (3) | 0.0031 (4) | 0.0033 (3) |
C11 | 0.0208 (4) | 0.0188 (4) | 0.0100 (4) | 0.0052 (3) | 0.0015 (3) | 0.0040 (3) |
O1W—H2W1 | 0.828 (19) | C4—C9 | 1.4160 (12) |
O1W—H1W1 | 0.806 (19) | C4—C5 | 1.4262 (12) |
O1—C8 | 1.3558 (11) | C5—C6 | 1.3735 (12) |
O1—H1O1 | 0.873 (19) | C5—C10 | 1.5079 (13) |
O2W—H2W2 | 0.86 (2) | C6—C7 | 1.4211 (12) |
O2W—H1W2 | 0.76 (2) | C6—H6A | 0.9500 |
N1—C1 | 1.3271 (11) | C7—C8 | 1.3809 (12) |
N1—C9 | 1.3686 (11) | C7—C11 | 1.5006 (12) |
N1—H1N1 | 0.828 (19) | C8—C9 | 1.4129 (12) |
C1—C2 | 1.3935 (13) | C10—H10A | 0.9800 |
C1—H1A | 0.9500 | C10—H10B | 0.9800 |
C2—C3 | 1.3768 (13) | C10—H10C | 0.9800 |
C2—H2A | 0.9500 | C11—H11A | 0.9800 |
C3—C4 | 1.4127 (12) | C11—H11B | 0.9800 |
C3—H3A | 0.9500 | C11—H11C | 0.9800 |
H2W1—O1W—H1W1 | 106.5 (17) | C7—C6—H6A | 118.0 |
C8—O1—H1O1 | 116.0 (11) | C8—C7—C6 | 118.69 (8) |
H2W2—O2W—H1W2 | 107.8 (19) | C8—C7—C11 | 121.56 (8) |
C1—N1—C9 | 123.25 (8) | C6—C7—C11 | 119.75 (8) |
C1—N1—H1N1 | 118.5 (12) | O1—C8—C7 | 126.20 (8) |
C9—N1—H1N1 | 118.2 (12) | O1—C8—C9 | 115.02 (8) |
N1—C1—C2 | 120.13 (8) | C7—C8—C9 | 118.75 (8) |
N1—C1—H1A | 119.9 | N1—C9—C8 | 118.85 (8) |
C2—C1—H1A | 119.9 | N1—C9—C4 | 118.90 (8) |
C3—C2—C1 | 119.17 (8) | C8—C9—C4 | 122.25 (8) |
C3—C2—H2A | 120.4 | C5—C10—H10A | 109.5 |
C1—C2—H2A | 120.4 | C5—C10—H10B | 109.5 |
C2—C3—C4 | 121.00 (8) | H10A—C10—H10B | 109.5 |
C2—C3—H3A | 119.5 | C5—C10—H10C | 109.5 |
C4—C3—H3A | 119.5 | H10A—C10—H10C | 109.5 |
C3—C4—C9 | 117.54 (8) | H10B—C10—H10C | 109.5 |
C3—C4—C5 | 123.88 (8) | C7—C11—H11A | 109.5 |
C9—C4—C5 | 118.58 (8) | C7—C11—H11B | 109.5 |
C6—C5—C4 | 117.73 (8) | H11A—C11—H11B | 109.5 |
C6—C5—C10 | 121.45 (8) | C7—C11—H11C | 109.5 |
C4—C5—C10 | 120.82 (8) | H11A—C11—H11C | 109.5 |
C5—C6—C7 | 123.99 (8) | H11B—C11—H11C | 109.5 |
C5—C6—H6A | 118.0 | ||
C9—N1—C1—C2 | −0.37 (14) | C11—C7—C8—O1 | 0.57 (14) |
N1—C1—C2—C3 | −0.04 (14) | C6—C7—C8—C9 | −1.01 (13) |
C1—C2—C3—C4 | 0.35 (14) | C11—C7—C8—C9 | 178.35 (8) |
C2—C3—C4—C9 | −0.27 (13) | C1—N1—C9—C8 | −179.47 (8) |
C2—C3—C4—C5 | 179.45 (8) | C1—N1—C9—C4 | 0.44 (13) |
C3—C4—C5—C6 | −179.96 (8) | O1—C8—C9—N1 | −1.49 (12) |
C9—C4—C5—C6 | −0.25 (12) | C7—C8—C9—N1 | −179.51 (8) |
C3—C4—C5—C10 | 0.53 (13) | O1—C8—C9—C4 | 178.60 (8) |
C9—C4—C5—C10 | −179.75 (8) | C7—C8—C9—C4 | 0.59 (13) |
C4—C5—C6—C7 | −0.21 (13) | C3—C4—C9—N1 | −0.12 (12) |
C10—C5—C6—C7 | 179.30 (8) | C5—C4—C9—N1 | −179.85 (8) |
C5—C6—C7—C8 | 0.86 (14) | C3—C4—C9—C8 | 179.79 (8) |
C5—C6—C7—C11 | −178.51 (9) | C5—C4—C9—C8 | 0.06 (13) |
C6—C7—C8—O1 | −178.78 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O2W | 0.95 | 2.55 | 3.2871 (13) | 134 |
O2W—H2W2···Cl1 | 0.858 (19) | 2.274 (19) | 3.1306 (10) | 177.4 (18) |
O1—H1O1···O1W | 0.874 (19) | 1.811 (19) | 2.6718 (10) | 167.9 (18) |
N1—H1N1···O1Wi | 0.826 (18) | 1.977 (18) | 2.7516 (11) | 155.9 (17) |
O1W—H2W1···Cl1i | 0.83 (2) | 2.27 (2) | 3.0758 (9) | 164.0 (18) |
O2W—H1W2···Cl1ii | 0.76 (2) | 2.36 (2) | 3.1187 (10) | 177.7 (18) |
O1W—H1W1···O2Wiii | 0.805 (19) | 1.86 (2) | 2.6690 (11) | 177.2 (19) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+2; (iii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C11H12NO+·Cl−·2H2O |
Mr | 245.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 6.7990 (5), 9.2215 (6), 10.2123 (7) |
α, β, γ (°) | 103.820 (1), 95.629 (1), 105.517 (1) |
V (Å3) | 590.04 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.38 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.889, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9368, 3410, 3153 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.092, 1.08 |
No. of reflections | 3410 |
No. of parameters | 171 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.43, −0.26 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O2W | 0.95 | 2.55 | 3.2871 (13) | 134 |
O2W—H2W2···Cl1 | 0.858 (19) | 2.274 (19) | 3.1306 (10) | 177.4 (18) |
O1—H1O1···O1W | 0.874 (19) | 1.811 (19) | 2.6718 (10) | 167.9 (18) |
N1—H1N1···O1Wi | 0.826 (18) | 1.977 (18) | 2.7516 (11) | 155.9 (17) |
O1W—H2W1···Cl1i | 0.83 (2) | 2.27 (2) | 3.0758 (9) | 164.0 (18) |
O2W—H1W2···Cl1ii | 0.76 (2) | 2.36 (2) | 3.1187 (10) | 177.7 (18) |
O1W—H1W1···O2Wiii | 0.805 (19) | 1.86 (2) | 2.6690 (11) | 177.2 (19) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+2; (iii) x, y, z−1. |
Footnotes
‡Thomson Reuters ResearcherID: A-5599-2009.
Acknowledgements
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant No. 304/PFIZIK/6312078 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS–USM fellowship.
References
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Recently, much attention has been devoted to the design and synthesis of supramolecular architectures assembled via various weak noncovalent interactions in the crystal structures of oxines (8-hydroxyquinoline), their derivatives and their complexes in a variety of crystalline environments (Balasubramanian & Muthiah, 1996a,b). Oxine is widely used as analytical reagent. Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991) and biologically active compounds (Markees et al., 1970). In order to study potential hydrogen bonding interactions the crystal structure determination of the title compound (I) was carried out.
The asymmetric unit of the title compound, (I) contains a 8-hydroxy-5,7-dimethylquinolin-1-ium cation, a chloride anion and two water molecules as shown in Fig. 1. One proton is transferred from the hydrochloric acid to the atom N1 of 8-hydroxy-5,7-dimethylquinoline during the crystallization, resulting the formation of salt. The quinoline ring system (N1/C1–C9) is planar with a maximum deviation of 0.005 (1) Å at atom C7. The bond lengths (Allen et al., 1987) and angles are normal.
In the crystal packing (Fig. 2), the ion pairs and water molecules are linked via O2W—H2W2···Cl1, O1—H1O1···O1W, N1—H1N1···O1Wi, O1W—H2W1···Cl1i, O2W—H1W2···Cl1ii, O1W—H1W1···O2Wiii and weak C1—H1A···O2W hydrogen bonds (symmetry codes in Table 1), forming a layer. Furthermore, the crystal structure is stabilized by the following π–π interactions: (a) between pyridine (N1/C1–C4/C9, centroid Cg1) and benzene (C4–C9, centroid Cg2) rings Cg1···Cg2 (1 - x, -y, 1 - z) 3.5213 (6) Å and (b) between benzene rings (C4–C9, centroid Cg2) Cg2···Cg2 (-x, -y, 1 - z) 3.7176 (6) Å.